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5,6-Dimethyl-2-(5-methyl­thio­phen-2-yl)-1-[(5-methyl­thio­phen-2-yl)meth­yl]-1H-benzimidazole

The title mol­ecule, C(20)H(20)N(2)S(2), is T-shaped and consists of a nearly flat 5,6-dimethyl-2-(5-methyl­thio­phen-2-yl)benzimidazole system approximately perpendicular to the 5-methyl­thio­phen-2-ylmethyl substituent. The 5,6-dimethyl-2-(5-meth­yl­thio­phen-2-yl)benzimidazole system is rotationa...

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Autores principales: Geiger, David K., Isaac, Ava L.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998620/
https://www.ncbi.nlm.nih.gov/pubmed/24826180
http://dx.doi.org/10.1107/S1600536814006333
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author Geiger, David K.
Isaac, Ava L.
author_facet Geiger, David K.
Isaac, Ava L.
author_sort Geiger, David K.
collection PubMed
description The title mol­ecule, C(20)H(20)N(2)S(2), is T-shaped and consists of a nearly flat 5,6-dimethyl-2-(5-methyl­thio­phen-2-yl)benzimidazole system approximately perpendicular to the 5-methyl­thio­phen-2-ylmethyl substituent. The 5,6-dimethyl-2-(5-meth­yl­thio­phen-2-yl)benzimidazole system is rotationally disordered about the two imidazole N atoms as approximated by a twofold rotation axis with a refined major/minor occupancy ratio of 0.884 (2):0.116 (2). The benzimidazole ring system is essentially planar, the largest deviations being 0.026 (2) and 0.044 (18) Å in the major and minor components, respectively. The inter­planar angles between the benzimidazole unit and the 5-methyl­thio­phen-2-yl substituent are 10.8 (3) and 8(3)° in the major and minor components, respectively, and the corresponding angles with the 5-methyl­thio­phen-2-ylmethyl substituent are 88.12 (8) and 89.5 (4)°. In the crystal, mol­ecules are oriented with their 2-(5-methyl­thio­phen-2-yl)benzimidazole mean planes approximately parallel to (11[Image: see text]) and appear to be held together by π–π [2-thiophene⋯imidazole centroid–centroid distance = 4.1383 (7) Å] and C—H⋯π contacts. A weak C—H⋯N hydrogen bond generates infinite chains parallel to [100].
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spelling pubmed-39986202014-05-13 5,6-Dimethyl-2-(5-methyl­thio­phen-2-yl)-1-[(5-methyl­thio­phen-2-yl)meth­yl]-1H-benzimidazole Geiger, David K. Isaac, Ava L. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title mol­ecule, C(20)H(20)N(2)S(2), is T-shaped and consists of a nearly flat 5,6-dimethyl-2-(5-methyl­thio­phen-2-yl)benzimidazole system approximately perpendicular to the 5-methyl­thio­phen-2-ylmethyl substituent. The 5,6-dimethyl-2-(5-meth­yl­thio­phen-2-yl)benzimidazole system is rotationally disordered about the two imidazole N atoms as approximated by a twofold rotation axis with a refined major/minor occupancy ratio of 0.884 (2):0.116 (2). The benzimidazole ring system is essentially planar, the largest deviations being 0.026 (2) and 0.044 (18) Å in the major and minor components, respectively. The inter­planar angles between the benzimidazole unit and the 5-methyl­thio­phen-2-yl substituent are 10.8 (3) and 8(3)° in the major and minor components, respectively, and the corresponding angles with the 5-methyl­thio­phen-2-ylmethyl substituent are 88.12 (8) and 89.5 (4)°. In the crystal, mol­ecules are oriented with their 2-(5-methyl­thio­phen-2-yl)benzimidazole mean planes approximately parallel to (11[Image: see text]) and appear to be held together by π–π [2-thiophene⋯imidazole centroid–centroid distance = 4.1383 (7) Å] and C—H⋯π contacts. A weak C—H⋯N hydrogen bond generates infinite chains parallel to [100]. International Union of Crystallography 2014-03-29 /pmc/articles/PMC3998620/ /pubmed/24826180 http://dx.doi.org/10.1107/S1600536814006333 Text en © Geiger and Isaac 2014 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
Geiger, David K.
Isaac, Ava L.
5,6-Dimethyl-2-(5-methyl­thio­phen-2-yl)-1-[(5-methyl­thio­phen-2-yl)meth­yl]-1H-benzimidazole
title 5,6-Dimethyl-2-(5-methyl­thio­phen-2-yl)-1-[(5-methyl­thio­phen-2-yl)meth­yl]-1H-benzimidazole
title_full 5,6-Dimethyl-2-(5-methyl­thio­phen-2-yl)-1-[(5-methyl­thio­phen-2-yl)meth­yl]-1H-benzimidazole
title_fullStr 5,6-Dimethyl-2-(5-methyl­thio­phen-2-yl)-1-[(5-methyl­thio­phen-2-yl)meth­yl]-1H-benzimidazole
title_full_unstemmed 5,6-Dimethyl-2-(5-methyl­thio­phen-2-yl)-1-[(5-methyl­thio­phen-2-yl)meth­yl]-1H-benzimidazole
title_short 5,6-Dimethyl-2-(5-methyl­thio­phen-2-yl)-1-[(5-methyl­thio­phen-2-yl)meth­yl]-1H-benzimidazole
title_sort 5,6-dimethyl-2-(5-methyl­thio­phen-2-yl)-1-[(5-methyl­thio­phen-2-yl)meth­yl]-1h-benzimidazole
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998620/
https://www.ncbi.nlm.nih.gov/pubmed/24826180
http://dx.doi.org/10.1107/S1600536814006333
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