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Acta Cryst. (2007). E63, o3953    [ doi:10.1107/S1600536807042353 ]

7-Methoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl acetate

H.-Q. Li, L. Shi, Z.-P. Xiao and H.-L. Zhu

Abstract top

In the genistein-related title compound, C19H16O6, the dihedral angle between the two benzene-ring planes is 52.81 (9)°.

Comment top

Genistein derivatives play an important role in organic chemistry (Kim et al., 2004; Li et al., 2006). In the genistein derived title compound, (I) (Fig. 1), the bond lengths and angles are within their normal ranges (Allen et al., 1987). The dihedral angle between the least-squares planes of the two benzene rings (C1—C6 and C9—C14) is 52.81 (9) °. The crystal packing for (I) is stabilized by van der Waals forces.

Related literature top

For background literature, see: Kim et al. (2004); Li et al. (2006). For reference structural data, see: Allen et al. (1987).

Experimental top

Genistein (0.27 g, 1 mmol), iodomethane (0.26 ml, 2 mmol) and potassium carbonate (0.14 g, 1 mmol) in 50 ml of dry acetone were sonicated. After the completion of reaction, the mixture was cooled to room temperature followed by filtration. The filtrate was distilled to give a yellow solid and the solid was dissolved in 15 ml dry pyridine, then acetic anhydride (0.22 ml, 11 mmol) was added, and the mixed solution was stirred at room temperature for 24 h. After that the solution was poured into a 10% solution of aqueous hydrochloric acid (50 ml). The white deposits that precipitated were separated from the solvents by filtration. 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 blocks 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 90% yield.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 30% probability displacement ellipsoids for the non-hydrogen atoms.
7-Methoxy-3-(4-methoxyphenyl)-4-oxo-4H-chromen-5-yl acetate top
Crystal data top
C19H16O6F000 = 712
Mr = 340.32Dx = 1.384 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 1520 reflections
a = 14.2159 (16) Åθ = 2.3–26.6º
b = 12.7207 (15) ŵ = 0.10 mm−1
c = 9.2200 (11) ÅT = 293 (2) K
β = 101.668 (2)ºBlock, colourless
V = 1632.9 (3) Å30.30 × 0.20 × 0.14 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		3720 independent reflections
Radiation source: fine-focus sealed tube2142 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.075
T = 293(2) Kθmax = 27.5º
ω scansθmin = 2.2º
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −15→18
Tmin = 0.970, Tmax = 0.986k = −16→16
11970 measured reflectionsl = −11→11
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.180  w = 1/[σ2(Fo2) + (0.0811P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
3720 reflectionsΔρmax = 0.31 e Å−3
229 parametersΔρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C19H16O6V = 1632.9 (3) Å3
Mr = 340.32Z = 4
Monoclinic, P21/cMo Kα
a = 14.2159 (16) ŵ = 0.10 mm−1
b = 12.7207 (15) ÅT = 293 (2) K
c = 9.2200 (11) Å0.30 × 0.20 × 0.14 mm
β = 101.668 (2)º
Data collection top
Bruker SMART CCD
diffractometer		3720 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2142 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.986Rint = 0.075
11970 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.064229 parameters
wR(F2) = 0.180H-atom parameters constrained
S = 1.03Δρmax = 0.31 e Å−3
3720 reflectionsΔρmin = −0.18 e Å−3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R– factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.46623 (14)0.37820 (16)0.9119 (2)0.0650 (6)
O20.30929 (12)0.56268 (14)0.2772 (2)0.0565 (5)
O30.10811 (12)0.33410 (13)0.15629 (19)0.0507 (5)
O40.00398 (13)0.47929 (15)−0.32341 (19)0.0602 (5)
O50.25889 (13)0.64147 (14)−0.00261 (19)0.0552 (5)
O60.17240 (16)0.73789 (15)0.1245 (2)0.0708 (6)
C10.40595 (19)0.38621 (19)0.7774 (3)0.0489 (7)
C20.44923 (19)0.3960 (2)0.6551 (3)0.0535 (7)
H20.51590.39690.66890.064*
C30.39525 (17)0.4043 (2)0.5159 (3)0.0498 (7)
H30.42570.41150.43620.060*
C40.29485 (17)0.40231 (18)0.4904 (3)0.0431 (6)
C50.25296 (19)0.3930 (2)0.6119 (3)0.0500 (7)
H50.18630.39140.59760.060*
C60.30669 (19)0.3859 (2)0.7548 (3)0.0529 (7)
H60.27630.38100.83490.063*
C70.23594 (17)0.40769 (19)0.3372 (3)0.0432 (6)
C80.25006 (16)0.49320 (18)0.2385 (3)0.0417 (6)
C90.18639 (16)0.49020 (18)0.0908 (3)0.0403 (6)
C100.18742 (17)0.56427 (18)−0.0231 (3)0.0441 (6)
C110.12689 (18)0.5588 (2)−0.1573 (3)0.0483 (6)
H110.12960.6096−0.22890.058*
C120.06065 (17)0.4767 (2)−0.1873 (3)0.0462 (6)
C130.05577 (17)0.40139 (19)−0.0815 (3)0.0448 (6)
H130.01210.3462−0.10080.054*
C140.11834 (17)0.41057 (18)0.0554 (3)0.0412 (6)
C150.16718 (18)0.3364 (2)0.2905 (3)0.0496 (7)
H150.15950.28350.35680.060*
C160.4267 (2)0.3860 (3)1.0399 (3)0.0706 (9)
H16A0.39350.45181.03910.106*
H16B0.47720.38231.12630.106*
H16C0.38240.32921.04160.106*
C17−0.0563 (2)0.3907 (2)−0.3728 (3)0.0623 (8)
H17A−0.01730.3291−0.37270.094*
H17B−0.09180.4036−0.47140.094*
H17C−0.10020.3802−0.30750.094*
C180.2461 (2)0.7245 (2)0.0823 (3)0.0543 (7)
C190.3320 (2)0.7942 (2)0.1069 (4)0.0750 (10)
H19A0.32870.84000.02330.113*
H19B0.38910.75200.11860.113*
H19C0.33370.83540.19460.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0571 (12)0.0754 (14)0.0582 (12)0.0086 (10)0.0014 (10)0.0018 (10)
O20.0502 (11)0.0498 (11)0.0642 (12)−0.0153 (9)−0.0011 (9)0.0073 (9)
O30.0487 (11)0.0431 (10)0.0573 (11)−0.0097 (8)0.0033 (9)0.0003 (8)
O40.0613 (12)0.0660 (12)0.0482 (10)−0.0073 (10)−0.0010 (9)−0.0054 (9)
O50.0584 (12)0.0506 (11)0.0569 (11)−0.0114 (9)0.0121 (9)0.0011 (9)
O60.0667 (14)0.0524 (12)0.0938 (16)0.0037 (10)0.0178 (12)−0.0104 (10)
C10.0451 (15)0.0412 (14)0.0562 (16)0.0037 (12)0.0007 (13)0.0012 (12)
C20.0360 (14)0.0598 (17)0.0639 (18)0.0006 (12)0.0082 (13)0.0043 (14)
C30.0389 (15)0.0543 (16)0.0579 (16)0.0031 (12)0.0137 (13)0.0056 (13)
C40.0407 (14)0.0363 (13)0.0526 (15)0.0006 (10)0.0099 (12)0.0036 (11)
C50.0354 (14)0.0516 (16)0.0620 (17)0.0008 (12)0.0073 (12)0.0033 (13)
C60.0469 (16)0.0551 (16)0.0584 (17)−0.0008 (13)0.0148 (13)0.0046 (13)
C70.0359 (13)0.0419 (14)0.0522 (15)0.0026 (11)0.0097 (11)0.0023 (11)
C80.0343 (13)0.0368 (13)0.0548 (15)0.0012 (11)0.0110 (11)−0.0019 (11)
C90.0340 (13)0.0369 (13)0.0502 (14)0.0026 (10)0.0089 (11)−0.0042 (11)
C100.0422 (14)0.0389 (13)0.0530 (15)−0.0046 (11)0.0139 (12)−0.0026 (11)
C110.0502 (15)0.0496 (15)0.0453 (14)−0.0018 (12)0.0097 (12)0.0015 (12)
C120.0443 (14)0.0480 (15)0.0459 (15)0.0064 (12)0.0084 (12)−0.0095 (12)
C130.0385 (14)0.0396 (13)0.0557 (15)0.0005 (11)0.0084 (12)−0.0107 (12)
C140.0404 (14)0.0334 (12)0.0510 (14)0.0029 (10)0.0121 (11)0.0004 (11)
C150.0462 (16)0.0431 (14)0.0573 (16)−0.0011 (12)0.0054 (13)0.0084 (12)
C160.080 (2)0.077 (2)0.0516 (17)0.0027 (17)0.0051 (16)0.0032 (15)
C170.0552 (18)0.0654 (19)0.0611 (17)−0.0015 (14)−0.0009 (14)−0.0127 (14)
C180.0589 (19)0.0414 (15)0.0598 (17)0.0042 (14)0.0053 (15)0.0091 (13)
C190.071 (2)0.0523 (17)0.093 (2)−0.0193 (16)−0.0043 (18)0.0041 (16)
Geometric parameters (Å, °) top
O1—C11.361 (3)C7—C81.458 (3)
O1—C161.410 (3)C8—C91.475 (3)
O2—C81.223 (3)C9—C141.393 (3)
O3—C151.348 (3)C9—C101.413 (3)
O3—C141.374 (3)C10—C111.359 (3)
O4—C121.348 (3)C11—C121.396 (3)
O4—C171.433 (3)C11—H110.9300
O5—C181.349 (3)C12—C131.380 (4)
O5—C101.398 (3)C13—C141.394 (3)
O6—C181.201 (3)C13—H130.9300
C1—C61.384 (4)C15—H150.9300
C1—C21.395 (4)C16—H16A0.9600
C2—C31.359 (3)C16—H16B0.9600
C2—H20.9300C16—H16C0.9600
C3—C41.399 (3)C17—H17A0.9600
C3—H30.9300C17—H17B0.9600
C4—C51.376 (4)C17—H17C0.9600
C4—C71.491 (3)C18—C191.489 (4)
C5—C61.386 (3)C19—H19A0.9600
C5—H50.9300C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C7—C151.339 (3)
C1—O1—C16118.3 (2)C10—C11—H11120.1
C15—O3—C14118.33 (19)C12—C11—H11120.1
C12—O4—C17118.9 (2)O4—C12—C13124.7 (2)
C18—O5—C10116.7 (2)O4—C12—C11114.8 (2)
O1—C1—C6124.9 (3)C13—C12—C11120.5 (2)
O1—C1—C2116.4 (2)C12—C13—C14117.9 (2)
C6—C1—C2118.8 (2)C12—C13—H13121.0
C3—C2—C1120.9 (2)C14—C13—H13121.0
C3—C2—H2119.6O3—C14—C9121.3 (2)
C1—C2—H2119.6O3—C14—C13114.7 (2)
C2—C3—C4121.3 (3)C9—C14—C13124.0 (2)
C2—C3—H3119.4C7—C15—O3126.1 (2)
C4—C3—H3119.4C7—C15—H15117.0
C5—C4—C3117.4 (2)O3—C15—H15117.0
C5—C4—C7121.5 (2)O1—C16—H16A109.5
C3—C4—C7121.1 (2)O1—C16—H16B109.5
C4—C5—C6122.2 (2)H16A—C16—H16B109.5
C4—C5—H5118.9O1—C16—H16C109.5
C6—C5—H5118.9H16A—C16—H16C109.5
C1—C6—C5119.5 (3)H16B—C16—H16C109.5
C1—C6—H6120.3O4—C17—H17A109.5
C5—C6—H6120.3O4—C17—H17B109.5
C15—C7—C8119.2 (2)H17A—C17—H17B109.5
C15—C7—C4120.5 (2)O4—C17—H17C109.5
C8—C7—C4120.3 (2)H17A—C17—H17C109.5
O2—C8—C7122.0 (2)H17B—C17—H17C109.5
O2—C8—C9123.1 (2)O6—C18—O5121.8 (3)
C7—C8—C9114.9 (2)O6—C18—C19127.5 (3)
C14—C9—C10115.0 (2)O5—C18—C19110.6 (3)
C14—C9—C8120.2 (2)C18—C19—H19A109.5
C10—C9—C8124.9 (2)C18—C19—H19B109.5
C11—C10—O5117.9 (2)H19A—C19—H19B109.5
C11—C10—C9122.9 (2)C18—C19—H19C109.5
O5—C10—C9119.0 (2)H19A—C19—H19C109.5
C10—C11—C12119.8 (2)H19B—C19—H19C109.5
C16—O1—C1—C6−10.1 (4)C14—C9—C10—C110.0 (3)
C16—O1—C1—C2169.5 (2)C8—C9—C10—C11−179.5 (2)
O1—C1—C2—C3179.9 (2)C14—C9—C10—O5−174.3 (2)
C6—C1—C2—C3−0.5 (4)C8—C9—C10—O56.2 (3)
C1—C2—C3—C4−0.6 (4)O5—C10—C11—C12173.8 (2)
C2—C3—C4—C50.8 (4)C9—C10—C11—C12−0.6 (4)
C2—C3—C4—C7−177.8 (2)C17—O4—C12—C13−9.8 (3)
C3—C4—C5—C60.1 (4)C17—O4—C12—C11170.9 (2)
C7—C4—C5—C6178.8 (2)C10—C11—C12—O4179.7 (2)
O1—C1—C6—C5−179.0 (2)C10—C11—C12—C130.4 (4)
C2—C1—C6—C51.4 (4)O4—C12—C13—C14−178.9 (2)
C4—C5—C6—C1−1.2 (4)C11—C12—C13—C140.4 (3)
C5—C4—C7—C15−50.3 (3)C15—O3—C14—C9−1.4 (3)
C3—C4—C7—C15128.4 (3)C15—O3—C14—C13178.8 (2)
C5—C4—C7—C8127.3 (3)C10—C9—C14—O3−178.9 (2)
C3—C4—C7—C8−54.1 (3)C8—C9—C14—O30.6 (3)
C15—C7—C8—O2177.2 (2)C10—C9—C14—C130.9 (3)
C4—C7—C8—O2−0.4 (4)C8—C9—C14—C13−179.6 (2)
C15—C7—C8—C9−1.6 (3)C12—C13—C14—O3178.7 (2)
C4—C7—C8—C9−179.2 (2)C12—C13—C14—C9−1.1 (3)
O2—C8—C9—C14−177.9 (2)C8—C7—C15—O31.0 (4)
C7—C8—C9—C140.9 (3)C4—C7—C15—O3178.5 (2)
O2—C8—C9—C101.5 (4)C14—O3—C15—C70.6 (4)
C7—C8—C9—C10−179.7 (2)C10—O5—C18—O6−8.3 (4)
C18—O5—C10—C11106.5 (3)C10—O5—C18—C19174.2 (2)
C18—O5—C10—C9−79.0 (3)
references
References top

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

Bruker (2001). SMART, SAINT, SADABS and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.

Kim, Y. W., Hackett, J. C. & Brueggemeier, R. W. (2004). J. Med. Chem. 47, 4032–4040.

Li, H.-Q., Ge, H.-M., Chen, Y.-X., Xu, C., Shi, L., Ding, H., Zhu, H.-L. & Tan, R. X. (2006). Chem. Biodiver. 3, 463–472.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.