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