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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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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. |
format | Online Article Text |
id | pubmed-3772488 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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