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

doi:10.1107/S2052520621002961

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 journal › Article (Academic Journal) › peer-review

2 Citations (Scopus)

Abstract

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 language	English
Pages (from-to)	347-356
Number of pages	10
Journal	Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
Volume	77
Issue number	Pt 3
DOIs	https://doi.org/10.1107/S2052520621002961
Publication status	Published - 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.

Keywords

iodochalcone
halogen bonding
crystal engineering
crystal structure

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Hamilton, V., Harris, C., Hall, C. L., Potticary, J., Cremeens, M. E., D'Ambruoso, G. D., Matsumoto, M., Warren, S. D., Pridmore, N. E., Sparkes, H. A., & Hall, S. R. (2021). Structural effects of halogen bonding in iodochalcones. Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials, 77(Pt 3), 347-356. https://doi.org/10.1107/S2052520621002961

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abstract = "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.",

keywords = "iodochalcone, halogen bonding, crystal engineering, crystal structure",

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

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{\textquoteright}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: {\textcopyright} 2021 International Union of Crystallography. All rights reserved.",

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AU - Hamilton, Victoria

AU - Harris, Connah

AU - Hall, Charlie L

AU - Potticary, Jason

AU - Cremeens, Matthew E

AU - D'Ambruoso, Gemma D

AU - Matsumoto, Masaomi

AU - Warren, Stephen D

AU - Pridmore, Natalie E

AU - Sparkes, Hazel A

AU - Hall, Simon R

N1 - 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.

PY - 2021/6/1

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N2 - 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.

AB - 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.

KW - iodochalcone

KW - halogen bonding

KW - crystal engineering

KW - crystal structure

U2 - 10.1107/S2052520621002961

DO - 10.1107/S2052520621002961

M3 - Article (Academic Journal)

C2 - 34096516

SN - 2052-5192

VL - 77

SP - 347

EP - 356

JO - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

JF - Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials

IS - Pt 3

ER -

Structural effects of halogen bonding in iodochalcones

Abstract

Bibliographical note

Keywords

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