1-(2-Bromophenyl)-3-(4-chlorobutanoyl)thiourea

The asymmetric unit of the title compound, C11H12BrClN2OS, consists of two crystallographically independent molecules. In each molecule, the butanoylthiourea unit is nearly planar, with maximum deviations of 0.1292 (19) and 0.3352 (18) Å from the mean plane defined by nine non-H atoms, and is twisted relative to the terminal benzene ring with dihedral angles of 69.26 (7) and 82.41 (7)°. An intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif in each butanoylthiourea unit. In the crystal, N—H⋯O hydrogen bonds link the two independent molecules together, forming an R 2 2(12) ring motif. The molecules are further connected into a tape along the c axis via N—H⋯S and C—H⋯S hydrogen bonds.

The asymmetric unit of the title compound ( Fig. 1), consists of two crystallographically independent molecules A and B.

Experimental
An equimolar amount of 2-bromoaniline (1.22 g, 7.09 mmol) in 20 ml acetone was added drop-wise into a stirring acetone solution (75 ml) containing 4-chlorobutanoylchloride (1.00 g, 7.09 mmol) and ammonium thiocyanate (0.54 g, 7.09 mmol). The mixture was refluxed for 1 h. Then, the solution was filtered-off and left to evaporate at room temperature.

Refinement
N-bound H atoms were located in a difference Fourier map and were fixed at their found locations using riding model with U iso (H) = 1.2 U eq (N) (N-H = 0.8391-0.8465 Å). The remaining H atoms were positioned geometrically (C-H = 0.95 or 0.99 Å) and refined using a riding model with U iso (H) = 1.2 U eq (C). Five outliners 11 1 15, 6 15 1, 10 1 13, 4 0 6 and 8 0 10 were omitted in the final refinement.

Figure 1
The molecular structure of the title compound with atom labels with 30% probability displacement ellipsoids.  The crystal packing of the title compound. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity.  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