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

The title compound, C(23)H(30)N(2)O(4), a di-Mannich base derived from 4-meth­oxy­phenol and cis-1,2-di­amine­cyclo­hexane, has a perhydro­benzimidazolidine nucleus, in which the cyclo­hexane ring adopts a chair conformation and the heterocyclic ring has a half-chair conformation with a C—N—C—C tors...

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Autores principales: Rivera, Augusto, Quiroga, Diego, Ríos-Motta, Jaime, Kučeraková, Monika, Dušek, Michal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772488/
https://www.ncbi.nlm.nih.gov/pubmed/24046631
http://dx.doi.org/10.1107/S1600536813015092
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author Rivera, Augusto
Quiroga, Diego
Ríos-Motta, Jaime
Kučeraková, Monika
Dušek, Michal
author_facet Rivera, Augusto
Quiroga, Diego
Ríos-Motta, Jaime
Kučeraková, Monika
Dušek, Michal
author_sort Rivera, Augusto
collection PubMed
description The title compound, C(23)H(30)N(2)O(4), a di-Mannich base derived from 4-meth­oxy­phenol and cis-1,2-di­amine­cyclo­hexane, has a perhydro­benzimidazolidine nucleus, in which the cyclo­hexane ring adopts a chair conformation and the heterocyclic ring has a half-chair conformation with a C—N—C—C torsion angles of −48.14 (15) and −14.57 (16)°. The mean plane of the heterocycle makes dihedral angles of 86.29 (6) and 78.92 (6)° with the pendant benzene rings. The mol­ecular structure of the title compound shows the presence of two inter­actions between the N atoms of the imidazolidine ring and the hydroxyl groups through intra­molecular O—H⋯N hydrogen bonds with graph-set motif S(6). The unobserved lone pairs of the N atoms are presumed to be disposed in a syn conformation, being only the second example of an exception to the typical ‘rabbit-ears’ effect in 1,2-di­amines.
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spelling pubmed-37724882013-09-17 meso-4,4′-Dimeth­oxy-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-benz­imidazole-1,3-di­yl]bis­(methyl­ene)}diphenol Rivera, Augusto Quiroga, Diego Ríos-Motta, Jaime Kučeraková, Monika Dušek, Michal Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(23)H(30)N(2)O(4), a di-Mannich base derived from 4-meth­oxy­phenol and cis-1,2-di­amine­cyclo­hexane, has a perhydro­benzimidazolidine nucleus, in which the cyclo­hexane ring adopts a chair conformation and the heterocyclic ring has a half-chair conformation with a C—N—C—C torsion angles of −48.14 (15) and −14.57 (16)°. The mean plane of the heterocycle makes dihedral angles of 86.29 (6) and 78.92 (6)° with the pendant benzene rings. The mol­ecular structure of the title compound shows the presence of two inter­actions between the N atoms of the imidazolidine ring and the hydroxyl groups through intra­molecular O—H⋯N hydrogen bonds with graph-set motif S(6). The unobserved lone pairs of the N atoms are presumed to be disposed in a syn conformation, being only the second example of an exception to the typical ‘rabbit-ears’ effect in 1,2-di­amines. International Union of Crystallography 2013-06-08 /pmc/articles/PMC3772488/ /pubmed/24046631 http://dx.doi.org/10.1107/S1600536813015092 Text en © Rivera et al. 2013 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
Kučeraková, Monika
Dušek, Michal
meso-4,4′-Dimeth­oxy-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-benz­imidazole-1,3-di­yl]bis­(methyl­ene)}diphenol
title meso-4,4′-Dimeth­oxy-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-benz­imidazole-1,3-di­yl]bis­(methyl­ene)}diphenol
title_full meso-4,4′-Dimeth­oxy-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-benz­imidazole-1,3-di­yl]bis­(methyl­ene)}diphenol
title_fullStr meso-4,4′-Dimeth­oxy-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-benz­imidazole-1,3-di­yl]bis­(methyl­ene)}diphenol
title_full_unstemmed meso-4,4′-Dimeth­oxy-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-benz­imidazole-1,3-di­yl]bis­(methyl­ene)}diphenol
title_short meso-4,4′-Dimeth­oxy-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octa­hydro-1H-benz­imidazole-1,3-di­yl]bis­(methyl­ene)}diphenol
title_sort meso-4,4′-dimeth­oxy-2,2′-{[(3ar,7as)-2,3,3a,4,5,6,7,7a-octa­hydro-1h-benz­imidazole-1,3-di­yl]bis­(methyl­ene)}diphenol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3772488/
https://www.ncbi.nlm.nih.gov/pubmed/24046631
http://dx.doi.org/10.1107/S1600536813015092
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