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A second polymorph of β-arteether
The crystal structure of the title compound, C(17)H(28)O(5), reported here is a polymorph of the structure first reported by El-Feraly, Al-Yahya, Orabi, McPhail & McPhail [J. Nat. Prod. (1992). 55, 878–883]. It is a derivative of the antimalaria compound artemisinin and consists primarily of th...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2008
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960847/ https://www.ncbi.nlm.nih.gov/pubmed/21201924 http://dx.doi.org/10.1107/S1600536807062812 |
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author | Jasinski, Jerry P. Butcher, Ray J. Yathirajan, H. S. Narayana, B. Sreevidya, T. V. |
author_facet | Jasinski, Jerry P. Butcher, Ray J. Yathirajan, H. S. Narayana, B. Sreevidya, T. V. |
author_sort | Jasinski, Jerry P. |
collection | PubMed |
description | The crystal structure of the title compound, C(17)H(28)O(5), reported here is a polymorph of the structure first reported by El-Feraly, Al-Yahya, Orabi, McPhail & McPhail [J. Nat. Prod. (1992). 55, 878–883]. It is a derivative of the antimalaria compound artemisinin and consists primarily of three substituted ring systems fused together. A cyclohexane ring (distorted chair conformation) fused to a tetrahydropyran group (distorted chair) is adjacent to an oxacycloheptane unit containing an endo-peroxide bridge, giving the molecule its particular three-dimensional arrangement. The crystal packing is stabilized by intermolecular C—H⋯O interactions between an O atom from the endo-peroxide bridge and H atoms from both the cyclohexane and seven-membered oxacycloheptane fused rings, as well as between an O atom and H atom from adjacent tetrahydropyran rings. The two polymorphs have the same space group and similar cell parameters for the a and b axes, but significantly different values for the c axis. |
format | Text |
id | pubmed-2960847 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2008 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29608472010-12-30 A second polymorph of β-arteether Jasinski, Jerry P. Butcher, Ray J. Yathirajan, H. S. Narayana, B. Sreevidya, T. V. Acta Crystallogr Sect E Struct Rep Online Organic Papers The crystal structure of the title compound, C(17)H(28)O(5), reported here is a polymorph of the structure first reported by El-Feraly, Al-Yahya, Orabi, McPhail & McPhail [J. Nat. Prod. (1992). 55, 878–883]. It is a derivative of the antimalaria compound artemisinin and consists primarily of three substituted ring systems fused together. A cyclohexane ring (distorted chair conformation) fused to a tetrahydropyran group (distorted chair) is adjacent to an oxacycloheptane unit containing an endo-peroxide bridge, giving the molecule its particular three-dimensional arrangement. The crystal packing is stabilized by intermolecular C—H⋯O interactions between an O atom from the endo-peroxide bridge and H atoms from both the cyclohexane and seven-membered oxacycloheptane fused rings, as well as between an O atom and H atom from adjacent tetrahydropyran rings. The two polymorphs have the same space group and similar cell parameters for the a and b axes, but significantly different values for the c axis. International Union of Crystallography 2008-02-13 /pmc/articles/PMC2960847/ /pubmed/21201924 http://dx.doi.org/10.1107/S1600536807062812 Text en © International Union of Crystallography 2008 http://journals.iucr.org/services/termsofuse.html This is an open-access article distributed under the terms described at http://journals.iucr.org/services/termsofuse.html. |
spellingShingle | Organic Papers Jasinski, Jerry P. Butcher, Ray J. Yathirajan, H. S. Narayana, B. Sreevidya, T. V. A second polymorph of β-arteether |
title | A second polymorph of β-arteether |
title_full | A second polymorph of β-arteether |
title_fullStr | A second polymorph of β-arteether |
title_full_unstemmed | A second polymorph of β-arteether |
title_short | A second polymorph of β-arteether |
title_sort | second polymorph of β-arteether |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2960847/ https://www.ncbi.nlm.nih.gov/pubmed/21201924 http://dx.doi.org/10.1107/S1600536807062812 |
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