Synthesis, Characterization, and Crystal Structure of N-p-Bromophenyl-N′-Phenylacetylthiourea

Abstract

N-p-bromophenyl-N′-phenylacetylthiourea was characterized by elemental analysis, IR and 1H NMR etc. Single crystal structure of the title compound was determined on X-ray diffraction instrument. The title compound crystallizes in monoclinic space group c2/c, with a = 21.442(5) A, b = 12.208(2) A, c = 11.955(2) A, β = 109.375(4)°, and Dcalc = 1.571 g/cm3 for Z = 8. An intermolecular hydrogen bond N–H···S which links two thiourea molecules as a dimer and an offset face-to-face π–π stacking interaction were observed in the title compound. The strong non-covalent interaction influences the conformation and property of thiourea derivatives. The title compound, N-p-bromophenyl-N′-phenylacetylthiourea, was synthesized by the treatment of phenylacetyl chloride with 4-bromoaniline and its crystal structure determined. Single crystal X-ray diffraction analysis reveals that hydrogen bonds and face-to-face π–π stacking interactions have strong influence on the conformation and molecular stacking of the title compound.