5-(3,4-dichlorophenyl)-3-{[4-(2-pyridyl)piperazine-1-yl]methyl}-1,3,4-oxadiazole-2(3H)-one: Synthesis, Characterization, X-Ray and DFT Structures

Abstract

5-(3,4-Dichlorophenyl)-3-{[4-(2-pyridyl)piperazine-1-yl)]methyl}-1,3, 4-oxadiazole-2(3H)-one C<inf>18</inf>H<inf>17</inf>Cl<inf>2</inf>N <inf>5</inf>O<inf>2</inf> (3) is synthesized and characterized by IR, 1H NMR, 13C NMR, elemental analyses, single-crystal X-ray diffraction, and the molecular structure is also optimized at the B3LYP/6-31G(d,p) level using density functional theory (DFT). All data obtained from the spectral studies support the structural properties of 3. The molecules are linked principally by C-H.O hydrogen bonds involving carbonyl atoms and carboxylate O atoms, forming R <inf>2</inf> 2 (16) and R <inf>4</inf> 2 (20) rings that link to give a one-dimensional network of molecules. An extensive two-dimensional network of C-H.O hydrogen bonds and π.π interactions are responsible for crystal stabilization. © 2012 Pleiades Publishing, Ltd.