2-Iodo-N-(3-nitrobenzyl)aniline and 3-iodo-N-(3-nitrobenzyl)aniline exhibit entirely different patterns of supramolecular aggregation

Christopher Glidewell; John N Low; Janet M S Skakle; Solange M S V Wardell; James L Wardell

doi:10.1107/s010827010201140x

2-Iodo-N-(3-nitrobenzyl)aniline and 3-iodo-N-(3-nitrobenzyl)aniline exhibit entirely different patterns of supramolecular aggregation

Acta Crystallogr C. 2002 Aug;58(Pt 8):o487-90. doi: 10.1107/s010827010201140x. Epub 2002 Jul 20.

Authors

Christopher Glidewell¹, John N Low, Janet M S Skakle, Solange M S V Wardell, James L Wardell

Affiliation

¹ School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland. cg@st-andrews.ac.uk

PMID: 12154307
DOI: 10.1107/s010827010201140x

Abstract

In 2-iodo-N-(3-nitrobenzyl)aniline, C(13)H(11)IN(2)O(2), the molecules are linked into a three-dimensional structure by a combination of C-H...O hydrogen bonds, iodo-nitro interactions and aromatic pi-pi-stacking interactions, but N-H...O and C-H...pi(arene) hydrogen bonds are absent. In the isomeric 3-iodo-N-(3-nitrobenzyl)aniline, a two-dimensional array is generated by a combination of N-H...O, C-H...O and C-H...pi(arene) hydrogen bonds, but iodo-nitro interactions and aromatic pi-pi-stacking interactions are both absent.