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Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and Hirshfeld surface analysis
The title compound, C(16)H(18)N(2)O(3), is constructed about a central oxopyridazinyl ring (r.m.s. deviation = 0.0047 Å), which is connected to an ethylacetate group at the N atom closest to the carbonyl group, and benzyl and methyl groups second furthest and furthest from the carbonyl group, respe...
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/PMC6399698/ https://www.ncbi.nlm.nih.gov/pubmed/30867956 http://dx.doi.org/10.1107/S205698901900241X |
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author | Zaoui, Younes Ramli, Youssef Taoufik, Jamal Mague, Joel T. Jotani, Mukesh M. Tiekink, Edward R. T. Ansar, M’hammed |
author_facet | Zaoui, Younes Ramli, Youssef Taoufik, Jamal Mague, Joel T. Jotani, Mukesh M. Tiekink, Edward R. T. Ansar, M’hammed |
author_sort | Zaoui, Younes |
collection | PubMed |
description | The title compound, C(16)H(18)N(2)O(3), is constructed about a central oxopyridazinyl ring (r.m.s. deviation = 0.0047 Å), which is connected to an ethylacetate group at the N atom closest to the carbonyl group, and benzyl and methyl groups second furthest and furthest from the carbonyl group, respectively. An approximately orthogonal relationship exists between the oxopyridazinyl ring and the best plane through the ethylacetate group [dihedral angle = 77.48 (3)°]; the latter lies to one side of the central plane [the N(r)—N(r)—C(m)—C(c) (r = ring, m = methylene, c = carbonyl) torsion angle being 104.34 (9)°]. In the crystal, both H atoms of the N-bound methylene group form methylene-C—H⋯O(ring carbonyl) or N(pyridazinyl) interactions, resulting in the formation of a supramolecular tape along the a-axis direction. The tapes are assembled into a three-dimensional architecture by methyl- and phenyl-C—H⋯O(ring carbonyl) and phenyl-C—H⋯O(ester carbonyl) interactions. The analysis of the calculated Hirshfeld surface indicates the dominance of H⋯H contacts to the overall surface (i.e. 52.2%). Reflecting other identified points of contact between molecules noted above, O⋯H/H⋯O (23.3%), C⋯H/H⋯C (14.7%) and N⋯H/H⋯N (6.6%) contacts also make significant contributions to the surface. |
format | Online Article Text |
id | pubmed-6399698 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-63996982019-03-13 Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and Hirshfeld surface analysis Zaoui, Younes Ramli, Youssef Taoufik, Jamal Mague, Joel T. Jotani, Mukesh M. Tiekink, Edward R. T. Ansar, M’hammed Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(16)H(18)N(2)O(3), is constructed about a central oxopyridazinyl ring (r.m.s. deviation = 0.0047 Å), which is connected to an ethylacetate group at the N atom closest to the carbonyl group, and benzyl and methyl groups second furthest and furthest from the carbonyl group, respectively. An approximately orthogonal relationship exists between the oxopyridazinyl ring and the best plane through the ethylacetate group [dihedral angle = 77.48 (3)°]; the latter lies to one side of the central plane [the N(r)—N(r)—C(m)—C(c) (r = ring, m = methylene, c = carbonyl) torsion angle being 104.34 (9)°]. In the crystal, both H atoms of the N-bound methylene group form methylene-C—H⋯O(ring carbonyl) or N(pyridazinyl) interactions, resulting in the formation of a supramolecular tape along the a-axis direction. The tapes are assembled into a three-dimensional architecture by methyl- and phenyl-C—H⋯O(ring carbonyl) and phenyl-C—H⋯O(ester carbonyl) interactions. The analysis of the calculated Hirshfeld surface indicates the dominance of H⋯H contacts to the overall surface (i.e. 52.2%). Reflecting other identified points of contact between molecules noted above, O⋯H/H⋯O (23.3%), C⋯H/H⋯C (14.7%) and N⋯H/H⋯N (6.6%) contacts also make significant contributions to the surface. International Union of Crystallography 2019-02-22 /pmc/articles/PMC6399698/ /pubmed/30867956 http://dx.doi.org/10.1107/S205698901900241X Text en © Zaoui 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 Zaoui, Younes Ramli, Youssef Taoufik, Jamal Mague, Joel T. Jotani, Mukesh M. Tiekink, Edward R. T. Ansar, M’hammed Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and Hirshfeld surface analysis |
title | Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and Hirshfeld surface analysis |
title_full | Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and Hirshfeld surface analysis |
title_fullStr | Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and Hirshfeld surface analysis |
title_full_unstemmed | Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and Hirshfeld surface analysis |
title_short | Ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and Hirshfeld surface analysis |
title_sort | ethyl 2-(4-benzyl-3-methyl-6-oxo-1,6-dihydropyridazin-1-yl)acetate: crystal structure and hirshfeld surface analysis |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6399698/ https://www.ncbi.nlm.nih.gov/pubmed/30867956 http://dx.doi.org/10.1107/S205698901900241X |
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