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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 Kousar, Summara Al-Qawasmeh, Raed Khanfar, Monther Saeed, Muhammad Synthesis Hirshfeld surfaces Interaction energies X-ray crystallography 1,3-Thiazolidin-4-one Supramolecular features 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. Atlanta Publishing House LLC 2026-06-30 info:eu-repo/semantics/article info:eu-repo/semantics/publishedVersion application/pdf text/plain https://www.eurjchem.com/index.php/eurjchem/article/view/2778 10.5155/eurjchem.17.2.99-108.2778 European Journal of Chemistry; Vol. 17 No. 2 (2026): June 2026; 99-108 2153-2257 2153-2249 eng https://www.eurjchem.com/index.php/eurjchem/article/view/2778/3030 https://www.eurjchem.com/index.php/eurjchem/article/view/2778/3035 Copyright (c) 2026 Summara Kousar, Raed Al-Qawasmeh, Monther Khanfar, Muhammad Saeed https://creativecommons.org/licenses/by-nc/4.0