Open AccessIsomeric N ‐(iodophenyl)nitrobenzamides form different three‐dimensional framework structures
Author(s) -
Wardell James L.,
Low John N.,
Skakle Janet M. S.,
Glidewell Christopher
Publication year - 2006
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
eISSN - 1600-5740
pISSN - 0108-7681
DOI - 10.1107/s0108768106029053
Subject(s) - hydrogen bond , stacking , supramolecular chemistry , chemistry , crystallography , stereochemistry , nitro , molecule , crystal structure , organic chemistry , alkyl
The isomeric N ‐(iodophenyl)nitrobenzamides, C 13 H 9 IN 2 O 3 , all form different three‐dimensional framework structures. Molecules of N ‐(2‐iodophenyl)‐3‐nitrobenzamide (II) are linked by a combination of N—H⋯O and C—H⋯O hydrogen bonds and a two‐centre iodo⋯carbonyl interaction. The supramolecular structure of N ‐(2‐iodophenyl)‐4‐nitrobenzamide (III) is built from one N—H⋯O and two C—H⋯O hydrogen bonds, but short I⋯O contacts are absent from the structure. In N ‐(3‐iodophenyl)‐2‐nitrobenzamide (IV), which crystallizes with Z ′ = 2 in space group P 2 1 , the structure contains two N—H⋯O hydrogen bonds, four C—H⋯O hydrogen bonds, two two‐centre iodo⋯nitro interactions and an aromatic π⋯π stacking interaction. The structure of N ‐(3‐iodophenyl)‐3‐nitrobenzamide (V) contains one N—H⋯O hydrogen bond and three C—H⋯O hydrogen bonds, together with a two‐centre iodo⋯nitro interaction and an aromatic π⋯π stacking interaction, while in N ‐(3‐iodophenyl)‐4‐nitrobenzamide (VI), the combination of one N—H⋯O hydrogen bond and two C—H⋯O hydrogen bonds is augmented not only by a two‐centre iodo⋯nitro interaction and an aromatic π⋯π stacking interaction, but also by a dipolar carbonyl⋯carbonyl interaction. In the supramolecular structure of N ‐(4‐iodophenyl)‐4‐nitrobenzamide (IX), which crystallizes with Z ′ = 2 in space group , there are two N—H⋯O hydrogen bonds, four C—H⋯O hydrogen bonds and two three‐centre iodo⋯nitro interactions.