3-(4-Acetoxy­phen­yl)-4-oxo-4H-1-benzopyran-5,7-diyl diacetate

Huan-Qiu Li; Yin Luo; Dong-Dong Li; Hai-Liang Zhu

doi:10.1107/S1600536809043670

. 2009 Oct 28;65(Pt 11):o2866. doi: 10.1107/S1600536809043670

3-(4-Acetoxyphenyl)-4-oxo-4H-1-benzopyran-5,7-diyl diacetate

Huan-Qiu Li ^a, Yin Luo ^a, Dong-Dong Li ^a, Hai-Liang Zhu ^a,^*

PMCID: PMC2971439 PMID: 21578453

Abstract

In the title molecule, C₂₁H₁₆O₈, the dihedral angle between the ring systems is 58.5 (1)°. In the crystal, C—H⋯O interactions help to establish the packing.

Related literature

For background to genistein derivatives, see: Li et al. (2006 ▶). For reference structural data, see: Allen et al. (1987 ▶). For related literature, see: Liu & Zhu (2005 ▶).

Experimental

Crystal data

C₂₁H₁₆O₈
M _r = 396.34
Triclinic,
a = 7.6144 (14) Å
b = 10.6755 (19) Å
c = 12.533 (2) Å
α = 72.489 (3)°
β = 73.848 (3)°
γ = 74.762 (3)°
V = 915.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.967, T _max = 0.989
4847 measured reflections
3043 independent reflections
1968 reflections with I > 2σ(I)
R _int = 0.025
200 standard reflections every 3 reflections intensity decay: 1%

Refinement

R[F ² > 2σ(F ²)] = 0.046
wR(F ²) = 0.113
S = 0.96
3043 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043670/hb5164sup1.cif

e-65-o2866-sup1.cif^{(20.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043670/hb5164Isup2.hkl

e-65-o2866-Isup2.hkl^{(149.3KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O8ⁱ	0.93	2.47	3.396 (3)	175
C19—H19A⋯O7ⁱⁱ	0.96	2.57	3.523 (3)	173
C21—H21B⋯O3ⁱⁱⁱ	0.96	2.44	3.328 (3)	154

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This work was financed by a grant (Project 30772627) from the National Natural Science Foundation of China and the China Postdoctoral Science Foundation (Project 20080441043).

supplementary crystallographic information

Comment

Genistein derivatives have been pharmacologically shown some biological activitites (Li et al., 2006). In the title compound, (I) (Fig. 1), the bond lengths and angles (Table 1) are within normal ranges (Allen et al., 1987). The dihedral angle between the least-squares planes of the two benzene rings is 123.8 °. The crystal packing is stabilized by van der Waals forces.

Experimental

Genistein (0.41 g, 1.5 mmol), iodomethane (0.62 ml, 6 mmol) and potassium carbonate (0.42 g, 3 mmol) in 50 ml of dry acetone were sonicated. After the completion of reaction, the given mixture was cooled to room temperature followed by filtration. The filtrate was distilled to give a yellow solid. They were washed with aqueous saturated sodium bicarbonate twice. The solid was dissolved in acetone (15 ml) and stirred for about 10 min to give a clear solution. After keeping the solution in air for 10 d, colorless block-shaped crystals of (I) were formed at the bottom of the vesssl on slow evaporation of the solvent.They were collected, washed three times with acetone and dried in a vacuum desiccator using CaCl₂. The compound was isolated in 98% yield.