Crystal structure of 2-(2-bromo­phen­yl)-4-(1H-indol-3-yl)-6-(thio­phen-2-yl)pyridine-3-carbo­nitrile

In the title compound, C₂₄H₁₄BrN₃S, the dihedral angles between the planes of the pyridine ring and the pendant thio­phene ring, the indole ring system (r.m.s. deviation = 0.022 Å) and the bromo­benzene ring are 9.37 (17), 21.90 (12) and 69.01 (15)°, respectively. The approximate coplanarity of the central ring and the indole ring system is supported by two intra­molecular C—H...N inter­actions. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generate R₂²(16) loops and the dimers are linked by C—H...π and aromatic π–π stacking [shortest centroid–centroid separation = 3.729 (3) Å] into a three-dimensional network.

Crystal structure of 2-(4-chloro­phen­yl)-4-(1H-indol-3-yl)-6-phenyl­pyridine-3-carbo­nitrile

In the title compound, C₂₆H₁₆ClN₃, the dihedral angles between the central pyridine ring and the pendant phenyl, chloro­benzene and indole rings are 18.52 (12), 48.97 (11) and 21.20 (10)°, respectively. An intra­molecular C—H...N_c (c = cyanide) hydrogen bond occurs. In the crystal, inversion dimers linked by pairs of N—H...N_c hydrogen bonds generate R₂²(16) loops.

Crystal structure of 4-(1H-indol-3-yl)-2-(4-meth­oxy­phen­yl)-6-phenyl­pyridine-3-carbo­nitrile

In the title compound, C₂₇H₁₉N₃O, the dihedral angles between the plane of the pyridine ring and those of the indole (r.m.s. deviation = 0.018 Å), phenyl and meth­oxy­benzene substituents are 33.60 (6), 25.28 (7) and 49.31 (7)°, respectively. The N atom of the carbo­nitrile group is significantly displaced [0.288 (2) Å] from the plane of the pyridine ring, perhaps due to steric crowding. In the crystal, inversion dimers linked by pairs of N—H...N_n (n = nitrile) hydrogen bonds generate R₂²(16) loops. Aromatic π–π stacking [centroid–centroid separation = 3.6906 (7) Å] and very weak C—H...π inter­actions are also observed".