Acta Cryst. (2010). E66, o704 [ doi:10.1107/S1600536810006628 ]
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-D-glucopyranosyloxy)butanolideThe title compound, C25H30O12, which demonstrates a significant hepatoprotective effect, has comparable geometrical parameters to those of similar compounds. The absolute configuration of the title compound, viz. 2R,3S, was identified from the Flack parameter of 0.05 (17) and the Hooft parameter of 0.04 (6).
To a solution of Ethyl (2R,3S)-3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-2- benzyl-4-hydroxybutanoate (1.0 equiv) in 1,4-dioxane (10 ml) was added 4-methylbenzenesulfonic acid (1.0 equiv), then the solution was stirred at room temperature for 2 days. After removal of the solvent in vacuo, the residue was purified by column chromatography. White crystals suitable for X-ray analysis were obtained by slow evaportion of a petroleum ether/EtOAc solution over a period of two weeks (Saito et al., 1992; Kazumasa et al., 2000; Schmidt, 1986; Corey & Venkateswarlu, 1972; Fernandez et al., 1997).
All H atoms were placed in geometrically idealised positions and constrained to ride on their parent atoms with C—H distances in the range of 0.95-1.00 Å, with a displacement parameter Uiso set to 1.2 (CH and CH2) or 1.5(CH3) times Ueq of the parent atom.
Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
![[Figure 1]](./vm2019fig1thm.gif)
| Fig. 1. View of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
| C25H30O12 | F(000) = 1104 |
| Mr = 522.49 | Dx = 1.282 Mg m−3 |
| Orthorhombic, P212121 | Cu Kα radiation, λ = 1.54178 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 5304 reflections |
| a = 10.6142 (2) Å | θ = 4.0–65.7° |
| b = 11.0984 (2) Å | µ = 0.87 mm−1 |
| c = 22.9714 (3) Å | T = 153 K |
| V = 2706.05 (8) Å3 | Block, white |
| Z = 4 | 0.15 × 0.15 × 0.10 mm |
| Mac dip 2030b diffractometer | 4102 independent reflections |
| Radiation source: rotating anode | 4015 reflections with I > 2σ(I) |
| graphite | Rint = 0.016 |
| Detector resolution: 0 pixels mm-1 | θmax = 66.0°, θmin = 4.4° |
| ω scans | h = −12→9 |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | k = −12→12 |
| Tmin = 0.880, Tmax = 0.918 | l = −26→26 |
| 7246 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.102 | w = 1/[σ2(Fo2) + (0.0654P)2 + 0.5803P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.07 | (Δ/σ)max < 0.001 |
| 4102 reflections | Δρmax = 0.34 e Å−3 |
| 334 parameters | Δρmin = −0.22 e Å−3 |
| 0 restraints | Absolute structure: Flack (1983), 1417 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: 0.05 (17) |
| C25H30O12 | V = 2706.05 (8) Å3 |
| Mr = 522.49 | Z = 4 |
| Orthorhombic, P212121 | Cu Kα radiation |
| a = 10.6142 (2) Å | µ = 0.87 mm−1 |
| b = 11.0984 (2) Å | T = 153 K |
| c = 22.9714 (3) Å | 0.15 × 0.15 × 0.10 mm |
| Mac dip 2030b diffractometer | 4102 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | 4015 reflections with I > 2σ(I) |
| Tmin = 0.880, Tmax = 0.918 | Rint = 0.016 |
| 7246 measured reflections | θmax = 66.0° |
| R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
| wR(F2) = 0.102 | Δρmax = 0.34 e Å−3 |
| S = 1.07 | Δρmin = −0.22 e Å−3 |
| 4102 reflections | Absolute structure: Flack (1983), 1417 Friedel pairs |
| 334 parameters | Flack parameter: 0.05 (17) |
| 0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 | 0.47650 (16) | 0.31851 (14) | 0.32119 (7) | 0.0442 (4) | |
| O2 | 0.58032 (14) | 0.48590 (14) | 0.29725 (6) | 0.0403 (3) | |
| O3 | 0.49559 (12) | 0.47669 (12) | 0.17568 (6) | 0.0311 (3) | |
| O4 | 0.44988 (12) | 0.58270 (12) | 0.09414 (6) | 0.0300 (3) | |
| O5 | 0.73101 (12) | 0.40529 (12) | 0.12561 (6) | 0.0319 (3) | |
| O6 | 0.71425 (13) | 0.39829 (13) | 0.00188 (6) | 0.0351 (3) | |
| O7 | 0.61363 (13) | 0.62268 (12) | −0.04400 (6) | 0.0325 (3) | |
| O8 | 0.29897 (12) | 0.61966 (13) | −0.00230 (6) | 0.0353 (3) | |
| O9 | 0.64011 (15) | 0.22826 (13) | 0.14807 (7) | 0.0427 (4) | |
| O10 | 0.89389 (19) | 0.49770 (18) | −0.01722 (12) | 0.0784 (7) | |
| O11 | 0.5236 (2) | 0.4937 (2) | −0.10623 (7) | 0.0675 (6) | |
| O12 | 0.2865 (2) | 0.7043 (2) | −0.09013 (8) | 0.0739 (7) | |
| C1 | 0.4778 (2) | 0.41371 (19) | 0.29662 (9) | 0.0341 (4) | |
| C2 | 0.37455 (19) | 0.47400 (18) | 0.26180 (8) | 0.0306 (4) | |
| H2A | 0.3281 | 0.5283 | 0.2891 | 0.037* | |
| C3 | 0.45018 (18) | 0.55428 (17) | 0.22133 (8) | 0.0297 (4) | |
| H3A | 0.4010 | 0.6247 | 0.2064 | 0.036* | |
| C4 | 0.5581 (2) | 0.59050 (19) | 0.26080 (9) | 0.0351 (4) | |
| H4A | 0.6341 | 0.6103 | 0.2377 | 0.042* | |
| H4B | 0.5350 | 0.6613 | 0.2847 | 0.042* | |
| C5 | 0.2771 (2) | 0.38840 (18) | 0.23518 (9) | 0.0346 (4) | |
| H5A | 0.3174 | 0.3409 | 0.2038 | 0.042* | |
| H5B | 0.2477 | 0.3314 | 0.2654 | 0.042* | |
| C6 | 0.16563 (19) | 0.45524 (18) | 0.21066 (10) | 0.0354 (4) | |
| C7 | 0.0715 (2) | 0.4974 (2) | 0.24720 (10) | 0.0421 (5) | |
| H7A | 0.0756 | 0.4808 | 0.2877 | 0.050* | |
| C8 | −0.0285 (2) | 0.5636 (2) | 0.22519 (15) | 0.0569 (7) | |
| H8A | −0.0916 | 0.5928 | 0.2509 | 0.068* | |
| C9 | −0.0377 (3) | 0.5875 (2) | 0.16642 (15) | 0.0616 (8) | |
| H9A | −0.1064 | 0.6328 | 0.1515 | 0.074* | |
| C10 | 0.0552 (3) | 0.5443 (3) | 0.12938 (13) | 0.0606 (8) | |
| H10A | 0.0493 | 0.5591 | 0.0887 | 0.073* | |
| C11 | 0.1569 (2) | 0.4795 (2) | 0.15118 (10) | 0.0456 (5) | |
| H11A | 0.2207 | 0.4516 | 0.1255 | 0.055* | |
| C1' | 0.54911 (18) | 0.53583 (18) | 0.12866 (8) | 0.0294 (4) | |
| H1'A | 0.6062 | 0.6018 | 0.1421 | 0.035* | |
| C2' | 0.62123 (18) | 0.44333 (18) | 0.09365 (8) | 0.0283 (4) | |
| H2'A | 0.5661 | 0.3723 | 0.0854 | 0.034* | |
| C3' | 0.66843 (17) | 0.49655 (17) | 0.03700 (8) | 0.0281 (4) | |
| H3'A | 0.7380 | 0.5551 | 0.0448 | 0.034* | |
| C4' | 0.56170 (18) | 0.55880 (17) | 0.00501 (8) | 0.0288 (4) | |
| H4'A | 0.4997 | 0.4974 | −0.0089 | 0.035* | |
| C5' | 0.49602 (18) | 0.64833 (18) | 0.04534 (8) | 0.0299 (4) | |
| H5'A | 0.5582 | 0.7100 | 0.0589 | 0.036* | |
| C6' | 0.38565 (19) | 0.71066 (19) | 0.01696 (9) | 0.0359 (5) | |
| H6'A | 0.3439 | 0.7650 | 0.0452 | 0.043* | |
| H6'B | 0.4148 | 0.7593 | −0.0166 | 0.043* | |
| C7' | 0.7291 (2) | 0.29459 (19) | 0.15016 (9) | 0.0351 (4) | |
| C8' | 0.8527 (3) | 0.2666 (2) | 0.17810 (13) | 0.0547 (6) | |
| H8'A | 0.8493 | 0.1860 | 0.1955 | 0.082* | |
| H8'B | 0.8703 | 0.3262 | 0.2085 | 0.082* | |
| H8'C | 0.9195 | 0.2692 | 0.1487 | 0.082* | |
| C9' | 0.8281 (2) | 0.4122 (2) | −0.02386 (12) | 0.0516 (6) | |
| C10' | 0.8550 (4) | 0.3043 (3) | −0.06145 (19) | 0.0899 (12) | |
| H10B | 0.9370 | 0.3143 | −0.0804 | 0.135* | |
| H10C | 0.7892 | 0.2967 | −0.0912 | 0.135* | |
| H10D | 0.8562 | 0.2315 | −0.0373 | 0.135* | |
| C11' | 0.5904 (2) | 0.5778 (2) | −0.09765 (9) | 0.0385 (5) | |
| C12' | 0.6610 (2) | 0.6479 (2) | −0.14304 (10) | 0.0464 (5) | |
| H12A | 0.6431 | 0.6142 | −0.1816 | 0.070* | |
| H12B | 0.7516 | 0.6428 | −0.1353 | 0.070* | |
| H12C | 0.6343 | 0.7324 | −0.1419 | 0.070* | |
| C13' | 0.26186 (19) | 0.6221 (2) | −0.05781 (9) | 0.0403 (5) | |
| C14' | 0.1842 (2) | 0.5152 (3) | −0.07186 (11) | 0.0526 (6) | |
| H14A | 0.1585 | 0.5186 | −0.1128 | 0.079* | |
| H14B | 0.1091 | 0.5144 | −0.0470 | 0.079* | |
| H14C | 0.2334 | 0.4419 | −0.0650 | 0.079* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0555 (9) | 0.0361 (8) | 0.0410 (8) | 0.0107 (7) | −0.0020 (7) | 0.0053 (7) |
| O2 | 0.0368 (8) | 0.0424 (9) | 0.0418 (7) | 0.0029 (7) | −0.0093 (6) | −0.0006 (7) |
| O3 | 0.0359 (7) | 0.0277 (7) | 0.0297 (6) | −0.0020 (5) | 0.0038 (5) | −0.0030 (6) |
| O4 | 0.0273 (7) | 0.0310 (7) | 0.0318 (6) | 0.0005 (6) | 0.0018 (5) | −0.0016 (6) |
| O5 | 0.0276 (7) | 0.0281 (7) | 0.0401 (7) | −0.0025 (6) | −0.0058 (6) | 0.0042 (6) |
| O6 | 0.0340 (7) | 0.0320 (7) | 0.0393 (7) | 0.0047 (6) | 0.0059 (6) | −0.0049 (6) |
| O7 | 0.0321 (7) | 0.0342 (7) | 0.0313 (6) | −0.0013 (6) | 0.0026 (6) | 0.0017 (6) |
| O8 | 0.0294 (7) | 0.0396 (8) | 0.0369 (7) | −0.0006 (6) | −0.0016 (6) | 0.0059 (6) |
| O9 | 0.0455 (9) | 0.0308 (8) | 0.0518 (8) | −0.0081 (7) | −0.0055 (7) | 0.0073 (7) |
| O10 | 0.0542 (11) | 0.0501 (12) | 0.1310 (19) | −0.0041 (10) | 0.0518 (12) | −0.0067 (12) |
| O11 | 0.0873 (14) | 0.0811 (15) | 0.0342 (8) | −0.0362 (13) | −0.0059 (8) | −0.0060 (9) |
| O12 | 0.0730 (13) | 0.0984 (17) | 0.0504 (10) | −0.0315 (12) | −0.0147 (9) | 0.0310 (11) |
| C1 | 0.0384 (11) | 0.0333 (11) | 0.0305 (9) | 0.0050 (9) | 0.0005 (8) | −0.0050 (9) |
| C2 | 0.0327 (10) | 0.0287 (10) | 0.0303 (9) | 0.0043 (8) | 0.0020 (8) | −0.0028 (8) |
| C3 | 0.0300 (10) | 0.0271 (10) | 0.0320 (9) | 0.0022 (8) | −0.0005 (8) | −0.0042 (8) |
| C4 | 0.0331 (10) | 0.0339 (11) | 0.0383 (10) | −0.0011 (8) | −0.0029 (8) | −0.0039 (9) |
| C5 | 0.0345 (10) | 0.0280 (10) | 0.0413 (10) | −0.0006 (9) | 0.0030 (9) | −0.0007 (9) |
| C6 | 0.0317 (10) | 0.0280 (10) | 0.0464 (11) | −0.0061 (8) | −0.0026 (9) | −0.0024 (9) |
| C7 | 0.0312 (10) | 0.0416 (12) | 0.0534 (12) | −0.0050 (9) | −0.0025 (9) | −0.0091 (11) |
| C8 | 0.0311 (12) | 0.0459 (14) | 0.094 (2) | −0.0005 (10) | −0.0113 (12) | −0.0126 (14) |
| C9 | 0.0429 (14) | 0.0391 (13) | 0.103 (2) | −0.0070 (11) | −0.0301 (15) | 0.0106 (15) |
| C10 | 0.0598 (17) | 0.0572 (16) | 0.0650 (16) | −0.0182 (14) | −0.0268 (14) | 0.0211 (14) |
| C11 | 0.0473 (12) | 0.0424 (13) | 0.0471 (12) | −0.0111 (11) | −0.0049 (10) | 0.0031 (10) |
| C1' | 0.0280 (9) | 0.0284 (10) | 0.0317 (9) | −0.0053 (8) | −0.0001 (8) | −0.0017 (8) |
| C2' | 0.0234 (9) | 0.0271 (10) | 0.0342 (9) | −0.0028 (7) | −0.0031 (8) | 0.0009 (8) |
| C3' | 0.0251 (9) | 0.0255 (9) | 0.0337 (9) | −0.0003 (7) | 0.0034 (7) | −0.0034 (8) |
| C4' | 0.0273 (9) | 0.0280 (10) | 0.0310 (9) | −0.0028 (7) | 0.0018 (8) | −0.0006 (8) |
| C5' | 0.0277 (10) | 0.0282 (10) | 0.0338 (9) | −0.0011 (7) | 0.0027 (8) | −0.0001 (8) |
| C6' | 0.0309 (10) | 0.0329 (11) | 0.0439 (11) | 0.0045 (9) | 0.0021 (9) | 0.0018 (9) |
| C7' | 0.0404 (11) | 0.0284 (10) | 0.0366 (10) | 0.0008 (9) | −0.0039 (9) | 0.0014 (8) |
| C8' | 0.0558 (15) | 0.0383 (13) | 0.0701 (15) | −0.0020 (11) | −0.0260 (13) | 0.0120 (12) |
| C9' | 0.0476 (13) | 0.0386 (13) | 0.0686 (15) | 0.0099 (11) | 0.0254 (12) | 0.0046 (12) |
| C10' | 0.087 (2) | 0.0606 (18) | 0.122 (3) | 0.0138 (17) | 0.060 (2) | −0.014 (2) |
| C11' | 0.0371 (12) | 0.0449 (13) | 0.0335 (10) | 0.0044 (10) | −0.0032 (9) | −0.0009 (9) |
| C12' | 0.0471 (13) | 0.0555 (14) | 0.0365 (10) | 0.0082 (11) | 0.0073 (10) | 0.0059 (10) |
| C13' | 0.0272 (10) | 0.0571 (14) | 0.0367 (10) | 0.0039 (9) | −0.0007 (9) | 0.0101 (10) |
| C14' | 0.0434 (13) | 0.0680 (17) | 0.0464 (12) | −0.0034 (12) | −0.0112 (10) | 0.0012 (12) |
| O1—C1 | 1.198 (3) | C8—H8A | 0.9500 |
| O2—C1 | 1.351 (3) | C9—C10 | 1.388 (5) |
| O2—C4 | 1.451 (3) | C9—H9A | 0.9500 |
| O3—C1' | 1.386 (2) | C10—C11 | 1.390 (4) |
| O3—C3 | 1.440 (2) | C10—H10A | 0.9500 |
| O4—C1' | 1.417 (2) | C11—H11A | 0.9500 |
| O4—C5' | 1.424 (2) | C1'—C2' | 1.512 (3) |
| O5—C7' | 1.352 (3) | C1'—H1'A | 1.0000 |
| O5—C2' | 1.440 (2) | C2'—C3' | 1.514 (3) |
| O6—C9' | 1.355 (3) | C2'—H2'A | 1.0000 |
| O6—C3' | 1.441 (2) | C3'—C4' | 1.517 (3) |
| O7—C11' | 1.352 (2) | C3'—H3'A | 1.0000 |
| O7—C4' | 1.440 (2) | C4'—C5' | 1.527 (3) |
| O8—C13' | 1.335 (3) | C4'—H4'A | 1.0000 |
| O8—C6' | 1.436 (3) | C5'—C6' | 1.509 (3) |
| O9—C7' | 1.199 (3) | C5'—H5'A | 1.0000 |
| O10—C9' | 1.188 (3) | C6'—H6'A | 0.9900 |
| O11—C11' | 1.189 (3) | C6'—H6'B | 0.9900 |
| O12—C13' | 1.205 (3) | C7'—C8' | 1.493 (3) |
| C1—C2 | 1.513 (3) | C8'—H8'A | 0.9800 |
| C2—C3 | 1.517 (3) | C8'—H8'B | 0.9800 |
| C2—C5 | 1.532 (3) | C8'—H8'C | 0.9800 |
| C2—H2A | 1.0000 | C9'—C10' | 1.504 (4) |
| C3—C4 | 1.515 (3) | C10'—H10B | 0.9800 |
| C3—H3A | 1.0000 | C10'—H10C | 0.9800 |
| C4—H4A | 0.9900 | C10'—H10D | 0.9800 |
| C4—H4B | 0.9900 | C11'—C12' | 1.501 (3) |
| C5—C6 | 1.506 (3) | C12'—H12A | 0.9800 |
| C5—H5A | 0.9900 | C12'—H12B | 0.9800 |
| C5—H5B | 0.9900 | C12'—H12C | 0.9800 |
| C6—C7 | 1.386 (3) | C13'—C14' | 1.480 (4) |
| C6—C11 | 1.396 (3) | C14'—H14A | 0.9800 |
| C7—C8 | 1.387 (3) | C14'—H14B | 0.9800 |
| C7—H7A | 0.9500 | C14'—H14C | 0.9800 |
| C8—C9 | 1.379 (5) | ||
| C1—O2—C4 | 109.73 (15) | C1'—C2'—H2'A | 109.8 |
| C1'—O3—C3 | 114.93 (15) | C3'—C2'—H2'A | 109.8 |
| C1'—O4—C5' | 111.88 (14) | O6—C3'—C2' | 107.32 (15) |
| C7'—O5—C2' | 117.84 (15) | O6—C3'—C4' | 108.99 (15) |
| C9'—O6—C3' | 117.33 (17) | C2'—C3'—C4' | 110.30 (15) |
| C11'—O7—C4' | 117.49 (16) | O6—C3'—H3'A | 110.1 |
| C13'—O8—C6' | 117.98 (17) | C2'—C3'—H3'A | 110.1 |
| O1—C1—O2 | 121.81 (19) | C4'—C3'—H3'A | 110.1 |
| O1—C1—C2 | 129.1 (2) | O7—C4'—C3' | 108.49 (15) |
| O2—C1—C2 | 109.08 (17) | O7—C4'—C5' | 109.19 (15) |
| C1—C2—C3 | 101.56 (16) | C3'—C4'—C5' | 110.08 (15) |
| C1—C2—C5 | 115.21 (17) | O7—C4'—H4'A | 109.7 |
| C3—C2—C5 | 118.49 (16) | C3'—C4'—H4'A | 109.7 |
| C1—C2—H2A | 106.9 | C5'—C4'—H4'A | 109.7 |
| C3—C2—H2A | 106.9 | O4—C5'—C6' | 107.93 (16) |
| C5—C2—H2A | 106.9 | O4—C5'—C4' | 107.57 (15) |
| O3—C3—C4 | 109.95 (16) | C6'—C5'—C4' | 112.99 (16) |
| O3—C3—C2 | 105.78 (15) | O4—C5'—H5'A | 109.4 |
| C4—C3—C2 | 100.91 (16) | C6'—C5'—H5'A | 109.4 |
| O3—C3—H3A | 113.1 | C4'—C5'—H5'A | 109.4 |
| C4—C3—H3A | 113.1 | O8—C6'—C5' | 107.95 (16) |
| C2—C3—H3A | 113.1 | O8—C6'—H6'A | 110.1 |
| O2—C4—C3 | 104.82 (16) | C5'—C6'—H6'A | 110.1 |
| O2—C4—H4A | 110.8 | O8—C6'—H6'B | 110.1 |
| C3—C4—H4A | 110.8 | C5'—C6'—H6'B | 110.1 |
| O2—C4—H4B | 110.8 | H6'A—C6'—H6'B | 108.4 |
| C3—C4—H4B | 110.8 | O9—C7'—O5 | 123.58 (19) |
| H4A—C4—H4B | 108.9 | O9—C7'—C8' | 125.6 (2) |
| C6—C5—C2 | 111.99 (16) | O5—C7'—C8' | 110.83 (18) |
| C6—C5—H5A | 109.2 | C7'—C8'—H8'A | 109.5 |
| C2—C5—H5A | 109.2 | C7'—C8'—H8'B | 109.5 |
| C6—C5—H5B | 109.2 | H8'A—C8'—H8'B | 109.5 |
| C2—C5—H5B | 109.2 | C7'—C8'—H8'C | 109.5 |
| H5A—C5—H5B | 107.9 | H8'A—C8'—H8'C | 109.5 |
| C7—C6—C11 | 118.7 (2) | H8'B—C8'—H8'C | 109.5 |
| C7—C6—C5 | 120.4 (2) | O10—C9'—O6 | 124.0 (2) |
| C11—C6—C5 | 120.9 (2) | O10—C9'—C10' | 126.8 (2) |
| C8—C7—C6 | 120.6 (2) | O6—C9'—C10' | 109.2 (2) |
| C8—C7—H7A | 119.7 | C9'—C10'—H10B | 109.5 |
| C6—C7—H7A | 119.7 | C9'—C10'—H10C | 109.5 |
| C9—C8—C7 | 120.9 (3) | H10B—C10'—H10C | 109.5 |
| C9—C8—H8A | 119.6 | C9'—C10'—H10D | 109.5 |
| C7—C8—H8A | 119.6 | H10B—C10'—H10D | 109.5 |
| C8—C9—C10 | 118.9 (2) | H10C—C10'—H10D | 109.5 |
| C8—C9—H9A | 120.5 | O11—C11'—O7 | 123.3 (2) |
| C10—C9—H9A | 120.5 | O11—C11'—C12' | 126.1 (2) |
| C9—C10—C11 | 120.6 (3) | O7—C11'—C12' | 110.57 (19) |
| C9—C10—H10A | 119.7 | C11'—C12'—H12A | 109.5 |
| C11—C10—H10A | 119.7 | C11'—C12'—H12B | 109.5 |
| C10—C11—C6 | 120.3 (3) | H12A—C12'—H12B | 109.5 |
| C10—C11—H11A | 119.9 | C11'—C12'—H12C | 109.5 |
| C6—C11—H11A | 119.9 | H12A—C12'—H12C | 109.5 |
| O3—C1'—O4 | 107.78 (15) | H12B—C12'—H12C | 109.5 |
| O3—C1'—C2' | 107.49 (16) | O12—C13'—O8 | 122.7 (2) |
| O4—C1'—C2' | 109.14 (14) | O12—C13'—C14' | 126.4 (2) |
| O3—C1'—H1'A | 110.8 | O8—C13'—C14' | 110.89 (19) |
| O4—C1'—H1'A | 110.8 | C13'—C14'—H14A | 109.5 |
| C2'—C1'—H1'A | 110.8 | C13'—C14'—H14B | 109.5 |
| O5—C2'—C1' | 109.72 (15) | H14A—C14'—H14B | 109.5 |
| O5—C2'—C3' | 106.54 (15) | C13'—C14'—H14C | 109.5 |
| C1'—C2'—C3' | 111.08 (16) | H14A—C14'—H14C | 109.5 |
| O5—C2'—H2'A | 109.8 | H14B—C14'—H14C | 109.5 |
| C4—O2—C1—O1 | 176.02 (19) | O3—C1'—C2'—O5 | −70.08 (18) |
| C4—O2—C1—C2 | −4.4 (2) | O4—C1'—C2'—O5 | 173.29 (14) |
| O1—C1—C2—C3 | −154.5 (2) | O3—C1'—C2'—C3' | 172.38 (15) |
| O2—C1—C2—C3 | 25.89 (19) | O4—C1'—C2'—C3' | 55.8 (2) |
| O1—C1—C2—C5 | −25.2 (3) | C9'—O6—C3'—C2' | −132.97 (19) |
| O2—C1—C2—C5 | 155.26 (16) | C9'—O6—C3'—C4' | 107.6 (2) |
| C1'—O3—C3—C4 | −82.37 (19) | O5—C2'—C3'—O6 | 71.25 (18) |
| C1'—O3—C3—C2 | 169.45 (14) | C1'—C2'—C3'—O6 | −169.29 (14) |
| C1—C2—C3—O3 | 79.21 (17) | O5—C2'—C3'—C4' | −170.14 (15) |
| C5—C2—C3—O3 | −48.1 (2) | C1'—C2'—C3'—C4' | −50.7 (2) |
| C1—C2—C3—C4 | −35.34 (18) | C11'—O7—C4'—C3' | 108.25 (18) |
| C5—C2—C3—C4 | −162.61 (17) | C11'—O7—C4'—C5' | −131.76 (18) |
| C1—O2—C4—C3 | −19.3 (2) | O6—C3'—C4'—O7 | −70.62 (18) |
| O3—C3—C4—O2 | −77.30 (19) | C2'—C3'—C4'—O7 | 171.80 (15) |
| C2—C3—C4—O2 | 34.09 (19) | O6—C3'—C4'—C5' | 169.95 (14) |
| C1—C2—C5—C6 | 169.70 (17) | C2'—C3'—C4'—C5' | 52.4 (2) |
| C3—C2—C5—C6 | −69.8 (2) | C1'—O4—C5'—C6' | −171.17 (16) |
| C2—C5—C6—C7 | −78.9 (2) | C1'—O4—C5'—C4' | 66.61 (18) |
| C2—C5—C6—C11 | 98.9 (2) | O7—C4'—C5'—O4 | −177.99 (14) |
| C11—C6—C7—C8 | −0.8 (3) | C3'—C4'—C5'—O4 | −58.99 (19) |
| C5—C6—C7—C8 | 177.1 (2) | O7—C4'—C5'—C6' | 63.0 (2) |
| C6—C7—C8—C9 | 0.9 (4) | C3'—C4'—C5'—C6' | −178.01 (16) |
| C7—C8—C9—C10 | −0.1 (4) | C13'—O8—C6'—C5' | −127.09 (18) |
| C8—C9—C10—C11 | −1.0 (4) | O4—C5'—C6'—O8 | −61.5 (2) |
| C9—C10—C11—C6 | 1.1 (4) | C4'—C5'—C6'—O8 | 57.4 (2) |
| C7—C6—C11—C10 | −0.3 (3) | C2'—O5—C7'—O9 | −2.1 (3) |
| C5—C6—C11—C10 | −178.1 (2) | C2'—O5—C7'—C8' | 176.30 (19) |
| C3—O3—C1'—O4 | −77.32 (18) | C3'—O6—C9'—O10 | 3.2 (4) |
| C3—O3—C1'—C2' | 165.16 (15) | C3'—O6—C9'—C10' | −176.3 (2) |
| C5'—O4—C1'—O3 | 178.36 (14) | C4'—O7—C11'—O11 | 4.8 (3) |
| C5'—O4—C1'—C2' | −65.20 (19) | C4'—O7—C11'—C12' | −174.66 (18) |
| C7'—O5—C2'—C1' | 106.05 (19) | C6'—O8—C13'—O12 | −8.6 (3) |
| C7'—O5—C2'—C3' | −133.61 (17) | C6'—O8—C13'—C14' | 173.88 (18) |
| O1—C1 | 1.198 (3) | C8—C9 | 1.379 (5) |
| O2—C1 | 1.351 (3) | C9—C10 | 1.388 (5) |
| O2—C4 | 1.451 (3) | C10—C11 | 1.390 (4) |
| O4—C1' | 1.417 (2) | C1'—C2' | 1.512 (3) |
| O4—C5' | 1.424 (2) | C2'—C3' | 1.514 (3) |
| C6—C7 | 1.386 (3) | C3'—C4' | 1.517 (3) |
| C6—C11 | 1.396 (3) | C4'—C5' | 1.527 (3) |
| C7—C8 | 1.387 (3) | ||
| O1—C1—O2 | 121.81 (19) | C9—C10—C11 | 120.6 (3) |
| C1—C2—C5 | 115.21 (17) | O3—C1'—O4 | 107.78 (15) |
| O3—C3—C4 | 109.95 (16) | O4—C1'—C2' | 109.14 (14) |
| C7—C6—C5 | 120.4 (2) | C3'—C4'—C5' | 110.08 (15) |
| C9—C8—C7 | 120.9 (3) |
The authors extend their hearty thanks to Ms Lin Ziyun and Mr Li Peng for their advice and encouragement during the work.
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The title compound was found to have a significant hepatoprotective effect, comparable to the natural product Goodyeroside A (Du & Irinon, 2008). Recently, the compound was successfully crystallized from a petroleum ether/EtOAc mixture, yielding crystals suitable for X-ray analysis.
Fig.1 shows the molecular structure of the title compound with atomic numbering scheme. The bond lengths and angles are in agreement with reported literature values (Table 1) (Allen et al., 1987). The benzene ring (C6—C11) is essentially planar, with r.m.s deviations of 0.0078 (14) Å. The five-membered ring (C1—C4/O2) has an envelope conformation with the C3 atom out of plane and the six-membered ring (C1'-C5'/O4) is in its chair conformation. The dihedral angles between the various rings in the title compound are as follows, where the first atom is used to identify its five- or six- membered ring: C1/C6 112.9 (1)°; C1/C1' 110.1 (1)°; C6/C1' 13.1 (1)°.
In order to determine the absolute configuration of the title compound, the data collection was performed using Cu Kα. The absolute configuration is confirmed by the Flack parameter 0.05 (17) and Hooft parameter 0.04 (6) (Flack, 1983; Hooft et al., 2008).