Synthesis, structure and computational study of 1-acetyl-3-(3,5-di-chloro-phen-yl)thio-urea.

Abstract

The title compound, C9H8Cl2N2OS, consists of di-chloro-phenyl and acetyl moieties attached to the N atoms of the bridging thio-urea group. The dihedral angle between the acetyl group and the thio-urea group is 5.6 (6)°, and they are oriented with respect to the phenyl ring at dihedral angles of 70.3 (4) and 69.1 (1)°, respectively. The mol-ecular conformation features an intra-molecular N-H⋯O hydrogen bond with an S(6) ring motif. In the crystal, C-H⋯Cl and double-acceptor N-H⋯S and C-H⋯S hydrogen bonds link the mol-ecules, enclosing R12(6), R22(8) and R22(20) ring motifs, into infinite chains running parallel to the b axis. Neither π⋯π nor C-H⋯π(ring) inter-actions are observed. Hirshfeld surface analysis revealed that the most important contributions for crystal packing are H⋯H (28.6%), H⋯Cl/Cl⋯H (22.9%), H⋯S/S⋯H (10.4%), H⋯O/O⋯H (9.6%) and H⋯C/C⋯H (9.0%) inter-actions. The volume of the crystal voids and the percentage of free space were calculated to be 62.7 Å3 and 10.9%. N-H⋯S, C-H⋯S and C-H⋯Cl hydrogen-bonding energies of -10.0, -3.9 and -7.7 kJ mol-1, respectively, were computed. Evaluations of the electrostatic, dispersion and total energy frameworks indicate that the crystal consolidation is dominated by dispersion energy contributions.

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