N-[4-Acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl]acetamide

Abstract

The title molecule, C 12 H 12 FN 3 O 2 S, shows a short intramolecular SÁ Á ÁO contact of 2.682 (18) Å. The dihedral angle between the thiadiazole ring and the benzene ring is 86.82 (11). In the crystal, N-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds generate an R 2 1 (6) graph-set motif between adjacent molecules. Pairs of futher C-HÁ Á ÁO hydrogen bonds form inversion dimers with R 2 2 (8) ring motifs. These combine to generate a three-dimensional network and stack the molecules along the b axis.

The crystal structures and Hirshfeld surface analyses of four 3,5-diacetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl derivatives

“…A search of the Cambridge Structural Database (Version 5.40, last update May 2019; Groom et al, 2016) for (5-acetamido-3acetyl-2-methyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)phenyl revealed the presence of three relevant compounds, viz. N-(4acetyl-5-(4-fluorophenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl) acetamide (CSD refcode IDOFOY; Kavitha et al, 2013), N-(4-acetyl-5-(3-methoxyphenyl)-4,5-dihydro-1,3,4-thiadiazol-2-yl) acetamide (IGAREO; Aridoss et al, 2008), that crystallized in space group P2 1 with two independent molecules in the asymmetric unit, and 2-acetylamino-4-acetyl-5-phenyl-Á 2 -1,3,4-thiadiazoline (YOLKAL; Usova et al, 1994). Here, the mean plane of the thiadiazole ring is almost normal to the 5phenyl ring with dihedral angles of ca 86.…”