Developments in the dehydrogenative electrochemical synthesis of 3,3′,5,5′-tetramethyl-2,2′-biphenol

Abstract The symmetric biphenol 3,3′,5,5′‐tetramethyl‐2,2′‐biphenol is a well‐known ligand building block and is used in transition‐metal catalysis. In the literature, there are several synthetic routes for the preparation of this exceptional molecule. Herein, the focus is on the sustainable electrochemical synthesis of 3,3′,5,5′‐tetramethyl‐2,2′‐biphenol. A brief overview of the developmental history of this inconspicuous molecule, which is of great interest for technical applications, but has many challenges for its synthesis, is provided. The electro‐organic method is a powerful, sustainable, and efficient alternative to conventional synthesis to obtain this symmetric biphenol up to the …

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.

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)

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…

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

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

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…

Scalable and Selective Preparation of 3,3′,5,5′-Tetramethyl-2,2′-biphenol

Biphenols are indispensable building blocks in ligand systems for organic catalysis. 3,3′5,5′-Tetramethyl-2,2′-biphenol is a particular versatile motif in different catalytic systems. We developed an easy to perform and scalable process to give access to large quantities of this important building block by the use of selenium dioxide, a common and readily available oxidizer.

Regioselektive metall‐ und reagenzfreie Arylierung von Benzothiophenen durch dehydrierende Elektrosynthese

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.

Synthesis of Optically Pure Arylamine Derivatives by Using the Bucherer Reaction

The Bucherer reaction is a common pathway for the conversion of 1- and 2-naphthols into the corresponding 1- or 2-naphthylamines, respectively. Mostly, only singular examples for its preparative use are reported since this particular transformation seems to be very sensitive to the reaction conditions. By choosing different phenolic substrates and chiral amines, we were able to prepare a broad scope of optically pure arylamines using this type of reaction. In contrast to alternative methods forming C−N aryl bonds such as Buchwald-Hartwig or Chan-Lam cross-coupling reactions, no palladium or copper catalysts are required. The use of water as solvent and the easily available starting material…

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.

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

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…

Metal‐ and Reagent‐Free Anodic Dehydrogenative Cross‐Coupling of Naphthylamines with Phenols

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

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).

A Decade of Electrochemical Dehydrogenative C,C-Coupling of Aryls.

The importance of sustainable and green synthetic protocols for the synthesis of fine chemicals has rapidly increased during the last decades in an effort to reduce the use of fossil fuels and other finite resources. The replacement of common reagents by electricity provides a cost- and atom-efficient, environmentally friendly, and inherently safe access to novel synthetic routes. The selective formation of carbon-carbon bonds between two distinct substrates is a crucial tool in organic chemistry. This fundamental transformation enables access to a broad variety of complex molecular architectures. In particular, the aryl-aryl bond formation has high significance for the preparation of organ…

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)

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

Direct Anodic Dehydrogenative Cross- and Homo-Coupling of Formanilides

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.

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…

6,6′-[(3,3′-Di-tert-butyl-5,5′-dimethoxy-1,1′-biphenyl-2,2′-diyl)bis(oxy)]bis(dibenzo[d,f][1,3,2]dioxaphosphepine) benzene monosolvate

The crystal structure of the benzene monosolvate of the well known organic diphosphite ligand BIPHEPHOS, C46H44O8P2·C6H6, is reported for the first time. Single crystals of BIPHEPHOS were obtained from a benzene solution after layering with n-heptane at room temperature. One specific property of this type of diphosphite structure is the twisting of the biphenyl units. In the crystal, C—H...π contacts and π–π stacking interactions [centroid-to-centroid distance = 3.8941 (15) Å] are observed.

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…

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

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.

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

Electro-organic Synthesis as a Sustainable Alternative for Dehydrogenative Cross-Coupling of Phenols and Naphthols

The dehydrogenative cross-coupling of phenols and naphthols can be achieved by several oxidative methods. However, the key is the use of fluorinated alcohols such as 1,1,1,3,3,3-hexafluoroisopropanol. The direct application of electricity represents an alternative synthetic approach, which is superior to other oxidizers (e.g., peroxides). The method is sustainable, inherently safe, and easily scalable.

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…

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)

Dehydrogenative Anodic Cyanation Reaction of Phenols in Benzylic Positions

Metall- und reagensfreie hochselektive anodische Kreuzkupplung von Phenolen

Front Cover: Metal‐ and Reagent‐Free Anodic Dehydrogenative Cross‐Coupling of Naphthylamines with Phenols (ChemElectroChem 9/2018)

Electrochemical Synthesis of 2-Hydroxy-para-terphenyls by Dehydrogenative Anodic C–C Cross-Coupling Reaction

The anodic C–C cross-coupling reaction provides fast access to a wide range of bi- and terarylic scaffolds by electrochemically mediated arylation reactions. Herein, a metal- and reagent-free electrosynthetic protocol for the synthesis of nonsymmetrical 2-hydroxy-para-teraryl derivatives is presented for the first time. It is scalable, easy to conduct, and allows the use of a broad variety of different functional groups.

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

Unexpected high robustness of electrochemical cross-coupling for a broad range of current density

Solvent effect enables electrosynthesis of organic compounds with strong variation of electric current at constant efficacy.

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

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

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

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 …

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.

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…

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.

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.

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

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…

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.

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…

Supporting-Electrolyte-Free and Scalable Flow Process for the Electrochemical Synthesis of 3,3′,5,5′-Tetramethyl-2,2′-biphenol

The most efficient electrochemical synthesis of 3,3′,5,5′-tetramethyl-2,2′-biphenol by dehydrogenative coupling is reported. The electrolysis is performed supporting-electrolyte-free in 1,1,1,3,3,3...

Electrosynthesis of 3,3′,5,5’-tetramethyl-2,2′-biphenol in flow

Abstract3,3′,5,5’-Tetramethyl-2,2′-biphenol is well known as an outstanding building block for ligands in transition-metal catalysis and is therefore of particular industrial interest. The electro-organic method is a powerful, sustainable, and efficient alternative to conventional synthetic approaches to obtain symmetric and non-symmetric biphenols. Here, we report the successive scale-up of the dehydrogenative anodic homocoupling of 2,4-dimethylphenol (4) from laboratory scale to the technically relevant scale in highly modular narrow gap flow electrolysis cells. The electrosynthesis was optimized in a manner that allows it to be easily adopted to different scales such as laboratory, semit…

CCDC 1485994: Experimental Crystal Structure Determination

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CCDC 1840041: Experimental Crystal Structure Determination

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CCDC 1429063: Experimental Crystal Structure Determination

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CCDC 1569308: Experimental Crystal Structure Determination

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CCDC 980571: Experimental Crystal Structure Determination

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CCDC 1517624: Experimental Crystal Structure Determination

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CCDC 1476308: Experimental Crystal Structure Determination

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CCDC 1920411: Experimental Crystal Structure Determination

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CCDC 1891216: Experimental Crystal Structure Determination

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CCDC 980570: Experimental Crystal Structure Determination

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CCDC 980563: Experimental Crystal Structure Determination

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CCDC 980565: Experimental Crystal Structure Determination

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CCDC 1485996: 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 1589070: Experimental Crystal Structure Determination

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CCDC 1476309: Experimental Crystal Structure Determination

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CCDC 1517625: Experimental Crystal Structure Determination

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CCDC 980564: Experimental Crystal Structure Determination

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CCDC 1920412: Experimental Crystal Structure Determination

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CCDC 980568: Experimental Crystal Structure Determination

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CCDC 1008816: Experimental Crystal Structure Determination

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CCDC 1008819: 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 1008820: Experimental Crystal Structure Determination

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CCDC 1846986: Experimental Crystal Structure Determination

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