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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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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%). |
format | Online Article Text |
id | pubmed-6944092 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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