Synthesis and molecular structure investigation by DFT and X-Ray diffraction of ARNO

Abstract

We report here the synthesis of (Z)-5-(4-nitrobenzyliden)- 3-N(2-ethoxyphenyl)-2-thioxo-thiazolidin-4-one (ARNO) compound. The crystal structure has been determined by X-ray diffraction. The compound crystallizes in the triclinic system with space group P 1 and cell parameters: a = 9.1289(19),b = 9.3717(7), c = 12.136(3) A ° ,a = 102.133 (11) , b = 90.99(2) , c = 117.165(9) , V = 895.4(3) A ° 3 and Z = 2. The structure has been refined to a final R = 0.05 for 2591 observed reflections. The refined structure was found to be significantly non planar. The molecule exhibits intermolecular hydrogen bond of type C–H_O and C–H_S. ab initio calculations were also were performed at Hartree–Fock and density functional theory levels. The full HF and DFT geometry optimization was carried out using LANL2DZ, 6-31G* and B3LYP/6-31?G** basis sets. The optimized geometry of the title compound was found to be consistent structure determined by X-ray diffraction. The minimumenergy of geometrical structure is obtained by using level HF/LANL2DZ basis sets.