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-ClC5H3NCONHC 6H4X-4′. When X = H, compound (I) (C 12H9ClN2O), the molecules are linked into sheets by N-H⋯N, C-H⋯π(pyridyl) and C-H⋯π(arene) hydrogen bonds. For X = CH3, compound (II) (C13H 11ClN2O, triclinic P1̄ with Z′ = 2), the molecules are linked into sheets by N-H⋯O, C-H⋯O and C-H⋯π(arene) hydrogen bonds. Compound (III), where X = F, crystallizes as a monohydrate (C12H8ClFN 2O·H2O) and sheets are formed by N-H⋯O, O-H⋯O and O-H⋯N hydrogen bonds and aromatic π⋯π stacking interactions. Crystals of compound (IV), where X = Cl (C 12H8Cl2N2O, 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⋯π(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⋯π(arene) hydrogen bonds and an iodo⋯N(pyridyl) interaction. For X = CH3O, compound (VII) (C13H11ClN 2O2), the molecules are linked into chains by a single N-H⋯O hydrogen bond. Compound (VIII) (C13H8ClN 3O, triclinic P1̄ 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 π⋯π stacking interactions. © 2006 International Union of Crystallography Printed in Great Britain - all rights reserved.