Synthesis, crystal structure determination, Hirshfeld surface and crystal void analyses, inter-action energy calculations and energy frameworks of N-(2-methyl-phen-yl)-N'-pivaloyl-thio-urea.

Abstract

The title compound [systematic name: 3-(2,2-di-methyl-propano-yl)-1-(2-methyl-phen-yl)thio-urea], C₁₃H₁₈N₂OS, consists of methyl-phenyl and pivaloyl moieties attached to the N atoms of thio-urea. The latter is twisted by 78.08 (10)° with respect to the phenyl ring. An intra-molecular N-H⋯O hydrogen bond with an S(6) ring motif consolidates the mol-ecular conformation. In the crystal, C-H⋯S hydrogen bonds link two mol-ecules, enclosing R ² ₂(14) ring motifs, into centrosymmetric dimers. Furthermore, π-π stacking and C-H⋯π(ring) inter-actions are present. Hirshfeld surface analysis revealed that the most important contributions to the crystal packing are from H⋯H (62.4%), H⋯S/S⋯H (13.6%) and H⋯C/C⋯H (12.9%) inter-actions. The volume of the crystal voids and the percentage of free space were calculated to be 91.57 ų and 13.35%, showing that there is no large cavity in the crystal packing. A C-H⋯S hydrogen-bonding energy of -5.4 kJ mol^-1 was calculated. Evaluation of the electrostatic, dispersion and total energy frameworks indicates that the packing is dominated by dispersion energy contributions.