Alisol F 24-acetate: (24R)-24-acet­oxy-11β,25-dihydr­oxy-16β,23β-ep­oxy­protost-13(17)-en-3-one

Wang, X.-B.; Kong, L.-Y.

doi:10.1107/S1600536807045126

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Alisol F 24-acetate: (24R)-24-acetoxy-11β,25-dihydroxy-16β,23β-epoxyprotost-13(17)-en-3-one

X.-B. Wang and L.-Y. Kong

The title compound, C₃₂H₅₀O₆, a known protostane-type triterpene, was isolated from the Chinese herbal medicine Lobelia chinensis Lour. The molecule contains five fused rings: four six-membered rings (A, B, C and E) and a five-membered ring (D). Rings A and B have slightly distorted boat conformations, while rings C and E adopt chair conformations. Ring D is almost planar. Rings A and B and rings B and C are both trans-fused. A chain running along the b axis is formed via classical intermolecular O—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807045126/is2209sup1.cif Contains datablocks I, New_Global_Publ_Block
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807045126/is2209Isup2.hkl Contains datablock I

CCDC reference: 663802

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.011 Å
R factor = 0.089
wR factor = 0.236
Data-to-parameter ratio = 7.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.25 Ratio
PLAT340_ALERT_3_B Low Bond Precision on C-C Bonds (x 1000) Ang ...         11

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       7.86
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.40 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C31
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H7B    ..  H29A    ..       1.85 Ang.

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           25.00
           From the CIF: _reflns_number_total               2697
           Count of symmetry unique reflns         2697
           Completeness (_total/calc)            100.00%
           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
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C18    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C20    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C21    = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         37

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
  12 ALERT level G = General alerts; check

  11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The title compound, C₃₂H₅₀O₆, a known protostane-type triterpene, named alisol F 24-acetate [systematic name: 16β, 23β-epoxy-11β, 25-dihydroxy-24(R)-acetoxy-protost-13 (17)-en-3-one], was isolated from the Chinese herbal medicine Lobelia chinensis Lour firstly obtained by Peng & Lou (2001) and found to possess activity for inhibiting formation of urinary oxalate calcium calculi. Its structure was elucidated on the basis of spectroscopic methods such as ¹H NMR, ¹³C NMR, two-dimensional NMR and chemical correlation (Peng & Lou, 2001; Zhou et al., 2005).

The molecule contains a five-fused ring system including four six-membered rings, A(C1—C5/C10), B(C5—C10), C(C8—C14) and E(O3/C16—C20) and a five-membered ring D(C13—C17) (Fig. 1). The junctions of the three fused six-membered rings A, B and C, two of which, A and B, adopt slightly distorted boat conformations and the C exhibits a perfect chair conformation, are all trans. The five-membered ring D is almost planar. Ring E adopts a chair conformation. A chain running along the b axis was formed via the classic intermolecular O—H···O hydrogen bonds as shown in Fig. 2.

Related literature top

For related literature, see: Peng & Lou (2001); Zhou et al. (2005).

Experimental top

The dried herb of Lobelia chinensis (18 kg) was extracted with refluxing 95% ethanol (3 × 20 L), after removal of the solvent under reduced pressure, the extract was suspended in water and then partitioned with light petroleum, EtOAc and n-BuOH successively. The EtOAc-soluble part (150 g) was chromatographed on a silica gel column, using a gradient mixture of light petroleum-EtOAc as eluent. The fraction eluted with petrol-EtOAc (9: 2, v/v) was further purified by sephadex LH-20 column chromatography using CHCl₃—CH₃OH (1:1 v/v) as eluent, to yield the title compound (10 mg). IR (KBr) cm^-1: 3450, 3310, 1740, 1698, 1459, 1375, 1248, 1100, 1053. ¹H NMR (500 MHz, DMSO-d₆) δ: 2.47 (1H, m, H-1a), 2.32 (1H, m, H-1 b), 2.87 (1H, m, H-2a), 2.44 (1H, m, H-2 b), 2.25 (1H, dd, J = 11.0, 5.1 Hz, H-5),1.41 (1H, m, H-6a), 1.98 (1H, m, H-7a), 1.26 (2H, m, H-6 b, 7 b), 1.95 (1H, d, J = 11.0 Hz, H-9), 4.0 4 (1H, m, H-11), 2.91 (1H, dd, J = 13.0, 5.8 Hz, H-12a), 2.39 (1H, dd, J = 13.0, 12.8 Hz, H-12b), 2.28 (1H, dd, J = 13.8, 6.5 Hz, H-15a), 1.40 (1H, dd, J = 13.8, 5.5 Hz, H-15b), 4.58 (1H, dd, J=9.1, 7.1 Hz, H-16), 1.01 (3H, s, H-18), 1.38 (3H, s, H-19), 2.84 (1H, m, H-20), 1.14 (3H, d, J = 7.1 Hz, H-21), 1.88 (1H, m, H-22a), 1.51 (1H, m, H-22b), 4.48 (1H, m, H-23), 5.21 (1H, d, J = 2.6 Hz, H-24), 1.56 (3H, s, H-26), 1.60 (3H, s, H-27), 1.11 (3H, s, H-28), 1.18 (3H, s, H-29), 1.19 (3H, s, H-30), 2.10 (3H, s, 24-OAc); ¹³C NMR (125 MHz, in DMSO-d₆) δ: 30.9 (C-1), 34.4 (C-2), 219.1 (C-3), 47.1 (C-4), 48.4 (C-5), 20.2 (C-6), 34.0 (C-7), 40.9 (C-8), 49.8 (C-9), 37.5 (C-10), 69.8 (C-11), 34.2 (C-12), 137.6 (C-13), 55.5 (C-14), 39.8 (C-15), 80.9 (C-16), 133.1 (C-17), 23.8 (C-18), 25.6 (C-19), 26.9 (C-20), 18.4 (C-21), 35.6 (C-22), 72.0 (C-23), 79.9 (C-24), 72.3 (C-25), 28.4 (C-26), 27.3 (C-27), 29.4 (C-28), 20.9 (C-29), 24.4 (C-30), 171.0 (24-OAc). Crystals suitable for X-ray structure analysis were obtained by slow evaporation of a methanol solution at room temperature.

Structure description top

For related literature, see: Peng & Lou (2001); Zhou et al. (2005).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

	Fig. 1. A drawing of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I) showing the formation of the chain running along the b axis via the classic intermolecular O—H···O hydrogen bonds.

(24R)-24-acetoxy-11β, 25-dihydroxy-16β,23β-epoxyprotost-13 (17)-en-3-one top

Crystal data top

C₃₂H₅₀O₆	F(000) = 580
M_r = 530.72	D_x = 1.201 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1829 reflections
a = 6.525 (4) Å	θ = 2.5–20.9°
b = 15.885 (10) Å	µ = 0.08 mm⁻¹
c = 14.401 (9) Å	T = 298 K
β = 100.475 (10)°	Prism, colourless
V = 1467.8 (16) Å³	0.50 × 0.47 × 0.40 mm
Z = 2

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2697 independent reflections
Radiation source: fine-focus sealed tube	1811 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
φ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
T_min = 0.959, T_max = 0.968	k = −16→18
7306 measured reflections	l = −17→16

Refinement top

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)] = 0.089	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.236	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1619P)²] where P = (F_o² + 2F_c²)/3
2697 reflections	(Δ/σ)_max < 0.001
343 parameters	Δρ_max = 0.48 e Å⁻³
37 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₃₂H₅₀O₆	V = 1467.8 (16) Å³
M_r = 530.72	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.525 (4) Å	µ = 0.08 mm⁻¹
b = 15.885 (10) Å	T = 298 K
c = 14.401 (9) Å	0.50 × 0.47 × 0.40 mm
β = 100.475 (10)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	2697 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1811 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.968	R_int = 0.072
7306 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.089	37 restraints
wR(F²) = 0.236	H-atom parameters constrained
S = 1.00	Δρ_max = 0.48 e Å⁻³
2697 reflections	Δρ_min = −0.26 e Å⁻³
343 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.5063 (9)	1.1516 (4)	0.2720 (4)	0.0555 (15)
O2	0.2109 (9)	0.8135 (3)	0.4045 (3)	0.0460 (14)
H2	0.2120	0.7918	0.4562	0.069*
O3	0.7078 (9)	0.4694 (3)	0.2211 (3)	0.0371 (13)
O4	1.0287 (8)	0.3572 (3)	0.2271 (4)	0.0428 (13)
O5	0.8746 (14)	0.2837 (6)	0.1019 (4)	0.085 (2)
O6	0.7817 (9)	0.2528 (3)	0.4048 (4)	0.0444 (13)
H6	0.6889	0.2314	0.3659	0.067*
C1	0.5384 (12)	0.9359 (5)	0.3534 (5)	0.0383 (18)
H1A	0.4649	0.9368	0.4062	0.046*
H1B	0.6501	0.8949	0.3675	0.046*
C2	0.6326 (15)	1.0232 (5)	0.3431 (6)	0.052 (2)
H2A	0.6314	1.0541	0.4010	0.062*
H2B	0.7773	1.0155	0.3374	0.062*
C3	0.5303 (11)	1.0768 (5)	0.2622 (5)	0.0349 (17)
C4	0.4809 (12)	1.0350 (5)	0.1647 (5)	0.0383 (18)
C5	0.4810 (11)	0.9379 (5)	0.1782 (5)	0.0331 (16)
H5	0.6285	0.9222	0.1935	0.040*
C6	0.3929 (13)	0.8873 (5)	0.0909 (5)	0.0389 (18)
H6A	0.4321	0.9132	0.0357	0.047*
H6B	0.2420	0.8864	0.0822	0.047*
C7	0.4770 (14)	0.7981 (5)	0.1020 (5)	0.0410 (19)
H7A	0.6161	0.7979	0.0871	0.049*
H7B	0.3903	0.7627	0.0559	0.049*
C8	0.4879 (10)	0.7578 (5)	0.2008 (5)	0.0314 (15)
C9	0.3477 (11)	0.8093 (5)	0.2591 (4)	0.0301 (16)
H9	0.2051	0.8026	0.2242	0.036*
C10	0.3867 (11)	0.9081 (5)	0.2639 (5)	0.0317 (16)
C11	0.3472 (12)	0.7679 (5)	0.3552 (5)	0.0331 (16)
H11	0.4887	0.7704	0.3923	0.040*
C12	0.2799 (12)	0.6763 (5)	0.3456 (5)	0.0385 (18)
H12A	0.2947	0.6509	0.4077	0.046*
H12B	0.1343	0.6730	0.3158	0.046*
C13	0.4099 (12)	0.6295 (4)	0.2876 (5)	0.0335 (17)
C14	0.4086 (11)	0.6647 (5)	0.1904 (5)	0.0327 (16)
C15	0.5620 (13)	0.6021 (5)	0.1531 (5)	0.0394 (18)
H15A	0.4849	0.5622	0.1090	0.047*
H15B	0.6580	0.6326	0.1214	0.047*
C16	0.6790 (12)	0.5568 (5)	0.2389 (5)	0.0351 (17)
H16	0.8152	0.5836	0.2591	0.042*
C17	0.5477 (12)	0.5702 (4)	0.3132 (5)	0.0345 (17)
C18	0.5973 (14)	0.5198 (5)	0.4025 (5)	0.0396 (19)
H18	0.4731	0.5186	0.4319	0.047*
C19	0.6453 (12)	0.4289 (5)	0.3749 (5)	0.0361 (17)
H19A	0.7017	0.3974	0.4315	0.043*
H19B	0.5168	0.4018	0.3451	0.043*
C20	0.7985 (12)	0.4269 (4)	0.3083 (5)	0.0333 (16)
H20	0.9246	0.4572	0.3375	0.040*
C21	0.8607 (11)	0.3405 (5)	0.2789 (5)	0.0356 (17)
H21	0.7430	0.3145	0.2366	0.043*
C22	0.9502 (11)	0.2777 (5)	0.3590 (5)	0.0343 (17)
C23	1.0319 (14)	0.2005 (5)	0.3158 (6)	0.050 (2)
H23A	0.9253	0.1784	0.2671	0.075*
H23B	1.0709	0.1585	0.3637	0.075*
H23C	1.1514	0.2157	0.2891	0.075*
C24	1.1135 (13)	0.3150 (6)	0.4342 (6)	0.052 (2)
H24A	1.0593	0.3647	0.4591	0.079*
H24B	1.2336	0.3296	0.4078	0.079*
H24C	1.1524	0.2748	0.4841	0.079*
C25	0.2861 (14)	1.0721 (5)	0.1050 (6)	0.053 (2)
H25A	0.2588	1.0445	0.0447	0.080*
H25B	0.3064	1.1312	0.0962	0.080*
H25C	0.1698	1.0640	0.1365	0.080*
C26	0.6698 (13)	1.0584 (6)	0.1182 (6)	0.050 (2)
H26A	0.6526	1.0337	0.0565	0.075*
H26B	0.7955	1.0375	0.1564	0.075*
H26C	0.6782	1.1185	0.1131	0.075*
C27	0.1778 (13)	0.9489 (6)	0.2643 (5)	0.045 (2)
H27A	0.1942	1.0090	0.2670	0.068*
H27B	0.1237	0.9300	0.3183	0.068*
H27C	0.0828	0.9338	0.2077	0.068*
C28	0.7171 (11)	0.7592 (5)	0.2526 (6)	0.0403 (18)
H28A	0.7263	0.7351	0.3143	0.060*
H28B	0.7663	0.8162	0.2582	0.060*
H28C	0.8012	0.7270	0.2173	0.060*
C29	0.1928 (12)	0.6566 (6)	0.1275 (5)	0.0452 (19)
H29A	0.1967	0.6800	0.0664	0.068*
H29B	0.0921	0.6865	0.1559	0.068*
H29C	0.1545	0.5983	0.1210	0.068*
C30	0.7728 (18)	0.5592 (6)	0.4713 (5)	0.067 (3)
H30A	0.7997	0.5264	0.5281	0.100*
H30B	0.7346	0.6154	0.4859	0.100*
H30C	0.8960	0.5611	0.4436	0.100*
C31	1.0144 (18)	0.3278 (7)	0.1390 (6)	0.060 (2)
C32	1.193 (2)	0.3555 (10)	0.0980 (8)	0.102 (4)
H32A	1.2844	0.3889	0.1434	0.153*
H32B	1.1447	0.3885	0.0425	0.153*
H32C	1.2671	0.3071	0.0814	0.153*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.056 (4)	0.039 (4)	0.072 (4)	0.002 (3)	0.015 (3)	0.002 (3)
O2	0.064 (4)	0.040 (3)	0.040 (3)	0.006 (3)	0.025 (3)	−0.004 (2)
O3	0.059 (4)	0.028 (3)	0.027 (2)	0.008 (2)	0.015 (2)	−0.001 (2)
O4	0.046 (3)	0.043 (3)	0.045 (3)	0.007 (2)	0.023 (2)	−0.005 (2)
O5	0.121 (7)	0.095 (6)	0.037 (3)	0.004 (5)	0.007 (4)	−0.010 (4)
O6	0.053 (3)	0.039 (3)	0.047 (3)	−0.006 (3)	0.023 (3)	−0.012 (2)
C1	0.042 (5)	0.040 (4)	0.031 (4)	0.000 (4)	0.003 (3)	0.001 (3)
C2	0.068 (6)	0.044 (5)	0.037 (4)	−0.016 (4)	−0.004 (4)	−0.008 (4)
C3	0.033 (4)	0.035 (5)	0.039 (4)	−0.004 (3)	0.012 (3)	0.003 (3)
C4	0.028 (4)	0.039 (4)	0.049 (4)	0.005 (3)	0.010 (3)	0.002 (3)
C5	0.033 (4)	0.034 (4)	0.032 (4)	0.007 (3)	0.007 (3)	0.001 (3)
C6	0.049 (5)	0.034 (4)	0.033 (4)	−0.005 (4)	0.007 (3)	−0.004 (3)
C7	0.050 (5)	0.045 (5)	0.030 (4)	0.004 (4)	0.012 (3)	−0.004 (3)
C8	0.021 (4)	0.029 (4)	0.044 (4)	0.004 (3)	0.004 (3)	0.004 (3)
C9	0.023 (4)	0.038 (4)	0.029 (3)	0.000 (3)	0.006 (3)	0.001 (3)
C10	0.025 (4)	0.038 (4)	0.033 (3)	0.002 (3)	0.008 (3)	−0.004 (3)
C11	0.039 (4)	0.029 (4)	0.033 (4)	0.001 (3)	0.010 (3)	−0.004 (3)
C12	0.041 (5)	0.037 (4)	0.043 (4)	−0.002 (3)	0.021 (3)	−0.001 (3)
C13	0.039 (4)	0.030 (4)	0.036 (4)	−0.001 (3)	0.018 (3)	0.002 (3)
C14	0.035 (4)	0.037 (4)	0.026 (3)	0.004 (3)	0.005 (3)	0.004 (3)
C15	0.050 (5)	0.037 (4)	0.035 (4)	0.003 (4)	0.017 (4)	0.001 (3)
C16	0.044 (5)	0.034 (4)	0.029 (3)	−0.002 (3)	0.013 (3)	−0.004 (3)
C17	0.052 (5)	0.026 (4)	0.029 (3)	−0.001 (3)	0.016 (3)	−0.001 (3)
C18	0.067 (6)	0.029 (4)	0.026 (3)	0.006 (3)	0.017 (4)	0.003 (3)
C19	0.045 (5)	0.033 (4)	0.034 (4)	0.003 (3)	0.017 (3)	0.003 (3)
C20	0.042 (4)	0.019 (3)	0.039 (4)	0.003 (3)	0.008 (3)	0.000 (3)
C21	0.031 (4)	0.038 (4)	0.038 (4)	0.005 (3)	0.006 (3)	−0.008 (3)
C22	0.027 (4)	0.031 (4)	0.044 (4)	0.000 (3)	0.007 (3)	−0.002 (3)
C23	0.055 (6)	0.044 (5)	0.051 (5)	0.018 (4)	0.011 (4)	0.010 (4)
C24	0.044 (5)	0.062 (6)	0.048 (5)	−0.003 (4)	−0.001 (4)	0.008 (4)
C25	0.053 (6)	0.045 (5)	0.059 (5)	0.010 (4)	0.003 (4)	0.015 (4)
C26	0.048 (5)	0.046 (5)	0.060 (5)	0.005 (4)	0.020 (4)	−0.002 (4)
C27	0.041 (5)	0.053 (5)	0.042 (4)	0.006 (4)	0.007 (4)	0.003 (4)
C28	0.031 (4)	0.038 (4)	0.055 (4)	0.010 (3)	0.020 (3)	0.006 (4)
C29	0.040 (5)	0.049 (5)	0.046 (4)	0.000 (4)	0.007 (4)	−0.006 (4)
C30	0.131 (9)	0.039 (5)	0.026 (4)	0.010 (5)	0.005 (5)	−0.008 (3)
C31	0.080 (7)	0.065 (6)	0.040 (5)	0.016 (5)	0.026 (5)	0.003 (4)
C32	0.118 (10)	0.134 (11)	0.070 (7)	−0.007 (9)	0.061 (7)	−0.006 (7)

Geometric parameters (Å, º) top

O1—C3	1.210 (9)	C15—C16	1.511 (11)
O2—C11	1.432 (8)	C15—H15A	0.9700
O2—H2	0.8200	C15—H15B	0.9700
O3—C16	1.430 (9)	C16—C17	1.502 (9)
O3—C20	1.455 (8)	C16—H16	0.9800
O4—C31	1.340 (11)	C17—C18	1.499 (10)
O4—C21	1.458 (9)	C18—C30	1.507 (13)
O5—C31	1.196 (13)	C18—C19	1.546 (10)
O6—C22	1.435 (9)	C18—H18	0.9800
O6—H6	0.8200	C19—C20	1.505 (10)
C1—C2	1.535 (12)	C19—H19A	0.9700
C1—C10	1.540 (10)	C19—H19B	0.9700
C1—H1A	0.9700	C20—C21	1.513 (10)
C1—H1B	0.9700	C20—H20	0.9800
C2—C3	1.499 (11)	C21—C22	1.557 (10)
C2—H2A	0.9700	C21—H21	0.9800
C2—H2B	0.9700	C22—C24	1.497 (11)
C3—C4	1.533 (11)	C22—C23	1.515 (11)
C4—C25	1.518 (11)	C23—H23A	0.9600
C4—C26	1.551 (10)	C23—H23B	0.9600
C4—C5	1.554 (11)	C23—H23C	0.9600
C5—C6	1.515 (10)	C24—H24A	0.9600
C5—C10	1.550 (10)	C24—H24B	0.9600
C5—H5	0.9800	C24—H24C	0.9600
C6—C7	1.518 (11)	C25—H25A	0.9600
C6—H6A	0.9700	C25—H25B	0.9600
C6—H6B	0.9700	C25—H25C	0.9600
C7—C8	1.549 (10)	C26—H26A	0.9600
C7—H7A	0.9700	C26—H26B	0.9600
C7—H7B	0.9700	C26—H26C	0.9600
C8—C28	1.545 (10)	C27—H27A	0.9600
C8—C14	1.564 (10)	C27—H27B	0.9600
C8—C9	1.579 (10)	C27—H27C	0.9600
C9—C11	1.533 (9)	C28—H28A	0.9600
C9—C10	1.589 (10)	C28—H28B	0.9600
C9—H9	0.9800	C28—H28C	0.9600
C10—C27	1.511 (10)	C29—H29A	0.9600
C11—C12	1.518 (10)	C29—H29B	0.9600
C11—H11	0.9800	C29—H29C	0.9600
C12—C13	1.492 (10)	C30—H30A	0.9600
C12—H12A	0.9700	C30—H30B	0.9600
C12—H12B	0.9700	C30—H30C	0.9600
C13—C17	1.308 (10)	C31—C32	1.466 (15)
C13—C14	1.507 (9)	C32—H32A	0.9600
C14—C29	1.535 (11)	C32—H32B	0.9600
C14—C15	1.573 (10)	C32—H32C	0.9600

C11—O2—H2	109.5	C17—C16—H16	109.4
C16—O3—C20	110.0 (5)	C15—C16—H16	109.4
C31—O4—C21	119.4 (7)	C13—C17—C18	131.0 (7)
C22—O6—H6	109.5	C13—C17—C16	110.7 (6)
C2—C1—C10	112.7 (6)	C18—C17—C16	118.2 (6)
C2—C1—H1A	109.1	C17—C18—C30	111.2 (7)
C10—C1—H1A	109.1	C17—C18—C19	107.5 (6)
C2—C1—H1B	109.1	C30—C18—C19	113.1 (7)
C10—C1—H1B	109.1	C17—C18—H18	108.3
H1A—C1—H1B	107.8	C30—C18—H18	108.3
C3—C2—C1	117.3 (7)	C19—C18—H18	108.3
C3—C2—H2A	108.0	C20—C19—C18	111.9 (6)
C1—C2—H2A	108.0	C20—C19—H19A	109.2
C3—C2—H2B	108.0	C18—C19—H19A	109.2
C1—C2—H2B	108.0	C20—C19—H19B	109.2
H2A—C2—H2B	107.2	C18—C19—H19B	109.2
O1—C3—C2	121.0 (7)	H19A—C19—H19B	107.9
O1—C3—C4	121.5 (7)	O3—C20—C19	109.1 (6)
C2—C3—C4	117.1 (7)	O3—C20—C21	105.5 (5)
C25—C4—C3	111.4 (6)	C19—C20—C21	116.1 (6)
C25—C4—C26	108.2 (7)	O3—C20—H20	108.6
C3—C4—C26	103.9 (6)	C19—C20—H20	108.6
C25—C4—C5	115.9 (7)	C21—C20—H20	108.6
C3—C4—C5	108.6 (6)	O4—C21—C20	104.0 (6)
C26—C4—C5	108.0 (6)	O4—C21—C22	106.3 (5)
C6—C5—C10	110.7 (6)	C20—C21—C22	117.2 (6)
C6—C5—C4	115.5 (6)	O4—C21—H21	109.7
C10—C5—C4	114.4 (6)	C20—C21—H21	109.7
C6—C5—H5	105.0	C22—C21—H21	109.7
C10—C5—H5	105.0	O6—C22—C24	106.3 (6)
C4—C5—H5	105.0	O6—C22—C23	108.8 (6)
C5—C6—C7	109.4 (6)	C24—C22—C23	111.1 (7)
C5—C6—H6A	109.8	O6—C22—C21	107.5 (5)
C7—C6—H6A	109.8	C24—C22—C21	113.8 (6)
C5—C6—H6B	109.8	C23—C22—C21	109.0 (6)
C7—C6—H6B	109.8	C22—C23—H23A	109.5
H6A—C6—H6B	108.2	C22—C23—H23B	109.5
C6—C7—C8	116.0 (6)	H23A—C23—H23B	109.5
C6—C7—H7A	108.3	C22—C23—H23C	109.5
C8—C7—H7A	108.3	H23A—C23—H23C	109.5
C6—C7—H7B	108.3	H23B—C23—H23C	109.5
C8—C7—H7B	108.3	C22—C24—H24A	109.5
H7A—C7—H7B	107.4	C22—C24—H24B	109.5
C28—C8—C7	108.4 (6)	H24A—C24—H24B	109.5
C28—C8—C14	109.5 (6)	C22—C24—H24C	109.5
C7—C8—C14	110.1 (6)	H24A—C24—H24C	109.5
C28—C8—C9	109.8 (6)	H24B—C24—H24C	109.5
C7—C8—C9	109.9 (6)	C4—C25—H25A	109.5
C14—C8—C9	109.1 (5)	C4—C25—H25B	109.5
C11—C9—C8	110.8 (6)	H25A—C25—H25B	109.5
C11—C9—C10	114.3 (5)	C4—C25—H25C	109.5
C8—C9—C10	115.5 (5)	H25A—C25—H25C	109.5
C11—C9—H9	105.0	H25B—C25—H25C	109.5
C8—C9—H9	105.0	C4—C26—H26A	109.5
C10—C9—H9	105.0	C4—C26—H26B	109.5
C27—C10—C1	108.5 (6)	H26A—C26—H26B	109.5
C27—C10—C5	111.1 (6)	C4—C26—H26C	109.5
C1—C10—C5	106.9 (6)	H26A—C26—H26C	109.5
C27—C10—C9	106.7 (6)	H26B—C26—H26C	109.5
C1—C10—C9	113.1 (6)	C10—C27—H27A	109.5
C5—C10—C9	110.6 (5)	C10—C27—H27B	109.5
O2—C11—C12	109.6 (6)	H27A—C27—H27B	109.5
O2—C11—C9	109.5 (6)	C10—C27—H27C	109.5
C12—C11—C9	112.1 (6)	H27A—C27—H27C	109.5
O2—C11—H11	108.5	H27B—C27—H27C	109.5
C12—C11—H11	108.5	C8—C28—H28A	109.5
C9—C11—H11	108.5	C8—C28—H28B	109.5
C13—C12—C11	110.1 (6)	H28A—C28—H28B	109.5
C13—C12—H12A	109.6	C8—C28—H28C	109.5
C11—C12—H12A	109.6	H28A—C28—H28C	109.5
C13—C12—H12B	109.6	H28B—C28—H28C	109.5
C11—C12—H12B	109.6	C14—C29—H29A	109.5
H12A—C12—H12B	108.2	C14—C29—H29B	109.5
C17—C13—C12	129.3 (7)	H29A—C29—H29B	109.5
C17—C13—C14	114.6 (6)	C14—C29—H29C	109.5
C12—C13—C14	115.3 (6)	H29A—C29—H29C	109.5
C13—C14—C29	111.5 (6)	H29B—C29—H29C	109.5
C13—C14—C8	108.4 (6)	C18—C30—H30A	109.5
C29—C14—C8	112.8 (6)	C18—C30—H30B	109.5
C13—C14—C15	100.7 (6)	H30A—C30—H30B	109.5
C29—C14—C15	108.5 (6)	C18—C30—H30C	109.5
C8—C14—C15	114.3 (6)	H30A—C30—H30C	109.5
C16—C15—C14	106.3 (5)	H30B—C30—H30C	109.5
C16—C15—H15A	110.5	O5—C31—O4	122.9 (9)
C14—C15—H15A	110.5	O5—C31—C32	126.4 (10)
C16—C15—H15B	110.5	O4—C31—C32	110.6 (10)
C14—C15—H15B	110.5	C31—C32—H32A	109.5
H15A—C15—H15B	108.7	C31—C32—H32B	109.5
O3—C16—C17	112.1 (6)	H32A—C32—H32B	109.5
O3—C16—C15	112.2 (6)	C31—C32—H32C	109.5
C17—C16—C15	104.2 (6)	H32A—C32—H32C	109.5
O3—C16—H16	109.4	H32B—C32—H32C	109.5

C10—C1—C2—C3	14.8 (10)	C17—C13—C14—C8	−112.1 (7)
C1—C2—C3—O1	139.2 (8)	C12—C13—C14—C8	58.6 (8)
C1—C2—C3—C4	−47.6 (10)	C17—C13—C14—C15	8.2 (9)
O1—C3—C4—C25	−38.8 (10)	C12—C13—C14—C15	178.8 (6)
C2—C3—C4—C25	148.1 (7)	C28—C8—C14—C13	64.1 (7)
O1—C3—C4—C26	77.4 (9)	C7—C8—C14—C13	−176.7 (6)
C2—C3—C4—C26	−95.7 (8)	C9—C8—C14—C13	−56.1 (7)
O1—C3—C4—C5	−167.7 (7)	C28—C8—C14—C29	−171.9 (6)
C2—C3—C4—C5	19.1 (9)	C7—C8—C14—C29	−52.8 (8)
C25—C4—C5—C6	41.8 (9)	C9—C8—C14—C29	67.9 (7)
C3—C4—C5—C6	168.2 (6)	C28—C8—C14—C15	−47.2 (7)
C26—C4—C5—C6	−79.7 (8)	C7—C8—C14—C15	71.9 (7)
C25—C4—C5—C10	−88.3 (8)	C9—C8—C14—C15	−167.5 (5)
C3—C4—C5—C10	38.0 (8)	C13—C14—C15—C16	−16.3 (8)
C26—C4—C5—C10	150.1 (6)	C29—C14—C15—C16	−133.5 (7)
C10—C5—C6—C7	−70.2 (8)	C8—C14—C15—C16	99.7 (7)
C4—C5—C6—C7	157.9 (6)	C20—O3—C16—C17	−56.3 (8)
C5—C6—C7—C8	41.4 (9)	C20—O3—C16—C15	−173.2 (6)
C6—C7—C8—C28	−103.5 (8)	C14—C15—C16—O3	140.1 (6)
C6—C7—C8—C14	136.8 (7)	C14—C15—C16—C17	18.6 (8)
C6—C7—C8—C9	16.6 (9)	C12—C13—C17—C18	11.1 (14)
C28—C8—C9—C11	−63.7 (8)	C14—C13—C17—C18	−179.8 (7)
C7—C8—C9—C11	177.1 (6)	C12—C13—C17—C16	−165.5 (7)
C14—C8—C9—C11	56.3 (7)	C14—C13—C17—C16	3.6 (9)
C28—C8—C9—C10	68.2 (7)	O3—C16—C17—C13	−135.9 (7)
C7—C8—C9—C10	−51.0 (8)	C15—C16—C17—C13	−14.3 (9)
C14—C8—C9—C10	−171.7 (6)	O3—C16—C17—C18	47.0 (9)
C2—C1—C10—C27	−81.3 (8)	C15—C16—C17—C18	168.6 (7)
C2—C1—C10—C5	38.6 (8)	C13—C17—C18—C30	−94.0 (11)
C2—C1—C10—C9	160.6 (6)	C16—C17—C18—C30	82.4 (8)
C6—C5—C10—C27	−83.3 (8)	C13—C17—C18—C19	141.7 (8)
C4—C5—C10—C27	49.3 (8)	C16—C17—C18—C19	−41.9 (9)
C6—C5—C10—C1	158.6 (6)	C17—C18—C19—C20	48.9 (9)
C4—C5—C10—C1	−68.9 (8)	C30—C18—C19—C20	−74.2 (8)
C6—C5—C10—C9	35.0 (8)	C16—O3—C20—C19	65.3 (7)
C4—C5—C10—C9	167.5 (6)	C16—O3—C20—C21	−169.3 (6)
C11—C9—C10—C27	−84.3 (7)	C18—C19—C20—O3	−62.6 (8)
C8—C9—C10—C27	145.4 (6)	C18—C19—C20—C21	178.4 (6)
C11—C9—C10—C1	34.9 (8)	C31—O4—C21—C20	−125.2 (7)
C8—C9—C10—C1	−95.4 (7)	C31—O4—C21—C22	110.5 (8)
C11—C9—C10—C5	154.8 (6)	O3—C20—C21—O4	66.9 (7)
C8—C9—C10—C5	24.5 (8)	C19—C20—C21—O4	−172.1 (6)
C8—C9—C11—O2	−177.1 (5)	O3—C20—C21—C22	−176.1 (6)
C10—C9—C11—O2	50.3 (8)	C19—C20—C21—C22	−55.1 (9)
C8—C9—C11—C12	−55.3 (8)	O4—C21—C22—O6	−173.8 (5)
C10—C9—C11—C12	172.1 (6)	C20—C21—C22—O6	70.5 (8)
O2—C11—C12—C13	175.4 (6)	O4—C21—C22—C24	68.7 (7)
C9—C11—C12—C13	53.7 (8)	C20—C21—C22—C24	−47.0 (9)
C11—C12—C13—C17	112.2 (9)	O4—C21—C22—C23	−56.0 (8)
C11—C12—C13—C14	−56.8 (9)	C20—C21—C22—C23	−171.7 (7)
C17—C13—C14—C29	123.1 (8)	C21—O4—C31—O5	−4.5 (13)
C12—C13—C14—C29	−66.2 (9)	C21—O4—C31—C32	176.9 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O6ⁱ	0.82	2.09	2.904 (7)	172
O6—H6···O1ⁱⁱ	0.82	2.07	2.867 (8)	165

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₃₂H₅₀O₆
M_r	530.72
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	6.525 (4), 15.885 (10), 14.401 (9)
β (°)	100.475 (10)
V (Å³)	1467.8 (16)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.47 × 0.40

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.959, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	7306, 2697, 1811
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.089, 0.236, 1.00
No. of reflections	2697
No. of parameters	343
No. of restraints	37
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O6ⁱ	0.82	2.09	2.904 (7)	172.3
O6—H6···O1ⁱⁱ	0.82	2.07	2.867 (8)	165.3

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x, y−1, z.

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