Syntheses, crystal structures and Hirshfeld surface analysis of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole
R. Ya. OkmanovNational University of Uzbekistan named after Mirzo Ulugbek, University Str. 4, Tashkent, 100174, UzbekistanA. A. ZiyaevS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent, 100170, UzbekistanAzimboy Sh. AbdukarimovNational University of Uzbekistan named after Mirzo Ulugbek, University Str. 4, Tashkent, 100174, UzbekistanT. T. ToshmurodovS. Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent, 100170, UzbekistanT.S. KholikovNational University of Uzbekistan named after Mirzo Ulugbek, University Str. 4, Tashkent, 100174, Uzbekistan
ABI
Abstract
The title compounds were synthesized by alkylation of 5-[(4-dimethylamino)phenyl]-1,3,4-oxadiazole-2-thiol with benzyl chloride or 2-chloro-6-fluorobenzyl chloride in the presence of potassium carbonate. The yields of 2-(benzylsulfanyl)-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C 17 H 17 N 3 OS (I), and 2-[(2-chloro-6-fluorobenzyl)sulfanyl]-5-[4-(dimethylamino)phenyl]-1,3,4-oxadiazole, C 17 H 15 ClFN 3 OS (II), were 96 and 92%, respectively. In the crystal structures of (I) and (II), C–H...π interactions are observed between neighboring molecules. Hirshfeld surface analysis indicates that H...H and H...C/C...H interactions make the most important contributions to the crystal packing.
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