Isomeric N-(iodophenyl)nitrophthalimides: interplay of C-H...O hydrogen bonds, iodo...nitro and iodo...carbonyl interactions, and aromatic p...p stacking

The six isomeric N-(iodophenyl)nitrophthalimides, C14H7IN2O4, have been synthesized and the structures of five of them are reported. In N-(4-iodophenyl)-4-nitrophthalimide [( I), orthorhombic P2(1)2(1)2(1)] the molecules are linked into sheets by a combination of four independent C - H center dot center dot center dot O hydrogen bonds, but I center dot center dot center dot O interactions are absent. The isomers N-(3-iodophenyl)-4-nitrophthalimide [(II), monoclinic P2(1)/c] and N-(2-iodophenyl)-4-nitrophthalimide [(III), monoclinic P2(1)/n] both form sheets, but in ( II) the molecules are linked by a combination of one two-centre iodo center dot center dot center dot nitro interaction and one C - H center dot center dot center dot O hydrogen bond into sheets containing R-4(4)(30) rings, while in (III) they are linked by an iodo center dot center dot center dot carbonyl interaction and a C - H center dot center dot center dot O hydrogen bond into sheets or R-4(4)(26) rings. Three-dimensional supramolecular structures are formed in both N-(4-iodophenyl)-3-nitrophthalimide [(IV), monoclinic P2(1)/n] and N-(3-iodophenyl)-3-nitrophthalimide [( V), orthorhombic, P2(1)2(1)2(1)]. In ( IV) the molecules are linked by a three-centre iodo center dot center dot center dot nitro interaction, three C - H center dot center dot center dot O hydrogen bonds and an aromatic pi center dot center dot center dot pi stacking interaction, but the framework in ( V) is generated by a two-centre iodo center dot center dot center dot nitro interaction and only two C - H center dot center dot center dot O hydrogen bonds: aromatic pi center dot center dot center dot pi stacking interactions are absent from (V).