Cargando…
Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one
The molecular structure of the title compound, C(13)H(6)Cl(4)OS, consists of a 2,5-dichlorothiophene ring and a 2,4-dichlorophenyl ring linked via a prop-2-en-1-one spacer. The dihedral angle between the 2,5-dichlorothiophene ring and the 2,4-dichlorophenyl ring is 12.24 (15)°. The molec...
Autores principales: | , , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2018
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6127697/ https://www.ncbi.nlm.nih.gov/pubmed/30225099 http://dx.doi.org/10.1107/S2056989018010976 |
_version_ | 1783353529055838208 |
---|---|
author | Murthy, T. N. Sanjeeva Atioğlu, Zeliha Akkurt, Mehmet Chidan Kumar, C. S. Veeraiah, M. K. Quah, Ching Kheng Siddaraju, B. P. |
author_facet | Murthy, T. N. Sanjeeva Atioğlu, Zeliha Akkurt, Mehmet Chidan Kumar, C. S. Veeraiah, M. K. Quah, Ching Kheng Siddaraju, B. P. |
author_sort | Murthy, T. N. Sanjeeva |
collection | PubMed |
description | The molecular structure of the title compound, C(13)H(6)Cl(4)OS, consists of a 2,5-dichlorothiophene ring and a 2,4-dichlorophenyl ring linked via a prop-2-en-1-one spacer. The dihedral angle between the 2,5-dichlorothiophene ring and the 2,4-dichlorophenyl ring is 12.24 (15)°. The molecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The molecular conformation is stabilized by intramolecular C—H⋯Cl contacts, producing S(6) and S(5) ring motifs. In the crystal, the molecules are linked along the a-axis direction through face-to-face π-stacking between the thiophene rings and the benzene rings of the molecules in zigzag sheets lying parallel to the bc plane along the c axis. The intermolecular interactions in the crystal packing were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are Cl⋯H/ H⋯Cl (20.8%), followed by Cl⋯Cl (18.7%), C⋯C (11.9%), Cl⋯S/S⋯Cl (10.9%), H⋯H (10.1%), C⋯H/H⋯C (9.3%) and O⋯H/H⋯O (7.6%). |
format | Online Article Text |
id | pubmed-6127697 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2018 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-61276972018-09-17 Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one Murthy, T. N. Sanjeeva Atioğlu, Zeliha Akkurt, Mehmet Chidan Kumar, C. S. Veeraiah, M. K. Quah, Ching Kheng Siddaraju, B. P. Acta Crystallogr E Crystallogr Commun Research Communications The molecular structure of the title compound, C(13)H(6)Cl(4)OS, consists of a 2,5-dichlorothiophene ring and a 2,4-dichlorophenyl ring linked via a prop-2-en-1-one spacer. The dihedral angle between the 2,5-dichlorothiophene ring and the 2,4-dichlorophenyl ring is 12.24 (15)°. The molecule has an E configuration about the C=C bond and the carbonyl group is syn with respect to the C=C bond. The molecular conformation is stabilized by intramolecular C—H⋯Cl contacts, producing S(6) and S(5) ring motifs. In the crystal, the molecules are linked along the a-axis direction through face-to-face π-stacking between the thiophene rings and the benzene rings of the molecules in zigzag sheets lying parallel to the bc plane along the c axis. The intermolecular interactions in the crystal packing were further analysed using Hirshfield surface analysis, which indicates that the most significant contacts are Cl⋯H/ H⋯Cl (20.8%), followed by Cl⋯Cl (18.7%), C⋯C (11.9%), Cl⋯S/S⋯Cl (10.9%), H⋯H (10.1%), C⋯H/H⋯C (9.3%) and O⋯H/H⋯O (7.6%). International Union of Crystallography 2018-08-10 /pmc/articles/PMC6127697/ /pubmed/30225099 http://dx.doi.org/10.1107/S2056989018010976 Text en © Murthy et al. 2018 http://creativecommons.org/licenses/by/2.0/uk/ 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/2.0/uk/ |
spellingShingle | Research Communications Murthy, T. N. Sanjeeva Atioğlu, Zeliha Akkurt, Mehmet Chidan Kumar, C. S. Veeraiah, M. K. Quah, Ching Kheng Siddaraju, B. P. Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one |
title | Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one |
title_full | Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one |
title_fullStr | Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one |
title_short | Crystal structure and Hirshfeld surface analysis of (2E)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one |
title_sort | crystal structure and hirshfeld surface analysis of (2e)-3-(2,4-dichlorophenyl)-1-(2,5-dichlorothiophen-3-yl)prop-2-en-1-one |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6127697/ https://www.ncbi.nlm.nih.gov/pubmed/30225099 http://dx.doi.org/10.1107/S2056989018010976 |
work_keys_str_mv | AT murthytnsanjeeva crystalstructureandhirshfeldsurfaceanalysisof2e324dichlorophenyl125dichlorothiophen3ylprop2en1one AT atiogluzeliha crystalstructureandhirshfeldsurfaceanalysisof2e324dichlorophenyl125dichlorothiophen3ylprop2en1one AT akkurtmehmet crystalstructureandhirshfeldsurfaceanalysisof2e324dichlorophenyl125dichlorothiophen3ylprop2en1one AT chidankumarcs crystalstructureandhirshfeldsurfaceanalysisof2e324dichlorophenyl125dichlorothiophen3ylprop2en1one AT veeraiahmk crystalstructureandhirshfeldsurfaceanalysisof2e324dichlorophenyl125dichlorothiophen3ylprop2en1one AT quahchingkheng crystalstructureandhirshfeldsurfaceanalysisof2e324dichlorophenyl125dichlorothiophen3ylprop2en1one AT siddarajubp crystalstructureandhirshfeldsurfaceanalysisof2e324dichlorophenyl125dichlorothiophen3ylprop2en1one |