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

Abstract

The six isomeric N-(iodophenyl)nitrophthalimides, C14H 7IN2O4, have been synthesized and the structures of five of them are reported. In N-(4-iodophenyl)-4-nitrophthalimide [(I), orthorhombic P212121] 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 P21/c] and N-(2-iodophenyl)-4- nitrophthalimide [(III), monoclinic P21/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 R44(30) rings, while in (III) they are linked by an iodo⋯carbonyl interaction and a C - H⋯O hydrogen bond into sheets or R44(26) rings. Three-dimensional supramolecular structures are formed in both N-(4-iodophenyl)-3-nitrophthalimide [(IV), monoclinic P21/n] and N-(3-iodophenyl)-3-nitrophthalimide [(V), orthorhombic, P212121]. In (IV) the molecules are linked by a three-centre iodo⋯nitro interaction, three C - H⋯O hydrogen bonds and an aromatic π⋯π 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 π⋯π stacking interactions are absent from (V). © 2005 International Union of Crystallography Printed in Great Britain - all rights reserved.