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 π-π inter-actions, forming columns [inter-centroid distance = 3.514 (4) Å].
Highlights
The title compound, C14H13BrO3 [systematic name: rac-(9S,10R)-9-bromo-10hydroxy-8,8-dimethyl-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-2-one], is a substituted pyranocoumarin, obtained by bromination of seselin [8,8dimethyl-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)
The dimers stack along the a-axis direction and are linked by offset – interactions, forming columns [intercentroid distance = 3.514 (4) Å]
Summary
The title compound, rac-(9S,10R)-9-bromo-10-hydroxy-8,8dimethyl-9,10-dihydro-2H,8H-pyrano[2,3-f]chromen-2-one, is a substituted product of the angular pyranocoumarin seselin, with a bromine atom and a hydroxy group at the asymmetric carbon atoms C3 and C4 in the pyrano ring (see Fig. 1). This class of pyranocoumarins have absorption bands in the near. This type of molecule has been combined with a porphyrin to obtain a scaffold-type macromolecule and employed to study of its interaction (host–guest interaction) with fullerenes, such as.
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