Solvent-dependent polymorphism in isomeric N-(nitrobenzylidene)iodoanilines

G Ferguson, C Glidewell, J N Low, J M S Skakle, J L Wardell

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10 Citations (Scopus)

Abstract

Three of the nine isomeric N-(nitrobenzylidene) iodoanilines, C13H9IN2O2, have been found, when crystallized from acetone, to yield polymorphs which differ from those obtained upon crystallization from ethanol. In the second polymorph of 2-iodo-N-(2-nitrobenzylidene) aniline, the molecules are disordered across inversion centres in space group C2/c, but there are no direction-specific interactions between the molecules. In the second polymorph of 2-iodo-N-(3-nitrobenzylidene) aniline, the molecules adopt a different conformation from those in the first polymorph, and they are linked into sheets by a combination of a three-centre iodo - nitro interaction and an aromatic pi-pi stacking interaction, both of which are absent from the supramolecular structure of the first polymorph. The second polymorph of 3-iodo-N-(2-nitrobenzylidene) aniline crystallizes with Z' = 2 in space group P2(1), and the molecules are linked into sheets by one C-H center dot center dot center dot O hydrogen bond and two C - H center dot center dot center dot pi( arene) hydrogen bonds.

Original languageEnglish
Number of pages5
JournalActa Crystallographica Section C-Crystal Structure Communications
Volume61
DOIs
Publication statusPublished - Jul 2005

Keywords

  • PI-STACKING INTERACTIONS
  • CENTER-DOT-NITRO
  • CRYSTAL-STRUCTURE PREDICTION
  • SMALL ORGANIC-MOLECULES
  • HYDROGEN-BONDS
  • INTERPLAY
  • 1,4-DIIODOBENZENE
  • PATTERNS

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