Synthesis, structural and spectroscopic studies of 1-(2-FUROYL)-3-phenylthiourea: a theoretical and experimental approach

Abstract

ABSTRACT The thiourea derivative 1-(2-Furoyl)-3-phenylthiourea (FPT) was synthesized and characterized by using spectroscopic (IR, Raman, UV–VIS, 1H and 13C NMR) and structural methods (powder X-ray diffraction data). The experimental measurements were complemented with quantum chemical calculations. FPT crystallizes in the monoclinic crystal system, space group P21/c, with cell parameters a = 4.7679(5) Å, b = 20.9704(2) Å, c = 12.5109(5) Å and β = 109.811(10)°, V = 1176.87(3) Å3. In the crystal structure, the thiourea group makes dihedral angle of 43.8(5)° with the furoyl group, whereas the benzene ring is inclined by 24.3(4)°. The anti-syn geometry of the thiourea unit is stabilized by intramolecular N–H … O hydrogen bond between the H atom of the syn thioamide and the carbonyl O atom. In the crystal structure, molecules of FPT are packed through N–H···S, C–H···O and C–H···C hydrogen bonds, and a π–π interaction with offset arrangement. Hirshfeld surface analysis was performed in order to evaluate and quantify intermolecular interactions. The Hirshfeld surface analysis indicated that the H···H interactions comprise the majority of interactions. Shape index and curvedness clearly indicate π–π interactions in the compound FPT.