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Crystal and mol­ecular structure of aflatrem

The crystal structure of the title compound, C(32)H(39)NO(4), confirms the absolute configuration of the seven chiral centres in the mol­ecule. The molecule has a 1,1-dimethylprop-2-enyl substituent on the indole nucleus and this nucleus shares one edge with the five-membered ring which is, in turn,...

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Autores principales: Lenta, Bruno N., Ngatchou, Jules, Kenfack, Patrice T., Neumann, Beate, Stammler, Hans-Georg, Sewald, Norbert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645010/
https://www.ncbi.nlm.nih.gov/pubmed/26594569
http://dx.doi.org/10.1107/S2056989015019040
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author Lenta, Bruno N.
Ngatchou, Jules
Kenfack, Patrice T.
Neumann, Beate
Stammler, Hans-Georg
Sewald, Norbert
author_facet Lenta, Bruno N.
Ngatchou, Jules
Kenfack, Patrice T.
Neumann, Beate
Stammler, Hans-Georg
Sewald, Norbert
author_sort Lenta, Bruno N.
collection PubMed
description The crystal structure of the title compound, C(32)H(39)NO(4), confirms the absolute configuration of the seven chiral centres in the mol­ecule. The molecule has a 1,1-dimethylprop-2-enyl substituent on the indole nucleus and this nucleus shares one edge with the five-membered ring which is, in turn, connected to a sequence of three edge-shared fused rings. The skeleton is completed by the 7,7-trimethyl-6,8-dioxabi­cyclo­[3.2.1]oct-3-en-2-one group connected to the terminal cyclohexene ring. The two cyclohexane rings adopt chair and half-chair conformations, while in the dioxabi­cyclo­[3.2.1]oct-3-en-2-one unit, the six-membered ring has a half-chair conformation. The indole system of the mol­ecule exhibits a tilt of 2.02 (1)° between its two rings. In the crystal, O—H⋯O hydrogen bonds connect mol­ecules into chains along [010]. Weak N—H⋯π inter­actions connect these chains, forming sheets parallel to (10-1).
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spelling pubmed-46450102015-11-20 Crystal and mol­ecular structure of aflatrem Lenta, Bruno N. Ngatchou, Jules Kenfack, Patrice T. Neumann, Beate Stammler, Hans-Georg Sewald, Norbert Acta Crystallogr E Crystallogr Commun Data Reports The crystal structure of the title compound, C(32)H(39)NO(4), confirms the absolute configuration of the seven chiral centres in the mol­ecule. The molecule has a 1,1-dimethylprop-2-enyl substituent on the indole nucleus and this nucleus shares one edge with the five-membered ring which is, in turn, connected to a sequence of three edge-shared fused rings. The skeleton is completed by the 7,7-trimethyl-6,8-dioxabi­cyclo­[3.2.1]oct-3-en-2-one group connected to the terminal cyclohexene ring. The two cyclohexane rings adopt chair and half-chair conformations, while in the dioxabi­cyclo­[3.2.1]oct-3-en-2-one unit, the six-membered ring has a half-chair conformation. The indole system of the mol­ecule exhibits a tilt of 2.02 (1)° between its two rings. In the crystal, O—H⋯O hydrogen bonds connect mol­ecules into chains along [010]. Weak N—H⋯π inter­actions connect these chains, forming sheets parallel to (10-1). International Union of Crystallography 2015-10-17 /pmc/articles/PMC4645010/ /pubmed/26594569 http://dx.doi.org/10.1107/S2056989015019040 Text en © Lenta 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 Data Reports
Lenta, Bruno N.
Ngatchou, Jules
Kenfack, Patrice T.
Neumann, Beate
Stammler, Hans-Georg
Sewald, Norbert
Crystal and mol­ecular structure of aflatrem
title Crystal and mol­ecular structure of aflatrem
title_full Crystal and mol­ecular structure of aflatrem
title_fullStr Crystal and mol­ecular structure of aflatrem
title_full_unstemmed Crystal and mol­ecular structure of aflatrem
title_short Crystal and mol­ecular structure of aflatrem
title_sort crystal and mol­ecular structure of aflatrem
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645010/
https://www.ncbi.nlm.nih.gov/pubmed/26594569
http://dx.doi.org/10.1107/S2056989015019040
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