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(3S,11Z)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1H-2-benz­oxacyclo­tetra­decine-1,7(8H)-dione (cis-zearalenone): a redetermination

The title compound, also known as cis-zearalenone (cis-ZEN), C(18)H(22)O(5), has already been reported elsewhere [Griffin et al. (1981 ▶). ACA Ser. 29, 35], but no atomic coordinates are publicly available. The mol­ecule is of inter­est with respect to its toxicity. In the crystal, intra­molecular O...

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Detalles Bibliográficos
Autores principales: Köppen, Robert, Riedel, Juliane, Emmerling, Franziska, Koch, Matthias
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297891/
https://www.ncbi.nlm.nih.gov/pubmed/22412694
http://dx.doi.org/10.1107/S1600536812002735
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author Köppen, Robert
Riedel, Juliane
Emmerling, Franziska
Koch, Matthias
author_facet Köppen, Robert
Riedel, Juliane
Emmerling, Franziska
Koch, Matthias
author_sort Köppen, Robert
collection PubMed
description The title compound, also known as cis-zearalenone (cis-ZEN), C(18)H(22)O(5), has already been reported elsewhere [Griffin et al. (1981 ▶). ACA Ser. 29, 35], but no atomic coordinates are publicly available. The mol­ecule is of inter­est with respect to its toxicity. In the crystal, intra­molecular O—H⋯O hydrogen bonds stabilize the mol­ecular conformation, while inter­molecular O—H⋯O hydrogen bonds link the mol­ecules to form infinite chains along the [110] and [1-10] directions. The absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.
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spelling pubmed-32978912012-03-12 (3S,11Z)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1H-2-benz­oxacyclo­tetra­decine-1,7(8H)-dione (cis-zearalenone): a redetermination Köppen, Robert Riedel, Juliane Emmerling, Franziska Koch, Matthias Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, also known as cis-zearalenone (cis-ZEN), C(18)H(22)O(5), has already been reported elsewhere [Griffin et al. (1981 ▶). ACA Ser. 29, 35], but no atomic coordinates are publicly available. The mol­ecule is of inter­est with respect to its toxicity. In the crystal, intra­molecular O—H⋯O hydrogen bonds stabilize the mol­ecular conformation, while inter­molecular O—H⋯O hydrogen bonds link the mol­ecules to form infinite chains along the [110] and [1-10] directions. The absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure. International Union of Crystallography 2012-02-24 /pmc/articles/PMC3297891/ /pubmed/22412694 http://dx.doi.org/10.1107/S1600536812002735 Text en © Köppen et al. 2012 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
Köppen, Robert
Riedel, Juliane
Emmerling, Franziska
Koch, Matthias
(3S,11Z)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1H-2-benz­oxacyclo­tetra­decine-1,7(8H)-dione (cis-zearalenone): a redetermination
title (3S,11Z)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1H-2-benz­oxacyclo­tetra­decine-1,7(8H)-dione (cis-zearalenone): a redetermination
title_full (3S,11Z)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1H-2-benz­oxacyclo­tetra­decine-1,7(8H)-dione (cis-zearalenone): a redetermination
title_fullStr (3S,11Z)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1H-2-benz­oxacyclo­tetra­decine-1,7(8H)-dione (cis-zearalenone): a redetermination
title_full_unstemmed (3S,11Z)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1H-2-benz­oxacyclo­tetra­decine-1,7(8H)-dione (cis-zearalenone): a redetermination
title_short (3S,11Z)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1H-2-benz­oxacyclo­tetra­decine-1,7(8H)-dione (cis-zearalenone): a redetermination
title_sort (3s,11z)-14,16-dihy­droxy-3-methyl-3,4,5,6,9,10-hexa­hydro-1h-2-benz­oxacyclo­tetra­decine-1,7(8h)-dione (cis-zearalenone): a redetermination
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3297891/
https://www.ncbi.nlm.nih.gov/pubmed/22412694
http://dx.doi.org/10.1107/S1600536812002735
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