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Acta Cryst. (2012). E68, o2731
[ doi:10.1107/S1600536812035076 ]

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

H. Pervez, N. Khan, M. S. Iqbal, M. Yaqub and M. N. Tahir

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 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 [pi]-[pi] stacking interactions between the centroids of heterocyclic five-membered and benzene rings [distance = 3.6866 (11) Å] are also observed.


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