Benzyl (E)-3-(2-methylbenzylidene)dithiocarbazate

The title compound, C16H16N2S2, was obtained from the condensation reaction of benzyl dithiocarbazate and 2-methylbenzaldehyde. The asymmetric unit contains two independent molecules. In both molecules, the methylphenyl ring and the dithiocarbazate fragment are located on opposite sides of the C=N bond, showing an E conformation. In each molecule, the dithiocarbazate fragment is approximately planar, the r.m.s deviations being 0.018 and 0.025 Å. The mean plane of dithiocarbazate group is oriented at dihedral angles of 7.9 (3) and 68.24 (12)°, respectively, to the methylphenyl and phenyl rings in one molecule, while the corresponding angles in the other molecule are 10.9 (3) and 69.76 (16)°. Intermolecular N—H⋯S hydrogen bonding occurs in the crystal structure to generate inversion dimers for both molecules.

The title compound, C 16 H 16 N 2 S 2 , was obtained from the condensation reaction of benzyl dithiocarbazate and 2methylbenzaldehyde. The asymmetric unit contains two independent molecules. In both molecules, the methylphenyl ring and the dithiocarbazate fragment are located on opposite sides of the C N bond, showing an E conformation. In each molecule, the dithiocarbazate fragment is approximately planar, the r.m.s deviations being 0.018 and 0.025 Å . The mean plane of dithiocarbazate group is oriented at dihedral angles of 7.9 (3) and 68.24 (12) , respectively, to the methylphenyl and phenyl rings in one molecule, while the corresponding angles in the other molecule are 10.9 (3) and 69.76 (16) . Intermolecular N-HÁ Á ÁS hydrogen bonding occurs in the crystal structure to generate inversion dimers for both molecules.

2001
). As part of the ongoing investigation on anti-cancer compounds, the title compound has recently been prepared in our laboratory and its crystal structure is presented here.
The asymmetric unit of the title compound contains two independent molecules. In both molecules, the methylphenyl ring and dithiocarbazate fragment are located on the opposite sides of the C═N bond, showing the E-configuration. This agrees with those found in the structures reported previously (Shan et al., 2006;Shan et al., 2008a,b). In each molecule, the dithiocarbazate fragment is approximately planar, the r.m.s deviation being 0.0177 and 0.0248 Å, respectively. The mean plane of dithiocarbazate is oriented with respect to the methylphenyl and phenyl rings at 7.9 (3) and 68.24 (12)° in the C1-containing molecule; while the corresponding angles are 10.9 (3) and 69.76 (16)° in the other molecule.
Intermolecular N-H···S hydrogen bonding occurs in the crystal structure (Table 1).

Experimental
Benzyl dithiocarbazate was synthesized as described previously (Hu et al., 2001). Benzyl dithiocarbazate (0.4 g, 2 mmol) and 2-methylbenzaldehyde (0.24 g, 2 mmol) were dissolved in ethanol (20 ml), then acetic acid (0.2 ml) was added to the ethanol solution with stirring. The mixture solution was refluxed for 6 h. After cooling to room temperature, yellow microcrystals appeared. The microcrystals were separated from the solution and washed with cold water three times. Recrystallization was performed twice with absolute methanol to obtain single crystals of the title compound.

Refinement
H atoms were placed in calculated positions with C-H = 0.93-0.97 Å and N-H = 0.86 Å, and refined in riding mode with U iso (H) = 1.5U eq (C) for methyl H atoms and 1.2U eq (C,N) for the others.