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The crystal structure of the title compound, C20H22O6, an intermediate in the synthesis of the flavone 2-(4-methoxy-phenyl)-5,7-di­methoxy-3,8-di­methyl-4H-1-benzo­pyran-4-one,has been determined. The mol­ecules are held together by van der Waals forces. There is an intramolecular hydrogen bond between the hydroxy group and the neighbouring keto O atom. The mol­ecules in the crystal structure are disordered, with significantly different orientations of the methyl group in the disordered 4-methoxy­phenyl substituent.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802016136/cf6205sup1.cif
Contains datablocks I, n

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802016136/cf6205Isup2.hkl
Contains datablock I

CCDC reference: 198962

Key indicators

  • Single-crystal X-ray study
  • T = 183 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.049
  • wR factor = 0.144
  • Data-to-parameter ratio = 16.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Comment top

In an investigation of the selective inhibition of certain rat heart enzymes caused by a series of lipophilic flavones, the inhibition effect of eight flavones, which are derivatives of either O-methylluteolin or O-methylapigenin, was studied (Gaillard et al., 1996). The crystal structure of one of the O-methylluteolin derivatives, 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-3,8-dimethyl-4H-1-benzopyran-4-one, has recently been determined by Stomberg et al. (2002). A second one of these flavones, the O-methylapigenin derivative 2-(4-methoxyphenyl)-5,7-dimethoxy-3,8-dimethyl-4H-1-benzopyran-4-one, was prepared by acid-catalyzed cyclization and dehydration of 1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-(4-methoxyphenyl)-2-methyl-1,3- propanedione, (I). This paper describes the crystal structure of this synthetic intermediate, (I).

A perspective view of (I), together with the atom-numbering scheme, is shown in Fig. 1. The disorder in the methoxyphenyl group is shown in Fig. 2, and the packing of the molecules in Fig. 3. The molecules are held together by van der Waals forces. There is an intramolecular hydrogen bond between the hydroxy hydrogen atom H(O1) and the oxygen atom O4 in the neighbouring carbonyl group. The benzylic carbon atom C7, the hydroxy oxygen atom O1, and the methyl carbon atom C10 are twisted out of the C1/C2/C3/C4/C5/C6 ring plane by −0.094 (2), −0.014 (2) and 0.018 (3) Å, respectively. The methyl carbon atoms in the methoxy groups are situated close to the respective benzene ring planes [torsion angles: C5–C4–O2–C11 − 4.8 (2)°, C5–C6–O3–C12 1.6 (2)°, C16–C17–O6–C20 11.4 (4)° and C16A–C17A–O6A–C20A 172.6 (10)°].

Experimental top

The synthesis of 1-(2-hydroxy-4,6-dimethoxy-3-methylphenyl)-3-(4- methoxyphenyl)-2-methyl-1,3-propanedione, (I), has been described by Gaillard et al. (1996), who also published 1H-NMR data for the substance. Crystals suitable for X-ray analysis were obtained from benzene (m.p. 445–446 K).

Refinement top

Initial efinement of the structure converged with unacceptably high R-values (R = 0.095 for observed reflections and wR2 = 0.306 for all reflections), and there were seven residual peaks in the electron density difference map larger than 0.42 e Å−3 (maximum 1.64 e Å−3). These peaks appeared close to the 4-methoxyphenyl group and indicated disorder. Six of the seven largest peaks formed a planar ring and they were taken to be the phenyl carbon atoms, while the largest residual peak could be attributed to the methoxy oxygen atom. The methoxy carbon atom was also found (peak height 0.26 e Å−3). No other atom, except the benzylic carbon atom attached to the 4-methoxyphenyl group, could be resolved into two parts. Another kind of disorder was found in the methyl group C10. Refinement with geometrical similarity restraints on disordered atoms led to occupancies of 0.806:0.194 (3).

Hydrogen atoms were refined isotropically and were constrained to the ideal geometry, using an appropriate riding model. For the hydroxyl group, the O–H distance (0.84 Å) and C–O–H angle (109.5°) were kept fixed, and the torsion angle was chosen to match the observed electron density. For methyl groups, the C–H distances (0.96 Å) and C–C–H angles (109.5°) were kept fixed, while the torsion angles were allowed to refine, with the starting position based on the threefold averaged circular Fourier synthesis. For methyl group C10, an idealized disordered methyl group was assumed, with two positions rotated from each other by 60 ° and with a half-occupancy for hydrogen atoms.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and SADABS (Sheldrick, 2001); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The atom-numbering scheme for (I). Displacement ellipsoids are shown at the 50% probability level. The disorder of the methyl group C10 is shown. A dashed line indicates the intramolecular hydrogen bond.
[Figure 2] Fig. 2. The disorder of the 4-methoxyphenyl group. The minor part, with occupancy 0.194 (3), is shown with smaller radii of atoms and dashed bonds.
[Figure 3] Fig. 3. A packing diagram, in projection along the c axis.
1-(2-Hydroxy-4,6-dimethoxy-3-methylphenyl)-3-(4-methoxyphenyl)- 2-methyl-1,3-propanedione top
Crystal data top
C20H22O6Dx = 1.332 Mg m3
Mr = 358.38Melting point: 445–446 K K
Monoclinic, I2/cMo Kα radiation, λ = 0.71073 Å
a = 12.2304 (2) ÅCell parameters from 8192 reflections
b = 16.4299 (2) Åθ = 1.7–30.6°
c = 17.8325 (2) ŵ = 0.10 mm1
β = 93.999 (1)°T = 183 K
V = 3574.61 (8) Å3Needle, colourless
Z = 80.60 × 0.12 × 0.10 mm
F(000) = 1520
Data collection top
Siemens SMART CCD
diffractometer
5495 independent reflections
Radiation source: fine-focus sealed tube3717 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 30.6°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1717
Tmin = 0.943, Tmax = 0.990k = 2323
24968 measured reflectionsl = 2525
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0721P)2 + 1.3054P]
where P = (Fo2 + 2Fc2)/3
5495 reflections(Δ/σ)max = 0.001
340 parametersΔρmax = 0.24 e Å3
472 restraintsΔρmin = 0.28 e Å3
Crystal data top
C20H22O6V = 3574.61 (8) Å3
Mr = 358.38Z = 8
Monoclinic, I2/cMo Kα radiation
a = 12.2304 (2) ŵ = 0.10 mm1
b = 16.4299 (2) ÅT = 183 K
c = 17.8325 (2) Å0.60 × 0.12 × 0.10 mm
β = 93.999 (1)°
Data collection top
Siemens SMART CCD
diffractometer
5495 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
3717 reflections with I > 2σ(I)
Tmin = 0.943, Tmax = 0.990Rint = 0.041
24968 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049472 restraints
wR(F2) = 0.144H-atom parameters constrained
S = 0.99Δρmax = 0.24 e Å3
5495 reflectionsΔρmin = 0.28 e Å3
340 parameters
Special details top

Experimental. Data were collected at low temperature using a Siemens SMART CCD diffractometer equiped with a LT-2 device. A full sphere of reciprocal space was scanned by 0.3° steps in ω with a crystal–to–detector distance of 3.97 cm, 30 s per frame. Preliminary orientation matrix was obtained from the first 100 frames using SMART (Siemens, 1995). The collected frames were integrated using the preliminary orientation matrix which was updated every 100 frames. Final cell parameters were obtained by refinement on the position of 8192 reflections with I>10σ(I) after integration of all the frames data using SAINT (Siemens, 1995).

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*/UeqOcc. (<1)
C10.92142 (9)1.03869 (7)0.58033 (7)0.0323 (2)
C20.91740 (10)1.12482 (7)0.58918 (7)0.0367 (3)
C30.99624 (11)1.16817 (7)0.63208 (7)0.0399 (3)
C41.08127 (10)1.12458 (7)0.66849 (7)0.0377 (3)
C51.09070 (10)1.04049 (7)0.66102 (7)0.0353 (3)
H51.15031.01220.68620.043 (4)*
C61.01266 (9)0.99870 (7)0.61681 (7)0.0322 (2)
C70.83167 (9)0.99771 (7)0.53715 (7)0.0360 (3)
C80.82704 (9)0.90604 (7)0.52657 (7)0.0330 (2)
H80.89540.88700.50430.035 (3)*
C100.98710 (15)1.25914 (8)0.63964 (10)0.0576 (4)
H10A1.05781.28140.65910.053 (4)*0.50
H10B0.93111.27220.67450.053 (4)*0.50
H10C0.96651.28300.59030.053 (4)*0.50
H10D0.91241.27630.62350.053 (4)*0.50
H10E1.03921.28560.60810.053 (4)*0.50
H10F1.00381.27470.69220.053 (4)*0.50
C111.24148 (13)1.12768 (10)0.75327 (9)0.0541 (4)
H11A1.20981.08780.78640.056 (5)*
H11B1.28551.16700.78370.076 (6)*
H11C1.28821.09960.71900.059 (5)*
C121.11015 (12)0.87425 (8)0.64192 (10)0.0540 (4)
H12A1.17910.89600.62530.063 (5)*
H12B1.10430.81640.62900.058 (5)*
H12C1.10890.88080.69650.062 (5)*
C130.72712 (11)0.88020 (8)0.47592 (8)0.0430 (3)
H13A0.72960.82130.46750.058 (5)*
H13B0.72760.90860.42760.053 (4)*
H13C0.66010.89410.50020.062 (5)*
O10.83414 (8)1.16840 (5)0.55614 (6)0.0506 (3)
H10.78991.13690.53260.086 (7)*
O21.15567 (8)1.16928 (6)0.71075 (6)0.0500 (3)
O31.02006 (7)0.91742 (5)0.60535 (6)0.0416 (2)
O40.75449 (8)1.03771 (6)0.50730 (7)0.0554 (3)
O50.77840 (9)0.90076 (7)0.65288 (6)0.0554 (3)
C90.8184 (5)0.8668 (2)0.6026 (3)0.0376 (8)0.806 (3)
C140.8560 (3)0.78139 (16)0.61556 (14)0.0328 (5)0.806 (3)
C150.90368 (19)0.73521 (13)0.56148 (14)0.0378 (4)0.806 (3)
H150.91380.75850.51370.051 (3)*0.806 (3)
C160.93689 (14)0.65544 (11)0.57579 (12)0.0386 (4)0.806 (3)
H160.97010.62480.53840.051 (3)*0.806 (3)
C170.9212 (3)0.62125 (14)0.64487 (16)0.0364 (6)0.806 (3)
C180.87338 (15)0.66671 (10)0.70002 (10)0.0410 (4)0.806 (3)
H180.86250.64320.74760.051 (3)*0.806 (3)
C190.84217 (16)0.74575 (11)0.68499 (11)0.0393 (4)0.806 (3)
H190.81040.77670.72290.051 (3)*0.806 (3)
C201.0117 (3)0.49795 (17)0.61708 (18)0.0544 (7)0.806 (3)
H20A0.97260.49290.56740.062 (4)*0.806 (3)
H20B1.02570.44360.63840.062 (4)*0.806 (3)
H20C1.08150.52600.61220.062 (4)*0.806 (3)
O60.94709 (11)0.54318 (7)0.66508 (7)0.0487 (4)0.806 (3)
C9A0.8296 (18)0.8539 (8)0.6017 (9)0.031 (2)0.194 (3)
C14A0.8693 (10)0.7689 (6)0.5924 (5)0.0260 (18)0.194 (3)
C15A0.8998 (7)0.7357 (5)0.5258 (5)0.0337 (16)0.194 (3)
H15A0.89460.76700.48090.051 (3)*0.194 (3)
C16A0.9378 (5)0.6564 (4)0.5249 (4)0.0363 (15)0.194 (3)
H16A0.95550.63180.47910.051 (3)*0.194 (3)
C17A0.9499 (5)0.6126 (4)0.5925 (4)0.0327 (15)0.194 (3)
C18A0.9202 (12)0.6454 (6)0.6605 (6)0.037 (2)0.194 (3)
H18A0.92690.61470.70570.051 (3)*0.194 (3)
C19A0.8804 (6)0.7251 (4)0.6593 (4)0.0375 (15)0.194 (3)
H19A0.86060.74970.70460.051 (3)*0.194 (3)
C20A1.0201 (15)0.4895 (8)0.6501 (7)0.068 (4)0.194 (3)
H20D1.06250.52350.68670.062 (4)*0.194 (3)
H20E1.06410.44240.63720.062 (4)*0.194 (3)
H20F0.95310.47080.67180.062 (4)*0.194 (3)
O6A0.9917 (4)0.5363 (3)0.5833 (3)0.0475 (15)0.194 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0288 (5)0.0261 (5)0.0411 (6)0.0020 (4)0.0048 (5)0.0004 (4)
C20.0374 (6)0.0286 (5)0.0428 (7)0.0056 (5)0.0063 (5)0.0012 (5)
C30.0464 (7)0.0279 (5)0.0441 (7)0.0005 (5)0.0054 (6)0.0041 (5)
C40.0373 (6)0.0356 (6)0.0390 (6)0.0066 (5)0.0045 (5)0.0022 (5)
C50.0294 (5)0.0332 (6)0.0420 (6)0.0020 (4)0.0063 (5)0.0043 (5)
C60.0282 (5)0.0262 (5)0.0416 (6)0.0000 (4)0.0027 (5)0.0037 (5)
C70.0285 (5)0.0312 (5)0.0470 (7)0.0036 (4)0.0065 (5)0.0010 (5)
C80.0252 (5)0.0289 (5)0.0443 (6)0.0007 (4)0.0013 (5)0.0033 (5)
C100.0738 (11)0.0310 (6)0.0652 (10)0.0027 (6)0.0156 (8)0.0101 (6)
C110.0460 (8)0.0586 (9)0.0547 (9)0.0098 (7)0.0179 (7)0.0046 (7)
C120.0397 (7)0.0337 (6)0.0849 (12)0.0070 (5)0.0220 (7)0.0097 (7)
C130.0327 (6)0.0424 (7)0.0529 (8)0.0056 (5)0.0055 (6)0.0063 (6)
O10.0509 (6)0.0295 (4)0.0678 (7)0.0124 (4)0.0211 (5)0.0053 (4)
O20.0506 (6)0.0415 (5)0.0549 (6)0.0081 (4)0.0173 (5)0.0073 (4)
O30.0310 (4)0.0251 (4)0.0663 (6)0.0027 (3)0.0139 (4)0.0039 (4)
O40.0429 (5)0.0373 (5)0.0816 (7)0.0093 (4)0.0281 (5)0.0045 (5)
O50.0574 (6)0.0579 (6)0.0521 (6)0.0026 (5)0.0134 (5)0.0057 (5)
C90.0279 (17)0.0278 (9)0.0561 (16)0.0016 (8)0.0048 (11)0.0031 (9)
C140.0285 (11)0.0293 (9)0.0404 (14)0.0044 (7)0.0006 (10)0.0056 (9)
C150.0400 (10)0.0338 (9)0.0407 (11)0.0010 (7)0.0103 (11)0.0015 (10)
C160.0384 (8)0.0331 (9)0.0448 (11)0.0006 (7)0.0059 (7)0.0007 (8)
C170.0317 (9)0.0343 (12)0.0419 (15)0.0048 (9)0.0056 (9)0.0000 (9)
C180.0460 (9)0.0423 (9)0.0338 (8)0.0056 (7)0.0039 (7)0.0001 (7)
C190.0425 (10)0.0383 (9)0.0365 (9)0.0048 (7)0.0005 (7)0.0086 (7)
C200.0545 (14)0.0325 (11)0.076 (2)0.0017 (10)0.0053 (15)0.0001 (14)
O60.0561 (8)0.0361 (6)0.0532 (7)0.0034 (5)0.0006 (6)0.0076 (5)
C9A0.019 (4)0.050 (5)0.026 (4)0.001 (5)0.014 (3)0.005 (4)
C14A0.023 (4)0.026 (4)0.030 (5)0.004 (3)0.007 (4)0.002 (3)
C15A0.032 (3)0.028 (3)0.042 (4)0.003 (2)0.008 (4)0.002 (3)
C16A0.039 (3)0.031 (3)0.039 (4)0.004 (2)0.001 (3)0.000 (3)
C17A0.034 (3)0.027 (3)0.036 (4)0.008 (2)0.007 (3)0.004 (3)
C18A0.044 (4)0.036 (5)0.030 (4)0.004 (4)0.008 (4)0.005 (3)
C19A0.041 (4)0.038 (3)0.033 (3)0.008 (3)0.003 (3)0.003 (3)
C20A0.103 (9)0.032 (5)0.066 (8)0.006 (5)0.017 (7)0.002 (5)
O6A0.052 (3)0.027 (2)0.062 (3)0.004 (2)0.014 (2)0.003 (2)
Geometric parameters (Å, º) top
C1—C61.4137 (15)O1—H10.840
C1—C21.4252 (16)O5—C9A1.377 (14)
C1—C71.4605 (16)O5—C91.189 (4)
C2—O11.3464 (14)C9—C141.490 (3)
C2—C31.3854 (17)C14—C191.391 (3)
C3—C41.3863 (18)C14—C151.387 (3)
C3—C101.5057 (18)C15—C161.390 (3)
C4—O21.3564 (14)C15—H150.950
C4—C51.3936 (17)C16—C171.379 (4)
C5—C61.3780 (16)C16—H160.950
C5—H50.950C17—O61.364 (3)
C6—O31.3550 (14)C17—C181.395 (3)
C7—O41.2394 (14)C18—C191.375 (3)
C7—C81.5184 (16)C18—H180.950
C8—C9A1.589 (14)C19—H190.950
C8—C91.512 (5)C20—O61.415 (3)
C8—C131.5282 (16)C20—H20A0.980
C8—H81.000C20—H20B0.980
C10—H10A0.980C20—H20C0.980
C10—H10B0.980C9A—C14A1.492 (12)
C10—H10C0.980C14A—C19A1.391 (10)
C10—H10D0.980C14A—C15A1.382 (9)
C10—H10E0.980C15A—C16A1.384 (9)
C10—H10F0.980C15A—H15A0.950
C11—O21.4257 (18)C16A—C17A1.402 (9)
C11—H11A0.980C16A—H16A0.950
C11—H11B0.980C17A—C18A1.398 (11)
C11—H11C0.980C17A—O6A1.368 (8)
C12—O31.4291 (14)C18A—C19A1.397 (11)
C12—H12A0.980C18A—H18A0.950
C12—H12B0.980C19A—H19A0.950
C12—H12C0.980C20A—O6A1.439 (10)
C13—H13A0.980C20A—H20D0.980
C13—H13B0.980C20A—H20E0.980
C13—H13C0.980C20A—H20F0.980
C6—C1—C2116.27 (10)C8—C13—H13C109.5
C6—C1—C7124.64 (10)H13A—C13—H13C109.5
C2—C1—C7119.06 (10)H13B—C13—H13C109.5
O1—C2—C3116.38 (11)C2—O1—H1109.5
O1—C2—C1120.69 (11)C4—O2—C11118.44 (11)
C3—C2—C1122.93 (11)C6—O3—C12118.55 (10)
C2—C3—C4117.62 (11)O5—C9—C14117.6 (4)
C2—C3—C10120.44 (12)O5—C9—C8122.3 (3)
C4—C3—C10121.93 (12)C14—C9—C8120.0 (3)
O2—C4—C5122.22 (11)C19—C14—C15118.1 (2)
O2—C4—C3115.65 (11)C19—C14—C9118.6 (2)
C5—C4—C3122.12 (11)C15—C14—C9123.2 (3)
C6—C5—C4119.34 (11)C14—C15—C16121.3 (2)
C6—C5—H5120.3C14—C15—H15119.3
C4—C5—H5120.3C16—C15—H15119.3
O3—C6—C5121.76 (10)C17—C16—C15119.38 (19)
O3—C6—C1116.58 (10)C17—C16—H16120.3
C5—C6—C1121.66 (10)C15—C16—H16120.3
O4—C7—C1120.25 (11)O6—C17—C16125.1 (2)
O4—C7—C8116.87 (10)O6—C17—C18114.7 (2)
C1—C7—C8122.88 (10)C16—C17—C18120.2 (2)
C9A—C8—C7115.6 (6)C17—C18—C19119.51 (19)
C9—C8—C7108.39 (17)C17—C18—H18120.2
C9A—C8—C13108.4 (9)C19—C18—H18120.2
C9—C8—C13108.0 (2)C14—C19—C18121.47 (19)
C7—C8—C13111.74 (10)C14—C19—H19119.3
C9A—C8—H8101.4C18—C19—H19119.3
C9—C8—H8109.6C17—O6—C20117.6 (2)
C7—C8—H8109.6O5—C9A—C8105.9 (8)
C13—C8—H8109.6O5—C9A—C14A139.8 (11)
C3—C10—H10A109.5C8—C9A—C14A113.5 (10)
C3—C10—H10B109.5C19A—C14A—C15A121.2 (8)
H10A—C10—H10B109.5C19A—C14A—C9A113.7 (9)
C3—C10—H10C109.5C15A—C14A—C9A125.1 (9)
H10A—C10—H10C109.5C14A—C15A—C16A119.5 (8)
H10B—C10—H10C109.5C14A—C15A—H15A120.3
C3—C10—H10D109.5C16A—C15A—H15A120.3
C3—C10—H10E109.5C17A—C16A—C15A119.3 (7)
H10D—C10—H10E109.5C17A—C16A—H16A120.4
C3—C10—H10F109.5C15A—C16A—H16A120.4
H10D—C10—H10F109.5C18A—C17A—C16A122.0 (7)
H10E—C10—H10F109.5C18A—C17A—O6A125.4 (7)
O2—C11—H11A109.5C16A—C17A—O6A112.7 (6)
O2—C11—H11B109.5C17A—C18A—C19A117.4 (9)
H11A—C11—H11B109.5C17A—C18A—H18A121.3
O2—C11—H11C109.5C19A—C18A—H18A121.3
H11A—C11—H11C109.5C14A—C19A—C18A120.7 (8)
H11B—C11—H11C109.5C14A—C19A—H19A119.7
O3—C12—H12A109.5C18A—C19A—H19A119.7
O3—C12—H12B109.5O6A—C20A—H20D109.5
H12A—C12—H12B109.5O6A—C20A—H20E109.5
O3—C12—H12C109.5H20D—C20A—H20E109.5
H12A—C12—H12C109.5O6A—C20A—H20F109.5
H12B—C12—H12C109.5H20D—C20A—H20F109.5
C8—C13—H13A109.5H20E—C20A—H20F109.5
C8—C13—H13B109.5C17A—O6A—C20A117.5 (8)
H13A—C13—H13B109.5
C6—C1—C2—O1179.52 (12)C7—C8—C9—C14155.7 (4)
C7—C1—C2—O12.29 (19)C13—C8—C9—C1483.1 (4)
C6—C1—C2—C31.29 (19)O5—C9—C14—C190.2 (6)
C7—C1—C2—C3176.89 (13)C8—C9—C14—C19177.0 (3)
O1—C2—C3—C4178.22 (13)O5—C9—C14—C15179.8 (4)
C1—C2—C3—C41.0 (2)C8—C9—C14—C152.6 (6)
O1—C2—C3—C100.4 (2)C19—C14—C15—C160.0 (4)
C1—C2—C3—C10179.65 (14)C9—C14—C15—C16179.5 (3)
C2—C3—C4—O2179.05 (12)C14—C15—C16—C170.6 (4)
C10—C3—C4—O20.4 (2)C15—C16—C17—O6178.0 (2)
C2—C3—C4—C52.1 (2)C15—C16—C17—C180.7 (4)
C10—C3—C4—C5179.30 (14)O6—C17—C18—C19178.81 (18)
O2—C4—C5—C6179.56 (12)C16—C17—C18—C190.0 (3)
C3—C4—C5—C60.8 (2)C15—C14—C19—C180.7 (4)
C4—C5—C6—O3177.49 (12)C9—C14—C19—C18178.9 (3)
C4—C5—C6—C11.73 (19)C17—C18—C19—C140.7 (3)
C2—C1—C6—O3176.58 (11)C16—C17—O6—C2011.4 (4)
C7—C1—C6—O35.35 (18)C18—C17—O6—C20169.9 (2)
C2—C1—C6—C52.67 (18)C7—C8—C9A—O531.4 (16)
C7—C1—C6—C5175.40 (12)C13—C8—C9A—O594.9 (12)
C6—C1—C7—O4179.63 (13)C7—C8—C9A—C14A156.9 (11)
C2—C1—C7—O41.6 (2)C13—C8—C9A—C14A76.8 (15)
C6—C1—C7—C80.1 (2)O5—C9A—C14A—C19A17 (3)
C2—C1—C7—C8178.16 (12)C8—C9A—C14A—C19A174.9 (11)
O4—C7—C8—C9A121.7 (9)O5—C9A—C14A—C15A166 (2)
C1—C7—C8—C9A58.1 (9)C8—C9A—C14A—C15A1 (2)
O4—C7—C8—C9115.9 (3)C19A—C14A—C15A—C16A2.7 (15)
C1—C7—C8—C963.9 (3)C9A—C14A—C15A—C16A178.5 (14)
O4—C7—C8—C132.97 (17)C14A—C15A—C16A—C17A3.2 (12)
C1—C7—C8—C13177.25 (12)C15A—C16A—C17A—C18A2.8 (12)
C5—C4—O2—C114.8 (2)C15A—C16A—C17A—O6A177.9 (6)
C3—C4—O2—C11176.27 (13)C16A—C17A—C18A—C19A1.7 (15)
C5—C6—O3—C121.58 (19)O6A—C17A—C18A—C19A179.0 (8)
C1—C6—O3—C12179.17 (13)C15A—C14A—C19A—C18A1.6 (16)
C9A—O5—C9—C1414 (9)C9A—C14A—C19A—C18A177.9 (13)
C9A—O5—C9—C8169 (10)C17A—C18A—C19A—C14A1.1 (16)
C7—C8—C9—O527.2 (6)C18A—C17A—O6A—C20A8.0 (14)
C13—C8—C9—O594.0 (5)C16A—C17A—O6A—C20A172.6 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.841.742.4899 (14)148

Experimental details

Crystal data
Chemical formulaC20H22O6
Mr358.38
Crystal system, space groupMonoclinic, I2/c
Temperature (K)183
a, b, c (Å)12.2304 (2), 16.4299 (2), 17.8325 (2)
β (°) 93.999 (1)
V3)3574.61 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.60 × 0.12 × 0.10
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.943, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
24968, 5495, 3717
Rint0.041
(sin θ/λ)max1)0.716
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.144, 0.99
No. of reflections5495
No. of parameters340
No. of restraints472
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.28

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SAINT and SADABS (Sheldrick, 2001), SHELXTL (Bruker, 1997), SHELXTL, DIAMOND (Brandenburg, 2000).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O40.841.742.4899 (14)148
 

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