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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

1,4a,7-Tri­methyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a-dodeca­hydro­phenanthrene-1-carboxylic acid

aInstitute of Chemical Industry of Forest Products, Chinese Academy of Forestry, Nanjing 210042, People's Republic of China
*Correspondence e-mail: sbkf@tom.com

(Received 19 May 2009; accepted 21 May 2009; online 29 May 2009)

The title compound, also known as isopimaric acid, C20H30O2, was isolated from slash pine rosin. There are two unique mol­ecules in the unit cell. The two cyclo­hexane rings have classical chair conformations. The cyclo­hexene ring represents a semi-chair. The mol­ecular conformation is stabilized by weak intra­molecular C—H⋯O hydrogen-bonding inter­actions. The mol­ecules are dimerized through their carboxyl groups by O—H⋯O hydrogen bonds, forming R22(8) rings.

Related literature

For physical and spectroscopic analysis, see: Baldwin et al. (1958[Baldwin, D. E., Loeblich, V. M. & Lawrence, R. V. (1958). J. Org. Chem. 23, 25-26.]); Harris & Sanderson (1948[Harris, G. C. & Sanderson, T. F. (1948). J. Am. Chem. Soc. 70, 2079-2081.]). For biological activities, see: Smith et al. (2005[Smith, E., Williamson, E., Zloh, M. & Gibbons, S. (2005). Phytother. Res. 19, 538-542.]); Russo et al. (2007[Russo, R., Loverme, J., Rana, G. L., D'Agostino, G., Sasso, O., Calignano, A. & Piomelli, D. (2007). Eur. J. Pharmacol. 566, 117-119.]).

[Scheme 1]

Experimental

Crystal data
  • C20H30O2

  • Mr = 302.44

  • Orthorhombic, P 21 21 21

  • a = 11.624 (2) Å

  • b = 11.803 (2) Å

  • c = 25.698 (5) Å

  • V = 3525.7 (12) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.986, Tmax = 0.993

  • 7031 measured reflections

  • 6382 independent reflections

  • 2613 reflections with I > 2σ(I)

  • Rint = 0.088

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.069

  • wR(F2) = 0.150

  • S = 1.00

  • 3598 reflections

  • 385 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.24 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2B⋯O4i 0.82 1.84 2.653 (7) 168
O3—H3D⋯O1ii 0.82 1.85 2.655 (7) 168
C11—H11A⋯O1 0.98 2.34 2.764 (7) 105
C32—H32B⋯O4 0.97 2.49 3.081 (9) 119
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+2]; (ii) [x-{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+2].

Data collection: CAD-4 Software (Enraf–Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound has been isolated from slash pine rosin. It was identified as isopimaric acid on the basis of the comparison of its physical and spectral data with literature values (Baldwin et al., 1958; Harris et al., 1948). Isopimaric acid exhibits a wide range of biological activities such as antibacterial activity (Smith et al., 2005), BK channels activity (Russo et al., 2007). Although much attention has been paid to the bioactivities of isopimaric acid, the crystal structure of the title compound has not yet been reported. In this work, we describe the crystal structure of the title compound (I).

The molecular structure of (I) is shown in Fig. 1 and its crystal packing in Fig.2. The atoms of C11, C12 in the cyclohexene ring and the atoms C10, C14 in the conjoint cyclohexane ring are in the same plane. The atoms of C11, C12 and the atoms of C16, C17 in the cyclohexane ring are in another plane. The dihedral angle of the two planes is 134.4 degree. The three methyl groups attached to the cyclohexane rings are in axial positions and in the same direction. The molecular conformation is stabilized by C—H···O intra-molecular hydrogen bonding interactions (Table 1). The molecules are dimerized through their carboxyl groups by O—H···O hydrogen bonds, forming R22(8) rings (Fig. 2).

Related literature top

For related literature, see: Baldwin et al. (1958); Harris & Sanderson (1948); Smith et al. (2005); Russo et al. (2007).

Experimental top

A mixture of slash pine rosin (150 g), acetone (300 ml) and 2-amino-2-methyl-1-propanol (0.1 mol) was stirred at room temperature for 2 h and then filtrated. The residue was recrystallized with 95% ethanol. The crystal obtained from the solution was acidified by 5% hydrochloric acid solution and then dissolved in ether. The solution was washed with water until it was neutral, dryed with sodium sulfate and then concentrated. The residue was recrystallized with acetone and the title compound was obtained as colourless solid.

Refinement top

All H atoms were placed geometrically with C—H = 0.93–0.98 Å and O—H = 0.82 Å, and included in the refinement in riding motion approximation with Uiso(H) = 1.2 or 1.5Ueq of the carrier atom. Because of no atom heavier than Si present in the structure, in the absence of significant anomalous dispersion effects, so Friedel pairs were averaged.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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
[Figure 1] Fig. 1. A view of the molecular structure of (I), showing displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. A view of the packing of the molecules dimerized through their carboxyl groups by O—H···O hydrogen bonds, forming R22(8) rings.
1,4a,7-Trimethyl-7-vinyl-1,2,3,4,4a,4b,5,6,7,8,10,10a- dodecahydrophenanthrene-1-carboxylic acid top
Crystal data top
C20H30O2Dx = 1.140 Mg m3
Mr = 302.44Melting point: 436 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 11.624 (2) Åθ = 9–12°
b = 11.803 (2) ŵ = 0.07 mm1
c = 25.698 (5) ÅT = 293 K
V = 3525.7 (12) Å3Quadrate, colourless
Z = 80.20 × 0.10 × 0.10 mm
F(000) = 1328
Data collection top
Enraf–Nonius CAD-4
diffractometer
2613 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.088
Graphite monochromatorθmax = 25.3°, θmin = 1.6°
ω/2θ scansh = 013
Absorption correction: ψ scan
(North et al., 1968)
k = 014
Tmin = 0.986, Tmax = 0.993l = 3030
7031 measured reflections3 standard reflections every 200 reflections
6382 independent reflections intensity decay: 1%
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)] = 0.069Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.045P)2]
where P = (Fo2 + 2Fc2)/3
3598 reflections(Δ/σ)max < 0.001
385 parametersΔρmax = 0.24 e Å3
1 restraintΔρmin = 0.26 e Å3
Crystal data top
C20H30O2V = 3525.7 (12) Å3
Mr = 302.44Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 11.624 (2) ŵ = 0.07 mm1
b = 11.803 (2) ÅT = 293 K
c = 25.698 (5) Å0.20 × 0.10 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
2613 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.088
Tmin = 0.986, Tmax = 0.9933 standard reflections every 200 reflections
7031 measured reflections intensity decay: 1%
6382 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0691 restraint
wR(F2) = 0.150H-atom parameters constrained
S = 1.00Δρmax = 0.24 e Å3
3598 reflectionsΔρmin = 0.26 e Å3
385 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
O10.7921 (4)0.8907 (4)0.96412 (19)0.0796 (17)
O20.6441 (4)1.0009 (4)0.97857 (19)0.0816 (16)
H2B0.67651.03860.95610.122*
C10.9481 (9)0.1236 (8)1.0193 (3)0.127
H1A0.88430.08571.00600.152*
H1B1.02040.08991.01780.152*
C20.9370 (8)0.2172 (8)1.0385 (3)0.110
H2A1.00800.24371.04990.132*
C30.7282 (7)0.2534 (6)1.0540 (3)0.088 (3)
H3A0.72680.19881.08170.132*
H3B0.70820.21701.02180.132*
H3C0.67380.31261.06120.132*
C40.8463 (7)0.3031 (6)1.0497 (3)0.064 (2)
C50.8871 (7)0.3611 (6)1.0991 (3)0.076 (2)
H5A0.96520.38811.09420.091*
H5B0.88740.30701.12750.091*
C60.8086 (6)0.4615 (5)1.1131 (3)0.069 (2)
H6A0.73090.43421.11870.083*
H6B0.83520.49571.14520.083*
C70.8077 (5)0.5512 (5)1.0699 (2)0.0449 (16)
H7A0.88640.58081.06760.054*
C80.7810 (6)0.4997 (5)1.0180 (3)0.0496 (17)
C90.8475 (6)0.3926 (5)1.0056 (3)0.066 (2)
H9A0.92670.41270.99810.080*
H9B0.81540.35880.97440.080*
C100.7276 (6)0.6559 (5)1.0837 (2)0.0461 (16)
C110.7174 (6)0.7258 (5)1.0326 (2)0.0469 (16)
H11A0.79650.73391.01990.056*
C120.6560 (6)0.6608 (5)0.9911 (2)0.0579 (19)
H12A0.65860.70270.95860.070*
H12B0.57590.65101.00070.070*
C130.7126 (6)0.5439 (5)0.9835 (3)0.0599 (19)
H13A0.69720.50350.95330.072*
C140.7876 (6)0.7254 (5)1.1253 (2)0.0577 (18)
H14A0.86740.73641.11540.069*
H14B0.78640.68391.15790.069*
C150.7310 (7)0.8406 (5)1.1333 (3)0.071 (2)
H15A0.77090.88111.16070.086*
H15B0.65180.82981.14410.086*
C160.7336 (7)0.9111 (6)1.0836 (3)0.071 (2)
H16A0.81290.92551.07390.085*
H16B0.69680.98351.09000.085*
C170.6704 (6)0.8497 (5)1.0371 (2)0.0523 (18)
C180.6102 (5)0.6120 (6)1.1030 (3)0.0601 (19)
H18A0.56110.67511.11090.090*
H18B0.62110.56701.13370.090*
H18C0.57520.56651.07640.090*
C190.5398 (6)0.8563 (6)1.0466 (3)0.071 (2)
H19A0.51710.93411.05000.106*
H19B0.52100.81621.07800.106*
H19C0.49990.82251.01780.106*
C200.7059 (7)0.9151 (5)0.9899 (3)0.0554 (19)
O30.3506 (4)1.4855 (4)1.11796 (19)0.0782 (16)
H3D0.32671.51631.09150.117*
O40.2231 (4)1.3579 (4)1.09334 (19)0.0715 (15)
C210.0730 (7)0.5800 (8)1.1914 (4)0.112 (3)
H21A0.07780.57511.22750.135*
H21B0.04140.52071.17240.135*
C220.1091 (7)0.6666 (6)1.1685 (4)0.087 (3)
H22A0.10170.66611.13250.104*
C230.1430 (6)0.7841 (7)1.2495 (3)0.090 (3)
H23A0.06210.78561.25690.134*
H23B0.17740.85401.26060.134*
H23C0.17810.72221.26780.134*
C240.1616 (7)0.7689 (6)1.1909 (3)0.064 (2)
C250.2897 (6)0.7684 (5)1.1787 (3)0.067 (2)
H25A0.32480.70521.19680.081*
H25B0.29930.75531.14170.081*
C260.3541 (6)0.8752 (5)1.1930 (3)0.065 (2)
H26A0.43350.86761.18190.078*
H26B0.35390.88311.23060.078*
C270.3037 (5)0.9826 (5)1.1690 (2)0.0489 (17)
H27A0.32180.97791.13180.059*
C280.1740 (6)0.9838 (6)1.1720 (2)0.0519 (18)
C290.1117 (6)0.8732 (5)1.1632 (3)0.066 (2)
H29A0.11070.85811.12610.080*
H29B0.03250.88251.17430.080*
C300.3612 (5)1.0954 (5)1.1883 (3)0.0486 (17)
C310.2935 (5)1.1915 (5)1.1639 (2)0.0467 (17)
H31A0.28701.17111.12700.056*
C320.1699 (6)1.1945 (6)1.1837 (3)0.0574 (19)
H32A0.16901.21971.21960.069*
H32B0.12551.24801.16330.069*
C330.1167 (6)1.0799 (6)1.1800 (3)0.067 (2)
H33A0.03721.07521.18340.081*
C340.4849 (5)1.0947 (6)1.1698 (3)0.061 (2)
H34A0.48701.07851.13280.074*
H34B0.52661.03511.18770.074*
C350.5446 (6)1.2105 (6)1.1803 (3)0.074 (2)
H35A0.54181.22831.21710.089*
H35B0.62461.20731.16960.089*
C360.4813 (5)1.3000 (6)1.1494 (3)0.061 (2)
H36A0.48621.28101.11270.073*
H36B0.51991.37211.15430.073*
C370.3535 (6)1.3142 (5)1.1640 (2)0.0509 (17)
C380.3546 (6)1.0973 (5)1.2479 (2)0.067 (2)
H38A0.38871.16601.26070.101*
H38B0.39541.03341.26180.101*
H38C0.27551.09381.25860.101*
C390.3395 (7)1.3764 (5)1.2144 (3)0.075 (2)
H39A0.37851.44801.21240.112*
H39B0.37191.33221.24220.112*
H39C0.25921.38891.22100.112*
C400.3037 (6)1.3882 (6)1.1227 (3)0.0529 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.085 (4)0.058 (3)0.096 (4)0.016 (3)0.042 (3)0.013 (3)
O20.082 (4)0.073 (3)0.089 (4)0.007 (3)0.022 (3)0.030 (3)
C10.1370.1070.1370.0000.0000.000
C20.1100.1100.1100.0000.0000.000
C30.093 (7)0.057 (5)0.114 (7)0.008 (5)0.022 (6)0.012 (5)
C40.079 (6)0.043 (4)0.070 (5)0.026 (4)0.023 (5)0.006 (4)
C50.094 (6)0.058 (5)0.076 (5)0.002 (5)0.002 (5)0.019 (5)
C60.087 (6)0.056 (4)0.064 (5)0.017 (4)0.005 (4)0.005 (4)
C70.049 (4)0.035 (3)0.051 (4)0.001 (3)0.000 (3)0.000 (3)
C80.063 (4)0.031 (3)0.054 (4)0.004 (4)0.001 (4)0.014 (3)
C90.060 (5)0.057 (4)0.082 (5)0.007 (4)0.012 (4)0.015 (4)
C100.052 (4)0.041 (3)0.046 (4)0.002 (4)0.003 (3)0.005 (3)
C110.057 (4)0.036 (3)0.048 (4)0.004 (3)0.004 (4)0.004 (3)
C120.073 (5)0.049 (4)0.052 (4)0.004 (4)0.005 (4)0.015 (3)
C130.073 (5)0.047 (4)0.059 (5)0.012 (4)0.004 (4)0.005 (4)
C140.070 (5)0.059 (4)0.044 (4)0.000 (4)0.009 (4)0.005 (4)
C150.101 (6)0.055 (4)0.058 (5)0.020 (5)0.000 (4)0.004 (4)
C160.088 (6)0.056 (4)0.068 (5)0.010 (5)0.005 (4)0.002 (4)
C170.072 (5)0.039 (4)0.045 (4)0.003 (4)0.008 (4)0.003 (3)
C180.052 (4)0.062 (5)0.066 (5)0.001 (4)0.019 (4)0.000 (4)
C190.072 (5)0.062 (5)0.078 (5)0.025 (4)0.016 (4)0.022 (4)
C200.070 (5)0.033 (4)0.064 (5)0.008 (4)0.002 (4)0.018 (4)
O30.097 (4)0.057 (3)0.080 (4)0.014 (3)0.028 (3)0.019 (3)
O40.075 (3)0.057 (3)0.083 (3)0.011 (3)0.036 (3)0.025 (3)
C210.121 (8)0.099 (7)0.116 (8)0.031 (7)0.020 (7)0.016 (7)
C220.092 (7)0.055 (5)0.113 (8)0.025 (5)0.032 (6)0.006 (5)
C230.096 (6)0.091 (6)0.082 (6)0.002 (6)0.001 (5)0.023 (5)
C240.075 (6)0.052 (5)0.065 (5)0.016 (4)0.012 (4)0.010 (4)
C250.075 (6)0.055 (5)0.072 (5)0.005 (4)0.017 (5)0.004 (4)
C260.051 (4)0.065 (5)0.079 (5)0.003 (4)0.004 (4)0.007 (4)
C270.045 (4)0.062 (4)0.039 (4)0.022 (4)0.003 (3)0.009 (3)
C280.061 (5)0.050 (4)0.044 (4)0.002 (4)0.008 (3)0.007 (4)
C290.073 (5)0.060 (5)0.066 (5)0.013 (4)0.007 (4)0.004 (4)
C300.045 (4)0.045 (4)0.056 (4)0.002 (3)0.000 (4)0.005 (3)
C310.043 (4)0.053 (4)0.044 (4)0.001 (3)0.003 (3)0.004 (3)
C320.058 (5)0.057 (5)0.057 (4)0.003 (4)0.012 (4)0.014 (4)
C330.055 (5)0.065 (5)0.082 (6)0.000 (4)0.016 (4)0.023 (5)
C340.060 (5)0.062 (5)0.062 (5)0.002 (4)0.005 (4)0.003 (4)
C350.056 (5)0.073 (5)0.092 (6)0.006 (4)0.007 (5)0.011 (5)
C360.053 (5)0.052 (4)0.076 (5)0.015 (4)0.010 (4)0.014 (4)
C370.060 (4)0.045 (4)0.048 (4)0.004 (4)0.009 (4)0.001 (3)
C380.103 (6)0.055 (4)0.043 (4)0.011 (5)0.008 (4)0.004 (4)
C390.104 (6)0.051 (4)0.070 (5)0.001 (5)0.000 (5)0.011 (4)
C400.050 (4)0.052 (5)0.057 (4)0.003 (4)0.002 (4)0.003 (4)
Geometric parameters (Å, º) top
O1—C201.235 (7)O3—C401.278 (7)
O2—C201.276 (7)O3—H3D0.8200
O2—H2B0.8200O4—C401.256 (7)
C1—C21.217 (8)C21—C221.252 (10)
C1—H1A0.9300C21—H21A0.9300
C1—H1B0.9300C21—H21B0.9300
C2—C41.491 (10)C22—C241.470 (9)
C2—H2A0.9300C22—H22A0.9300
C3—C41.496 (9)C23—C241.532 (10)
C3—H3A0.9600C23—H23A0.9600
C3—H3B0.9600C23—H23B0.9600
C3—H3C0.9600C23—H23C0.9600
C4—C51.518 (10)C24—C251.522 (10)
C4—C91.549 (9)C24—C291.536 (9)
C5—C61.538 (9)C25—C261.511 (8)
C5—H5A0.9700C25—H25A0.9700
C5—H5B0.9700C25—H25B0.9700
C6—C71.534 (8)C26—C271.528 (8)
C6—H6A0.9700C26—H26A0.9700
C6—H6B0.9700C26—H26B0.9700
C7—C81.498 (8)C27—C281.510 (8)
C7—C101.587 (8)C27—C301.570 (8)
C7—H7A0.9800C27—H27A0.9800
C8—C131.299 (8)C28—C331.331 (8)
C8—C91.516 (8)C28—C291.510 (8)
C9—H9A0.9700C29—H29A0.9700
C9—H9B0.9700C29—H29B0.9700
C10—C141.517 (8)C30—C341.514 (8)
C10—C181.542 (8)C30—C311.516 (8)
C10—C111.555 (7)C30—C381.536 (8)
C11—C121.496 (8)C31—C321.525 (8)
C11—C171.565 (8)C31—C371.607 (8)
C11—H11A0.9800C31—H31A0.9800
C12—C131.541 (8)C32—C331.491 (9)
C12—H12A0.9700C32—H32A0.9700
C12—H12B0.9700C32—H32B0.9700
C13—H13A0.9300C33—H33A0.9300
C14—C151.524 (8)C34—C351.556 (8)
C14—H14A0.9700C34—H34A0.9700
C14—H14B0.9700C34—H34B0.9700
C15—C161.525 (9)C35—C361.514 (9)
C15—H15A0.9700C35—H35A0.9700
C15—H15B0.9700C35—H35B0.9700
C16—C171.578 (9)C36—C371.541 (9)
C16—H16A0.9700C36—H36A0.9700
C16—H16B0.9700C36—H36B0.9700
C17—C201.496 (9)C37—C401.491 (8)
C17—C191.540 (8)C37—C391.498 (8)
C18—H18A0.9600C38—H38A0.9600
C18—H18B0.9600C38—H38B0.9600
C18—H18C0.9600C38—H38C0.9600
C19—H19A0.9600C39—H39A0.9600
C19—H19B0.9600C39—H39B0.9600
C19—H19C0.9600C39—H39C0.9600
C20—O2—H2B109.5C40—O3—H3D109.5
C2—C1—H1A120.0C22—C21—H21A120.0
C2—C1—H1B120.0C22—C21—H21B120.0
H1A—C1—H1B120.0H21A—C21—H21B120.0
C1—C2—C4140.4 (11)C21—C22—C24128.7 (9)
C1—C2—H2A109.8C21—C22—H22A115.6
C4—C2—H2A109.8C24—C22—H22A115.6
C4—C3—H3A109.5C24—C23—H23A109.5
C4—C3—H3B109.5C24—C23—H23B109.5
H3A—C3—H3B109.5H23A—C23—H23B109.5
C4—C3—H3C109.5C24—C23—H23C109.5
H3A—C3—H3C109.5H23A—C23—H23C109.5
H3B—C3—H3C109.5H23B—C23—H23C109.5
C2—C4—C3113.4 (7)C22—C24—C25108.8 (7)
C2—C4—C5104.3 (7)C22—C24—C23115.0 (7)
C3—C4—C5113.7 (6)C25—C24—C23109.9 (6)
C2—C4—C9108.4 (6)C22—C24—C29108.7 (6)
C3—C4—C9109.2 (6)C25—C24—C29106.1 (6)
C5—C4—C9107.5 (6)C23—C24—C29108.0 (6)
C4—C5—C6111.0 (6)C26—C25—C24115.6 (6)
C4—C5—H5A109.4C26—C25—H25A108.4
C6—C5—H5A109.4C24—C25—H25A108.4
C4—C5—H5B109.4C26—C25—H25B108.4
C6—C5—H5B109.4C24—C25—H25B108.4
H5A—C5—H5B108.0H25A—C25—H25B107.5
C7—C6—C5111.5 (5)C25—C26—C27113.8 (6)
C7—C6—H6A109.3C25—C26—H26A108.8
C5—C6—H6A109.3C27—C26—H26A108.8
C7—C6—H6B109.3C25—C26—H26B108.8
C5—C6—H6B109.3C27—C26—H26B108.8
H6A—C6—H6B108.0H26A—C26—H26B107.7
C8—C7—C6111.4 (5)C28—C27—C26111.7 (6)
C8—C7—C10113.1 (5)C28—C27—C30113.6 (5)
C6—C7—C10112.3 (5)C26—C27—C30114.4 (5)
C8—C7—H7A106.5C28—C27—H27A105.4
C6—C7—H7A106.5C26—C27—H27A105.4
C10—C7—H7A106.5C30—C27—H27A105.4
C13—C8—C7124.8 (6)C33—C28—C29121.3 (6)
C13—C8—C9120.2 (7)C33—C28—C27121.0 (7)
C7—C8—C9114.8 (6)C29—C28—C27117.6 (6)
C8—C9—C4114.2 (5)C28—C29—C24116.2 (6)
C8—C9—H9A108.7C28—C29—H29A108.2
C4—C9—H9A108.7C24—C29—H29A108.2
C8—C9—H9B108.7C28—C29—H29B108.2
C4—C9—H9B108.7C24—C29—H29B108.2
H9A—C9—H9B107.6H29A—C29—H29B107.4
C14—C10—C18111.2 (6)C34—C30—C31111.6 (6)
C14—C10—C11110.0 (5)C34—C30—C38111.1 (6)
C18—C10—C11112.4 (5)C31—C30—C38112.0 (5)
C14—C10—C7108.0 (5)C34—C30—C27107.5 (5)
C18—C10—C7109.3 (5)C31—C30—C27106.5 (5)
C11—C10—C7105.6 (5)C38—C30—C27107.9 (5)
C12—C11—C10111.5 (5)C30—C31—C32111.6 (6)
C12—C11—C17111.4 (5)C30—C31—C37116.7 (5)
C10—C11—C17117.4 (5)C32—C31—C37112.7 (5)
C12—C11—H11A105.1C30—C31—H31A104.8
C10—C11—H11A105.1C32—C31—H31A104.8
C17—C11—H11A105.1C37—C31—H31A104.8
C11—C12—C13110.2 (5)C33—C32—C31110.4 (6)
C11—C12—H12A109.6C33—C32—H32A109.6
C13—C12—H12A109.6C31—C32—H32A109.6
C11—C12—H12B109.6C33—C32—H32B109.6
C13—C12—H12B109.6C31—C32—H32B109.6
H12A—C12—H12B108.1H32A—C32—H32B108.1
C8—C13—C12122.3 (6)C28—C33—C32125.2 (7)
C8—C13—H13A118.8C28—C33—H33A117.4
C12—C13—H13A118.8C32—C33—H33A117.4
C10—C14—C15112.3 (6)C30—C34—C35111.4 (6)
C10—C14—H14A109.2C30—C34—H34A109.3
C15—C14—H14A109.2C35—C34—H34A109.3
C10—C14—H14B109.2C30—C34—H34B109.3
C15—C14—H14B109.2C35—C34—H34B109.3
H14A—C14—H14B107.9H34A—C34—H34B108.0
C14—C15—C16111.4 (6)C36—C35—C34107.8 (6)
C14—C15—H15A109.3C36—C35—H35A110.1
C16—C15—H15A109.3C34—C35—H35A110.1
C14—C15—H15B109.3C36—C35—H35B110.1
C16—C15—H15B109.3C34—C35—H35B110.1
H15A—C15—H15B108.0H35A—C35—H35B108.5
C15—C16—C17112.0 (6)C35—C36—C37114.6 (6)
C15—C16—H16A109.2C35—C36—H36A108.6
C17—C16—H16A109.2C37—C36—H36A108.6
C15—C16—H16B109.2C35—C36—H36B108.6
C17—C16—H16B109.2C37—C36—H36B108.6
H16A—C16—H16B107.9H36A—C36—H36B107.6
C20—C17—C19112.0 (6)C40—C37—C39106.6 (5)
C20—C17—C11109.0 (5)C40—C37—C36105.3 (6)
C19—C17—C11113.8 (6)C39—C37—C36111.6 (6)
C20—C17—C16104.3 (5)C40—C37—C31111.0 (5)
C19—C17—C16108.4 (6)C39—C37—C31113.4 (6)
C11—C17—C16108.8 (6)C36—C37—C31108.6 (5)
C10—C18—H18A109.5C30—C38—H38A109.5
C10—C18—H18B109.5C30—C38—H38B109.5
H18A—C18—H18B109.5H38A—C38—H38B109.5
C10—C18—H18C109.5C30—C38—H38C109.5
H18A—C18—H18C109.5H38A—C38—H38C109.5
H18B—C18—H18C109.5H38B—C38—H38C109.5
C17—C19—H19A109.5C37—C39—H39A109.5
C17—C19—H19B109.5C37—C39—H39B109.5
H19A—C19—H19B109.5H39A—C39—H39B109.5
C17—C19—H19C109.5C37—C39—H39C109.5
H19A—C19—H19C109.5H39A—C39—H39C109.5
H19B—C19—H19C109.5H39B—C39—H39C109.5
O1—C20—O2121.3 (7)O4—C40—O3121.1 (7)
O1—C20—C17122.6 (6)O4—C40—C37123.4 (7)
O2—C20—C17116.1 (7)O3—C40—C37115.4 (6)
C1—C2—C4—C324.1 (17)C21—C22—C24—C25107.4 (11)
C1—C2—C4—C5148.3 (13)C21—C22—C24—C2316.4 (14)
C1—C2—C4—C997.4 (14)C21—C22—C24—C29137.6 (10)
C2—C4—C5—C6174.2 (6)C22—C24—C25—C26172.6 (6)
C3—C4—C5—C661.8 (7)C23—C24—C25—C2660.7 (9)
C9—C4—C5—C659.2 (8)C29—C24—C25—C2655.8 (8)
C4—C5—C6—C760.6 (8)C24—C25—C26—C2755.4 (9)
C5—C6—C7—C852.2 (8)C25—C26—C27—C2842.9 (8)
C5—C6—C7—C10179.8 (6)C25—C26—C27—C30173.7 (6)
C6—C7—C8—C13137.7 (7)C26—C27—C28—C33144.3 (7)
C10—C7—C8—C1310.1 (9)C30—C27—C28—C3313.1 (9)
C6—C7—C8—C946.6 (7)C26—C27—C28—C2938.6 (8)
C10—C7—C8—C9174.3 (5)C30—C27—C28—C29169.8 (5)
C13—C8—C9—C4135.3 (7)C33—C28—C29—C24138.2 (7)
C7—C8—C9—C448.8 (8)C27—C28—C29—C2444.7 (9)
C2—C4—C9—C8165.8 (6)C22—C24—C29—C28166.6 (7)
C3—C4—C9—C870.2 (8)C25—C24—C29—C2849.7 (8)
C5—C4—C9—C853.6 (8)C23—C24—C29—C2868.1 (8)
C8—C7—C10—C14159.8 (5)C28—C27—C30—C34165.1 (5)
C6—C7—C10—C1473.1 (6)C26—C27—C30—C3465.1 (7)
C8—C7—C10—C1879.1 (6)C28—C27—C30—C3145.4 (7)
C6—C7—C10—C1848.0 (7)C26—C27—C30—C31175.2 (6)
C8—C7—C10—C1142.0 (7)C28—C27—C30—C3875.0 (6)
C6—C7—C10—C11169.2 (5)C26—C27—C30—C3854.8 (7)
C14—C10—C11—C12178.6 (5)C34—C30—C31—C32178.2 (5)
C18—C10—C11—C1254.0 (7)C38—C30—C31—C3252.9 (7)
C7—C10—C11—C1265.1 (7)C27—C30—C31—C3264.8 (7)
C14—C10—C11—C1748.3 (8)C34—C30—C31—C3746.6 (8)
C18—C10—C11—C1776.3 (7)C38—C30—C31—C3778.7 (7)
C7—C10—C11—C17164.6 (5)C27—C30—C31—C37163.6 (5)
C10—C11—C12—C1352.7 (7)C30—C31—C32—C3349.6 (7)
C17—C11—C12—C13173.9 (5)C37—C31—C32—C33176.9 (5)
C7—C8—C13—C124.0 (10)C29—C28—C33—C32173.5 (7)
C9—C8—C13—C12171.4 (6)C27—C28—C33—C323.5 (11)
C11—C12—C13—C817.2 (9)C31—C32—C33—C2814.2 (10)
C18—C10—C14—C1572.3 (7)C31—C30—C34—C3555.7 (8)
C11—C10—C14—C1553.0 (8)C38—C30—C34—C3570.2 (7)
C7—C10—C14—C15167.9 (5)C27—C30—C34—C35172.0 (5)
C10—C14—C15—C1660.5 (8)C30—C34—C35—C3662.2 (8)
C14—C15—C16—C1758.8 (9)C34—C35—C36—C3761.0 (8)
C12—C11—C17—C2070.0 (7)C35—C36—C37—C40169.2 (6)
C10—C11—C17—C20159.7 (6)C35—C36—C37—C3975.5 (8)
C12—C11—C17—C1955.8 (7)C35—C36—C37—C3150.3 (7)
C10—C11—C17—C1974.5 (8)C30—C31—C37—C40157.9 (6)
C12—C11—C17—C16176.8 (5)C32—C31—C37—C4071.0 (7)
C10—C11—C17—C1646.5 (8)C30—C31—C37—C3982.1 (7)
C15—C16—C17—C20166.5 (6)C32—C31—C37—C3949.0 (8)
C15—C16—C17—C1974.0 (7)C30—C31—C37—C3642.5 (7)
C15—C16—C17—C1150.2 (8)C32—C31—C37—C36173.6 (5)
C19—C17—C20—O1152.8 (7)C39—C37—C40—O4121.8 (7)
C11—C17—C20—O126.0 (10)C36—C37—C40—O4119.5 (7)
C16—C17—C20—O190.1 (8)C31—C37—C40—O42.2 (9)
C19—C17—C20—O229.6 (9)C39—C37—C40—O359.8 (8)
C11—C17—C20—O2156.4 (6)C36—C37—C40—O358.9 (7)
C16—C17—C20—O287.4 (7)C31—C37—C40—O3176.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···O4i0.821.842.653 (7)168
O3—H3D···O1ii0.821.852.655 (7)168
C11—H11A···O10.982.342.764 (7)105
C32—H32B···O40.972.493.081 (9)119
Symmetry codes: (i) x+1/2, y+5/2, z+2; (ii) x1/2, y+5/2, z+2.

Experimental details

Crystal data
Chemical formulaC20H30O2
Mr302.44
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)11.624 (2), 11.803 (2), 25.698 (5)
V3)3525.7 (12)
Z8
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
diffractometer
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.986, 0.993
No. of measured, independent and
observed [I > 2σ(I)] reflections
7031, 6382, 2613
Rint0.088
(sin θ/λ)max1)0.601
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.069, 0.150, 1.00
No. of reflections3598
No. of parameters385
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.26

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···O4i0.821.842.653 (7)168
O3—H3D···O1ii0.821.852.655 (7)168
C11—H11A···O10.982.342.764 (7)105
C32—H32B···O40.972.493.081 (9)119
Symmetry codes: (i) x+1/2, y+5/2, z+2; (ii) x1/2, y+5/2, z+2.
 

Acknowledgements

This work was supported by the Natural Science Fund of Jiangsu Province under grant No. BK2006011 and the National Natural Science Foundation of China under grant No. 30571466.

References

First citationBaldwin, D. E., Loeblich, V. M. & Lawrence, R. V. (1958). J. Org. Chem. 23, 25–26.  CrossRef CAS Web of Science Google Scholar
First citationEnraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands.  Google Scholar
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.  Google Scholar
First citationHarris, G. C. & Sanderson, T. F. (1948). J. Am. Chem. Soc. 70, 2079–2081.  CrossRef PubMed CAS Web of Science Google Scholar
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science Google Scholar
First citationRusso, R., Loverme, J., Rana, G. L., D'Agostino, G., Sasso, O., Calignano, A. & Piomelli, D. (2007). Eur. J. Pharmacol. 566, 117–119.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSmith, E., Williamson, E., Zloh, M. & Gibbons, S. (2005). Phytother. Res. 19, 538–542.  Web of Science CrossRef PubMed CAS Google Scholar

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