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4,4′-Dimeth­oxy-2,2′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-diyl]bis(methyl­ene)}diphenol

The title compound, C(23)H(30)N(2)O(4), is a Mannich base useful for studying the effect of an electron-donating phenol substituent on intra­molecular hydrogen bonding. In the mol­ecular structure, the cyclo­hexane ring adopts a chair conformation and the five-membered ring has a twisted envelope co...

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Autores principales: Rivera, Augusto, Quiroga, Diego, Ríos-Motta, Jaime, Fejfarová, Karla, Dušek, Michal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3200725/
https://www.ncbi.nlm.nih.gov/pubmed/22065834
http://dx.doi.org/10.1107/S1600536811031436
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author Rivera, Augusto
Quiroga, Diego
Ríos-Motta, Jaime
Fejfarová, Karla
Dušek, Michal
author_facet Rivera, Augusto
Quiroga, Diego
Ríos-Motta, Jaime
Fejfarová, Karla
Dušek, Michal
author_sort Rivera, Augusto
collection PubMed
description The title compound, C(23)H(30)N(2)O(4), is a Mannich base useful for studying the effect of an electron-donating phenol substituent on intra­molecular hydrogen bonding. In the mol­ecular structure, the cyclo­hexane ring adopts a chair conformation and the five-membered ring has a twisted envelope conformation. Each meth­oxy group is oriented in the same plane of the respective aromatic ring, showing torsion angles below 11.8 (3)° and bond angles between the meth­oxy group and the aromatic ring of 116.6 (2) and 116.6 (1)°. The structure shows inter­actions between two the N atoms of the heterocyclic ring and the hy­droxy groups by intra­molecular O—H⋯N hydrogen-bonding inter­actions. In the crystal, C—H⋯O inter­actions are observed. The crystal studied was a racemic mixture of RR and SS enanti­omers.
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spelling pubmed-32007252011-11-06 4,4′-Dimeth­oxy-2,2′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-diyl]bis(methyl­ene)}diphenol Rivera, Augusto Quiroga, Diego Ríos-Motta, Jaime Fejfarová, Karla Dušek, Michal Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(23)H(30)N(2)O(4), is a Mannich base useful for studying the effect of an electron-donating phenol substituent on intra­molecular hydrogen bonding. In the mol­ecular structure, the cyclo­hexane ring adopts a chair conformation and the five-membered ring has a twisted envelope conformation. Each meth­oxy group is oriented in the same plane of the respective aromatic ring, showing torsion angles below 11.8 (3)° and bond angles between the meth­oxy group and the aromatic ring of 116.6 (2) and 116.6 (1)°. The structure shows inter­actions between two the N atoms of the heterocyclic ring and the hy­droxy groups by intra­molecular O—H⋯N hydrogen-bonding inter­actions. In the crystal, C—H⋯O inter­actions are observed. The crystal studied was a racemic mixture of RR and SS enanti­omers. International Union of Crystallography 2011-08-11 /pmc/articles/PMC3200725/ /pubmed/22065834 http://dx.doi.org/10.1107/S1600536811031436 Text en © Rivera et al. 2011 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Rivera, Augusto
Quiroga, Diego
Ríos-Motta, Jaime
Fejfarová, Karla
Dušek, Michal
4,4′-Dimeth­oxy-2,2′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-diyl]bis(methyl­ene)}diphenol
title 4,4′-Dimeth­oxy-2,2′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-diyl]bis(methyl­ene)}diphenol
title_full 4,4′-Dimeth­oxy-2,2′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-diyl]bis(methyl­ene)}diphenol
title_fullStr 4,4′-Dimeth­oxy-2,2′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-diyl]bis(methyl­ene)}diphenol
title_full_unstemmed 4,4′-Dimeth­oxy-2,2′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-diyl]bis(methyl­ene)}diphenol
title_short 4,4′-Dimeth­oxy-2,2′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-diyl]bis(methyl­ene)}diphenol
title_sort 4,4′-dimeth­oxy-2,2′-{[(3ars,7ars)-2,3,3a,4,5,6,7,7a-octa­hydro-1h-1,3-benzimidazole-1,3-diyl]bis(methyl­ene)}diphenol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3200725/
https://www.ncbi.nlm.nih.gov/pubmed/22065834
http://dx.doi.org/10.1107/S1600536811031436
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