title: 2-Iodo-N-(3-nitrobenzyl)aniline and 3-iodo-N-(3-nitrobenzyl)aniline exhibit entirely different patterns of supramolecular aggregation.
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.
authors.affiliation: School of Chemistry, University of St Andrews, St Andrews, Fife KY16 9ST, Scotland. cg@st-andrews.ac.uk
authors.forename: Christopher
authors.initials: C
authors.lastname: Glidewell
authors.forename: John N
authors.initials: JN
authors.lastname: Low
authors.forename: Janet M S
authors.initials: JM
authors.lastname: Skakle
authors.forename: Solange M S V
authors.initials: SM
authors.lastname: Wardell
authors.forename: James L
authors.initials: JL
authors.lastname: Wardell