1-(4-Bromophenyl)-3-(3-chloropropanoyl)thiourea

The title compound, C10H10BrClN2OS, adopts a trans–cis conformation with respect to the position of the 3-chloropropanoyl and 4-bromophenyl groups, respectively, against the thiono C=S bond across their C—N bonds. The benzene ring makes a dihedral angle of 9.55 (16)° with the N2CS thiourea moiety. Intramolecular N—H⋯O and C—H⋯S hydrogen bonds occur. In the crystal, molecules are linked into chains along the c-axis direction by N—H⋯S, C—H⋯S and C—H⋯O hydrogen bonds.


Experimental
An acetone solution (30 mL) of 4-bromoaniline (0.01 mol, 1.72 g) was added dropwise into a two-necked roundbottomed flask containing 3-chloropropanoylisothiocyanate (0.01 mol). The mixture was refluxed for about 4 h, filtered into a beaker and left to evaporate at room temperature. The filtrate gave colourless crystals after 5 days on slow evaporation of the solvent (yield 79%).

Refinement
The C based H atoms were positioned geometrically with C-H = 0.93-0.97 Å and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (C). The amino H atoms ware located in difference Fourier map and refined freely with using SHELXL instruction ′DFIX 0.87 0.01′.  The molecular structure of title compound with the atom numbering scheme. The displacement ellipsoids are drawn at 50% probability level. The H atoms are presented as a small spheres of arbitrary radius. The dashed lines indicate intramolecular hydrogen bonds.

Figure 2
The crystal packing of the title compound viewed down a axis. The dashes lines indicate hydrogen bonds.

Special details
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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.

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