Synthesis, structure and computational study of N -acetyl -N ′-(4-chlorophenyl)thiourea

The title compound, C 9 H 9 ClN 2 OS, consists of a chlorophenyl ring and acetyl moiety bridged over a thiourea functional group. The dihedral angle between the acetyl group and the planar thiourea group is 1.9 (5)°, and they are oriented at dihedral angles of 57.9 (5) and 59.77 (16)°, respectively, with respect to the phenyl ring. An intramolecular N—H...O hydrogen bond forms an S (6) ring motif. In the crystal, N—H...S and N—H...O hydrogen bonds link the molecules, enclosing R 2 2 (8) and R 2 2 (12) ring motifs, into infinite chains along the a -axis direction. Hirshfeld surface analysis revealed that the most important contributions for crystal packing are H...H (31.1%), H...Cl/Cl...H (16.9%), H...S/S...H (14.4%), H...C/C...H (12.9%) and H...O/O...H (9.4%) interactions. Computational methods revealed N—H...S and N—H...O hydrogen-bonding energies of −13.8 and −10.1 kJ mol −1 , respectively. Evaluations of the electrostatic, dispersion and total energy frameworks indicate that the crystal stabilization is dominated by dispersion energy contributions.