Crystal structure of 3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one trihydrate

Abstract

The title compound, 3-(β-D-glucopyranosyloxy)-5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-4H-1-benzopyran-4-one trihydrate, C22H22O12·3H2O, is a natural β-D-glucosylflavone (1) isolated from Argemone mexicana Linn. (Papaveraceae). The compound crystallizes in the monoclinic space group C2 with unit-cell parameters: a = 24.2721(9), b = 11.6227(4), c = 9.3193(4)Å, β = 107.489(4)°, Z = 4. The crystal structure was refined to a final R-value of 0.0523 for 3733 observed reflections. The dihedral angle between the benzopyran moiety and the 4-hydroxy-3-methoxyphenyl ring is 9.95(8)°. The basal plane of the glucose moiety is nearly perpendicular to the benzopyran ring system. Molecules are held together in the crystal by O-H·O hydrogen bonds and C-H·π and π-π interactions. 2012 © The Japan Society for Analytical Chemistry.