5,6-Dimethyl-2-(5-methylthiophen-2-yl)-1-[(5-methylthiophen-2-yl)methyl]-1H-benzimidazole
The title molecule, C20H20N2S2, 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 a...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2014-04-01
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| Series: | Acta Crystallographica Section E |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S1600536814006333 |
| _version_ | 1818974151344390144 |
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| author | David K. Geiger Ava L. Isaac |
| author_facet | David K. Geiger Ava L. Isaac |
| author_sort | David K. Geiger |
| collection | DOAJ |
| description | The title molecule, C20H20N2S2, 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\overline{3}) 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]. |
| first_indexed | 2024-12-20T15:35:30Z |
| format | Article |
| id | doaj.art-6f849905ad2f42ecb245e916527cfa23 |
| institution | Directory Open Access Journal |
| issn | 1600-5368 |
| language | English |
| last_indexed | 2024-12-20T15:35:30Z |
| publishDate | 2014-04-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E |
| spelling | doaj.art-6f849905ad2f42ecb245e916527cfa232022-12-21T19:35:27ZengInternational Union of CrystallographyActa Crystallographica Section E1600-53682014-04-01704o488o48910.1107/S1600536814006333qk20655,6-Dimethyl-2-(5-methylthiophen-2-yl)-1-[(5-methylthiophen-2-yl)methyl]-1H-benzimidazoleDavid K. Geiger0Ava L. Isaac1Department of Chemistry, State University of New York-College at Geneseo, 1 College Circle, Geneseo, NY 14454, USADepartment of Chemistry, State University of New York-College at Geneseo, 1 College Circle, Geneseo, NY 14454, USAThe title molecule, C20H20N2S2, 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\overline{3}) 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].http://scripts.iucr.org/cgi-bin/paper?S1600536814006333 |
| spellingShingle | David K. Geiger Ava L. Isaac 5,6-Dimethyl-2-(5-methylthiophen-2-yl)-1-[(5-methylthiophen-2-yl)methyl]-1H-benzimidazole Acta Crystallographica Section E |
| 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 |
| url | http://scripts.iucr.org/cgi-bin/paper?S1600536814006333 |
| work_keys_str_mv | AT davidkgeiger 56dimethyl25methylthiophen2yl15methylthiophen2ylmethyl1hbenzimidazole AT avalisaac 56dimethyl25methylthiophen2yl15methylthiophen2ylmethyl1hbenzimidazole |