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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Eth­oxy­carbonyl­methyl ursolate

aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China
*Correspondence e-mail: chuandayouji217@163.com

(Received 9 November 2008; accepted 25 November 2008; online 29 November 2008)

The title compound, C34H54O5, was synthesized by the reaction of ursolic acid with ethyl chloro­acetate in the presence of DMA. All six-membered rings of the penta­cyclic triterpene skeleton adopt chair conformations. In the crystal structure, mol­ecules are linked by inter­molecular O—H⋯O hydrogen-bond inter­actions, forming zigzag chains along the c axis.

Related literature

For the pharmacological activity of ursolic acid, see: Es-saady et al. (1996[Es-saady, D., Simon, A., Ollier, M., Maurizis, J. C., Chulia, A. J. & Delage, C. (1996). Cancer Lett. 106, 193-197.]); Kashiwada et al. (2000[Kashiwada, Y., Nagao, T., Hashimoto, A., Ikeshiro, Y., Okabe, H. & Cosention, L. M. H. (2000). J. Nat. Prod. 63, 1619-1622.]). For the crystal structure of ursolic acid, see: Simon et al. (1992[Simon, A., Delage, C., Saux, M., Chulia, A. J., Najid, A. & Rigaud, M. (1992). Acta Cryst. C48, 726-728.]). For the synthesis and characterization of the title compound and other ursolic acid derivatives, see: Yang et al. (2008[Yang, D. J., Li, Y. & Yin, S. F. (2008). Chin. J. Org. Chem. 28, 1055-1060.]); Liu et al. (2007[Liu, D., Meng, Y. Q. & Zhao, J. (2007). Huaxue Tongbao 70, 14-20.]).

[Scheme 1]

Experimental

Crystal data
  • C34H54O5

  • Mr = 542.77

  • Orthorhombic, P 21 21 21

  • a = 11.624 (3) Å

  • b = 12.465 (4) Å

  • c = 21.478 (3) Å

  • V = 3112.0 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 292 (2) K

  • 0.60 × 0.56 × 0.44 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: none

  • 3435 measured reflections

  • 3116 independent reflections

  • 1818 reflections with I > 2σ(I)

  • Rint = 0.009

  • 3 standard reflections every 200 reflections intensity decay: 0.8%

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.125

  • S = 0.97

  • 3116 reflections

  • 362 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.17 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O3i 0.82 2.14 2.944 (4) 165
Symmetry code: (i) [-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}].

Data collection: DIFRAC (Gabe & White, 1993[Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association, Pittsburgh meeting. Abstract PA 104.]); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989[Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

Ursolic acid, a pentacyclic triterpene existing abundantly in the plant kingdom, has been reported to possess pharmacological activities, such as anti-tumor, anti-inflammatory and anti-HIV activities (Es-saady et al., 1996; Kashiwada et al., 2000). The synthesis and characterization of some derivatives of this compound have been recently reported (Liu et al., 2007). We report herein the crystal structure of the title compound, whose synthetic method has been already reported elsewhere (Yang et al., 2008).

In the molecule of the title compound (Fig.1) bond lengths and angles within the six-membered rings are very similar to those given in the literature for ursolic acid (Simon et al., 1992). The C(sp2)—C(sp2) bond distance (C16—C17) is 1.317 (5) Å, the C(sp3)—C(sp3) bond lengths range from 1.506 (6) Å to 1.592 (5) Å, and the three C(sp3)—C(sp2) bond distances (C17—C18, C16—C23 and C16—C15) are 1.491 (5), 1.528 (5) and 1.545 (5) Å, respectively. The five six-membered rings adopt a chair conformation. The carboxy group at C22 and the methyl groups C7, C9, C14 and C19 are axially oriented, while the hydroxy groups and the methyl groups C8, C28 and C29 are in equatorial positions. The O2–C30–C22–C27 and C2–C30–C22–C21 torsion angles are -72.1 (4) Å and 47.8 Å, respectively. In the crystal packing, intermolecular O—H···O hydrogen bonds (Table 1) link molecules to form zig-zag chains extending along the c axis.

Related literature top

For the pharmacological activities of ursolic acid, see: Es-saady et al. (1996); Kashiwada et al. (2000). For the crystal structure of ursolic acid, see: Simon et al. (1992). For the synthesis and characterization of the title compound and other ursoic acid derivatives, see: Yang et al. (2008); Liu et al. (2007).

Experimental top

To a solution of ursolid acid (456 mg, 1 mmol) in DMF (10 ml) was added K2CO3 (300 mg, 2.2 mmol), KI (50 mg, 0.3 mmol) and NEt3 (0.5 ml). After stirring at room temperature for 10 minutes, a solution of ethyl chlorocetate (0.4 ml, 3 mmol) in DMF was added dropwise, and the reaction monitored by TLC. After completion of the reaction, satured brines and ehtyl acetate were added. The organic layer was separated, washed with water until neutral, dried with Na2SO4, filtered and evaporated in vacuo to get the solid title compound. Colourless crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution at room temperature.

Refinement top

H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93–0.98 Å, O—H = 0.82 Å and with Uiso(H) = 1.2Ueq(C) or 1.5 Ueq(C, O) for hydroxy and methyl H atoms. In the absence of significant anomalous dispersion effects, Friedel pairs were merged.

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, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
Ethoxycarbonylmethyl ursolate top
Crystal data top
C34H54O5F(000) = 1192
Mr = 542.77Dx = 1.158 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 14 reflections
a = 11.624 (3) Åθ = 4.3–5.6°
b = 12.465 (4) ŵ = 0.08 mm1
c = 21.478 (3) ÅT = 292 K
V = 3112.0 (14) Å3Block, colourless
Z = 40.60 × 0.56 × 0.44 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.009
Radiation source: fine-focus sealed tubeθmax = 25.2°, θmin = 1.9°
Graphite monochromatorh = 213
ω/2θ scansk = 614
3435 measured reflectionsl = 325
3116 independent reflections3 standard reflections every 200 reflections
1818 reflections with I > 2σ(I) intensity decay: 0.9%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0695P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
3116 reflectionsΔρmax = 0.19 e Å3
362 parametersΔρmin = 0.17 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0090 (12)
Crystal data top
C34H54O5V = 3112.0 (14) Å3
Mr = 542.77Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.624 (3) ŵ = 0.08 mm1
b = 12.465 (4) ÅT = 292 K
c = 21.478 (3) Å0.60 × 0.56 × 0.44 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.009
3435 measured reflections3 standard reflections every 200 reflections
3116 independent reflections intensity decay: 0.9%
1818 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 0.97Δρmax = 0.19 e Å3
3116 reflectionsΔρmin = 0.17 e Å3
362 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 > 2σ(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
O10.3112 (2)0.0655 (2)0.43876 (11)0.0676 (8)
H10.26320.11280.44420.101*
O20.5639 (2)0.28015 (19)0.04823 (12)0.0593 (7)
O30.3922 (2)0.20169 (19)0.04048 (12)0.0554 (7)
O40.4470 (3)0.4876 (2)0.14161 (14)0.0785 (9)
O50.4757 (3)0.3145 (2)0.16352 (13)0.0855 (10)
C10.3267 (3)0.0359 (3)0.24624 (16)0.0457 (9)
C20.4278 (3)0.0554 (3)0.29194 (16)0.0465 (9)
H20.48000.00490.28410.056*
C30.4019 (3)0.0475 (3)0.36250 (16)0.0495 (10)
C40.3383 (3)0.0584 (3)0.37360 (17)0.0516 (10)
H40.39220.11660.36410.062*
C50.2331 (4)0.0748 (3)0.33319 (18)0.0597 (11)
H5A0.17640.02010.34250.072*
H5B0.19930.14430.34210.072*
C60.2661 (3)0.0687 (3)0.26447 (16)0.0527 (10)
H6A0.19700.07640.23950.063*
H6B0.31640.12850.25470.063*
C70.3321 (4)0.1428 (3)0.38858 (18)0.0654 (11)
H7A0.25380.13740.37490.098*
H7B0.36470.20890.37380.098*
H7C0.33460.14140.43330.098*
C80.5167 (4)0.0419 (3)0.39817 (19)0.0649 (12)
H8A0.50180.03030.44160.097*
H8B0.55780.10810.39290.097*
H8C0.56220.01630.38220.097*
C90.2352 (4)0.1256 (3)0.24777 (19)0.0648 (12)
H9A0.18470.11450.28250.097*
H9B0.19150.12420.20990.097*
H9C0.27260.19390.25190.097*
C100.4969 (4)0.1536 (3)0.27172 (17)0.0579 (11)
H10A0.55520.16930.30270.069*
H10B0.44610.21520.26880.069*
C110.5544 (3)0.1341 (3)0.20874 (16)0.0537 (10)
H11A0.61050.07700.21320.064*
H11B0.59550.19850.19660.064*
C120.4692 (3)0.1036 (3)0.15636 (17)0.0478 (9)
C130.3811 (3)0.0197 (3)0.18028 (16)0.0472 (9)
H130.42510.04710.18370.057*
C140.4064 (4)0.2061 (3)0.13466 (18)0.0583 (11)
H14A0.35720.18920.10010.087*
H14B0.46200.25880.12210.087*
H14C0.36100.23410.16830.087*
C150.5377 (3)0.0506 (3)0.10000 (17)0.0472 (9)
C160.4504 (3)0.0129 (2)0.05037 (16)0.0450 (9)
C170.3432 (3)0.0089 (3)0.06576 (17)0.0521 (10)
H170.29460.03050.03370.063*
C180.2915 (3)0.0026 (3)0.12919 (18)0.0597 (11)
H18A0.25280.06970.13830.072*
H18B0.23420.05400.12970.072*
C190.6073 (4)0.0486 (3)0.12069 (19)0.0615 (11)
H19A0.55540.10460.13320.092*
H19B0.65590.02970.15510.092*
H19C0.65380.07340.08670.092*
C200.6231 (3)0.1324 (3)0.07259 (18)0.0599 (11)
H20A0.58600.20210.07120.072*
H20B0.68860.13810.10040.072*
C210.6667 (3)0.1052 (3)0.00753 (17)0.0597 (11)
H21A0.71110.03940.00910.072*
H21B0.71680.16210.00710.072*
C220.5655 (3)0.0913 (3)0.03835 (17)0.0495 (10)
C230.4897 (3)0.0026 (3)0.01690 (16)0.0482 (9)
H230.41990.00080.04240.058*
C240.5438 (4)0.1142 (3)0.02978 (18)0.0640 (12)
H240.61260.12070.00370.077*
C250.5818 (4)0.1250 (3)0.0978 (2)0.0719 (13)
H250.51310.12060.12410.086*
C260.6616 (4)0.0351 (4)0.1159 (2)0.0772 (14)
H26A0.68210.04270.15950.093*
H26B0.73170.04030.09160.093*
C270.6083 (4)0.0742 (3)0.10584 (18)0.0615 (11)
H27A0.54400.08290.13420.074*
H27B0.66470.12900.11570.074*
C280.6415 (5)0.2339 (4)0.1107 (2)0.114 (2)
H28A0.66800.23570.15300.171*
H28B0.58780.29120.10400.171*
H28C0.70580.24220.08300.171*
C290.4606 (4)0.2040 (3)0.0109 (2)0.0799 (14)
H29A0.39230.19980.03590.120*
H29B0.44060.19620.03220.120*
H29C0.49690.27240.01730.120*
C300.4959 (4)0.1934 (3)0.04108 (16)0.0479 (9)
C310.5087 (4)0.3793 (3)0.06002 (19)0.0600 (11)
H31A0.56010.43770.04910.072*
H31B0.44040.38510.03430.072*
C320.4757 (4)0.3882 (4)0.1274 (2)0.0605 (11)
C330.4120 (5)0.5073 (4)0.2062 (2)0.0857 (15)
H33A0.47060.48130.23460.103*
H33B0.34070.46980.21510.103*
C340.3961 (6)0.6224 (4)0.2142 (2)0.1113 (19)
H34A0.34880.64970.18120.167*
H34B0.35930.63590.25350.167*
H34C0.46960.65750.21340.167*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.076 (2)0.083 (2)0.0439 (16)0.0207 (18)0.0043 (15)0.0021 (13)
O20.0541 (16)0.0551 (16)0.0687 (18)0.0096 (14)0.0000 (15)0.0092 (13)
O30.0504 (17)0.0527 (15)0.0631 (18)0.0007 (14)0.0040 (15)0.0057 (13)
O40.100 (2)0.0616 (18)0.074 (2)0.0112 (19)0.0051 (18)0.0084 (15)
O50.124 (3)0.073 (2)0.0590 (18)0.004 (2)0.009 (2)0.0028 (16)
C10.044 (2)0.043 (2)0.050 (2)0.0025 (19)0.0064 (19)0.0030 (16)
C20.049 (2)0.0384 (19)0.052 (2)0.0028 (19)0.002 (2)0.0017 (16)
C30.051 (2)0.054 (2)0.044 (2)0.000 (2)0.002 (2)0.0035 (17)
C40.053 (2)0.053 (2)0.049 (2)0.004 (2)0.001 (2)0.0001 (18)
C50.060 (3)0.061 (3)0.057 (2)0.019 (2)0.007 (2)0.004 (2)
C60.052 (2)0.057 (2)0.048 (2)0.015 (2)0.001 (2)0.0026 (18)
C70.073 (3)0.062 (2)0.062 (3)0.008 (2)0.008 (2)0.013 (2)
C80.064 (3)0.079 (3)0.051 (2)0.012 (2)0.008 (2)0.000 (2)
C90.066 (3)0.063 (3)0.065 (3)0.010 (2)0.012 (2)0.004 (2)
C100.064 (3)0.054 (2)0.056 (2)0.014 (2)0.003 (2)0.0048 (19)
C110.049 (2)0.058 (2)0.054 (2)0.015 (2)0.000 (2)0.0023 (18)
C120.048 (2)0.046 (2)0.049 (2)0.0072 (19)0.0035 (19)0.0031 (17)
C130.041 (2)0.046 (2)0.055 (2)0.0082 (18)0.0107 (18)0.0003 (18)
C140.065 (3)0.050 (2)0.060 (2)0.005 (2)0.002 (2)0.0080 (19)
C150.043 (2)0.045 (2)0.053 (2)0.0041 (19)0.0038 (19)0.0013 (18)
C160.050 (2)0.0393 (19)0.046 (2)0.0048 (19)0.0056 (19)0.0028 (17)
C170.051 (3)0.055 (2)0.050 (2)0.013 (2)0.010 (2)0.0068 (18)
C180.052 (2)0.073 (3)0.054 (3)0.016 (2)0.004 (2)0.004 (2)
C190.059 (3)0.067 (3)0.058 (3)0.006 (2)0.011 (2)0.003 (2)
C200.049 (2)0.078 (3)0.053 (3)0.010 (2)0.009 (2)0.002 (2)
C210.046 (2)0.069 (3)0.064 (3)0.005 (2)0.001 (2)0.003 (2)
C220.049 (2)0.053 (2)0.047 (2)0.000 (2)0.004 (2)0.0011 (17)
C230.045 (2)0.052 (2)0.048 (2)0.0040 (19)0.0065 (19)0.0016 (17)
C240.073 (3)0.058 (2)0.062 (3)0.020 (2)0.017 (2)0.0056 (19)
C250.067 (3)0.067 (3)0.081 (3)0.022 (3)0.015 (3)0.018 (2)
C260.064 (3)0.100 (4)0.068 (3)0.014 (3)0.008 (3)0.020 (3)
C270.051 (2)0.076 (3)0.057 (3)0.001 (2)0.006 (2)0.001 (2)
C280.129 (5)0.093 (3)0.121 (5)0.045 (4)0.004 (4)0.029 (3)
C290.103 (4)0.050 (2)0.087 (3)0.002 (3)0.017 (3)0.001 (2)
C300.049 (3)0.059 (2)0.035 (2)0.008 (2)0.003 (2)0.0008 (18)
C310.073 (3)0.047 (2)0.060 (3)0.008 (2)0.003 (2)0.0049 (19)
C320.062 (3)0.055 (3)0.064 (3)0.007 (2)0.010 (2)0.006 (2)
C330.090 (4)0.105 (4)0.063 (3)0.018 (3)0.001 (3)0.021 (3)
C340.142 (5)0.093 (4)0.100 (4)0.030 (4)0.009 (4)0.036 (3)
Geometric parameters (Å, º) top
O1—C41.437 (4)C15—C191.543 (5)
O1—H10.8200C15—C161.545 (5)
O2—C301.348 (4)C16—C171.317 (5)
O2—C311.415 (4)C16—C231.528 (5)
O3—C301.210 (4)C17—C181.491 (5)
O4—C321.319 (5)C17—H170.9300
O4—C331.466 (5)C18—H18A0.9700
O5—C321.203 (5)C18—H18B0.9700
C1—C61.533 (5)C19—H19A0.9600
C1—C91.543 (5)C19—H19B0.9600
C1—C21.551 (5)C19—H19C0.9600
C1—C131.565 (5)C20—C211.525 (5)
C2—C101.527 (5)C20—H20A0.9700
C2—C31.548 (5)C20—H20B0.9700
C2—H20.9800C21—C221.544 (5)
C3—C41.531 (5)C21—H21A0.9700
C3—C81.540 (5)C21—H21B0.9700
C3—C71.544 (5)C22—C301.510 (5)
C4—C51.513 (5)C22—C231.535 (5)
C4—H40.9800C22—C271.547 (5)
C5—C61.527 (5)C23—C241.552 (5)
C5—H5A0.9700C23—H230.9800
C5—H5B0.9700C24—C251.531 (6)
C6—H6A0.9700C24—C291.534 (6)
C6—H6B0.9700C24—H240.9800
C7—H7A0.9600C25—C261.506 (6)
C7—H7B0.9600C25—C281.550 (5)
C7—H7C0.9600C25—H250.9800
C8—H8A0.9600C26—C271.512 (5)
C8—H8B0.9600C26—H26A0.9700
C8—H8C0.9600C26—H26B0.9700
C9—H9A0.9600C27—H27A0.9700
C9—H9B0.9600C27—H27B0.9700
C9—H9C0.9600C28—H28A0.9600
C10—C111.528 (5)C28—H28B0.9600
C10—H10A0.9700C28—H28C0.9600
C10—H10B0.9700C29—H29A0.9600
C11—C121.546 (5)C29—H29B0.9600
C11—H11A0.9700C29—H29C0.9600
C11—H11B0.9700C31—C321.501 (6)
C12—C141.544 (5)C31—H31A0.9700
C12—C131.551 (5)C31—H31B0.9700
C12—C151.592 (5)C33—C341.457 (6)
C13—C181.538 (5)C33—H33A0.9700
C13—H130.9800C33—H33B0.9700
C14—H14A0.9600C34—H34A0.9600
C14—H14B0.9600C34—H34B0.9600
C14—H14C0.9600C34—H34C0.9600
C15—C201.541 (5)
C4—O1—H1109.5C18—C17—H17116.6
C30—O2—C31117.1 (3)C17—C18—C13112.9 (3)
C32—O4—C33116.5 (4)C17—C18—H18A109.0
C6—C1—C9107.1 (3)C13—C18—H18A109.0
C6—C1—C2108.6 (3)C17—C18—H18B109.0
C9—C1—C2113.3 (3)C13—C18—H18B109.0
C6—C1—C13107.9 (3)H18A—C18—H18B107.8
C9—C1—C13113.1 (3)C15—C19—H19A109.5
C2—C1—C13106.7 (3)C15—C19—H19B109.5
C10—C2—C3115.6 (3)H19A—C19—H19B109.5
C10—C2—C1110.1 (3)C15—C19—H19C109.5
C3—C2—C1117.5 (3)H19A—C19—H19C109.5
C10—C2—H2103.9H19B—C19—H19C109.5
C3—C2—H2103.9C21—C20—C15114.7 (3)
C1—C2—H2103.9C21—C20—H20A108.6
C4—C3—C8107.6 (3)C15—C20—H20A108.6
C4—C3—C7110.7 (3)C21—C20—H20B108.6
C8—C3—C7108.0 (3)C15—C20—H20B108.6
C4—C3—C2107.5 (3)H20A—C20—H20B107.6
C8—C3—C2108.7 (3)C20—C21—C22110.9 (3)
C7—C3—C2114.1 (3)C20—C21—H21A109.5
O1—C4—C5111.9 (3)C22—C21—H21A109.5
O1—C4—C3108.1 (3)C20—C21—H21B109.5
C5—C4—C3114.7 (3)C22—C21—H21B109.5
O1—C4—H4107.3H21A—C21—H21B108.1
C5—C4—H4107.3C30—C22—C23110.3 (3)
C3—C4—H4107.3C30—C22—C21109.8 (3)
C4—C5—C6110.2 (3)C23—C22—C21109.3 (3)
C4—C5—H5A109.6C30—C22—C27104.6 (3)
C6—C5—H5A109.6C23—C22—C27111.1 (3)
C4—C5—H5B109.6C21—C22—C27111.6 (3)
C6—C5—H5B109.6C16—C23—C22111.1 (3)
H5A—C5—H5B108.1C16—C23—C24113.8 (3)
C5—C6—C1113.9 (3)C22—C23—C24113.4 (3)
C5—C6—H6A108.8C16—C23—H23105.9
C1—C6—H6A108.8C22—C23—H23105.9
C5—C6—H6B108.8C24—C23—H23105.9
C1—C6—H6B108.8C25—C24—C29111.7 (3)
H6A—C6—H6B107.7C25—C24—C23111.4 (3)
C3—C7—H7A109.5C29—C24—C23110.6 (3)
C3—C7—H7B109.5C25—C24—H24107.6
H7A—C7—H7B109.5C29—C24—H24107.6
C3—C7—H7C109.5C23—C24—H24107.6
H7A—C7—H7C109.5C26—C25—C24111.1 (3)
H7B—C7—H7C109.5C26—C25—C28109.3 (4)
C3—C8—H8A109.5C24—C25—C28112.1 (4)
C3—C8—H8B109.5C26—C25—H25108.1
H8A—C8—H8B109.5C24—C25—H25108.1
C3—C8—H8C109.5C28—C25—H25108.1
H8A—C8—H8C109.5C25—C26—C27112.4 (3)
H8B—C8—H8C109.5C25—C26—H26A109.1
C1—C9—H9A109.5C27—C26—H26A109.1
C1—C9—H9B109.5C25—C26—H26B109.1
H9A—C9—H9B109.5C27—C26—H26B109.1
C1—C9—H9C109.5H26A—C26—H26B107.9
H9A—C9—H9C109.5C26—C27—C22113.0 (3)
H9B—C9—H9C109.5C26—C27—H27A109.0
C2—C10—C11110.7 (3)C22—C27—H27A109.0
C2—C10—H10A109.5C26—C27—H27B109.0
C11—C10—H10A109.5C22—C27—H27B109.0
C2—C10—H10B109.5H27A—C27—H27B107.8
C11—C10—H10B109.5C25—C28—H28A109.5
H10A—C10—H10B108.1C25—C28—H28B109.5
C10—C11—C12113.7 (3)H28A—C28—H28B109.5
C10—C11—H11A108.8C25—C28—H28C109.5
C12—C11—H11A108.8H28A—C28—H28C109.5
C10—C11—H11B108.8H28B—C28—H28C109.5
C12—C11—H11B108.8C24—C29—H29A109.5
H11A—C11—H11B107.7C24—C29—H29B109.5
C14—C12—C11108.6 (3)H29A—C29—H29B109.5
C14—C12—C13110.3 (3)C24—C29—H29C109.5
C11—C12—C13110.3 (3)H29A—C29—H29C109.5
C14—C12—C15110.5 (3)H29B—C29—H29C109.5
C11—C12—C15109.6 (3)O3—C30—O2121.2 (4)
C13—C12—C15107.6 (3)O3—C30—C22127.2 (4)
C18—C13—C12109.4 (3)O2—C30—C22111.5 (3)
C18—C13—C1113.3 (3)O2—C31—C32110.7 (3)
C12—C13—C1118.7 (3)O2—C31—H31A109.5
C18—C13—H13104.7C32—C31—H31A109.5
C12—C13—H13104.7O2—C31—H31B109.5
C1—C13—H13104.7C32—C31—H31B109.5
C12—C14—H14A109.5H31A—C31—H31B108.1
C12—C14—H14B109.5O5—C32—O4124.6 (4)
H14A—C14—H14B109.5O5—C32—C31124.5 (4)
C12—C14—H14C109.5O4—C32—C31110.9 (4)
H14A—C14—H14C109.5C34—C33—O4108.2 (4)
H14B—C14—H14C109.5C34—C33—H33A110.1
C20—C15—C19107.6 (3)O4—C33—H33A110.1
C20—C15—C16111.2 (3)C34—C33—H33B110.1
C19—C15—C16107.4 (3)O4—C33—H33B110.1
C20—C15—C12109.7 (3)H33A—C33—H33B108.4
C19—C15—C12112.1 (3)C33—C34—H34A109.5
C16—C15—C12108.8 (3)C33—C34—H34B109.5
C17—C16—C23119.7 (3)H34A—C34—H34B109.5
C17—C16—C15120.7 (3)C33—C34—H34C109.5
C23—C16—C15119.6 (3)H34A—C34—H34C109.5
C16—C17—C18126.8 (4)H34B—C34—H34C109.5
C16—C17—H17116.6
C6—C1—C2—C10174.9 (3)C20—C15—C16—C2336.8 (4)
C9—C1—C2—C1066.1 (4)C19—C15—C16—C2380.7 (4)
C13—C1—C2—C1058.9 (3)C12—C15—C16—C23157.7 (3)
C6—C1—C2—C349.9 (4)C23—C16—C17—C18177.5 (3)
C9—C1—C2—C369.0 (4)C15—C16—C17—C180.7 (6)
C13—C1—C2—C3165.9 (3)C16—C17—C18—C137.3 (6)
C10—C2—C3—C4177.0 (3)C12—C13—C18—C1740.4 (4)
C1—C2—C3—C450.2 (4)C1—C13—C18—C17175.2 (3)
C10—C2—C3—C860.8 (4)C19—C15—C20—C2175.6 (4)
C1—C2—C3—C8166.4 (3)C16—C15—C20—C2141.8 (4)
C10—C2—C3—C759.8 (4)C12—C15—C20—C21162.2 (3)
C1—C2—C3—C773.0 (4)C15—C20—C21—C2256.4 (4)
C8—C3—C4—O164.5 (4)C20—C21—C22—C3059.1 (4)
C7—C3—C4—O153.3 (4)C20—C21—C22—C2362.0 (4)
C2—C3—C4—O1178.6 (3)C20—C21—C22—C27174.6 (3)
C8—C3—C4—C5170.0 (3)C17—C16—C23—C22137.4 (4)
C7—C3—C4—C572.2 (4)C15—C16—C23—C2244.5 (4)
C2—C3—C4—C553.0 (4)C17—C16—C23—C2493.2 (4)
O1—C4—C5—C6179.0 (3)C15—C16—C23—C2485.0 (4)
C3—C4—C5—C657.5 (4)C30—C22—C23—C1666.1 (4)
C4—C5—C6—C156.1 (4)C21—C22—C23—C1654.8 (4)
C9—C1—C6—C571.5 (4)C27—C22—C23—C16178.4 (3)
C2—C1—C6—C551.2 (4)C30—C22—C23—C24164.3 (3)
C13—C1—C6—C5166.4 (3)C21—C22—C23—C2474.9 (4)
C3—C2—C10—C11159.2 (3)C27—C22—C23—C2448.8 (4)
C1—C2—C10—C1164.7 (4)C16—C23—C24—C25179.9 (4)
C2—C10—C11—C1256.7 (4)C22—C23—C24—C2551.7 (4)
C10—C11—C12—C1476.7 (4)C16—C23—C24—C2955.2 (4)
C10—C11—C12—C1344.3 (4)C22—C23—C24—C29176.5 (3)
C10—C11—C12—C15162.5 (3)C29—C24—C25—C26178.9 (3)
C14—C12—C13—C1855.5 (4)C23—C24—C25—C2654.6 (5)
C11—C12—C13—C18175.4 (3)C29—C24—C25—C2858.6 (5)
C15—C12—C13—C1865.1 (4)C23—C24—C25—C28177.2 (4)
C14—C12—C13—C176.6 (4)C24—C25—C26—C2756.9 (5)
C11—C12—C13—C143.4 (4)C28—C25—C26—C27178.9 (4)
C15—C12—C13—C1162.9 (3)C25—C26—C27—C2255.1 (5)
C6—C1—C13—C1862.5 (4)C30—C22—C27—C26169.3 (3)
C9—C1—C13—C1855.8 (4)C23—C22—C27—C2650.2 (5)
C2—C1—C13—C18179.1 (3)C21—C22—C27—C2672.1 (4)
C6—C1—C13—C12167.1 (3)C31—O2—C30—O35.0 (5)
C9—C1—C13—C1274.6 (4)C31—O2—C30—C22171.6 (3)
C2—C1—C13—C1250.6 (4)C23—C22—C30—O315.3 (5)
C14—C12—C15—C2057.2 (4)C21—C22—C30—O3135.9 (4)
C11—C12—C15—C2062.4 (4)C27—C22—C30—O3104.2 (4)
C13—C12—C15—C20177.6 (3)C23—C22—C30—O2168.3 (3)
C14—C12—C15—C19176.7 (3)C21—C22—C30—O247.8 (4)
C11—C12—C15—C1957.1 (4)C27—C22—C30—O272.1 (4)
C13—C12—C15—C1962.8 (4)C30—O2—C31—C3280.2 (4)
C14—C12—C15—C1664.7 (3)C33—O4—C32—O50.6 (7)
C11—C12—C15—C16175.7 (3)C33—O4—C32—C31179.6 (4)
C13—C12—C15—C1655.8 (3)O2—C31—C32—O513.2 (6)
C20—C15—C16—C17145.1 (4)O2—C31—C32—O4166.6 (3)
C19—C15—C16—C1797.4 (4)C32—O4—C33—C34173.9 (4)
C12—C15—C16—C1724.1 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.822.142.944 (4)165
Symmetry code: (i) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC34H54O5
Mr542.77
Crystal system, space groupOrthorhombic, P212121
Temperature (K)292
a, b, c (Å)11.624 (3), 12.465 (4), 21.478 (3)
V3)3112.0 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.60 × 0.56 × 0.44
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3435, 3116, 1818
Rint0.009
(sin θ/λ)max1)0.600
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.125, 0.97
No. of reflections3116
No. of parameters362
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.17

Computer programs: DIFRAC (Gabe & White, 1993), NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.822.142.944 (4)165.1
Symmetry code: (i) x+1/2, y, z+1/2.
 

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

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First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
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First citationSimon, A., Delage, C., Saux, M., Chulia, A. J., Najid, A. & Rigaud, M. (1992). Acta Cryst. C48, 726–728.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationYang, D. J., Li, Y. & Yin, S. F. (2008). Chin. J. Org. Chem. 28, 1055–1060.  CAS Google Scholar

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