organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803027880/lh6146sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803027880/lh61461sup2.hkl |
CCDC reference: 232158
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
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 |