Synthesis, crystal structure, Hirshfeld surface and interaction energies analysis of 3-(benzo[d][1,3]dioxol-5-yl)-2-(pyridin-3-yl)thiazolidin-4-one

Abstract

3-(Benzo[d][1,3]dioxol-5-yl)-2-(pyridin-3-yl)thiazolidin-4-one, a novel derivative of 1,3-thiazolidin-4-one, was synthesized by Schiff base formation followed by cyclocondensation with thioglycolic acid. The structure of the synthesized compound was characterized by spectroscopic techniques, including NMR, GC-MS, and HRMS. The molecular structure was unambiguously established by single-crystal X-ray diffraction. The compound crystallizes in the monoclinic crystal system with space group C2/c (No. 15) and unit-cell parameters a = 14.69 Å, b = 9.615 Å, c = 22.198 Å, and β = 98.49°. The molecular geometry reveals that the sulfur atom of the 1,3-thiazolidin-4-one ring is significantly out of the plane of the remaining ring atoms and adopts a puckered conformation. In the solid state, the supramolecular architecture is stabilized by a combination of interactions, including hydrogen bonding and weak π···π interactions. Furthermore, Hirshfeld surface analysis and two-dimensional fingerprint plots were used to quantify the intermolecular interactions, revealing that H···H (32.4%), O···H/H···O (20.2%) C···H/H···C (18.1%) contacts make the most significant contribution to Hirshfeld surfaces. Energy framework calculations indicated that dispersion energy, arising mainly from π···π interactions, is the dominant contributor to stabilization of the crystal packing.