title: Nine N-aryl-2-chloronicotinamides: supramolecular structures in one, two and three dimensions.
abstract: Structures are reported here for eight further substituted N-aryl-2-chloronicotinamides, 2-ClC(5)H(3)NCONHC(6)H(4)X-4'. When X = H, compound (I) (C(12)H(9)ClN(2)O), the molecules are linked into sheets by N-H...N, C-H...pi(pyridyl) and C-H...pi(arene) hydrogen bonds. For X = CH(3), compound (II) (C(13)H(11)ClN(2)O, triclinic P1 with Z' = 2), the molecules are linked into sheets by N-H...O, C-H...O and C-H...pi(arene) hydrogen bonds. Compound (III), where X = F, crystallizes as a monohydrate (C(12)H(8)ClFN(2)O.H(2)O) and sheets are formed by N-H...O, O-H...O and O-H...N hydrogen bonds and aromatic pi...pi stacking interactions. Crystals of compound (IV), where X = Cl (C(12)H(8)Cl(2)N(2)O, monoclinic P2(1) with Z' = 4) exhibit inversion twinning: the molecules are linked by N-H...O hydrogen bonds into four independent chains, linked in pairs by C-H...pi(arene) hydrogen bonds. When X = Br, compound (V) (C(12)H(8)BrClN(2)O), the molecules are linked into sheets by N-H...O and C-H...N hydrogen bonds, while in compound (VI), where X = I (C(12)H(8)ClIN(2)O), the molecules are linked into a three-dimensional framework by N-H...O and C-H...pi(arene) hydrogen bonds and an iodo...N(pyridyl) interaction. For X = CH(3)O, compound (VII) (C(13)H(11)ClN(2)O(2)), the molecules are linked into chains by a single N-H...O hydrogen bond. Compound (VIII) (C(13)H(8)ClN(3)O, triclinic P1 with Z' = 2), where X = CN, forms a complex three-dimensional framework by N-H...N, C-H...N and C-H...O hydrogen bonds and two independent aromatic pi...pi stacking interactions.
authors.affiliation: Agência Córdoba Ciência-Unidad Ceprocor, Córdoba, Argentina.
authors.forename: Silvia
authors.initials: S
authors.lastname: Cuffini
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
authors.forename: John N
authors.initials: JN
authors.lastname: Low
authors.forename: Aline G
authors.initials: AG
authors.lastname: de Oliveira
authors.forename: Marcus V N
authors.initials: MV
authors.lastname: de Souza
authors.forename: Thatyana R A
authors.initials: TR
authors.lastname: Vasconcelos
authors.forename: Solange M S V
authors.initials: SM
authors.lastname: Wardell
authors.forename: James L
authors.initials: JL
authors.lastname: Wardell
mesh_terms: D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D009536:Niacinamide / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D009536:Niacinamide