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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1401.
Published online 2010 May 22. doi:  10.1107/S1600536810012298
PMCID: PMC2979424

4-Oxo-2-phenylchroman-6-yl propionate

Abstract

In the structure of the title compound, C18H16O4, both the S and R enanti­omers appear to occupy in a random way four symmetry-equivalent sites of the unit cell in an approximately 4:1/1:4 ratio. The chiral C atom of the pyrone ring together with the phenyl ring bonded to this atom are disordered over two positions, the occupancy factor of the major component being 0.809 (5). Adjacent molecules are linked by weak C—H(...)O hydrogen bonds.

Related literature

For background to flavonoids and their properties, see: Harborne & Baxter (1999 [triangle]); Harborne & Williams (2000 [triangle]); Di Carlo et al.,(1999 [triangle]); Rice-Evans (2004 [triangle]); Wang (2000 [triangle]); Halliwell (1996 [triangle]); Rice-Evans et al. (1996 [triangle]); Kostrzewa-Susłow et al. (2008 [triangle]). For related structures, see: Shoja et al. (1998 [triangle]); Białońska et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1401-scheme1.jpg

Experimental

Crystal data

  • C18H16O4
  • M r = 296.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1401-efi1.jpg
  • a = 7.863 (2) Å
  • b = 17.876 (4) Å
  • c = 10.731 (2) Å
  • β = 101.28 (3)°
  • V = 1479.2 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 K
  • 0.32 × 0.15 × 0.09 mm

Data collection

  • Kuma KM4 CCD diffractometer
  • 23501 measured reflections
  • 5512 independent reflections
  • 1906 reflections with I > 2σ(I)
  • R int = 0.126

Refinement

  • R[F 2 > 2σ(F 2)] = 0.063
  • wR(F 2) = 0.140
  • S = 0.86
  • 5512 reflections
  • 263 parameters
  • 186 restraints
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: CrysAlis CCD, (Oxford Diffraction, 2009 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP (Bruker, 1999 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810012298/hg2666sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810012298/hg2666Isup2.hkl

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

Acknowledgments

Publication/Project "Biotransformations for pharmaceutical and cosmetics industry" No. POIG.01.03.01-00-158/09-00 was part-financed by the European Union within the European Regional Development Fund.

supplementary crystallographic information

Comment

Flavonoids, which are the subject of our research, are biologically active substances naturally occuring in plants. The colour of flowers and leaves and its intensity is correlated with their presence. Due to the strong UV absorption, flavonoids play protective role in plants. They are also nectar indicators. Flavonoids protect plants from pathogens, act as inhibitors of auxins transport and also initiate formation of root nodules in papilionaceous plants [Harborne & Baxter, 1999; Harborne & Williams, 2000].

So far, flavonoids have not been found in organisms of animals and humans, however worldwide research proved wide range of valuable biological activities of these compounds. These include antiallergic, antiatherogenic, antidiabetic, antidiarrheic, antiinflammatory, antihepatotoxic and anticancerogenic properties [Di Carlo et al., 1999; Rice-Evans, 2004; Wang, 2000]. The wide spectrum of their pharmacological activities depends on chemical structures. Especially important is presence of carbonyl group, as well as presence, number and location of hydroxyl groups. For example, the presence of hydroxyl groups in the B ring is the main factor determining antioxidant activity of flavonoids [Halliwell, 1996; Rice-Evans et al., 1996].

Transformation of flavonoids by means of microorganisms is a way of modification of their structure, as well as a helpful tool for elucidation of their metabolism in mammals [Kostrzewa-Susłow et al., 2008].

The crystal structure of 6-propionoxyflavanone, together with numbering scheme employed, is presented in Fig. 1. In the present analysis, atoms at position 2 in the pyrone ring [C2 and H2 (major component) and C2A and H2A (minor component)] and phenyl ring [C11—C16 (major component) and C11A—C16A (minor component)] are clearly resolved. The C11—C16 (or C11A—C16A) phenyl ring is oriented almost perpendicular to the plane of the C5—C10 arene ring. The angle between the plane of the C11—C16 (C11A—C16A) ring and the plane of the C5—C10 ring is equal to 79.79 (12) ° (89.8 (5) °). The angle between the plane of carboxylate group and the plane of the C5—C10 ring is equal to 75.62 (8) °. The O1, C3, C4 O17 atoms are situated approximately in the plane of the C5—C10 arene ring (maximum deviation is equal to 0.040 (3) Å for O1). While deviation of the C18 and C2 atoms from the plane formed by the C5—C10 arene ring are equal to 1.140 (4) and 0.676 (4) Å, respectively, deviation of the C2A atom from the plane is equal to -0.403 (13) Å. Thus, two enantiomers revealing various conformations occupy equivalent sites, however somewhat randomly, not systematically, arranged in the unit cell. The ratio of the two enantiomers (R:S) in an asymmetric part of the unit cell is approximately equal to 0.8:0.2, which gives a 4:1/1:4 ratio in the crystal structure overall.

Experimental

The title compound was obtained during esterification of 6-hydroksyflavanone using propionyl chloride (Fig.2). Crystals of 6-propionoxyflavanone were grown from a THF (tetrahydrofurane) solution under ambient conditions.

Refinement

Occupancy factors for C2, C2A, C11—C16 and C11A—C16A were refined. The C11A—C16A atoms were refined using ISOR restrain. All H atoms were placed at calculated positions. H atoms attached to carbons were constrained as riding atoms, with C–H set to 0.95 - 0.99 Å. Uiso(H) values were set to 1.2Ueq of the parent atom.

Figures

Fig. 1.
Structure of 6-propionoxyflavanone. Disordered part with occupancy factor equal to 0.2 is marked by open line.
Fig. 2.
The title compound was obtained during esterification of 6-hydroksyflavanone using propionyl chloride.

Crystal data

C18H16O4F(000) = 624
Mr = 296.31Dx = 1.331 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2758 reflections
a = 7.863 (2) Åθ = 2.9–36.8°
b = 17.876 (4) ŵ = 0.09 mm1
c = 10.731 (2) ÅT = 100 K
β = 101.28 (3)°Plate, colorless
V = 1479.2 (6) Å30.32 × 0.15 × 0.09 mm
Z = 4

Data collection

Kuma KM4 CCD diffractometer1906 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.126
graphiteθmax = 33.0°, θmin = 2.9°
ω scanh = −9→12
23501 measured reflectionsk = −27→27
5512 independent reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 0.86w = 1/[σ2(Fo2) + (0.0501P)2] where P = (Fo2 + 2Fc2)/3
5512 reflections(Δ/σ)max < 0.001
263 parametersΔρmax = 0.26 e Å3
186 restraintsΔρmin = −0.20 e Å3

Special details

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

xyzUiso*/UeqOcc. (<1)
O10.08199 (17)0.09868 (7)0.26522 (11)0.0360 (3)
C3−0.2206 (2)0.11679 (11)0.28343 (16)0.0333 (5)
H3C−0.24050.17020.26070.040*0.191 (5)
H3D−0.33120.08990.25390.040*0.191 (5)
H3A−0.31990.15160.26120.040*0.809 (5)
H3B−0.25830.06720.24690.040*0.809 (5)
C2−0.0717 (3)0.14510 (17)0.2248 (2)0.0291 (7)0.809 (5)
H2−0.04370.19750.25440.035*0.809 (5)
C2A−0.0799 (12)0.0847 (7)0.2107 (8)0.029 (3)0.191 (5)
H2A−0.09350.02900.20910.034*0.191 (5)
O4−0.27867 (17)0.11284 (9)0.49357 (12)0.0510 (4)
C4−0.1720 (3)0.11027 (12)0.42566 (17)0.0367 (5)
C50.0761 (3)0.09439 (11)0.60752 (17)0.0354 (5)
H5−0.00240.09860.66410.042*
C60.2489 (2)0.08326 (10)0.65442 (16)0.0325 (5)
C70.3650 (3)0.07588 (11)0.57403 (18)0.0378 (5)
H70.48450.06800.60800.045*
C80.3072 (2)0.07993 (11)0.44393 (17)0.0375 (5)
H80.38650.07400.38830.045*
C90.1325 (2)0.09266 (10)0.39496 (16)0.0300 (4)
C100.0149 (2)0.09958 (10)0.47656 (16)0.0310 (4)
C11−0.1170 (4)0.1450 (3)0.0831 (3)0.0303 (7)0.809 (5)
C12−0.1411 (5)0.0793 (2)0.0138 (4)0.0366 (9)0.809 (5)
H12−0.12190.03270.05700.044*0.809 (5)
C13−0.1934 (7)0.0798 (3)−0.1190 (4)0.0397 (10)0.809 (5)
H13−0.20600.0342−0.16520.048*0.809 (5)
C14−0.2265 (7)0.1475 (3)−0.1823 (5)0.0382 (11)0.809 (5)
H14−0.26490.1483−0.27190.046*0.809 (5)
C15−0.2034 (5)0.2140 (2)−0.1141 (3)0.0417 (8)0.809 (5)
H15−0.22510.2605−0.15720.050*0.809 (5)
C16−0.1478 (4)0.2128 (2)0.0186 (3)0.0376 (7)0.809 (5)
H16−0.13110.25850.06460.045*0.809 (5)
C11A−0.119 (2)0.1114 (11)0.0698 (17)0.034 (3)0.191 (5)
C12A−0.172 (2)0.0636 (11)−0.0273 (17)0.037 (3)0.191 (5)
H12A−0.17520.0112−0.01360.045*0.191 (5)
C13A−0.220 (3)0.0935 (16)−0.147 (2)0.040 (3)0.191 (5)
H13A−0.26850.0616−0.21530.048*0.191 (5)
C14A−0.201 (3)0.1676 (14)−0.170 (2)0.035 (2)0.191 (5)
H14A−0.22920.1866−0.25410.042*0.191 (5)
C15A−0.142 (2)0.2133 (9)−0.0714 (15)0.038 (2)0.191 (5)
H15A−0.12620.2652−0.08470.046*0.191 (5)
C16A−0.1042 (19)0.1832 (10)0.0494 (14)0.033 (2)0.191 (5)
H16A−0.06620.21540.11970.040*0.191 (5)
O170.30900 (16)0.07682 (7)0.78730 (11)0.0366 (3)
O180.28558 (19)0.20177 (8)0.80597 (12)0.0481 (4)
C180.3155 (2)0.14193 (13)0.85498 (18)0.0368 (5)
C190.3615 (3)0.12719 (12)0.99504 (17)0.0429 (5)
H19A0.47430.10081.01430.051*
H19B0.27290.09371.01920.051*
C200.3734 (3)0.19745 (13)1.07435 (19)0.0525 (6)
H20A0.40300.18421.16460.079*
H20B0.26150.22341.05700.079*
H20C0.46320.23031.05290.079*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0336 (8)0.0530 (9)0.0217 (7)0.0076 (6)0.0058 (6)0.0035 (6)
C30.0309 (10)0.0463 (12)0.0221 (9)−0.0009 (9)0.0037 (8)0.0026 (8)
C20.0281 (13)0.0357 (18)0.0218 (11)0.0042 (12)0.0009 (9)0.0039 (11)
C2A0.029 (6)0.044 (8)0.015 (4)−0.001 (5)0.009 (4)0.006 (4)
O40.0312 (8)0.0941 (12)0.0288 (7)−0.0055 (8)0.0086 (6)0.0014 (8)
C40.0309 (10)0.0531 (13)0.0255 (10)−0.0048 (10)0.0045 (9)−0.0011 (9)
C50.0328 (11)0.0499 (14)0.0244 (10)−0.0013 (9)0.0081 (8)0.0012 (9)
C60.0368 (11)0.0385 (12)0.0220 (9)0.0016 (9)0.0050 (8)0.0033 (8)
C70.0312 (11)0.0504 (13)0.0309 (10)0.0068 (10)0.0037 (8)0.0064 (9)
C80.0321 (11)0.0543 (14)0.0264 (10)0.0089 (10)0.0062 (8)0.0044 (9)
C90.0351 (11)0.0333 (11)0.0207 (9)0.0024 (9)0.0030 (8)0.0024 (8)
C100.0297 (10)0.0398 (12)0.0235 (10)−0.0008 (8)0.0051 (8)0.0019 (8)
C110.0287 (13)0.039 (2)0.0252 (14)0.0019 (18)0.0085 (10)−0.0011 (15)
C120.0418 (19)0.041 (2)0.0261 (19)0.0011 (16)0.0045 (16)0.0034 (16)
C130.042 (2)0.050 (2)0.027 (2)0.0019 (17)0.0054 (16)0.0004 (16)
C140.036 (2)0.057 (3)0.0211 (15)0.0063 (19)0.0045 (13)−0.0009 (18)
C150.049 (2)0.0538 (18)0.0220 (16)0.0168 (16)0.0050 (13)0.0067 (15)
C160.0494 (18)0.0398 (18)0.0238 (15)0.0082 (14)0.0077 (12)0.0030 (13)
C11A0.038 (4)0.036 (5)0.028 (4)0.003 (4)0.004 (4)−0.004 (4)
C12A0.040 (4)0.045 (4)0.026 (5)0.003 (4)0.004 (4)−0.004 (4)
C13A0.038 (4)0.052 (5)0.029 (5)0.006 (4)0.005 (4)0.004 (4)
C14A0.037 (4)0.047 (4)0.023 (4)0.006 (4)0.011 (4)0.005 (4)
C15A0.043 (4)0.041 (4)0.028 (4)0.008 (4)0.001 (4)0.003 (4)
C16A0.041 (4)0.032 (5)0.025 (4)0.012 (4)0.003 (4)−0.001 (4)
O170.0386 (8)0.0457 (9)0.0231 (7)0.0039 (7)−0.0001 (6)0.0015 (6)
O180.0642 (10)0.0454 (9)0.0318 (8)−0.0007 (8)0.0023 (7)0.0045 (7)
C180.0311 (11)0.0506 (14)0.0284 (10)0.0003 (10)0.0047 (8)0.0015 (10)
C190.0454 (12)0.0564 (14)0.0252 (10)0.0072 (11)0.0027 (9)0.0026 (9)
C200.0544 (14)0.0722 (17)0.0289 (11)0.0118 (12)0.0032 (10)−0.0057 (11)

Geometric parameters (Å, °)

O1—C2A1.317 (10)C12—C131.404 (5)
O1—C91.375 (2)C12—H120.9500
O1—C21.460 (3)C13—C141.386 (6)
C3—C41.504 (2)C13—H130.9500
C3—C21.520 (3)C14—C151.390 (6)
C3—C2A1.581 (10)C14—H140.9500
C3—H3C0.9900C15—C161.405 (4)
C3—H3D0.9900C15—H150.9500
C3—H3A0.9899C16—H160.9500
C3—H3B0.9901C11A—C16A1.31 (2)
C2—C111.492 (4)C11A—C12A1.35 (2)
C2—H21.0000C12A—C13A1.37 (2)
C2A—C11A1.558 (19)C12A—H12A0.9500
C2A—H3B1.5579C13A—C14A1.36 (3)
C2A—H2A1.0000C13A—H13A0.9500
O4—C41.215 (2)C14A—C15A1.35 (3)
C4—C101.476 (3)C14A—H14A0.9500
C5—C61.368 (3)C15A—C16A1.381 (19)
C5—C101.397 (2)C15A—H15A0.9500
C5—H50.9500C16A—H16A0.9500
C6—C71.379 (3)O17—C181.367 (2)
C6—O171.416 (2)O18—C181.195 (2)
C7—C81.383 (3)C18—C191.499 (3)
C7—H70.9500C19—C201.510 (3)
C8—C91.390 (3)C19—H19A0.9900
C8—H80.9500C19—H19B0.9900
C9—C101.398 (2)C20—H20A0.9800
C11—C121.383 (4)C20—H20B0.9800
C11—C161.394 (4)C20—H20C0.9800
C2A—O1—C9119.8 (4)C8—C9—C10120.23 (16)
C2A—O1—C245.9 (5)C5—C10—C9118.98 (18)
C9—O1—C2113.80 (15)C5—C10—C4120.20 (17)
C4—C3—C2112.49 (16)C9—C10—C4120.80 (16)
C4—C3—C2A114.1 (4)C12—C11—C16118.7 (3)
C2—C3—C2A41.1 (4)C12—C11—C2122.0 (4)
C4—C3—H3C108.7C16—C11—C2119.2 (3)
C2—C3—H3C71.0C11—C12—C13121.4 (4)
C2A—C3—H3C108.7C11—C12—H12119.3
C4—C3—H3D108.7C13—C12—H12119.3
C2—C3—H3D136.7C14—C13—C12119.6 (5)
C2A—C3—H3D108.7C14—C13—H13120.2
H3C—C3—H3D107.6C12—C13—H13120.2
C4—C3—H3A109.0C13—C14—C15119.7 (5)
C2—C3—H3A109.0C13—C14—H14120.1
C2A—C3—H3A134.8C15—C14—H14120.1
H3C—C3—H3A41.9C14—C15—C16120.2 (4)
H3D—C3—H3A68.1C14—C15—H15119.9
C4—C3—H3B109.3C16—C15—H15119.9
C2—C3—H3B109.2C11—C16—C15120.4 (3)
C2A—C3—H3B70.3C11—C16—H16119.8
H3C—C3—H3B138.1C15—C16—H16119.8
H3D—C3—H3B42.5C16A—C11A—C12A121.0 (17)
H3A—C3—H3B107.8C16A—C11A—C2A117.1 (16)
O1—C2—C11108.7 (2)C12A—C11A—C2A121.9 (17)
O1—C2—C3110.33 (18)C11A—C12A—C13A118 (2)
C11—C2—C3111.8 (2)C11A—C12A—H12A121.2
O1—C2—H2108.6C13A—C12A—H12A121.2
C11—C2—H2108.6C14A—C13A—C12A122 (2)
C3—C2—H2108.6C14A—C13A—H13A119.0
O1—C2A—C11A111.4 (9)C12A—C13A—H13A119.0
O1—C2A—C3114.9 (7)C15A—C14A—C13A119 (2)
C11A—C2A—C3109.9 (9)C15A—C14A—H14A120.6
O1—C2A—H3B140.0C13A—C14A—H14A120.6
C11A—C2A—H3B106.5C14A—C15A—C16A118.6 (16)
C3—C2A—H3B36.8C14A—C15A—H15A120.7
O1—C2A—H2A106.7C16A—C15A—H15A120.7
C11A—C2A—H2A106.7C11A—C16A—C15A121.9 (14)
C3—C2A—H2A106.7C11A—C16A—H16A119.0
H3B—C2A—H2A73.0C15A—C16A—H16A119.0
O4—C4—C10122.48 (16)C18—O17—C6115.85 (15)
O4—C4—C3122.51 (18)O18—C18—O17122.98 (18)
C10—C4—C3115.01 (16)O18—C18—C19125.9 (2)
C6—C5—C10120.12 (18)O17—C18—C19111.08 (18)
C6—C5—H5119.9C18—C19—C20113.28 (19)
C10—C5—H5119.9C18—C19—H19A108.9
C5—C6—C7120.98 (17)C20—C19—H19A108.9
C5—C6—O17119.59 (17)C18—C19—H19B108.9
C7—C6—O17119.39 (17)C20—C19—H19B108.9
C6—C7—C8119.97 (19)H19A—C19—H19B107.7
C6—C7—H7120.0C19—C20—H20A109.5
C8—C7—H7120.0C19—C20—H20B109.5
C7—C8—C9119.70 (18)H20A—C20—H20B109.5
C7—C8—H8120.1C19—C20—H20C109.5
C9—C8—H8120.1H20A—C20—H20C109.5
O1—C9—C8117.62 (17)H20B—C20—H20C109.5
O1—C9—C10122.15 (17)
C2A—O1—C2—C11−68.7 (5)C8—C9—C10—C4−177.69 (18)
C9—O1—C2—C11−177.9 (2)O4—C4—C10—C5−2.1 (3)
C2A—O1—C2—C354.2 (5)C3—C4—C10—C5178.64 (18)
C9—O1—C2—C3−55.0 (2)O4—C4—C10—C9176.33 (19)
C4—C3—C2—O153.9 (3)C3—C4—C10—C9−2.9 (3)
C2A—C3—C2—O1−47.5 (5)O1—C2—C11—C1253.9 (4)
C4—C3—C2—C11175.0 (2)C3—C2—C11—C12−68.2 (4)
C2A—C3—C2—C1173.6 (5)O1—C2—C11—C16−130.7 (3)
C9—O1—C2A—C11A167.4 (8)C3—C2—C11—C16107.3 (3)
C2—O1—C2A—C11A72.1 (9)C16—C11—C12—C130.8 (5)
C9—O1—C2A—C341.6 (10)C2—C11—C12—C13176.3 (4)
C2—O1—C2A—C3−53.7 (7)C11—C12—C13—C14−1.9 (7)
C4—C3—C2A—O1−39.4 (10)C12—C13—C14—C151.7 (8)
C2—C3—C2A—O157.7 (7)C13—C14—C15—C16−0.5 (7)
C4—C3—C2A—C11A−165.9 (8)C12—C11—C16—C150.4 (5)
C2—C3—C2A—C11A−68.8 (9)C2—C11—C16—C15−175.2 (3)
C2—C3—C4—O4155.4 (2)C14—C15—C16—C11−0.6 (5)
C2A—C3—C4—O4−159.7 (5)O1—C2A—C11A—C16A−61.9 (18)
C2—C3—C4—C10−25.4 (3)C3—C2A—C11A—C16A66.6 (17)
C2A—C3—C4—C1019.6 (6)O1—C2A—C11A—C12A119.9 (17)
C10—C5—C6—C7−1.0 (3)C3—C2A—C11A—C12A−111.6 (17)
C10—C5—C6—O17−178.93 (17)C16A—C11A—C12A—C13A−5(3)
C5—C6—C7—C80.2 (3)C2A—C11A—C12A—C13A173.6 (17)
O17—C6—C7—C8178.17 (18)C11A—C12A—C13A—C14A6(4)
C6—C7—C8—C91.0 (3)C12A—C13A—C14A—C15A−4(4)
C2A—O1—C9—C8156.3 (7)C13A—C14A—C15A—C16A−1(3)
C2—O1—C9—C8−152.26 (19)C12A—C11A—C16A—C15A0(3)
C2A—O1—C9—C10−24.2 (7)C2A—C11A—C16A—C15A−177.7 (12)
C2—O1—C9—C1027.2 (3)C14A—C15A—C16A—C11A2(3)
C7—C8—C9—O1177.93 (18)C5—C6—O17—C18−74.2 (2)
C7—C8—C9—C10−1.5 (3)C7—C6—O17—C18107.8 (2)
C6—C5—C10—C90.5 (3)C6—O17—C18—O18−5.5 (3)
C6—C5—C10—C4178.93 (18)C6—O17—C18—C19173.63 (16)
O1—C9—C10—C5−178.66 (17)O18—C18—C19—C20−1.8 (3)
C8—C9—C10—C50.8 (3)O17—C18—C19—C20179.05 (17)
O1—C9—C10—C42.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O18i1.002.373.145 (3)133

Symmetry codes: (i) x−1/2, −y+1/2, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2666).

References

  • Białońska, A., Ciunik, Z., Kostrzewa-Susłow, E. & Dmochowska-Gładysz, J. (2007). Acta Cryst. E63, o430–o431.
  • Bruker (1999). XP. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Di Carlo, G., Mascolo, N., Izzo, A. A. & Capasso, F. (1999). Life Science, 65, 337–353. [PubMed]
  • Halliwell, B. (1996). Annu. Rev. Nutr 16, 33–50. [PubMed]
  • Harborne, J. B. & Baxter, H. (1999). The Handbook of Natural Flavonoids. Chichester: John Wiley & Sons.
  • Harborne, J. B. & Williams, C. A. (2000). Phytochemistry, 55, 481–504. [PubMed]
  • Kostrzewa-Susłow, E., Dmochowska-Gładysz, J., Białońska, A. & Ciunik, Z. (2008). J. Mol. Catal. B Enzym 52–53, 34–39.
  • Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd., Abingdon, England.
  • Rice-Evans, C. (2004). Free Radical Bio. Med 36, 827–828. [PubMed]
  • Rice-Evans, C. A., Miller, N. J. & Paganga, G. (1996). Free Radic. Biol. Med.20, 933–956. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shoja, M., Samuel, K. & Athanasopoulos, D. (1998). Z. Kristallogr. New Cryst. Struct 213, 373–374.
  • Wang, H. K. (2000). Expert. Opin. Investig. Drugs 9, 2103–2119. [PubMed]

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