3-Chloro-N-[N-(furan-2-carbonyl)hydrazinocarbothioyl]benzamide

In the title compound C13H10ClN3O3S, the benzoyl group maintains its trans conformation against the thiono group about the C—N bond and the intramolecular hydrogen bond between the benzoyl O atom and thioamide H atom. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds link the molecules, forming chains along the b-axis direction. In addition, C—H⋯π interactions occur between a phenyl H atom and the furan ring.

In the title compound C 13 H 10 ClN 3 O 3 S, the benzoyl group maintains its trans conformation against the thiono group about the C-N bond and the intramolecular hydrogen bond between the benzoyl O atom and thioamide H atom. In the crystal, N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds link the molecules, forming chains along the b-axis direction. In addition, C-HÁ Á Á interactions occur between a phenyl H atom and the furan ring.   Table 1 Hydrogen-bond geometry (Å , ).

Experimental
An acetone (30 ml) solution of tetrahydrofuran-2-carboxamide (0.18 g, 2 mmol) was added into a round-bottom flask containing 3-chlorobenzoyl isothiocyanate (0.58 g,2 mmol). The mixture was refluxed for 3h. After cooling, the solution was filtered off and the filtrate was left to evaporate at room temperature. The solid formed was washed with water and cold ethanol. Crystals suitable for X-ray study were obtained by recrystallization from DMSO.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 1. All H atoms attached to C and N atoms were fixed geometrically and treated as riding with C-H= 0.93-0.97Å and N-H = 0.86Å with U iso (H)= 1.2U eq (C and N).

Figure 1
The molecular structure of (I), with displacement ellipsods drawn at the 50% probability level. The dashed line indicates intramolecular hydrogen bond.

Figure 2
Molecular packing of (I) viewed down the c-axis. Dashed lines indicate intermolecular hydrogen bonds. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.24 e Å −3 Δρ min = −0.19 e Å −3 Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq