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

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The six isomeric N-(iodophenyl)nitrophthalimides, C(14)H(7)IN(2)O(4), 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...O hydrogen bonds, but I...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...nitro interaction and one C-H...O hydrogen bond into sheets containing R_4/4(30) rings, while in (III) they are linked by an iodo...carbonyl interaction and a C-H...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...nitro interaction, three C-H...O hydrogen bonds and an aromatic pi...pi stacking interaction, but the framework in (V) is generated by a two-centre iodo...nitro interaction and only two C-H...O hydrogen bonds: aromatic pi...pi stacking interactions are absent from (V).