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Crystal structure of dibromomethoxyseselin (DBMS), a photobiologically active pyranocoumarin
The title compound, C(15)H(14)Br(2)O(4) [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 pyranocoumarin derivative formed by the bromination of seselin, which is a naturally occurring angular pyranocoumarin isolated from the India...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5418804/ https://www.ncbi.nlm.nih.gov/pubmed/28529796 http://dx.doi.org/10.1107/S2056989017006132 |
Sumario: | The title compound, C(15)H(14)Br(2)O(4) [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 pyranocoumarin derivative formed by the bromination of seselin, which is a naturally occurring angular pyranocoumarin isolated from the Indian herb Trachyspermum stictocarpum. In the molecule, the benzopyran ring system is essentially planar, with a maximum deviation of 0.044 (2) Å for the O atom. The dihydropyran 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 benzopyran ring system. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming chains propagating along [010]. In addition, π–π stacking interactions, with centroid–centroid distances of 3.902 (2) and 3.908 (2) Å, link the hydrogen-bonded chains into layers parallel to (001). |
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