Synthesis and crystal structures of N-H, N-phenyl and N-benzyl-2-(4-hexyloxyphenyl)benzimidazoles

The title compounds, 2-(4-hexyloxyphenyl)-1H-benzimidazole (C₁₉H₂₂N₂O; 1), 2-(4-hexyloxyphenyl)-1-phenyl-1H-benzimidazole (C₂₅H₂₆N₂O; 2) and 1-benzyl-2-(4-hexyloxyphenyl)-1H-benzimidazole (C₂₆H₂₈N₂O; 3) were synthesized and their structures were determined by single-crystal X-ray analysis. The N-substituent at the imidazole moiety slightly affects the interplanar angle between the 4-hexyloxyphenyl ring and the benzimidazole system. The unsubstituted benzimidazole (1) forms intermolecular N—H...N bonds while in the crystal structures of 2 and 3, the molecules are assembled only through π–π and C—H...π interactions.