organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

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

aDepartment of Chemistry, Faculty of Mathematics and Natural Sciences, Padjadjaran University, Jatinangor 45363, West Java, Indonesia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 15 January 2010; accepted 16 January 2010; online 23 January 2010)

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[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 et al. (2000[Luo, X.-D., Wu, S.-H., Ma, Y.-B. & Wu, D.-G. (2000). Heterocycles, 53, 2795-2802.]); Mohamad et al. (1999[Mohamad, K., Sévent, T., Dumontet, V., Pais, M., Van Tri, M., Hadi, H., Awang, K. & Martin, M. T. (1999). Phytochemistry, 51, 1031-1037.]).

[Scheme 1]

Experimental

Crystal data
  • C30H50O5

  • Mr = 490.70

  • Orthorhombic, P 21 21 21

  • 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)

  • Rint = 0.058

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O10 0.84 1.91 2.709 (4) 158
O4—H4⋯O7i 0.84 1.96 2.770 (4) 160
O5—H5⋯O7i 0.84 2.45 3.205 (5) 149
O6—H6⋯O5ii 0.84 1.99 2.780 (5) 157
O9—H9⋯O2 0.84 1.98 2.807 (5) 171
O10—H10⋯O5iii 0.84 2.15 2.829 (4) 138
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) [-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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). publCIF. In preparation.]).

Supporting information


Comment top

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.

Related literature top

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); Luo et al. (2000); Mohamad et al. (1999).

Experimental top

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 top

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.

Structure description top

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.

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); Luo et al. (2000); Mohamad et al. (1999).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. 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.
[Figure 2] 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.
(20S)-24,25-Dihydroxy-20,24-epoxy-3,4-secodammar-4(28)-en-3-oic acid top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
5590 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.058
Graphite monochromatorθmax = 27.5°, θmin = 1.1°
ω scansh = 910
52832 measured reflectionsk = 2829
7026 independent reflectionsl = 4141
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175H-atom parameters constrained
S = 1.09 w = 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 = 0.26 e Å3
Crystal data top
C30H50O5V = 5497.76 (15) Å3
Mr = 490.70Z = 8
Orthorhombic, P212121Mo Kα radiation
a = 7.7322 (1) ŵ = 0.08 mm1
b = 22.4976 (4) ÅT = 123 K
c = 31.6043 (5) Å0.45 × 0.15 × 0.10 mm
Data collection top
Bruker SMART APEX
diffractometer
5590 reflections with I > 2σ(I)
52832 measured reflectionsRint = 0.058
7026 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.175H-atom parameters constrained
S = 1.09Δρmax = 0.64 e Å3
7026 reflectionsΔρmin = 0.26 e Å3
651 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, º) top
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—C3145.4 (4)O6—C31—C32—C33138.8 (4)
C1—C2—C3—C4169.3 (4)C31—C32—C33—C34164.4 (4)
C2—C3—C4—C5173.1 (4)C32—C33—C34—C35172.0 (4)
C2—C3—C4—C666.1 (4)C32—C33—C34—C3667.2 (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—C760.1 (4)C33—C34—C36—C3760.1 (4)
C22—C4—C6—C7178.3 (3)C52—C34—C36—C37178.5 (3)
C5—C4—C6—C1071.7 (4)C35—C34—C36—C4072.7 (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—C38122.2 (4)
C4—C6—C7—C979.2 (5)C34—C36—C37—C38108.6 (4)
C10—C6—C7—C8126.1 (4)C40—C36—C37—C3953.7 (5)
C4—C6—C7—C8105.5 (4)C34—C36—C37—C3975.5 (5)
C7—C6—C10—C11170.8 (3)C37—C36—C40—C41169.7 (4)
C4—C6—C10—C1158.7 (4)C34—C36—C40—C4159.2 (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—C2250.6 (4)C40—C41—C42—C5252.3 (4)
C10—C11—C12—C14168.2 (3)C40—C41—C42—C44169.0 (3)
C11—C12—C14—C19179.8 (3)C43—C42—C44—C4650.1 (4)
C13—C12—C14—C1961.1 (4)C41—C42—C44—C4669.4 (4)
C22—C12—C14—C1961.0 (4)C52—C42—C44—C46172.3 (3)
C11—C12—C14—C1556.2 (4)C43—C42—C44—C4962.5 (4)
C13—C12—C14—C15175.4 (3)C41—C42—C44—C49177.9 (3)
C22—C12—C14—C1562.6 (4)C52—C42—C44—C4959.7 (4)
C11—C12—C14—C1666.6 (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—C4564.3 (4)
C19—C14—C16—C1741.8 (4)C49—C44—C46—C4743.5 (4)
C15—C14—C16—C1773.0 (4)C45—C44—C46—C4772.0 (4)
C12—C14—C16—C17160.7 (3)C42—C44—C46—C47161.6 (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—C491.3 (4)
C23—C18—C19—C2082.3 (4)C46—C44—C49—C50174.8 (3)
C17—C18—C19—C20152.9 (4)C45—C44—C49—C5062.8 (4)
C23—C18—C19—C14152.3 (3)C42—C44—C49—C5062.2 (4)
C17—C18—C19—C1427.6 (4)C46—C44—C49—C4843.2 (4)
C15—C14—C19—C2062.8 (4)C45—C44—C49—C4868.8 (4)
C16—C14—C19—C20173.6 (3)C42—C44—C49—C48166.2 (3)
C12—C14—C19—C2061.9 (4)C53—C48—C49—C5083.0 (4)
C15—C14—C19—C1867.8 (4)C47—C48—C49—C50153.1 (4)
C16—C14—C19—C1843.0 (4)C53—C48—C49—C44150.1 (3)
C12—C14—C19—C18167.5 (3)C47—C48—C49—C4426.2 (4)
C18—C19—C20—C21178.1 (3)C44—C49—C50—C5157.0 (4)
C14—C19—C20—C2155.5 (4)C48—C49—C50—C51179.2 (3)
C19—C20—C21—C2251.7 (5)C49—C50—C51—C5253.5 (4)
C20—C21—C22—C1253.7 (4)C50—C51—C52—C4255.6 (4)
C20—C21—C22—C4171.3 (3)C50—C51—C52—C34169.0 (3)
C11—C12—C22—C21176.7 (3)C43—C42—C52—C5164.1 (4)
C13—C12—C22—C2163.7 (4)C41—C42—C52—C51176.5 (3)
C14—C12—C22—C2156.9 (4)C44—C42—C52—C5156.9 (4)
C11—C12—C22—C450.0 (4)C43—C42—C52—C3469.4 (4)
C13—C12—C22—C469.6 (4)C41—C42—C52—C3450.0 (4)
C14—C12—C22—C4169.8 (3)C44—C42—C52—C34169.6 (3)
C5—C4—C22—C2159.4 (4)C35—C34—C52—C5157.8 (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—C12170.1 (3)C33—C34—C52—C42168.5 (3)
C6—C4—C22—C1251.7 (4)C36—C34—C52—C4250.3 (4)
C27—O3—C23—C24112.4 (4)C57—O8—C53—C54113.8 (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—C2461.5 (5)C47—C48—C53—C5460.6 (4)
C19—C18—C23—C2570.2 (4)C49—C48—C53—C5570.2 (4)
C17—C18—C23—C25169.7 (4)C47—C48—C53—C55170.9 (3)
O3—C23—C25—C2627.0 (4)O8—C53—C55—C5626.8 (4)
C24—C23—C25—C2687.4 (4)C54—C53—C55—C5688.1 (4)
C18—C23—C25—C26142.5 (3)C48—C53—C55—C56142.3 (3)
C23—C25—C26—C2737.5 (4)C53—C55—C56—C5738.0 (4)
C23—O3—C27—O496.1 (3)C53—O8—C57—O995.0 (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—O335.0 (4)C55—C56—C57—O836.1 (4)
C25—C26—C27—C28155.8 (4)C55—C56—C57—C58155.2 (3)
O4—C27—C28—O551.0 (4)O9—C57—C58—O1061.4 (4)
O3—C27—C28—O569.3 (4)O8—C57—C58—O1059.5 (4)
C26—C27—C28—O5171.8 (3)C56—C57—C58—O10176.8 (3)
O4—C27—C28—C30166.5 (3)O9—C57—C58—C5959.7 (4)
O3—C27—C28—C3046.2 (4)O8—C57—C58—C59179.5 (3)
C26—C27—C28—C3072.7 (5)C56—C57—C58—C5962.1 (5)
O4—C27—C28—C2967.3 (4)O9—C57—C58—C60176.3 (4)
O3—C27—C28—C29172.5 (3)O8—C57—C58—C6055.5 (4)
C26—C27—C28—C2953.5 (5)C56—C57—C58—C6061.8 (5)
Hydrogen-bond geometry (Å, º) top
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) x1, y, z; (ii) x+1, y, z; (iii) x+3/2, y+1, z+1/2.

Experimental details

Crystal data
Chemical formulaC30H50O5
Mr490.70
Crystal system, space groupOrthorhombic, P212121
Temperature (K)123
a, b, c (Å)7.7322 (1), 22.4976 (4), 31.6043 (5)
V3)5497.76 (15)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.45 × 0.15 × 0.10
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
52832, 7026, 5590
Rint0.058
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.175, 1.09
No. of reflections7026
No. of parameters651
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.26

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), 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···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) x1, y, z; (ii) x+1, y, z; (iii) x+3/2, y+1, z+1/2.
 

Acknowledgements

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.

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCampos 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.  Google Scholar
First citationLuo, X.-D., Wu, S.-H., Ma, Y.-B. & Wu, D.-G. (2000). Heterocycles, 53, 2795–2802.  CrossRef CAS Google Scholar
First citationMohamad, K., Sévent, T., Dumontet, V., Pais, M., Van Tri, M., Hadi, H., Awang, K. & Martin, M. T. (1999). Phytochemistry, 51, 1031–1037.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2010). publCIF. In preparation.  Google Scholar

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