(E)-1-(2-Nitrobenzylidene)-4-phenylthiosemicarbazide

In the title molecule, C14H12N4O2S, the conformation about the imine bond is trans. The dihedral angle between the two rings is 88.22 (11)°. An intramolecular N—H⋯N contact occurs. The crystal structure features N—H⋯S and C—H⋯O hydrogen bonds.

In a continuation of our research on the development of synthetic methods in heterocyclic chemistry (Shaabani et al., 2011;Sardari et al., 1999) here we report the synthesis and structure of the title compound.
The asymmetric unit of the title compound is shown in Fig. 1 Table 1).

Experimental
To a magnetically stirred solution of 4-phenylthiosemicarbazide (0.167 g, 1.0 mmol) in MeOH (30 ml) in round bottom flask was added a solution of 2-nitrobenzaldehyde (0.151 g, 1 mmol) at room temperature. The mixture was stirred for 48 h. After completion of the reaction, the Precipitate product was filtered and washed with MeOH (20 ml) and dried at room temperature. The final product is a yellow solid (yield 70%).

Refinement
The hydrogen atom attached to nitrogen atoms and C-H of imine moiety were found in difference Fourier map and refined isotropically without restraint. Aromatic C-H protons were positioned geometrically and refined as riding atoms with C-H = 0.93 Å and Uiso(H) = 1.2 Ueq(C).  The asymmetric unit of the title compound with displacement ellipsoids drawn at 30% probability level.

Figure 2
The packing diagram of the title compound. The intermolecular N-H···S and C-H···O hydrogen bonds are shown as blue dashed lines. Special details Experimental. shape of crystal determined optically 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.