Crystal structure and Hirshfeld analysis of (1a S ,3a R ,4a S ,5a R )-15-acetoxylinden-7(11),8-trieno-12,8-lactone

• Published in: Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2022-06, Vol.78 (6), p.642-646
• Main Authors: Lu, Qiang-Qiang, Shi, Xin-Wei, Zhou, Ya-Fu, Cui, Xin-Ai, Wang, Hong
• Format: Article
• Language: English
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989022004625

The structure of the title compound, C 17 H 20 O 4 [systematic name: (1a S ,3a R ,4a S ,5a R )-15-(acetoxy)linden-7(11),8-trieno-12,8-lactone or (4a R ,5 S ,5a R ,6a S ,6b R )-5-(acetoxymethyl)-4a,5,5a,6,6a,6b-hexahydro-3,6b-dimethylcyclopropa[2,3]indeno[5,6- b ]furan-2(4 H )-one, ent -chloranthalactone C], a natural product isolated from the whole plant Chloranthus japonicus Sieb., is a typical lindenane-type sesquiterpenoid. The molecule comprises a bicyclo[3.1.0]hexane ring ( A / B system) bearing an acetoxymethyl (C-4) group, a bicyclo[4.3.0]nonane ring ( B / C system) containing a double bond (C-8/9) and a chiral quaternary carbon (C-10), and a 7(11)-en-12,8-olide structural moiety on the cyclohexan-8-ene ( C ring). In the tetracyclic skeleton, the 1,3-cyclopropane ring has a β-configuration, and atoms H-5 and H 3 -14 have α- and β-orientations, respectively. In the crystal, the molecules are assembled into a two-dimensional network by weak O...H/H...O interactions. Hirshfeld surface analysis illustrates that the greatest contributions are from H...H (55.2%), O...H/H...O (34.6%) and C...H/H...C (8.9%) contacts.