(3S,12R,20S,24R)-20,24-Ep­oxy­dammarane-3,12,25-triol

Li, W.-J.; Guo, H.-M.; Ji, C.-M.; Bi, Y.; Meng, Q.-G.

doi:10.1107/S1600536811028418

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2112

doi:10.1107/S1600536811028418

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(3S,12R,20S,24R)-20,24-Epoxydammarane-3,12,25-triol

Wen-Juan Li,^a Huan-Mei Guo,^b Chun-Mei Ji,^c Yi Bi ^a and Qing-Guo Meng ^a ^*

^aSchool of Pharmacy, Yantai University, Yantai 264005, People's Republic of China, ^bMicroscale Science Institute, Weifang University, Weifang 261041, People's Republic of China, and ^cWeifang People's Hospital, Weifang 261041, People's Republic of China
^*Correspondence e-mail: mqg@ytu.edu.cn

(Received 24 May 2011; accepted 15 July 2011; online 23 July 2011)

In the title molecule, C₃₀H₅₂O₄, the three six-membered rings are in chair conformations, the cyclopentane ring is in an envelope form and the tetrahydrofuran ring has a conformation intermediate between half-chair and sofa. In the crystal, molecules are linked by intermolecular O—H⋯O hydrogen bonds into helical chains along [100]. Two intramolecular O—H⋯O hydrogen bonds are also present. One C atom of the tetrahydrofuran ring and its attached H atoms are equally disordered over two sets of sites.

Related literature

For the medicinal properties of Panax ginseng and Panax quinquefolium, see: Shibata et al. (1985 ); Takano et al. (1999 ); Yu et al. (2007 ); Wang et al. (2010 ). For related structures, see: Guo et al. (2011 ); Iljin et al. (1982 ); Meng et al. (2010 ).

Experimental

Crystal data

C₃₀H₅₂O₄
M_r = 476.72
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.6795 (14) Å
b = 13.067 (3) Å
c = 28.084 (5) Å
V = 2818.1 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
14876 measured reflections
5250 independent reflections
3460 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.128
S = 1.06
5250 reflections
318 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O1ⁱ	0.82	2.09	2.905 (3)	172
O3—H3⋯O2	0.82	1.95	2.677 (3)	147
O1—H1⋯O3	0.82	2.14	2.948 (3)	170
Symmetry code: (i) $[x+{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811028418/lh5260sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028418/lh5260Isup2.hkl

checkCIF report

Comment top

Both Panax ginseng and Panax quinquefolium, belonging to the Araliaceae, are well known traditional medicinal herbs. They are used as tonics and the treatment for diseases, such as tumor and myocardial ischemia. Panax ginseng contains numbers of ginsenoside, including an oleanolic acid-type saponin in addition to the major protopanaxadiol and protopanaxatriol-type saponins (Shibata et al., 1985). Panax quinquefolium contains an ocotillol-type (20S, 24R-epoxyside) saponin with high anti-tumor activity (Takano et al., 1999), as well as an oleanolic acid-type saponin, protopanaxadiol and protopanaxatriol-type saponins. (3S,6S,12R,20S,24R)-20,24-epoxy-dammarane-3,6,12,25-tetraol and (3S,12R,20S,24R)-20,24-epoxy-dammarane-3,12,25-triol are found to possess cardioprotective effect on myocardial injury induced by isoproterenol in rats (Yu et al., 2007; Wang et al., 2010). As part of our ongoing investigation of ocotillol-type compounds and their cardioprotective effect on myocardial injury, we report herein the crystal structure of the title compound, (I).

In the molecule (Fig. 1), all bond lengths and angles are within normal ranges (Guo et al., 2011; Iljin et al., 1982; Meng et al., 2010) Rings A(C10/C11/C15-C18), B(C15/C16/C20-C23), and C(C22/C23/C25-C28) are in chair conformations. Ring D(C9-C13) has an envelope form with C11 as the flap. The tetrahydrofuran ring has a conformation intermediate between the half-chair and envelope forms. In the crystal, molecules are linked by intermolecular O—H···O hydrogen bonds into helical chains along [100]. Two intramolecular O—H···O hydrogen bonds are also present.

Related literature top

For the medicinal properties of Panax ginseng and Panax quinquefolium, see: Shibata et al. (1985); Takano et al. (1999); Yu et al. (2007); Wang et al. (2010). For related structures, see: Guo et al. (2011); Iljin et al. (1982); Meng et al. (2010).

Experimental top

20(S)-protopanaxadiol was degraded from Panax quinquefolium saponin with sodium methylate in DMSO at about 463-473K and seperated by silica colum chromatography. (3S,12R,20S,24R)-20,24-epoxy-dammarane-3,12,25-triol was synthesized from 20(S)-protopanaxadiol in the presence of N,N-dimethylaminopyridine, pyridine and acetic anhydride. The intermediate esters were oxidized by hydrogen dioxide 30% solution in methanoic acid, and the title compound was prepared by saponification with sodium hydroxide in methanol and seperated by silica colum chromatography. Finally, the crystals were dried at room temperature the title compound was crystallized from ethyl acetate and petroleum ether. Single crystals of compound (I) suitable for X-ray measurements were obtained by recrystallization from ethyl acetate and petroleum ether at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

(3S,12R,20S,24R)-20,24-Epoxydammarane-3,12,25-triol top

Crystal data top

C₃₀H₅₂O₄	F(000) = 1056
M_r = 476.72	D_x = 1.124 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2282 reflections
a = 7.6795 (14) Å	θ = 2.7–20.8°
b = 13.067 (3) Å	µ = 0.07 mm⁻¹
c = 28.084 (5) Å	T = 298 K
V = 2818.1 (9) Å³	Block, colourless
Z = 4	0.20 × 0.20 × 0.16 mm

Data collection top

Bruker SMART CCD diffractometer	3460 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 25.5°, θ_min = 1.7°
ϕ and ω scans	h = −8→9
14876 measured reflections	k = −15→13
5250 independent reflections	l = −34→34

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0537P)²] where P = (F_o² + 2F_c²)/3
5250 reflections	(Δ/σ)_max < 0.001
318 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₃₀H₅₂O₄	V = 2818.1 (9) Å³
M_r = 476.72	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.6795 (14) Å	µ = 0.07 mm⁻¹
b = 13.067 (3) Å	T = 298 K
c = 28.084 (5) Å	0.20 × 0.20 × 0.16 mm

Data collection top

Bruker SMART CCD diffractometer	3460 reflections with I > 2σ(I)
14876 measured reflections	R_int = 0.048
5250 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.128	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
5250 reflections	Δρ_min = −0.20 e Å⁻³
318 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	Occ. (<1)
C1	0.4251 (4)	−0.0332 (3)	0.21114 (13)	0.0847 (12)
H1A	0.4198	0.0041	0.1817	0.127*
H1B	0.3868	0.0099	0.2367	0.127*
H1C	0.3511	−0.0923	0.2092	0.127*
C2	0.6196 (5)	−0.1359 (3)	0.26373 (10)	0.0736 (11)
H2A	0.5505	−0.1960	0.2584	0.110*
H2B	0.5759	−0.0998	0.2910	0.110*
H2C	0.7384	−0.1554	0.2693	0.110*
C3	0.6101 (4)	−0.0668 (2)	0.22022 (10)	0.0507 (8)
C4	0.7278 (4)	0.0254 (3)	0.22727 (10)	0.0558 (9)
H4	0.6876	0.0642	0.2550	0.067*
C5	0.9203 (5)	0.0014 (3)	0.23315 (15)	0.1004 (14)	0.50
H5A	0.9496	−0.0060	0.2666	0.120*	0.50
H5B	0.9498	−0.0617	0.2168	0.120*	0.50
C5'	0.9203 (5)	0.0014 (3)	0.23315 (15)	0.1004 (14)	0.50
H5'1	0.9496	−0.0060	0.2666	0.120*	0.50
H5'2	0.9498	−0.0617	0.2168	0.120*	0.50
C6	1.0160 (4)	0.0894 (3)	0.21188 (11)	0.0649 (10)
H6A	1.1036	0.0655	0.1896	0.078*
H6B	1.0729	0.1293	0.2365	0.078*
C7	0.8793 (4)	0.1540 (2)	0.18612 (11)	0.0528 (8)
C8	0.8352 (5)	0.2515 (3)	0.21402 (12)	0.0794 (11)
H8A	0.7426	0.2874	0.1983	0.119*
H8B	0.9362	0.2947	0.2156	0.119*
H8C	0.7992	0.2335	0.2457	0.119*
C9	0.9254 (4)	0.1805 (2)	0.13455 (10)	0.0510 (8)
H9	0.8368	0.2274	0.1222	0.061*
C10	0.9449 (3)	0.0904 (2)	0.09921 (9)	0.0418 (7)
H10	0.9894	0.0319	0.1173	0.050*
C11	1.0907 (3)	0.1237 (2)	0.06455 (10)	0.0411 (7)
C12	1.2203 (4)	0.1710 (2)	0.09937 (10)	0.0523 (8)
H12A	1.3044	0.2134	0.0828	0.063*
H12B	1.2819	0.1184	0.1170	0.063*
C13	1.1069 (4)	0.2358 (2)	0.13266 (11)	0.0635 (9)
H13A	1.0944	0.3048	0.1204	0.076*
H13B	1.1582	0.2393	0.1642	0.076*
C14	1.0295 (4)	0.2132 (2)	0.03248 (11)	0.0607 (9)
H14A	0.9573	0.2587	0.0507	0.091*
H14B	0.9643	0.1866	0.0061	0.091*
H14C	1.1291	0.2498	0.0208	0.091*
C15	1.1547 (3)	0.0288 (2)	0.03503 (9)	0.0360 (6)
C16	0.9957 (3)	−0.0086 (2)	0.00506 (8)	0.0389 (7)
H16	0.9580	0.0524	−0.0124	0.047*
C17	0.8403 (3)	−0.0340 (2)	0.03794 (10)	0.0480 (8)
H17A	0.7410	−0.0521	0.0183	0.058*
H17B	0.8700	−0.0935	0.0570	0.058*
C18	0.7877 (3)	0.0529 (2)	0.07120 (10)	0.0464 (7)
H18	0.7421	0.1096	0.0521	0.056*
C19	1.2256 (3)	−0.0554 (2)	0.06845 (10)	0.0435 (7)
H19A	1.2910	−0.1042	0.0502	0.065*
H19B	1.1301	−0.0893	0.0839	0.065*
H19C	1.2997	−0.0250	0.0921	0.065*
C20	1.3025 (4)	0.0595 (2)	0.00172 (10)	0.0513 (8)
H20A	1.2722	0.1236	−0.0136	0.062*
H20B	1.4066	0.0713	0.0205	0.062*
C21	1.3433 (3)	−0.0191 (2)	−0.03635 (10)	0.0498 (8)
H21A	1.3851	−0.0815	−0.0215	0.060*
H21B	1.4346	0.0067	−0.0569	0.060*
C22	1.1812 (4)	−0.0429 (2)	−0.06606 (9)	0.0452 (7)
H22	1.1364	0.0246	−0.0750	0.054*
C23	1.0341 (3)	−0.0895 (2)	−0.03472 (9)	0.0394 (7)
C24	1.0780 (4)	−0.1959 (2)	−0.01420 (9)	0.0462 (8)
H24A	1.0064	−0.2089	0.0132	0.069*
H24B	1.1984	−0.1977	−0.0051	0.069*
H24C	1.0565	−0.2472	−0.0379	0.069*
C25	0.8724 (4)	−0.1010 (2)	−0.06637 (10)	0.0535 (8)
H25A	0.7823	−0.1361	−0.0485	0.064*
H25B	0.8289	−0.0334	−0.0744	0.064*
C26	0.9066 (4)	−0.1596 (3)	−0.11209 (10)	0.0617 (9)
H26A	0.9409	−0.2291	−0.1044	0.074*
H26B	0.8003	−0.1629	−0.1307	0.074*
C27	1.0486 (5)	−0.1094 (3)	−0.14150 (9)	0.0606 (9)
H27	1.0068	−0.0402	−0.1485	0.073*
C28	1.2207 (4)	−0.0958 (2)	−0.11462 (10)	0.0515 (8)
C29	1.3187 (4)	−0.1977 (3)	−0.10958 (11)	0.0630 (9)
H29A	1.3576	−0.2201	−0.1404	0.095*
H29B	1.2423	−0.2483	−0.0962	0.095*
H29C	1.4174	−0.1885	−0.0890	0.095*
C30	1.3365 (5)	−0.0241 (3)	−0.14445 (11)	0.0851 (13)
H30A	1.3411	−0.0484	−0.1767	0.128*
H30B	1.4519	−0.0230	−0.1313	0.128*
H30C	1.2887	0.0438	−0.1439	0.128*
O1	0.6710 (4)	−0.12800 (17)	0.18183 (7)	0.0698 (7)
H1	0.6729	−0.0937	0.1574	0.105*
O2	0.7239 (2)	0.09040 (15)	0.18631 (6)	0.0488 (5)
O3	0.6511 (3)	0.01346 (19)	0.10025 (7)	0.0650 (7)
H3	0.6383	0.0504	0.1236	0.097*
O4	1.0687 (4)	−0.15820 (18)	−0.18635 (7)	0.0770 (7)
H4A	1.0998	−0.2176	−0.1823	0.115*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.056 (2)	0.111 (3)	0.087 (2)	0.004 (2)	0.007 (2)	0.025 (2)
C2	0.075 (2)	0.087 (3)	0.0594 (19)	0.008 (2)	0.0038 (19)	0.009 (2)
C3	0.0429 (17)	0.064 (2)	0.0448 (16)	0.0055 (17)	0.0008 (15)	−0.0015 (17)
C4	0.066 (2)	0.062 (2)	0.0399 (16)	0.0061 (18)	−0.0051 (15)	−0.0050 (16)
C5	0.072 (3)	0.099 (3)	0.130 (3)	−0.009 (3)	−0.058 (3)	0.024 (3)
C5'	0.072 (3)	0.099 (3)	0.130 (3)	−0.009 (3)	−0.058 (3)	0.024 (3)
C6	0.058 (2)	0.080 (3)	0.0566 (18)	0.005 (2)	−0.0118 (17)	−0.013 (2)
C7	0.0473 (18)	0.055 (2)	0.0561 (18)	0.0073 (16)	−0.0029 (17)	−0.0101 (17)
C8	0.082 (3)	0.066 (3)	0.090 (2)	0.001 (2)	0.019 (2)	−0.026 (2)
C9	0.0442 (18)	0.0472 (19)	0.0617 (18)	0.0097 (15)	−0.0022 (16)	−0.0082 (16)
C10	0.0372 (15)	0.0433 (17)	0.0450 (15)	0.0043 (14)	−0.0079 (13)	0.0029 (15)
C11	0.0358 (15)	0.0369 (16)	0.0507 (16)	0.0018 (14)	−0.0012 (14)	0.0071 (14)
C12	0.0475 (18)	0.0480 (19)	0.0614 (18)	−0.0089 (15)	0.0041 (16)	−0.0069 (16)
C13	0.061 (2)	0.051 (2)	0.078 (2)	−0.0041 (18)	−0.0013 (19)	−0.0137 (19)
C14	0.062 (2)	0.0457 (19)	0.075 (2)	0.0087 (17)	0.0024 (18)	0.0109 (18)
C15	0.0314 (14)	0.0343 (16)	0.0423 (14)	−0.0033 (13)	−0.0005 (12)	0.0082 (14)
C16	0.0377 (16)	0.0377 (16)	0.0412 (14)	−0.0032 (13)	−0.0020 (13)	0.0103 (14)
C17	0.0356 (16)	0.061 (2)	0.0468 (16)	−0.0084 (15)	−0.0057 (14)	0.0044 (16)
C18	0.0306 (15)	0.064 (2)	0.0442 (15)	0.0011 (15)	−0.0011 (14)	0.0065 (16)
C19	0.0383 (15)	0.0446 (17)	0.0478 (15)	0.0022 (14)	−0.0060 (14)	−0.0002 (14)
C20	0.0465 (18)	0.0463 (19)	0.0612 (18)	−0.0102 (15)	0.0022 (16)	0.0030 (17)
C21	0.0440 (17)	0.0532 (19)	0.0523 (17)	−0.0088 (16)	0.0101 (15)	0.0035 (17)
C22	0.0527 (18)	0.0391 (17)	0.0439 (15)	−0.0001 (14)	0.0001 (15)	0.0078 (14)
C23	0.0394 (15)	0.0405 (17)	0.0382 (14)	−0.0008 (14)	−0.0027 (13)	0.0064 (14)
C24	0.0552 (18)	0.0429 (18)	0.0406 (15)	−0.0081 (16)	−0.0002 (14)	0.0038 (14)
C25	0.0486 (18)	0.061 (2)	0.0509 (17)	−0.0009 (16)	−0.0091 (15)	0.0038 (17)
C26	0.063 (2)	0.073 (2)	0.0494 (17)	−0.003 (2)	−0.0159 (18)	−0.0017 (18)
C27	0.088 (3)	0.054 (2)	0.0396 (16)	0.0147 (19)	−0.0100 (18)	0.0059 (16)
C28	0.064 (2)	0.0480 (19)	0.0426 (16)	0.0005 (17)	0.0096 (16)	0.0080 (15)
C29	0.068 (2)	0.068 (2)	0.0530 (18)	0.0092 (18)	0.0011 (17)	−0.0062 (18)
C30	0.118 (3)	0.081 (3)	0.056 (2)	−0.016 (3)	0.032 (2)	0.006 (2)
O1	0.0909 (17)	0.0602 (15)	0.0584 (13)	−0.0018 (13)	0.0175 (14)	−0.0123 (12)
O2	0.0416 (11)	0.0558 (13)	0.0489 (11)	0.0111 (10)	−0.0024 (10)	0.0000 (11)
O3	0.0363 (11)	0.106 (2)	0.0525 (12)	−0.0134 (13)	0.0044 (10)	−0.0117 (13)
O4	0.118 (2)	0.0746 (17)	0.0383 (11)	0.0122 (17)	−0.0075 (13)	−0.0009 (12)

Geometric parameters (Å, º) top

C1—C3	1.508 (4)	C16—C17	1.545 (3)
C1—H1A	0.9600	C16—C23	1.566 (4)
C1—H1B	0.9600	C16—H16	0.9800
C1—H1C	0.9600	C17—C18	1.525 (4)
C2—C3	1.521 (4)	C17—H17A	0.9700
C2—H2A	0.9600	C17—H17B	0.9700
C2—H2B	0.9600	C18—O3	1.425 (3)
C2—H2C	0.9600	C18—H18	0.9800
C3—O1	1.421 (3)	C19—H19A	0.9600
C3—C4	1.519 (4)	C19—H19B	0.9600
C4—O2	1.430 (3)	C19—H19C	0.9600
C4—C5	1.521 (5)	C20—C21	1.516 (4)
C4—H4	0.9800	C20—H20A	0.9700
C5—C6	1.491 (5)	C20—H20B	0.9700
C5—H5A	0.9700	C21—C22	1.531 (4)
C5—H5B	0.9700	C21—H21A	0.9700
C6—C7	1.529 (4)	C21—H21B	0.9700
C6—H6A	0.9700	C22—C23	1.556 (3)
C6—H6B	0.9700	C22—C28	1.559 (4)
C7—O2	1.454 (3)	C22—H22	0.9800
C7—C9	1.530 (4)	C23—C25	1.534 (4)
C7—C8	1.533 (4)	C23—C24	1.542 (4)
C8—H8A	0.9600	C24—H24A	0.9600
C8—H8B	0.9600	C24—H24B	0.9600
C8—H8C	0.9600	C24—H24C	0.9600
C9—C10	1.547 (4)	C25—C26	1.518 (4)
C9—C13	1.571 (4)	C25—H25A	0.9700
C9—H9	0.9800	C25—H25B	0.9700
C10—C18	1.522 (3)	C26—C27	1.517 (4)
C10—C11	1.547 (4)	C26—H26A	0.9700
C10—H10	0.9800	C26—H26B	0.9700
C11—C12	1.526 (4)	C27—O4	1.420 (3)
C11—C14	1.549 (4)	C27—C28	1.533 (4)
C11—C15	1.570 (4)	C27—H27	0.9800
C12—C13	1.533 (4)	C28—C29	1.536 (4)
C12—H12A	0.9700	C28—C30	1.539 (4)
C12—H12B	0.9700	C29—H29A	0.9600
C13—H13A	0.9700	C29—H29B	0.9600
C13—H13B	0.9700	C29—H29C	0.9600
C14—H14A	0.9600	C30—H30A	0.9600
C14—H14B	0.9600	C30—H30B	0.9600
C14—H14C	0.9600	C30—H30C	0.9600
C15—C20	1.525 (3)	O1—H1	0.8200
C15—C19	1.545 (3)	O3—H3	0.8200
C15—C16	1.562 (3)	O4—H4A	0.8200

C3—C1—H1A	109.5	C15—C16—C23	116.6 (2)
C3—C1—H1B	109.5	C17—C16—H16	104.3
H1A—C1—H1B	109.5	C15—C16—H16	104.3
C3—C1—H1C	109.5	C23—C16—H16	104.3
H1A—C1—H1C	109.5	C18—C17—C16	114.2 (2)
H1B—C1—H1C	109.5	C18—C17—H17A	108.7
C3—C2—H2A	109.5	C16—C17—H17A	108.7
C3—C2—H2B	109.5	C18—C17—H17B	108.7
H2A—C2—H2B	109.5	C16—C17—H17B	108.7
C3—C2—H2C	109.5	H17A—C17—H17B	107.6
H2A—C2—H2C	109.5	O3—C18—C10	113.8 (2)
H2B—C2—H2C	109.5	O3—C18—C17	106.0 (2)
O1—C3—C1	110.2 (3)	C10—C18—C17	110.3 (2)
O1—C3—C4	110.4 (2)	O3—C18—H18	108.9
C1—C3—C4	110.6 (3)	C10—C18—H18	108.9
O1—C3—C2	105.1 (2)	C17—C18—H18	108.9
C1—C3—C2	110.7 (3)	C15—C19—H19A	109.5
C4—C3—C2	109.7 (2)	C15—C19—H19B	109.5
O2—C4—C3	110.7 (2)	H19A—C19—H19B	109.5
O2—C4—C5	103.3 (3)	C15—C19—H19C	109.5
C3—C4—C5	115.4 (3)	H19A—C19—H19C	109.5
O2—C4—H4	109.1	H19B—C19—H19C	109.5
C3—C4—H4	109.1	C21—C20—C15	114.1 (2)
C5—C4—H4	109.1	C21—C20—H20A	108.7
C6—C5—C4	106.0 (3)	C15—C20—H20A	108.7
C6—C5—H5A	110.5	C21—C20—H20B	108.7
C4—C5—H5A	110.5	C15—C20—H20B	108.7
C6—C5—H5B	110.5	H20A—C20—H20B	107.6
C4—C5—H5B	110.5	C20—C21—C22	110.8 (2)
H5A—C5—H5B	108.7	C20—C21—H21A	109.5
C5—C6—C7	106.1 (3)	C22—C21—H21A	109.5
C5—C6—H6A	110.5	C20—C21—H21B	109.5
C7—C6—H6A	110.5	C22—C21—H21B	109.5
C5—C6—H6B	110.5	H21A—C21—H21B	108.1
C7—C6—H6B	110.5	C21—C22—C23	111.2 (2)
H6A—C6—H6B	108.7	C21—C22—C28	114.1 (2)
O2—C7—C6	104.3 (2)	C23—C22—C28	117.6 (2)
O2—C7—C9	108.8 (2)	C21—C22—H22	104.1
C6—C7—C9	114.4 (3)	C23—C22—H22	104.1
O2—C7—C8	107.0 (2)	C28—C22—H22	104.1
C6—C7—C8	111.6 (3)	C25—C23—C24	107.8 (2)
C9—C7—C8	110.3 (3)	C25—C23—C22	107.3 (2)
C7—C8—H8A	109.5	C24—C23—C22	113.9 (2)
C7—C8—H8B	109.5	C25—C23—C16	109.1 (2)
H8A—C8—H8B	109.5	C24—C23—C16	112.5 (2)
C7—C8—H8C	109.5	C22—C23—C16	106.0 (2)
H8A—C8—H8C	109.5	C23—C24—H24A	109.5
H8B—C8—H8C	109.5	C23—C24—H24B	109.5
C7—C9—C10	117.2 (3)	H24A—C24—H24B	109.5
C7—C9—C13	109.9 (3)	C23—C24—H24C	109.5
C10—C9—C13	104.0 (2)	H24A—C24—H24C	109.5
C7—C9—H9	108.4	H24B—C24—H24C	109.5
C10—C9—H9	108.4	C26—C25—C23	113.5 (2)
C13—C9—H9	108.4	C26—C25—H25A	108.9
C18—C10—C11	109.8 (2)	C23—C25—H25A	108.9
C18—C10—C9	120.0 (2)	C26—C25—H25B	108.9
C11—C10—C9	105.1 (2)	C23—C25—H25B	108.9
C18—C10—H10	107.1	H25A—C25—H25B	107.7
C11—C10—H10	107.1	C27—C26—C25	111.5 (3)
C9—C10—H10	107.1	C27—C26—H26A	109.3
C12—C11—C10	100.5 (2)	C25—C26—H26A	109.3
C12—C11—C14	105.3 (2)	C27—C26—H26B	109.3
C10—C11—C14	111.0 (2)	C25—C26—H26B	109.3
C12—C11—C15	117.0 (2)	H26A—C26—H26B	108.0
C10—C11—C15	109.7 (2)	O4—C27—C26	111.5 (3)
C14—C11—C15	112.6 (2)	O4—C27—C28	113.3 (3)
C11—C12—C13	104.1 (2)	C26—C27—C28	113.7 (2)
C11—C12—H12A	110.9	O4—C27—H27	105.9
C13—C12—H12A	110.9	C26—C27—H27	105.9
C11—C12—H12B	110.9	C28—C27—H27	105.9
C13—C12—H12B	110.9	C27—C28—C29	111.6 (3)
H12A—C12—H12B	108.9	C27—C28—C30	107.5 (2)
C12—C13—C9	105.7 (2)	C29—C28—C30	107.2 (3)
C12—C13—H13A	110.6	C27—C28—C22	108.3 (2)
C9—C13—H13A	110.6	C29—C28—C22	113.5 (2)
C12—C13—H13B	110.6	C30—C28—C22	108.6 (2)
C9—C13—H13B	110.6	C28—C29—H29A	109.5
H13A—C13—H13B	108.7	C28—C29—H29B	109.5
C11—C14—H14A	109.5	H29A—C29—H29B	109.5
C11—C14—H14B	109.5	C28—C29—H29C	109.5
H14A—C14—H14B	109.5	H29A—C29—H29C	109.5
C11—C14—H14C	109.5	H29B—C29—H29C	109.5
H14A—C14—H14C	109.5	C28—C30—H30A	109.5
H14B—C14—H14C	109.5	C28—C30—H30B	109.5
C20—C15—C19	107.3 (2)	H30A—C30—H30B	109.5
C20—C15—C16	109.5 (2)	C28—C30—H30C	109.5
C19—C15—C16	112.4 (2)	H30A—C30—H30C	109.5
C20—C15—C11	110.4 (2)	H30B—C30—H30C	109.5
C19—C15—C11	110.6 (2)	C3—O1—H1	109.5
C16—C15—C11	106.6 (2)	C4—O2—C7	109.0 (2)
C17—C16—C15	110.42 (18)	C18—O3—H3	109.5
C17—C16—C23	115.2 (2)	C27—O4—H4A	109.5

O1—C3—C4—O2	63.4 (3)	C15—C16—C17—C18	54.3 (3)
C1—C3—C4—O2	−58.9 (3)	C23—C16—C17—C18	−170.9 (2)
C2—C3—C4—O2	178.7 (2)	C11—C10—C18—O3	175.7 (2)
O1—C3—C4—C5	−53.5 (4)	C9—C10—C18—O3	−62.5 (4)
C1—C3—C4—C5	−175.7 (3)	C11—C10—C18—C17	56.6 (3)
C2—C3—C4—C5	61.8 (4)	C9—C10—C18—C17	178.4 (2)
O2—C4—C5—C6	26.9 (4)	C16—C17—C18—O3	−176.7 (2)
C3—C4—C5—C6	147.8 (3)	C16—C17—C18—C10	−53.0 (3)
C4—C5—C6—C7	−9.9 (4)	C19—C15—C20—C21	73.4 (3)
C5—C6—C7—O2	−10.5 (3)	C16—C15—C20—C21	−48.8 (3)
C5—C6—C7—C9	−129.2 (3)	C11—C15—C20—C21	−165.9 (2)
C5—C6—C7—C8	104.6 (3)	C15—C20—C21—C22	56.7 (3)
O2—C7—C9—C10	−53.5 (3)	C20—C21—C22—C23	−61.8 (3)
C6—C7—C9—C10	62.6 (4)	C20—C21—C22—C28	162.3 (2)
C8—C7—C9—C10	−170.5 (3)	C21—C22—C23—C25	174.7 (2)
O2—C7—C9—C13	−172.0 (2)	C28—C22—C23—C25	−51.2 (3)
C6—C7—C9—C13	−55.9 (3)	C21—C22—C23—C24	−66.1 (3)
C8—C7—C9—C13	71.0 (3)	C28—C22—C23—C24	68.0 (3)
C7—C9—C10—C18	90.3 (3)	C21—C22—C23—C16	58.2 (3)
C13—C9—C10—C18	−148.1 (3)	C28—C22—C23—C16	−167.7 (2)
C7—C9—C10—C11	−145.5 (2)	C17—C16—C23—C25	59.1 (3)
C13—C9—C10—C11	−23.9 (3)	C15—C16—C23—C25	−169.0 (2)
C18—C10—C11—C12	172.5 (2)	C17—C16—C23—C24	−60.5 (3)
C9—C10—C11—C12	42.1 (3)	C15—C16—C23—C24	71.4 (3)
C18—C10—C11—C14	61.4 (3)	C17—C16—C23—C22	174.4 (2)
C9—C10—C11—C14	−68.9 (3)	C15—C16—C23—C22	−53.7 (3)
C18—C10—C11—C15	−63.6 (3)	C24—C23—C25—C26	−70.0 (3)
C9—C10—C11—C15	166.0 (2)	C22—C23—C25—C26	53.1 (3)
C10—C11—C12—C13	−44.1 (3)	C16—C23—C25—C26	167.5 (2)
C14—C11—C12—C13	71.4 (3)	C23—C25—C26—C27	−57.8 (3)
C15—C11—C12—C13	−162.7 (2)	C25—C26—C27—O4	−174.2 (2)
C11—C12—C13—C9	29.9 (3)	C25—C26—C27—C28	56.3 (4)
C7—C9—C13—C12	122.9 (3)	O4—C27—C28—C29	−53.7 (3)
C10—C9—C13—C12	−3.4 (3)	C26—C27—C28—C29	75.0 (3)
C12—C11—C15—C20	−64.7 (3)	O4—C27—C28—C30	63.5 (3)
C10—C11—C15—C20	−178.3 (2)	C26—C27—C28—C30	−167.8 (3)
C14—C11—C15—C20	57.6 (3)	O4—C27—C28—C22	−179.4 (2)
C12—C11—C15—C19	54.0 (3)	C26—C27—C28—C22	−50.7 (3)
C10—C11—C15—C19	−59.6 (3)	C21—C22—C28—C27	−176.9 (2)
C14—C11—C15—C19	176.3 (2)	C23—C22—C28—C27	50.2 (3)
C12—C11—C15—C16	176.5 (2)	C21—C22—C28—C29	58.6 (3)
C10—C11—C15—C16	62.9 (2)	C23—C22—C28—C29	−74.3 (3)
C14—C11—C15—C16	−61.3 (3)	C21—C22—C28—C30	−60.5 (3)
C20—C15—C16—C17	−176.6 (2)	C23—C22—C28—C30	166.7 (3)
C19—C15—C16—C17	64.2 (3)	C3—C4—O2—C7	−159.0 (2)
C11—C15—C16—C17	−57.2 (3)	C5—C4—O2—C7	−34.9 (3)
C20—C15—C16—C23	49.3 (3)	C6—C7—O2—C4	28.8 (3)
C19—C15—C16—C23	−69.9 (3)	C9—C7—O2—C4	151.3 (2)
C11—C15—C16—C23	168.8 (2)	C8—C7—O2—C4	−89.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1ⁱ	0.82	2.09	2.905 (3)	172
O3—H3···O2	0.82	1.95	2.677 (3)	147
O1—H1···O3	0.82	2.14	2.948 (3)	170

Symmetry code: (i) x+1/2, −y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₃₀H₅₂O₄
M_r	476.72
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.6795 (14), 13.067 (3), 28.084 (5)
V (Å³)	2818.1 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14876, 5250, 3460
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.128, 1.06
No. of reflections	5250
No. of parameters	318
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1ⁱ	0.82	2.09	2.905 (3)	172.1
O3—H3···O2	0.82	1.95	2.677 (3)	147.0
O1—H1···O3	0.82	2.14	2.948 (3)	170.3

Symmetry code: (i) x+1/2, −y−1/2, −z.

Acknowledgements

The authors thank Mr Lian-dong Liu (College of Chemistry, Chemical Engineering and Materials Science, Shandong Normal University, Jinan 250014, People's Republic of China) for his invaluable support of the X-ray data collection. The authors would like to thank Shandong Provincial Natural Science Foundation, China (Y2007C138), the National Natural Science Foundation of China (No. 81001358) and the Promotive Research Fund for Excellent Young and Middle-aged Scientisits of Shandong Province (No. BS2010YY073) for research grants.

References

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Volume 67| Part 8| August 2011| Page o2112

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