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The title compounds, 4-(5-acetamido-3-acetyl-2-methyl-2,3-di-hydro-1,3,4-thia-diazol-2-yl)phenyl benzoate, C 20 H 19 N 3 O 4 S ( I ), 4-(5-acetamido-3-acetyl-2-methyl-2,3-di-hydro-1,3,4-thia-diazol-2-yl)phenyl isobutyrate 0.25-hydrate, C 17 H 21 N 3 O 4 S·0.25H 2 O ( II ), 4-(5-acetamido-3-acetyl-2-methyl-2,3-di-hydro-1,3,4-thia-diazol-2-yl)phenyl propionate, C 16 H 19 N 3 O 4 S ( III ) and 4-(5-acetamido-3-acetyl-2-methyl-2,3-di-hydro-1,3,4-thia-diazol-2-yl)phenyl cinnamate chloro-form hemisolvate, C 22 H 21 N 3 O 4 S·0.5CHCl 3 ( IV ), all crystallize with two independent mol-ecules ( A and B ) in the asymmetric unit in the triclinic P space group. Compound II crystallizes as a quaterhydrate, while compound IV crystallizes as a chloro-form hemisolvate. In compounds I , II , III (mol-ecules A and B ) and IV (mol-ecule A ) the five-membered thia-diazole ring adopts an envelope conformation, with the tetra-substituted C atom as the flap. In mol-ecule B of IV this ring is flat (r.m.s. deviation 0.044 Å). The central benzene ring is in general almost normal to the mean plane of the thia-diazole ring in each mol-ecule, with dihedral angles ranging from 75.8 (1) to 85.5 (2)°. In the crystals of all four compounds, the A and B mol-ecules are linked via strong N-H⋯O hydrogen bonds and generate centrosymmetric four-membered R  4  4 (28) ring motifs. There are C-H⋯O hydrogen bonds present in the crystals of all four compounds, and in I and II there are also C-H⋯π inter-actions present. The inter-molecular contacts in the crystals of all four compounds were analysed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

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