Euphorbia factor L8: a diterpenoid from the seeds of Euphorbia lathyris

Jiao, W.; Mao, Z.; Dong, W.; Deng, M.; Lu, R.

doi:10.1107/S1600536807066901

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o331

https://doi.org/10.1107/S1600536807066901

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Euphorbia factor L₈: a diterpenoid from the seeds of Euphorbia lathyris

Wei Jiao,^a Zhi-hua Mao,^b Wei-wei Dong,^a Mei-cai Deng ^a and Run-hua Lu ^a ^*

^aChengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, People's Republic of China, and ^bCenter for Testing and Analysis, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: lurh@cib.ac.cn

(Received 3 October 2007; accepted 14 December 2007; online 21 December 2007)

The title compound [systematic name: (2S*,3S*,4R*,5R*,9S*,11S*,15R*)-5,15-diacetoxy-3-nicotinoyloxy-14-oxolathyra-6(17),12(E)-diene], C₃₀H₃₇NO₇, was isolated from the seeds of Euphorbia lathyris. The tricyclic diterpenoid molecule contains an 11-membered ring, a five-membered ring exhibiting an envelope conformation and a three-membered ring. The 11-membered ring is cis-fused with the three-membered ring and trans-fused with the five-membered ring.

Related literature

For related literature, see: Appendino et al. (1999 ); Fujiwara et al. (1996 ); Kupchan et al. (1976 ); the Pharmacopoeia Commission of the People's Republic of China (2005 ).

Experimental

Crystal data

C₃₀H₃₇NO₇
M_r = 523.61
Orthorhombic, P 2₁ 2₁ 2₁
a = 10.162 (6) Å
b = 15.249 (5) Å
c = 18.802 (9) Å
V = 2914 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.36 × 0.34 × 0.25 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3444 measured reflections
3065 independent reflections
1462 reflections with I > 2σ(I)
R_int = 0.003
3 standard reflections every 300 reflections intensity decay: 0.3%

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.118
S = 0.93
3065 reflections
354 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: DIFRAC (Gabe & White, 1993 ); cell refinement: DIFRAC; 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 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807066901/ww2099sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807066901/ww2099Isup2.hkl

checkCIF report

Comment top

The seed of Euphorbia lathyris is a traditional Chinese medicine which has been used for the treatment of hydropsy, ascites, amenorrhea, scabies (Pharmacopoeia Commission of the People's Republic of China, 2005). Several constituents in this plant proved to have significant activity (Kupchan et al., 1976; Fujiwara et al., 1996) and this medicine has been used to treat tumors and cancer in many countries. In our current investigation, Euphorbia Factor L₈ (I) was isolated from the seeds of this plant. The structure of (I) was elucidated by comprehensive spectroscopic analysis, and was confirmed by single-crystal X-ray diffraction analysis reported here (Fig. 1). The title compound shows the tricyclic terpenoid skeleton of lathyrane, 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 (torsion angle H4–C4–C15–O3 = -152.8°), while rings B and C are cis-joined (H9–C9–C11–H11 = 0.99°). Ring A adopts an envelope conformation, with atom C3 0.64 Å out of the plane defined by atoms C1/C2/C4/C15.

Related literature top

For related literature, see: Appendino et al. (1999); Fujiwara et al. (1996); Kupchan et al. (1976); the Pharmacopoeia Commission of the People's Republic of China (2005).

Experimental top

The seeds of E. lathyris (10 kg) were collected in Sichuan province, People's Republic of China and extracted with 95% EtOH at room temperature. The extract was concentrated in vacuo and filtered. The filtrate was partitioned between EtOAc and H₂O. The EtOAc soluble materials (1 kg) were subjected to silica-gel column chromatography (160–200 mesh, 4 kg) with petrol-EtOAc stepwise elution. The column chromatographic fractions (500 ml each) were combined into 12 fractions according to thin-layer chromatography monitoring analysis. Fraction 5 (7.5 g) was applied to a RP-18 silica-gel column and eluted with MeOH/H₂O (7:3) to yield five fractions. Fraction 5.2 (1.4 g) was subjected to silica-gel column chromatography (200–300 mesh, 50 g) and eluted with petrol-EtOAc (5:1) to afford the compound (I). The isolated product was recrystallized at room temperature from acetone to afford the block crytals. ¹³C NMR (150 MHz, CDCl₃, δ, p.p.m.): 48.6(C1), 37.7(C2), 81.6(C3), 52.3(C4), 65.5(C5), 144.4(C6), 34.9(C7), 21.0(C8), 35.4(C9), 25.3(C10), 28.5(C11), 146.6(C12), 134.3(C13), 196.6(C14), 92.5(C15), 14.2(C16), 115.5(C17), 29.0(C18), 16.8(C19), 12.4(C20), 164.9(C21), 126.0(C22), 137.0(C23), 123.3(C24), 153.5(C25), 151.0(C26), 170.2(C27), 21.6(C28), 169.7(C29), 22.1(C30).

Structure description top

For related literature, see: Appendino et al. (1999); Fujiwara et al. (1996); Kupchan et al. (1976); the Pharmacopoeia Commission of the People's Republic of China (2005).

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 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. ORTEP plot of compound (I) showing the atom-numbering scheme and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The crystal packing of (I), viewed down the a axis. H-atoms omitted for clarity.

(2S*,3S*,4R*,5R*,9S*,11S*, 15R*)-5,15-diacetoxy-3-nicotinoyloxy-14-oxolathyra-6(17),12(E)- diene top

Crystal data top

C₃₀H₃₇NO₇	D_x = 1.194 Mg m⁻³
M_r = 523.61	Melting point: 469(1) K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 24 reflections
a = 10.162 (6) Å	θ = 4.5–5.5°
b = 15.249 (5) Å	µ = 0.08 mm⁻¹
c = 18.802 (9) Å	T = 298 K
V = 2914 (2) Å³	Block, colourless
Z = 4	0.36 × 0.34 × 0.25 mm
F(000) = 1120

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.003
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 1.7°
Graphite monochromator	h = −1→12
ω/2θ scans	k = −3→18
3444 measured reflections	l = −1→22
3065 independent reflections	3 standard reflections every 300 reflections
1462 reflections with I > 2σ(I)	intensity decay: 0.3%

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 0.93	w = 1/[σ²(F_o²) + (0.0541P)²] where P = (F_o² + 2F_c²)/3
3065 reflections	(Δ/σ)_max < 0.001
354 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₃₀H₃₇NO₇	V = 2914 (2) Å³
M_r = 523.61	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 10.162 (6) Å	µ = 0.08 mm⁻¹
b = 15.249 (5) Å	T = 298 K
c = 18.802 (9) Å	0.36 × 0.34 × 0.25 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.003
3444 measured reflections	3 standard reflections every 300 reflections
3065 independent reflections	intensity decay: 0.3%
1462 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 0.93	Δρ_max = 0.18 e Å⁻³
3065 reflections	Δρ_min = −0.24 e Å⁻³
354 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	0.4410 (3)	0.60363 (17)	0.75057 (16)	0.0422 (8)
O2	0.3383 (4)	0.6889 (2)	0.67028 (18)	0.0745 (12)
O3	0.6027 (3)	0.50915 (17)	0.86366 (15)	0.0442 (8)
O4	0.5648 (4)	0.4774 (2)	0.97859 (19)	0.0725 (11)
O5	0.6858 (4)	0.6902 (2)	0.97413 (16)	0.0600 (10)
O6	0.6894 (4)	0.63864 (19)	0.68532 (16)	0.0539 (9)
O7	0.6709 (5)	0.4992 (3)	0.6477 (2)	0.0887 (14)
N1	0.3198 (5)	0.3782 (2)	0.6543 (2)	0.0653 (13)
C1	0.4680 (5)	0.6336 (3)	0.9021 (2)	0.0463 (13)
H1A	0.4056	0.5857	0.8985	0.071 (7)*
H1B	0.4675	0.6552	0.9506	0.071 (7)*
C2	0.4308 (5)	0.7065 (3)	0.8509 (2)	0.0465 (12)
H2	0.4703	0.7610	0.8684	0.045 (5)*
C3	0.5024 (5)	0.6806 (3)	0.7833 (2)	0.0401 (12)
H3	0.5082	0.7297	0.7498	0.045 (5)*
C4	0.6377 (5)	0.6534 (3)	0.8103 (2)	0.0405 (12)
H4	0.6821	0.7076	0.8246	0.045 (5)*
C5	0.7290 (5)	0.6088 (3)	0.7565 (2)	0.0441 (12)
H5	0.7175	0.5451	0.7596	0.045 (5)*
C6	0.8749 (5)	0.6304 (3)	0.7607 (3)	0.0491 (14)
C7	0.9639 (6)	0.5689 (4)	0.7203 (3)	0.0763 (18)
H7A	1.0510	0.5950	0.7184	0.071 (7)*
H7B	0.9318	0.5648	0.6718	0.071 (7)*
C8	0.9773 (6)	0.4764 (4)	0.7498 (3)	0.0732 (17)
H8A	0.8901	0.4547	0.7612	0.071 (7)*
H8B	1.0129	0.4391	0.7127	0.071 (7)*
C9	1.0623 (6)	0.4677 (4)	0.8146 (3)	0.0686 (15)
H9	1.1538	0.4847	0.8055	0.045 (5)*
C10	1.0512 (6)	0.3977 (4)	0.8693 (3)	0.0697 (17)
C11	1.0173 (5)	0.4919 (3)	0.8887 (3)	0.0586 (16)
H11	1.0834	0.5220	0.9178	0.045 (5)*
C12	0.8824 (5)	0.5235 (3)	0.8982 (2)	0.0454 (12)
H12	0.8184	0.4984	0.8693	0.064 (7)*
C13	0.8419 (5)	0.5850 (3)	0.9442 (2)	0.0446 (12)
C14	0.7110 (5)	0.6257 (3)	0.9385 (2)	0.0443 (12)
C15	0.6070 (5)	0.6020 (3)	0.8815 (2)	0.0410 (12)
C16	0.2825 (5)	0.7213 (3)	0.8442 (3)	0.0612 (15)
H16A	0.2414	0.6687	0.8271	0.129 (6)*
H16B	0.2661	0.7683	0.8115	0.129 (6)*
H16C	0.2468	0.7361	0.8899	0.129 (6)*
C17	0.9201 (6)	0.7006 (4)	0.7918 (3)	0.0720 (16)
H17A	1.0093	0.7138	0.7894	0.089 (15)*
H17B	0.8631	0.7374	0.8164	0.089 (15)*
C18	0.9437 (7)	0.3300 (4)	0.8661 (3)	0.090 (2)
H18A	0.9760	0.2784	0.8426	0.129 (6)*
H18B	0.8702	0.3532	0.8401	0.129 (6)*
H18C	0.9164	0.3153	0.9134	0.129 (6)*
C19	1.1778 (7)	0.3627 (5)	0.9013 (4)	0.112 (3)
H19A	1.2163	0.3207	0.8694	0.129 (6)*
H19B	1.1591	0.3350	0.9460	0.129 (6)*
H19C	1.2382	0.4102	0.9086	0.129 (6)*
C20	0.9313 (6)	0.6255 (3)	0.9990 (3)	0.0698 (16)
H20A	0.9596	0.6822	0.9829	0.129 (6)*
H20B	1.0067	0.5885	1.0059	0.129 (6)*
H20C	0.8847	0.6316	1.0431	0.129 (6)*
C21	0.3664 (5)	0.6179 (3)	0.6929 (3)	0.0453 (12)
C22	0.3204 (5)	0.5350 (3)	0.6607 (2)	0.0411 (12)
C23	0.2381 (5)	0.5386 (3)	0.6026 (3)	0.0531 (13)
H23	0.2099	0.5925	0.5852	0.064 (7)*
C24	0.1981 (6)	0.4628 (4)	0.5708 (3)	0.0655 (15)
H24	0.1428	0.4639	0.5314	0.064 (7)*
C25	0.2414 (6)	0.3849 (4)	0.5984 (3)	0.0697 (17)
H25	0.2141	0.3334	0.5764	0.064 (7)*
C26	0.3572 (5)	0.4531 (3)	0.6841 (3)	0.0511 (13)
H26	0.4121	0.4500	0.7236	0.064 (7)*
C27	0.6664 (6)	0.5762 (4)	0.6360 (3)	0.0630 (16)
C28	0.6346 (7)	0.6157 (4)	0.5654 (2)	0.089 (2)
H28A	0.6076	0.5703	0.5332	0.129 (6)*
H28B	0.7111	0.6447	0.5469	0.129 (6)*
H28C	0.5646	0.6575	0.5709	0.129 (6)*
C29	0.5746 (5)	0.4539 (3)	0.9179 (3)	0.0548 (13)
C30	0.5620 (7)	0.3613 (3)	0.8920 (4)	0.085 (2)
H30A	0.5472	0.3230	0.9318	0.129 (6)*
H30B	0.6414	0.3444	0.8681	0.129 (6)*
H30C	0.4891	0.3572	0.8597	0.129 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.043 (2)	0.0396 (17)	0.0435 (17)	−0.0049 (17)	−0.0102 (19)	−0.0047 (16)
O2	0.093 (3)	0.0434 (18)	0.088 (3)	−0.003 (2)	−0.046 (3)	0.0091 (19)
O3	0.046 (2)	0.0370 (17)	0.0495 (18)	−0.0018 (16)	0.0047 (19)	−0.0033 (15)
O4	0.087 (3)	0.067 (2)	0.063 (2)	0.003 (2)	0.026 (3)	0.013 (2)
O5	0.070 (3)	0.0543 (18)	0.0553 (18)	0.013 (2)	−0.012 (2)	−0.0226 (17)
O6	0.059 (2)	0.065 (2)	0.0376 (17)	0.0056 (19)	0.004 (2)	−0.0063 (17)
O7	0.119 (4)	0.076 (3)	0.072 (2)	0.003 (3)	0.004 (3)	−0.026 (2)
N1	0.080 (4)	0.044 (2)	0.072 (3)	0.000 (3)	−0.014 (3)	−0.010 (2)
C1	0.043 (3)	0.046 (3)	0.050 (3)	−0.001 (2)	0.006 (3)	−0.006 (2)
C2	0.042 (3)	0.044 (3)	0.054 (3)	0.001 (3)	0.000 (3)	−0.010 (2)
C3	0.032 (3)	0.040 (3)	0.049 (3)	−0.003 (2)	−0.002 (3)	−0.001 (2)
C4	0.037 (3)	0.044 (2)	0.040 (2)	−0.007 (2)	0.001 (3)	−0.005 (2)
C5	0.046 (3)	0.052 (3)	0.034 (3)	0.002 (3)	0.007 (3)	0.001 (2)
C6	0.036 (3)	0.068 (3)	0.044 (3)	0.003 (3)	0.004 (3)	0.008 (3)
C7	0.055 (4)	0.107 (5)	0.067 (4)	0.016 (4)	0.019 (4)	0.004 (4)
C8	0.061 (4)	0.094 (4)	0.065 (3)	0.024 (4)	0.013 (4)	−0.018 (3)
C9	0.038 (3)	0.096 (4)	0.072 (4)	0.016 (4)	0.006 (3)	−0.008 (4)
C10	0.056 (4)	0.079 (4)	0.074 (4)	0.026 (4)	0.002 (4)	−0.009 (3)
C11	0.042 (4)	0.067 (4)	0.067 (3)	0.011 (3)	−0.005 (3)	−0.016 (3)
C12	0.039 (3)	0.052 (3)	0.046 (3)	−0.004 (3)	−0.003 (3)	−0.005 (2)
C13	0.042 (3)	0.050 (3)	0.042 (3)	0.008 (3)	0.001 (3)	−0.004 (2)
C14	0.052 (4)	0.043 (3)	0.037 (3)	0.001 (3)	0.004 (3)	−0.002 (3)
C15	0.046 (3)	0.035 (2)	0.042 (3)	0.000 (2)	0.004 (3)	−0.007 (2)
C16	0.037 (3)	0.075 (3)	0.072 (4)	0.010 (3)	−0.002 (3)	−0.007 (3)
C17	0.036 (4)	0.097 (4)	0.082 (4)	−0.013 (4)	0.006 (4)	0.011 (4)
C18	0.098 (5)	0.074 (4)	0.097 (4)	0.020 (4)	0.012 (5)	−0.023 (3)
C19	0.092 (6)	0.132 (6)	0.111 (5)	0.060 (5)	−0.011 (5)	−0.021 (5)
C20	0.061 (4)	0.073 (3)	0.075 (3)	0.006 (3)	−0.017 (4)	−0.026 (3)
C21	0.046 (3)	0.042 (3)	0.048 (3)	0.002 (3)	−0.008 (3)	−0.002 (3)
C22	0.039 (3)	0.039 (2)	0.046 (3)	0.002 (3)	−0.002 (3)	−0.002 (2)
C23	0.053 (4)	0.053 (3)	0.053 (3)	0.004 (3)	−0.006 (3)	0.000 (3)
C24	0.073 (4)	0.071 (3)	0.053 (3)	0.002 (4)	−0.029 (3)	−0.014 (3)
C25	0.082 (5)	0.058 (4)	0.069 (3)	−0.015 (4)	−0.016 (4)	−0.025 (3)
C26	0.051 (3)	0.050 (3)	0.052 (3)	0.000 (3)	−0.014 (3)	−0.002 (2)
C27	0.058 (4)	0.079 (4)	0.052 (3)	0.009 (4)	0.007 (3)	−0.016 (3)
C28	0.104 (5)	0.117 (5)	0.045 (3)	0.003 (5)	−0.004 (4)	−0.006 (3)
C29	0.044 (3)	0.044 (3)	0.077 (4)	−0.004 (3)	0.007 (3)	0.007 (3)
C30	0.085 (5)	0.045 (3)	0.126 (5)	−0.011 (4)	0.011 (5)	−0.004 (3)

Geometric parameters (Å, º) top

O1—C21	1.340 (5)	C10—C11	1.522 (7)
O1—C3	1.465 (5)	C11—C12	1.463 (7)
O2—C21	1.198 (5)	C11—H11	0.9800
O3—C29	1.354 (6)	C12—C13	1.341 (6)
O3—C15	1.457 (5)	C12—H12	0.9300
O4—C29	1.199 (6)	C13—C14	1.471 (7)
O5—C14	1.217 (5)	C13—C20	1.507 (7)
O6—C27	1.349 (6)	C14—C15	1.547 (6)
O6—C5	1.470 (5)	C16—H16A	0.9600
O7—C27	1.196 (6)	C16—H16B	0.9600
N1—C25	1.323 (6)	C16—H16C	0.9600
N1—C26	1.328 (5)	C17—H17A	0.9300
C1—C2	1.518 (6)	C17—H17B	0.9300
C1—C15	1.542 (6)	C18—H18A	0.9600
C1—H1A	0.9700	C18—H18B	0.9600
C1—H1B	0.9700	C18—H18C	0.9600
C2—C3	1.516 (6)	C19—H19A	0.9600
C2—C16	1.529 (7)	C19—H19B	0.9600
C2—H2	0.9800	C19—H19C	0.9600
C3—C4	1.523 (6)	C20—H20A	0.9600
C3—H3	0.9800	C20—H20B	0.9600
C4—C5	1.532 (6)	C20—H20C	0.9600
C4—C15	1.582 (6)	C21—C22	1.478 (6)
C4—H4	0.9800	C22—C26	1.375 (6)
C5—C6	1.521 (7)	C22—C23	1.377 (6)
C5—H5	0.9800	C23—C24	1.364 (6)
C6—C17	1.303 (7)	C23—H23	0.9300
C6—C7	1.508 (7)	C24—C25	1.368 (7)
C7—C8	1.521 (7)	C24—H24	0.9300
C7—H7A	0.9700	C25—H25	0.9300
C7—H7B	0.9700	C26—H26	0.9300
C8—C9	1.500 (7)	C27—C28	1.492 (7)
C8—H8A	0.9700	C28—H28A	0.9600
C8—H8B	0.9700	C28—H28B	0.9600
C9—C10	1.487 (7)	C28—H28C	0.9600
C9—C11	1.513 (7)	C29—C30	1.499 (7)
C9—H9	0.9800	C30—H30A	0.9600
C10—C18	1.504 (8)	C30—H30B	0.9600
C10—C19	1.518 (8)	C30—H30C	0.9600

C21—O1—C3	116.8 (3)	O5—C14—C13	119.4 (5)
C29—O3—C15	115.9 (3)	O5—C14—C15	115.2 (4)
C27—O6—C5	117.0 (4)	C13—C14—C15	124.7 (4)
C25—N1—C26	116.1 (4)	O3—C15—C1	109.5 (4)
C2—C1—C15	107.4 (4)	O3—C15—C14	114.0 (4)
C2—C1—H1A	110.2	C1—C15—C14	112.4 (4)
C15—C1—H1A	110.2	O3—C15—C4	106.9 (3)
C2—C1—H1B	110.2	C1—C15—C4	103.7 (4)
C15—C1—H1B	110.2	C14—C15—C4	109.6 (4)
H1A—C1—H1B	108.5	C2—C16—H16A	109.5
C3—C2—C1	102.8 (3)	C2—C16—H16B	109.5
C3—C2—C16	116.3 (4)	H16A—C16—H16B	109.5
C1—C2—C16	113.9 (4)	C2—C16—H16C	109.5
C3—C2—H2	107.8	H16A—C16—H16C	109.5
C1—C2—H2	107.8	H16B—C16—H16C	109.5
C16—C2—H2	107.8	C6—C17—H17A	120.0
O1—C3—C2	110.9 (4)	C6—C17—H17B	120.0
O1—C3—C4	107.8 (3)	H17A—C17—H17B	120.0
C2—C3—C4	103.0 (4)	C10—C18—H18A	109.5
O1—C3—H3	111.6	C10—C18—H18B	109.5
C2—C3—H3	111.6	H18A—C18—H18B	109.5
C4—C3—H3	111.6	C10—C18—H18C	109.5
C3—C4—C5	116.6 (4)	H18A—C18—H18C	109.5
C3—C4—C15	103.8 (4)	H18B—C18—H18C	109.5
C5—C4—C15	117.3 (4)	C10—C19—H19A	109.5
C3—C4—H4	106.1	C10—C19—H19B	109.5
C5—C4—H4	106.1	H19A—C19—H19B	109.5
C15—C4—H4	106.1	C10—C19—H19C	109.5
O6—C5—C6	104.4 (4)	H19A—C19—H19C	109.5
O6—C5—C4	107.3 (4)	H19B—C19—H19C	109.5
C6—C5—C4	117.4 (4)	C13—C20—H20A	109.5
O6—C5—H5	109.2	C13—C20—H20B	109.5
C6—C5—H5	109.2	H20A—C20—H20B	109.5
C4—C5—H5	109.2	C13—C20—H20C	109.5
C17—C6—C7	121.7 (5)	H20A—C20—H20C	109.5
C17—C6—C5	123.0 (5)	H20B—C20—H20C	109.5
C7—C6—C5	115.1 (5)	O2—C21—O1	124.7 (4)
C6—C7—C8	116.5 (4)	O2—C21—C22	123.5 (4)
C6—C7—H7A	108.2	O1—C21—C22	111.8 (4)
C8—C7—H7A	108.2	C26—C22—C23	117.1 (4)
C6—C7—H7B	108.2	C26—C22—C21	124.0 (4)
C8—C7—H7B	108.2	C23—C22—C21	118.8 (4)
H7A—C7—H7B	107.3	C24—C23—C22	119.6 (5)
C9—C8—C7	115.4 (5)	C24—C23—H23	120.2
C9—C8—H8A	108.4	C22—C23—H23	120.2
C7—C8—H8A	108.4	C23—C24—C25	118.3 (5)
C9—C8—H8B	108.4	C23—C24—H24	120.9
C7—C8—H8B	108.4	C25—C24—H24	120.9
H8A—C8—H8B	107.5	N1—C25—C24	124.2 (5)
C10—C9—C8	125.6 (5)	N1—C25—H25	117.9
C10—C9—C11	61.0 (3)	C24—C25—H25	117.9
C8—C9—C11	123.5 (5)	N1—C26—C22	124.6 (4)
C10—C9—H9	112.5	N1—C26—H26	117.7
C8—C9—H9	112.5	C22—C26—H26	117.7
C11—C9—H9	112.5	O7—C27—O6	124.0 (5)
C9—C10—C18	121.3 (5)	O7—C27—C28	124.7 (5)
C9—C10—C19	117.5 (6)	O6—C27—C28	111.4 (5)
C18—C10—C19	113.0 (5)	C27—C28—H28A	109.5
C9—C10—C11	60.4 (4)	C27—C28—H28B	109.5
C18—C10—C11	119.6 (5)	H28A—C28—H28B	109.5
C19—C10—C11	115.4 (5)	C27—C28—H28C	109.5
C12—C11—C9	118.4 (5)	H28A—C28—H28C	109.5
C12—C11—C10	123.5 (5)	H28B—C28—H28C	109.5
C9—C11—C10	58.7 (3)	O4—C29—O3	123.3 (4)
C12—C11—H11	114.9	O4—C29—C30	125.7 (5)
C9—C11—H11	114.9	O3—C29—C30	111.0 (5)
C10—C11—H11	114.9	C29—C30—H30A	109.5
C13—C12—C11	126.6 (5)	C29—C30—H30B	109.5
C13—C12—H12	116.7	H30A—C30—H30B	109.5
C11—C12—H12	116.7	C29—C30—H30C	109.5
C12—C13—C14	121.7 (4)	H30A—C30—H30C	109.5
C12—C13—C20	122.9 (5)	H30B—C30—H30C	109.5
C14—C13—C20	115.0 (4)

Experimental details

Crystal data
Chemical formula	C₃₀H₃₇NO₇
M_r	523.61
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	10.162 (6), 15.249 (5), 18.802 (9)
V (Å³)	2914 (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
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3444, 3065, 1462
R_int	0.003
(sin θ/λ)_max (Å⁻¹)	0.607

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.118, 0.93
No. of reflections	3065
No. of parameters	354
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.24

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

Acknowledgements

Support by the `Western Light' Joint Research Program of the Chinese Academy of Sciences is acknowledged. The authors are also grateful to the staff of the analytical group of Chengdu Institute of Biology, Chinese Academy of Sciences, for the NMR spectroscopic data.

References

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