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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,...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2015
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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). |
format | Online Article Text |
id | pubmed-4645010 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2015 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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