(E)-1-(4-Chlorobenzylidene)thiosemicarbazide

In the crystal of the title compound, C8H8ClN3S, molecules are connected by N—H⋯S hydrogen bonds into strips parallel to the (112) planes and running along [10]. One of the amino H atoms is not involved in a classical hydrogen bond. In addition, there is a rather short intermolecular Cl⋯S distance of 3.3814 (5) Å.

In the crystal of the title compound, C 8 H 8 ClN 3 S, molecules are connected by N-HÁ Á ÁS hydrogen bonds into strips parallel to the (112) planes and running along [110]. One of the amino H atoms is not involved in a classical hydrogen bond. In addition, there is a rather short intermolecular ClÁ Á ÁS distance of 3.3814 (5) Å .
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2386).

Comment
Schiff bases derived from semicarbazide and aromatic aldehydes are an important class of organic compounds because of their applications in many fields including inorganic, biological, and analytical chemistry (Mobinikhaledi et al., 2010;Thangadurai et al., 2002). Schiff bases are known to be versatile ligands in coordination chemistry (Ji & Lu, 2010a,2010bHamaker et al., 2010;Mirkhani et al., 2010). Shiff bases and their complexes are also important in material science applications like organic light emitting diodes (Lü et al., 2008).
The title compound features an essentially planar molecule: the largest deviation of a torsion angle from 0 or 180Å is 13.02 (19)° for N1-C1-C11-C12. Bond lengths and angles do not show any unusual values. In the crystal, the molecules are connected by N-H···S hydrogen bonds into strips parallel to the (1 1 2) planes and running along [1 1 0]. One of the amino H atoms is not involved in a classical hydrogen bond. In addition there is a rather short intermolecular Cl···S i distance of 3.3814 (5)Å (symmetry operator (i): x -2, y, z + 1).

Experimental
Semicarbazide, 0.137 g (1 mmol) dissolved in 5 ml e thanol was added dropwise to a solution of 4-chlorobenzaldehyde, 0.122 g (1.1 mmol) in 10 ml e thanol at room temperature with continuous stirring. The reaction mixture was refluxed for 4 h and completion monitored by TLC. The reaction mixture was concentrated and the resulting product was separated.
Colourless single crystals of the compound, suitable for X-ray crystallography, were grown by slow evaporation from a

Refinement
H atoms bonded to N were freely refined. H atoms bonded to C were geometrically positioned and refined using a riding model with C-H = 0.95Å and U(H) set to 1.2U eq (C). Fig. 1. Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.  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 Rfactors(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.