supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, o219    [ doi:10.1107/S1600536808042189 ]

3,3,6,6,9,9-Hexamethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione

X. Xie, Y. Zhang, J. Liang and Y. Zhu

Abstract top

The title compound, C19H26O3, was synthesized directly from the condensation of 5,5-dimethylcyclohexane-1,3-dione with malononitrile catalysed by palladium chloride: there are two molecules in the asymmetric unit.

Comment top

The title compound, 3,4,5,6,7,9-hexahydro-3,3,6,6,9,9-hexamethyl-1H-xanthene-1,8(2H)-dione, was reported in 1946 (Hirsjarvi,1946; Sellstedt,1972). In our experiment, The reaction between 5,5-dimethyl-1,3-cyclohexanedione with malononitrile afforded 3,4,5,6,7,9-hexahydro-3,3,6,6,9,9-hexamethyl-1H-xanthene-1,8(2H)-dione in excellent yield in the presence of palladium chloride at 353 K for 5 h. (Fig. 1). The single crystals of the compound were obtained from ethanol as colourless block-shaped and crystallized in the space group P 21/c. There are no unusual bond lengths and angles in the compound. The O1—C11—C10—C1 torsion angle of 171.8 together with the O1—C12—C13—C8 torsion angle of 173.1 comfirms the bonds around the O1 atom are not coplanar. The O2—C8—C13—C12 torsion angle of 174.5 together with normal O2=C8 and C12=C13 bond lengths and the O3—C1—C10—C11 torsion angle of 177.0 together with normal O3=C1 and C10=C11 bond lengths indicate the presence of conjugation between these two double bonds. The C7—C8—C13—C12 torsion angle of -6.7 (3) together with the C5—C12—C13—C8 torsion angle of -5.9 (3) and the C2—C1—C10—C11 torsion angle of -0.3 (3) together with the C1—C10—C11—C4 torsion angle of -8.0 (3) exhibited the two rings are in a half-chair or envelope conformation. The C16 and C17 methyls were on the opposite to the C18 and C19 methyls, together with the C35 and C36 methyls were on the opposite to the C37 and C38 methyls,these confirmed the molecules conformation were trans. X-ray single-crystal diffraction reveals that there are crystallographically two independent mirror-image structures in the asymmetric unit.

Related literature top

For previous reports of the title compound, see: Hirsjarvi (1946); Sellstedt (1972).

Experimental top

A mixture of 5,5-dimethyl-1,3-cyclohexanedione (10 mmol), malononitrile (10 mmol), and palladium chloride (0.01 mmol) was refluxed in acetonitrile(12 ml) under 353 K for 5 h. After being cooled to room temperature, the reaction mixture was poured into water. The residue was filtered through a silica pad, washed twice with water, and then dried under vacuum to yield the product in yield 92%. The crystalloid product was dissolved in ethanol. Colourless block-shaped single crystals suitable for X-ray structure analysis were obtained by slow evaporation from ethanol at room temperature.

Refinement top

The H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.93–0.97 Å, and Uiso = 1.2–1.5 Ueq(parent atom).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Palladium-catalyzed Synthesis of 3,4,5,6,7,9-hexahydro-3,3,6,6,9,9-hexamethyl-1H-xanthene-1,8(2H)-dione.
[Figure 2] Fig. 2. View of the title compound showing the atom-labelling scheme. Ellipsoids are drawn at the 50% probability level.
3,3,6,6,9,9-Hexamethyl-2,3,4,5,6,7,8,9-octahydro-1H-xanthene-1,8-dione top
Crystal data top
C19H26O3F(000) = 1312.0
Mr = 302.40Dx = 1.191 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3174 reflections
a = 12.1688 (19) Åθ = 2.5–21.9°
b = 11.7055 (18) ŵ = 0.08 mm−1
c = 24.365 (4) ÅT = 298 K
β = 103.595 (2)°Block, colourless
V = 3373.4 (9) Å30.30 × 0.20 × 0.15 mm
Z = 8
Data collection top
Bruker APEXII area-detector
diffractometer		7856 independent reflections
Radiation source: fine-focus sealed tube4312 reflections with I > 2σ(I)
graphiteRint = 0.042
φ and ω scansθmax = 27.9°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		h = −15→16
Tmin = 0.970, Tmax = 0.981k = −15→15
20408 measured reflectionsl = −28→32
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)] = 0.058H-atom parameters constrained
wR(F2) = 0.165 w = 1/[σ2(Fo2) + (0.0568P)2 + 0.7487P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
7856 reflectionsΔρmax = 0.22 e Å−3
410 parametersΔρmin = −0.16 e Å−3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0012 (4)
Crystal data top
C19H26O3V = 3373.4 (9) Å3
Mr = 302.40Z = 8
Monoclinic, P21/cMo Kα radiation
a = 12.1688 (19) ŵ = 0.08 mm−1
b = 11.7055 (18) ÅT = 298 K
c = 24.365 (4) Å0.30 × 0.20 × 0.15 mm
β = 103.595 (2)°
Data collection top
Bruker APEXII area-detector
diffractometer		7856 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)		4312 reflections with I > 2σ(I)
Tmin = 0.970, Tmax = 0.981Rint = 0.042
20408 measured reflectionsθmax = 27.9°
Refinement top
R[F2 > 2σ(F2)] = 0.058H-atom parameters constrained
wR(F2) = 0.165Δρmax = 0.22 e Å−3
S = 1.05Δρmin = −0.16 e Å−3
7856 reflectionsAbsolute structure: ?
410 parametersFlack parameter: ?
0 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
C10.46830 (19)0.7292 (2)0.14266 (11)0.0522 (6)
C20.4840 (2)0.8027 (2)0.09431 (11)0.0595 (7)
H2A0.43960.87180.09350.071*
H2B0.45450.76210.05930.071*
C30.60593 (19)0.83619 (19)0.09702 (9)0.0467 (6)
C40.64836 (19)0.89530 (18)0.15383 (9)0.0435 (5)
H4A0.72970.90450.16090.052*
H4B0.61510.97090.15210.052*
C50.76147 (19)0.8708 (2)0.34933 (9)0.0458 (5)
H5A0.75220.95290.34540.055*
H5B0.83880.85270.34830.055*
C60.74147 (19)0.8344 (2)0.40666 (9)0.0457 (5)
C70.7276 (2)0.7050 (2)0.40465 (10)0.0546 (6)
H7A0.79770.67050.40060.066*
H7B0.71350.67900.44020.066*
C80.6324 (2)0.6646 (2)0.35692 (11)0.0514 (6)
C90.53208 (17)0.67934 (18)0.25027 (10)0.0428 (5)
C100.54395 (17)0.74911 (18)0.19899 (9)0.0408 (5)
C110.62087 (17)0.83152 (17)0.20159 (9)0.0369 (5)
C120.68309 (17)0.81411 (18)0.30053 (9)0.0379 (5)
C130.61809 (17)0.72250 (17)0.30206 (9)0.0404 (5)
C140.41224 (19)0.6936 (2)0.26027 (12)0.0615 (7)
H14A0.39570.77340.26260.092*
H14B0.40840.65660.29490.092*
H14C0.35800.65970.22950.092*
C150.5559 (2)0.55184 (19)0.23925 (12)0.0607 (7)
H15A0.50400.52650.20540.091*
H15B0.54630.50630.27060.091*
H15C0.63200.54400.23500.091*
C160.8430 (2)0.8683 (2)0.45361 (10)0.0656 (7)
H16A0.83060.84460.48940.098*
H16B0.85250.94970.45360.098*
H16C0.90980.83200.44740.098*
C170.6351 (2)0.8909 (2)0.41695 (10)0.0584 (7)
H17A0.57180.87230.38650.088*
H17B0.64530.97230.41890.088*
H17C0.62130.86370.45190.088*
C180.6127 (2)0.9184 (2)0.04973 (10)0.0707 (8)
H18A0.58370.88200.01400.106*
H18B0.69000.94000.05290.106*
H18C0.56860.98530.05250.106*
C190.6760 (2)0.7294 (2)0.09236 (11)0.0636 (7)
H19A0.67390.67840.12290.095*
H19B0.75280.75120.09410.095*
H19C0.64520.69180.05710.095*
C200.0368 (2)0.67067 (19)0.14075 (11)0.0510 (6)
C210.0876 (2)0.7132 (2)0.09394 (10)0.0540 (6)
H21A0.04150.68720.05810.065*
H21B0.16240.68040.09840.065*
C220.0969 (2)0.84297 (19)0.09278 (9)0.0479 (6)
C230.16921 (19)0.87919 (19)0.15058 (9)0.0465 (6)
H23A0.24800.86350.15180.056*
H23B0.16140.96090.15500.056*
C240.23595 (19)0.89884 (18)0.34621 (9)0.0430 (5)
H24A0.20420.97450.34750.052*
H24B0.31160.90770.34040.052*
C250.24293 (19)0.83916 (18)0.40265 (9)0.0446 (5)
C260.1227 (2)0.8058 (2)0.40333 (10)0.0545 (6)
H26A0.12360.76650.43850.065*
H26B0.07820.87480.40260.065*
C270.06587 (19)0.7305 (2)0.35496 (10)0.0488 (6)
C280.03382 (17)0.68151 (17)0.24750 (10)0.0422 (5)
C290.07195 (17)0.72731 (17)0.19632 (9)0.0406 (5)
C300.13723 (17)0.81928 (17)0.19853 (9)0.0383 (5)
C310.16534 (17)0.83464 (17)0.29759 (9)0.0360 (5)
C320.09154 (17)0.75143 (17)0.29926 (9)0.0394 (5)
C33−0.09545 (18)0.6935 (2)0.23688 (11)0.0588 (7)
H33A−0.12090.65840.26730.088*
H33B−0.13060.65660.20200.088*
H33C−0.11540.77300.23470.088*
C340.0699 (2)0.55488 (18)0.25848 (11)0.0587 (7)
H34A0.15020.54850.26300.088*
H34B0.03200.50900.22700.088*
H34C0.04990.52870.29220.088*
C350.2903 (3)0.9214 (2)0.45098 (10)0.0679 (8)
H35A0.24270.98770.44760.102*
H35B0.36530.94420.44930.102*
H35C0.29280.88420.48640.102*
C360.3184 (2)0.7331 (2)0.40887 (11)0.0617 (7)
H36A0.31890.69610.44410.093*
H36B0.39390.75540.40810.093*
H36C0.28950.68140.37830.093*
C370.1548 (3)0.8809 (3)0.04655 (10)0.0747 (9)
H37A0.22460.84000.05040.112*
H37B0.17000.96140.05000.112*
H37C0.10630.86510.01020.112*
C38−0.0209 (2)0.8958 (2)0.08221 (11)0.0671 (8)
H38A−0.06630.86800.04710.101*
H38B−0.01500.97750.08050.101*
H38C−0.05550.87530.11240.101*
O10.68792 (12)0.86994 (12)0.25180 (6)0.0404 (4)
O20.57242 (17)0.58530 (16)0.36467 (8)0.0799 (6)
O30.39140 (15)0.65934 (16)0.13512 (8)0.0762 (6)
O40.18654 (12)0.87463 (11)0.24804 (6)0.0397 (3)
O5−0.00287 (15)0.65889 (16)0.36175 (8)0.0731 (6)
O6−0.02878 (17)0.58965 (16)0.13253 (8)0.0789 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0433 (13)0.0515 (14)0.0581 (16)0.0010 (11)0.0050 (12)−0.0166 (12)
C20.0574 (16)0.0614 (16)0.0499 (15)0.0057 (12)−0.0073 (12)−0.0104 (13)
C30.0528 (14)0.0484 (13)0.0344 (12)0.0088 (11)0.0015 (10)−0.0056 (10)
C40.0479 (13)0.0440 (13)0.0369 (12)−0.0008 (10)0.0066 (10)−0.0031 (10)
C50.0502 (13)0.0510 (13)0.0354 (12)−0.0079 (11)0.0082 (10)−0.0010 (10)
C60.0504 (13)0.0521 (14)0.0348 (12)0.0028 (11)0.0104 (10)0.0053 (10)
C70.0612 (15)0.0549 (15)0.0500 (15)0.0085 (12)0.0176 (12)0.0129 (12)
C80.0574 (15)0.0407 (13)0.0609 (16)0.0021 (11)0.0235 (13)0.0060 (12)
C90.0393 (12)0.0371 (11)0.0535 (14)−0.0044 (9)0.0140 (11)−0.0071 (10)
C100.0368 (11)0.0378 (12)0.0467 (14)−0.0008 (9)0.0078 (10)−0.0111 (10)
C110.0353 (11)0.0389 (11)0.0351 (12)0.0021 (9)0.0053 (9)−0.0082 (9)
C120.0418 (12)0.0390 (12)0.0350 (12)0.0011 (9)0.0136 (9)−0.0007 (9)
C130.0422 (12)0.0349 (11)0.0468 (14)0.0015 (9)0.0157 (10)0.0002 (10)
C140.0454 (14)0.0652 (17)0.0780 (19)−0.0044 (12)0.0229 (13)−0.0024 (14)
C150.0700 (17)0.0360 (13)0.0767 (19)−0.0017 (12)0.0187 (14)−0.0094 (13)
C160.0697 (18)0.086 (2)0.0382 (14)−0.0047 (15)0.0060 (13)0.0042 (14)
C170.0675 (17)0.0632 (17)0.0479 (15)0.0094 (13)0.0202 (13)−0.0003 (12)
C180.090 (2)0.080 (2)0.0361 (15)0.0091 (16)0.0020 (14)0.0058 (14)
C190.0747 (18)0.0656 (17)0.0505 (16)0.0179 (14)0.0149 (14)−0.0094 (13)
C200.0508 (14)0.0369 (12)0.0601 (16)−0.0020 (11)0.0028 (12)−0.0080 (11)
C210.0586 (15)0.0504 (14)0.0481 (15)0.0023 (12)0.0026 (12)−0.0144 (12)
C220.0593 (15)0.0455 (13)0.0347 (13)−0.0023 (11)0.0028 (11)−0.0064 (10)
C230.0540 (14)0.0470 (13)0.0367 (13)−0.0097 (11)0.0071 (11)−0.0031 (10)
C240.0509 (13)0.0408 (12)0.0376 (12)−0.0035 (10)0.0108 (10)0.0011 (10)
C250.0578 (14)0.0406 (12)0.0355 (12)0.0040 (10)0.0110 (11)0.0043 (10)
C260.0688 (16)0.0521 (15)0.0492 (15)0.0086 (12)0.0272 (13)0.0120 (12)
C270.0480 (13)0.0439 (13)0.0578 (16)0.0043 (11)0.0189 (12)0.0135 (12)
C280.0379 (12)0.0334 (11)0.0535 (14)−0.0015 (9)0.0073 (10)0.0046 (10)
C290.0368 (11)0.0338 (11)0.0483 (14)0.0000 (9)0.0043 (10)−0.0015 (10)
C300.0384 (11)0.0366 (11)0.0377 (12)−0.0017 (9)0.0044 (9)−0.0024 (10)
C310.0394 (11)0.0342 (11)0.0353 (12)0.0035 (9)0.0106 (9)0.0040 (9)
C320.0361 (11)0.0345 (11)0.0484 (14)0.0035 (9)0.0115 (10)0.0072 (10)
C330.0401 (13)0.0623 (16)0.0722 (18)−0.0040 (11)0.0093 (12)0.0045 (14)
C340.0663 (16)0.0340 (12)0.0734 (18)0.0012 (11)0.0113 (14)0.0067 (12)
C350.102 (2)0.0620 (17)0.0390 (15)−0.0051 (15)0.0151 (14)−0.0038 (13)
C360.0672 (17)0.0568 (16)0.0556 (17)0.0152 (13)0.0033 (13)0.0064 (13)
C370.106 (2)0.080 (2)0.0388 (15)−0.0223 (17)0.0170 (15)−0.0121 (14)
C380.0777 (19)0.0567 (16)0.0566 (17)0.0112 (14)−0.0052 (14)−0.0057 (13)
O10.0464 (8)0.0427 (8)0.0314 (8)−0.0093 (7)0.0077 (7)−0.0036 (7)
O20.0988 (15)0.0631 (12)0.0806 (14)−0.0254 (11)0.0266 (12)0.0180 (10)
O30.0629 (12)0.0746 (13)0.0823 (14)−0.0251 (10)−0.0007 (10)−0.0200 (11)
O40.0473 (8)0.0386 (8)0.0323 (8)−0.0099 (6)0.0074 (7)−0.0015 (7)
O50.0756 (13)0.0690 (12)0.0833 (14)−0.0177 (10)0.0358 (11)0.0164 (10)
O60.0907 (14)0.0615 (12)0.0799 (14)−0.0332 (11)0.0106 (11)−0.0219 (10)
Geometric parameters (Å, °) top
C1—O31.224 (3)C20—O61.226 (3)
C1—C101.480 (3)C20—C291.478 (3)
C1—C21.507 (4)C20—C211.504 (3)
C2—C31.521 (3)C21—C221.524 (3)
C2—H2A0.9700C21—H21A0.9700
C2—H2B0.9700C21—H21B0.9700
C3—C181.518 (3)C22—C371.528 (3)
C3—C41.525 (3)C22—C381.527 (3)
C3—C191.532 (3)C22—C231.535 (3)
C4—C111.485 (3)C23—C301.491 (3)
C4—H4A0.9700C23—H23A0.9700
C4—H4B0.9700C23—H23B0.9700
C5—C121.493 (3)C24—C311.493 (3)
C5—C61.533 (3)C24—C251.527 (3)
C5—H5A0.9700C24—H24A0.9700
C5—H5B0.9700C24—H24B0.9700
C6—C71.524 (3)C25—C261.518 (3)
C6—C171.526 (3)C25—C351.526 (3)
C6—C161.526 (3)C25—C361.530 (3)
C7—C81.511 (3)C26—C271.504 (3)
C7—H7A0.9700C26—H26A0.9700
C7—H7B0.9700C26—H26B0.9700
C8—O21.223 (3)C27—O51.223 (3)
C8—C131.472 (3)C27—C321.483 (3)
C9—C131.524 (3)C28—C291.526 (3)
C9—C101.528 (3)C28—C321.529 (3)
C9—C141.543 (3)C28—C331.539 (3)
C9—C151.556 (3)C28—C341.551 (3)
C10—C111.335 (3)C29—C301.332 (3)
C11—O11.377 (2)C30—O41.376 (2)
C12—C131.338 (3)C31—C321.332 (3)
C12—O11.369 (2)C31—O41.375 (2)
C14—H14A0.9600C33—H33A0.9600
C14—H14B0.9600C33—H33B0.9600
C14—H14C0.9600C33—H33C0.9600
C15—H15A0.9600C34—H34A0.9600
C15—H15B0.9600C34—H34B0.9600
C15—H15C0.9600C34—H34C0.9600
C16—H16A0.9600C35—H35A0.9600
C16—H16B0.9600C35—H35B0.9600
C16—H16C0.9600C35—H35C0.9600
C17—H17A0.9600C36—H36A0.9600
C17—H17B0.9600C36—H36B0.9600
C17—H17C0.9600C36—H36C0.9600
C18—H18A0.9600C37—H37A0.9600
C18—H18B0.9600C37—H37B0.9600
C18—H18C0.9600C37—H37C0.9600
C19—H19A0.9600C38—H38A0.9600
C19—H19B0.9600C38—H38B0.9600
C19—H19C0.9600C38—H38C0.9600
O3—C1—C10122.1 (2)O6—C20—C21120.0 (2)
O3—C1—C2119.8 (2)C29—C20—C21117.68 (19)
C10—C1—C2118.0 (2)C20—C21—C22112.91 (19)
C1—C2—C3114.49 (19)C20—C21—H21A109.0
C1—C2—H2A108.6C22—C21—H21A109.0
C3—C2—H2A108.6C20—C21—H21B109.0
C1—C2—H2B108.6C22—C21—H21B109.0
C3—C2—H2B108.6H21A—C21—H21B107.8
H2A—C2—H2B107.6C21—C22—C37110.6 (2)
C18—C3—C4109.5 (2)C21—C22—C38109.7 (2)
C18—C3—C2110.9 (2)C37—C22—C38109.6 (2)
C4—C3—C2105.95 (19)C21—C22—C23106.69 (18)
C18—C3—C19109.3 (2)C37—C22—C23109.4 (2)
C4—C3—C19111.21 (19)C38—C22—C23110.8 (2)
C2—C3—C19110.0 (2)C30—C23—C22112.98 (18)
C11—C4—C3113.11 (18)C30—C23—H23A109.0
C11—C4—H4A109.0C22—C23—H23A109.0
C3—C4—H4A109.0C30—C23—H23B109.0
C11—C4—H4B109.0C22—C23—H23B109.0
C3—C4—H4B109.0H23A—C23—H23B107.8
H4A—C4—H4B107.8C31—C24—C25112.59 (18)
C12—C5—C6113.17 (18)C31—C24—H24A109.1
C12—C5—H5A108.9C25—C24—H24A109.1
C6—C5—H5A108.9C31—C24—H24B109.1
C12—C5—H5B108.9C25—C24—H24B109.1
C6—C5—H5B108.9H24A—C24—H24B107.8
H5A—C5—H5B107.8C26—C25—C35110.2 (2)
C7—C6—C17110.1 (2)C26—C25—C24106.12 (18)
C7—C6—C5106.66 (19)C35—C25—C24109.70 (19)
C17—C6—C5110.60 (19)C26—C25—C36110.35 (19)
C7—C6—C16110.3 (2)C35—C25—C36109.1 (2)
C17—C6—C16109.4 (2)C24—C25—C36111.43 (19)
C5—C6—C16109.68 (19)C27—C26—C25114.16 (19)
C8—C7—C6113.27 (19)C27—C26—H26A108.7
C8—C7—H7A108.9C25—C26—H26A108.7
C6—C7—H7A108.9C27—C26—H26B108.7
C8—C7—H7B108.9C25—C26—H26B108.7
C6—C7—H7B108.9H26A—C26—H26B107.6
H7A—C7—H7B107.7O5—C27—C32122.4 (2)
O2—C8—C13122.8 (2)O5—C27—C26120.0 (2)
O2—C8—C7119.8 (2)C32—C27—C26117.6 (2)
C13—C8—C7117.4 (2)C29—C28—C32108.48 (17)
C13—C9—C10108.75 (17)C29—C28—C33108.99 (18)
C13—C9—C14108.91 (19)C32—C28—C33110.06 (18)
C10—C9—C14110.23 (19)C29—C28—C34110.38 (19)
C13—C9—C15109.97 (19)C32—C28—C34108.23 (18)
C10—C9—C15108.33 (19)C33—C28—C34110.68 (18)
C14—C9—C15110.63 (18)C30—C29—C20116.2 (2)
C11—C10—C1115.7 (2)C30—C29—C28123.0 (2)
C11—C10—C9123.2 (2)C20—C29—C28120.87 (18)
C1—C10—C9121.10 (19)C29—C30—O4123.3 (2)
C10—C11—O1122.7 (2)C29—C30—C23127.7 (2)
C10—C11—C4127.6 (2)O4—C30—C23108.98 (17)
O1—C11—C4109.66 (17)C32—C31—O4122.88 (19)
C13—C12—O1123.57 (19)C32—C31—C24127.6 (2)
C13—C12—C5127.2 (2)O4—C31—C24109.50 (17)
O1—C12—C5109.20 (17)C31—C32—C27115.9 (2)
C12—C13—C8116.7 (2)C31—C32—C28123.3 (2)
C12—C13—C9122.6 (2)C27—C32—C28120.78 (18)
C8—C13—C9120.74 (19)C28—C33—H33A109.5
C9—C14—H14A109.5C28—C33—H33B109.5
C9—C14—H14B109.5H33A—C33—H33B109.5
H14A—C14—H14B109.5C28—C33—H33C109.5
C9—C14—H14C109.5H33A—C33—H33C109.5
H14A—C14—H14C109.5H33B—C33—H33C109.5
H14B—C14—H14C109.5C28—C34—H34A109.5
C9—C15—H15A109.5C28—C34—H34B109.5
C9—C15—H15B109.5H34A—C34—H34B109.5
H15A—C15—H15B109.5C28—C34—H34C109.5
C9—C15—H15C109.5H34A—C34—H34C109.5
H15A—C15—H15C109.5H34B—C34—H34C109.5
H15B—C15—H15C109.5C25—C35—H35A109.5
C6—C16—H16A109.5C25—C35—H35B109.5
C6—C16—H16B109.5H35A—C35—H35B109.5
H16A—C16—H16B109.5C25—C35—H35C109.5
C6—C16—H16C109.5H35A—C35—H35C109.5
H16A—C16—H16C109.5H35B—C35—H35C109.5
H16B—C16—H16C109.5C25—C36—H36A109.5
C6—C17—H17A109.5C25—C36—H36B109.5
C6—C17—H17B109.5H36A—C36—H36B109.5
H17A—C17—H17B109.5C25—C36—H36C109.5
C6—C17—H17C109.5H36A—C36—H36C109.5
H17A—C17—H17C109.5H36B—C36—H36C109.5
H17B—C17—H17C109.5C22—C37—H37A109.5
C3—C18—H18A109.5C22—C37—H37B109.5
C3—C18—H18B109.5H37A—C37—H37B109.5
H18A—C18—H18B109.5C22—C37—H37C109.5
C3—C18—H18C109.5H37A—C37—H37C109.5
H18A—C18—H18C109.5H37B—C37—H37C109.5
H18B—C18—H18C109.5C22—C38—H38A109.5
C3—C19—H19A109.5C22—C38—H38B109.5
C3—C19—H19B109.5H38A—C38—H38B109.5
H19A—C19—H19B109.5C22—C38—H38C109.5
C3—C19—H19C109.5H38A—C38—H38C109.5
H19A—C19—H19C109.5H38B—C38—H38C109.5
H19B—C19—H19C109.5C12—O1—C11118.53 (16)
O6—C20—C29122.3 (2)C31—O4—C30118.45 (16)
O3—C1—C2—C3−148.9 (2)C20—C21—C22—C2358.0 (3)
C10—C1—C2—C334.3 (3)C38—C22—C23—C3074.9 (3)
C1—C2—C3—C18−174.9 (2)C21—C22—C23—C30−44.4 (3)
C1—C2—C3—C4−56.2 (3)C37—C22—C23—C30−164.1 (2)
C1—C2—C3—C1964.1 (3)C31—C24—C25—C26−47.1 (2)
C18—C3—C4—C11166.9 (2)C31—C24—C25—C35−166.0 (2)
C2—C3—C4—C1147.2 (2)C31—C24—C25—C3673.1 (2)
C19—C3—C4—C11−72.1 (3)C35—C25—C26—C27176.28 (19)
C12—C5—C6—C744.7 (3)C24—C25—C26—C2757.6 (2)
C12—C5—C6—C16164.3 (2)C36—C25—C26—C27−63.2 (3)
C12—C5—C6—C17−75.0 (3)C25—C26—C27—O5147.3 (2)
C16—C6—C7—C8−176.7 (2)C25—C26—C27—C32−36.1 (3)
C17—C6—C7—C862.4 (3)O6—C20—C29—C30−175.4 (2)
C5—C6—C7—C8−57.6 (2)C21—C20—C29—C306.6 (3)
C6—C7—C8—O2−140.9 (2)O6—C20—C29—C284.2 (3)
C6—C7—C8—C1340.3 (3)C21—C20—C29—C28−173.7 (2)
O3—C1—C10—C11−177.1 (2)C32—C28—C29—C30−5.1 (3)
C2—C1—C10—C11−0.3 (3)C33—C28—C29—C30114.7 (2)
O3—C1—C10—C92.4 (3)C34—C28—C29—C30−123.5 (2)
C2—C1—C10—C9179.08 (19)C32—C28—C29—C20175.29 (18)
C13—C9—C10—C111.6 (3)C33—C28—C29—C20−64.9 (2)
C14—C9—C10—C11120.9 (2)C34—C28—C29—C2056.8 (3)
C15—C9—C10—C11−117.9 (2)C20—C29—C30—O4−173.07 (18)
C13—C9—C10—C1−177.80 (18)C28—C29—C30—O47.3 (3)
C14—C9—C10—C1−58.5 (3)C20—C29—C30—C237.0 (3)
C15—C9—C10—C162.7 (3)C28—C29—C30—C23−172.6 (2)
C1—C10—C11—O1171.77 (18)C22—C23—C30—C2913.8 (3)
C9—C10—C11—O1−7.6 (3)C22—C23—C30—O4−166.12 (18)
C1—C10—C11—C4−8.0 (3)C25—C24—C31—C3216.4 (3)
C9—C10—C11—C4172.54 (19)C25—C24—C31—O4−163.89 (17)
C3—C4—C11—C10−17.6 (3)O4—C31—C32—C27−171.10 (18)
C3—C4—C11—O1162.54 (17)C24—C31—C32—C278.5 (3)
C6—C5—C12—C13−15.0 (3)O4—C31—C32—C288.0 (3)
C6—C5—C12—O1165.85 (17)C24—C31—C32—C28−172.42 (19)
O1—C12—C13—C8173.11 (18)O5—C27—C32—C31177.8 (2)
C5—C12—C13—C8−5.9 (3)C26—C27—C32—C311.3 (3)
O1—C12—C13—C9−7.5 (3)O5—C27—C32—C28−1.2 (3)
C5—C12—C13—C9173.5 (2)C26—C27—C32—C28−177.77 (19)
O2—C8—C13—C12174.5 (2)C29—C28—C32—C31−2.3 (3)
C7—C8—C13—C12−6.7 (3)C33—C28—C32—C31−121.5 (2)
O2—C8—C13—C9−5.0 (3)C34—C28—C32—C31117.5 (2)
C7—C8—C13—C9173.8 (2)C29—C28—C32—C27176.71 (18)
C10—C9—C13—C125.7 (3)C33—C28—C32—C2757.6 (2)
C14—C9—C13—C12−114.5 (2)C34—C28—C32—C27−63.5 (2)
C15—C9—C13—C12124.2 (2)C13—C12—O1—C111.3 (3)
C10—C9—C13—C8−174.88 (18)C5—C12—O1—C11−179.51 (17)
C14—C9—C13—C865.0 (2)C10—C11—O1—C126.4 (3)
C15—C9—C13—C8−56.4 (3)C4—C11—O1—C12−173.77 (17)
O6—C20—C21—C22141.3 (2)C32—C31—O4—C30−6.1 (3)
C29—C20—C21—C22−40.8 (3)C24—C31—O4—C30174.20 (17)
C20—C21—C22—C38−62.1 (3)C29—C30—O4—C31−1.6 (3)
C20—C21—C22—C37176.9 (2)C23—C30—O4—C31178.31 (17)
Acknowledgements top

The authors thank South China Normal University for financial support.

references
References top

Bruker (2004). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Hirsjarvi, V. P. (1946). Chemica, 23, 108.

Sellstedt, J. H. (1972). J. Org. Chem. 37, 1337–1340.

Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.