Synthesis and crystal structure of (±)-Goniotamirenone C

Authors

Pornphimol Meesakul, University of Wollongong
Christopher Richardson, University of WollongongFollow
Surat Laphookhieo
Stephen G. Pyne, University of WollongongFollow

RIS ID

146532

Publication Details

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

Abstract

2020 International Union of Crystallography. All rights reserved. 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].