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

Abstract

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.

Keywords

• crystal structure
• pyridine-3-carbonitrile
• hydrogen bonding
• π–π stacking