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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...

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Detalles Bibliográficos
Autores principales: Bauri, A. K., Foro, Sabine, Rahman, A. F. M. M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
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
Descripción
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).