(2Z)-N-(2-Chlorobenzyl)-2-(2-oxo-2,3- dihydro-1H-indol-3-ylidene)hydrazine carbothioamide

Abstract

In the title compound, C16H13ClN4OS, the isatin ring system is oriented at dihedral angles of 10.60 (7) and 72.60 (3) with respect to the thiosemicarbazide and 2-chlorobenzyl groups, respectively. The near planarity of the isatin and thio semicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 A˚ , respectively] is reinforced by intramolecular N— H O and N—H N hydrogen bonds, which generate S(6) and S(5) rings, respectively. In the crystal, inversion dimers linked by pairs of N—H O hydrogen bonds generate R2 2 (8) loops. Aromatic – stacking interactions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) A˚ ] are also observed