Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Previous article
Next article
Previous article
Issue contents
Download PDF of article
Download CIF
3D view
Navigation
Highlighting
Dictionary of Crystallography reference
IUPAC Gold Book reference
more ...
Download citation
FormatBIBTeX
EndNote
RefMan
Refer
Medline
CIF
SGML
Plain Text
share
Next article

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2866
https://doi.org/10.1107/S1600536809043670

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

Huan-Qiu Li,a Yin Luo,a Dong-Dong Lia and Hai-Liang Zhua*

aSchool of Life Science, Nanjing University, Nanjing 210093, People's Republic of China
*Correspondence e-mail: owengoal13@163.com

(Received 21 October 2009; accepted 22 October 2009; online 28 October 2009)

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[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.]). For reference structural data, see: Allen et al. (1987[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.]). For related literature, see: Liu & Zhu (2005[Liu, X.-Y. & Zhu, H.-L. (2005). Syn. React. Inorg. Met. Org. Nano-Met. Chem. 35, 325-332.]).

[Scheme 1]

Experimental

Crystal data

  • C21H16O8

  • Mr = 396.34

  • Triclinic, [P \overline 1]

  • 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[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.967, Tmax = 0.989

  • 4847 measured reflections

  • 3043 independent reflections

  • 1968 reflections with I > 2σ(I)

  • Rint = 0.025

  • 200 standard reflections every 3 reflections intensity decay: 1%
Refinement

  • R[F2 > 2σ(F2)] = 0.046

  • wR(F2) = 0.113

  • S = 0.96

  • 3043 reflections

  • 265 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.17 e Å−3

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
Symmetry codes: (i) x, y, z-1; (ii) -x+1, -y+1, -z-1; (iii) -x+1, -y, -z+1.

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809043670/hb5164Isup2.hkl

checkCIF report


Comment top

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.

Related literature top

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 top

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.

Refinement top

All H atoms were positioned geometrically (C—H = 0.93 Å for the aromatic H atoms and C—H = 0.96 Å for the aliphatic H atoms) and were refined as riding, with Uiso(H) = 1.2Ueq(C) and Uiso(H) = 1.2Ueq(N).

Structure description top

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.

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).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 30% probability displacement ellipsoids.
3-(4-Acetoxyphenyl)-4-oxo-4H-1-benzopyran-5,7-diyl diacetate top
Crystal data top
C21H16O8Z = 2
Mr = 396.34F(000) = 412
Triclinic, P1Dx = 1.438 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.6144 (14) ÅCell parameters from 25 reflections
b = 10.6755 (19) Åθ = 9–12°
c = 12.533 (2) ŵ = 0.11 mm−1
α = 72.489 (3)°T = 298 K
β = 73.848 (3)°Block, colourless
γ = 74.762 (3)°0.30 × 0.20 × 0.10 mm
V = 915.2 (3) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer		1968 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ω/2θ scansh = −8→9
Absorption correction: ψ scan
(North et al., 1968)		k = −12→11
Tmin = 0.967, Tmax = 0.989l = −14→14
4847 measured reflections200 standard reflections every 3 reflections
3043 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0486P)2]
where P = (Fo2 + 2Fc2)/3
3043 reflections(Δ/σ)max = 0.008
265 parametersΔρmax = 0.17 e Å−3
0 restraintsΔρmin = −0.17 e Å−3
Crystal data top
C21H16O8γ = 74.762 (3)°
Mr = 396.34V = 915.2 (3) Å3
Triclinic, P1Z = 2
a = 7.6144 (14) ÅMo Kα radiation
b = 10.6755 (19) ŵ = 0.11 mm−1
c = 12.533 (2) ÅT = 298 K
α = 72.489 (3)°0.30 × 0.20 × 0.10 mm
β = 73.848 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer		1968 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.025
Tmin = 0.967, Tmax = 0.989200 standard reflections every 3 reflections
4847 measured reflections intensity decay: 1%
3043 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.113H-atom parameters constrained
S = 0.96Δρmax = 0.17 e Å−3
3043 reflectionsΔρmin = −0.17 e Å−3
265 parameters
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 > σ(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
C10.2549 (3)−0.0952 (3)0.18430 (19)0.0501 (6)
H10.2405−0.18330.21860.060*
C20.2866 (3)−0.0287 (2)0.24896 (17)0.0396 (6)
C30.3137 (3)0.1090 (2)0.19959 (17)0.0384 (6)
C40.2951 (3)0.2985 (2)0.01826 (17)0.0359 (5)
C50.2684 (3)0.3459 (2)−0.09068 (17)0.0400 (6)
H50.27050.4350−0.12890.048*
C60.2379 (3)0.2591 (2)−0.14434 (17)0.0396 (6)
C70.2302 (3)0.1288 (2)−0.08973 (17)0.0419 (6)
H70.20950.0718−0.12630.050*
C80.2545 (3)0.0838 (2)0.02250 (17)0.0397 (6)
C90.2890 (3)0.1646 (2)0.08047 (17)0.0353 (5)
C100.2867 (3)−0.0925 (2)0.37225 (18)0.0401 (6)
C110.1331 (3)−0.1409 (3)0.44474 (19)0.0489 (6)
H110.0303−0.13460.41580.059*
C120.1296 (3)−0.1986 (3)0.55972 (19)0.0494 (6)
H120.0259−0.23150.60810.059*
C130.2823 (3)−0.2065 (2)0.60117 (18)0.0433 (6)
C140.4364 (3)−0.1589 (2)0.53217 (18)0.0463 (6)
H140.5384−0.16550.56200.056*
C150.4382 (3)−0.1008 (2)0.41701 (19)0.0468 (6)
H150.5417−0.06710.36940.056*
C160.2072 (3)0.4303 (2)0.15330 (19)0.0408 (6)
C170.2872 (4)0.5041 (3)0.2056 (2)0.0600 (7)
H17A0.18810.55420.25180.090*
H17B0.35700.56430.14620.090*
H17C0.36800.44150.25270.090*
C180.3122 (4)0.3839 (3)−0.33891 (19)0.0513 (7)
C190.2309 (4)0.4375 (3)−0.4425 (2)0.0703 (8)
H19A0.32180.4743−0.50660.105*
H19B0.12320.5063−0.42910.105*
H19C0.19530.3665−0.45880.105*
C200.2196 (3)−0.1878 (3)0.79073 (19)0.0423 (6)
C210.2206 (3)−0.2675 (3)0.91124 (17)0.0501 (7)
H21A0.1991−0.20790.95970.075*
H21B0.3393−0.32670.91410.075*
H21C0.1240−0.31910.93730.075*
O10.2418 (2)−0.04736 (16)0.07344 (12)0.0517 (5)
O20.3515 (2)0.17371 (16)0.25336 (13)0.0543 (5)
O30.3377 (2)0.38639 (15)0.06600 (12)0.0400 (4)
O40.1996 (2)0.30585 (17)−0.25361 (12)0.0496 (4)
O50.2817 (2)−0.26831 (16)0.71821 (12)0.0491 (4)
O60.0523 (2)0.41095 (18)0.17983 (14)0.0587 (5)
O70.4524 (3)0.4012 (2)−0.32773 (14)0.0704 (6)
O80.1702 (2)−0.06907 (19)0.76094 (14)0.0620 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0721 (17)0.0365 (15)0.0389 (14)−0.0123 (13)−0.0165 (12)0.0003 (11)
C20.0428 (13)0.0343 (14)0.0396 (13)−0.0042 (11)−0.0109 (11)−0.0070 (11)
C30.0342 (12)0.0426 (15)0.0383 (12)−0.0040 (11)−0.0100 (10)−0.0108 (11)
C40.0325 (12)0.0384 (14)0.0384 (13)−0.0076 (10)−0.0090 (10)−0.0100 (10)
C50.0410 (13)0.0381 (14)0.0386 (13)−0.0093 (11)−0.0085 (10)−0.0049 (11)
C60.0407 (13)0.0469 (16)0.0314 (12)−0.0075 (11)−0.0085 (10)−0.0101 (11)
C70.0486 (14)0.0438 (16)0.0386 (13)−0.0120 (12)−0.0096 (11)−0.0152 (11)
C80.0431 (14)0.0363 (15)0.0372 (13)−0.0069 (11)−0.0075 (10)−0.0073 (10)
C90.0329 (12)0.0344 (14)0.0372 (12)−0.0050 (10)−0.0075 (10)−0.0082 (10)
C100.0490 (14)0.0318 (14)0.0376 (13)−0.0028 (11)−0.0114 (11)−0.0083 (10)
C110.0512 (15)0.0510 (17)0.0447 (14)−0.0123 (13)−0.0168 (12)−0.0041 (12)
C120.0512 (15)0.0505 (17)0.0421 (14)−0.0154 (12)−0.0050 (12)−0.0049 (12)
C130.0594 (16)0.0364 (15)0.0332 (12)−0.0075 (12)−0.0129 (11)−0.0064 (10)
C140.0513 (15)0.0454 (16)0.0429 (14)−0.0091 (12)−0.0181 (12)−0.0049 (12)
C150.0486 (15)0.0447 (16)0.0452 (14)−0.0128 (12)−0.0095 (12)−0.0058 (12)
C160.0457 (15)0.0366 (15)0.0408 (13)−0.0067 (11)−0.0142 (11)−0.0071 (11)
C170.0672 (18)0.0626 (19)0.0603 (16)−0.0176 (15)−0.0137 (14)−0.0256 (14)
C180.0628 (18)0.0495 (17)0.0384 (14)−0.0102 (14)−0.0084 (13)−0.0095 (12)
C190.088 (2)0.071 (2)0.0444 (15)−0.0077 (16)−0.0230 (15)−0.0021 (14)
C200.0391 (13)0.0459 (17)0.0446 (14)−0.0077 (12)−0.0108 (11)−0.0139 (12)
C210.0490 (14)0.0631 (18)0.0385 (13)−0.0107 (13)−0.0128 (11)−0.0100 (12)
O10.0822 (12)0.0373 (10)0.0410 (9)−0.0177 (9)−0.0192 (8)−0.0071 (7)
O20.0783 (12)0.0447 (11)0.0495 (10)−0.0160 (9)−0.0333 (9)−0.0042 (8)
O30.0431 (9)0.0406 (10)0.0403 (8)−0.0140 (7)−0.0096 (7)−0.0102 (7)
O40.0595 (10)0.0558 (11)0.0355 (9)−0.0138 (9)−0.0180 (8)−0.0050 (8)
O50.0678 (11)0.0410 (10)0.0363 (9)−0.0091 (8)−0.0147 (8)−0.0043 (8)
O60.0420 (10)0.0676 (13)0.0711 (12)−0.0153 (9)−0.0061 (9)−0.0254 (10)
O70.0757 (13)0.0925 (16)0.0483 (11)−0.0369 (12)−0.0087 (10)−0.0113 (10)
O80.0805 (13)0.0464 (12)0.0555 (11)0.0031 (10)−0.0225 (10)−0.0136 (9)
Geometric parameters (Å, º) top
C1—C21.328 (3)C13—C141.366 (3)
C1—O11.351 (2)C13—O51.415 (2)
C1—H10.9300C14—C151.387 (3)
C2—C31.459 (3)C14—H140.9300
C2—C101.490 (3)C15—H150.9300
C3—O21.227 (2)C16—O61.189 (2)
C3—C91.477 (3)C16—O31.365 (3)
C4—C51.359 (3)C16—C171.485 (3)
C4—O31.396 (2)C17—H17A0.9600
C4—C91.414 (3)C17—H17B0.9600
C5—C61.392 (3)C17—H17C0.9600
C5—H50.9300C18—O71.182 (3)
C6—C71.362 (3)C18—O41.379 (3)
C6—O41.394 (2)C18—C191.487 (3)
C7—C81.391 (3)C19—H19A0.9600
C7—H70.9300C19—H19B0.9600
C8—O11.370 (3)C19—H19C0.9600
C8—C91.394 (3)C20—O81.196 (3)
C10—C111.380 (3)C20—O51.344 (3)
C10—C151.389 (3)C20—C211.495 (3)
C11—C121.382 (3)C21—H21A0.9600
C11—H110.9300C21—H21B0.9600
C12—C131.374 (3)C21—H21C0.9600
C12—H120.9300
C2—C1—O1126.3 (2)C12—C13—O5119.0 (2)
C2—C1—H1116.9C13—C14—C15118.9 (2)
O1—C1—H1116.9C13—C14—H14120.5
C1—C2—C3119.5 (2)C15—C14—H14120.5
C1—C2—C10120.2 (2)C14—C15—C10120.5 (2)
C3—C2—C10120.22 (19)C14—C15—H15119.7
O2—C3—C2122.63 (19)C10—C15—H15119.7
O2—C3—C9122.9 (2)O6—C16—O3122.7 (2)
C2—C3—C9114.48 (19)O6—C16—C17126.9 (2)
C5—C4—O3117.23 (19)O3—C16—C17110.41 (19)
C5—C4—C9122.3 (2)C16—C17—H17A109.5
O3—C4—C9120.37 (17)C16—C17—H17B109.5
C4—C5—C6119.1 (2)H17A—C17—H17B109.5
C4—C5—H5120.4C16—C17—H17C109.5
C6—C5—H5120.4H17A—C17—H17C109.5
C7—C6—C5121.76 (19)H17B—C17—H17C109.5
C7—C6—O4117.3 (2)O7—C18—O4123.0 (2)
C5—C6—O4120.7 (2)O7—C18—C19127.3 (2)
C6—C7—C8117.9 (2)O4—C18—C19109.8 (2)
C6—C7—H7121.1C18—C19—H19A109.5
C8—C7—H7121.1C18—C19—H19B109.5
O1—C8—C7115.1 (2)H19A—C19—H19B109.5
O1—C8—C9121.63 (18)C18—C19—H19C109.5
C7—C8—C9123.3 (2)H19A—C19—H19C109.5
C8—C9—C4115.59 (18)H19B—C19—H19C109.5
C8—C9—C3120.0 (2)O8—C20—O5123.6 (2)
C4—C9—C3124.43 (19)O8—C20—C21125.8 (2)
C11—C10—C15118.88 (19)O5—C20—C21110.6 (2)
C11—C10—C2120.20 (19)C20—C21—H21A109.5
C15—C10—C2120.9 (2)C20—C21—H21B109.5
C10—C11—C12121.0 (2)H21A—C21—H21B109.5
C10—C11—H11119.5C20—C21—H21C109.5
C12—C11—H11119.5H21A—C21—H21C109.5
C13—C12—C11118.7 (2)H21B—C21—H21C109.5
C13—C12—H12120.7C1—O1—C8117.90 (18)
C11—C12—H12120.7C16—O3—C4117.96 (15)
C14—C13—C12121.9 (2)C18—O4—C6119.08 (18)
C14—C13—O5119.02 (19)C20—O5—C13116.67 (18)
O1—C1—C2—C3−1.0 (4)C1—C2—C10—C15125.7 (3)
O1—C1—C2—C10176.5 (2)C3—C2—C10—C15−56.8 (3)
C1—C2—C3—O2−176.7 (2)C15—C10—C11—C12−0.9 (4)
C10—C2—C3—O25.7 (3)C2—C10—C11—C12−179.1 (2)
C1—C2—C3—C94.2 (3)C10—C11—C12—C130.3 (4)
C10—C2—C3—C9−173.35 (19)C11—C12—C13—C140.1 (4)
O3—C4—C5—C6175.77 (18)C11—C12—C13—O5−178.5 (2)
C9—C4—C5—C6−1.4 (3)C12—C13—C14—C150.2 (4)
C4—C5—C6—C71.4 (3)O5—C13—C14—C15178.7 (2)
C4—C5—C6—O4176.38 (18)C13—C14—C15—C10−0.8 (4)
C5—C6—C7—C8−0.2 (3)C11—C10—C15—C141.1 (4)
O4—C6—C7—C8−175.31 (19)C2—C10—C15—C14179.3 (2)
C6—C7—C8—O1178.82 (19)C2—C1—O1—C8−2.8 (4)
C6—C7—C8—C9−1.1 (3)C7—C8—O1—C1−176.8 (2)
O1—C8—C9—C4−178.87 (18)C9—C8—O1—C13.1 (3)
C7—C8—C9—C41.0 (3)O6—C16—O3—C4−9.9 (3)
O1—C8—C9—C30.3 (3)C17—C16—O3—C4170.81 (18)
C7—C8—C9—C3−179.8 (2)C5—C4—O3—C16111.1 (2)
C5—C4—C9—C80.3 (3)C9—C4—O3—C16−71.6 (2)
O3—C4—C9—C8−176.86 (18)O7—C18—O4—C68.7 (4)
C5—C4—C9—C3−178.8 (2)C19—C18—O4—C6−172.2 (2)
O3—C4—C9—C34.0 (3)C7—C6—O4—C18−136.0 (2)
O2—C3—C9—C8177.1 (2)C5—C6—O4—C1848.8 (3)
C2—C3—C9—C8−3.8 (3)O8—C20—O5—C13−1.6 (3)
O2—C3—C9—C4−3.8 (3)C21—C20—O5—C13177.94 (18)
C2—C3—C9—C4175.25 (19)C14—C13—O5—C2089.1 (3)
C1—C2—C10—C11−56.2 (3)C12—C13—O5—C20−92.3 (3)
C3—C2—C10—C11121.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O8i0.932.473.396 (3)175
C19—H19A···O7ii0.962.573.523 (3)173
C21—H21B···O3iii0.962.443.328 (3)154
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z−1; (iii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC21H16O8
Mr396.34
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)7.6144 (14), 10.6755 (19), 12.533 (2)
α, β, γ (°)72.489 (3), 73.848 (3), 74.762 (3)
V (Å3)915.2 (3)
Z2
Radiation typeMo Kα
µ (mm−1)0.11
Crystal size (mm)0.30 × 0.20 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.967, 0.989
No. of measured, independent and
observed [I > 2σ(I)] reflections		4847, 3043, 1968
Rint0.025
(sin θ/λ)max (Å−1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.113, 0.96
No. of reflections3043
No. of parameters265
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.17, −0.17

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O8i0.932.473.396 (3)175
C19—H19A···O7ii0.962.573.523 (3)173
C21—H21B···O3iii0.962.443.328 (3)154
Symmetry codes: (i) x, y, z−1; (ii) −x+1, −y+1, −z−1; (iii) −x+1, −y, −z+1.
 

Acknowledgements

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).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
 First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
 First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
 First citationLi, 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.  Web of Science CrossRef Google Scholar
 First citationLiu, X.-Y. & Zhu, H.-L. (2005). Syn. React. Inorg. Met. Org. Nano-Met. Chem. 35, 325–332.  Web of Science CrossRef CAS Google Scholar
 First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 11| November 2009| Page o2866
https://doi.org/10.1107/S1600536809043670
Follow Acta Cryst. E
Sign up for e-alerts
E-alerts
Follow Acta Cryst. on Twitter
Twitter
Follow us on facebook
Facebook
Sign up for RSS feeds
RSS