Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 3 (March 2013)

organic compounds

Acta Cryst. (2013). C69, 293-298    [ doi:10.1107/S0108270113004344 ]

Three 2-(methysulfanyl)­nicotinamides

L. R. Gomes, J. N. Low, J. L. Wardell, A. C. Pinheiro, T. C. N. de Mendonça and M. V. N. de Souza

Abstract: 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.

Formula: C13H18N2OS, C10H14N2OS and C9H12N2O2S·2H2O

hkldisplay filedownload file

Structure factor file (CIF format) (134.1 kbytes)
[ doi:10.1107/S0108270113004344/sk3475Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (220.1 kbytes)
[ doi:10.1107/S0108270113004344/sk3475IIsup4.hkl ]
Contains datablock II

hkldisplay filedownload file

Structure factor file (CIF format) (101.5 kbytes)
[ doi:10.1107/S0108270113004344/sk3475IIIsup3.hkl ]
Contains datablock III


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