title: Three 2-(methysulfanyl)nicotinamides.
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.
authors: REQUIMTE, Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade do Porto, Rua do Campo Alegre, 687, P-4169-007 Porto, Portugal.
authors: Ligia R
authors: LR
authors: Gomes
authors: John Nicolson
authors: JN
authors: Low
authors: James L
authors: JL
authors: Wardell
authors: Alessandra C
authors: AC
authors: Pinheiro
authors: Thais C N
authors: TC
authors: de Mendonça
authors: Marcus V N
authors: MV
authors: de Souza
mesh_terms: D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008968:Molecular Conformation; D015394:Molecular Structure; D009536:Niacinamide / Q000031:analogs & derivatives* / Q000737:chemistry*
chemical_list: C580904:N-(2-hydroxyethyl)-2-(methylsulfanyl)nicotinamide dihydrate; C580902:N-cyclohexyl-2-(methylsulfanyl)nicotinamide; C580903:N-isopropyl-2-(methylsulfanyl)nicotinamide; D009536:Niacinamide