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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2014
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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]. |
format | Online Article Text |
id | pubmed-3998620 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2014 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT geigerdavidk 56dimethyl25methylthiophen2yl15methylthiophen2ylmethyl1hbenzimidazole AT isaacaval 56dimethyl25methylthiophen2yl15methylthiophen2ylmethyl1hbenzimidazole |