Acta Crystallographica Section B

Structural Science

Volume 62, Part 5 (October 2006)

research papers

Acta Cryst. (2006). B62, 931-943 [ doi:10.1107/S0108768106029053 ]

Isomeric N-(iodophenyl)nitrobenzamides form different three-dimensional framework structures

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

Abstract: The isomeric N-(iodophenyl)nitrobenzamides, C₁₃H₉IN₂O₃, all form different three-dimensional framework structures. Molecules of N-(2-iodophenyl)-3-nitrobenzamide (II) are linked by a combination of N-HO and C-HO hydrogen bonds and a two-centre iodocarbonyl interaction. The supramolecular structure of N-(2-iodophenyl)-4-nitrobenzamide (III) is built from one N-HO and two C-HO hydrogen bonds, but short IO contacts are absent from the structure. In N-(3-iodophenyl)-2-nitrobenzamide (IV), which crystallizes with Z' = 2 in space group P2₁, the structure contains two N-HO hydrogen bonds, four C-HO hydrogen bonds, two two-centre iodonitro interactions and an aromatic [pi] [pi] stacking interaction. The structure of N-(3-iodophenyl)-3-nitrobenzamide (V) contains one N-HO hydrogen bond and three C-HO hydrogen bonds, together with a two-centre iodonitro interaction and an aromatic [pi] [pi] stacking interaction, while in N-(3-iodophenyl)-4-nitrobenzamide (VI), the combination of one N-HO hydrogen bond and two C-HO hydrogen bonds is augmented not only by a two-centre iodonitro interaction and an aromatic [pi] [pi] stacking interaction, but also by a dipolar carbonylcarbonyl interaction. In the supramolecular structure of N-(4-iodophenyl)-4-nitrobenzamide (IX), which crystallizes with Z' = 2 in space group $P\overline 1$ , there are two N-HO hydrogen bonds, four C-HO hydrogen bonds and two three-centre iodonitro interactions.

Keywords: N-(iodophenyl)nitrobenzamides.


	Structure factor file (CIF format) (144.4 kbytes) [ doi:10.1107/S0108768106029053/bm5035IIsup2.hkl ] Contains datablock 758

	Structure factor file (CIF format) (135.8 kbytes) [ doi:10.1107/S0108768106029053/bm5035IIIsup3.hkl ] Contains datablock 747

	Structure factor file (CIF format) (277.7 kbytes) [ doi:10.1107/S0108768106029053/bm5035IVsup4.hkl ] Contains datablock 763

	Structure factor file (CIF format) (137.3 kbytes) [ doi:10.1107/S0108768106029053/bm5035Vsup5.hkl ] Contains datablock V

	Structure factor file (CIF format) (139.6 kbytes) [ doi:10.1107/S0108768106029053/bm5035VIsup6.hkl ] Contains datablock 746t

	Structure factor file (CIF format) (359.5 kbytes) [ doi:10.1107/S0108768106029053/bm5035IXsup7.hkl ] Contains datablock 748

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