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

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-HÁ Á ÁO hydrogen bonds, but IÁ Á ÁO 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 iodoÁ Á Ánitro interaction and one C-HÁ Á ÁO hydrogen bond into sheets containing R 4 4 ð30Þ rings, while in (III) they are linked by an iodoÁ Á Ácarbonyl interaction and a C-HÁ Á ÁO hydrogen bond into sheets or R 4 4 ð26Þ rings. Three-dimensional supramolecular structures are formed in both N-(4-iodophenyl)-3-nitrophthalimide [(IV), monoclinic P2 1 /n] and N-(3-iodophenyl)-3nitrophthalimide [(V), orthorhombic, P2 1 2 1 2 1 ]. In (IV) the molecules are linked by a three-centre iodoÁ Á Ánitro interaction, three C-HÁ Á ÁO hydrogen bonds and an aromatic Á Á Á stacking interaction, but the framework in (V) is generated by a two-centre iodoÁ Á Ánitro interaction and only two C-HÁ Á ÁO hydrogen bonds: aromatic Á Á Á stacking interactions are absent from (V).