Structural and spectral studies of N-(4-chloro)benzoyl-N'-2-tolylthiourea

Abstract The crystal and molecular structure of the N -(4-chloro)benzoyl- N ′-(4-tolyl)thiourea (C 15 H 13 N 2 OSCl, M r =304.79) is determined by X-ray diffraction. The crystal structure is monoclinic, space group: P 2 1 / n , a =16.097(6), b =4.5989(2), c=19.388(7) A and β =89.299(6)° V=1434.7(9) A 3 , Z =4. FTIR and NMR spectra have been characterized. The interactions of intramolecular and intermolecular hydrogen bonds have been discussed. Density functional theory (DFT) (B3LYP) methods have been used to determine the structure and energies of stable conformers. Minimum energy conformations are calculated as a function of the torsion angle θ (C13–N1–C14–N2) varied every 30°. The optimized geometry corresponding to crystal structure is the most stable conformation. This has partly been attributed to intramolecular hydrogen bonds. With the basis sets of the 6-311G* quality, the DFT calculated bond parameters and harmonic vibrations are predicted in a very good agreement with experimental data.