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...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 P\overline 1, there are two N—H...O hydrogen bonds, four C—H...O hydrogen bonds and two three-centre iodo...nitro interactions.