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Crystal structure of a photobiologically active brominated angular pyran-ocoumarin: bromo-hy-droxy-seselin.

ABSTRACT: The title compound, C₁₄H₁₃BrO₃ [systematic name: rac-(9S,10R)-9-bromo-10-hy-droxy-8,8-dimethyl-9,10-di-hydro-2H,8H-pyrano[2,3-f]chromen-2-one], is a substituted pyran-ocoumarin, obtained by bromination of seselin [8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one], which was isolated from the Indian herb Trachyspermum stictocarpum (Aajmod). The pyrano ring has a distorted half-chair conformation and its mean plane is inclined to the coumarin mean plane by 1.6?(2)°. In the crystal, mol-ecules are linked by pairs of O-H?O hydrogen bonds, forming inversion dimers with an R²₂(16) ring motif. The dimers stack along the a-axis direction and are linked by offset ?-? inter-actions, forming columns [inter-centroid distance = 3.514?(4)?Å].

SUBMITTER: Bauri AK

PROVIDER: S-EPMC5347075 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Crystal structure of a photobiologically active brominated angular pyran-ocoumarin: bromo-hy-droxy-seselin.

Bauri A K AK Foro Sabine S Rahman A F M Mustafizur AF

Acta crystallographica. Section E, Crystallographic communications 20170228 Pt 3

The title compound, C14H13BrO3 [systematic name: rac-(9S,10R)-9-bromo-10-hy-droxy-8,8-dimethyl-9,10-di-hydro-2H,8H-pyrano[2,3-f]chromen-2-one], is a substituted pyran-ocoumarin, obtained by bromination of seselin [8,8-dimethyl-2H,8H-pyrano[2,3-f]chromen-2-one], which was isolated from the Indian herb Trachyspermum stictocarpum (Aajmod). The pyrano ring has a distorted half-chair conformation an ...[more]

PMID: 28316830

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Crystal structure of 4,6-dimethyl-2-{[3,4,5-trihy-droxy-6-(hy-droxy-meth-yl)tetra-hydro-2H-pyran-2-yl]sulfan-yl}nicotino-nitrile.

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