Synthesis, structure and computational study of N-acetyl-N'-(4-chloro-phen-yl)-thio-urea

The title compound, C₉H₉ClN₂OS, consists of a chloro-phenyl ring and acetyl moiety bridged over a thio-urea functional group. The dihedral angle between the acetyl group and the planar thio-urea 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 intra-molecular 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 mol-ecules, 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%) inter-actions. 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.