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ISSN: 2056-9890

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

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and bDepartment of Pharmacology, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 20 July 2010; accepted 22 July 2010; online 31 July 2010)

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 (10[\overline2]).

Related literature

For the spectroscopic characterization of the title compound, see: Anjaneyulu et al. (1985[Anjaneyulu, V., Prasad, K., Harischandra, R. K. & Connolly, J. D. (1985). Phytochemistry, 24, 2359-2367.], 1994[Anjaneyulu, V., Babu, J. S. & Jyothi, G. (1994). Acta Ciencia Indica Chem. 20, 109-112.]); Parveen et al. (1990[Parveen, M., Khan, N. U., Achari, B. & Dutta, P. K. (1990). Fitoterapia, 61, 86-87.]); Takahashi & Takani (1975[Takahashi, K. & Takani, M. (1975). Chem. Pharm. Bull. 23, 538-542.]).

[Scheme 1]

Experimental

Crystal data
  • C30H50O2

  • Mr = 442.70

  • Monoclinic, P 21

  • 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)

  • Rint = 0.085

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2i 0.84 2.11 2.807 (5) 140
O2—H2⋯O3ii 0.84 1.97 2.784 (5) 162
O3—H3⋯O4iii 0.84 2.00 2.747 (5) 148
O4—H4⋯O1 0.84 1.89 2.722 (4) 173
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) x-2, y-1, z-1; (iii) [-x+3, y+{\script{1\over 2}}, -z+2].

Data collection: APEX2 software (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Structure description top

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.

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

Computing details top

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

Figures top
[Figure 1] 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.
[Figure 2] 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.
Cycloart-24-ene-3β,26-diol top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
3318 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.085
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
ω scansh = 1111
16958 measured reflectionsk = 88
4970 independent reflectionsl = 3641
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143H-atom parameters constrained
S = 0.96 w = 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
Crystal data top
C30H50O2V = 2614.0 (6) Å3
Mr = 442.70Z = 4
Monoclinic, P21Mo Kα radiation
a = 9.9950 (14) ŵ = 0.07 mm1
b = 7.512 (1) ÅT = 100 K
c = 34.820 (5) Å0.45 × 0.15 × 0.02 mm
β = 91.029 (2)°
Data collection top
Bruker SMART APEX
diffractometer
3318 reflections with I > 2σ(I)
16958 measured reflectionsRint = 0.085
4970 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0551 restraint
wR(F2) = 0.143H-atom parameters constrained
S = 0.96Δρmax = 0.18 e Å3
4970 reflectionsΔρmin = 0.19 e Å3
593 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.8196 (3)0.5009 (4)0.73269 (10)0.0366 (9)
H10.88420.50890.71770.055*
O20.0926 (3)0.0538 (5)0.28107 (9)0.0421 (9)
H20.14240.01870.26930.063*
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*
H9B0.53820.00740.67030.038*
C100.4054 (4)0.0867 (6)0.62840 (13)0.0292 (11)
H10A0.33570.13590.64530.035*
H10B0.37930.03620.62130.035*
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)
H20A0.21520.06270.55970.027*
H20B0.35800.03680.53980.027*
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*
H25B0.00350.29750.44900.030*
C260.0835 (4)0.3098 (6)0.39569 (12)0.0256 (11)
H26A0.05240.43420.39260.031*
H26B0.17630.30320.38630.031*
C270.0035 (4)0.1910 (7)0.37175 (13)0.0307 (12)
H270.01610.07400.38140.037*
C280.0663 (4)0.2285 (7)0.33829 (13)0.0292 (11)
C290.0642 (6)0.4038 (7)0.31926 (16)0.0541 (17)
H29A0.01830.49000.33600.081*
H29B0.15620.44360.31410.081*
H29C0.01660.39420.29500.081*
C300.1459 (5)0.0885 (8)0.31816 (15)0.0462 (15)
H30A0.14420.02220.33360.055*
H30B0.24010.12780.31540.055*
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) top
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, º) top
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—C3179.9 (4)O3—C31—C32—C33179.7 (4)
C6—C1—C2—C353.4 (5)C36—C31—C32—C3355.1 (6)
C1—C2—C3—C453.2 (5)C31—C32—C33—C3456.6 (6)
C2—C3—C4—C1387.5 (5)C32—C33—C34—C3558.7 (5)
C2—C3—C4—C557.1 (5)C32—C33—C34—C4386.3 (5)
C2—C3—C4—C12156.4 (4)C32—C33—C34—C42154.2 (4)
C13—C4—C5—C951.6 (5)C33—C34—C35—C39166.6 (4)
C3—C4—C5—C9166.2 (4)C43—C34—C35—C3951.5 (6)
C12—C4—C5—C919.9 (6)C42—C34—C35—C3919.6 (6)
C13—C4—C5—C679.5 (5)C33—C34—C35—C3660.6 (5)
C3—C4—C5—C662.7 (5)C43—C34—C35—C3681.2 (5)
C12—C4—C5—C6151.0 (4)C42—C34—C35—C36152.4 (4)
O1—C1—C6—C856.3 (5)O3—C31—C36—C3853.7 (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—C7172.3 (4)C32—C31—C36—C37169.9 (5)
O1—C1—C6—C5179.1 (4)O3—C31—C36—C35176.1 (4)
C2—C1—C6—C554.9 (5)C32—C31—C36—C3551.3 (6)
C4—C5—C6—C861.4 (5)C34—C35—C36—C3867.2 (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—C753.1 (6)C39—C35—C36—C3756.7 (6)
C4—C5—C6—C159.8 (5)C34—C35—C36—C3154.2 (6)
C9—C5—C6—C1170.3 (4)C39—C35—C36—C31173.3 (5)
C4—C5—C9—C1049.5 (5)C34—C35—C39—C4047.9 (6)
C6—C5—C9—C10178.9 (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—C1256.8 (5)C39—C40—C41—C4256.5 (5)
C3—C4—C12—C13105.3 (5)C35—C34—C42—C43112.7 (5)
C5—C4—C12—C13112.1 (5)C33—C34—C42—C43103.4 (5)
C13—C4—C12—C14107.6 (4)C35—C34—C42—C44138.6 (4)
C3—C4—C12—C142.3 (6)C33—C34—C42—C445.3 (7)
C5—C4—C12—C14140.2 (4)C43—C34—C42—C44108.8 (5)
C13—C4—C12—C11103.9 (5)C35—C34—C42—C419.3 (6)
C3—C4—C12—C11150.8 (4)C33—C34—C42—C41153.2 (4)
C5—C4—C12—C118.2 (6)C43—C34—C42—C41103.3 (5)
C10—C11—C12—C1392.5 (5)C40—C41—C42—C4394.8 (5)
C18—C11—C12—C13137.0 (4)C48—C41—C42—C43135.2 (4)
C10—C11—C12—C14122.3 (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—C44120.8 (4)
C18—C11—C12—C4156.5 (4)C48—C41—C42—C449.2 (6)
C3—C4—C13—C12111.2 (4)C44—C42—C43—C34106.9 (5)
C5—C4—C13—C12109.4 (4)C41—C42—C43—C34109.5 (4)
C14—C12—C13—C4106.6 (4)C35—C34—C43—C42108.4 (5)
C11—C12—C13—C4108.3 (4)C33—C34—C43—C42111.4 (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—C1537.2 (6)C41—C42—C44—C4539.0 (6)
C12—C14—C15—C1610.9 (5)C42—C44—C45—C4612.5 (6)
C14—C15—C16—C1781.3 (4)C44—C45—C46—C4782.4 (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—C2071.9 (5)C40—C41—C48—C5073.8 (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—C1979.2 (5)C42—C41—C48—C4981.0 (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—C5070.8 (4)
C17—C16—C18—C2071.6 (4)C45—C46—C48—C50169.4 (3)
C22—C16—C18—C2043.1 (4)C52—C46—C48—C5044.4 (4)
C15—C16—C18—C1170.5 (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—C4970.6 (4)
C15—C16—C18—C1952.9 (4)C47—C46—C48—C4149.9 (5)
C17—C16—C18—C19173.2 (3)C45—C46—C48—C4169.8 (4)
C22—C16—C18—C1972.1 (4)C52—C46—C48—C41165.2 (4)
C11—C18—C20—C21149.6 (4)C49—C48—C50—C5186.1 (4)
C19—C18—C20—C2186.8 (4)C41—C48—C50—C51150.4 (4)
C16—C18—C20—C2130.8 (4)C46—C48—C50—C5131.8 (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—C2346.5 (5)C50—C51—C52—C4620.4 (5)
C18—C16—C22—C23163.8 (4)C47—C46—C52—C5348.1 (5)
C15—C16—C22—C21157.7 (4)C45—C46—C52—C5375.0 (5)
C17—C16—C22—C2179.1 (4)C48—C46—C52—C53165.9 (4)
C18—C16—C22—C2138.3 (4)C47—C46—C52—C5178.3 (4)
C20—C21—C22—C23149.7 (3)C45—C46—C52—C51158.6 (4)
C20—C21—C22—C1619.8 (4)C48—C46—C52—C5139.5 (4)
C16—C22—C23—C25176.3 (4)C51—C52—C53—C54178.0 (4)
C21—C22—C23—C2555.4 (5)C46—C52—C53—C5460.7 (5)
C16—C22—C23—C2459.0 (5)C51—C52—C53—C5553.9 (5)
C21—C22—C23—C24179.8 (3)C46—C52—C53—C55175.2 (4)
C22—C23—C25—C26175.7 (4)C54—C53—C55—C5659.1 (5)
C24—C23—C25—C2658.8 (5)C52—C53—C55—C56175.5 (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—C292.5 (8)C56—C57—C58—C590.3 (9)
C26—C27—C28—C30178.1 (5)C56—C57—C58—C60178.1 (5)
C27—C28—C30—O2119.1 (5)C57—C58—C60—O4119.2 (5)
C29—C28—C30—O261.5 (6)C59—C58—C60—O458.8 (6)
Hydrogen-bond geometry (Å, º) top
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) x2, y1, z1; (iii) x+3, y+1/2, z+2.

Experimental details

Crystal data
Chemical formulaC30H50O2
Mr442.70
Crystal system, space groupMonoclinic, P21
Temperature (K)100
a, b, c (Å)9.9950 (14), 7.512 (1), 34.820 (5)
β (°) 91.029 (2)
V3)2614.0 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.45 × 0.15 × 0.02
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
16958, 4970, 3318
Rint0.085
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.143, 0.96
No. of reflections4970
No. of parameters593
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.19

Computer programs: APEX2 software (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
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) x2, y1, z1; (iii) x+3, y+1/2, z+2.
 

Acknowledgements

We thank the University of Malaya for supporting this study.

References

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First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationParveen, M., Khan, N. U., Achari, B. & Dutta, P. K. (1990). Fitoterapia, 61, 86–87.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTakahashi, K. & Takani, M. (1975). Chem. Pharm. Bull. 23, 538–542.  CrossRef CAS Google Scholar
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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