Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101013695/ta1324sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101013695/ta1324Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101013695/ta1324IIsup3.hkl |
CCDC references: 175103; 175104
For related literature, see: Hartley (1981); Higa et al. (1987); Nasim (1999).
Fresh fruit from Melicope ellyrana (1.5 kg) was extracted with n-hexane (4.5 l) for 72 h at room temperature and the extract concentrated by rotary evaporation. The extract (20 g) was subjected to GFC (please give full form of abbreviation) separation using methanol (monitored at λ = 254 nm), the eluent yielding 23 separate fractions. Two of these fractions gave crystals of the title compound in morphologically different and visually identifiable forms; one monoclinic (polymorph A) and the other triclinic (polymorph B).
With the exception of those H atoms involved in hydrogen-bonding interactions, H atoms were included at calculated positions and were constrained in the refinement (C—H = 0.94–0.96 Å).
[Author, there is a C72—H72 distance of 1.10 Å for form A in the CIF. Is this correct or should it be 0.95 Å ?]
For both compounds, data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1999b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON for Windows (Spek, 1999); software used to prepare material for publication: TEXSAN for Windows.
C23H24O8 | F(000) = 904 |
Mr = 428.42 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
a = 14.238 (4) Å | Cell parameters from 25 reflections |
b = 11.053 (5) Å | θ = 20.1–27.2° |
c = 14.426 (5) Å | µ = 0.10 mm−1 |
β = 111.979 (18)° | T = 293 K |
V = 2105.3 (13) Å3 | Prism, yellow |
Z = 4 | 0.40 × 0.30 × 0.30 mm |
Rigaku AFC-7R diffractometer | Rint = 0.026 |
Radiation source: Rigaku rotating anode | θmax = 25.0°, θmin = 2.5° |
Graphite monochromator | h = 0→16 |
ω–2θ scans | k = 0→13 |
3865 measured reflections | l = −17→15 |
3709 independent reflections | 3 standard reflections every 150 reflections |
1532 reflections with I > 2σ(I) | intensity decay: 0.3% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0873P)2 + 0.3178P] where P = (Fo2 + 2Fc2)/3 |
3709 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C23H24O8 | V = 2105.3 (13) Å3 |
Mr = 428.42 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 14.238 (4) Å | µ = 0.10 mm−1 |
b = 11.053 (5) Å | T = 293 K |
c = 14.426 (5) Å | 0.40 × 0.30 × 0.30 mm |
β = 111.979 (18)° |
Rigaku AFC-7R diffractometer | Rint = 0.026 |
3865 measured reflections | 3 standard reflections every 150 reflections |
3709 independent reflections | intensity decay: 0.3% |
1532 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 0.95 | Δρmax = 0.22 e Å−3 |
3709 reflections | Δρmin = −0.27 e Å−3 |
280 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.89228 (17) | 0.3923 (2) | 0.44099 (16) | 0.0475 (6) | |
O3 | 0.65547 (19) | 0.4142 (2) | 0.4787 (2) | 0.0654 (8) | |
O4 | 0.63618 (19) | 0.5967 (2) | 0.34305 (19) | 0.0594 (7) | |
O5 | 0.7059 (2) | 0.7113 (3) | 0.2249 (2) | 0.0714 (8) | |
O7 | 1.02792 (19) | 0.5804 (2) | 0.22994 (18) | 0.0616 (7) | |
O8 | 1.04877 (19) | 0.4269 (2) | 0.38221 (19) | 0.0624 (8) | |
O42 | 0.9373 (2) | −0.0175 (3) | 0.7492 (2) | 0.0760 (9) | |
O52 | 1.0576 (2) | 0.0509 (3) | 0.6524 (2) | 0.0752 (9) | |
C2 | 0.8175 (3) | 0.3697 (3) | 0.4759 (3) | 0.0477 (9) | |
C3 | 0.7317 (3) | 0.4379 (3) | 0.4447 (3) | 0.0495 (9) | |
C4A | 0.7954 (3) | 0.5524 (3) | 0.3357 (3) | 0.0489 (9) | |
C4 | 0.7154 (3) | 0.5336 (3) | 0.3729 (3) | 0.0484 (9) | |
C5 | 0.7887 (3) | 0.6385 (4) | 0.2618 (3) | 0.0536 (10) | |
C6 | 0.8642 (3) | 0.6486 (4) | 0.2244 (3) | 0.0554 (10) | |
C7 | 0.9503 (3) | 0.5759 (3) | 0.2630 (3) | 0.0519 (10) | |
C8 | 0.9599 (3) | 0.4918 (3) | 0.3375 (3) | 0.0468 (9) | |
C8A | 0.8814 (3) | 0.4793 (3) | 0.3710 (2) | 0.0444 (9) | |
C12 | 0.8455 (3) | 0.2667 (3) | 0.5461 (3) | 0.0469 (9) | |
C22 | 0.7850 (3) | 0.2239 (4) | 0.5956 (3) | 0.0625 (11) | |
C31 | 0.6522 (4) | 0.4982 (5) | 0.5538 (4) | 0.1048 (19) | |
C32 | 0.8165 (3) | 0.1295 (4) | 0.6624 (3) | 0.0679 (12) | |
C42 | 0.9089 (3) | 0.0741 (4) | 0.6817 (3) | 0.0569 (10) | |
C52 | 0.9685 (3) | 0.1134 (4) | 0.6302 (3) | 0.0520 (10) | |
C62 | 0.9375 (3) | 0.2080 (3) | 0.5650 (3) | 0.0509 (9) | |
C71 | 1.0187 (3) | 0.6635 (4) | 0.1501 (3) | 0.0693 (12) | |
C72 | 1.1069 (3) | 0.6438 (4) | 0.1204 (3) | 0.0686 (12) | |
C73 | 1.1036 (3) | 0.6505 (4) | 0.0282 (3) | 0.0666 (12) | |
C81 | 1.0535 (4) | 0.3132 (5) | 0.3396 (4) | 0.0952 (16) | |
C521 | 1.1204 (3) | 0.0803 (4) | 0.5997 (3) | 0.0686 (12) | |
C731 | 1.1957 (4) | 0.6311 (5) | 0.0036 (4) | 0.0990 (17) | |
C732 | 1.0096 (4) | 0.6792 (5) | −0.0598 (3) | 0.0966 (17) | |
H5 | 0.6594 | 0.6862 | 0.2617 | 0.050* | |
H6 | 0.8579 | 0.7052 | 0.1726 | 0.065* | |
H22 | 0.7210 | 0.2600 | 0.5832 | 0.074* | |
H32 | 0.7746 | 0.1024 | 0.6960 | 0.081* | |
H42 | 1.0031 | −0.0544 | 0.7624 | 0.095* | |
H62 | 0.9800 | 0.2343 | 0.5313 | 0.061* | |
H72 | 1.1810 | 0.6280 | 0.1803 | 0.067* | |
H311 | 0.7099 | 0.4858 | 0.6140 | 0.126* | |
H312 | 0.6531 | 0.5788 | 0.5315 | 0.126* | |
H313 | 0.5924 | 0.4853 | 0.5670 | 0.126* | |
H521 | 1.1882 | 0.0574 | 0.6384 | 0.083* | |
H522 | 1.0978 | 0.0386 | 0.5378 | 0.083* | |
H523 | 1.1176 | 0.1651 | 0.5880 | 0.083* | |
H711 | 0.9572 | 0.6473 | 0.0941 | 0.082* | |
H712 | 1.0177 | 0.7441 | 0.1711 | 0.082* | |
H731 | 1.2529 | 0.6182 | 0.0635 | 0.120* | |
H732 | 1.1860 | 0.5628 | −0.0388 | 0.120* | |
H733 | 1.2070 | 0.7009 | −0.0295 | 0.120* | |
H734 | 0.9559 | 0.6968 | −0.0379 | 0.116* | |
H735 | 1.0215 | 0.7470 | −0.0942 | 0.116* | |
H736 | 0.9913 | 0.6114 | −0.1037 | 0.116* | |
H811 | 0.9887 | 0.2748 | 0.3194 | 0.114* | |
H812 | 1.0701 | 0.3244 | 0.2819 | 0.114* | |
H813 | 1.1027 | 0.2640 | 0.3863 | 0.114* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0472 (14) | 0.0515 (15) | 0.0442 (14) | 0.0005 (12) | 0.0176 (12) | 0.0019 (12) |
O3 | 0.0568 (17) | 0.0674 (19) | 0.079 (2) | 0.0027 (14) | 0.0330 (16) | 0.0053 (16) |
O4 | 0.0522 (16) | 0.0613 (18) | 0.0632 (17) | 0.0122 (14) | 0.0198 (13) | −0.0006 (14) |
O5 | 0.0658 (18) | 0.073 (2) | 0.076 (2) | 0.0184 (16) | 0.0272 (15) | 0.0218 (16) |
O7 | 0.0651 (17) | 0.0697 (19) | 0.0549 (16) | 0.0028 (14) | 0.0283 (14) | 0.0099 (14) |
O8 | 0.0576 (17) | 0.0646 (19) | 0.0631 (17) | 0.0017 (14) | 0.0203 (14) | 0.0002 (15) |
O42 | 0.0738 (19) | 0.080 (2) | 0.086 (2) | 0.0101 (16) | 0.0432 (17) | 0.0337 (18) |
O52 | 0.0747 (19) | 0.086 (2) | 0.082 (2) | 0.0232 (17) | 0.0489 (17) | 0.0338 (17) |
C2 | 0.050 (2) | 0.049 (2) | 0.044 (2) | −0.0103 (19) | 0.0175 (18) | −0.0087 (18) |
C3 | 0.047 (2) | 0.052 (2) | 0.052 (2) | −0.0048 (19) | 0.0209 (19) | −0.0040 (19) |
C4A | 0.052 (2) | 0.047 (2) | 0.044 (2) | −0.0002 (19) | 0.0127 (18) | −0.0074 (18) |
C4 | 0.048 (2) | 0.048 (2) | 0.042 (2) | 0.0025 (19) | 0.0094 (18) | −0.0100 (18) |
C5 | 0.055 (2) | 0.051 (2) | 0.049 (2) | 0.005 (2) | 0.012 (2) | −0.002 (2) |
C6 | 0.060 (3) | 0.056 (3) | 0.046 (2) | 0.003 (2) | 0.016 (2) | 0.006 (2) |
C7 | 0.056 (2) | 0.055 (2) | 0.044 (2) | −0.006 (2) | 0.0170 (19) | −0.0034 (19) |
C8 | 0.047 (2) | 0.045 (2) | 0.043 (2) | 0.0048 (18) | 0.0107 (18) | −0.0021 (18) |
C8A | 0.048 (2) | 0.045 (2) | 0.037 (2) | −0.0020 (17) | 0.0128 (18) | −0.0027 (17) |
C12 | 0.050 (2) | 0.047 (2) | 0.046 (2) | −0.0045 (18) | 0.0196 (18) | −0.0044 (18) |
C22 | 0.051 (2) | 0.067 (3) | 0.072 (3) | 0.002 (2) | 0.026 (2) | 0.012 (2) |
C31 | 0.144 (5) | 0.091 (4) | 0.119 (4) | 0.020 (3) | 0.095 (4) | 0.001 (3) |
C32 | 0.059 (3) | 0.076 (3) | 0.079 (3) | −0.001 (2) | 0.037 (2) | 0.017 (3) |
C42 | 0.056 (3) | 0.061 (3) | 0.054 (2) | −0.005 (2) | 0.022 (2) | 0.015 (2) |
C52 | 0.055 (2) | 0.054 (2) | 0.050 (2) | 0.0052 (19) | 0.024 (2) | 0.006 (2) |
C62 | 0.057 (2) | 0.051 (2) | 0.051 (2) | 0.0008 (19) | 0.0272 (19) | 0.0051 (19) |
C71 | 0.082 (3) | 0.069 (3) | 0.064 (3) | −0.002 (2) | 0.036 (2) | 0.010 (2) |
C72 | 0.068 (3) | 0.075 (3) | 0.071 (3) | −0.001 (2) | 0.035 (2) | 0.016 (2) |
C73 | 0.084 (3) | 0.052 (3) | 0.078 (3) | −0.005 (2) | 0.047 (3) | 0.003 (2) |
C81 | 0.099 (4) | 0.082 (4) | 0.090 (4) | 0.030 (3) | 0.018 (3) | −0.009 (3) |
C521 | 0.069 (3) | 0.079 (3) | 0.069 (3) | 0.021 (2) | 0.038 (2) | 0.018 (2) |
C731 | 0.109 (4) | 0.092 (4) | 0.126 (4) | 0.008 (3) | 0.077 (4) | 0.018 (3) |
C732 | 0.103 (4) | 0.131 (5) | 0.065 (3) | −0.013 (3) | 0.041 (3) | −0.001 (3) |
O1—C8A | 1.360 (4) | C22—H22 | 0.95 |
O1—C2 | 1.361 (4) | C31—H311 | 0.96 |
O3—C3 | 1.373 (4) | C31—H312 | 0.95 |
O3—C31 | 1.441 (5) | C31—H313 | 0.95 |
O4—C4 | 1.257 (4) | C32—C42 | 1.381 (5) |
O5—C5 | 1.361 (4) | C32—H32 | 0.95 |
O5—H5 | 1.03 | C42—C52 | 1.389 (5) |
O7—C7 | 1.359 (4) | C52—C62 | 1.365 (5) |
O7—C71 | 1.441 (5) | C62—H62 | 0.95 |
O8—C8 | 1.387 (4) | C71—C72 | 1.486 (6) |
O8—C81 | 1.411 (5) | C71—H711 | 0.96 |
O42—C42 | 1.358 (4) | C71—H712 | 0.94 |
O42—H42 | 0.97 | C72—C73 | 1.315 (5) |
O52—C52 | 1.373 (4) | C72—H72 | 1.10 |
O52—C521 | 1.412 (4) | C73—C732 | 1.493 (6) |
C2—C3 | 1.360 (5) | C73—C731 | 1.496 (6) |
C2—C12 | 1.476 (5) | C81—H811 | 0.96 |
C3—C4 | 1.438 (5) | C81—H812 | 0.96 |
C4A—C8A | 1.394 (5) | C81—H813 | 0.94 |
C4A—C5 | 1.406 (5) | C521—H522 | 0.95 |
C4A—C4 | 1.444 (5) | C521—H523 | 0.95 |
C5—C6 | 1.374 (5) | C521—H521 | 0.95 |
C6—C7 | 1.396 (5) | C731—H731 | 0.95 |
C6—H6 | 0.95 | C731—H732 | 0.95 |
C7—C8 | 1.389 (5) | C731—H733 | 0.95 |
C8—C8A | 1.381 (5) | C732—H734 | 0.95 |
C12—C22 | 1.391 (5) | C732—H735 | 0.95 |
C12—C62 | 1.394 (5) | C732—H736 | 0.95 |
C22—C32 | 1.376 (6) | ||
C8A—O1—C2 | 121.1 (3) | C22—C32—H32 | 120 |
C3—O3—C31 | 113.5 (3) | C42—C32—H32 | 119 |
C5—O5—H5 | 106 | O42—C42—C32 | 118.7 (3) |
C7—O7—C71 | 117.5 (3) | O42—C42—C52 | 122.6 (4) |
C8—O8—C81 | 116.3 (3) | C32—C42—C52 | 118.7 (4) |
C42—O42—H42 | 117 | C62—C52—O52 | 125.3 (3) |
C52—O52—C521 | 118.4 (3) | C62—C52—C42 | 120.2 (3) |
C3—C2—O1 | 120.4 (3) | O52—C52—C42 | 114.5 (3) |
C3—C2—C12 | 129.3 (3) | C52—C62—C12 | 122.0 (3) |
O1—C2—C12 | 110.4 (3) | C52—C62—H62 | 119 |
C2—C3—O3 | 120.5 (3) | C12—C62—H62 | 119 |
C2—C3—C4 | 122.0 (3) | O7—C71—C72 | 107.6 (3) |
O3—C3—C4 | 117.5 (3) | O7—C71—H711 | 110 |
C8A—C4A—C5 | 118.1 (3) | C72—C71—H711 | 109 |
C8A—C4A—C4 | 119.2 (3) | O7—C71—H712 | 111 |
C5—C4A—C4 | 122.7 (3) | C72—C71—H712 | 110 |
O4—C4—C3 | 122.5 (3) | H711—C71—H712 | 109 |
O4—C4—C4A | 121.6 (3) | C73—C72—C71 | 124.7 (4) |
C3—C4—C4A | 115.9 (3) | C73—C72—H72 | 118 |
O5—C5—C6 | 119.3 (3) | C71—C72—H72 | 118 |
O5—C5—C4A | 119.9 (3) | C72—C73—C732 | 123.5 (4) |
C6—C5—C4A | 120.8 (4) | C72—C73—C731 | 121.9 (4) |
C5—C6—C7 | 119.7 (4) | C732—C73—C731 | 114.5 (4) |
C5—C6—H6 | 120 | O8—C81—H811 | 109 |
C7—C6—H6 | 120 | O8—C81—H812 | 109 |
O7—C7—C8 | 116.0 (3) | H811—C81—H812 | 109 |
O7—C7—C6 | 123.2 (3) | O8—C81—H813 | 110 |
C8—C7—C6 | 120.7 (3) | H811—C81—H813 | 110 |
C8A—C8—O8 | 120.2 (3) | H812—C81—H813 | 110 |
C8A—C8—C7 | 118.7 (3) | O52—C521—H522 | 110 |
O8—C8—C7 | 121.0 (3) | O52—C521—H523 | 109 |
O1—C8A—C8 | 116.6 (3) | H522—C521—H523 | 110 |
O1—C8A—C4A | 121.5 (3) | O52—C521—H521 | 109 |
C8—C8A—C4A | 121.9 (3) | H522—C521—H521 | 110 |
C22—C12—C62 | 117.2 (3) | H523—C521—H521 | 109 |
C22—C12—C2 | 123.7 (3) | C73—C731—H731 | 110 |
C62—C12—C2 | 119.1 (3) | C73—C731—H732 | 110 |
C32—C22—C12 | 121.0 (4) | H731—C731—H732 | 110 |
C32—C22—H22 | 119 | C73—C731—H733 | 109 |
C12—C22—H22 | 120 | H731—C731—H733 | 109 |
O3—C31—H311 | 109 | H732—C731—H733 | 109 |
O3—C31—H312 | 110 | C73—C732—H734 | 110 |
H311—C31—H312 | 109 | C73—C732—H735 | 110 |
O3—C31—H313 | 110 | H734—C732—H735 | 110 |
H311—C31—H313 | 109 | C73—C732—H736 | 110 |
H312—C31—H313 | 110 | H734—C732—H736 | 109 |
C22—C32—C42 | 120.9 (4) | H735—C732—H736 | 109 |
C8A—O1—C2—C3 | −3.0 (5) | C2—O1—C8A—C4A | 3.0 (5) |
C8A—O1—C2—C12 | 176.5 (3) | O8—C8—C8A—O1 | −6.8 (5) |
O1—C2—C3—O3 | 179.1 (3) | C7—C8—C8A—O1 | 177.3 (3) |
C12—C2—C3—O3 | −0.4 (6) | O8—C8—C8A—C4A | 172.9 (3) |
O1—C2—C3—C4 | 1.4 (5) | C7—C8—C8A—C4A | −3.1 (5) |
C12—C2—C3—C4 | −178.0 (3) | C5—C4A—C8A—O1 | −178.6 (3) |
C31—O3—C3—C2 | 103.4 (4) | C4—C4A—C8A—O1 | −1.2 (5) |
C31—O3—C3—C4 | −78.8 (4) | C5—C4A—C8A—C8 | 1.8 (5) |
C2—C3—C4—O4 | 179.6 (3) | C4—C4A—C8A—C8 | 179.2 (3) |
O3—C3—C4—O4 | 1.8 (5) | C3—C2—C12—C22 | −1.9 (6) |
C2—C3—C4—C4A | 0.2 (5) | O1—C2—C12—C22 | 178.6 (3) |
O3—C3—C4—C4A | −177.5 (3) | C3—C2—C12—C62 | 178.3 (4) |
C8A—C4A—C4—O4 | −179.7 (3) | O1—C2—C12—C62 | −1.2 (4) |
C5—C4A—C4—O4 | −2.4 (5) | C62—C12—C22—C32 | 1.7 (6) |
C8A—C4A—C4—C3 | −0.3 (5) | C2—C12—C22—C32 | −178.1 (4) |
C5—C4A—C4—C3 | 176.9 (3) | C12—C22—C32—C42 | −0.4 (7) |
C8A—C4A—C5—O5 | 179.7 (3) | C22—C32—C42—O42 | 179.1 (4) |
C4—C4A—C5—O5 | 2.4 (5) | C22—C32—C42—C52 | −1.7 (6) |
C8A—C4A—C5—C6 | 1.1 (5) | C521—O52—C52—C62 | −4.2 (6) |
C4—C4A—C5—C6 | −176.2 (3) | C521—O52—C52—C42 | 176.7 (4) |
O5—C5—C6—C7 | 178.9 (3) | O42—C42—C52—C62 | −178.3 (4) |
C4A—C5—C6—C7 | −2.5 (6) | C32—C42—C52—C62 | 2.6 (6) |
C71—O7—C7—C8 | 177.8 (3) | O42—C42—C52—O52 | 0.8 (6) |
C71—O7—C7—C6 | −1.1 (5) | C32—C42—C52—O52 | −178.3 (4) |
C5—C6—C7—O7 | 179.9 (3) | O52—C52—C62—C12 | 179.7 (4) |
C5—C6—C7—C8 | 1.1 (6) | C42—C52—C62—C12 | −1.2 (6) |
C81—O8—C8—C8A | 91.3 (4) | C22—C12—C62—C52 | −0.9 (6) |
C81—O8—C8—C7 | −92.8 (4) | C2—C12—C62—C52 | 179.0 (4) |
O7—C7—C8—C8A | −177.2 (3) | C7—O7—C71—C72 | −174.6 (3) |
C6—C7—C8—C8A | 1.7 (5) | O7—C71—C72—C73 | 143.5 (4) |
O7—C7—C8—O8 | 6.8 (5) | C71—C72—C73—C732 | 0.0 (7) |
C6—C7—C8—O8 | −174.3 (3) | C71—C72—C73—C731 | 179.3 (4) |
C2—O1—C8A—C8 | −177.4 (3) |
C23H24O8 | Z = 2 |
Mr = 428.44 | F(000) = 452 |
Triclinic, P1 | Dx = 1.405 Mg m−3 |
a = 12.291 (5) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 13.075 (5) Å | Cell parameters from 17 reflections |
c = 7.099 (3) Å | θ = 20.1–25.6° |
α = 93.85 (5)° | µ = 0.11 mm−1 |
β = 104.33 (4)° | T = 293 K |
γ = 111.52 (3)° | Prism, yellow |
V = 1012.3 (7) Å3 | 0.45 × 0.10 × 0.10 mm |
Rigaku AFC-7R diffractometer | Rint = 0.097 |
Radiation source: Rigaku rotating anode | θmax = 25.0°, θmin = 3.0° |
Graphite monochromator | h = 0→14 |
ω–2θ scans | k = −15→14 |
3754 measured reflections | l = −8→8 |
3571 independent reflections | 3 standard reflections every 150 reflections |
1609 reflections with I > 2σ(I) | intensity decay: 3.5% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
3571 reflections | (Δ/σ)max < 0.001 |
280 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
C23H24O8 | γ = 111.52 (3)° |
Mr = 428.44 | V = 1012.3 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 12.291 (5) Å | Mo Kα radiation |
b = 13.075 (5) Å | µ = 0.11 mm−1 |
c = 7.099 (3) Å | T = 293 K |
α = 93.85 (5)° | 0.45 × 0.10 × 0.10 mm |
β = 104.33 (4)° |
Rigaku AFC-7R diffractometer | Rint = 0.097 |
3754 measured reflections | 3 standard reflections every 150 reflections |
3571 independent reflections | intensity decay: 3.5% |
1609 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.199 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.32 e Å−3 |
3571 reflections | Δρmin = −0.28 e Å−3 |
280 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.4223 (2) | 0.03091 (19) | 0.7148 (4) | 0.0405 (7) | |
O3 | 0.7498 (2) | 0.1101 (2) | 0.9082 (4) | 0.0460 (7) | |
O4 | 0.7320 (2) | 0.3132 (2) | 0.9353 (4) | 0.0531 (8) | |
O5 | 0.6002 (2) | 0.4297 (2) | 0.9128 (5) | 0.0577 (8) | |
O7 | 0.1660 (2) | 0.2245 (2) | 0.6717 (4) | 0.0467 (7) | |
O8 | 0.1964 (2) | 0.0345 (2) | 0.5843 (4) | 0.0483 (7) | |
O42 | 0.4692 (3) | −0.4288 (2) | 0.6347 (5) | 0.0616 (9) | |
O52 | 0.6955 (3) | −0.2726 (2) | 0.7537 (5) | 0.0559 (8) | |
C2 | 0.5336 (3) | 0.0236 (3) | 0.7676 (5) | 0.0371 (9) | |
C3 | 0.6379 (3) | 0.1166 (3) | 0.8400 (5) | 0.0346 (9) | |
C4 | 0.6353 (4) | 0.2267 (3) | 0.8677 (5) | 0.0382 (9) | |
C4A | 0.5172 (3) | 0.2307 (3) | 0.8167 (5) | 0.0361 (9) | |
C5 | 0.4999 (4) | 0.3315 (3) | 0.8430 (6) | 0.0410 (10) | |
C6 | 0.3852 (4) | 0.3316 (3) | 0.7983 (6) | 0.0424 (10) | |
C7 | 0.2830 (3) | 0.2322 (3) | 0.7211 (5) | 0.0384 (9) | |
C8 | 0.2965 (3) | 0.1307 (3) | 0.6872 (5) | 0.0369 (9) | |
C8A | 0.4119 (3) | 0.1318 (3) | 0.7402 (5) | 0.0350 (9) | |
C12 | 0.5197 (3) | −0.0950 (3) | 0.7339 (5) | 0.0353 (9) | |
C22 | 0.4030 (3) | −0.1796 (3) | 0.6737 (6) | 0.0424 (10) | |
C31 | 0.8331 (4) | 0.1554 (4) | 0.7951 (7) | 0.0624 (13) | |
C32 | 0.3868 (4) | −0.2908 (3) | 0.6400 (6) | 0.0499 (11) | |
C42 | 0.4867 (4) | −0.3177 (3) | 0.6693 (6) | 0.0424 (10) | |
C52 | 0.6040 (4) | −0.2347 (3) | 0.7301 (6) | 0.0420 (10) | |
C62 | 0.6202 (3) | −0.1242 (3) | 0.7626 (5) | 0.0396 (9) | |
C71 | 0.1444 (4) | 0.3265 (3) | 0.6974 (6) | 0.0497 (11) | |
C72 | 0.1579 (4) | 0.3862 (3) | 0.5292 (7) | 0.0504 (11) | |
C73 | 0.0691 (4) | 0.3937 (3) | 0.3880 (6) | 0.0501 (11) | |
C81 | 0.1175 (4) | −0.0233 (4) | 0.6933 (7) | 0.0676 (13) | |
C521 | 0.8180 (4) | −0.1927 (4) | 0.8194 (6) | 0.0570 (12) | |
C731 | −0.0636 (5) | 0.3422 (4) | 0.3712 (8) | 0.0762 (15) | |
C732 | 0.0984 (5) | 0.4556 (4) | 0.2252 (9) | 0.0855 (17) | |
H5 | 0.6798 | 0.4180 | 0.9669 | 0.074* | |
H6 | 0.3753 | 0.3997 | 0.8201 | 0.051* | |
H22 | 0.3345 | −0.1597 | 0.6543 | 0.074* | |
H32 | 0.3066 | −0.3482 | 0.5970 | 0.060* | |
H42 | 0.5612 | −0.4226 | 0.6715 | 0.074* | |
H62 | 0.7001 | −0.0660 | 0.8039 | 0.074* | |
H72 | 0.2389 | 0.4232 | 0.5219 | 0.060* | |
H311 | 0.8065 | 0.1069 | 0.6721 | 0.075* | |
H312 | 0.8352 | 0.2268 | 0.7721 | 0.075* | |
H313 | 0.9127 | 0.1625 | 0.8660 | 0.075* | |
H521 | 0.8320 | −0.1507 | 0.9438 | 0.069* | |
H522 | 0.8319 | −0.1441 | 0.7264 | 0.069* | |
H523 | 0.8722 | −0.2300 | 0.8322 | 0.069* | |
H711 | 0.0638 | 0.3076 | 0.7069 | 0.060* | |
H712 | 0.2018 | 0.3740 | 0.8155 | 0.060* | |
H731 | −0.0774 | 0.3711 | 0.4854 | 0.092* | |
H732 | −0.1089 | 0.3589 | 0.2574 | 0.092* | |
H733 | −0.0894 | 0.2634 | 0.3605 | 0.092* | |
H734 | 0.1521 | 0.5311 | 0.2795 | 0.102* | |
H735 | 0.1365 | 0.4217 | 0.1551 | 0.102* | |
H736 | 0.0250 | 0.4535 | 0.1374 | 0.102* | |
H811 | 0.0568 | −0.0910 | 0.6129 | 0.081* | |
H812 | 0.0791 | 0.0220 | 0.7334 | 0.081* | |
H813 | 0.1637 | −0.0397 | 0.8068 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0455 (16) | 0.0295 (14) | 0.0486 (17) | 0.0178 (12) | 0.0134 (13) | 0.0045 (11) |
O3 | 0.0405 (17) | 0.0400 (15) | 0.0576 (18) | 0.0171 (13) | 0.0129 (14) | 0.0083 (13) |
O4 | 0.0471 (18) | 0.0360 (16) | 0.070 (2) | 0.0123 (14) | 0.0148 (15) | 0.0026 (14) |
O5 | 0.0502 (18) | 0.0312 (15) | 0.085 (2) | 0.0139 (14) | 0.0147 (16) | 0.0004 (14) |
O7 | 0.0493 (18) | 0.0366 (15) | 0.0578 (18) | 0.0232 (13) | 0.0123 (14) | 0.0078 (13) |
O8 | 0.0484 (17) | 0.0378 (15) | 0.0549 (19) | 0.0151 (14) | 0.0135 (14) | 0.0008 (13) |
O42 | 0.0596 (19) | 0.0307 (15) | 0.100 (2) | 0.0220 (14) | 0.0271 (17) | 0.0084 (15) |
O52 | 0.0527 (19) | 0.0421 (16) | 0.085 (2) | 0.0285 (15) | 0.0265 (16) | 0.0091 (15) |
C2 | 0.045 (2) | 0.037 (2) | 0.035 (2) | 0.022 (2) | 0.0130 (18) | 0.0085 (17) |
C3 | 0.037 (2) | 0.035 (2) | 0.032 (2) | 0.0155 (19) | 0.0095 (17) | 0.0051 (17) |
C4 | 0.050 (2) | 0.033 (2) | 0.033 (2) | 0.016 (2) | 0.0149 (18) | 0.0083 (17) |
C4A | 0.041 (2) | 0.031 (2) | 0.040 (2) | 0.0145 (18) | 0.0165 (18) | 0.0092 (17) |
C5 | 0.046 (3) | 0.032 (2) | 0.041 (2) | 0.0120 (19) | 0.0116 (19) | 0.0056 (17) |
C6 | 0.054 (3) | 0.029 (2) | 0.046 (2) | 0.021 (2) | 0.015 (2) | 0.0046 (18) |
C7 | 0.043 (2) | 0.038 (2) | 0.038 (2) | 0.0206 (19) | 0.0100 (18) | 0.0097 (17) |
C8 | 0.046 (2) | 0.027 (2) | 0.036 (2) | 0.0131 (18) | 0.0114 (18) | 0.0042 (16) |
C8A | 0.049 (2) | 0.029 (2) | 0.034 (2) | 0.0203 (19) | 0.0164 (18) | 0.0061 (16) |
C12 | 0.044 (2) | 0.033 (2) | 0.034 (2) | 0.0171 (18) | 0.0170 (18) | 0.0115 (16) |
C22 | 0.044 (2) | 0.038 (2) | 0.049 (3) | 0.021 (2) | 0.0109 (19) | 0.0088 (18) |
C31 | 0.051 (3) | 0.059 (3) | 0.084 (4) | 0.022 (2) | 0.032 (3) | 0.010 (3) |
C32 | 0.047 (3) | 0.036 (2) | 0.066 (3) | 0.015 (2) | 0.017 (2) | 0.009 (2) |
C42 | 0.053 (3) | 0.029 (2) | 0.051 (3) | 0.020 (2) | 0.017 (2) | 0.0087 (18) |
C52 | 0.048 (2) | 0.042 (2) | 0.047 (2) | 0.025 (2) | 0.020 (2) | 0.0127 (19) |
C62 | 0.040 (2) | 0.038 (2) | 0.043 (2) | 0.0159 (18) | 0.0160 (18) | 0.0092 (18) |
C71 | 0.056 (3) | 0.045 (2) | 0.064 (3) | 0.034 (2) | 0.023 (2) | 0.011 (2) |
C72 | 0.048 (3) | 0.042 (2) | 0.068 (3) | 0.021 (2) | 0.023 (2) | 0.012 (2) |
C73 | 0.056 (3) | 0.038 (2) | 0.058 (3) | 0.024 (2) | 0.012 (2) | 0.005 (2) |
C81 | 0.066 (3) | 0.049 (3) | 0.074 (3) | 0.009 (2) | 0.019 (3) | 0.011 (2) |
C521 | 0.058 (3) | 0.066 (3) | 0.060 (3) | 0.038 (3) | 0.020 (2) | 0.007 (2) |
C731 | 0.067 (3) | 0.079 (4) | 0.076 (4) | 0.036 (3) | 0.001 (3) | 0.007 (3) |
C732 | 0.114 (5) | 0.068 (4) | 0.085 (4) | 0.044 (3) | 0.032 (3) | 0.030 (3) |
O1—C2 | 1.367 (4) | C22—H22 | 0.95 |
O1—C8A | 1.376 (4) | C31—H311 | 0.95 |
O3—C3 | 1.377 (4) | C31—H312 | 0.95 |
O3—C31 | 1.439 (5) | C31—H313 | 0.95 |
O4—C4 | 1.257 (4) | C32—C42 | 1.369 (5) |
O5—C5 | 1.366 (4) | C32—H32 | 0.95 |
O5—H5 | 1.03 | C42—C52 | 1.388 (5) |
O7—C7 | 1.358 (4) | C52—C62 | 1.378 (5) |
O7—C71 | 1.460 (4) | C62—H62 | 0.95 |
O8—C8 | 1.388 (4) | C71—C72 | 1.480 (6) |
O8—C81 | 1.422 (5) | C71—H711 | 0.95 |
O42—C42 | 1.383 (4) | C71—H712 | 0.95 |
O42—H42 | 1.07 | C72—C73 | 1.325 (5) |
O52—C52 | 1.366 (5) | C72—H72 | 0.95 |
O52—C521 | 1.417 (5) | C73—C731 | 1.489 (7) |
C2—C3 | 1.354 (5) | C73—C732 | 1.496 (6) |
C2—C12 | 1.492 (5) | C81—H811 | 0.95 |
C3—C4 | 1.452 (5) | C81—H812 | 0.95 |
C4—C4A | 1.429 (5) | C81—H813 | 0.95 |
C4A—C8A | 1.404 (5) | C521—H521 | 0.95 |
C4A—C5 | 1.418 (5) | C521—H522 | 0.95 |
C5—C6 | 1.367 (5) | C521—H523 | 0.95 |
C6—C7 | 1.390 (5) | C731—H731 | 0.95 |
C6—H6 | 0.95 | C731—H732 | 0.95 |
C7—C8 | 1.408 (5) | C731—H733 | 0.95 |
C8—C8A | 1.369 (5) | C732—H734 | 0.95 |
C12—C22 | 1.390 (5) | C732—H735 | 0.95 |
C12—C62 | 1.396 (5) | C732—H736 | 0.95 |
C22—C32 | 1.389 (5) | ||
C2—O1—C8A | 121.5 (3) | C42—C32—H32 | 120 |
C3—O3—C31 | 114.7 (3) | C22—C32—H32 | 120 |
C5—O5—H5 | 113 | C32—C42—O42 | 119.2 (4) |
C7—O7—C71 | 118.7 (3) | C32—C42—C52 | 120.5 (3) |
C8—O8—C81 | 116.5 (3) | O42—C42—C52 | 120.3 (3) |
C42—O42—H42 | 102 | O52—C52—C62 | 125.6 (4) |
C52—O52—C521 | 118.0 (3) | O52—C52—C42 | 114.7 (3) |
C3—C2—O1 | 120.7 (3) | C62—C52—C42 | 119.8 (4) |
C3—C2—C12 | 128.3 (3) | C52—C62—C12 | 120.7 (4) |
O1—C2—C12 | 111.0 (3) | C52—C62—H62 | 121 |
C2—C3—O3 | 121.3 (3) | C12—C62—H62 | 118 |
C2—C3—C4 | 121.4 (3) | O7—C71—C72 | 111.3 (3) |
O3—C3—C4 | 117.0 (3) | O7—C71—H711 | 109 |
O4—C4—C4A | 122.1 (3) | C72—C71—H711 | 109 |
O4—C4—C3 | 121.6 (4) | O7—C71—H712 | 109 |
C4A—C4—C3 | 116.3 (3) | C72—C71—H712 | 109 |
C8A—C4A—C5 | 117.2 (3) | H711—C71—H712 | 109 |
C8A—C4A—C4 | 120.0 (3) | C73—C72—C71 | 127.0 (4) |
C5—C4A—C4 | 122.8 (3) | C73—C72—H72 | 117 |
O5—C5—C6 | 120.0 (3) | C71—C72—H72 | 117 |
O5—C5—C4A | 118.9 (3) | C72—C73—C731 | 125.3 (4) |
C6—C5—C4A | 121.1 (3) | C72—C73—C732 | 120.2 (4) |
C5—C6—C7 | 120.1 (3) | C731—C73—C732 | 114.5 (4) |
C5—C6—H6 | 120 | O8—C81—H811 | 110 |
C7—C6—H6 | 120 | O8—C81—H812 | 110 |
O7—C7—C6 | 124.1 (3) | H811—C81—H812 | 109 |
O7—C7—C8 | 115.4 (3) | O8—C81—H813 | 110 |
C6—C7—C8 | 120.5 (4) | H811—C81—H813 | 109 |
C8A—C8—O8 | 120.8 (3) | H812—C81—H813 | 109 |
C8A—C8—C7 | 118.4 (3) | O52—C521—H521 | 109 |
O8—C8—C7 | 120.4 (3) | O52—C521—H522 | 110 |
C8—C8A—O1 | 117.4 (3) | H521—C521—H522 | 110 |
C8—C8A—C4A | 122.5 (3) | O52—C521—H523 | 109 |
O1—C8A—C4A | 120.1 (3) | H521—C521—H523 | 110 |
C22—C12—C62 | 118.6 (3) | H522—C521—H523 | 110 |
C22—C12—C2 | 119.3 (3) | C73—C731—H731 | 110 |
C62—C12—C2 | 122.1 (3) | C73—C731—H732 | 110 |
C32—C22—C12 | 120.7 (4) | H731—C731—H732 | 109 |
C32—C22—H22 | 121 | C73—C731—H733 | 110 |
C12—C22—H22 | 119 | H731—C731—H733 | 109 |
O3—C31—H311 | 110 | H732—C731—H733 | 109 |
O3—C31—H312 | 110 | C73—C732—H734 | 110 |
H311—C31—H312 | 109 | C73—C732—H735 | 110 |
O3—C31—H313 | 110 | H734—C732—H735 | 110 |
H311—C31—H313 | 109 | C73—C732—H736 | 109 |
H312—C31—H313 | 110 | H734—C732—H736 | 109 |
C42—C32—C22 | 119.8 (4) | H735—C732—H736 | 110 |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C23H24O8 | C23H24O8 |
Mr | 428.42 | 428.44 |
Crystal system, space group | Monoclinic, P21/n | Triclinic, P1 |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 14.238 (4), 11.053 (5), 14.426 (5) | 12.291 (5), 13.075 (5), 7.099 (3) |
α, β, γ (°) | 90, 111.979 (18), 90 | 93.85 (5), 104.33 (4), 111.52 (3) |
V (Å3) | 2105.3 (13) | 1012.3 (7) |
Z | 4 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 0.11 |
Crystal size (mm) | 0.40 × 0.30 × 0.30 | 0.45 × 0.10 × 0.10 |
Data collection | ||
Diffractometer | Rigaku AFC-7R diffractometer | Rigaku AFC-7R diffractometer |
Absorption correction | – | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3865, 3709, 1532 | 3754, 3571, 1609 |
Rint | 0.026 | 0.097 |
(sin θ/λ)max (Å−1) | 0.595 | 0.595 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.180, 0.95 | 0.055, 0.199, 1.00 |
No. of reflections | 3709 | 3571 |
No. of parameters | 280 | 280 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.27 | 0.32, −0.28 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a), MSC/AFC Diffractometer Control Software, TEXSAN for Windows (Molecular Structure Corporation, 1999b), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON for Windows (Spek, 1999), TEXSAN for Windows.
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Investigation of the hexane extract of the fruit of the indigenous Australian tree Melicope ellyrana (formerly Euodia ellyrana F. Meull) (Hartley, 1981) resulted in the isolation of three flavonoids, namely 4',5-dihydroxy-3,3',8-trimethoxy-7-(3-methylbut-2-enyloxy)flavone, (I), pachypodol (4',5-dihydroxy-3,3',7-trimethoxyflavone), (II), and tenatin (4',5-dihydroxy-3,3',7,8-tetramethoxyflavone), (III). Although compound (I) has previously been isolated from Boronia coerulescens (Ashan et al., 1994), and other prenylated flavones similar to (I) have been reported, i.e. from M. triphylla (Higa et al., 1987) and M. micrococca (Nasim, 1999), this represents the first report and cystallographic characterization of (I) from M. ellyrana.
Two morphologically different crystalline forms of (I) obtained from n-hexane (monoclinic polymorph A) and ethyl acetate (triclinic polymorph B) extracts allowed, in the first instance (because of the minute quantities of the available sample involved), determination of the identity of both polymorphs as the title compound and, in the second instance, confirmation of the existence of two significantly different molecular conformations (Figs. 1 and 2). Triclinic form B has a more compact molecular form than is found for monoclinic form A due mainly to the more convoluted enyloxy side chain (comparative molecular volumes of 506 and 526 Å3, respectively). This is reflected particularly in the C7—O7—C71—C72 and O7—C71—C72—C73 torsion angles of 81.9 (4) and 107.4 (5)°, respectively, in form B, and -174.6 (3) and 143.5 (4)° in polymorph A. In addition, the benzene ring substituent at C2, although essentially coplanar with the parent ring, is rotated about the C2—C12 bond vector such that the meta-substituted methoxy groups in the two polymorphs are ca 180° apart. Intramolecular C—H···O(methoxy) and C—H···O(ether) interactions are significant in maintaining the coplanarity of the two ring systems [C22–H22···O3 2.888 (5) Å and C62–H62···O1 2.627 (4) Å for form A; C22–H22···O1 2.664 (5) Å and C62–H62···O3 2.858 (5) Å for form B]. Relatively minor conformational differences are found in the methoxy substituents at C3, C8 and C52, while in each, there are intramolecular hydrogen-bonding interactions involving the hydroxyl group at C5 and the adjacent ketone O atom at C4 [O5—H5···O4: 2.600 (4) Å in form A and 2.586 (4) Å in form B], and the hydroxyl group at C42 and the adjacent methoxy O atom at C52 [O42—H42···O52: 2.692 (4) Å in form A and 2.657 (4) Å in form B].
A major difference between polymorphs A and B lies in the packing; in A, a single intermolecular hydrogen-bond interaction is found between the H atom of the hydroxyl group at C42 and a ketone O atom of a glide-related neighbour [O42—H42···O4i 2.784 (4) Å; symmetry code: (i) 1/2 + x, 1/2 - y, 1/2 + z]. This completes a three-centred hydrogen-bond association about H42, with a relatively long H42···O4i separation of 1.87 Å.