Acta Crystallographica Section B

Structural Science

Volume 62, Part 4 (August 2006)

research papers

Acta Cryst. (2006). B62, 651-665 [ doi:10.1107/S0108768106015497 ]

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

S. Cuffini, C. Glidewell, J. N. Low, A. G. de Oliveira, M. V. N. de Souza, T. R. A. Vasconcelos, S. M. S. V. Wardell and J. L. Wardell

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 [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-HO, C-HO and C-H [pi] (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 [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-HO 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-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 [pi] (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 $P\bar 1$ 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 [pi] [pi] stacking interactions.

Keywords: supramolecular structures; direction-specific intermolecular interactions; hydrogen bonds; vitamin B.


	Structure factor file (CIF format) (120.3 kbytes) [ doi:10.1107/S0108768106015497/bm5033Isup2.fcf ] Contains datablock I

	Structure factor file (CIF format) (336.7 kbytes) [ doi:10.1107/S0108768106015497/bm5033IIsup3.fcf ] Contains datablock 527

	Structure factor file (CIF format) (133.5 kbytes) [ doi:10.1107/S0108768106015497/bm5033IIIsup4.fcf ] Contains datablock 569

	Structure factor file (CIF format) (478.6 kbytes) [ doi:10.1107/S0108768106015497/bm5033IVsup5.fcf ] Contains datablock 743m

	Structure factor file (CIF format) (134.4 kbytes) [ doi:10.1107/S0108768106015497/bm5033Vsup6.fcf ] Contains datablock V

	Structure factor file (CIF format) (142.9 kbytes) [ doi:10.1107/S0108768106015497/bm5033VIsup7.fcf ] Contains datablock 744

	Structure factor file (CIF format) (130.7 kbytes) [ doi:10.1107/S0108768106015497/bm5033VIIsup8.fcf ] Contains datablock 594

	Structure factor file (CIF format) (262.7 kbytes) [ doi:10.1107/S0108768106015497/bm5033VIIIsup9.fcf ] Contains datablock 745

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