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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...

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Autores principales: Jasinski, Jerry P., Butcher, Ray J., Yathirajan, H. S., Narayana, B., Sreevidya, T. V.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
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.
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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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