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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): o63.
Published online 2009 December 4. doi:  10.1107/S1600536809051678
PMCID: PMC2980130

5,7-Bis(benz­yloxy)-2-[4-(benz­yloxy)phen­yl]-4H-chromen-4-one

Abstract

In the title compound, C36H28O5, the terminal benzene rings are twisted at dihedral angles of 6.75 (12), 70.86 (14) and 82.02 (12)° with the respect to the central plana r[maximum deviation = 0.070 (3) Å] chromen-4-one ring system. In the crystal structure, π–π stacking is observed between parallel benzene rings of adjacent mol­ecules [centroid–centroid distance = 3.7459 (16) Å].

Related literature

For general background to the biological effects of flavones, see: Formica & Regelson (1995 [triangle]); Medina et al. (1998 [triangle]); Cotelle et al. (1992 [triangle]). For a related structure, see: Waller et al. (2003 [triangle]).

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Object name is e-66-00o63-scheme1.jpg

Experimental

Crystal data

  • C36H28O5
  • M r = 540.58
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00o63-efi1.jpg
  • a = 7.3176 (12) Å
  • b = 12.818 (2) Å
  • c = 14.933 (2) Å
  • α = 82.542 (3)°
  • β = 83.861 (3)°
  • γ = 85.600 (3)°
  • V = 1378.0 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 293 K
  • 0.35 × 0.22 × 0.08 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • 7198 measured reflections
  • 4786 independent reflections
  • 2505 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.140
  • S = 0.99
  • 4786 reflections
  • 370 parameters
  • H-atom parameters constrained
  • Δρmax = 0.13 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1999 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809051678/xu2692sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809051678/xu2692Isup2.hkl

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

supplementary crystallographic information

Comment

Flavones are among the most ubiquitous groups of polyphenolic compounds in foods of plant origin. As integral constituents of the diet, they may exert a wide range of beneficial effects on human health, including protection against cardiovascular disease, certain forms of cancer (Formica & Regelson 1995) and modulatory activities at GABA-A receptors (Medina et al., 1998). Flavones likely produce such biological effects through their free radical-scavenging antioxidative activities and metal ion-chelating a bilities (Cotelle et al.1992). Some flavones are more potent than ascorbic acid and tocopherols in scavenging reactive oxygen species. The title compound was crystallized as part of an ongoing structure-activity study to determine the properties of those compounds that confer this activity in order to aid the design of more active compounds.

The molecular is shown in shown in Fig. 1, the bond lengths and angles are within normal ranges. The bond length of the carbonyl group C7=O2 of 1.228 Å is somewhat longer than typical carbonyl bond. This may be due to the fact that atom O2 participate in intermolecular Van der Waals forces. And the bond lengths of C1—O3, C3—O4 and C27—O5 are 1.353 Å, 1.369 Å and 1.375 Å, respectively. In the crystal structure π-π stacking is observed between parallel C24-benzene and C24i-benzene rings of adjacent molecules [centroids distance 3.7459 (16) Å; symmetry code: (i) 2-x, 1-y, 2-z].

Experimental

E-3-(4-Phenoxyphenyl)-1-(2,4-bisphenoxy-6-hydroxyphenyl) propenone (2 g, 3.40 mmol) was dissolved in DMSO (40 ml). I2 (96 mg, 0.377 mmol) was added to the solution. The reaction mixture was heated at 400 K for 2 h under N2, then coolded to room temperature. The mixture was pured to 200 ml 1M HCl solution. The aqueous layer was extracted with ethyl acetate. The organic layer was washed with NaHCO3 solution, watre and brine, and dried by MgSO4 and concentrated under diminished pressure. The residue was purified by flash chromatography on a silica gel column (elutant: hexanesethyl /acetate, 4:1). Single crystals suitable for X-ray diffraction were obtained by solw evaporation of a dilute solution of the title compound in methanol/dichloromethane (1:5).

Refinement

The H atoms were placed in calculated positions and refined in riding mode with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme.

Crystal data

C36H28O5Z = 2
Mr = 540.58F(000) = 568
Triclinic, P1Dx = 1.303 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3176 (12) ÅCell parameters from 1081 reflections
b = 12.818 (2) Åθ = 2.2–21.3°
c = 14.933 (2) ŵ = 0.09 mm1
α = 82.542 (3)°T = 293 K
β = 83.861 (3)°Platelet, colorless
γ = 85.600 (3)°0.35 × 0.22 × 0.08 mm
V = 1378.0 (4) Å3

Data collection

Bruker SMART APEX CCD area-detector diffractometer2505 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
graphiteθmax = 25.0°, θmin = 1.4°
[var phi] and ω scansh = −8→7
7198 measured reflectionsk = −15→14
4786 independent reflectionsl = −17→15

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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 0.99w = 1/[σ2(Fo2) + (0.0563P)2 + 0.0156P] where P = (Fo2 + 2Fc2)/3
4786 reflections(Δ/σ)max < 0.001
370 parametersΔρmax = 0.13 e Å3
0 restraintsΔρmin = −0.14 e Å3

Special details

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)

xyzUiso*/Ueq
C10.4399 (4)0.5313 (2)0.65974 (17)0.0615 (7)
C20.3089 (3)0.6140 (2)0.65568 (17)0.0637 (7)
H20.20780.61180.62330.076*
C30.3274 (4)0.7009 (2)0.69977 (19)0.0650 (8)
C40.4748 (3)0.7066 (2)0.74818 (18)0.0666 (8)
H40.48820.76530.77700.080*
C50.6029 (3)0.6210 (2)0.75215 (17)0.0569 (7)
C60.5971 (3)0.5329 (2)0.70836 (17)0.0578 (7)
C70.7481 (4)0.4513 (2)0.71387 (19)0.0646 (7)
C80.8810 (4)0.4680 (2)0.77456 (18)0.0649 (7)
H80.97510.41610.78450.078*
C90.8767 (3)0.5535 (2)0.81716 (17)0.0567 (7)
C100.2776 (4)0.4369 (2)0.56895 (18)0.0717 (8)
H10A0.27590.49390.51950.086*
H10B0.16310.44280.60780.086*
C110.2968 (4)0.3326 (2)0.53217 (17)0.0658 (7)
C120.4499 (4)0.2647 (2)0.53946 (18)0.0764 (8)
H120.54620.28170.56970.092*
C130.4618 (5)0.1707 (3)0.5019 (2)0.0919 (10)
H130.56590.12480.50730.110*
C140.3212 (6)0.1451 (3)0.4571 (2)0.1017 (11)
H140.32970.08210.43160.122*
C150.1680 (6)0.2126 (3)0.4499 (2)0.1067 (12)
H150.07200.19560.41940.128*
C160.1558 (4)0.3050 (3)0.4874 (2)0.0909 (10)
H160.05050.35000.48260.109*
C170.1970 (4)0.8678 (2)0.7378 (2)0.0819 (9)
H17A0.30490.90570.71390.098*
H17B0.20550.84520.80180.098*
C180.0252 (4)0.9384 (2)0.7251 (2)0.0664 (8)
C190.0278 (4)1.0262 (2)0.6621 (2)0.0863 (10)
H190.13491.04020.62440.104*
C20−0.1269 (6)1.0941 (3)0.6540 (2)0.1007 (11)
H20−0.12301.15390.61150.121*
C21−0.2839 (5)1.0739 (3)0.7077 (2)0.0919 (11)
H21−0.38781.11990.70210.110*
C22−0.2905 (4)0.9869 (3)0.7696 (2)0.0881 (10)
H22−0.39900.97300.80630.106*
C23−0.1360 (4)0.9187 (2)0.7783 (2)0.0807 (9)
H23−0.14140.85880.82070.097*
C241.0066 (3)0.5790 (2)0.87816 (17)0.0545 (7)
C251.1804 (3)0.5272 (2)0.88121 (17)0.0605 (7)
H251.21170.47140.84730.073*
C261.3063 (4)0.5567 (2)0.93301 (17)0.0638 (7)
H261.42200.52130.93350.077*
C271.2622 (4)0.6387 (2)0.98449 (17)0.0610 (7)
C281.0861 (4)0.6875 (2)0.98691 (18)0.0695 (8)
H281.05240.74011.02400.083*
C290.9617 (4)0.6573 (2)0.93393 (18)0.0656 (7)
H290.84400.69050.93560.079*
C301.3635 (4)0.7560 (2)1.0795 (2)0.0817 (9)
H30A1.28650.73591.13510.098*
H30B1.29810.81271.04390.098*
C311.5407 (4)0.7924 (2)1.1012 (2)0.0676 (8)
C321.6274 (5)0.8700 (3)1.0444 (2)0.0886 (10)
H321.57820.89730.99070.106*
C331.7863 (6)0.9085 (3)1.0654 (3)0.1061 (12)
H331.84390.96131.02630.127*
C341.8587 (5)0.8682 (4)1.1447 (4)0.1072 (13)
H341.96510.89411.15980.129*
C351.7749 (5)0.7903 (3)1.2013 (3)0.0928 (10)
H351.82570.76241.25440.111*
C361.6151 (4)0.7525 (2)1.1804 (2)0.0796 (9)
H361.55760.70001.21980.096*
O10.7420 (2)0.63213 (13)0.80484 (12)0.0647 (5)
O20.7642 (3)0.37370 (17)0.67264 (15)0.0968 (7)
O30.4297 (2)0.44352 (14)0.61951 (12)0.0745 (6)
O40.1888 (2)0.77832 (14)0.69079 (13)0.0772 (6)
O51.4013 (2)0.66769 (14)1.02937 (13)0.0767 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0644 (18)0.0570 (18)0.0630 (18)0.0071 (15)−0.0114 (15)−0.0095 (14)
C20.0628 (18)0.0577 (18)0.0724 (19)0.0051 (15)−0.0217 (14)−0.0080 (14)
C30.0576 (17)0.0521 (17)0.084 (2)0.0097 (15)−0.0182 (15)−0.0008 (15)
C40.0617 (18)0.0525 (17)0.087 (2)0.0054 (15)−0.0198 (16)−0.0087 (14)
C50.0465 (16)0.0557 (17)0.0681 (18)−0.0016 (14)−0.0129 (14)−0.0010 (14)
C60.0569 (17)0.0540 (17)0.0605 (17)0.0012 (14)−0.0054 (14)−0.0028 (13)
C70.0580 (18)0.0626 (19)0.072 (2)0.0110 (15)−0.0102 (15)−0.0101 (15)
C80.0578 (17)0.0625 (19)0.0726 (19)0.0160 (14)−0.0137 (15)−0.0076 (15)
C90.0478 (16)0.0530 (17)0.0656 (18)0.0075 (14)−0.0063 (14)0.0016 (14)
C100.0716 (19)0.076 (2)0.0697 (19)0.0089 (16)−0.0236 (16)−0.0123 (15)
C110.078 (2)0.0660 (19)0.0535 (17)0.0057 (17)−0.0148 (15)−0.0061 (14)
C120.091 (2)0.071 (2)0.0679 (19)0.0125 (18)−0.0205 (16)−0.0140 (16)
C130.120 (3)0.081 (2)0.075 (2)0.018 (2)−0.014 (2)−0.0175 (18)
C140.160 (4)0.080 (2)0.069 (2)−0.002 (3)−0.021 (2)−0.0232 (18)
C150.140 (3)0.099 (3)0.092 (3)−0.011 (3)−0.043 (2)−0.024 (2)
C160.098 (3)0.091 (3)0.090 (2)0.010 (2)−0.041 (2)−0.020 (2)
C170.078 (2)0.066 (2)0.109 (2)0.0175 (16)−0.0397 (18)−0.0230 (18)
C180.068 (2)0.0559 (18)0.079 (2)0.0085 (16)−0.0256 (17)−0.0155 (15)
C190.083 (2)0.083 (2)0.089 (2)0.0090 (19)−0.0125 (18)−0.0008 (19)
C200.116 (3)0.077 (2)0.105 (3)0.024 (2)−0.028 (2)0.005 (2)
C210.099 (3)0.085 (3)0.093 (3)0.038 (2)−0.032 (2)−0.026 (2)
C220.072 (2)0.105 (3)0.088 (2)0.014 (2)−0.0149 (18)−0.023 (2)
C230.087 (2)0.069 (2)0.086 (2)0.0047 (19)−0.0244 (19)−0.0023 (16)
C240.0492 (16)0.0534 (16)0.0576 (17)0.0075 (13)−0.0050 (13)−0.0003 (13)
C250.0590 (17)0.0578 (17)0.0649 (18)0.0097 (14)−0.0118 (14)−0.0120 (13)
C260.0600 (17)0.0620 (18)0.0685 (19)0.0157 (15)−0.0137 (15)−0.0101 (15)
C270.0597 (18)0.0608 (18)0.0623 (18)0.0112 (15)−0.0166 (14)−0.0071 (14)
C280.0677 (19)0.0695 (19)0.072 (2)0.0157 (16)−0.0138 (16)−0.0195 (15)
C290.0576 (17)0.0646 (19)0.0727 (19)0.0156 (14)−0.0132 (15)−0.0072 (15)
C300.079 (2)0.073 (2)0.097 (2)0.0116 (17)−0.0174 (18)−0.0276 (18)
C310.0644 (19)0.0577 (19)0.082 (2)0.0105 (16)−0.0081 (17)−0.0223 (16)
C320.091 (3)0.079 (2)0.094 (2)0.005 (2)−0.005 (2)−0.011 (2)
C330.091 (3)0.081 (3)0.144 (4)−0.015 (2)0.018 (3)−0.028 (3)
C340.076 (3)0.107 (3)0.153 (4)0.000 (2)−0.008 (3)−0.077 (3)
C350.085 (3)0.101 (3)0.100 (3)0.016 (2)−0.023 (2)−0.038 (2)
C360.081 (2)0.072 (2)0.087 (2)0.0076 (18)−0.0140 (18)−0.0186 (17)
O10.0524 (10)0.0543 (11)0.0878 (13)0.0077 (9)−0.0182 (10)−0.0081 (9)
O20.0871 (15)0.0890 (16)0.1244 (18)0.0318 (12)−0.0368 (13)−0.0515 (14)
O30.0747 (13)0.0691 (13)0.0845 (14)0.0159 (10)−0.0314 (11)−0.0211 (11)
O40.0724 (13)0.0595 (12)0.1057 (15)0.0187 (10)−0.0378 (11)−0.0223 (11)
O50.0711 (13)0.0715 (13)0.0933 (14)0.0202 (10)−0.0288 (11)−0.0291 (11)

Geometric parameters (Å, °)

C1—O31.352 (3)C18—C191.370 (4)
C1—C21.374 (3)C18—C231.371 (4)
C1—C61.427 (3)C19—C201.380 (4)
C2—C31.388 (3)C19—H190.9300
C2—H20.9300C20—C211.351 (4)
C3—O41.368 (3)C20—H200.9300
C3—C41.373 (3)C21—C221.353 (4)
C4—C51.387 (3)C21—H210.9300
C4—H40.9300C22—C231.382 (4)
C5—O11.378 (3)C22—H220.9300
C5—C61.382 (3)C23—H230.9300
C6—C71.463 (3)C24—C291.384 (3)
C7—O21.228 (3)C24—C251.392 (3)
C7—C81.443 (4)C25—C261.368 (3)
C8—C91.334 (3)C25—H250.9300
C8—H80.9300C26—C271.380 (3)
C9—O11.363 (3)C26—H260.9300
C9—C241.466 (3)C27—O51.375 (3)
C10—O31.424 (3)C27—C281.388 (3)
C10—C111.501 (4)C28—C291.375 (3)
C10—H10A0.9700C28—H280.9300
C10—H10B0.9700C29—H290.9300
C11—C121.370 (3)C30—O51.430 (3)
C11—C161.379 (4)C30—C311.492 (4)
C12—C131.387 (4)C30—H30A0.9700
C12—H120.9300C30—H30B0.9700
C13—C141.368 (4)C31—C321.370 (4)
C13—H130.9300C31—C361.376 (4)
C14—C151.368 (4)C32—C331.378 (4)
C14—H140.9300C32—H320.9300
C15—C161.368 (4)C33—C341.372 (5)
C15—H150.9300C33—H330.9300
C16—H160.9300C34—C351.360 (5)
C17—O41.428 (3)C34—H340.9300
C17—C181.505 (3)C35—C361.380 (4)
C17—H17A0.9700C35—H350.9300
C17—H17B0.9700C36—H360.9300
O3—C1—C2123.3 (2)C18—C19—H19119.7
O3—C1—C6115.5 (2)C20—C19—H19119.7
C2—C1—C6121.2 (3)C21—C20—C19120.2 (3)
C1—C2—C3120.0 (3)C21—C20—H20119.9
C1—C2—H2120.0C19—C20—H20119.9
C3—C2—H2120.0C20—C21—C22120.2 (3)
O4—C3—C4123.8 (3)C20—C21—H21119.9
O4—C3—C2114.8 (2)C22—C21—H21119.9
C4—C3—C2121.5 (2)C21—C22—C23119.9 (3)
C3—C4—C5117.0 (3)C21—C22—H22120.0
C3—C4—H4121.5C23—C22—H22120.0
C5—C4—H4121.5C18—C23—C22120.7 (3)
O1—C5—C6122.0 (2)C18—C23—H23119.6
O1—C5—C4112.9 (2)C22—C23—H23119.6
C6—C5—C4125.1 (2)C29—C24—C25117.4 (2)
C5—C6—C1115.2 (2)C29—C24—C9121.0 (2)
C5—C6—C7119.2 (2)C25—C24—C9121.6 (2)
C1—C6—C7125.6 (3)C26—C25—C24121.4 (3)
O2—C7—C8121.1 (2)C26—C25—H25119.3
O2—C7—C6124.9 (3)C24—C25—H25119.3
C8—C7—C6114.0 (3)C25—C26—C27120.3 (2)
C9—C8—C7123.8 (2)C25—C26—H26119.9
C9—C8—H8118.1C27—C26—H26119.9
C7—C8—H8118.1O5—C27—C26116.3 (2)
C8—C9—O1120.5 (2)O5—C27—C28124.3 (3)
C8—C9—C24128.1 (2)C26—C27—C28119.4 (3)
O1—C9—C24111.4 (2)C29—C28—C27119.4 (3)
O3—C10—C11108.4 (2)C29—C28—H28120.3
O3—C10—H10A110.0C27—C28—H28120.3
C11—C10—H10A110.0C28—C29—C24121.9 (2)
O3—C10—H10B110.0C28—C29—H29119.0
C11—C10—H10B110.0C24—C29—H29119.0
H10A—C10—H10B108.4O5—C30—C31109.2 (2)
C12—C11—C16118.6 (3)O5—C30—H30A109.8
C12—C11—C10122.9 (3)C31—C30—H30A109.8
C16—C11—C10118.6 (3)O5—C30—H30B109.8
C11—C12—C13120.2 (3)C31—C30—H30B109.8
C11—C12—H12119.9H30A—C30—H30B108.3
C13—C12—H12119.9C32—C31—C36118.9 (3)
C14—C13—C12120.4 (3)C32—C31—C30120.2 (3)
C14—C13—H13119.8C36—C31—C30120.9 (3)
C12—C13—H13119.8C31—C32—C33121.2 (3)
C15—C14—C13119.5 (3)C31—C32—H32119.4
C15—C14—H14120.2C33—C32—H32119.4
C13—C14—H14120.2C34—C33—C32119.3 (4)
C14—C15—C16120.1 (3)C34—C33—H33120.3
C14—C15—H15120.0C32—C33—H33120.3
C16—C15—H15120.0C35—C34—C33120.1 (4)
C15—C16—C11121.2 (3)C35—C34—H34120.0
C15—C16—H16119.4C33—C34—H34120.0
C11—C16—H16119.4C34—C35—C36120.5 (4)
O4—C17—C18108.5 (2)C34—C35—H35119.8
O4—C17—H17A110.0C36—C35—H35119.8
C18—C17—H17A110.0C31—C36—C35120.1 (3)
O4—C17—H17B110.0C31—C36—H36120.0
C18—C17—H17B110.0C35—C36—H36120.0
H17A—C17—H17B108.4C9—O1—C5120.0 (2)
C19—C18—C23118.2 (3)C1—O3—C10118.6 (2)
C19—C18—C17120.7 (3)C3—O4—C17117.2 (2)
C23—C18—C17121.0 (3)C27—O5—C30117.8 (2)
C18—C19—C20120.7 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2692).

References

  • Bruker (1997). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (1999). SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cotelle, N., Bernien, J. L., Henichart, J. P., Catteau, J. P., Gaydou, E. & Wallet, J. C. (1992). Free Rad. Biol. Med 13, 211–219. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Formica, J. V. & Regelson, W. (1995). Food Chem. Toxicol.33, 1061–1080. [PubMed]
  • Medina, J. H., Viola, H., Wolfman, C., Marder, M., Wasowski, C., Calvo, D. & Paladini, A. C. (1998). Phytomedicine, 5, 235–243. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Waller, M. P., Hibbs, D. E., Overgaard, J., Hanrahan, J. R. & Hambley, T. W. (2003). Acta Cryst. E59, o767–o768.

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