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Nine N-aryl-2-chloronicotinamides: supramolecular structures in one, two and three dimensions

Authors: De Souza, M.V.N.; Cuffini, S.; Wardell, S.M.S.V.; Wardell, J.L.; Vasconcelos, T.A.; Oliveira, A.G.; Glidewell, C.


Abstract

Structures are reported here for eight further substituted N-aryl-2-chloronicotinamides, 2-ClC5H3NCONHC6H4X-4′. When X = H, compound (I) (C12H9ClN2O), the molecules are linked into sheets by N-H...N, C-H...[pi](pyridyl) and C-H...[pi](arene) hydrogen bonds. For X = CH3, compound (II) (C13H11ClN2O, triclinic P\bar 1 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 (C12H8ClFN2O·H2O) 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 (C12H8Cl2N2O, monoclinic P21 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) (C12H8BrClN2O), the molecules are linked into sheets by N-H...O and C-H...N hydrogen bonds, while in compound (VI), where X = I (C12H8ClIN2O), 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 = CH3O, compound (VII) (C13H11ClN2O2), the molecules are linked into chains by a single N-H...O hydrogen bond. Compound (VIII) (C13H8ClN3O, triclinic P\bar 1 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.
Keywords: None Document Type: Research Article DOI: http://dx.doi.org/10.1107/S0108768106015497 Publication date: 1 de Janeiro de 2006

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