Narsimha Reddy Penthala, Shobanbabu Bommagani, Venumadhav Janganati, Sean Parkin, Peter A. Crooks

Research output: Contribution to journalArticlepeer-review


The title compound, C21H23BrO3 [systematic name: (3E,3aS,6Z,9R,9aS,9bS)-3-(2-bromobenzylidene)-9-hydroxy-6,9-dimethyl-3, 3a,4,5,7,8,9,9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] was prepared by the reaction of 1-bromo-2-iodobenzene with micheliolide [systematic name: (3aS,R,9aS,9bS,Z)-9-hydroxy-6,9-dimethyl-3-methylene-3,3a,4,5,7,8,9, 9a-octahydroazuleno[4,5-b]furan-2(9bH)-one] under Heck reaction conditions. The title compound exhibits intramolecular O - H⋯O hydrogen bonding between the hydroxy group and the lactone ring O atom, forming a ring of graph-set motif S(6). The 2-bromophenyl group is trans to the lactone ring, indicating that this is the E isomer (geometry of the exocyclic C=C bond). The dihedral angle between the benzene ring of the 2-bromophenyl moiety and the mean plane of the lactone ring is 51.68 (7)°.

Original languageEnglish
Pages (from-to)o251-o252
JournalActa Crystallographica Section E: Structure Reports Online
Issue number3
StatePublished - Mar 2014


  • Data-to-parameter ratio = 18.0
  • Mean σ(C-C) = 0.004 Å
  • R factor = 0.025
  • Single-crystal X-ray study
  • T = 90 K
  • wR factor = 0.064

ASJC Scopus subject areas

  • Chemistry (all)
  • Materials Science (all)
  • Condensed Matter Physics


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