Euphorbia Factor L2: an ester of 7-hydroxy­lathyrol

Jiao, W.; Mao, Z.; Lu, R.

doi:10.1107/S1600536807055900

Euphorbia Factor L₂: an ester of 7-hydroxylathyrol

In the crystal structure of the title macrocyclic diterpenoid [systematic name: (2S*,3S*,4R*,5R*,7R*,9S*,11S*,15R*)-5,15-diacetoxy-14-oxolathyra-6(17),12(E)-diene-3,7-diyl dibenzoate], C₃₈H₄₂O₉, the molecule exhibits the tricyclic terpenoid skeleton of lathyrane, consisting of fused five-, 11- and three-membered rings. The five-membered ring adopts an envelope conformation. Intra- and intermolecular weak C—H

O hydrogen bonding helps to stabilize the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055900/xu2355sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055900/xu2355Isup2.hkl Contains datablock I

CCDC reference: 672874

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.010 Å
R factor = 0.054
wR factor = 0.171
Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.73 Ratio
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for        C26
PLAT245_ALERT_2_B U(iso) H26     Smaller than U(eq) C26     by ...       0.06 AngSq
PLAT410_ALERT_2_B Short Intra H...H Contact  H4     ..  H17B    ..       1.87 Ang.

Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         41 Perc.
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O2     -   C21     ..       5.27 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O3     -   C15     ..       5.17 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C28
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C37
PLAT245_ALERT_2_C U(iso) H1A     Smaller than U(eq) C1      by ...       0.02 AngSq
PLAT245_ALERT_2_C U(iso) H1B     Smaller than U(eq) C1      by ...       0.02 AngSq
PLAT245_ALERT_2_C U(iso) H27     Smaller than U(eq) C27     by ...       0.04 AngSq
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10

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           25.53
           From the CIF: _reflns_number_total               3765
           Count of symmetry unique reflns         3811
           Completeness (_total/calc)             98.79%
           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 C2     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          R

   0 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
  11 ALERT level C = Check and explain
   9 ALERT level G = General alerts; check

   8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  13 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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

Euphorbia is the genus in the family Euphorbiaceae, and is widely distributed throughout the world. Many species of this genus are being used as traditional drugs in China such as Euphorbia Fischeriana Steud. and Euphorbia kansui L.. Plants belonging to Euphorbia are known to be rich sources of terpenoids, especially various diterpenoids. Previous chemical investigations on the seeds of Euphorbia lathyris were focused on lathyrol and ingenol diterpenoids (Bicchi, et al. 2001). As a part of our research on the chemical constituents from this medicine, the title compound was isolated. Its structure was elucidated by spectroscopic analysis and was confirmed by single-crystal X-ray diffraction analysis.

The title compound shows the tricyclic terpenoid skeleton of lathyrane (Fig. 1), consisting of fused five-, eleven- and three-membered rings (A: C1–C4/C15, B: C4–C9/C11–C15, C: C9–C11). Rings A and B are trans-joined (H4–C4–C15–O3 = -153.7°), while rings B and C are cis-joined (H9–C9–C11–H11 = 1.13°). Ring A adopts an envelope conformation, with atom C3 0.65 Å out of the plane defined by atoms C1/C2/C4/C15. Intra-molecular and inter-molecular weak C—H···O hydrogen bonding helps to stabilize the crystal structure (Table 1).

Related literature top

For general background, see: Bicchi, et al. (2001); For a related structure, see: Appendino et al. (1999).

Experimental top

The seeds of Euphorbia lathyris were collected in Sichuan province of China. The powdered seeds (10 kg) were extracted with EtOH three times and filtered. The filtrate was evaporated in vacuo, the residue was suspended in H₂O and partitioned successively with EtOA. This EtOA extract was subjected to column chromatography on Si gel eluted with petroleum-EtOA (15:1, 10:1, 8:1, 4:1, 2:1 and 1:1) and methanol to yield fractions 1–10. Fraction 3 (10 g) was chromatographed over Si gel (petroleum ether-EtOA, 4:1) to give three fractions. The second fraction was eluted with petroleum-acetone (5:1) on Si gel, followed by RP18 (MeOH-H₂O, 85:15) to provide the pure title compound as colorless crystals. Suitable crystals were obtained by slow evaporation of a methanol solution at room temperature.

Computing details top

Data collection: DIFRAC (Gabe & White, 1993); cell refinement: DIFRAC (Gabe & White, 1993); data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Frarrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. View of the molecule of (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I), viewed down the A axis. H-atoms were omitted for clarity.

(I) top

Crystal data top

C₃₈H₄₂O₉	F(000) = 1368
M_r = 642.72	D_x = 1.171 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 27 reflections
a = 13.418 (6) Å	θ = 4.5–5.7°
b = 14.989 (4) Å	µ = 0.08 mm⁻¹
c = 18.126 (5) Å	T = 298 K
V = 3646 (2) Å³	Block, colourless
Z = 4	0.36 × 0.34 × 0.25 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.006
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.8°
Graphite monochromator	h = −1→16
ω/2–θ scans	k = −3→18
3800 measured reflections	l = −2→21
3765 independent reflections	3 standard reflections every 300 reflections
1525 reflections with I > 2σ(I)	intensity decay: 1.2%

Refinement top

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)] = 0.054	H-atom parameters constrained
wR(F²) = 0.171	w = 1/[σ²(F_o²) + (0.092P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max = 0.001
3765 reflections	Δρ_max = 0.18 e Å⁻³
436 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0043 (9)

Crystal data top

C₃₈H₄₂O₉	V = 3646 (2) Å³
M_r = 642.72	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 13.418 (6) Å	µ = 0.08 mm⁻¹
b = 14.989 (4) Å	T = 298 K
c = 18.126 (5) Å	0.36 × 0.34 × 0.25 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.006
3800 measured reflections	3 standard reflections every 300 reflections
3765 independent reflections	intensity decay: 1.2%
1525 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 0.91	Δρ_max = 0.18 e Å⁻³
3765 reflections	Δρ_min = −0.18 e Å⁻³
436 parameters

Special details top

Experimental. ¹³C NMR (150 MHz, CDCl₃, δ, p.p.m.): 47.88(C1), 37.63(C2), 79.55(C3), 52.92(C4), 64.24(C5), 142.09 (C6), 78.57(C7), 28.79(C8), 31.54(C9), 24.65(C10), 27.78(C11), 142.61 (C12), 135.56(C13), 197.53(C14), 91.98 (C15), 14.12(C16), 119.60(C17), 28.68(C18), 16.61(C19), 12.73(C20), 165.97(C21), 130.34(C22),129.65(C23), 128.31(C24), 135.56(C25), 128.31(C26), 129.65(C27), 169.69(C28), 21.83(C29), 165.60(C30), 130.16(C31), 129.60(C32), 128.32(C33), 135.56(C34), 128.32(C35), 129.60(C36), 169.33(C37), 20.91(C38).

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	1.0377 (5)	0.2624 (4)	0.7591 (3)	0.122 (2)
O2	0.9735 (3)	0.3457 (3)	0.8502 (2)	0.0665 (12)
O3	0.9039 (3)	0.4391 (2)	0.9900 (2)	0.0678 (12)
O4	0.9028 (5)	0.5847 (3)	1.0151 (4)	0.124 (2)
O5	1.1394 (4)	0.5087 (4)	1.0605 (3)	0.114 (2)
O6	0.9231 (3)	0.0905 (2)	1.0792 (2)	0.0647 (12)
O7	1.0540 (4)	0.0179 (3)	1.1286 (3)	0.0835 (14)
O8	0.9920 (3)	0.1948 (2)	0.9494 (2)	0.0651 (12)
O9	0.8264 (4)	0.1850 (4)	0.9472 (4)	0.108 (2)
C1	1.0492 (6)	0.4971 (4)	0.9242 (4)	0.083 (2)
H1A	0.9928	0.5168	0.8949	0.066 (9)*
H1B	1.0856	0.5491	0.9410	0.066 (9)*
C2	1.1172 (5)	0.4361 (4)	0.8783 (4)	0.074 (2)
H2	1.1830	0.4345	0.9016	0.074 (7)*
C3	1.0681 (5)	0.3479 (4)	0.8898 (3)	0.0649 (18)
H3	1.1117	0.2991	0.8740	0.074 (7)*
C4	1.0490 (4)	0.3439 (3)	0.9722 (3)	0.0511 (15)
H4	1.1150	0.3385	0.9948	0.074 (7)*
C5	0.9883 (4)	0.2666 (3)	1.0035 (3)	0.0490 (15)
H5	0.9189	0.2861	1.0084	0.074 (7)*
C6	1.0215 (5)	0.2276 (4)	1.0770 (3)	0.0541 (15)
C7	0.9500 (5)	0.1715 (3)	1.1211 (3)	0.0543 (16)
H7	0.9843	0.1526	1.1663	0.074 (7)*
C8	0.8521 (5)	0.2145 (4)	1.1434 (3)	0.0622 (17)
H8A	0.8298	0.2522	1.1032	0.066 (9)*
H8B	0.8028	0.1678	1.1497	0.066 (9)*
C9	0.8550 (5)	0.2695 (5)	1.2126 (3)	0.0660 (19)
H9	0.8699	0.2341	1.2567	0.074 (7)*
C10	0.7880 (5)	0.3469 (5)	1.2283 (4)	0.0680 (19)
C11	0.9000 (5)	0.3631 (4)	1.2156 (3)	0.0696 (19)
H11	0.9391	0.3768	1.2599	0.074 (7)*
C12	0.9366 (5)	0.4015 (4)	1.1477 (4)	0.0618 (17)
H12	0.9004	0.3881	1.1054	0.118 (9)*
C13	1.0172 (5)	0.4546 (4)	1.1383 (4)	0.0719 (19)
C14	1.0577 (5)	0.4734 (4)	1.0657 (4)	0.0721 (19)
C15	1.0136 (5)	0.4413 (4)	0.9903 (4)	0.0613 (18)
C16	1.1299 (6)	0.4676 (6)	0.7974 (4)	0.106 (3)
H16A	1.0657	0.4811	0.7768	0.143 (8)*
H16B	1.1608	0.4211	0.7691	0.143 (8)*
H16C	1.1710	0.5199	0.7962	0.143 (8)*
C17	1.1122 (5)	0.2392 (5)	1.1031 (4)	0.086 (2)
H17A	1.1305	0.2131	1.1476	0.12 (2)*
H17B	1.1579	0.2736	1.0770	0.12 (2)*
C18	0.7534 (6)	0.3568 (6)	1.3075 (4)	0.105 (3)
H18A	0.6909	0.3266	1.3137	0.143 (8)*
H18B	0.7452	0.4189	1.3188	0.143 (8)*
H18C	0.8021	0.3312	1.3400	0.143 (8)*
C19	0.7140 (5)	0.3800 (5)	1.1713 (4)	0.085 (2)
H19A	0.6511	0.3507	1.1785	0.143 (8)*
H19B	0.7385	0.3671	1.1227	0.143 (8)*
H19C	0.7055	0.4433	1.1766	0.143 (8)*
C20	1.0775 (6)	0.4896 (7)	1.2024 (4)	0.126 (4)
H20A	1.1420	0.4617	1.2025	0.143 (8)*
H20B	1.0437	0.4762	1.2478	0.143 (8)*
H20C	1.0853	0.5530	1.1977	0.143 (8)*
C21	0.9704 (6)	0.3046 (5)	0.7848 (4)	0.082 (2)
C22	0.8711 (6)	0.3159 (5)	0.7483 (4)	0.081 (2)
C23	0.8010 (6)	0.3731 (5)	0.7735 (4)	0.075 (2)
H23	0.8130	0.4059	0.8162	0.118 (9)*
C24	0.7110 (7)	0.3833 (6)	0.7363 (6)	0.097 (3)
H24	0.6632	0.4223	0.7547	0.118 (9)*
C25	0.6925 (8)	0.3379 (8)	0.6745 (6)	0.128 (4)
H25	0.6323	0.3456	0.6499	0.118 (9)*
C26	0.7630 (10)	0.2791 (9)	0.6470 (6)	0.183 (6)
H26	0.7503	0.2470	0.6041	0.118 (9)*
C27	0.8542 (8)	0.2686 (8)	0.6849 (5)	0.153 (5)
H27	0.9024	0.2297	0.6669	0.118 (9)*
C28	0.9038 (7)	0.1608 (5)	0.9250 (4)	0.080 (2)
C29	0.9208 (7)	0.0912 (6)	0.8680 (4)	0.123 (3)
H29A	0.9411	0.1189	0.8227	0.143 (8)*
H29B	0.8602	0.0585	0.8601	0.143 (8)*
H29C	0.9720	0.0511	0.8845	0.143 (8)*
C30	0.9808 (6)	0.0189 (4)	1.0890 (4)	0.0637 (17)
C31	0.9457 (5)	−0.0591 (4)	1.0448 (3)	0.0580 (16)
C32	1.0046 (5)	−0.1350 (4)	1.0458 (4)	0.082 (2)
H32	1.0637	−0.1356	1.0726	0.118 (9)*
C33	0.9758 (7)	−0.2095 (5)	1.0072 (5)	0.105 (3)
H33	1.0148	−0.2607	1.0085	0.118 (9)*
C34	0.8890 (6)	−0.2084 (5)	0.9664 (5)	0.104 (3)
H34	0.8708	−0.2579	0.9386	0.118 (9)*
C35	0.8301 (6)	−0.1345 (4)	0.9672 (5)	0.094 (3)
H35	0.7704	−0.1345	0.9412	0.118 (9)*
C36	0.8580 (5)	−0.0600 (4)	1.0059 (4)	0.075 (2)
H36	0.8172	−0.0098	1.0058	0.118 (9)*
C37	0.8580 (7)	0.5183 (6)	1.0018 (4)	0.086 (2)
C38	0.7478 (6)	0.5077 (6)	0.9931 (5)	0.116 (3)
H38A	0.7319	0.5012	0.9417	0.143 (8)*
H38B	0.7146	0.5594	1.0124	0.143 (8)*
H38C	0.7261	0.4557	1.0194	0.143 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.132 (5)	0.157 (5)	0.076 (3)	0.091 (5)	−0.009 (4)	−0.026 (4)
O2	0.061 (3)	0.080 (3)	0.058 (3)	0.030 (2)	0.003 (2)	−0.006 (2)
O3	0.074 (3)	0.052 (2)	0.078 (3)	0.017 (2)	0.012 (3)	0.002 (2)
O4	0.165 (6)	0.045 (3)	0.163 (6)	0.014 (4)	0.063 (5)	0.003 (3)
O5	0.087 (4)	0.128 (4)	0.128 (4)	−0.074 (4)	0.042 (3)	−0.038 (4)
O6	0.065 (3)	0.046 (2)	0.083 (3)	−0.010 (2)	−0.021 (3)	0.001 (2)
O7	0.069 (3)	0.080 (3)	0.102 (4)	0.010 (3)	−0.025 (3)	−0.007 (3)
O8	0.072 (3)	0.056 (2)	0.067 (3)	−0.007 (2)	−0.004 (2)	−0.014 (2)
O9	0.066 (3)	0.115 (4)	0.142 (5)	−0.005 (3)	−0.036 (4)	−0.002 (4)
C1	0.096 (5)	0.049 (4)	0.105 (5)	0.005 (4)	0.020 (5)	0.008 (4)
C2	0.067 (5)	0.069 (4)	0.087 (5)	0.008 (4)	0.023 (4)	0.015 (4)
C3	0.055 (4)	0.067 (4)	0.073 (5)	0.018 (4)	0.012 (4)	0.004 (4)
C4	0.046 (3)	0.046 (3)	0.061 (4)	0.004 (3)	0.004 (3)	0.002 (3)
C5	0.045 (3)	0.044 (3)	0.058 (4)	0.000 (3)	0.005 (3)	−0.008 (3)
C6	0.056 (4)	0.046 (3)	0.061 (4)	−0.002 (3)	−0.009 (3)	0.005 (3)
C7	0.062 (4)	0.048 (3)	0.052 (3)	−0.003 (3)	−0.009 (3)	0.004 (3)
C8	0.059 (4)	0.059 (4)	0.069 (4)	−0.015 (3)	−0.001 (3)	0.006 (4)
C9	0.057 (4)	0.086 (5)	0.055 (4)	−0.024 (4)	0.003 (3)	0.010 (4)
C10	0.063 (4)	0.081 (5)	0.060 (4)	−0.026 (4)	0.018 (4)	−0.012 (4)
C11	0.069 (5)	0.086 (5)	0.054 (4)	−0.032 (4)	−0.001 (4)	−0.009 (4)
C12	0.055 (4)	0.058 (4)	0.072 (4)	−0.018 (3)	0.013 (4)	−0.011 (3)
C13	0.067 (4)	0.077 (4)	0.072 (5)	−0.018 (4)	0.007 (4)	−0.025 (4)
C14	0.075 (5)	0.050 (3)	0.091 (5)	−0.023 (4)	0.031 (4)	−0.024 (4)
C15	0.050 (4)	0.051 (3)	0.082 (5)	−0.004 (3)	0.025 (4)	0.012 (3)
C16	0.112 (7)	0.119 (7)	0.087 (5)	0.015 (6)	0.042 (5)	0.032 (5)
C17	0.057 (4)	0.094 (5)	0.107 (6)	−0.011 (4)	−0.015 (4)	0.037 (5)
C18	0.093 (6)	0.127 (7)	0.095 (6)	−0.057 (5)	0.027 (5)	−0.018 (5)
C19	0.077 (5)	0.090 (5)	0.089 (5)	−0.017 (5)	0.009 (5)	−0.020 (4)
C20	0.096 (6)	0.183 (9)	0.099 (6)	−0.080 (7)	0.016 (5)	−0.053 (6)
C21	0.078 (5)	0.094 (5)	0.072 (5)	0.041 (5)	0.001 (4)	0.014 (4)
C22	0.100 (6)	0.086 (5)	0.058 (5)	0.009 (5)	0.001 (4)	0.004 (4)
C23	0.066 (5)	0.081 (5)	0.078 (5)	0.008 (4)	0.009 (4)	0.018 (4)
C24	0.075 (6)	0.108 (6)	0.107 (7)	0.007 (5)	0.008 (6)	0.037 (6)
C25	0.105 (8)	0.175 (11)	0.103 (8)	0.009 (8)	−0.029 (7)	0.033 (8)
C26	0.167 (12)	0.256 (15)	0.126 (9)	0.086 (12)	−0.072 (9)	−0.065 (10)
C27	0.157 (10)	0.196 (11)	0.105 (7)	0.092 (9)	−0.041 (7)	−0.049 (8)
C28	0.101 (6)	0.078 (5)	0.061 (5)	−0.026 (5)	−0.030 (5)	−0.006 (4)
C29	0.162 (9)	0.127 (7)	0.080 (5)	−0.042 (7)	−0.010 (6)	−0.036 (5)
C30	0.062 (4)	0.056 (4)	0.073 (4)	−0.004 (4)	0.000 (4)	0.016 (4)
C31	0.048 (4)	0.048 (3)	0.078 (4)	−0.002 (3)	−0.002 (4)	0.005 (3)
C32	0.055 (4)	0.068 (4)	0.122 (6)	−0.003 (4)	−0.014 (4)	0.000 (4)
C33	0.093 (6)	0.055 (4)	0.166 (8)	0.019 (5)	−0.022 (6)	−0.011 (5)
C34	0.082 (6)	0.068 (5)	0.161 (8)	0.000 (5)	−0.030 (6)	−0.038 (5)
C35	0.083 (6)	0.058 (4)	0.140 (7)	0.005 (4)	−0.042 (5)	−0.015 (5)
C36	0.066 (5)	0.061 (4)	0.096 (5)	0.009 (4)	−0.019 (4)	0.003 (4)
C37	0.107 (7)	0.065 (5)	0.088 (5)	0.039 (5)	0.029 (5)	0.021 (5)
C38	0.096 (7)	0.132 (7)	0.120 (7)	0.062 (6)	0.019 (5)	0.022 (6)

Geometric parameters (Å, º) top

O1—C21	1.198 (8)	C16—H16A	0.9600
O2—C21	1.337 (8)	C16—H16B	0.9600
O2—C3	1.458 (7)	C16—H16C	0.9600
O3—C37	1.355 (8)	C17—H17A	0.9300
O3—C15	1.472 (7)	C17—H17B	0.9300
O4—C37	1.187 (9)	C18—H18A	0.9600
O5—C14	1.222 (7)	C18—H18B	0.9600
O6—C30	1.336 (7)	C18—H18C	0.9600
O6—C7	1.477 (6)	C19—H19A	0.9600
O7—C30	1.216 (7)	C19—H19B	0.9600
O8—C28	1.363 (8)	C19—H19C	0.9600
O8—C5	1.456 (6)	C20—H20A	0.9600
O9—C28	1.171 (9)	C20—H20B	0.9600
C1—C2	1.536 (8)	C20—H20C	0.9600
C1—C15	1.537 (8)	C21—C22	1.498 (10)
C1—H1A	0.9700	C22—C23	1.353 (9)
C1—H1B	0.9700	C22—C27	1.369 (11)
C2—C3	1.491 (8)	C23—C24	1.391 (10)
C2—C16	1.549 (8)	C23—H23	0.9300
C2—H2	0.9800	C24—C25	1.333 (12)
C3—C4	1.517 (7)	C24—H24	0.9300
C3—H3	0.9800	C25—C26	1.385 (13)
C4—C5	1.527 (7)	C25—H25	0.9300
C4—C15	1.570 (8)	C26—C27	1.412 (14)
C4—H4	0.9800	C26—H26	0.9300
C5—C6	1.520 (8)	C27—H27	0.9300
C5—H5	0.9800	C28—C29	1.486 (10)
C6—C17	1.317 (8)	C29—H29A	0.9600
C6—C7	1.507 (8)	C29—H29B	0.9600
C7—C8	1.518 (8)	C29—H29C	0.9600
C7—H7	0.9800	C30—C31	1.493 (8)
C8—C9	1.503 (8)	C31—C36	1.371 (9)
C8—H8A	0.9700	C31—C32	1.386 (8)
C8—H8B	0.9700	C32—C33	1.373 (9)
C9—C10	1.495 (10)	C32—H32	0.9300
C9—C11	1.528 (9)	C33—C34	1.379 (11)
C9—H9	0.9800	C33—H33	0.9300
C10—C19	1.516 (10)	C34—C35	1.361 (9)
C10—C18	1.516 (9)	C34—H34	0.9300
C10—C11	1.540 (9)	C35—C36	1.370 (9)
C11—C12	1.445 (8)	C35—H35	0.9300
C11—H11	0.9800	C36—H36	0.9300
C12—C13	1.354 (8)	C37—C38	1.495 (12)
C12—H12	0.9300	C38—H38A	0.9600
C13—C14	1.451 (9)	C38—H38B	0.9600
C13—C20	1.510 (9)	C38—H38C	0.9600
C14—C15	1.566 (9)

C21—O2—C3	118.3 (5)	C2—C16—H16C	109.5
C37—O3—C15	115.7 (6)	H16A—C16—H16C	109.5
C30—O6—C7	116.8 (5)	H16B—C16—H16C	109.5
C28—O8—C5	117.7 (5)	C6—C17—H17A	120.0
C2—C1—C15	106.5 (5)	C6—C17—H17B	120.0
C2—C1—H1A	110.4	H17A—C17—H17B	120.0
C15—C1—H1A	110.4	C10—C18—H18A	109.5
C2—C1—H1B	110.4	C10—C18—H18B	109.5
C15—C1—H1B	110.4	H18A—C18—H18B	109.5
H1A—C1—H1B	108.6	C10—C18—H18C	109.5
C3—C2—C1	100.9 (5)	H18A—C18—H18C	109.5
C3—C2—C16	116.8 (6)	H18B—C18—H18C	109.5
C1—C2—C16	113.4 (6)	C10—C19—H19A	109.5
C3—C2—H2	108.4	C10—C19—H19B	109.5
C1—C2—H2	108.4	H19A—C19—H19B	109.5
C16—C2—H2	108.4	C10—C19—H19C	109.5
O2—C3—C2	109.6 (5)	H19A—C19—H19C	109.5
O2—C3—C4	109.7 (5)	H19B—C19—H19C	109.5
C2—C3—C4	104.3 (5)	C13—C20—H20A	109.5
O2—C3—H3	111.0	C13—C20—H20B	109.5
C2—C3—H3	111.0	H20A—C20—H20B	109.5
C4—C3—H3	111.0	C13—C20—H20C	109.5
C3—C4—C5	119.2 (5)	H20A—C20—H20C	109.5
C3—C4—C15	102.7 (5)	H20B—C20—H20C	109.5
C5—C4—C15	117.8 (4)	O1—C21—O2	124.4 (7)
C3—C4—H4	105.3	O1—C21—C22	124.0 (7)
C5—C4—H4	105.3	O2—C21—C22	111.6 (6)
C15—C4—H4	105.3	C23—C22—C27	119.8 (8)
O8—C5—C6	107.2 (4)	C23—C22—C21	122.7 (7)
O8—C5—C4	106.9 (4)	C27—C22—C21	117.4 (8)
C6—C5—C4	117.5 (5)	C22—C23—C24	120.5 (8)
O8—C5—H5	108.3	C22—C23—H23	119.7
C6—C5—H5	108.3	C24—C23—H23	119.7
C4—C5—H5	108.3	C25—C24—C23	120.9 (9)
C17—C6—C7	118.1 (6)	C25—C24—H24	119.6
C17—C6—C5	122.3 (6)	C23—C24—H24	119.6
C7—C6—C5	119.5 (5)	C24—C25—C26	120.0 (10)
O6—C7—C6	110.0 (5)	C24—C25—H25	120.0
O6—C7—C8	105.9 (5)	C26—C25—H25	120.0
C6—C7—C8	117.1 (4)	C25—C26—C27	119.2 (10)
O6—C7—H7	107.9	C25—C26—H26	120.4
C6—C7—H7	107.9	C27—C26—H26	120.4
C8—C7—H7	107.9	C22—C27—C26	119.6 (9)
C9—C8—C7	115.7 (5)	C22—C27—H27	120.2
C9—C8—H8A	108.4	C26—C27—H27	120.2
C7—C8—H8A	108.4	O9—C28—O8	122.8 (7)
C9—C8—H8B	108.4	O9—C28—C29	126.3 (8)
C7—C8—H8B	108.4	O8—C28—C29	110.8 (8)
H8A—C8—H8B	107.4	C28—C29—H29A	109.5
C10—C9—C8	124.7 (6)	C28—C29—H29B	109.5
C10—C9—C11	61.3 (4)	H29A—C29—H29B	109.5
C8—C9—C11	122.9 (5)	C28—C29—H29C	109.5
C10—C9—H9	112.9	H29A—C29—H29C	109.5
C8—C9—H9	112.9	H29B—C29—H29C	109.5
C11—C9—H9	112.9	O7—C30—O6	123.8 (6)
C9—C10—C19	121.3 (6)	O7—C30—C31	124.2 (6)
C9—C10—C18	116.1 (7)	O6—C30—C31	112.0 (6)
C19—C10—C18	114.3 (7)	C36—C31—C32	119.2 (6)
C9—C10—C11	60.4 (4)	C36—C31—C30	123.7 (6)
C19—C10—C11	119.1 (6)	C32—C31—C30	117.1 (6)
C18—C10—C11	115.1 (6)	C33—C32—C31	120.0 (7)
C12—C11—C9	118.0 (5)	C33—C32—H32	120.0
C12—C11—C10	121.4 (6)	C31—C32—H32	120.0
C9—C11—C10	58.3 (4)	C32—C33—C34	120.1 (7)
C12—C11—H11	115.6	C32—C33—H33	120.0
C9—C11—H11	115.6	C34—C33—H33	120.0
C10—C11—H11	115.6	C35—C34—C33	119.6 (7)
C13—C12—C11	127.8 (6)	C35—C34—H34	120.2
C13—C12—H12	116.1	C33—C34—H34	120.2
C11—C12—H12	116.1	C34—C35—C36	120.7 (7)
C12—C13—C14	121.8 (6)	C34—C35—H35	119.6
C12—C13—C20	122.4 (6)	C36—C35—H35	119.6
C14—C13—C20	115.4 (6)	C35—C36—C31	120.3 (6)
O5—C14—C13	119.4 (7)	C35—C36—H36	119.8
O5—C14—C15	113.9 (6)	C31—C36—H36	119.8
C13—C14—C15	126.2 (5)	O4—C37—O3	122.4 (8)
O3—C15—C1	108.7 (5)	O4—C37—C38	127.7 (8)
O3—C15—C14	112.8 (5)	O3—C37—C38	109.9 (8)
C1—C15—C14	113.4 (5)	C37—C38—H38A	109.5
O3—C15—C4	106.3 (5)	C37—C38—H38B	109.5
C1—C15—C4	104.4 (5)	H38A—C38—H38B	109.5
C14—C15—C4	110.7 (5)	C37—C38—H38C	109.5
C2—C16—H16A	109.5	H38A—C38—H38C	109.5
C2—C16—H16B	109.5	H38B—C38—H38C	109.5
H16A—C16—H16B	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O3	0.93	2.23	2.946 (8)	134
C17—H17B···O9ⁱ	0.93	2.39	3.222 (9)	150
C19—H19A···O1ⁱⁱ	0.96	2.54	3.427 (10)	153
C35—H35···O5ⁱⁱ	0.93	2.58	3.218 (9)	126

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

Experimental details

Crystal data
Chemical formula	C₃₈H₄₂O₉
M_r	642.72
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	13.418 (6), 14.989 (4), 18.126 (5)
V (Å³)	3646 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.36 × 0.34 × 0.25

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3800, 3765, 1525
R_int	0.006
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.171, 0.91
No. of reflections	3765
No. of parameters	436
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Frarrugia, 1997).