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Thiobenzamide and thionicotnamide S-oxide were prepared as intermediates in the dimerization of corresponding thioamides to 1,2,4-thiadiazoles and the X-ray crystal structure of thionicotinamide S-oxide water solvate was determined. Crystals belong to orthorhombic Pbca space group with a = 14.129(3), b = 7.299(2), c = 15.277(3)Å, and Z = 8. The geometry of the molecule accords well with that found in similar compounds; an intramolecular N–H···O hydrogen bond is present, while the packing is mainly determined by the hydrogen bond system involving the water molecule and the side-chain of the organic molecule. The contacts between pyridine moieties, stacked along the  axis, complete the packing.