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Isolation and crystal structure of lawinal

Journal Article


Abstract


  • The structure of the natural product lawinal [systematic name: (-)-(2S)-5,7-dihydroxy-6-methyl-4-oxo-2-phenylchromane-8-carbaldehyde, C17H14O5] at 150K is reported. The compound crystallizes with monoclinic (I2) symmetry and with Z′ = 2. The absolute configuration could not be determined reliably from X-ray analysis only. However, our analysis returns the S-configuration at the C-2 position, consistent with previous stereochemical assignment from specific rotation. The independent molecules form into alternating hydrogen-bonded chains with C - H⋯O=CH intermolecular linkages that run parallel to the crystallographic a axis and are extended into the ac plane by π-π interactions between their phenyl substituents.

Publication Date


  • 2021

Citation


  • Suthiphasilp, V., Meesakul, P., Richardson, C., Pyne, S. G., & Laphookhieo, S. (2021). Isolation and crystal structure of lawinal. Acta Crystallographica Section E: Crystallographic Communications, 77, 75-78. doi:10.1107/S2056989020016540

Scopus Eid


  • 2-s2.0-85099042296

Web Of Science Accession Number


Start Page


  • 75

End Page


  • 78

Volume


  • 77

Abstract


  • The structure of the natural product lawinal [systematic name: (-)-(2S)-5,7-dihydroxy-6-methyl-4-oxo-2-phenylchromane-8-carbaldehyde, C17H14O5] at 150K is reported. The compound crystallizes with monoclinic (I2) symmetry and with Z′ = 2. The absolute configuration could not be determined reliably from X-ray analysis only. However, our analysis returns the S-configuration at the C-2 position, consistent with previous stereochemical assignment from specific rotation. The independent molecules form into alternating hydrogen-bonded chains with C - H⋯O=CH intermolecular linkages that run parallel to the crystallographic a axis and are extended into the ac plane by π-π interactions between their phenyl substituents.

Publication Date


  • 2021

Citation


  • Suthiphasilp, V., Meesakul, P., Richardson, C., Pyne, S. G., & Laphookhieo, S. (2021). Isolation and crystal structure of lawinal. Acta Crystallographica Section E: Crystallographic Communications, 77, 75-78. doi:10.1107/S2056989020016540

Scopus Eid


  • 2-s2.0-85099042296

Web Of Science Accession Number


Start Page


  • 75

End Page


  • 78

Volume


  • 77