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

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).