Ethyl (Z)-4′-(4-eth­oxy-1-hy­droxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate

The 1,3-diketone group of the title compound, C(21)H(20)O(6), exists in a keto–enol form stabilized by a strong intra­molecular O—H⋯O hydrogen bond. As a result, a planar (mean deviation = 0.0099 Å) six-membered hydrogen-bonded ring is formed. The C—O and C—C bond lengths suggest significant electro...

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Detalles Bibliográficos
Autores principales: Ishikawa, Yoshinobu, Ugai, Atsushi
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793735/
https://www.ncbi.nlm.nih.gov/pubmed/24109322
http://dx.doi.org/10.1107/S1600536813018503
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author Ishikawa, Yoshinobu
Ugai, Atsushi
author_facet Ishikawa, Yoshinobu
Ugai, Atsushi
author_sort Ishikawa, Yoshinobu
collection PubMed
description The 1,3-diketone group of the title compound, C(21)H(20)O(6), exists in a keto–enol form stabilized by a strong intra­molecular O—H⋯O hydrogen bond. As a result, a planar (mean deviation = 0.0099 Å) six-membered hydrogen-bonded ring is formed. The C—O and C—C bond lengths suggest significant electron delocalization in the ring. The dihedral angle between the six-membered hydrogen-bonded ring and its adjacent benzene ring is 8.78 (5)° and that between the benzene rings is 19.70 (5)°. In the crystal, mol­ecules are packed in a layered structure parallel to the b axis through C—H⋯O and π–π inter­actions [centroid–centroid distance between stacked benzene rings = 3.868 (2) Å].
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spelling pubmed-37937352013-10-09 Ethyl (Z)-4′-(4-eth­oxy-1-hy­droxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate Ishikawa, Yoshinobu Ugai, Atsushi Acta Crystallogr Sect E Struct Rep Online Organic Papers The 1,3-diketone group of the title compound, C(21)H(20)O(6), exists in a keto–enol form stabilized by a strong intra­molecular O—H⋯O hydrogen bond. As a result, a planar (mean deviation = 0.0099 Å) six-membered hydrogen-bonded ring is formed. The C—O and C—C bond lengths suggest significant electron delocalization in the ring. The dihedral angle between the six-membered hydrogen-bonded ring and its adjacent benzene ring is 8.78 (5)° and that between the benzene rings is 19.70 (5)°. In the crystal, mol­ecules are packed in a layered structure parallel to the b axis through C—H⋯O and π–π inter­actions [centroid–centroid distance between stacked benzene rings = 3.868 (2) Å]. International Union of Crystallography 2013-07-10 /pmc/articles/PMC3793735/ /pubmed/24109322 http://dx.doi.org/10.1107/S1600536813018503 Text en © Ishikawa and Ugai 2013 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 Organic Papers
Ishikawa, Yoshinobu
Ugai, Atsushi
Ethyl (Z)-4′-(4-eth­oxy-1-hy­droxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate
title Ethyl (Z)-4′-(4-eth­oxy-1-hy­droxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate
title_full Ethyl (Z)-4′-(4-eth­oxy-1-hy­droxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate
title_fullStr Ethyl (Z)-4′-(4-eth­oxy-1-hy­droxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate
title_full_unstemmed Ethyl (Z)-4′-(4-eth­oxy-1-hy­droxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate
title_short Ethyl (Z)-4′-(4-eth­oxy-1-hy­droxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate
title_sort ethyl (z)-4′-(4-eth­oxy-1-hy­droxy-3,4-dioxobut-1-en-1-yl)-[1,1′-biphen­yl]-3-carboxyl­ate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793735/
https://www.ncbi.nlm.nih.gov/pubmed/24109322
http://dx.doi.org/10.1107/S1600536813018503
work_keys_str_mv AT ishikawayoshinobu ethylz44ethoxy1hydroxy34dioxobut1en1yl11biphenyl3carboxylate
AT ugaiatsushi ethylz44ethoxy1hydroxy34dioxobut1en1yl11biphenyl3carboxylate

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