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Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate

The mol­ecule of the title compound, C(16)H(17)N(5)O(3), is build up from two fused six-membered rings linked to a 1,2,3-triazole ring, which is attached to an ethyl azido-acetate group. The di­hydro­qinoxalinone portion is planar to within 0.0512 (12) Å and is oriented at a dihedral angle of 87.83 ...

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Autores principales: Abad, Nadeem, Ramli, Youssef, Hökelek, Tuncer, Sebbar, Nada Kheira, Mague, Joel T., Essassi, El Mokhtar
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6218907/
https://www.ncbi.nlm.nih.gov/pubmed/30443399
http://dx.doi.org/10.1107/S2056989018014561
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author Abad, Nadeem
Ramli, Youssef
Hökelek, Tuncer
Sebbar, Nada Kheira
Mague, Joel T.
Essassi, El Mokhtar
author_facet Abad, Nadeem
Ramli, Youssef
Hökelek, Tuncer
Sebbar, Nada Kheira
Mague, Joel T.
Essassi, El Mokhtar
author_sort Abad, Nadeem
collection PubMed
description The mol­ecule of the title compound, C(16)H(17)N(5)O(3), is build up from two fused six-membered rings linked to a 1,2,3-triazole ring, which is attached to an ethyl azido-acetate group. The di­hydro­qinoxalinone portion is planar to within 0.0512 (12) Å and is oriented at a dihedral angle of 87.83 (5)° with respect to the pendant triazole ring. In the crystal, a combination of inter­molecular C—H⋯O and C—H⋯N hydrogen bonds together with slipped π-stacking [centroid–centroid distance = 3.7772 (12) Å] and C—H⋯π (ring) inter­actions lead to the formation of chains extending along the c-axis direction. Additional C—H⋯O hydrogen bonds link these chains into layers parallel to the bc plane and the layers are tied together by complementary π-stacking [centroid–centroid distance = 3.5444 (12) Å] inter­actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (44.5%), H⋯O/O⋯H (18.8%), H⋯N/N⋯H (17.0%) and H⋯C/C⋯H (10.4%) inter­actions.
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spelling pubmed-62189072018-11-15 Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate Abad, Nadeem Ramli, Youssef Hökelek, Tuncer Sebbar, Nada Kheira Mague, Joel T. Essassi, El Mokhtar Acta Crystallogr E Crystallogr Commun Research Communications The mol­ecule of the title compound, C(16)H(17)N(5)O(3), is build up from two fused six-membered rings linked to a 1,2,3-triazole ring, which is attached to an ethyl azido-acetate group. The di­hydro­qinoxalinone portion is planar to within 0.0512 (12) Å and is oriented at a dihedral angle of 87.83 (5)° with respect to the pendant triazole ring. In the crystal, a combination of inter­molecular C—H⋯O and C—H⋯N hydrogen bonds together with slipped π-stacking [centroid–centroid distance = 3.7772 (12) Å] and C—H⋯π (ring) inter­actions lead to the formation of chains extending along the c-axis direction. Additional C—H⋯O hydrogen bonds link these chains into layers parallel to the bc plane and the layers are tied together by complementary π-stacking [centroid–centroid distance = 3.5444 (12) Å] inter­actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (44.5%), H⋯O/O⋯H (18.8%), H⋯N/N⋯H (17.0%) and H⋯C/C⋯H (10.4%) inter­actions. International Union of Crystallography 2018-10-23 /pmc/articles/PMC6218907/ /pubmed/30443399 http://dx.doi.org/10.1107/S2056989018014561 Text en © Abad 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
Abad, Nadeem
Ramli, Youssef
Hökelek, Tuncer
Sebbar, Nada Kheira
Mague, Joel T.
Essassi, El Mokhtar
Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate
title Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate
title_full Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate
title_fullStr Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate
title_full_unstemmed Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate
title_short Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1H-1,2,3-triazol-1-yl}acetate
title_sort crystal structure and hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-di­hydro­quinoxalin-1-yl)meth­yl]-1h-1,2,3-triazol-1-yl}acetate
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6218907/
https://www.ncbi.nlm.nih.gov/pubmed/30443399
http://dx.doi.org/10.1107/S2056989018014561
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