title: Two drimane lactones, valdiviolide and 11-epivaldiviolide, in the form of a 1:1 cocrystal obtained from Drimys winteri extracts.
abstract: A cocrystal, C15H22O3·C15H22O3, (I), obtained from Drimys winteri, is composed of two isomeric drimane sesquiterpene lactones, namely valdiviolide, (Ia), and 11-epivaldiviolide, (Ib), neither of which has been reported in the crystal form. Both diastereoisomers present three chiral centres at sites 5, 10 and 11, with an SSR sequence in (Ia) and an SSS sequence in (Ib). O-H···O hydrogen bonds bind molecules into chains running along [120] and the chains are in turn linked by π-π stacking interactions to define planar weakly interacting arrays parallel to (001).
authors.affiliation: Departamento de Ciencias Químicas y Recursos Naturales, Facultad de Ingeniería, Universidad de La Frontera, Temuco, Chile.
authors.forename: Cristian
authors.initials: C
authors.lastname: Paz Robles
authors.affiliation: Departamento de Ciencias Químicas y Recursos Naturales, Facultad de Ingeniería, Universidad de La Frontera, Temuco, Chile.
authors.forename: Darío
authors.initials: D
authors.lastname: Mercado
authors.affiliation: Departamento de Química Inorgánica, Analítica y Química, Física/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina.
authors.forename: Sebastián
authors.initials: S
authors.lastname: Suarez
authors.affiliation: Gerencia de Investigación y Aplicaciones, Centro Atómico Constituyentes, Comisión Nacional de Energía Atómica, Buenos Aires, Argentina.
authors.forename: Ricardo
authors.initials: R
authors.lastname: Baggio
mesh_terms: D018360:Crystallography, X-Ray; D032424:Drimys / Q000737:chemistry*; D006860:Hydrogen Bonding; D007536:Isomerism; D007783:Lactones / Q000737:chemistry* / Q000302:isolation & purification; D015394:Molecular Structure; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: C000595900:11-epivaldiviolide; D007783:Lactones; D000081223:Polycyclic Sesquiterpenes; D012717:Sesquiterpenes; C437376:drimane
keywords: 11-epivaldiviolide; Drimys winteri extracts; cocrystal; crystal structure; drimane lactone; natural products; sesquiterpenes; valdiviolide