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

Abstract

Key indicators: single-crystal X-ray study; T = 296 K; mean (C-C) = 0.003 Å; R factor = 0.043; wR factor = 0.105; data-to-parameter ratio = 18.9.In the title compound, C 16 H 13 ClN 4 OS, 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 thiosemicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 Å , respectively] is reinforced by intramolecular N-HÁ Á ÁO and N-HÁ Á ÁN hydrogen bonds, which generate S(6) and S(5) rings, respectively. In the crystal, inversion dimers linked by pairs of N-HÁ Á ÁO hydrogen bonds generate R 2 2 (8) loops. Aromatic -stacking interactions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å ] are also observed. Related literature