Open AccessIsomeric iodo‐ N ‐(nitrobenzyl)anilines: interplay of hard and soft hydrogen bonds, iodo⋯nitro interactions and aromatic π⋯π stacking interactions
Author(s) -
Glidewell Christopher,
Low John N.,
Skakle Janet M. S.,
Wardell Solange M. S. V.,
Wardell James L.
Publication year - 2004
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
eISSN - 1600-5740
pISSN - 0108-7681
DOI - 10.1107/s0108768104012017
Subject(s) - stacking , supramolecular chemistry , hydrogen bond , aniline , aromaticity , molecule , intermolecular force , chemistry , nitro , stereochemistry , crystallography , supramolecular assembly , crystal structure , organic chemistry , alkyl
Molecules of 2‐iodo‐ N ‐(4‐nitrobenzyl)aniline, 4‐O 2 NC 6 H 4 CH 2 NHC 6 H 4 I‐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 π⋯π 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⋯π(arene) hydrogen bonds and aromatic π⋯π 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 π⋯π 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.