Acta Crystallographica Section B

Structural Science

Volume 60, Part 4 (August 2004)


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Acta Cryst. (2004). B60, 472-480    [doi:10.1107/S0108768104012017]

Isomeric iodo-N-(nitrobenzyl)anilines: interplay of hard and soft hydrogen bonds, iodo...nitro interactions and aromatic [bold pi]...[bold pi] stacking interactions

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

Abstract: Molecules of 2-iodo-N-(4-nitrobenzyl)aniline, 4-O2NC6H4CH2NHC6H4I-2' (1) are linked into chains by C-H...O hydrogen bonds. In the isomeric compound 3-iodo-N-(4-nitrobenzyl)aniline (2) a combination of N-H...O and C-H...O hydrogen bonds and iodo...nitro and aromatic [bold pi]...[bold pi] stacking interactions links the molecules into a three-dimensional framework structure. The two-dimensional supramolecular structure of 4-iodo-N-(4-nitrobenzyl)aniline (6) is built from a combination of C-H...O and N-H...[bold pi](arene) hydrogen bonds and aromatic [bold pi]...[bold pi] stacking interactions. 2-Iodo-N-(2-nitrobenzyl)aniline (7) crystallizes with two molecules in the asymmetric unit and these molecules are linked into ladders by a combination of N-H...O and C-H...O hydrogen bonds and iodo...nitro and aromatic [bold pi]...[bold pi] stacking interactions. Comparisons are made between the supramolecular structures of these compounds and those of other isomers, in terms both of the types of direction-specific intermolecular interactions exhibited and the dimensionality of the resulting supramolecular structures.

Online 19 July 2004

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