Acta Crystallographica Section B

Structural Science

Volume 61, Part 2 (April 2005)

research papers

Acta Cryst. (2005). B61, 227-237 [ doi:10.1107/S0108768105004234 ]

Isomeric N-(iodophenyl)nitrophthalimides: interplay of C-HO hydrogen bonds, iodonitro and iodocarbonyl interactions, and aromatic stacking interactions

C. Glidewell, J. N. Low, J. M. S. Skakle, S. M. S. V. Wardell and J. L. Wardell

Abstract: 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 P2₁2₁2₁] the molecules are linked into sheets by a combination of four independent C-HO hydrogen bonds, but IO 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 iodonitro interaction and one C-HO hydrogen bond into sheets containing rings, while in (III) they are linked by an iodocarbonyl interaction and a C-HO hydrogen bond into sheets or 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 iodonitro interaction, three C-HO hydrogen bonds and an aromatic [pi] [pi] stacking interaction, but the framework in (V) is generated by a two-centre iodonitro interaction and only two C-HO hydrogen bonds: aromatic [pi] [pi] stacking interactions are absent from (V).

Keywords: hydrogen bonds; stacking interactions; supramolecular structures.


	Structure factor file (CIF format) (148.0 kbytes) Contains datablock I

	Structure factor file (CIF format) (235.5 kbytes) Contains datablock js302

	Structure factor file (CIF format) (246.9 kbytes) Contains datablock js344

	Structure factor file (CIF format) (143.3 kbytes) Contains datablock fin357

	Structure factor file (CIF format) (146.5 kbytes) Contains datablock V

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