4-(3-(1H-imidazol-1-yl)propyl)-(thiophen-2-ylmethyl)-1H-1.2,4-triazol-5(4H)-one (IPTT), C13H15N5OS, was synthesized and characterized by C-13 NMR, H-1 NMR, IR and single-crystal X-ray diffraction. The structure of IPTT is stabilized by three intermolecular hydrogen bonds and by intermolecular C-H center dot center dot center dot pi interaction. The compound IPTT was modelled by using DFT method. Calculations of vibrational frequencies, gauge including atomic orbital (GIAO), H-1 and C-13 NMR chemical shifts of IPTF in the ground state, total electronic charge density map and frontier molecular orbitals were performed at B3LYP/6-31 G(d) level of theory were carried out by using OFF method with 6-31 G(d) basis set. The structural parameters obtained by geometry optimization, the theoretical vibrational frequencies and chemical shift values are in good agreement with experimental ones. FT-IR, NMR and X-ray analytical results of IPTT show that the compound exists as keto form, that was supported by OFT calculations. In addition, in vitro studies showed hopeful antitumoral activity of the title IPTT compound. (c) 2011 Elsevier B.V. All rights reserved.