Crystal structure of 2-(4-chloro-3-fluorophenyl)-1H-benzimidazole

Abstract

In the title compound, C13H8ClFN2, the dihedral angle between the plane of the benzimidazole ring system (r.m.s. deviation = 0.022 Å) and the benzene ring is 26.90 (8)°. The F atom at the meta position of the benzene ring is disordered over two sites in a 0.843 (4):0.157 (4) ratio. In the crystal, molecules are linked by N—H...N hydrogen bonds, forming infinite C(4) chains propagating along [010]. In addition, weak C—H...π and π–π interactions [shortest centroid–centroid separation = 3.6838 (12) Å] are observed, which link the chains into a three-dimensional network.

Keywords

• crystal structure
• benzimidazole
• fluorine-containing compound
• hydrogen bonding
• C—H...π interactions
• π–π interactions