title: (4R,4aR,6S,7S,7aS)-6-Hydroxy-7-hydroxymethyl-4-methylperhydrocyclopenta[c]pyran-1-one chloroform solvate from Valeriana laxiflora.
abstract: The structure of an iridolactone isolated from Valeriana laxiflora was established as (4R,4aR,6S,7S,7aS)-6-hydroxy-7-hydroxymethyl-4-methylperhydrocyclopenta[c]pyran-1-one chloroform solvate, C(10)H(16)O(4).CHCl(3). The two rings are cis-fused. The delta-lactone ring adopts a slightly twisted half-chair conformation with approximate planarity of the lactone group and the cyclopentane ring adopts an envelope conformation. The hydroxy group, the hydroxymethyl group and the methyl group all have beta orientations. The absolute configuration was determined using anomalous dispersion data enhanced by the adventitious inclusion of a chloroform solvent molecule. Hydrogen bonding, crystal packing and ring conformations are discussed in detail.
authors.affiliation: University of Arizona, Department of Pharmacology and Toxicology, 1703 E. Mabel St., Tucson, AZ 85721-0207, USA.
authors.forename: Smriti
authors.initials: S
authors.lastname: Khera
authors.forename: Michael D
authors.initials: MD
authors.lastname: Carducci
authors.forename: Jian-Qiao
authors.initials: JQ
authors.lastname: Gu
authors.forename: Barbara N
authors.initials: BN
authors.lastname: Timmermann
mesh_terms: D002725:Chloroform; D018360:Crystallography, X-Ray; D003517:Cyclopentanes / Q000737:chemistry*; D006860:Hydrogen Bonding; D008958:Models, Molecular; D018515:Plant Leaves / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D011714:Pyrans / Q000737:chemistry*; D012997:Solvents; D014632:Valerian / Q000737:chemistry*
chemical_list: C500650:(4R,4aR,6S,7S,7aS)-6-hydroxy-7-hydroxymethyl-4-methylperhydrocyclopenta(c)pyran-1-one; D003517:Cyclopentanes; D011714:Pyrans; D012997:Solvents; D002725:Chloroform