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The structure of the title compound, C20H20O8, which was extracted from Rhodomyrtus tomentosa, confirms the connectivity and is consistent with the results from spectroscopy. The structure, notable for the crowded sequence of (3',4',5') tri­methoxy substituents, is compared with that of its previously recorded analogue lacking the methyl at the 4'-oxy­gen (two polymorphs), and with myricetin which lacks all O-methyl­ation (cocrystallized with tri­phenyl­phosphine oxide). The latter, interestingly, has a dihedral angle of 36.4 (3)° between its planar aromatic components, but the overall cyclic framework of the title mol­ecule is essentially planar. In the crystal structure, the mol­ecules stack obliquely along the short [4.244 (2) Å] c axis of the orthogonal cell.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027880/lh6146sup1.cif
Contains datablocks global, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027880/lh61461sup2.hkl
Contains datablock 1

CCDC reference: 232158

Key indicators

  • Single-crystal X-ray study
  • T = 150 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.053
  • wR factor = 0.059
  • Data-to-parameter ratio = 6.1

checkCIF/PLATON results

No syntax errors found



Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5991 Proportion of unique data used 0.8530 Ratio reflections to parameters 6.0556 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.06 PLAT163_ALERT_4_C Missing or Zero su (esd) on z-coordinate for ... O1 PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.14 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 9
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.20 From the CIF: _reflns_number_total 1789 Count of symmetry unique reflns 1809 Completeness (_total/calc) 98.89% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: Xtal3.5 User's Manual (Hall et al., 1995); program(s) used to solve structure: Xtal3.5; program(s) used to refine structure: Xtal3.5 CRYLSQ; molecular graphics: Xtal3.5; software used to prepare material for publication: Xtal3.5 BONDLA CIFIO.

(1) top
Crystal data top
C20H20O8F(000) = 816
Mr = 388.37Dx = 1.47 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 1050 reflections
a = 13.827 (6) Åθ = 2.4–24.5°
b = 29.900 (14) ŵ = 0.12 mm1
c = 4.244 (2) ÅT = 150 K
V = 1754.6 (14) Å3Splinter, yellow
Z = 40.3 × 0.06 × 0.03 mm
Data collection top
Bruker SMART CCD
diffractometer
1789 independent reflections
Radiation source: sealed tube1526 reflections with I > σ(I)
Graphite monochromatorRint = 0.077
ω scansθmax = 25.2°, θmin = 1.4°
Absorption correction: multi-scan
SADABS; Sheldrick, 1996
h = 1616
Tmin = 0.957, Tmax = 0.998k = 3535
13745 measured reflectionsl = 55
Refinement top
Refinement on FPrimary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: difference Fourier map
wR(F2) = 0.059H-atom parameters not refined
S = 1.06 w = 1/[σ2(Fo) + 0.0013F2]
where σ(I) = [σ(I)meas + 0.0004(Inet)2]1/2
1526 reflections(Δ/σ)max = 0.009
252 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.36 e Å3
0 constraints
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.6483 (3)0.10368 (12)0.500000.035 (3)
C20.5996 (4)0.13477 (19)0.319 (2)0.034 (4)
C30.6482 (4)0.17278 (19)0.224 (2)0.032 (4)
O30.6037 (3)0.20226 (12)0.019 (2)0.041 (3)
C310.5771 (5)0.24460 (19)0.168 (3)0.061 (5)
C40.7449 (5)0.18179 (19)0.319 (2)0.034 (4)
O40.7892 (3)0.21698 (13)0.236 (2)0.050 (3)
C4a0.7925 (4)0.14885 (17)0.512 (2)0.031 (4)
C50.8870 (5)0.15326 (19)0.621 (2)0.036 (4)
O50.9390 (3)0.19077 (13)0.546 (2)0.054 (3)
C60.9305 (4)0.1201 (2)0.794 (2)0.035 (4)
C70.8784 (5)0.08063 (19)0.862 (2)0.032 (4)
O70.9301 (3)0.05004 (12)1.029 (2)0.042 (3)
C710.8823 (5)0.00809 (18)1.097 (3)0.048 (5)
C80.7850 (4)0.07549 (18)0.765 (2)0.034 (4)
C8a0.7409 (4)0.10933 (19)0.590 (2)0.032 (4)
C1'0.4999 (5)0.12145 (19)0.263 (2)0.033 (4)
C2'0.4361 (5)0.14687 (18)0.074 (3)0.036 (4)
C3'0.3412 (5)0.13520 (19)0.040 (2)0.033 (4)
O3'0.2736 (3)0.15831 (13)0.1267 (19)0.047 (3)
C31'0.3046 (5)0.1992 (2)0.274 (3)0.051 (5)
C4'0.3052 (5)0.09560 (19)0.185 (2)0.037 (4)
O4'0.2120 (3)0.08239 (12)0.1372 (19)0.040 (3)
C41'0.1442 (5)0.1029 (2)0.352 (3)0.046 (5)
C5'0.3683 (4)0.07053 (19)0.365 (2)0.033 (4)
O5'0.3261 (3)0.03256 (13)0.498 (2)0.042 (3)
C51'0.3856 (5)0.0058 (2)0.689 (3)0.040 (4)
C6'0.4634 (4)0.08254 (18)0.411 (2)0.033 (4)
H31a0.544800.264000.017040.09500*
H31b0.631240.259880.248300.09500*
H31c0.531510.239700.337170.09500*
H50.895910.207460.421620.08100*
H60.997200.123940.868100.04100*
H71a0.923570.011301.217860.07500*
H71b0.864640.007270.908120.07500*
H71c0.824220.012781.218420.07500*
H80.750190.048980.822840.04000*
H2'0.462160.172790.036820.04700*
H31'a0.254850.213210.388820.07100*
H31'b0.357610.192970.423740.07100*
H31'c0.330590.219710.123070.07100*
H41'a0.079840.092780.305200.06200*
H41'b0.145340.134780.326820.06200*
H41'c0.159370.095620.562240.06200*
H51'a0.351580.018700.776820.06200*
H51'b0.410600.023520.867190.06200*
H51'c0.440560.004800.576890.06200*
H6'0.505440.064590.549350.03600*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.030 (2)0.023 (2)0.051 (3)0.0044 (18)0.006 (3)0.003 (3)
C20.040 (4)0.022 (3)0.038 (5)0.009 (3)0.000 (4)0.006 (4)
C30.034 (4)0.025 (3)0.038 (5)0.006 (3)0.000 (4)0.000 (4)
O30.047 (3)0.020 (2)0.056 (4)0.000 (2)0.005 (3)0.001 (3)
C310.061 (5)0.022 (3)0.100 (8)0.004 (3)0.013 (6)0.004 (5)
C40.040 (4)0.023 (3)0.039 (5)0.000 (3)0.005 (4)0.006 (4)
O40.049 (3)0.025 (2)0.076 (4)0.006 (2)0.003 (3)0.008 (3)
C4a0.034 (4)0.019 (3)0.041 (5)0.003 (3)0.009 (4)0.004 (4)
C50.033 (4)0.024 (3)0.052 (5)0.001 (3)0.000 (4)0.009 (4)
O50.044 (3)0.032 (2)0.085 (4)0.016 (2)0.011 (4)0.013 (3)
C60.028 (4)0.034 (3)0.044 (5)0.003 (3)0.001 (4)0.006 (4)
C70.033 (4)0.028 (3)0.034 (5)0.002 (3)0.004 (4)0.002 (4)
O70.036 (3)0.028 (2)0.061 (4)0.003 (2)0.005 (3)0.003 (3)
C710.042 (4)0.020 (3)0.081 (7)0.002 (3)0.002 (5)0.007 (4)
C80.028 (4)0.021 (3)0.051 (5)0.000 (3)0.001 (4)0.001 (4)
C8a0.031 (4)0.026 (3)0.039 (5)0.002 (3)0.002 (3)0.005 (4)
C1'0.029 (4)0.026 (3)0.044 (5)0.003 (3)0.002 (4)0.006 (4)
C2'0.034 (4)0.023 (3)0.051 (5)0.001 (3)0.007 (4)0.001 (4)
C3'0.039 (4)0.024 (3)0.037 (5)0.006 (3)0.014 (4)0.004 (4)
O3'0.054 (3)0.024 (2)0.062 (4)0.003 (2)0.012 (3)0.009 (3)
C31'0.061 (5)0.030 (4)0.062 (6)0.009 (3)0.005 (5)0.003 (5)
C4'0.038 (4)0.026 (3)0.047 (5)0.003 (3)0.003 (4)0.009 (4)
O4'0.029 (3)0.031 (2)0.059 (4)0.0015 (19)0.009 (3)0.006 (3)
C41'0.030 (4)0.041 (4)0.068 (6)0.002 (3)0.001 (4)0.004 (4)
C5'0.032 (4)0.023 (3)0.043 (5)0.003 (3)0.002 (4)0.005 (4)
O5'0.033 (3)0.033 (2)0.060 (4)0.003 (2)0.005 (3)0.008 (3)
C51'0.040 (4)0.030 (3)0.049 (5)0.004 (3)0.003 (4)0.005 (4)
C6'0.033 (4)0.016 (3)0.049 (6)0.006 (3)0.002 (4)0.001 (3)
Geometric parameters (Å, º) top
O1—C21.382 (8)C8—C8a1.396 (10)
O1—C8a1.348 (7)C8—H80.959
C2—C31.380 (9)C1'—C2'1.414 (11)
C2—C1'1.454 (9)C1'—C6'1.415 (9)
C3—O31.381 (10)C2'—C3'1.365 (9)
C3—C41.423 (9)C2'—H2'0.976
O3—C311.461 (9)C3'—O3'1.361 (9)
C31—H31a0.971C3'—C4'1.425 (10)
C31—H31b0.942O3'—C31'1.439 (9)
C31—H31c0.968C31'—H31'a0.940
C4—O41.267 (8)C31'—H31'b0.987
C4—C4a1.442 (10)C31'—H31'c0.958
C4a—C51.391 (9)C4'—O4'1.363 (8)
C4a—C8a1.418 (8)C4'—C5'1.380 (11)
C5—O51.370 (8)O4'—C41'1.444 (10)
C5—C61.374 (10)C41'—H41'a0.961
O5—H50.939C41'—H41'b0.960
C6—C71.412 (9)C41'—H41'c0.941
C6—H60.982C5'—O5'1.396 (8)
C7—O71.359 (9)C5'—C6'1.377 (9)
C7—C81.363 (9)O5'—C51'1.405 (10)
O7—C711.447 (7)C51'—H51'a0.946
C71—H71a0.962C51'—H51'b0.985
C71—H71b0.955C51'—H51'c0.952
C71—H71c0.964C6'—H6'0.985
C2—O1—C8a122.5 (5)O1—C8a—C8118.4 (5)
O1—C2—C3118.6 (6)C4a—C8a—C8120.5 (6)
O1—C2—C1'111.6 (5)C2—C1'—C2'122.5 (6)
C3—C2—C1'129.7 (7)C2—C1'—C6'119.4 (7)
C2—C3—O3119.5 (6)C2'—C1'—C6'118.1 (6)
C2—C3—C4122.1 (7)C1'—C2'—C3'121.5 (7)
O3—C3—C4118.4 (6)C1'—C2'—H2'118.0
C3—O3—C31113.2 (8)C3'—C2'—H2'120.5
O3—C31—H31a110.5C2'—C3'—O3'125.8 (6)
O3—C31—H31b112.1C2'—C3'—C4'120.2 (7)
O3—C31—H31c110.7O3'—C3'—C4'114.0 (6)
H31a—C31—H31b108.4C3'—O3'—C31'117.0 (5)
H31a—C31—H31c106.3O3'—C31'—H31'a112.7
H31b—C31—H31c108.7O3'—C31'—H31'b109.9
C3—C4—O4122.2 (7)O3'—C31'—H31'c111.3
C3—C4—C4a117.5 (6)H31'a—C31'—H31'b107.2
O4—C4—C4a120.3 (6)H31'a—C31'—H31'c109.6
C4—C4a—C5123.5 (6)H31'b—C31'—H31'c105.8
C4—C4a—C8a118.1 (6)C3'—C4'—O4'120.5 (6)
C5—C4a—C8a118.3 (6)C3'—C4'—C5'118.0 (6)
C4a—C5—O5119.6 (6)O4'—C4'—C5'121.5 (6)
C4a—C5—C6121.3 (6)C4'—O4'—C41'113.4 (6)
O5—C5—C6119.1 (6)O4'—C41'—H41'a109.7
C5—O5—H5103.4O4'—C41'—H41'b109.9
C5—C6—C7119.3 (6)O4'—C41'—H41'c110.9
C5—C6—H6119.9H41'a—C41'—H41'b107.7
C7—C6—H6120.8H41'a—C41'—H41'c109.3
C6—C7—O7113.6 (6)H41'b—C41'—H41'c109.4
C6—C7—C8121.1 (6)C4'—C5'—O5'113.7 (5)
O7—C7—C8125.4 (6)C4'—C5'—C6'122.7 (6)
C7—O7—C71116.6 (5)O5'—C5'—C6'123.6 (7)
O7—C71—H71a111.0C5'—O5'—C51'116.9 (5)
O7—C71—H71b111.4O5'—C51'—H51'a112.2
O7—C71—H71c111.2O5'—C51'—H51'b110.0
H71a—C71—H71b108.0O5'—C51'—H51'c111.5
H71a—C71—H71c107.3H51'a—C51'—H51'b106.9
H71b—C71—H71c107.8H51'a—C51'—H51'c109.6
C7—C8—C8a119.5 (6)H51'b—C51'—H51'c106.4
C7—C8—H8119.5C1'—C6'—C5'119.4 (7)
C8a—C8—H8121.0C1'—C6'—H6'120.1
O1—C8a—C4a121.1 (6)C5'—C6'—H6'120.4
 

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