0000000001306206

AUTHOR

Sandra Kaabel

showing 32 related works from this author

CaCl2, Bisoxazoline, and Malonate: A Protocol for an Asymmetric Michael Reaction

2015

A mild protocol for the asymmetric Michael addition of dimethyl malonate to various α,β-unsaturated carbonyl compounds was developed. The salient feature of this methodology is that a cheap and environmentally friendly Lewis acid, CaCl2, was used as a catalyst. An aminoindanol- and pyridine-derived ligand provided in the presence of CaCl2 Michael adducts in moderate to high enantioselectivities. The scope of the reaction was demonstrated.

Bisoxazolineinorganic chemicalsAminoindanol010405 organic chemistryChemistryLigandOrganic ChemistryMalonateCaCl2macromolecular substances010402 general chemistrybehavioral disciplines and activities01 natural sciencesDimethyl malonatehumanities0104 chemical sciencesCatalysisAdductchemistry.chemical_compoundMalonateMichael reactionOrganic chemistryLewis acids and basesta116The Journal of Organic Chemistry
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Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution

2017

A novel eight-membered macrocycle of the hemicucurbit[n]uril family, chiral (all-R)-cyclohexanohemicucurbit[8]uril (cycHC[8]) binds anions in a purely protic solvent with remarkable selectivity. The cycHC[8] portals open and close to fully encapsulate anions in a 1 : 1 ratio, resembling a molecular Pac-Man™. Comprehensive gas, solution and solid phase studies prove that the binding is governed by the size, shape and charge distribution of the bound anion. Gas phase studies show an order of SbF6− ≈ PF6− > ReO4− > ClO4− > SCN− > BF4− > HSO4− > CF3SO3− for anion complexation strength. An extensive crystallographic study reveals the preferred orientations of the anions within the octahedral cav…

macrocyclesanion receptorsvalikoivuushemicucurbituril
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Formation and trapping of the thermodynamically unfavoured inverted-hemicucurbit[6]uril

2019

Amplification of a thermodynamically unfavoured macrocyclic product through the directed shift of the equilibrium between dynamic covalent chemistry library members is difficult to achieve. We show for the first time that during condensation of formaldehyde and cis-N,N'-cyclohexa-1,2-diylurea formation of inverted-cis-cyclohexanohemicucurbit[6]uril (i-cis-cycHC[6]) can be induced at the expense of thermodynamically favoured cis-cyclohexanohemicucurbit[6]uril (cis-cycHC[6]). The formation of i-cis-cycHC[6] is enhanced in low concentration of the templating chloride anion and suppressed in excess of this template. We found that reaction selectivity is governed by the solution-based template-a…

010405 organic chemistryPrecipitation (chemistry)Metals and AlloysDiastereomerGeneral ChemistryTrapping010402 general chemistry01 natural sciencesCatalysis0104 chemical sciencesSurfaces Coatings and FilmsElectronic Optical and Magnetic Materialschemistry.chemical_compoundchemistryComputational chemistryYield (chemistry)Materials ChemistryCeramics and CompositesTrifluoroacetic acidDynamic combinatorial chemistrySelectivityBinding affinitiesChemical Communications
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Synthesis and Characterisation of Chiral Triazole-Based Halogen-Bond Donors: Halogen Bonds in the Solid State and in Solution

2017

A general platform for the synthesis of various chiral halogen-bond (XB) donors based on the triazole core and the characterisation of factors that influence the strength of the halogen bond in the solid state and in solution are reported. The characterisation of XB donors in the solid state by X-ray crystallography and in solution by 1H NMR titration can be used to aid the design of new XB donors. We describe the first example of a XB between iodotriazoles and thioureas in solution. In addition, the enantiodiscrimination of acceptors in solution through halogen-bond participation is described.

TriazoleSolid-state010402 general chemistry01 natural scienceschemical bondsCatalysiskemialliset sidoksetchemistry.chemical_compoundNMR spectroscopyhalogensOrganic chemistryNMR-spektroskopiata116x-ray crystallographykemiallinen synteesiHalogen bondhalogeenit010405 organic chemistryOrganic ChemistryGeneral ChemistryCombinatorial chemistry0104 chemical scienceschemistryHalogenTitrationröntgenkristallografiachemical synthesisChemistry - A European Journal
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Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution

2017

A novel eight-membered macrocycle of the hemicucurbit[n]uril family, chiral (all-R)-cyclohexanohemicucurbit[8]uril (cycHC[8]) binds anions in a purely protic solvent with remarkable selectivity. The cycHC[8] portals open and close to fully encapsulate anions in a 1 : 1 ratio, resembling a molecular Pac-Man™. Comprehensive gas, solution and solid phase studies prove that the binding is governed by the size, shape and charge distribution of the bound anion. Gas phase studies show an order of SbF6− ≈ PF6− > ReO4− > ClO4− > SCN− > BF4− > HSO4− > CF3SO3− for anion complexation strength. An extensive crystallographic study reveals the preferred orientations of the anions within the octahedral cav…

anion receptors010405 organic chemistryStereochemistryselectivityCharge densityIsothermal titration calorimetryGeneral Chemistryhemicucurbituril010402 general chemistry01 natural sciences0104 chemical sciencesIonSolventCrystallographychemistry.chemical_compoundmacrocyclesOctahedronchemistryPhase (matter)Selectivityta116Protic solventChemical Science
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Template-controlled synthesis of chiral cyclohexylhemicucurbit[8]uril

2015

Enantiomerically pure cyclohexylhemicucurbit[8]uril (cycHC[8]), possessing a barrel-shaped cavity, has been prepared in high yield on a gram scale from either (R,R,N,N')-cyclohex-1,2-diylurea and formaldehyde or cycHC[6]. In either case, a dynamic covalent library is first generated from which the desired cycHC can be amplified using a suitable anion template.

Metals and AlloysFormaldehydeGeneral Chemistryhost-guest sytemscycHC synthesisCombinatorial chemistryCatalysisSurfaces Coatings and FilmsElectronic Optical and Magnetic Materialschemistry.chemical_compoundchemistryCovalent bondYield (chemistry)Materials ChemistryCeramics and Compositesta116Chemical Communications
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Asymmetric Organocatalytic Wittig [2,3]-Rearrangement of Oxindoles

2016

A highly enantioselective organocatalytic [2,3]-rearrangement of oxindole derivatives is presented. The reaction was catalyzed by squaramide, and this provides access to 3-hydroxy 3-substituted oxindoles in high enantiomeric purities.

asymmetric organocatalytic wittigIndolesStereoisomerism010402 general chemistry01 natural sciencesBiochemistryCatalysisCatalysischemistry.chemical_compoundCombinatorial Chemistry TechniquesOrganic chemistryOxindolePhysical and Theoretical Chemistryta116Molecular Structure010405 organic chemistryOrganic ChemistrySquaramideEnantioselective synthesisStereoisomerismAmidesOxindoles0104 chemical scienceschemistryWittig reactionEnantiomerOrganic Letters
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Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution† †Electronic supplementary information (ESI) avai…

2016

Chiral (all-R)-cyclohexanohemicucurbit[8]uril binds anions in a 1 : 1 ratio in pure methanol like a molecular Pac-Man™ with remarkable selectivity based on the size, shape and charge distribution of the anion.

ChemistryChemical Science
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Asymmetric Organocatalytic Michael Addition–Cyclization Cascade of Cyclopentane-1,2-dione with Substituted α,β-Unsaturated Aldehydes

2017

An asymmetric organocatalytic Michael addition–cyclization cascade reaction has been developed using cyclopentane-1,2-dione as a Michael donor and α,β-unsaturated aldehydes as Michael acceptors. Bicyclic hemiacetals were obtained in excellent yields and enantioselectivities. On the basis of the results, a one-pot reaction has been developed to obtain chiral 3-substituted cyclopentane-1,2-diones and substituted dihydropyrans in good yields and excellent enantioselectivity.

Bicyclic molecule010405 organic chemistryDihydropyranOrganic Chemistry010402 general chemistry01 natural sciencesCatalysis0104 chemical scienceschemistry.chemical_compoundchemistryCascade reactionCascadeOrganocatalysisMichael reactionOrganic chemistryCyclopentaneSynthesis
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CCDC 1569570: Experimental Crystal Structure Determination

2019

Related Article: Elena Prigorchenko, Sandra Kaabel, Triin Narva, Anastassia Baškir, Maria Fomitšenko, Jasper Adamson, Ivar Järving, Kari Rissanen, Toomas Tamm, Riina Aav|2019|Chem.Commun.|55|9307|doi:10.1039/C9CC04990H

Space GroupCrystallography1310121921283037394648-dodecaazatridecacyclo[46.6.1.1310.11219.12128.13037.13946.049.01318.02227.03136.04045.04954]hexacontane-555657585960-hexone deuterochloroform solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1514740: Experimental Crystal Structure Determination

2016

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

Space GroupCrystallographytetra-n-butylphosphonium cycloocta(1-methylene-(octahydro-2H-benzimidazol-2-one-3-yl)) periodate methanol solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1056977: Experimental Crystal Structure Determination

2015

Related Article: Kristin Lippur , Sandra Kaabel , Ivar Järving , Kari Rissanen , and Tõnis Kanger|2015|J.Org.Chem.|80|6336|doi:10.1021/acs.joc.5b00769

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D CoordinatesDimethyl (S)-2-(1-(4-nitrophenyl)-14-dioxopentan-3-yl)malonate
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CCDC 1514737: Experimental Crystal Structure Determination

2016

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinatestetra-n-butylphosphonium cycloocta(1-methylene-(octahydro-2H-benzimidazol-2-one-3-yl)) hexafluoroantimonate methanol solvate
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CCDC 1522088: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

9-(4-(35-bis(trifluoromethyl)phenyl)-5-iodo-3-methyl-1H-123-triazol-3-ium-1-yl)-6'-methoxy-11'-dimethylcinchonan-11'-diium tris(trifluoromethanesulfonate) methanol solvateSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1522089: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

Space GroupCrystallography5-(35-bis(trifluoromethyl)phenyl)-4-iodo-1-methyl-3-(1-phenylethyl)-1H-123-triazol-3-ium tetrafluoroborate propan-2-ol solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1522081: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

Space GroupCrystallography9-(4-(35-bis(trifluoromethyl)phenyl)-5-iodo-1H-123-triazol-1-yl)-6'-methoxycinchonanCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1447017: Experimental Crystal Structure Determination

2016

Related Article: Maksim Ošeka, Mariliis Kimm, Sandra Kaabel, Ivar Järving, Kari Rissanen, and Tõnis Kanger|2016|Org.Lett.|18|1358|doi:10.1021/acs.orglett.6b00291

Space GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates3-(1-(4-chlorophenyl)prop-2-en-1-yl)-3-hydroxy-1-(4-methylbenzyl)-13-dihydro-2H-indol-2-one
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CCDC 1522087: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

Space GroupCrystallography5-(35-bis(trifluoromethyl)phenyl)-4-iodo-3-(2-methoxy-2-oxo-1-phenylethyl)-1-methyl-1H-123-triazol-3-ium trifluoromethanesulfonateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1522085: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters4-(35-bis(trifluoromethyl)phenyl)-5-chloro-3-methyl-1-(1-phenylethyl)-1H-123-triazol-3-ium trifluoromethanesulfonateExperimental 3D Coordinates
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CCDC 1447018: Experimental Crystal Structure Determination

2016

Related Article: Maksim Ošeka, Mariliis Kimm, Sandra Kaabel, Ivar Järving, Kari Rissanen, and Tõnis Kanger|2016|Org.Lett.|18|1358|doi:10.1021/acs.orglett.6b00291

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters7-fluoro-3-hydroxy-1-(4-methylbenzyl)-3-(1-phenylprop-2-en-1-yl)-13-dihydro-2H-indol-2-oneExperimental 3D Coordinates
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CCDC 1514738: Experimental Crystal Structure Determination

2016

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

Space GroupCrystallographytetra-n-butylammonium cycloocta(1-methylene-(octahydro-2H-benzimidazol-2-one-3-yl)) tetrafluoroborate methanol solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1514739: Experimental Crystal Structure Determination

2016

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

Space GroupCrystallographytetra-n-butylammonium cycloocta(1-methylene-(octahydro-2H-benzimidazol-2-one-3-yl)) oxido-trioxo-rhenium(vii) methanol solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1522082: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters99'-(13-phenylenebis(5-iodo-1H-123-triazole-41-diyl))bis(6'-methoxycinchonan) tetrachloromethane solvateExperimental 3D Coordinates
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Chiral hemicucurbit[8]uril as an anion receptor: selectivity to size, shape and charge distribution

2023

Chiral (all-R)-cyclohexanohemicucurbit[8]uril binds anions in a 1 : 1 ratio in pure methanol like a molecular Pac-Man™ with remarkable selectivity based on the size, shape and charge distribution of the anion.

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CCDC 1522086: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

Space GroupCrystallographyCrystal SystemCrystal Structure5-iodo-3-methyl-1-(1-phenylethyl)-4-[4-(trifluoromethyl)phenyl]-1H-123-triazol-3-ium trifluoromethanesulfonateCell ParametersExperimental 3D Coordinates
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CCDC 1522080: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

5-iodo-4-phenyl-1-(1-phenylethyl)-1H-123-triazoleSpace GroupCrystallographyCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1522079: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

Space GroupCrystallography4-(35-bis(trifluoromethyl)phenyl)-5-iodo-1-(1-phenylethyl)-1H-123-triazoleCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1522084: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters4-(35-bis(trifluoromethyl)phenyl)-5-bromo-3-methyl-1-(1-phenylethyl)-1H-123-triazol-3-ium trifluoromethanesulfonateExperimental 3D Coordinates
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CCDC 1522083: Experimental Crystal Structure Determination

2017

Related Article: Mikk Kaasik, Sandra Kaabel, Kadri Kriis, Ivar Järving, Riina Aav, Kari Rissanen, Tönis Kanger|2017|Chem.-Eur.J.|23|7337|doi:10.1002/chem.201700618

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameters4-(35-bis(trifluoromethyl)phenyl)-5-iodo-3-methyl-1-(1-phenylethyl)-1H-123-triazol-3-ium trifluoromethanesulfonateExperimental 3D Coordinates
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CCDC 1521388: Experimental Crystal Structure Determination

2016

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

Space GroupCrystallographyCrystal SystemCrystal StructureCell Parameterstetra-n-butylammonium (all-R)-cyclohexanohemicucurbit[8]uril perchlorate methanol solvateExperimental 3D Coordinates
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CCDC 1514736: Experimental Crystal Structure Determination

2016

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

Space GroupCrystallographytetra-n-butylammonium cycloocta(1-methylene-(octahydro-2H-benzimidazol-2-one-3-yl)) hexafluorophosphate methanol solvateCrystal SystemCrystal StructureCell ParametersExperimental 3D Coordinates
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CCDC 1514741: Experimental Crystal Structure Determination

2016

Related Article: Sandra Kaabel, Jasper Adamson, Filip Topić, Anniina Kiesilä, Elina Kalenius, Mario Öeren, Mart Reimund, Elena Prigorchenko, Aivar Lõokene, Hans J. Reich, Kari Rissanen, Riina Aav|2017|Chemical Science|8|2184|doi:10.1039/C6SC05058A

Space GroupCrystallographyCrystal SystemCrystal Structuretetra-n-butylammonium cycloocta(1-methylene-(octahydro-2H-benzimidazol-2-one-3-yl)) trifluoromethanesulfonate methanol solvateCell ParametersExperimental 3D Coordinates
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