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

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ISSN: 2056-9890

Schizandrol A: a lignan from Schisandra chinensis

aSchool of Food Science, Henan Institute of Science and Technology, Xinxiang 453003, People's Republic of China
*Correspondence e-mail: l_zhaohn@yahoo.cn

(Received 2 July 2008; accepted 11 July 2008; online 16 July 2008)

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[Lee, I. S., Jung, K. Y., Oh, S. R., Park, S. H., Ahn, K. S. & Lee, H. K. (1999). Biol. Pharm. Bull. 22, 265-267.], 2003[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.]). For a similar structure, see: Wang et al. (2004[Wang, L.-W., Chen, T., Sun, H.-X., Xiong, Y., Zhou, C.-X. & Zhao, Y. (2004). Acta Cryst. E60, o513-o514.]).

[Scheme 1]

Experimental

Crystal data
  • C24H32O7

  • Mr = 432.50

  • Orthorhombic, P 21 21 21

  • 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[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.982, Tmax = 0.987

  • 48456 measured reflections

  • 8487 independent reflections

  • 7852 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.044

  • wR(F2) = 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

Table 1
Selected torsion angles (°)

C7—O3—C2—C3 98.2 (2)
C46—O11—C42—C43 46.7 (3)
C55—O17—C50—C51 93.0 (2)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C49–C54 ring, Cg2 is the centroid of the C40–C45 ring and Cg3 is the centroid of the C1–C6 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
O7—H7⋯O2i 0.84 2.10 2.836 (2) 146
O14—H14⋯O16ii 0.84 2.14 2.889 (2) 149
O21—H21⋯O12iii 0.84 2.00 2.793 (2) 156
C11—H11⋯O3i 1.00 2.58 3.469 (3) 148
C37—H37A⋯O8iv 0.98 2.60 3.490 (3) 151
C37—H37C⋯O5v 0.98 2.58 3.498 (3) 157
C38—H38B⋯O18ii 0.98 2.51 3.389 (3) 150
C24—H24BCg1ii 0.98 2.80 3.710 (3) 156
C31—H31BCg2vi 0.98 2.71 3.653 (3) 181
C72—H72BCg3ii 0.98 2.94 3.894 (3) 164
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (iii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (iv) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]; (v) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (vi) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, 2-z].

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: CrystalStructure (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan.]).

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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

Refinement top

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.

Computing details top

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

Figures top
[Figure 1] Fig. 1. View of the first molecule in the asymmetric unit with the atom-numbering scheme and 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. View of the second molecule in the asymmetric unit with the atom-numbering scheme and 50% probability displacement ellipsoids.
[Figure 3] Fig. 3. View of the third molecule in the asymmetric unit with the atom-numbering scheme and 50% probability displacement ellipsoids.
1,2,3,10,11,12-hexamethoxy-6,7-dimethyl-5,6,7,8-tetrahydrodibenzo[a,c]cycloocten-6-ol top
Crystal data top
C24H32O7F(000) = 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 = 1.5–27.6°
b = 18.107 (4) ŵ = 0.09 mm1
c = 23.229 (5) ÅT = 113 K
V = 6765 (2) Å3Block, colourless
Z = 120.20 × 0.18 × 0.14 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
8487 independent reflections
Radiation source: rotating anode7852 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.051
Detector resolution: 7.31 pixels mm-1θmax = 27.5°, θmin = 1.5°
ω scansh = 2017
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 2321
Tmin = 0.982, Tmax = 0.987l = 3027
48456 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0626P)2 + 0.2401P]
where P = (Fo2 + 2Fc2)/3
8487 reflections(Δ/σ)max = 0.001
865 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.24 e Å3
Crystal data top
C24H32O7V = 6765 (2) Å3
Mr = 432.50Z = 12
Orthorhombic, P212121Mo Kα radiation
a = 16.084 (3) ŵ = 0.09 mm1
b = 18.107 (4) ÅT = 113 K
c = 23.229 (5) Å0.20 × 0.18 × 0.14 mm
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
8487 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
7852 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.987Rint = 0.051
48456 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.110H-atom parameters constrained
S = 1.09Δρmax = 0.18 e Å3
8487 reflectionsΔρmin = 0.24 e Å3
865 parameters
Special details top

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) top
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)
H70A0.55020.34960.04160.048*
H70B0.63870.38500.05700.048*
H70C0.55620.43400.06160.048*
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) top
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, º) top
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—C182.4 (3)C37—C36—C39—C4045.8 (3)
C6—C1—C2—O3179.31 (18)C35—C36—C39—C4085.7 (2)
C21—C1—C2—O31.5 (3)C36—C39—C40—C4193.5 (2)
C6—C1—C2—C30.1 (3)C36—C39—C40—C4588.7 (2)
C21—C1—C2—C3179.17 (19)C45—C40—C41—C421.7 (3)
C8—O2—C3—C2108.5 (2)C39—C40—C41—C42179.51 (19)
C8—O2—C3—C475.8 (3)C45—C40—C41—C25174.68 (19)
O3—C2—C3—O21.9 (3)C39—C40—C41—C253.1 (3)
C1—C2—C3—O2177.46 (19)C30—C25—C41—C4061.6 (3)
O3—C2—C3—C4177.69 (18)C26—C25—C41—C40114.1 (2)
C1—C2—C3—C41.7 (3)C30—C25—C41—C42122.1 (2)
C9—O1—C4—C510.2 (3)C26—C25—C41—C4262.2 (3)
C9—O1—C4—C3169.88 (19)C46—O11—C42—C4346.7 (3)
O2—C3—C4—O12.9 (3)C46—O11—C42—C41136.1 (2)
C2—C3—C4—O1178.58 (19)C40—C41—C42—O11179.92 (18)
O2—C3—C4—C5177.21 (18)C25—C41—C42—O113.5 (3)
C2—C3—C4—C51.5 (3)C40—C41—C42—C432.7 (3)
O1—C4—C5—C6179.6 (2)C25—C41—C42—C43173.8 (2)
C3—C4—C5—C60.3 (3)C47—O12—C43—C42118.2 (2)
C4—C5—C6—C11.9 (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—O12171.60 (18)
C21—C1—C6—C5179.1 (2)O11—C42—C43—C44178.75 (19)
C2—C1—C6—C10179.47 (19)C41—C42—C43—C441.6 (3)
C21—C1—C6—C100.3 (3)C48—O13—C44—C458.3 (3)
C5—C6—C10—C1186.6 (2)C48—O13—C44—C43170.97 (19)
C1—C6—C10—C1194.6 (2)O12—C43—C44—O135.8 (3)
C6—C10—C11—C1448.3 (3)C42—C43—C44—O13178.96 (19)
C6—C10—C11—C1283.8 (2)O12—C43—C44—C45173.53 (19)
C14—C11—C12—O7163.45 (18)C42—C43—C44—C450.4 (3)
C10—C11—C12—O766.0 (2)O13—C44—C45—C40177.9 (2)
C14—C11—C12—C1343.0 (2)C43—C44—C45—C401.3 (3)
C10—C11—C12—C13173.61 (18)C41—C40—C45—C440.3 (3)
C14—C11—C12—C1579.3 (2)C39—C40—C45—C44177.63 (18)
C10—C11—C12—C1551.3 (2)C55—O17—C50—C5193.0 (2)
O7—C12—C15—C1632.4 (2)C55—O17—C50—C4988.6 (2)
C13—C12—C15—C16149.82 (18)C54—C49—C50—O17178.97 (18)
C11—C12—C15—C1686.6 (2)C65—C49—C50—O170.6 (3)
C12—C15—C16—C2194.2 (2)C54—C49—C50—C510.7 (3)
C12—C15—C16—C1785.6 (2)C65—C49—C50—C51178.9 (2)
C21—C16—C17—C180.6 (3)C56—O16—C51—C50114.1 (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—C19158.52 (19)C49—C50—C51—O16175.26 (18)
C16—C17—C18—O6176.9 (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—C536.6 (3)
C23—O5—C19—C1885.5 (3)C57—O15—C52—C51173.24 (18)
O6—C18—C19—O51.6 (3)O16—C51—C52—O154.8 (3)
C17—C18—C19—O5176.7 (2)C50—C51—C52—O15179.91 (18)
O6—C18—C19—C20176.6 (2)O16—C51—C52—C53175.10 (18)
C17—C18—C19—C201.8 (3)C50—C51—C52—C530.1 (3)
C22—O4—C20—C1974.9 (3)O15—C52—C53—C54179.4 (2)
C22—O4—C20—C21103.9 (2)C51—C52—C53—C540.7 (3)
O5—C19—C20—O42.1 (3)C52—C53—C54—C491.3 (3)
C18—C19—C20—O4177.12 (19)C52—C53—C54—C58179.38 (18)
O5—C19—C20—C21176.7 (2)C50—C49—C54—C531.3 (3)
C18—C19—C20—C211.7 (3)C65—C49—C54—C53178.28 (19)
C17—C16—C21—C200.5 (3)C50—C49—C54—C58179.24 (18)
C15—C16—C21—C20179.2 (2)C65—C49—C54—C580.3 (3)
C17—C16—C21—C1177.6 (2)C53—C54—C58—C5987.2 (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—C161.0 (3)C54—C58—C59—C6084.8 (2)
O4—C20—C21—C14.1 (3)C62—C59—C60—O21165.15 (18)
C19—C20—C21—C1177.1 (2)C58—C59—C60—O2164.6 (2)
C2—C1—C21—C16116.6 (2)C62—C59—C60—C6145.6 (2)
C6—C1—C21—C1662.6 (3)C58—C59—C60—C61175.81 (18)
C2—C1—C21—C2061.5 (3)C62—C59—C60—C6377.5 (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—C2598.7 (2)C61—C60—C63—C64148.91 (19)
C30—C25—C26—C271.0 (3)C59—C60—C63—C6487.4 (2)
C41—C25—C26—C27174.8 (2)C60—C63—C64—C6595.4 (2)
C30—C25—C26—O10178.85 (18)C60—C63—C64—C6982.5 (2)
C41—C25—C26—O103.0 (3)C69—C64—C65—C660.3 (3)
C32—O9—C27—C2689.7 (3)C63—C64—C65—C66178.14 (19)
C32—O9—C27—C2896.0 (2)C69—C64—C65—C49178.6 (2)
O10—C26—C27—O93.6 (3)C63—C64—C65—C490.8 (3)
C25—C26—C27—O9174.21 (18)C50—C49—C65—C64119.6 (2)
O10—C26—C27—C28177.96 (18)C54—C49—C65—C6460.9 (3)
C25—C26—C27—C280.1 (3)C50—C49—C65—C6661.5 (3)
C31—O8—C28—C2917.8 (3)C54—C49—C65—C66118.0 (2)
C31—O8—C28—C27160.08 (19)C70—O18—C66—C6782.9 (2)
O9—C27—C28—O81.8 (3)C70—O18—C66—C6596.0 (2)
C26—C27—C28—O8176.14 (19)C64—C65—C66—O18179.24 (18)
O9—C27—C28—C29176.21 (19)C49—C65—C66—O181.8 (3)
C26—C27—C28—C291.9 (3)C64—C65—C66—C671.9 (3)
O8—C28—C29—C30174.84 (19)C49—C65—C66—C67177.08 (19)
C27—C28—C29—C303.0 (3)C71—O19—C67—C6697.4 (2)
C26—C25—C30—C290.0 (3)C71—O19—C67—C6888.1 (3)
C41—C25—C30—C29175.8 (2)O18—C66—C67—O195.6 (3)
C26—C25—C30—C34177.49 (19)C65—C66—C67—O19173.29 (19)
C41—C25—C30—C341.8 (3)O18—C66—C67—C68179.85 (18)
C28—C29—C30—C252.1 (3)C65—C66—C67—C681.3 (3)
C28—C29—C30—C34175.57 (18)C72—O20—C68—C6919.1 (3)
C25—C30—C34—C3596.9 (2)C72—O20—C68—C67159.31 (19)
C29—C30—C34—C3580.7 (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—C69175.47 (19)
C30—C34—C35—C3684.2 (2)C66—C67—C68—C691.0 (3)
O14—C35—C36—C37162.56 (18)O20—C68—C69—C64175.8 (2)
C38—C35—C36—C3743.0 (2)C67—C68—C69—C642.6 (3)
C34—C35—C36—C3779.6 (2)C65—C64—C69—C681.9 (3)
O14—C35—C36—C3967.2 (2)C63—C64—C69—C68176.02 (19)
C38—C35—C36—C39173.16 (18)
Hydrogen-bond geometry (Å, º) top
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, y1/2, z+3/2; (ii) x+1/2, y+3/2, z+1; (iii) x1/2, 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) x1/2, y+3/2, z+2.

Experimental details

Crystal data
Chemical formulaC24H32O7
Mr432.50
Crystal system, space groupOrthorhombic, P212121
Temperature (K)113
a, b, c (Å)16.084 (3), 18.107 (4), 23.229 (5)
V3)6765 (2)
Z12
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.18 × 0.14
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.982, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
48456, 8487, 7852
Rint0.051
(sin θ/λ)max1)0.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.110, 1.09
No. of reflections8487
No. of parameters865
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.24

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku/MSC, 2005).

Selected torsion angles (º) top
C7—O3—C2—C398.2 (2)C55—O17—C50—C5193.0 (2)
C46—O11—C42—C4346.7 (3)
Hydrogen-bond geometry (Å, º) top
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, y1/2, z+3/2; (ii) x+1/2, y+3/2, z+1; (iii) x1/2, 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) x1/2, y+3/2, z+2.
 

References

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