Crystal structure of 1-(1,3-benzo-thia-zol-2-yl)-3-(4-bromo-benzo-yl)thio-urea

Abstract

The chemical reaction of 4-bromo-benzoyl-chloride and 2-amino-thia-zole in the presence of potassium thio-cyanate yielded a white solid formulated as C₁₅H₁₀BrN₃OS₂, which consists of 4-bromo-benzamido and 2-benzo-thia-zolyl moieties connected by a thio-urea group. The 4-bromo-benzamido and 2-benzo-thia-zolyl moieties are in a trans conformtion (sometimes also called s-trans due to the single bond) with respect to the N-C bond. The dihedral angle between the mean planes of the 4-bromo-phenyl and the 2-benzo-thia-zolyl units is 10.45 (11)°. The thio-urea moiety, -C-NH-C(=S) -NH- fragment forms a dihedral angle of 8.64 (12)° with the 4-bromo-phenyl ring and is almost coplanar with the 2-benzo-thia-zolyl moiety, with a dihedral angle of 1.94 (11)°. The mol-ecular structure is stabilized by intra-molecular N-H⋯O hydrogen bonds, resulting in the formation of an S(6) ring. In the crystal, pairs of adjacent mol-ecules inter-act via inter-molecular hydrogen bonds of type C-H⋯N, C-H⋯S and N-H⋯S, resulting in mol-ecular layers parallel to the ac plane.

Keywords: 2-benzo­thia­zole; 4-bromo­benzoyl­chloride; crystal structure; potassium cyanate; thio­urea.

Figure 1

A view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are plotted at the 30% probability level.

Figure 2

Partial packing view along the a axis, H atoms are omitted for clarity.

Figure 3

Partial packing view down the b axis showing the formation of (8) graph-set motifs. Hydrogen bonds are drawn as dashed lines.