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

Abstract

The isomeric N-(iodophenyl)nitrobenzamides, C13H 9IN2O3, 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 P21, 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 P1̄, there are two N-H⋯O hydrogen bonds, four C-H⋯O hydrogen bonds and two three-centre iodo⋯nitro interactions. © 2006 International Union of Crystallography Printed in Great Britain - all rights reserved.