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Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate
The title pyridazinone derivative, C(21)H(19)ClN(2)O(3), is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°]. In the cr...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658951/ https://www.ncbi.nlm.nih.gov/pubmed/31391989 http://dx.doi.org/10.1107/S2056989019007424 |
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author | El Kalai, Fouad Baydere, Cemile Daoui, Said Saddik, Rafik Dege, Necmi Karrouchi, Khalid Benchat, Noureddine |
author_facet | El Kalai, Fouad Baydere, Cemile Daoui, Said Saddik, Rafik Dege, Necmi Karrouchi, Khalid Benchat, Noureddine |
author_sort | El Kalai, Fouad |
collection | PubMed |
description | The title pyridazinone derivative, C(21)H(19)ClN(2)O(3), is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°]. In the crystal, C—H⋯O hydrogen bonds generate dimers with R (2) (2)(10) and R (2) (2)(24) ring motifs which are linked by C—H⋯O interactions, forming chains extending parallel to the c-axis direction. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most significant contributions to the crystal packing are from H⋯H (44.5%), C⋯H/H⋯C (18.5%), H⋯O/H⋯O (15.6%), Cl⋯H/H⋯Cl (10.6%) and C⋯C (2.8%) contacts. |
format | Online Article Text |
id | pubmed-6658951 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-66589512019-08-07 Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate El Kalai, Fouad Baydere, Cemile Daoui, Said Saddik, Rafik Dege, Necmi Karrouchi, Khalid Benchat, Noureddine Acta Crystallogr E Crystallogr Commun Research Communications The title pyridazinone derivative, C(21)H(19)ClN(2)O(3), is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°]. In the crystal, C—H⋯O hydrogen bonds generate dimers with R (2) (2)(10) and R (2) (2)(24) ring motifs which are linked by C—H⋯O interactions, forming chains extending parallel to the c-axis direction. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most significant contributions to the crystal packing are from H⋯H (44.5%), C⋯H/H⋯C (18.5%), H⋯O/H⋯O (15.6%), Cl⋯H/H⋯Cl (10.6%) and C⋯C (2.8%) contacts. International Union of Crystallography 2019-05-24 /pmc/articles/PMC6658951/ /pubmed/31391989 http://dx.doi.org/10.1107/S2056989019007424 Text en © El Kalai et al. 2019 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 El Kalai, Fouad Baydere, Cemile Daoui, Said Saddik, Rafik Dege, Necmi Karrouchi, Khalid Benchat, Noureddine Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate |
title | Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate |
title_full | Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate |
title_fullStr | Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate |
title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate |
title_short | Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate |
title_sort | crystal structure and hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6658951/ https://www.ncbi.nlm.nih.gov/pubmed/31391989 http://dx.doi.org/10.1107/S2056989019007424 |
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