Abstract

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) 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].

Highlights

  • 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 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)

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Summary

Structure Reports

Key indicators: single-crystal X-ray study; T = 200 K; mean (C–C) = 0.004 Å; disorder in main residue; R factor = 0.043; wR factor = 0.123; data-to-parameter ratio = 11.3

Data collection
Related literature
Geiger and Isaac
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