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Structural effects of halogen bonding in iodochalcones
Author(s) -
Hamilton Victoria,
Harris Connah,
Hall Charlie L.,
Potticary Jason,
Cremeens Matthew E.,
D'Ambruoso Gemma D.,
Matsumoto Masaomi,
Warren Stephen D.,
Pridmore Natalie E.,
Sparkes Hazel A.,
Hall Simon R.
Publication year - 2021
Publication title -
acta crystallographica section b
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.604
H-Index - 33
ISSN - 2052-5206
DOI - 10.1107/s2052520621002961
Subject(s) - synthon , halogen bond , halogen , acceptor , nitro , fluorine , chemistry , crystal engineering , crystal structure , crystallography , molecule , stereochemistry , organic chemistry , supramolecular chemistry , alkyl , physics , condensed matter physics
The structures of three iodochalcones, functionalized with fluorine or a nitro group, have been investigated to explore the impact of different molecular electrostatic distributions on the halogen bonding within each crystal structure. The strongly withdrawing nitro group presented a switch of the halogen bond from a lateral to a linear motif. Surprisingly, this appears to be influenced by a net positive shift in charge distribution around the lateral edges of the σ‐hole, making the lateral I…I bonding motif less preferable. A channel of amphoteric I…I type II halogen bonds is observed for a chalcone molecule, which was not previously reported in chalcones, alongside an example of the common synthon involving extended linear chains of I…O 2 N donor–acceptor halogen bonds. This work shows that halogenated chalcones may be an interesting target for developing halogen bonding as a significant tool within crystal engineering, a thus far underexplored area for this common structural motif.