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The structures of 3β-acet­oxy-9α,11α-ep­oxy-5α-lanost-9(11)-en-7-one and 3β-acet­oxy-9β,11β-ep­oxy-5α-lanost-9(11)-en-7-one, C32H52O4, differ in their respective substituted cyclo­hexa­none rings but adopt similar conformations in the other three rings. In both of the crystal structures, weak inter­molecular C—H...O inter­actions are present.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107009754/gg3071sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107009754/gg3071Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107009754/gg3071IIsup3.hkl
Contains datablock II

CCDC references: 645583; 645584

Computing details top

For both compounds, data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(I) 3β-acetoxy-9α,11-epoxy-5α-lanost-9(11)-en-7-one top
Crystal data top
C32H52O4F(000) = 552
Mr = 500.74Dx = 1.131 Mg m3
Monoclinic, P21Melting point: 446(2) K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 11.483 (4) ÅCell parameters from 5281 reflections
b = 7.612 (3) Åθ = 2.9–27.5°
c = 16.903 (6) ŵ = 0.07 mm1
β = 95.79 (3)°T = 173 K
V = 1469.9 (9) Å3Block, colorless
Z = 20.14 × 0.12 × 0.10 mm
Data collection top
Nonius KappaCCD
diffractometer
3578 independent reflections
Radiation source: fine-focus sealed tube3157 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.020
ω and φ scansθmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1414
Tmin = 0.990, Tmax = 0.993k = 98
5281 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0455P)2 + 0.2611P]
where P = (Fo2 + 2Fc2)/3
3578 reflections(Δ/σ)max = 0.001
334 parametersΔρmax = 0.22 e Å3
1 restraintΔρmin = 0.15 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.37522 (13)0.2718 (2)0.89785 (7)0.0330 (4)
O20.21373 (16)0.1687 (3)0.94688 (10)0.0530 (5)
O30.47605 (12)0.0335 (3)0.49951 (9)0.0393 (4)
O40.15405 (11)0.0900 (2)0.57223 (8)0.0258 (3)
C10.18057 (17)0.3326 (3)0.70439 (11)0.0260 (4)
H1A0.12090.42220.68710.031*
H1B0.14080.21720.70450.031*
C20.23381 (18)0.3754 (3)0.78908 (11)0.0295 (5)
H2A0.27130.49250.79000.035*
H2B0.17140.37800.82540.035*
C30.32393 (17)0.2370 (3)0.81652 (11)0.0280 (5)
H30.28390.12020.81570.034*
C40.42668 (16)0.2244 (3)0.76522 (11)0.0269 (4)
C50.37306 (16)0.1999 (3)0.67696 (10)0.0245 (4)
H50.33650.08060.67500.029*
C60.46894 (17)0.1908 (3)0.61981 (11)0.0293 (5)
H6A0.50670.30740.61770.035*
H6B0.52950.10570.64080.035*
C70.42253 (16)0.1367 (3)0.53669 (11)0.0269 (5)
C80.31151 (15)0.2289 (3)0.50202 (10)0.0220 (4)
H80.33610.35200.49140.026*
C90.22390 (15)0.2457 (3)0.56472 (11)0.0212 (4)
C100.27347 (16)0.3274 (3)0.64460 (11)0.0226 (4)
C110.09759 (16)0.2459 (3)0.53682 (11)0.0238 (4)
H110.04710.31060.57190.029*
C120.04955 (16)0.2371 (3)0.45004 (10)0.0247 (4)
H12A0.01330.32560.43980.030*
H12B0.01460.11970.43880.030*
C130.14384 (16)0.2703 (3)0.39334 (11)0.0219 (4)
C140.25612 (17)0.1595 (3)0.42123 (11)0.0238 (4)
C150.33239 (17)0.1907 (3)0.35238 (11)0.0289 (5)
H15A0.38940.09410.34910.035*
H15B0.37540.30320.35940.035*
C160.24332 (16)0.1957 (4)0.27715 (11)0.0304 (5)
H16A0.25080.08860.24480.036*
H16B0.25790.29940.24420.036*
C170.11836 (16)0.2061 (3)0.30577 (10)0.0246 (4)
H170.08840.08300.30780.030*
C180.16847 (19)0.4693 (3)0.39447 (12)0.0278 (5)
H18A0.23420.49410.36350.042*
H18B0.18810.50820.44950.042*
H18C0.09880.53210.37120.042*
C190.31041 (18)0.5177 (3)0.62800 (12)0.0273 (5)
H19A0.24630.57790.59630.041*
H19B0.37980.51620.59870.041*
H19C0.32860.57990.67850.041*
C200.03244 (17)0.3078 (3)0.24644 (11)0.0264 (4)
H200.06570.42730.23900.032*
C210.08823 (18)0.3298 (3)0.27620 (12)0.0310 (5)
H21A0.08040.39520.32640.047*
H21B0.12190.21390.28470.047*
H21C0.13960.39450.23650.047*
C220.02258 (18)0.2125 (4)0.16574 (11)0.0306 (5)
H22A0.09970.21730.14440.037*
H22B0.00440.08740.17460.037*
C230.06952 (19)0.2864 (4)0.10319 (11)0.0335 (5)
H23A0.14770.27260.12230.040*
H23B0.05520.41370.09700.040*
C240.07022 (19)0.1980 (4)0.02238 (11)0.0377 (6)
H24A0.08390.07060.02860.045*
H24B0.00770.21290.00290.045*
C250.1639 (2)0.2720 (4)0.03989 (12)0.0428 (6)
H250.15130.40160.04360.051*
C260.1510 (3)0.1925 (6)0.12106 (14)0.0665 (10)
H26A0.21060.24190.16040.100*
H26B0.16090.06480.11850.100*
H26C0.07300.21940.13660.100*
C270.2871 (2)0.2420 (5)0.01583 (17)0.0588 (8)
H27A0.34490.28690.05760.088*
H27B0.29570.30390.03410.088*
H27C0.29980.11600.00850.088*
C280.22973 (19)0.0400 (3)0.42300 (13)0.0286 (5)
H28A0.21680.08470.36840.043*
H28B0.15940.06000.45020.043*
H28C0.29620.10150.45150.043*
C290.4973 (2)0.0593 (4)0.79145 (13)0.0387 (6)
H29A0.56610.05110.76180.058*
H29B0.44820.04510.78080.058*
H29C0.52260.06650.84850.058*
C300.5077 (2)0.3840 (4)0.77713 (13)0.0346 (5)
H30A0.57280.37100.74430.052*
H30B0.53850.39230.83320.052*
H30C0.46370.49090.76150.052*
C310.3125 (2)0.2224 (4)0.95714 (12)0.0373 (5)
C320.3827 (2)0.2425 (5)1.03695 (13)0.0515 (7)
H32A0.32970.24451.07890.077*
H32B0.42710.35261.03800.077*
H32C0.43700.14351.04580.078*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0376 (8)0.0435 (10)0.0173 (6)0.0068 (8)0.0005 (6)0.0004 (7)
O20.0535 (11)0.0696 (14)0.0375 (9)0.0166 (11)0.0124 (8)0.0051 (10)
O30.0288 (9)0.0573 (12)0.0313 (7)0.0160 (8)0.0012 (6)0.0082 (8)
O40.0249 (7)0.0254 (8)0.0264 (7)0.0029 (6)0.0001 (5)0.0048 (6)
C10.0221 (9)0.0335 (12)0.0224 (9)0.0011 (9)0.0022 (7)0.0001 (9)
C20.0298 (10)0.0368 (13)0.0223 (9)0.0010 (10)0.0049 (8)0.0009 (9)
C30.0314 (10)0.0337 (12)0.0183 (8)0.0037 (10)0.0001 (7)0.0014 (9)
C40.0256 (9)0.0337 (12)0.0207 (9)0.0006 (9)0.0007 (7)0.0018 (9)
C50.0231 (9)0.0294 (11)0.0208 (8)0.0017 (9)0.0009 (7)0.0000 (9)
C60.0214 (9)0.0420 (13)0.0239 (9)0.0044 (9)0.0006 (7)0.0007 (10)
C70.0214 (9)0.0367 (13)0.0230 (9)0.0030 (9)0.0048 (7)0.0025 (9)
C80.0200 (8)0.0263 (11)0.0194 (8)0.0012 (8)0.0008 (6)0.0012 (8)
C90.0200 (9)0.0220 (10)0.0218 (8)0.0000 (8)0.0027 (7)0.0018 (8)
C100.0215 (9)0.0264 (11)0.0199 (8)0.0000 (8)0.0015 (7)0.0004 (8)
C110.0210 (9)0.0278 (11)0.0226 (9)0.0005 (9)0.0018 (7)0.0028 (9)
C120.0209 (9)0.0301 (11)0.0224 (9)0.0009 (9)0.0008 (7)0.0003 (9)
C130.0194 (9)0.0248 (11)0.0211 (9)0.0007 (8)0.0007 (7)0.0000 (8)
C140.0221 (9)0.0281 (11)0.0212 (9)0.0015 (8)0.0018 (7)0.0000 (8)
C150.0250 (9)0.0406 (13)0.0213 (9)0.0008 (10)0.0026 (7)0.0014 (10)
C160.0260 (10)0.0421 (14)0.0232 (9)0.0020 (10)0.0028 (7)0.0020 (10)
C170.0249 (9)0.0269 (11)0.0216 (9)0.0008 (9)0.0004 (7)0.0003 (9)
C180.0319 (11)0.0273 (11)0.0237 (9)0.0019 (9)0.0004 (8)0.0007 (9)
C190.0290 (10)0.0291 (12)0.0236 (9)0.0016 (9)0.0013 (8)0.0013 (9)
C200.0283 (10)0.0286 (11)0.0211 (9)0.0011 (9)0.0025 (8)0.0005 (9)
C210.0310 (10)0.0339 (13)0.0268 (10)0.0092 (10)0.0036 (8)0.0021 (10)
C220.0299 (10)0.0373 (13)0.0235 (9)0.0031 (10)0.0026 (7)0.0021 (10)
C230.0328 (11)0.0412 (14)0.0247 (10)0.0041 (10)0.0052 (8)0.0036 (10)
C240.0372 (11)0.0491 (15)0.0252 (10)0.0069 (12)0.0044 (8)0.0069 (11)
C250.0497 (14)0.0473 (16)0.0285 (11)0.0071 (12)0.0103 (10)0.0074 (12)
C260.085 (2)0.079 (2)0.0309 (12)0.024 (2)0.0172 (13)0.0137 (16)
C270.0442 (14)0.073 (2)0.0546 (15)0.0001 (16)0.0189 (12)0.0077 (17)
C280.0299 (11)0.0282 (12)0.0272 (10)0.0059 (9)0.0001 (8)0.0010 (9)
C290.0413 (13)0.0446 (15)0.0285 (11)0.0121 (12)0.0051 (9)0.0039 (11)
C300.0297 (11)0.0491 (15)0.0241 (10)0.0069 (11)0.0022 (8)0.0008 (10)
C310.0497 (13)0.0401 (14)0.0224 (10)0.0015 (13)0.0053 (9)0.0044 (10)
C320.0665 (16)0.064 (2)0.0226 (10)0.0014 (17)0.0014 (10)0.0019 (13)
Geometric parameters (Å, º) top
O1—C311.345 (3)C16—H16B0.9900
O1—C31.464 (2)C17—C201.542 (3)
O2—C311.202 (3)C17—H171.0000
O3—C71.212 (3)C18—H18A0.9800
O4—C91.444 (2)C18—H18B0.9800
O4—C111.452 (3)C18—H18C0.9800
C1—C21.534 (3)C19—H19A0.9800
C1—C101.542 (3)C19—H19B0.9800
C1—H1A0.9900C19—H19C0.9800
C1—H1B0.9900C20—C211.530 (3)
C2—C31.516 (3)C20—C221.539 (3)
C2—H2A0.9900C20—H201.0000
C2—H2B0.9900C21—H21A0.9800
C3—C41.536 (3)C21—H21B0.9800
C3—H31.0000C21—H21C0.9800
C4—C301.532 (3)C22—C231.525 (3)
C4—C291.537 (3)C22—H22A0.9900
C4—C51.567 (3)C22—H22B0.9900
C5—C61.538 (3)C23—C241.522 (3)
C5—C101.556 (3)C23—H23A0.9900
C5—H51.0000C23—H23B0.9900
C6—C71.509 (3)C24—C251.534 (3)
C6—H6A0.9900C24—H24A0.9900
C6—H6B0.9900C24—H24B0.9900
C7—C81.520 (3)C25—C261.521 (3)
C8—C91.538 (2)C25—C271.528 (4)
C8—C141.541 (3)C25—H251.0000
C8—H81.0000C26—H26A0.9800
C9—C111.479 (3)C26—H26B0.9800
C9—C101.542 (3)C26—H26C0.9800
C10—C191.544 (3)C27—H27A0.9800
C11—C121.516 (3)C27—H27B0.9800
C11—H111.0000C27—H27C0.9800
C12—C131.537 (2)C28—H28A0.9800
C12—H12A0.9900C28—H28B0.9800
C12—H12B0.9900C28—H28C0.9800
C13—C181.541 (3)C29—H29A0.9800
C13—C171.558 (3)C29—H29B0.9800
C13—C141.573 (3)C29—H29C0.9800
C14—C151.544 (3)C30—H30A0.9800
C14—C281.549 (3)C30—H30B0.9800
C15—C161.550 (3)C30—H30C0.9800
C15—H15A0.9900C31—C321.508 (3)
C15—H15B0.9900C32—H32A0.9800
C16—C171.562 (3)C32—H32B0.9800
C16—H16A0.9900C32—H32C0.9800
C31—O1—C3116.99 (17)H16A—C16—H16B108.5
C9—O4—C1161.44 (12)C20—C17—C13120.46 (18)
C2—C1—C10112.34 (15)C20—C17—C16111.82 (16)
C2—C1—H1A109.1C13—C17—C16102.70 (14)
C10—C1—H1A109.1C20—C17—H17107.0
C2—C1—H1B109.1C13—C17—H17107.0
C10—C1—H1B109.1C16—C17—H17107.0
H1A—C1—H1B107.9C13—C18—H18A109.5
C3—C2—C1109.48 (18)C13—C18—H18B109.5
C3—C2—H2A109.8H18A—C18—H18B109.5
C1—C2—H2A109.8C13—C18—H18C109.5
C3—C2—H2B109.8H18A—C18—H18C109.5
C1—C2—H2B109.8H18B—C18—H18C109.5
H2A—C2—H2B108.2C10—C19—H19A109.5
O1—C3—C2111.03 (18)C10—C19—H19B109.5
O1—C3—C4106.39 (15)H19A—C19—H19B109.5
C2—C3—C4114.22 (17)C10—C19—H19C109.5
O1—C3—H3108.3H19A—C19—H19C109.5
C2—C3—H3108.3H19B—C19—H19C109.5
C4—C3—H3108.3C21—C20—C22110.80 (16)
C30—C4—C3111.56 (18)C21—C20—C17112.48 (16)
C30—C4—C29108.36 (17)C22—C20—C17108.97 (18)
C3—C4—C29107.54 (18)C21—C20—H20108.2
C30—C4—C5113.24 (17)C22—C20—H20108.2
C3—C4—C5107.13 (15)C17—C20—H20108.2
C29—C4—C5108.83 (18)C20—C21—H21A109.5
C6—C5—C10110.78 (16)C20—C21—H21B109.5
C6—C5—C4111.48 (15)H21A—C21—H21B109.5
C10—C5—C4117.70 (17)C20—C21—H21C109.5
C6—C5—H5105.3H21A—C21—H21C109.5
C10—C5—H5105.3H21B—C21—H21C109.5
C4—C5—H5105.3C23—C22—C20115.14 (19)
C7—C6—C5112.91 (16)C23—C22—H22A108.5
C7—C6—H6A109.0C20—C22—H22A108.5
C5—C6—H6A109.0C23—C22—H22B108.5
C7—C6—H6B109.0C20—C22—H22B108.5
C5—C6—H6B109.0H22A—C22—H22B107.5
H6A—C6—H6B107.8C24—C23—C22113.6 (2)
O3—C7—C6120.65 (18)C24—C23—H23A108.9
O3—C7—C8123.30 (18)C22—C23—H23A108.9
C6—C7—C8115.91 (17)C24—C23—H23B108.9
C7—C8—C9110.75 (15)C22—C23—H23B108.9
C7—C8—C14116.02 (17)H23A—C23—H23B107.7
C9—C8—C14113.52 (15)C23—C24—C25113.2 (2)
C7—C8—H8105.1C23—C24—H24A108.9
C9—C8—H8105.1C25—C24—H24A108.9
C14—C8—H8105.1C23—C24—H24B108.9
O4—C9—C1159.54 (12)C25—C24—H24B108.9
O4—C9—C8113.57 (16)H24A—C24—H24B107.8
C11—C9—C8117.96 (15)C26—C25—C27111.0 (2)
O4—C9—C10114.39 (15)C26—C25—C24110.3 (2)
C11—C9—C10122.83 (15)C27—C25—C24111.5 (2)
C8—C9—C10115.31 (14)C26—C25—H25108.0
C1—C10—C9111.44 (15)C27—C25—H25108.0
C1—C10—C19108.42 (16)C24—C25—H25108.0
C9—C10—C19107.65 (16)C25—C26—H26A109.5
C1—C10—C5108.54 (15)C25—C26—H26B109.5
C9—C10—C5104.46 (16)H26A—C26—H26B109.5
C19—C10—C5116.33 (17)C25—C26—H26C109.5
O4—C11—C959.02 (12)H26A—C26—H26C109.5
O4—C11—C12117.82 (18)H26B—C26—H26C109.5
C9—C11—C12123.91 (15)C25—C27—H27A109.5
O4—C11—H11114.8C25—C27—H27B109.5
C9—C11—H11114.8H27A—C27—H27B109.5
C12—C11—H11114.8C25—C27—H27C109.5
C11—C12—C13112.68 (15)H27A—C27—H27C109.5
C11—C12—H12A109.1H27B—C27—H27C109.5
C13—C12—H12A109.1C14—C28—H28A109.5
C11—C12—H12B109.1C14—C28—H28B109.5
C13—C12—H12B109.1H28A—C28—H28B109.5
H12A—C12—H12B107.8C14—C28—H28C109.5
C12—C13—C18107.09 (17)H28A—C28—H28C109.5
C12—C13—C17117.65 (15)H28B—C28—H28C109.5
C18—C13—C17109.68 (17)C4—C29—H29A109.5
C12—C13—C14109.42 (15)C4—C29—H29B109.5
C18—C13—C14112.32 (17)H29A—C29—H29B109.5
C17—C13—C14100.73 (15)C4—C29—H29C109.5
C8—C14—C15113.61 (16)H29A—C29—H29C109.5
C8—C14—C28112.53 (17)H29B—C29—H29C109.5
C15—C14—C28107.00 (18)C4—C30—H30A109.5
C8—C14—C13109.53 (16)C4—C30—H30B109.5
C15—C14—C13101.64 (15)H30A—C30—H30B109.5
C28—C14—C13112.05 (17)C4—C30—H30C109.5
C14—C15—C16104.16 (16)H30A—C30—H30C109.5
C14—C15—H15A110.9H30B—C30—H30C109.5
C16—C15—H15A110.9O2—C31—O1123.78 (19)
C14—C15—H15B110.9O2—C31—C32125.1 (2)
C16—C15—H15B110.9O1—C31—C32111.1 (2)
H15A—C15—H15B108.9C31—C32—H32A109.5
C15—C16—C17107.34 (15)C31—C32—H32B109.5
C15—C16—H16A110.2H32A—C32—H32B109.5
C17—C16—H16A110.2C31—C32—H32C109.5
C15—C16—H16B110.2H32A—C32—H32C109.5
C17—C16—H16B110.2H32B—C32—H32C109.5
C10—C1—C2—C359.7 (2)C9—O4—C11—C12114.76 (18)
C31—O1—C3—C280.2 (2)C8—C9—C11—O4102.30 (19)
C31—O1—C3—C4154.9 (2)C10—C9—C11—O4101.0 (2)
C1—C2—C3—O1178.97 (16)O4—C9—C11—C12104.6 (2)
C1—C2—C3—C460.7 (2)C8—C9—C11—C122.3 (3)
O1—C3—C4—C3051.8 (2)C10—C9—C11—C12154.4 (2)
C2—C3—C4—C3071.1 (2)O4—C11—C12—C1382.8 (2)
O1—C3—C4—C2966.9 (2)C9—C11—C12—C1313.1 (3)
C2—C3—C4—C29170.21 (19)C11—C12—C13—C1875.7 (2)
O1—C3—C4—C5176.21 (18)C11—C12—C13—C17160.28 (19)
C2—C3—C4—C553.4 (2)C11—C12—C13—C1446.2 (2)
C30—C4—C5—C655.0 (3)C7—C8—C14—C1566.3 (2)
C3—C4—C5—C6178.4 (2)C9—C8—C14—C15163.78 (18)
C29—C4—C5—C665.6 (2)C7—C8—C14—C2855.5 (2)
C30—C4—C5—C1074.6 (2)C9—C8—C14—C2874.4 (2)
C3—C4—C5—C1048.9 (2)C7—C8—C14—C13179.12 (16)
C29—C4—C5—C10164.86 (18)C9—C8—C14—C1350.9 (2)
C10—C5—C6—C756.7 (3)C12—C13—C14—C866.6 (2)
C4—C5—C6—C7170.22 (19)C18—C13—C14—C852.2 (2)
C5—C6—C7—O3138.1 (2)C17—C13—C14—C8168.86 (16)
C5—C6—C7—C846.1 (3)C12—C13—C14—C15172.98 (17)
O3—C7—C8—C9142.2 (2)C18—C13—C14—C1568.2 (2)
C6—C7—C8—C942.0 (2)C17—C13—C14—C1548.40 (19)
O3—C7—C8—C1411.0 (3)C12—C13—C14—C2859.1 (2)
C6—C7—C8—C14173.30 (18)C18—C13—C14—C28177.84 (17)
C11—O4—C9—C8109.69 (17)C17—C13—C14—C2865.53 (19)
C11—O4—C9—C10115.09 (17)C8—C14—C15—C16154.24 (18)
C7—C8—C9—O483.12 (19)C28—C14—C15—C1680.9 (2)
C14—C8—C9—O449.4 (2)C13—C14—C15—C1636.7 (2)
C7—C8—C9—C11149.89 (19)C14—C15—C16—C1711.4 (2)
C14—C8—C9—C1117.3 (3)C12—C13—C17—C2075.4 (2)
C7—C8—C9—C1051.7 (2)C18—C13—C17—C2047.2 (2)
C14—C8—C9—C10175.75 (17)C14—C13—C17—C20165.78 (17)
C2—C1—C10—C9167.63 (18)C12—C13—C17—C16159.50 (19)
C2—C1—C10—C1974.1 (2)C18—C13—C17—C1677.8 (2)
C2—C1—C10—C553.1 (2)C14—C13—C17—C1640.7 (2)
O4—C9—C10—C143.5 (2)C15—C16—C17—C20149.18 (19)
C11—C9—C10—C124.8 (3)C15—C16—C17—C1318.6 (2)
C8—C9—C10—C1177.95 (17)C13—C17—C20—C2155.5 (3)
O4—C9—C10—C19162.28 (15)C16—C17—C20—C21176.17 (19)
C11—C9—C10—C1994.0 (2)C13—C17—C20—C22178.78 (17)
C8—C9—C10—C1963.3 (2)C16—C17—C20—C2260.6 (2)
O4—C9—C10—C573.48 (18)C21—C20—C22—C2349.4 (3)
C11—C9—C10—C5141.78 (19)C17—C20—C22—C23173.67 (18)
C8—C9—C10—C561.0 (2)C20—C22—C23—C24175.5 (2)
C6—C5—C10—C1179.55 (17)C22—C23—C24—C25179.4 (2)
C4—C5—C10—C149.6 (2)C23—C24—C25—C26173.8 (3)
C6—C5—C10—C961.5 (2)C23—C24—C25—C2762.4 (3)
C4—C5—C10—C9168.62 (16)C3—O1—C31—O27.7 (4)
C6—C5—C10—C1957.0 (2)C3—O1—C31—C32171.9 (2)
C4—C5—C10—C1972.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C8—H8···O3i1.002.553.368 (3)138
C12—H12A···O4ii0.992.583.556 (3)171
C19—H19B···O3i0.982.463.426 (3)167
C21—H21A···O4ii0.982.483.383 (3)154
C1—H1B···O40.992.462.891 (3)106
C5—H5···O41.002.583.043 (3)108
C28—H28B···O40.982.362.922 (3)115
C28—H28C···O30.982.383.041 (3)125
C29—H29C···O10.982.512.885 (3)103
C30—H30B···O10.982.442.799 (3)101
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x, y+1/2, z+1.
(II) 3β-acetoxy-9β,11-epoxy-5α-lanost-9(11)-en-7-one top
Crystal data top
C32H52O4F(000) = 552
Mr = 500.74Dx = 1.104 Mg m3
Monoclinic, P21Melting point: 489(2) K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 13.356 (6) ÅCell parameters from 2892 reflections
b = 6.233 (13) Åθ = 3.3–25.0°
c = 18.104 (16) ŵ = 0.07 mm1
β = 92.14 (7)°T = 173 K
V = 1506 (3) Å3Plate, colorless
Z = 20.26 × 0.08 × 0.03 mm
Data collection top
Nonius KappaCCD
diffractometer
2892 independent reflections
Radiation source: fine-focus sealed tube2108 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
ω and φ scansθmax = 25.0°, θmin = 3.3°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1515
Tmin = 0.982, Tmax = 0.998k = 07
2892 measured reflectionsl = 021
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)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154 w = 1/[σ2(Fo2) + (0.0826P)2 + 0.2139P]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.05
2892 reflectionsΔρmax = 0.35 e Å3
419 parametersΔρmin = 0.20 e Å3
115 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.047 (11)
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.6620 (2)0.8609 (6)0.28097 (16)0.0597 (9)
O20.5689 (3)1.1604 (7)0.2711 (2)0.0816 (12)
O30.9434 (2)0.4370 (5)0.04190 (19)0.0634 (9)
O40.5989 (2)0.5614 (5)0.06375 (17)0.0546 (8)
C10.5835 (3)0.7219 (7)0.0906 (2)0.0454 (10)
H1A0.52310.64880.07290.058 (13)*
H1B0.58220.87180.07270.034 (10)*
C20.5789 (3)0.7230 (8)0.1741 (2)0.0510 (11)
H2A0.51650.79400.19250.045 (11)*
H2B0.57910.57410.19310.042 (10)*
C30.6691 (3)0.8433 (8)0.2006 (2)0.0502 (11)
H30.66850.99110.17920.064 (14)*
C40.7691 (3)0.7356 (7)0.1773 (2)0.0478 (10)
C50.7715 (3)0.7101 (7)0.0917 (2)0.0435 (10)
H50.77570.85960.07170.031 (9)*
C60.8675 (3)0.5989 (7)0.0629 (2)0.0485 (11)
H6A0.87780.46940.09330.048 (11)*
H6B0.92460.69660.07080.047 (11)*
C70.8711 (3)0.5332 (7)0.0165 (2)0.0464 (10)
C80.7853 (3)0.5811 (7)0.0670 (2)0.0449 (10)
H80.77230.44650.09500.042 (11)*
C90.6856 (3)0.6441 (6)0.0268 (2)0.0421 (10)
C100.6771 (3)0.6095 (7)0.0571 (2)0.0444 (10)
C110.6174 (3)0.7911 (7)0.0662 (3)0.0489 (11)
H110.57170.87850.03320.049 (12)*
C120.6409 (3)0.8880 (8)0.1403 (2)0.0497 (11)
H12A0.58170.87170.17110.051 (12)*
H12B0.65281.04350.13380.048 (12)*
C130.7324 (3)0.7894 (7)0.1818 (2)0.0467 (10)
C140.8170 (3)0.7548 (7)0.1249 (2)0.0451 (10)
C150.9075 (3)0.6987 (9)0.1759 (3)0.0614 (13)
H15A0.90650.54530.19000.065 (14)*
H15B0.97110.72990.15160.054 (13)*
C160.8957 (4)0.8428 (10)0.2437 (3)0.0687 (15)
H16A0.94530.96080.24360.10 (2)*
H16B0.90700.75850.28960.060 (14)*
C170.7863 (3)0.9366 (8)0.2401 (2)0.0512 (11)
H170.79021.08300.21770.035 (10)*
C180.7023 (4)0.5780 (9)0.2181 (3)0.0637 (14)
H18A0.76070.51590.24470.080 (17)*
H18B0.67770.47750.18000.071 (16)*
H18C0.64930.60540.25290.074 (16)*
C190.6679 (3)0.3633 (7)0.0689 (3)0.0500 (11)
H19A0.73280.29530.05740.067 (14)*
H19B0.64750.33390.12040.13 (3)*
H19C0.61770.30550.03620.073 (15)*
C200.7437 (4)0.9634 (9)0.3168 (3)0.0654 (14)
H200.75040.82590.34510.064 (14)*
C210.6335 (4)1.0365 (10)0.3135 (3)0.0634 (13)
H21A0.61061.05710.36380.083 (17)*
H21B0.59220.92690.28840.079 (17)*
H21C0.62761.17200.28630.080 (17)*
C22a0.8064 (12)1.145 (3)0.3575 (8)0.069 (4)0.657 (12)
H22A0.79041.28620.33510.082*0.657 (12)
H22B0.87901.11770.35310.082*0.657 (12)
C23a0.7765 (14)1.143 (3)0.4466 (7)0.129 (7)0.657 (12)
H23A0.70401.16920.45180.155*0.657 (12)
H23B0.79441.00410.47020.155*0.657 (12)
C24a0.8406 (11)1.331 (3)0.4817 (6)0.161 (8)0.657 (12)
H24A0.91121.29770.47150.193*0.657 (12)
H24B0.82291.46050.45240.193*0.657 (12)
C25a0.8403 (9)1.394 (2)0.5563 (6)0.096 (4)0.657 (12)
H25A0.76911.39840.57160.116*0.657 (12)
C26a0.8955 (11)1.231 (2)0.6033 (5)0.121 (5)0.657 (12)
H26A0.86401.09000.59620.182*0.657 (12)
H26B0.89321.27220.65550.182*0.657 (12)
H26C0.96551.22350.58890.182*0.657 (12)
C27a0.887 (2)1.619 (3)0.5704 (11)0.165 (10)0.657 (12)
H27A0.95891.61360.56240.248*0.657 (12)
H27B0.87561.66320.62140.248*0.657 (12)
H27C0.85521.72320.53620.248*0.657 (12)
C22b0.810 (3)1.083 (5)0.3720 (17)0.084 (12)0.343 (12)
H22C0.86750.98370.38030.101*0.343 (12)
H22D0.83701.20180.34220.101*0.343 (12)
C23b0.802 (2)1.168 (4)0.4343 (11)0.068 (7)0.343 (12)
H23C0.81511.05100.47040.081*0.343 (12)
H23D0.72981.20280.43730.081*0.343 (12)
C24b0.8592 (19)1.369 (3)0.4670 (11)0.090 (8)0.343 (12)
H24C0.93151.33500.47230.109*0.343 (12)
H24D0.85101.49010.43200.109*0.343 (12)
C25b0.822 (2)1.432 (6)0.5390 (16)0.177 (17)0.343 (12)
H25B0.80971.29390.56510.213*0.343 (12)
C26b0.902 (3)1.544 (7)0.5861 (16)0.145 (13)0.343 (12)
H26D0.96561.46760.58250.217*0.343 (12)
H26E0.88211.54460.63770.217*0.343 (12)
H26F0.90941.69170.56890.217*0.343 (12)
C27b0.723 (2)1.538 (6)0.5325 (19)0.197 (15)0.343 (12)
H27D0.67411.45440.55930.295*0.343 (12)
H27E0.70151.54830.48030.295*0.343 (12)
H27F0.72791.68290.55380.295*0.343 (12)
C280.8430 (3)0.9627 (7)0.0834 (2)0.0478 (11)
H28A0.86391.07340.11920.072*
H28B0.78391.01240.05460.072*
H28C0.89760.93430.05020.072*
C290.8547 (3)0.8879 (8)0.1987 (3)0.0586 (12)
H29A0.91940.82010.18650.088*
H29B0.84961.02270.17120.088*
H29C0.84930.91760.25180.088*
C300.7826 (4)0.5253 (8)0.2203 (3)0.0574 (12)
H30A0.84800.46270.20670.086*
H30B0.77890.55500.27350.086*
H30C0.72950.42430.20800.086*
C310.6055 (4)1.0228 (11)0.3080 (3)0.0696 (15)
C320.5914 (5)1.0061 (15)0.3902 (3)0.100 (2)
H32A0.57861.14900.41110.150*
H32B0.53440.91210.40240.150*
H32C0.65210.94630.41110.150*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0509 (18)0.065 (2)0.063 (2)0.0031 (17)0.0019 (15)0.0006 (16)
O20.073 (3)0.067 (3)0.104 (3)0.017 (2)0.005 (2)0.011 (2)
O30.0399 (18)0.061 (2)0.090 (2)0.0182 (17)0.0104 (15)0.0111 (18)
O40.0361 (16)0.0538 (19)0.075 (2)0.0136 (14)0.0160 (13)0.0107 (16)
C10.027 (2)0.037 (2)0.072 (3)0.0017 (18)0.0021 (18)0.008 (2)
C20.035 (2)0.047 (3)0.071 (3)0.000 (2)0.0014 (19)0.009 (2)
C30.041 (2)0.046 (3)0.064 (3)0.002 (2)0.000 (2)0.007 (2)
C40.033 (2)0.042 (2)0.069 (3)0.0008 (19)0.0062 (18)0.005 (2)
C50.030 (2)0.033 (2)0.068 (3)0.0032 (18)0.0065 (17)0.005 (2)
C60.027 (2)0.046 (3)0.074 (3)0.0018 (18)0.0073 (19)0.009 (2)
C70.030 (2)0.034 (2)0.075 (3)0.0024 (19)0.0088 (19)0.001 (2)
C80.035 (2)0.031 (2)0.069 (3)0.0039 (17)0.0097 (18)0.004 (2)
C90.0230 (19)0.034 (2)0.069 (3)0.0048 (16)0.0077 (17)0.0004 (19)
C100.029 (2)0.036 (2)0.069 (3)0.0026 (17)0.0074 (18)0.005 (2)
C110.028 (2)0.048 (3)0.070 (3)0.0002 (19)0.0001 (19)0.007 (2)
C120.033 (2)0.050 (3)0.066 (3)0.0056 (19)0.0006 (19)0.008 (2)
C130.039 (2)0.040 (2)0.062 (3)0.0036 (19)0.0028 (19)0.002 (2)
C140.027 (2)0.044 (2)0.065 (3)0.0036 (18)0.0014 (18)0.004 (2)
C150.042 (3)0.068 (3)0.073 (3)0.018 (2)0.007 (2)0.007 (3)
C160.051 (3)0.081 (4)0.073 (3)0.019 (3)0.014 (2)0.001 (3)
C170.044 (2)0.054 (3)0.056 (3)0.003 (2)0.0052 (19)0.002 (2)
C180.063 (3)0.054 (3)0.076 (3)0.003 (3)0.017 (3)0.011 (3)
C190.035 (2)0.034 (2)0.082 (3)0.0033 (18)0.006 (2)0.006 (2)
C200.067 (3)0.072 (3)0.056 (3)0.017 (3)0.001 (2)0.007 (3)
C210.059 (3)0.069 (3)0.063 (3)0.002 (3)0.004 (2)0.006 (3)
C22a0.052 (6)0.106 (10)0.046 (6)0.011 (7)0.015 (4)0.013 (6)
C23a0.115 (13)0.221 (18)0.049 (6)0.066 (11)0.021 (7)0.032 (9)
C24a0.062 (7)0.33 (2)0.089 (8)0.014 (12)0.019 (7)0.081 (12)
C25a0.072 (7)0.122 (11)0.095 (7)0.009 (7)0.013 (5)0.001 (7)
C26a0.143 (11)0.143 (11)0.076 (6)0.037 (9)0.015 (6)0.016 (7)
C27a0.21 (2)0.161 (14)0.128 (15)0.058 (15)0.000 (13)0.024 (12)
C22b0.092 (16)0.096 (19)0.061 (16)0.049 (14)0.040 (12)0.031 (16)
C23b0.053 (11)0.052 (10)0.099 (16)0.016 (9)0.027 (10)0.009 (9)
C24b0.102 (17)0.050 (10)0.117 (15)0.037 (10)0.034 (12)0.035 (9)
C25b0.19 (3)0.12 (3)0.22 (3)0.04 (2)0.01 (2)0.04 (2)
C26b0.13 (2)0.21 (3)0.087 (15)0.10 (2)0.016 (14)0.041 (18)
C27b0.136 (18)0.17 (3)0.28 (3)0.025 (19)0.023 (18)0.03 (2)
C280.038 (2)0.040 (2)0.066 (3)0.0056 (19)0.0006 (19)0.002 (2)
C290.043 (2)0.060 (3)0.073 (3)0.006 (2)0.007 (2)0.000 (2)
C300.049 (3)0.050 (3)0.073 (3)0.002 (2)0.008 (2)0.013 (2)
C310.048 (3)0.074 (4)0.086 (4)0.006 (3)0.004 (3)0.012 (3)
C320.086 (4)0.135 (6)0.080 (4)0.016 (5)0.005 (3)0.013 (4)
Geometric parameters (Å, º) top
O1—C311.341 (7)C20—C211.540 (7)
O1—C31.459 (5)C20—C22a1.573 (12)
O2—C311.203 (7)C20—H201.0000
O3—C71.212 (5)C21—H21A0.9800
O4—C111.453 (6)C21—H21B0.9800
O4—C91.454 (5)C21—H21C0.9800
C1—C21.510 (6)C22a—C23a1.68 (2)
C1—C101.539 (6)C22a—H22A0.9900
C1—H1A0.9900C22a—H22B0.9900
C1—H1B0.9900C23a—C24a1.572 (16)
C2—C31.512 (6)C23a—H23A0.9900
C2—H2A0.9900C23a—H23B0.9900
C2—H2B0.9900C24a—C25a1.407 (12)
C3—C41.538 (6)C24a—H24A0.9900
C3—H31.0000C24a—H24B0.9900
C4—C301.538 (7)C25a—C26a1.504 (15)
C4—C291.546 (6)C25a—C27a1.550 (15)
C4—C51.558 (6)C25a—H25A1.0000
C5—C61.531 (6)C26a—H26A0.9800
C5—C101.560 (6)C26a—H26B0.9800
C5—H51.0000C26a—H26C0.9800
C6—C71.494 (6)C27a—H27A0.9800
C6—H6A0.9900C27a—H27B0.9800
C6—H6B0.9900C27a—H27C0.9800
C7—C81.521 (6)C22b—C23b1.25 (3)
C8—C91.543 (6)C22b—H22C0.9900
C8—C141.555 (6)C22b—H22D0.9900
C8—H81.0000C23b—C24b1.571 (16)
C9—C111.492 (6)C23b—H23C0.9900
C9—C101.535 (6)C23b—H23D0.9900
C10—C191.554 (7)C24b—C25b1.47 (2)
C11—C121.493 (6)C24b—H24C0.9900
C11—H111.0000C24b—H24D0.9900
C12—C131.538 (6)C25b—C27b1.48 (2)
C12—H12A0.9900C25b—C26b1.508 (19)
C12—H12B0.9900C25b—H25B1.0000
C13—C181.533 (7)C26b—H26D0.9800
C13—C171.555 (6)C26b—H26E0.9800
C13—C141.572 (6)C26b—H26F0.9800
C14—C151.535 (6)C27b—H27D0.9800
C14—C281.544 (7)C27b—H27E0.9800
C15—C161.534 (7)C27b—H27F0.9800
C15—H15A0.9900C28—H28A0.9800
C15—H15B0.9900C28—H28B0.9800
C16—C171.573 (6)C28—H28C0.9800
C16—H16A0.9900C29—H29A0.9800
C16—H16B0.9900C29—H29B0.9800
C17—C201.531 (7)C29—H29C0.9800
C17—H171.0000C30—H30A0.9800
C18—H18A0.9800C30—H30B0.9800
C18—H18B0.9800C30—H30C0.9800
C18—H18C0.9800C31—C321.497 (8)
C19—H19A0.9800C32—H32A0.9800
C19—H19B0.9800C32—H32B0.9800
C19—H19C0.9800C32—H32C0.9800
C20—C22b1.510 (17)
C31—O1—C3115.8 (4)C10—C19—H19B109.5
C11—O4—C961.8 (3)H19A—C19—H19B109.5
C2—C1—C10113.5 (3)C10—C19—H19C109.5
C2—C1—H1A108.9H19A—C19—H19C109.5
C10—C1—H1A108.9H19B—C19—H19C109.5
C2—C1—H1B108.9C22b—C20—C17115.1 (16)
C10—C1—H1B108.9C22b—C20—C21114.8 (14)
H1A—C1—H1B107.7C17—C20—C21112.6 (4)
C1—C2—C3108.5 (3)C17—C20—C22a107.1 (7)
C1—C2—H2A110.0C21—C20—C22a107.3 (8)
C3—C2—H2A110.0C22b—C20—H2092.6
C1—C2—H2B110.0C17—C20—H20109.9
C3—C2—H2B110.0C21—C20—H20109.9
H2A—C2—H2B108.4C22a—C20—H20109.9
O1—C3—C2109.3 (3)C20—C21—H21A109.5
O1—C3—C4109.2 (3)C20—C21—H21B109.5
C2—C3—C4113.0 (4)H21A—C21—H21B109.5
O1—C3—H3108.4C20—C21—H21C109.5
C2—C3—H3108.4H21A—C21—H21C109.5
C4—C3—H3108.4H21B—C21—H21C109.5
C30—C4—C3110.5 (4)C20—C22a—C23a107.7 (11)
C30—C4—C29107.2 (4)C20—C22a—H22A110.2
C3—C4—C29107.8 (4)C23a—C22a—H22A110.2
C30—C4—C5114.7 (4)C20—C22a—H22B110.2
C3—C4—C5107.6 (3)C23a—C22a—H22B110.2
C29—C4—C5108.8 (3)H22A—C22a—H22B108.5
C6—C5—C4111.8 (3)C24a—C23a—C22a103.8 (12)
C6—C5—C10111.1 (4)C24a—C23a—H23A111.0
C4—C5—C10116.9 (3)C22a—C23a—H23A111.0
C6—C5—H5105.3C24a—C23a—H23B111.0
C4—C5—H5105.3C22a—C23a—H23B111.0
C10—C5—H5105.3H23A—C23a—H23B109.0
C7—C6—C5116.6 (3)C25a—C24a—C23a125.2 (13)
C7—C6—H6A108.1C25a—C24a—H24A106.0
C5—C6—H6A108.1C23a—C24a—H24A106.0
C7—C6—H6B108.1C25a—C24a—H24B106.0
C5—C6—H6B108.1C23a—C24a—H24B106.0
H6A—C6—H6B107.3H24A—C24a—H24B106.3
O3—C7—C6119.7 (4)C24a—C25a—C26a109.5 (11)
O3—C7—C8118.5 (4)C24a—C25a—C27a113.3 (13)
C6—C7—C8121.7 (4)C26a—C25a—C27a109.6 (11)
C7—C8—C9115.0 (4)C24a—C25a—H25A108.1
C7—C8—C14110.5 (3)C26a—C25a—H25A108.1
C9—C8—C14110.4 (3)C27a—C25a—H25A108.1
C7—C8—H8106.8C23b—C22b—C20137 (3)
C9—C8—H8106.8C23b—C22b—H22C102.9
C14—C8—H8106.8C20—C22b—H22C102.9
O4—C9—C1159.1 (3)C23b—C22b—H22D102.9
O4—C9—C10112.0 (3)C20—C22b—H22D102.9
C11—C9—C10122.4 (4)H22C—C22b—H22D105.1
O4—C9—C8112.4 (3)C22b—C23b—C24b128 (2)
C11—C9—C8117.6 (4)C22b—C23b—H23C105.3
C10—C9—C8117.4 (3)C24b—C23b—H23C105.3
C9—C10—C1110.8 (3)C22b—C23b—H23D105.3
C9—C10—C19106.1 (4)C24b—C23b—H23D105.3
C1—C10—C19109.7 (4)H23C—C23b—H23D106.0
C9—C10—C5108.1 (3)C25b—C24b—C23b112.0 (16)
C1—C10—C5108.4 (4)C25b—C24b—H24C109.2
C19—C10—C5113.8 (3)C23b—C24b—H24C109.2
O4—C11—C959.1 (3)C25b—C24b—H24D109.2
O4—C11—C12117.1 (4)C23b—C24b—H24D109.2
C9—C11—C12124.4 (4)H24C—C24b—H24D107.9
O4—C11—H11114.8C24b—C25b—C27b112 (2)
C9—C11—H11114.8C24b—C25b—C26b112.1 (19)
C12—C11—H11114.8C27b—C25b—C26b117 (2)
C11—C12—C13114.4 (4)C24b—C25b—H25B104.9
C11—C12—H12A108.7C27b—C25b—H25B104.9
C13—C12—H12A108.7C26b—C25b—H25B104.9
C11—C12—H12B108.7C25b—C26b—H26D109.5
C13—C12—H12B108.7C25b—C26b—H26E109.5
H12A—C12—H12B107.6H26D—C26b—H26E109.5
C18—C13—C12109.7 (4)C25b—C26b—H26F109.5
C18—C13—C17109.7 (4)H26D—C26b—H26F109.5
C12—C13—C17115.8 (4)H26E—C26b—H26F109.5
C18—C13—C14111.7 (4)C25b—C27b—H27D109.5
C12—C13—C14108.2 (3)C25b—C27b—H27E109.5
C17—C13—C14101.5 (3)H27D—C27b—H27E109.5
C15—C14—C28107.3 (4)C25b—C27b—H27F109.5
C15—C14—C8115.8 (4)H27D—C27b—H27F109.5
C28—C14—C8108.5 (3)H27E—C27b—H27F109.5
C15—C14—C13101.9 (3)C14—C28—H28A109.5
C28—C14—C13112.6 (3)C14—C28—H28B109.5
C8—C14—C13110.7 (3)H28A—C28—H28B109.5
C16—C15—C14104.3 (4)C14—C28—H28C109.5
C16—C15—H15A110.9H28A—C28—H28C109.5
C14—C15—H15A110.9H28B—C28—H28C109.5
C16—C15—H15B110.9C4—C29—H29A109.5
C14—C15—H15B110.9C4—C29—H29B109.5
H15A—C15—H15B108.9H29A—C29—H29B109.5
C15—C16—C17107.9 (4)C4—C29—H29C109.5
C15—C16—H16A110.1H29A—C29—H29C109.5
C17—C16—H16A110.1H29B—C29—H29C109.5
C15—C16—H16B110.1C4—C30—H30A109.5
C17—C16—H16B110.1C4—C30—H30B109.5
H16A—C16—H16B108.4H30A—C30—H30B109.5
C20—C17—C13120.2 (4)C4—C30—H30C109.5
C20—C17—C16112.2 (4)H30A—C30—H30C109.5
C13—C17—C16102.5 (4)H30B—C30—H30C109.5
C20—C17—H17107.1O2—C31—O1124.6 (5)
C13—C17—H17107.1O2—C31—C32124.3 (6)
C16—C17—H17107.1O1—C31—C32111.0 (6)
C13—C18—H18A109.5C31—C32—H32A109.5
C13—C18—H18B109.5C31—C32—H32B109.5
H18A—C18—H18B109.5H32A—C32—H32B109.5
C13—C18—H18C109.5C31—C32—H32C109.5
H18A—C18—H18C109.5H32A—C32—H32C109.5
H18B—C18—H18C109.5H32B—C32—H32C109.5
C10—C19—H19A109.5
C10—C1—C2—C361.0 (5)C8—C9—C11—C122.6 (6)
C31—O1—C3—C283.3 (5)O4—C11—C12—C1357.5 (5)
C31—O1—C3—C4152.7 (4)C9—C11—C12—C1312.2 (6)
C1—C2—C3—O1175.6 (3)C11—C12—C13—C1879.9 (5)
C1—C2—C3—C462.6 (5)C11—C12—C13—C17155.3 (4)
O1—C3—C4—C3051.5 (5)C11—C12—C13—C1442.2 (5)
C2—C3—C4—C3070.4 (5)C7—C8—C14—C1559.3 (5)
O1—C3—C4—C2965.4 (4)C9—C8—C14—C15172.3 (4)
C2—C3—C4—C29172.8 (4)C7—C8—C14—C2861.4 (4)
O1—C3—C4—C5177.4 (3)C9—C8—C14—C2867.0 (4)
C2—C3—C4—C555.5 (4)C7—C8—C14—C13174.7 (3)
C30—C4—C5—C655.2 (5)C9—C8—C14—C1357.0 (4)
C3—C4—C5—C6178.6 (3)C18—C13—C14—C1569.6 (5)
C29—C4—C5—C664.8 (5)C12—C13—C14—C15169.6 (4)
C30—C4—C5—C1074.5 (5)C17—C13—C14—C1547.3 (4)
C3—C4—C5—C1049.0 (5)C18—C13—C14—C28175.8 (4)
C29—C4—C5—C10165.5 (4)C12—C13—C14—C2855.0 (4)
C4—C5—C6—C7170.2 (3)C17—C13—C14—C2867.3 (4)
C10—C5—C6—C737.6 (5)C18—C13—C14—C854.2 (5)
C5—C6—C7—O3177.1 (4)C12—C13—C14—C866.6 (4)
C5—C6—C7—C82.1 (6)C17—C13—C14—C8171.1 (3)
O3—C7—C8—C9163.4 (4)C28—C14—C15—C1681.0 (5)
C6—C7—C8—C915.8 (6)C8—C14—C15—C16157.6 (4)
O3—C7—C8—C1470.8 (5)C13—C14—C15—C1637.4 (5)
C6—C7—C8—C14110.0 (4)C14—C15—C16—C1713.9 (6)
C11—O4—C9—C10115.5 (4)C18—C13—C17—C2044.8 (5)
C11—O4—C9—C8109.7 (4)C12—C13—C17—C2080.1 (5)
C7—C8—C9—O4143.8 (3)C14—C13—C17—C20163.0 (4)
C14—C8—C9—O490.4 (4)C18—C13—C17—C1680.4 (4)
C7—C8—C9—C11150.5 (4)C12—C13—C17—C16154.7 (4)
C14—C8—C9—C1124.6 (5)C14—C13—C17—C1637.8 (4)
C7—C8—C9—C1011.7 (5)C15—C16—C17—C20145.7 (5)
C14—C8—C9—C10137.5 (4)C15—C16—C17—C1315.4 (5)
O4—C9—C10—C159.4 (4)C13—C17—C20—C22b171.3 (15)
C11—C9—C10—C17.0 (5)C16—C17—C20—C22b50.9 (15)
C8—C9—C10—C1168.2 (3)C13—C17—C20—C2154.6 (6)
O4—C9—C10—C1959.5 (4)C16—C17—C20—C21175.0 (5)
C11—C9—C10—C19126.0 (4)C13—C17—C20—C22a172.2 (7)
C8—C9—C10—C1972.8 (4)C16—C17—C20—C22a67.3 (8)
O4—C9—C10—C5178.1 (3)C22b—C20—C22a—C23a48 (6)
C11—C9—C10—C5111.7 (4)C17—C20—C22a—C23a169.0 (10)
C8—C9—C10—C549.5 (5)C21—C20—C22a—C23a70.0 (12)
C2—C1—C10—C9171.2 (3)C20—C22a—C23a—C24a178.8 (12)
C2—C1—C10—C1972.0 (5)C22a—C23a—C24a—C25a179.3 (15)
C2—C1—C10—C552.8 (5)C23a—C24a—C25a—C26a73.4 (18)
C6—C5—C10—C962.1 (4)C23a—C24a—C25a—C27a164.0 (17)
C4—C5—C10—C9167.9 (3)C17—C20—C22b—C23b167 (4)
C6—C5—C10—C1177.7 (3)C21—C20—C22b—C23b34 (5)
C4—C5—C10—C147.7 (5)C22a—C20—C22b—C23b101 (8)
C6—C5—C10—C1955.4 (5)C20—C22b—C23b—C24b149 (3)
C4—C5—C10—C1974.6 (5)C22b—C23b—C24b—C25b175 (3)
C9—O4—C11—C12115.7 (4)C23b—C24b—C25b—C27b74 (3)
C10—C9—C11—O497.9 (4)C23b—C24b—C25b—C26b153 (3)
C8—C9—C11—O4100.9 (4)C3—O1—C31—O26.6 (7)
O4—C9—C11—C12103.5 (5)C3—O1—C31—C32171.7 (4)
C10—C9—C11—C12158.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6B···O3i0.992.363.300 (9)159
C18—H18B···O40.982.383.072 (9)128
C19—H19C···O40.982.432.882 (8)107
C29—H29C···O10.982.562.930 (8)102
C30—H30B···O10.982.462.836 (9)102
Symmetry code: (i) x+2, y+1/2, z.
 

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