organic papers
o3544
Liuet al. C32H52O2 doi:10.1107/S1600536806028340 Acta Cryst.(2006). E62, o3544–o3546
Acta Crystallographica Section E
Structure Reports
Online
ISSN 1600-5368
Dammaradienyl acetate
Rui Liu, Xiao-Bing Wang and Ling-Yi Kong*
Department of Natural Medicinal Chemistry, China Pharmaceutical University, Nanjing 210009, People’s Republic of China
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 298 K
Mean(C–C) = 0.009 A˚ Rfactor = 0.056 wRfactor = 0.192 Data-to-parameter ratio = 8.9
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
Received 7 July 2006 Accepted 21 July 2006
#2006 International Union of Crystallography
All rights reserved
The title compound [systematic name: 4,4,8,10,14-penta-methyl-17-(6-methylhepta-1,5-dien-2-yl)hexadecahydro-1H -cyclopenta[a]phenanthren-3-yl acetate], C32H52O2, contains a fused four-ring system. All three six-membered rings adopt chair conformations and the five-membered ring is twisted. The A/B, B/CandC/Dring junctions are all trans-fused. A chain running along the b axis is formed via C—H O hydrogen bonds, and translation of the chain along theaandc
axes generates the three-dimensional structure.
Comment
The title compound dammaradienyl acetate, (I), was originally isolated from the Indian plantCommelina undulata, which was shown to possess anticancer activity against lymphoid leukaemia in mice (PS 388) in the screening programme of the US National Institutes of Health (Sharma & Tandon, 1982). We have now isolated this compound from Inula nervosa. Here, the crystal structure of (I) is reported.
The skeleton of (I) is composed of a fused four-ring system, including three six-membered rings, A(C3–C7/C12),B(C7– C12) and C (C10–C16), and a five-membered ring,D(C15– C19). All the junctions aretrans-fused, as indicated by their torsion angles (Table 1), which is similar to what is observed in 1-acetyl-24-epi-polacandrin (Simirgiotiset al., 2003). All three six-membered rings,A,BandC, adopt chair conformations, as shown by their puckering parameters (Cremer & Pople, 1975) [q2= 0.039 (5),q3= 0.553 (5),Q= 0.554 (5) A˚ ,= 4.4 (5) and’ = 70 (8) for ring A; q
2 = 0.083 (5), q3 = 0.564 (5), Q = 0.570 (5) A˚ ,= 8.4 (5) and’= 5(3)for ringB;q
2= 0.071 (5),
q3= 0.585 (5),Q= 0.589 (5) A˚ ,= 6.9 (5) and’= 311 (4)for ringC. The value forof 704.2suggests that ringDis twisted about the C15—C16 bond [ = 2P(Altona et al. 1968),P = 352.1 (4),(M) = 44.0 (3) for reference bond C15—C16, where
attached to rings A andD, respectively. The methyl groups C22, C23 and C24 are axially attached to ringsBandC.
The hydrogen bond C21—H21A O2ilinks the molecules of (I) into a chain running along the b axis [C21 O2 = 3.432 (8) A˚ , H21A O2 = 2.57 A˚ and C21—H21A O2 = 149; symmetry code: (i)x,y 1,z; Fig. 2].
Experimental
The dried powdered herbInula nervosaWall. (14.8 kg) was extracted three times with hot ethanol (50 l3). The extract was evaporated under reduced pressure to yield a dark-green mass. This was treated with petroleum ether, chloroform and ethyl acetate. The petroleum ether fraction was chromatographed on a silica-gel column. The
compound eluted with petroleum ether–ethyl acetate (10:1) crystal-lized from chloroform as needles (m.p. 422 K). Spectroscopic analysis:1H NMR (500 MHz, CDCl3,, p.p.m.): 5.13 (1 H,t sept,J=
1.4 and 7.0 Hz, H24), 4.74 (1 H,s, H21), 4.70 (1 H,s,J= 1.5 Hz, H21), 4.49 (1 H,dd,J= 5.5 and 11.3 Hz, H3), 2.04, 1.63, 1.61 (each 3 H,s, – COCH3, H26 and H27), 0.98, 0.88, 0.87,0.86, 0.85 (each 3 H,s), 0.83
(1 H, m, H5); 13C NMR (125 MHz, CDCl3, , p.p.m.): 170.9 (–
COCH3), 152.7 (C20), 131.3 (C25), 124.5 (C24), 107.5 (C21), 80.9
(C3), 55.9 (C5), 50.9 (C9), 49.4 (C14), 47.8 (C17), 45.3 (C13), 40.5 (C8), 38.8 (C22), 37.9 (C4), 37.1 (C10), 35.4 (C7), 34.2 (C1), 31.4 (C15), 28.9 (C23), 27.9 (C28), 27.1 (C2), 25.7 (C26), 24.9 (C16), 23.7 (C2), 21.4 (C11), 21.3 (–COCH3), 18.2 (C6), 17.7 (C27), 16.5 (C30),
16.3 (C19), 15.9 (C18), 15.6 (C29). Crystals of (I) suitable for X-ray analysis were obtained from a chloroform solution by slow evaporation at room temperature.
Crystal data
C32H52O2
Mr= 468.74 Monoclinic, P21
a= 11.660 (4) A˚
b= 7.400 (3) A˚
c= 16.632 (6) A˚ = 91.654 (6)
V= 1434.5 (9) A˚3
Z= 2
Dx= 1.085 Mg m 3 MoKradiation = 0.07 mm 1
T= 298 (2) K Prism, colourless 0.580.410.19 mm
Data collection
Bruker SMART CCD area-detector diffractometer
’and!scans
Absorption correction: multi-scan (SADABS; Bruker, 2000)
Tmin= 0.963,Tmax= 0.988
7593 measured reflections 2735 independent reflections 1529 reflections withI> 2(I)
Rint= 0.052 max= 25.0
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.056
wR(F2) = 0.192
S= 1.00 2735 reflections 307 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.1093P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.20 e A˚ 3
[image:2.610.46.300.75.196.2]min= 0.20 e A˚ 3
Table 1
Selected torsion angles ().
C9—C10—C11—C13 176.9 (3)
C23—C10—C11—C13 65.1 (5)
C16—C10—C11—C13 56.1 (4)
C8—C7—C12—C3 174.7 (4)
C6—C7—C12—C3 51.5 (5)
C8—C7—C12—C22 65.8 (5)
The methyl H atoms were constrained to an ideal geometry, with C—H = 0.96 A˚ andUiso(H) = 1.5Ueq(C), but were allowed to rotate
freely about the C—C bonds. All remaining H atoms were placed in geometrically idealized positions (C—H = 0.93–0.97 A˚ ) and constrained to ride on their parent atoms, withUiso(H) = 1.2Ueq(C).
In the absence of any significant anomalous scattering, Friedel pairs were merged during the final refinement and the absolute config-uration is unknown.
Data collection:SMART(Bruker, 2000); cell refinement:SAINT (Bruker, 2000); data reduction:SAINT; program(s) used to solve structure:SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication:SHELXTLandPLATON(Spek, 2003).
organic papers
Acta Cryst.(2006). E62, o3544–o3546 Liuet al. C
32H52O2
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Figure 1
The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
[image:2.610.95.256.256.531.2]The research work was supported by the Teaching and Research Award Program for Outstanding Young Teachers in Higher Education Institutions of MOE, China (to LYK).
References
Altona, C., Geise, H. J. & Romers, C. (1968).Tetrahedron,24, 13–32.
Bruker (2000).SADABS,SAINT,SHELXTLandSMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975).J. Am. Chem. Soc.97, 1354–1358. Rao, S. T., Westhof, E. & Sundaralingam, M. (1981).Acta Cryst.A37, 421–425. Sharma, S. C. & Tandon, J. S. (1982).Phytochemistry,21, 2420–2421. Sheldrick, G. M. (1997). SHELXL97 and SHELXS97. University of
Go¨ttingen, Germany.
Simirgiotis, M. J., Jime’nez, C., Rodrı´guez, J., Giordano, O. S. & Tonn, C. E. (2003).J. Nat. Prod.66, 1586–1592.
Spek, A. L. (2003).J. Appl. Cryst.36, 7–13.
organic papers
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Liuet al. Csupporting information
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Acta Cryst. (2006). E62, o3544–o3546
supporting information
Acta Cryst. (2006). E62, o3544–o3546 [https://doi.org/10.1107/S1600536806028340]
Dammaradienyl acetate
Rui Liu, Xiao-Bing Wang and Ling-Yi Kong
4,4,8,10,14-pentamethyl-17-(6-methylhepta-1,5-dien-2-yl) hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl
acetate
Crystal data C32H52O2
Mr = 468.74
Monoclinic, P21
Hall symbol: P 2yb a = 11.660 (4) Å b = 7.400 (3) Å c = 16.632 (6) Å β = 91.654 (6)° V = 1434.5 (9) Å3
Z = 2
F(000) = 520 Dx = 1.085 Mg m−3
Melting point: 422 K
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 1389 reflections θ = 2.5–20.3°
µ = 0.07 mm−1
T = 298 K Prism, colourless 0.58 × 0.41 × 0.19 mm
Data collection
Bruker SMART CCD area-detector diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
φ and ω scans
Absorption correction: multi-scan (SADABS; Bruker, 2000) Tmin = 0.963, Tmax = 0.988
7593 measured reflections 2735 independent reflections 1529 reflections with I > 2σ(I) Rint = 0.052
θmax = 25.0°, θmin = 1.8°
h = −13→13 k = −8→8 l = −19→17
Refinement Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.056
wR(F2) = 0.192
S = 1.00 2735 reflections 307 parameters 1 restraint
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained w = 1/[σ2(F
o2) + (0.1093P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.20 e Å−3
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Acta Cryst. (2006). E62, o3544–o3546 Special details
Experimental. Spectroscopic analysis: 1H NMR (500 MHz, CDCl
3, δ, p.p.m.): 5.13 (1H, t sept, J = 1.4 and 7.0 Hz, H24),
4.74 (1H, s, H21), 4.70 (1H, s, J = 1.5 Hz, H21), 4.49 (1H, dd, J = 5.5 and 11.3 Hz, H3), 2.04, 1.63, 1.61 (each 3H, s, – COCH3, H26 and H27), 0.98, 0.88, 0.87,0.86, 0.85 (each 3H, s), 0.83 (1H, m, H5); 13C NMR (125 MHz, CDCl3, δ,
p.p.m.): 170.9 (–COCH3), 152.7 (C20), 131.3 (C25), 124.5 (C24), 107.5 (C21), 80.9 (C3), 55.9 (C5), 50.9 (C9), 49.4
(C14), 47.8 (C17), 45.3 (C13), 40.5 (C8), 38.8 (C22), 37.9 (C4), 37.1 (C10), 35.4 (C7), 34.2 (C1), 31.4 (C15), 28.9 (C23), 27.9 (C28), 27.1 (C2), 25.7 (C26), 24.9 (C16), 23.7 (C2), 21.4 (C11), 21.3 (–COCH3), 18.2 (C6), 17.7 (C27), 16.5
(C30), 16.3 (C19), 15.9 (C18), 15.6 (C29).
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)
x y z Uiso*/Ueq
O1 0.5647 (3) 0.5536 (6) 0.8636 (2) 0.0684 (11)
O2 0.4546 (4) 0.7930 (7) 0.8332 (3) 0.0951 (15)
C1 0.4915 (6) 0.6872 (9) 0.8819 (4) 0.0706 (17)
C2 0.4648 (7) 0.6839 (12) 0.9690 (4) 0.118 (3)
H2A 0.5037 0.5840 0.9946 0.177*
H2B 0.3835 0.6709 0.9748 0.177*
H2C 0.4900 0.7947 0.9938 0.177*
C3 0.7177 (4) 0.6243 (7) 0.6692 (3) 0.0523 (14)
H3A 0.7826 0.7003 0.6566 0.063*
H3B 0.6523 0.6654 0.6367 0.063*
C4 0.6911 (5) 0.6477 (7) 0.7579 (3) 0.0575 (14)
H4A 0.7577 0.6146 0.7909 0.069*
H4B 0.6730 0.7732 0.7686 0.069*
C5 0.5909 (4) 0.5300 (7) 0.7787 (3) 0.0512 (13)
H5 0.5240 0.5686 0.7461 0.061*
C6 0.6101 (4) 0.3251 (8) 0.7641 (3) 0.0506 (13)
C7 0.6454 (4) 0.3082 (7) 0.6752 (3) 0.0436 (12)
H7 0.5781 0.3513 0.6442 0.052*
C8 0.6594 (4) 0.1125 (7) 0.6482 (3) 0.0510 (13)
H8A 0.7321 0.0655 0.6688 0.061*
H8B 0.5985 0.0393 0.6697 0.061*
C9 0.6553 (4) 0.1014 (7) 0.5571 (3) 0.0511 (13)
H9A 0.5798 0.1387 0.5375 0.061*
H9B 0.6662 −0.0235 0.5413 0.061*
C10 0.7468 (4) 0.2195 (7) 0.5167 (3) 0.0431 (12)
C11 0.7429 (4) 0.4135 (7) 0.5526 (3) 0.0412 (12)
H11 0.6670 0.4592 0.5359 0.049*
C12 0.7451 (4) 0.4295 (7) 0.6464 (3) 0.0425 (12)
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Acta Cryst. (2006). E62, o3544–o3546
H13A 0.8167 0.6625 0.5314 0.066*
H13B 0.9050 0.5039 0.5255 0.066*
C14 0.8123 (4) 0.5430 (7) 0.4192 (3) 0.0542 (14)
H14A 0.7400 0.6002 0.4041 0.065*
H14B 0.8737 0.6128 0.3962 0.065*
C15 0.8142 (4) 0.3538 (7) 0.3864 (3) 0.0471 (13)
H15 0.8889 0.3021 0.4021 0.057*
C16 0.7222 (4) 0.2327 (7) 0.4236 (3) 0.0446 (12)
C17 0.7350 (5) 0.0577 (9) 0.3742 (3) 0.0664 (16)
H17A 0.7921 −0.0211 0.3993 0.080*
H17B 0.6625 −0.0065 0.3701 0.080*
C18 0.7729 (5) 0.1186 (9) 0.2908 (3) 0.0710 (17)
H18A 0.7128 0.0945 0.2507 0.085*
H18B 0.8413 0.0535 0.2759 0.085*
C19 0.7980 (4) 0.3242 (8) 0.2952 (3) 0.0563 (14)
H19 0.7294 0.3899 0.2764 0.068*
C20 0.6972 (5) 0.2468 (8) 0.8254 (3) 0.0712 (17)
H20A 0.7702 0.3046 0.8193 0.107*
H20B 0.7050 0.1193 0.8166 0.107*
H20C 0.6711 0.2675 0.8789 0.107*
C21 0.4943 (5) 0.2331 (9) 0.7756 (3) 0.0729 (17)
H21A 0.5020 0.1055 0.7670 0.109*
H21B 0.4388 0.2815 0.7377 0.109*
H21C 0.4695 0.2547 0.8293 0.109*
C22 0.8634 (4) 0.3825 (9) 0.6849 (3) 0.0631 (16)
H22A 0.8829 0.2601 0.6718 0.095*
H22B 0.8606 0.3953 0.7422 0.095*
H22C 0.9203 0.4627 0.6645 0.095*
C23 0.8653 (4) 0.1265 (8) 0.5334 (3) 0.0599 (15)
H23A 0.9247 0.1966 0.5095 0.090*
H23B 0.8643 0.0074 0.5105 0.090*
H23C 0.8799 0.1183 0.5903 0.090*
C24 0.6006 (4) 0.3036 (9) 0.4033 (3) 0.0620 (15)
H24A 0.5451 0.2269 0.4277 0.093*
H24B 0.5878 0.3036 0.3460 0.093*
H24C 0.5931 0.4244 0.4234 0.093*
C25 0.8967 (5) 0.3793 (8) 0.2451 (3) 0.0618 (15)
C26 0.8634 (7) 0.4438 (15) 0.1623 (4) 0.115 (3)
H26A 0.8020 0.3686 0.1403 0.138*
H26B 0.9285 0.4326 0.1276 0.138*
C27 0.8242 (10) 0.6382 (19) 0.1635 (7) 0.181 (6)
H27A 0.7542 0.6435 0.1935 0.218*
H27B 0.8818 0.7074 0.1935 0.218*
C28 0.8037 (8) 0.7249 (19) 0.0903 (6) 0.161 (5)
H28 0.7347 0.6907 0.0654 0.193*
C29 0.8598 (8) 0.8431 (15) 0.0489 (5) 0.117 (3)
C30 0.9619 (11) 0.941 (2) 0.0785 (6) 0.178 (5)
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Acta Cryst. (2006). E62, o3544–o3546
H30B 1.0221 0.8560 0.0911 0.266*
H30C 0.9437 1.0074 0.1260 0.266*
C31 1.0030 (5) 0.3742 (10) 0.2672 (4) 0.084 (2)
H31A 1.0241 0.3337 0.3185 0.101*
H31B 1.0589 0.4111 0.2320 0.101*
C32 0.8214 (8) 0.895 (2) −0.0327 (5) 0.194 (6)
H32A 0.8732 0.9829 −0.0536 0.290*
H32B 0.7457 0.9456 −0.0312 0.290*
H32C 0.8202 0.7902 −0.0668 0.290*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
O1 0.088 (2) 0.066 (3) 0.051 (2) 0.004 (2) 0.0175 (18) −0.004 (2)
O2 0.129 (4) 0.069 (3) 0.089 (3) 0.021 (3) 0.029 (3) 0.004 (3)
C1 0.097 (4) 0.049 (4) 0.067 (4) −0.006 (4) 0.028 (3) −0.010 (3)
C2 0.190 (8) 0.086 (6) 0.081 (5) 0.014 (6) 0.064 (5) −0.012 (4)
C3 0.053 (3) 0.043 (3) 0.061 (3) −0.006 (3) 0.005 (2) −0.001 (3)
C4 0.074 (3) 0.047 (4) 0.051 (3) −0.002 (3) 0.013 (3) −0.002 (3)
C5 0.063 (3) 0.047 (4) 0.044 (3) −0.003 (3) 0.005 (2) 0.008 (3)
C6 0.056 (3) 0.045 (3) 0.051 (3) −0.002 (3) 0.008 (2) 0.010 (3)
C7 0.046 (3) 0.033 (3) 0.052 (3) −0.004 (2) 0.004 (2) 0.007 (2)
C8 0.057 (3) 0.042 (3) 0.054 (3) −0.003 (3) 0.008 (2) 0.007 (3)
C9 0.064 (3) 0.031 (3) 0.059 (3) −0.008 (3) 0.008 (2) 0.000 (3)
C10 0.048 (3) 0.034 (3) 0.048 (3) −0.002 (2) 0.002 (2) 0.003 (2)
C11 0.036 (2) 0.035 (3) 0.053 (3) −0.003 (2) 0.002 (2) 0.006 (2)
C12 0.042 (3) 0.037 (3) 0.048 (3) 0.000 (3) 0.002 (2) 0.002 (2)
C13 0.063 (3) 0.041 (3) 0.061 (3) −0.012 (3) 0.018 (2) 0.002 (3)
C14 0.063 (3) 0.038 (3) 0.062 (3) −0.008 (3) 0.018 (2) 0.001 (3)
C15 0.049 (3) 0.037 (3) 0.055 (3) −0.004 (2) 0.009 (2) 0.000 (2)
C16 0.044 (3) 0.037 (3) 0.053 (3) −0.003 (2) 0.009 (2) 0.004 (2)
C17 0.079 (4) 0.058 (4) 0.063 (4) −0.003 (3) 0.007 (3) −0.010 (3)
C18 0.087 (4) 0.060 (4) 0.067 (4) −0.007 (3) 0.019 (3) −0.008 (3)
C19 0.055 (3) 0.056 (4) 0.059 (3) 0.007 (3) 0.013 (2) 0.006 (3)
C20 0.093 (4) 0.056 (4) 0.064 (4) 0.011 (4) 0.006 (3) 0.020 (3)
C21 0.081 (4) 0.067 (4) 0.072 (4) −0.013 (4) 0.030 (3) 0.002 (3)
C22 0.048 (3) 0.074 (4) 0.067 (3) 0.001 (3) 0.000 (2) −0.002 (3)
C23 0.064 (3) 0.047 (4) 0.069 (3) 0.015 (3) 0.010 (3) 0.007 (3)
C24 0.044 (3) 0.080 (4) 0.062 (3) −0.003 (3) 0.000 (2) 0.003 (3)
C25 0.060 (3) 0.061 (4) 0.065 (4) 0.007 (3) 0.013 (3) 0.006 (3)
C26 0.092 (5) 0.163 (9) 0.092 (5) 0.020 (6) 0.027 (4) 0.054 (6)
C27 0.185 (10) 0.178 (12) 0.184 (11) 0.099 (10) 0.069 (8) 0.098 (9)
C28 0.138 (8) 0.226 (14) 0.120 (7) 0.036 (10) 0.021 (6) 0.067 (9)
C29 0.119 (6) 0.138 (9) 0.098 (6) 0.030 (6) 0.041 (5) 0.046 (6)
C30 0.225 (12) 0.152 (11) 0.155 (10) −0.027 (11) −0.001 (9) 0.030 (8)
C31 0.073 (4) 0.100 (6) 0.081 (4) 0.004 (4) 0.026 (3) 0.009 (4)
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Acta Cryst. (2006). E62, o3544–o3546 Geometric parameters (Å, º)
O1—C1 1.346 (7) C16—C17 1.542 (8)
O1—C5 1.462 (5) C17—C18 1.537 (8)
O2—C1 1.197 (7) C17—H17A 0.9700
C1—C2 1.492 (8) C17—H17B 0.9700
C2—H2A 0.9600 C18—C19 1.550 (9)
C2—H2B 0.9600 C18—H18A 0.9700
C2—H2C 0.9600 C18—H18B 0.9700
C3—C4 1.526 (6) C19—C25 1.498 (7)
C3—C12 1.527 (7) C19—H19 0.9800
C3—H3A 0.9700 C20—H20A 0.9600
C3—H3B 0.9700 C20—H20B 0.9600
C4—C5 1.506 (7) C20—H20C 0.9600
C4—H4A 0.9700 C21—H21A 0.9600
C4—H4B 0.9700 C21—H21B 0.9600
C5—C6 1.553 (8) C21—H21C 0.9600
C5—H5 0.9800 C22—H22A 0.9600
C6—C21 1.529 (7) C22—H22B 0.9600
C6—C20 1.532 (7) C22—H22C 0.9600
C6—C7 1.551 (6) C23—H23A 0.9600
C7—C8 1.526 (7) C23—H23B 0.9600
C7—C12 1.555 (6) C23—H23C 0.9600
C7—H7 0.9800 C24—H24A 0.9600
C8—C9 1.516 (6) C24—H24B 0.9600
C8—H8A 0.9700 C24—H24C 0.9600
C8—H8B 0.9700 C25—C31 1.283 (7)
C9—C10 1.548 (6) C25—C26 1.498 (9)
C9—H9A 0.9700 C26—C27 1.509 (15)
C9—H9B 0.9700 C26—H26A 0.9700
C10—C11 1.556 (7) C26—H26B 0.9700
C10—C23 1.561 (7) C27—C28 1.391 (12)
C10—C16 1.571 (6) C27—H27A 0.9700
C11—C13 1.539 (7) C27—H27B 0.9700
C11—C12 1.564 (6) C28—C29 1.301 (13)
C11—H11 0.9800 C28—H28 0.9300
C12—C22 1.544 (6) C29—C30 1.465 (13)
C13—C14 1.536 (7) C29—C32 1.468 (10)
C13—H13A 0.9700 C30—H30A 0.9600
C13—H13B 0.9700 C30—H30B 0.9600
C14—C15 1.502 (7) C30—H30C 0.9600
C14—H14A 0.9700 C31—H31A 0.9300
C14—H14B 0.9700 C31—H31B 0.9300
C15—C19 1.539 (7) C32—H32A 0.9600
C15—C16 1.541 (6) C32—H32B 0.9600
C15—H15 0.9800 C32—H32C 0.9600
supporting information
sup-6
Acta Cryst. (2006). E62, o3544–o3546
C1—O1—C5 117.2 (4) C24—C16—C17 105.8 (4)
O2—C1—O1 123.1 (5) C15—C16—C17 101.3 (4)
O2—C1—C2 125.9 (7) C24—C16—C10 112.2 (3)
O1—C1—C2 111.1 (6) C15—C16—C10 108.8 (4)
C1—C2—H2A 109.5 C17—C16—C10 117.0 (4)
C1—C2—H2B 109.5 C18—C17—C16 105.6 (5)
H2A—C2—H2B 109.5 C18—C17—H17A 110.6
C1—C2—H2C 109.5 C16—C17—H17A 110.6
H2A—C2—H2C 109.5 C18—C17—H17B 110.6
H2B—C2—H2C 109.5 C16—C17—H17B 110.6
C4—C3—C12 113.4 (4) H17A—C17—H17B 108.8
C4—C3—H3A 108.9 C17—C18—C19 107.7 (5)
C12—C3—H3A 108.9 C17—C18—H18A 110.2
C4—C3—H3B 108.9 C19—C18—H18A 110.2
C12—C3—H3B 108.9 C17—C18—H18B 110.2
H3A—C3—H3B 107.7 C19—C18—H18B 110.2
C5—C4—C3 109.8 (4) H18A—C18—H18B 108.5
C5—C4—H4A 109.7 C25—C19—C15 115.8 (5)
C3—C4—H4A 109.7 C25—C19—C18 112.8 (5)
C5—C4—H4B 109.7 C15—C19—C18 101.8 (4)
C3—C4—H4B 109.7 C25—C19—H19 108.7
H4A—C4—H4B 108.2 C15—C19—H19 108.7
O1—C5—C4 109.8 (4) C18—C19—H19 108.7
O1—C5—C6 107.6 (4) C6—C20—H20A 109.5
C4—C5—C6 114.3 (4) C6—C20—H20B 109.5
O1—C5—H5 108.3 H20A—C20—H20B 109.5
C4—C5—H5 108.3 C6—C20—H20C 109.5
C6—C5—H5 108.3 H20A—C20—H20C 109.5
C21—C6—C20 108.6 (5) H20B—C20—H20C 109.5
C21—C6—C7 110.0 (4) C6—C21—H21A 109.5
C20—C6—C7 114.5 (4) C6—C21—H21B 109.5
C21—C6—C5 106.4 (4) H21A—C21—H21B 109.5
C20—C6—C5 111.2 (4) C6—C21—H21C 109.5
C7—C6—C5 105.8 (4) H21A—C21—H21C 109.5
C8—C7—C6 113.0 (4) H21B—C21—H21C 109.5
C8—C7—C12 111.7 (4) C12—C22—H22A 109.5
C6—C7—C12 117.9 (4) C12—C22—H22B 109.5
C8—C7—H7 104.2 H22A—C22—H22B 109.5
C6—C7—H7 104.2 C12—C22—H22C 109.5
C12—C7—H7 104.2 H22A—C22—H22C 109.5
C9—C8—C7 110.2 (4) H22B—C22—H22C 109.5
C9—C8—H8A 109.6 C10—C23—H23A 109.5
C7—C8—H8A 109.6 C10—C23—H23B 109.5
C9—C8—H8B 109.6 H23A—C23—H23B 109.5
C7—C8—H8B 109.6 C10—C23—H23C 109.5
H8A—C8—H8B 108.1 H23A—C23—H23C 109.5
C8—C9—C10 113.6 (4) H23B—C23—H23C 109.5
supporting information
sup-7
Acta Cryst. (2006). E62, o3544–o3546
C10—C9—H9A 108.8 C16—C24—H24B 109.5
C8—C9—H9B 108.8 H24A—C24—H24B 109.5
C10—C9—H9B 108.8 C16—C24—H24C 109.5
H9A—C9—H9B 107.7 H24A—C24—H24C 109.5
C9—C10—C11 109.1 (4) H24B—C24—H24C 109.5
C9—C10—C23 107.0 (4) C31—C25—C19 125.7 (5)
C11—C10—C23 112.0 (4) C31—C25—C26 119.7 (5)
C9—C10—C16 110.8 (4) C19—C25—C26 114.5 (5)
C11—C10—C16 108.3 (4) C25—C26—C27 111.2 (8)
C23—C10—C16 109.8 (4) C25—C26—H26A 109.4
C13—C11—C10 111.5 (4) C27—C26—H26A 109.4
C13—C11—C12 114.0 (4) C25—C26—H26B 109.4
C10—C11—C12 116.9 (4) C27—C26—H26B 109.4
C13—C11—H11 104.2 H26A—C26—H26B 108.0
C10—C11—H11 104.2 C28—C27—C26 118.1 (11)
C12—C11—H11 104.2 C28—C27—H27A 107.8
C3—C12—C22 107.5 (4) C26—C27—H27A 107.8
C3—C12—C7 107.8 (4) C28—C27—H27B 107.8
C22—C12—C7 114.2 (4) C26—C27—H27B 107.8
C3—C12—C11 108.7 (4) H27A—C27—H27B 107.1
C22—C12—C11 112.7 (4) C29—C28—C27 134.2 (12)
C7—C12—C11 105.8 (3) C29—C28—H28 112.9
C14—C13—C11 113.3 (4) C27—C28—H28 112.9
C14—C13—H13A 108.9 C28—C29—C30 124.7 (10)
C11—C13—H13A 108.9 C28—C29—C32 121.4 (11)
C14—C13—H13B 108.9 C30—C29—C32 113.9 (9)
C11—C13—H13B 108.9 C29—C30—H30A 109.5
H13A—C13—H13B 107.7 C29—C30—H30B 109.5
C15—C14—C13 110.4 (4) H30A—C30—H30B 109.5
C15—C14—H14A 109.6 C29—C30—H30C 109.5
C13—C14—H14A 109.6 H30A—C30—H30C 109.5
C15—C14—H14B 109.6 H30B—C30—H30C 109.5
C13—C14—H14B 109.6 C25—C31—H31A 120.0
H14A—C14—H14B 108.1 C25—C31—H31B 120.0
C14—C15—C19 119.2 (4) H31A—C31—H31B 120.0
C14—C15—C16 112.3 (4) C29—C32—H32A 109.5
C19—C15—C16 104.2 (4) C29—C32—H32B 109.5
C14—C15—H15 106.9 H32A—C32—H32B 109.5
C19—C15—H15 106.9 C29—C32—H32C 109.5
C16—C15—H15 106.9 H32A—C32—H32C 109.5
C24—C16—C15 111.2 (4) H32B—C32—H32C 109.5
C5—O1—C1—O2 −5.4 (8) C10—C11—C12—C22 72.0 (5)
C5—O1—C1—C2 175.8 (5) C13—C11—C12—C7 173.5 (4)
C12—C3—C4—C5 −57.8 (5) C10—C11—C12—C7 −53.5 (4)
C1—O1—C5—C4 87.7 (5) C10—C11—C13—C14 53.1 (5)
C1—O1—C5—C6 −146.9 (4) C12—C11—C13—C14 −171.6 (4)
supporting information
sup-8
Acta Cryst. (2006). E62, o3544–o3546
C3—C4—C5—C6 59.0 (5) C13—C14—C15—C19 178.8 (3)
O1—C5—C6—C21 66.7 (5) C13—C14—C15—C16 56.4 (5)
C4—C5—C6—C21 −170.5 (4) C14—C15—C16—C24 62.7 (5)
O1—C5—C6—C20 −51.6 (5) C19—C15—C16—C24 −68.0 (4)
C4—C5—C6—C20 71.2 (5) C14—C15—C16—C17 174.5 (4)
O1—C5—C6—C7 −176.5 (3) C19—C15—C16—C17 43.8 (4)
C4—C5—C6—C7 −53.7 (5) C14—C15—C16—C10 −61.5 (5)
C21—C6—C7—C8 −61.0 (5) C19—C15—C16—C10 167.8 (3)
C20—C6—C7—C8 61.2 (5) C9—C10—C16—C24 55.9 (5)
C5—C6—C7—C8 −175.7 (4) C11—C10—C16—C24 −63.8 (5)
C21—C6—C7—C12 166.0 (4) C23—C10—C16—C24 173.4 (4)
C20—C6—C7—C12 −71.9 (5) C9—C10—C16—C15 179.2 (4)
C5—C6—C7—C12 51.2 (5) C11—C10—C16—C15 59.5 (4)
C6—C7—C8—C9 161.8 (3) C23—C10—C16—C15 −63.3 (5)
C12—C7—C8—C9 −62.3 (5) C9—C10—C16—C17 −66.7 (5)
C7—C8—C9—C10 56.8 (5) C11—C10—C16—C17 173.5 (4)
C8—C9—C10—C11 −49.0 (5) C23—C10—C16—C17 50.7 (5)
C8—C9—C10—C23 72.5 (5) C24—C16—C17—C18 84.5 (4)
C8—C9—C10—C16 −168.1 (4) C15—C16—C17—C18 −31.2 (5)
C9—C10—C11—C13 −176.9 (3) C10—C16—C17—C18 −149.5 (4)
C23—C10—C11—C13 65.1 (5) C16—C17—C18—C19 7.8 (5)
C16—C10—C11—C13 −56.1 (4) C14—C15—C19—C25 71.4 (6)
C9—C10—C11—C12 49.2 (5) C16—C15—C19—C25 −162.3 (4)
C23—C10—C11—C12 −68.7 (4) C14—C15—C19—C18 −165.2 (4)
C16—C10—C11—C12 170.1 (3) C16—C15—C19—C18 −38.9 (5)
C4—C3—C12—C22 −71.3 (4) C17—C18—C19—C25 144.3 (4)
C4—C3—C12—C7 52.6 (5) C17—C18—C19—C15 18.9 (5)
C4—C3—C12—C11 167.1 (3) C15—C19—C25—C31 32.0 (8)
C8—C7—C12—C3 174.7 (4) C18—C19—C25—C31 −85.6 (7)
C6—C7—C12—C3 −51.5 (5) C15—C19—C25—C26 −148.2 (5)
C8—C7—C12—C22 −65.8 (5) C18—C19—C25—C26 94.2 (7)
C6—C7—C12—C22 68.0 (5) C31—C25—C26—C27 −99.4 (8)
C8—C7—C12—C11 58.3 (4) C19—C25—C26—C27 80.9 (8)
C6—C7—C12—C11 −167.9 (4) C25—C26—C27—C28 172.1 (8)
C13—C11—C12—C3 57.9 (5) C26—C27—C28—C29 −102.1 (18)
C10—C11—C12—C3 −169.2 (3) C27—C28—C29—C30 −10 (2)
