Columnar supramolecular architecture of crystals of 2-(4-Iodophenyl)-1,10-phenanthroline derived from values of intermolecular interaction energy

Using results of X-ray diffraction study supramolecular architecture of crystals of 2-(4-iodophenyl)-1,10-phenanthroline has been analyzed on the basis of quantum-chemical calculations of intermolecular interactions energy. It is demonstrated that these crystals have three levels of organization. Molecules form stacked dimers with the highest binding energy (first level). These dimers represent basic unit of infinite columns stabilized by stacking interactions between dimers (second level). The energy of intermolecular interactions between neighbouring stacked columns is very close. This does not allow to figure out any layers in the crystal. Therefore crystals of this compound have columna…

Unexpected Scholl Reaction of 6,7,13,14-Tetraarylbenzo[k]tetraphene: Selective Formation of Five-Membered Rings in Polycyclic Aromatic Hydrocarbons

Cyclodehydrogenation is a versatile reaction that has enabled the syntheses of numerous polycyclic aromatic hydrocarbons (PAHs). We now describe a unique Scholl reaction of 6,7,13,14-tetraarylbenzo[k]tetraphene, which "unexpectedly" forms five-membered rings accompanying highly selective 1,2-shift of aryl groups. The geometric and optoelectronic nature of the resulting bistetracene analogue with five-membered rings is comprehensively investigated by single-crystal X-ray, NMR, UV-vis absorption, and cyclic voltammetry analyses. Furthermore, a possible mechanism is proposed to account for the selective five-membered-ring formation with the rearrangement of the aryl groups, which can be ration…

Dibenzo[hi,st]ovalene as Highly Luminescent Nanographene: Efficient Synthesis via Photochemical Cyclodehydroiodination, Optoelectronic Properties, and Single-Molecule Spectroscopy

Dibenzo[hi,st]ovalene (DBOV), as a new nanographene, has demonstrated promising optical properties, such as red emission with a high fluorescence quantum yield of 79% and stimulated emission, as well as high thermal stability and photostability, which indicated its promise as a light-emitting and optical gain material. However, the previous synthetic routes required at least 12 steps. This obstructed access to different derivatives, e.g., to obtain crystals suitable for X-ray diffraction analysis and to tune the optoelectronic properties. Here, we report an efficient synthetic pathway to DBOV based on a sequential iodination-benzannulation of bi(naphthylphenyl)diyne, followed by photochemic…

Naphthyridine Derivatives as a Model System for Potential Lithium-Sulfur Energy-Storage Applications

Naphthyridines have been identified as structural elements in sulfurized polyacrylonitrile, which is a common electrode material in lithium–sulfur batteries. Some dibenzonaphthyridine derivatives with a fused dithiolo moiety were prepared as model compounds for battery studies. These heterocyclic systems were prepared via the corresponding diphenyldicarbamide intermediate. Followed by naphthyridione formation, stepwise installation of the dithiolane subunit occurred in a straightforward manner. In the solid state, the heteroaromatic system is completely planar and was thoroughly characterized. Initial battery cycling tests indicated a potential use of such structural motifs in sulfur–lithiu…

ChemInform Abstract: Powerful Fluoroalkoxy Molybdenum(V) Reagent for Selective Oxidative Arene Coupling Reaction.

A novel dinuclear fluoroalkoxy Mo(V)-complex is efficient as reagent for the oxidative arene coupling of electron-rich arenes with superior reactivity compared to MoCl5 and MoCl5/TiCl4.

(3RS,1SR)-3-Bromo-3-(1-phenylpropyl)chroman-2,4-dione

The title compound, C18H15BrO3, was obtained by bromination of phenprocoumone with N-bromo­succin­imide. The X-ray structure confirms an earlier proposal concerning the regioselectivity of the reaction to introduce the Br atom at the 3-position.

Triphenanthro‐anellierte [18]Annulene mit Alkoxy‐Seitenketten — Eine neue Klasse discotischer Flüssigkristalle

Triphenanthro-Anellated [18]Annulenes with Alkoxy Side Chains - A Novel Class of Discotic Liquid Crystals Two different types 6 and 16 of [18]annulenes condensed with phenanthrene systems were prepared by cyclocondensation reactions (Schemes 2 and 3). The central 18-membered rings do not show a macrocyclic diamagnetic ring current. Conformational analyses and X-ray analyses in the solid state reveal non-planar structures in which aromatic “islands” are connected by (E)-configurated olefinic bridges. The introduction of long alkoxy side chains yields a new class of discotic liquid crystals; either ND or hexagonal columnar phases are generated, which were characterized by DSC, microscopy with…

Palladium-catalyzed domino C-H/N-H functionalization: an efficient approach to nitrogen-bridged heteroacenes.

Palladium-catalyzed domino C-H/N-H functionalization for the synthesis of novel nitrogen-bridged thienoacenes and 10H-benzo[4,5]thieno[3,2-b]indole derivatives from dihaloarene is reported. This domino sequence consists of initial C-H functionalization of the benzo[b]thiophene moiety, followed by Buchwald-Hartwig coupling. This transformation is also useful for the synthesis of highly π-extended compounds.

π-Extended Pyrene-Fused Double [7]Carbohelicene as a Chiral Polycyclic Aromatic Hydrocarbon

A π-extended double [7]carbohelicene 2 with fused pyrene units was synthesized, revealing considerable intra- and intermolecular π–π interactions as confirmed with X-ray crystallography. As compared to the previous double [7]carbohelicene 1, the π-extended homologue 2 demonstrated considerably red-shifted absorption with an onset at 645 nm (1: 550 nm) corresponding to a smaller optical gap of 1.90 eV (1: 2.25 eV). A broad near-infrared emission from 600 to 900 nm with a large Stokes shift of ∼100 nm (2.3 × 103 cm–1) was recorded for 2, implying formation of an intramolecular excimer upon excitation, which was corroborated with femtosecond transient absorption spectroscopy. Moreover, 2 revea…

(2S,3′S,3a'R,5′R,7a'R)-5′-[(E)-5-(Furan-3-yl)-2-methylpent-1-en-1-yl]-3-hydroxy-3′,4,7′-trimethyl-1′,2′,3′,3a',5′,7a'-hexahydro-5H-spiro[furan-2,4′-inden]-5-one

The title compound, ircinianin, C25H32O4, belongs to the sesterterpene tetronic acid compound family and was isolated from the marine sponge Ircinia wistarii. These chemical scaffolds are pharmacologically relevant, since they represent a new class of glycine receptor modulators. The furan ring makes a dihedral angle of 35.14 (12)° to the 4-hydroxy-3-methylfuran-2(5H)-one ring. The crystal packing is characterized by intermolecular O—H...O hydrogen bonds, which generate [010] chains.

Cyclic Dinuclear Organotin Cations Stabilized by Bulky Substituents

The syntheses of sterically congested 2,2-bis(diorganochloridostannyl)propane, Me2C(SnClR2)2 (1; R = CH(SiMe3)2), the related salts [cyclo-{Me2C(SnR2)2X}B(ArF)4] (2, X = Cl; 3, X = OAc; 4, X = OH; ArF = 3,5-(CF3)2C6H3), and the four-membered-ring cyclo-{Me2C(SnR2)2O} (5) are reported. The compounds have been characterized by elemental and EDX analyses, 1H, 11B, 13C, 19F, 29Si, and 119Sn NMR and IR spectroscopy, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction analysis.

1-[2-(Benzyl­amino)-4-pyrid­yl]-2-(4-fluoro­phen­yl)ethane-1,2-dione

The crystal structure of the title compound, C20H15FN2O2, contains two crystallographically independent molecules, which are related by a pseudo-inversion center and linked into dimersviaintermolecular N—H...N hydrogen bonds. The 4-fluorophenyl ring of moleculeAmakes dihedral angles of 17.17 (16) and 62.25 (15)°, respectively, with the phenyl and pyridine rings. The 4-fluorophenyl ring of moleculeBmakes dihedral angles of 8.50 (16) and 64.59 (15)°, respectively, with the phenyl and pyridine rings. The dihedral angle between the pyridine ring and the phenyl ring of moleculeA[60.97 (15)°] is bigger than in moleculeB[59.49 (15)°]. The dihedral angle between the two pyridine rings is 1.37 (14)°…

The First Examples of a Crown Ether Intramolecularly Encapsulating Mono- and Diorganotin Dications: Synthesis and Structures of [PhSnCH2([16]crown-5)][ClO4]2and [HOSnCH2([16]crown-5)][Y]2(Y=ClO4, CF3SO3)

The reaction of silver perchlorate with [PhI 2 SnCH 2 ([16]crown-5)] (1) and [I 3 SnCH 2 ([16]crown-5)] (2) gave the organotin(IV)-substituted crown ether complexes [PhSnCH 2 ([16]crown-5)][ClO 4 ] 2 (3) and [HOSnCH 2 ([16]crown-5)][Y] 2 (4: Y= ClO 4 , 5: Y=CF3 S 03 ) , respectively. All compounds have been isolated as air-stable materials and characterised by 1 H, 13 C, 119 Sn and 119 Sn MAS (5) NMR spectroscopy, ESIMS spectrometry, elemental analysis and by single-crystal X-ray diffraction analysis. The molecular structures of 3-5 show that the tin(IV) cation fits perfectly into the crown ether cavity and is coordinated by the five oxygen atoms of the ring to give a pentagonal bipyramidal…

Fused Dibenzo[ a , m ]rubicene: A New Bowl-Shaped Subunit of C 70 Containing Two Pentagons

Total synthetic approaches of fullerenes are the holy grail for organic chemistry. So far, the main attempts have focused on the synthesis of the buckminsterfullerene C60. In contrast, access to subunits of the homologue C70 remains challenging. Here, we demonstrate an efficient bottom-up strategy toward a novel bowl-shaped polycyclic aromatic hydrocarbons (PAH) C34 with two pentagons. This PAH represents a subunit for C70 and of other higher fullerenes. The bowl-shaped structure was unambiguously determined by X-ray crystallography. A bowl-to-bowl inversion for a C70 fragment in solution was investigated by dynamic NMR analysis, showing a bowl-to-bowl inversion energy (ΔG(⧧)) of 16.7 kcal …

Ethyl (2,3-dihydro-1H,1′H-2,3′-biindol-1-yl)glyoxylate

The crystal structure of the title compound, C20H18N2O3, was determined in the course of our studies of the synthesis of 3-acylindole derivatives. We obtained it as an unexpected racemic side product. The crystal structure contains chains of dimers along the a axis.

Synthesis of the Racemates of the b-Carboline Alkaloid Chrysotricine and its Diastereomer

The racemates of the rubiacea alkaloid Chrysotricine (1) and its diastereomer are synthesized from the isomeric mixture of linalyl oxides 3 and tryptamine in six steps, followed by separation of the diastereomers.

Metal- and Reagent-Free Anodic C−C Cross-Coupling of Phenols with Benzofurans leading to a Furan Metathesis

Heterobiaryls consisting of a phenol and a benzofuran motif are of significant importance for pharmaceutical applications. An attractive sustainable, metal- and reagent-free, electrosynthetic, and highly efficient method, that allows access to (2-hydroxyphenyl)benzofurans is presented. Upon the electrochemical dehydrogenative C-C cross-coupling reaction, a metathesis of the benzo moiety at the benzofuran occurs. This gives rise to a substitution pattern at the hydroxyphenyl moiety which would not be compatible by a direct coupling process. The single-step protocol is easy to conduct in an undivided electrolysis cell, therefore scalable, and inherently safe.

Leistungsstarkes Fluoralkoxy-Molybdän(V)-Reagens für die selektive oxidative Arenkupplung

Wir stellen ein neues Fluoralkoxy-Molybdan(V)-Reagens 1, mit im Vergleich zu MoCl5 oder MoCl5/TiCl4 hoherer Reaktivitat und Selektivitat in der oxidativen Kupplung von Arenen vor. Haufige Nebenreaktionen wie Chlorierung und/oder Oligomerenbildung werden erheblich reduziert, sodass ein leistungsstarkes und nutzliches Reagens fur die oxidative Kupplung erhalten wird. Theoretische Untersuchungen der Wechselwirkung des Reagens mit 1,2-Dimethoxybenzol-artigen Substraten deuten auf einen Innenspharen-Elektronentransfer gefolgt von einem radikalkationischen Reaktionspfad fur den oxidativen Kupplungsprozess hin. ESR-spektroskopische und elektrochemische Untersuchungen, Rontgenkristallstrukturanalys…

Selective mono-de-O-acetylation of the per-O-acetylated brasilicardin carbohydrate side chain

Abstract Methanol dried over powdered 4 A molecular sieves can be used for a selective mono-de-O-acetylation of the phenolic acetyl group of the per-O-acetyl protected brasilicardin A carbohydrate side chain. This reaction opens a practical procedure for a synthetic access to derivates of the immunosuppressive and cytotoxic natural product brasilicardin A.

Synthesis, Structural and Spectroscopic Characterization of Cr III , Fe III , Co III , Ni II and Cu II Complexes with an Asymmetric 1,3,4‐Thiadiazole Ligand

The reaction of the new asymmetric 1,3,4-thiadiazole-based ligand 2-[(5-ethylthio-1,3,4-thiadiazol-2-yl)hydrazonomethyl]phenol (H1ETHP) with various third-row transition metal salts resulted in the formation of six new mononuclear complexes [Cr(ETHP)2]ClO4 (1), [Fe(ETHP)2][FeCl4] (2), [Co(ETHP)(ETHP–H)] (3), [Ni(ETHP)(H1ETHP)]Cl (4), [Ni(ETHP)(H1ETHP)](ClO4) (5), [Ni(ETHP)(H1ETHP)]Br (6), and one tetranuclear complex [Cu2Cl3(ETHP)(H1ETHP)]2 (7). H1ETHP and all complexes have been analyzed by single crystal X-ray diffraction. Structural analysis of 1–6 reveals complexes of the [ML2]n+-type (n = 0,1), in which the mono anionic ligand ETHP coordinates in a tridentate NNO fashion via its imine,…

Innenrücktitelbild: Metall- und reagensfreie dehydrierende formale Benzyl-Aryl-Kreuzkupplung durch anodische Aktivierung in 1,1,1,3,3,3-Hexafluorpropan-2-ol (Angew. Chem. 37/2018)

Thieme Chemistry Journals Awardees – Where Are They Now? Molybdenum(V)-Mediated Synthesis of Nonsymmetric Diaryl and Aryl Alkyl Chalcogenides

Oxidative chalcogenation reaction using molybdenum(V) reagents provides fast access to a wide range of nonsymmetric aryl sulfides and selenides. The established protocol is tolerated by a variety of labile functions, protecting groups, and aromatic heterocycles. In particular, when labile moieties are present, the use of molybdenum(V) reagents provides superior yields compared to other oxidants.

Preparation of 5‐bromo‐6‐phenylimidazo[2,1‐b][1,3,4]thiadiazol‐2‐ylamines

The reaction of primary or secondary amines with 2,5-dibromo-6-phenylimidazo[2,1-b][1,3,4]-thiadiazole (5) leads to a chemoselective replacement of the 2-Br substituent. The process represents a convenient route to the corresponding 2-ylamines 7a-d. Hydrazine reacts in an analogous fashion (5 → 7e). The structure determinations are based on an X-ray crystal structure analysis and on one- and two-dimensional NMR measurements.

Experimental Investigations and Ab Initio Studies of Tellurium(II) Dithiolates, Te(SR)2

The reaction between Te(O(i)Pr)(4) and HSR offers a new and effective route to tellurium dithiolates, Te(SR)(2). Te(S(i)Pr)(2) (1) and Te(S(t)Bu)(2) (2) are stable compounds whereas Te(SPh)(2) (3) slowly decomposes at room temperature to give Te and Ph(2)S(2). IR spectra of 1-3 and ab initio calculations (HF/3-21G(d) and MP2 with double-zeta polarization effective core potential basis set) show nu(as)(Te-S) and nu(s)(Te-S) to be around 340 and 380 cm(-)(1), respectively. UV spectra exhibit similar lambda(max) (346-348 nm) for all three compounds, with the greater extinction coefficient of 3 accounting for its different and more intense color. Analysis of the molecular orbitals of the model …

4-(4-Fluoro­phen­yl)-3-(pyridin-4-yl)-1-(2,4,6-trichloro­phen­yl)-1H-pyrazol-5-amine

In the title compound, C20H12Cl3FN4, the pyrazole ring forms dihedral angles of 47.51 (9), 47.37 (9) and 74.37 (9)° with the directly attached 4-fluorophenyl, pyridine and 2,4,6-trichlorophenyl rings, respectively. Only one of the two amino H atoms is involved in hydrogen bonding. The crystal packing is characterized by N—H...N hydrogen bonds, which result in infinite chains parallel to the c axis.

Synthesis of pyrrolo[3′,4′:2,3]azepino[4,5,6-cd]indole-8,10-diones

3-Amino-4-(3-indolyl)pyrrolin-2,5-diones are condensed with various aldehydes and ketones to the cor responding imines. Under Pictet-Spengler conditions, the latter do not cyclize to pyrrolo-β-carbolines, but readily yield pyrrolo[3′,4′:2,3]azepino[4,5,6-cd]indole-8,10-diones.

ChemInform Abstract: Two Strained Hexahelicenophanes.

The crystal structures of the [6]­helicenes 4,13-(1,10-deca­methyl­ene­dioxy)­hexahelicene, C36H34O2, (I), and 4,13-(1,8-octa­methyl­ene­dioxy)­hexahelicene, C34H30O2, (II), show strong steric interactions between the terminal benzene rings and the poly­methyl­ene­dioxy chains. The shortest ring A and F distances amount to 2.941 (3) and 2.902 (3) A, respectively. The increased steric energy of the ground state is responsible for a significantly lower racemization barrier of (I) and (II) in comparison to the unsubstituted [6]­helicene.

Synthesis of and structural studies on lead(II) cysteamin complexes.

The novel compounds PbCl(2).(SCH(2)CH(2)NH(3)) (1), Pb(SCH(2)CH(2)NH(2))(2).2PbCl(SCH(2)CH(2)NH(2)) (2), and Pb(SCH(2)CH(2)NH(2))(2) (3) were synthesized by reaction of PbO or PbCl(2) with [HSCH(2)CH(2)NH(3)]Cl and NaOH, and were characterized by elemental analysis, IR-, and UV/vis-spectroscopy. Single-crystal X-ray diffraction revealed different coordination modes for the two Pb atoms in 2. The Pb atom in the Pb(SCH(2)CH(2)NH(2))(2) unit forms two covalent Pb-S and two intramolecular dative Pb...N bonds, leading to a pseudo trigonal bipyramidal configuration with a stereochemically active lone pair. The Pb atom in the PbCl(SCH(2)CH(2)NH(2)) unit, the first moiety structurally characterized…

(1aR,2aS,5aS,5bS)-Perhydro-4H-oxireno[3,4]cyclopenta[1,2-b]furan-4-one

The structure of the title compound, C7H8O3, was determined in the course of our studies of the synthesis of cyclopenta[1,2-b]furan-4-one derivatives. The molecule has four chiral C atoms. The X-ray crystal structure analysis shows the compound to possess an epoxide group with an endo orientation with respect to the lactone group.

Einfache und doppelte metall- und reagensfreie anodische C-C-Kreuzkupplung von Phenolen mit Thiophenen

Erstmals ist es gelungen, eine elektrochemische dehydrierende C-C-Kreuzkupplung von Thiophenen mit Phenolen durchzufuhren. Diese nachhaltige und einfache anodische Kreuzkupplung eroffnet den Zugang zu zwei besonders interessanten Substanzklassen. Das Anwendungsgebiet der C-H-aktivierenden elektrochemischen Kreuzkupplung wurde dabei um Schwefelheterocyclen erweitert. Bisher konnten nur verschiedene benzoide aromatische Systeme umgesetzt werden, wohingegen die Verwendung von Heterocyclen bei der C-H-aktivierenden elektrochemischen Kreuzkupplung nicht erfolgreich war. In diesem Fall bieten reagens- und metallfreie Bedingungen einen nachhaltigen elektrochemischen Weg und damit einen vielverspre…

catena-Poly[[(18-crown-6-κ6O)potassium]-μ-chlorido-[(1H-benzotriazol-1-ol-κN3)chloridoplatinum(II)]-μ-(benzotriazol-1-olato-κ2N3:O)]

In the structure of the title compound, [KPt(C6H4N3O)Cl2(C6H5N3O)(C12H24O6)], the PtII atom is in a distorted square-planar geometry. The crystal structure is consolidated by O—H⋯O hydrogen bonds. The measured crystal was a non-merohedral twin with four components.

Syntheses, Structures and Reactivity of New Intramolecularly Coordinated Tin Alkoxides Based on an Enantiopure Ephedrine Derivative

The syntheses of the tin compounds [LSn]2 (2), spiro-L2Sn (3), [LSnW(CO)5]2 (4), [LSnBr2]2 (5), spiro-L2Sn·SnBr4 (6) and LSn[OC(O)Ph]2 (8), where L = MeN(CH2CMe2O)[(S)-CH(Me)-(R)-CH(Ph)O], and (Ph4P)2SnBr6 (7) are reported. The compounds were characterized by elemental analysis, multinuclear NMR spectroscopy including 119Sn cross polarisation–magic angle spinning NMR (CP–MAS) (2, 3–6), electrospray ionization mass spectrometry (2–4) and single crystal X-ray diffraction analysis (2, 2·C7H8, 3a, 3b, 4·C7H8, 5, 6·C7H8, 7).

Regioselective substitution of 6,7-dichloroquinoline-5,8-dione: synthesis and X-ray crystal structure of 4a,10,11-triazabenzo[3,2-a]fluorene-5,6-diones

6,7-Dichloroquinoline-5,8-dione (1) was reacted with a number of 2-aminopyridine derivatives. Of the several possible products of this reaction, 4a,10,11-triazabenzo[3,2-a]fluorene-5,6-dione (6), produced by condensation and rearrangement, was obtained as the major product, and its structure was subsequently unambigously determined by X-ray crystallographic study. Ortho-quinones were produced via nucleophilic substitution at position C7, which was unexpected, considering that para-quinones were produced via C6 substitution in the reaction between compound 1 and ethyl acetoacetate in our previous work. Such unexpected nucleophilic substitution at C7 provides an effective, yet simple route, t…

4-[5-(4-Fluorophenyl)-3-isopropylisoxazol-4-yl]pyridin-2(1H)-one

The crystal structure of the title compound, C17H15FN2O2, was determined as part of a study of the biological activity of pyridine-substituted isoxazole derivatives as mitogen-activated protein kinase (MAPK) inhibitors. In the crystal structure of the title compound, the compound exists in the lactam and not in the tautomeric pyridin-2-ol form. As the aromatic pyridine nitrogen is considered to be important for accepting a hydrogen bond from p38MAPK, the structure of the lactam unit is correlated with the loss of biological activity of the title compound in the p38MAPK assay. In the crystal structure, the lactam is involved in hydrogen bonds, forming chains along the b axis.

Bulky, Dendronized Iridium Complexes and their Photoluminescence

Solution-processed blue emitters are essential for low-cost organic light-emitting diodes (OLEDs) but still face challenges due to their poor color purity, low efficiency and limited operational stability. Herein, by extending the conjugation of ultraviolet-emissive, facial tris(diphenylbenzimidazolyl)iridium (Ir) (fac-(dpbic)3Ir), we introduce two new types of solution-processed emitters, i.e. triisopropylsilylethynyl(TIPSE)-substituted fac-(dpbic)3Ir (2) and fac-(dpbic)3Ir-based polyphenylene dendrimers D1 and D2. The emissions of Ir-complex 2 and the dendrimers were successfully pushed toward a pure and sky blue color, respectively, due to the dominant 3π–π* nature of their emissive exci…

5,8,13,13-Tetrachloro-13H-dibenzo[a,i]fluorene cyclohexane hemisolvate

In the crystal structure of the solvated pentacyclic title compound, C21H10Cl4·0.5C6H12, the pentacyclic chloroaromatic rings are arranged in parallel layers, with the chlorine atoms protruding from these planes. Channels orthogonal to these layers are filled with disordered cyclohexane molecules.

Efficient Resolution of Menthylamine with Inexpensive (R,R)-Tartaric Acid by Dielectrically Controlled Resolution (DCR)

A practical procedure for the resolution of menthylamine 2 with (R,R)-tartaric acid [(R,R)-3] as resolving agent is presented. Variation of the solvent system allows both enantiomers of 2 to be selectively crystallized. Performing the resolution in methanol containing 6 % water leads to (–)-2·(R,R)-3·MeOH. The other, less-soluble diastereomeric salt is obtained by applying a solvent system consisting of methanol with 19 % water with a yield of 14 %. Subsequent basic workup with aqueous sodium hydroxide gave the free menthylamine compounds. Further workup of the mother liquors and an additional recrystallization step allowed the (–)-2·(R,R)-3·MeOH salt to be obtained in an overall yield of 2…

Dehydrierende anodische C‐C‐Kupplung von Phenolen mit elektronenziehenden Substituenten

Oxidative (Cross-)Coupling Reactions Mediated by C-H Activation of Thiophene Derivatives by Using Molybdenum(V) Reagents

Oxidative coupling by using molybdenum pentachloride provides fast and modular access to sophisticated thienoacenes in excellent yields. The coupling process can be accomplished with thiophene and benzothiophene derivatives and provides various complex skeletons such as spirocyclic compounds. In this approach, the first cross-coupling reactions with the use of MoCl5 were established and important motifs for semiconducting materials were synthesized.

A Phenylene-Bridged Cyclohexa-meta-phenylene as Hexa-peri-hexabenzocoronene Precursor.

A phenylene-bridged cyclohexa-meta-phenylene was synthesized via intramolecular Yamamoto coupling of an appropriate p-quinquephenyl derivative carrying four m-chlorophenyl substituents. The structural proof could be obtained by single-crystal X-ray diffraction analysis, which also revealed a slightly strained structure with an internal phenylene bridge. Notably, this cyclo-meta-phenylene served as a novel precursor for hexa-peri-hexabenzocoronene (HBC). The cyclodehydrogenation proceeded smoothly, providing the corresponding HBC derivative as confirmed by MALDI-TOF-MS, and UV/Vis spectroscopy.

N-{4-[3-(4-Fluorophenyl)pyrido[2,3-b]pyrazin-2-yl]-2-pyridyl}isopropylamine

In the crystal structure of the title compound, C21H18FN5, the pyridopyrazine ring system forms dihedral angles of 33.27 (7) and 48.69 (9)° with the 4-fluorophenyl and pyridine ring, respectively. The dihedral angle of the 4-fluorophenyl and pyridine rings is 57.45 (8)°. The crystal packing is characterized by an intermolecular N—H...N hydrogen bond.

Cover Feature: Mannose-Decorated Multicomponent Supramolecular Polymers Trigger Effective Uptake into Antigen-Presenting Cells (ChemBioChem 9/2018)

Bis(4-aminopyridinium) tetrachloridocobaltate(II)

In the title compound, (C(5)H(7)N(2))(2)[CoCl(4)], the cobalt(II) ion is coordinated by four chloride ions in a slightly distorted tetra-hedral geometry. The crystal packing is stabilized by inter-molecular N-H⋯Cl hydrogen bonding, forming a three-dimensional network. The crystal was a non-merohedral twin emulating tetra-gonal symmetry, but being in fact ortho-rhom-bic.

Selektive Synthese teilgeschützter unsymmetrischer Biphenole durch reagens‐ und metallfreie anodische Kreuzkupplung

Structure Determination of Photoproducts of Anthracenes with (Arylmethoxymethyl) Sidechains

Irradiation of 9-(arylmethoxymethyl)anthracenes 3 leads either to a cyclomer and cyclodimer mixture (3a  4a,5a), to selectively formed dimers (3b  5b), or a selectively formed cyclomer (3c  4c). The [4π+4π]cyclodimerization is under the conditions used a regioselective head-to-tail process. In the crystals of the dimers 5a,b, the sidechains are attached in an antiperiplanar position related to the CC bonds generated in the dimerization. In solutions, however, the structures consist of three rotamers the equilibration of which was studied by temperature-dependent NMR spectra. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)

tert-Butyl N-benzyl-N-(4-methyl-2-pyrid­yl)carbamate

In the crystal structure of the title compound, C18H22N2O2, the pyridine ring makes dihedral angles of 83.71 (6) and 9.2 (1)° with the phenyl ring and the carbamate plane, respectively. The phenyl ring and the carbamate plane are nearly perpendicular to one another, with a dihedral angle of 87.17 (7)°.

2-[(1-Methyl-1H-pyrrol-2-yl)carbonyl-meth-yl]isoindoline-1,3-dione.

The asymmetric unit of the title compound, C15H12N2O3, contains two almost identical molecules forming an nearly C2-symmetric dimeric pattern. The dihedral angles between the pyrrole ring and the phthalimide unit are 82.95 (8) and 86.57 (8)° for the two molecules. Within such a dimer, the phthalimide units of the two molecules form a dihedral angle of 1.5 (5)°.

5-(4-Fluoro-phen-yl)-4-(4-pyrid-yl)-1,3-oxazol-2-amine.

In the crystal structure of the title compound, C14H10FN3O, the plane of the isoxazole ring makes dihedral angles of 35.72 (9) and 30.00 (9)°, respectively, with those of the 4-fluorophenyl and pyridine rings. The plane of the 4-fluorophenyl ring makes a dihedral angle of 45.85 (8)° with that of the pyridine ring. The crystal structure is stabilized by intermolecular N—H...N hydrogen bonding. The two types of hydrogen bonds result in two chains, extending along the a axis, which are related by centres of symmetry.

ChemInform Abstract: Cycloaddition Reactions of 2H-1-Benzothietes and 1,3,5,7-Tetrathio-s-indacene-2,6-dithiones.

A Precursor Route to Supramolecular Oligo(p-phenylene terephthalamide) Block Copolymers

New soluble precursors for the step-wise synthesis of oligo(p-phenylene terephthalamide) block copolymers are described. Kevlar-like aramide oligomers up to the hexamer (six phenyl groups) were prepared in a polymer-analogous manner. Activating the carboxylic-acid-carrying oligomers as carbonyl chlorides while reversibly transforming the aromatic amides into imidoyl chlorides gave access to soluble precursors. The dimer and tetramer precursor were prepared and used in block copolymer synthesis. Single-crystal XRD confirmed the structure of the dimer precursor. Above a critical rod length, the Kevlar-like rod-coil block copolymers show strong aggregation in non-polar solvents such as chlorof…

Synthesis and Oxidant Properties of Phase 1 Benzepine N-Oxides of Common Antipsychotic Drugs

There is increasing evidence that cell constituents are oxidized by widely used antipsychotic drugs but until now the underlying chemistry has remained unclear. It is well known that such drugs readily undergo N-oxidation as a first key metabolic step. To gain insight into the problem, the tertiary phase 1 N-oxides of clozapine, olanzapine, quetiapine, and zotepine were synthesized, together with the N,S-dioxides of quetiapine and zotepine. These N-oxides were then subjected to well-established chemical transformations to test their oxidant properties in group VIII transition-metal­-catalyzed reactions. In the osmium tetroxide catalyzed dihydroxylation of styrene or cinnamyl alcohol and in …

Ligand mediated structural diversity of copper(II)-azido moiety: Synthesis, structure and magnetic study

Abstract Two copper azido complexes [Cu4(L1)4(µ1,1-N3)3(N3)] (1) and [{Cu2(L2)(N-benzylen)(µ1,1-N3)3(µ1,1,3-N3(N3)]n (2) have been synthesized by the reaction of aqueous solution of sodium azide to a methanolic solution of copper perchlorate hexahydrate and corresponding Schiff-base ligands. Schiff bases HL1 and HL2 act as blocking coligands are derived from the 1:1 condensation of N-benzyl ethylenediamine with Salicyldehyde and 2-hydroxy-5-chloroacetophenone respectively (N-benzylen is the N-benzyl ethylenediamine). These two complexes are characterized by the elemental analysis, FT-IR, single crystal X-ray diffraction, powder XRD and also TGA. Single crystal X-ray structural study reveals…

3-(2,4-Dimethoxyanilino)-8-methoxydibenz[b,e]oxepin-11(6H)-one

In the title compound, C23H21NO5, the two benzene rings of the tricyclic unit are oriented at a dihedral angle of 37.5 (8)°. The 2,4-dimethoxyanilino residue is oriented at a dihedral angle of 60.2 (8)° towards the phenoxy ring. In the crystal, the central carbonyl O atom accepts two hydrogen bonds from the N—H and C—H groups. A further intermolecular C—H...O interaction involving one of the methoxy O atoms is also observed.

5,12-Diselena-3,4,13,14-tetraazatricyclo[9.3.0.02,6]tetradeca-3,13-diene

The title compound, C8H8N4Se2, crystallizes in a non-symmetrical conformation with a dihedral angle between the heterocycles of 45.0 (3)° and a nearly strain-free tetramethylene tether. The crystal studied was non-merohedrally twinned with a fractional contribution of 0.342 (3) for the minor twin component.

Synthesis of optically pure alkynols

Abstract (R,S)-1-alkylprop-2-yn-1-ols have been separated by a 2-step procedure, esterification with N-p-tosyl-(L)-phenylalanine (or valine), recrystallisation of the diastereomeric esters from ethanol/hexane and saponification of the optically pure esters.

3-(2,4-Difluoro-anilino)-9-nitro-dibenzo[b,e]oxepin-11(6H)-one.

In the title compound, C20H12F2N2O4, the two benzene rings of the tricyclic unit are oriented at a dihedral angle of 30.6 (1)°. The 2,4-difluoroanilino residue is oriented at a dihedral angle of 68.2 (1)° with respect to the phenoxy ring. In the crystal, N—H...O hydrogen bonds between the amino group and the carbonyl O atom of the oxepinone ring link the molecules into infinte chains along the c axis.

Structural Optimization of a Pyridinylimidazole Scaffold: Shifting the Selectivity from p38α Mitogen-Activated Protein Kinase to c-Jun N-Terminal Kinase 3

Starting from known p38α mitogen-activated protein kinase (MAPK) inhibitors, a series of inhibitors of the c-Jun N-terminal kinase (JNK) 3 was obtained. Altering the substitution pattern of the pyridinylimidazole scaffold proved to be effective in shifting the inhibitory activity from the original target p38α MAPK to the closely related JNK3. In particular, a significant improvement for JNK3 selectivity could be achieved by addressing the hydrophobic region I with a small methyl group. Furthermore, additional structural modifications permitted to explore structure–activity relationships. The most potent inhibitor 4-(4-methyl-2-(methylthio)-1H-imidazol-5-yl)-N-(4-morpholinophenyl)pyridin-2-a…

The Influence of Intramolecular Coordination and Ring Strain on the Polymerization Potential of Cyclic Stannasiloxanes

N-[3-(5-Oxo-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-ylamino)phenyl]furan-3-carboxamide

In the title compound, C26H20N2O3, the two aromatic rings of the tricyclic unit are oriented at a dihedral angle of 54.53 (9)°. The crystal structure displays intermolecular N—H...O hydrogen bonding.

Solid-Phase Synthesis of Oligo(p-benzamide) Foldamers

[reaction: see text] A coupling protocol has been developed which allows the synthesis of oligo(p-benzamide)s on solid support. Aromatic carboxylic acids are activated in situ with thionyl chloride and used to acylate secondary aromatic amines. N-p-Methoxy benzyl (PMB) as well as N-hexyl protected monomers were investigated. Heterosequences of both monomers were synthesized. Such nanoscale objects are important building blocks for supramolecular chemistry.

Single-Crystal Structures of Model Compounds for Poly(2,5-dialkoxy-1,4-phenylenevinylene)

Syntheses and Crystal Structures of two Non-isostructural Copper(I) Chloride and Bromide π-Complexes with (2-Allylthio)benzimidazole of 1:1 Composition

By alternating-current electrochemical synthesis crystals of C10H10N2S · CuCl (I) and C10H10N2S · CuBr (II) π-complexes have been obtained and structurally investigated. The symmetry of I is orthorhombic, space group Pbcn, a = 16.799(2) A, b = 7.302(2) A, c = 18.214(2) A, V = 2234.1(9) A3, Z = 8 for C10H10N2S · CuCl composition, R = 0.0635, Rw = 0.0683 for 970 reflections. Crystals of II are monoclinic, space group P21/n, a = 7.4439(5) A, b = 17.6952(3) A, c = 17.0420(7) A, s = 94.662(2)°, V = 2237.4(2) A<3, Z = 4 for (Cu · C10H10N2S)2Br2 composition, R = 0.0463 for 4123 reflections. (2-Allylthio)benzimidazole moiety acts in both structures discussed as a bidentate ligand, chelating the cop…

ChemInform Abstract: Access to Pyrazolidin-3,5-diones Through Anodic N-N Bond Formation.

Pyrazolidin-3,5-diones are important motifs in heterocyclic chemistry and are of high interest for pharmaceutical applications. In classic organic synthesis, the hydrazinic moiety is installed through condensation using the corresponding hydrazine building blocks. However, most N,N'-diaryl hydrazines are toxic and require upstream preparation owing to their low commercial availability. We present an alternative and sustainable synthetic approach to pyrazolidin-3,5-diones that employs readily accessible dianilides as precursors, which are anodically converted to furnish the N-N bond. The electroconversion is conducted in a simple undivided cell under constant-current conditions.

(2S,3S)-2-Azaniumyl-4-[(1S,4aS,4bS,6S,7S,8aS,10aS)-6,7-dihydroxy-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]-3-methoxybutanoate–methanol–water (1/1/1)

The title compound, which crystallized as a methanol and water solvate, C24H41NO5·CH4O·H2O, was obtained by heterologous expression of the brasilicardin gene cluster in the bacterium Amycolatopsis japonicum. In the crystal, the components are linked by numerous hydrogen bonds, generating a three-dimensional network.

[a]-Anellated carbazoles with antitumor activity: Synthesis and cytotoxicity

The cycloadducts3,5, and7, readily available from methoxy-substituted 3-vinylindoles1 and2, were dehydrogenated withDDQ to the coplanar [a]-anellated carbazoles4,6, and8. Compound4a, also characterized by X-ray structural analysis, shows significant cytotoxicity against K562 und RXF393 human tumor cell lines.

Oligophenyls with Multiple Disulfide Bridges as Higher Homologues of Dibenzo[c,e][1,2]dithiin: Synthesis and Application in Lithium-Ion Batteries.

Abstract Higher homologues of dibenzo[c,e][1,2]dithiin were synthesized from oligophenyls bearing multiple methylthio groups. Single‐crystal X‐ray analyses revealed their nonplanar structures and helical enantiomers of higher meta‐congener 6. Such dibenzo[1,2]dithiin homologues are demonstrated to be applicable to lithium‐ion batteries as cathode, displaying a high capacity of 118 mAh g−1 at a current density of 50 mA g−1.

tert-Butyl N-benzyl-N-[4-(4-fluorobenzoylmethyl)-2-pyridyl]carbamate

In the crystal structure of the title compound, C25H25FN2O3, the pyridine ring makes dihedral angles of 75.1&#8197;(3), 39.4&#8197;(3) and 74.6&#8197;(3)&#176; with the phenyl ring, the carbamate plane and the 4-fluorophenyl ring, respectively. The phenyl ring makes dihedral angles of 77.2&#8197;(3) and 23.6&#8197;(3)&#176; with the carbamate plane and the 4-fluorophenyl ring, respectively. The 4-fluorophenyl ring is perpendicular to the carbamate plane, the dihedral angle between them being 89.5&#8197;(3)&#176;.

Enantioselektive Strecker-Reaktion mit einem Organokatalysator ohne Wasserstoffbrückendonor-Funktion

A Light-Induced Vinylogous Nazarov-Type Cyclization

The first examples of a photochemically induced vinylogous Nazarov-type cyclization forming a cycloheptadienone core are described. The reaction can be included in a three-step cascade consisting of a photochemical isoxazole-azirine ring contraction, cobalt(II)-catalyzed ring expansion, and the photochemical cyclization. Furthermore, the first representative of the hitherto unknown 1-azatricyclo[2.2.0.0(2,6)]hexanes has been identified as a side product of the azirine formation.

Metallfreie, elektrochemische Synthese von Sulfonamiden direkt aus (Hetero)arenen, SO 2 und Aminen

5,6,7-Trimethoxy-2,3-dihydro-1H,8H-benzo[a]pyrrolo[3,4-c]carbazole-1,3-dione dimethyl sulfoxide solvate

The crystal structure of the title compound, C21H16N2O5·C2H6OS, was determined to investigate the electrocyclic reactivity of 3,4-di­aryl-1H-pyrrole-2,5-diones (3,4-bisarylmal­eimides) to the yield corresponding carbazole derivatives.

Synthesis and Conformational Properties of Nonsymmetric Pillar[5]arenes and Their Acetonitrile Inclusion Compounds

The catalytic cyclocondensation of 1-butoxy-4-methoxy-2,5-bis(methoxymethyl)benzene (1d) affords a statistical mixture of the regioisomeric pillar[5]arenes 3a–d in high yield. The alkoxy groups are arranged stereoselectively in a mode so that they avoid steric interactions. The rotation of the benzene rings is, at room temperature, fast in terms of the NMR timescale and leads to a de facto Cs symmetry for 3a–c and a C5h symmetry for 3d. All four structural isomers can encapsulate two CH3CN guest molecules. The structure determinations are based on four crystal structure analyses (constitutions) and NMR spectroscopic measurements (conformations).

2,2′-[2,3,5,6-Tetramethyl-p-phenylenebis(methylenethio)]bis(pyridineN-oxide)

Mol-ecules of the title compound, C(22)H(24)N(2)O(2)S(2), lie across centres of inversion. The two thio-pyridine N-oxide groups adopt a stepped trans configuration with respect to the benzene ring, by virtue of the symmetry. The oxopyridinium ring forms a dihedral angle of 79.9 (2)° with the benzene ring. The crystal structure is stabilized by a strong π-π inter-action between the pyridinium rings of adjacent mol-ecules [ring centroid-centroid distance = 3.464 (3) Å].

The LIESST state of [Fe(pic)3]Cl2.EtOH – the superstructure under continuous irradiation

The superstructure recently discovered in [Fe(pic)3]Cl2.EtOH at temperatures inside the step region of the high-spin–low-spin transition curve sheds new light on the anomalous transition behaviour in spin crossover compounds. The structure of the metastable LIESST state of [Fe(pic)3]Cl2.EtOH at 10 K has been measured. The decay has been followed by X-ray diffraction using a CCD camera in order to detect reflections of the superstructure building up during the decay. No signal above the noise of the CCD camera was observed, so that even diffuse scattering could not be detected. This finding is in agreement with correlation lengths of pair correlations of molecules in the HS and LS states bei…

Metal- and Reagent-Free Dehydrogenative Formal Benzyl-Aryl Cross-Coupling by Anodic Activation in 1,1,1,3,3,3-Hexafluoropropan-2-ol

A selective dehydrogenative electrochemical functionalization of benzylic positions that employs 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP) has been developed. The electrogenerated products are versatile intermediates for subsequent functionalizations as they act as masked benzylic cations that can be easily activated. Herein, we report a sustainable, scalable, and reagent- and metal-free dehydrogenative formal benzyl-aryl cross-coupling. Liberation of the benzylic cation was accomplished through the use of acid. Valuable diarylmethanes are accessible in the presence of aromatic nucleophiles. The direct application of electricity enables a safe and environmentally benign chemical transformati…

One-Pot Synthesis to Quinone-Based Diaza[3.3]cyclophanes

A simple one-pot synthesis to [3.3]cyclophanes that involves quinone moieties was found. The protocol tolerates a variety of amines that include aliphatic and aromatic structures with different functional groups, such as hydroxy groups, amides, and terminal double and triple bonds. The straightforward synthesis can be performed by a twofold N-alkylation reaction with 2,5-bis(bromomethyl)-3,6-dimethyl-1,4-benzoquinone (1). Neither anhydrous nor inert conditions are required. Various amines can be employed without any activating groups, several functionalities at end groups are tolerated, and the cyclophanes generated can be easily modified or embedded into larger molecular architectures. The…

Straightforward Electrochemical Sulfonylation of Arenes and Aniline Derivatives using Sodium Sulfinates

Regioselektive metall‐ und reagenzfreie Arylierung von Benzothiophenen durch dehydrierende Elektrosynthese

Design, synthesis, and biological evaluation of novel disubstituted dibenzosuberones as highly potent and selective inhibitors of p38 mitogen activated protein kinase.

Synthesis, biological testing, structure-activity relationships (SARs), and selectivity of novel disubstituted dibenzosuberone derivatives as p38 MAP kinase inhibitors are described. Hydrophilic moieties were introduced at the 7-, 8-, and 9-position of the 2-phenylamino-dibenzosuberones, improving physicochemical properties as well as potency. Extremely potent inhibitors were obtained, with half-maximal inhibitory concentration (IC(50)) values in the low nM range in a whole blood assay measuring the inhibition of cytokine release. The high potency of the target compounds together with the outstanding selectivity of this novel class of compounds toward p38 mitogen activated protein (MAP) kin…

Adducts of Tellurium Tetrachloride with Allyl Alcohol and Allyl Acetate:  1,2- vs 1,3-Addition and Structure and Dynamics of Te···O Interactions in Different Phases

The compounds Cl 3 Te[CH 2 CH(Cl)CH 2 O(H)...].Cl 2 Te[-CH 2 CH(Cl)CH 2 O-] (1) and Cl 3 Te-[CH 2 CH(CH 2 Cl)OC(CH 3 )=O...] (2) were prepared by the reaction of TeCl 4 with allyl alcohol and allyl acetate, respectively. Their molecular and crystal structures were investigated by single-crystal X-ray analysis, 1 H- 1 H-NOESY experiments, IR spectroscopy, and ab initio geometry optimization. 1 is a composite compound, whose subunits Cl 2 Te[-CH 2 CH(Cl)-CH 2 O-] (1A) and Cl 3 Te[CH 2 CH(Cl)CH 2 O(H))...] (1B) are linked in the solid state via Te...Cl-Te and O...H-O bridges. Both Te atoms are involved in similar five-membered rings, having a covalent Te-O bond in one case (1A) and a dative Te…

Metal- and reagent-free highly selective anodic cross-coupling reaction of phenols.

The direct oxidative cross-coupling of phenols is a very challenging transformation, as homo-coupling is usually strongly preferred. Electrochemical methods circumvent the use of oxidizing reagents or metal catalysts and are therefore highly attractive. Employing electrolytes with a high capacity for hydrogen bonding, such as methanol with formic acid or 1,1,1,3,3,3-hexafluoro-2-propanol, a direct electrolysis in an undivided cell provides mixed 2,2′-biphenols with high selectivity. This mild method tolerates a variety of moieties, for example, tert-butyl groups, which are not compatible with other strong electrophilic media but vital for later catalytic applications of the formed products.

1-(Pyridin-4-yl)-3-(2,4,6-trichlorophenyl)benz[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

In the title compound, C20H10Cl3N5O, the 13-membered ring system makes dihedral angles of 78.64 (9)° with the trichlorophenyl ring and 62.60 (10)° with the pyridine ring. The crystal packing is dominated by π–π interactions between the 13-membered ring systems [centroid–centroid distance = 3.6655 (11)°].

Cooperative Effects in Aminothiols: Acid-Base Equilibria and the Molecular Structure of 2-(N, N-Dimethylaminomethyl)thiophenol

Abstract 2-(N,N-Dimethylaminomethyl)thiophenol, (1, HL), is present as a non-zwitterionic aminothiol in the solid state, exhibiting an intramolecular S-H···N hydrogen bond. The S···N distances of the two independent molecules in the asymmetric unit are 2.929(10) and 3.050(10) Å. This structural feature is also present in an ab initio (MP2/6-31G*) optimized molecular structure. The investigation of the hydrogen bond by ab initio methods supports an n(N)-σ *(S-H) interaction as the reason for this bond type. On the basis of data from potentiometric acid-base titrations of a 0.01 M aqueous solution of [H2L]Cl with a 0.1 M aqueous solution of sodium hydroxide, values of 4.09±0.01 and 11.50±0.01…

Crystal structures of pure 3-(4-bromo-2-chloro­phen­yl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one and contaminated with 3-(4-bromo­phen­yl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

The side product of the cyclo­condensation reaction between ethyl benzimidazole-2-carboxyl­ate and the nitrile imine of the corresponding hydrazonyl chloride, C20H11BrClN5O, crystallized in two crystal forms. Form (1) is a co-crystal of the target compound (without any chlorine substituent) and a side product containing a Cl atom in position 2 of the bromo­phenyl group, C20H12BrN5O·0.143C20H11BrClN5O. (2) contains the pure side product. The slightly different conformation of the ring systems leads to a different packing of (1) and (2), but both crystal structures are dominated by p-p inter­actions.

First Protection of a Wide-Rim Tetraamino Calix[4]arene in Opposite Positions

The importance of tetraamino calix[4]arenes as starting materials is distinctly increased by the first versatile protective group for opposite amino functions. Reaction with trityl chloride leads to the 1,3-dialkylated derivative easily isolated in 34% yield; after a first acylation of the remaining amino groups, the trityl residues can be removed by TFA to introduce a second acyl group. [reaction: see text]

Negatively Curved Nanographene with Heptagonal and [5]Helicene Units

Negatively curved nanographene (NG) 4, having two heptagons and a [5]helicene, was unexpectedly obtained by aryl rearrangement and stepwise cyclodehydrogenations. X-ray crystallography confirmed the saddle-shaped structures of intermediate 3 and NG 4. The favorability of rearrangement over helicene formation following radical cation or arenium cation mechanisms is supported by theoretical calculations. NG 4 demonstrates a reversible mechanochromic color change and solid-state emission, presumably benefiting from its loose crystal packing. After resolution by chiral high-performance liquid chromatography, the circular dichroism spectra of enantiomers 4-(P) and 4-(M) were measured and showed …

3-(4-Fluorophenyl)-4-(4-pyridyl)quinolin-2(1H)-one

The title compound, C20H13FN2O, has the quinolin-2(1H)-one unit in the lactam form. The mol­ecules form rows along the b axis via N—H⋯N hydrogen bonds

2,6,10-Trichlorotris[1,2,4]triazolo[1,5-a:1′,5′-c:1′′,5′′-e][1,3,5]triazine

Three very similar and nearly planar molecules are present in the asymmetric unit of the title compound, C6Cl3N9. Whereas the threefold 1,5-annulation of the chlorotriazole moieties is obvious, all of the C and N atoms in the central triazine ring are equally disordered on the same site, approachingD3hsymmetry for each of the molecules.

Metal- and Reagent-Free Electrochemical Synthesis of Alkyl Arylsulfonates in a Multi-Component Reaction.

Abstract This work presents the first electrochemical preparation of alkyl arylsulfonates by direct anodic oxidation of electron‐rich arenes. The reaction mechanism features a multi‐component reaction consisting of electron‐rich arenes, an alcohol of choice and excess SO2 in an acetonitrile‐HFIP reaction mixture. In‐situ formed monoalkyl sulfites are considered as key intermediates with bifunctional purpose. Firstly, this species functions as nucleophile and secondly, excellent conductivity is provided. Several primary and secondary alcohols and electron‐rich arenes are implemented in this reaction to form the alkyl arylsulfonates in yields up to 73 % with exquisite selectivity. Boron‐doped…

4-[3-(4-Fluorophenyl)quinoxalin-2-yl]-N-isopropylpyridin-2-amine

In the crystal structure of the title compound, C22H19FN4, the quinoxaline system makes dihedral angles of 32.07 (13) and 69.64 (13)° with the 4-fluorophenyl and pyridine rings, respectively. The 4-fluorophenyl ring makes a dihedral angle of 71.77 (16)° with the pyridine ring. The crystal structure is stabilized by intermolecular N—H...N hydrogen bonding.

Planar Benzo[1,2-b:4,5-b′]dithiophene Derivatives Decorated with Nitronyl and Imino Nitroxides

Four weakly antiferromagnetic interacting biradicals of benzo[1,2- b:4,5- b']dithiophene (BDT) and BDT extended with two thiophenes (BDTTh2) linked with nitronyl and imino nitroxides (NN and IN) as BDT-NN, BDT-IN, BDTTh2-NN, and BDTTh2-IN were designed, synthesized, and characterized. Short intermolecular π-π distances were found (3.42 A) for BDT-NN, whereas larger ones were found for BDT-IN (3.54 A) and BDTTh2-NN (3.67 A), respectively. Intramolecular magnetic interaction ( Jintra,exp/ kB) of BDT-NN (-26 K) is much larger than for BDT-IN (-5.3 K), while it is reduced for the dithiophene-extended molecule BDTTh2-NN (-2.3 K). Intermolecular interactions ( zJinter,exp/ kB) of BDT-NN (-6.5 K) …

Step growth polymerization via tandem ene and diels-alder reactions

In contrast to other electron deficient enophiles or dienophiles which react with 1,4-cyclohexadiene (1,4-CHD) under aromatization, 1,2,4-triazoline-3,5-diones react in a defined reaction sequence. In a first step the 1,4-cyclohexadiene reacts via an ene-reaction. The intermediately formed substituted 1,3-cyclohexadiene immediately reacts in a Diels-Alder reaction. The regiochemistry of the Diels-Alder reaction is controlled by the solvent polarity. This reaction sequence can be used to synthesize polymers. Low-molar-mass model compounds were synthesized to elucidate the stereochemistry of the polymers. By varying the bistriazolinedione, polymers with backbones of different rigidity are ava…

About the selectivity and reactivity of active nickel electrodes in C–C coupling reactions

Active anodes which are operating in highly stable protic media such as 1,1,1,3,3,3-hexafluoroisopropanol are rare. Nickel forms, within this unique solvent, a non-sacrificial active anode at constant current conditions, which is superior to the reported powerful molybdenum system. The reactivity for dehydrogenative coupling reactions of this novel active anode increases when the electrolyte is not stirred during electrolysis. Besides the aryl-aryl coupling, a dehydrogenative arylation reaction of benzylic nitriles was found while stirring the mixture providing quick access to synthetically useful building blocks.

3-(2-Fluorophenyl)-6-(phenoxymethyl)-1,2,4-triazolo[3,4-b][1,3,4]thiadiazole

The crystal structure of the title compound, C16H11FN4OS, was synthesized in the course of our studies on 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles as inhibitors of p38 mitogen-activated protein kinase (MAPK). The three-dimensional data obtained were used to generate a three-dimensional pharmacophore model for in silico database screening. The dihedral angles between the central heterocylic system and the fluorophenyl and phenyl rings are 20.21&#8197;(3) and 5.43&#8197;(1)&#176;, respectively; the dihedral angle between the two benzene rings is 15.80&#8197;(4)&#176;.

Tetra-μ-chlorido-bis(18-crown-6)platinum(II)dipotassium(I)

In the title compound, [K(2)PtCl(4)(C(12)H(24)O(6))(2)], the Pt(II) ion is located on an inversion centre and is coordinated by four Cl atoms, forming a square-planar geometry. The K(I) ion is coordinated by six O atoms of the crown ether and two bridging Cl atoms. The K(I) ion is displaced by 0.756 (2) Å from the mean plane of the six O atoms of the crown ether. The mol-ecules are connected by weak C-H⋯O hydrogen bonds, forming an infinite two-dimensional network parallel to the (10) plane. Intra- and inter-molecular C-H⋯Cl hydrogen bonds are also observed.

Synthesis, Spectroscopic Characterization, and Crystal Structure Determination of Cationic [(Cyclopentadienyl)dicarbonyliron](alkynyl)‐aminocarbene Complexes

(Alkynoyl)iron complexes 1, Cp(CO)2Fe(OCCCR) (R = CH3, Ph, SiMe3), were synthesized by applying a mixed anhydride procedure and transformed into the cationic methoxycarbene complexes 2, [Cp(CO)2 Fe(C(OMe)CCR)+]-[PF6–]. Primary amines H2NR′ react with the methoxycarbene complexes to furnish exclusively cationic aminocarbene complexes 3, [Cp(CO)2 Fe(C(NHR′)CCR)+][PF6–], or (2-methoxyvinyl)aminocarbene complexes 5. The spectroscopic properties of the new complexes are discussed. The (alkynyl)-aminocarbene complexes 3e and 3f were characterized by X-ray crystal structure analysis.

Direct Metal‐ and Reagent‐Free Sulfonylation of Phenols with Sodium Sulfinates by Electrosynthesis

A novel electrochemical strategy for the synthesis of aryl sulfones by direct sulfonylation of phenols with sodium sulfinates has been developed. The C,S-coupling products are of particular interest for chemical synthesis, material sciences and pharmaceutical sciences. By using this metal- and reagent-free electrochemical method, aryl and diaryl sulfones can be obtained directly in good yields. The established one-step protocol is easy to perform, scalable, inherently safe, and enables a broad scope, which is not limited by quinoid-forming substrates.

ChemInform Abstract: Synthesis and Isolation of Enantiomerically Enriched Cyclopenta[b]benzofurans Based on Products from Anodic Oxidation of 2,4-Dimethylphenol.

Tetramer (I) is obtained by anodic oxidation of 2,4-dimethylphenol as reported in a previous paper.

Efficient Synthesis and X-ray Structure of [1,2,4]Triazolo[4,3-a]pyridines via Oxidative Cyclization Using N-Chlorosuccinimide (NCS)

Triazolopyridines are a family of compounds that, owing to their biological activity, have many pharmaceutical applications. In this study, 3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-a]pyridine and 6-bromo-3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-a]pyridine were synthesized by using the chlorinated agent NCS for hydrazones under very mild conditions. The characterization of these compounds was achieved by 1H NMR, 13C NMR, FTIR, MS and X-ray diffraction. The compound 3-(pyridine-4-yl)-[1,2,4]triazolo[4,3-a]pyridine was crystallized in the monoclinic space group P 21/c with a = 15.1413(12), b = 6.9179(4), c = 13.0938(8) Å, β = 105.102(6)°, V = 1324.16(16)Å3, Z = 4, and R = 0.0337. Also compound 6-bro…

Innentitelbild: Regioselektive metall‐ und reagenzfreie Arylierung von Benzothiophenen durch dehydrierende Elektrosynthese (Angew. Chem. 40/2018)

Total Synthesis of (-)-Oxycodone via Anodic Aryl-Aryl Coupling.

A fully regio- and diastereoselective electrochemical 4a–2′-coupling of a 3′,4′,5′-trioxygenated laudanosine derivative enables the synthesis of the corresponding morphinandienone. This key intermediate is further transformed into (−)-oxycodone through conjugate nucleophilic substitution for E-ring closure and [4 + 2] cycloaddition with photogenerated singlet oxygen to accomplish diastereoselective hydroxylation at C-14. The anodic transformation provides high yields and can be performed under constant current conditions both in a simple undivided cell or in continuous flow.

2-(4-Fluorophenyl)-3-(4-pyridyl)pyrido[2,3-b]pyrazine

In the crystal structure of the title compound, C18H11FN4, the pyridopyrazine system makes dihedral angles of 45.51&amp;#8197;(7) and 44.75&amp;#8197;(7)&amp;#176; with the attached 4-fluorophenyl ring and the pyridine ring, respectively. The 4-fluorophenyl ring makes a dihedral angle of 54.54&amp;#8197;(8)&amp;#176; with the pyridine ring. The pyridine ring part of the pyridopyrazine ring and the pyrazine ring of two c-glide-plane-related molecules form &amp;#960;&amp;#8211;&amp;#960; interactions. The angle between the planes is 2.09&amp;#8197;(7)&amp;#176; and the distance between the centroids is 3.557&amp;#8197;(1)&amp;#197;.

Selective Formation of 4,4'-Biphenols by Anodic Dehydrogenative Cross- and Homo-Coupling Reaction.

A simple and selective electrochemical synthesis by dehydrogenative coupling of unprotected 2,6- or 2,5-substituted phenols to the desired 4,4'-biphenols is reported. Using electricity as the oxidizing reagent avoids pre-functionalization of the starting materials, since a selective activation of the substrates takes place. Without the necessity for metal-catalysts or the use of stoichiometric reagents it is an economic and environmentally friendly transformation. The elaborated electrochemical protocol leads to a broad variety of the desired 4,4'-biphenols in a very simplified manner compared to classical approaches. This is particular the case for the cross-coupled products.

Selective Synthesis of Partially Protected Nonsymmetric Biphenols by Reagent‐ and Metal‐Free Anodic Cross‐Coupling Reaction

The oxidative cross-coupling of aromatic substrates without the necessity of leaving groups or catalysts is described. The selective formation of partially protected nonsymmetric 2,2'-biphenols via electroorganic synthesis was accomplished with a high yield of isolated product. Since electric current is employed as the terminal oxidant, the reaction is reagent-free; no reagent waste is generated as only electrons are involved. The reaction is conducted in an undivided cell, and is suitable for scale-up and inherently safe. The implementation of O-silyl-protected phenols in this transformation results in both significantly enhanced yields and higher selectivity for the desired nonsymmetric 2…

ChemInform Abstract: Oxidative (Cross-)Coupling Reactions Mediated by C-H Activation of Thiophene Derivatives by Using Molybdenum(V) Reagents.

The use of MoCl5 renders possible the preparation of various synthetically important polycyclic thienoacenes.

Synthesis of Enantiopure ω-(4-Fluorophenyl)-6,11-Methylene Lipoxin B4 Methyl Ester

AbstractThe synthesis of Lipoxin B4 analogues (LXB4) to gain access to stabilized inflammation-resolving compounds is an active field of research. Focusing on variation and stabilization of the conjugated E,Z,E,E C6–C13 tetraene moiety of natural LXB4, a methylene bridge introduced between C6 and C11 suppresses any Z/E isomerization of the C8–C9 olefin. Furthermore, rapid ω-oxidation (C20) should be avoided by replacing the C18–C20 segment by an aromatic moiety. Optically active C1–C12 building blocks were accessed from methyl cycloheptatriene-1-carboxylate (C6–C11, C21) and glutaryl chloride (C1–C5) as described earlier. The ω-segment was generated via a five-step sequence starting from 4-…

Zwitterionic Aza-Claisen Rearrangements Controlled by Pyrrolidine Auxiliaries - Useful Key Steps in Convergent Enantioselective Syntheses

Chiral pyrrolidine substituents served as efficient auxiliaries in diastereoselective zwitterionic ketene aza-Claisen rearrangements. Palladium-catalysed N-allylation starting from optically active proline and prolinol derivatives, as well as from (2S,5S)-2,5-dimethoxymethylpyrrolidine, gave various allylamines bearing trisubstituted olefin moieties. Treatment with complex carboxylic acid fluorides in the presence of trimethylaluminium induced activated ketene addition to the nitrogen and subsequent [3,3] sigmatropic rearrangement to give γ,δ-unsaturated amides with excellent simple diastereoselectivities and up to 11:1 auxiliary-induced diastereomeric ratios. Cleavage of the pyrrolidine am…

Electrochemical synthesis of benzoxazoles from anilides - a new approach to employ amidyl radical intermediates.

A novel electrochemical method for the synthesis of benzoxazoles from readily available anilides is reported. Various functionalities are tolerated and good yields can be achieved. By employing common electrode materials and a simple constant current protocol, this method is an attractive new alternative to conventional pathways.

Innentitelbild: Reagens- und metallfreie anodische C-C-Kreuzkupplung von Anilinderivaten (Angew. Chem. 17/2017)

tert-ButylN-(4-methyl-2-pyridyl)carbamate

The crystal structure of the title compound, C11H16N2O2, contains two crystallographically independent molecules forming dimers by pairs of intermolecular N&#8212;H...N hydrogen bonds. The two molecules are related by a pseudo-twofold axis. The dihedral angle between the pyridine ring and the carbamate plane differs in the two molecules [12.1&#8197;(3) and 3.5&#8197;(3)&#176;].

(2S,3S)-2-Azaniumyl-4-[(1S,4aS,4bS,6S,7S,8aS,10aS)-6,7-dihydroxy-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydrophenanthren-1-yl]-3-methoxybutanoate–methanol–water (1/1/1)

The title compound, which crystallized as a methanol and water solvate, C24H41NO5·CH4O·H2O, was obtained by heterologous expression of the brasilicardin gene cluster in the bacterium Amycolatopsis japonicum. In the crystal, the components are linked by numerous hydrogen bonds, generating a three-dimensional network.

The [Fe(etz)6](BF4)2 Spin-Crossover System—Part One: High-Spin ⇌ Low-Spin Transition in Two Lattice Sites

The [Fe(etz),](BF,), spin-cross-over system (etz = 1-ethyl-1 H-tetrazole) crystallizes in space group P1, with the following lattice constants at 298 K: a 10.419(3), b=15.709(1), c = 18.890(2) A = = 71.223(9), =77.986(10), and = 84.62(1)° V = 2862.0(9) A3 and Z = 3. Two nonequivalent lattice sites, one without (site A) and one with (site B) inversion symmetry, are observed. The population of the two sites nA:nB is 2:l. Iron(II) on site A undergoes a thermal low-spin (LS) high-spin (HS) transition with T1/2I, = 105 K. whereas that on site B remains in the high-spin state down to cryogenic temperatures. Application of external pressure of up to 1200 bar between 200 and 60 K does not cause for…

Poly[bis(μ-pentafluorobenzenethiolato)lead(II)]

The title compound, [Pb(SC6F5)2]n, exhibits a layered structure containing two differently hexa­coordinated PbII atoms. One is situated on a centre of inversion and is coordinated by six S atoms, its valence lone pair of electrons being consequently stereochemically inactive. The other Pb atom is pyramidally coordinated by three S atoms and forms three contacts to adjacent F atoms, the stereochemically active lone pair pointing towards the F3 plane.

ChemInform Abstract: Solvent-Dependent Facile Synthesis of Diaryl Selenides and Biphenols Employing Selenium Dioxide.

The reaction of phenols (I) with selenium dioxide in pyridine leads to diaryl selenides (IIa-d), whilst the reaction in acetic acid gives rise to biphenols (III).

Flexible minerals: self-assembled calcite spicules with extreme bending strength.

Flexi-Fibers Glass or metal fibers can show incredible flexibility. Natalio et al. (p. 1298 ; see the Perspective by Sethmann ) used the protein silicatein-α, which is responsible for the biomineralization of silicates in sponges, to guide the formation of spicules made of calcite. These synthetic spicules could be bent to a high degree because of their inherent elasticity, whilst retaining the ability to guide light.

trans-Bis(1H-benzimidazole-1-thione-κS)tetrachlorotellurium methanol disolvate

The Te atom in the title complex, trans-[TeCl4(C6H4N2H2CS)2]·2CH4O or C16H20Cl4N4O2S2Te, occupies a special position at a crystallographic inversion centre and has an octahedral coordination formed by four chloro ligands and the S atoms of two benz­imidazole–thione mol­ecules. The hydrogen-bond system involving the disordered solvent methanol mol­ecules links the tellurium complexes into the infinite two-dimensional aggregates in the crystal.

Hydrogen bonding in dimers of tritolyl and tritosylurea derivatives of triphenylmethanes.

The crystal structure of the homodimer formed by the tritolylurea 3a proves the existence of a belt of six bifurcated hydrogen bonds between both NH and the O=C groups of the adjacent urea residues. For the tritosylurea 3b, four additional three-center hydrogen bonds, also involving the SO2 oxygen, are found in the crystalline state. Molecular dynamics simulations in a chloroform box confirm these patterns of the hydrogen bonds and the resulting elongation of the dimer 3b. 3b in comparison to 3a x 3a. The calculated complexation energies for the three dimeric combinations are nearly identical in agreement with the simultaneous formation of heterodimer 3a x 3b in a mixture of 3a and 3b.

Frontispiece: Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO 2 , and Amines

ChemInform Abstract: Flexible Synthesis of Planar Chiral Azoninones and Optically Active Indolizidinones.

Stereoselective Synthesis of Enantiomerically Pure Piperidine Derivatives by N-Galactosylation of Pyridones.

Stereoselective desymmetrization of 4-pyridone has been achieved through selective N-galactosylation, activation of the N-(galactosyl)pyridone by O-silylation and immediate addition of Grignard compounds. Chiral piperidine derivatives, e.g. (S)-(+)-coniine and (5S,9S)-(+)-indolozidine 167B, were synthesised in enantiomerically pure form using these highly regio- and stereoselective reactions. After N-galactosylation of 2-pyridone and O-silylation of the N-galactosyl-2-pyridone, addition of a Grignard compound proceeded with high 1,4-regioselectivity and complete diastereoselectivity, to furnish 4-substituted 5,6-dehydro-2-piperidones. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Ger…

N,1-Bis(4-ethoxyphenyl)-2,6-dimethyl-4-oxo-1,4-dihydropyridine-3-carboxamide

Condensation of ethyl acetoacetate and phenetidine gives the title compound, C24H26N2O4. The planar ethoxyphenyl group attached to the pyridine ring is twisted about 77.96 (11)° out of the plane of the N-ethoxycarboxamidopyridine unit. The carboxamide unit forms a dihedral angle of about 28.1 (2)° with the pyridine ring.

Synthesis of Naturally Occurring Pyrazine and Imidazole Alkaloids from Botryllus LeachiRID=?a?ID=?a? Dedicated to Prof. G . Märkl on the occasion of his 75 th birthday

The synthesis of the naturally occurring and biologically active alkaloids 1 and 2, first isolated from the red ascidian Botryllus leachi by Duran et al. [1], is described and the structure proposed for Botryllazine B (1) is confirmed. The analytical data for 2-(p-hydroxybenzoyl)-4-(p-hydroxyphenyl)imidazole (2) are discussed and compared with the literature. With special emphasis of 1H NMR data the tautomerism of aroylimidazolemethanones is described.

First Synthesis of Medium-Sized Ring Allenyl Lactams

Medium-sized lactams bearing an axially chiral allene unit have been synthesized by using an aza-ketene Claisen rearrangement. Starting from 2-alkynylpiperidines or 2-alkynylazepines, ring enlargement enabled the highly diastereoselective formation of 10- or 11-membered lactams with a 4,5-allene subunit. X-ray analysis of the allenylacezinone showed the presence of a strained cumulated olefin system with a defined arrangement of the functional groups. The cyclic allenes were found to be stable upon heating up to 50 °C.

Molecular Recognition-Induced Function and Competitive Replacement by Hydrogen-Bonding Interactions:  Amphiphilic Barbituric Acid Derivatives, 2,4,6-Triaminopyrimidine, and Related Structures at the Air−Water Interface

The phenomenon of molecular recognition inducing further function is common in nature. However, there are few synthetic systems which achieve this cascade type mechanism, and those are generally ca...

The head-to-head photodimer of indeno-indene.

Irradiation of 1-(1-benzocyclobutenylidene)benzocyclobutene gives indenoindene and its head-to-head photodimer nonacyclo[9.7.7.72,10.01,11.02,10.03,8.012,17.019,24.026,31]dotriaconta-3,5,7,12,14,16,19,21,23,26,28,30-dodecaene, C32H24. The molecule is built from four essentially planar indane units attached to an elongated cyclobutane ring. In the crystal, C—H...π interactions connect molecules into layers parallel to the bc plane.

6-Amino-1-benzyl-4-(4-chloro-phen-yl)-3-(4-pyrid-yl)-1,4-dihydro-pyrano[2,3-c]pyrazole-5-carbonitrile.

The crystal structure of the title compound, C25H18ClN5O, was determined in the course of our studies on the synthesis of 1,4-dihydropyrano[2,3-c]pyrazole as an inhibitor of the p38 mitogen-activated protein kinase (MAPK). The compound was prepared via a base-catalysed synthesis from 1-benzyl-3-(4-pyridyl)-1H-pyrazol-5(4H)-one with p-chloroaldehyde and malononitrile. The crystal data obtained were used to generate a three-dimensional pharmacophore model for in silico database screening. The phenyl ring is disordered over two positions, with site occupancy factors of 0.55 and 0.45. The dihedral angles between the 1,4-dihydropyrano[2,3-c]pyrazole unit and the chlorophenyl and pyridine rings a…

(-)-(3a ' S,4 ' S,9b ' S,1R,2S,5R)-4 '-ethyl-3a ',4 ',5 ',7 ',8 ',9b '-hexahydro-2-isopropyl-5-methyl-2 '-phenylspiro[cyclo-hexane-1,7 '-dioxino[3,2-e]isoindole]-1 ',3 ',9 '-trione

The title compound, C27H33NO5, obtained from diethyl ether, crystallizes in space group P2(1) with four molecules in the asymmetric unit. The dioxinone and imide rings are almost planar, whereas the cyclohexane and cyclohexene rings form distorted conformations. The crystal structure confirms an earlier proposal about the stereoselectivity of Diels - Alder reactions to spirocyclic chiral 1,3- dienes.

ChemInform Abstract: An Efficient Synthesis of Rubin′s Aldehyde and Its Precursor 1,3,5-Tribromo-2,4,6-tris(dichloromethyl)benzene.

The title compound (IV) serves as precursor of hexaethynylbenzenes and other [6]star compounds.

Crystal structure of a dimeric 1-benzothiepin

AbstractThe crystal structure of the 1-benzothiepin derivativemeso-5is presented. Compound5is the first dimeric 1-benzothiepin system.

Cover Picture: Source of Selectivity in Oxidative Cross-Coupling of Aryls by Solvent Effect of 1,1,1,3,3,3-Hexafluoropropan-2-ol (Chem. Eur. J. 35/2015)

Amplification of Dissymmetry Factors in π-Extended [7]- and [9]Helicenes

International audience; $\pi$-Extended helicenes constitute an important class of polycyclic aromatic hydrocarbons with intrinsic chirality. Herein, we report the syntheses of $\pi$extended [7]helicene $4$ and $\pi$-extended [9]helicene $6$ through regioselective cyclodehydrogenation in high yields, where a "prefusion" strategy plays a key role in preventing undesirable aryl rearrangements. The unique helical structures are unambiguously confirmed by X-ray crystal structure analysis. Compared to the parent pristine [7]helicene and [9]helicene, these novel $\pi$-extended helicenes display significantly improved photophysical properties, with a quantum yield of 0.41 for $6$. After optical res…

Metal‐Free Twofold Electrochemical C−H Amination of Activated Arenes: Application to Medicinally Relevant Precursor Synthesis

Abstract The efficient production of many medicinally or synthetically important starting materials suffers from wasteful or toxic precursors for the synthesis. In particular, the aromatic non‐protected primary amine function represents a versatile synthetic precursor, but its synthesis typically requires toxic oxidizing agents and transition metal catalysts. The twofold electrochemical amination of activated benzene derivatives via Zincke intermediates provides an alternative sustainable strategy for the formation of new C−N bonds of high synthetic value. As a proof of concept, we use our approach to generate a benzoxazinone scaffold that gained attention as a starting structure against ca…

Methyl 4-[5-(4-fluorophenyl)-4-(pyridin-4-yl)-1H-imidazol-2-ylsulfanyl]butanoate

The title compound, C19H18FN3O2S, was synthesized in the course of studies on 2-alkylsufanylimidazoles as p38 mitogen-activated protein kinase inhibitors. The synthesis was achieved by nucleophilic substitution of 4-(4-fluorophenyl)-5-(pyridin-4-yl)-1,3-dihydroimidazole-2-thione with methyl 4-bromobutanoate. The five-membered heterocycle makes dihedral angles of 32.4&#8197;(2) and 18.3&#8197;(2)&#176; with the fluorophenyl and pyridinyl rings, respectively, indicating a low degree of conjugation between these rings. Intramolecular C&#8212;H...N and intermolecular N&#8212;H...N hydrogen bonds as well as C&#8212;H...&#960; interactions seem to be effective in stabilization of the crystal stru…

Molecular structure of Te(OMe)4.ClTe(OMe)3, a model for ligand exchange between Te(IV) centers.

ClTe(OiPr)3 could be prepared from stoichiometric amounts of TeCl4 and Te(OiPr)4, a reaction that requires the exchange of ligands between different Te centers. Ligand redistribution between telluranes was studied, and rapid exchange of -Cl and -OR (R = Me, iPr) ligands in solutions of several binary mixtures of Te(OMe)4, Te(OiPr)4, ClTe(OMe)3, and ClTe(OMe)3, and ClTe(OiPr)3 was established by multinuclear NMR spectroscopy. The solid-state structure of Te(OMe)4.ClTe(OMe)3, the first structurally characterized adduct between different telluranes, was investigated by single-crystal X-ray diffraction. It exhibits a very short Te-O...Te bridge between the two Te centers and additional Te...O a…

Organotin(IV) derivatives containing heteroditopic pyridyl-quinolin-8-olate ligands: Synthesis and structures

Abstract Six novel neutral organotin(IV) complexes, viz. [n-Bu2Sn(L4-PyAQ)2] 1, [Bz2Sn(L4-PyAQ)2] 2, [Ph2Sn(L4-PyAQ)2] 3, [Ph2Sn(L3-PyAQ)2] 4, [Bz3Sn(L4-PyAQ)] 5 and [Ph3Sn(L4-PyAQ)] 6 have been synthesized via reactions of 3/4-pyridyl-quinolin-8-ol pro-ligands, with appropriate diorganotin oxide and triorganotin hydroxide precursors, respectively. The compounds 1-6 were characterized in solution by means of NMR spectroscopy while the solid-state structures of 1, 6, and of the solvates 2·1.5C6H6, 3·0.25C6H6, 2·4·C6H6, and 5·0.5H2O were authenticated by single crystal X-ray diffraction analysis. In the solid-state, the tin centers in 1-2·4·C6H6 are hexacoordinated and reveal a distorted cis-…

Investigation of Diketopiperazines Containing a Guanidino-Functionalized Sidechain as Potential Catalysts of Enantioselective Strecker Reactions

Diketopiperazine 1 consisting of L-(γ-guanidino-α-amino)butyric acid and L-phenylalanine was synthesized as the hydroacetate and as the hydronitrate. Its structure was confirmed by X-ray analysis. In contrast to reports in the literature (Lipton et al.), compound 1 does not induce enantioselevtive catalysis of Strecker reactions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

Inside Cover: Regioselective Metal‐ and Reagent‐Free Arylation of Benzothiophenes by Dehydrogenative Electrosynthesis (Angew. Chem. Int. Ed. 40/2018)

4-(4-Fluorophenyl)-1-(4-nitrophenyl)-3-(pyridin-4-yl)-1H-pyrazol-5-amine

In the crystal structure of the title compound, C20H14FN5O2, the pyrazole ring forms dihedral angles of 59.3&amp;#8197;(2), 25.6&amp;#8197;(2) and 46.0&amp;#8197;(2)&amp;#176; with the directly attached 4-fluorophenyl, pyridine and nitrophenyl rings, respectively. The crystal packing is characterized by intermolecular N&amp;#8212;H...N and N&amp;#8212;H...O hydrogen bonds.

Synthesis and molecular properties of donor–π-spacer–acceptor ynamides with up to four conjugated alkyne units

A set of push-pull ynamides with up to four conjugated triple bonds has been synthesized and the molecular properties of these new carbon rods have been characterised showing effective intramolecular charge transfers and high values for the change of the electrical dipole moment after transition from the ground to the Franck-Condon excited state.

Electrochemical synthesis of carbazoles by dehydrogenative coupling reaction

Abstract A constant current protocol, employing undivided cells, a remarkably low supporting electrolyte concentration, inexpensive electrode materials, and a straightforward precursor synthesis enabling a novel access to N‐protected carbazoles by anodic N,C bond formation using directly generated amidyl radicals is reported. Scalability of the reaction is demonstrated and an easy deblocking of the benzoyl protecting group is presented.

From Five- to Six-Membered Rings:  3,4-Diarylquinolinone as Lead for Novel p38MAP Kinase Inhibitors

In this study we describe the design, synthesis, and biological evaluation of 3-(4-fluorophenyl)-4-pyridin-4-ylquinoline-2(1H)-one (5) as a new inhibitor of MAPK with a p38alphaMAPK IC50 of 1.8 muM. By keeping the common vicinal pyridine/4-F-phenyl pharmacophore, such as in prototypical imidazole 20 or isoxazole 13 but in 5 connected to the six-membered quinoline core, we were particularly interested in comparing biological activity, details of molecular geometry, and different binding modes of these compounds. Compounds 20 and 13 were active both in the p38alpha- and JNK3-assay, whereas 5 was selective for p38alpha, with no JNK3 inhibition. By comparing the X-ray structures of the compound…

Cysteamine and its homoleptic complexes with group 12 metal ions. Differences in the coordination chemistry of ZnII, CdII, and HgII with a small N,S-donor ligand.

2-Ammoniumethanethiolate, (-)SCH(2)CH(2)NH(3)(+), the first structurally characterized zwitterionic ammoniumthiolate, is the stable form of cysteamine (HL) in the solid state and in aqueous solution. Reactions of ZnCl(2), Cd(Oac)(2), and HgCl(2) with cysteamine and NaOH in a 1:2:2 ratio, respectively, lead to the homoleptic complexes ML(2). Their single-crystal X-ray structures demonstrate basic differences in the coordination chemistry of Zn(II), Cd(II), and Hg(II). While chelating N,S-coordination modes are found for all metal ions, Zn(II) forms a mononuclear complex with a distorted tetrahedral Zn(N(2)S(2)) coordination mode, whereas Hg(II) displays a dimer with Hg(N(2)S(2)) coordinated …

Back Cover: A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (−)-Thebaine (Angew. Chem. Int. Ed. 34/2018)

2-(2,3,5,6-Tetra­methyl­benzyl­sulfan­yl)pyridine N-oxide

In the title compound, C16H19NOS, the durene ring and the oxopyridyl ring form a dihedral angle of 82.26&#8197;(7)&#176;. The crystal structure is stabilized by intermolecular C&#8212;H...O hydrogen bonds, weak C&#8212;H...&#960; interactions and &#960;&#8211;&#960; interactions [centroid&#8211;centroid distance of 3.4432&#8197;(19)&#8197;&#197;], together with intramolecular S...O [2.657&#8197;(2)&#8197;&#197;] short contacts.

Modular Access to 9,9-Spirobifluorenes by Oxidative Coupling Using Molybdenum Pentachloride

The strong oxidizing agent molybdenum pentachloride was used for an efficient direct C–C bond formation of 9,9-diarylfluorenes to the corresponding 9,9-spirobifluorenes. Thus, a versatile method that is compatible with labile groups, such as iodo moieties, was established. By this approach important building blocks for light emitting polymers were synthesized in high yields.

Stereoselective Synthesis of Polycyclic Thiopyrans

The reaction of benzothiete (1) and the bicyclic alkenes 5, 7, 9, or 12 shows a very high π side selectivity (de > 95%) in the formation of the polycyclic thiopyrans 6, 8, 10, 11, 13, and 14.

[2,5-Bis(dipropylamino)-4-(hydroxymethyl)phenyl]methanol

The centrosymmetric title compound, C22H36N2O2, was prepared in five steps from diethyl succinate. The dipropylamino groups are almost orthogonal to the central phenylenedimethanol ring [dihedral angle = 87.62 (9)°]. In the crystal, the molecules are connected by O—H...N hydrogen bonds, forming (101) layers separated by the propyl chains.

Unique Bridging Function of the Triazole Core in Copper(II) Chloride Complexes with 1-Allylbenzotriazole

During alternating-current electrochemical synthesis of copper(I) π-complex of [CuCl{C6H4N3(C3H5)}] composition, starting from ethanol solution, containing CuCl2·2H2O and 1-allylbenzotriazole, green crystals of intermediate [CuII3Cl6{C6H4N3(C3H5)}4] (I) compound has been obtained upon 24 h. After some days these crystals transform into red ones of [CuII2Cl4{C6H4N3(C3H5)}3] (II). Both compounds were X-Ray structurally investigated. Crystals of I are triclinic, sp.gr. a = 9.1329(9), b = 10.0352(4), c = 12.239(3) A, α = 76.443(13), β = 84.470(14), γ = 76.808(7)°, V = 1060.5(3) A3, R = 0.0414 for 3311 reflections. II: monoclinic, C2/c, a = 13.828(1), b = 15.044(2), c = 10.702(1) A, β = 91.36(1)…

4-(3-Hydroxy-4-methoxyphenyl)-3-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrole-2,5-dione

The title compound, C20H19NO7, crystallizes in the space group Pna21. X-ray analysis shows the compound has the desired 3′-hydroxy and 4′-methoxy substitution pattern, as in the natural template combretastatin A-4.

Synthesis of a Naphtho-pyrido-Annulated Iodonium Salt and Pd-Catalyzed Transformation to 7H-Naphtho[1,8-bc][1,5]naphthyridine

Nitropyridylnaphthalene is the central intermediate for the synthesis of naphthonaphthyridine and benzo-δ-carboline. Whereas the Cadogan reaction gives the carboline, transformation of the nitro group to iodo followed by oxidation and cyclization results in an iodonium salt. A twofold Pd-catalyzed amination leads to the naphthyridine.

Band-Shaped Structures by Repetitive Cycloaddition Reactions of Benzo[1,2-b:4,5-b′]bisthiete

Benzo[1,2-b:4,5-b′]bisthiete (1) undergoes stepwise thermal opening of the 4-membered rings, thereby generating two highly reactive 8π systems (Scheme 1). In the presence of 1,4-dihydro-1,4-epoxynaphthalenes 2, the dithiaheptacene derivatives 3 are formed, dehydration of which leads to the compounds 4 and 5 (Scheme 2). Repetitive cycloaddition reactions of 1 with the twofold 2π component 11 (Scheme 3) yield the oligomers 15 with statistically bent (and possibly cyclic) structures (Schemes 4 and 5). While 15 and the related oligomers 14 are freely soluble in many organic solvents, the dehydrated systems 16 (Scheme 6) are totally insoluble.

First total synthesis of antiostatin A1, a potent carbazole-based naturally occurring antioxidant.

The first total synthesis of the potent antioxidant antiostatin A1 is reported, where its key features rely on a chemo- and regioselective rhodium-catalysed crossed alkyne cyclotrimerisation reaction applying functionalised ynamides and a palladium-catalysed arylamidation reaction.

ChemInform Abstract: Synthesis of meta-Terphenyl-2,2′′-diols by Anodic C-C Cross-Coupling Reactions.

The anodic C−C cross-coupling reaction is a versatile synthetic approach to symmetric and non-symmetric biphenols and arylated phenols. We herein present a metal-free electrosynthetic method that provides access to symmetric and non-symmetric meta-terphenyl-2,2′′-diols in good yields and high selectivity. Symmetric derivatives can be obtained by direct electrolysis in an undivided cell. The synthesis of non-symmetric meta-terphenyl-2,2′′-diols required two electrochemical steps. The reactions are easy to conduct and scalable. The method also features a broad substrate scope, and a large variety of functional groups are tolerated. The target molecules may serve as [OCO]3− pincer ligands.

Regioselective Bromination and Functionalization of Dibenzo[hi,st]ovalene as Highly Luminescent Nanographene with Zigzag Edges.

Dibenzo[hi,st]ovalene (DBOV) is a nanographene with a combination of zigzag and armchair edges, consisting of 38 sp2 carbons. Excellent optical properties with strong red emission have been demonstrated. Here we report the regioselective bromination of DBOV bearing two mesityl groups (DBOV-Mes) by treatment with N-bromosuccinimide (NBS) under mild conditions. The dibrominated DBOV was further subjected to transition-metal-catalyzed cross-coupling reactions, that is, Suzuki and Sonogashira coupling, demonstrating the edge-decoration of DBOV with different functional groups. Notably, DBOVs arylated at the bay regions showed intense red emission and enhanced fluorescence quantum yields of up t…

Double azido-bridged and mixed-bridged binuclear copper(II) and nickel(II) compounds with N,N,O-donor Schiff bases: Synthesis, structure, magnetic and DFT study

Abstract Two dinuclear complexes μ1,1-azido bridged [Cu(L1)(N3)]2 (1) and μ-phenoxo, μ1,1-azido bridged [Ni2(L2)2(μ1,1-N3)(N3) H2O] (2) bearing HL1 and HL2 as a blocking co-ligands produced by the 1:1 condensation of N-benzyl ethylenediamine with ortho-hydroxy acetophenone and N-methyl propanediamine with 3-methoxy salicylaldehyde respectively, have been synthesized and successfully characterized by elemental analyses, IR and electronic spectroscopy, single-crystal X-ray diffraction, variable temperature magnetic study and DFT studies. X-ray crystal structures of 1 reveal that the Cu(II) ion displays a five-coordinate square pyramidal coordination with a centro-symmetric μ1,1-azido bridging…

Source of Selectivity in Oxidative Cross-Coupling of Aryls by Solvent Effect of 1,1,1,3,3,3-Hexafluoropropan-2-ol

Abstract Solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) with a high capacity for donating hydrogen bonds generate solvates that enter into selective cross-coupling reactions of aryls upon oxidation. When electric current is employed for oxidation, reagent effects can be excluded and a decoupling of nucleophilicity from oxidation potential can be achieved. The addition of water or methanol to the electrolyte allows a shift of oxidation potentials in a specific range, creating suitable systems for selective anodic cross-coupling reactions. The shift in the redox potentials depends on the substitution pattern of the substrate employed. The concept has been expanded from arene-phenol…

Formation of meso-1,2-Bis(dimethylamino)-1,2-diphenylethane by Oxidative C-C Coupling Reaction

The title compound was obtained from the reaction of N,N-dimethylbenzylamine with n-butyl lithium and sulfur in tetrahydrofuran at room temperature. Its molecular structure was investigated by means of single crystal X-ray diffraction and quantum chemical DFT methods. The formation of meso-1,2-bis(dimethylamino)-1,2-diphenylethane is likely to be due to an unusual α-deprotonation of N,N-dimethylbenzylamine, instead of the well known ortho-lithiation, with a subsequent oxidative C-C coupling of the anions. Ab initio calculations of the corresponding α- and o-deprotonated anions of N,N-dimethylbenzylamine showed the former to be more stable than the latter, due to delocalisation of the negati…

1-[4-(2-Aminoanilino)phenyl]-2,2,2-trifluoroethanone

In the title compound, C14H11F3N2O, the two aromatic rings are oriented at a dihedral angle of 70.84&amp;#8197;(8)&amp;#176;. The crystal structure displays intermolecular N&amp;#8212;H...O and N&amp;#8212;H...F interactions.

Highly Fluorinated 2,2′-Biphenols and Related Compounds: Relationship between Substitution Pattern and Herbicidal Activity

A broad range of halogenated 2,2'-biphenols was tested for applicability as crop protection agents. The activity of these compounds toward four typical pest plants was observed after application by spraying of diluted solutions. Despite their rather simple structure, it was found that the studied compounds reveal a surprisingly high herbicidal impact. To gain a better understanding of the structure-activity relationship, specific sites of the molecule were chemically modified and the core structures thus gradually changed. The influence of the substitution pattern on the herbicidal properties is discussed, and conclusions on the active site of the biphenol structure are drawn. It was observ…

From Hexaphenylbenzene to 1,2,3,4,5,6-Hexacyclohexylcyclohexane

The hydrogenation of hexaphenylbenzene was studied, affording novel partially hydrogenated hexacyclohexylbenzene (HCB) as well as fully hydrogenated 1,2,3,4,5,6-hexacyclohexylcyclohexane (HCC) as an unprecedented “oligocyclohexyl” molecule. The reaction process was analyzed by mass spectrometry with atmospheric pressure chemical ionization and high-performance liquid chromatography. From a crude product mixture, two different crystals with flake- and block-shapes could be grown and analyzed by X-ray crystallography, revealing their structures as HCB and HCC. While a geared arrangement of cyclohexyl substitutes was found in HCB, two isomeric structures were identified in HCC crystal with cha…

Diorganotin Compounds Containing α‐Aminoacidato Schiff Base Ligands Derived from Functionalized 2‐Hydroxy‐5‐(aryldiazenyl)benzaldehyde. Syntheses, Structures and Sensing of Hydrogen Sulfide

ChemInform Abstract: Synthesis of a Tetraazido-Substituted 2-Tetrazene from 1,5- Cyclooctadiene and Iodine Azide.

In contrast to the addition of iodine azide to cyclooctene (1) or 1,3-cyclooctadiene (5), its reaction with 1,5-cyclooctadiene (12) leads mainly to the surprisingly stable tetraazido-substituted 2-tetrazene 14 The structure of this was established by 15N-NMR studies and an X-ray structural analysis. Treatment of 14 with hydrochloric acid yields the diazido-substituted 9-azabicyclo[3.3.1]nonane 20.

Monoester copillar[5]arenes: synthesis, unusual self-inclusion behavior, and molecular recognition.

The self-inclusion behavior of monoester copillar[5]arenes depends on the position of the ester group, which causes different guest selectivities. Monoester copillar[5]arenes bearing an acetate chain can form stable self-inclusion complexes in low- and high-concentration solution and exhibit high guest selectivity. However, a monoester copillar[5]arene bearing a butyrate chain can not form a self-inclusion complex and exhibits low guest selectivity. Thus, a new class of stable self-inclusion complexes of copillar[5]arenes was explored to improve the selectivity of molecular recognition.

ChemInform Abstract: Source of Selectivity in Oxidative Cross-Coupling of Aryls by Solvent Effect of 1,1,1,3,3,3-Hexafluoropropan-2-ol.

Abstract Solvents such as 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) with a high capacity for donating hydrogen bonds generate solvates that enter into selective cross-coupling reactions of aryls upon oxidation. When electric current is employed for oxidation, reagent effects can be excluded and a decoupling of nucleophilicity from oxidation potential can be achieved. The addition of water or methanol to the electrolyte allows a shift of oxidation potentials in a specific range, creating suitable systems for selective anodic cross-coupling reactions. The shift in the redox potentials depends on the substitution pattern of the substrate employed. The concept has been expanded from arene-phenol…

Synthesis of a Tetraazido-Substituted 2-Tetrazene from 1,5-Cyclooctadiene and Iodine Azide

In contrast to the addition of iodine azide to cyclooctene (1) or 1,3-cyclooctadiene (5), its reaction with 1,5-cyclooctadiene (12) leads mainly to the surprisingly stable tetraazido-substituted 2-tetrazene 14 The structure of this was established by 15N-NMR studies and an X-ray structural analysis. Treatment of 14 with hydrochloric acid yields the diazido-substituted 9-azabicyclo[3.3.1]nonane 20.

Stereoselective Synthesis of Enantiomerically Pure Piperidine Derivatives byN-Galactosylation of Pyridones

Stereoselective desymmetrization of 4-pyridone has been achieved through selective N-galactosylation, activation of the N-(galactosyl)pyridone by O-silylation and immediate addition of Grignard compounds. Chiral piperidine derivatives, e.g. (S)-(+)-coniine and (5S,9S)-(+)-indolozidine 167B, were synthesised in enantiomerically pure form using these highly regio- and stereoselective reactions. After N-galactosylation of 2-pyridone and O-silylation of the N-galactosyl-2-pyridone, addition of a Grignard compound proceeded with high 1,4-regioselectivity and complete diastereoselectivity, to furnish 4-substituted 5,6-dehydro-2-piperidones. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Ger…

Structural diversity within analogous compounds: syntheses and studies of M(SCH2CH2NH2)Cl (M = Zn, Cd, Hg).

The novel complexes [Zn(L)Cl] (1), [Cd(L)Cl] (2), [Hg(L)Cl] (3), {[Hg(L)Cl]·NaOH·2H 2 O} (3·NaOH·2H 2 O), and {[Hg 3 (HL) 2 Cl 6 ]·2H 2 O} (4) (L = -SCH 2 CH 2 NH 2 ) were prepared and investigated by means of IR spectroscopy and single-crystal X-ray diffraction. The crystal structures of 1, 2, and 3·NaOH·2H 2 O show chelating N,S-coordination of the cysteaminate ligand, bridging S, and terminally coordinating Cl. Apart from these common features, the coordination geometries and modes of intermolecular association are different. 1 forms a cyclic tetramer with a Zn 4 S 4 ring, and 3·NaOH·2H 2 O contains one-dimensional [Hg(L)Cl] n chains with S-bridged Hg atoms. Zn and Hg atoms in 1 and 3·Na…

Investigations on isomerization and rearrangement of polycyclic arenes under oxidative conditions – Anodic versus reagent-mediated reactions

Abstract Electro-organic conversions at an active molybdenum anode enable the formation of fused arenes. High chemoselectivity was achieved under anodic conditions, and a reagent-induced selectivity was observed by comparison with results of MoCl5-mediated reactions. Polycyclic arenes like phenanthrenes, triphenylenes, chrysenes, or helicenes were selectively obtained in yields up to 87% and in some cases unusual rearrangements were crucial for the product formation.

2,7-Di-tert-butyl-9,9-dimethyl-4,5-bis(4-tritylanilinocarbonyl)-9H-xanthene methanol trisolvate monohydrate

The title compound, C75H68N2O3·3CH3OH·H2O, was synthesized starting from the corresponding acid and p-tritylaniline. Single crystals were obtained from a methanol solution as a solvate, with three methanol mol­ecules and one water mol­ecule. The solid-state structure proves the existence of an intra­molecular bifurcated hydrogen bond between one amide H atom and the carbonyl and xanthene O atoms. The packing is stabilized by inter­molecular hydrogen bonds.

4-Methyl-N-(4-methylpyridin-2-yl)-N-(3,4,5,6-tetrahydro-2H-pyran-4-yl)pyridin-2-amine

In the title compound, C17H21N3O, the pyridine rings make a dihedral angle of 84.44 (5)°. In the crystal, a C—H...N interaction forms a chain of molecules propagating along the twofold screw axis.

Pollutant Adsorbtion and Detection: Methyl-Substituted α-Cyclodextrin as Affinity Material for Storage, Separation, and Detection of Trichlorofluoromethane (Global Challenges 8/2018)

The cover image depicts the hazard caused by chlorofluorocarbons such as CFC‐11, which are used, for example, as blowing agents for polyurethane foams, and the protective effect of the oligosaccharide, hexakis‐(2,3,6‐tri‐O‐methyl)‐α‐cyclodextrin, which is capable of binding CFC‐11 by supramolecular complexation and thus protecting the stratospheric ozone layer from the harmful trichlorofluoromethane. Further details can be found in article number 1800057 by Ralf Hellmann, Siegfried R. Waldvogel, and co‐workers.

3-(2,4-Difluorophenyl)-1-(pyridin-4-yl)benzo[4,5]imidazo[1,2-d][1,2,4]triazin-4(3H)-one

In the title compound, C20H11F2N5O, the central 13-membered ring system (r.m.s. deviation = 0.028 Å) makes a dihedral angle of 53.13 (7)° with the difluorophenyl ring and 79.98 (7)° with the pyridine ring. The crystal packing features aromatic π–π interactions between the 13-membered rings [shortest distance between ring centroids = 3.5682 (8) Å].

Reversible Covalent and Supramolecular Functionalization of Water-Soluble Gold(I) Complexes.

The ligation of gold(I) metalloamphiphiles with biomolecules is reported, using water-soluble AuI -N-alkynyl substituted maleimide complexes. For this purpose, two different polar ligands were applied: 1) a neutral, dendritic tetraethylene glycol-functionalized phosphane and 2) a charged, sulfonated N-heterocyclic carbene (NHC). The retro Diels-Alder reaction of a furan-protected maleimide gold(I) complex, followed by cycloaddition with a diene-functionalized biotin under mild conditions leads to a novel gold(I) metalloamphiphile. The strong streptavidin-biotin binding affinity in buffered aqueous solution of the resulting biotin alkynyl gold(I) phosphane conjugate remains intact. The cytot…

Metall- und reagensfreie dehydrierende formale Benzyl-Aryl-Kreuzkupplung durch anodische Aktivierung in 1,1,1,3,3,3-Hexafluorpropan-2-ol

2-(Benzylsulfanyl)pyridineN-oxide

In the title compound, C12H11NOS, the dihedral angle between the oxopyridinium and phenyl rings is 58.40&#8197;(1)&#176;. The crystal structure is stabilized by C&#8212;H...O hydrogen bonds, &#960;&#8211;&#960; stacking interactions involving the pyridinium rings [centroid&#8211;centroid distance = 3.6891&#8197;(9)&#8197;&#197;] and C&#8212;H...&#960; interactions.

Synthesis ofmeta-Terphenyl-2,2′′-diols by Anodic C−C Cross-Coupling Reactions

The anodic C-C cross-coupling reaction is a versatile synthetic approach to symmetric and non-symmetric biphenols and arylated phenols. We herein present a metal-free electrosynthetic method that provides access to symmetric and non-symmetric meta-terphenyl-2,2''-diols in good yields and high selectivity. Symmetric derivatives can be obtained by direct electrolysis in an undivided cell. The synthesis of non-symmetric meta-terphenyl-2,2''-diols required two electrochemical steps. The reactions are easy to conduct and scalable. The method also features a broad substrate scope, and a large variety of functional groups are tolerated. The target molecules may serve as [OCO](3-) pincer ligands.

Methyl [4-methoxy-3-(methylsulfonyloxy)benzoyl]formate

The crystal structure of the title compound, C11H12O7S, confirms an earlier proposal concerning the regioselectivity of electrophilic substitution reactions of mesyl guaiacol.

Synthesis of bis(indolylmaleimide) macrocycles

The synthesis of a novel class of macrocyclic bis(indolylmaleimides) is reported. The key step involves the intermolecular connection of 2,2′-bridged indoles with 3,4-dibromo-2,5-dihydro-1H-2,5-pyrroledione (dibromomaleimide) derivatives. The bis(indolylmaleimides) afforded by this method were further processed by intramolecular nucleophilic substitution of the remaining bromo substituents forming flexible N-substituted macrocycles (9a-9j, 10a-10e) and, by connecting both maleimides, semi rigid macrocycles (7a-7xx).

Inside Cover: Reagent- and Metal-Free Anodic C−C Cross-Coupling of Aniline Derivatives (Angew. Chem. Int. Ed. 17/2017)

N-[(1S,2S)-2-Amino-1,2-diphenyl­eth­yl]-4-methyl­benzene­sulfonamide [(S,S)-TsDPEN]

The crystal structure of the title compound, C21H22N2O2S, shows a network of N&amp;#8212;H...N and N&amp;#8212;H...O hydrogen bonds. The tolyl and 1-phenyl rings are almost mutually coplanar [7.89&amp;#8197;(9)&amp;#176;], while the 2-phenyl ring makes a dihedral angle of 50.8&amp;#8197;(1) &amp;#176; with the 1-phenyl ring. An intramolecular N&amp;#8212;H...N hydrogen bond stabilizes the molecular conformation.

2-(4-Fluorophenyl)-1-(4-pyridyl)cyclopentan-1-ol

The crystal structure of the title compound, C16H16FNO, was determined as part of a study of the biological activity of pyridine-substituted cyclo­pentene derivatives as p38 mitogen-activated protein kinase (MAPK) inhibitors. The 4-fluoro­phenyl and 4-pyridyl rings are trans positioned with respect to each other. The compound exists as a racemic mixture. The synthesis was achieved via direct inter­action between the reactive complex Grignard reagent PyMgCl·LiCl and the enolizable ketone 4-fluoro­phenyl­cyclo­penta­none with the assistance of the neodymium salt catalyst NdCl3·2LiCl. The crystal packing is characterized by zigzag chains of mol­ecules, which are connected by O—H⋯N hydrogen bon…

A frozen analogue approach to aminopyridinylimidazoles leading to novel and promising p38 MAP kinase inhibitors.

In this study we report the design, synthesis, and biological evaluation of constrained aminopyridinylimidazoles as p38α MAP kinase inhibitors. The frozen analogue approach focused on the pyridinyl unit, using purine bioisosteres as constrained structure analogues. The identification of the most potent bioisostere was followed by a further derivatization to address hydrophobic region II. In combination with C-2 modifications of the imidazole core, we were able to design highly active inhibitors on the p38α MAP kinase. The inhibitor design presented herein represents a promising and highly efficient advancement of recent stages of development in this class of p38 MAP kinase inhibitors. In co…

Oligofluorene with multiple spiro-connections: its and their use in blue and white OLEDs

Bond rotation within molecules is regarded as one of the nonradiative decay pathways and is detrimental to high photoluminescence quantum yields. In this work, a bulky and rigid blue emitter (Spiro-F) with five spiro-carbon linkages is synthesized. Spiro-F can serve not only as an active component of blue organic light-emitting diodes (OLEDs), but also as a host and blue emitter of white OLEDs. The WOLED offers a low turn-on voltage of 3.5 V and a high current efficiency of 3.6 cd A−1, together with CIE coordinates of (0.29, 0.33). This work proves the potential of super-rigid oligofluorene emitters for OLEDs.

Synthesis, crystal structure and magnetic properties of bis[μ-bis(3-(pyridin-2-yl)-1,2,4-triazole-N′,N1,N2)] bis[triaqua nickel(II)] tetranitrate

Abstract A new dinuclear nickel(II) coordination compound of formula Ni2(Hpt)2(H2O)6(NO3)4 (Hpt=3-(pyridin-2-yl)-1,2,4-triazole) was synthesized. The structure was solved at 298 K by single-crystal X-ray analysis. Bisμ-bis(3-(pyridin-2-yl)-1,2,4-triazole-N′,N1,N2) bistriaqua nickel(II) tetranitrate (C14H24N12O18Ni2) crystallizes in the triclinic space group P-1, a=7.2266(1), b=9.9144(1), c=11.2647(1) A, α=66.854(1)°, β=74.000(1)°, γ=86.400(2)°, V=712.42(1) A3, Z=1 (dinuclear units), 2823 reflections (1 > 2σ(I)), R1=0.0442, wR2=0.1197. The Ni(II) ions are bridged by two neutral Hpt ligands coordinating via N1 and N2 in the equatorial plane, Ni(1)-Ni(1)′=4.098(1) A. The Hpt bridging mode is a…

4-[5-Amino-4-(4-fluorophenyl)-3-(pyridin-4-yl)-1H-pyrazol-1-yl]benzonitrile

In the crystal structure of the title compound, C21H14FN5, the pyrazole ring forms dihedral angles of 38.0 (1), 40.0 (1) and 28.5 (1)° with the directly attached 4-fluorophenyl, pyridine and benzonitrile rings, respectively. The crystal packing is characterized by N—H...N hydrogen bonds, which result in a two-dimensional network parallel to theac-plane.

3-(4-Fluorophenyl)-2-(4-pyridyl)pyrido[2,3-b]pyrazine

In the crystal structure of the title compound, C18H11FN4, the pyridopyrazine ring makes dihedral angles of 34.67&amp;#8197;(7) and 52.24&amp;#8197;(7)&amp;#176; with the 4-fluorophenyl and pyridine rings, respectively. The 4-fluorophenyl ring makes a dihedral angle of 59.56&amp;#8197;(9)&amp;#176; with the pyridine ring.

Donellanic acids A–C: new cyclopropanic oleanane derivatives from Donella ubanguiensis (Sapotaceae)

Abstract Three new cyclopropanic oleanane triterpenoids and ten known compounds were obtained from Donella ubanguiensis using chromatographic methods. The structures were established on the basis of mass spectrometric and NMR data and by comparison with values reported in the literature. The structures of the new compounds were confirmed by X-ray crystallography. A part of the isolated compounds was evaluated for cytotoxic and antimicrobial activities.

Step-growth Polymerization ofBistriazolinediones with1,1-Diphenylethylene

The reactions of 4-ethyl-1,2,4-triazoline-3,5-dione (ETD) (1) and 4-phenyl-1,2,4-triazoline-3,5-dione (PhTD) (2) with 1,1-diphenylethylene (DPE) (3) were investigated at room temperature. The reactions are very fast and are completed in less than 4 min. These reactions lead to the formation of two 2 :1 adducts via double Diels-Alder and Diels-Alder-ene reactions in a ratio of 1.35 : 1. The structure of these adducts where R = Et were determined by X-ray analysis of a single crystal. These compounds were used as models for the polymerization reactions. The reaction of bistriazolinediones (1,6-bis-(3,5-dioxo-1,2,4-triazoline-4-yl)hexane and bis-(p-3,5-dioxo-1,2,4-triazoline-4-ylphenyl)methane…

Synthesis of iodobiaryls and dibenzofurans by direct coupling at BDD anodes.

The first direct oxidative phenol-arene cross-coupling reactions of an iodine-containing guaiacol derivative and the possible over-oxidation products of electron-rich phenols are described. Hereby, a "green" and targeted synthesis for dibenzofurans was developed.

Electrochemical C−H Functionalization of (Hetero)Arenes—Optimized by DoE

Abstract A novel approach towards the activation of different arenes and purines including caffeine and theophylline is presented. The simple, safe and scalable electrochemical synthesis of 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) aryl ethers was conducted using an easy electrolysis setup with boron‐doped diamond (BDD) electrodes. Good yields up to 59 % were achieved. Triethylamine was used as a base as it forms a highly conductive media with HFIP, making additional supporting electrolytes superfluous. The synthesis was optimized using Design of Experiment (DoE) techniques giving a detailed insight to the significance of the reaction parameters. The mechanism was investigated by cyclic volt…

On the Reaction of (tBu2SnO)3 with Organochlorosilanes. Simple Formation of [(tBu2SnO)2(tBu2SiO)]

Azido bridged binuclear copper(ii) Schiff base compound: synthesis, structure and electrical properties

An azido bridged dinuclear complex [Cu(L−)(μ1,1N3)]2 (1) was synthesized by a 1 : 1 condensation of N-cyclohexyl-1,3-propanediamine and 5-bromosalicylaldehyde (HL). The complex was subsequently characterized based on elemental analyses, IR, single-crystal X-ray diffraction, a Hirshfeld study, FESEM, ESI-MS, powder XRD and also DFT studies successfully. The X-ray crystal structure of complex 1 revealed that the Cu(II) ion exhibited a definite five-coordinate square pyramidal coordination arrangement with a centro-symmetric μ 1,1-azido bridging in the end-on mode and formed a dimeric structure. The optical direct band gap of complex 1 was estimated to be 2.84 eV. The current–voltage character…

1-Benzyl-1H-benzotriazole

In the title compound, C13H11N3, the benzotriazole ring system is essentially planar, with a maximum deviation of 0.0173&amp;#8197;(18)&amp;#8197;&amp;#197;, and forms a dihedral angle of 75.08&amp;#8197;(8)&amp;#197; with the phenyl ring. In the crystal, pairs of weak C&amp;#8212;H...N hydrogen bonds form inversion dimers. In addition, there are weak C&amp;#8212;H...&amp;#960;(arene) interactions and weak &amp;#960;&amp;#8211;&amp;#960; stacking interactions, with a centroid&amp;#8211;centroid distance of 3.673&amp;#8197;(11)&amp;#8197;&amp;#197;.

Eine regio- und diastereoselektive anodische Aryl-Aryl-Kupplung in der biomimetischen Totalsynthese von (−)-Thebain

1-Benzyl-1H-benzotriazole 3-oxide monohydrate

In the title hydrate, C13H11N3O&amp;#183;H2O, the benzotriazole ring system is planar (r.m.s. deviation = 0.007&amp;#8197;&amp;#197;) and is almost orthogonal to the phenyl ring to which it is linked by a methylene group, forming a dihedral angle of 81.87&amp;#8197;(15)&amp;#176;. In the crystal, molecules are linked into chains along [001] by O&amp;#8212;H...O hydrogen bonds. The chains are consolidated into a three-dimensional architecture by C&amp;#8212;H...O, C&amp;#8212;H...&amp;#960; and &amp;#960;&amp;#8211;&amp;#960; [centroid&amp;#8211;centroid distance between the five- and six-membered rings of the benzotriazole ring system = 3.595&amp;#8197;(3)&amp;#8197;&amp;#197;] interactions.

Design, Synthesis, and Biological Evaluation of 3,4-Diarylmaleimides as Angiogenesis Inhibitors

The new analogue 2 of combretastatin A-4 was discovered to be an inhibitor of tubulin polymerization with an IC50 of 7.6 microM and reduced angiogenesis in the in vivo chick embryo model. Interestingly, in a series of 2,3-diarylmaleimides closely related to this lead, no other compound was found to be active in the tubulin polymerization assay. However, by screening in the in vivo chick embryo assay 10 was identified as a potent angiogenesis inhibitor indicating an alternative target. Indeed, molecular modeling studies suggest a reasonable binding mode of 10 at the ATP-binding site of the model kinase CDK2. Motivated by these results, analogues of 10 were screened for inhibitory activity in…

3,4′,5,5′-Tetramethoxy-2′-methylbiphenyl-4-ol

The asymmetric unit of the title compound, C17H20O5, contains two independent molecules, A and B, with similar geometries [dihedral angles between the phenyl rings = 56.19 (8) and 54.98 (7)°, respectively]. Intramolecular O—H...O hydrogen bonds occur in both molecules. In the crystal, the A molecules form [1\overline{1}0] chains linked by O—H...O hydrogen bonds from the hydroxyl group to one of the methoxy O atoms. The B molecules form O—H...O hydrogen bonds to the hydroxyl O atoms of the A molecules and thus act as fixed spacers between the chains of molecule A. Some weak C—H...O contacts are also present.

Omphalocarpoidone, a new lanostane-type furano-spiro-γ-lactone from the wood of Tridesmostemon omphalocarpoides Engl. (Sapotaceae)

Abstract Phytochemical studies of the wood and the stem bark of Tridesmostemon omphalocarpoides Engl. (Sapotaceae) led to the isolation of omphalocarpoidone (1), a new lanostane-type furano-spiro-γ-lactone together with β-amyrin acetate (2), taraxerol (3), spinasterol (4), lichexanthone (5), epi-catechin (6), spinasterol 3-O-β- d -glucopyranoside (7), tormentic acid (8), and 1,2,3,4-tetrahydronorharman-1-one (9). Their structures were established on the basis of extensive NMR studies, mass spectrometry, and by comparison of the data with those previously reported in the literature. The structure of the new secondary metabolite was later confirmed by X-ray crystallography. Except for spinast…

Synthesis of Pyrrolidin-2-ones and of Staurosporine Aglycon (K-252c) by Intermolecular Michael Reaction

Indolo[2,3-a]pyrrolo[3,4-c]carbazoles were isolated from nature, e.g., from low plants, especially fungi, as structurally rare natural substances. Responsible for naming and also the most important representative of this type is staurosporine (1), isolated from Streptomyces staurosporeus, and its aglycon (2), also known as staurosporinone or K-252c. 3,4-Disubstituted pyrrolidin-2-ones, a group of compounds with many interesting biological properties are related to staurosporinone. The most important property is the inhibition of protein kinase C (PKC), so that this antiproliferative agent can interfere with the cell cycle. The synthetic strategy, developed by us, allows the synthesis of pyr…

ChemInform Abstract: Methods for Preparing Cyclic β-Cyclopentadienyl(dicarbonyl)iron-Substituted α,β-Unsaturated Carbonyl Compounds: Precursors to Annulated α,β-Butenolides and γ-Lactams.

Derivatives of (-)-Isosteviol with Expanded Ring D and Various Oxygen Functionalities

(–)-Isosteviol is a unique ex-chiral-pool building block that is readily available. Both functional groups are aligned in a concave manner. The methyl moiety on the backbone also points in this direction, creating a strong asymmetric environment close to these functional groups. The slightly divergent orientation of the keto and carboxy functions limits its use in the construction of supramolecular architectures as optically pure divalent building blocks. By selective transformations, ring D of (–)-isosteviol can be expanded and equipped with oxygen-containing functionalities, providing a variety of useful and rigid building blocks with defined stereochemistry.

Methyl-Substituted α-Cyclodextrin as Affinity Material for Storage, Separation, and Detection of Trichlorofluoromethane

Abstract The severely ozone‐depleting trichlorofluoromethane is still appearing in several recycling processes or industrial applications. A simple and selective supramolecular complex formation of per‐methylated α‐cyclodextrin (1) with the highly volatile trichlorofluoromethane (2) is reported. This interaction moreover leads to thermally stable crystals. Per‐methylated α‐cyclodextrin is successfully exploited as a reversible and selective adsorption material for liquid and airborne trichlorofluoromethane as well as an affinity material for the chemical sensing and detection of this particular volatile organic component.

ChemInform Abstract: Synthetic and Mechanistic Aspects of the Course of the Color Reaction of Iminodibenzyl with Aryl- or Hetaryl-aldehydes: An Access to New Hetaryl-/Aryl-methanes and 4,5-Diamino-cyclopentenones.

Cycloadditions of vinylindoles with chiral carbodienophiles: the first asymmetric Diels-Alder reactions in the vinylhetarane series

Abstract The first asymmetric Diels-Alder reactions of some 3- and 2-vinylindoles with (N-propenoyl)bornane-10,2-sultam are described. With one exception, the experimental results are indicative of a high π-facial diastereoselectivity. Following a related procedure, 3-vinylindoles were also allowed to react with a racemic bis(naphthylsulfonyl)-dienophile to furnish tetrahydrocarbazoles with endo-diastereoselectivity.

Synthese vonmeta-Terphenyl-2,2′′-diolen durch anodische C-C-Kreuzkupplungen

Die anodische C-C-Kreuzkupplung ist eine vielseitig einsetzbare Transformation, die eine gezielte Synthese von Biphenolen und arylierten Phenolen ermoglicht. Wir berichten uber einen ebenfalls elektrosynthetischen, metallfreien Ansatz, der einen Zugang zu symmetrischen und nichtsymmetrischen meta-Terphenyl-2,2′′-diolen in guten Ausbeuten und hoher Selektivitat ermoglicht. Symmetrische Derivate konnen durch eine direkte Synthese in einer ungeteilten Zelle gewonnen werden, wohingegen nichtsymmetrische meta-Terphenyl-2,2′′-diole zwei elektrochemische Stufen benotigen. Die milde Methode ist einfach durchzufuhren und skalierbar. Auserdem konnte erstmalig eine breite Substratvariabilitat aufgezei…

Molecular and Crystal Structures of TeCl4-Allylalcohol and -Allylacetate Adducts

Poly[[tetramethanolbis[4-oxo-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-olato]disodium]–diethyl ether–methanol (1/1/2)]

In the title compound, [Na2(C16H7Cl3N5O2)2(CH3OH)4]·C4H10O·2CH3OH, the central pyrazolo[3,4-d]pyrimidine system makes dihedral angles of 82.98 (7)° with the trichlorophenyl ring and 13.11 (15)° with the pyridine ring. The sodium ion has an octahedral environment, being coordinated by four methanol molecules and one O and one N atom of two different heterocyclic ring systems.

Spiro-fused bis-hexa-peri-hexabenzocoronene.

A spiro-fused hexa-peri-hexabenzocoronene dimer was synthesized, and its physicochemical properties were studied by UV-Vis absorption and emission spectroscopy as well as cyclic voltammetry. Chemical oxidation of SB-HBC afforded its radical cation and dication derivatives, which could be reversibly reduced to the neutral state.

ChemInform Abstract: Iodocyclization of o-Alkynylbenzamides Revisited: Formation of Isobenzofuran-1(3H)-imines and 1H-Isochromen-1-imines Instead of Lactams.

Remarkably, isobenzofuran and benzopyran derivatives are obtained by the title reaction and not as described in earlier publications five- or six-membered lactams.

Inside Back Cover: Metal- and Reagent-Free Dehydrogenative Formal Benzyl-Aryl Cross-Coupling by Anodic Activation in 1,1,1,3,3,3-Hexafluoropropan-2-ol (Angew. Chem. Int. Ed. 37/2018)

3-(1H-Indol-3-yl)-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrole-2,5-dione

The crystal structure of the title compound, C21H18N2O5, was determined in order to study the electrocyclic reactivity of 3,4-di­aryl-1H-pyrrole-2,5-dione derivatives. Intermolecular hydrogen bonds form sheets.

Thermal and Light-Induced Spin Transition in the High- and Low-Temperature Structure of [Fe0.35Ni0.65(mtz)6](ClO4)2

The thermal and light induced spin transition in [Fe(0.35)Ni(0.65)(mtz)(6)](ClO(4))(2) (mtz = 1-methyl-1H-tetrazole) was studied by (57)Fe Mössbauer spectroscopy and magnetic susceptibility measurements. In addition to the spin transition of the iron(II) complexes the compound undergoes a structural phase transition. The high-temperature structure could be determined by X-ray crystallography of the isomorphous [Fe(0.25)Ni(0.75)(mtz)(6)](ClO(4))(2) complex at room temperature. The X-ray structural analysis shows this complex to be rhombohedric, space group Rthremacr;, with a = 10.865(2) Å and c = 23.65(1) Å with three molecules in the unit cell. The transition to the low-temperature structur…

Synthesis and Unusual NMR-Spectroscopic Behavior of a Strained Bicyclic Ammonium Salt

(2aRS,3RS,4aSR,6aRS,6bSR)-3-Hydroxy-2a,3,4a,6,6a,6b-hexahydro-1,4-dioxacyclopenta[cd]pentalen-2(5H)-one

The mol­ecular structure of the title compound [enanti­omers (VIII) and (VIIIa)], C8H10O4, was determined in the course of our studies on the synthesis of cyclo­penta­[1,2-b]furan-4-one derivatives. Tricyclic (VIIIa) consists of a planar bridged lactone unit and the two other ring systems in the envelope conformation. It contains five chiral C atoms and was obtained as a racemic mixture. The X-ray analysis showed the compound to possess a half-acetal unit with an endo orientation of the half-acetal ether bridge with respect to the lactone unit.

Electrochemical Synthesis of Fluorinated Orthoesters from 1,3‐Benzodioxoles

Abstract Invited for this month's cover picture is the group of Professor Siegfried Waldvogel. The cover picture displays the robustness achieved by the installation of fluorinated alcohols on 1,3‐benzodioxoles, protecting the obtained orthoesters against acids and bases, like the shield of a knight. The simple protocol allows access to interesting compounds, whose lipophilicity is tremendously increased by the incorporation of fluorinated groups. This makes it possible to adjust the physicochemical properties of the biologically active 1,3‐benzodioxole motif. The surprisingly high stability against acids and bases gives rise to subsequent functionalizations or direct application in medicin…

(E)-1-(Pyridin-4-yl)propan-1-one O-tosyl oxime

The title compound, C15H16N2O3S, was obtained by the reaction of (E)-1-(pyridin-4-yl)propan-1-one oxime andpara-toluenesulfonic acid. The pyridine ring makes a dihedral angle of 54.70 (10)° with the benzene ring. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming a chain along thec-axis direction.

PyridiniumD(+)-10-camphorsulfonate hemihydrate

In the crystal structure of pyridinium d(+)-10-camphor­sulfonate hemihydrate, C5H6N+·C10H15O4S−·0.5H2O, a water mol­ecule lying on a twofold axis serves as a donor of two hydrogen bonds, thus linking two camphor­sulfonate anions. Each anion in its turn acts as a hydrogen-bond acceptor for the NH group of a pyridinium cation.

Visible Light-Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three-Component Photoredox Reaction

Simultaneous sulfonylation/arylation of styrene derivatives is achieved in a photoredox-catalyzed three-component reaction using visible light. A broad variety of difunctionalized products is accessible in mostly excellent yields and high diastereoselectivity. The developed reaction is scalable and suitable for the modification of styrene-functionalized biomolecules. Mechanistic investigations suggest the transformation to be operating through a designed sequence of radical formation and radical combination.

Hydrophobic Encapsulated Phosphonium Salts-Synthesis of Weakly Coordinating Cations and their Application in Wittig Reactions

Large and rigid tetraarylphosphonium tetrafluoroborate salts have been synthesized representing weakly coordinating cations with diameters of several nanometers. Divergent dendritic growth by means of thermal Diels-Alder cycloaddition was employed for the construction of the hydrophobic polyphenylene framework up to the third generation. X-ray crystal structure analysis of first-generation phosphonium tetrafluoroborate supported the rigidity of the non-collapsible shell around the phosphorus center and gave insight into solid-state packing and cation-anion distances. Copper(I)-catalyzed azide-alkyne ligation served as reliable method for the preparation of a first-generation triazolylphenyl…

Dipolar Relaxation in Functionalized Poly-p-phenylenes Bearing Ultrastrong Dipoles Perpendicular to the Backbone

Local polymer dynamics are studied in polymers bearing dipoles rigidly attached to the backbone. The compounds are based on cyano-substituted dihydrobenzimidazoles bearing ultrastrong dipole moments (∼12 D per repeat unit) incorporated in a poly-p-phenylene backbone, giving rise to polymers with rigid dipoles perpendicular to the chain. They belong to type B polymers according to the Stockmayer classification. They are ideal model systems for studying rotational isomers in the gas phase and the self-assembly and local dynamics in the solid state. Gas phase calculations (DFT) provided the dipole moments, the energetic barriers, and the backbone conformation as a function of the dipole streng…

The Role of Side-Arms for Supramolecular Affinity Materials Based on 9,9′-Spirobifluorenes

An eightfold functionalized D2d-symmetric 9,9' spirobifluorene was condensed with a collection of diketones with elaborated structural features to form three-dimensional supramolecular architectures with active surfaces. Gas sorption measurements by quartz crystal microbalances revealed remarkable indications about the molecular interactions for the application as affinity materials for the detection of volatile organic compounds. Single-crystal X-ray structure analysis further gave insight by packing motifs and for potential host-guest interactions.

Synthesis of (+) and (‐)‐Streptomyces coelicolor Butanolide 5 (SCB‐5)

ChemInform Abstract: Reactions of (η5-C5H5) (CO)2Fe-Substituted N-Sulfonyl Azadienes with C-Nucleophiles. A Route to 5-Substituted Dihydropyrrolones.

ChemInform Abstract: Stereoselective Synthesis of Polycyclic Thiopyrans.

Reactions of benzothiete (I) with bicyclic alkenes exhibit very high π-side selectivity in the formation of polycyclic thiopyrans.

Metall- und reagensfreie hochselektive anodische Kreuzkupplung von Phenolen

ChemInform Abstract: (a)-Anellated Carbazoles with Antitumor Activity: Synthesis and Cytotoxicity.

The cycloadducts3,5, and7, readily available from methoxy-substituted 3-vinylindoles1 and2, were dehydrogenated withDDQ to the coplanar [a]-anellated carbazoles4,6, and8. Compound4a, also characterized by X-ray structural analysis, shows significant cytotoxicity against K562 und RXF393 human tumor cell lines.

Diethyl [(2,5-diiodo-4-methylphenyl)methyl]phosphonate

The title compound, C12H17I2O3P, was prepared in three steps from p-xylene. Heterodimers between nearly identical molecules are connected via three hydrogen bonds from benzylic and ester methylene groups to phosphonate. The dimers form chains along the a-axis direction, stabilized by C—H...O bridges.

Mo-Based Oxidizers as Powerful Tools for the Synthesis of Thia- and Selenaheterocycles.

A highly efficient synthetic protocol for the synthesis of thia- and selenaheterocycles has been developed. By employing a MoCl5 -mediated intramolecular dehydrogenative coupling reaction, a broad variety of structural motifs was isolated in yields up to 94 %. The electrophilic key transformation is tolerated by several labile moieties like halides and tertiary alkyl groups. Due to the use of disulfide or diselenide precursors, a high atom efficiency was achieved.

Electrophilic substitution and cyclization of 2,2′-bis(N-methylindolyl): A simple access to potential protein kinase C inhibitor

A strategy is described for the synthesis of functionalized and cyclized 2,2′-bisindolyl derivatives related to several basic systems of natural products. The starting 2,2′-bis(N-methylindolyl) (8) reacts with a variety of electrophiles and electrophilic dienophiles to furnish the novel, functionalized and cyclized bisindolyl derivatives 9–16. In addition, some reactivity and structural aspects are discussed; an X-ray crystallographic analysis of the 2,2′-bisindolyl 8 provided valuable information for the conformational analyses.

Tetra­kis{2,4-bis­[(1-oxo-2-pyridyl)­sulfanyl­methyl]mesitylene} acetone hemisolvate 11.5-hydrate

In the crystal structure of the title compound, 4C21H22N2O2S2&#183;0.5C3H6O&#183;11.5H2O, there are four crystallographically independent molecules (A, B, C, D) with similar geometries, 11 water molecules and a solvent acetone molecule which is disordered with a water molecule with occupancy factors of 0.5:0.5. The dihedral angles formed by the mesitylene ring with the two pyridyl rings are 82.07&#8197;(3) and 78.39&#8197;(3)&#176; in molecule A, 86.20&#8197;(3) and 82.29&#8197;(3)&#176; in molecule B, 81.05&#8197;(3) and 76.0&#8197;(4)&#176; in molecule C, 86.0&#8197;(3) and 80.9&#8197;(3)&#176; in moleule D. The two pyridyl rings form dihedral angles of 41.17&#8197;(4), 64.01&#8197;(3), 8…

A surprising switch in absolute configuration of anti-inflammatory macrolactones.

Oxacyclododecindione-type macrolactones exhibit highly potent anti-inflammatory activities even at nanomolar concentration. After the determination of the relative configuration of the stereocenters at C14 and C15 by total synthesis of 4-dechloro-14-deoxyoxacyclododecindione and 14-deoxyoxacyclododecindione, the absolute configuration has now been assigned by X-ray crystallography. Surprisingly, the absolute configuration is (14S,15R) which differs for C15 from that of the well-known derivatives of (S)-curvularin. The biological activities of both enantiomers of 14-deoxyoxacyclododecindione, obtained by racemic synthesis and optical resolution, were investigated and the ring conformation of…

Molybdenum Pentachloride Mediated Synthesis of Spirocyclic Compounds by Intramolecular Oxidative Coupling

The oxidative treatment of (m)ethyl 2-aryl cinnamates equipped with methoxy groups in position 4 of the phenyl moiety promote the formation of cyclohexadienone substructures. This dealkylative oxidative C–C coupling gives access to spirocyclic compounds and avoids the construction of the corresponding phenanthrenes. Furthermore, the transformation can be expanded to other spirocyclic systems.

ChemInform Abstract: Modular Access to 9,9-Spirobifluorenes by Oxidative Coupling Using Molybdenum Pentachloride.

The reactions of diarylfluorenes and substrates (III) or (V) result in formation of spirobifluorenes and fluorene derivatives.

Electrochemical Formation of 3,5-Diimido-1,2-dithiolanes by Dehydrogenative Coupling

A synthetic approach to the cyclic disulfide moiety of 3,5-diimido-1,2-dithiolane derivatives starting with readily available precursors including the electrochemical coupling of dithioanilides is developed. The electrochemical key step provides sustainable synthetic access in high yields, using a very simple electrolysis setup.

X-ray Crystal Structure of Woodinine and Conformational Analysis by Semiempirical and 1H-NMR Methods

The mol. structure of (-)-woodinine (I), a carboline-based alkaloid with antibacterial and antimycobacterial activities, was investigated by X-ray crystallog., NMR, and semiempirical quantum chem. methods. The X-ray crystal structure of I showed the indole ring in the expected planar conformation, the pyrrolidine ring in an envelope conformation, and a weak intramol. hydrogen bond between the pyrrolidine nitrogen and the proton of the indole nitrogen. NMR expts. indicated that this hydrogen bond is not present in soln. and that further differences exist between the crystal and the soln. structures of I. By semiempirical quantum chem. methods, different local energy min. conformations of I, …

Simple chiral urea gelators, (R)- and (S)-2-heptylurea: their gelling ability enhanced by chirality.

Abstract We present the first report on the synthesis of chiral ureas, ( R )- and ( S )-2-heptylurea, and their gelling behaviors. The ureas were prepared by the reactions of chiral amines and phenyl carbamate in the presence of triethylamine. On cooling from homogeneous solutions, the chiral ureas form gels in water and various nonpolar organic solvents, such as cyclohexane, toluene, and tetrachloromethane, while the racemate gelatinize only toluene and tetrachloromethane among the solvents we examined. The gelling ability of the enantiomeric urea is higher than the racemate, as the critical gelling concentrations in toluene, for example, were 0.2% and 0.7% (wt/wt), respectively. The enhan…

Selective access to either a doubly boron-doped tetrabenzopentacene or an oxadiborepin from the same precursor

Depending on the solvent, a brominated arylborane gave the multiple helicene B2-TBPA (pyridine) or the oxadiborepin ODBE (THF) after intramolecular Yamamoto coupling.

4-[5-(4-Fluorophenyl)-3-isopropylisoxazol-4-yl]pyridine

In the title compound, C17H15FN2O, the exocyclic bond angles at the C atoms of the isoxazole ring bearing the pyridyl and 4-fluoro­phenyl substituents are 129.66 (17) and 134.58 (16)°, respectively. The structure was determined in a study of the mol­ecular geometry of isoxazole derivatives with biological activity as MAPK inhibitors.

A New Co-Ni-Heterometallic Butterfly Complex Obtained via a Novel Synthesis Approach

Abstract. The heterometallic complex [Co2Ni2(OH)2(O2CtBu)6(HOEt)6]·2EtOH (1) with a so called butterfly structural motif was prepared by reaction of the homometallic precursor complexes [Co2(H2O)(O2CtBu)4(HO2CtBu)4] and [Ni2(H2O)(O2CtBu)4(HO2CtBu)4] in an one to one ratio under elevate temperature. Complex 1 was characterized by single-crystal X-ray diffraction, atomic absorption spectroscopy, elemental analyses, IR spectroscopy, and mass spectrometry. The magnetic data show an overall antiferromagnetic behavior, which can be explained with three different coupling constants, resulting in a paramagnetic ground state.

Soluble oligoaramide precursors--a novel class of building blocks for rod-coil architectures.

A new synthetic route is described that allows the reversible conversion of the inherently insoluble oligo-p-benzamides into soluble materials through the formation of imidoyl chlorides. Syntheses of the corresponding dimer, trimer, and tetramer are reported; these compounds can easily be purified by crystallization and are accessible on the multigram scale. Structural proof was obtained by single-crystal X-ray structures of the trimer and tetramer precursors. They can be selectively functionalized into amides or esters at the terminal carboxylic acid group followed by hydrolysis of the imidoyl chlorides to the parent amides. This new class of compounds gives access to strongly aggregating …

C-Glycosyl amino acids through hydroboration-cross-coupling of exo-glycals and their application in automated solid-phase synthesis.

O-Glycosylation is one of the most important post-translational modifications of proteins. The attachment of carbohydrates to the peptide backbone influences the conformation as well as the solubility of the conjugates and can even be essential for binding to specific ligands in cell-cell interactions or for active transport over membranes. This makes glycopeptides an interesting class of compounds for medical applications. To enhance the long-term availability of these molecules in vivo, the stabilization of the glycosidic bond between the amino acid residue and the carbohydrate is of interest. The described modular approach affords β-linked C-glycosyl amino acids by a sequence of Petasis …

Conformation versus coordination: synthesis and structural investigations of tellurium(II) dithiolates derived from beta-donor-substituted thiols.

New methods of preparing tellurium(II) dithiolates, Te(SR)(2), are presented. Te(SCH(2)CH(2)OAc)(2), 1, was made from Te(SCH(2)CH(2)OH)(2) by acetylation of the hydroxyl groups. Te(SCH(2)CH(2)SAc)(2), 2, [Te(SCH(2)CH(2)NH(3))(2)]Cl(2), 3, and Te(SC(6)H(4)(o-NH(2)))(2), 4, were synthesized by ligand exchange reactions of Te(S(t)Bu)(2) with 2 equiv of HSCH(2)CH(2)SAc, [HSCH(2)CH(2)NH(3)]Cl, and HSC(6)H(4)(o-NH(2)), respectively. Of all compounds, 4 exhibits the strongest thermal sensitivity toward decomposition and the largest low-field shift of the (125)Te NMR signal, two features that are attributed to weak Te.N interactions. The structural parameters of the CSTeSC unit exhibit very similar…

ChemInform Abstract: Enantioselective Syntheses of 2-Alkyl-, 2,6-Dialkylpiperidines and Indolizidine Alkaloids Through Diastereoselective Mannich-Michael Reactions.

Methyl 3,3,6,6-tetramethyl-1,8-dioxo-4,5,7,9-tetrahydro-2H-xanthene-9-carboxylate

The title molecule, C19H24O5, is built by annulation of a half-chair cyclohexenone and a twist-cyclohexenone to a flat 4-H-pyrane boat. In the crystal, molecules are connected via van der Waals interactions and C—H...O hydrogen bonds.

Cover Feature: Direct Metal‐ and Reagent‐Free Sulfonylation of Phenols with Sodium Sulfinates by Electrosynthesis (Chem. Eur. J. 28/2019)

Cyclodextrins in Polymer Synthesis: Enantiodiscrimination in Free-Radical Polymerization of Cyclodextrin-Complexed Racemic N -Methacryloyl-D,L -phenylalanine Methyl Ester

The enantiodiscriminating polymerization of racemic cyclodextrin-complexed N-methacryloylphenylalanine methyl ester is investigated 1 H NMR spectra of the complexes with methylated β-cyclodextrin in D 2 O manifest splittings due to chiral recognition. The different stabilities of the diastereomeric complexes influence the kinetics of the homopolymerization, particularly at 0°C. An enrichment of the residual N-methacryloyl-L-phenylalanine methyl ester of 14% was achieved after 21 h of polymerization.

Layered Thiadiazoloquinoxaline-Containing Long Pyrene-Fused N-Heteroacenes

Three thiadiazoloquinoxaline-containing long pyrene-fused N-heteroacenes with 8, 13, and 18 rings were designed and synthesized. They show high electron affinities (EAs) of approximately 4.1 eV, which were derived from the onset of the reduction peaks in cyclic voltammetry. Crystal structure analysis revealed in-plane extension through close contacts between thiadiazole units as well as layered packing, enabling in-plane and interlayer electron transport. Organic field-effect transistor devices provided electron mobilities, which suggest a potential way to enhance the charge transport in long N-heteroacenes.

4-(4-Fluorophenyl)-1-phenyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine

In the title compound, C20H15FN4, the pyrazole ring forms dihedral angles of 43.51&amp;#8197;(6), 39.95&amp;#8197;(6) and 32.23&amp;#8197;(6)&amp;#176; with the directly attached 4-fluorophenyl, pyridine and phenyl rings, respectively. The crystal packing is stabilized by intermolecular N&amp;#8212;H...N and N&amp;#8212;H...F hydrogen bonds.

Total Synthesis of (-)-C/D-cis-De­hydro-3-O-methyl-estradiols

A convergent synthesis of (–)-dehydro-3-O-methyl-C/D-cis-estradiol started from stereochemically defined substituted optically active 3-(2-arylethyl)-γ-butyrolactones. Regioselective bromination of the anisyl moiety, reductive ring opening of the iodolactone, and protecting-group changes led to a Weinreb amide. This then underwent an intramolecular Grignard reaction closing the B-ring to give a tetralone with defined configuration. Introduction of C-11 through an allyl Grignard addition and subsequent ring-closing metathesis gave a tetrahydro phenanthrene derivative. Oxidation of the side-chain alcohol resulted in the key aldehyde group, and a final samarium-diiodide-mediated reductive D-ri…

ChemInform Abstract: Synthesis of a Naphtho-pyrido-Annulated Iodonium Salt and Pd-Catalyzed Transformation to 7H-Naphtho[1,8-bc][1,5]naphthyridine.

Nitropyridylnaphthalene is the central intermediate for the synthesis of naphthonaphthyridine and benzo-δ-carboline. Whereas the Cadogan reaction gives the carboline, transformation of the nitro group to iodo followed by oxidation and cyclization results in an iodonium salt. A twofold Pd-catalyzed amination leads to the naphthyridine.

Hexasubstituted Benzenes with Ultrastrong Dipole Moments

Hexasubstituted benzenes have been synthesized with the highest known dipole moments, as determined by dielectric spectroscopy and DFT methods. Based on the preparation of 4,5-diamino-3,6-dibromophthalonitrile, combined with a novel method to synthesize dihydrobenzimidazoles, these benzene derivatives have dipole moments in excess of 10 debye. Such dipole moments are desirable in ferroelectrics, nonlinear optics, and in organic photovoltaics. Structure determination was achieved through single-crystal X-ray crystallography, and the optical properties were determined by UV/Vis absorption and fluorescence spectroscopy.

Guest-Host Systems of 1,3,5-Tristyrylbenzenes

(E,E,E)-1,3,5-Tris(3,4,5-trimethoxystyryl)benzene (1a) forms monoclinic crystals of the space group P21/c. Incorporation of three transoid diacetyl guest molecules between the three arms leads to triclinic crystals of the space group P1. The styryl groups, originally present in a nonsymmetrical conformation, are simultaneously transformed to a C3 arrangement. (E,E,E)-1,3,5-Tris- (3,4,5-tripropoxystyryl)benzene (1b) forms monoclinic crystals of the space group P21/c. The C3 arrangement of the styryl groups is present in the first, the unsymmetrical arrangement in the second modification. Incorporation of two acetone guests in the largest and the middle-sized angle space between the styryl ar…

Reaction of 2,2′-bis(N-methylindolyl) with dimethyl acetylenedicarboxylate and thermally- and photochemically-induced cyclizations of the product

2,2′-Bis(N-methylindolyl) 1 reacts with dimethyl acetylenedicarboxylate to furnish the 3-dimethyl maleoyl-substituted 2,2′-bisindolyl 2. Compound 2 cyclizes under aluminum trichloride catalysis according to a polar process to give a cyclopenta[2,1-b:3,4-b′]diindole derivative 4. Reaction of compound 4 with benzyl-amine yields the spiro derivative 5. Photochemically-induced 1,6-electrocyclization of compound 2 gives rise to the indolo[2,3-a]carbazole 6 directly, which is readily transformed to the pyrrolo-annelated carbazole 7 by treatment with benzylamine.

Bis(2-methylbenzimidazole-κN1)copper(I) dichlorocuprate(I)

By using alternating-current electrochemical synthesis, crystals of the copper(I) ionic compound composed of [Cu(C8H8N2)2]+ and [CuCl2]− ions have been obtained and structurally investigated. Both crystallographically independent Cu atoms lie on centres of inversion and exhibit the less-common coordination number 2. A linear arrangement of the metal atoms includes two N atoms of the different organic moieties in the [Cu(2-methyl­benz­imidazole)2]+ cation and two Cl atoms in the case of the inorganic anion.

Tellurium(IV) Tetraalkoxides and Chlorotellurium(IV) Alkoxides Derived from β-Donor Alcohols

Abyssomicin E, a highly functionalized polycyclic metabolite from Streptomyces species.

Abyssomicin E (1), a new polycyclic metabolite with a C19 skeleton, was isolated from Streptomyces sp. (HKI0381). Its chemical structure was determined by comprehensive NMR and MS spectroscopic analyses. For the first time in this recently discovered class of compounds, the absolute stereochemistry was directly established by subsequent single-crystal X-ray diffraction study using anomalous dispersion with copper radiation.

1-(2,3,5,6-Tetramethylbenzyloxy)-1H-benzotriazole

In the title compound, C17H19N3O, the benzotriazole ring is essentially planar, with a maximum deviation of 0.0069&amp;#8197;(15)&amp;#8197;&amp;#197;. The mean plane of the benzotriazole ring forms a dihedral angle of 13.16&amp;#8197;(4)&amp;#176; with the mean plane of the benzene ring. The crystal packing is stabilized by &amp;#960;&amp;#8211;&amp;#960; stacking interactions, with a centroid&amp;#8211;centroid distance of 3.8077&amp;#8197;(12)&amp;#8197;&amp;#197;, together with weak C&amp;#8212;H...&amp;#960; interactions. Molecules are stacked along the a axis.

2-(6-Methoxy-7H-purin-7-yl)-1-phenylethanone monohydrate

The crystal structure of the title compound, C14H12N4O2·H2O, was determined in the course of our studies of the synthesis and optimization of 7-aryl-7H-purines as inhibitors of the vascular endothelial growth factor receptor (VEGF-R), c-Jun NH2-terminal protein kinase 3 (JNK3) and the p38α mitogen-activated protein kinase (MAPK). In the title compound, two mol­ecules are associated with each other through O—H⋯N hydrogen bonds to different N atoms in the purine ring system. The compound was prepared via a regioselective synthesis using the meth­yl(aqua)cobaloxime complex, CH3Co(DH)2OH2, as a temporary auxiliary. The X-ray crystallographic results confirmed the regioselective N-7 alkyl­ation …

ChemInform Abstract: A Light-Induced Vinylogous Nazarov-Type Cyclization.

The title reaction is incorporated in a three-step cascade transformation providing novel tetracyclic ring structures containing a seven-membered ring.

Cover Feature: Metal‐ and Reagent‐Free Electrochemical Synthesis of Alkyl Arylsulfonates in a Multi‐Component Reaction (Chem. Eur. J. 38/2020)

Non-Isomorphic Chlorine—Bromine Substitution in the Copper(I) Halideπ-Complexes with 1-Allyl-4-aminopyridinium

By alternating-current electrochemical synthesis crystals of {Cu[H2NC5H4N(C3H5)]Br2}˙H2O (I), {Cu[H2NC5H4N(C3H5)]Br0.65Cl1.35}˙H2O (II) and {Cu[H2NC5H4N(C3H5)]Cl2} (III) π-complexes have been obtained and structurally investigated. The I and II compounds are isostructural and crystallize in a monoclinic sp. gr. P21/c, I: a = 7.359(2)A, b = 12.3880(6)A, c = 13.637(3)A, β = 107.03(1)°, V = 1188.7(4)A3, Z = 4 for C8H13N2OBr2Cu composition, R = 0.0293 for 2140 reflections. II: a = 7.2771(6)A, b = 12.3338(3)A, c = 13.4366(7)A, β = 107.632(2)°, V = 1149.3(1)A3, Z = 4 for C8H13N2Br0.65Cl1.35Cu composition, R = 0.0463 for 2185 reflections. Metal and halogen atoms form centrosymmetric Cu2X4 dimers. …

Funktionalisierte Tellur(II)-thiolate: Tellurbis(2-hydroxyethanthiolat)-Hydrat, der erste H2O-TeII-Komplex

Strategies for structure solution and refinement of small organic molecules from electron diffraction data and limitations of the simulation approach

In recent years, a series of non-linear optically active bis(benzylidene) ketones have been synthesized and investigated by electron crystallography. In most cases, structure refinement was possible by combining electron diffraction analysis and quantum-mechanical calculations with maximum-entropy methods. However, when the torsional angles between the phenyl rings and the C=C double bonds are strongly affected by the crystal field, this method fails because packing-energy calculations are not sufficiently sensitive. This problem can be solved by refining the approximate model with SHELXL, if the data set is sufficiently accurate and the model close to the correct structure. Here it is show…

catena-Poly[bis[(eta2-1-allyl-3-aminopyridinium)copper(I)]-di-mu-chloro-copper(I)-di-mu-chloro-copper(I)-di-mu-chloro].

Crystals of the title pi-complex, [Cu4Cl6(C8H11N2)2]n, were obtained by means of alternating-current electrochemical synthesis. The structure consists of infinite copper-chlorine chains to which 1-allyl-3-aminopyridinium moieties are attached via a eta2 Cu-(C=C) interaction. The two independent Cu atoms have distinct coordination environments. One is three-coordinate, surrounded by two chloro ligands and the olefinic bond, whereas the second copper center is surrounded by a tetrahedral arrangement of four Cl atoms. The lower basicity of 3-aminopyridine as compared with 2- and 4-aminopyridine lowers the capacity of the organic ligand for donating to N-H...Cl hydrogen bonds and results in the…

Iodocyclization of o-Alkynylbenzamides Revisited: Formation of Isobenzofuran-1(3H)-imines and 1H-Isochromen-1-imines Instead of Lactams

The iodocyclization of o-alkynylbenzamides with various electrophiles has been reported to yield five- or six-membered lactams by nucleophilic attack of the amide nitrogen onto the triple bond. While the formation of an isobenzofuran-1(3H)-imine with two bulky substituents under Larock conditions was initially attributed to steric hindrance, we found out that cyclization via the amide oxygen is the rule rather than the exception. Thus, the structures of the products reported in the literature need to be revised.

Unexpected Formation of a 1,2-Dichloroacenaphthylene in a Friedel-Crafts Reaction with Chloral Hydrate

An unprecedented rearrangement was encountered during an attempted alkylation of an electron-rich naphthalene with chloral hydrate. The reaction produced a dichlorinated acenaphthylene and presumably involves the intermediate formation of a chloronium ion which is opened to produce the five-membered ring of the final product.

Cover Picture: Metal‐ and Reagent‐Free Highly Selective Anodic Cross‐Coupling Reaction of Phenols (Angew. Chem. Int. Ed. 20/2014)

Front Cover: Electrochemical Synthesis of Fluorinated Orthoesters from 1,3‐Benzodioxoles (ChemistryOpen 9/2019)

The Front Cover shows the robustness achieved by the installation of fluorinated alcohols on 1,3‐benzodioxoles, which appears like the shield of a knight protecting the obtained orthoesters against acids and bases. The simple protocol allows access to interesting compounds, whose lipophilicity is tremendously increased by the incorporation of fluorinated groups. This makes it possible to adjust the physicochemical properties of the biologically active 1,3‐benzodioxole motif. The surprisingly high stability against acids and bases gives rise to subsequent functionalizations or direct application in medicinal or agrochemistry. More information can be found in the Communication by J. L. Röckl …

4-[2-(4-Fluorophenyl)furan-3-yl]pyridine

In the crystal structure of the title compound, C(15)H(10)FNO, the furan ring makes dihedral angles of 40.04 (11) and 25.71 (11)° with the pyridine and 4-fluoro-phenyl rings, respectively. The pyridine ring makes a dihedral angle of 49.51 (10)° with the 4-fluoro-phenyl ring. Non-conventional C-H⋯F and C-H⋯N hydrogen bonds are effective in the stabilization of the crystal structure.

Crystal structure of ethyl 2-(di-eth-oxy-phosphor-yl)-2-(2,3,4-tri-meth-oxy-phen-yl)acetate.

The title compound, C17H27O8P, was prepared by Michaelis–Arbuzov reaction of ethyl 2-bromo-2-(2,3,4-trimethoxyphenyl)acetate and triethyl phosphite. Such compounds rarely crystallize, but single crystals were recovered after the initial oil was left for approximately 10 years. The bond angle of thesp3-hybridized C atom connecting the benzene derivative with the phospho unit is widened marginally [112.5 (2)°]. The terminal P—O bond length of 1.464 (2) Å clearly indicates a double bond, whereas the two O atoms of the ethoxy groups connected to the phosphorous atom have bond lengths of 1.580 (2) Å and 1.581 (3) Å. The three methoxy groups emerge out of the benzene-ring plane due to steric hind…

Insights into the Mechanism of Anodic N–N Bond Formation by Dehydrogenative Coupling

The electrochemical synthesis of pyrazolidine-3,5-diones and benzoxazoles by N-N bond formation and C,O linkage, respectively, represents an easy access to medicinally relevant structures. Electrochemistry as a key technology ensures a safe and sustainable approach. We gained insights in the mechanism of these reactions by combining cyclovoltammetric and synthetic studies. The electron-transfer behavior of anilides and dianilides was studied and led to the following conclusion: The N-N bond formation involves a diradical as intermediate, whereas the benzoxazole formation is based on a cationic mechanism. Besides these studies, we developed a synthetic route to mixed dianilides as starting m…

ChemInform Abstract: Molybdenum Pentachloride Mediated Synthesis of Spirocyclic Compounds by Intramolecular Oxidative Coupling.

Oxidative treatment of 4-methoxy substituted 2-aryl cinnamates leads to an dealkylative C—C coupling and gives access to spirocyclic compounds.

Shape-persistent V-shaped mesogens—formation of nematic phases with biaxial order

A homologous series of shape-persistent V-shaped molecules has been designed to form the biaxial nematic phase. Phenyleneethynylene moieties are attached to a bent fluorenone unit to create an apex angle of about 90°, which is determined from the single crystal structure. Two mesogens, one symmetric and another unsymmetric, have been synthesized by attaching a cyano group to one or both of the peripheral phenyl units, respectively. These groups introduce local dipoles essential for the formation of the nematic phases. The tendency to form a crystalline phase is reduced by laterally substituted hexyloxy chains which allow the nematic phase to be supercooled to a glassy state. Two of the thre…

Tailoring the Emission of Fluorinated Bipyridine-Chelated Iridium Complexes

New functionalized tris(2′,6′-difluoro-2,3′-bipyridinato-N,C4′)iridium(III) ((dfpypy)3Irs) complexes, including small molecules and their dendrimer embedded analogoues, were synthesized and characterized. It is demonstrated that both the fac-(dfpypy)3Ir-based polyphenylene dendrimers and (triisopropylsilyl)ethynyl (TIPSE)-substituted (dfpypy)3Ir complexes induce large bathochromic shifts (∼50 nm) of emission bands compared with fac-(dfpypy)3Ir. This is due to the pronounced 3π–π* character of emissive excited states and the extended conjugation. A further remarkable feature is the small bathochromic shift of the emissions of fac-tris(2-phenylpyridine)iridium (fac-(ppy)3Ir)-based polyphenyle…

Synthesis and X-ray crystal structure of manganese(II) pyridine-2-thiolate

2:1 complexes of pyridine-2(1H)-thione (LH) with manganese(II) were prepared: (LH)2MnCl2, (LH)2MnBr2 and [L2Mn]n. The polymeric chain structure of [L2Mn]n contains a distorted octahedrally coordinated manganese (MnN2S4) with chelating ligands, the N-atoms are in cis positions and the S-atoms of the pyridine-2-thiolates bridging; crystallographic data for [C10H8MnN2S2]n: space group C2/c (monoclinic), and R1 = 0.0571 for 1326 reflexes with Fo4σ(Fo).

4-(4-Fluorophenyl)-2-methyl-3-(1-oxy-4-pyridyl)isoxazol-5(2H)-one

The crystal structure of the title compound, C15H11FN2O3, was determined as part of a study on the biological activity of isoxazolone derivatives as p38 mitogen-activated protein kinase (MAPK) inhibitors. The dihedral angles between rings are isoxazole/benzene = 55.0&#8197;(3)&#176;, isoxazole/pyridine = 33.8&#8197;(2)&#176; and benzene/pyridine = 58.1&#8197;(2)&#176;.

Cover Picture: Selective Synthesis of Partially Protected Nonsymmetric Biphenols by Reagent‐ and Metal‐Free Anodic Cross‐Coupling Reaction (Angew. Chem. Int. Ed. 39/2016)

On the reaction of [Ph2(OH)Si]2O with t-Bu2SnCl2: Synthesis and characterization of the first well defined polystannasiloxane [(t-Bu2SnO)(Ph2SiO)2]n

Abstract The high yield synthesis of [(t-Bu2SnO)(Ph2SiO)2], 1 is reported. Compound 1 is a linear polymer in the solid state but a six-membered ring in solution.

(Z)-1-Chloro-1-[2-(2-nitrophenyl)hydrazinylidene]propan-2-one

The title molecule, C9H8ClN3O3, lies on a mirror plane. Intramolecular N&#8212;H...O and N&#8212;H...Cl hydrogen bonds occur. One of the nitro O atoms is disordered (site occupancy ratio = 0.40:0.10).

Electrochemical formation of N,N′-diarylhydrazines by dehydrogenative N–N homocoupling reaction

Hydrazines represent a class of compounds of high interest due to their applicability as versatile starting materials in many important transformations. Herein, we report a synthetic approach to hydrazine derivatives using commercially available anilines and an anodic dehydrogenative N-N coupling reaction as the key step.

ChemInform Abstract: Unexpected Formation of a 1,2-Dichloroacenaphthylene in a Friedel-Crafts Reaction with Chloral Hydrate.

An Efficient Synthesis of Rubin’s Aldehyde and its Precursor 1,3,5-Tribromo-2,4,6-tris(dichloromethyl)benzene

2,4,6-Tribromobenzene-1,3,5-tricarboxaldehyde (4) can be efficiently prepared in two reaction steps from 1,3,5-tribromobenzene. The intermediate 1,3,5-tribromo-2,4,6-tris(dichloromethyl)benzene (3) crystallizes from petroleum ether in its C3h structure. However, in CDCl3 solution it exists at room temperature in two isomeric forms: 3a (C3h) and 3b (Cs) (1:1.15).The intramolecular Br・・・Cldistances are much smaller than the sum of the van der Waals radii. Therefore, the exocyclic C-C bonds show a hindered rotation.

Ethanedithiol diacetate

Ethane-1,2-diyl S,S′-bis­(thio­acetate), H3CC(O)SCH2CH2SC(O)CH3 or C6H10O2S2, forms centrosymmetric mol­ecules in the solid state and the molecular structure determined by X-ray crystallography is in good agreement with that obtained by density functional geometry optimization. The planarity of the O=C—S—C fragment, which is also found in structures of other thio­acetates, is attributed to a strong np(S)–π*(C—O) orbital interaction.

Intramolecularly Coordinated Bis(crown ether)-Substituted Organotin Halides as Ditopic Salt Receptors

The synthesis of the bis(crown ether)-substituted organostannanes X2Sn(CH2-[16]-crown-5)2 (3, X = I; 4, X = Br; 5, X = Cl; 6, X = F) and X2Sn(CH2-[13]-crown-4)2 (10, X = I; 11, X = Br; 12, X = F) is reported. The compounds have been characterized by 1H, 13C, 19F, and 119Sn NMR spectroscopy, elemental analyses, and electrospray ionization mass spectrometry (ESI-MS). Single-crystal X-ray diffraction analyses reveal a distorted-octahedral cis,cis,trans configuration of the tin atoms in compounds 4–6 and 10–12 as a result of intramolecular O→Sn coordination. The ability of the host molecules to form mono- and ditopic complexes with various halide salts in different solvents, including water, ha…

Two strained hexahelicenophanes

The crystal structures of the [6]­helicenes 4,13-(1,10-deca­methyl­ene­dioxy)­hexahelicene, C36H34O2, (I), and 4,13-(1,8-octa­methyl­ene­dioxy)­hexahelicene, C34H30O2, (II), show strong steric interactions between the terminal benzene rings and the poly­methyl­ene­dioxy chains. The shortest ring A and F distances amount to 2.941 (3) and 2.902 (3) A, respectively. The increased steric energy of the ground state is responsible for a significantly lower racemization barrier of (I) and (II) in comparison to the unsubstituted [6]­helicene.

A Tetrameric Nickel(II) “Chair” with both Antiferromagnetic Internal Coupling and Ferromagnetic Spin Alignment

Phenylethynyl- and Phenylethenylmetacyclophanes with π,π Interactions

1-Benzyl-1H-benzotriazole 3-oxide-1-hy-droxy-1H-benzotriazole (1/1).

In the title compound, C6H5N3O·C13H11N3O, the benzotriazole ring system in the 1-benzyl-1H-benzotriazole 3-oxide (A) molecule is close to being planar (r.m.s. deviation = 0.011 Å); its mean plane forms a dihedral angle of 67.56 (7)° with that of the attached phenyl ring. The benzotriazole ring system in the 1-hydroxybenzotriazole (B) molecule is also close to being planar (r.m.s. deviation = 0.010 Å). In the crystal, weak C—H...O and C—H...π interactions are present. TheAandBmolecules are linked by an O—H...N hydrogen bond.

Electrochemical Synthesis of 5-Aryl-phenanthridin-6-one by Dehydrogenative N,C Bond Formation.

Currently, the general synthesis of 5-aryl-phenanthridin-6-ones relies on the involvement of metal catalysis. Despite the urgent demand for green alternatives, avoiding synthetic routes that require transition metals for key roles is still challenging. Electrochemical efforts employing a constant potential protocol in divided cells revealed a possible alternative to the catalytic approach. A constant current protocol, undivided cells, and a remarkably low supporting electrolyte concentration enable a novel access to N-aryl-phenanthridin-6-ones by anodic N,C bond formation using directly generated amidyl radicals. Easy accessible starting materials, a broad scope of applicable functional gro…

1-Mesitylmethyl-1Hbenzotriazole 3-oxide.

In the title compound, C16H17N3O, the benzotriazole ring forms a dihedral angle of 77.25&amp;#8197;(6)&amp;#176; with the phenyl ring. The benzotriazole ring is essentially planar with a maximum deviation of 0.012&amp;#8197;(19)&amp;#8197;&amp;#197;. Weak intermolecular C&amp;#8212;H...O hydrogen bonds form R22(10) motifs. The crystal packing is consolidated by &amp;#960;&amp;#8212;&amp;#960; interactions with centroid&amp;#8211;centroid distances of 3.5994&amp;#8197;(12)&amp;#8197;&amp;#197; together with very weak C&amp;#8212;H...&amp;#960; interactions.

rac-11-Selena-12,13-diazabicyclo[10.3.0]pentadeca-10a(13a),12-dien-1-ol

The title compound, C12H20N2OSe, crystallizes in strands of enantiomeric molecules connected via O—H...N hydrogen bonds. There are only slight deviations from an ideal gauche conformation in the decamethylene chain, indicating just a little strain.

Functionalized Tellurium(II) Thiolates: Tellurium Bis(2-hydroxyethanethiolate) Hydrate, the First H2O–TeII Complex

Synthesis and pharmacological characterization of beta2-adrenergic agonist enantiomers: zilpaterol.

The beta-adrenergic agonist 1 (zilpaterol) is used as production enhancer in cattle. Binding experiments of separated enantiomers on recombinant human beta(2)-adrenergic and mu-opioid receptors and functional studies showed that the (-)-1 enantiomer accounts for essentially all the beta(2)-adrenergic agonist activity and that it exhibits less affinity toward the mu-opioid receptor than (+)-1, which is a mu-opioid receptor antagonist. X-ray crystallography revealed the absolute configuration of (-)-1 to be 6R,7R.

3,4-Bis(4-fluorophenyl)-1,2,5-oxadiazole 2-oxide

The title compound, C14H8F2N2O2, also known as di(4-F-phen­yl)furazan N-oxide, was found as a side product in the synthesis of isoxazole derivatives. The are two molecules in the asymmetric unit. The bond length of the dipolar N—O unit is 1.107 (7) A. X-ray analysis confirmed the compound to have the desired structure

Metal‐Free Electrochemical Synthesis of Sulfonamides Directly from (Hetero)arenes, SO2, and Amines

Abstract Sulfonamides are among the most important chemical motifs in pharmaceuticals and agrochemicals. However, there is no methodology to directly introduce the sulfonamide group to a non‐prefunctionalized aromatic compound. Herein, we present the first dehydrogenative electrochemical sulfonamide synthesis protocol by exploiting the inherent reactivity of (hetero)arenes in a highly convergent reaction with SO2 and amines via amidosulfinate intermediate. The amidosulfinate serves a dual role as reactant and supporting electrolyte. Direct anodic oxidation of the aromatic compound triggers the reaction, followed by nucleophilic attack of the amidosulfinate. Boron‐doped diamond (BDD) electro…

Titelbild: Selektive Synthese teilgeschützter unsymmetrischer Biphenole durch reagens‐ und metallfreie anodische Kreuzkupplung (Angew. Chem. 39/2016)

Ethyl 5-amino-3-(pyridin-4-yl)-1-(2,4,6-trichlorophenyl)-1H-pyrazole-4-carboxylate dimethyl sulfoxide hemisolvate

The asymmetric unit of the title compound, C17H13Cl3N4O2&amp;#183;0.5C2H6OS, contains two almost identical molecules and one dimethyl sulfoxide (DMSO-d6) solvent molecule. The pyrazole ring forms dihedral angles of 54.6&amp;#8197;(4) and 80.0&amp;#8197;(4)&amp;#176; in one molecule, and dihedral angles of 54.2&amp;#8197;(4) and 81.2&amp;#8197;(4)&amp;#176; in the other molecule, with the directly attached pyridine and trichlorophenyl rings, respectively. The dihedral angles of the pyridine and trichlorophenyl rings are 51.2&amp;#8197;(4) and 52.0&amp;#8197;(4)&amp;#176;, respectively. The crystal packing is characterized by intra- and intermolecular hydrogen bonds. The crystal is a nonmeroh…

ChemInform Abstract: First Synthesis of Medium-Sized Ring Allenyl Lactams.

Medium-sized lactams bearing an axially chiral allene unit have been synthesized by using an aza-ketene Claisen rearrangement. Starting from 2-alkynylpiperidines or 2-alkynylazepines, ring enlargement enabled the highly diastereoselective formation of 10- or 11-membered lactams with a 4,5-allene subunit. X-ray analysis of the allenylacezinone showed the presence of a strained cumulated olefin system with a defined arrangement of the functional groups. The cyclic allenes were found to be stable upon heating up to 50 °C.

Electrochemical synthesis of sulfamides.

Herein we demonstrate the first electrochemical synthesis protocol of symmetrical sulfamides directly from anilines and SO2 mediated by iodide. Sulfamides are an emerging functional group in drug design. Highlights are the direct use of SO2 from a stock solution and no necessity of any supporting electrolyte. Overall, the reaction has been demonstrated for 15 examples with yields up to 93%.

Trapping Molecular SnBr 2 (OH) 2 by Tin Alkoxide Coordination: Syntheses and Molecular Structures of [MeN(CH 2 CMe 2 O) 2 SnBr 2 ] 2 ·SnBr 2 (OH) 2 and RN(CH 2 CMe 2 O) 2 SnL [R = Me, n ‐Octyl; L = Lone Pair, Cr(CO) 5 , W(CO) 5 , Fe(CO) 4 , Br 2 ]

The synthesis of the intramolecularly coordinated stannylenes and their transition-metal complexes of the type RN(CH2CMe2O)2SnL [1: L = lone pair, R = Me; 2: L = lone pair, R = n-octyl; 5: L =W(CO)5, R = Me; 6: L = Cr(CO)5, R = Me; 7: L =W(CO)5, R = n-octyl; 8: L = Fe(CO)4, R = Me], and of the tin(IV) compounds RN(CH2CMe2O)2SnBr2 (9: R = Me), [MeN(CH2CMe2O)2SnBr2]2·SnBr2(OH)2 (10) and spiro-[RN(CH2CMe2O)2]2Sn (3: R = Me; 4: R = n-octyl) is reported. The compounds were characterized by elemental analyses, 1H, 13C, 119Sn, and 119Sn magic-angle spinning (5, 6) NMR spectroscopy, electrospray mass spectrometry, and single-crystal X-ray diffraction analysis.

Single and Twofold Metal- and Reagent-Free Anodic C-C Cross-Coupling of Phenols with Thiophenes.

The first electrochemical dehydrogenative C-C cross-coupling of thiophenes with phenols has been realized. This sustainable and very simple to perform anodic coupling reaction enables access to two classes of compounds of significant interest. The scope for electrochemical C-H-activating cross-coupling reactions was expanded to sulfur heterocycles. Previously, only various benzoid aromatic systems could be converted, while the application of heterocycles was not successful in the electrochemical C-H-activating cross-coupling reaction. Here, reagent- and metal-free reaction conditions offer a sustainable electrochemical pathway that provides an attractive synthetic method to a broad variety …

Photochemical Generation of Cyclophanes from 1,3,5-Trisubstituted Benzenes with Chalcone Chromophores

(E,E,E)-1,3,5-Tricinnamoylbenzene (7a) photodimerizes in solution to the [4.4.4](1,3,5)cyclophane 8a. The process consists of three consecutive steps in which cisoid enone conformations of 7a react in regio- and stereoselective anti-head-to-head cycloadditions. (E,E,E)-1,3,5-Tris(3-oxo-3-phenylpropenyl)benzene (13a), an isomer of 7 with reversed enone units, shows a single [2π+2π] cycloaddition of the same type. Due to steric reasons, it is afterwards not capable of intramolecular processes and oligomerizes by intermolecular photocycloadditions. Photolyses in the crystalline state yield dimers by topochemically controlled syn-head-to-tail processes (7a → 10a, 13a → 15a). An efficient dimeri…

Differences between smectic homo‐ and co‐polysiloxanes as a consequence of microphase separation

This paper compares smectic phases formed from LC‐homo‐ and LC‐co‐polysiloxanes. In the homopolysiloxane, each repeating unit of the polymer chain is substituted with a mesogen, whereas in the copolysiloxanes mesogenic repeating units are separated by dimethylsiloxane units. Despite a rather similiar phase sequence of the homo‐ and co‐polysiloxanes—higher ordered smectic, smectic C* (SmC*), smectic A (SmA) and isotropic—the nature of their phases differs strongly. For the copolymers the phase transition SmC* to SmA is second order and of the ‘de Vries’ type with a very small thickness change of the smectic layers. Inside the SmA phase, however, the smectic thickness decreases strongly on ap…

Syntheses, structures, and magnetic properties of diphenoxo-bridged Cu(II)Ln(III) and Ni(II)(low-spin)Ln(III) compounds derived from a compartmental ligand (Ln = Ce-Yb).

Syntheses, characterization, and magnetic properties of a series of diphenoxo-bridged discrete dinuclear M(II)Ln(III) complexes (M = Cu or Ni, Ln = Ce-Yb) derived from the compartmental Schiff base ligand, H(2)L, obtained on condensation of 3-ethoxysalicylaldehyde with trans-1,2-diaminocyclohexane, are described. Single crystal X-ray structures of eight Cu(II)Ln(III) compounds (Ln = Ce (1), Pr (2), Nd (3), Sm (4), Tb (7), Ho (9), Er (10), and Yb (12)) and three Ni(II)Ln(III) (Ln = Ce (13), Sm (16), and Gd (18)) compounds have been determined. Considering the previously reported structure of the Cu(II)Gd(III) (6) compound (Eur. J. Inorg. Chem. 2005, 1500), a total of twelve structures are di…

Investigation of α-amino acid N-carboxyanhydrides by X-ray diffraction for controlled ring-opening polymerization

Abstract The need for a scalable synthesis of not sequence defined polypeptides as biomaterials is met by the ring-opening polymerization of α-amino acid N-carboxyanhydrides (NCAs). Even though this polymerization technique appears straight forward, it holds pitfalls in terms of reproducibility and overall control over the polymerization conditions, which depends, beside choice of solvent or initiator, significantly on reagent purity. In addition, the synthesis of monomers can lead to the formation of racemic amino acids. Thus, in this work, we describe the benefits of highly pure monomers in order to control nucleophilic ring-opening polymerization NCAs. Hereby, monomer purity is investiga…

(E)-1-(Pyridin-4-yl)propan-1-one oxime

The asymmetric unit of the title compound, C8H10N2O, contains two crystallographically independent molecules of slightly different conformation, which are linkedviaan intermolecular O—H...N hydrogen bond. The dihedral angle between the pyridine ring and the oxime plane of moleculeA[2.09 (19)°] is smaller than in moleculeB[16.50 (18)°].

Dimeric Capsules Formed by Tetra-CMPO Derivatives of (Thia)Calix[4]arenes

Thiacalix[4]arene 2, calix[4]arene 3 a and its tetraether fixed in the cone conformation 3 b form homo- and heterodimeric capsules in apolar solvents, which are held together by a seam of NH⋅⋅⋅O=P hydrogen bonds between carbamoylmethyl phospine oxide functions attached to their wide rim. Their internal volume of ∼370 A3 requires the inclusion of a suitable guest. Although neutral molecules such as adamantane (derivatives) or tetraethylammonium cations form kinetically stable complexes (1H- and 31P-time scale), the included solvent is rapidly exchanged. The internal mobility of the included tetraethylammonium cation is distinctly higher (ΔG=42.5 and 49.7 kJ mol−1 for 3 a and 3 b) than that f…

rac-(E,trans)-4-Bromo-10,10-dimethyl-9,11-dioxabicyclo[6.3.0]undec-4-ene

In the title compound, a cyclooctene ring in a twist-boat conformation and a dioxolane ring with a distorted envelope conformation are annulated in a trans configuration. Alternating strands of single enantiomers build up the crystal. Within the strands, the molecules are connected by weak C—H...O hydrogen bonds.

ChemInform Abstract: Metal- and Reagent-Free Highly Selective Anodic Cross-Coupling Reaction of Phenols.

Boron-doped diamond electrodes allow the direct anodic cross-coupling of phenols in hexafluoroisopropanol without using leaving functions or protecting groups.

rac-12-Selena-13,14-diazatricyclo[9.3.0.02,4]tetradeca-11,13-diene

The centrosymmetric crystal structure of the title compound, C11H16N2Se, is built up from alternating strands of (R,R)- and (S,S)-enantiomers. These strands, which propagate along the c-axis direction, are composed of homochiral molecules related to each other by twofold screw axes. The shape of the molecule is an almost planar unit around the selenadiazole ring with a hexamethylene chain as an arched handle.

Synthesis and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives

6,11-Dihydro-pyrido[2,3-b]phenazine-6,11-diones and 6,11-dihydro-benzo[2,3-b]phenazine-6,11-diones were synthesized from 6,7-dichloro-5,8-quinolinedione and 2,3-dichloro-1,4-naphthoquinone. The study on the cytotoxicity on these products revealed that the pyridophenazinediones, tetracyclic heteroquinone analogues with three nitrogen atoms exhibited a high cytotoxicity on several human tumor cell lines. Compound 9c and 9e showed in vitro antitumor activity comparable or superior to doxorubicin against the human ovarian tumor cells (SK-OV-3) and the human CNS cells (XF 498). The IC(50) value for compound 9e was 0.06 microM against the human CNS cells (XF 498), which was 2.6 times higher than …

2,2-Dimethyl-N-[3-(3,4,5-trimethoxybenzoyl)pyridin-4-yl]propanamide

The title compound, C20H24N2O5, was found to have an intra­molecular N—H⋯O bond with an N⋯O distance of 2.646 (2) A. In the crystal structure, mol­ecules form dimers along the c axis by aromatic stacking inter­actions. The X-ray crystallographic analysis was carried out to correlate the solid-state geometry with virtual structural information obtained by modelling.

Synthesis of Circumpyrene by Alkyne Benzannulation of Brominated Dibenzo[hi,st]ovalene

A transition-metal catalyzed alkyne benzannulation allowed an unprecedented synthesis of circumpyrene, starting from 3,11-dibromo-6,14-dimesityldibenzo[hi,st]ovalene (DBOV). The circumpyrene was characterized by a combination of NMR, mass spectrometry, and single-crystal X-ray diffraction analysis, revealing its multizigzag-edged structure. Two newly introduced C═C bonds in circumpyrene strongly perturbed the electronic structures of DBOV, as evidenced by increased optical and electrochemical energy gaps. This is in good agreement with an increased number of Clar's sextets as well as a decreased number of π-electrons in the conjugation pathway of circumpyrene, according to anisotropy of the…

Cycloaddition reactions of 2H-1-benzothietes and 1,3,5,7-tetrathio-s-indacene-2,6-dithiones

Abstract 2H-1-benzothiete (1) and 2H,5H-benzo[1,2-b:4,5-b′]bisthiete (3) react in form of their open valence isomers with the trithiocarbonic acid esters 2a–c. The one- or twofold cycloaddition reactions yield 1,3-dithiin rings, in which C-2 is a spiro-C atom, that bears four sulfur groups. The bifunctional reactant 3 gives additionally band-shaped, hardly soluble oligomers.

3-(4-Fluorophenyl)-6-methoxy-2-(4-pyridyl)quinoxaline

In the title compound, C20H14FN3O, the quinoxaline system makes dihedral angles of 32.38&amp;#8197;(7) and 48.04&amp;#8197;(7)&amp;#176; with the 4-fluorophenyl and pyridine rings, respectively. The 4-fluorophenyl ring makes a dihedral angle of 57.77&amp;#8197;(9)&amp;#176; with the pyridine ring. In the crystal, the molecules form dimeric C&amp;#8212;H...N hydrogen-bonded R22(20) ring motifs lying about crystallographic inversion centers. The dimeric units stack via &amp;#960;&amp;#8211;&amp;#960; interactions between methoxyphenyl rings and pyridine&amp;#8211;fluorophenyl rings with centroid&amp;#8211;centroid distances of 3.720&amp;#8197;(1) and 3.823&amp;#8197;(1)&amp;#8197;&amp;#197;, …

Characterization of the synthetic cannabinoid MDMB-CHMCZCA

The synthetic cannabinoid MDMB-CHMCZCA was characterized by various spectroscopic techniques including NMR spectroscopy and tandem mass spectrometry. The synthetic sample was found to be of S-configuration by VCD spectroscopy and comparison of the data with DFT calculations, while ECD spectroscopy was found to be inconclusive in this case. The enantiomeric purity of samples from test purchases and police seizures was assessed by a self-developed chiral HPLC method.

1,1′-[2,3,5,6-Tetramethyl-p-phenylenebis(methyleneoxy)]di-1H-benzotriazole

The complete molecule of the title compound, C(24)H(24)N(6)O(2), is generated by a crystallographic inversion centre. The benzotriazole rings form dihedral angles of 2.10 (7)° with the central aromatic ring. The crystal packing is consolidated by π-π inter-actions, with centroid-centroid distances of 3.6234 (10) Å, together with weak C-H⋯π inter-actions.

Cis versus Trans: The Coordination Environment about the Tin(IV) Atom in Spirocyclic Amino Alcohol Derivatives.

The syntheses of amino alcohols MeN(CH2 CH2 CMe2 OH)2 (1), MeN(CMe2 CH2 OH)(CH2 CMe2 OH) (2), MeN(CH2 CH2 CH2 OH)(CH2 CMe2 OH) (3), MeN(CH2 CH2 CMe2 OH)(CH2 CMe2 OH) (4), MeN(CH2 CH2 CMe2 OH)(CH2 CH2 OH) (5), and MeN(CH2 CH2 OH) (CH2 CH2 CH2 OH) (6) as well as spirocyclic tin(IV) alkoxides spiro-[nBuN(CH2 CMe2 O)2 ]2 Sn (7), spiro-[MeN(CH2 CH2 CMe2 O)2 ]2 Sn (8), spiro-[para-FC6 H4 N (CH2 CMe2 O)2 ]2 Sn (9), spiro-[MeN(CMe2 CH2 O)(CH2 CMe2 O)]2 Sn (10), spiro-[MeN(CH2 CH2 CH2 O)(CH2 CMe2 O)]2 Sn (11), spiro-[MeN(CH2 CH2 CMe2 O)(CH2 CMe2 O)]2 Sn (12), spiro-[MeN(CH2 CH2 CMe2 O)(CH2 CH2 O)]2 Sn (13) and spiro-[MeN(CH2 CH2 O)(CH2 CH2 CH2 O)]2 Sn (14) are reported. The compounds were characteri…

Tellurium( II ) Dialkanethiolates: n p (S)‐σ*(Te−S′) Orbital Interactions Determine the 125 Te NMR Chemical Shift, and the Molecular and Crystal Structure

Tellurium(II) dimethanethiolate, Te(SMe)(2), and tellurium(II) diethanethiolate, Te(SEt)(2), were synthesized by reaction of TeO2 and Te(OiPr)(4) with HSMe and HSEt, respectively. In the solid state, Te(SMe)(2) exhibits a cis-conformation of the methyl groups with respect to the TeS2 plane - an unprecedented situation for nonfunctionalized organotrichalcogenides - whereas Te(SEt)(2) shows a trans-conformation. Ab initio calculations performed for Te(SMe)(2) and Te(SEt)(2) show that the cis- and trans-conformers represent minima on the potential energy surface and are stabilized by intramolecular pi-type n(S)-sigma* (Te-S') orbital interactions. In the solid state, the molecules of each comp…

Design, Synthesis and Biological Evaluation of Novel Pyrazolo[1,2,4]triazolopyrimidine Derivatives as Potential Anticancer Agents

Three novel pyrazolo-[4,3-e][1,2,4]triazolopyrimidine derivatives (1, 2, and 3) were designed, synthesized, and evaluated for their in vitro biological activity. All three compounds exhibited different levels of cytotoxicity against cervical and breast cancer cell lines. However, compound 1 showed the best antiproliferative activity against all tested tumor cell lines, including HCC1937 and HeLa cells, which express high levels of wild-type epidermal growth factor receptor (EGFR). Western blot analyses demonstrated that compound 1 inhibited the activation of EGFR, protein kinase B (Akt), and extracellular signal-regulated kinase (Erk)1/2 in breast and cervical cancer cells at concentrations…

ChemInform Abstract: Palladium-Catalyzed Domino C-H/N-H Functionalization: An Efficient Approach to Nitrogen-Bridged Heteroacenes.

Palladium-catalyzed domino CH/NH functionalization for the synthesis of novel nitrogen-bridged thienoacenes and 10H-benzo[4,5]thieno[3,2-b]indole derivatives from dihaloarene is reported. This domino sequence consists of initial CH functionalization of the benzo[b]thiophene moiety, followed by Buchwald–Hartwig coupling. This transformation is also useful for the synthesis of highly π-extended compounds.

αα- and αβ-Zinc-meso-A2B2-tetraarylporphyrins with large optical responses to triethylamine

Synthesis and separation of αα- and αβ-meso-A(2)B(2)-zinc(II) tetraarylporphyrin atropisomers with A = mesityl and B = ortho-phenylethynyl-phenyl are reported. Both isomers exhibit large optical responses upon axial NEt(3) coordination which are visible to the human eye and could therefore be beneficial for the design of smart amine sensing materials. The larger spectral changes as compared to Zn(TPP) are attributed to pronounced distortions of the porphyrin π-system due to steric interactions of the coordinating amine with the porphyrin periphery. This effect as well as the coordination site of NEt(3) at the αα-isomer have been studied by NMR experiments and were rationalized by DFT calcul…

Regioselective Metal- and Reagent-Free Arylation of Benzothiophenes by Dehydrogenative Electrosynthesis.

A novel strategy for the synthesis of biaryls consisting of a benzothiophene and a phenol moiety is reported. These heterobiaryls are of utmost interest for pharmaceutical, biological, and high-performance optoelectronic applications. The metal- and reagent-free, electrosynthetic, and highly efficient method enables the generation of 2- and 3-(hydroxyphenyl)benzo[b]thiophenes in a regioselective fashion. The described one-step synthesis is easy to conduct, scalable, and inherently safe. The products are afforded in high yields of up to 88 % and with exquisite selectivity. The reaction also features a broad scope and tolerates a large variety of functional groups.

Reagens- und metallfreie anodische C-C-Kreuzkupplung von Anilinderivaten

Vorgestellt wird die oxidative Kreuzkupplung von Anilinderivaten zu 2,2′-Diaminobiarylen. Der Oxidationsschritt wird elektrochemisch durchgefuhrt, ohne die Notwendigkeit von Metallen und Reagenzien. Ein breites Spektrum an Biphenyldiaminen konnte hergestellt werden. Die besten Resultate wurden mit Glaskohlenstoff als Anodenmaterial erhalten. Die elektrochemische Umsetzung kann problemlos in einer ungeteilten Zelle bei leicht erhohten Temperaturen durchgefuhrt werden. Auserdem wurden gebrauchliche, auf Carbonsauren basierende, Schutzgruppen verwendet, die nach der Kreuzkupplung unter milden Bedingungen selektiv abgespalten werden konnen. Auf diese Weise erhalt man schnell und effizient Zugan…

ChemInform Abstract: Preparation of 5-Bromo-6-phenylimidazo[2,1-b][1,3,4]thiadiazol-2-ylamines.

The reaction of primary or secondary amines with 2,5-dibromo-6-phenylimidazo[2,1-b][1,3,4]-thiadiazole (5) leads to a chemoselective replacement of the 2-Br substituent. The process represents a convenient route to the corresponding 2-ylamines 7a-d. Hydrazine reacts in an analogous fashion (5 → 7e). The structure determinations are based on an X-ray crystal structure analysis and on one- and two-dimensional NMR measurements.

Isomerization of perchlorohexatriene in three consecutive rearrangements to perchloro-2-vinylbutadiene

Perchlorohexatriene isomerizes in three subsequent rearrangements to perchloro-2-vinylbutadiene. A radical-induced Z-E-equilibration of linear perchlorohexatrienes is followed by cyclization to a methylenecyclopentene. Under flash-vacuum pyrolysis conditions, a ring contraction to 1,2-dimethylenecyclobutane occurs. In the condensed phase, a radical-induced ring opening generates the branched perchloro-vinylbutadiene. All compounds are converted to hexachlorobenzene, but only at very high temperatures.

Enantioselective Strecker Reaction Catalyzed by an Organocatalyst Lacking a Hydrogen-Bond-Donor Function

Tetraaquabis[3-(2-pyridylsulfanyl)propionato N-oxide]nickel(II)

In the centrosymmetric title compound, [Ni(C8H8NO3S)2(H2O)4], the NiII ion, which lies on an inversion centre, is six coordinated by four water molecules and two propionate O atoms from two 2-pyridylsulfanylpropionate N-oxide ligands, forming a slightly distorted octahedral geometry. An intramolecular O&amp;#8212;H...O hydrogen bond stabilizes the molecular conformation. The crystal packing is consolidated by intermolecular O&amp;#8212;H...O and C&amp;#8212;H...O hydrogen bonding.

A black-box approach to the construction of metal-radical multispin systems and analysis of their magnetic properties

An interaction of M(hfac)2 (M = Mn or Ni) with N-(bis(4,4,5,5-tetramethyl-3-oxido-1-oxyl-4,5-dihydro-1H-imidazol-2-yl)methylene)-2-methyl-propan-2-amine oxide (a nitronyl nitroxide diradical with theC[double bond, length as m-dash]N(O)-tert-Bu coupler) was investigated under various conditions. It was found that prolongation of reaction time caused transformation of the initial diradical into new diradicals with the uniqueC[double bond, length as m-dash]N-OH coupling unit and formation of binuclear Mn(ii) and Ni(ii) complexes, which were characterized by X-ray diffraction analysis. The resulting binuclear heterospin complexes have a complicated magnetic structure with six paramagnetic cente…

Rücktitelbild: Eine regio- und diastereoselektive anodische Aryl-Aryl-Kupplung in der biomimetischen Totalsynthese von (−)-Thebain (Angew. Chem. 34/2018)

Synthesis and Isolation of Enantiomerically Enriched Cyclopenta[b]benzofurans Based on Products from Anodic Oxidation of 2,4-Dimethylphenol

The anodic treatment of 2,4-dimethylphenol offers a powerful and direct method for the construction of a dehydrotetramer with four contiguous stereocentres on a multigram scale. The installation of propellanes on this scaffold using enantiomerically pure carbonyl compounds leads to a mixture of diastereomers. This mixture is easily separable using standard chromatography and gives rise to optically pure cyclopenta[b]benzofurans which are important scaffolds in a variety of natural products. The synthesis is easy to perform and allows a reliable access to chiral compounds with very high enantiomeric excess. It was possible to determine the absolute configuration of these compounds by compari…

Flexible Synthesis of Planar Chiral Azoninones and Optically Active Indolizidinones

The flexible synthesis of defined substituted optically active indolizidinones starting from chiral pool (S)-proline and trans 4-hydroxy-(S)-proline is described. Several defined 2-vinylpyrrolidines were generated in short sequences. The aza-Claisen rearrangement using chloro and phenylketene equivalents delivered nine-membered-ring lactams with up to three stereogenic centres and pS-arranged E olefins. Depending on the substitution pattern, certain azoninones had a flexible conformation and showed pS/pR double-bond flipping. Treatment of the unsaturated lactams with the soft electrophile iodine induced diastereoselective transannular ring contractions. Here, the planar chiral arrangement o…

2-(Mesitylmethylsulfanyl)pyridine N-oxide monohydrate

In the title compound, C15H17NOS&#183;H2O, the benzene and pyridine rings form a dihedral angle of 71.18&#8197;(2)&#176;. The intramolecular S...O distance [2.737&#8197;(3)&#8197;&#197;] is shorter than expected and, in terms of hybridization principles, the N&#8212;C&#8212;S angle [114.1&#8197;(2)&#176;] is smaller than expected. The crystal structure is stabilized by intermolecular O&#8212;H...O and weak C&#8212;H...O hydrogen bonds. In addition, weak &#960;&#8211;&#960; stacking interactions with a centroid&#8211;centroid distance of 3.778&#8197;(3)&#8197;&#197; are also observed.

N-{4-[4-(4-Fluorophenyl)-1-(2-methoxyethyl)-2-methylsulfanyl-1H-imidazol-5-yl]-2-pyridyl}-2-methyl-3-phenylpropionamide

In the crystal structure of the title compound, C28H29FN4O2S, the imidazole ring makes dihedral angles of 11.85&amp;#8197;(7), 73.33&amp;#8197;(7) and 22.83&amp;#8197;(8)&amp;#176; with the 4-fluorophenyl, pyridine and phenyl rings, respectively. The 4-fluorophenyl ring makes dihedral angles of 77.91&amp;#8197;(7) and 26.93&amp;#8197;(8)&amp;#176; with the pyridine and phenyl rings, respectively. The phenyl and pyridine rings are nearly perpendicular, making a dihedral angle of 86.47&amp;#8197;(9)&amp;#176;. The crystal packing shows an intermolecular N&amp;#8212;H...O hydrogen-bonding interaction between the N&amp;#8212;H and carbonyl groups of the amide functions.

N-{(Z)-2-[1-(Triisopropylsilyl)-1H-indol-3-yl]-2-(triisopropylsilyloxy)vinyl}-2-(3,4,5-trimethoxyphenyl)acetamide

The molecular structure of the title compound, C39H62N2O5Si2, obtained as an unexpected side product, was determined in the course of our studies on the synthesis of N-triisopropyl-1H-indol-3-yl derivatives. Interestingly, although the triisopropylsilyl group was intended as a temporary protecting group, the compound comprises a remarkably stable N—Si bond. The vinyl C=C double bond possesses a Z configuration.

From anthraquinone to heterocoronene as stable red chromophore

Using the commercially available 1,4,5,8-tetrachloroanthraquinone (1) as starting material, a N-heterocoronene derivative 3 was synthesized via a straightforward two-step reaction. Compound 3 shows a similar photostability as perylene dyes, qualifying it as a promising colorant.

4-[5-(4-Fluoro­phen­yl)-1H-imidazol-4-yl]pyridine

In the title compound, C(14)H(10)FN(3), the imidazole ring makes dihedral angles of 28.2 (1) and 36.60 (9)° with the pyridine ring and the 4-fluoro-phenyl ring, respectively. The pyridine ring forms a dihedral angle of 44.68 (9)° with the 4-fluoro-phenyl ring. Inter-molecular N-H⋯N hydrogen bonds are observed in the crystal structure.

A Regio- and Diastereoselective Anodic Aryl-Aryl Coupling in the Biomimetic Total Synthesis of (-)-Thebaine.

The biosynthesis of thebaine is based on the regioselective, intramolecular, oxidative coupling of (R)-reticuline. For decades, chemists have sought to mimic this coupling by using stoichiometric oxidants. However, all approaches to date have suffered from low yields or the formation of undesired regioisomers. Electrochemistry would represent a sustainable alternative in this respect but all attempts to accomplish an electrochemical synthesis of thebaine have failed so far. Herein, a regio- and diastereoselective anodic coupling of 3',4',5'-trioxygenated laudanosine derivatives is presented, which finally enables electrochemical access to (-)-thebaine.

Dehydrogenative Anodic C−C Coupling of Phenols Bearing Electron‐Withdrawing Groups

Abstract We herein present a metal‐free, electrosynthetic method that enables the direct dehydrogenative coupling reactions of phenols carrying electron‐withdrawing groups for the first time. The reactions are easy to conduct and scalable, as they are carried out in undivided cells and obviate the necessity for additional supporting electrolyte. As such, this conversion is efficient, practical, and thereby environmentally friendly, as production of waste is minimized. The method features a broad substrate scope, and a variety of functional groups are tolerated, providing easy access to precursors for novel polydentate ligands and even heterocycles such as dibenzofurans.

Unexplored analytics of some novel 3d–4f heterometallic Schiff base complexes

Three heterometallic Schiff-base complexes of Cu having Pr, Nd and Sm as the heteroatoms have been synthesized. The compounds have also been characterized by their IR spectra and CHN analysis. The single crystal structures of these compounds have been studied from the X-ray crystallographic data. To the best of our knowledge the article describes the possibility of application of these compounds in the field of species dependent anion sensing for the first time. Amongst a number of anionic species, certain sulphur species were found to have greater reactivity towards a Schiff-base complex as they can incur probable changes in the molecular complexity. The S2O82−and S2O32− species could modi…

4-[4-(4-Fluoro-phen-yl)-2-methyl-5-oxo-2,5-dihydro-isoxazol-3-yl]-1-methyl-pyridinium iodide-4-[3-(4-fluoro-phen-yl)-2-methyl-5-oxo-2,5-dihydro-isoxazol-4-yl]-1-methyl-pyridinium iodide (0.6/0.4).

The crystal structure of the title compound, C(16)H(16)FN(2)O(2) (+)·I(-), was determined as part of a study of the biological activity of isoxazolone derivatives as p38 mitogen-activated protein kinase (MAPK) inhibitors. The X-ray crystal structure of 4-[4-(4-fluoro-phenyl)-2-methyl-5-oxo-2,5-dihydro-isoxazol-3-yl]-1-methyl-pyridinium iodide showed the presence of the regioisomer 4-[3-(4-fluoro-phenyl)-2-methyl-5-oxo-2,5-dihydro-isoxazol-4-yl]-1-methyl-pyridinium iodide. The synthesis of the former compound was achieved by reacting 4-(4-fluoro-phenyl)-3-(4-pyridyl)isoxazol-5(2H)-one after treatment with Et(3)N in dimethyl-formamide, with iodo-methane. The unexpected formation of the regioi…

catena-Poly[[aquasodium(I)]-μ-[2,2′-(disulfanediyl)bis(pyridineN-oxide)]-μ-(pyridine-2-thiolato 1-oxide)]

There are two monomeric units in the asymmetric unit of the polymeric title compound, [Na(C(5)H(4)NOS)(C(10)H(8)N(2)O(2)S(2))(H(2)O)](n). The Na(I) ions are six coordinated by four O atoms, one S atom and one water mol-ecule, forming a slightly distorted octa-hedral geometry. An intra-molecular O-H⋯O hydrogen bond stabilizes the conformation of the mol-ecule. The crystal packing is consolidated by inter-molecular O-H⋯O, O-H⋯N and O-H⋯S hydrogen bonds, π-π inter-actions [with centroid-centroid distances of 3.587 (2) Å] together with weak C-H⋯π inter-actions. The mol-ecules are linked into polymeric chains along the b-axis direction.

Cover Feature: Visible Light‐Induced Sulfonylation/Arylation of Styrenes in a Double Radical Three‐Component Photoredox Reaction (Chem. Eur. J. 38/2019)

1-(3′,6′-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthen]-5-yl)-3-[4-({4-[1-(4-fluorophenyl)-1H-imidazol-5-yl]pyridin-2-yl}amino)phenyl]thiourea methanol monosolvate

The title compound, which crystallized as a methanol monosolvate, C41H27FN6O5S·CH3OH, was synthesized as a probe for a fluorescence polarization-based competition binding assay. The isobenzofuran fused-ring system is close to planar and orientated almost perpendicular to the central ring of the xanthene system. The dihedral angle between the benzene rings of the xanthene system is 10.0 (2)°, indicating a butterfly-like orientation. A short intramolecular C—F...π contact [F...π = 3.100 (4) Å and C—F...π = 139.9 (3)°] to the six-membered ring of the isobenzofuran system may influence the molecular conformation. The methanol solvent molecule is disordered over two orientations in a 0.6:0.4 rat…

Taste, a new incentive to switch to (R)-praziquantel in schistosomiasis treatment.

Background Praziquantel (PZQ) is the drug compound of choice in the control and treatment of schistosomiasis. PZQ is administered as a racemate, i. e. 1∶1 mixture of enantiomers. The schistosomicidal activity arises from one PZQ-enantiomer, whereas the other enantiomer does not contribute to the activity. The WHO's Special Programme for Research and Training in Tropical Diseases (TDR) has assigned the low-cost preparation of pure schistosomicidal (−)-PZQ a key priority for future R&D on PZQ, but so far this transition has not happened. PZQ has two major administration drawbacks, the first being the high dose needed, and its well documented bitter and disgusting taste. Attempts of taste-mask…

Racemic S ‐(ethylsulfonyl)‐ dl ‐cysteine N ‐Carboxyanhydrides Improve Chain Lengths and Monomer Conversion for β‐Sheet‐Controlled Ring‐Opening Polymerization

The secondary structure formation of polypeptides not only governs folding and solution self-assembly but also affects the nucleophilic ring-opening polymerization of alpha-amino acid-N-carboxyanhydrides (NCAs). Whereby helical structures are known to enhance polymerization rates, beta-sheet-like assemblies reduce the propagation rate or may even terminate chain growth by precipitation or gelation. To overcome these unfavorable properties, racemic mixtures of NCAs can be applied. In this work, racemicS-(ethylsulfonyl)-dl-cysteine NCA is investigated for the synthesis of polypeptides, diblock and triblock copolypept(o)ides. In contrast to the polymerization of stereoregularS-(ethylsulfonyl)-…

Chlorido(dimethyl sulfoxide)(pyridine-2-thiolato N-oxide-κ2S,O)platinum(II)

The asymmetric unit of the title compound, [Pt(C5H4NOS)Cl(C2H6OS)], contains two independent complex molecules having similar geometries. Each PtII atom is four-coordinated in a distorted square-planar geometry by S and O atoms of one pyridine N-oxide ligand, the S atom of one dimethyl sulfoxide molecule and one terminal Cl− ion. The molecules are linked into a three-dimensional framework by C—H...O and C—H...Cl hydrogen bonds.

2-(Mesitylmethylsulfanyl)pyridineN-oxide–18-crown-6 (2/1)

In the title compound, 2C(15)H(17)NOS·C(12)H(24)O(6), the asymmetric unit consists of one N-oxide derivative and one-half of the 18-crown-6 ether, which lies on an inversion centre. In the crown ether, the O-C-C-O torsion angles indicate a gauche conformation of the ethyl-eneoxy units, while the C-O-C-C torsion angles indicate planarity of these segments. In the N-oxide unit, the dihedral angle between the pyridine and benzene rings is 85.88 (12)°. The crystal packing is stabilized by weak C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

Cruciform Electron Acceptors Based on Tetraindeno-Fused Spirofluorene

Two cruciform tetraindenospirofluorene-based acceptors embedding carbonyl (Spiro-4O) and dicyanovinylene (Spiro-8CN) functionalities are synthesized in high yields. Single-crystal X-ray analysis reveals a one-dimensional π–π stacking arrangement for Spiro-4O, while Spiro-8CN adopts a unique two-dimensional isotropic π-interaction. Cyclic voltammetry suggests a high electron affinity of −3.76 eV for Spiro-8CN. Such a packing motif and low LUMO energy for Spiro-8CN are important for bulk electron transport.

Spectroscopic Investigation of the System TeCl4/[NEt4]PF6 in Solution and the Crystal Structure of [NEt4]2[Te2Cl10].

Solutions containing TeCl 4 and [NEt 4 ][PF 6 ] in CH 2 Cl 2 were investigated by means of UV/vis and NMR spectroscopy in order to study the complex chemistry of TeCl 4 with the [PF 6 ] - anion. The results show formation of [TeCl 5 ] - and strong interactions of [PF 6 ] - with a tellurium containing species, presumably [TeCl 3 ] + . The life time of the Te I V -PF 6 complex is long enough to give different signals in the 1 9 F NMR spectrum of a solution containing excess [PF 6 ] - . Even a fivefold excess of Cl - ions over [PF 6 ] - does hardly lead to a dissociation of [TeCl 3 ...PF 6 ]. Crystals of [NEt 4 ] 2 [Te 2 Cl 1 0 ] were obtained from a 4:1 solution of [NEt 4 ]PF 6 and TeCl 4 in …

1,2-Asymmetric Induction in Diastereo­selective Zwitterionic Aza-Claisen Rearrangements: Key Steps in Optically Active Alkaloid Synthesis

The zwitterionic aza-Claisen rearrangement of optically active N-allylpyrrolidines and α-phenoxyacetyl fluorides proceeds with complete simple diastereoselectivity (internal asymmetric induction) and complete 1,2-asymmetric induction to generate a new C–C bond adjacent to a chiral C-N-Boc functionality. The resulting γ,δ-unsaturated amides were cyclised to give the corresponding pyrrolizidinones, which enabled the determination of the relative configuration of the stereotriads. Vinyl group degradation and a final lactam reduction gave an optically active analogue of (+)-petasinine (a pyrrolizidine alkaloid). Furthermore, the stereotriad-containing amides should be useful key intermediates f…

1-{3-[(7-Fluoro-9H-pyrimido[4,5-b]indol-4-yl)(methyl)amino]piperidin-1-yl}propan-1-one

The title compound, C19H22FN5O, has been synthesized as an inhibitor of glycogen synthase kinase-3β. Two molecules interact via two N—H...N hydrogen bonds, forming centrosymmetric dimers.

3-(4-Fluorophenyl)-1-methyl-4-(4-pyridyl)quinolin-2(1H)-one

The title compound, C21H15FN2O, was synthesized in the course of our studies of p38 mitogen-activated protein kinase inhibitors. It has been investigated by 1H and 13C NMR spectroscopy and was proven by X-ray crystallographic analysis to be the N-methyl rather than the O-methyl isomer. In the crystal structure, a three-dimensional network is formed consisting of quinolinone aromatic stacking inter­actions and weak C—H⋯O and C—H⋯N hydrogen bonds.

On-surface Synthesis of a Chiral Graphene Nanoribbon with Mixed Edge Structure.

Abstract Chiral graphene nanoribbons represent an important class of graphene nanomaterials with varying combinations of armchair and zigzag edges conferring them unique structure‐dependent electronic properties. Here, we describe the on‐surface synthesis of an unprecedented cove‐edge chiral GNR with a benzo‐fused backbone on a Au(111) surface using 2,6‐dibromo‐1,5‐diphenylnaphthalene as precursor. The initial precursor self‐assembly and the formation of the chiral GNRs upon annealing are revealed, along with a relatively small electronic bandgap of approximately 1.6 eV, by scanning tunnelling microscopy and spectroscopy.

(4R)-4-Hydroxy-1-[(2S)-2-hydroxydodecyl]-L-proline monohydrate

The title compound, C17H33NO4·H2O, was found to be the S diastereoisomer with respect to the asymmetric C atom at the OH group on the chain. The X-ray structure was determined as part of a study of the mol­ecular geometry and stereochemistry of l-proline derivatives for pre-coating thin-layer chromatography plates intended for enantiomeric separation.

cis-Bis(2-sulfidopyridine N-oxide)platinum(II).

In the crystal structure of the title complex, [Pt(C5H4NOS)2], the Pt atom is coordinated by two O atoms and two S atoms in a cis configuration, forming a distorted square-planar coordination geometry. The molecule exhibits pseudo-C2v symmetry and is essentially planar, with a maximum deviation from planarity of 0.0124&#8197;(2)&#8197;&#197;. The dihedral angle between the two pyridine rings is 5.85&#8197;(2)&#176;.

Hexasubstituierte Benzolderivate mit ultrastarken Dipolmomenten

Synthesis of Highly Functionalized N , N ‐Diarylamides by an Anodic C, N ‐Coupling Reaction

We report an innovative, sustainable and straightforward protocol for the synthesis of N,N-diarylamides equipped with nonprotected hydroxyl groups by using electrosynthesis. The concept allows the application of various substrates furnishing diarylamides with yields up to 57 % within a single and direct electrolytic protocol. The method is thereby easy to conduct in an undivided cell with constant current conditions offering a versatile and short-cut alternative to conventional pathways.

Rearrangement of the carbon skeleton in the intramolecular photoadduct of anthracene and benzene rings

Abstract The effectivity of optical switching between anthracene derivatives 3a,b and their intramolecular photocycloadducts 4a,b is impaired by traces of acid. The systematic treatment of 4a,b with an increasing excess of formic acid revealed that—apart from the normal enolether cleavage 4a,b → 6a,b → 7a,b —a cleavage with rearrangement of the carbon skeleton can occur: 5b → 6b′ . The driving force is a stability enhancement of the involved carbenium ions 5b → 5b′ . A further increased excess of formic acid leads finally to a competitive ether cleavage in the tetrahydrofuran ring 5b → 8 .

Mannose-Decorated Multicomponent Supramolecular Polymers Trigger Effective Uptake into Antigen-Presenting Cells

A modular route to prepare functional self-assembling dendritic peptide amphiphiles decorated with mannosides, to effectively target antigen-presenting cells, such as macrophages, is reported. The monomeric building blocks were equipped with tetra(ethylene glycol)s (TEGs) or labeled with a Cy3 fluorescent probe. Experiments on the uptake of the multifunctional supramolecular particles into murine macrophages (Mφs) were monitored by confocal microscopy and fluorescence-activated cell sorting. Mannose-decorated supramolecular polymers trigger a significantly higher cellular uptake and distribution, relative to TEG carrying bare polymers. No cytotoxicity or negative impact on cytokine producti…

1-Benz­yloxy-1H-benzotriazole

In the title compound, C13H11N3O, the dihedral angle between the benzotriazole ring system [maximum deviation = 0.027&amp;#8197;(16)&amp;#8197;&amp;#197;] and the benzene ring is 10.28&amp;#8197;(9)&amp;#176;. The C&amp;#8212;C&amp;#8212;O&amp;#8212;N bond adopts an anti conformation [torsion angle = &amp;#8722;177.11&amp;#8197;(16)&amp;#176;]. In the crystal, the molecules interact via weak C&amp;#8212;H...&amp;#960; interactions and aromatic &amp;#960;&amp;#8211;&amp;#960; stacking [centroid-to-centroid distance = 3.731&amp;#8197;(12)&amp;#8197;&amp;#197;].

Inhibitors of inducible NO synthase expression: total synthesis of (S)-curvularin and its ring homologues.

(S)-Curvularin and its 13-, 14-, and 16-membered lactone homologues were synthesized through a uniform strategy in which a Kochi oxidative decarboxylation and ring-closing metathesis reactions constitute the key processes. In the evaluation of the anti-inflammatory effects of the synthesized compounds in assays using cells stably transfected with a human iNOS promoter-luciferase reporter gene construct, the 14- and 16-membered homologues showed a slightly higher inhibitory effect towards iNOS promoter activity than curvularin itself. However, the larger ring homologues also exhibited higher cytotoxicity, manifest in downregulated eNOS promoter activity. In contrast, the di-O-acetyl and 4-ch…

2,5-Bis[(E)-2-phenylethenyl]-3,6-bis(pyridin-2-yl)pyrazine

The molecule of the title compound, C30H22N4, exhibits inversion symmetry adopting the shape of a St Andrew's Cross. It shows dihedral angles between adjacent aryl units of around 50° whereas torsion angles of ca 10° are found along the arylene vinylene path.

Powerful Fluoroalkoxy Molybdenum(V) Reagent for Selective Oxidative Arene Coupling Reaction

We introduce the novel fluoroalkoxy molybdenum(V) reagent 1 which has superior reactivity and selectivity in comparison to MoCl5 or the MoCl5 /TiCl4 reagent mixture in the oxidative coupling reactions of aryls. Common side reactions, such as chlorination and/or oligomer formation, are drastically diminished creating a powerful and useful reagent for oxidative coupling. Theoretical treatment of the reagent interaction with 1,2-dimethoxybenzene-type substrates indicates an inner-sphere electron transfer followed by a radical cationic reaction pathway for the oxidative-coupling process. EPR spectroscopic and electrochemical studies, X-ray analyses, computational investigations, and the experim…

ChemInform Abstract: Synthesis of Pyrrolidin-2-ones and of Staurosporine Aglycon (K-252c) by Intermolecular Michael Reaction.

Indolo[2,3-a]pyrrolo[3,4-c]carbazoles were isolated from nature, e.g., from low plants, especially fungi, as structurally rare natural substances. Responsible for naming and also the most important representative of this type is staurosporine (1), isolated from Streptomyces staurosporeus, and its aglycon (2), also known as staurosporinone or K-252c. 3,4-Disubstituted pyrrolidin-2-ones, a group of compounds with many interesting biological properties are related to staurosporinone. The most important property is the inhibition of protein kinase C (PKC), so that this antiproliferative agent can interfere with the cell cycle. The synthetic strategy, developed by us, allows the synthesis of pyr…

Titelbild: Metall- und reagensfreie hochselektive anodische Kreuzkupplung von Phenolen (Angew. Chem. 20/2014)

Structural, magnetic and related attributes of some oximate-bridged tetranuclear nickel(ii) rhombs and a dinuclear congenerElectronic supplementary information (ESI) available: mass spectra, χT vs. T, response of magnetic properties, low-lying spin levels and UV-VIS data. See http://www.rsc.org/suppdata/dt/b3/b300539a/

New oximate-bridged tetranuclear nickel(II) complexes of compositions {Ni(Dien)}2(μ3-OH)2{Ni2(Moda)4}(ClO4)2·Solv (Solv = H2O, 1a; Solv = 2CH3NO2, 1b; Solv = 2H2O·2C4H8O2, 1c), {Ni(Sdien)}2(μ3-OH)2{Ni2(Moda)4}(ClO4)2·H2O (2), {Ni(Odien)}2(μ3-OH)2{Ni2(Moda)4}(ClO4)2·0.6H2O (3), {Ni(Dien)}2(μ3-OH)2{Ni2(Inaf)4}(ClO4)2·CH3NO2 (4) and {Ni(Odien)}2(μ3-OH)2{Ni2(Inaf)4}(ClO4)2·2NaClO4·2H2O (5) and the dinuclear complex (Ni{Odien})2(Moda)2(ClO4)2 (6) have been prepared (Dien = 1,5-diamino-3-azapentane, Odien = 1,5-diamino-3-oxapentane, Sdien = 1,5-diamino-3-thiapentane, ModaH = butane-2,3-dione monooxime, InafH = phenylglyoxaldoxime). X-ray examination revealed similar structures for 1a, 1b, 1c, 2 a…

N-{2-Methyl-5-[(5-oxo-10,11-dihydro-5H-dibenzo[a,d]cyclo­hepten-2-yl)amino]­phen­yl}benzamide

In the title compound, C29H24N2O2, the two aromatic rings of the tricyclic unit are oriented at a dihedral angle of 32.27&amp;#8197;(8)&amp;#176;. In the crystal N&amp;#8212;H...O hydrogen bonds link the molecules into chains along the a axis. Further N&amp;#8212;H...&amp;#183;O interactions link the chains.

Hockey-Puck micelles from oligo(p-benzamide)-b-PEG rod-coil block copolymers.

Synthesis, structure and magnetic properties of oligometallic systems derived from di- and trinuclear copper(ii) amido-oximate complexes

Three heterometallic complexes [M(H(2)O)(n)][Cu(3)L(2)(H(2)O)] (M = Mn(2+), Co(2+) or Ba(2+)) and one dinuclear compound (CuDien)(CuL{H(2)O}) were prepared by interaction of anionic compounds Cu(3)L(2)(2-) or CuL(2-) with the corresponding cations (H(4)L = 1,9-dicyano-1,9-bis(hydroximino)-3,7-diazanonane-2,8-dione; Dien = 1,5-diamino-3-azapentane). The complexes [M(H(2)O)(n)][Cu(3)L(2)(H(2)O)] have a polymeric structure, formed via oligomerization of Cu(3)L(2)(2-) units and additionally, in the case of the Ba-salt, by binding of Cu(3)L(2)(2-) units through Ba(2+). Antiferromagnetic interactions occur in all the complexes, while for [Co(H(2)O)(6)][Cu(3)L(2)(H(2)O)] there is evidence of some …

4-Aminopyridinium 4-aminobenzoate dihydrate and 4-aminopyridinium nicotinate.

In the title compounds, 4-aminopyridinium 4-aminobenzoate dihydrate, C(7)H(6)NO(2)(-).C(5)H(7)N(2)(+).2H(2)O, (I), and 4-aminopyridinium nicotinate, C(5)H(7)N(2)(+).C(6)H(4)NO(2)(-), (II), the aromatic N atoms of the 4-aminopyridinium cations are protonated. In (I), the asymmetric unit is composed of two 4-aminopyridinium cations, two 4-aminobenzoate anions and four water molecules, and the compound crystallizes in a noncentrosymmetric space group. The two sets of independent molecules of (I) are related by a centre of symmetry which is not part of the space group. In (I), the protonated pyridinium ring H atoms are involved in bifurcated hydrogen bonding with carboxylate O atoms to form an …

4-[3-(4-Fluorophenyl)-5-isopropylisoxazol-4-yl]pyridine

The mol­ecular structure of the title compound, C17H15FN2O, was determined in the course of our studies on mitogen-activated protein kinase inhibitors. The exocyclic bond angles at the carbon atoms of the isoxazole ring bearing the pyridyl and 4-fluoro­phenyl rings are 130.0 (2) and 129.2 (2)°, respectively. The pyridine and 4-fluoro­phenyl rings are twisted relative to the isoxazole ring by 80.2 (2) and 19.1 (1)°, respectively.

Frontispiz: Metallfreie, elektrochemische Synthese von Sulfonamiden direkt aus (Hetero)arenen, SO 2 und Aminen

2,4,6-Tris(1-oxo-2-pyridylsulfanylmeth­yl)mesitylene methanol solvate

In the title compound, C(27)H(27)N(3)O(3)S(3)·CH(4)O, the dihedral angles formed by the mesitylene ring with the three oxopyridyl rings are 89.6 (1), 75.5 (1) and 80.69 (1)°, indicating that all three are nearly perpendicular to the mesitylene ring. Intra-molecular C-H⋯S hydrogen bonds generate S(6) ring motifs. The crystal structure is stabilized by intra-molecular C-H⋯S and inter-molecular C-H⋯O hydrogen bonds and weak C-H⋯π inter-actions.

Carbamoylmethylphosphinoxide derivatives based on the triphenylmethane skeleton. Synthesis and extraction properties.

Two different strategies were used to synthesize tri(2-alkoxy-5-nitrophenyl)methanes 6a,b. The X-ray structures of 6a and its precursor 5 show the molecules in a conformation with a syn-orientation of the nitro and alkoxy groups. Hydrogenation and acylation by the appropriate active ester gave the corresponding tri-CMPO derivatives 4a,b. Their ability to complex lanthanide ions was studied by NMR spectroscopy and by nuclear magnetic relaxation dispersion and further characterized by quantum mechanical calculations. Extraction experiments from acidic solution to dichloromethane reveal a reasonable selectivity of Am(III) over Eu(III), but in contrast to similar tetra-CMPOs derivatives of cali…

Formation of the Cationic [(2‐Aminoethenyl)carbine]iron Complexes by Treatment of (2‐Methoxyethenyl)carbene Complexes with Primary Amines:Synthesis and Characterisation

Cationic (2-methoxyethenyl)methoxycarbene iron complexes 2, [Cp(CO)2Fe(C(OMe)CHCR(OMe))+][PF6−], are obtained by the addition of methanol to the corresponding (alkynyl)-methoxycarbene complexes 1, [Cp(CO)2Fe(C(OMe)CCR)+][PF6−]. Primary amines, H2NR', react with these 1,3-dimethoxy-substituted (alkenyl)carbene complexes, 2, through an addition/elimination process to yield cationic (2-aminoethenyl)methoxycarbene iron complexes, 3, [Cp(CO)2Fe(C(OMe)CHCR(NHR'))+][PF6−] in an isolated yield of 71–90%. The complexes 3a–c were characterized by X-ray structural analyses. Thus, previously isolated products, from the reaction, of the (alkynyl)methoxycarbene complexes 1a and 1c, with aniline at room t…

Synthese und Kristallstrukturanalyse eines 2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepins / Synthesis and Crystal Structure Analysis of a 2,4-Diaryl-2,3-dihydro-1H-1,5-benzodiazepine

Abstract The enone unit of chalcones is a synthetically valuable substructure for the formation of heterocycles. Whereas propoxy groups as solubilizing side chains on the phenyl groups do not much affect the generation of pyrazole and pyridine rings, they reduce significantly the yield of the diazepine ring system 4. We attribute this effect to the large twist angles between the ring planes, which are demonstrated by a crystal structure analysis.

ChemInform Abstract: Selective Synthesis of Partially Protected Nonsymmetric Biphenols by Reagent- and Metal-Free Anodic Cross-Coupling Reaction.

The oxidative cross-coupling of aromatic substrates without the necessity of leaving groups or catalysts is described. The selective formation of partially protected nonsymmetric 2,2'-biphenols via electroorganic synthesis was accomplished with a high yield of isolated product. Since electric current is employed as the terminal oxidant, the reaction is reagent-free; no reagent waste is generated as only electrons are involved. The reaction is conducted in an undivided cell, and is suitable for scale-up and inherently safe. The implementation of O-silyl-protected phenols in this transformation results in both significantly enhanced yields and higher selectivity for the desired nonsymmetric 2…

Novel Stannatrane N(CH2CMe2O)2(CMe2CH2O)SnO-t-Bu and Related Oligonuclear Tin(IV) Oxoclusters. Two Isomers in One Crystal

The syntheses of the alkanolamine N(CH2CMe2OH)2(CMe2CH2OH) (1), of the stannatrane N(CH2CMe2O)2(CMe2CH2O)SnO-t-Bu (2), and of the trinuclear tin oxocluster 3 consisting of the two isomers [(μ3-O)(O-t-Bu){Sn(OCH2CMe2)(OCMe2CH2)2N}3] (3a) and [(μ3-O)(μ3-O-t-Bu){Sn(OCH2CMe2)(OCMe2CH2)2N}3] (3b) as well as the isolation of a few crystals of the hexanuclear tin oxocluster [LSnOSn(OH)3LSnOH]2 [L = N(CH2CMe2O)2(CMe2CH2O)] (4) are reported. The compounds were characterized by 1H, 13C, 15N, and 119Sn (1–3) nuclear magnetic resonance and infrared spectroscopy, electrospray ionization mass spectrometry, and single-crystal X-ray diffraction analysis (1–4). A graph set analysis was performed for compoun…

Semicarbazides as gel forming agents for common solvents and liquid crystals

This paper describes the synthesis of 14 new gelling agents with semicarbazide groups as H-bonding motifs and alkyl- and/or azobenzene side groups. They gel solvents like decaline, 1,2-dichlorobenzene and toluene and liquid crystalline mixtures. X-Ray structure analysis shows that the semicarbazides are connected by H-bonds, each molecule to four neighbours. As a result a ribbon is formed with a core of H-bonded semicarbazide groups and alkyl chains sticking to the side. IR measurements show an unchanged H-bonding motif in large crystals and in the gel fibres, even in LC-mixture. During heating the gel melts (rheology), while the H-bonding motif of the crystal disappears (IR and DSC measure…

Synthesis of Nonplanar Graphene Nanoribbon with Fjord Edges

As a new family of semiconductors, graphene nanoribbons (GNRs), nanometer-wide strips of graphene, have appeared as promising candidates for next-generation nanoelectronics. Out-of-plane deformation of π-frames in GNRs brings further opportunities for optical and electronic property tuning. Here we demonstrate a novel fjord-edged GNR (FGNR) with a nonplanar geometry obtained by regioselective cyclodehydrogenation. Triphenanthro-fused teropyrene 1 and pentaphenanthro-fused quateropyrene 2 were synthesized as model compounds, and single-crystal X-ray analysis revealed their helically twisted conformations arising from the [5]helicene substructures. The structures and photophysical properties …

ChemInform Abstract: Reaction of 2,2′-Bis(N-methylindolyl) with Dimethyl Acetylenedicarboxylate and Thermally and Photochemically Induced Cyclizations of the Product.

2,2′-Bis(N-methylindolyl) 1 reacts with dimethyl acetylenedicarboxylate to furnish the 3-dimethyl maleoyl-substituted 2,2′-bisindolyl 2. Compound 2 cyclizes under aluminum trichloride catalysis according to a polar process to give a cyclopenta[2,1-b:3,4-b′]diindole derivative 4. Reaction of compound 4 with benzyl-amine yields the spiro derivative 5. Photochemically-induced 1,6-electrocyclization of compound 2 gives rise to the indolo[2,3-a]carbazole 6 directly, which is readily transformed to the pyrrolo-annelated carbazole 7 by treatment with benzylamine.

Quantitative estimation of the antiferromagnetic interaction between Cu(II) and Sm(III) in two dimensional heterometallic coordination polymer with isonicotinic acid as tectons

Abstract The syntheses, structure and magnetic property of a novel two dimensional 3d–4f coordination polymer 2∞[CuSmL(NO3)2(IN)], 1 (L2−  = N, N′- propylenedi (3-ehoxysalicylideneiminato), the dianion of the Schiff base obtained from the 2:1 condensation of 3-ethoxysalicylaldehyde with 1,3-propanediamine, IN− = the isonicotinate ion) has been reported. The heterobinuclear units are connected through exo-bidentate ligands IN−, leading to an extended 2D structure. A fit of the magnetic susceptibility data yields gCu = 2.109, gSm = 0.476, JCuSm = − 0.893 cm− 1, θ = − 3.37 K, and TIP = 0.001257 emu K mol− 1 with a good discrepancy factor of Rχ = 4.4 × 10− 5. This is the first quantitative esti…

Synthesis, Structure and Solvatochromism of the Emission of Cyano-Substituted Oligo(phenylenevinylene)s

Strongly luminescent and highly soluble oligo(phenylenevinylene)s with five benzene rings and cyano groups in different positions of the terminal styrene units were prepared by means of Horner and Knoevenagel reactions. The substitution pattern − cyanide moieties on the vinyl or on the aromatic regions, together with the effect of auxochromic groups − has distinct influences on the electronic spectra, particularly on the fluorescence. Polar solvents induce red shifts and strongly reduce the fluorescence intensity of the vinyl-substituted oligomers. Cyano substitution increases the electron affinity of the oligomers; this effect is more pronounced for molecules with vinyl cyanides and can be…

Reagent- and Metal-Free Anodic C-C Cross-Coupling of Aniline Derivatives.

The dehydrogenative cross-coupling of aniline derivatives to 2,2′-diaminobiaryls is reported. The oxidation is carried out electrochemically, which avoids the use of metals and reagents. A large variety of biphenyldiamines were thus prepared. The best results were obtained when glassy carbon was used as the anode material. The electrosynthetic reaction is easily performed in an undivided cell at slightly elevated temperature. In addition, common amine protecting groups based on carboxylic acids were employed that can be selectively removed under mild conditions after the cross-coupling, which provides quick and efficient access to important building blocks featuring free amine moieties.

(Z)-Amino­(2-methyl-3-oxoisoindolin-1-yl­idene)acetonitrile

The asymmetric unit of the title compound, C11H9N3O, contains two independent and nearly identical molecules (A and B). Molecule A can be transformed to B using a rotation of approximately 85&amp;#176; around the [111] direction. Each A molecule is connected to three B molecules via N&amp;#8212;H...N and N&amp;#8212;H...O hydrogen bonds and vice versa. Centrosymmetrically related molecules of the same residue form &amp;#960;&amp;#8211;&amp;#960; interactions with centroid&amp;#8211;centroid distances of 4.326&amp;#8197;(1) and 3.826&amp;#8197;(1)&amp;#8197;&amp;#197; for the benzene rings of molecules A and B, respectively.

ChemInform Abstract: Electrophilic Substitution and Cyclization of 2,2′-Bis(N-methylindolyl) : A Simple Access to Potential Protein Kinase C Inhibitor.

A strategy is described for the synthesis of functionalized and cyclized 2,2′-bisindolyl derivatives related to several basic systems of natural products. The starting 2,2′-bis(N-methylindolyl) (8) reacts with a variety of electrophiles and electrophilic dienophiles to furnish the novel, functionalized and cyclized bisindolyl derivatives 9–16. In addition, some reactivity and structural aspects are discussed; an X-ray crystallographic analysis of the 2,2′-bisindolyl 8 provided valuable information for the conformational analyses.

Mixed phenoxo and azido bridged dinuclear nickel(II) and copper(II) compounds with N,N,O-donor schiff bases: Synthesis, structure, DNA binding, DFT and molecular docking study

Abstract Two dinuclear complexes, µ-phenoxo, µ1,1-azido bridged [Ni2(L)2(µ1,1-N3)(N3)(CH3OH)] (1) and µ-phenoxo, µ1,1-azido bridged [Cu2(L)2(µ1,1-N3)(N3)] (2) bearing HL as a blocking co-ligand produced by the 1:1 condensation of N-methyl 1,3 propanediamine with o-vanillin have been synthesized and successfully characterized by elemental analyses, IR and electronic spectroscopy, single-crystal X-ray diffraction for 1 and DFT optimization for 2. X-ray crystal structure discloses that the asymmetric unit of 1 consists of two nickel(II) ions exhibiting a six-coordinate octahedral coordination with µ-phenoxo, µ1,1-azido bridging dimeric structure. The DFT optimization of 2 reveals the five-coor…

rac-1,1,1,6,6,6-Hexachlorohex-3-yne-2,5-diol hemihydrate

The asymmetric unit of the title compound, C6H4Cl6O2·0.5H2O, contains one molecule of 1,1,1,6,6,6-hexachlorohex-3-yne-2,5-diol and half a water molecule located on a twofold rotation axis. In the crystal, pairs of hexachlorohexynediol molecules form centrosymmetric dimers connectedviapairwise O—H...O hydrogen bonds. These dimers are connected by water molecules, resulting in layers parallel to theabplane.

OH–π and halogen–π interactions as driving forces in the crystal organisations of tri-bromo and tri-iodo trityl alcohols

The trityl alcohols bearing three bromine or three iodine atoms at the para-positions of the aromatic units, have been known for more than a hundred years. In our case these compounds have been synthesized in one-pot sequence starting from the 1,4-dihalogenobenzenes via mono-lithiation and the successive reaction with diethylcarbonate. The compounds have been crystallized from different solvent mixtures leading to one structure of bromo- (A) and three structures of iodo trityl alcohols (B–D). The inclusion of dichloromethane (C) or benzene (D) in the crystalline lattices has been observed. In all cases the OH–π and halogen–π (and in one case the halogen-halogen and CH-O weak) contacts play …

Selective and Scalable Dehydrogenative Electrochemical Synthesis of 3,3′,5,5′-Tetramethyl-2,2′-biphenol

3,3′,5,5′-Tetramethyl-2,2′-biphenol is a compound of high technical significance, as it exhibits superior properties as building block for ligands in the transition-metal catalysis. However, side reactions and overoxidation are challenging issues in the conventional synthesis of this particular biphenol. Here, an electrochemical method is presented as powerful and sustainable alternative to conventional chemical strategies, which gives good yields up to 51%. Despite using inexpensive and well-available bromide-containing supporting electrolytes, the issue of bromination and general byproduct formation is effectively suppressed by adding water to the electrolyte. Additionally, the scalabilit…

The rel-R,R-enantiomer of 7-[7-hydroxybicyclo[4.2.0]octa-1(6),2,4-trien-7-yl]bicyclo[4.2.0]octa-1(6),2,4-trien-7-ol

A single crystal of the rel-R,R-enantiomer of the title compound, C16H14O2, was analyzed. The molecular structure is characterized by nearly planar cyclobutene rings and a torsion angle of the diol unit of 68.3 (2)°. Strands parallel to the b axis are built from diols connected via hydrogen bonds.

5,10-Dihydroindeno[2,1-a]indene

The title compound, C16H12, crystallizes with four half molecules in the asymmetric unit, each of which is located on a crystallographic centre of inversion. The molecules are essentially planar. The crystal studied was a non-merohedral twin.

ChemInform Abstract: Synthesis of Bis(indolylmaleimide) Macrocycles

The synthesis of a novel class of macrocyclic bis(indolylmaleimides) is reported. The key step involves the intermolecular connection of 2,2′-bridged indoles with 3,4-dibromo-2,5-dihydro-1H-2,5-pyrroledione (dibromomaleimide) derivatives. The bis(indolylmaleimides) afforded by this method were further processed by intramolecular nucleophilic substitution of the remaining bromo substituents forming flexible N-substituted macrocycles (9a-9j, 10a-10e) and, by connecting both maleimides, semi rigid macrocycles (7a-7xx).

Dicyanobenzothiadiazole Derivatives Possessing Switchable Dielectric Permittivities

Benzothiadiazoles are important electron acceptors and are frequently employed as electron-deficient components of donor-acceptor polymers. We report the effect of nitrile functionalities on the reactivity, steric hindrance, optoelectronic properties, and dielectric permittivity in dicyanobenzothioadiazole (DCNBT). Dielectric spectroscopy in the bulk and in solution assisted by DFT-calculations revealed that these molecules can be engineered to engender maximum values of the dipole moment and of dielectric permittivity due to the strong electron-withdrawing effect of the nitrile groups. The self-assembly in the bulk was investigated by X-ray scattering performed on single crystals, fibers (…

1,1′-[(2,3,5,6-Tetramethyl-1,4-phenylene)bis(methylene)]dipiperidine

The asymmetric unit of the title compound, C22H36N2, comprises one half-molecule, the other half being generated by a center of inversion. The piperidine ring adopts a chair conformation, with the exocyclic N—C bond in an equatorial orientation. A short intramolecular C—H...N hydrogen bond occurs and forms an S(6) motif. No directional interactions beyond van der Waals contacts are observed between the molecules, which form a wave-like supramolecular architecture.

Crystal structure of 12-benzylsulfanyl-2,9-dibromo-6H-dibenzo[b,g][1,8]naphthyridin-11-one

The hetero-tetra-cene skeleton of the title mol-ecule, C23H14Br2N2OS, is defined by linear annulation of four six-membered rings, including two N heteroatoms. This moiety is nearly planar (r.m.s. deviation = 0.055 Å), with a slight twist of 4.1 (2)° between the two halves of the aromatic system. The dihedral angle between the least-squares plane of the skeleton and the benzyl group is 24.5 (3)°; the C-S-C angle involving the benzyl-sulfanyl group is 99.2 (4)°. In the crystal, mol-ecules are π-stacked in an anti-parallel fashion along [110], with a distance between the aromatic planes of 3.47 (2) Å. Inter-molecular N-H⋯O hydrogen bonds form chains extending parallel to [001] and bridge the a…

4-[2-(4-Fluorophenyl)-1H-pyrrol-3-yl]pyridine

In the crystal structure of the title compound, C(15)H(11)FN(2), the pyrrole ring makes dihedral angles of 33.19 (9) and 36.33 (10)° with the pyridine and 4-fluoro-phenyl rings, respectively. The pyridine ring makes a dihedral angle of 46.59 (9)° with the 4-fluoro-phenyl ring. In the crystal structure, an N-H⋯N hydrogen bond joins the mol-ecules into chains.

rac-(3E,3aR,6aR)-3-(Hydroxymethylene)-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

The crystal structure of the title compound, C8H8O3, was determined in the course of our studies of the synthesis of cyclo­penta­[1,2-b]furan-4-one derivatives. The title compound has two chiral C atoms and was obtained as a racemic mixture. It was found to possess a vinylogous acid group with an E configuration at the double bond. The compound exists in the hydroxy­methyl­ene and not in the tautomeric carbaldehyde form. The asymmetric unit consists of two molecules.

Hockeypuck-Micellen aus Oligo(p-benzamid)-b-PEG-Stab-Knäuel-Blockcopolymeren

Front Cover: Synthesis and Unusual NMR-Spectroscopic Behavior of a Strained Bicyclic Ammonium Salt (Eur. J. Org. Chem. 10/2018)

ChemInform Abstract: Inhibitors of Inducible NO Synthase Expression: Total Synthesis of (S)-Curvularin (Ia) and Its Ring Homologues.

CCDC 1421613: Experimental Crystal Structure Determination

Related Article: Jakob Wudarczyk, George Papamokos, Vasilis Margaritis, Dieter Schollmeyer, Felix Hinkel, Martin Baumgarten, George Floudas, Klaus Müllen|2016|Angew.Chem.,Int.Ed.|55|3220|doi:10.1002/anie.201508249

CCDC 1831234: Experimental Crystal Structure Determination

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CCDC 1910693: Experimental Crystal Structure Determination

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CCDC 1409484: Experimental Crystal Structure Determination

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CCDC 1485994: Experimental Crystal Structure Determination

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CCDC 966732: Experimental Crystal Structure Determination

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CCDC 1415863: Experimental Crystal Structure Determination

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CCDC 1409486: Experimental Crystal Structure Determination

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CCDC 1874607: Experimental Crystal Structure Determination

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CCDC 1040031: Experimental Crystal Structure Determination

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CCDC 1520081: Experimental Crystal Structure Determination

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CCDC 926977: Experimental Crystal Structure Determination

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CCDC 907670: Experimental Crystal Structure Determination

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CCDC 897109: Experimental Crystal Structure Determination

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CCDC 1840041: Experimental Crystal Structure Determination

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CCDC 2070594: Experimental Crystal Structure Determination

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CCDC 1429063: Experimental Crystal Structure Determination

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CCDC 2077847: Experimental Crystal Structure Determination

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CCDC 2066256: Experimental Crystal Structure Determination

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CCDC 2066261: Experimental Crystal Structure Determination

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CCDC 1874606: Experimental Crystal Structure Determination

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CCDC 1910690: Experimental Crystal Structure Determination

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CCDC 977382: Experimental Crystal Structure Determination

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CCDC 937393: Experimental Crystal Structure Determination

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CCDC 1533973: Experimental Crystal Structure Determination

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CCDC 1569308: Experimental Crystal Structure Determination

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CCDC 1891336: Experimental Crystal Structure Determination

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CCDC 898755: Experimental Crystal Structure Determination

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CCDC 980571: Experimental Crystal Structure Determination

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CCDC 2047542: Experimental Crystal Structure Determination

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CCDC 1922191: Experimental Crystal Structure Determination

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CCDC 1517624: Experimental Crystal Structure Determination

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CCDC 1852851: Experimental Crystal Structure Determination

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CCDC 1866675: Experimental Crystal Structure Determination

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CCDC 1047644: Experimental Crystal Structure Determination

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CCDC 1551854: Experimental Crystal Structure Determination

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CCDC 2058115: Experimental Crystal Structure Determination

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CCDC 1476308: Experimental Crystal Structure Determination

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CCDC 1483889: Experimental Crystal Structure Determination

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CCDC 1520080: Experimental Crystal Structure Determination

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CCDC 1858288: Experimental Crystal Structure Determination

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CCDC 1920411: Experimental Crystal Structure Determination

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CCDC 1408336: Experimental Crystal Structure Determination

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CCDC 1891216: Experimental Crystal Structure Determination

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CCDC 2004421: Experimental Crystal Structure Determination

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CCDC 1816642: Experimental Crystal Structure Determination

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CCDC 1567670: Experimental Crystal Structure Determination

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CCDC 1567667: Experimental Crystal Structure Determination

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CCDC 1533972: Experimental Crystal Structure Determination

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CCDC 1862382: Experimental Crystal Structure Determination

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CCDC 895382: Experimental Crystal Structure Determination

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CCDC 980570: Experimental Crystal Structure Determination

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CCDC 1936179: Experimental Crystal Structure Determination

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CCDC 1567665: Experimental Crystal Structure Determination

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CCDC 1882077: Experimental Crystal Structure Determination

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CCDC 1894341: Experimental Crystal Structure Determination

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CCDC 2021182: Experimental Crystal Structure Determination

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CCDC 977085: Experimental Crystal Structure Determination

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CCDC 1421614: Experimental Crystal Structure Determination

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CCDC 980563: Experimental Crystal Structure Determination

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CCDC 1858294: Experimental Crystal Structure Determination

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CCDC 1520078: Experimental Crystal Structure Determination

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CCDC 980565: Experimental Crystal Structure Determination

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CCDC 1551855: Experimental Crystal Structure Determination

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CCDC 1862545: Experimental Crystal Structure Determination

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CSD 2099609: Experimental Crystal Structure Determination

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CCDC 1979131: Experimental Crystal Structure Determination

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CCDC 1428696: Experimental Crystal Structure Determination

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CCDC 1936182: Experimental Crystal Structure Determination

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CCDC 1421615: Experimental Crystal Structure Determination

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CCDC 1047645: Experimental Crystal Structure Determination

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CCDC 902177: Experimental Crystal Structure Determination

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CCDC 2021698: Experimental Crystal Structure Determination

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CCDC 966311: Experimental Crystal Structure Determination

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CCDC 897110: Experimental Crystal Structure Determination

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CCDC 2076144: Experimental Crystal Structure Determination

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CCDC 1485996: Experimental Crystal Structure Determination

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CCDC 1520082: Experimental Crystal Structure Determination

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CCDC 1998477: Experimental Crystal Structure Determination

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CCDC 2021692: Experimental Crystal Structure Determination

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CCDC 902179: Experimental Crystal Structure Determination

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CCDC 1532063: Experimental Crystal Structure Determination

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CCDC 1862543: Experimental Crystal Structure Determination

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CCDC 2032478: Experimental Crystal Structure Determination

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CCDC 1857365: Experimental Crystal Structure Determination

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CCDC 1998478: Experimental Crystal Structure Determination

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CCDC 1039421: Experimental Crystal Structure Determination

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CCDC 897106: Experimental Crystal Structure Determination

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CCDC 1581941: Experimental Crystal Structure Determination

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CCDC 1542681: Experimental Crystal Structure Determination

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CCDC 1910691: Experimental Crystal Structure Determination

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CCDC 902174: Experimental Crystal Structure Determination

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CCDC 1039422: Experimental Crystal Structure Determination

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CCDC 1936180: Experimental Crystal Structure Determination

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CCDC 1903303: Experimental Crystal Structure Determination

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CCDC 1857364: Experimental Crystal Structure Determination

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CCDC 1872281: Experimental Crystal Structure Determination

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CCDC 2047540: Experimental Crystal Structure Determination

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CCDC 1862542: Experimental Crystal Structure Determination

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CCDC 1914718: Experimental Crystal Structure Determination

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CCDC 902178: Experimental Crystal Structure Determination

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CCDC 1998475: Experimental Crystal Structure Determination

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CCDC 980569: Experimental Crystal Structure Determination

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CCDC 1899693: Experimental Crystal Structure Determination

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CCDC 2004419: Experimental Crystal Structure Determination

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CCDC 1533971: Experimental Crystal Structure Determination

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CCDC 1421617: Experimental Crystal Structure Determination

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CCDC 902175: Experimental Crystal Structure Determination

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CCDC 1484250: Experimental Crystal Structure Determination

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CCDC 920035: Experimental Crystal Structure Determination

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CCDC 1858697: Experimental Crystal Structure Determination

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CCDC 1533733: Experimental Crystal Structure Determination

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CCDC 1428732: Experimental Crystal Structure Determination

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CSD 2099612: Experimental Crystal Structure Determination

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CCDC 1589070: Experimental Crystal Structure Determination

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CCDC 1882075: Experimental Crystal Structure Determination

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CCDC 1533970: Experimental Crystal Structure Determination

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CCDC 1472204: Experimental Crystal Structure Determination

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CCDC 1454207: Experimental Crystal Structure Determination

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CCDC 2047541: Experimental Crystal Structure Determination

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CCDC 2058017: Experimental Crystal Structure Determination

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CCDC 1476309: Experimental Crystal Structure Determination

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CCDC 998456: Experimental Crystal Structure Determination

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CCDC 1824231: Experimental Crystal Structure Determination

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CCDC 985005: Experimental Crystal Structure Determination

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CCDC 1517625: Experimental Crystal Structure Determination

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CCDC 1483890: Experimental Crystal Structure Determination

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CCDC 1858297: Experimental Crystal Structure Determination

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CCDC 985006: Experimental Crystal Structure Determination

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CCDC 1408347: Experimental Crystal Structure Determination

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CCDC 1483888: Experimental Crystal Structure Determination

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CCDC 1415860: Experimental Crystal Structure Determination

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CCDC 1415861: Experimental Crystal Structure Determination

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CCDC 2066260: Experimental Crystal Structure Determination

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CCDC 977386: Experimental Crystal Structure Determination

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CCDC 977380: Experimental Crystal Structure Determination

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CCDC 1998476: Experimental Crystal Structure Determination

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CCDC 1428694: Experimental Crystal Structure Determination

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CCDC 980564: Experimental Crystal Structure Determination

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CCDC 1489370: Experimental Crystal Structure Determination

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CCDC 1025809: Experimental Crystal Structure Determination

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CCDC 1496144: Experimental Crystal Structure Determination

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CCDC 1910694: Experimental Crystal Structure Determination

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CCDC 2066257: Experimental Crystal Structure Determination

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CCDC 1948965: Experimental Crystal Structure Determination

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CSD 2099610: Experimental Crystal Structure Determination

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CCDC 1894340: Experimental Crystal Structure Determination

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CCDC 2049251: Experimental Crystal Structure Determination

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CCDC 977406: Experimental Crystal Structure Determination

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CCDC 1920412: Experimental Crystal Structure Determination

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CCDC 1910692: Experimental Crystal Structure Determination

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CCDC 977392: Experimental Crystal Structure Determination

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CCDC 1567666: Experimental Crystal Structure Determination

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CCDC 1561793: Experimental Crystal Structure Determination

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CCDC 2000869: Experimental Crystal Structure Determination

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CCDC 1427947: Experimental Crystal Structure Determination

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CCDC 1922189: Experimental Crystal Structure Determination

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CCDC 1910695: Experimental Crystal Structure Determination

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CCDC 980568: Experimental Crystal Structure Determination

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CCDC 1882076: Experimental Crystal Structure Determination

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CCDC 2058018: Experimental Crystal Structure Determination

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CCDC 1858291: Experimental Crystal Structure Determination

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CCDC 1427184: Experimental Crystal Structure Determination

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CCDC 1008816: Experimental Crystal Structure Determination

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CCDC 1858296: Experimental Crystal Structure Determination

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CCDC 2004420: Experimental Crystal Structure Determination

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CCDC 1862544: Experimental Crystal Structure Determination

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CCDC 1988067: Experimental Crystal Structure Determination

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CCDC 1008819: Experimental Crystal Structure Determination

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CCDC 907672: Experimental Crystal Structure Determination

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CCDC 1874603: Experimental Crystal Structure Determination

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CCDC 1542680: Experimental Crystal Structure Determination

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CCDC 1484249: Experimental Crystal Structure Determination

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CCDC 1561794: Experimental Crystal Structure Determination

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CCDC 1882073: Experimental Crystal Structure Determination

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CCDC 1831233: Experimental Crystal Structure Determination

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CCDC 1428734: Experimental Crystal Structure Determination

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CCDC 1910698: Experimental Crystal Structure Determination

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CCDC 1816643: Experimental Crystal Structure Determination

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CCDC 1484253: Experimental Crystal Structure Determination

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CCDC 1561792: Experimental Crystal Structure Determination

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CCDC 1814647: Experimental Crystal Structure Determination

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CCDC 1841752: Experimental Crystal Structure Determination

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CCDC 1936181: Experimental Crystal Structure Determination

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CCDC 1583576: Experimental Crystal Structure Determination

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CCDC 1485995: Experimental Crystal Structure Determination

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CCDC 1846985: Experimental Crystal Structure Determination

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CCDC 1945339: Experimental Crystal Structure Determination

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CCDC 2000868: Experimental Crystal Structure Determination

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CCDC 1008820: Experimental Crystal Structure Determination

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CCDC 1047647: Experimental Crystal Structure Determination

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CCDC 902176: Experimental Crystal Structure Determination

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CCDC 1846986: Experimental Crystal Structure Determination

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CCDC 1428695: Experimental Crystal Structure Determination

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CCDC 1988057: Experimental Crystal Structure Determination

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CCDC 1922192: Experimental Crystal Structure Determination

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CCDC 902683: Experimental Crystal Structure Determination

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CCDC 980566: Experimental Crystal Structure Determination

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CCDC 2021183: Experimental Crystal Structure Determination

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CCDC 1896228: Experimental Crystal Structure Determination

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CCDC 1917242: Experimental Crystal Structure Determination

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CCDC 1891217: Experimental Crystal Structure Determination

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CCDC 1920410: Experimental Crystal Structure Determination

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CCDC 1567668: Experimental Crystal Structure Determination

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CCDC 895383: Experimental Crystal Structure Determination

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CCDC 2042388: Experimental Crystal Structure Determination

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CCDC 1894339: Experimental Crystal Structure Determination

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CCDC 1831232: Experimental Crystal Structure Determination

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CCDC 1567669: Experimental Crystal Structure Determination

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CCDC 1874604: Experimental Crystal Structure Determination

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CCDC 1472205: Experimental Crystal Structure Determination

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CCDC 2076145: Experimental Crystal Structure Determination

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CCDC 973932: Experimental Crystal Structure Determination

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CCDC 2066259: Experimental Crystal Structure Determination

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CCDC 1533734: Experimental Crystal Structure Determination

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CCDC 1858292: Experimental Crystal Structure Determination

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CCDC 1409487: Experimental Crystal Structure Determination

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CCDC 1976461: Experimental Crystal Structure Determination

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CCDC 1879738: Experimental Crystal Structure Determination

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CCDC 1848515: Experimental Crystal Structure Determination

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CCDC 1837456: Experimental Crystal Structure Determination

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CCDC 1893173: Experimental Crystal Structure Determination

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CCDC 1910697: Experimental Crystal Structure Determination

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CCDC 1922190: Experimental Crystal Structure Determination

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CCDC 1831236: Experimental Crystal Structure Determination

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CCDC 1589072: Experimental Crystal Structure Determination

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CCDC 1585828: Experimental Crystal Structure Determination

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CCDC 1569307: Experimental Crystal Structure Determination

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CCDC 897107: Experimental Crystal Structure Determination

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CCDC 1428733: Experimental Crystal Structure Determination

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CCDC 1945340: Experimental Crystal Structure Determination

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CCDC 1858290: Experimental Crystal Structure Determination

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CCDC 973931: Experimental Crystal Structure Determination

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CCDC 2049252: Experimental Crystal Structure Determination

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CCDC 942767: Experimental Crystal Structure Determination

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CCDC 1484252: Experimental Crystal Structure Determination

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CCDC 973930: Experimental Crystal Structure Determination

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CCDC 2066258: Experimental Crystal Structure Determination

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CCDC 1814646: Experimental Crystal Structure Determination

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CCDC 977454: Experimental Crystal Structure Determination

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CCDC 1484251: Experimental Crystal Structure Determination

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CCDC 1882074: Experimental Crystal Structure Determination

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CCDC 1520079: Experimental Crystal Structure Determination

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CCDC 1831235: Experimental Crystal Structure Determination

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CCDC 1421616: Experimental Crystal Structure Determination

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CCDC 966733: Experimental Crystal Structure Determination

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CCDC 1530094: Experimental Crystal Structure Determination

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CCDC 1858293: Experimental Crystal Structure Determination

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CCDC 1872280: Experimental Crystal Structure Determination

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CCDC 1542682: Experimental Crystal Structure Determination

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CCDC 1866690: Experimental Crystal Structure Determination

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CCDC 1415862: Experimental Crystal Structure Determination

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CCDC 1589071: Experimental Crystal Structure Determination

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CCDC 1008818: Experimental Crystal Structure Determination

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CCDC 1922188: Experimental Crystal Structure Determination

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CCDC 907671: Experimental Crystal Structure Determination

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CCDC 1852850: Experimental Crystal Structure Determination

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CSD 2099611: Experimental Crystal Structure Determination

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CCDC 926976: Experimental Crystal Structure Determination

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CCDC 2002425: Experimental Crystal Structure Determination

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CCDC 1008817: Experimental Crystal Structure Determination

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CCDC 1858295: Experimental Crystal Structure Determination

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CCDC 816417: Experimental Crystal Structure Determination

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CCDC 977381: Experimental Crystal Structure Determination

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CCDC 1814648: Experimental Crystal Structure Determination

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CCDC 1409488: Experimental Crystal Structure Determination

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CCDC 1427185: Experimental Crystal Structure Determination

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CCDC 1419863: Experimental Crystal Structure Determination

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CCDC 1047646: Experimental Crystal Structure Determination

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CCDC 1409485: Experimental Crystal Structure Determination

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CCDC 1882078: Experimental Crystal Structure Determination

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CCDC 1521512: Experimental Crystal Structure Determination

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CCDC 1484248: Experimental Crystal Structure Determination

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CCDC 1485997: Experimental Crystal Structure Determination

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CCDC 966309: Experimental Crystal Structure Determination

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CCDC 1946099: Experimental Crystal Structure Determination

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CCDC 1010016: Experimental Crystal Structure Determination

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CCDC 998455: Experimental Crystal Structure Determination

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CCDC 1986341: Experimental Crystal Structure Determination

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CCDC 980567: Experimental Crystal Structure Determination

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CCDC 1910696: Experimental Crystal Structure Determination

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CCDC 966310: Experimental Crystal Structure Determination

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CCDC 1858698: Experimental Crystal Structure Determination

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CCDC 1841753: Experimental Crystal Structure Determination

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CCDC 1858289: Experimental Crystal Structure Determination

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CCDC 1840040: Experimental Crystal Structure Determination

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