Redetermination of dihydro-artemisinin at 103 (2) K.

Tthe structure of the title compound, C(15)H(24)O(5), 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 anti-malaria compound artemisinin and consists primarily of three substituted ring systems fused together. A cyclo-hexane ring (with a distorted chair conformation), is fused to a tetra-hydro-pyran group (also with a distorted chair conformation), and is adjacent to an oxacyclo-heptane unit containing an endoperoxide bridge. This gives the mol-ecule a unique three-dimensional arrangement. The crystal packing is stabilized by inter-molecular C-H⋯O and O-H⋯O inter-actions between an H atom from the cyclo-hexane ring and an O atom from the endoperoxide bridge, as well as between the hydroxyl H atom and an O atom from a tetra-hydro-pyran ring.