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Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate
The asymmetric units of the title compounds both contain one nonplanar molecule. In 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one, C(17)H(14)N(2)O, (I), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 46.69 (9)°; the phenyl ring of the benzyl...
Autores principales: | , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829710/ https://www.ncbi.nlm.nih.gov/pubmed/31709089 http://dx.doi.org/10.1107/S2056989019013707 |
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author | Dadou, Said Kansiz, Sevgi Daoui, Said El Kalai, Fouad Baydere, Cemile Saddik, Rafik Karrouchi, Khalid Dege, Necmi Benchat, Noureddine |
author_facet | Dadou, Said Kansiz, Sevgi Daoui, Said El Kalai, Fouad Baydere, Cemile Saddik, Rafik Karrouchi, Khalid Dege, Necmi Benchat, Noureddine |
author_sort | Dadou, Said |
collection | PubMed |
description | The asymmetric units of the title compounds both contain one nonplanar molecule. In 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one, C(17)H(14)N(2)O, (I), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 46.69 (9)°; the phenyl ring of the benzyl group is nearly perpendicular to the plane of the pyridazine ring, the dihedral angle being 78.31 (10)°. In methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate, C(20)H(16)Cl(2)N(2)O(3), (II), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 21.76 (18)°, whereas the phenyl ring of the dichlorobenzyl group is inclined to the pyridazine ring by 79.61 (19)°. In the crystal structure of (I), pairs of N—H⋯O hydrogen bonds link the molecules into inversion dimers with an R (2) (2)(8) ring motif. In the crystal structure of (II), C—H⋯O hydrogen bonds generate dimers with R (1) (2)(7), R (2) (2)(16) and R (2) (2)(18) ring motifs. The Hirshfeld surface analyses of compound (I) suggests that the most significant contributions to the crystal packing are by H⋯H (48.2%), C⋯H/H⋯C (29.9%) and O⋯H/H⋯O (8.9%) contacts. For compound (II), H⋯H (34.4%), C⋯H/H⋯C (21.3%) and O⋯H/H⋯O (16.5%) interactions are the most important contributions. |
format | Online Article Text |
id | pubmed-6829710 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-68297102019-11-08 Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate Dadou, Said Kansiz, Sevgi Daoui, Said El Kalai, Fouad Baydere, Cemile Saddik, Rafik Karrouchi, Khalid Dege, Necmi Benchat, Noureddine Acta Crystallogr E Crystallogr Commun Research Communications The asymmetric units of the title compounds both contain one nonplanar molecule. In 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one, C(17)H(14)N(2)O, (I), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 46.69 (9)°; the phenyl ring of the benzyl group is nearly perpendicular to the plane of the pyridazine ring, the dihedral angle being 78.31 (10)°. In methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate, C(20)H(16)Cl(2)N(2)O(3), (II), the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 21.76 (18)°, whereas the phenyl ring of the dichlorobenzyl group is inclined to the pyridazine ring by 79.61 (19)°. In the crystal structure of (I), pairs of N—H⋯O hydrogen bonds link the molecules into inversion dimers with an R (2) (2)(8) ring motif. In the crystal structure of (II), C—H⋯O hydrogen bonds generate dimers with R (1) (2)(7), R (2) (2)(16) and R (2) (2)(18) ring motifs. The Hirshfeld surface analyses of compound (I) suggests that the most significant contributions to the crystal packing are by H⋯H (48.2%), C⋯H/H⋯C (29.9%) and O⋯H/H⋯O (8.9%) contacts. For compound (II), H⋯H (34.4%), C⋯H/H⋯C (21.3%) and O⋯H/H⋯O (16.5%) interactions are the most important contributions. International Union of Crystallography 2019-10-22 /pmc/articles/PMC6829710/ /pubmed/31709089 http://dx.doi.org/10.1107/S2056989019013707 Text en © Dadou 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 Dadou, Said Kansiz, Sevgi Daoui, Said El Kalai, Fouad Baydere, Cemile Saddik, Rafik Karrouchi, Khalid Dege, Necmi Benchat, Noureddine Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate |
title | Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate |
title_full | Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate |
title_fullStr | Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate |
title_full_unstemmed | Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate |
title_short | Crystal structures and Hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2H)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate |
title_sort | crystal structures and hirshfeld surface analyses of 4-benzyl-6-phenyl-4,5-dihydropyridazin-3(2h)-one and methyl 2-[5-(2,6-dichlorobenzyl)-6-oxo-3-phenyl-1,4,5,6-tetrahydropyridazin-1-yl]acetate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829710/ https://www.ncbi.nlm.nih.gov/pubmed/31709089 http://dx.doi.org/10.1107/S2056989019013707 |
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