Crystal structure, Hirshfeld surface analysis and computational studies of thiazolidin-4-one derivative: (Z)-5-(4-chlorobenzylidene)-3-(2-ethoxyphenyl)-2-thioxothiazolidin-4-one

Abstract

The title compound (Z)-5-(4-chlorobenzylidene)-3-(2-ethoxyphenyl)-2-thioxothiazolidin-4-one, called (CBBTZ) was characterized by X-ray single crystal diffraction, 1H-NMR and 13C-NMR spectra. The compound crystallizes in the triclinic space group P-1 with the following cell parameters: a = 9.2171(19), b = 8.4612(7), c = 11.935(3) Å, a = 101.623(11)°, β = 90.89(2)°, g = 118.148 (9)°, V = 797.3(3) Å3 and Z = 2. A data set of 2591 observed reflections were used in the refinement leading to a structure with a refinement factor of 0.05. Theoretical investigations were carried out using HF and DFT levels of theory at 6-31G(d,p) basis set. The X-ray structure is compared with that computed. The calculated geometrical parameters are in good agreement with those determined by X-ray diffraction. The dihedral angle between the two benzene rings is 16.89(5)° indicating that the structure is non planar. The molecule exhibits intra- and intermolecular contacts of type C–H⋅⋅⋅O, C–H⋅⋅⋅S and C–H⋅⋅⋅Cl. The intercontacts in crystal structure are explored using Hirshfeld Surfaces analysis method.

Keywords

• Structure
• thiazolidin-4-one
• theoretical calculations
• Intermolecular interactions
• Hirshfeld Surface