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Acta Cryst. (2008). E64, o604-o605    [ doi:10.1107/S1600536808004546 ]

(4aS,10aS)-7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene: a new diterpenoid compound

A. Zeroual, N. Mazoir, J.-C. Daran, M. Akssira and A. Benharref

Abstract top

The new title diterpenoid compound, C20H30O, is a natural product isolated from Tetraclinis articulata wood via chloroform extraction. The asymmetric unit contains four molecules with the same S,S configuration, deduced from the chemical synthesis. Indeed, an overlay analysis, calculated using structure-matching software, shows that the four molecules can be superimposed. The central ring has a half-chair conformation, whereas the saturated ring displays a chair conformation.

Comment top

Among tricyclic diterpenoids, the class based on the phenanthrene skeleton is of great interest in alimentary, agricultural and cosmetic industries. Many of these substances exhibit biological activities that have been recently reported (Hedden & Philips, 2000; Duan et al., 2001; Rundle et al., 2001; Yang et al., 2002).

Within the context of our research for the chemical constituents of Tetraclinis articulata (Barrero et al., 2003), we have isolated two components structurally related to the diterpenoid skeletons (Zeroual, Mazoir, Berraho et al. (2007); Zeroual, Mazoir, Maya et al. (2007). The title compound (I), was isolated from Tetraclinis articulata wood using extraction with chloroform in a sohxlet apparatus.

The structure of (I) was established by 1H and 13C NMR and confirmed by its single-Crystal X-ray structure. The unit cell in space group P1 contains four identical molecules having the same configuration (S,S). Indeed an overlay analyses calculated using the structure matching software (Watkin et al., 2003; Collins et al., 2006) shows that the four molecules could be superimposed (Table 1).

Each of these molecules is built up from three six-membered fused rings, a saturated one and two unsaturated (Fig. 1). The central rings display a half-chair conformation whereas the other unsaturated six-membered ring has a chair conformation (Cremer & Pople, 1975; Table 2).

Related literature top

For related literature, see: Barrero et al. (2003); Collins et al. (2006); Cremer & Pople (1975); Duan et al. (2001); Hedden & Philips (2000); Rundle et al. (2001); Watkin et al. (2003); Yang et al. (2002); Zeroual, Mazoir, Berraho et al. (2007); Zeroual, Mazoir, Maya et al. (2007).

Experimental top

50 g of Tetraclinis articulata wood was extracted with chloroform (300 ml) in a Sohxlet apparatus during 24 h. The CHCl3 solution was cooled to yield, after solvent removal, one fraction (3.2 g) which was then subjected to silica gel column chromatography using hexane as an eluent afforded compound (I) in 64% yield. Suitable crystals of (I) were obtained by evaporation of a hexane solution at 277 K. m.p. = 373–374 K (hexane); Spectroscopic analysis: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 1.51 (2H2, m), 1.58 (2H3, m), 1.60 (2H4, m), 7.02 (1H5, d, J = 8.7 Hz), 6.60 (1H6, d, J = 8.7 Hz), 4.50 (OH, s), 2.84 (2H9, m), 1.58 (2H10, m), 1.76 (1H10a, dd, J1 = 10.6 Hz, J2 = 2.0 Hz), 3.11 (1H11, m), 1.30 (3H12, d, J = 10 Hz), 1.31 (3H13, d, J = 10 Hz), 0.97 (3H14, s), 0.98 (3H15, s), 1.11 (3H16, s); 13C NMR (75 MHz, CDCl3, d, p.p.m.): 37.8 (C1), 41.6 (C2), 19.6 (C3), 39.6 (C4),37.5 (C4a), 131.1 (C4b), 123.0 (C5), 114.4 (C6), 152.1 (C7), 143.3 (C8), 134.1(C8a), 28.8 (C9), 19.5 (C10), 49.6 (C10a), 33.3 (C11), 20.1 (C12), 20.2 (C13), 22.4 (C14), 25.5 (C15), 24.6 (C16).

Refinement top

All H atoms attached to C and O atoms were fixed geometrically and treated as riding with C—H = 0.99 Å (methyl), 0.98 Å (methylene), 1.0 Å(methine) or 0.95 Å (aromatic) and O—H = 0.84 Å with Uiso(H) = 1.2Ueq(C or O) or Uiso(H) = 1.5Ueq(methyl).

In the absence of significant anomalous scattering, the absolute configuration could not determined by X-ray analyses and then the Friedel pairs were merged and any references to the Flack parameter were removed. The absolute configuration was deduced from the chemical syntheses.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular view of one of the four molecules of the title compound with the atom-labelling scheme. Ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
(4aS,10aS)-7-Hydroxy-8-isopropyl-1,1,4a-trimethyl-1,2,3,4,4a,9,10,10a- octahydrophenanthrene top
Crystal data top
C20H30O1Z = 4
Mr = 286.44F000 = 632
Triclinic, P1Dx = 1.141 Mg m−3
Hall symbol: P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.5422 (5) ÅCell parameters from 6230 reflections
b = 12.1343 (5) Åθ = 2.8–32.1º
c = 14.8245 (6) ŵ = 0.07 mm−1
α = 70.578 (4)ºT = 180 (2) K
β = 70.096 (4)ºBlock, colourless
γ = 89.968 (3)º0.48 × 0.40 × 0.22 mm
V = 1668.01 (14) Å3
Data collection top
Oxford Diffraction Xcalibur
diffractometer		6812 independent reflections
Radiation source: fine-focus sealed tube4589 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.028
Detector resolution: 8.2632 pixels mm-1θmax = 26.4º
T = 180(2) Kθmin = 2.8º
ω and φ scansh = −13→13
Absorption correction: nonek = −14→15
13146 measured reflectionsl = −16→18
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)] = 0.040H-atom parameters constrained
wR(F2) = 0.109  w = 1/[σ2(Fo2) + (0.0625P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max = 0.001
6812 reflectionsΔρmax = 0.16 e Å−3
781 parametersΔρmin = −0.21 e Å−3
3 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
C20H30O1γ = 89.968 (3)º
Mr = 286.44V = 1668.01 (14) Å3
Triclinic, P1Z = 4
a = 10.5422 (5) ÅMo Kα
b = 12.1343 (5) ŵ = 0.07 mm−1
c = 14.8245 (6) ÅT = 180 (2) K
α = 70.578 (4)º0.48 × 0.40 × 0.22 mm
β = 70.096 (4)º
Data collection top
Oxford Diffraction Xcalibur
diffractometer		6812 independent reflections
Absorption correction: none4589 reflections with I > 2σ(I)
13146 measured reflectionsRint = 0.028
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.16 e Å−3
S = 0.98Δρmin = −0.21 e Å−3
6812 reflectionsAbsolute structure: ?
781 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
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
O10.1167 (3)0.09842 (18)0.96490 (17)0.0523 (7)
H10.08020.07581.02910.078*
C10.3301 (3)0.7807 (2)0.6414 (2)0.0315 (7)
C20.3671 (3)0.8211 (3)0.7172 (2)0.0386 (8)
H2A0.45130.78930.72370.046*
H2B0.38620.90820.68960.046*
C30.2567 (3)0.7828 (3)0.8224 (2)0.0404 (8)
H3A0.17460.82000.81740.048*
H3B0.28800.80970.86840.048*
C40.2208 (3)0.6491 (3)0.8680 (2)0.0349 (7)
H4A0.14770.62720.93640.042*
H4B0.30140.61250.87750.042*
C4A0.1733 (3)0.5998 (2)0.80008 (19)0.0231 (6)
C4B0.1609 (3)0.4646 (2)0.8406 (2)0.0243 (6)
C50.1037 (3)0.4046 (3)0.9454 (2)0.0365 (8)
H50.07400.44830.98980.044*
C60.0887 (3)0.2847 (3)0.9868 (2)0.0425 (8)
H60.04860.24601.05900.051*
C70.1316 (3)0.2202 (3)0.9243 (2)0.0350 (7)
C80.1919 (3)0.2750 (2)0.8182 (2)0.0280 (7)
C8A0.2012 (3)0.3984 (2)0.7770 (2)0.0239 (6)
C90.2569 (3)0.4581 (2)0.6617 (2)0.0285 (7)
H9A0.20760.41910.63210.034*
H9B0.35380.44670.63540.034*
C100.2455 (3)0.5897 (2)0.6247 (2)0.0298 (7)
H10B0.30700.62740.55240.036*
H10C0.15120.60190.62860.036*
C10A0.2836 (3)0.6453 (2)0.69120 (19)0.0232 (6)
H10A0.36620.60980.70000.028*
C110.2451 (3)0.2019 (2)0.7505 (2)0.0317 (7)
H110.29000.25880.67880.038*
C120.3523 (3)0.1277 (3)0.7767 (3)0.0465 (9)
H12A0.31160.06850.84570.070*
H12B0.42660.17850.77420.070*
H12C0.38800.08820.72700.070*
C130.1324 (4)0.1245 (3)0.7495 (3)0.0537 (10)
H13A0.06480.17310.73060.081*
H13B0.08870.06450.81790.081*
H13C0.17110.08590.69950.081*
C140.0312 (3)0.6331 (3)0.8057 (2)0.0340 (7)
H14A−0.03410.59310.87540.051*
H14B0.00430.60890.75730.051*
H14C0.03270.71860.78790.051*
C150.2264 (4)0.8541 (3)0.6058 (3)0.0441 (8)
H15A0.19090.81770.56780.066*
H15B0.27060.93410.56120.066*
H15C0.15130.85740.66570.066*
C160.4607 (4)0.8047 (3)0.5459 (3)0.0500 (9)
H16A0.49980.88720.52110.075*
H16B0.43840.78890.49200.075*
H16C0.52660.75320.56410.075*
O20.8528 (3)0.97439 (18)0.60117 (17)0.0518 (6)
H20.89890.99800.53810.078*
C210.6785 (3)0.2891 (2)0.9123 (2)0.0320 (7)
C220.7924 (3)0.2434 (3)0.8428 (2)0.0413 (8)
H22A0.88030.26760.84560.050*
H22B0.77710.15620.86950.050*
C230.8020 (4)0.2876 (3)0.7326 (2)0.0422 (8)
H23A0.71670.25920.72860.051*
H23B0.87770.25550.69190.051*
C240.8258 (3)0.4220 (3)0.6870 (2)0.0347 (7)
H24A0.83270.44810.61450.042*
H24B0.91310.45010.68830.042*
C24A0.7099 (3)0.4774 (2)0.7467 (2)0.0248 (6)
C24B0.7475 (3)0.6111 (2)0.7106 (2)0.0257 (6)
C250.8194 (3)0.6739 (3)0.6071 (2)0.0364 (7)
H250.84470.63280.56040.044*
C260.8542 (3)0.7929 (3)0.5712 (2)0.0431 (9)
H260.90290.83390.50020.052*
C270.8190 (3)0.8534 (3)0.6376 (2)0.0348 (7)
C280.7493 (3)0.7974 (2)0.7412 (2)0.0258 (6)
C28A0.7106 (3)0.6744 (2)0.7776 (2)0.0238 (6)
C290.6309 (3)0.6123 (2)0.8901 (2)0.0299 (7)
H29A0.55090.65360.91050.036*
H29B0.68850.61930.92910.036*
C300.5816 (3)0.4823 (2)0.9215 (2)0.0308 (7)
H30B0.49770.47420.90710.037*
H30C0.56030.44230.99600.037*
C30A0.6923 (3)0.4254 (2)0.8615 (2)0.0249 (6)
H30A0.77850.45530.86460.030*
C2110.7177 (3)0.8651 (2)0.8143 (2)0.0299 (7)
H2110.67400.80590.88510.036*
C2120.8445 (3)0.9267 (3)0.8120 (3)0.0511 (9)
H12D0.88500.99190.74640.077*
H12E0.91020.87050.82010.077*
H12F0.82030.95750.86820.077*
C2130.6172 (3)0.9520 (3)0.7982 (3)0.0457 (8)
H13D0.53170.90990.80760.068*
H13E0.65481.01040.72860.068*
H13F0.60000.99190.84810.068*
C2140.5822 (3)0.4567 (3)0.7231 (2)0.0373 (7)
H14D0.59930.50000.65050.056*
H14E0.50540.48470.76540.056*
H14F0.56080.37240.73850.056*
C2150.5373 (3)0.2246 (3)0.9368 (3)0.0485 (9)
H15D0.53410.14020.97330.073*
H15E0.52240.23600.87270.073*
H15F0.46630.25670.97990.073*
C2160.7010 (4)0.2589 (3)1.0143 (2)0.0470 (9)
H16D0.78640.30281.00290.070*
H16E0.70560.17421.04210.070*
H16F0.62530.28031.06320.070*
O30.8840 (3)0.9285 (2)0.07938 (18)0.0581 (7)
H30.93110.94640.01690.087*
C310.6454 (3)0.2602 (2)0.4319 (2)0.0359 (7)
C320.7527 (3)0.2014 (3)0.3711 (2)0.0432 (8)
H32A0.84170.22200.37390.052*
H32B0.72900.11490.40420.052*
C330.7665 (3)0.2360 (3)0.2608 (2)0.0411 (8)
H33A0.67960.21120.25680.049*
H33B0.83790.19530.22600.049*
C340.8037 (3)0.3691 (3)0.2065 (2)0.0352 (7)
H34A0.81470.38970.13360.042*
H34B0.89190.39290.20900.042*
C34A0.6952 (3)0.4374 (2)0.2557 (2)0.0261 (6)
C34B0.7445 (3)0.5702 (2)0.2100 (2)0.0264 (7)
C350.8292 (3)0.6205 (3)0.1079 (2)0.0401 (8)
H350.85600.57230.06740.048*
C360.8749 (4)0.7386 (3)0.0648 (2)0.0481 (9)
H360.93320.7712−0.00510.058*
C370.8372 (3)0.8099 (3)0.1215 (2)0.0379 (8)
C380.7512 (3)0.7654 (2)0.2229 (2)0.0290 (7)
C38A0.7050 (3)0.6438 (2)0.2673 (2)0.0244 (6)
C390.6157 (3)0.5934 (2)0.3800 (2)0.0333 (7)
H39A0.53610.63740.39110.040*
H39B0.66760.60730.42040.040*
C40A0.6711 (3)0.3950 (2)0.3713 (2)0.0264 (6)
H40A0.75760.42300.37530.032*
C400.5640 (3)0.4620 (2)0.4216 (2)0.0327 (7)
H40B0.54140.43030.49680.039*
H40C0.48010.45080.40810.039*
C3110.7120 (3)0.8454 (3)0.2858 (3)0.0394 (8)
H3110.64490.79580.35440.047*
C3120.8296 (4)0.8890 (4)0.3053 (3)0.0646 (12)
H12G0.89860.93830.24000.097*
H12H0.86920.82170.33890.097*
H12I0.79790.93550.34970.097*
C3130.6415 (4)0.9483 (3)0.2425 (4)0.0693 (13)
H13G0.56650.91920.22810.104*
H13H0.70681.00460.17890.104*
H13I0.60570.98740.29250.104*
C3140.5678 (3)0.4218 (3)0.2302 (2)0.0392 (8)
H14G0.53630.33770.25330.059*
H14H0.59030.45720.15590.059*
H14I0.49580.46060.26510.059*
C3150.5018 (3)0.2012 (3)0.4569 (3)0.0465 (9)
H15G0.49010.11900.50240.070*
H15H0.49070.20370.39330.070*
H15I0.43330.24340.49100.070*
C3160.6655 (4)0.2384 (3)0.5336 (2)0.0543 (10)
H16G0.66170.15360.56860.081*
H16H0.59350.26940.57710.081*
H16I0.75430.27830.52040.081*
O40.1205 (2)0.05884 (18)0.44649 (17)0.0487 (6)
H40.11590.03220.50770.073*
C410.3018 (3)0.7513 (2)0.1661 (2)0.0337 (7)
C420.3250 (3)0.7861 (3)0.2501 (3)0.0434 (8)
H42A0.40990.75760.25830.052*
H42B0.33780.87310.22780.052*
C430.2094 (4)0.7374 (3)0.3533 (3)0.0451 (9)
H43A0.12550.77020.34710.054*
H43B0.23190.76200.40400.054*
C440.1849 (3)0.6035 (3)0.3906 (2)0.0367 (7)
H44A0.10920.57410.45790.044*
H44B0.26740.57100.40030.044*
C44A0.1501 (3)0.5599 (2)0.3150 (2)0.0252 (6)
C44B0.1458 (3)0.4254 (2)0.3473 (2)0.0254 (6)
C450.0939 (3)0.3564 (3)0.4506 (2)0.0406 (8)
H450.06360.39370.50000.049*
C460.0850 (3)0.2350 (3)0.4839 (2)0.0435 (9)
H460.04790.18950.55510.052*
C470.1301 (3)0.1814 (3)0.4134 (2)0.0345 (7)
C480.1831 (3)0.2444 (2)0.3093 (2)0.0285 (7)
C48A0.1886 (3)0.3683 (2)0.2761 (2)0.0248 (6)
C490.2438 (3)0.4377 (2)0.1625 (2)0.0300 (7)
H49A0.19530.40390.12910.036*
H49B0.34110.42810.13450.036*
C500.2309 (3)0.5683 (2)0.1341 (2)0.0312 (7)
H50B0.29480.61130.06340.037*
H50C0.13740.58130.13610.037*
C50A0.2621 (3)0.6154 (2)0.2079 (2)0.0270 (6)
H50A0.34600.58140.21540.032*
C4110.2381 (3)0.1805 (2)0.2333 (2)0.0344 (7)
H4110.27050.24200.16300.041*
C4120.3594 (3)0.1187 (3)0.2459 (3)0.0468 (9)
H12J0.39560.08510.19200.070*
H12K0.33100.05570.31320.070*
H12L0.43000.17560.24060.070*
C4130.1285 (4)0.0942 (3)0.2377 (3)0.0526 (10)
H13J0.10450.02580.30140.079*
H13K0.16310.06820.17880.079*
H13L0.04760.13330.23580.079*
C4140.0053 (3)0.5861 (3)0.3207 (2)0.0358 (7)
H14J−0.05900.54530.39070.054*
H14K−0.01920.55850.27300.054*
H14L0.00180.67110.30210.054*
C4150.1991 (4)0.8224 (3)0.1279 (2)0.0451 (9)
H15J0.17960.79380.07890.068*
H15K0.23680.90580.09420.068*
H15L0.11490.81330.18610.068*
C4160.4386 (4)0.7830 (3)0.0761 (3)0.0577 (11)
H16J0.47170.86630.05580.087*
H16K0.42660.76890.01800.087*
H16L0.50480.73410.09710.087*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0690 (18)0.0265 (12)0.0444 (14)−0.0080 (11)−0.0136 (13)0.0012 (11)
C10.0334 (18)0.0237 (16)0.0343 (17)0.0028 (13)−0.0072 (14)−0.0116 (13)
C20.0403 (19)0.0297 (17)0.053 (2)0.0025 (14)−0.0212 (16)−0.0187 (15)
C30.050 (2)0.0388 (19)0.046 (2)0.0084 (15)−0.0215 (17)−0.0271 (16)
C40.0388 (18)0.0408 (18)0.0320 (17)0.0077 (14)−0.0142 (14)−0.0202 (14)
C4A0.0229 (15)0.0256 (15)0.0246 (15)0.0092 (12)−0.0100 (12)−0.0120 (12)
C4B0.0227 (15)0.0256 (15)0.0249 (16)0.0017 (12)−0.0095 (12)−0.0083 (13)
C50.0428 (19)0.0385 (19)0.0252 (17)0.0061 (15)−0.0056 (14)−0.0143 (14)
C60.046 (2)0.042 (2)0.0223 (17)−0.0045 (15)−0.0025 (15)−0.0008 (15)
C70.0370 (18)0.0240 (17)0.0361 (19)−0.0018 (14)−0.0120 (15)−0.0019 (14)
C80.0267 (16)0.0258 (16)0.0307 (17)0.0037 (12)−0.0106 (13)−0.0086 (13)
C8A0.0212 (15)0.0265 (16)0.0238 (15)0.0040 (12)−0.0080 (12)−0.0089 (12)
C90.0370 (17)0.0240 (15)0.0244 (15)0.0050 (12)−0.0092 (13)−0.0103 (12)
C100.0418 (18)0.0241 (15)0.0232 (15)0.0060 (13)−0.0118 (13)−0.0078 (12)
C10A0.0272 (16)0.0228 (14)0.0242 (15)0.0101 (12)−0.0111 (13)−0.0119 (12)
C110.0353 (18)0.0188 (15)0.0413 (18)0.0027 (12)−0.0130 (14)−0.0118 (13)
C120.041 (2)0.044 (2)0.069 (2)0.0158 (16)−0.0246 (18)−0.0334 (18)
C130.046 (2)0.060 (2)0.076 (3)0.0112 (18)−0.033 (2)−0.039 (2)
C140.0277 (16)0.0359 (17)0.0420 (18)0.0090 (13)−0.0134 (14)−0.0175 (14)
C150.060 (2)0.0293 (17)0.046 (2)0.0110 (16)−0.0255 (17)−0.0111 (15)
C160.047 (2)0.0361 (19)0.051 (2)−0.0003 (15)−0.0007 (17)−0.0143 (16)
O20.0609 (16)0.0286 (13)0.0434 (14)−0.0068 (11)−0.0008 (12)−0.0033 (11)
C210.0470 (19)0.0214 (15)0.0352 (17)0.0072 (13)−0.0218 (15)−0.0122 (13)
C220.057 (2)0.0292 (17)0.048 (2)0.0200 (15)−0.0255 (17)−0.0186 (15)
C230.055 (2)0.0405 (19)0.043 (2)0.0218 (16)−0.0192 (16)−0.0271 (16)
C240.0419 (19)0.0368 (18)0.0296 (17)0.0160 (14)−0.0118 (14)−0.0182 (14)
C24A0.0285 (16)0.0235 (15)0.0255 (15)0.0094 (12)−0.0107 (13)−0.0114 (12)
C24B0.0273 (16)0.0247 (15)0.0257 (16)0.0054 (12)−0.0113 (13)−0.0076 (13)
C250.047 (2)0.0361 (18)0.0234 (16)0.0052 (15)−0.0076 (14)−0.0123 (14)
C260.049 (2)0.041 (2)0.0228 (17)0.0005 (16)−0.0025 (15)−0.0022 (15)
C270.0365 (18)0.0248 (16)0.0328 (18)−0.0020 (13)−0.0065 (14)−0.0036 (14)
C280.0243 (15)0.0213 (15)0.0312 (17)0.0019 (12)−0.0107 (13)−0.0077 (13)
C28A0.0227 (15)0.0226 (15)0.0265 (15)0.0036 (12)−0.0102 (12)−0.0079 (12)
C290.0349 (17)0.0243 (15)0.0276 (16)0.0058 (13)−0.0048 (13)−0.0123 (13)
C300.0360 (17)0.0215 (15)0.0282 (16)0.0017 (13)−0.0037 (13)−0.0086 (13)
C30A0.0311 (16)0.0201 (14)0.0240 (15)0.0022 (12)−0.0095 (13)−0.0089 (12)
C2110.0338 (17)0.0215 (15)0.0372 (17)0.0045 (12)−0.0149 (14)−0.0118 (13)
C2120.044 (2)0.054 (2)0.078 (3)0.0183 (17)−0.0318 (19)−0.041 (2)
C2130.0367 (19)0.045 (2)0.065 (2)0.0143 (15)−0.0224 (17)−0.0269 (18)
C2140.0428 (19)0.0368 (18)0.0455 (19)0.0095 (14)−0.0291 (15)−0.0173 (15)
C2150.059 (2)0.0337 (19)0.050 (2)−0.0116 (17)−0.0182 (18)−0.0118 (16)
C2160.071 (2)0.0310 (18)0.040 (2)0.0073 (16)−0.0253 (18)−0.0076 (15)
O30.0732 (19)0.0369 (13)0.0404 (14)−0.0227 (12)−0.0078 (13)0.0025 (11)
C310.049 (2)0.0244 (16)0.0346 (18)0.0052 (14)−0.0157 (15)−0.0101 (14)
C320.050 (2)0.0289 (17)0.056 (2)0.0148 (15)−0.0251 (17)−0.0153 (16)
C330.0430 (19)0.0364 (19)0.049 (2)0.0137 (15)−0.0133 (16)−0.0242 (16)
C340.0371 (18)0.0391 (19)0.0335 (17)0.0076 (14)−0.0095 (14)−0.0213 (15)
C34A0.0297 (16)0.0264 (15)0.0277 (16)0.0052 (12)−0.0146 (13)−0.0123 (13)
C34B0.0263 (16)0.0287 (16)0.0240 (16)0.0016 (12)−0.0109 (13)−0.0073 (13)
C350.051 (2)0.043 (2)0.0251 (17)−0.0014 (16)−0.0099 (15)−0.0149 (15)
C360.056 (2)0.048 (2)0.0235 (18)−0.0130 (17)−0.0019 (16)−0.0049 (16)
C370.044 (2)0.0277 (17)0.0319 (19)−0.0099 (15)−0.0132 (15)0.0012 (15)
C380.0258 (16)0.0267 (16)0.0353 (18)0.0041 (12)−0.0134 (14)−0.0094 (14)
C38A0.0178 (14)0.0281 (16)0.0259 (15)0.0047 (12)−0.0083 (12)−0.0073 (13)
C390.0329 (17)0.0253 (16)0.0330 (17)0.0047 (13)0.0000 (14)−0.0117 (13)
C40A0.0274 (16)0.0249 (15)0.0272 (16)0.0059 (12)−0.0087 (13)−0.0109 (13)
C400.0318 (17)0.0270 (16)0.0302 (16)0.0010 (13)−0.0010 (13)−0.0094 (13)
C3110.039 (2)0.0181 (16)0.047 (2)0.0015 (13)−0.0045 (16)−0.0055 (14)
C3120.077 (3)0.075 (3)0.087 (3)0.045 (2)−0.056 (2)−0.058 (2)
C3130.055 (2)0.037 (2)0.142 (4)0.0200 (18)−0.061 (3)−0.039 (2)
C3140.0421 (19)0.0372 (18)0.049 (2)0.0082 (14)−0.0263 (16)−0.0179 (16)
C3150.049 (2)0.0277 (18)0.049 (2)−0.0077 (15)−0.0050 (17)−0.0097 (15)
C3160.082 (3)0.036 (2)0.041 (2)0.0088 (18)−0.0267 (19)−0.0034 (16)
O40.0583 (15)0.0266 (12)0.0436 (14)0.0055 (11)−0.0105 (13)0.0013 (10)
C410.0371 (18)0.0245 (16)0.0375 (18)0.0056 (13)−0.0079 (14)−0.0141 (14)
C420.049 (2)0.0264 (17)0.065 (2)0.0059 (15)−0.0290 (18)−0.0201 (16)
C430.070 (2)0.0374 (19)0.046 (2)0.0100 (17)−0.0294 (18)−0.0284 (16)
C440.0460 (19)0.0383 (18)0.0364 (18)0.0137 (15)−0.0195 (15)−0.0216 (15)
C44A0.0276 (16)0.0233 (15)0.0272 (16)0.0067 (12)−0.0106 (13)−0.0113 (13)
C44B0.0260 (16)0.0280 (16)0.0239 (15)0.0051 (12)−0.0106 (13)−0.0095 (13)
C450.049 (2)0.041 (2)0.0278 (18)0.0073 (16)−0.0065 (15)−0.0156 (16)
C460.054 (2)0.0368 (19)0.0243 (17)0.0050 (16)−0.0043 (16)−0.0014 (15)
C470.0353 (18)0.0238 (16)0.0343 (18)0.0059 (13)−0.0098 (15)−0.0005 (14)
C480.0247 (15)0.0278 (17)0.0316 (17)0.0053 (12)−0.0075 (13)−0.0115 (14)
C48A0.0213 (14)0.0253 (15)0.0271 (15)0.0016 (12)−0.0102 (12)−0.0069 (12)
C490.0402 (18)0.0253 (16)0.0243 (15)0.0042 (13)−0.0101 (13)−0.0101 (12)
C500.0445 (19)0.0248 (16)0.0234 (15)0.0066 (13)−0.0119 (14)−0.0078 (12)
C50A0.0303 (16)0.0240 (15)0.0307 (16)0.0082 (12)−0.0114 (13)−0.0140 (13)
C4110.0422 (19)0.0222 (16)0.0370 (18)0.0044 (13)−0.0106 (15)−0.0121 (13)
C4120.0348 (19)0.044 (2)0.068 (2)0.0086 (15)−0.0116 (17)−0.0356 (18)
C4130.056 (2)0.047 (2)0.076 (3)0.0144 (18)−0.037 (2)−0.033 (2)
C4140.0292 (17)0.0363 (17)0.0450 (19)0.0095 (13)−0.0147 (14)−0.0169 (15)
C4150.068 (2)0.0279 (18)0.043 (2)0.0154 (16)−0.0241 (18)−0.0126 (15)
C4160.053 (2)0.0322 (19)0.064 (3)−0.0053 (16)0.0056 (19)−0.0148 (18)
Geometric parameters (Å, °) top
O1—C71.384 (3)O3—C371.378 (4)
O1—H10.8400O3—H30.8400
C1—C21.524 (4)C31—C321.528 (4)
C1—C151.532 (4)C31—C3161.530 (4)
C1—C161.543 (4)C31—C3151.544 (4)
C1—C10A1.559 (4)C31—C40A1.553 (4)
C2—C31.512 (4)C32—C331.501 (4)
C2—H2A0.9900C32—H32A0.9900
C2—H2B0.9900C32—H32B0.9900
C3—C41.526 (4)C33—C341.527 (4)
C3—H3A0.9900C33—H33A0.9900
C3—H3B0.9900C33—H33B0.9900
C4—C4A1.538 (4)C34—C34A1.537 (4)
C4—H4A0.9900C34—H34A0.9900
C4—H4B0.9900C34—H34B0.9900
C4A—C141.533 (4)C34A—C34B1.537 (4)
C4A—C4B1.537 (4)C34A—C3141.541 (4)
C4A—C10A1.547 (4)C34A—C40A1.545 (4)
C4B—C51.385 (4)C34B—C351.387 (4)
C4B—C8A1.395 (4)C34B—C38A1.398 (4)
C5—C61.363 (4)C35—C361.369 (4)
C5—H50.9500C35—H350.9500
C6—C71.369 (4)C36—C371.367 (5)
C6—H60.9500C36—H360.9500
C7—C81.394 (4)C37—C381.382 (4)
C8—C8A1.406 (4)C38—C38A1.409 (4)
C8—C111.521 (4)C38—C3111.523 (4)
C8A—C91.511 (4)C38A—C391.517 (4)
C9—C101.526 (4)C39—C401.528 (4)
C9—H9A0.9900C39—H39A0.9900
C9—H9B0.9900C39—H39B0.9900
C10—C10A1.517 (4)C40A—C401.524 (4)
C10—H10B0.9900C40A—H40A1.0000
C10—H10C0.9900C40—H40B0.9900
C10A—H10A1.0000C40—H40C0.9900
C11—C121.518 (4)C311—C3121.499 (5)
C11—C131.522 (4)C311—C3131.522 (4)
C11—H111.0000C311—H3111.0000
C12—H12A0.9800C312—H12G0.9800
C12—H12B0.9800C312—H12H0.9800
C12—H12C0.9800C312—H12I0.9800
C13—H13A0.9800C313—H13G0.9800
C13—H13B0.9800C313—H13H0.9800
C13—H13C0.9800C313—H13I0.9800
C14—H14A0.9800C314—H14G0.9800
C14—H14B0.9800C314—H14H0.9800
C14—H14C0.9800C314—H14I0.9800
C15—H15A0.9800C315—H15G0.9800
C15—H15B0.9800C315—H15H0.9800
C15—H15C0.9800C315—H15I0.9800
C16—H16A0.9800C316—H16G0.9800
C16—H16B0.9800C316—H16H0.9800
C16—H16C0.9800C316—H16I0.9800
O2—C271.384 (3)O4—C471.394 (3)
O2—H20.8400O4—H40.8400
C21—C221.532 (4)C41—C4151.526 (4)
C21—C2161.534 (4)C41—C421.531 (4)
C21—C2151.550 (4)C41—C4161.535 (4)
C21—C30A1.557 (4)C41—C50A1.557 (4)
C22—C231.507 (4)C42—C431.518 (5)
C22—H22A0.9900C42—H42A0.9900
C22—H22B0.9900C42—H42B0.9900
C23—C241.527 (4)C43—C441.523 (4)
C23—H23A0.9900C43—H43A0.9900
C23—H23B0.9900C43—H43B0.9900
C24—C24A1.544 (4)C44—C44A1.532 (4)
C24—H24A0.9900C44—H44A0.9900
C24—H24B0.9900C44—H44B0.9900
C24A—C24B1.535 (4)C44A—C44B1.535 (4)
C24A—C2141.541 (4)C44A—C4141.539 (4)
C24A—C30A1.549 (4)C44A—C50A1.543 (4)
C24B—C251.393 (4)C44B—C451.387 (4)
C24B—C28A1.403 (4)C44B—C48A1.400 (4)
C25—C261.364 (4)C45—C461.381 (4)
C25—H250.9500C45—H450.9500
C26—C271.370 (4)C46—C471.362 (4)
C26—H260.9500C46—H460.9500
C27—C281.378 (4)C47—C481.382 (4)
C28—C28A1.414 (4)C48—C48A1.412 (4)
C28—C2111.519 (4)C48—C4111.530 (4)
C28A—C291.506 (4)C48A—C491.509 (4)
C29—C301.525 (4)C49—C501.517 (4)
C29—H29A0.9900C49—H49A0.9900
C29—H29B0.9900C49—H49B0.9900
C30—C30A1.527 (4)C50—C50A1.515 (4)
C30—H30B0.9900C50—H50B0.9900
C30—H30C0.9900C50—H50C0.9900
C30A—H30A1.0000C50A—H50A1.0000
C211—C2131.514 (4)C411—C4121.517 (4)
C211—C2121.517 (4)C411—C4131.530 (4)
C211—H2111.0000C411—H4111.0000
C212—H12D0.9800C412—H12J0.9800
C212—H12E0.9800C412—H12K0.9800
C212—H12F0.9800C412—H12L0.9800
C213—H13D0.9800C413—H13J0.9800
C213—H13E0.9800C413—H13K0.9800
C213—H13F0.9800C413—H13L0.9800
C214—H14D0.9800C414—H14J0.9800
C214—H14E0.9800C414—H14K0.9800
C214—H14F0.9800C414—H14L0.9800
C215—H15D0.9800C415—H15J0.9800
C215—H15E0.9800C415—H15K0.9800
C215—H15F0.9800C415—H15L0.9800
C216—H16D0.9800C416—H16J0.9800
C216—H16E0.9800C416—H16K0.9800
C216—H16F0.9800C416—H16L0.9800
C7—O1—H1109.5C37—O3—H3109.5
C2—C1—C15110.6 (2)C32—C31—C316107.3 (3)
C2—C1—C16107.2 (3)C32—C31—C315109.8 (3)
C15—C1—C16107.0 (3)C316—C31—C315107.6 (3)
C2—C1—C10A108.4 (2)C32—C31—C40A108.6 (2)
C15—C1—C10A114.7 (2)C316—C31—C40A108.5 (2)
C16—C1—C10A108.8 (2)C315—C31—C40A114.8 (2)
C3—C2—C1113.4 (2)C33—C32—C31113.9 (3)
C3—C2—H2A108.9C33—C32—H32A108.8
C1—C2—H2A108.9C31—C32—H32A108.8
C3—C2—H2B108.9C33—C32—H32B108.8
C1—C2—H2B108.9C31—C32—H32B108.8
H2A—C2—H2B107.7H32A—C32—H32B107.7
C2—C3—C4111.3 (2)C32—C33—C34110.5 (3)
C2—C3—H3A109.4C32—C33—H33A109.6
C4—C3—H3A109.4C34—C33—H33A109.6
C2—C3—H3B109.4C32—C33—H33B109.6
C4—C3—H3B109.4C34—C33—H33B109.6
H3A—C3—H3B108.0H33A—C33—H33B108.1
C3—C4—C4A112.6 (2)C33—C34—C34A112.1 (2)
C3—C4—H4A109.1C33—C34—H34A109.2
C4A—C4—H4A109.1C34A—C34—H34A109.2
C3—C4—H4B109.1C33—C34—H34B109.2
C4A—C4—H4B109.1C34A—C34—H34B109.2
H4A—C4—H4B107.8H34A—C34—H34B107.9
C14—C4A—C4B107.0 (2)C34B—C34A—C34110.9 (2)
C14—C4A—C4109.1 (2)C34B—C34A—C314106.3 (2)
C4B—C4A—C4110.2 (2)C34—C34A—C314108.9 (2)
C14—C4A—C10A114.9 (2)C34B—C34A—C40A107.8 (2)
C4B—C4A—C10A107.8 (2)C34—C34A—C40A107.9 (2)
C4—C4A—C10A107.8 (2)C314—C34A—C40A115.0 (2)
C5—C4B—C8A117.9 (3)C35—C34B—C38A118.2 (3)
C5—C4B—C4A118.7 (2)C35—C34B—C34A119.6 (3)
C8A—C4B—C4A123.4 (2)C38A—C34B—C34A122.2 (2)
C6—C5—C4B121.9 (3)C36—C35—C34B121.1 (3)
C6—C5—H5119.0C36—C35—H35119.5
C4B—C5—H5119.0C34B—C35—H35119.5
C5—C6—C7119.9 (3)C37—C36—C35120.5 (3)
C5—C6—H6120.0C37—C36—H36119.7
C7—C6—H6120.0C35—C36—H36119.7
C6—C7—O1120.7 (3)C36—C37—O3121.1 (3)
C6—C7—C8121.1 (3)C36—C37—C38121.1 (3)
O1—C7—C8118.1 (3)O3—C37—C38117.8 (3)
C7—C8—C8A117.9 (3)C37—C38—C38A118.2 (3)
C7—C8—C11120.3 (3)C37—C38—C311120.6 (3)
C8A—C8—C11121.9 (3)C38A—C38—C311121.2 (3)
C4B—C8A—C8121.1 (2)C34B—C38A—C38120.9 (3)
C4B—C8A—C9120.6 (2)C34B—C38A—C39120.6 (2)
C8—C8A—C9118.3 (2)C38—C38A—C39118.5 (3)
C8A—C9—C10114.2 (2)C38A—C39—C40115.6 (2)
C8A—C9—H9A108.7C38A—C39—H39A108.4
C10—C9—H9A108.7C40—C39—H39A108.4
C8A—C9—H9B108.7C38A—C39—H39B108.4
C10—C9—H9B108.7C40—C39—H39B108.4
H9A—C9—H9B107.6H39A—C39—H39B107.4
C10A—C10—C9109.5 (2)C40—C40A—C34A108.8 (2)
C10A—C10—H10B109.8C40—C40A—C31113.1 (2)
C9—C10—H10B109.8C34A—C40A—C31118.1 (2)
C10A—C10—H10C109.8C40—C40A—H40A105.2
C9—C10—H10C109.8C34A—C40A—H40A105.2
H10B—C10—H10C108.2C31—C40A—H40A105.2
C10—C10A—C4A109.0 (2)C40A—C40—C39110.7 (2)
C10—C10A—C1115.4 (2)C40A—C40—H40B109.5
C4A—C10A—C1116.9 (2)C39—C40—H40B109.5
C10—C10A—H10A104.7C40A—C40—H40C109.5
C4A—C10A—H10A104.7C39—C40—H40C109.5
C1—C10A—H10A104.7H40B—C40—H40C108.1
C12—C11—C8113.4 (3)C312—C311—C313110.1 (3)
C12—C11—C13109.8 (3)C312—C311—C38112.7 (3)
C8—C11—C13112.9 (3)C313—C311—C38114.3 (3)
C12—C11—H11106.8C312—C311—H311106.4
C8—C11—H11106.8C313—C311—H311106.4
C13—C11—H11106.8C38—C311—H311106.4
C11—C12—H12A109.5C311—C312—H12G109.5
C11—C12—H12B109.5C311—C312—H12H109.5
H12A—C12—H12B109.5H12G—C312—H12H109.5
C11—C12—H12C109.5C311—C312—H12I109.5
H12A—C12—H12C109.5H12G—C312—H12I109.5
H12B—C12—H12C109.5H12H—C312—H12I109.5
C11—C13—H13A109.5C311—C313—H13G109.5
C11—C13—H13B109.5C311—C313—H13H109.5
H13A—C13—H13B109.5H13G—C313—H13H109.5
C11—C13—H13C109.5C311—C313—H13I109.5
H13A—C13—H13C109.5H13G—C313—H13I109.5
H13B—C13—H13C109.5H13H—C313—H13I109.5
C4A—C14—H14A109.5C34A—C314—H14G109.5
C4A—C14—H14B109.5C34A—C314—H14H109.5
H14A—C14—H14B109.5H14G—C314—H14H109.5
C4A—C14—H14C109.5C34A—C314—H14I109.5
H14A—C14—H14C109.5H14G—C314—H14I109.5
H14B—C14—H14C109.5H14H—C314—H14I109.5
C1—C15—H15A109.5C31—C315—H15G109.5
C1—C15—H15B109.5C31—C315—H15H109.5
H15A—C15—H15B109.5H15G—C315—H15H109.5
C1—C15—H15C109.5C31—C315—H15I109.5
H15A—C15—H15C109.5H15G—C315—H15I109.5
H15B—C15—H15C109.5H15H—C315—H15I109.5
C1—C16—H16A109.5C31—C316—H16G109.5
C1—C16—H16B109.5C31—C316—H16H109.5
H16A—C16—H16B109.5H16G—C316—H16H109.5
C1—C16—H16C109.5C31—C316—H16I109.5
H16A—C16—H16C109.5H16G—C316—H16I109.5
H16B—C16—H16C109.5H16H—C316—H16I109.5
C27—O2—H2109.5C47—O4—H4109.5
C22—C21—C216107.1 (2)C415—C41—C42110.9 (2)
C22—C21—C215111.1 (3)C415—C41—C416107.8 (3)
C216—C21—C215106.9 (3)C42—C41—C416106.7 (3)
C22—C21—C30A108.3 (2)C415—C41—C50A114.3 (3)
C216—C21—C30A108.9 (2)C42—C41—C50A108.3 (2)
C215—C21—C30A114.3 (2)C416—C41—C50A108.6 (2)
C23—C22—C21113.6 (2)C43—C42—C41113.8 (3)
C23—C22—H22A108.9C43—C42—H42A108.8
C21—C22—H22A108.9C41—C42—H42A108.8
C23—C22—H22B108.9C43—C42—H42B108.8
C21—C22—H22B108.9C41—C42—H42B108.8
H22A—C22—H22B107.7H42A—C42—H42B107.7
C22—C23—C24111.2 (3)C42—C43—C44110.8 (3)
C22—C23—H23A109.4C42—C43—H43A109.5
C24—C23—H23A109.4C44—C43—H43A109.5
C22—C23—H23B109.4C42—C43—H43B109.5
C24—C23—H23B109.4C44—C43—H43B109.5
H23A—C23—H23B108.0H43A—C43—H43B108.1
C23—C24—C24A111.8 (2)C43—C44—C44A112.0 (2)
C23—C24—H24A109.3C43—C44—H44A109.2
C24A—C24—H24A109.3C44A—C44—H44A109.2
C23—C24—H24B109.3C43—C44—H44B109.2
C24A—C24—H24B109.3C44A—C44—H44B109.2
H24A—C24—H24B107.9H44A—C44—H44B107.9
C24B—C24A—C214107.2 (2)C44—C44A—C44B110.5 (2)
C24B—C24A—C24110.5 (2)C44—C44A—C414108.1 (2)
C214—C24A—C24108.5 (2)C44B—C44A—C414106.1 (2)
C24B—C24A—C30A107.4 (2)C44—C44A—C50A108.9 (2)
C214—C24A—C30A115.1 (2)C44B—C44A—C50A107.9 (2)
C24—C24A—C30A108.1 (2)C414—C44A—C50A115.3 (2)
C25—C24B—C28A117.9 (3)C45—C44B—C48A117.9 (3)
C25—C24B—C24A119.4 (3)C45—C44B—C44A119.5 (2)
C28A—C24B—C24A122.7 (2)C48A—C44B—C44A122.5 (2)
C26—C25—C24B121.6 (3)C46—C45—C44B121.9 (3)
C26—C25—H25119.2C46—C45—H45119.0
C24B—C25—H25119.2C44B—C45—H45119.0
C25—C26—C27120.0 (3)C47—C46—C45119.2 (3)
C25—C26—H26120.0C47—C46—H46120.4
C27—C26—H26120.0C45—C46—H46120.4
C26—C27—C28121.9 (3)C46—C47—C48122.1 (3)
C26—C27—O2120.1 (3)C46—C47—O4119.5 (3)
C28—C27—O2118.0 (3)C48—C47—O4118.4 (3)
C27—C28—C28A117.9 (3)C47—C48—C48A118.1 (3)
C27—C28—C211121.0 (3)C47—C48—C411120.2 (3)
C28A—C28—C211121.1 (2)C48A—C48—C411121.6 (2)
C24B—C28A—C28120.8 (2)C44B—C48A—C48120.6 (2)
C24B—C28A—C29120.7 (2)C44B—C48A—C49120.8 (2)
C28—C28A—C29118.5 (2)C48—C48A—C49118.5 (2)
C28A—C29—C30115.3 (2)C48A—C49—C50114.7 (2)
C28A—C29—H29A108.5C48A—C49—H49A108.6
C30—C29—H29A108.5C50—C49—H49A108.6
C28A—C29—H29B108.5C48A—C49—H49B108.6
C30—C29—H29B108.5C50—C49—H49B108.6
H29A—C29—H29B107.5H49A—C49—H49B107.6
C29—C30—C30A109.3 (2)C50A—C50—C49110.4 (2)
C29—C30—H30B109.8C50A—C50—H50B109.6
C30A—C30—H30B109.8C49—C50—H50B109.6
C29—C30—H30C109.8C50A—C50—H50C109.6
C30A—C30—H30C109.8C49—C50—H50C109.6
H30B—C30—H30C108.3H50B—C50—H50C108.1
C30—C30A—C24A109.0 (2)C50—C50A—C44A108.9 (2)
C30—C30A—C21113.8 (2)C50—C50A—C41114.3 (2)
C24A—C30A—C21117.8 (2)C44A—C50A—C41117.4 (2)
C30—C30A—H30A105.0C50—C50A—H50A105.0
C24A—C30A—H30A105.0C44A—C50A—H50A105.0
C21—C30A—H30A105.0C41—C50A—H50A105.0
C213—C211—C212110.1 (2)C412—C411—C48112.6 (3)
C213—C211—C28113.4 (2)C412—C411—C413110.3 (3)
C212—C211—C28112.7 (2)C48—C411—C413112.6 (3)
C213—C211—H211106.7C412—C411—H411107.0
C212—C211—H211106.7C48—C411—H411107.0
C28—C211—H211106.7C413—C411—H411107.0
C211—C212—H12D109.5C411—C412—H12J109.5
C211—C212—H12E109.5C411—C412—H12K109.5
H12D—C212—H12E109.5H12J—C412—H12K109.5
C211—C212—H12F109.5C411—C412—H12L109.5
H12D—C212—H12F109.5H12J—C412—H12L109.5
H12E—C212—H12F109.5H12K—C412—H12L109.5
C211—C213—H13D109.5C411—C413—H13J109.5
C211—C213—H13E109.5C411—C413—H13K109.5
H13D—C213—H13E109.5H13J—C413—H13K109.5
C211—C213—H13F109.5C411—C413—H13L109.5
H13D—C213—H13F109.5H13J—C413—H13L109.5
H13E—C213—H13F109.5H13K—C413—H13L109.5
C24A—C214—H14D109.5C44A—C414—H14J109.5
C24A—C214—H14E109.5C44A—C414—H14K109.5
H14D—C214—H14E109.5H14J—C414—H14K109.5
C24A—C214—H14F109.5C44A—C414—H14L109.5
H14D—C214—H14F109.5H14J—C414—H14L109.5
H14E—C214—H14F109.5H14K—C414—H14L109.5
C21—C215—H15D109.5C41—C415—H15J109.5
C21—C215—H15E109.5C41—C415—H15K109.5
H15D—C215—H15E109.5H15J—C415—H15K109.5
C21—C215—H15F109.5C41—C415—H15L109.5
H15D—C215—H15F109.5H15J—C415—H15L109.5
H15E—C215—H15F109.5H15K—C415—H15L109.5
C21—C216—H16D109.5C41—C416—H16J109.5
C21—C216—H16E109.5C41—C416—H16K109.5
H16D—C216—H16E109.5H16J—C416—H16K109.5
C21—C216—H16F109.5C41—C416—H16L109.5
H16D—C216—H16F109.5H16J—C416—H16L109.5
H16E—C216—H16F109.5H16K—C416—H16L109.5
Table 1
Puckering amplitudes (Cremer & Pople, 1975) for the unsaturated six-membered rings within the four independent molecules top
C1/C2/C3/C4/C4a/C10aC4a/C4b/C8a/C9/C10/C10a
MoleculeQ (Å)θ (°)φ (°)Q (Å)θ (°)φ (°)
10.553 (3)4.2 (3)140 (5)0.553 (3)52.3 (3)284.7 (4)
20.550 (3)6.8 (3)141 (3)0.555 (3)51.9 (3)289.8 (4)
30.548 (4)7.9 (4)142 (3)0.543 (3)51.0 (3)296.2 (4)
40.547 (4)6.6 (4)139 (3)0.543 (3)51.0 (3)289.2 (4)
Table 2
Structure matching between the four independent molecules top
A is the structure match between molecules 1 and 2, B is that between molecules 1 and 3, C is that between molecules 1 and 4, D is that between molecules 2 and 3, E is that between molecules 2 and 4 and F is that between molecules 3 and 4.
Overlayr.m.s. position (Å)r.m.s. bond (Å)r.m.s. torsion (°)
A0.07070.00742.1002
B0.17540.00745.0807
C0.09170.00732.7283
D0.11740.00633.479
E0.05050.00931.5649
F0.08960.00912.6273
references
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