[PDF][PDF] Redetermination of dihydroartemisinin at 103 (2) K

JP Jasinski, RJ Butcher, HS Yathirajan… - … Section E: Structure …, 2008 - journals.iucr.org
JP Jasinski, RJ Butcher, HS Yathirajan, B Narayana, TV Sreevidya
Acta Crystallographica Section E: Structure Reports Online, 2008journals.iucr.org
Tthe structure of the title compound, C15H24O5, has been redetermined at 103 (2) K, with
much improved precision. The title compound was first reported by Luo, Yeh, Brossi, Flippen-
Anderson & Gillardi [Helv. Chim. Acta (1984). 67, 1515–1522]. It is a derivative of the
antimalaria compound artemisinin and consists primarily of three substituted ring systems
fused together. A cyclohexane ring (with a distorted chair conformation), is fused to a
tetrahydropyran group (also with a distorted chair conformation), and is adjacent to an …
Tthe structure of the title compound, C15H24O5, has been redetermined at 103 (2) K, with much improved precision. The title compound was first reported by Luo, Yeh, Brossi, Flippen-Anderson & Gillardi [Helv. Chim. Acta (1984). 67, 1515–1522]. It is a derivative of the antimalaria compound artemisinin and consists primarily of three substituted ring systems fused together. A cyclohexane ring (with a distorted chair conformation), is fused to a tetrahydropyran group (also with a distorted chair conformation), and is adjacent to an oxacycloheptane unit containing an endoperoxide bridge. This gives the molecule a unique three-dimensional arrangement. The crystal packing is stabilized by intermolecular C–H⋯O and O–H⋯O interactions between an H atom from the cyclohexane ring and an O atom from the endoperoxide bridge, as well as between the hydroxyl H atom and an O atom from a tetrahydropyran ring.
International Union of Crystallography
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