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Crystal structure of 3-[(4-benzylpiperazin-1-yl)methyl]-5-(thiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazole-2-thione

2015; International Union of Crystallography; Volume: 71; Issue: 3 Linguagem: Inglês

10.1107/s2056989015002273

2056-9890

Fatmah A. M. Al-Omary, Ali A. El‐Emam, Hazem A. Ghabbour, C. S. Chidan Kumar, Ching Kheng Quah, Hoong‐Kun Fun,

Structural and Chemical Analysis of Organic and Inorganic Compounds

The title 1,3,4-oxadiazole-2-thione derivative, C 18 H 20 N 4 OS 2 , crystallized with two independent molecules ( A and B ) in the asymmetric unit. The 2-thienyl rings in both molecules are rotationally disordered over two orientations by approximately 180° about the single C—C bond that connects it to the oxadiazole thione ring; the ratios of site occupancies for the major and minor components were fixed in the structure refinement at 0.8:0.2 and 0.9:0.1 in molecules A and B , respectively. The 1,3,4-oxadiazole-2-thione ring forms dihedral angles of 7.71 (16), 10.0 (11) and 77.50 (12)° (molecule A ), and 6.5 (3), 6.0 (9) and 55.30 (12)° (molecule B ) with the major and minor parts of the disordered thiophene ring and the mean plane of the adjacent piperazine ring, respectively, resulting in approximately V-shaped conformations for the molecules. The piperazine ring in both molecules adopts a chair conformation. The terminal benzene ring is inclined towards the mean plane of the piperazine ring with N—C—C—C torsion angles of −58.2 (3) and −66.2 (3)° in molecules A and B , respectively. In the crystal, no intermolecular hydrogen bonds are observed. The crystal packing features short S...S contacts [3.4792 (9) Å] and π–π interactions [3.661 (3), 3.664 (11) and 3.5727 (10) Å], producing a three-dimensional network.