Title of article :
Crystal structure of 3-{[4-(2-methoxyphenyl)piperazin-1-yl]methyl}-5-(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione
Author/Authors :
Al-Alshaikh, Monirah A. Department of Chemistry - College of Sciences - King Saud University, Saudi Arabia , Abuelizz, Hatem A. Department of Pharmaceutical Chemistry - College of Pharmacy, Saudi Arabia , El-Emam, Ali A. Department of Pharmaceutical Chemistry - College of Pharmacy, Saudi Arabia , Abdelbaky, Mohammed S. M. Department of Physical and Analytical Chemistry - Faculty of Chemistry, Spain , Garcia-Granda, Santiago Department of Physical and Analytical Chemistry - Faculty of Chemistry, Spain
Abstract :
The title compound, C18H20N4O2S2, is a new 1,3,4-oxadiazole and a key pharmacophore of several biologically active agents. It is composed of a methyl(thiophen-2-yl)-1,3,4-oxadiazole-2(3H)-thione moiety linked to a 2-methoxyphenyl unit via a piperazine ring that has a chair conformation. The thiophene ring mean plane lies almost in the plane of the oxadiazole ring, with a dihedral angle of 4.35 (9)°. The 2-methoxyphenyl ring is almost normal to the oxadiazole ring, with a dihedral angle of 84.17 (10)°. In the crystal, molecules are linked by weak C—H⋯S hydrogen bonds and C—H⋯π interactions, forming layers parallel to the bc plane. The layers are linked via weak C—H⋯O hydrogen bonds and slipped parallel π–π interactions [intercentroid distance = 3.6729 (10) Å], forming a three-dimensional structure. The thiophene ring has an approximate 180° rotational disorder about the bridging C—C bond.
Keywords :
hydrogen bonding , crystal structure , disorder , piperazine , thiophene , 1,3,4-oxadiazole
Journal title :
Acta Crystallographica Section E: Crystallographic Communications