Synthesis, structure and computational study of N-acetyl-N′-(4-chlorophenyl)thiourea
Acta Crystallographica Section E: Crystallographic Communications, cilt.82, ss.1066-1070, 2026 (ESCI, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 82
- Basım Tarihi: 2026
- Doi Numarası: 10.1107/s2056989026008315
- Dergi Adı: Acta Crystallographica Section E: Crystallographic Communications
- Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
- Sayfa Sayıları: ss.1066-1070
- Anahtar Kelimeler: 4-chlorophenyl, acetyl, crystal structure, thiourea
- Hacettepe Üniversitesi Adresli: Evet
Özet
The title compound, C9H9ClN2OS, consists of a chlorophenyl ring and acetyl moiety bridged over a thiourea functional group. The dihedral angle between the acetyl group and the planar thiourea 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 intramolecular 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 molecules, enclosing R 22(8) and R 22(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%) interactions. 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.