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The molecular and crystal structures of a series of 5-Ph-2-(arylCH=NNH)-1,3,4-thiadiazoles [ 2 : aryl = 4-XC 6 H 4  (X = H [ 2a ], 4-Cl [ 2b ], 4-Br [ 2c ], 4-F 3 CO [ 2d ], 2-HO [ 2e ], 2-HO-3-MeO [ 2f ] as well as [5-Ph-2-(4-HOC 6 H 4 CH=NNH)-1,3,4-thiadiazole] 3 (H 2 O) 2 ] [( 2g ) 3  · 2 (H 2 O)] are reported. The compounds were prepared as part of a study on typanocide reagents as possible treatments for Chagas‘ disease. The asymmetric unit of [( 2g ) 3  · 2 (H 2 O)] consists of three independent molecules and two water molecules, in contrast to the single molecules comprising the asymmetric units of  2a – 2f . In all cases, N–H · · · N intermolecular hydrogen bonding results in the formation of dimers linked by R 2  2 (8) rings. As well as the hydrogen-bonded dimers, the molecules of  2a–2f  are also linked by other weak interactions including aromatic π–π stacking and C–H · · · X bonds.

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5-Phenyl-2-(benzalhydrazonyl)-1,3,4-thiadiazoles, potential trypanocidal agents: consistent dimer formation via N–H  · · ·  N intermolecular hydrogen bonds