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

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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-HN, C-H(pyridyl) and C-H(arene) hydrogen bonds. For X = CH₃, compound (II) (C₁₃H₁₁ClN₂O, triclinic with Z‘ = 2), the molecules are linked into sheets by N-HO, C-HO and C-H(arene) hydrogen bonds. Compound (III), where X = F, crystallizes as a monohydrate (C₁₂H₈ClFN₂O·H₂O) and sheets are formed by N-HO, O-HO and O-HN hydrogen bonds and aromatic stacking interactions. Crystals of compound (IV), where X = Cl (C₁₂H₈Cl₂N₂O, monoclinic P2₁ with Z‘ = 4) exhibit inversion twinning: the molecules are linked by N-HO hydrogen bonds into four independent chains, linked in pairs by C-H(arene) hydrogen bonds. When X = Br, compound (V) (C₁₂H₈BrClN₂O), the molecules are linked into sheets by N-HO and C-HN hydrogen bonds, while in compound (VI), where X = I (C₁₂H₈ClIN₂O), the molecules are linked into a three-dimensional framework by N-HO and C-H(arene) hydrogen bonds and an iodoN(pyridyl) interaction. For X = CH₃O, compound (VII) (C₁₃H₁₁ClN₂O₂), the molecules are linked into chains by a single N-HO hydrogen bond. Compound (VIII) (C₁₃H₈ClN₃O, triclinic with Z‘ = 2), where X = CN, forms a complex three-dimensional framework by N-HN, C-HN and C-HO hydrogen bonds and two independent aromatic stacking interactions.

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Keywords: None Document Type: Research Article DOI: http://dx.doi.org/10.1107/S0108768106015497 Publication date: 1 de Janeiro de 2006