Acta Crystallographica Section B

Structural Science

Volume 58, Part 5 (October 2002)

Acta Cryst. (2002). B58, 864-876 [doi:10.1107/S0108768102009941]

Nine isomeric nitrobenzylidene-iodoanilines: interplay of C-HO hydrogen bonds, iodonitro interactions and aromatic stacking interactions

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

Abstract: Nine isomeric nitrobenzylidene-iodoanilines, O₂NC₆H₄CH= NC₆H₄I [(I)-(IX)], have been synthesized and the structures of all except 4-nitrobenzylidene-4'-iodoaniline (IX) have been analyzed. 2-Nitrobenzylidene-2'-iodoaniline (I) contains isolated molecules, while 3-nitrobenzylidene-2'-iodoaniline (II) and 2-nitrobenzylidene-3'-iodoaniline (IV) both contain chains of molecules linked by C-HO hydrogen bonds: similar chains in 4-nitrobenzylidene-2'-iodoaniline (III) are further linked by aromatic [bold pi] stacking interactions, forming sheets. In both 3-nitrobenzylidene-3'-iodoaniline and 4-nitrobenzylidene-3'-iodoaniline, (V) and (VI), a combination of C-HO hydrogen bonds and iodonitro interactions generates molecular ladders that are linked into sheets by aromatic stacking interactions, while in 2-nitrobenzylidene-4'-iodoaniline and 3-nitrobenzylidene-4'-iodoaniline, (VII) and (VIII), which both crystallize with Z' = 2 in C2/c and P $\bar 1$ , respectively, the combination of C-HO hydrogen bonds and iodonitro interactions generates sheets, which in (VIII) are further linked by [bold pi] stacking interactions to form a three-dimensional structure. The 4,4'-isomer (IX) crystallizes in Fdd2 with Z' = 2, but both molecules are intractably disordered.

Online 24 September 2002


	Structure factor file (CIF format) (136.4 kbytes) Contains datablock I

	Structure factor file (CIF format) (131.9 kbytes) Contains datablock II

	Structure factor file (CIF format) (138.9 kbytes) Contains datablock III

	Structure factor file (CIF format) (134.1 kbytes) Contains datablock IV

	Structure factor file (CIF format) (135.1 kbytes) Contains datablock V

	Structure factor file (CIF format) (129.0 kbytes) Contains datablock VI

	Structure factor file (CIF format) (265.3 kbytes) Contains datablock VII

	Structure factor file (CIF format) (274.3 kbytes) Contains datablock VIII

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