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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 thiosemicarbazide groups [r.m.s. deviations of 0.0420 and 0.0163 Å, 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 R22(8) loops. Aromatic π–π stacking interactions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å] are also observed.