Crystal structure of di-bromo-meth-oxy-seselin (DBMS), a photobiologically active pyran-ocoumarin

Acta Crystallographica. Section E, Crystallographic Communications
A K BauriA F M Mustafizur Rahman

Abstract

The title compound, C15H14Br2O4 [systematic name: rac-(9S,10R)-3,9-dibromo-10-methoxy-8,8-dimethyl-9,10-dihydropyrano[2,3-h]chromen-2(8H)-one], is a pyran-ocoumarin derivative formed by the bromination of seselin, which is a naturally occurring angular pyran-ocoumarin isolated from the Indian herb Trachyspermum stictocarpum. In the mol-ecule, the benzo-pyran ring system is essentially planar, with a maximum deviation of 0.044 (2) Å for the O atom. The di-hydro-pyran ring is in a half-chair conformation and the four essentially planar atoms of this ring form a dihedral angle of 4.6 (2)° with the benzo-pyran ring system. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming chains propagating along [010]. In addition, π-π stacking inter-actions, with centroid-centroid distances of 3.902 (2) and 3.908 (2) Å, link the hydrogen-bonded chains into layers parallel to (001).

References

Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Jan 28, 2009·Acta Crystallographica. Section D, Biological Crystallography·Anthony L Spek
Feb 18, 2014·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·B K GhoshS Banerjee
Apr 7, 2016·Acta Crystallographica Section B, Structural Science, Crystal Engineering and Materials·Colin R GroomSuzanna C Ward
Mar 21, 2017·Acta Crystallographica. Section E, Crystallographic Communications·A K BauriA F M Mustafizur Rahman

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Citations

Aug 17, 2019·Acta Crystallographica. Section E, Crystallographic Communications·S Syed AbuthahirK Subramanian

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Methods Mentioned

BETA
column chromatography

Software Mentioned

FUGVOS

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