Structural effects of halogen bonding in iodochalcones

Victoria Hamilton, Connah Harris, Charlie L Hall, Jason Potticary, Matthew E Cremeens, Gemma D D'Ambruoso, Masaomi Matsumoto, Stephen D Warren, Natalie E Pridmore, Hazel A Sparkes, Simon R Hall*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

2 Citations (Scopus)


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...O2N 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.

Original languageEnglish
Pages (from-to)347-356
Number of pages10
JournalActa Crystallographica Section B: Structural Science, Crystal Engineering and Materials
Issue numberPt 3
Publication statusPublished - 1 Jun 2021

Bibliographical note

Funding Information:
The following funding is acknowledged: Engineering and Physical Sciences Research Council (grant Nos. EP/L016648/1 and EP/L015544/1); European Union Horizon (grant agreement No. 73689).

Funding Information:
SRH, VH, JP and CH would like to acknowledge funding from the Engineering and Physical Sciences Research Council UK with support from the Bristol Centre for Functional Nano-materials, the Centre for Doctoral Training In Condensed Matter Physics and the MagnaPharm project, which has received funding from the European Union’s Horizon 2020 Research and Innovation programme. Gonzaga University coauthors thank S. Economu, B. Hendricks, J. Hazen, J. Grisaffi, C. Held, E. Harmston, C. McCormick, K. Okubo and M. Ortiz for their assistance, as well as the Howard Hughes Medical Institute through its Undergraduate Science Education Program for supporting equipment acquisition. Support also

Publisher Copyright:
© 2021 International Union of Crystallography. All rights reserved.


  • iodochalcone
  • halogen bonding
  • crystal engineering
  • crystal structure


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