Synthesis and crystal structures of two cocrystals of imidazo[1,2-a]pyridine-3-carbonitrile with nitro-substituted benzoic acid and phenol

Two 1:1 cocrystals of imidazo[1,2- a ]pyridine-3-carbonitrile (IPC) with 4-nitrobenzoic acid (4-NBA) and 4-nitrophenol (4-NP), namely, imidazo[1,2- a ]pyridine-3-carbonitrile–4-nitrobenzoic acid (1/1), C 8 H 5 N 3 ·C 7 H 5 NO 4 or (IPC)·(4-NBA) ( I ), and imidazo[1,2- a ]pyridine-3-carbonitrile–4-nitrophenol (1/1), C 8 H 5 N 3 ·C 6 H 5 NO 3 or (IPC)·(4-NP) ( II ), were obtained and their crystal structures determined by single-crystal X-ray diffraction. Molecules of I and II are both linked by O—H...N, C—H...O and C—H...N hydrogen bonds to form two-dimensional planes, which are further connected into three-dimensional frameworks by C—H...π interactions (in I ) and π–π interactions (in II ).