1-(3-Chlorophenyl)thiourea

In the title compound, C7H7ClN2S, the thiourea N—C(=S)—N plane forms a dihedral angle of 64.80 (6)° with the benzene ring. In the crystal, molecules are linked via intermolecular N—H⋯S and N—H⋯Cl hydrogen bonds into a sheet extending parallel to the (101) plane.

In the title compound, C 7 H 7 ClN 2 S, the thiourea N-C( S)-N plane forms a dihedral angle of 64.80 (6) with the benzene ring. In the crystal, molecules are linked via intermolecular N-HÁ Á ÁS and N-HÁ Á ÁCl hydrogen bonds into a sheet extending parallel to the (101) plane.

Comment
In view of importance of thiourea derivatives (Saleem & Yamin, 2010;Sarojini et al., 2007), the title compound (I) is prepared and its crystal structure is reported.

Experimental
3-Chloroaniline (0.65 ml, 0.0081 mol) was refluxed with potassium thiocyanate (1.4 g, 0.0142 mol) in 20 ml of water and 1.6 ml of conc. HCl for 3 h. The reaction mixture was then cooled to room temperature and stirred overnight. The precipitated product was then filetred, washed with water, dried and single crystals were grown from toluene and acetone (1:1) mixture by the slow evaporation method (m.p. 402 K).

Refinement
N-bound hydrogen atoms were located in a difference Fourier map and refined freely [N-H = 0.80 (2)-0.84 (2) Å]. The remaining H atoms were positioned geometrically and refined using a riding model with C-H = 0.93 Å and U iso (H) = 1.2U eq (C).

Computing details
Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009  The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms.  (Cosier & Glazer, 1986) operating at 100.0 (1) K. 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.