International Union of Crystallography, 2013
Acta Crystallographica Section C
Volume 69, Issue 3, pages 293–298, March 2013
How to Cite
Gomes, L. R., Low, J. N., Wardell, J. L., Pinheiro, A. C., Mendonça, T. C. N. d. and Souza, M. V. N. d. (2013), Three 2-(methysulfanyl)nicotinamides. Acta Crystallographica Section C, 69: 293–298. doi: 10.1107/S0108270113004344
The molecular conformations of three N-alkyl-2-(methylsulfanyl)nicotinamide derivatives, namely N-cyclohexyl-2-(methylsulfanyl)nicotinamide, C13H18N2OS, (I), N-isopropyl-2-(methylsulfanyl)nicotinamide, C10H14N2OS, (II), in which there are two molecules in the asymmetric unit which were chosen to form a hydrogen-bonded pair, and N-(2-hydroxyethyl)-2-(methylsulfanyl)nicotinamide dihydrate, C9H12N2O2S·2H2O, (III), are compared with those of four unsubstituted N-alkylnicotinamide compounds. The substituted compounds show a higher degree of torsion of the pyridine ring with respect to the amide group than do the unsubstituted compounds, with dihedral angles in the range 40–60° for the former and 20–35° for the latter. In (I) and (II), the supramolecular structure is defined by amide-N to carbonyl-O chains. In (III), the nicotinamide molecules are linked by hydrogen bonds to two water molecules resulting in two linked chains of rings which form the three-dimensional network.