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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2142.
Published online 2010 July 31. doi:  10.1107/S1600536810029168
PMCID: PMC3007388

Cyclo­art-24-ene-3β,26-diol from the leaves of Aglaia exima

Abstract

Cyclo­art-24-ene-3β,26-diol, C30H50O2, isolated from the leaves of Aglaia exima, has three six-membered rings fused together that adopt chair conformations. There are two independent mol­ecules in the asymmetric unit. O—H(...)O hydrogen bond inter­actions between the hydroxyl groups in the 3β and 26 positions lead to the formation of a layer structure parallel to (10An external file that holds a picture, illustration, etc.
Object name is e-66-o2142-efi1.jpg).

Related literature

For the spectroscopic characterization of the title compound, see: Anjaneyulu et al. (1985 [triangle], 1994 [triangle]); Parveen et al. (1990 [triangle]); Takahashi & Takani (1975 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2142-scheme1.jpg

Experimental

Crystal data

  • C30H50O2
  • M r = 442.70
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2142-efi2.jpg
  • a = 9.9950 (14) Å
  • b = 7.512 (1) Å
  • c = 34.820 (5) Å
  • β = 91.029 (2)°
  • V = 2614.0 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 100 K
  • 0.45 × 0.15 × 0.02 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 16958 measured reflections
  • 4970 independent reflections
  • 3318 reflections with I > 2σ(I)
  • R int = 0.085

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.143
  • S = 0.96
  • 4970 reflections
  • 593 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.19 e Å−3

Data collection: APEX2 software (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029168/jh2187sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029168/jh2187Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Cycloart-24-ene-3β,26-diol (Scheme I) has been isolated from the leaves of Garcinia magnostana (Parveeen et al., 1990), the stem-bark of Mangifera indica (Anjaneyulu et al., 1985, 1994) and from the wood of Schizandar nigra (Takahashi & Takani, 1975). The structure was elucidated in the studies by spectroscopic methods. The absolute configuration in the present crystal structure analysis is assumed to be that reported in the studies. Cycloart-24-ene-3β,26-diol (Fig. 1) in this study was isolated from the leaves of Aglaia exima.

Experimental

The leaves of Algaia exima were collected from Kampung Kepayang, Pahang, Malaysia. The leaves (1 kg) were extracted at room temperature with n-hexane successively; the insoluble material was removed by filtration after four days. The solvent was evaporated to dryness to give a residue of 25 g; a 15 g portion was subjected to column chromatography over silica gel at a gradient mixture of n-hexane and ethyl acetate. Of the 123 fractions, fraction 92 gave a colorless solid, identified by solution NMR, as cycloart-24-ene-3β,26-diol. Single crystals were obtained by recrystallization from ethyl acetate.

Refinement

Carbon-bound H-atoms were placed in calculated positions [C—H 0.95 to 1.00 Å, U(H) 1.2 to 1.5U(C)] and were included in the refinement in the riding model approximation. The hydroxy H-atoms were similarly placed [O–H 0.84 Å] and their temperature factor similarly tied.

Some 4185 Friedel pairs were merged.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of one of the two independent molecules of C30H50O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Thermal ellipsoid plot (Barbour, 2001) of the second independent molecule of C30H50O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C30H50O2F(000) = 984
Mr = 442.70Dx = 1.125 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1946 reflections
a = 9.9950 (14) Åθ = 2.3–21.1°
b = 7.512 (1) ŵ = 0.07 mm1
c = 34.820 (5) ÅT = 100 K
β = 91.029 (2)°Plate, colorless
V = 2614.0 (6) Å30.45 × 0.15 × 0.02 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3318 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.085
graphiteθmax = 25.0°, θmin = 1.8°
ω scansh = −11→11
16958 measured reflectionsk = −8→8
4970 independent reflectionsl = −36→41

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.0758P)2 + 0.1056P] where P = (Fo2 + 2Fc2)/3
4970 reflections(Δ/σ)max = 0.001
593 parametersΔρmax = 0.18 e Å3
1 restraintΔρmin = −0.19 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.8196 (3)0.5009 (4)0.73269 (10)0.0366 (9)
H10.88420.50890.71770.055*
O2−0.0926 (3)0.0538 (5)0.28107 (9)0.0421 (9)
H2−0.1424−0.01870.26930.063*
O31.7903 (3)0.7649 (5)1.24335 (10)0.0485 (10)
H31.85340.79271.22890.073*
O40.9518 (4)0.2801 (5)0.78237 (9)0.0436 (9)
H40.90510.34380.76750.065*
C10.6990 (5)0.4641 (6)0.71105 (14)0.0298 (12)
H1a0.62460.45760.72980.036*
C20.6698 (5)0.6209 (6)0.68482 (13)0.0278 (11)
H2A0.74630.63870.66760.033*
H2B0.66030.72970.70060.033*
C30.5413 (4)0.5941 (6)0.66033 (14)0.0280 (11)
H3A0.46260.59510.67720.034*
H3B0.53150.69330.64180.034*
C40.5463 (4)0.4196 (6)0.63883 (13)0.0254 (11)
C50.5667 (5)0.2676 (6)0.66768 (13)0.0267 (11)
H50.49610.28430.68740.032*
C60.7025 (5)0.2847 (7)0.68988 (14)0.0339 (12)
C70.7133 (6)0.1353 (7)0.71945 (17)0.0524 (18)
H7A0.72880.02200.70630.079*
H7B0.63000.12820.73380.079*
H7C0.78810.15980.73730.079*
C80.8233 (4)0.2766 (7)0.66345 (15)0.0433 (14)
H8A0.81660.17040.64720.065*
H8B0.90580.27090.67900.065*
H8C0.82480.38320.64720.065*
C90.5395 (5)0.0842 (6)0.64985 (14)0.0320 (12)
H9A0.61170.05370.63190.038*
H9B0.5382−0.00740.67030.038*
C100.4054 (4)0.0867 (6)0.62840 (13)0.0292 (11)
H10A0.33570.13590.64530.035*
H10B0.3793−0.03620.62130.035*
C110.4152 (4)0.2002 (6)0.59238 (13)0.0238 (11)
H110.48850.14620.57710.029*
C120.4619 (4)0.3924 (6)0.60191 (13)0.0226 (10)
C130.6114 (4)0.4216 (6)0.60022 (12)0.0272 (11)
H13A0.66780.31840.59340.033*
H13B0.64310.53750.59040.033*
C140.3700 (4)0.5463 (6)0.58923 (13)0.0255 (11)
H14A0.42440.65620.58810.031*
H14B0.30210.56400.60920.031*
C150.2956 (4)0.5231 (6)0.54978 (12)0.0216 (10)
H15A0.20010.55360.55290.026*
H15B0.33350.60820.53120.026*
C160.3052 (4)0.3349 (5)0.53316 (12)0.0193 (10)
C170.4415 (4)0.3143 (6)0.51311 (13)0.0233 (10)
H17A0.51380.35030.53080.035*
H17B0.44270.38990.49020.035*
H17C0.45410.18970.50560.035*
C180.2899 (4)0.1969 (6)0.56606 (13)0.0219 (10)
C190.1616 (4)0.2328 (6)0.58904 (13)0.0238 (10)
H19A0.14650.13410.60680.036*
H19B0.08490.24330.57120.036*
H19C0.17210.34380.60360.036*
C200.2706 (4)0.0201 (5)0.54461 (12)0.0224 (10)
H20A0.2152−0.06270.55970.027*
H20B0.3580−0.03680.53980.027*
C210.1991 (4)0.0684 (6)0.50638 (12)0.0216 (10)
H21A0.10760.01810.50560.026*
H21B0.24910.01970.48450.026*
C220.1935 (4)0.2760 (6)0.50405 (12)0.0209 (10)
H220.10600.31360.51490.025*
C230.1965 (4)0.3444 (5)0.46270 (13)0.0221 (10)
H230.28320.30560.45150.027*
C240.1913 (4)0.5507 (6)0.46055 (13)0.0247 (10)
H24A0.27260.60040.47240.037*
H24B0.11280.59380.47420.037*
H24C0.18500.58800.43360.037*
C250.0833 (4)0.2608 (6)0.43826 (12)0.0249 (10)
H25A0.08950.12960.44060.030*
H25B−0.00350.29750.44900.030*
C260.0835 (4)0.3098 (6)0.39569 (12)0.0256 (11)
H26A0.05240.43420.39260.031*
H26B0.17630.30320.38630.031*
C27−0.0035 (4)0.1910 (7)0.37175 (13)0.0307 (12)
H27−0.01610.07400.38140.037*
C28−0.0663 (4)0.2285 (7)0.33829 (13)0.0292 (11)
C29−0.0642 (6)0.4038 (7)0.31926 (16)0.0541 (17)
H29A−0.01830.49000.33600.081*
H29B−0.15620.44360.31410.081*
H29C−0.01660.39420.29500.081*
C30−0.1459 (5)0.0885 (8)0.31816 (15)0.0462 (15)
H30A−0.1442−0.02220.33360.055*
H30B−0.24010.12780.31540.055*
C311.6695 (5)0.7436 (7)1.22082 (15)0.0388 (13)
H311.59270.75651.23860.047*
C321.6570 (5)0.8907 (6)1.19104 (14)0.0338 (12)
H32A1.73590.88771.17430.041*
H32B1.65621.00741.20420.041*
C331.5287 (5)0.8723 (6)1.16604 (14)0.0314 (12)
H33A1.44870.88561.18220.038*
H33B1.52620.96611.14610.038*
C341.5290 (5)0.6896 (6)1.14735 (14)0.0297 (12)
C351.5352 (5)0.5445 (6)1.17769 (14)0.0320 (12)
H351.45980.57221.19520.038*
C361.6625 (5)0.5531 (7)1.20379 (14)0.0355 (13)
C371.6508 (6)0.4222 (7)1.23772 (16)0.0543 (17)
H37A1.56320.43631.24950.082*
H37B1.72150.44731.25680.082*
H37C1.66030.29991.22840.082*
C381.7893 (5)0.5113 (8)1.18178 (16)0.0503 (16)
H38A1.80320.60311.16230.075*
H38B1.78000.39491.16930.075*
H38C1.86610.50901.19970.075*
C391.5035 (5)0.3581 (6)1.16203 (15)0.0354 (13)
H39A1.57920.31491.14660.043*
H39B1.49110.27451.18370.043*
C401.3760 (5)0.3636 (6)1.13696 (14)0.0319 (12)
H40A1.34810.24081.13030.038*
H40B1.30290.42031.15140.038*
C411.4014 (4)0.4681 (6)1.10048 (13)0.0246 (11)
H411.47670.40601.08750.030*
C421.4523 (4)0.6587 (6)1.10937 (14)0.0268 (11)
C431.6032 (4)0.6776 (7)1.10967 (13)0.0331 (12)
H43A1.64120.78871.09920.040*
H43B1.65690.56921.10500.040*
C441.3665 (4)0.8139 (6)1.09347 (13)0.0272 (11)
H44A1.42310.92211.09330.033*
H44B1.29330.83581.11160.033*
C451.3034 (4)0.7912 (6)1.05290 (13)0.0252 (10)
H45A1.20850.82851.05350.030*
H45B1.34990.87111.03490.030*
C461.3107 (4)0.5989 (6)1.03765 (12)0.0209 (10)
C471.4503 (4)0.5699 (6)1.02068 (13)0.0263 (11)
H47A1.51900.60881.03930.039*
H47B1.45800.63910.99700.039*
H47C1.46270.44321.01500.039*
C481.2828 (4)0.4665 (6)1.07123 (13)0.0245 (11)
C491.1492 (4)0.5086 (6)1.09087 (13)0.0280 (11)
H49A1.12950.41521.10960.042*
H49B1.07710.51381.07140.042*
H49C1.15620.62361.10400.042*
C501.2662 (4)0.2873 (6)1.05027 (13)0.0260 (11)
H50A1.20610.20731.06460.031*
H50B1.35390.22781.04740.031*
C511.2046 (4)0.3346 (6)1.01051 (14)0.0282 (11)
H51A1.25870.28190.98990.034*
H51B1.11240.28721.00820.034*
C521.2033 (4)0.5400 (6)1.00700 (13)0.0239 (10)
H521.11460.58141.01640.029*
C531.2148 (4)0.6056 (6)0.96550 (13)0.0248 (11)
H531.30360.56630.95580.030*
C541.2084 (5)0.8091 (6)0.96208 (14)0.0322 (12)
H54A1.28650.86160.97520.048*
H54B1.12650.85260.97400.048*
H54C1.20830.84300.93490.048*
C551.1061 (4)0.5187 (6)0.94001 (12)0.0289 (11)
H55A1.11200.38790.94310.035*
H55B1.01740.55650.94930.035*
C561.1143 (4)0.5629 (7)0.89736 (12)0.0287 (11)
H56A1.07590.68260.89270.034*
H56B1.20940.56580.88990.034*
C571.0402 (5)0.4284 (7)0.87294 (13)0.0347 (12)
H571.04640.30830.88140.042*
C580.9668 (4)0.4553 (7)0.84101 (13)0.0341 (12)
C590.9430 (6)0.6328 (8)0.82220 (16)0.0490 (16)
H59A0.97260.72800.83960.074*
H59B0.84740.64690.81630.074*
H59C0.99360.63940.79840.074*
C600.9049 (5)0.2981 (8)0.82061 (14)0.0441 (14)
H60A0.92630.18820.83520.053*
H60B0.80640.31210.81990.053*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0353 (19)0.030 (2)0.044 (2)−0.0015 (16)−0.0179 (17)−0.0067 (17)
O20.048 (2)0.046 (2)0.033 (2)−0.0128 (18)0.0014 (17)−0.0135 (18)
O30.050 (2)0.044 (2)0.050 (2)−0.001 (2)−0.0276 (19)−0.009 (2)
O40.061 (2)0.041 (2)0.028 (2)0.0001 (19)−0.0149 (17)0.0036 (17)
C10.026 (3)0.026 (3)0.037 (3)−0.003 (2)−0.011 (2)0.000 (2)
C20.031 (3)0.024 (3)0.029 (3)−0.004 (2)−0.003 (2)−0.002 (2)
C30.024 (2)0.023 (3)0.037 (3)0.004 (2)−0.005 (2)0.000 (2)
C40.023 (2)0.022 (3)0.030 (3)0.001 (2)−0.008 (2)−0.006 (2)
C50.035 (3)0.015 (2)0.029 (3)0.000 (2)−0.011 (2)−0.001 (2)
C60.033 (3)0.028 (3)0.040 (3)0.002 (2)−0.014 (2)0.002 (2)
C70.071 (4)0.024 (3)0.061 (4)−0.008 (3)−0.042 (3)0.007 (3)
C80.029 (3)0.043 (3)0.057 (3)0.013 (2)−0.018 (2)−0.021 (3)
C90.038 (3)0.019 (3)0.038 (3)−0.001 (2)−0.015 (2)0.000 (2)
C100.030 (2)0.017 (2)0.040 (3)−0.007 (2)−0.014 (2)0.002 (2)
C110.021 (2)0.023 (3)0.028 (3)0.0027 (19)−0.006 (2)−0.001 (2)
C120.020 (2)0.020 (2)0.028 (3)−0.0056 (18)−0.005 (2)0.000 (2)
C130.023 (2)0.029 (3)0.030 (3)−0.005 (2)−0.004 (2)−0.005 (2)
C140.023 (2)0.018 (2)0.035 (3)0.0005 (19)−0.003 (2)−0.001 (2)
C150.022 (2)0.018 (2)0.025 (3)0.0038 (18)−0.001 (2)−0.006 (2)
C160.010 (2)0.022 (2)0.026 (3)0.0001 (17)0.0004 (18)−0.003 (2)
C170.016 (2)0.022 (2)0.032 (3)−0.0010 (19)0.0014 (19)−0.001 (2)
C180.017 (2)0.017 (2)0.032 (3)−0.0007 (18)−0.0018 (19)0.000 (2)
C190.020 (2)0.023 (3)0.028 (3)−0.0021 (18)−0.0008 (19)−0.001 (2)
C200.022 (2)0.014 (2)0.031 (3)−0.0048 (18)0.000 (2)0.003 (2)
C210.017 (2)0.020 (2)0.027 (3)−0.0037 (19)0.0011 (19)−0.002 (2)
C220.017 (2)0.024 (2)0.022 (2)0.0003 (19)0.0012 (18)−0.001 (2)
C230.017 (2)0.019 (2)0.030 (3)−0.0030 (18)−0.0026 (19)−0.005 (2)
C240.022 (2)0.026 (3)0.027 (3)−0.004 (2)−0.005 (2)0.002 (2)
C250.020 (2)0.028 (3)0.027 (3)−0.0027 (19)0.0003 (19)−0.002 (2)
C260.017 (2)0.032 (3)0.028 (3)−0.001 (2)−0.0001 (19)−0.002 (2)
C270.034 (3)0.033 (3)0.025 (3)−0.016 (2)0.005 (2)−0.001 (2)
C280.022 (2)0.038 (3)0.028 (3)−0.006 (2)0.004 (2)−0.010 (2)
C290.069 (4)0.048 (4)0.045 (4)0.003 (3)−0.031 (3)−0.009 (3)
C300.036 (3)0.071 (4)0.031 (3)−0.022 (3)−0.003 (2)−0.017 (3)
C310.036 (3)0.042 (3)0.038 (3)0.002 (2)−0.018 (2)−0.008 (3)
C320.039 (3)0.025 (3)0.037 (3)0.001 (2)−0.013 (2)−0.006 (2)
C330.030 (3)0.027 (3)0.037 (3)0.003 (2)−0.007 (2)−0.005 (2)
C340.033 (3)0.021 (3)0.035 (3)0.003 (2)−0.010 (2)−0.003 (2)
C350.036 (3)0.024 (3)0.036 (3)0.006 (2)−0.014 (2)−0.005 (2)
C360.038 (3)0.027 (3)0.040 (3)0.004 (2)−0.020 (2)−0.007 (2)
C370.077 (4)0.031 (3)0.053 (4)0.000 (3)−0.040 (3)0.001 (3)
C380.039 (3)0.047 (4)0.063 (4)0.013 (3)−0.024 (3)−0.025 (3)
C390.045 (3)0.021 (3)0.039 (3)0.002 (2)−0.018 (2)−0.004 (2)
C400.038 (3)0.021 (3)0.037 (3)−0.003 (2)−0.014 (2)0.000 (2)
C410.024 (2)0.018 (2)0.032 (3)0.0019 (19)−0.008 (2)0.000 (2)
C420.024 (2)0.020 (2)0.036 (3)−0.0025 (19)−0.005 (2)0.001 (2)
C430.025 (2)0.034 (3)0.040 (3)−0.002 (2)−0.003 (2)−0.005 (2)
C440.023 (2)0.025 (3)0.034 (3)−0.001 (2)−0.005 (2)−0.002 (2)
C450.022 (2)0.022 (2)0.031 (3)−0.002 (2)−0.003 (2)−0.006 (2)
C460.018 (2)0.025 (3)0.020 (2)−0.0017 (19)0.0013 (18)0.000 (2)
C470.016 (2)0.029 (3)0.034 (3)0.001 (2)0.0000 (19)−0.009 (2)
C480.020 (2)0.022 (3)0.031 (3)−0.0010 (19)−0.004 (2)0.000 (2)
C490.022 (2)0.031 (3)0.031 (3)−0.0029 (19)−0.001 (2)0.000 (2)
C500.022 (2)0.025 (3)0.030 (3)−0.005 (2)−0.005 (2)−0.003 (2)
C510.021 (2)0.029 (3)0.034 (3)−0.005 (2)−0.006 (2)0.000 (2)
C520.017 (2)0.024 (3)0.030 (3)0.0017 (19)−0.002 (2)−0.003 (2)
C530.016 (2)0.030 (3)0.028 (3)−0.0027 (19)0.000 (2)−0.002 (2)
C540.032 (3)0.033 (3)0.031 (3)−0.004 (2)−0.005 (2)0.006 (2)
C550.025 (2)0.035 (3)0.027 (3)−0.005 (2)−0.003 (2)0.000 (2)
C560.026 (2)0.037 (3)0.023 (3)−0.001 (2)−0.003 (2)−0.001 (2)
C570.034 (3)0.042 (3)0.028 (3)−0.009 (2)−0.001 (2)0.005 (2)
C580.025 (2)0.052 (3)0.025 (3)−0.009 (2)0.003 (2)0.005 (3)
C590.053 (3)0.056 (4)0.038 (3)0.018 (3)−0.014 (3)−0.006 (3)
C600.042 (3)0.057 (4)0.032 (3)−0.021 (3)−0.008 (2)0.009 (3)

Geometric parameters (Å, °)

O1—C11.437 (5)C29—H29B0.9800
O1—H10.8400C29—H29C0.9800
O2—C301.430 (6)C30—H30A0.9900
O2—H20.8400C30—H30B0.9900
O3—C311.437 (5)C31—C321.519 (7)
O3—H30.8400C31—C361.550 (7)
O4—C601.426 (6)C31—H311.0000
O4—H40.8400C32—C331.543 (6)
C1—C21.516 (6)C32—H32A0.9900
C1—C61.537 (7)C32—H32B0.9900
C1—H1a1.0000C33—C341.519 (6)
C2—C31.542 (6)C33—H33A0.9900
C2—H2A0.9900C33—H33B0.9900
C2—H2B0.9900C34—C351.518 (7)
C3—C41.510 (6)C34—C431.521 (7)
C3—H3A0.9900C34—C421.534 (6)
C3—H3B0.9900C35—C391.534 (6)
C4—C131.504 (6)C35—C361.551 (6)
C4—C51.532 (6)C35—H351.0000
C4—C121.538 (6)C36—C381.525 (7)
C5—C91.534 (6)C36—C371.543 (7)
C5—C61.555 (6)C37—H37A0.9800
C5—H51.0000C37—H37B0.9800
C6—C81.533 (7)C37—H37C0.9800
C6—C71.525 (7)C38—H38A0.9800
C7—H7A0.9800C38—H38B0.9800
C7—H7B0.9800C38—H38C0.9800
C7—H7C0.9800C39—C401.532 (6)
C8—H8A0.9800C39—H39A0.9900
C8—H8B0.9800C39—H39B0.9900
C8—H8C0.9800C40—C411.519 (6)
C9—C101.523 (6)C40—H40A0.9900
C9—H9A0.9900C40—H40B0.9900
C9—H9B0.9900C41—C481.549 (5)
C10—C111.521 (6)C41—C421.549 (6)
C10—H10A0.9900C41—H411.0000
C10—H10B0.9900C42—C431.514 (6)
C11—C181.539 (5)C42—C441.544 (6)
C11—C121.552 (6)C43—H43A0.9900
C11—H111.0000C43—H43B0.9900
C12—C131.513 (6)C44—C451.546 (6)
C12—C141.536 (6)C44—H44A0.9900
C13—H13A0.9900C44—H44B0.9900
C13—H13B0.9900C45—C461.541 (6)
C14—C151.560 (6)C45—H45A0.9900
C14—H14A0.9900C45—H45B0.9900
C14—H14B0.9900C46—C471.541 (6)
C15—C161.531 (6)C46—C521.564 (6)
C15—H15A0.9900C46—C481.564 (6)
C15—H15B0.9900C47—H47A0.9800
C16—C171.550 (6)C47—H47B0.9800
C16—C181.554 (6)C47—H47C0.9800
C16—C221.558 (5)C48—C501.539 (6)
C17—H17A0.9800C48—C491.543 (6)
C17—H17B0.9800C49—H49A0.9800
C17—H17C0.9800C49—H49B0.9800
C18—C201.534 (6)C49—H49C0.9800
C18—C191.548 (6)C50—C511.546 (6)
C19—H19A0.9800C50—H50A0.9900
C19—H19B0.9800C50—H50B0.9900
C19—H19C0.9800C51—C521.548 (6)
C20—C211.542 (6)C51—H51A0.9900
C20—H20A0.9900C51—H51B0.9900
C20—H20B0.9900C52—C531.533 (6)
C21—C221.563 (6)C52—H521.0000
C21—H21A0.9900C53—C541.535 (6)
C21—H21B0.9900C53—C551.536 (6)
C22—C231.530 (6)C53—H531.0000
C22—H221.0000C54—H54A0.9800
C23—C251.538 (5)C54—H54B0.9800
C23—C241.552 (6)C54—H54C0.9800
C23—H231.0000C55—C561.526 (6)
C24—H24A0.9800C55—H55A0.9900
C24—H24B0.9800C55—H55B0.9900
C24—H24C0.9800C56—C571.507 (6)
C25—C261.528 (6)C56—H56A0.9900
C25—H25A0.9900C56—H56B0.9900
C25—H25B0.9900C57—C581.336 (6)
C26—C271.490 (6)C57—H570.9500
C26—H26A0.9900C58—C591.503 (7)
C26—H26B0.9900C58—C601.506 (7)
C27—C281.344 (6)C59—H59A0.9800
C27—H270.9500C59—H59B0.9800
C28—C291.474 (7)C59—H59C0.9800
C28—C301.486 (7)C60—H60A0.9900
C29—H29A0.9800C60—H60B0.9900
C1—O1—H1109.5C28—C30—H30B109.6
C30—O2—H2109.5H30A—C30—H30B108.1
C31—O3—H3109.5O3—C31—C32110.5 (4)
C60—O4—H4109.5O3—C31—C36110.1 (4)
O1—C1—C2108.5 (4)C32—C31—C36114.1 (4)
O1—C1—C6113.2 (4)O3—C31—H31107.3
C2—C1—C6113.5 (4)C32—C31—H31107.3
O1—C1—H1a107.1C36—C31—H31107.3
C2—C1—H1a107.1C31—C32—C33112.1 (4)
C6—C1—H1a107.1C31—C32—H32A109.2
C1—C2—C3112.4 (4)C33—C32—H32A109.2
C1—C2—H2A109.1C31—C32—H32B109.2
C3—C2—H2A109.1C33—C32—H32B109.2
C1—C2—H2B109.1H32A—C32—H32B107.9
C3—C2—H2B109.1C34—C33—C32108.4 (4)
H2A—C2—H2B107.8C34—C33—H33A110.0
C4—C3—C2110.7 (4)C32—C33—H33A110.0
C4—C3—H3A109.5C34—C33—H33B110.0
C2—C3—H3A109.5C32—C33—H33B110.0
C4—C3—H3B109.5H33A—C33—H33B108.4
C2—C3—H3B109.5C35—C34—C33110.5 (4)
H3A—C3—H3B108.1C35—C34—C43122.9 (4)
C13—C4—C3116.9 (4)C33—C34—C43115.4 (4)
C13—C4—C5122.6 (4)C35—C34—C42120.3 (4)
C3—C4—C5109.1 (4)C33—C34—C42120.1 (4)
C13—C4—C1259.6 (3)C43—C34—C4259.4 (3)
C3—C4—C12120.5 (4)C34—C35—C39113.7 (4)
C5—C4—C12120.9 (4)C34—C35—C36113.6 (4)
C4—C5—C9112.6 (4)C39—C35—C36114.1 (4)
C4—C5—C6111.7 (4)C34—C35—H35104.7
C9—C5—C6115.0 (4)C39—C35—H35104.7
C4—C5—H5105.6C36—C35—H35104.7
C9—C5—H5105.6C38—C36—C37109.2 (4)
C6—C5—H5105.6C38—C36—C31110.5 (4)
C8—C6—C7109.2 (4)C37—C36—C31107.4 (4)
C8—C6—C1110.3 (4)C38—C36—C35112.2 (4)
C7—C6—C1108.9 (4)C37—C36—C35110.5 (4)
C8—C6—C5112.9 (4)C31—C36—C35107.0 (4)
C7—C6—C5109.0 (4)C36—C37—H37A109.5
C1—C6—C5106.5 (4)C36—C37—H37B109.5
C6—C7—H7A109.5H37A—C37—H37B109.5
C6—C7—H7B109.5C36—C37—H37C109.5
H7A—C7—H7B109.5H37A—C37—H37C109.5
C6—C7—H7C109.5H37B—C37—H37C109.5
H7A—C7—H7C109.5C36—C38—H38A109.5
H7B—C7—H7C109.5C36—C38—H38B109.5
C6—C8—H8A109.5H38A—C38—H38B109.5
C6—C8—H8B109.5C36—C38—H38C109.5
H8A—C8—H8B109.5H38A—C38—H38C109.5
C6—C8—H8C109.5H38B—C38—H38C109.5
H8A—C8—H8C109.5C40—C39—C35110.0 (4)
H8B—C8—H8C109.5C40—C39—H39A109.7
C10—C9—C5109.6 (4)C35—C39—H39A109.7
C10—C9—H9A109.8C40—C39—H39B109.7
C5—C9—H9A109.8C35—C39—H39B109.7
C10—C9—H9B109.8H39A—C39—H39B108.2
C5—C9—H9B109.8C41—C40—C39109.9 (4)
H9A—C9—H9B108.2C41—C40—H40A109.7
C9—C10—C11110.0 (4)C39—C40—H40A109.7
C9—C10—H10A109.7C41—C40—H40B109.7
C11—C10—H10A109.7C39—C40—H40B109.7
C9—C10—H10B109.7H40A—C40—H40B108.2
C11—C10—H10B109.7C40—C41—C48114.1 (4)
H10A—C10—H10B108.2C40—C41—C42111.7 (4)
C10—C11—C18114.7 (4)C48—C41—C42112.6 (3)
C10—C11—C12111.6 (4)C40—C41—H41105.9
C18—C11—C12112.4 (3)C48—C41—H41105.9
C10—C11—H11105.8C42—C41—H41105.9
C18—C11—H11105.8C43—C42—C3459.9 (3)
C12—C11—H11105.8C43—C42—C44118.6 (4)
C13—C12—C14117.8 (4)C34—C42—C44117.4 (4)
C13—C12—C459.1 (3)C43—C42—C41114.3 (4)
C14—C12—C4117.1 (4)C34—C42—C41118.0 (4)
C13—C12—C11114.8 (4)C44—C42—C41116.6 (3)
C14—C12—C11117.6 (3)C42—C43—C3460.7 (3)
C4—C12—C11117.4 (4)C42—C43—H43A117.7
C4—C13—C1261.3 (3)C34—C43—H43A117.7
C4—C13—H13A117.6C42—C43—H43B117.7
C12—C13—H13A117.6C34—C43—H43B117.7
C4—C13—H13B117.6H43A—C43—H43B114.8
C12—C13—H13B117.6C42—C44—C45117.4 (4)
H13A—C13—H13B114.7C42—C44—H44A108.0
C12—C14—C15116.2 (4)C45—C44—H44A108.0
C12—C14—H14A108.2C42—C44—H44B108.0
C15—C14—H14A108.2C45—C44—H44B108.0
C12—C14—H14B108.2H44A—C44—H44B107.2
C15—C14—H14B108.2C46—C45—C44113.4 (4)
H14A—C14—H14B107.4C46—C45—H45A108.9
C16—C15—C14113.8 (3)C44—C45—H45A108.9
C16—C15—H15A108.8C46—C45—H45B108.9
C14—C15—H15A108.8C44—C45—H45B108.9
C16—C15—H15B108.8H45A—C45—H45B107.7
C14—C15—H15B108.8C47—C46—C45108.3 (3)
H15A—C15—H15B107.7C47—C46—C52108.3 (3)
C15—C16—C17108.9 (3)C45—C46—C52117.7 (3)
C15—C16—C18109.3 (3)C47—C46—C48111.8 (3)
C17—C16—C18111.4 (3)C45—C46—C48109.2 (4)
C15—C16—C22117.3 (3)C52—C46—C48101.6 (3)
C17—C16—C22107.7 (3)C46—C47—H47A109.5
C18—C16—C22102.2 (3)C46—C47—H47B109.5
C16—C17—H17A109.5H47A—C47—H47B109.5
C16—C17—H17B109.5C46—C47—H47C109.5
H17A—C17—H17B109.5H47A—C47—H47C109.5
C16—C17—H17C109.5H47B—C47—H47C109.5
H17A—C17—H17C109.5C50—C48—C49107.6 (4)
H17B—C17—H17C109.5C50—C48—C41113.2 (4)
C20—C18—C11113.5 (3)C49—C48—C41111.4 (4)
C20—C18—C19107.7 (3)C50—C48—C46102.8 (3)
C11—C18—C19111.2 (4)C49—C48—C46111.6 (3)
C20—C18—C16103.4 (3)C41—C48—C46110.0 (3)
C11—C18—C16109.8 (3)C48—C49—H49A109.5
C19—C18—C16111.0 (3)C48—C49—H49B109.5
C18—C19—H19A109.5H49A—C49—H49B109.5
C18—C19—H19B109.5C48—C49—H49C109.5
H19A—C19—H19B109.5H49A—C49—H49C109.5
C18—C19—H19C109.5H49B—C49—H49C109.5
H19A—C19—H19C109.5C48—C50—C51105.1 (4)
H19B—C19—H19C109.5C48—C50—H50A110.7
C18—C20—C21105.6 (3)C51—C50—H50A110.7
C18—C20—H20A110.6C48—C50—H50B110.7
C21—C20—H20A110.6C51—C50—H50B110.7
C18—C20—H20B110.6H50A—C50—H50B108.8
C21—C20—H20B110.6C52—C51—C50107.6 (4)
H20A—C20—H20B108.7C52—C51—H51A110.2
C20—C21—C22107.2 (3)C50—C51—H51A110.2
C20—C21—H21A110.3C52—C51—H51B110.2
C22—C21—H21A110.3C50—C51—H51B110.2
C20—C21—H21B110.3H51A—C51—H51B108.5
C22—C21—H21B110.3C53—C52—C51113.2 (4)
H21A—C21—H21B108.5C53—C52—C46119.4 (4)
C23—C22—C16119.4 (4)C51—C52—C46102.9 (3)
C23—C22—C21112.5 (4)C53—C52—H52106.9
C16—C22—C21103.0 (3)C51—C52—H52106.9
C23—C22—H22107.1C46—C52—H52106.9
C16—C22—H22107.1C54—C53—C55110.5 (4)
C21—C22—H22107.1C54—C53—C52112.9 (4)
C22—C23—C25110.9 (3)C55—C53—C52110.1 (4)
C22—C23—C24112.3 (4)C54—C53—H53107.7
C25—C23—C24110.9 (4)C55—C53—H53107.7
C22—C23—H23107.5C52—C53—H53107.7
C25—C23—H23107.5C53—C54—H54A109.5
C24—C23—H23107.5C53—C54—H54B109.5
C23—C24—H24A109.5H54A—C54—H54B109.5
C23—C24—H24B109.5C53—C54—H54C109.5
H24A—C24—H24B109.5H54A—C54—H54C109.5
C23—C24—H24C109.5H54B—C54—H54C109.5
H24A—C24—H24C109.5C56—C55—C53114.8 (4)
H24B—C24—H24C109.5C56—C55—H55A108.6
C26—C25—C23115.1 (4)C53—C55—H55A108.6
C26—C25—H25A108.5C56—C55—H55B108.6
C23—C25—H25A108.5C53—C55—H55B108.6
C26—C25—H25B108.5H55A—C55—H55B107.5
C23—C25—H25B108.5C57—C56—C55111.6 (4)
H25A—C25—H25B107.5C57—C56—H56A109.3
C27—C26—C25112.8 (4)C55—C56—H56A109.3
C27—C26—H26A109.0C57—C56—H56B109.3
C25—C26—H26A109.0C55—C56—H56B109.3
C27—C26—H26B109.0H56A—C56—H56B108.0
C25—C26—H26B109.0C58—C57—C56128.7 (5)
H26A—C26—H26B107.8C58—C57—H57115.7
C28—C27—C26128.2 (4)C56—C57—H57115.7
C28—C27—H27115.9C57—C58—C59125.3 (5)
C26—C27—H27115.9C57—C58—C60119.2 (5)
C27—C28—C29124.5 (4)C59—C58—C60115.5 (4)
C27—C28—C30119.9 (5)C58—C59—H59A109.5
C29—C28—C30115.6 (4)C58—C59—H59B109.5
C28—C29—H29A109.5H59A—C59—H59B109.5
C28—C29—H29B109.5C58—C59—H59C109.5
H29A—C29—H29B109.5H59A—C59—H59C109.5
C28—C29—H29C109.5H59B—C59—H59C109.5
H29A—C29—H29C109.5O4—C60—C58112.1 (4)
H29B—C29—H29C109.5O4—C60—H60A109.2
O2—C30—C28110.5 (4)C58—C60—H60A109.2
O2—C30—H30A109.6O4—C60—H60B109.2
C28—C30—H30A109.6C58—C60—H60B109.2
O2—C30—H30B109.6H60A—C60—H60B107.9
O1—C1—C2—C3−179.9 (4)O3—C31—C32—C33179.7 (4)
C6—C1—C2—C353.4 (5)C36—C31—C32—C3355.1 (6)
C1—C2—C3—C4−53.2 (5)C31—C32—C33—C34−56.6 (6)
C2—C3—C4—C13−87.5 (5)C32—C33—C34—C3558.7 (5)
C2—C3—C4—C557.1 (5)C32—C33—C34—C43−86.3 (5)
C2—C3—C4—C12−156.4 (4)C32—C33—C34—C42−154.2 (4)
C13—C4—C5—C9−51.6 (5)C33—C34—C35—C39166.6 (4)
C3—C4—C5—C9166.2 (4)C43—C34—C35—C39−51.5 (6)
C12—C4—C5—C919.9 (6)C42—C34—C35—C3919.6 (6)
C13—C4—C5—C679.5 (5)C33—C34—C35—C36−60.6 (5)
C3—C4—C5—C6−62.7 (5)C43—C34—C35—C3681.2 (5)
C12—C4—C5—C6151.0 (4)C42—C34—C35—C36152.4 (4)
O1—C1—C6—C8−56.3 (5)O3—C31—C36—C38−53.7 (5)
C2—C1—C6—C867.9 (5)C32—C31—C36—C3871.1 (5)
O1—C1—C6—C763.5 (5)O3—C31—C36—C3765.3 (5)
C2—C1—C6—C7−172.3 (4)C32—C31—C36—C37−169.9 (5)
O1—C1—C6—C5−179.1 (4)O3—C31—C36—C35−176.1 (4)
C2—C1—C6—C5−54.9 (5)C32—C31—C36—C35−51.3 (6)
C4—C5—C6—C8−61.4 (5)C34—C35—C36—C38−67.2 (5)
C9—C5—C6—C868.4 (6)C39—C35—C36—C3865.4 (6)
C4—C5—C6—C7177.1 (4)C34—C35—C36—C37170.8 (4)
C9—C5—C6—C7−53.1 (6)C39—C35—C36—C37−56.7 (6)
C4—C5—C6—C159.8 (5)C34—C35—C36—C3154.2 (6)
C9—C5—C6—C1−170.3 (4)C39—C35—C36—C31−173.3 (5)
C4—C5—C9—C10−49.5 (5)C34—C35—C39—C40−47.9 (6)
C6—C5—C9—C10−178.9 (4)C36—C35—C39—C40179.6 (4)
C5—C9—C10—C1170.3 (5)C35—C39—C40—C4168.2 (5)
C9—C10—C11—C18173.8 (4)C39—C40—C41—C48174.4 (4)
C9—C10—C11—C12−56.8 (5)C39—C40—C41—C42−56.5 (5)
C3—C4—C12—C13105.3 (5)C35—C34—C42—C43−112.7 (5)
C5—C4—C12—C13−112.1 (5)C33—C34—C42—C43103.4 (5)
C13—C4—C12—C14−107.6 (4)C35—C34—C42—C44138.6 (4)
C3—C4—C12—C14−2.3 (6)C33—C34—C42—C44−5.3 (7)
C5—C4—C12—C14140.2 (4)C43—C34—C42—C44−108.8 (5)
C13—C4—C12—C11103.9 (5)C35—C34—C42—C41−9.3 (6)
C3—C4—C12—C11−150.8 (4)C33—C34—C42—C41−153.2 (4)
C5—C4—C12—C11−8.2 (6)C43—C34—C42—C41103.3 (5)
C10—C11—C12—C1392.5 (5)C40—C41—C42—C4394.8 (5)
C18—C11—C12—C13−137.0 (4)C48—C41—C42—C43−135.2 (4)
C10—C11—C12—C14−122.3 (4)C40—C41—C42—C3427.4 (6)
C18—C11—C12—C148.2 (6)C48—C41—C42—C34157.3 (4)
C10—C11—C12—C426.0 (6)C40—C41—C42—C44−120.8 (4)
C18—C11—C12—C4156.5 (4)C48—C41—C42—C449.2 (6)
C3—C4—C13—C12−111.2 (4)C44—C42—C43—C34106.9 (5)
C5—C4—C13—C12109.4 (4)C41—C42—C43—C34−109.5 (4)
C14—C12—C13—C4106.6 (4)C35—C34—C43—C42108.4 (5)
C11—C12—C13—C4−108.3 (4)C33—C34—C43—C42−111.4 (4)
C13—C12—C14—C15106.9 (4)C43—C42—C44—C45103.8 (5)
C4—C12—C14—C15174.4 (4)C34—C42—C44—C45172.7 (4)
C11—C12—C14—C15−37.2 (6)C41—C42—C44—C45−39.0 (6)
C12—C14—C15—C1610.9 (5)C42—C44—C45—C4612.5 (6)
C14—C15—C16—C17−81.3 (4)C44—C45—C46—C47−82.4 (4)
C14—C15—C16—C1840.5 (5)C44—C45—C46—C52154.6 (4)
C14—C15—C16—C22156.2 (4)C44—C45—C46—C4839.6 (5)
C10—C11—C18—C20−71.9 (5)C40—C41—C48—C50−73.8 (5)
C12—C11—C18—C20159.2 (4)C42—C41—C48—C50157.5 (4)
C10—C11—C18—C1949.8 (5)C40—C41—C48—C4947.7 (5)
C12—C11—C18—C19−79.2 (5)C42—C41—C48—C49−81.0 (5)
C10—C11—C18—C16173.0 (4)C40—C41—C48—C46171.9 (4)
C12—C11—C18—C1644.1 (5)C42—C41—C48—C4643.3 (5)
C15—C16—C18—C20168.1 (3)C47—C46—C48—C50−70.8 (4)
C17—C16—C18—C20−71.6 (4)C45—C46—C48—C50169.4 (3)
C22—C16—C18—C2043.1 (4)C52—C46—C48—C5044.4 (4)
C15—C16—C18—C11−70.5 (4)C47—C46—C48—C49174.1 (3)
C17—C16—C18—C1149.8 (5)C45—C46—C48—C4954.3 (4)
C22—C16—C18—C11164.5 (3)C52—C46—C48—C49−70.6 (4)
C15—C16—C18—C1952.9 (4)C47—C46—C48—C4149.9 (5)
C17—C16—C18—C19173.2 (3)C45—C46—C48—C41−69.8 (4)
C22—C16—C18—C19−72.1 (4)C52—C46—C48—C41165.2 (4)
C11—C18—C20—C21−149.6 (4)C49—C48—C50—C5186.1 (4)
C19—C18—C20—C2186.8 (4)C41—C48—C50—C51−150.4 (4)
C16—C18—C20—C21−30.8 (4)C46—C48—C50—C51−31.8 (4)
C18—C20—C21—C226.7 (4)C48—C50—C51—C527.1 (5)
C15—C16—C22—C2376.7 (5)C50—C51—C52—C53150.6 (4)
C17—C16—C22—C23−46.5 (5)C50—C51—C52—C4620.4 (5)
C18—C16—C22—C23−163.8 (4)C47—C46—C52—C53−48.1 (5)
C15—C16—C22—C21−157.7 (4)C45—C46—C52—C5375.0 (5)
C17—C16—C22—C2179.1 (4)C48—C46—C52—C53−165.9 (4)
C18—C16—C22—C21−38.3 (4)C47—C46—C52—C5178.3 (4)
C20—C21—C22—C23149.7 (3)C45—C46—C52—C51−158.6 (4)
C20—C21—C22—C1619.8 (4)C48—C46—C52—C51−39.5 (4)
C16—C22—C23—C25176.3 (4)C51—C52—C53—C54178.0 (4)
C21—C22—C23—C2555.4 (5)C46—C52—C53—C54−60.7 (5)
C16—C22—C23—C24−59.0 (5)C51—C52—C53—C5553.9 (5)
C21—C22—C23—C24−179.8 (3)C46—C52—C53—C55175.2 (4)
C22—C23—C25—C26−175.7 (4)C54—C53—C55—C5659.1 (5)
C24—C23—C25—C2658.8 (5)C52—C53—C55—C56−175.5 (4)
C23—C25—C26—C27164.9 (4)C53—C55—C56—C57159.8 (4)
C25—C26—C27—C28152.7 (5)C55—C56—C57—C58142.3 (5)
C26—C27—C28—C29−2.5 (8)C56—C57—C58—C590.3 (9)
C26—C27—C28—C30178.1 (5)C56—C57—C58—C60178.1 (5)
C27—C28—C30—O2−119.1 (5)C57—C58—C60—O4−119.2 (5)
C29—C28—C30—O261.5 (6)C59—C58—C60—O458.8 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.842.112.807 (5)140
O2—H2···O3ii0.841.972.784 (5)162
O3—H3···O4iii0.842.002.747 (5)148
O4—H4···O10.841.892.722 (4)173

Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x−2, y−1, z−1; (iii) −x+3, y+1/2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2187).

References

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