Crystal structure of 1-(1,3-benzothiazol-2-yl)-3-(4-bromobenzoyl)thiourea

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 <i>trans</i> conformtion (sometimes also called <i>s</i>-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 <i>S</i>(6) ring. In the crystal, pairs of adjacent mol-ecules inter-act <i>via</i> inter-molecular hydrogen bonds of type C-H⋯N, C-H⋯S and N-H⋯S, resulting in mol-ecular layers parallel to the <i>ac</i> plane.