Author/Authors :
Meesakul, Pornphimol Center of Chemical Innovation for Sustainability (CIS) and School of Science - Mae Fah Luang University, Thailand , Richardson, Christopher School of Chemistry and Molecular Bioscience - University of Wollongong, Australia , Laphookhieo, Surat Center of Chemical Innovation for Sustainability (CIS) and School of Science - Mae Fah Luang University, Thailand , Pyne, Stephen G. School of Chemistry and Molecular Bioscience - University of Wollongong, Australia
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 Z′ = 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[Meesakul, P., Jaidee, W., Richardson, C., Andersen, R. J., Patrick, B. O., Willis, A. C., Muanprasat, C., Wang, J., Lei, X., Hadsadee, S., Jungsuttiwong, S., Pyne, S. G. & Laphookhieo, S. (2020). Phytochemistry, 171, 112248-112255.]). Phytochemistry, 171, 112248–112255].
Keywords :
crystal structure , Goniotamirenone C , natural product , semi-synthesis , chlorohydrin
