Cargando…

The crystal structures of four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides

Four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides (halo = F, Cl, Br and I), N-(4-fluoro­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)FNO(3), N-(4-chloro­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)ClNO(3), N-(4-bromo­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)BrNO(3), N...

Descripción completa

Detalles Bibliográficos
Autores principales: Gomes, Ligia R., Low, John Nicolson, Cagide, Fernando, Borges, Fernanda
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4331845/
https://www.ncbi.nlm.nih.gov/pubmed/25705460
http://dx.doi.org/10.1107/S2056989014027054
_version_ 1782357792260096000
author Gomes, Ligia R.
Low, John Nicolson
Cagide, Fernando
Borges, Fernanda
author_facet Gomes, Ligia R.
Low, John Nicolson
Cagide, Fernando
Borges, Fernanda
author_sort Gomes, Ligia R.
collection PubMed
description Four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides (halo = F, Cl, Br and I), N-(4-fluoro­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)FNO(3), N-(4-chloro­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)ClNO(3), N-(4-bromo­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)BrNO(3), N-(4-iodo­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)INO(3), have been structurally characterized. The mol­ecules are essentially planar and each exhibits an anti conformation with respect to the C—N rotamer of the amide and a cis geometry with respect to the relative positions of the C(arom)—C(arom) bond of the chromone ring and the carbonyl group of the amide. The structures each exhibit an intra­molecular hydrogen-bonding network comprising an N—H⋯O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming an S(6) ring, and a weak C(arom)—H⋯O inter­action with the O atom of the carbonyl group of the amide as acceptor, which forms another S(6) ring. All four compounds have the same supra­molecular structure, consisting of R (2) (2)(13) rings that are propagated along the a-axis direction by unit translation. There is π–π stacking involving inversion-related mol­ecules in each structure.
format Online
Article
Text
id pubmed-4331845
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-43318452015-02-20 The crystal structures of four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides Gomes, Ligia R. Low, John Nicolson Cagide, Fernando Borges, Fernanda Acta Crystallogr E Crystallogr Commun Research Communications Four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides (halo = F, Cl, Br and I), N-(4-fluoro­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)FNO(3), N-(4-chloro­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)ClNO(3), N-(4-bromo­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)BrNO(3), N-(4-iodo­phen­yl)-4-oxo-4H-chromene-3-carboxamide, C(16)H(10)INO(3), have been structurally characterized. The mol­ecules are essentially planar and each exhibits an anti conformation with respect to the C—N rotamer of the amide and a cis geometry with respect to the relative positions of the C(arom)—C(arom) bond of the chromone ring and the carbonyl group of the amide. The structures each exhibit an intra­molecular hydrogen-bonding network comprising an N—H⋯O hydrogen bond between the amide N atom and the O atom of the carbonyl group of the pyrone ring, forming an S(6) ring, and a weak C(arom)—H⋯O inter­action with the O atom of the carbonyl group of the amide as acceptor, which forms another S(6) ring. All four compounds have the same supra­molecular structure, consisting of R (2) (2)(13) rings that are propagated along the a-axis direction by unit translation. There is π–π stacking involving inversion-related mol­ecules in each structure. International Union of Crystallography 2015-01-01 /pmc/articles/PMC4331845/ /pubmed/25705460 http://dx.doi.org/10.1107/S2056989014027054 Text en © Gomes et al. 2015 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Research Communications
Gomes, Ligia R.
Low, John Nicolson
Cagide, Fernando
Borges, Fernanda
The crystal structures of four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides
title The crystal structures of four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides
title_full The crystal structures of four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides
title_fullStr The crystal structures of four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides
title_full_unstemmed The crystal structures of four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides
title_short The crystal structures of four N-(4-halophen­yl)-4-oxo-4H-chromene-3-carboxamides
title_sort crystal structures of four n-(4-halophen­yl)-4-oxo-4h-chromene-3-carboxamides
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4331845/
https://www.ncbi.nlm.nih.gov/pubmed/25705460
http://dx.doi.org/10.1107/S2056989014027054
work_keys_str_mv AT gomesligiar thecrystalstructuresoffourn4halophenyl4oxo4hchromene3carboxamides
AT lowjohnnicolson thecrystalstructuresoffourn4halophenyl4oxo4hchromene3carboxamides
AT cagidefernando thecrystalstructuresoffourn4halophenyl4oxo4hchromene3carboxamides
AT borgesfernanda thecrystalstructuresoffourn4halophenyl4oxo4hchromene3carboxamides
AT gomesligiar crystalstructuresoffourn4halophenyl4oxo4hchromene3carboxamides
AT lowjohnnicolson crystalstructuresoffourn4halophenyl4oxo4hchromene3carboxamides
AT cagidefernando crystalstructuresoffourn4halophenyl4oxo4hchromene3carboxamides
AT borgesfernanda crystalstructuresoffourn4halophenyl4oxo4hchromene3carboxamides