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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...

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Autores principales: Zaoui, Younes, Ramli, Youssef, Taoufik, Jamal, Mague, Joel T., Jotani, Mukesh M., Tiekink, Edward R. T., Ansar, M’hammed
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
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.
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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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