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Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo­phen­yl)-1-(4-iodo­phen­yl)prop-2-en-1-one

The title compound, C(15)H(10)I(2)O, is a halogenated chalcone formed from two iodine substituted rings, one para-substituted and the other meta-substituted, linked through a prop-2-en-1-one spacer. In the mol­ecule, the mean planes of the 3-iodo­phenyl and the 4-iodo­phenyl groups are twisted by 46...

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Autores principales: Spruce, Kieran J., Hall, Charlie L., Potticary, Jason, Pridmore, Natalie E., Cremeens, Matthew E., D’ambruoso, Gemma D., Matsumoto, Masaomi, Warren, Gabrielle I., Warren, Stephen D., Hall, Simon R.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6944092/
https://www.ncbi.nlm.nih.gov/pubmed/31921455
http://dx.doi.org/10.1107/S2056989019016402
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author Spruce, Kieran J.
Hall, Charlie L.
Potticary, Jason
Pridmore, Natalie E.
Cremeens, Matthew E.
D’ambruoso, Gemma D.
Matsumoto, Masaomi
Warren, Gabrielle I.
Warren, Stephen D.
Hall, Simon R.
author_facet Spruce, Kieran J.
Hall, Charlie L.
Potticary, Jason
Pridmore, Natalie E.
Cremeens, Matthew E.
D’ambruoso, Gemma D.
Matsumoto, Masaomi
Warren, Gabrielle I.
Warren, Stephen D.
Hall, Simon R.
author_sort Spruce, Kieran J.
collection PubMed
description The title compound, C(15)H(10)I(2)O, is a halogenated chalcone formed from two iodine substituted rings, one para-substituted and the other meta-substituted, linked through a prop-2-en-1-one spacer. In the mol­ecule, the mean planes of the 3-iodo­phenyl and the 4-iodo­phenyl groups are twisted by 46.51 (15)°. The calculated electrostatic potential surfaces show the presence of σ-holes on both substituted iodines. In the crystal, the mol­ecules are linked through type II halogen bonds, forming a sheet structure parallel to the bc plane. Between the sheets, weak inter­molecular C—H⋯π inter­actions are observed. Hirshfeld surface analysis showed that the most significant contacts in the structure are C⋯H/H⋯C (31.9%), followed by H⋯H (21.4%), I⋯H/H⋯I (18.4%). I⋯I (14.5%) and O⋯H/H⋯O (8.1%).
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spelling pubmed-69440922020-01-09 Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo­phen­yl)-1-(4-iodo­phen­yl)prop-2-en-1-one Spruce, Kieran J. Hall, Charlie L. Potticary, Jason Pridmore, Natalie E. Cremeens, Matthew E. D’ambruoso, Gemma D. Matsumoto, Masaomi Warren, Gabrielle I. Warren, Stephen D. Hall, Simon R. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(15)H(10)I(2)O, is a halogenated chalcone formed from two iodine substituted rings, one para-substituted and the other meta-substituted, linked through a prop-2-en-1-one spacer. In the mol­ecule, the mean planes of the 3-iodo­phenyl and the 4-iodo­phenyl groups are twisted by 46.51 (15)°. The calculated electrostatic potential surfaces show the presence of σ-holes on both substituted iodines. In the crystal, the mol­ecules are linked through type II halogen bonds, forming a sheet structure parallel to the bc plane. Between the sheets, weak inter­molecular C—H⋯π inter­actions are observed. Hirshfeld surface analysis showed that the most significant contacts in the structure are C⋯H/H⋯C (31.9%), followed by H⋯H (21.4%), I⋯H/H⋯I (18.4%). I⋯I (14.5%) and O⋯H/H⋯O (8.1%). International Union of Crystallography 2020-01-01 /pmc/articles/PMC6944092/ /pubmed/31921455 http://dx.doi.org/10.1107/S2056989019016402 Text en © Spruce et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Spruce, Kieran J.
Hall, Charlie L.
Potticary, Jason
Pridmore, Natalie E.
Cremeens, Matthew E.
D’ambruoso, Gemma D.
Matsumoto, Masaomi
Warren, Gabrielle I.
Warren, Stephen D.
Hall, Simon R.
Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo­phen­yl)-1-(4-iodo­phen­yl)prop-2-en-1-one
title Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo­phen­yl)-1-(4-iodo­phen­yl)prop-2-en-1-one
title_full Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo­phen­yl)-1-(4-iodo­phen­yl)prop-2-en-1-one
title_fullStr Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo­phen­yl)-1-(4-iodo­phen­yl)prop-2-en-1-one
title_full_unstemmed Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo­phen­yl)-1-(4-iodo­phen­yl)prop-2-en-1-one
title_short Crystal structure and Hirshfeld surface analysis of (E)-3-(3-iodo­phen­yl)-1-(4-iodo­phen­yl)prop-2-en-1-one
title_sort crystal structure and hirshfeld surface analysis of (e)-3-(3-iodo­phen­yl)-1-(4-iodo­phen­yl)prop-2-en-1-one
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6944092/
https://www.ncbi.nlm.nih.gov/pubmed/31921455
http://dx.doi.org/10.1107/S2056989019016402
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