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Isolation and crystal structure of lawinal.

ABSTRACT: The structure of the natural product lawinal [systematic name: (-)-(2S)-5,7-dihy-droxy-6-methyl-4-oxo-2-phenyl-chromane-8-carbaldehyde, C₁₇H₁₄O₅] at 150?K 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 mol-ecules form into alternating hydrogen-bonded chains with C-H?O=CH inter-molecular linkages that run parallel to the crystallographic a axis and are extended into the ac plane by ?-? inter-actions between their phenyl substituents.

SUBMITTER: Suthiphasilp V

PROVIDER: S-EPMC7784046 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Isolation and crystal structure of lawinal.

Suthiphasilp Virayu V Meesakul Pornphimol P Richardson Christopher C Pyne Stephen G SG Laphookhieo Surat S

Acta crystallographica. Section E, Crystallographic communications 20210101 Pt 1

The structure of the natural product lawinal [systematic name: (-)-(2S)-5,7-dihy-droxy-6-methyl-4-oxo-2-phenyl-chromane-8-carbaldehyde, C17H14O5] at 150 K 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 a ...[more]

PMID: 33520287

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