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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1514.
Published online 2008 July 16. doi:  10.1107/S1600536808021545
PMCID: PMC2962140

Schizandrol A: a lignan from Schisandra chinensis

Abstract

The title compound (systematic name: 1,2,3,10,11,12-hexa­meth­oxy-6,7-dimethyl-5,6,7,8-tetra­hydro­dibenzo[a,c]cyclo­oc­ten-6-ol), C24H32O7, has a dibenzocyclo­octa­diene skeleton. There are three mol­ecules in the asymmetric unit, which are related by a pseudo-translation in the direction of the c axis. Nevertheless, the three mol­ecules differ in the torsion angle of one of the meth­oxy groups. The dihedral angles between the two aromatic rings are 62.39 (10), 62.65 (10) and 61.84 (10)° for the three mol­ecules. The crystal packing is stabilized by a series of O—H(...)O and C—H(...)O hydrogen bonds, as well as C—H(...)π inter­actions.

Related literature

For the pharmacology of schizandrol A, see Lee et al. (1999 [triangle], 2003 [triangle]). For a similar structure, see: Wang et al. (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1514-scheme1.jpg

Experimental

Crystal data

  • C24H32O7
  • M r = 432.50
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1514-efi1.jpg
  • a = 16.084 (3) Å
  • b = 18.107 (4) Å
  • c = 23.229 (5) Å
  • V = 6765 (2) Å3
  • Z = 12
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 113 (2) K
  • 0.20 × 0.18 × 0.14 mm

Data collection

  • Rigaku Saturn CCD area-detector diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 [triangle]) T min = 0.982, T max = 0.987
  • 48456 measured reflections
  • 8487 independent reflections
  • 7852 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.044
  • wR(F 2) = 0.110
  • S = 1.09
  • 8487 reflections
  • 865 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005 [triangle]).

Table 1
Selected torsion angles (°)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808021545/bt2738sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808021545/bt2738Isup2.hkl

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

supplementary crystallographic information

Comment

Schizandrol A, with a special multi-pharmacological activity, has been found to have a relatively large potential in the application of cancer treatment (Lee et al., 1999, 2003).

The title compound has the eight-membered ring in a twisted-boat-chair conformation. There are three molecules in the asymmetric unit, which are related by a pseudo-translation in direction of the c-axis. Nevertheless, the three molecules differ in the torsion angle of one of the methoxy groups (Table 1).

For the first molecule (Fig. 1), the two benzene rings form a dihedral angle of 62.39 (10)°, for the second (Fig. 2), the two benzene rings form an angle of 62.65 (10)°, and for the third (Fig. 3), the two benzene rings form an angle of 61.84 (10)°.

The crystal packing is stabilized by O—H···O and C—H···O hydrogen bonds (Table 1) as well as C—H···π interactions (H24B···Cg1i 2.80Å, C24—H24B···Cg1i 156°, H31B···Cg2ii 2.71Å, C31—H31B···Cg2ii 161° H72B···Cg3i 2.94Å, C72—H72B···Cg3i 164°; symmetry operators: (i) x + 1/2, -y + 1/2, -z + 1, (ii) x - 1/2, -y + 3/2, -z + 2; Cg1 is the centroid of the ring composed of C49—C54, Cg2 is the centroid of the ring composed of C40—C45, Cg3 is the centroid of the ring composed of C1—C6 ring).

Experimental

Schizandrol A was isolated from Schisandra chinensis. Crystals were obtained by evaporation of a methanolic solution.

Refinement

In the absence of anomalous scatterers Friedel pairs were merged and the absolute configuration was set according to the literature. All H atoms were positioned geometrically and refined as riding atoms, with U(H) = 1.2 Ueq(CH and CH2) and with C—H ranging from 0.95 to 1.0 Å and U(H) = 1.5 Ueq(CH3 and O) with C-H = 0.99Å and O-H = 0.84Å. The methyl and hydroxyl groups were allowed to rotate but not to tip.

Figures

Fig. 1.
View of the first molecule in the asymmetric unit with the atom-numbering scheme and 50% probability displacement ellipsoids.
Fig. 2.
View of the second molecule in the asymmetric unit with the atom-numbering scheme and 50% probability displacement ellipsoids.
Fig. 3.
View of the third molecule in the asymmetric unit with the atom-numbering scheme and 50% probability displacement ellipsoids.

Crystal data

C24H32O7F000 = 2784
Mr = 432.50Dx = 1.274 Mg m3
Orthorhombic, P212121Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 18705 reflections
a = 16.084 (3) Åθ = 1.5–27.6º
b = 18.107 (4) ŵ = 0.09 mm1
c = 23.229 (5) ÅT = 113 (2) K
V = 6765 (2) Å3Block, colourless
Z = 120.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer8487 independent reflections
Radiation source: rotating anode7852 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.051
Detector resolution: 7.31 pixels mm-1θmax = 27.5º
T = 113(2) Kθmin = 1.5º
ω scansh = −20→17
Absorption correction: multi-scan(CrystalClear; Rigaku/MSC, 2005)k = −23→21
Tmin = 0.982, Tmax = 0.987l = −30→27
48456 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H-atom parameters constrained
wR(F2) = 0.110  w = 1/[σ2(Fo2) + (0.0626P)2 + 0.2401P] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.001
8487 reflectionsΔρmax = 0.18 e Å3
865 parametersΔρmin = −0.24 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

xyzUiso*/Ueq
O10.22101 (9)0.35381 (8)0.73077 (7)0.0232 (3)
O20.32692 (9)0.45994 (8)0.76569 (7)0.0239 (3)
O30.49211 (9)0.43468 (8)0.77143 (6)0.0230 (3)
O40.58793 (9)0.39176 (9)0.66990 (7)0.0291 (4)
O50.75662 (9)0.37642 (9)0.67774 (7)0.0292 (4)
O60.82536 (9)0.27751 (9)0.74939 (7)0.0237 (3)
O70.60082 (9)0.09979 (8)0.75711 (7)0.0249 (3)
H70.60080.05410.75090.037*
O80.67403 (9)0.71666 (9)0.91986 (7)0.0227 (3)
O90.74232 (9)0.60393 (9)0.86118 (7)0.0255 (3)
O100.90954 (9)0.57743 (8)0.86623 (6)0.0215 (3)
O111.00471 (9)0.55230 (8)0.96847 (7)0.0248 (4)
O121.17213 (9)0.51920 (8)0.94694 (7)0.0221 (3)
O131.27229 (9)0.62086 (9)0.90144 (7)0.0244 (3)
O140.89486 (9)0.88450 (9)0.92657 (7)0.0234 (3)
H140.89600.92910.91650.035*
O150.22728 (9)0.36321 (8)0.07007 (7)0.0221 (3)
O160.33017 (9)0.47290 (8)0.10673 (6)0.0215 (3)
O170.49504 (9)0.44981 (8)0.11691 (6)0.0205 (3)
O180.59386 (9)0.41675 (8)0.01820 (6)0.0217 (3)
O190.76177 (9)0.39393 (9)0.01571 (7)0.0259 (3)
O200.83295 (9)0.29020 (9)0.08307 (7)0.0243 (3)
O210.61530 (9)0.11886 (9)0.08946 (7)0.0261 (3)
H210.61910.07340.08280.039*
C10.47537 (13)0.30913 (12)0.73820 (9)0.0200 (4)
C20.44148 (13)0.37730 (12)0.75383 (9)0.0197 (4)
C30.35660 (13)0.39076 (11)0.75195 (9)0.0192 (4)
C40.30337 (12)0.33497 (12)0.73236 (9)0.0189 (4)
C50.33611 (13)0.26724 (12)0.71663 (9)0.0201 (4)
H50.29990.22960.70320.024*
C60.42133 (13)0.25307 (12)0.72008 (9)0.0189 (4)
C70.51498 (16)0.42987 (14)0.83038 (10)0.0317 (6)
H7A0.55100.38690.83610.048*
H7B0.46490.42460.85400.048*
H7C0.54480.47480.84170.048*
C80.28384 (15)0.46474 (14)0.81940 (11)0.0339 (6)
H8A0.32290.45580.85100.051*
H8B0.23950.42760.82050.051*
H8C0.25960.51410.82350.051*
C90.16586 (13)0.30434 (14)0.70256 (10)0.0279 (5)
H9A0.16600.25680.72270.042*
H9B0.18400.29720.66270.042*
H9C0.10950.32500.70290.042*
C100.45252 (13)0.17746 (11)0.70287 (9)0.0205 (4)
H10A0.51020.18270.68850.025*
H10B0.41810.15950.67040.025*
C110.45200 (13)0.11750 (12)0.75076 (9)0.0213 (4)
H110.45560.06940.72980.026*
C120.52938 (13)0.11905 (12)0.79049 (9)0.0204 (4)
C130.51924 (14)0.06450 (13)0.84006 (10)0.0276 (5)
H13A0.57280.05790.85950.041*
H13B0.50010.01690.82500.041*
H13C0.47830.08370.86750.041*
C140.36875 (13)0.11516 (14)0.78232 (11)0.0285 (5)
H14A0.36340.15900.80680.043*
H14B0.36610.07060.80620.043*
H14C0.32340.11440.75420.043*
C150.54875 (13)0.19628 (12)0.81623 (9)0.0201 (4)
H15A0.49540.22170.82390.024*
H15B0.57700.18920.85370.024*
C160.60180 (13)0.24614 (11)0.77951 (9)0.0193 (4)
C170.68839 (13)0.23942 (12)0.78333 (9)0.0201 (4)
H170.71170.20440.80910.024*
C180.74031 (13)0.28263 (12)0.75035 (9)0.0204 (4)
C190.70630 (13)0.33534 (12)0.71306 (9)0.0211 (4)
C200.62032 (13)0.34205 (12)0.70857 (10)0.0224 (4)
C210.56694 (13)0.29808 (12)0.74200 (9)0.0201 (4)
C220.59403 (17)0.36666 (18)0.61177 (10)0.0438 (7)
H22A0.56380.32000.60760.066*
H22B0.65260.35910.60180.066*
H22C0.56990.40370.58600.066*
C230.78962 (18)0.44071 (16)0.70428 (15)0.0513 (8)
H23A0.82860.42630.73470.077*
H23B0.74420.46970.72100.077*
H23C0.81880.47050.67540.077*
C240.86011 (14)0.21001 (13)0.76977 (10)0.0270 (5)
H24A0.83100.16830.75200.040*
H24B0.85400.20730.81170.040*
H24C0.91920.20800.75970.040*
C250.93024 (13)0.68169 (11)0.92894 (9)0.0180 (4)
C260.87680 (13)0.63516 (11)0.89785 (9)0.0180 (4)
C270.79197 (13)0.64683 (12)0.89631 (9)0.0198 (4)
C280.75777 (13)0.70615 (12)0.92637 (9)0.0191 (4)
C290.80935 (13)0.75110 (12)0.95864 (9)0.0189 (4)
H290.78580.79010.98060.023*
C300.89546 (13)0.74027 (11)0.95958 (9)0.0183 (4)
C310.64328 (14)0.78833 (13)0.93384 (10)0.0262 (5)
H31A0.67830.82590.91560.039*
H31B0.64430.79510.97570.039*
H31C0.58610.79330.91980.039*
C320.71267 (17)0.53897 (15)0.88860 (12)0.0400 (6)
H32A0.67400.55250.91940.060*
H32B0.75970.51160.90490.060*
H32C0.68390.50790.86040.060*
C330.91734 (17)0.59558 (14)0.80678 (10)0.0336 (6)
H33A0.95430.63830.80250.050*
H33B0.86250.60760.79100.050*
H33C0.94060.55340.78590.050*
C340.94773 (13)0.79501 (12)0.99228 (9)0.0195 (4)
H34A1.00100.77101.00250.023*
H34B0.91880.80721.02870.023*
C350.96723 (13)0.86801 (12)0.96016 (9)0.0204 (4)
C361.04299 (13)0.86312 (12)0.91930 (9)0.0202 (4)
H361.03930.90790.89430.024*
C371.12733 (13)0.86895 (13)0.94948 (10)0.0257 (5)
H37A1.13230.82950.97820.039*
H37B1.13180.91700.96860.039*
H37C1.17190.86400.92100.039*
C380.97951 (14)0.92885 (13)1.00476 (10)0.0259 (5)
H38A0.92680.93841.02450.039*
H38B0.99830.97400.98550.039*
H38C1.02140.91321.03290.039*
C391.03961 (13)0.79643 (12)0.87733 (9)0.0201 (4)
H39A0.98100.78900.86580.024*
H39B1.07110.80980.84220.024*
C401.07303 (13)0.72303 (12)0.89929 (9)0.0190 (4)
C411.02178 (12)0.66995 (12)0.92481 (9)0.0175 (4)
C421.05705 (12)0.60297 (12)0.94374 (9)0.0193 (4)
C431.14118 (12)0.58866 (11)0.93495 (9)0.0187 (4)
C441.19131 (12)0.64162 (12)0.90858 (9)0.0198 (4)
C451.15784 (13)0.70844 (12)0.89145 (9)0.0195 (4)
H451.19260.74470.87430.023*
C461.03229 (14)0.51599 (13)1.01966 (10)0.0270 (5)
H46A1.06380.55081.04340.041*
H46B1.06790.47421.00930.041*
H46C0.98400.49811.04130.041*
C471.23501 (14)0.51537 (14)0.99111 (11)0.0316 (6)
H47A1.20900.52131.02900.047*
H47B1.27580.55480.98510.047*
H47C1.26300.46740.98920.047*
C481.32394 (14)0.66689 (15)0.86767 (10)0.0311 (5)
H48A1.32630.71620.88490.047*
H48B1.30120.67050.82860.047*
H48C1.38000.64590.86600.047*
C490.48299 (13)0.32529 (12)0.08063 (9)0.0184 (4)
C500.44632 (12)0.39210 (12)0.09731 (9)0.0175 (4)
C510.36115 (13)0.40387 (11)0.09355 (9)0.0183 (4)
C520.31019 (12)0.34727 (12)0.07249 (9)0.0186 (4)
C530.34539 (13)0.28111 (12)0.05587 (9)0.0193 (4)
H530.31070.24310.04120.023*
C540.43121 (13)0.26873 (12)0.06014 (9)0.0183 (4)
C550.50873 (17)0.44691 (16)0.17689 (10)0.0373 (6)
H55A0.54170.40300.18620.056*
H55B0.45520.44440.19690.056*
H55C0.53880.49130.18910.056*
C560.27811 (15)0.47761 (14)0.15661 (11)0.0321 (6)
H56A0.30970.46240.19070.048*
H56B0.22990.44510.15180.048*
H56C0.25910.52860.16150.048*
C570.17460 (13)0.31027 (14)0.04303 (10)0.0264 (5)
H57A0.17740.26350.06410.040*
H57B0.19290.30250.00330.040*
H57C0.11720.32840.04310.040*
C580.46477 (13)0.19487 (12)0.04038 (9)0.0211 (4)
H58A0.52240.20240.02660.025*
H58B0.43130.17840.00700.025*
C590.46560 (13)0.13179 (12)0.08538 (10)0.0221 (4)
H590.46980.08520.06250.026*
C600.54366 (13)0.13266 (12)0.12440 (9)0.0222 (4)
C610.53711 (15)0.07272 (13)0.17034 (11)0.0300 (5)
H61A0.59060.06770.19010.045*
H61B0.52240.02570.15210.045*
H61C0.49410.08630.19830.045*
C620.38356 (13)0.12603 (13)0.11798 (10)0.0268 (5)
H62A0.33720.12880.09070.040*
H62B0.37940.16680.14560.040*
H62C0.38140.07890.13860.040*
C630.55992 (13)0.20784 (12)0.15394 (9)0.0215 (4)
H63A0.50570.23110.16290.026*
H63B0.58880.19880.19090.026*
C640.61102 (13)0.26150 (12)0.11891 (9)0.0190 (4)
C650.57462 (13)0.31591 (12)0.08451 (9)0.0183 (4)
C660.62727 (13)0.36206 (12)0.05202 (9)0.0186 (4)
C670.71315 (13)0.35299 (12)0.05239 (9)0.0197 (4)
C680.74847 (13)0.29777 (12)0.08662 (9)0.0207 (4)
C690.69748 (13)0.25376 (12)0.12022 (9)0.0198 (4)
H690.72170.21760.14460.024*
C700.58397 (17)0.39464 (14)−0.04001 (10)0.0320 (6)
H70A0.55020.3496−0.04160.048*
H70B0.63870.3850−0.05700.048*
H70C0.55620.4340−0.06160.048*
C710.79704 (17)0.45794 (15)0.04198 (12)0.0389 (6)
H71A0.83350.44290.07370.058*
H71B0.75240.48940.05690.058*
H71C0.82940.48540.01340.058*
C720.86633 (14)0.22107 (13)0.10102 (11)0.0286 (5)
H72A0.83530.18090.08270.043*
H72B0.86180.21670.14300.043*
H72C0.92490.21800.08970.043*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0161 (7)0.0227 (8)0.0309 (8)0.0009 (6)−0.0032 (6)−0.0025 (7)
O20.0243 (8)0.0170 (8)0.0305 (8)0.0024 (6)0.0019 (7)−0.0013 (7)
O30.0228 (7)0.0172 (8)0.0291 (8)−0.0053 (6)−0.0044 (7)0.0007 (6)
O40.0250 (8)0.0254 (9)0.0369 (9)0.0034 (7)−0.0004 (7)0.0144 (7)
O50.0214 (8)0.0282 (9)0.0379 (9)−0.0047 (7)0.0035 (7)0.0105 (8)
O60.0158 (7)0.0260 (8)0.0293 (8)0.0013 (6)−0.0026 (6)0.0044 (7)
O70.0253 (8)0.0178 (8)0.0315 (8)0.0044 (6)0.0042 (7)−0.0003 (7)
O80.0158 (7)0.0242 (8)0.0283 (8)0.0024 (6)0.0002 (6)−0.0022 (7)
O90.0238 (8)0.0236 (8)0.0292 (8)−0.0030 (7)−0.0066 (7)−0.0053 (7)
O100.0233 (7)0.0171 (8)0.0240 (7)0.0023 (6)−0.0018 (6)−0.0037 (6)
O110.0221 (8)0.0174 (8)0.0351 (9)−0.0041 (6)−0.0058 (7)0.0081 (7)
O120.0209 (7)0.0137 (7)0.0317 (8)0.0016 (6)−0.0055 (7)0.0003 (6)
O130.0188 (7)0.0236 (8)0.0307 (8)0.0036 (6)0.0025 (6)0.0043 (7)
O140.0230 (8)0.0174 (8)0.0299 (8)0.0026 (6)−0.0043 (7)0.0016 (7)
O150.0166 (7)0.0203 (8)0.0295 (8)0.0003 (6)−0.0016 (6)−0.0024 (7)
O160.0233 (7)0.0151 (7)0.0262 (8)0.0024 (6)0.0040 (6)−0.0007 (6)
O170.0225 (7)0.0164 (7)0.0225 (7)−0.0044 (6)−0.0003 (6)−0.0017 (6)
O180.0243 (7)0.0202 (8)0.0205 (7)0.0029 (6)−0.0005 (6)0.0034 (6)
O190.0233 (8)0.0271 (9)0.0273 (8)−0.0037 (7)0.0027 (7)0.0038 (7)
O200.0160 (7)0.0262 (8)0.0306 (8)0.0032 (6)−0.0009 (6)0.0009 (7)
O210.0235 (8)0.0176 (8)0.0373 (9)0.0032 (6)0.0048 (7)−0.0010 (7)
C10.0186 (10)0.0193 (11)0.0221 (10)0.0009 (8)−0.0016 (8)0.0034 (9)
C20.0212 (10)0.0168 (10)0.0212 (10)−0.0039 (8)−0.0017 (8)0.0017 (9)
C30.0215 (10)0.0143 (10)0.0217 (10)−0.0006 (8)0.0006 (8)0.0007 (8)
C40.0167 (9)0.0208 (11)0.0191 (9)0.0011 (8)−0.0018 (8)0.0013 (9)
C50.0206 (10)0.0178 (10)0.0218 (10)−0.0023 (8)−0.0026 (8)0.0000 (8)
C60.0204 (10)0.0174 (10)0.0190 (10)0.0015 (8)0.0008 (8)0.0003 (8)
C70.0370 (13)0.0292 (13)0.0288 (12)−0.0094 (11)−0.0119 (11)0.0005 (10)
C80.0348 (13)0.0309 (13)0.0359 (13)−0.0009 (11)0.0128 (11)−0.0080 (11)
C90.0197 (10)0.0358 (13)0.0281 (11)−0.0012 (9)−0.0023 (9)−0.0113 (10)
C100.0218 (10)0.0192 (11)0.0206 (10)0.0023 (8)0.0009 (9)−0.0013 (8)
C110.0236 (10)0.0144 (10)0.0259 (10)0.0000 (8)−0.0017 (9)−0.0011 (9)
C120.0220 (10)0.0179 (10)0.0212 (10)0.0010 (8)0.0009 (9)0.0018 (9)
C130.0290 (12)0.0225 (12)0.0313 (12)−0.0027 (9)−0.0024 (10)0.0065 (10)
C140.0250 (11)0.0261 (12)0.0345 (12)−0.0048 (9)0.0008 (10)0.0059 (10)
C150.0206 (10)0.0188 (10)0.0210 (10)0.0006 (8)0.0004 (8)0.0002 (9)
C160.0220 (10)0.0138 (10)0.0222 (10)0.0002 (8)−0.0006 (8)−0.0018 (8)
C170.0222 (10)0.0186 (10)0.0195 (10)0.0025 (8)−0.0029 (8)0.0007 (8)
C180.0181 (10)0.0189 (10)0.0243 (10)0.0007 (8)−0.0027 (9)−0.0016 (9)
C190.0207 (10)0.0178 (10)0.0248 (10)−0.0020 (8)0.0009 (9)0.0025 (9)
C200.0228 (10)0.0165 (10)0.0279 (11)0.0010 (8)0.0004 (9)0.0042 (9)
C210.0191 (10)0.0155 (10)0.0258 (11)0.0000 (8)−0.0024 (8)0.0018 (9)
C220.0406 (15)0.0576 (19)0.0330 (13)0.0066 (14)−0.0050 (12)0.0194 (13)
C230.0438 (16)0.0314 (15)0.079 (2)−0.0165 (13)0.0047 (16)0.0067 (16)
C240.0217 (11)0.0276 (12)0.0316 (12)0.0047 (9)−0.0041 (9)0.0022 (10)
C250.0179 (10)0.0135 (10)0.0227 (10)0.0006 (8)−0.0001 (8)0.0024 (8)
C260.0207 (10)0.0129 (10)0.0204 (10)0.0011 (8)−0.0001 (8)0.0002 (8)
C270.0203 (10)0.0183 (10)0.0210 (10)−0.0007 (8)−0.0012 (8)−0.0014 (8)
C280.0177 (10)0.0209 (11)0.0187 (10)0.0001 (8)0.0004 (8)0.0034 (8)
C290.0213 (10)0.0151 (10)0.0203 (10)0.0005 (8)0.0012 (8)−0.0010 (8)
C300.0212 (10)0.0155 (10)0.0180 (9)−0.0004 (8)−0.0012 (8)0.0017 (8)
C310.0193 (10)0.0247 (12)0.0346 (12)0.0061 (9)0.0017 (9)−0.0022 (10)
C320.0373 (14)0.0304 (14)0.0524 (17)−0.0146 (11)−0.0016 (13)−0.0042 (13)
C330.0456 (15)0.0306 (13)0.0247 (11)0.0133 (11)0.0032 (11)−0.0012 (10)
C340.0206 (10)0.0165 (10)0.0215 (10)0.0000 (8)−0.0010 (8)−0.0002 (8)
C350.0210 (10)0.0175 (10)0.0228 (10)0.0005 (8)−0.0005 (8)−0.0016 (9)
C360.0228 (10)0.0134 (10)0.0246 (10)0.0005 (8)0.0015 (9)0.0014 (8)
C370.0221 (11)0.0234 (12)0.0316 (12)−0.0053 (9)0.0000 (9)−0.0004 (10)
C380.0276 (11)0.0198 (11)0.0302 (12)−0.0039 (9)0.0012 (9)−0.0061 (10)
C390.0230 (10)0.0169 (10)0.0203 (10)0.0014 (9)−0.0019 (8)0.0015 (8)
C400.0220 (10)0.0166 (10)0.0185 (9)0.0022 (8)−0.0016 (8)−0.0019 (8)
C410.0169 (9)0.0165 (10)0.0190 (9)0.0001 (8)−0.0023 (8)−0.0008 (8)
C420.0177 (10)0.0161 (10)0.0242 (10)−0.0033 (8)−0.0040 (8)0.0005 (9)
C430.0187 (10)0.0133 (10)0.0243 (10)0.0022 (8)−0.0035 (8)−0.0002 (8)
C440.0179 (10)0.0205 (11)0.0209 (10)0.0019 (8)−0.0010 (8)−0.0017 (9)
C450.0192 (10)0.0174 (10)0.0219 (10)−0.0006 (8)0.0008 (8)0.0008 (9)
C460.0284 (12)0.0242 (12)0.0284 (11)0.0023 (9)−0.0003 (10)0.0056 (10)
C470.0243 (11)0.0264 (13)0.0440 (14)−0.0003 (9)−0.0113 (11)0.0089 (11)
C480.0225 (11)0.0400 (15)0.0308 (12)0.0050 (10)0.0047 (10)0.0112 (11)
C490.0203 (10)0.0184 (10)0.0164 (9)0.0007 (8)−0.0010 (8)0.0010 (8)
C500.0194 (10)0.0147 (10)0.0183 (9)−0.0029 (8)−0.0007 (8)−0.0001 (8)
C510.0209 (10)0.0151 (10)0.0189 (10)0.0017 (8)0.0013 (8)0.0022 (8)
C520.0175 (10)0.0201 (11)0.0181 (10)0.0002 (8)0.0004 (8)0.0007 (8)
C530.0183 (10)0.0188 (11)0.0208 (10)−0.0025 (8)−0.0019 (8)−0.0014 (8)
C540.0186 (10)0.0174 (10)0.0189 (9)−0.0003 (8)−0.0002 (8)0.0006 (8)
C550.0488 (16)0.0411 (15)0.0221 (11)−0.0188 (13)−0.0064 (11)−0.0029 (11)
C560.0343 (13)0.0287 (13)0.0333 (12)0.0009 (10)0.0114 (11)−0.0056 (11)
C570.0178 (10)0.0321 (13)0.0294 (12)−0.0030 (9)−0.0025 (9)−0.0066 (10)
C580.0215 (10)0.0184 (11)0.0233 (10)0.0012 (8)0.0015 (9)−0.0025 (9)
C590.0210 (10)0.0152 (10)0.0300 (11)0.0012 (8)0.0002 (9)−0.0018 (9)
C600.0212 (10)0.0178 (11)0.0275 (11)0.0014 (8)0.0018 (9)0.0003 (9)
C610.0285 (12)0.0228 (12)0.0388 (13)−0.0041 (10)−0.0039 (10)0.0099 (11)
C620.0238 (11)0.0207 (11)0.0360 (13)−0.0022 (9)0.0007 (10)0.0006 (10)
C630.0222 (10)0.0202 (11)0.0220 (10)0.0003 (8)0.0017 (9)0.0021 (9)
C640.0208 (10)0.0179 (10)0.0182 (10)−0.0002 (8)−0.0014 (8)−0.0031 (8)
C650.0183 (10)0.0171 (10)0.0194 (10)−0.0004 (8)−0.0005 (8)−0.0023 (8)
C660.0201 (10)0.0161 (10)0.0196 (10)0.0018 (8)−0.0010 (8)−0.0006 (8)
C670.0198 (10)0.0192 (11)0.0202 (10)−0.0020 (8)0.0013 (8)0.0001 (9)
C680.0171 (10)0.0214 (11)0.0237 (10)0.0013 (8)−0.0004 (8)−0.0047 (9)
C690.0219 (10)0.0178 (10)0.0197 (10)0.0013 (8)−0.0028 (8)−0.0020 (8)
C700.0443 (15)0.0289 (13)0.0227 (11)0.0053 (11)−0.0063 (10)0.0015 (10)
C710.0367 (14)0.0343 (15)0.0456 (15)−0.0152 (12)−0.0042 (12)0.0064 (12)
C720.0200 (11)0.0292 (13)0.0365 (12)0.0074 (9)−0.0045 (10)0.0008 (11)

Geometric parameters (Å, °)

O1—C41.368 (2)C28—C291.383 (3)
O1—C91.421 (3)C29—C301.399 (3)
O2—C31.378 (2)C29—H290.9500
O2—C81.430 (3)C30—C341.505 (3)
O3—C21.382 (2)C31—H31A0.9800
O3—C71.421 (3)C31—H31B0.9800
O4—C201.374 (3)C31—H31C0.9800
O4—C221.428 (3)C32—H32A0.9800
O5—C191.372 (3)C32—H32B0.9800
O5—C231.420 (3)C32—H32C0.9800
O6—C181.371 (2)C33—H33A0.9800
O6—C241.425 (3)C33—H33B0.9800
O7—C121.429 (2)C33—H33C0.9800
O7—H70.8400C34—C351.550 (3)
O8—C281.369 (2)C34—H34A0.9900
O8—C311.426 (3)C34—H34B0.9900
O9—C271.381 (2)C35—C381.525 (3)
O9—C321.420 (3)C35—C361.547 (3)
O10—C261.382 (2)C36—C371.530 (3)
O10—C331.425 (3)C36—C391.553 (3)
O11—C421.371 (3)C36—H361.0000
O11—C461.429 (3)C37—H37A0.9800
O12—C431.381 (2)C37—H37B0.9800
O12—C471.442 (3)C37—H37C0.9800
O13—C441.366 (2)C38—H38A0.9800
O13—C481.414 (3)C38—H38B0.9800
O14—C351.433 (2)C38—H38C0.9800
O14—H140.8400C39—C401.522 (3)
O15—C521.366 (2)C39—H39A0.9900
O15—C571.425 (3)C39—H39B0.9900
O16—C511.380 (2)C40—C411.398 (3)
O16—C561.432 (3)C40—C451.401 (3)
O17—C501.383 (2)C41—C421.409 (3)
O17—C551.411 (3)C42—C431.393 (3)
O18—C661.373 (2)C43—C441.395 (3)
O18—C701.419 (3)C44—C451.383 (3)
O19—C671.374 (2)C45—H450.9500
O19—C711.427 (3)C46—H46A0.9800
O20—C681.368 (2)C46—H46B0.9800
O20—C721.425 (3)C46—H46C0.9800
O21—C601.431 (3)C47—H47A0.9800
O21—H210.8400C47—H47B0.9800
C1—C21.397 (3)C47—H47C0.9800
C1—C61.401 (3)C48—H48A0.9800
C1—C211.489 (3)C48—H48B0.9800
C2—C31.388 (3)C48—H48C0.9800
C3—C41.400 (3)C49—C501.400 (3)
C4—C51.384 (3)C49—C541.403 (3)
C5—C61.397 (3)C49—C651.486 (3)
C5—H50.9500C50—C511.389 (3)
C6—C101.512 (3)C51—C521.401 (3)
C7—H7A0.9800C52—C531.380 (3)
C7—H7B0.9800C53—C541.402 (3)
C7—H7C0.9800C53—H530.9500
C8—H8A0.9800C54—C581.514 (3)
C8—H8B0.9800C55—H55A0.9800
C8—H8C0.9800C55—H55B0.9800
C9—H9A0.9800C55—H55C0.9800
C9—H9B0.9800C56—H56A0.9800
C9—H9C0.9800C56—H56B0.9800
C10—C111.554 (3)C56—H56C0.9800
C10—H10A0.9900C57—H57A0.9800
C10—H10B0.9900C57—H57B0.9800
C11—C141.527 (3)C57—H57C0.9800
C11—C121.550 (3)C58—C591.549 (3)
C11—H111.0000C58—H58A0.9900
C12—C131.526 (3)C58—H58B0.9900
C12—C151.552 (3)C59—C621.525 (3)
C13—H13A0.9800C59—C601.549 (3)
C13—H13B0.9800C59—H591.0000
C13—H13C0.9800C60—C611.526 (3)
C14—H14A0.9800C60—C631.547 (3)
C14—H14B0.9800C61—H61A0.9800
C14—H14C0.9800C61—H61B0.9800
C15—C161.507 (3)C61—H61C0.9800
C15—H15A0.9900C62—H62A0.9800
C15—H15B0.9900C62—H62B0.9800
C16—C211.399 (3)C62—H62C0.9800
C16—C171.401 (3)C63—C641.510 (3)
C17—C181.377 (3)C63—H63A0.9900
C17—H170.9500C63—H63B0.9900
C18—C191.400 (3)C64—C651.397 (3)
C19—C201.392 (3)C64—C691.398 (3)
C20—C211.405 (3)C65—C661.409 (3)
C22—H22A0.9800C66—C671.391 (3)
C22—H22B0.9800C67—C681.398 (3)
C22—H22C0.9800C68—C691.384 (3)
C23—H23A0.9800C69—H690.9500
C23—H23B0.9800C70—H70A0.9800
C23—H23C0.9800C70—H70B0.9800
C24—H24A0.9800C70—H70C0.9800
C24—H24B0.9800C71—H71A0.9800
C24—H24C0.9800C71—H71B0.9800
C25—C301.394 (3)C71—H71C0.9800
C25—C261.404 (3)C72—H72A0.9800
C25—C411.491 (3)C72—H72B0.9800
C26—C271.381 (3)C72—H72C0.9800
C27—C281.394 (3)
C4—O1—C9117.36 (17)C38—C35—C36110.86 (18)
C3—O2—C8115.17 (17)O14—C35—C34105.99 (17)
C2—O3—C7113.05 (17)C38—C35—C34108.38 (17)
C20—O4—C22112.56 (19)C36—C35—C34113.95 (17)
C19—O5—C23113.9 (2)C37—C36—C35114.40 (18)
C18—O6—C24116.35 (17)C37—C36—C39111.85 (18)
C12—O7—H7109.5C35—C36—C39113.71 (17)
C28—O8—C31116.27 (17)C37—C36—H36105.3
C27—O9—C32113.27 (18)C35—C36—H36105.3
C26—O10—C33111.97 (16)C39—C36—H36105.3
C42—O11—C46117.76 (16)C36—C37—H37A109.5
C43—O12—C47116.11 (16)C36—C37—H37B109.5
C44—O13—C48117.73 (17)H37A—C37—H37B109.5
C35—O14—H14109.5C36—C37—H37C109.5
C52—O15—C57117.17 (17)H37A—C37—H37C109.5
C51—O16—C56116.40 (17)H37B—C37—H37C109.5
C50—O17—C55112.66 (17)C35—C38—H38A109.5
C66—O18—C70112.67 (17)C35—C38—H38B109.5
C67—O19—C71113.53 (18)H38A—C38—H38B109.5
C68—O20—C72116.40 (17)C35—C38—H38C109.5
C60—O21—H21109.5H38A—C38—H38C109.5
C2—C1—C6118.42 (19)H38B—C38—H38C109.5
C2—C1—C21119.29 (19)C40—C39—C36117.14 (17)
C6—C1—C21122.29 (19)C40—C39—H39A108.0
O3—C2—C3117.20 (19)C36—C39—H39A108.0
O3—C2—C1120.73 (18)C40—C39—H39B108.0
C3—C2—C1122.06 (19)C36—C39—H39B108.0
O2—C3—C2119.56 (18)H39A—C39—H39B107.3
O2—C3—C4121.28 (18)C41—C40—C45119.96 (19)
C2—C3—C4119.02 (19)C41—C40—C39122.30 (18)
O1—C4—C5125.60 (19)C45—C40—C39117.71 (19)
O1—C4—C3114.89 (19)C40—C41—C42119.11 (18)
C5—C4—C3119.51 (19)C40—C41—C25120.76 (19)
C4—C5—C6121.4 (2)C42—C41—C25120.02 (19)
C4—C5—H5119.3O11—C42—C43122.23 (19)
C6—C5—H5119.3O11—C42—C41117.34 (18)
C5—C6—C1119.54 (19)C43—C42—C41120.4 (2)
C5—C6—C10118.47 (19)O12—C43—C42119.34 (19)
C1—C6—C10121.98 (18)O12—C43—C44120.43 (18)
O3—C7—H7A109.5C42—C43—C44119.88 (19)
O3—C7—H7B109.5O13—C44—C45125.3 (2)
H7A—C7—H7B109.5O13—C44—C43114.55 (19)
O3—C7—H7C109.5C45—C44—C43120.20 (19)
H7A—C7—H7C109.5C44—C45—C40120.4 (2)
H7B—C7—H7C109.5C44—C45—H45119.8
O2—C8—H8A109.5C40—C45—H45119.8
O2—C8—H8B109.5O11—C46—H46A109.5
H8A—C8—H8B109.5O11—C46—H46B109.5
O2—C8—H8C109.5H46A—C46—H46B109.5
H8A—C8—H8C109.5O11—C46—H46C109.5
H8B—C8—H8C109.5H46A—C46—H46C109.5
O1—C9—H9A109.5H46B—C46—H46C109.5
O1—C9—H9B109.5O12—C47—H47A109.5
H9A—C9—H9B109.5O12—C47—H47B109.5
O1—C9—H9C109.5H47A—C47—H47B109.5
H9A—C9—H9C109.5O12—C47—H47C109.5
H9B—C9—H9C109.5H47A—C47—H47C109.5
C6—C10—C11116.20 (17)H47B—C47—H47C109.5
C6—C10—H10A108.2O13—C48—H48A109.5
C11—C10—H10A108.2O13—C48—H48B109.5
C6—C10—H10B108.2H48A—C48—H48B109.5
C11—C10—H10B108.2O13—C48—H48C109.5
H10A—C10—H10B107.4H48A—C48—H48C109.5
C14—C11—C12114.76 (18)H48B—C48—H48C109.5
C14—C11—C10111.57 (18)C50—C49—C54118.31 (19)
C12—C11—C10114.15 (17)C50—C49—C65119.97 (19)
C14—C11—H11105.1C54—C49—C65121.72 (19)
C12—C11—H11105.1O17—C50—C51117.61 (19)
C10—C11—H11105.1O17—C50—C49120.33 (18)
O7—C12—C13109.72 (17)C51—C50—C49122.04 (19)
O7—C12—C11108.55 (17)O16—C51—C50118.76 (18)
C13—C12—C11110.60 (18)O16—C51—C52121.94 (18)
O7—C12—C15105.51 (16)C50—C51—C52119.13 (19)
C13—C12—C15108.30 (17)O15—C52—C53124.93 (19)
C11—C12—C15114.00 (17)O15—C52—C51115.55 (18)
C12—C13—H13A109.5C53—C52—C51119.52 (18)
C12—C13—H13B109.5C52—C53—C54121.5 (2)
H13A—C13—H13B109.5C52—C53—H53119.2
C12—C13—H13C109.5C54—C53—H53119.2
H13A—C13—H13C109.5C53—C54—C49119.5 (2)
H13B—C13—H13C109.5C53—C54—C58118.10 (19)
C11—C14—H14A109.5C49—C54—C58122.42 (18)
C11—C14—H14B109.5O17—C55—H55A109.5
H14A—C14—H14B109.5O17—C55—H55B109.5
C11—C14—H14C109.5H55A—C55—H55B109.5
H14A—C14—H14C109.5O17—C55—H55C109.5
H14B—C14—H14C109.5H55A—C55—H55C109.5
C16—C15—C12115.80 (17)H55B—C55—H55C109.5
C16—C15—H15A108.3O16—C56—H56A109.5
C12—C15—H15A108.3O16—C56—H56B109.5
C16—C15—H15B108.3H56A—C56—H56B109.5
C12—C15—H15B108.3O16—C56—H56C109.5
H15A—C15—H15B107.4H56A—C56—H56C109.5
C21—C16—C17119.7 (2)H56B—C56—H56C109.5
C21—C16—C15121.89 (19)O15—C57—H57A109.5
C17—C16—C15118.36 (19)O15—C57—H57B109.5
C18—C17—C16121.22 (19)H57A—C57—H57B109.5
C18—C17—H17119.4O15—C57—H57C109.5
C16—C17—H17119.4H57A—C57—H57C109.5
O6—C18—C17125.14 (19)H57B—C57—H57C109.5
O6—C18—C19115.19 (18)C54—C58—C59116.76 (18)
C17—C18—C19119.64 (19)C54—C58—H58A108.1
O5—C19—C20119.61 (19)C59—C58—H58A108.1
O5—C19—C18120.61 (18)C54—C58—H58B108.1
C20—C19—C18119.59 (19)C59—C58—H58B108.1
O4—C20—C19118.86 (19)H58A—C58—H58B107.3
O4—C20—C21120.05 (18)C62—C59—C58112.21 (18)
C19—C20—C21121.1 (2)C62—C59—C60114.31 (18)
C16—C21—C20118.70 (19)C58—C59—C60113.24 (17)
C16—C21—C1121.56 (19)C62—C59—H59105.4
C20—C21—C1119.71 (19)C58—C59—H59105.4
O4—C22—H22A109.5C60—C59—H59105.4
O4—C22—H22B109.5O21—C60—C61109.15 (18)
H22A—C22—H22B109.5O21—C60—C63105.61 (17)
O4—C22—H22C109.5C61—C60—C63109.12 (18)
H22A—C22—H22C109.5O21—C60—C59108.60 (17)
H22B—C22—H22C109.5C61—C60—C59110.25 (18)
O5—C23—H23A109.5C63—C60—C59113.93 (17)
O5—C23—H23B109.5C60—C61—H61A109.5
H23A—C23—H23B109.5C60—C61—H61B109.5
O5—C23—H23C109.5H61A—C61—H61B109.5
H23A—C23—H23C109.5C60—C61—H61C109.5
H23B—C23—H23C109.5H61A—C61—H61C109.5
O6—C24—H24A109.5H61B—C61—H61C109.5
O6—C24—H24B109.5C59—C62—H62A109.5
H24A—C24—H24B109.5C59—C62—H62B109.5
O6—C24—H24C109.5H62A—C62—H62B109.5
H24A—C24—H24C109.5C59—C62—H62C109.5
H24B—C24—H24C109.5H62A—C62—H62C109.5
C30—C25—C26118.26 (18)H62B—C62—H62C109.5
C30—C25—C41122.52 (19)C64—C63—C60114.78 (18)
C26—C25—C41119.08 (19)C64—C63—H63A108.6
C27—C26—O10118.59 (18)C60—C63—H63A108.6
C27—C26—C25121.77 (19)C64—C63—H63B108.6
O10—C26—C25119.61 (18)C60—C63—H63B108.6
O9—C27—C26120.04 (19)H63A—C63—H63B107.5
O9—C27—C28120.07 (18)C65—C64—C69119.99 (19)
C26—C27—C28119.64 (19)C65—C64—C63122.26 (18)
O8—C28—C29124.65 (19)C69—C64—C63117.72 (19)
O8—C28—C27116.10 (19)C64—C65—C66118.22 (18)
C29—C28—C27119.22 (19)C64—C65—C49122.05 (19)
C28—C29—C30121.3 (2)C66—C65—C49119.72 (19)
C28—C29—H29119.3O18—C66—C67118.50 (19)
C30—C29—H29119.3O18—C66—C65119.93 (18)
C25—C30—C29119.72 (19)C67—C66—C65121.56 (19)
C25—C30—C34122.30 (19)O19—C67—C66119.84 (19)
C29—C30—C34117.94 (19)O19—C67—C68120.49 (18)
O8—C31—H31A109.5C66—C67—C68119.44 (19)
O8—C31—H31B109.5O20—C68—C69124.4 (2)
H31A—C31—H31B109.5O20—C68—C67116.16 (19)
O8—C31—H31C109.5C69—C68—C67119.44 (19)
H31A—C31—H31C109.5C68—C69—C64121.3 (2)
H31B—C31—H31C109.5C68—C69—H69119.4
O9—C32—H32A109.5C64—C69—H69119.4
O9—C32—H32B109.5O18—C70—H70A109.5
H32A—C32—H32B109.5O18—C70—H70B109.5
O9—C32—H32C109.5H70A—C70—H70B109.5
H32A—C32—H32C109.5O18—C70—H70C109.5
H32B—C32—H32C109.5H70A—C70—H70C109.5
O10—C33—H33A109.5H70B—C70—H70C109.5
O10—C33—H33B109.5O19—C71—H71A109.5
H33A—C33—H33B109.5O19—C71—H71B109.5
O10—C33—H33C109.5H71A—C71—H71B109.5
H33A—C33—H33C109.5O19—C71—H71C109.5
H33B—C33—H33C109.5H71A—C71—H71C109.5
C30—C34—C35115.58 (17)H71B—C71—H71C109.5
C30—C34—H34A108.4O20—C72—H72A109.5
C35—C34—H34A108.4O20—C72—H72B109.5
C30—C34—H34B108.4H72A—C72—H72B109.5
C35—C34—H34B108.4O20—C72—H72C109.5
H34A—C34—H34B107.4H72A—C72—H72C109.5
O14—C35—C38108.95 (18)H72B—C72—H72C109.5
O14—C35—C36108.52 (17)
C7—O3—C2—C398.2 (2)C34—C35—C36—C3950.6 (2)
C7—O3—C2—C1−82.4 (3)C37—C36—C39—C4045.8 (3)
C6—C1—C2—O3−179.31 (18)C35—C36—C39—C40−85.7 (2)
C21—C1—C2—O31.5 (3)C36—C39—C40—C4193.5 (2)
C6—C1—C2—C30.1 (3)C36—C39—C40—C45−88.7 (2)
C21—C1—C2—C3−179.17 (19)C45—C40—C41—C421.7 (3)
C8—O2—C3—C2−108.5 (2)C39—C40—C41—C42179.51 (19)
C8—O2—C3—C475.8 (3)C45—C40—C41—C25−174.68 (19)
O3—C2—C3—O21.9 (3)C39—C40—C41—C253.1 (3)
C1—C2—C3—O2−177.46 (19)C30—C25—C41—C40−61.6 (3)
O3—C2—C3—C4177.69 (18)C26—C25—C41—C40114.1 (2)
C1—C2—C3—C4−1.7 (3)C30—C25—C41—C42122.1 (2)
C9—O1—C4—C5−10.2 (3)C26—C25—C41—C42−62.2 (3)
C9—O1—C4—C3169.88 (19)C46—O11—C42—C4346.7 (3)
O2—C3—C4—O1−2.9 (3)C46—O11—C42—C41−136.1 (2)
C2—C3—C4—O1−178.58 (19)C40—C41—C42—O11−179.92 (18)
O2—C3—C4—C5177.21 (18)C25—C41—C42—O11−3.5 (3)
C2—C3—C4—C51.5 (3)C40—C41—C42—C43−2.7 (3)
O1—C4—C5—C6−179.6 (2)C25—C41—C42—C43173.8 (2)
C3—C4—C5—C60.3 (3)C47—O12—C43—C42−118.2 (2)
C4—C5—C6—C1−1.9 (3)C47—O12—C43—C4468.6 (3)
C4—C5—C6—C10179.24 (19)O11—C42—C43—O125.5 (3)
C2—C1—C6—C51.7 (3)C41—C42—C43—O12−171.60 (18)
C21—C1—C6—C5−179.1 (2)O11—C42—C43—C44178.75 (19)
C2—C1—C6—C10−179.47 (19)C41—C42—C43—C441.6 (3)
C21—C1—C6—C10−0.3 (3)C48—O13—C44—C45−8.3 (3)
C5—C6—C10—C11−86.6 (2)C48—O13—C44—C43170.97 (19)
C1—C6—C10—C1194.6 (2)O12—C43—C44—O13−5.8 (3)
C6—C10—C11—C1448.3 (3)C42—C43—C44—O13−178.96 (19)
C6—C10—C11—C12−83.8 (2)O12—C43—C44—C45173.53 (19)
C14—C11—C12—O7163.45 (18)C42—C43—C44—C450.4 (3)
C10—C11—C12—O7−66.0 (2)O13—C44—C45—C40177.9 (2)
C14—C11—C12—C1343.0 (2)C43—C44—C45—C40−1.3 (3)
C10—C11—C12—C13173.61 (18)C41—C40—C45—C440.3 (3)
C14—C11—C12—C15−79.3 (2)C39—C40—C45—C44−177.63 (18)
C10—C11—C12—C1551.3 (2)C55—O17—C50—C5193.0 (2)
O7—C12—C15—C1632.4 (2)C55—O17—C50—C49−88.6 (2)
C13—C12—C15—C16149.82 (18)C54—C49—C50—O17−178.97 (18)
C11—C12—C15—C16−86.6 (2)C65—C49—C50—O170.6 (3)
C12—C15—C16—C2194.2 (2)C54—C49—C50—C51−0.7 (3)
C12—C15—C16—C17−85.6 (2)C65—C49—C50—C51178.9 (2)
C21—C16—C17—C18−0.6 (3)C56—O16—C51—C50−114.1 (2)
C15—C16—C17—C18179.11 (19)C56—O16—C51—C5270.7 (3)
C24—O6—C18—C1719.7 (3)O17—C50—C51—O163.1 (3)
C24—O6—C18—C19−158.52 (19)C49—C50—C51—O16−175.26 (18)
C16—C17—C18—O6−176.9 (2)O17—C50—C51—C52178.40 (18)
C16—C17—C18—C191.3 (3)C49—C50—C51—C520.0 (3)
C23—O5—C19—C2099.6 (3)C57—O15—C52—C53−6.6 (3)
C23—O5—C19—C18−85.5 (3)C57—O15—C52—C51173.24 (18)
O6—C18—C19—O51.6 (3)O16—C51—C52—O15−4.8 (3)
C17—C18—C19—O5−176.7 (2)C50—C51—C52—O15−179.91 (18)
O6—C18—C19—C20176.6 (2)O16—C51—C52—C53175.10 (18)
C17—C18—C19—C20−1.8 (3)C50—C51—C52—C53−0.1 (3)
C22—O4—C20—C1974.9 (3)O15—C52—C53—C54−179.4 (2)
C22—O4—C20—C21−103.9 (2)C51—C52—C53—C540.7 (3)
O5—C19—C20—O4−2.1 (3)C52—C53—C54—C49−1.3 (3)
C18—C19—C20—O4−177.12 (19)C52—C53—C54—C58−179.38 (18)
O5—C19—C20—C21176.7 (2)C50—C49—C54—C531.3 (3)
C18—C19—C20—C211.7 (3)C65—C49—C54—C53−178.28 (19)
C17—C16—C21—C200.5 (3)C50—C49—C54—C58179.24 (18)
C15—C16—C21—C20−179.2 (2)C65—C49—C54—C58−0.3 (3)
C17—C16—C21—C1−177.6 (2)C53—C54—C58—C59−87.2 (2)
C15—C16—C21—C12.7 (3)C49—C54—C58—C5994.8 (2)
O4—C20—C21—C16177.7 (2)C54—C58—C59—C6246.5 (3)
C19—C20—C21—C16−1.0 (3)C54—C58—C59—C60−84.8 (2)
O4—C20—C21—C1−4.1 (3)C62—C59—C60—O21165.15 (18)
C19—C20—C21—C1177.1 (2)C58—C59—C60—O21−64.6 (2)
C2—C1—C21—C16116.6 (2)C62—C59—C60—C6145.6 (2)
C6—C1—C21—C16−62.6 (3)C58—C59—C60—C61175.81 (18)
C2—C1—C21—C20−61.5 (3)C62—C59—C60—C63−77.5 (2)
C6—C1—C21—C20119.3 (2)C58—C59—C60—C6352.7 (2)
C33—O10—C26—C2779.2 (2)O21—C60—C63—C6431.7 (2)
C33—O10—C26—C25−98.7 (2)C61—C60—C63—C64148.91 (19)
C30—C25—C26—C271.0 (3)C59—C60—C63—C64−87.4 (2)
C41—C25—C26—C27−174.8 (2)C60—C63—C64—C6595.4 (2)
C30—C25—C26—O10178.85 (18)C60—C63—C64—C69−82.5 (2)
C41—C25—C26—O103.0 (3)C69—C64—C65—C66−0.3 (3)
C32—O9—C27—C2689.7 (3)C63—C64—C65—C66−178.14 (19)
C32—O9—C27—C28−96.0 (2)C69—C64—C65—C49178.6 (2)
O10—C26—C27—O9−3.6 (3)C63—C64—C65—C490.8 (3)
C25—C26—C27—O9174.21 (18)C50—C49—C65—C64119.6 (2)
O10—C26—C27—C28−177.96 (18)C54—C49—C65—C64−60.9 (3)
C25—C26—C27—C28−0.1 (3)C50—C49—C65—C66−61.5 (3)
C31—O8—C28—C2917.8 (3)C54—C49—C65—C66118.0 (2)
C31—O8—C28—C27−160.08 (19)C70—O18—C66—C6782.9 (2)
O9—C27—C28—O81.8 (3)C70—O18—C66—C65−96.0 (2)
C26—C27—C28—O8176.14 (19)C64—C65—C66—O18−179.24 (18)
O9—C27—C28—C29−176.21 (19)C49—C65—C66—O181.8 (3)
C26—C27—C28—C29−1.9 (3)C64—C65—C66—C671.9 (3)
O8—C28—C29—C30−174.84 (19)C49—C65—C66—C67−177.08 (19)
C27—C28—C29—C303.0 (3)C71—O19—C67—C6697.4 (2)
C26—C25—C30—C290.0 (3)C71—O19—C67—C68−88.1 (3)
C41—C25—C30—C29175.8 (2)O18—C66—C67—O19−5.6 (3)
C26—C25—C30—C34−177.49 (19)C65—C66—C67—O19173.29 (19)
C41—C25—C30—C34−1.8 (3)O18—C66—C67—C68179.85 (18)
C28—C29—C30—C25−2.1 (3)C65—C66—C67—C68−1.3 (3)
C28—C29—C30—C34175.57 (18)C72—O20—C68—C6919.1 (3)
C25—C30—C34—C3596.9 (2)C72—O20—C68—C67−159.31 (19)
C29—C30—C34—C35−80.7 (2)O19—C67—C68—O203.0 (3)
C30—C34—C35—O1435.0 (2)C66—C67—C68—O20177.51 (19)
C30—C34—C35—C38151.82 (19)O19—C67—C68—C69−175.47 (19)
C30—C34—C35—C36−84.2 (2)C66—C67—C68—C69−1.0 (3)
O14—C35—C36—C37162.56 (18)O20—C68—C69—C64−175.8 (2)
C38—C35—C36—C3743.0 (2)C67—C68—C69—C642.6 (3)
C34—C35—C36—C37−79.6 (2)C65—C64—C69—C68−1.9 (3)
O14—C35—C36—C39−67.2 (2)C63—C64—C69—C68176.02 (19)
C38—C35—C36—C39173.16 (18)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O7—H7···O2i0.842.102.836 (2)146
O14—H14···O16ii0.842.142.889 (2)149
O21—H21···O12iii0.842.002.793 (2)156
C11—H11···O3i1.002.583.469 (3)148
C37—H37A···O8iv0.982.603.490 (3)151
C37—H37C···O5v0.982.583.498 (3)157
C38—H38B···O18ii0.982.513.389 (3)150
C24—H24B···Cg1vi0.982.803.710 (3)156
C31—H31B···Cg2vii0.982.713.653 (3)181
C72—H72B···Cg3vi0.982.943.894 (3)164

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2738).

References

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  • Lee, I. S., Lee, H. K., Dat, N. T., Lee, M. S., Kim, J. W., Na, D. S. & Kim, Y. H. (2003). Planta Med.69, 63–64. [PubMed]
  • Rigaku/MSC (2005). CrystalClear and CrystalStructure Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, L.-W., Chen, T., Sun, H.-X., Xiong, Y., Zhou, C.-X. & Zhao, Y. (2004). Acta Cryst. E60, o513–o514.

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