Benzyl (E)-3-(4-methoxybenzylidene)dithiocarbazate

The title compound, C16H16N2OS2, was obtained from a condensation reaction of benzyl dithiocarbazate and 4-methoxybenzaldehyde. In the molecule, the methoxyphenyl ring and dithiocarbazate fragment are located on opposite sides of the C=N double bond, showing an E configuration. The dithiocarbazate fragment is approximately planar (r.m.s. deviation = 0.0052 Å); its mean plane is oriented at dihedral angles of 8.19 (15) and 85.70 (13)°, respectively, to the methoxyphenyl and phenyl rings. Intermolecular N—H⋯S hydrogen bonds and weak C—H⋯π interactions are observed in the crystal structure.

The title compound, C 16 H 16 N 2 OS 2 , was obtained from a condensation reaction of benzyl dithiocarbazate and 4-methoxybenzaldehyde. In the molecule, the methoxyphenyl ring and dithiocarbazate fragment are located on opposite sides of the C N double bond, showing an E configuration. The dithiocarbazate fragment is approximately planar (r.m.s. deviation = 0.0052 Å ); its mean plane is oriented at dihedral angles of 8.19 (15) and 85.70 (13) , respectively, to the methoxyphenyl and phenyl rings. Intermolecular N-HÁ Á ÁS hydrogen bonds and weak C-HÁ Á Á interactions are observed in the crystal structure.

Comment
Hydrazone and its derivatives have shown the potential application in the biological field (Okabe et al., 1993;Hu et al., 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.
In the molecules, the methoxylphenyl ring and dithiocarbazate fragment are located on the opposite sides of the C═N double bond, showing the E-configuration. The dithiocarbazate fragment is approximately planar [r.m.s deviation 0.0052 Å]; the mean plane of dithiocarbazate is oriented with respect to the methoxylphenyl and phenyl rings at 8.19 (15) and 85.70 (13)°, similar to those found in related structures (Shan et al. 2008a,b). Intermolecular N-H···S hydrogen bonding and weak C-H···π interaction are observed in the crystal structure (Table 1).

Experimental
Benzyl dithiocarbazate was synthesized as described previously (Hu et al., 2001). Benzyl dithiocarbazate (0.40 g, 2 mmol) and 4-methoxybenzaldehyde (0.27 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, 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 colourless 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. Fig. 1. The molecular structure of the title compound with 30% probability displacement (arbitrary spheres for H atoms).