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

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

Research output: Contribution to journalArticle

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

Cite this

Isomeric N-(iodophenyl) nitrobenzamides form different three-dimensional framework structures. / Wardell, James L.; Low, John N.; Skakle, Jan; Glidewell, Christopher.

In: Acta Crystallographica Section B, Structural Science, Vol. 62, No. 5, 10.2006, p. 931-943.

Research output: Contribution to journalArticle

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title = "Isomeric N-(iodophenyl) nitrobenzamides form different three-dimensional framework structures",
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.",
keywords = "PI-stacking interactions, Center-dot-nitro, Crystal-structure prediction, O hydrogen bonds, small organic molecules, carbonyl interactions, blind test, interplay, design, crystallography",
author = "Wardell, {James L.} and Low, {John N.} and Jan Skakle and Christopher Glidewell",
year = "2006",
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T1 - Isomeric N-(iodophenyl) nitrobenzamides form different three-dimensional framework structures

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N2 - 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.

AB - 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.

KW - PI-stacking interactions

KW - Center-dot-nitro

KW - Crystal-structure prediction

KW - O hydrogen bonds

KW - small organic molecules

KW - carbonyl interactions

KW - blind test

KW - interplay

KW - design

KW - crystallography

U2 - 10.1107/S0108768106029053

DO - 10.1107/S0108768106029053

M3 - Article

VL - 62

SP - 931

EP - 943

JO - Acta Crystallographica Section B, Structural Science

JF - Acta Crystallographica Section B, Structural Science

SN - 0108-7681

IS - 5

ER -