Ethoxycarbonylmethyl 3-(4-chlorobenzylidene)dithiocarbazate

Molecules of the title compound, C12H13ClN2O2S2, are linked into centrosymmetric dimers by pairs of intermolecular N—H⋯S hydrogen bonds. In the crystal structure, there are π–π stacking interactions between symmetry-related benzene rings with a centroid–centroid distance of 3.7305 (13) Å, a perpendicular distance between the planes of 3.2851 (9) Å and a slippage of 1.768 Å. The structure is further stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Molecules of the title compound, C 12 H 13 ClN 2 O 2 S 2 , are linked into centrosymmetric dimers by pairs of intermolecular N-HÁ Á ÁS hydrogen bonds. In the crystal structure, there arestacking interactions between symmetry-related benzene rings with a centroid-centroid distance of 3.7305 (13) Å , a perpendicular distance between the planes of 3.2851 (9) Å and a slippage of 1.768 Å . The structure is further stabilized by weak intermolecular C-HÁ Á ÁO hydrogen bonds.
In the title molecule ( Fig. 1) bond distances and angles are unexceptional and agree with the corresponding bond distances and angles reported in the related compounds (Tabatabaee et al., 2006;2007;2008;2009). In the solid state, intermolecular N-H···S hydrogen bonds in the title compound link the molecules lying about inversion centers leading to centrosymmetric dimers (Tab. 1 & Fig. 2). Moreover, the benzene rings C1-C6 and C1 i -C6 i ( i = 2 -x, 1 -y, 1 -z) show π-π stacking interactions ( Fig. 3) with centroid-centroid distance 3.7305 (13) Å, the angle between the planes 0 °; the perpendicular distance between the planes 3.2851 (9) Å and the slippage 1.768 Å. The structure is further stabilized by intermolecular hydrogen bonding of C-H···O type (Tab. 1); unit cell packing showing hydrogen bonding interactions has been presented in Figure 4.

Experimental
A solution of N-aminorhodanine (5 mmol) in EtOH (20 ml) was treated with 2-chlorobenzaldehyde (5 mmol) and the resulting mixture was acidified with 37% hydrochloric acid (0.2 ml). The reaction mixture was refluxed for 8 h. After completion of the reaction, the solid residue was filtered, washed with cold ethanol (10 ml) and recrystallized from EtOH.

Refinement
The H-atoms were visible in difference Fourier maps but were included in the refinement in geometrically idealized positions with distances N-H = 0.88 Å and C-H = 0.95, 0.98 and 0.99 Å for aryl, methyl and methylene type H-atoms, respectively.
The H-atoms were assigned U iso = 1.2 × U eq of the parent atoms. The final difference map was free of chemically significant features.