PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1166.
Published online 2009 April 30. doi:  10.1107/S1600536809015086
PMCID: PMC2977831

3-Oxoolean-1-en-28-oic acid–n-hexa­ne–water (4/1/1) from the bark of Walsura pinnata Hassk

Abstract

3-Oxoolean-1-en-28-oic acid, isolated from the bark of Walsura pinnata Hassk, crystallized from n-hexane as an n-hexane 0.25-solvent 0.25-hydrate, C30H46O3·0.25C6H14·0.25H2O. There are two independent mol­ecules in the asymmetric unit of the title compound. The three six-membered cyclo­hexane rings in each mol­ecule adopt chair conformations and the carboxyl substituent occupies an axial/equatorial position. The two independent mol­ecules are linked by a pair of O—Hcarbox­yl(...)O hydrogen bonds into a dimer. The n-hexane mol­ecule is disordered about a twofold rotation axis and the water mol­ecule lies on a twofold rotation axis. In addition, the cyclo­hexone carbonyl group of one of the independent mol­ecules is disordered over two sites with occupancies of 0.75 and 0.25.

Related literature

There are no reports of chemicals from Walsura pinnata Hassk. For the action of a fungus on this compound, isolated from another source, see: Shirane et al. (1996 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1166-scheme1.jpg

Experimental

Crystal data

  • C30H46O3·0.25C6H14·0.25H2O
  • M r = 480.71
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1166-efi1.jpg
  • a = 28.5864 (7) Å
  • b = 12.2408 (3) Å
  • c = 19.3545 (4) Å
  • β = 120.552 (1)°
  • V = 5832.3 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.07 mm−1
  • T = 100 K
  • 0.45 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 20554 measured reflections
  • 6997 independent reflections
  • 5441 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.068
  • wR(F 2) = 0.204
  • S = 1.07
  • 6997 reflections
  • 676 parameters
  • 71 restraints
  • H-atom parameters constrained
  • Δρmax = 0.81 e Å−3
  • Δρmin = −0.62 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [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, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015086/lh2809sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015086/lh2809Isup2.hkl

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

Acknowledgments

We thank the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The two independent molecules are shown in Fig. 1.

Experimental

The dried and ground bark of Walsura pinnata Hassk (2.3 kg) was extracted with n-hexane for 72 h at room temperature. The solvent was evaporated to give a crude extract, which was subjected to column chromatography on silica gel (60 GF254) by using n-hexane with increasing amounts of ethyl acetate as eluent. Of the twenty-four fractions collected, the twenty-second fraction, eluted with ethyl acetate:n-hexane, 14:86 gave 2 g of the product, which was further purified by column chromatography (n-hexane:ethyl acetate 80:20) to give the title compound (10 mg).

The formulation was established by satisfactory solution NMR spectroscopy.

Refinement

The carbonyl group of one of the two independent molecules is disordered over two positions. For this unit – C17–C18(=O3)–C19 – the 1,2- and 1,3-related distances of the umprimed and primed atoms were restrained to within 0.01 Å of each other. The temperature factors of the umprimed atoms were set to those of the prime ones for the C18/C18' and O3/O3' atoms. The four-atom unit was restrained to be nearly planar.

The hexane molecule lies on a twofold rotation axis; the molecule was instead refined as a six-carbon species, with 1,2- and 1,3-related distances being restrained to 1.54±0.01 and 2.51±0.01 Å. The anisotropic temperature factors of the six carbon atoms were restrained to be nearly isotropic.

The water molecules lies on a twofold rotation axis; the oxygen atom showed large anisotropic temperature factors.

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95–0.99 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C). The acid H-atoms were placed in chemically sensible positions but were not refined.

In the absence of heavy scatterers, Friedel pairs were merged.

Figures

Fig. 1.
70% Probability thermal-ellipsoid plot (Barbour, 2001) of the two independent molecules of C30H46O3.1/4C6H14.1/4H2O. Hydrogen atoms are drawn as spheres of arbitrary radii. The disorder in one of the cyclohexanone carbonyl groups and the solvent molecules ...

Crystal data

C30H46O3·0.25C6H14·0.25H2OF(000) = 2120
Mr = 480.71Dx = 1.095 Mg m3
Monoclinic, C2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2yCell parameters from 4238 reflections
a = 28.5864 (7) Åθ = 2.4–22.7°
b = 12.2408 (3) ŵ = 0.07 mm1
c = 19.3545 (4) ÅT = 100 K
β = 120.552 (1)°Colorless, prism
V = 5832.3 (2) Å30.45 × 0.15 × 0.10 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer5441 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.038
graphiteθmax = 27.5°, θmin = 1.2°
ω scansh = −37→36
20554 measured reflectionsk = −15→15
6997 independent reflectionsl = −25→24

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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.204H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.1276P)2 + 2.2067P] where P = (Fo2 + 2Fc2)/3
6997 reflections(Δ/σ)max = 0.001
676 parametersΔρmax = 0.81 e Å3
71 restraintsΔρmin = −0.62 e Å3

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

xyzUiso*/UeqOcc. (<1)
O10.64169 (14)0.4999 (3)0.06365 (17)0.0372 (7)
H10.66260.50790.11330.056*
O20.64271 (12)0.6807 (3)0.06809 (17)0.0338 (7)
O30.9328 (2)0.6613 (5)−0.1228 (4)0.0706 (16)0.75
O3'0.8798 (6)0.6340 (10)−0.2241 (7)0.0706 (16)0.25
O40.71245 (16)0.5134 (3)0.21228 (19)0.0543 (10)
O50.70076 (14)0.6881 (3)0.22605 (19)0.0427 (8)
H50.67630.68140.17770.064*
O61.12997 (15)0.6700 (4)0.3873 (3)0.0672 (12)
O1W1.00000.834 (2)0.00000.248 (9)
H1W0.97890.7934−0.03850.371*
C10.62647 (15)0.5947 (4)0.0301 (2)0.0268 (8)
C20.58412 (15)0.5936 (4)−0.0588 (2)0.0258 (8)
C30.52936 (16)0.5977 (4)−0.0593 (3)0.0338 (9)
H3A0.52400.5273−0.03910.041*
H3B0.53140.6560−0.02240.041*
C40.48058 (17)0.6192 (4)−0.1430 (3)0.0399 (11)
H4A0.47580.5562−0.17810.048*
H4B0.44740.6253−0.13920.048*
C50.48699 (17)0.7227 (4)−0.1809 (3)0.0371 (10)
C60.4882 (2)0.8240 (5)−0.1331 (3)0.0462 (12)
H6A0.45480.8267−0.13050.069*
H6B0.49080.8899−0.15960.069*
H6C0.51970.8198−0.07860.069*
C70.43893 (19)0.7325 (5)−0.2667 (3)0.0505 (13)
H7A0.40510.7373−0.26570.076*
H7B0.43770.6681−0.29770.076*
H7C0.44320.7984−0.29180.076*
C80.54003 (16)0.7146 (4)−0.1828 (2)0.0308 (9)
H8A0.54500.7833−0.20540.037*
H8B0.53640.6544−0.21930.037*
C90.59140 (15)0.6944 (3)−0.1001 (2)0.0252 (8)
H90.59600.7592−0.06570.030*
C100.64277 (14)0.6855 (3)−0.1054 (2)0.0213 (7)
C110.67132 (16)0.7747 (3)−0.0975 (2)0.0247 (8)
H110.65850.8412−0.08780.030*
C120.72209 (16)0.7808 (3)−0.1023 (2)0.0265 (8)
H12A0.75220.8074−0.05030.032*
H12B0.71650.8349−0.14390.032*
C130.73895 (15)0.6714 (3)−0.1223 (2)0.0215 (7)
H130.71430.6629−0.18150.026*
C140.79755 (15)0.6718 (3)−0.1098 (2)0.0248 (8)
C150.84201 (17)0.7066 (4)−0.0258 (3)0.0335 (9)
H15A0.87620.7167−0.02520.050*
H15B0.84670.65000.01300.050*
H15C0.83160.7755−0.01150.050*
C160.79644 (18)0.7532 (4)−0.1717 (3)0.0363 (10)
H16A0.76630.7334−0.22580.044*
H16B0.78920.8274−0.15910.044*
C170.8498 (2)0.7548 (4)−0.1727 (3)0.0431 (12)
H17A0.84120.7684−0.22840.052*
H17B0.87220.8166−0.13940.052*
C180.8821 (3)0.6541 (6)−0.1435 (3)0.0526 (19)0.75
C18'0.8654 (3)0.6426 (8)−0.1818 (6)0.0526 (19)0.25
C190.86193 (19)0.5453 (4)−0.1348 (3)0.0376 (10)
C200.8513 (2)0.4719 (6)−0.2056 (3)0.0541 (15)
H20A0.88540.4606−0.20530.081*
H20B0.82470.5070−0.25600.081*
H20C0.83710.4013−0.20070.081*
C210.9086 (2)0.4917 (8)−0.0581 (3)0.070 (2)
H21A0.94070.4844−0.06360.104*
H21B0.89720.4193−0.05070.104*
H21C0.91750.5376−0.01150.104*
C220.80785 (16)0.5581 (3)−0.1335 (2)0.0257 (8)
H220.77800.5468−0.19020.031*
C230.80078 (17)0.4670 (3)−0.0851 (2)0.0291 (8)
H23A0.80980.3956−0.09930.035*
H23B0.82580.4795−0.02700.035*
C240.74204 (17)0.4658 (3)−0.1034 (2)0.0273 (8)
H24A0.73810.4075−0.07120.033*
H24B0.71770.4476−0.16070.033*
C250.72373 (15)0.5751 (3)−0.0854 (2)0.0225 (7)
C260.75144 (15)0.5890 (4)0.0067 (2)0.0259 (8)
H26A0.79070.57910.03120.039*
H26B0.73710.53430.02810.039*
H26C0.74400.66230.01900.039*
C270.65940 (15)0.5761 (3)−0.1251 (2)0.0225 (7)
C280.62911 (16)0.5670 (3)−0.2184 (2)0.0275 (8)
H28A0.59080.5494−0.23890.041*
H28B0.64580.5091−0.23380.041*
H28C0.63170.6366−0.24120.041*
C290.64230 (16)0.4771 (3)−0.0940 (2)0.0251 (8)
H29A0.64120.4117−0.12480.030*
H29B0.67040.4643−0.03720.030*
C300.58735 (16)0.4889 (3)−0.0997 (2)0.0259 (8)
H30A0.58110.4250−0.07410.031*
H30B0.55830.4900−0.15690.031*
C310.72161 (17)0.5932 (4)0.2551 (2)0.0339 (9)
C320.75531 (17)0.5834 (4)0.3459 (2)0.0339 (9)
C330.7125 (2)0.5534 (5)0.3692 (3)0.0433 (11)
H33A0.68990.61850.36230.052*
H33B0.68830.49590.33240.052*
C340.7382 (2)0.5129 (6)0.4555 (3)0.0551 (15)
H34A0.70900.48930.46550.066*
H34B0.75780.57410.49240.066*
C350.7776 (2)0.4181 (6)0.4742 (3)0.0597 (17)
C360.7479 (3)0.3152 (6)0.4269 (4)0.071 (2)
H36A0.77360.25420.44380.106*
H36B0.73260.32850.36940.106*
H36C0.71860.29720.43720.106*
C370.8052 (3)0.3955 (8)0.5653 (4)0.084 (3)
H37A0.83020.33360.57950.126*
H37B0.77750.37820.57910.126*
H37C0.82550.46040.59520.126*
C380.8213 (2)0.4554 (5)0.4546 (3)0.0468 (13)
H38A0.84220.51630.49070.056*
H38B0.84680.39420.46540.056*
C390.79764 (18)0.4926 (4)0.3673 (2)0.0359 (10)
H390.77780.42850.33270.043*
C400.84081 (17)0.5249 (4)0.3471 (2)0.0314 (9)
C410.85843 (19)0.4506 (4)0.3156 (3)0.0413 (11)
H410.84280.37980.30680.050*
C420.9010 (2)0.4683 (5)0.2927 (3)0.0489 (13)
H42A0.88390.46060.23380.059*
H42B0.92900.41050.31790.059*
C430.92871 (16)0.5796 (4)0.3176 (2)0.0305 (9)
H430.95360.57410.37700.037*
C440.96696 (16)0.6060 (4)0.2835 (2)0.0329 (10)
C450.9375 (2)0.6018 (6)0.1903 (3)0.0561 (16)
H45A0.91820.67070.16800.084*
H45B0.91140.54130.17060.084*
H45C0.96430.59060.17360.084*
C461.01230 (18)0.5192 (4)0.3172 (3)0.0396 (11)
H46A1.02650.51030.37540.048*
H46B0.99690.44830.29080.048*
C471.0592 (2)0.5498 (5)0.3042 (3)0.0451 (12)
H47A1.08790.49350.32930.054*
H47B1.04590.55060.24600.054*
C481.08275 (19)0.6585 (5)0.3391 (3)0.0419 (11)
C491.0432 (2)0.7552 (4)0.3119 (3)0.0423 (11)
C501.0716 (3)0.8501 (5)0.3670 (5)0.0698 (19)
H50A1.07480.83660.41910.105*
H50B1.05050.91700.34350.105*
H50C1.10790.85860.37420.105*
C511.0297 (3)0.7881 (7)0.2266 (4)0.073 (2)
H51A1.06340.80570.22730.109*
H51B1.00590.85220.20890.109*
H51C1.01140.72730.18960.109*
C520.99266 (18)0.7183 (4)0.3177 (2)0.0339 (10)
H521.00730.71090.37660.041*
C530.9495 (2)0.8059 (4)0.2916 (3)0.0425 (12)
H53A0.92730.80780.23230.051*
H53B0.96700.87820.31040.051*
C540.9129 (2)0.7824 (4)0.3265 (3)0.0370 (10)
H54A0.88390.83830.30620.044*
H54B0.93480.79010.38550.044*
C550.88640 (17)0.6687 (4)0.3064 (2)0.0302 (9)
C560.83882 (18)0.6701 (5)0.2192 (2)0.0452 (13)
H56A0.85260.68490.18300.068*
H56B0.81300.72740.21300.068*
H56C0.82050.59910.20600.068*
C570.86480 (17)0.6396 (4)0.3657 (2)0.0298 (9)
C580.91077 (17)0.6397 (4)0.4546 (2)0.0330 (9)
H58A0.89490.63900.48910.050*
H58B0.93310.70540.46560.050*
H58C0.93350.57470.46540.050*
C590.82326 (18)0.7272 (4)0.3573 (3)0.0332 (9)
H59A0.84330.79240.38870.040*
H59B0.80160.74940.30030.040*
C600.78427 (18)0.6904 (4)0.3852 (3)0.0359 (10)
H60A0.80490.68090.44420.043*
H60B0.75680.74820.37240.043*
C610.8146 (6)1.0554 (15)0.3756 (8)0.092 (5)0.50
H61A0.79830.99410.33820.138*0.50
H61B0.82071.11640.34830.138*0.50
H61C0.79001.07860.39410.138*0.50
C630.8949 (7)1.1153 (17)0.5058 (10)0.139 (8)0.50
H63A0.92531.08800.55730.167*0.50
H63B0.86831.15170.51630.167*0.50
C640.9164 (11)1.197 (2)0.4664 (11)0.179 (12)0.50
H64A0.93151.15710.43760.215*0.50
H64B0.88661.24490.42770.215*0.50
C620.8679 (7)1.0202 (13)0.4464 (10)0.128 (7)0.50
H62A0.89240.99470.42750.153*0.50
H62B0.86180.95850.47390.153*0.50
C650.9612 (9)1.2658 (19)0.5355 (12)0.142 (9)0.50
H65A0.94581.30530.56400.170*0.50
H65B0.99051.21720.57430.170*0.50
C660.9844 (11)1.347 (2)0.5009 (18)0.160 (12)0.50
H66A1.01321.39010.54460.240*0.50
H66B0.95541.39660.46360.240*0.50
H66C0.99921.30790.47230.240*0.50

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0479 (19)0.0291 (17)0.0274 (14)0.0008 (14)0.0138 (14)−0.0006 (13)
O20.0416 (17)0.0257 (15)0.0323 (14)0.0010 (13)0.0173 (13)−0.0036 (13)
O30.050 (3)0.062 (3)0.116 (4)0.006 (3)0.054 (3)0.021 (3)
O3'0.050 (3)0.062 (3)0.116 (4)0.006 (3)0.054 (3)0.021 (3)
O40.064 (2)0.038 (2)0.0313 (16)0.0119 (18)0.0029 (16)−0.0100 (15)
O50.049 (2)0.0372 (19)0.0327 (15)0.0086 (16)0.0144 (14)−0.0053 (14)
O60.037 (2)0.050 (2)0.083 (3)−0.0008 (18)0.0078 (19)0.010 (2)
O1W0.249 (12)0.228 (13)0.248 (12)0.0000.113 (9)0.000
C10.0260 (18)0.027 (2)0.0327 (18)0.0002 (17)0.0190 (16)−0.0016 (18)
C20.0213 (17)0.028 (2)0.0282 (17)−0.0006 (16)0.0130 (14)−0.0018 (17)
C30.0272 (19)0.039 (2)0.041 (2)−0.0017 (19)0.0220 (17)−0.003 (2)
C40.0219 (19)0.046 (3)0.048 (2)0.0007 (19)0.0152 (18)−0.006 (2)
C50.0222 (19)0.040 (3)0.041 (2)0.0043 (19)0.0099 (18)−0.001 (2)
C60.031 (2)0.044 (3)0.059 (3)0.009 (2)0.020 (2)−0.004 (2)
C70.026 (2)0.051 (3)0.050 (3)0.001 (2)0.002 (2)−0.001 (2)
C80.0259 (19)0.030 (2)0.0295 (18)0.0019 (17)0.0092 (16)−0.0008 (17)
C90.0223 (18)0.025 (2)0.0264 (17)0.0028 (16)0.0110 (15)−0.0024 (16)
C100.0214 (17)0.0225 (19)0.0170 (15)0.0055 (15)0.0074 (13)0.0003 (14)
C110.0284 (19)0.0195 (19)0.0262 (17)0.0072 (16)0.0138 (15)0.0011 (15)
C120.0295 (19)0.020 (2)0.0328 (19)−0.0033 (17)0.0182 (17)−0.0036 (16)
C130.0237 (17)0.0172 (17)0.0238 (16)0.0019 (15)0.0121 (14)0.0024 (15)
C140.0228 (17)0.0236 (19)0.0287 (18)0.0016 (16)0.0136 (15)0.0042 (16)
C150.0264 (19)0.031 (2)0.036 (2)−0.0015 (18)0.0104 (17)−0.0014 (18)
C160.031 (2)0.034 (2)0.047 (2)0.0059 (19)0.022 (2)0.017 (2)
C170.039 (2)0.043 (3)0.057 (3)0.005 (2)0.030 (2)0.019 (2)
C180.074 (5)0.045 (3)0.071 (5)−0.004 (3)0.060 (4)−0.006 (4)
C18'0.074 (5)0.045 (3)0.071 (5)−0.004 (3)0.060 (4)−0.006 (4)
C190.043 (2)0.037 (2)0.048 (3)0.005 (2)0.034 (2)0.003 (2)
C200.044 (3)0.074 (4)0.049 (3)0.021 (3)0.027 (2)−0.009 (3)
C210.035 (3)0.123 (6)0.052 (3)0.021 (3)0.023 (2)−0.004 (4)
C220.0254 (18)0.028 (2)0.0261 (18)0.0005 (16)0.0147 (15)0.0033 (15)
C230.035 (2)0.023 (2)0.035 (2)0.0045 (18)0.0221 (18)0.0053 (17)
C240.034 (2)0.0180 (18)0.036 (2)0.0050 (17)0.0220 (17)0.0046 (16)
C250.0258 (17)0.0184 (18)0.0254 (17)0.0012 (15)0.0144 (14)0.0009 (15)
C260.0252 (17)0.029 (2)0.0246 (16)0.0035 (17)0.0132 (14)0.0060 (16)
C270.0264 (17)0.0184 (18)0.0245 (17)0.0018 (16)0.0142 (14)−0.0009 (15)
C280.0300 (19)0.027 (2)0.0245 (17)−0.0022 (17)0.0135 (15)−0.0049 (16)
C290.032 (2)0.0163 (18)0.0310 (19)−0.0024 (16)0.0189 (17)−0.0027 (15)
C300.028 (2)0.025 (2)0.0266 (17)−0.0041 (16)0.0152 (16)−0.0007 (16)
C310.036 (2)0.032 (2)0.0308 (19)0.001 (2)0.0149 (17)−0.0063 (19)
C320.034 (2)0.040 (3)0.0271 (18)−0.006 (2)0.0146 (16)−0.0055 (19)
C330.039 (2)0.053 (3)0.040 (2)−0.011 (2)0.022 (2)−0.006 (2)
C340.048 (3)0.079 (4)0.038 (2)−0.025 (3)0.022 (2)−0.003 (3)
C350.044 (3)0.077 (4)0.040 (3)−0.032 (3)0.009 (2)0.009 (3)
C360.049 (3)0.068 (4)0.071 (4)−0.024 (3)0.012 (3)0.018 (3)
C370.059 (4)0.125 (7)0.051 (3)−0.041 (4)0.016 (3)0.030 (4)
C380.037 (2)0.053 (3)0.036 (2)−0.018 (2)0.008 (2)0.008 (2)
C390.030 (2)0.038 (3)0.0291 (19)−0.0081 (19)0.0073 (17)0.0003 (19)
C400.0247 (19)0.033 (2)0.0253 (18)0.0014 (18)0.0048 (16)−0.0008 (17)
C410.033 (2)0.030 (2)0.050 (3)−0.0028 (19)0.014 (2)−0.013 (2)
C420.035 (2)0.042 (3)0.063 (3)−0.002 (2)0.020 (2)−0.025 (3)
C430.0274 (19)0.034 (2)0.0240 (17)0.0042 (18)0.0086 (15)−0.0036 (17)
C440.0255 (19)0.043 (3)0.0225 (17)0.0096 (19)0.0070 (15)0.0010 (18)
C450.034 (2)0.100 (5)0.029 (2)0.013 (3)0.0128 (18)−0.012 (3)
C460.029 (2)0.043 (3)0.038 (2)0.006 (2)0.0109 (18)−0.010 (2)
C470.031 (2)0.048 (3)0.051 (3)0.011 (2)0.017 (2)−0.002 (2)
C480.037 (2)0.049 (3)0.039 (2)0.010 (2)0.019 (2)0.012 (2)
C490.043 (3)0.048 (3)0.044 (2)0.015 (2)0.027 (2)0.021 (2)
C500.074 (4)0.038 (3)0.126 (6)−0.005 (3)0.072 (4)0.003 (3)
C510.064 (4)0.105 (6)0.070 (4)0.044 (4)0.049 (3)0.058 (4)
C520.034 (2)0.042 (3)0.0283 (19)0.012 (2)0.0177 (17)0.0119 (18)
C530.044 (3)0.045 (3)0.046 (3)0.019 (2)0.028 (2)0.023 (2)
C540.046 (3)0.032 (2)0.044 (2)0.014 (2)0.031 (2)0.012 (2)
C550.032 (2)0.036 (2)0.0225 (17)0.0056 (19)0.0133 (16)0.0011 (17)
C560.034 (2)0.075 (4)0.0233 (18)0.019 (2)0.0122 (17)0.006 (2)
C570.031 (2)0.035 (2)0.0225 (17)0.0000 (18)0.0128 (16)−0.0034 (16)
C580.032 (2)0.043 (2)0.0237 (18)−0.0104 (19)0.0139 (16)−0.0022 (17)
C590.035 (2)0.034 (2)0.036 (2)−0.0038 (19)0.0217 (18)−0.0114 (18)
C600.034 (2)0.041 (3)0.036 (2)−0.004 (2)0.0209 (18)−0.010 (2)
C610.119 (9)0.086 (9)0.066 (7)0.030 (7)0.044 (7)−0.007 (6)
C630.130 (11)0.126 (12)0.155 (12)0.005 (9)0.067 (9)−0.010 (9)
C640.182 (15)0.173 (16)0.178 (15)0.007 (10)0.089 (11)0.008 (10)
C620.140 (11)0.131 (12)0.113 (10)0.002 (9)0.065 (9)−0.018 (9)
C650.135 (12)0.124 (12)0.142 (12)0.000 (9)0.053 (9)−0.013 (9)
C660.157 (16)0.163 (14)0.161 (13)−0.013 (9)0.081 (10)0.006 (10)

Geometric parameters (Å, °)

O1—C11.292 (5)C33—C341.527 (7)
O1—H10.8400C33—H33A0.9900
O2—C11.233 (5)C33—H33B0.9900
O3—C181.294 (8)C34—C351.528 (10)
O3'—C18'1.091 (15)C34—H34A0.9900
O4—C311.220 (6)C34—H34B0.9900
O5—C311.297 (6)C35—C361.534 (9)
O5—H50.8400C35—C381.546 (7)
O6—C481.197 (6)C35—C371.548 (8)
O1W—H1W0.8399C36—H36A0.9800
C1—C21.519 (5)C36—H36B0.9800
C2—C301.533 (6)C36—H36C0.9800
C2—C91.540 (6)C37—H37A0.9800
C2—C31.562 (5)C37—H37B0.9800
C3—C41.530 (6)C37—H37C0.9800
C3—H3A0.9900C38—C391.535 (6)
C3—H3B0.9900C38—H38A0.9900
C4—C51.521 (7)C38—H38B0.9900
C4—H4A0.9900C39—C401.525 (6)
C4—H4B0.9900C39—H391.0000
C5—C71.531 (6)C40—C411.327 (6)
C5—C61.537 (7)C40—C571.524 (6)
C5—C81.538 (6)C41—C421.510 (7)
C6—H6A0.9800C41—H410.9500
C6—H6B0.9800C42—C431.525 (7)
C6—H6C0.9800C42—H42A0.9900
C7—H7A0.9800C42—H42B0.9900
C7—H7B0.9800C43—C551.560 (6)
C7—H7C0.9800C43—C441.572 (6)
C8—C91.546 (5)C43—H431.0000
C8—H8A0.9900C44—C461.541 (6)
C8—H8B0.9900C44—C521.540 (7)
C9—C101.528 (5)C44—C451.556 (6)
C9—H91.0000C45—H45A0.9800
C10—C111.325 (6)C45—H45B0.9800
C10—C271.532 (5)C45—H45C0.9800
C11—C121.503 (5)C46—C471.529 (7)
C11—H110.9500C46—H46A0.9900
C12—C131.537 (5)C46—H46B0.9900
C12—H12A0.9900C47—C481.490 (8)
C12—H12B0.9900C47—H47A0.9900
C13—C251.550 (5)C47—H47B0.9900
C13—C141.566 (5)C48—C491.533 (7)
C13—H131.0000C49—C501.504 (9)
C14—C151.530 (6)C49—C511.545 (7)
C14—C221.540 (6)C49—C521.571 (6)
C14—C161.545 (6)C50—H50A0.9800
C15—H15A0.9800C50—H50B0.9800
C15—H15B0.9800C50—H50C0.9800
C15—H15C0.9800C51—H51A0.9800
C16—C171.535 (6)C51—H51B0.9800
C16—H16A0.9900C51—H51C0.9800
C16—H16B0.9900C52—C531.515 (6)
C17—C181.471 (9)C52—H521.0000
C17—C18'1.481 (12)C53—C541.532 (6)
C17—H17A0.9900C53—H53A0.9900
C17—H17B0.9900C53—H53B0.9900
C18—C191.495 (8)C54—C551.538 (7)
C18'—C191.533 (12)C54—H54A0.9900
C19—C201.535 (7)C54—H54B0.9900
C19—C211.550 (8)C55—C561.537 (5)
C19—C221.566 (6)C55—C571.596 (5)
C20—H20A0.9800C56—H56A0.9800
C20—H20B0.9800C56—H56B0.9800
C20—H20C0.9800C56—H56C0.9800
C21—H21A0.9800C57—C591.546 (6)
C21—H21B0.9800C57—C581.546 (5)
C21—H21C0.9800C58—H58A0.9800
C22—C231.534 (5)C58—H58B0.9800
C22—H221.0000C58—H58C0.9800
C23—C241.530 (6)C59—C601.533 (6)
C23—H23A0.9900C59—H59A0.9900
C23—H23B0.9900C59—H59B0.9900
C24—C251.540 (5)C60—H60A0.9900
C24—H24A0.9900C60—H60B0.9900
C24—H24B0.9900C61—C621.504 (10)
C25—C261.548 (5)C61—H61A0.9800
C25—C271.592 (5)C61—H61B0.9800
C26—H26A0.9800C61—H61C0.9800
C26—H26B0.9800C63—C621.540 (10)
C26—H26C0.9800C63—C641.560 (11)
C27—C291.540 (5)C63—H63A0.9900
C27—C281.560 (5)C63—H63B0.9900
C28—H28A0.9800C64—C651.548 (11)
C28—H28B0.9800C64—H64A0.9900
C28—H28C0.9800C64—H64B0.9900
C29—C301.525 (5)C62—H62A0.9900
C29—H29A0.9900C62—H62B0.9900
C29—H29B0.9900C65—C661.527 (11)
C30—H30A0.9900C65—H65A0.9900
C30—H30B0.9900C65—H65B0.9900
C31—C321.519 (6)C66—H66A0.9800
C32—C601.530 (7)C66—H66B0.9800
C32—C391.537 (7)C66—H66C0.9800
C32—C331.548 (6)
C1—O1—H1109.5C34—C33—H33B109.1
C31—O5—H5109.5C32—C33—H33B109.1
O2—C1—O1122.6 (3)H33A—C33—H33B107.8
O2—C1—C2121.6 (4)C33—C34—C35113.1 (5)
O1—C1—C2115.7 (4)C33—C34—H34A109.0
C1—C2—C30111.6 (3)C35—C34—H34A109.0
C1—C2—C9109.9 (3)C33—C34—H34B109.0
C30—C2—C9110.1 (3)C35—C34—H34B109.0
C1—C2—C3103.1 (3)H34A—C34—H34B107.8
C30—C2—C3110.3 (3)C34—C35—C36111.4 (5)
C9—C2—C3111.8 (3)C34—C35—C38108.0 (5)
C4—C3—C2112.5 (3)C36—C35—C38111.5 (6)
C4—C3—H3A109.1C34—C35—C37107.0 (6)
C2—C3—H3A109.1C36—C35—C37109.9 (5)
C4—C3—H3B109.1C38—C35—C37108.9 (4)
C2—C3—H3B109.1C35—C36—H36A109.5
H3A—C3—H3B107.8C35—C36—H36B109.5
C5—C4—C3112.7 (4)H36A—C36—H36B109.5
C5—C4—H4A109.1C35—C36—H36C109.5
C3—C4—H4A109.1H36A—C36—H36C109.5
C5—C4—H4B109.1H36B—C36—H36C109.5
C3—C4—H4B109.1C35—C37—H37A109.5
H4A—C4—H4B107.8C35—C37—H37B109.5
C4—C5—C7109.1 (4)H37A—C37—H37B109.5
C4—C5—C6110.7 (4)C35—C37—H37C109.5
C7—C5—C6108.8 (4)H37A—C37—H37C109.5
C4—C5—C8108.7 (4)H37B—C37—H37C109.5
C7—C5—C8109.3 (4)C39—C38—C35113.5 (4)
C6—C5—C8110.2 (4)C39—C38—H38A108.9
C5—C6—H6A109.5C35—C38—H38A108.9
C5—C6—H6B109.5C39—C38—H38B108.9
H6A—C6—H6B109.5C35—C38—H38B108.9
C5—C6—H6C109.5H38A—C38—H38B107.7
H6A—C6—H6C109.5C40—C39—C38113.5 (4)
H6B—C6—H6C109.5C40—C39—C32111.9 (4)
C5—C7—H7A109.5C38—C39—C32111.0 (4)
C5—C7—H7B109.5C40—C39—H39106.7
H7A—C7—H7B109.5C38—C39—H39106.7
C5—C7—H7C109.5C32—C39—H39106.7
H7A—C7—H7C109.5C41—C40—C57120.7 (4)
H7B—C7—H7C109.5C41—C40—C39119.1 (4)
C5—C8—C9114.5 (3)C57—C40—C39120.2 (4)
C5—C8—H8A108.6C40—C41—C42126.0 (4)
C9—C8—H8A108.6C40—C41—H41117.0
C5—C8—H8B108.6C42—C41—H41117.0
C9—C8—H8B108.6C41—C42—C43113.7 (4)
H8A—C8—H8B107.6C41—C42—H42A108.8
C10—C9—C2111.4 (3)C43—C42—H42A108.8
C10—C9—C8112.4 (3)C41—C42—H42B108.8
C2—C9—C8110.9 (3)C43—C42—H42B108.8
C10—C9—H9107.3H42A—C42—H42B107.7
C2—C9—H9107.3C42—C43—C55109.9 (3)
C8—C9—H9107.3C42—C43—C44114.2 (4)
C11—C10—C9119.3 (3)C55—C43—C44116.9 (4)
C11—C10—C27119.9 (3)C42—C43—H43104.8
C9—C10—C27120.7 (3)C55—C43—H43104.8
C10—C11—C12126.2 (3)C44—C43—H43104.8
C10—C11—H11116.9C46—C44—C52108.6 (3)
C12—C11—H11116.9C46—C44—C45108.1 (4)
C11—C12—C13114.1 (3)C52—C44—C45112.8 (4)
C11—C12—H12A108.7C46—C44—C43107.2 (4)
C13—C12—H12A108.7C52—C44—C43106.5 (3)
C11—C12—H12B108.7C45—C44—C43113.5 (4)
C13—C12—H12B108.7C44—C45—H45A109.5
H12A—C12—H12B107.6C44—C45—H45B109.5
C12—C13—C25110.4 (3)H45A—C45—H45B109.5
C12—C13—C14113.9 (3)C44—C45—H45C109.5
C25—C13—C14117.4 (3)H45A—C45—H45C109.5
C12—C13—H13104.5H45B—C45—H45C109.5
C25—C13—H13104.5C47—C46—C44112.4 (4)
C14—C13—H13104.5C47—C46—H46A109.1
C15—C14—C22112.8 (3)C44—C46—H46A109.1
C15—C14—C16108.8 (4)C47—C46—H46B109.1
C22—C14—C16106.5 (3)C44—C46—H46B109.1
C15—C14—C13114.2 (3)H46A—C46—H46B107.9
C22—C14—C13107.6 (3)C48—C47—C46112.2 (4)
C16—C14—C13106.5 (3)C48—C47—H47A109.2
C14—C15—H15A109.5C46—C47—H47A109.2
C14—C15—H15B109.5C48—C47—H47B109.2
H15A—C15—H15B109.5C46—C47—H47B109.2
C14—C15—H15C109.5H47A—C47—H47B107.9
H15A—C15—H15C109.5O6—C48—C47122.0 (5)
H15B—C15—H15C109.5O6—C48—C49121.3 (5)
C17—C16—C14112.9 (3)C47—C48—C49116.7 (4)
C17—C16—H16A109.0C50—C49—C48108.4 (5)
C14—C16—H16A109.0C50—C49—C51107.9 (5)
C17—C16—H16B109.0C48—C49—C51107.9 (4)
C14—C16—H16B109.0C50—C49—C52110.8 (4)
H16A—C16—H16B107.8C48—C49—C52107.3 (4)
C18—C17—C18'25.9 (4)C51—C49—C52114.3 (4)
C18—C17—C16114.8 (4)C49—C50—H50A109.5
C18'—C17—C16110.6 (5)C49—C50—H50B109.5
C18—C17—H17A108.6H50A—C50—H50B109.5
C18'—C17—H17A87.1C49—C50—H50C109.5
C16—C17—H17A108.6H50A—C50—H50C109.5
C18—C17—H17B108.6H50B—C50—H50C109.5
C18'—C17—H17B130.7C49—C51—H51A109.5
C16—C17—H17B108.6C49—C51—H51B109.5
H17A—C17—H17B107.5H51A—C51—H51B109.5
O3—C18—C17116.7 (6)C49—C51—H51C109.5
O3—C18—C19117.5 (6)H51A—C51—H51C109.5
C17—C18—C19125.9 (5)H51B—C51—H51C109.5
O3'—C18'—C17115.5 (10)C53—C52—C44111.0 (4)
O3'—C18'—C19122.2 (11)C53—C52—C49113.3 (4)
C17—C18'—C19122.3 (9)C44—C52—C49118.8 (4)
C18—C19—C18'25.2 (3)C53—C52—H52104.0
C18—C19—C20109.4 (4)C44—C52—H52104.0
C18'—C19—C2088.1 (5)C49—C52—H52104.0
C18—C19—C21106.9 (5)C52—C53—C54110.1 (4)
C18'—C19—C21127.8 (5)C52—C53—H53A109.6
C20—C19—C21106.9 (5)C54—C53—H53A109.6
C18—C19—C22110.8 (4)C52—C53—H53B109.6
C18'—C19—C22107.1 (5)C54—C53—H53B109.6
C20—C19—C22108.9 (4)H53A—C53—H53B108.2
C21—C19—C22113.9 (4)C53—C54—C55114.6 (4)
C19—C20—H20A109.5C53—C54—H54A108.6
C19—C20—H20B109.5C55—C54—H54A108.6
H20A—C20—H20B109.5C53—C54—H54B108.6
C19—C20—H20C109.5C55—C54—H54B108.6
H20A—C20—H20C109.5H54A—C54—H54B107.6
H20B—C20—H20C109.5C56—C55—C54108.3 (4)
C19—C21—H21A109.5C56—C55—C43110.6 (3)
C19—C21—H21B109.5C54—C55—C43110.5 (3)
H21A—C21—H21B109.5C56—C55—C57110.0 (3)
C19—C21—H21C109.5C54—C55—C57109.9 (3)
H21A—C21—H21C109.5C43—C55—C57107.5 (3)
H21B—C21—H21C109.5C55—C56—H56A109.5
C23—C22—C14111.7 (3)C55—C56—H56B109.5
C23—C22—C19112.0 (3)H56A—C56—H56B109.5
C14—C22—C19115.8 (3)C55—C56—H56C109.5
C23—C22—H22105.5H56A—C56—H56C109.5
C14—C22—H22105.5H56B—C56—H56C109.5
C19—C22—H22105.5C40—C57—C59112.7 (3)
C24—C23—C22109.6 (3)C40—C57—C58106.8 (3)
C24—C23—H23A109.7C59—C57—C58106.8 (3)
C22—C23—H23A109.7C40—C57—C55109.1 (3)
C24—C23—H23B109.7C59—C57—C55109.1 (3)
C22—C23—H23B109.7C58—C57—C55112.3 (3)
H23A—C23—H23B108.2C57—C58—H58A109.5
C23—C24—C25113.5 (3)C57—C58—H58B109.5
C23—C24—H24A108.9H58A—C58—H58B109.5
C25—C24—H24A108.9C57—C58—H58C109.5
C23—C24—H24B108.9H58A—C58—H58C109.5
C25—C24—H24B108.9H58B—C58—H58C109.5
H24A—C24—H24B107.7C60—C59—C57114.6 (4)
C24—C25—C26108.8 (3)C60—C59—H59A108.6
C24—C25—C13110.4 (3)C57—C59—H59A108.6
C26—C25—C13110.4 (3)C60—C59—H59B108.6
C24—C25—C27109.8 (3)C57—C59—H59B108.6
C26—C25—C27110.2 (3)H59A—C59—H59B107.6
C13—C25—C27107.3 (3)C32—C60—C59112.5 (3)
C25—C26—H26A109.5C32—C60—H60A109.1
C25—C26—H26B109.5C59—C60—H60A109.1
H26A—C26—H26B109.5C32—C60—H60B109.1
C25—C26—H26C109.5C59—C60—H60B109.1
H26A—C26—H26C109.5H60A—C60—H60B107.8
H26B—C26—H26C109.5C62—C61—H61A109.5
C10—C27—C29113.0 (3)C62—C61—H61B109.5
C10—C27—C28106.9 (3)H61A—C61—H61B109.5
C29—C27—C28107.3 (3)C62—C61—H61C109.5
C10—C27—C25108.3 (3)H61A—C61—H61C109.5
C29—C27—C25108.9 (3)H61B—C61—H61C109.5
C28—C27—C25112.6 (3)C62—C63—C64107.0 (9)
C27—C28—H28A109.5C62—C63—H63A110.3
C27—C28—H28B109.5C64—C63—H63A110.3
H28A—C28—H28B109.5C62—C63—H63B110.3
C27—C28—H28C109.5C64—C63—H63B110.3
H28A—C28—H28C109.5H63A—C63—H63B108.6
H28B—C28—H28C109.5C65—C64—C63106.6 (9)
C30—C29—C27114.6 (3)C65—C64—H64A110.4
C30—C29—H29A108.6C63—C64—H64A110.4
C27—C29—H29A108.6C65—C64—H64B110.4
C30—C29—H29B108.6C63—C64—H64B110.4
C27—C29—H29B108.6H64A—C64—H64B108.6
H29A—C29—H29B107.6C61—C62—C63110.8 (10)
C29—C30—C2111.9 (3)C61—C62—H62A109.5
C29—C30—H30A109.2C63—C62—H62A109.5
C2—C30—H30A109.2C61—C62—H62B109.5
C29—C30—H30B109.2C63—C62—H62B109.5
C2—C30—H30B109.2H62A—C62—H62B108.1
H30A—C30—H30B107.9C66—C65—C64109.2 (10)
O4—C31—O5122.0 (4)C66—C65—H65A109.8
O4—C31—C32120.9 (4)C64—C65—H65A109.8
O5—C31—C32117.0 (4)C66—C65—H65B109.8
C31—C32—C60111.9 (4)C64—C65—H65B109.8
C31—C32—C39108.6 (3)H65A—C65—H65B108.3
C60—C32—C39109.4 (3)C65—C66—H66A109.5
C31—C32—C33103.0 (3)C65—C66—H66B109.5
C60—C32—C33111.5 (4)H66A—C66—H66B109.5
C39—C32—C33112.4 (4)C65—C66—H66C109.5
C34—C33—C32112.6 (4)H66A—C66—H66C109.5
C34—C33—H33A109.1H66B—C66—H66C109.5
C32—C33—H33A109.1
O2—C1—C2—C30156.5 (4)C13—C25—C27—C2857.6 (4)
O1—C1—C2—C30−27.4 (5)C10—C27—C29—C3037.2 (4)
O2—C1—C2—C934.1 (5)C28—C27—C29—C30−80.3 (4)
O1—C1—C2—C9−149.9 (3)C25—C27—C29—C30157.6 (3)
O2—C1—C2—C3−85.2 (5)C27—C29—C30—C2−53.9 (4)
O1—C1—C2—C390.9 (4)C1—C2—C30—C29−61.1 (4)
C1—C2—C3—C4169.1 (4)C9—C2—C30—C2961.2 (4)
C30—C2—C3—C4−71.6 (5)C3—C2—C30—C29−175.0 (3)
C9—C2—C3—C451.2 (5)O4—C31—C32—C60152.6 (5)
C2—C3—C4—C5−55.4 (5)O5—C31—C32—C60−31.2 (6)
C3—C4—C5—C7175.2 (4)O4—C31—C32—C3931.8 (6)
C3—C4—C5—C6−65.1 (5)O5—C31—C32—C39−152.0 (4)
C3—C4—C5—C856.1 (5)O4—C31—C32—C33−87.5 (6)
C4—C5—C8—C9−56.1 (5)O5—C31—C32—C3388.7 (5)
C7—C5—C8—C9−175.0 (4)C31—C32—C33—C34166.4 (5)
C6—C5—C8—C965.3 (5)C60—C32—C33—C34−73.4 (6)
C1—C2—C9—C1070.8 (4)C39—C32—C33—C3449.8 (6)
C30—C2—C9—C10−52.5 (4)C32—C33—C34—C35−54.0 (6)
C3—C2—C9—C10−175.4 (3)C33—C34—C35—C36−66.5 (6)
C1—C2—C9—C8−163.1 (3)C33—C34—C35—C3856.2 (6)
C30—C2—C9—C873.5 (4)C33—C34—C35—C37173.4 (4)
C3—C2—C9—C8−49.3 (4)C34—C35—C38—C39−57.6 (6)
C5—C8—C9—C10179.2 (4)C36—C35—C38—C3965.1 (7)
C5—C8—C9—C253.7 (5)C37—C35—C38—C39−173.4 (6)
C2—C9—C10—C11−144.3 (3)C35—C38—C39—C40−177.6 (5)
C8—C9—C10—C1190.4 (4)C35—C38—C39—C3255.4 (6)
C2—C9—C10—C2739.6 (4)C31—C32—C39—C4068.9 (4)
C8—C9—C10—C27−85.6 (4)C60—C32—C39—C40−53.4 (4)
C9—C10—C11—C12−179.0 (3)C33—C32—C39—C40−177.8 (3)
C27—C10—C11—C12−2.9 (6)C31—C32—C39—C38−163.2 (4)
C10—C11—C12—C132.9 (5)C60—C32—C39—C3874.5 (4)
C11—C12—C13—C25−33.3 (4)C33—C32—C39—C38−49.9 (5)
C11—C12—C13—C14−167.9 (3)C38—C39—C40—C4193.5 (5)
C12—C13—C14—C1554.9 (4)C32—C39—C40—C41−139.9 (4)
C25—C13—C14—C15−76.4 (4)C38—C39—C40—C57−84.2 (5)
C12—C13—C14—C22−179.0 (3)C32—C39—C40—C5742.3 (5)
C25—C13—C14—C2249.6 (4)C57—C40—C41—C42−1.8 (7)
C12—C13—C14—C16−65.2 (4)C39—C40—C41—C42−179.5 (4)
C25—C13—C14—C16163.5 (3)C40—C41—C42—C436.7 (7)
C15—C14—C16—C1762.0 (5)C41—C42—C43—C55−37.9 (5)
C22—C14—C16—C17−59.8 (5)C41—C42—C43—C44−171.6 (4)
C13—C14—C16—C17−174.4 (4)C42—C43—C44—C46−61.7 (5)
C14—C16—C17—C1824.3 (6)C55—C43—C44—C46168.0 (3)
C14—C16—C17—C18'52.0 (6)C42—C43—C44—C52−177.7 (4)
C18'—C17—C18—O3111.9 (11)C55—C43—C44—C5252.0 (4)
C16—C17—C18—O3−161.8 (5)C42—C43—C44—C4557.6 (6)
C18'—C17—C18—C19−69.0 (11)C55—C43—C44—C45−72.7 (5)
C16—C17—C18—C1917.3 (5)C52—C44—C46—C47−52.4 (5)
C18—C17—C18'—O3'−119.0 (10)C45—C44—C46—C4770.2 (5)
C16—C17—C18'—O3'136.4 (6)C43—C44—C46—C47−167.1 (4)
C18—C17—C18'—C1960.8 (10)C44—C46—C47—C4856.1 (5)
C16—C17—C18'—C19−43.8 (6)C46—C47—C48—O6123.7 (6)
O3—C18—C19—C18'−113.2 (11)C46—C47—C48—C49−54.6 (6)
C17—C18—C19—C18'67.7 (11)O6—C48—C49—C50−11.4 (7)
O3—C18—C19—C20−79.3 (4)C47—C48—C49—C50166.9 (5)
C17—C18—C19—C20101.6 (4)O6—C48—C49—C51105.2 (6)
O3—C18—C19—C2136.0 (4)C47—C48—C49—C51−76.5 (6)
C17—C18—C19—C21−143.1 (4)O6—C48—C49—C52−131.1 (5)
O3—C18—C19—C22160.6 (4)C47—C48—C49—C5247.1 (5)
C17—C18—C19—C22−18.5 (4)C46—C44—C52—C53−175.7 (4)
O3'—C18'—C19—C18118.0 (10)C45—C44—C52—C5364.5 (5)
C17—C18'—C19—C18−61.7 (10)C43—C44—C52—C53−60.6 (4)
O3'—C18'—C19—C20−30.2 (6)C46—C44—C52—C4950.3 (5)
C17—C18'—C19—C20150.0 (5)C45—C44—C52—C49−69.5 (5)
O3'—C18'—C19—C2179.8 (8)C43—C44—C52—C49165.4 (3)
C17—C18'—C19—C21−100.0 (7)C50—C49—C52—C5362.5 (5)
O3'—C18'—C19—C22−139.5 (6)C48—C49—C52—C53−179.3 (4)
C17—C18'—C19—C2240.8 (6)C51—C49—C52—C53−59.7 (6)
C15—C14—C22—C2369.9 (4)C50—C49—C52—C44−164.6 (4)
C16—C14—C22—C23−170.8 (3)C48—C49—C52—C44−46.4 (5)
C13—C14—C22—C23−56.9 (4)C51—C49—C52—C4473.2 (6)
C15—C14—C22—C19−59.8 (4)C44—C52—C53—C5464.0 (5)
C16—C14—C22—C1959.4 (4)C49—C52—C53—C54−159.4 (4)
C13—C14—C22—C19173.3 (3)C52—C53—C54—C55−55.3 (5)
C18—C19—C22—C23−151.5 (3)C53—C54—C55—C56−76.9 (5)
C18'—C19—C22—C23−177.9 (5)C53—C54—C55—C4344.4 (5)
C20—C19—C22—C2388.1 (5)C53—C54—C55—C57162.9 (4)
C21—C19—C22—C23−31.0 (6)C42—C43—C55—C56−56.7 (5)
C18—C19—C22—C14−21.9 (4)C44—C43—C55—C5675.7 (5)
C18'—C19—C22—C14−48.2 (5)C42—C43—C55—C54−176.6 (4)
C20—C19—C22—C14−142.2 (4)C44—C43—C55—C54−44.3 (4)
C21—C19—C22—C1498.7 (5)C42—C43—C55—C5763.4 (4)
C14—C22—C23—C2462.8 (4)C44—C43—C55—C57−164.2 (3)
C19—C22—C23—C24−165.5 (3)C41—C40—C57—C59149.0 (4)
C22—C23—C24—C25−57.7 (4)C39—C40—C57—C59−33.3 (5)
C23—C24—C25—C26−72.9 (4)C41—C40—C57—C58−94.0 (5)
C23—C24—C25—C1348.3 (4)C39—C40—C57—C5883.7 (4)
C23—C24—C25—C27166.4 (3)C41—C40—C57—C5527.7 (5)
C12—C13—C25—C24−178.4 (3)C39—C40—C57—C55−154.6 (4)
C14—C13—C25—C24−45.5 (4)C56—C55—C57—C4063.1 (5)
C12—C13—C25—C26−58.2 (4)C54—C55—C57—C40−177.7 (3)
C14—C13—C25—C2674.7 (4)C43—C55—C57—C40−57.4 (4)
C12—C13—C25—C2761.9 (4)C56—C55—C57—C59−60.3 (5)
C14—C13—C25—C27−165.2 (3)C54—C55—C57—C5958.9 (4)
C11—C10—C27—C29152.6 (3)C43—C55—C57—C59179.2 (3)
C9—C10—C27—C29−31.4 (4)C56—C55—C57—C58−178.6 (4)
C11—C10—C27—C28−89.6 (4)C54—C55—C57—C58−59.4 (5)
C9—C10—C27—C2886.4 (4)C43—C55—C57—C5860.9 (4)
C11—C10—C27—C2531.9 (4)C40—C57—C59—C6037.2 (5)
C9—C10—C27—C25−152.1 (3)C58—C57—C59—C60−79.8 (4)
C24—C25—C27—C10179.6 (3)C55—C57—C59—C60158.5 (3)
C26—C25—C27—C1059.8 (4)C31—C32—C60—C59−60.2 (5)
C13—C25—C27—C10−60.4 (3)C39—C32—C60—C5960.2 (5)
C24—C25—C27—C2956.4 (4)C33—C32—C60—C59−174.9 (4)
C26—C25—C27—C29−63.4 (4)C57—C59—C60—C32−52.8 (5)
C13—C25—C27—C29176.4 (3)C62—C63—C64—C65−159 (2)
C24—C25—C27—C28−62.4 (4)C64—C63—C62—C61−73 (2)
C26—C25—C27—C28177.8 (3)C63—C64—C65—C66180 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O40.841.712.545 (4)171
O5—H5···O20.841.832.637 (4)160
O1w—H1w···O30.842.203.03 (2)169

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2809).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shirane, N., Hashimoto, Y., Ueda, K., Takenaka, H. & Katoh, K. (1996). Phytochemistry, 43, 99–104.
  • Westrip, S. P. (2009). publCIF In preparation.

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