PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o416.
Published online 2010 January 23. doi:  10.1107/S1600536810002072
PMCID: PMC2979682

(20S)-24,25-Dihydr­oxy-20,24-ep­oxy-3,4-secodammar-4(28)-en-3-oic acid from Aglaia smithii

Abstract

The title compound, C30H50O5, was isolated from the bark of Aglaia smithii. There are two independent mol­ecules in the asymmetric unit that differ in the orientation of the isopropenyl group attached to the cyclo­hexane ring. The cyclo­hexane rings in both mol­ecules adopt chair conformations, whereas the cyclo­pentane and tetra­hydro­furan rings adopt envelope conformations. The independent mol­ecules are linked into a layer parallel to (010) by O—H(...)O hydrogen bonds.

Related literature

For the spectroscopic characterization of 24-ep­oxy-24,25-dihydr­oxy-3,4-secodammar-4(28)-en-3-oic acid from different plants, see: de Campos Braga et al. (2006 [triangle]); Luo et al. (2000 [triangle]); Mohamad et al. (1999 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o416-scheme1.jpg

Experimental

Crystal data

  • C30H50O5
  • M r = 490.70
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o416-efi1.jpg
  • a = 7.7322 (1) Å
  • b = 22.4976 (4) Å
  • c = 31.6043 (5) Å
  • V = 5497.76 (15) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 123 K
  • 0.45 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • 52832 measured reflections
  • 7026 independent reflections
  • 5590 reflections with I > 2σ(I)
  • R int = 0.058

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.175
  • S = 1.09
  • 7026 reflections
  • 651 parameters
  • H-atom parameters constrained
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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/S1600536810002072/ci5019sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002072/ci5019Isup2.hkl

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

Acknowledgments

This work was supported by the Directorate of Higher Education, Ministry of National Education, Indonesia (BPPS-Doctoral Program), the I-MHERE Project of Padjadjaran University and the Science Fund of Malaysia (12–02-03–2063). We also thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Aglaia is a genus of more than 100 species belonging to the Mahagony family (Meliaceae). The trees are found in the tropical and subtropical forests of Southeast Asia, Northern Australia and the Pacific. Some are commercially important timber trees; others yield edible fruit and scented flowers whereas others are used for medicinal purposes.

Experimental

Aglaia smithii was collected in the Bogor Botanical Garden, West Java, Indonesia; the plant was identified by the Herbarium Bogoriense in Bogor. The dried and milled bark of A. smithii (5 kg) was extracted exhaustively by methanol at room temperature to yield a concentrated methanol extract (0.7 kg); 300 g of the extract was subjected to vacuum column chromatography on silica gel 60 by using a step gradient of n-hexane–ethylacetate–methanol. The fraction eluted by n-hexane–ethylacetate (1:1) was further separated by column chromatography on silica gel (chloroform: methanol 9.75:0.25) to give 20S,24-epoxy-24,25-dihydroxy-3,4-secodammar-4(28)-en-3-oic acid (34 mg). The structure was established by 1H-NMR spectroscopic analysis. The IR spectrum showed the carbonyl stretching at 1710 cm-1.

Refinement

H-atoms were placed in calculated positions (O-H = 0.84 Å and C-H = 0.95–1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O,Cmethyl). A rotating group model was used for the –OH and –CH3 groups. The structure features a short H5···H6 (x-1,y,z) contact of 1.83 Å.

In the absence of significant anomalous dispersion effects, Friedel pairs were merged before the final refinement. Therefore, the absolute configuration reported in the literature (de Campos Braga et al., 2006; Luo et al., 2000; Mohamad et al., 1999) has been assigned.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of one of the two independent molecules in the title compound, at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.
Fig. 2.
Displacement ellipsoid plot (Barbour, 2001) of second independent molecule in the title compound, at the 70% probability level. H atoms are drawn as spheres of arbitrary radius.

Crystal data

C30H50O5F(000) = 2160
Mr = 490.70Dx = 1.186 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 8963 reflections
a = 7.7322 (1) Åθ = 2.6–27.6°
b = 22.4976 (4) ŵ = 0.08 mm1
c = 31.6043 (5) ÅT = 123 K
V = 5497.76 (15) Å3Block, colourless
Z = 80.45 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer5590 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
graphiteθmax = 27.5°, θmin = 1.1°
ω scansh = −9→10
52832 measured reflectionsk = −28→29
7026 independent reflectionsl = −41→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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0818P)2 + 3.9232P] where P = (Fo2 + 2Fc2)/3
7026 reflections(Δ/σ)max = 0.001
651 parametersΔρmax = 0.64 e Å3
0 restraintsΔρmin = −0.25 e Å3

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

xyzUiso*/Ueq
O10.7294 (4)0.59393 (14)0.80831 (11)0.0442 (8)
H10.82400.61110.81280.066*
O20.9021 (5)0.51630 (17)0.79778 (18)0.0762 (14)
O30.5230 (3)0.36487 (13)0.51958 (8)0.0286 (6)
O40.6886 (4)0.44300 (12)0.49404 (9)0.0321 (6)
H40.59220.45920.49820.048*
O50.5052 (4)0.39226 (15)0.43025 (9)0.0431 (8)
H50.50620.42670.44050.065*
O61.1987 (4)0.42773 (16)0.46868 (13)0.0564 (10)
H61.29290.41090.46310.085*
O71.3750 (4)0.50166 (15)0.48684 (13)0.0498 (9)
O81.0443 (3)0.65801 (13)0.75888 (8)0.0287 (6)
O91.2105 (4)0.57900 (12)0.78355 (10)0.0329 (6)
H91.11250.56340.78640.049*
O101.0195 (4)0.63938 (18)0.84383 (9)0.0468 (9)
H101.04470.61610.86370.070*
C10.7578 (6)0.5385 (2)0.79858 (16)0.0397 (11)
C20.5988 (5)0.50533 (19)0.78545 (15)0.0360 (10)
H2A0.58780.50710.75430.043*
H2B0.49600.52500.79780.043*
C30.6021 (5)0.44070 (16)0.79936 (13)0.0259 (8)
H3A0.59260.43970.83060.031*
H3B0.71660.42400.79190.031*
C40.4605 (5)0.39870 (16)0.78083 (12)0.0233 (8)
C50.5108 (5)0.33588 (16)0.79598 (13)0.0298 (9)
H5A0.53720.33700.82630.045*
H5B0.61280.32220.78030.045*
H5C0.41440.30850.79090.045*
C60.2795 (5)0.41845 (16)0.79768 (12)0.0243 (8)
H6A0.26580.46100.78910.029*
C70.2572 (5)0.41713 (19)0.84555 (13)0.0312 (9)
C80.2569 (7)0.4730 (2)0.86775 (15)0.0464 (12)
H8A0.22660.46630.89750.070*
H8B0.17180.49970.85480.070*
H8C0.37200.49100.86610.070*
C90.2250 (7)0.3648 (2)0.86775 (15)0.0442 (11)
H9A0.20300.36620.89730.053*
H9B0.22500.32780.85330.053*
C100.1322 (5)0.38449 (19)0.77585 (13)0.0300 (9)
H10A0.14320.34160.78230.036*
H10B0.02000.39840.78730.036*
C110.1343 (5)0.39333 (19)0.72812 (13)0.0282 (8)
H11A0.11190.43570.72180.034*
H11B0.03930.36980.71540.034*
C120.3060 (4)0.37500 (15)0.70726 (12)0.0213 (7)
C130.3180 (5)0.30636 (16)0.70847 (13)0.0283 (8)
H13A0.24700.28960.68570.042*
H13B0.27600.29190.73580.042*
H13C0.43860.29420.70460.042*
C140.3139 (5)0.39729 (16)0.66023 (12)0.0244 (8)
C150.2875 (6)0.46553 (18)0.65651 (14)0.0356 (9)
H15A0.36910.48600.67530.053*
H15B0.16890.47570.66470.053*
H15C0.30790.47800.62720.053*
C160.1854 (5)0.3694 (2)0.62816 (13)0.0342 (9)
H16A0.17470.32610.63270.041*
H16B0.06960.38790.63070.041*
C170.2658 (5)0.3828 (2)0.58458 (13)0.0358 (10)
H17A0.21690.41990.57270.043*
H17B0.24260.34980.56460.043*
C180.4646 (5)0.38968 (18)0.59222 (12)0.0265 (8)
H180.49630.43200.58640.032*
C190.4877 (5)0.37863 (17)0.63995 (11)0.0240 (8)
H190.49840.33470.64380.029*
C200.6392 (5)0.4069 (2)0.66317 (13)0.0341 (10)
H20A0.63510.45060.65950.041*
H20B0.74910.39230.65090.041*
C210.6333 (5)0.39158 (19)0.71061 (12)0.0277 (8)
H21A0.65950.34880.71420.033*
H21B0.72450.41440.72540.033*
C220.4582 (4)0.40510 (16)0.73132 (12)0.0215 (7)
H220.44070.44860.72640.026*
C230.5735 (5)0.35016 (18)0.56319 (12)0.0267 (8)
C240.5401 (6)0.28394 (18)0.56902 (14)0.0360 (9)
H24A0.41660.27580.56510.054*
H24B0.57490.27200.59760.054*
H24C0.60720.26150.54810.054*
C250.7685 (5)0.3640 (2)0.56435 (13)0.0313 (9)
H25A0.78980.40520.57400.038*
H25B0.83030.33620.58330.038*
C260.8245 (5)0.3557 (2)0.51893 (13)0.0331 (9)
H26A0.84390.31320.51220.040*
H26B0.93090.37850.51260.040*
C270.6690 (5)0.38041 (18)0.49500 (12)0.0279 (8)
C280.6429 (5)0.3572 (2)0.44935 (13)0.0324 (9)
C290.8056 (6)0.3656 (2)0.42355 (13)0.0385 (10)
H29A0.78450.35300.39430.058*
H29B0.89910.34170.43570.058*
H29C0.83880.40760.42390.058*
C300.5795 (7)0.2937 (2)0.44868 (17)0.0481 (12)
H30A0.58980.27770.41990.072*
H30B0.45810.29240.45760.072*
H30C0.64940.26970.46810.072*
C311.2290 (5)0.48154 (19)0.48244 (14)0.0343 (9)
C321.0690 (5)0.51515 (19)0.49387 (15)0.0352 (10)
H32A1.05320.51400.52490.042*
H32B0.96770.49560.48070.042*
C331.0769 (5)0.57956 (18)0.47940 (12)0.0265 (8)
H33A1.06210.58020.44830.032*
H33B1.19440.59480.48550.032*
C340.9440 (5)0.62359 (16)0.49894 (12)0.0230 (8)
C351.0015 (6)0.68495 (18)0.48339 (13)0.0322 (9)
H35A1.09920.69880.50050.048*
H35B0.90520.71300.48600.048*
H35C1.03700.68230.45370.048*
C360.7585 (5)0.60654 (18)0.48330 (12)0.0267 (8)
H360.74120.56420.49180.032*
C370.7305 (5)0.6083 (2)0.43542 (13)0.0349 (10)
C380.7119 (7)0.5543 (2)0.41364 (14)0.0483 (12)
H38A0.68710.55430.38420.058*
H38B0.72410.51770.42830.058*
C390.7118 (7)0.6628 (2)0.41294 (16)0.0533 (13)
H39A0.67500.65450.38390.080*
H39B0.82280.68380.41250.080*
H39C0.62470.68750.42700.080*
C400.6166 (5)0.6419 (2)0.50618 (13)0.0332 (9)
H40A0.63170.68480.50030.040*
H40B0.50190.62970.49530.040*
C410.6240 (5)0.6313 (2)0.55383 (13)0.0313 (9)
H41A0.60170.58870.55950.038*
H41B0.53100.65450.56760.038*
C420.7977 (4)0.64850 (16)0.57358 (12)0.0234 (7)
C430.8121 (6)0.71613 (18)0.57232 (13)0.0348 (9)
H43A0.80050.72990.54300.052*
H43B0.92490.72830.58350.052*
H43C0.72000.73360.58960.052*
C440.8111 (5)0.62521 (17)0.62067 (11)0.0246 (8)
C450.7762 (6)0.55771 (18)0.62425 (13)0.0374 (10)
H45A0.81670.54340.65180.056*
H45B0.83810.53680.60170.056*
H45C0.65190.55020.62160.056*
C460.6928 (5)0.6556 (2)0.65346 (13)0.0367 (10)
H46A0.69040.69920.64920.044*
H46B0.57320.64010.65160.044*
C470.7754 (5)0.6398 (2)0.69631 (13)0.0337 (9)
H48A0.72410.60280.70780.040*
H48B0.75690.67230.71700.040*
C480.9731 (5)0.63108 (18)0.68749 (12)0.0258 (8)
H481.00340.58880.69370.031*
C490.9898 (4)0.64121 (16)0.63916 (11)0.0229 (7)
H491.00440.68500.63510.027*
C501.1350 (5)0.61177 (19)0.61497 (12)0.0281 (8)
H50A1.12590.56800.61770.034*
H50B1.24780.62430.62680.034*
C511.1247 (4)0.62944 (18)0.56807 (12)0.0254 (8)
H51A1.15150.67230.56530.030*
H51B1.21350.60710.55210.030*
C520.9462 (4)0.61729 (16)0.54841 (11)0.0200 (7)
H520.92650.57390.55350.024*
C531.0877 (5)0.67116 (17)0.71490 (12)0.0250 (8)
C541.0552 (6)0.73665 (18)0.70817 (14)0.0361 (10)
H54A1.11750.75950.72970.054*
H54B0.93100.74470.71040.054*
H54C1.09610.74820.68000.054*
C551.2821 (5)0.65641 (19)0.71187 (13)0.0295 (8)
H55A1.30020.61490.70260.035*
H55B1.34150.68350.69190.035*
C561.3465 (5)0.66561 (19)0.75689 (13)0.0307 (9)
H56A1.36730.70820.76300.037*
H56B1.45370.64280.76240.037*
C571.1936 (5)0.64126 (17)0.78243 (12)0.0272 (8)
C581.1739 (5)0.6655 (2)0.82744 (13)0.0328 (9)
C591.3286 (6)0.6499 (2)0.85434 (14)0.0377 (10)
H59A1.30990.66420.88330.057*
H59B1.43220.66880.84260.057*
H59C1.34420.60670.85470.057*
C601.1432 (7)0.7328 (2)0.82780 (17)0.0512 (13)
H60A1.11970.74600.85680.077*
H60B1.04400.74240.80970.077*
H60C1.24630.75320.81710.077*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0224 (14)0.0460 (19)0.064 (2)−0.0072 (13)0.0018 (15)−0.0262 (16)
O20.0296 (19)0.038 (2)0.161 (5)−0.0036 (16)−0.015 (2)−0.004 (2)
O30.0162 (12)0.0399 (16)0.0296 (14)0.0005 (12)−0.0025 (11)0.0011 (12)
O40.0264 (14)0.0343 (15)0.0357 (15)0.0027 (12)−0.0001 (13)0.0000 (12)
O50.0375 (17)0.057 (2)0.0344 (16)0.0252 (16)−0.0121 (14)−0.0182 (15)
O60.0272 (16)0.055 (2)0.087 (3)0.0113 (16)−0.0014 (18)−0.0274 (19)
O70.0229 (15)0.044 (2)0.083 (3)0.0030 (14)0.0006 (16)−0.0024 (18)
O80.0155 (12)0.0454 (17)0.0251 (13)−0.0011 (12)0.0031 (10)−0.0009 (12)
O90.0328 (15)0.0230 (14)0.0429 (16)0.0003 (12)−0.0072 (14)0.0010 (12)
O100.0361 (17)0.077 (3)0.0274 (15)−0.0305 (18)0.0053 (13)−0.0096 (15)
C10.026 (2)0.034 (2)0.059 (3)−0.0063 (18)−0.013 (2)0.007 (2)
C20.025 (2)0.031 (2)0.052 (3)−0.0075 (17)−0.0110 (19)0.0033 (19)
C30.0172 (17)0.0254 (19)0.035 (2)−0.0022 (14)−0.0071 (15)0.0023 (16)
C40.0184 (16)0.0224 (18)0.0290 (19)−0.0026 (14)−0.0040 (14)0.0052 (15)
C50.0274 (19)0.0218 (19)0.040 (2)0.0037 (16)−0.0041 (17)0.0077 (16)
C60.0204 (17)0.0210 (18)0.0315 (19)0.0002 (14)−0.0013 (15)−0.0008 (15)
C70.0199 (18)0.040 (2)0.034 (2)−0.0004 (17)−0.0030 (16)−0.0002 (17)
C80.057 (3)0.044 (3)0.038 (2)0.004 (2)−0.003 (2)0.000 (2)
C90.051 (3)0.045 (3)0.037 (2)−0.013 (2)0.011 (2)0.004 (2)
C100.0153 (17)0.037 (2)0.038 (2)−0.0020 (16)0.0020 (16)0.0000 (18)
C110.0137 (16)0.036 (2)0.035 (2)−0.0027 (16)−0.0040 (15)−0.0016 (17)
C120.0119 (15)0.0186 (17)0.0336 (19)−0.0001 (13)−0.0025 (14)0.0006 (14)
C130.0263 (19)0.0213 (18)0.037 (2)−0.0052 (15)0.0003 (17)−0.0005 (16)
C140.0166 (16)0.0253 (19)0.0312 (19)−0.0001 (14)−0.0043 (15)0.0012 (15)
C150.040 (2)0.031 (2)0.035 (2)0.0110 (19)−0.006 (2)0.0033 (17)
C160.0162 (17)0.051 (3)0.035 (2)0.0011 (18)−0.0040 (16)−0.0054 (19)
C170.0211 (19)0.050 (3)0.036 (2)0.0044 (18)−0.0061 (17)−0.0037 (19)
C180.0198 (17)0.029 (2)0.031 (2)−0.0028 (15)−0.0044 (15)0.0031 (16)
C190.0160 (16)0.0280 (19)0.0280 (19)0.0000 (15)−0.0019 (14)0.0019 (15)
C200.0164 (17)0.051 (3)0.035 (2)−0.0099 (18)−0.0019 (16)0.0046 (19)
C210.0147 (16)0.036 (2)0.032 (2)0.0000 (15)−0.0041 (15)−0.0007 (17)
C220.0162 (16)0.0172 (17)0.0312 (19)−0.0044 (14)−0.0049 (14)0.0044 (14)
C230.0206 (18)0.033 (2)0.0264 (19)−0.0018 (15)−0.0035 (15)0.0044 (16)
C240.037 (2)0.032 (2)0.039 (2)−0.0037 (19)0.0009 (19)0.0018 (18)
C250.0211 (18)0.040 (2)0.033 (2)0.0024 (17)−0.0060 (16)0.0050 (17)
C260.0167 (18)0.039 (2)0.043 (2)0.0027 (17)−0.0018 (17)0.0003 (19)
C270.0190 (17)0.033 (2)0.032 (2)0.0029 (16)0.0004 (15)0.0013 (16)
C280.0219 (18)0.044 (2)0.032 (2)0.0107 (18)−0.0011 (16)−0.0043 (19)
C290.034 (2)0.051 (3)0.030 (2)0.008 (2)0.0037 (18)0.0006 (19)
C300.034 (2)0.054 (3)0.056 (3)−0.005 (2)0.005 (2)−0.019 (2)
C310.027 (2)0.037 (2)0.039 (2)0.0070 (18)0.0017 (18)0.0046 (18)
C320.0238 (19)0.032 (2)0.049 (3)0.0037 (17)0.0128 (18)0.0014 (19)
C330.0146 (16)0.034 (2)0.031 (2)−0.0004 (15)0.0043 (15)−0.0001 (16)
C340.0174 (16)0.0246 (19)0.0268 (19)−0.0001 (14)0.0018 (14)0.0032 (15)
C350.029 (2)0.036 (2)0.031 (2)−0.0009 (18)0.0025 (17)0.0097 (17)
C360.0178 (17)0.037 (2)0.0257 (18)0.0026 (16)0.0007 (14)0.0024 (16)
C370.0167 (18)0.056 (3)0.032 (2)0.0015 (18)−0.0026 (16)0.0107 (19)
C380.049 (3)0.071 (3)0.025 (2)−0.004 (3)0.004 (2)−0.002 (2)
C390.045 (3)0.067 (3)0.048 (3)0.005 (3)−0.013 (2)0.018 (2)
C400.0159 (17)0.044 (2)0.040 (2)0.0071 (17)−0.0058 (16)−0.006 (2)
C410.0137 (16)0.047 (2)0.033 (2)0.0036 (17)0.0050 (15)−0.0090 (19)
C420.0117 (15)0.0279 (19)0.0305 (19)0.0025 (14)0.0003 (14)−0.0017 (15)
C430.036 (2)0.033 (2)0.035 (2)0.0115 (19)−0.0056 (19)−0.0004 (17)
C440.0163 (16)0.032 (2)0.0254 (18)−0.0035 (15)0.0037 (14)0.0011 (15)
C450.044 (3)0.035 (2)0.034 (2)−0.019 (2)0.008 (2)0.0038 (18)
C460.0126 (17)0.062 (3)0.036 (2)0.0050 (18)0.0047 (16)−0.003 (2)
C470.0208 (19)0.049 (3)0.032 (2)−0.0058 (18)0.0072 (16)−0.0024 (18)
C480.0176 (17)0.032 (2)0.0278 (19)−0.0023 (15)0.0043 (15)0.0022 (16)
C490.0169 (16)0.0241 (18)0.0277 (18)0.0015 (15)0.0026 (14)0.0027 (15)
C500.0155 (16)0.041 (2)0.028 (2)0.0077 (16)0.0015 (14)0.0045 (17)
C510.0133 (16)0.036 (2)0.0268 (19)−0.0013 (15)0.0024 (14)0.0031 (16)
C520.0160 (16)0.0182 (17)0.0259 (18)0.0008 (13)0.0025 (14)0.0030 (14)
C530.0200 (17)0.031 (2)0.0242 (18)0.0007 (15)0.0039 (15)0.0031 (15)
C540.036 (2)0.032 (2)0.041 (2)0.0001 (18)−0.0008 (19)−0.0029 (18)
C550.0184 (17)0.038 (2)0.033 (2)0.0011 (16)0.0062 (16)0.0020 (17)
C560.0168 (17)0.038 (2)0.037 (2)0.0036 (16)0.0029 (16)−0.0001 (18)
C570.0223 (18)0.0259 (19)0.034 (2)0.0010 (16)−0.0015 (16)0.0042 (16)
C580.0206 (18)0.046 (2)0.032 (2)−0.0077 (18)−0.0003 (16)0.0062 (18)
C590.035 (2)0.036 (2)0.042 (2)−0.0033 (19)−0.0108 (19)−0.0029 (19)
C600.042 (3)0.054 (3)0.057 (3)0.011 (2)−0.008 (2)−0.019 (2)

Geometric parameters (Å, °)

O1—C11.304 (5)C27—C281.547 (6)
O1—H10.84C28—C301.512 (7)
O2—C11.223 (6)C28—C291.511 (6)
O3—C271.414 (5)C29—H29A0.98
O3—C231.470 (5)C29—H29B0.98
O4—C271.417 (5)C29—H29C0.98
O4—H40.84C30—H30A0.98
O5—C281.456 (5)C30—H30B0.98
O5—H50.84C30—H30C0.98
O6—C311.308 (5)C31—C321.494 (6)
O6—H60.84C32—C331.521 (6)
O7—C311.224 (5)C32—H32A0.99
O8—C571.424 (5)C32—H32B0.99
O8—C531.460 (5)C33—C341.556 (5)
O9—C571.407 (5)C33—H33A0.99
O9—H90.84C33—H33B0.99
O10—C581.427 (5)C34—C351.531 (5)
O10—H100.84C34—C361.564 (5)
C1—C21.496 (5)C34—C521.570 (5)
C2—C31.519 (5)C35—H35A0.98
C2—H2A0.99C35—H35B0.98
C2—H2B0.99C35—H35C0.98
C3—C41.560 (5)C36—C371.529 (5)
C3—H3A0.99C36—C401.536 (5)
C3—H3B0.99C36—H361.00
C4—C51.542 (5)C37—C381.404 (7)
C4—C61.562 (5)C37—C391.424 (6)
C4—C221.571 (5)C38—H38A0.95
C5—H5A0.98C38—H38B0.95
C5—H5B0.98C39—H39A0.98
C5—H5C0.98C39—H39B0.98
C6—C71.523 (5)C39—H39C0.98
C6—C101.535 (5)C40—C411.526 (6)
C6—H6A1.00C40—H40A0.99
C7—C91.392 (6)C40—H40B0.99
C7—C81.439 (6)C41—C421.531 (5)
C8—H8A0.98C41—H41A0.99
C8—H8B0.98C41—H41B0.99
C8—H8C0.98C42—C431.526 (5)
C9—H9A0.95C42—C521.563 (5)
C9—H9B0.95C42—C441.581 (5)
C10—C111.522 (6)C43—H43A0.98
C10—H10A0.99C43—H43B0.98
C10—H10B0.99C43—H43C0.98
C11—C121.539 (5)C44—C461.542 (5)
C11—H11A0.99C44—C491.543 (5)
C11—H11B0.99C44—C451.546 (5)
C12—C131.547 (5)C45—H45A0.98
C12—C221.557 (5)C45—H45B0.98
C12—C141.570 (5)C45—H45C0.98
C13—H13A0.98C46—C471.539 (6)
C13—H13B0.98C46—H46A0.99
C13—H13C0.98C46—H46B0.99
C14—C191.547 (5)C47—C481.566 (5)
C14—C151.553 (5)C47—H48A0.99
C14—C161.551 (5)C47—H48B0.99
C15—H15A0.98C48—C531.533 (5)
C15—H15B0.98C48—C491.550 (5)
C15—H15C0.98C48—H481.00
C16—C171.540 (6)C49—C501.512 (5)
C16—H16A0.99C49—H491.00
C16—H16B0.99C50—C511.537 (5)
C17—C181.564 (5)C50—H50A0.99
C17—H17A0.99C50—H50B0.99
C17—H17B0.99C51—C521.538 (5)
C18—C231.530 (6)C51—H51A0.99
C18—C191.539 (5)C51—H51B0.99
C18—H181.00C52—H521.00
C19—C201.522 (5)C53—C541.510 (6)
C19—H191.00C53—C551.542 (5)
C20—C211.539 (6)C54—H54A0.98
C20—H20A0.99C54—H54B0.98
C20—H20B0.99C54—H54C0.98
C21—C221.534 (5)C55—C561.522 (6)
C21—H21A0.99C55—H55A0.99
C21—H21B0.99C55—H55B0.99
C22—H221.00C56—C571.533 (5)
C23—C241.523 (6)C56—H56A0.99
C23—C251.540 (5)C56—H56B0.99
C24—H24A0.98C57—C581.531 (6)
C24—H24B0.98C58—C591.509 (6)
C24—H24C0.98C58—C601.534 (7)
C25—C261.511 (6)C59—H59A0.98
C25—H25A0.99C59—H59B0.98
C25—H25B0.99C59—H59C0.98
C26—C271.526 (5)C60—H60A0.98
C26—H26A0.99C60—H60B0.98
C26—H26B0.99C60—H60C0.98
C1—O1—H1109.5H30A—C30—H30B109.5
C27—O3—C23111.0 (3)C28—C30—H30C109.5
C27—O4—H4109.5H30A—C30—H30C109.5
C28—O5—H5109.5H30B—C30—H30C109.5
C31—O6—H6109.5O7—C31—O6123.1 (4)
C57—O8—C53111.4 (3)O7—C31—C32123.3 (4)
C57—O9—H9109.5O6—C31—C32113.6 (4)
C58—O10—H10109.5C31—C32—C33112.1 (3)
O2—C1—O1123.3 (4)C31—C32—H32A109.2
O2—C1—C2122.7 (4)C33—C32—H32A109.2
O1—C1—C2113.8 (4)C31—C32—H32B109.2
C1—C2—C3112.5 (3)C33—C32—H32B109.2
C1—C2—H2A109.1H32A—C32—H32B107.9
C3—C2—H2A109.1C32—C33—C34117.4 (3)
C1—C2—H2B109.1C32—C33—H33A107.9
C3—C2—H2B109.1C34—C33—H33A107.9
H2A—C2—H2B107.8C32—C33—H33B107.9
C2—C3—C4117.3 (3)C34—C33—H33B107.9
C2—C3—H3A108.0H33A—C33—H33B107.2
C4—C3—H3A108.0C35—C34—C33104.7 (3)
C2—C3—H3B108.0C35—C34—C36112.7 (3)
C4—C3—H3B108.0C33—C34—C36108.9 (3)
H3A—C3—H3B107.2C35—C34—C52113.4 (3)
C5—C4—C3105.1 (3)C33—C34—C52109.3 (3)
C5—C4—C6112.4 (3)C36—C34—C52107.6 (3)
C3—C4—C6109.2 (3)C34—C35—H35A109.5
C5—C4—C22113.3 (3)C34—C35—H35B109.5
C3—C4—C22109.0 (3)H35A—C35—H35B109.5
C6—C4—C22107.7 (3)C34—C35—H35C109.5
C4—C5—H5A109.5H35A—C35—H35C109.5
C4—C5—H5B109.5H35B—C35—H35C109.5
H5A—C5—H5B109.5C37—C36—C40110.6 (3)
C4—C5—H5C109.5C37—C36—C34115.9 (3)
H5A—C5—H5C109.5C40—C36—C34112.3 (3)
H5B—C5—H5C109.5C37—C36—H36105.8
C7—C6—C10110.7 (3)C40—C36—H36105.8
C7—C6—C4115.8 (3)C34—C36—H36105.8
C10—C6—C4111.7 (3)C38—C37—C39119.3 (4)
C7—C6—H6A106.0C38—C37—C36118.5 (4)
C10—C6—H6A106.0C39—C37—C36122.0 (4)
C4—C6—H6A106.0C37—C38—H38A120.0
C9—C7—C8119.5 (4)C37—C38—H38B120.0
C9—C7—C6122.5 (4)H38A—C38—H38B120.0
C8—C7—C6117.9 (4)C37—C39—H39A109.5
C7—C8—H8A109.5C37—C39—H39B109.5
C7—C8—H8B109.5H39A—C39—H39B109.5
H8A—C8—H8B109.5C37—C39—H39C109.5
C7—C8—H8C109.5H39A—C39—H39C109.5
H8A—C8—H8C109.5H39B—C39—H39C109.5
H8B—C8—H8C109.5C41—C40—C36110.9 (3)
C7—C9—H9A120.0C41—C40—H40A109.5
C7—C9—H9B120.0C36—C40—H40A109.5
H9A—C9—H9B120.0C41—C40—H40B109.5
C11—C10—C6111.9 (3)C36—C40—H40B109.5
C11—C10—H10A109.2H40A—C40—H40B108.0
C6—C10—H10A109.2C40—C41—C42113.3 (3)
C11—C10—H10B109.2C40—C41—H41A108.9
C6—C10—H10B109.2C42—C41—H41A108.9
H10A—C10—H10B107.9C40—C41—H41B108.9
C10—C11—C12113.5 (3)C42—C41—H41B108.9
C10—C11—H11A108.9H41A—C41—H41B107.7
C12—C11—H11A108.9C43—C42—C41107.8 (3)
C10—C11—H11B108.9C43—C42—C52112.4 (3)
C12—C11—H11B108.9C41—C42—C52108.9 (3)
H11A—C11—H11B107.7C43—C42—C44110.5 (3)
C11—C12—C13108.0 (3)C41—C42—C44110.9 (3)
C11—C12—C22109.1 (3)C52—C42—C44106.4 (3)
C13—C12—C22112.1 (3)C42—C43—H43A109.5
C11—C12—C14110.7 (3)C42—C43—H43B109.5
C13—C12—C14109.9 (3)H43A—C43—H43B109.5
C22—C12—C14107.1 (3)C42—C43—H43C109.5
C12—C13—H13A109.5H43A—C43—H43C109.5
C12—C13—H13B109.5H43B—C43—H43C109.5
H13A—C13—H13B109.5C46—C44—C49100.0 (3)
C12—C13—H13C109.5C46—C44—C45106.4 (3)
H13A—C13—H13C109.5C49—C44—C45110.9 (3)
H13B—C13—H13C109.5C46—C44—C42116.5 (3)
C19—C14—C15110.5 (3)C49—C44—C42109.7 (3)
C19—C14—C16100.1 (3)C45—C44—C42112.5 (3)
C15—C14—C16105.4 (3)C44—C45—H45A109.5
C19—C14—C12109.9 (3)C44—C45—H45B109.5
C15—C14—C12112.5 (3)H45A—C45—H45B109.5
C16—C14—C12117.7 (3)C44—C45—H45C109.5
C14—C15—H15A109.5H45A—C45—H45C109.5
C14—C15—H15B109.5H45B—C45—H45C109.5
H15A—C15—H15B109.5C47—C46—C44104.0 (3)
C14—C15—H15C109.5C47—C46—H46A110.9
H15A—C15—H15C109.5C44—C46—H46A110.9
H15B—C15—H15C109.5C47—C46—H46B110.9
C17—C16—C14104.3 (3)C44—C46—H46B110.9
C17—C16—H16A110.9H46A—C46—H46B109.0
C14—C16—H16A110.9C46—C47—C48106.1 (3)
C17—C16—H16B110.9C46—C47—H48A110.5
C14—C16—H16B110.9C48—C47—H48A110.5
H16A—C16—H16B108.9C46—C47—H48B110.5
C16—C17—C18106.1 (3)C48—C47—H48B110.5
C16—C17—H17A110.5H48A—C47—H48B108.7
C18—C17—H17A110.5C53—C48—C49115.0 (3)
C16—C17—H17B110.5C53—C48—C47112.9 (3)
C18—C17—H17B110.5C49—C48—C47103.8 (3)
H17A—C17—H17B108.7C53—C48—H48108.3
C23—C18—C19115.5 (3)C49—C48—H48108.3
C23—C18—C17113.0 (3)C47—C48—H48108.3
C19—C18—C17104.4 (3)C50—C49—C44111.8 (3)
C23—C18—H18107.9C50—C49—C48119.7 (3)
C19—C18—H18107.9C44—C49—C48105.3 (3)
C17—C18—H18107.9C50—C49—H49106.4
C20—C19—C18119.6 (3)C44—C49—H49106.4
C20—C19—C14110.8 (3)C48—C49—H49106.4
C18—C19—C14105.2 (3)C49—C50—C51109.6 (3)
C20—C19—H19106.8C49—C50—H50A109.7
C18—C19—H19106.8C51—C50—H50A109.7
C14—C19—H19106.8C49—C50—H50B109.7
C19—C20—C21110.7 (3)C51—C50—H50B109.7
C19—C20—H20A109.5H50A—C50—H50B108.2
C21—C20—H20A109.5C52—C51—C50112.9 (3)
C19—C20—H20B109.5C52—C51—H51A109.0
C21—C20—H20B109.5C50—C51—H51A109.0
H20A—C20—H20B108.1C52—C51—H51B109.0
C22—C21—C20113.4 (3)C50—C51—H51B109.0
C22—C21—H21A108.9H51A—C51—H51B107.8
C20—C21—H21A108.9C51—C52—C42112.0 (3)
C22—C21—H21B108.9C51—C52—C34113.3 (3)
C20—C21—H21B108.9C42—C52—C34117.3 (3)
H21A—C21—H21B107.7C51—C52—H52104.2
C21—C22—C12111.9 (3)C42—C52—H52104.2
C21—C22—C4113.4 (3)C34—C52—H52104.2
C12—C22—C4117.1 (3)O8—C53—C54107.1 (3)
C21—C22—H22104.3O8—C53—C48106.6 (3)
C12—C22—H22104.3C54—C53—C48113.5 (3)
C4—C22—H22104.3O8—C53—C55103.8 (3)
O3—C23—C24106.8 (3)C54—C53—C55111.3 (3)
O3—C23—C18106.6 (3)C48—C53—C55113.7 (3)
C24—C23—C18113.7 (3)C53—C54—H54A109.5
O3—C23—C25103.7 (3)C53—C54—H54B109.5
C24—C23—C25111.1 (4)H54A—C54—H54B109.5
C18—C23—C25114.0 (3)C53—C54—H54C109.5
C23—C24—H24A109.5H54A—C54—H54C109.5
C23—C24—H24B109.5H54B—C54—H54C109.5
H24A—C24—H24B109.5C56—C55—C53103.4 (3)
C23—C24—H24C109.5C56—C55—H55A111.1
H24A—C24—H24C109.5C53—C55—H55A111.1
H24B—C24—H24C109.5C56—C55—H55B111.1
C26—C25—C23103.5 (3)C53—C55—H55B111.1
C26—C25—H25A111.1H55A—C55—H55B109.0
C23—C25—H25A111.1C55—C56—C57101.0 (3)
C26—C25—H25B111.1C55—C56—H56A111.6
C23—C25—H25B111.1C57—C56—H56A111.6
H25A—C25—H25B109.0C55—C56—H56B111.6
C25—C26—C27101.5 (3)C57—C56—H56B111.6
C25—C26—H26A111.5H56A—C56—H56B109.4
C27—C26—H26A111.5O9—C57—O8110.6 (3)
C25—C26—H26B111.5O9—C57—C58109.9 (3)
C27—C26—H26B111.5O8—C57—C58108.1 (3)
H26A—C26—H26B109.3O9—C57—C56107.3 (3)
O4—C27—O3110.0 (3)O8—C57—C56104.8 (3)
O4—C27—C26106.8 (3)C58—C57—C56116.0 (3)
O3—C27—C26105.5 (3)O10—C58—C59111.3 (3)
O4—C27—C28109.2 (3)O10—C58—C60105.9 (4)
O3—C27—C28108.9 (3)C59—C58—C60110.3 (4)
C26—C27—C28116.2 (3)O10—C58—C57105.9 (3)
O5—C28—C30105.6 (4)C59—C58—C57111.3 (4)
O5—C28—C29108.5 (3)C60—C58—C57111.9 (4)
C30—C28—C29112.4 (4)C58—C59—H59A109.5
O5—C28—C27107.4 (3)C58—C59—H59B109.5
C30—C28—C27112.0 (4)H59A—C59—H59B109.5
C29—C28—C27110.6 (3)C58—C59—H59C109.5
C28—C29—H29A109.5H59A—C59—H59C109.5
C28—C29—H29B109.5H59B—C59—H59C109.5
H29A—C29—H29B109.5C58—C60—H60A109.5
C28—C29—H29C109.5C58—C60—H60B109.5
H29A—C29—H29C109.5H60A—C60—H60B109.5
H29B—C29—H29C109.5C58—C60—H60C109.5
C28—C30—H30A109.5H60A—C60—H60C109.5
C28—C30—H30B109.5H60B—C60—H60C109.5
O2—C1—C2—C338.6 (7)O7—C31—C32—C3343.5 (6)
O1—C1—C2—C3−145.4 (4)O6—C31—C32—C33−138.8 (4)
C1—C2—C3—C4−169.3 (4)C31—C32—C33—C34−164.4 (4)
C2—C3—C4—C5173.1 (4)C32—C33—C34—C35172.0 (4)
C2—C3—C4—C6−66.1 (4)C32—C33—C34—C36−67.2 (4)
C2—C3—C4—C2251.3 (4)C32—C33—C34—C5250.1 (4)
C5—C4—C6—C756.2 (4)C35—C34—C36—C3755.7 (4)
C3—C4—C6—C7−60.1 (4)C33—C34—C36—C37−60.1 (4)
C22—C4—C6—C7−178.3 (3)C52—C34—C36—C37−178.5 (3)
C5—C4—C6—C10−71.7 (4)C35—C34—C36—C40−72.7 (4)
C3—C4—C6—C10172.1 (3)C33—C34—C36—C40171.6 (3)
C22—C4—C6—C1053.8 (4)C52—C34—C36—C4053.1 (4)
C10—C6—C7—C949.1 (5)C40—C36—C37—C38−122.2 (4)
C4—C6—C7—C9−79.2 (5)C34—C36—C37—C38108.6 (4)
C10—C6—C7—C8−126.1 (4)C40—C36—C37—C3953.7 (5)
C4—C6—C7—C8105.5 (4)C34—C36—C37—C39−75.5 (5)
C7—C6—C10—C11170.8 (3)C37—C36—C40—C41169.7 (4)
C4—C6—C10—C11−58.7 (4)C34—C36—C40—C41−59.2 (4)
C6—C10—C11—C1257.0 (5)C36—C40—C41—C4258.8 (5)
C10—C11—C12—C1371.5 (4)C40—C41—C42—C4369.9 (4)
C10—C11—C12—C22−50.6 (4)C40—C41—C42—C52−52.3 (4)
C10—C11—C12—C14−168.2 (3)C40—C41—C42—C44−169.0 (3)
C11—C12—C14—C19179.8 (3)C43—C42—C44—C4650.1 (4)
C13—C12—C14—C19−61.1 (4)C41—C42—C44—C46−69.4 (4)
C22—C12—C14—C1961.0 (4)C52—C42—C44—C46172.3 (3)
C11—C12—C14—C1556.2 (4)C43—C42—C44—C49−62.5 (4)
C13—C12—C14—C15175.4 (3)C41—C42—C44—C49177.9 (3)
C22—C12—C14—C15−62.6 (4)C52—C42—C44—C4959.7 (4)
C11—C12—C14—C16−66.6 (4)C43—C42—C44—C45173.4 (3)
C13—C12—C14—C1652.6 (4)C41—C42—C44—C4553.9 (4)
C22—C12—C14—C16174.6 (3)C52—C42—C44—C45−64.3 (4)
C19—C14—C16—C17−41.8 (4)C49—C44—C46—C47−43.5 (4)
C15—C14—C16—C1773.0 (4)C45—C44—C46—C4772.0 (4)
C12—C14—C16—C17−160.7 (3)C42—C44—C46—C47−161.6 (3)
C14—C16—C17—C1825.7 (4)C44—C46—C47—C4828.2 (4)
C16—C17—C18—C23127.3 (4)C46—C47—C48—C53123.9 (4)
C16—C17—C18—C191.1 (5)C46—C47—C48—C49−1.3 (4)
C23—C18—C19—C2082.3 (4)C46—C44—C49—C50174.8 (3)
C17—C18—C19—C20−152.9 (4)C45—C44—C49—C5062.8 (4)
C23—C18—C19—C14−152.3 (3)C42—C44—C49—C50−62.2 (4)
C17—C18—C19—C14−27.6 (4)C46—C44—C49—C4843.2 (4)
C15—C14—C19—C2062.8 (4)C45—C44—C49—C48−68.8 (4)
C16—C14—C19—C20173.6 (3)C42—C44—C49—C48166.2 (3)
C12—C14—C19—C20−61.9 (4)C53—C48—C49—C5083.0 (4)
C15—C14—C19—C18−67.8 (4)C47—C48—C49—C50−153.1 (4)
C16—C14—C19—C1843.0 (4)C53—C48—C49—C44−150.1 (3)
C12—C14—C19—C18167.5 (3)C47—C48—C49—C44−26.2 (4)
C18—C19—C20—C21178.1 (3)C44—C49—C50—C5157.0 (4)
C14—C19—C20—C2155.5 (4)C48—C49—C50—C51−179.2 (3)
C19—C20—C21—C22−51.7 (5)C49—C50—C51—C52−53.5 (4)
C20—C21—C22—C1253.7 (4)C50—C51—C52—C4255.6 (4)
C20—C21—C22—C4−171.3 (3)C50—C51—C52—C34−169.0 (3)
C11—C12—C22—C21−176.7 (3)C43—C42—C52—C5164.1 (4)
C13—C12—C22—C2163.7 (4)C41—C42—C52—C51−176.5 (3)
C14—C12—C22—C21−56.9 (4)C44—C42—C52—C51−56.9 (4)
C11—C12—C22—C450.0 (4)C43—C42—C52—C34−69.4 (4)
C13—C12—C22—C4−69.6 (4)C41—C42—C52—C3450.0 (4)
C14—C12—C22—C4169.8 (3)C44—C42—C52—C34169.6 (3)
C5—C4—C22—C21−59.4 (4)C35—C34—C52—C51−57.8 (4)
C3—C4—C22—C2157.3 (4)C33—C34—C52—C5158.7 (4)
C6—C4—C22—C21175.7 (3)C36—C34—C52—C51176.8 (3)
C5—C4—C22—C1273.2 (4)C35—C34—C52—C4275.1 (4)
C3—C4—C22—C12−170.1 (3)C33—C34—C52—C42−168.5 (3)
C6—C4—C22—C12−51.7 (4)C36—C34—C52—C42−50.3 (4)
C27—O3—C23—C24−112.4 (4)C57—O8—C53—C54−113.8 (3)
C27—O3—C23—C18125.8 (3)C57—O8—C53—C48124.4 (3)
C27—O3—C23—C255.1 (4)C57—O8—C53—C554.0 (4)
C19—C18—C23—O3176.0 (3)C49—C48—C53—O8175.9 (3)
C17—C18—C23—O355.9 (4)C47—C48—C53—O857.1 (4)
C19—C18—C23—C2458.7 (4)C49—C48—C53—C5458.3 (4)
C17—C18—C23—C24−61.5 (5)C47—C48—C53—C54−60.6 (4)
C19—C18—C23—C25−70.2 (4)C49—C48—C53—C55−70.2 (4)
C17—C18—C23—C25169.7 (4)C47—C48—C53—C55170.9 (3)
O3—C23—C25—C26−27.0 (4)O8—C53—C55—C56−26.8 (4)
C24—C23—C25—C2687.4 (4)C54—C53—C55—C5688.1 (4)
C18—C23—C25—C26−142.5 (3)C48—C53—C55—C56−142.3 (3)
C23—C25—C26—C2737.5 (4)C53—C55—C56—C5738.0 (4)
C23—O3—C27—O4−96.1 (3)C53—O8—C57—O9−95.0 (4)
C23—O3—C27—C2618.8 (4)C53—O8—C57—C58144.7 (3)
C23—O3—C27—C28144.2 (3)C53—O8—C57—C5620.3 (4)
C25—C26—C27—O482.0 (4)C55—C56—C57—O981.5 (4)
C25—C26—C27—O3−35.0 (4)C55—C56—C57—O8−36.1 (4)
C25—C26—C27—C28−155.8 (4)C55—C56—C57—C58−155.2 (3)
O4—C27—C28—O5−51.0 (4)O9—C57—C58—O10−61.4 (4)
O3—C27—C28—O569.3 (4)O8—C57—C58—O1059.5 (4)
C26—C27—C28—O5−171.8 (3)C56—C57—C58—O10176.8 (3)
O4—C27—C28—C30−166.5 (3)O9—C57—C58—C5959.7 (4)
O3—C27—C28—C30−46.2 (4)O8—C57—C58—C59−179.5 (3)
C26—C27—C28—C3072.7 (5)C56—C57—C58—C59−62.1 (5)
O4—C27—C28—C2967.3 (4)O9—C57—C58—C60−176.3 (4)
O3—C27—C28—C29−172.5 (3)O8—C57—C58—C60−55.5 (4)
C26—C27—C28—C29−53.5 (5)C56—C57—C58—C6061.8 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O100.841.912.709 (4)158
O4—H4···O7i0.841.962.770 (4)160
O5—H5···O7i0.842.453.205 (5)149
O6—H6···O5ii0.841.992.780 (5)157
O9—H9···O20.841.982.807 (5)171
O10—H10···O5iii0.842.152.829 (4)138

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5019).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Campos Braga, P. A. de, Soares, M. S., da das, G. F., Silva, M. F., Vieira, P. C., Fernandes, J. B. & Pinheiro, A. L. (2006). Biochem. Syst. Ecol.34, 282–290.
  • Luo, X.-D., Wu, S.-H., Ma, Y.-B. & Wu, D.-G. (2000). Heterocycles, 53, 2795–2802.
  • Mohamad, K., Sévent, T., Dumontet, V., Pais, M., Van Tri, M., Hadi, H., Awang, K. & Martin, M. T. (1999). Phytochemistry, 51, 1031–1037.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography