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Synthesis and crystal structure of (±)-Goniotamirenone C

Journal Article


Abstract

  • The structure of the racemic version of the natural product Goniotamirenone C [racemic anti-6-(2-chloro-1-hydroxy-2-phenylethyl)-2H-pyran-2-one, C13H11ClO3] at 150 K is reported. The compound crystallizes with monoclinic (P21/n) symmetry and with Z0 = 2. One independent molecule is ordered while the other independent molecule exhibits an interesting whole-molecule enantiomeric disorder with occupancies of 0.846 (4) and 0.154 (4). The independent molecules are hydrogen bonded with -OH... O=C linkages into chains that run parallel to the a axis. This structural analysis corrects our previous assignment as the syn isomer [Meesakul et al. (2020). Phytochemistry, 171, 112248-112255].

Publication Date

  • 2020

Citation

  • Meesakul, P., Richardson, C., Laphookhieo, S., & Pyne, S. G. (2020). Synthesis and crystal structure of (±)-Goniotamirenone C. Acta Crystallographica Section E: Crystallographic Communications, 76, 1728-1731. doi:10.1107/S2056989020013298

Scopus Eid

  • 2-s2.0-85095878648

Start Page

  • 1728

End Page

  • 1731

Volume

  • 76

Abstract

  • The structure of the racemic version of the natural product Goniotamirenone C [racemic anti-6-(2-chloro-1-hydroxy-2-phenylethyl)-2H-pyran-2-one, C13H11ClO3] at 150 K is reported. The compound crystallizes with monoclinic (P21/n) symmetry and with Z0 = 2. One independent molecule is ordered while the other independent molecule exhibits an interesting whole-molecule enantiomeric disorder with occupancies of 0.846 (4) and 0.154 (4). The independent molecules are hydrogen bonded with -OH... O=C linkages into chains that run parallel to the a axis. This structural analysis corrects our previous assignment as the syn isomer [Meesakul et al. (2020). Phytochemistry, 171, 112248-112255].

Publication Date

  • 2020

Citation

  • Meesakul, P., Richardson, C., Laphookhieo, S., & Pyne, S. G. (2020). Synthesis and crystal structure of (±)-Goniotamirenone C. Acta Crystallographica Section E: Crystallographic Communications, 76, 1728-1731. doi:10.1107/S2056989020013298

Scopus Eid

  • 2-s2.0-85095878648

Start Page

  • 1728

End Page

  • 1731

Volume

  • 76