Synthesis, crystal structure determination, Hirshfeld surface and crystal void analyses, interaction energy calculations and energy frameworks of N-(2-chlorophenyl)-N′-propanoylthiourea
Acta Crystallographica Section E: Crystallographic Communications, vol.82, pp.816-820, 2026 (ESCI, Scopus)
- Publication Type: Article / Article
- Volume: 82
- Publication Date: 2026
- Doi Number: 10.1107/s205698902600602x
- Journal Name: Acta Crystallographica Section E: Crystallographic Communications
- Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
- Page Numbers: pp.816-820
- Keywords: 2-chlorophenyl, crystal structure, propinoyl, thiourea
- Hacettepe University Affiliated: Yes
Abstract
The title compound, C10H11ClN2S, 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 22(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 Å3 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.