Synthesis and Crystal Structures of Halogen-Substituted 2-Aryl-N-phenylbenzimidazoles

Four 2-arylbenzimidazoles (aryl = 4-Br-phenyl (1), 3-Br-phenyl (2), 4-I-phenyl (3), 3-I-phenyl (4)) were synthesized and characterized by 1H, 13C{1H} NMR, UV–Vis spectroscopy and single-crystal X-ray diffraction. Both pairs of benzimidazoles bearing the halogen atom at the same position form isostructural crystals, in which para-substituted compounds 1 and 3 are assembled by weak C–H···π and π···π interactions while their meta-isomers 2 and 4 are linked via intermolecular halogen···nitrogen and C–H···π contacts.