(3-Chlorophenyl)[(E)-2-(1,3-dithiolan-2-ylidene)hydrazinylidene]methyl 3-chlorobenzoate

In the title compound, C17H12Cl2N2O2S2, the dithiacyclopentane ring has an envelope conformation with one of the methylene C atoms as the flap. The chlorophenyl rings make a dihedral angle of 82.63 (7)°. In the crystal, π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.547 (2) Å] link the molecules into inversion dimers. Weak non-classical C—H⋯X (X = O, N, Cl) interactions further consolidate the packing, forming a layer structure parallel to (110).

In the title compound, C 17 H 12 Cl 2 N 2 O 2 S 2 , the dithiacyclopentane ring has an envelope conformation with one of the methylene C atoms as the flap. The chlorophenyl rings make a dihedral angle of 82.63 (7) . In the crystal,interactions between the benzene rings of neighbouring molecules [centroid-centroid distance = 3.547 (2) Å ] link the molecules into inversion dimers. Weak non-classical C-HÁ Á ÁX (X = O, N, Cl) interactions further consolidate the packing, forming a layer structure parallel to (110).
In (I) (Fig. 1), the dithiacyclopentane ring has an envelope conformation with C16 atom as a flap. Two chlorophenyl rings (C1-C6 and C9-C14) in the molecule form a dihedral angle of 82.63 (7)°. All bond lengths and angles are normal and in a good agreement with those reported previously for related compounds (Yin, 2013) In the crystal, π-π interactions between the benzene rings from two neighbouring molecules [centroid-centroid distance of 3.547 (2) Å] link the latters into centrosymmetric dimer, and weak non-classical C-H···X (X=O, N, Cl) interactions (Table 1) consolidate further the packing.
The reaction mixture was stirred vigorously at 0 centigrade for 4 h. The reaction mixture was poured into 200 ml of water and extracted with three 50-ml portions of dichloromethane. The combined extracts were washed with saturated brine, dried over anhydrous sodium sulfate and evaporated on a rotary evaporator to afford the crude product, which was purified by column chromatography to yield the pure product as colorless crystals. Single crystals suitable for X-ray diffraction were obtained through slow evaporation of a solution of the pure title compound in ethanol.

Refinement
All H atoms bonded on carbon were found on difference maps, with C-H = 0.93 or 0.97 Å, and included in the final cycles of refinement using a riding model, with U iso (H) = 1.2U eq (C).  View of the title compound showing the atomic numbering and 50% probability displacement ellipsoids. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.46 e Å −3 Δρ min = −0.22 e Å −3

Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.