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

The heterocyclic ring in the title compound, C(27)H(34)N(2)O(6), has an envelope conformation on one of the bridgehead C atoms [Q(2) = 0.4487 (19) Å and ϕ = 291.3 (2)°]. Two strong intra­molecular O—H⋯N hydrogen bonds stabilize the mol­ecular conformation. The benzoate groups differ in the relative...

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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/PMC3247559/
https://www.ncbi.nlm.nih.gov/pubmed/22219864
http://dx.doi.org/10.1107/S1600536811039559
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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 heterocyclic ring in the title compound, C(27)H(34)N(2)O(6), has an envelope conformation on one of the bridgehead C atoms [Q(2) = 0.4487 (19) Å and ϕ = 291.3 (2)°]. Two strong intra­molecular O—H⋯N hydrogen bonds stabilize the mol­ecular conformation. The benzoate groups differ in the relative orientations of the ethyl groups, as quanti­fied by the values of the C—O—C—C torsion angles of −86.5 (2) and −178.97 (17)°. The carbonyl groups are nearly coplanar with the benzene rings, forming C—C—C—O torsion angles of 0.9 (3) and 3.4 (3)°. The crystal structure is stabilized by weak inter­molecular C—H⋯O inter­actions.
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spelling pubmed-32475592012-01-04 Diethyl 4,4′-dihy­droxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}dibenzoate Rivera, Augusto Quiroga, Diego Ríos-Motta, Jaime Fejfarová, Karla Dušek, Michal Acta Crystallogr Sect E Struct Rep Online Organic Papers The heterocyclic ring in the title compound, C(27)H(34)N(2)O(6), has an envelope conformation on one of the bridgehead C atoms [Q(2) = 0.4487 (19) Å and ϕ = 291.3 (2)°]. Two strong intra­molecular O—H⋯N hydrogen bonds stabilize the mol­ecular conformation. The benzoate groups differ in the relative orientations of the ethyl groups, as quanti­fied by the values of the C—O—C—C torsion angles of −86.5 (2) and −178.97 (17)°. The carbonyl groups are nearly coplanar with the benzene rings, forming C—C—C—O torsion angles of 0.9 (3) and 3.4 (3)°. The crystal structure is stabilized by weak inter­molecular C—H⋯O inter­actions. International Union of Crystallography 2011-10-05 /pmc/articles/PMC3247559/ /pubmed/22219864 http://dx.doi.org/10.1107/S1600536811039559 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
Diethyl 4,4′-dihy­droxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}dibenzoate
title Diethyl 4,4′-dihy­droxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}dibenzoate
title_full Diethyl 4,4′-dihy­droxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}dibenzoate
title_fullStr Diethyl 4,4′-dihy­droxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}dibenzoate
title_full_unstemmed Diethyl 4,4′-dihy­droxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}dibenzoate
title_short Diethyl 4,4′-dihy­droxy-3,3′-{[(3aRS,7aRS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}dibenzoate
title_sort diethyl 4,4′-dihy­droxy-3,3′-{[(3ars,7ars)-2,3,3a,4,5,6,7,7a-octa­hydro-1h-1,3-benzimidazole-1,3-di­yl]bis­(methyl­ene)}dibenzoate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247559/
https://www.ncbi.nlm.nih.gov/pubmed/22219864
http://dx.doi.org/10.1107/S1600536811039559
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