N-(2-Bromophenyl)thiourea

In the title compound, C7H7BrN2S, the thiourea unit is almost perpendicular to the bromobenzene fragment, making a dihedral angle of 80.82 (16)°. The crystal structure is stabilized by N—H⋯S intermolecular hydrogen bonds, which form linear chains along the ab diagonal.

In the title compound, C 7 H 7 BrN 2 S, the thiourea unit is almost perpendicular to the bromobenzene fragment, making a dihedral angle of 80.82 (16) . The crystal structure is stabilized by N-HÁ Á ÁS intermolecular hydrogen bonds, which form linear chains along the ab diagonal.

Comment
The number of publications including patents on the application of thiourea compounds in the field of pharmaceutical is increasing at a considerable rate. The antivarial activities of a series of phenylthioureas as none-nucleoside inhibitors HIV-1 reverse transcriptase (NNRTIs) with efficacy against multi-drug resistant viruses (Sudbeck et al., 1998;Mao et al., 2000;D'Cruz & Uckun, 2005) are some of the interesting examples. Several N-thiourea compounds of the type H 2 NC(S)NHR are now commercially available.

Experimental
The compound was prepared by the method described by Frank & Smith (1955) with a slight modification. Ammonium thiocyante (0.38 g, 0.005 mol) in 15 ml acetone was added into 20 ml acetone solution of containing benzoylchloride (0.70 g, 0.005 mole). The solution was filtered and the filtrate was kept into a 100 ml two neck round bottom flask. o-Bromoaniline (0.86 g, 0.005 mole) was added into the flask and the mixture was refluxed for 2 hours. The final solution was poured into a baker containing some ice cubes. The precipitate formed was filtered. The precipitate was then added into a beaker containing 50 ml aqueous solution of sodium hydroxide (7 g). The solution was heated to boiling for 10 minutes. After a week on standing at room temperature some colourless crystals were obtained and found suitable for X-ray investigation.

Refinement
H atoms on the C atoms were positioned geometrically with C-H= 0.93 for aromatic group and constrained to ride on their parent atoms with U iso (H)= 1.2 x U eq (C parent atom). The hydrogen atoms attached to the nitrogen atoms were located from the Fourier map and initially refined with U iso (H)= 1.2 x U eq (N) . In the last stage of refinement, they were treated as riding on their parent N atoms.
supplementary materials sup-2 Figures   Fig. 1. The nolecular structure of (I), with the atom labeling scheme. Displacement ellipsods are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

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 > 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.