Date Published: May 01, 2012
Publisher: International Union of Crystallography
Author(s): Song-Lei Zhu, Jun-Nian Zheng.
In the title compound, C29H18ClN5·C2H6O, the dihydropyridine ring adopts a strongly flattened envelope conformation, with a maximum deviation of 0.139 (2) Å from its best plane for the Csp3 atom. The dihedral angles between the dihydropyridine ring plane and the two indole rings in positions 2 and 6 are 34.28 (5) and 40.50 (6)°, respectively. In turn, the benzene ring and the dihydropyridine ring are oriented at a dihedral angle of 74.69 (6)°. An intramolecular C—H⋯Cl hydrogen bond occurs. In the crystal, molecules are linked by N—H⋯N, N—H⋯O and O—H⋯N hydrogen bonds into layers parallel to (001). There are short C—H⋯Cl contacts between molecules in neighboring layers.
For the biological activity of indole and 1,4-dihydropyridine derivatives, see: da Silva et al. (2001 ▶); Joshi & Chand (1982 ▶); Janis & Triggle (1983 ▶). For the synthesis of a series of bisindoles derivatives of 1,4-dihydropyridine, see: Zhu et al. (2008 ▶).