Isomeric N-(iodophenyl) nitrobenzamides form different three-dimensional framework structures

James L. Wardell, John N. Low, Jan Skakle, Christopher Glidewell

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18 Citations (Scopus)

Abstract

The isomeric N-(iodophenyl)nitrobenzamides, C13H9IN2O3, all form different three-dimensional framework structures. Molecules of N-(2-iodophenyl)-3-nitrobenzamide (II) are linked by a combination of N-H center dot center dot center dot O and C-H center dot center dot center dot O hydrogen bonds and a two-centre iodo center dot center dot center dot carbonyl interaction. The supramolecular structure of N-(2-iodophenyl)-4-nitrobenzamide (III) is built from one N-H center dot center dot center dot O and two C-H center dot center dot center dot O hydrogen bonds, but short I center dot center dot center dot O contacts are absent from the structure. In N-(3-iodophenyl)-2-nitrobenzamide (IV), which crystallizes with Z' = 2 in space group P2(1), the structure contains two N-H center dot center dot center dot O hydrogen bonds, four C-H center dot center dot center dot O hydrogen bonds, two two-centre iodo center dot center dot center dot nitro interactions and an aromatic pi center dot center dot center dot pi stacking interaction. The structure of N-(3-iodophenyl)-3-nitrobenzamide (V) contains one N-H center dot center dot center dot O hydrogen bond and three C-H center dot center dot center dot O hydrogen bonds, together with a two-centre iodo center dot center dot center dot nitro interaction and an aromatic pi center dot center dot center dot pi stacking interaction, while in N-(3-iodophenyl)-4-nitrobenzamide ( VI), the combination of one N-H center dot center dot center dot O hydrogen bond and two C-H center dot center dot center dot O hydrogen bonds is augmented not only by a two-centre iodo center dot center dot center dot nitro interaction and an aromatic pi center dot center dot center dot pi stacking interaction, but also by a dipolar carbonyl center dot center dot center dot carbonyl interaction. In the supramolecular structure of N-(4-iodophenyl)-4-nitrobenzamide (IX), which crystallizes with Z' = 2 in space group P (1) over bar, there are two N-H center dot center dot center dot O hydrogen bonds, four C-H center dot center dot center dot O hydrogen bonds and two three-centre iodo center dot center dot center dot nitro interactions.

Original languageEnglish
Pages (from-to)931-943
Number of pages13
JournalActa Crystallographica Section B, Structural Science
Volume62
Issue number5
DOIs
Publication statusPublished - Oct 2006

Keywords

  • PI-stacking interactions
  • Center-dot-nitro
  • Crystal-structure prediction
  • O hydrogen bonds
  • small organic molecules
  • carbonyl interactions
  • blind test
  • interplay
  • design
  • crystallography

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