organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

3β,11α-Dihy­dr­oxy-12-ursen-3-yl palmitate

aSchool of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453000, People's Republic of China
*Correspondence e-mail: baisuping@xxmu.edu.cn

(Received 28 October 2011; accepted 8 November 2011; online 19 November 2011)

In the title compound, C46H80O3, a natural ursane-type triperpenoid, four of the five six-membered rings adopt chair conformations; the fifth, which has a C=C double bond, adopts an approximate half-boat conformation. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming chains along [010].

Related literature

For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For spectroscopic properties of the title compound, see: Kakuda et al. (2003[Kakuda, R., Machida, K., Yaoita, Y., Kikuchi, M. & Kikuchi, M. (2003). Chem. Pharm. Bull. (Tokyo), 51, 885-887.]).

[Scheme 1]

Experimental

Crystal data
  • C46H80O3

  • Mr = 681.10

  • Monoclinic, P 21

  • a = 11.389 (2) Å

  • b = 15.714 (3) Å

  • c = 11.766 (2) Å

  • β = 98.925 (3)°

  • V = 2080.3 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 93 K

  • 0.60 × 0.50 × 0.30 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • 16995 measured reflections

  • 4832 independent reflections

  • 4397 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.098

  • S = 1.00

  • 4832 reflections

  • 455 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.22 e Å−3

  • Δρmin = −0.15 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1O⋯O3i 0.79 (4) 2.13 (4) 2.886 (3) 161 (3)
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+1].

Data collection: CrystalClear (Rigaku, 2008[Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound, (I), is a naturally occurring ursene-type triterpene isolated from the medicinal plant Saussurea nivea Turcz. This plant has been used as antibacterial, inflammation-diminishing drugs and febrifuge. The structure of compound (I) has been reported previously based on spectroscopic methods (Kakuda, et al., 2003). In order to further confirm the structure and conformation of (I), a crystal structure analysis, reported here, was undertaken.

The X-ray crystallographic analysis of (I) confirms the previously proposed molecular structure of (I) as an ursane-type triterpene. Fig. 1 shows its conformation: the palmitoyl group and the hydroxyl group is connected to C3 and C11 in β and α-orientation, respectively; while the Me-20 and Me-30 adopted β and α-orientation at C19 and C20, respectively; and the double bond is located at C12 and C13.The molecule contains five six-membered rings. The A/B and B/C ring junctions show trans fusion and the geometry of the rings is cis at the D/E ring junction. The bond lengths and angles of (I) have normal values (Allen et al., 1987), with the following average values (Å): Csp3—Csp3 = 1.533 (3), Csp3—Csp2 = 1.522 (3), Csp2—Csp2 = 1.333 (3), CO = 1.211 (3), Csp2—O = 1.330(3, Csp3—O = 1.452 (3)). Rings A, B and E have slightly flattened chair conformations, with average torsion angles of 53.6 (3), 53.4 (3) and 54.2 °, respectively. Chair conformations of ring D are twisted, with torsion angle range from 34.1 to 63.0 °. Ring C adopts an approximate half-boat conformation. The long carbon chain connected to C3, which takes anti-conformations in C4'-C9' and C10'-C16' with average dihedral angles of 176.9 and 177.0 °, has two turns on C3'-C4' and C9'-C10' in gauche-conformations with torsion angles of 73.9 and 69.4°, respectively. The crystal packing is stabilized by intermolecular O—H···O hydrogen bonds involving the carbonyl and hydroxyl groups (Table1 and Fig.2). The hydrogen bonds link the molecules into chains along the b axis.

Related literature top

For standard bond lengths, see: Allen et al. (1987). For spectroscopic properties of the title compound, see: Kakuda et al. (2003).

Experimental top

The dried and crushed leaves of Saussurea nivea Turcz (10 kg, collected from Tongbai Mountain, Henan Province, China) were extracted three times with Me2CO at room temperature for seven days. The extract was filtered and the solvent was removed under reduced pressure. The residue was partitioned between water and ethylacetate. After removing the solvent, the ethyl acetate residue was separated by repeated silica gel (200–300 mesh) column chromatography and recrystallization in CHCl3/Me2CO (30:1) to afford 20 mg of compound (I) (Optical rotation: [α]D25 +31.1 ° (c 0.27,CHCl3). Crystals suitable for x-ray experiment were obtained by slow evaporation of a solution of the compound (I) in Me2CO at room temperature.

Refinement top

All H atoms were included in calculated position and refined as riding atoms,with C—H = 0.95Å (CH3), 0.93 and 0.97 Å(CH2), 0.98 Å(CH), and with Uiso(H) =1.2Ueq(C). In the absence of significant anomalous scattering effects,Friedel pairs were merged. The choice of enantiomer was based on comparison of the optical rotation with that of related compounds with known stereochemistry.

Structure description top

The title compound, (I), is a naturally occurring ursene-type triterpene isolated from the medicinal plant Saussurea nivea Turcz. This plant has been used as antibacterial, inflammation-diminishing drugs and febrifuge. The structure of compound (I) has been reported previously based on spectroscopic methods (Kakuda, et al., 2003). In order to further confirm the structure and conformation of (I), a crystal structure analysis, reported here, was undertaken.

The X-ray crystallographic analysis of (I) confirms the previously proposed molecular structure of (I) as an ursane-type triterpene. Fig. 1 shows its conformation: the palmitoyl group and the hydroxyl group is connected to C3 and C11 in β and α-orientation, respectively; while the Me-20 and Me-30 adopted β and α-orientation at C19 and C20, respectively; and the double bond is located at C12 and C13.The molecule contains five six-membered rings. The A/B and B/C ring junctions show trans fusion and the geometry of the rings is cis at the D/E ring junction. The bond lengths and angles of (I) have normal values (Allen et al., 1987), with the following average values (Å): Csp3—Csp3 = 1.533 (3), Csp3—Csp2 = 1.522 (3), Csp2—Csp2 = 1.333 (3), CO = 1.211 (3), Csp2—O = 1.330(3, Csp3—O = 1.452 (3)). Rings A, B and E have slightly flattened chair conformations, with average torsion angles of 53.6 (3), 53.4 (3) and 54.2 °, respectively. Chair conformations of ring D are twisted, with torsion angle range from 34.1 to 63.0 °. Ring C adopts an approximate half-boat conformation. The long carbon chain connected to C3, which takes anti-conformations in C4'-C9' and C10'-C16' with average dihedral angles of 176.9 and 177.0 °, has two turns on C3'-C4' and C9'-C10' in gauche-conformations with torsion angles of 73.9 and 69.4°, respectively. The crystal packing is stabilized by intermolecular O—H···O hydrogen bonds involving the carbonyl and hydroxyl groups (Table1 and Fig.2). The hydrogen bonds link the molecules into chains along the b axis.

For standard bond lengths, see: Allen et al. (1987). For spectroscopic properties of the title compound, see: Kakuda et al. (2003).

Computing details top

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of compound (I). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the a axis, showing the O—H···O hydrogen bonds as dashed lines.Symmetry code: (i) -x+1, y-1/2, -z+1.
3β,11α-Dihydroxy-12-ursen-3-yl palmitate top
Crystal data top
C46H80O3F(000) = 760
Mr = 681.10Dx = 1.087 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 11.389 (2) ÅCell parameters from 7345 reflections
b = 15.714 (3) Åθ = 3.0–27.5°
c = 11.766 (2) ŵ = 0.07 mm1
β = 98.925 (3)°T = 93 K
V = 2080.3 (7) Å3Block, colourless
Z = 20.60 × 0.50 × 0.30 mm
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
4397 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.032
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
Detector resolution: 28.5714 pixels mm-1h = 1414
phi and ω scansk = 2020
16995 measured reflectionsl = 1414
4832 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0286P)2 + 0.860P]
where P = (Fo2 + 2Fc2)/3
4832 reflections(Δ/σ)max < 0.001
455 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = 0.15 e Å3
Crystal data top
C46H80O3V = 2080.3 (7) Å3
Mr = 681.10Z = 2
Monoclinic, P21Mo Kα radiation
a = 11.389 (2) ŵ = 0.07 mm1
b = 15.714 (3) ÅT = 93 K
c = 11.766 (2) Å0.60 × 0.50 × 0.30 mm
β = 98.925 (3)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
4397 reflections with I > 2σ(I)
16995 measured reflectionsRint = 0.032
4832 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0431 restraint
wR(F2) = 0.098H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.22 e Å3
4832 reflectionsΔρmin = 0.15 e Å3
455 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
xyzUiso*/Ueq
O10.7358 (2)0.09757 (13)0.56526 (16)0.0423 (5)
O20.66023 (16)0.51467 (12)0.64282 (16)0.0373 (4)
O30.48079 (18)0.51257 (14)0.53336 (17)0.0469 (5)
C10.7086 (2)0.27759 (15)0.6092 (2)0.0282 (5)
H1A0.74940.24680.55310.034*
H1B0.62480.25840.59800.034*
C20.7121 (2)0.37373 (16)0.5849 (2)0.0321 (6)
H2A0.79580.39250.59030.039*
H2B0.67160.38530.50570.039*
C30.6522 (2)0.42345 (17)0.6692 (2)0.0328 (6)
H30.56640.40690.65900.039*
C40.7061 (2)0.41063 (16)0.7958 (2)0.0302 (5)
C50.7115 (2)0.31251 (16)0.8183 (2)0.0263 (5)
H50.62640.29440.80850.032*
C60.7608 (2)0.28945 (16)0.9424 (2)0.0298 (5)
H6A0.73000.32990.99520.036*
H6B0.84850.29400.95450.036*
C70.7248 (2)0.19890 (16)0.9696 (2)0.0286 (5)
H7A0.63740.19670.96510.034*
H7B0.76050.18501.04960.034*
C80.76315 (19)0.13074 (16)0.8885 (2)0.0245 (5)
C90.73602 (19)0.15932 (16)0.76015 (19)0.0238 (5)
H90.64760.15580.73940.029*
C100.7685 (2)0.25440 (16)0.7329 (2)0.0253 (5)
C110.7853 (2)0.09126 (17)0.6844 (2)0.0288 (5)
H110.87270.10160.69030.035*
C120.7700 (2)0.00159 (16)0.7251 (2)0.0274 (5)
H120.79200.04270.67750.033*
C130.72899 (19)0.02268 (15)0.8202 (2)0.0241 (5)
C140.6930 (2)0.04465 (16)0.9029 (2)0.0251 (5)
C150.7157 (2)0.01434 (17)1.0297 (2)0.0307 (5)
H15A0.79930.02701.06260.037*
H15B0.66410.04731.07400.037*
C160.6926 (2)0.08099 (17)1.0454 (2)0.0318 (5)
H16A0.60640.09221.02490.038*
H16B0.71640.09621.12730.038*
C170.7605 (2)0.13792 (17)0.9712 (2)0.0293 (5)
C180.7145 (2)0.11755 (16)0.8435 (2)0.0268 (5)
H180.76810.14830.79760.032*
C190.5867 (2)0.15270 (16)0.8029 (2)0.0288 (5)
H190.53150.12300.84820.035*
C200.5810 (2)0.24905 (17)0.8281 (2)0.0320 (5)
H200.63850.27860.78540.038*
C210.6193 (2)0.26572 (17)0.9567 (2)0.0350 (6)
H21A0.56300.23751.00080.042*
H21B0.61700.32760.97170.042*
C220.7438 (2)0.23238 (18)0.9970 (2)0.0351 (6)
H22A0.80060.26610.95960.042*
H22B0.76380.24141.08100.042*
C230.8264 (2)0.45627 (17)0.8259 (2)0.0326 (6)
H23A0.87910.43890.77160.039*
H23B0.86280.44100.90420.039*
H23C0.81420.51800.82090.039*
C240.6193 (2)0.45184 (18)0.8686 (3)0.0413 (7)
H24A0.60900.51220.84850.050*
H24B0.65160.44650.95050.050*
H24C0.54220.42290.85310.050*
C250.9039 (2)0.26877 (17)0.7378 (2)0.0289 (5)
H25A0.93800.22110.70030.035*
H25B0.94200.27250.81820.035*
H25C0.91720.32180.69790.035*
C260.8995 (2)0.11656 (17)0.9255 (2)0.0294 (5)
H26A0.94190.16980.91650.035*
H26B0.92710.07250.87700.035*
H26C0.91500.09851.00620.035*
C270.5556 (2)0.05609 (17)0.8704 (2)0.0296 (5)
H27A0.53490.06290.78690.036*
H27B0.53040.10670.90900.036*
H27C0.51520.00580.89490.036*
C280.8948 (2)0.11911 (19)0.9984 (2)0.0394 (6)
H28A0.93830.15960.95700.047*
H28B0.92150.12481.08130.047*
H28C0.91010.06100.97410.047*
C290.5451 (3)0.13413 (19)0.6761 (2)0.0426 (7)
H29A0.59840.16200.62980.051*
H29B0.54580.07250.66310.051*
H29C0.46420.15590.65370.051*
C300.4576 (2)0.28749 (19)0.7892 (2)0.0398 (6)
H30A0.45770.34730.81270.048*
H30B0.43790.28360.70530.048*
H30C0.39850.25610.82480.048*
C1'0.5716 (2)0.54980 (18)0.5713 (2)0.0350 (6)
C2'0.5993 (3)0.64035 (18)0.5409 (2)0.0390 (6)
H2'10.52720.67590.53790.047*
H2'20.66150.66390.60070.047*
C3'0.6418 (3)0.6424 (2)0.4257 (3)0.0492 (8)
H3'10.58340.61220.36870.059*
H3'20.71810.61130.43200.059*
C4'0.6596 (3)0.7331 (2)0.3812 (3)0.0549 (9)
H4'10.66510.72960.29820.066*
H4'20.58830.76720.38910.066*
C5'0.7677 (3)0.77948 (19)0.4411 (2)0.0403 (6)
H5'10.83920.74440.43760.048*
H5'20.76010.78740.52310.048*
C6'0.7836 (3)0.8663 (2)0.3869 (3)0.0511 (8)
H6'10.78640.85770.30400.061*
H6'20.71250.90120.39300.061*
C7'0.8925 (2)0.91628 (18)0.4381 (2)0.0369 (6)
H7'10.96420.88080.43670.044*
H7'20.88750.92960.51950.044*
C8'0.9052 (3)0.99922 (19)0.3730 (3)0.0407 (6)
H8'10.90870.98540.29150.049*
H8'20.83331.03420.37500.049*
C9'1.0140 (3)1.05190 (18)0.4201 (3)0.0413 (7)
H9'11.08561.01560.42440.050*
H9'21.00711.07040.49920.050*
C10'1.0300 (2)1.13012 (18)0.3475 (3)0.0414 (7)
H10A1.02741.11230.26650.050*
H10B1.10961.15470.37400.050*
C11'0.9365 (3)1.19878 (19)0.3527 (3)0.0424 (7)
H11A0.93641.21460.43410.051*
H11B0.85731.17500.32250.051*
C12'0.9563 (2)1.27902 (18)0.2846 (2)0.0382 (6)
H12A1.03461.30380.31560.046*
H12B0.95741.26350.20320.046*
C13'0.8604 (2)1.34523 (19)0.2901 (3)0.0396 (6)
H13A0.85641.35760.37190.048*
H13B0.78291.32080.25560.048*
C14'0.8783 (2)1.42849 (18)0.2295 (2)0.0357 (6)
H14A0.95171.45620.26860.043*
H14B0.88941.41620.14930.043*
C15'0.7755 (3)1.4889 (2)0.2281 (3)0.0464 (7)
H15C0.76191.49830.30820.056*
H15D0.70321.46180.18570.056*
C16'0.7929 (3)1.5745 (2)0.1735 (3)0.0502 (8)
H16'A0.86131.60350.21780.060*
H16'B0.72151.60930.17330.060*
H16'C0.80721.56600.09430.060*
H1O0.674 (3)0.074 (3)0.554 (3)0.057 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0667 (14)0.0380 (11)0.0214 (10)0.0177 (11)0.0045 (9)0.0005 (8)
O20.0324 (9)0.0323 (10)0.0443 (11)0.0016 (8)0.0027 (8)0.0066 (9)
O30.0447 (11)0.0427 (11)0.0469 (12)0.0035 (10)0.0134 (9)0.0033 (10)
C10.0303 (12)0.0304 (13)0.0224 (12)0.0072 (10)0.0010 (9)0.0018 (10)
C20.0325 (12)0.0337 (14)0.0284 (13)0.0080 (11)0.0006 (10)0.0063 (11)
C30.0245 (12)0.0316 (13)0.0411 (15)0.0042 (10)0.0009 (10)0.0036 (12)
C40.0253 (12)0.0293 (13)0.0364 (14)0.0021 (10)0.0057 (10)0.0010 (11)
C50.0221 (11)0.0303 (12)0.0267 (13)0.0026 (9)0.0039 (9)0.0001 (10)
C60.0312 (12)0.0323 (13)0.0261 (13)0.0021 (10)0.0054 (10)0.0045 (10)
C70.0304 (12)0.0346 (14)0.0208 (12)0.0002 (10)0.0044 (9)0.0002 (10)
C80.0205 (10)0.0308 (12)0.0219 (12)0.0010 (9)0.0026 (8)0.0005 (10)
C90.0204 (10)0.0305 (12)0.0196 (11)0.0041 (9)0.0005 (8)0.0008 (9)
C100.0224 (11)0.0291 (12)0.0242 (12)0.0053 (9)0.0031 (9)0.0001 (10)
C110.0304 (12)0.0333 (13)0.0231 (12)0.0075 (10)0.0057 (10)0.0007 (10)
C120.0264 (11)0.0304 (13)0.0262 (12)0.0026 (10)0.0067 (9)0.0030 (10)
C130.0199 (10)0.0300 (12)0.0214 (12)0.0007 (9)0.0003 (9)0.0020 (9)
C140.0224 (11)0.0310 (12)0.0223 (12)0.0010 (9)0.0047 (9)0.0019 (9)
C150.0321 (12)0.0385 (14)0.0218 (12)0.0015 (11)0.0053 (10)0.0030 (11)
C160.0321 (12)0.0404 (14)0.0224 (12)0.0015 (11)0.0027 (10)0.0089 (11)
C170.0235 (11)0.0346 (13)0.0285 (13)0.0035 (10)0.0000 (9)0.0103 (11)
C180.0240 (11)0.0299 (13)0.0271 (13)0.0036 (9)0.0059 (9)0.0046 (10)
C190.0283 (12)0.0307 (13)0.0271 (13)0.0011 (10)0.0031 (9)0.0049 (10)
C200.0317 (13)0.0320 (13)0.0329 (14)0.0004 (10)0.0071 (10)0.0066 (11)
C210.0369 (14)0.0334 (14)0.0355 (15)0.0008 (11)0.0081 (11)0.0118 (11)
C220.0320 (13)0.0382 (15)0.0341 (14)0.0056 (11)0.0024 (11)0.0119 (12)
C230.0313 (13)0.0309 (13)0.0349 (14)0.0039 (10)0.0028 (10)0.0002 (11)
C240.0387 (15)0.0358 (15)0.0519 (18)0.0037 (12)0.0152 (13)0.0013 (13)
C250.0236 (11)0.0329 (13)0.0306 (13)0.0055 (10)0.0052 (9)0.0002 (10)
C260.0235 (11)0.0376 (14)0.0256 (12)0.0009 (10)0.0006 (9)0.0008 (10)
C270.0217 (11)0.0323 (13)0.0357 (14)0.0027 (10)0.0072 (10)0.0030 (11)
C280.0277 (13)0.0424 (16)0.0453 (16)0.0058 (12)0.0034 (11)0.0110 (13)
C290.0504 (16)0.0360 (15)0.0366 (15)0.0131 (13)0.0082 (12)0.0079 (12)
C300.0389 (15)0.0412 (16)0.0398 (16)0.0052 (12)0.0074 (12)0.0088 (13)
C1'0.0362 (13)0.0364 (14)0.0313 (14)0.0044 (11)0.0018 (11)0.0012 (11)
C2'0.0428 (15)0.0351 (15)0.0373 (15)0.0054 (12)0.0005 (12)0.0027 (12)
C3'0.0579 (19)0.0502 (19)0.0373 (17)0.0116 (15)0.0007 (13)0.0043 (14)
C4'0.057 (2)0.066 (2)0.0379 (17)0.0130 (17)0.0059 (14)0.0150 (16)
C5'0.0404 (15)0.0463 (17)0.0338 (15)0.0011 (12)0.0046 (11)0.0078 (13)
C6'0.0489 (17)0.054 (2)0.0472 (18)0.0057 (15)0.0046 (14)0.0187 (15)
C7'0.0400 (14)0.0384 (15)0.0336 (14)0.0072 (12)0.0104 (11)0.0007 (12)
C8'0.0456 (15)0.0388 (15)0.0388 (15)0.0046 (13)0.0101 (12)0.0040 (12)
C9'0.0404 (15)0.0389 (15)0.0439 (17)0.0098 (12)0.0046 (12)0.0022 (13)
C10'0.0367 (14)0.0356 (15)0.0534 (18)0.0005 (12)0.0115 (13)0.0058 (14)
C11'0.0398 (15)0.0373 (15)0.0516 (18)0.0040 (12)0.0114 (13)0.0041 (13)
C12'0.0379 (14)0.0349 (15)0.0420 (16)0.0005 (11)0.0075 (12)0.0010 (12)
C13'0.0332 (14)0.0396 (15)0.0454 (16)0.0024 (12)0.0042 (12)0.0044 (13)
C14'0.0322 (13)0.0344 (14)0.0399 (15)0.0026 (11)0.0036 (11)0.0013 (12)
C15'0.0385 (15)0.0436 (17)0.0577 (19)0.0051 (13)0.0095 (14)0.0114 (14)
C16'0.0411 (16)0.0417 (17)0.068 (2)0.0077 (13)0.0100 (15)0.0155 (16)
Geometric parameters (Å, º) top
O1—C111.431 (3)C24—H24B0.9800
O1—H1O0.79 (4)C24—H24C0.9800
O2—C1'1.330 (3)C25—H25A0.9800
O2—C31.473 (3)C25—H25B0.9800
O3—C1'1.211 (3)C25—H25C0.9800
C1—C21.539 (3)C26—H26A0.9800
C1—C101.552 (3)C26—H26B0.9800
C1—H1A0.9900C26—H26C0.9800
C1—H1B0.9900C27—H27A0.9800
C2—C31.507 (4)C27—H27B0.9800
C2—H2A0.9900C27—H27C0.9800
C2—H2B0.9900C28—H28A0.9800
C3—C41.533 (4)C28—H28B0.9800
C3—H31.0000C28—H28C0.9800
C4—C231.539 (3)C29—H29A0.9800
C4—C241.547 (4)C29—H29B0.9800
C4—C51.564 (3)C29—H29C0.9800
C5—C61.524 (3)C30—H30A0.9800
C5—C101.571 (3)C30—H30B0.9800
C5—H51.0000C30—H30C0.9800
C6—C71.528 (3)C1'—C2'1.513 (4)
C6—H6A0.9900C2'—C3'1.508 (4)
C6—H6B0.9900C2'—H2'10.9900
C7—C81.542 (3)C2'—H2'20.9900
C7—H7A0.9900C3'—C4'1.542 (5)
C7—H7B0.9900C3'—H3'10.9900
C8—C91.559 (3)C3'—H3'20.9900
C8—C261.562 (3)C4'—C5'1.508 (4)
C8—C141.594 (3)C4'—H4'10.9900
C9—C111.552 (3)C4'—H4'20.9900
C9—C101.584 (3)C5'—C6'1.528 (4)
C9—H91.0000C5'—H5'10.9900
C10—C251.550 (3)C5'—H5'20.9900
C11—C121.507 (4)C6'—C7'1.512 (4)
C11—H111.0000C6'—H6'10.9900
C12—C131.333 (3)C6'—H6'20.9900
C12—H120.9500C7'—C8'1.530 (4)
C13—C181.530 (3)C7'—H7'10.9900
C13—C141.536 (3)C7'—H7'20.9900
C14—C151.549 (3)C8'—C9'1.521 (4)
C14—C271.563 (3)C8'—H8'10.9900
C15—C161.537 (4)C8'—H8'20.9900
C15—H15A0.9900C9'—C10'1.524 (4)
C15—H15B0.9900C9'—H9'10.9900
C16—C171.539 (4)C9'—H9'20.9900
C16—H16A0.9900C10'—C11'1.524 (4)
C16—H16B0.9900C10'—H10A0.9900
C17—C221.533 (4)C10'—H10B0.9900
C17—C281.542 (3)C11'—C12'1.529 (4)
C17—C181.546 (3)C11'—H11A0.9900
C18—C191.561 (3)C11'—H11B0.9900
C18—H181.0000C12'—C13'1.517 (4)
C19—C291.522 (3)C12'—H12A0.9900
C19—C201.546 (4)C12'—H12B0.9900
C19—H191.0000C13'—C14'1.519 (4)
C20—C211.531 (4)C13'—H13A0.9900
C20—C301.533 (4)C13'—H13B0.9900
C20—H201.0000C14'—C15'1.505 (4)
C21—C221.517 (4)C14'—H14A0.9900
C21—H21A0.9900C14'—H14B0.9900
C21—H21B0.9900C15'—C16'1.517 (4)
C22—H22A0.9900C15'—H15C0.9900
C22—H22B0.9900C15'—H15D0.9900
C23—H23A0.9800C16'—H16'A0.9800
C23—H23B0.9800C16'—H16'B0.9800
C23—H23C0.9800C16'—H16'C0.9800
C24—H24A0.9800
C11—O1—H1O110 (3)C4—C24—H24B109.5
C1'—O2—C3118.1 (2)H24A—C24—H24B109.5
C2—C1—C10112.6 (2)C4—C24—H24C109.5
C2—C1—H1A109.1H24A—C24—H24C109.5
C10—C1—H1A109.1H24B—C24—H24C109.5
C2—C1—H1B109.1C10—C25—H25A109.5
C10—C1—H1B109.1C10—C25—H25B109.5
H1A—C1—H1B107.8H25A—C25—H25B109.5
C3—C2—C1111.0 (2)C10—C25—H25C109.5
C3—C2—H2A109.4H25A—C25—H25C109.5
C1—C2—H2A109.4H25B—C25—H25C109.5
C3—C2—H2B109.4C8—C26—H26A109.5
C1—C2—H2B109.4C8—C26—H26B109.5
H2A—C2—H2B108.0H26A—C26—H26B109.5
O2—C3—C2108.4 (2)C8—C26—H26C109.5
O2—C3—C4107.7 (2)H26A—C26—H26C109.5
C2—C3—C4114.7 (2)H26B—C26—H26C109.5
O2—C3—H3108.6C14—C27—H27A109.5
C2—C3—H3108.6C14—C27—H27B109.5
C4—C3—H3108.6H27A—C27—H27B109.5
C3—C4—C23111.7 (2)C14—C27—H27C109.5
C3—C4—C24106.8 (2)H27A—C27—H27C109.5
C23—C4—C24107.5 (2)H27B—C27—H27C109.5
C3—C4—C5107.1 (2)C17—C28—H28A109.5
C23—C4—C5114.2 (2)C17—C28—H28B109.5
C24—C4—C5109.3 (2)H28A—C28—H28B109.5
C6—C5—C4113.3 (2)C17—C28—H28C109.5
C6—C5—C10110.3 (2)H28A—C28—H28C109.5
C4—C5—C10118.3 (2)H28B—C28—H28C109.5
C6—C5—H5104.4C19—C29—H29A109.5
C4—C5—H5104.4C19—C29—H29B109.5
C10—C5—H5104.4H29A—C29—H29B109.5
C5—C6—C7110.6 (2)C19—C29—H29C109.5
C5—C6—H6A109.5H29A—C29—H29C109.5
C7—C6—H6A109.5H29B—C29—H29C109.5
C5—C6—H6B109.5C20—C30—H30A109.5
C7—C6—H6B109.5C20—C30—H30B109.5
H6A—C6—H6B108.1H30A—C30—H30B109.5
C6—C7—C8113.97 (19)C20—C30—H30C109.5
C6—C7—H7A108.8H30A—C30—H30C109.5
C8—C7—H7A108.8H30B—C30—H30C109.5
C6—C7—H7B108.8O3—C1'—O2123.6 (3)
C8—C7—H7B108.8O3—C1'—C2'124.4 (3)
H7A—C7—H7B107.7O2—C1'—C2'112.0 (2)
C7—C8—C9111.5 (2)C3'—C2'—C1'109.9 (2)
C7—C8—C26106.91 (19)C3'—C2'—H2'1109.7
C9—C8—C26110.50 (18)C1'—C2'—H2'1109.7
C7—C8—C14109.20 (18)C3'—C2'—H2'2109.7
C9—C8—C14108.69 (18)C1'—C2'—H2'2109.7
C26—C8—C14110.02 (19)H2'1—C2'—H2'2108.2
C11—C9—C8108.81 (19)C2'—C3'—C4'113.7 (3)
C11—C9—C10114.66 (18)C2'—C3'—H3'1108.8
C8—C9—C10116.76 (18)C4'—C3'—H3'1108.8
C11—C9—H9105.1C2'—C3'—H3'2108.8
C8—C9—H9105.1C4'—C3'—H3'2108.8
C10—C9—H9105.1H3'1—C3'—H3'2107.7
C25—C10—C1106.87 (19)C5'—C4'—C3'115.4 (3)
C25—C10—C5113.51 (19)C5'—C4'—H4'1108.4
C1—C10—C5107.37 (19)C3'—C4'—H4'1108.4
C25—C10—C9113.08 (19)C5'—C4'—H4'2108.4
C1—C10—C9109.20 (18)C3'—C4'—H4'2108.4
C5—C10—C9106.63 (18)H4'1—C4'—H4'2107.5
O1—C11—C12109.2 (2)C4'—C5'—C6'112.2 (2)
O1—C11—C9113.1 (2)C4'—C5'—H5'1109.2
C12—C11—C9113.08 (19)C6'—C5'—H5'1109.2
O1—C11—H11107.0C4'—C5'—H5'2109.2
C12—C11—H11107.0C6'—C5'—H5'2109.2
C9—C11—H11107.0H5'1—C5'—H5'2107.9
C13—C12—C11127.4 (2)C7'—C6'—C5'116.1 (2)
C13—C12—H12116.3C7'—C6'—H6'1108.3
C11—C12—H12116.3C5'—C6'—H6'1108.3
C12—C13—C18119.4 (2)C7'—C6'—H6'2108.3
C12—C13—C14119.8 (2)C5'—C6'—H6'2108.3
C18—C13—C14120.69 (19)H6'1—C6'—H6'2107.4
C13—C14—C15112.2 (2)C6'—C7'—C8'112.2 (2)
C13—C14—C27106.24 (19)C6'—C7'—H7'1109.2
C15—C14—C27106.42 (19)C8'—C7'—H7'1109.2
C13—C14—C8109.24 (18)C6'—C7'—H7'2109.2
C15—C14—C8110.61 (19)C8'—C7'—H7'2109.2
C27—C14—C8112.09 (19)H7'1—C7'—H7'2107.9
C16—C15—C14114.1 (2)C9'—C8'—C7'114.6 (2)
C16—C15—H15A108.7C9'—C8'—H8'1108.6
C14—C15—H15A108.7C7'—C8'—H8'1108.6
C16—C15—H15B108.7C9'—C8'—H8'2108.6
C14—C15—H15B108.7C7'—C8'—H8'2108.6
H15A—C15—H15B107.6H8'1—C8'—H8'2107.6
C15—C16—C17112.8 (2)C8'—C9'—C10'113.4 (2)
C15—C16—H16A109.0C8'—C9'—H9'1108.9
C17—C16—H16A109.0C10'—C9'—H9'1108.9
C15—C16—H16B109.0C8'—C9'—H9'2108.9
C17—C16—H16B109.0C10'—C9'—H9'2108.9
H16A—C16—H16B107.8H9'1—C9'—H9'2107.7
C22—C17—C16111.3 (2)C9'—C10'—C11'113.8 (2)
C22—C17—C28107.1 (2)C9'—C10'—H10A108.8
C16—C17—C28109.9 (2)C11'—C10'—H10A108.8
C22—C17—C18111.0 (2)C9'—C10'—H10B108.8
C16—C17—C18107.82 (19)C11'—C10'—H10B108.8
C28—C17—C18109.7 (2)H10A—C10'—H10B107.7
C13—C18—C17110.3 (2)C10'—C11'—C12'113.7 (2)
C13—C18—C19114.29 (19)C10'—C11'—H11A108.8
C17—C18—C19112.55 (19)C12'—C11'—H11A108.8
C13—C18—H18106.4C10'—C11'—H11B108.8
C17—C18—H18106.4C12'—C11'—H11B108.8
C19—C18—H18106.4H11A—C11'—H11B107.7
C29—C19—C20111.1 (2)C13'—C12'—C11'112.2 (2)
C29—C19—C18111.5 (2)C13'—C12'—H12A109.2
C20—C19—C18110.7 (2)C11'—C12'—H12A109.2
C29—C19—H19107.8C13'—C12'—H12B109.2
C20—C19—H19107.8C11'—C12'—H12B109.2
C18—C19—H19107.8H12A—C12'—H12B107.9
C21—C20—C30109.6 (2)C12'—C13'—C14'114.9 (2)
C21—C20—C19110.1 (2)C12'—C13'—H13A108.5
C30—C20—C19113.1 (2)C14'—C13'—H13A108.5
C21—C20—H20108.0C12'—C13'—H13B108.5
C30—C20—H20108.0C14'—C13'—H13B108.5
C19—C20—H20108.0H13A—C13'—H13B107.5
C22—C21—C20111.0 (2)C15'—C14'—C13'112.8 (2)
C22—C21—H21A109.4C15'—C14'—H14A109.0
C20—C21—H21A109.4C13'—C14'—H14A109.0
C22—C21—H21B109.4C15'—C14'—H14B109.0
C20—C21—H21B109.4C13'—C14'—H14B109.0
H21A—C21—H21B108.0H14A—C14'—H14B107.8
C21—C22—C17114.3 (2)C14'—C15'—C16'114.3 (2)
C21—C22—H22A108.7C14'—C15'—H15C108.7
C17—C22—H22A108.7C16'—C15'—H15C108.7
C21—C22—H22B108.7C14'—C15'—H15D108.7
C17—C22—H22B108.7C16'—C15'—H15D108.7
H22A—C22—H22B107.6H15C—C15'—H15D107.6
C4—C23—H23A109.5C15'—C16'—H16'A109.5
C4—C23—H23B109.5C15'—C16'—H16'B109.5
H23A—C23—H23B109.5H16'A—C16'—H16'B109.5
C4—C23—H23C109.5C15'—C16'—H16'C109.5
H23A—C23—H23C109.5H16'A—C16'—H16'C109.5
H23B—C23—H23C109.5H16'B—C16'—H16'C109.5
C4—C24—H24A109.5
C10—C1—C2—C358.1 (3)C7—C8—C14—C13178.74 (18)
C1'—O2—C3—C291.8 (3)C9—C8—C14—C1356.9 (2)
C1'—O2—C3—C4143.6 (2)C26—C8—C14—C1364.2 (2)
C1—C2—C3—O2179.05 (19)C7—C8—C14—C1557.3 (2)
C1—C2—C3—C458.7 (3)C9—C8—C14—C15179.17 (19)
O2—C3—C4—C2347.3 (3)C26—C8—C14—C1559.7 (2)
C2—C3—C4—C2373.5 (3)C7—C8—C14—C2761.3 (2)
O2—C3—C4—C2470.0 (2)C9—C8—C14—C2760.6 (2)
C2—C3—C4—C24169.2 (2)C26—C8—C14—C27178.31 (19)
O2—C3—C4—C5173.05 (19)C13—C14—C15—C1636.2 (3)
C2—C3—C4—C552.2 (3)C27—C14—C15—C1679.6 (2)
C3—C4—C5—C6178.62 (19)C8—C14—C15—C16158.42 (19)
C23—C4—C5—C657.2 (3)C14—C15—C16—C1753.3 (3)
C24—C4—C5—C663.3 (3)C15—C16—C17—C22175.0 (2)
C3—C4—C5—C1050.0 (3)C15—C16—C17—C2856.6 (3)
C23—C4—C5—C1074.2 (3)C15—C16—C17—C1863.0 (3)
C24—C4—C5—C10165.3 (2)C12—C13—C18—C17136.7 (2)
C4—C5—C6—C7160.3 (2)C14—C13—C18—C1745.3 (3)
C10—C5—C6—C764.5 (2)C12—C13—C18—C1995.3 (3)
C5—C6—C7—C856.4 (3)C14—C13—C18—C1982.7 (3)
C6—C7—C8—C945.0 (3)C22—C17—C18—C13178.59 (19)
C6—C7—C8—C2675.8 (2)C16—C17—C18—C1356.5 (2)
C6—C7—C8—C14165.16 (19)C28—C17—C18—C1363.2 (3)
C7—C8—C9—C11175.71 (19)C22—C17—C18—C1949.6 (3)
C26—C8—C9—C1157.0 (2)C16—C17—C18—C1972.5 (3)
C14—C8—C9—C1163.9 (2)C28—C17—C18—C19167.8 (2)
C7—C8—C9—C1044.0 (2)C13—C18—C19—C2954.9 (3)
C26—C8—C9—C1074.8 (2)C17—C18—C19—C29178.3 (2)
C14—C8—C9—C10164.42 (17)C13—C18—C19—C20179.0 (2)
C2—C1—C10—C2570.0 (3)C17—C18—C19—C2054.1 (3)
C2—C1—C10—C552.1 (3)C29—C19—C20—C21178.1 (2)
C2—C1—C10—C9167.35 (19)C18—C19—C20—C2157.5 (3)
C6—C5—C10—C2565.6 (3)C29—C19—C20—C3055.2 (3)
C4—C5—C10—C2567.2 (3)C18—C19—C20—C30179.5 (2)
C6—C5—C10—C1176.55 (19)C30—C20—C21—C22177.1 (2)
C4—C5—C10—C150.7 (3)C19—C20—C21—C2257.9 (3)
C6—C5—C10—C959.6 (2)C20—C21—C22—C1755.4 (3)
C4—C5—C10—C9167.66 (19)C16—C17—C22—C2169.4 (3)
C11—C9—C10—C2554.3 (3)C28—C17—C22—C21170.5 (2)
C8—C9—C10—C2574.7 (2)C18—C17—C22—C2150.7 (3)
C11—C9—C10—C164.6 (2)C3—O2—C1'—O35.6 (4)
C8—C9—C10—C1166.46 (19)C3—O2—C1'—C2'172.8 (2)
C11—C9—C10—C5179.70 (19)O3—C1'—C2'—C3'79.7 (3)
C8—C9—C10—C550.7 (2)O2—C1'—C2'—C3'98.7 (3)
C8—C9—C11—O1162.55 (19)C1'—C2'—C3'—C4'173.8 (3)
C10—C9—C11—O164.6 (2)C2'—C3'—C4'—C5'73.9 (4)
C8—C9—C11—C1237.8 (3)C3'—C4'—C5'—C6'176.2 (3)
C10—C9—C11—C12170.67 (18)C4'—C5'—C6'—C7'177.6 (3)
O1—C11—C12—C13132.5 (3)C5'—C6'—C7'—C8'176.1 (3)
C9—C11—C12—C135.7 (3)C6'—C7'—C8'—C9'179.5 (3)
C11—C12—C13—C18177.1 (2)C7'—C8'—C9'—C10'175.0 (2)
C11—C12—C13—C140.9 (4)C8'—C9'—C10'—C11'69.4 (3)
C12—C13—C14—C15147.9 (2)C9'—C10'—C11'—C12'177.2 (2)
C18—C13—C14—C1534.1 (3)C10'—C11'—C12'—C13'179.0 (3)
C12—C13—C14—C2796.2 (2)C11'—C12'—C13'—C14'176.9 (2)
C18—C13—C14—C2781.7 (2)C12'—C13'—C14'—C15'174.7 (3)
C12—C13—C14—C824.9 (3)C13'—C14'—C15'—C16'177.1 (3)
C18—C13—C14—C8157.2 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O3i0.79 (4)2.13 (4)2.886 (3)161 (3)
Symmetry code: (i) x+1, y1/2, z+1.

Experimental details

Crystal data
Chemical formulaC46H80O3
Mr681.10
Crystal system, space groupMonoclinic, P21
Temperature (K)93
a, b, c (Å)11.389 (2), 15.714 (3), 11.766 (2)
β (°) 98.925 (3)
V3)2080.3 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.60 × 0.50 × 0.30
Data collection
DiffractometerRigaku AFC10/Saturn724+
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16995, 4832, 4397
Rint0.032
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.098, 1.00
No. of reflections4832
No. of parameters455
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.22, 0.15

Computer programs: CrystalClear (Rigaku, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O3i0.79 (4)2.13 (4)2.886 (3)161 (3)
Symmetry code: (i) x+1, y1/2, z+1.
 

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 81072552) and the Henan Province Science and Technology Innovation Funndation for Outstanding Young Scholars (No. 104100510016).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
First citationKakuda, R., Machida, K., Yaoita, Y., Kikuchi, M. & Kikuchi, M. (2003). Chem. Pharm. Bull. (Tokyo), 51, 885–887.  CrossRef PubMed CAS Google Scholar
First citationRigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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