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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
CCDC reference: 232158
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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.
Crystal data top
C20H20O8 | F(000) = 816 |
Mr = 388.37 | Dx = 1.47 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 1050 reflections |
a = 13.827 (6) Å | θ = 2.4–24.5° |
b = 29.900 (14) Å | µ = 0.12 mm−1 |
c = 4.244 (2) Å | T = 150 K |
V = 1754.6 (14) Å3 | Splinter, yellow |
Z = 4 | 0.3 × 0.06 × 0.03 mm |
Data collection top
Bruker SMART CCD diffractometer | 1789 independent reflections |
Radiation source: sealed tube | 1526 reflections with I > σ(I) |
Graphite monochromator | Rint = 0.077 |
ω scans | θmax = 25.2°, θmin = 1.4° |
Absorption correction: multi-scan SADABS; Sheldrick, 1996 | h = −16→16 |
Tmin = 0.957, Tmax = 0.998 | k = −35→35 |
13745 measured reflections | l = −5→5 |
Refinement top
Refinement on F | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.053 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.059 | H-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 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
0 constraints | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 0.6483 (3) | 0.10368 (12) | 0.50000 | 0.035 (3) | |
C2 | 0.5996 (4) | 0.13477 (19) | 0.319 (2) | 0.034 (4) | |
C3 | 0.6482 (4) | 0.17278 (19) | 0.224 (2) | 0.032 (4) | |
O3 | 0.6037 (3) | 0.20226 (12) | 0.019 (2) | 0.041 (3) | |
C31 | 0.5771 (5) | 0.24460 (19) | 0.168 (3) | 0.061 (5) | |
C4 | 0.7449 (5) | 0.18179 (19) | 0.319 (2) | 0.034 (4) | |
O4 | 0.7892 (3) | 0.21698 (13) | 0.236 (2) | 0.050 (3) | |
C4a | 0.7925 (4) | 0.14885 (17) | 0.512 (2) | 0.031 (4) | |
C5 | 0.8870 (5) | 0.15326 (19) | 0.621 (2) | 0.036 (4) | |
O5 | 0.9390 (3) | 0.19077 (13) | 0.546 (2) | 0.054 (3) | |
C6 | 0.9305 (4) | 0.1201 (2) | 0.794 (2) | 0.035 (4) | |
C7 | 0.8784 (5) | 0.08063 (19) | 0.862 (2) | 0.032 (4) | |
O7 | 0.9301 (3) | 0.05004 (12) | 1.029 (2) | 0.042 (3) | |
C71 | 0.8823 (5) | 0.00809 (18) | 1.097 (3) | 0.048 (5) | |
C8 | 0.7850 (4) | 0.07549 (18) | 0.765 (2) | 0.034 (4) | |
C8a | 0.7409 (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) | |
H31a | 0.54480 | 0.26400 | 0.01704 | 0.09500* | |
H31b | 0.63124 | 0.25988 | 0.24830 | 0.09500* | |
H31c | 0.53151 | 0.23970 | 0.33717 | 0.09500* | |
H5 | 0.89591 | 0.20746 | 0.42162 | 0.08100* | |
H6 | 0.99720 | 0.12394 | 0.86810 | 0.04100* | |
H71a | 0.92357 | −0.01130 | 1.21786 | 0.07500* | |
H71b | 0.86464 | −0.00727 | 0.90812 | 0.07500* | |
H71c | 0.82422 | 0.01278 | 1.21842 | 0.07500* | |
H8 | 0.75019 | 0.04898 | 0.82284 | 0.04000* | |
H2' | 0.46216 | 0.17279 | −0.03682 | 0.04700* | |
H31'a | 0.25485 | 0.21321 | −0.38882 | 0.07100* | |
H31'b | 0.35761 | 0.19297 | −0.42374 | 0.07100* | |
H31'c | 0.33059 | 0.21971 | −0.12307 | 0.07100* | |
H41'a | 0.07984 | 0.09278 | 0.30520 | 0.06200* | |
H41'b | 0.14534 | 0.13478 | 0.32682 | 0.06200* | |
H41'c | 0.15937 | 0.09562 | 0.56224 | 0.06200* | |
H51'a | 0.35158 | −0.01870 | 0.77682 | 0.06200* | |
H51'b | 0.41060 | 0.02352 | 0.86719 | 0.06200* | |
H51'c | 0.44056 | −0.00480 | 0.57689 | 0.06200* | |
H6' | 0.50544 | 0.06459 | 0.54935 | 0.03600* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.030 (2) | 0.023 (2) | 0.051 (3) | −0.0044 (18) | −0.006 (3) | 0.003 (3) |
C2 | 0.040 (4) | 0.022 (3) | 0.038 (5) | 0.009 (3) | −0.000 (4) | −0.006 (4) |
C3 | 0.034 (4) | 0.025 (3) | 0.038 (5) | 0.006 (3) | −0.000 (4) | −0.000 (4) |
O3 | 0.047 (3) | 0.020 (2) | 0.056 (4) | −0.000 (2) | −0.005 (3) | 0.001 (3) |
C31 | 0.061 (5) | 0.022 (3) | 0.100 (8) | 0.004 (3) | −0.013 (6) | −0.004 (5) |
C4 | 0.040 (4) | 0.023 (3) | 0.039 (5) | −0.000 (3) | 0.005 (4) | −0.006 (4) |
O4 | 0.049 (3) | 0.025 (2) | 0.076 (4) | −0.006 (2) | −0.003 (3) | 0.008 (3) |
C4a | 0.034 (4) | 0.019 (3) | 0.041 (5) | −0.003 (3) | 0.009 (4) | −0.004 (4) |
C5 | 0.033 (4) | 0.024 (3) | 0.052 (5) | −0.001 (3) | 0.000 (4) | −0.009 (4) |
O5 | 0.044 (3) | 0.032 (2) | 0.085 (4) | −0.016 (2) | −0.011 (4) | 0.013 (3) |
C6 | 0.028 (4) | 0.034 (3) | 0.044 (5) | −0.003 (3) | −0.001 (4) | −0.006 (4) |
C7 | 0.033 (4) | 0.028 (3) | 0.034 (5) | 0.002 (3) | −0.004 (4) | −0.002 (4) |
O7 | 0.036 (3) | 0.028 (2) | 0.061 (4) | −0.003 (2) | −0.005 (3) | 0.003 (3) |
C71 | 0.042 (4) | 0.020 (3) | 0.081 (7) | −0.002 (3) | −0.002 (5) | 0.007 (4) |
C8 | 0.028 (4) | 0.021 (3) | 0.051 (5) | 0.000 (3) | −0.001 (4) | −0.001 (4) |
C8a | 0.031 (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—C2 | 1.382 (8) | C8—C8a | 1.396 (10) |
O1—C8a | 1.348 (7) | C8—H8 | 0.959 |
C2—C3 | 1.380 (9) | C1'—C2' | 1.414 (11) |
C2—C1' | 1.454 (9) | C1'—C6' | 1.415 (9) |
C3—O3 | 1.381 (10) | C2'—C3' | 1.365 (9) |
C3—C4 | 1.423 (9) | C2'—H2' | 0.976 |
O3—C31 | 1.461 (9) | C3'—O3' | 1.361 (9) |
C31—H31a | 0.971 | C3'—C4' | 1.425 (10) |
C31—H31b | 0.942 | O3'—C31' | 1.439 (9) |
C31—H31c | 0.968 | C31'—H31'a | 0.940 |
C4—O4 | 1.267 (8) | C31'—H31'b | 0.987 |
C4—C4a | 1.442 (10) | C31'—H31'c | 0.958 |
C4a—C5 | 1.391 (9) | C4'—O4' | 1.363 (8) |
C4a—C8a | 1.418 (8) | C4'—C5' | 1.380 (11) |
C5—O5 | 1.370 (8) | O4'—C41' | 1.444 (10) |
C5—C6 | 1.374 (10) | C41'—H41'a | 0.961 |
O5—H5 | 0.939 | C41'—H41'b | 0.960 |
C6—C7 | 1.412 (9) | C41'—H41'c | 0.941 |
C6—H6 | 0.982 | C5'—O5' | 1.396 (8) |
C7—O7 | 1.359 (9) | C5'—C6' | 1.377 (9) |
C7—C8 | 1.363 (9) | O5'—C51' | 1.405 (10) |
O7—C71 | 1.447 (7) | C51'—H51'a | 0.946 |
C71—H71a | 0.962 | C51'—H51'b | 0.985 |
C71—H71b | 0.955 | C51'—H51'c | 0.952 |
C71—H71c | 0.964 | C6'—H6' | 0.985 |
| | | |
C2—O1—C8a | 122.5 (5) | O1—C8a—C8 | 118.4 (5) |
O1—C2—C3 | 118.6 (6) | C4a—C8a—C8 | 120.5 (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—O3 | 119.5 (6) | C2'—C1'—C6' | 118.1 (6) |
C2—C3—C4 | 122.1 (7) | C1'—C2'—C3' | 121.5 (7) |
O3—C3—C4 | 118.4 (6) | C1'—C2'—H2' | 118.0 |
C3—O3—C31 | 113.2 (8) | C3'—C2'—H2' | 120.5 |
O3—C31—H31a | 110.5 | C2'—C3'—O3' | 125.8 (6) |
O3—C31—H31b | 112.1 | C2'—C3'—C4' | 120.2 (7) |
O3—C31—H31c | 110.7 | O3'—C3'—C4' | 114.0 (6) |
H31a—C31—H31b | 108.4 | C3'—O3'—C31' | 117.0 (5) |
H31a—C31—H31c | 106.3 | O3'—C31'—H31'a | 112.7 |
H31b—C31—H31c | 108.7 | O3'—C31'—H31'b | 109.9 |
C3—C4—O4 | 122.2 (7) | O3'—C31'—H31'c | 111.3 |
C3—C4—C4a | 117.5 (6) | H31'a—C31'—H31'b | 107.2 |
O4—C4—C4a | 120.3 (6) | H31'a—C31'—H31'c | 109.6 |
C4—C4a—C5 | 123.5 (6) | H31'b—C31'—H31'c | 105.8 |
C4—C4a—C8a | 118.1 (6) | C3'—C4'—O4' | 120.5 (6) |
C5—C4a—C8a | 118.3 (6) | C3'—C4'—C5' | 118.0 (6) |
C4a—C5—O5 | 119.6 (6) | O4'—C4'—C5' | 121.5 (6) |
C4a—C5—C6 | 121.3 (6) | C4'—O4'—C41' | 113.4 (6) |
O5—C5—C6 | 119.1 (6) | O4'—C41'—H41'a | 109.7 |
C5—O5—H5 | 103.4 | O4'—C41'—H41'b | 109.9 |
C5—C6—C7 | 119.3 (6) | O4'—C41'—H41'c | 110.9 |
C5—C6—H6 | 119.9 | H41'a—C41'—H41'b | 107.7 |
C7—C6—H6 | 120.8 | H41'a—C41'—H41'c | 109.3 |
C6—C7—O7 | 113.6 (6) | H41'b—C41'—H41'c | 109.4 |
C6—C7—C8 | 121.1 (6) | C4'—C5'—O5' | 113.7 (5) |
O7—C7—C8 | 125.4 (6) | C4'—C5'—C6' | 122.7 (6) |
C7—O7—C71 | 116.6 (5) | O5'—C5'—C6' | 123.6 (7) |
O7—C71—H71a | 111.0 | C5'—O5'—C51' | 116.9 (5) |
O7—C71—H71b | 111.4 | O5'—C51'—H51'a | 112.2 |
O7—C71—H71c | 111.2 | O5'—C51'—H51'b | 110.0 |
H71a—C71—H71b | 108.0 | O5'—C51'—H51'c | 111.5 |
H71a—C71—H71c | 107.3 | H51'a—C51'—H51'b | 106.9 |
H71b—C71—H71c | 107.8 | H51'a—C51'—H51'c | 109.6 |
C7—C8—C8a | 119.5 (6) | H51'b—C51'—H51'c | 106.4 |
C7—C8—H8 | 119.5 | C1'—C6'—C5' | 119.4 (7) |
C8a—C8—H8 | 121.0 | C1'—C6'—H6' | 120.1 |
O1—C8a—C4a | 121.1 (6) | C5'—C6'—H6' | 120.4 |
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