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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1362.
Published online 2009 May 23. doi:  10.1107/S1600536809018856
PMCID: PMC2969565

2α-Acet­oxy-5α-methoxy­caryophyll-8(15)-en-3-one

Abstract

The title compound, C18H28O4, crystallizes with two mol­ecules in the asymmetric unit. Both mol­ecules have similar conformations of nine-membered rings, which are trans-fused with cyclo­butane fragments. The puckering amplitudes (q2) of the cyclo­butane rings are 0.2451 (2) and 0.2526 (2) Å.

Related literature

For the biological activity of the title compound, see: Houghton (1984 [triangle]); Yamamoto et al. (1993 [triangle]); Yoshida et al. (1978 [triangle]). For puckering amplitude, see: Cremer & Pople (1975 [triangle]). For a related structure of the carryophyllane type, see: Collado et al. (1997 [triangle]).

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Object name is e-65-o1362-scheme1.jpg

Experimental

Crystal data

  • C18H28O4
  • M r = 308.40
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1362-efi1.jpg
  • a = 9.2924 (19) Å
  • b = 17.858 (4) Å
  • c = 21.451 (4) Å
  • V = 3559.6 (12) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 113 K
  • 0.18 × 0.16 × 0.08 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.986, T max = 0.994
  • 21386 measured reflections
  • 3534 independent reflections
  • 3031 reflections with I > 2σ(I)
  • R int = 0.066

Refinement

  • R[F 2 > 2σ(F 2)] = 0.049
  • wR(F 2) = 0.123
  • S = 1.08
  • 3534 reflections
  • 408 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018856/ya2089sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018856/ya2089Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

The genus Buddleja has widespread use in folk medicine (Houghton, 1984). B. davidii have been reported to have bactericidal and cannabimimetic antiinflammatory properties (Yamamoto et al., 1993; Yoshida et al., 1978). The present paper reports the structure of the title compound, a caryophyllane-type sesquiterpene, isolated from the bark of Buddleja davidii Franch.

The asymmetric unit contains two chemically identical and conformationally similar molecules (Fig. 1). The 9-membered ring is trans-fused with cyclobutane; the Cremer & Pople puckering amplitudes (q2) of the cyclobutane rings are 0.2451 (2) and 0.2526 (2)Å (Cremer & Pople, 1975).

Experimental

Air-dried roots (2 kg) were extracted with 95% EtOH. The extract was suspended in water and extracted with petroleum ether, EtOAc and n-BuOH, respectively. The EtOAc extract was evaporated to dryness under reduced pressure. The residue (48.2 g) was chromatographed on a silica gel column with a gradient of petroleum ether–EtOAc –MeOH (3: 1: 0→0: 0: 1, v/v) to afford 34 fractions (F1– F34), pooled by common TLC characteristics. F5 (4.2 g) was separated by a Toyopearl HW-40 column (CH2Cl2–MeOH, 1: 1, v/v) to afford 7 fractions (Fractions a-g). Fraction b (0.4 g) was separated by preparative HPLC with MeOH–H2O (7: 3, v/v) to give 17 fractions (F1– F17). Fraction 14 (0.1 g) was separated by preparative TLC with CH2Cl2–MeOH, (9: 1, v/v) to give 2α-acetoxy-5α-methoxy-enantio-caryophylla-8(15)-en-3-one (20.0 mg, 3.0 ml/min, tR = 36.3 min) as colourless plate-shaped crystals. The structure of compound is consistent with its IR, MS, 1H-NMR, 13C-NMR and two-dimensional-NMR spectra.

Refinement

With no anomalous scatterers with ZSi present in the molecule and the use of Mo irraditaion, all Friedel equivalents were merged. The absolute configuration of the molecule was assigned on the basis of the known configuration of carryophyllane-type sesquiterpene skeleton, e.g. see Collado et al., 1997.

All H atoms were placed in calculated positions, with C—H = 0.93–0.98 Å, and included in the final cycles of refinement in a riding model approximation, with Uiso(H) = 1.2 times Ueq(C) (1.5 Ueq(C) for methyl H atoms).

Figures

Fig. 1.
Molecular structure of the title compound (I). Displacement ellipsoids are drawn at the 35% probability level; H atoms are omitted for clarity.

Crystal data

C18H28O4F(000) = 1344
Mr = 308.40Dx = 1.151 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7216 reflections
a = 9.2924 (19) Åθ = 1.9–27.8°
b = 17.858 (4) ŵ = 0.08 mm1
c = 21.451 (4) ÅT = 113 K
V = 3559.6 (12) Å3Plate, colourless
Z = 80.18 × 0.16 × 0.08 mm

Data collection

Rigaku Saturn diffractometer3534 independent reflections
Radiation source: rotating anode3031 reflections with I > 2σ(I)
confocalRint = 0.066
ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)h = −11→7
Tmin = 0.986, Tmax = 0.994k = −21→18
21386 measured reflectionsl = −25→25

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049H-atom parameters constrained
wR(F2) = 0.123w = 1/[σ2(Fo2) + (0.0685P)2 + 0.2388P] where P = (Fo2 + 2Fc2)/3
S = 1.08(Δ/σ)max < 0.001
3534 reflectionsΔρmax = 0.19 e Å3
408 parametersΔρmin = −0.20 e Å3
0 restraintsExtinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0185 (15)

Special details

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)

xyzUiso*/Ueq
O10.5582 (3)0.12567 (11)0.81709 (10)0.0301 (5)
O20.7395 (3)0.20496 (12)0.83806 (13)0.0437 (7)
O30.6143 (3)0.17341 (12)0.69939 (10)0.0344 (6)
O40.4326 (3)0.42123 (11)0.71852 (11)0.0363 (6)
O50.8704 (3)0.08791 (11)0.03030 (10)0.0305 (5)
O60.8493 (3)0.16830 (12)0.11031 (12)0.0406 (6)
O70.5906 (3)0.12357 (12)0.00668 (11)0.0407 (6)
O80.4325 (3)0.03567 (13)0.20611 (11)0.0408 (6)
C10.0120 (5)0.2194 (2)0.6862 (2)0.0520 (11)
H1A−0.05710.20550.71540.062*
H1B−0.01530.23110.64570.062*
C20.1489 (4)0.22230 (19)0.70240 (18)0.0372 (9)
C30.1944 (4)0.20341 (18)0.76783 (17)0.0326 (8)
H30.20340.24960.79220.039*
C40.3297 (4)0.15383 (17)0.77841 (15)0.0301 (7)
H40.33860.11880.74340.036*
C50.4763 (4)0.18797 (15)0.79133 (15)0.0269 (7)
H50.46740.22780.82250.032*
C60.5546 (4)0.21756 (17)0.73375 (15)0.0288 (7)
C70.5603 (4)0.30145 (16)0.72253 (16)0.0316 (8)
H70.61090.32250.75860.038*
C80.4135 (4)0.34110 (16)0.72065 (16)0.0314 (8)
H80.35900.32800.75820.038*
C90.3222 (4)0.32443 (19)0.66349 (18)0.0387 (9)
H9A0.37930.33580.62690.046*
H9B0.24120.35870.66370.046*
C100.2631 (4)0.24503 (19)0.65604 (16)0.0369 (8)
H10A0.22340.24020.61440.044*
H10B0.34270.21010.65930.044*
C110.1069 (4)0.1455 (2)0.80510 (18)0.0415 (9)
H11A0.05520.11010.77910.050*
H11B0.04340.16760.83590.050*
C120.2483 (4)0.11359 (18)0.83302 (16)0.0338 (8)
C130.2632 (4)0.02850 (17)0.83394 (17)0.0371 (8)
H13A0.19780.00790.86400.056*
H13B0.36000.01530.84500.056*
H13C0.24120.00880.79340.056*
C140.2787 (5)0.1458 (2)0.89726 (17)0.0424 (9)
H14A0.37610.13470.90890.064*
H14B0.21400.12390.92700.064*
H14C0.26510.19900.89640.064*
C150.6904 (4)0.14231 (19)0.83953 (16)0.0325 (8)
C160.7598 (4)0.07496 (18)0.86604 (17)0.0380 (8)
H16A0.77090.08110.91020.057*
H16B0.85270.06820.84720.057*
H16C0.70100.03190.85790.057*
C170.6540 (4)0.31971 (19)0.6662 (2)0.0456 (10)
H17A0.64940.37250.65790.068*
H17B0.61980.29250.63060.068*
H17C0.75180.30570.67480.068*
C180.4817 (5)0.45335 (18)0.77483 (17)0.0456 (10)
H18A0.58070.44000.78140.068*
H18B0.42460.43500.80890.068*
H18C0.47320.50690.77250.068*
C190.4679 (5)−0.1737 (2)0.00807 (18)0.0519 (11)
H19A0.3720−0.1800−0.00320.062*
H19B0.5337−0.21210.00140.062*
C200.5109 (4)−0.10977 (19)0.03360 (16)0.0382 (9)
C210.6660 (4)−0.09676 (17)0.05160 (15)0.0317 (8)
H210.6735−0.09540.09720.038*
C220.7481 (4)−0.02867 (16)0.02388 (14)0.0286 (7)
H220.7126−0.0188−0.01830.034*
C230.7560 (4)0.04451 (16)0.05969 (15)0.0264 (7)
H230.77960.03480.10350.032*
C240.6160 (4)0.09050 (17)0.05509 (16)0.0300 (8)
C250.5209 (4)0.09690 (19)0.11215 (17)0.0388 (9)
H250.57580.12680.14220.047*
C260.4905 (4)0.02218 (17)0.14503 (15)0.0331 (8)
H260.5805−0.00600.14890.040*
C270.3779 (4)−0.0270 (2)0.11343 (17)0.0411 (9)
H27A0.2858−0.00160.11620.049*
H27B0.3699−0.07310.13700.049*
C280.4044 (4)−0.0475 (2)0.04438 (16)0.0410 (9)
H28A0.3133−0.06180.02580.049*
H28B0.4382−0.00320.02270.049*
C290.7857 (4)−0.14730 (18)0.02549 (18)0.0407 (9)
H29A0.7620−0.1700−0.01430.049*
H29B0.8193−0.18470.05490.049*
C300.8868 (4)−0.07856 (17)0.01989 (16)0.0338 (8)
C310.9849 (4)−0.0714 (2)0.07619 (16)0.0391 (9)
H31A1.0303−0.02320.07590.059*
H31B1.0572−0.10980.07470.059*
H31C0.9292−0.07690.11360.059*
C320.9716 (5)−0.0720 (2)−0.04019 (17)0.0429 (10)
H32A1.0432−0.1107−0.04170.064*
H32B1.0177−0.0239−0.04190.064*
H32C0.9076−0.0772−0.07510.064*
C330.9055 (4)0.15150 (17)0.06118 (16)0.0333 (8)
C341.0164 (5)0.19589 (19)0.0281 (2)0.0503 (11)
H34A0.99480.24820.03210.075*
H34B1.01710.1823−0.01520.075*
H34C1.10910.18590.04600.075*
C350.3847 (5)0.1418 (2)0.0989 (2)0.0607 (12)
H35A0.33420.11970.06440.091*
H35B0.41020.19240.08870.091*
H35C0.32410.14150.13510.091*
C360.5340 (5)0.0672 (2)0.24869 (17)0.0557 (12)
H36A0.55560.11760.23650.084*
H36B0.62070.03790.24820.084*
H36C0.49400.06710.28990.084*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0312 (13)0.0250 (11)0.0341 (12)−0.0012 (10)−0.0041 (10)0.0012 (9)
O20.0355 (15)0.0323 (13)0.0633 (17)−0.0060 (13)−0.0092 (14)0.0009 (12)
O30.0398 (15)0.0303 (11)0.0331 (12)0.0031 (11)0.0057 (11)−0.0027 (10)
O40.0465 (16)0.0248 (11)0.0375 (13)0.0036 (11)0.0041 (12)−0.0005 (10)
O50.0358 (14)0.0260 (11)0.0298 (12)−0.0039 (11)0.0045 (11)−0.0010 (9)
O60.0532 (17)0.0298 (12)0.0389 (14)−0.0106 (13)0.0117 (13)−0.0071 (10)
O70.0459 (16)0.0385 (13)0.0376 (14)0.0101 (12)0.0036 (12)0.0097 (11)
O80.0409 (15)0.0476 (14)0.0340 (13)−0.0134 (13)0.0081 (12)−0.0094 (11)
C10.040 (2)0.052 (2)0.065 (3)0.003 (2)−0.013 (2)0.005 (2)
C20.030 (2)0.0335 (18)0.048 (2)0.0053 (16)−0.0019 (18)−0.0046 (16)
C30.0274 (19)0.0268 (16)0.044 (2)0.0030 (14)0.0025 (16)−0.0029 (14)
C40.0279 (18)0.0309 (16)0.0317 (17)0.0019 (15)0.0027 (15)−0.0044 (14)
C50.0294 (18)0.0210 (15)0.0302 (16)0.0021 (14)−0.0006 (15)−0.0007 (12)
C60.0263 (18)0.0302 (16)0.0300 (17)0.0004 (15)−0.0038 (15)−0.0006 (14)
C70.0302 (19)0.0271 (16)0.0374 (19)−0.0007 (15)0.0027 (15)0.0018 (14)
C80.034 (2)0.0235 (16)0.0365 (18)0.0009 (15)0.0045 (16)−0.0028 (14)
C90.038 (2)0.0407 (19)0.0371 (19)0.0023 (18)−0.0005 (17)0.0021 (16)
C100.036 (2)0.0413 (19)0.0331 (17)0.0040 (18)−0.0087 (17)−0.0056 (15)
C110.032 (2)0.0402 (19)0.052 (2)−0.0053 (17)0.0044 (18)−0.0064 (17)
C120.0300 (19)0.0341 (17)0.0374 (19)−0.0022 (16)0.0041 (17)−0.0033 (14)
C130.036 (2)0.0348 (17)0.040 (2)−0.0078 (17)0.0043 (18)−0.0029 (15)
C140.046 (2)0.0402 (19)0.041 (2)−0.0071 (18)0.0114 (18)−0.0039 (16)
C150.0314 (19)0.0374 (19)0.0286 (16)0.0009 (16)0.0033 (15)0.0006 (15)
C160.036 (2)0.0395 (19)0.0381 (19)0.0001 (18)−0.0002 (18)0.0076 (15)
C170.041 (2)0.0347 (19)0.061 (3)0.0099 (19)0.018 (2)0.0110 (18)
C180.069 (3)0.0293 (17)0.039 (2)−0.0051 (19)0.015 (2)−0.0036 (15)
C190.056 (3)0.051 (2)0.048 (2)−0.026 (2)0.008 (2)−0.0148 (18)
C200.044 (2)0.0401 (19)0.0303 (18)−0.0108 (18)0.0044 (17)−0.0048 (14)
C210.043 (2)0.0243 (16)0.0275 (17)−0.0042 (16)0.0050 (16)−0.0017 (13)
C220.0347 (19)0.0265 (15)0.0245 (16)0.0016 (16)−0.0016 (16)−0.0009 (13)
C230.0259 (18)0.0272 (15)0.0261 (16)−0.0035 (15)0.0042 (14)0.0011 (12)
C240.034 (2)0.0220 (15)0.0337 (18)0.0007 (15)0.0018 (16)−0.0006 (14)
C250.040 (2)0.0369 (18)0.0399 (19)0.0042 (17)0.0093 (18)−0.0034 (15)
C260.034 (2)0.0336 (16)0.0320 (17)−0.0040 (17)0.0044 (16)−0.0056 (13)
C270.034 (2)0.047 (2)0.043 (2)−0.0084 (18)0.0052 (18)−0.0137 (17)
C280.035 (2)0.052 (2)0.036 (2)−0.0084 (19)−0.0053 (17)−0.0073 (16)
C290.055 (3)0.0266 (16)0.040 (2)0.0016 (17)0.0062 (19)0.0008 (15)
C300.042 (2)0.0277 (17)0.0315 (18)0.0037 (16)0.0026 (17)−0.0026 (14)
C310.038 (2)0.041 (2)0.038 (2)0.0105 (18)−0.0021 (17)0.0048 (15)
C320.052 (3)0.039 (2)0.037 (2)0.0101 (19)0.0075 (19)0.0000 (15)
C330.038 (2)0.0227 (16)0.0398 (19)−0.0014 (15)0.0030 (17)0.0014 (15)
C340.050 (3)0.0349 (19)0.066 (3)−0.0073 (19)0.022 (2)−0.0037 (17)
C350.058 (3)0.055 (3)0.069 (3)0.020 (2)0.018 (3)0.007 (2)
C360.060 (3)0.074 (3)0.033 (2)−0.030 (2)0.007 (2)−0.0087 (18)

Geometric parameters (Å, °)

O1—C151.353 (4)C17—H17A0.9600
O1—C51.456 (4)C17—H17B0.9600
O2—C151.209 (4)C17—H17C0.9600
O3—C61.214 (4)C18—H18A0.9600
O4—C181.413 (4)C18—H18B0.9600
O4—C81.443 (4)C18—H18C0.9600
O5—C331.355 (4)C19—C201.328 (5)
O5—C231.459 (4)C19—H19A0.9300
O6—C331.214 (4)C19—H19B0.9300
O7—C241.218 (4)C20—C281.507 (5)
O8—C361.428 (5)C20—C211.510 (5)
O8—C261.437 (4)C21—C291.538 (5)
C1—C21.319 (6)C21—C221.554 (4)
C1—H1A0.9300C21—H210.9800
C1—H1B0.9300C22—C231.517 (4)
C2—C31.504 (5)C22—C301.569 (5)
C2—C101.510 (5)C22—H220.9800
C3—C111.540 (5)C23—C241.542 (5)
C3—C41.554 (5)C23—H230.9800
C3—H30.9800C24—C251.514 (5)
C4—C51.518 (5)C25—C351.525 (6)
C4—C121.569 (5)C25—C261.535 (5)
C4—H40.9800C25—H250.9800
C5—C61.528 (4)C26—C271.525 (5)
C5—H50.9800C26—H260.9800
C6—C71.518 (4)C27—C281.546 (5)
C7—C171.524 (5)C27—H27A0.9700
C7—C81.537 (5)C27—H27B0.9700
C7—H70.9800C28—H28A0.9700
C8—C91.521 (5)C28—H28B0.9700
C8—H80.9800C29—C301.550 (5)
C9—C101.529 (5)C29—H29A0.9700
C9—H9A0.9700C29—H29B0.9700
C9—H9B0.9700C30—C321.515 (5)
C10—H10A0.9700C30—C311.518 (5)
C10—H10B0.9700C31—H31A0.9600
C11—C121.553 (5)C31—H31B0.9600
C11—H11A0.9700C31—H31C0.9600
C11—H11B0.9700C32—H32A0.9600
C12—C141.519 (5)C32—H32B0.9600
C12—C131.526 (5)C32—H32C0.9600
C13—H13A0.9600C33—C341.481 (5)
C13—H13B0.9600C34—H34A0.9600
C13—H13C0.9600C34—H34B0.9600
C14—H14A0.9600C34—H34C0.9600
C14—H14B0.9600C35—H35A0.9600
C14—H14C0.9600C35—H35B0.9600
C15—C161.478 (5)C35—H35C0.9600
C16—H16A0.9600C36—H36A0.9600
C16—H16B0.9600C36—H36B0.9600
C16—H16C0.9600C36—H36C0.9600
C15—O1—C5116.2 (2)H18A—C18—H18C109.5
C18—O4—C8114.5 (2)H18B—C18—H18C109.5
C33—O5—C23114.2 (2)C20—C19—H19A120.0
C36—O8—C26113.7 (3)C20—C19—H19B120.0
C2—C1—H1A120.0H19A—C19—H19B120.0
C2—C1—H1B120.0C19—C20—C28120.0 (4)
H1A—C1—H1B120.0C19—C20—C21121.7 (4)
C1—C2—C3120.5 (4)C28—C20—C21118.3 (3)
C1—C2—C10121.0 (4)C20—C21—C29120.4 (3)
C3—C2—C10118.5 (3)C20—C21—C22119.4 (3)
C2—C3—C11119.1 (3)C29—C21—C2288.0 (2)
C2—C3—C4119.4 (3)C20—C21—H21109.1
C11—C3—C488.2 (3)C29—C21—H21109.1
C2—C3—H3109.4C22—C21—H21109.1
C11—C3—H3109.4C23—C22—C21120.3 (3)
C4—C3—H3109.4C23—C22—C30118.5 (3)
C5—C4—C3121.6 (3)C21—C22—C3088.8 (2)
C5—C4—C12118.7 (3)C23—C22—H22109.2
C3—C4—C1288.9 (3)C21—C22—H22109.2
C5—C4—H4108.7C30—C22—H22109.2
C3—C4—H4108.7O5—C23—C22105.9 (2)
C12—C4—H4108.7O5—C23—C24107.7 (2)
O1—C5—C4103.4 (2)C22—C23—C24112.7 (3)
O1—C5—C6108.8 (3)O5—C23—H23110.1
C4—C5—C6114.7 (3)C22—C23—H23110.1
O1—C5—H5109.9C24—C23—H23110.1
C4—C5—H5109.9O7—C24—C25122.6 (3)
C6—C5—H5109.9O7—C24—C23118.5 (3)
O3—C6—C7121.9 (3)C25—C24—C23118.8 (3)
O3—C6—C5118.9 (3)C24—C25—C35111.9 (3)
C7—C6—C5119.1 (3)C24—C25—C26114.4 (3)
C6—C7—C17110.9 (3)C35—C25—C26112.9 (3)
C6—C7—C8115.3 (3)C24—C25—H25105.6
C17—C7—C8112.8 (3)C35—C25—H25105.6
C6—C7—H7105.6C26—C25—H25105.6
C17—C7—H7105.6O8—C26—C27104.2 (3)
C8—C7—H7105.6O8—C26—C25110.0 (3)
O4—C8—C9103.7 (3)C27—C26—C25115.0 (3)
O4—C8—C7110.4 (3)O8—C26—H26109.2
C9—C8—C7115.2 (3)C27—C26—H26109.2
O4—C8—H8109.1C25—C26—H26109.2
C9—C8—H8109.1C26—C27—C28116.9 (3)
C7—C8—H8109.1C26—C27—H27A108.1
C8—C9—C10117.8 (3)C28—C27—H27A108.1
C8—C9—H9A107.9C26—C27—H27B108.1
C10—C9—H9A107.9C28—C27—H27B108.1
C8—C9—H9B107.9H27A—C27—H27B107.3
C10—C9—H9B107.9C20—C28—C27115.3 (3)
H9A—C9—H9B107.2C20—C28—H28A108.5
C2—C10—C9115.6 (3)C27—C28—H28A108.5
C2—C10—H10A108.4C20—C28—H28B108.5
C9—C10—H10A108.4C27—C28—H28B108.5
C2—C10—H10B108.4H28A—C28—H28B107.5
C9—C10—H10B108.4C21—C29—C3090.1 (2)
H10A—C10—H10B107.4C21—C29—H29A113.6
C3—C11—C1290.0 (3)C30—C29—H29A113.6
C3—C11—H11A113.6C21—C29—H29B113.6
C12—C11—H11A113.6C30—C29—H29B113.6
C3—C11—H11B113.6H29A—C29—H29B110.9
C12—C11—H11B113.6C32—C30—C31111.0 (3)
H11A—C11—H11B110.9C32—C30—C29116.2 (3)
C14—C12—C13110.4 (3)C31—C30—C29111.6 (3)
C14—C12—C11111.6 (3)C32—C30—C22115.4 (3)
C13—C12—C11116.6 (3)C31—C30—C22113.7 (3)
C14—C12—C4114.5 (3)C29—C30—C2287.0 (3)
C13—C12—C4115.0 (3)C30—C31—H31A109.5
C11—C12—C487.2 (3)C30—C31—H31B109.5
C12—C13—H13A109.5H31A—C31—H31B109.5
C12—C13—H13B109.5C30—C31—H31C109.5
H13A—C13—H13B109.5H31A—C31—H31C109.5
C12—C13—H13C109.5H31B—C31—H31C109.5
H13A—C13—H13C109.5C30—C32—H32A109.5
H13B—C13—H13C109.5C30—C32—H32B109.5
C12—C14—H14A109.5H32A—C32—H32B109.5
C12—C14—H14B109.5C30—C32—H32C109.5
H14A—C14—H14B109.5H32A—C32—H32C109.5
C12—C14—H14C109.5H32B—C32—H32C109.5
H14A—C14—H14C109.5O6—C33—O5121.9 (3)
H14B—C14—H14C109.5O6—C33—C34125.6 (3)
O2—C15—O1122.5 (3)O5—C33—C34112.5 (3)
O2—C15—C16126.8 (3)C33—C34—H34A109.5
O1—C15—C16110.8 (3)C33—C34—H34B109.5
C15—C16—H16A109.5H34A—C34—H34B109.5
C15—C16—H16B109.5C33—C34—H34C109.5
H16A—C16—H16B109.5H34A—C34—H34C109.5
C15—C16—H16C109.5H34B—C34—H34C109.5
H16A—C16—H16C109.5C25—C35—H35A109.5
H16B—C16—H16C109.5C25—C35—H35B109.5
C7—C17—H17A109.5H35A—C35—H35B109.5
C7—C17—H17B109.5C25—C35—H35C109.5
H17A—C17—H17B109.5H35A—C35—H35C109.5
C7—C17—H17C109.5H35B—C35—H35C109.5
H17A—C17—H17C109.5O8—C36—H36A109.5
H17B—C17—H17C109.5O8—C36—H36B109.5
O4—C18—H18A109.5H36A—C36—H36B109.5
O4—C18—H18B109.5O8—C36—H36C109.5
H18A—C18—H18B109.5H36A—C36—H36C109.5
O4—C18—H18C109.5H36B—C36—H36C109.5
C1—C2—C3—C1130.8 (5)C19—C20—C21—C2916.6 (5)
C10—C2—C3—C11−149.5 (3)C28—C20—C21—C29−162.5 (3)
C1—C2—C3—C4136.7 (4)C19—C20—C21—C22123.1 (4)
C10—C2—C3—C4−43.7 (4)C28—C20—C21—C22−56.0 (4)
C2—C3—C4—C595.8 (4)C20—C21—C22—C2394.6 (4)
C11—C3—C4—C5−141.4 (3)C29—C21—C22—C23−141.2 (3)
C2—C3—C4—C12−140.7 (3)C20—C21—C22—C30−142.7 (3)
C11—C3—C4—C12−17.9 (3)C29—C21—C22—C30−18.5 (3)
C15—O1—C5—C4−172.9 (3)C33—O5—C23—C22−172.0 (3)
C15—O1—C5—C664.7 (3)C33—O5—C23—C2467.2 (3)
C3—C4—C5—O1162.8 (3)C21—C22—C23—O5164.6 (3)
C12—C4—C5—O154.8 (3)C30—C22—C23—O557.8 (3)
C3—C4—C5—C6−78.9 (4)C21—C22—C23—C24−77.9 (4)
C12—C4—C5—C6173.1 (3)C30—C22—C23—C24175.3 (3)
O1—C5—C6—O337.1 (4)O5—C23—C24—O741.2 (4)
C4—C5—C6—O3−78.1 (4)C22—C23—C24—O7−75.2 (4)
O1—C5—C6—C7−140.5 (3)O5—C23—C24—C25−134.8 (3)
C4—C5—C6—C7104.3 (3)C22—C23—C24—C25108.8 (3)
O3—C6—C7—C17−2.6 (5)O7—C24—C25—C356.2 (5)
C5—C6—C7—C17174.9 (3)C23—C24—C25—C35−177.9 (3)
O3—C6—C7—C8127.1 (4)O7—C24—C25—C26136.3 (3)
C5—C6—C7—C8−55.3 (4)C23—C24—C25—C26−47.9 (4)
C18—O4—C8—C9164.3 (3)C36—O8—C26—C27167.2 (3)
C18—O4—C8—C7−71.8 (4)C36—O8—C26—C25−69.1 (4)
C6—C7—C8—O4172.0 (3)C24—C25—C26—O8165.2 (3)
C17—C7—C8—O4−59.2 (4)C35—C25—C26—O8−65.3 (4)
C6—C7—C8—C9−70.9 (4)C24—C25—C26—C27−77.6 (4)
C17—C7—C8—C957.9 (4)C35—C25—C26—C2751.9 (4)
O4—C8—C9—C10−171.6 (3)O8—C26—C27—C28176.2 (3)
C7—C8—C9—C1067.6 (4)C25—C26—C27—C2855.8 (4)
C1—C2—C10—C9104.1 (4)C19—C20—C28—C27115.6 (4)
C3—C2—C10—C9−75.6 (4)C21—C20—C28—C27−65.4 (4)
C8—C9—C10—C268.8 (4)C26—C27—C28—C2079.2 (4)
C2—C3—C11—C12141.2 (3)C20—C21—C29—C30142.0 (3)
C4—C3—C11—C1218.1 (3)C22—C21—C29—C3018.7 (3)
C3—C11—C12—C1497.3 (3)C21—C29—C30—C32−135.5 (3)
C3—C11—C12—C13−134.6 (3)C21—C29—C30—C3195.8 (3)
C3—C11—C12—C4−17.9 (2)C21—C29—C30—C22−18.5 (3)
C5—C4—C12—C1431.1 (4)C23—C22—C30—C32−99.7 (4)
C3—C4—C12—C14−94.8 (3)C21—C22—C30—C32136.1 (3)
C5—C4—C12—C13−98.2 (4)C23—C22—C30—C3130.2 (4)
C3—C4—C12—C13135.9 (3)C21—C22—C30—C31−94.0 (3)
C5—C4—C12—C11143.7 (3)C23—C22—C30—C29142.5 (3)
C3—C4—C12—C1117.8 (2)C21—C22—C30—C2918.3 (2)
C5—O1—C15—O2−0.6 (5)C23—O5—C33—O62.8 (5)
C5—O1—C15—C16178.2 (3)C23—O5—C33—C34−177.0 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2089).

References

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