Open AccessNine N ‐aryl‐2‐chloronicotinamides: supramolecular structures in one, two and three dimensions
Author(s) -
Cuffini Silvia,
Glidewell Christopher,
Low John N.,
De Oliveira Aline G.,
De Souza Marcus V. N.,
Vasconcelos Thatyana R. A.,
Wardell Solange M. S. V.,
Wardell James L.
Publication year - 2006
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
eISSN - 1600-5740
pISSN - 0108-7681
DOI - 10.1107/s0108768106015497
Subject(s) - triclinic crystal system , hydrogen bond , molecule , crystallography , monoclinic crystal system , chemistry , aryl , crystal structure , supramolecular chemistry , stereochemistry , stacking , alkyl , organic chemistry
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⋯π(pyridyl) and C—H⋯π(arene) hydrogen bonds. For X = CH 3 , compound (II) (C 13 H 11 ClN 2 O, triclinic 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 (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 π⋯π stacking interactions. Crystals of compound (IV), where X = Cl (C 12 H 8 Cl 2 N 2 O, monoclinic P 2 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) (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⋯π(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 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.