Open AccessThree isomeric 1‐(2‐chloronicotinoyl)‐2‐(nitrophenyl)hydrazines, including three polymorphs of 1‐(2‐chloronicotinoyl)‐2‐(2‐nitrophenyl)hydrazine: hydrogen‐bonded supramolecular structures in two and three dimensions
Author(s) -
Wardell Solange M. S. V.,
Souza Marcus V. N. de,
Wardell James L.,
Low John N.,
Glidewell Christopher
Publication year - 2007
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
eISSN - 1600-5740
pISSN - 0108-7681
DOI - 10.1107/s0108768106041358
Subject(s) - hydrogen bond , orthorhombic crystal system , monoclinic crystal system , molecule , stacking , crystallography , chemistry , supramolecular chemistry , hydrazine (antidepressant) , crystal structure , stereochemistry , organic chemistry , chromatography
1‐(2‐Chloronicotinoyl)‐2‐(2‐nitrophenyl)hydrazine, C 12 H 9 ClN 4 O 3 , crystallizes in three polymorphic forms, two monoclinic forms in space groups Cc (I a ) and P 2 1 (I b ), and an orthorhombic form in space group Pbcn (I c ). In the Cc polymorph (I a ) the molecules are linked into sheets by combinations of one N—H⋯O and two C—H⋯O hydrogen bonds, while in the P 2 1 polymorph (I b ) the molecules are linked into sheets by combinations of three hydrogen bonds, one each of N—H⋯O, C—H⋯N and C—H⋯O types. In the orthorhombic polymorph (I c ) the molecules are linked into a complex three‐dimensional framework structure by a combination of one N—H⋯O, one N—H⋯N and three C—H⋯O hydrogen bonds, and an aromatic π⋯π stacking interaction. In the isomeric compound 1‐(2‐chloronicotinoyl)‐2‐(3‐nitrophenyl)hydrazine (II) the molecules are again linked into a three‐dimensional framework, this time by a combination of three hydrogen bonds, one each of N—H⋯O, N—H⋯N and C—H⋯O types, weakly augmented by a π⋯π stacking interaction. The molecules of 1‐(2‐chloronicotinoyl)‐2‐(4‐nitrophenyl)hydrazine (III) are linked into sheets by a combination of three hydrogen bonds, one each of N—H⋯O, N—H⋯N and C—H⋯O types.