Contrasting three-dimensional framework structures in the isomeric pair 2-iodo-N-(2-nitrophenyl)benzamide and N-(2-iodophenyl)-2-nitrobenzamide.

In 2-iodo-N-(2-nitrophenyl)benzamide, C(13)H(9)IN(2)O(3), the molecules are linked into a three-dimensional framework structure by a combination of a C-H...O hydrogen bond, and iodo-nitro, carbonyl-carbonyl and aromatic pi-pi stacking interactions. In the isomeric compound N-(2-iodophenyl)-2-nitrobenzamide, the framework structure is built from N-H...O, C-H...O and C-H...pi(arene) hydrogen bonds and an iodo-nitro interaction.