Synthesis, crystal structure determination, Hirshfeld surface and crystal void analyses, interaction energy calculations and energy frameworks of N -(2-chlorophenyl)- N ′-propanoylthiourea

The title compound, C 10 H 11 ClN 2 S, consists of a chlorophenyl ring and a propanoyl moiety bridged over a thiourea functional group. The dihedral angle between the planar propinoyl and thiourea groups is 8.33 (14)°, and they are oriented at 48.50 (14) and 56.09 (6)° with respect to the phenyl ring. The intramolecular N—H...O hydrogen bond forms an S(6) ring motif. In the crystal, N—H...S hydrogen bonds link two molecules, enclosing R 2 2 (8) ring motifs, into centrosymmetric dimers. π–π stacking interactions help to consolidate the packing. Hirshfeld surface analysis revealed that the most important contributions for crystal packing are H...H (39.2%), H...Cl/Cl...H (15.8%), H...S/S...H (14.2%) and H...C/C...H (9.9%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 105.62 Å 3 and 9.33%, showing that there is no large cavity in the crystal packing. Computational methods indicated an N—H...S hydrogen-bonding energy of −53.5 kJ mol −1 . Evaluations of the electrostatic, dispersion and total energy frameworks indicate that the crystal cohesion is dominated by electrostatic energy contributions.