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ISSN: 2056-9890

2,2,5,7,8-Penta­methyl­chroman-6-yl 2,3,4,6-tetra-O-acetyl-α-D-gluco­pyran­oside from synchrotron data

aSynchrotron Radiation Research Section, MCL, National Cancer Institute, Argonne National Laboratory, Biosciences Division, Bldg 202, Argonne, IL 60439, USA, and bInstitute of Chemistry, University of Białystok, Piłsudskiego 11/4, 15-443 Białystok, Poland
*Correspondence e-mail: kbrzezinski@anl.gov

(Received 12 January 2011; accepted 18 February 2011; online 26 February 2011)

The crystal structure of the title compound, C28H38O11, solved and refined against synchrotron diffraction data, contains two formula units in the asymmetric unit. In both mol­ecules, the dihydro­pyran ring along with its methyl substituents is disordered and adopts two alternative half-chair conformations. The occupancy of the major conformers of the two mol­ecules refined to 0.858 (5) and 0.523 (5).

Related literature

For background to the chemistry of α-tocopherol [systematic name 2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro­chromen-6-ol] and its derivatives and their applications, see: Dubbs & Gupta (1998[Dubbs, M. D. & Gupta, R. B. (1998). J. Chem. Eng. Data, 43, 590-591.]); Azzi & Stoker (2000[Azzi, A. & Stoker, A. (2000). Progr. Lipid Res. 39, 231-255.]); Traber & Atkinson (2007[Traber, M. G. & Atkinson, J. (2007). Free Rad. Biol. Med. 43, 4-15.]). For the preparation, see: Witkowski & Walejko (2002[Witkowski, S. & Walejko, P. (2002). Z. Naturforsch. Teil B, 57, 571-578.]).

[Scheme 1]

Experimental

Crystal data
  • C28H38O11

  • Mr = 550.58

  • Triclinic, P 1

  • a = 8.66 (1) Å

  • b = 11.30 (1) Å

  • c = 14.55 (1) Å

  • α = 85.74 (5)°

  • β = 89.13 (5)°

  • γ = 88.16 (5)°

  • V = 1419 (2) Å3

  • Z = 2

  • Synchrotron radiation

  • λ = 0.59040 Å

  • μ = 0.06 mm−1

  • T = 100 K

  • 0.25 × 0.15 × 0.09 mm

Data collection
  • Mar Research MAR315 CCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 2003[Otwinowski, Z., Borek, D., Majewski, W. & Minor, W. (2003). Acta Cryst. A59, 228-234.]) Tmin = 0.985, Tmax = 0.995

  • 8538 measured reflections

  • 5956 independent reflections

  • 5260 reflections with I > 2σ(I)

  • Rint = 0.023

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.118

  • S = 0.99

  • 5956 reflections

  • 795 parameters

  • 752 restraints

  • H-atom parameters constrained

  • Δρmax = 0.21 e Å−3

  • Δρmin = −0.23 e Å−3

Data collection: NECAT APS beamline software (unpublished); cell refinement: HKL-2000 (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: HKL-2000; program(s) used to solve structure: SHELXD (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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and pyMOL (DeLano, 2002[DeLano, W. L. (2002). The pyMOL Molecular Graphics System. DeLano Scientific, San Carlos, CA, USA.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

α-Tocopherol (vitamin E) is a lipophilic compound, poorly soluble in water (Dubbs & Gupta, 1998). It is also poorly absorbed after oral administration. 2,2,5,7,8-Pentamethyl-6-hydroxychroman in which the lipophylic phytyl chain was replaced with a methyl group is often used as a model compound for structural and biological investigations. Enhancing of aqueous solubility is of interest because of challenges in supplying the vitamin E preparations. In order to improve pharmacological properties, the model compound was converted into the water-soluble glucoside which is easy cleavable by the appropriate enzymes or acidic medium (Witkowski & Walejko, 2002).

In both symmetrically independent molecules, the heterocyclic ring of chroman system exists in the approximate half-chair conformation with two possible alternative positions, exo or endo, of the out of plane atom C03 (C53), as illustrated in the packing diagram, Fig. 2. As a consequence, there are also two alternative positions of the methyl substituents at C02 (C52) atoms. The occupancy ratio is 0.858:0.142 (0.005) and 0.523:0.477 (0.005), in the first and the second molecule, respectively. Two independent molecules in the cell are in the relation resembling the 21 axis parallel to a direction, Fig. 2. This effect is emphasized by the β and γ unit-cell angles being close to 90°.

Related literature top

For background to the chemistry of α-tocopherol and its derivatives and their applications, see: Dubbs & Gupta (1998); Azzi & Stoker (2000); Traber & Atkinson (2007). For the preparation of 2,2,5,7,8-pentamethyl-chroman-6-yl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside, see: Witkowski & Walejko (2002).

Experimental top

The title glucoside was synthesized by a modified Helferich method according to the published procedure (Witkowski & Walejko, 2002). The crystallization was carried out at room temperature by slow evaporation of 2,2,5,7,8-pentamethyl-6-hydroxychromanyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside solution in ethanol.

Refinement top

Fridel related reflections were averaged. The D configuration and anomeric state of the sugar moiety has been attributed according to synthesis and NMR studies (Witkowski & Walejko, 2002). Distance and angle restraints were only applied to the disordered parts of chroman moieties. All hydrogen atoms were constrained to idealized positions with C—H distances fixed at 0.98–1.00 Å and Uiso(H) = 1.5Ueq(C) for methyl hydrogen atoms and 1.2Ueq(C) for others. The sum of occupancies of alternative positions of disordered atoms of was constrained to unity.

Computing details top

Data collection: NECAT APS beamline software; cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data reduction: HKL-2000 (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and pyMOL (DeLano, 2002); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. For clarity, two symmetrically independent molecules are shown separately (a and b) with hydrogen atoms omitted. Carbon atoms of the chroman systems which adopt two different conformations, are shown in green and blue, respectively. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The packing diagram viewed along a axis. Only non-hydrogen atoms are shown.
2,2,5,7,8-Pentamethylchroman-6-yl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside top
Crystal data top
C28H38O11Z = 2
Mr = 550.58F(000) = 588
Triclinic, P1Dx = 1.289 Mg m3
Hall symbol: P 1Synchrotron radiation, λ = 0.59040 Å
a = 8.66 (1) ÅCell parameters from 5956 reflections
b = 11.30 (1) Åθ = 1.5–22.6°
c = 14.55 (1) ŵ = 0.06 mm1
α = 85.74 (5)°T = 100 K
β = 89.13 (5)°Needle, colourless
γ = 88.16 (5)°0.25 × 0.15 × 0.09 mm
V = 1419 (2) Å3
Data collection top
Mar Research MAR315 CCD
diffractometer
5956 independent reflections
Radiation source: NECAT 24ID-C synchrotron beamline APS, USA5260 reflections with I > 2σ(I)
Si111 double crystal monochromatorRint = 0.023
ω scansθmax = 22.6°, θmin = 1.5°
Absorption correction: multi-scan
(SCALEPACK; Otwinowski et al., 2003)
h = 011
Tmin = 0.985, Tmax = 0.995k = 1414
8538 measured reflectionsl = 1818
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0671P)2]
where P = (Fo2 + 2Fc2)/3
5956 reflections(Δ/σ)max < 0.001
795 parametersΔρmax = 0.21 e Å3
752 restraintsΔρmin = 0.23 e Å3
Crystal data top
C28H38O11γ = 88.16 (5)°
Mr = 550.58V = 1419 (2) Å3
Triclinic, P1Z = 2
a = 8.66 (1) ÅSynchrotron radiation, λ = 0.59040 Å
b = 11.30 (1) ŵ = 0.06 mm1
c = 14.55 (1) ÅT = 100 K
α = 85.74 (5)°0.25 × 0.15 × 0.09 mm
β = 89.13 (5)°
Data collection top
Mar Research MAR315 CCD
diffractometer
5956 independent reflections
Absorption correction: multi-scan
(SCALEPACK; Otwinowski et al., 2003)
5260 reflections with I > 2σ(I)
Tmin = 0.985, Tmax = 0.995Rint = 0.023
8538 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045752 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 0.99Δρmax = 0.21 e Å3
5956 reflectionsΔρmin = 0.23 e Å3
795 parameters
Special details top

Experimental. The crystal was mounted with vaseline on a pin attached capillary. Upon mounting, the crystal was quenched to 100 K in a nitrogen-gas stream supplied by an Oxford Cryo-Jet. Diffraction data were measured at the station 24-ID—C of the APS synchrotron by rotation method.

Geometry. All e.s.d.'s 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.

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 > 2σ(F2) is used only for calculating R-factors 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O010.7561 (2)0.6151 (2)0.69759 (14)0.0488 (5)
C02A0.9136 (8)0.6057 (5)0.7333 (3)0.0389 (13)0.858 (5)
C03A1.0148 (4)0.5345 (3)0.6699 (2)0.0389 (8)0.858 (5)
HA03A0.97470.45360.66890.047*0.858 (5)
HA03B1.12100.52720.69440.047*0.858 (5)
C04A1.0197 (5)0.5922 (4)0.5721 (4)0.0409 (10)0.858 (5)
HA04A1.08660.66180.56970.049*0.858 (5)
HA04B1.06470.53500.53010.049*0.858 (5)
C02B0.885 (5)0.612 (2)0.7368 (19)0.051 (9)0.142 (5)
C03B1.013 (3)0.672 (2)0.6797 (13)0.064 (6)0.142 (5)
HB03A1.11380.65060.70900.077*0.142 (5)
HB03B0.99750.75940.68030.077*0.142 (5)
C04B1.020 (2)0.639 (3)0.5796 (15)0.048 (6)0.142 (5)
HB04A1.07860.69920.54170.058*0.142 (5)
HB04B1.07580.56140.57650.058*0.142 (5)
C050.8296 (3)0.6572 (2)0.4453 (2)0.0394 (6)
C060.6793 (3)0.6888 (2)0.41880 (19)0.0353 (5)
C070.5552 (3)0.6891 (2)0.48235 (19)0.0366 (6)
C080.5853 (3)0.6646 (2)0.5762 (2)0.0392 (6)
C090.7371 (3)0.6387 (2)0.6032 (2)0.0400 (6)
C100.8588 (3)0.6314 (3)0.5404 (2)0.0415 (6)
C11A0.9684 (4)0.7319 (3)0.7378 (3)0.0473 (9)0.858 (5)
HA11A0.97100.77150.67560.071*0.858 (5)
HA11B1.07220.72950.76390.071*0.858 (5)
HA11C0.89720.77580.77680.071*0.858 (5)
C12A0.8999 (4)0.5440 (4)0.8282 (3)0.0474 (9)0.858 (5)
HA12A0.86270.46370.82350.071*0.858 (5)
HA12B0.82670.58880.86530.071*0.858 (5)
HA12C1.00130.53940.85740.071*0.858 (5)
C11B0.902 (3)0.4772 (19)0.7345 (14)0.051 (6)0.142 (5)
HB11A0.87100.43920.79430.077*0.142 (5)
HB11B1.01030.45520.72140.077*0.142 (5)
HB11C0.83650.45070.68620.077*0.142 (5)
C12B0.892 (3)0.646 (3)0.8367 (16)0.061 (7)0.142 (5)
HB12A0.90000.73240.83720.092*0.142 (5)
HB12B0.98190.60670.86690.092*0.142 (5)
HB12C0.79750.62130.86990.092*0.142 (5)
C130.9577 (3)0.6458 (3)0.3752 (2)0.0443 (7)
H13A0.91350.64400.31370.066*
H13B1.01810.57220.39010.066*
H13C1.02500.71380.37610.066*
O140.6441 (2)0.71514 (15)0.32506 (13)0.0379 (4)
C150.3903 (3)0.7082 (2)0.4519 (2)0.0403 (6)
H15A0.38800.72580.38500.060*
H15B0.34280.77500.48240.060*
H15C0.33270.63640.46850.060*
C160.4554 (4)0.6646 (3)0.6465 (2)0.0442 (6)
H16A0.49850.66020.70860.066*
H16B0.39130.59580.64010.066*
H16C0.39210.73770.63640.066*
C170.7064 (3)0.8206 (2)0.28211 (18)0.0366 (6)
H17A0.79120.84800.32050.044*
C180.5803 (3)0.9181 (2)0.26962 (19)0.0370 (6)
H18A0.62530.99140.23870.044*
C190.4521 (3)0.8772 (2)0.21147 (19)0.0376 (6)
H19A0.40100.80780.24430.045*
C200.5187 (3)0.8427 (2)0.11993 (19)0.0367 (6)
H20A0.55210.91450.08130.044*
C210.6533 (3)0.7531 (2)0.13481 (19)0.0369 (6)
H21A0.61430.67620.16320.044*
C220.7377 (3)0.7323 (2)0.0457 (2)0.0412 (6)
H22A0.66620.69910.00260.049*
H22B0.77350.80890.01700.049*
O230.7644 (2)0.79836 (16)0.19401 (13)0.0378 (4)
O240.5137 (2)0.94463 (16)0.35732 (13)0.0395 (4)
C250.5971 (3)1.0157 (2)0.4072 (2)0.0409 (6)
O260.7141 (2)1.05995 (18)0.37950 (15)0.0467 (5)
C270.5227 (4)1.0309 (3)0.4989 (2)0.0516 (8)
H27A0.48630.95420.52500.077*
H27B0.43501.08760.49150.077*
H27C0.59811.06090.54030.077*
O280.3402 (2)0.97388 (16)0.19391 (13)0.0397 (4)
C290.1984 (3)0.9609 (2)0.2340 (2)0.0419 (6)
O300.1621 (3)0.8758 (2)0.28195 (16)0.0535 (5)
C310.0959 (4)1.0682 (3)0.2114 (3)0.0538 (8)
H31A0.13921.13730.23740.081*
H31B0.00741.05460.23780.081*
H31C0.08881.08280.14440.081*
O320.3995 (2)0.78273 (16)0.07392 (13)0.0403 (4)
C330.3230 (4)0.8441 (3)0.0039 (2)0.0435 (6)
C340.1947 (4)0.7725 (3)0.0281 (3)0.0618 (9)
H34A0.12070.82490.06300.093*
H34B0.14230.73310.02540.093*
H34C0.23710.71250.06770.093*
O350.3556 (3)0.94005 (19)0.02650 (15)0.0519 (5)
O360.8680 (2)0.65193 (17)0.06139 (14)0.0443 (5)
C370.8400 (4)0.5356 (3)0.0729 (2)0.0458 (7)
C380.9850 (4)0.4649 (3)0.0940 (3)0.0607 (9)
H38A1.06190.48240.04520.091*
H38B0.96320.38010.09760.091*
H38C1.02520.48560.15320.091*
O390.7119 (3)0.49706 (19)0.06786 (16)0.0533 (5)
O510.2336 (2)0.3517 (3)0.28927 (15)0.0623 (7)
C52A0.371 (2)0.3815 (16)0.2494 (14)0.037 (3)0.523 (5)
C53A0.5086 (7)0.3217 (6)0.3023 (4)0.0447 (14)0.523 (5)
HA53A0.50850.23480.29710.054*0.523 (5)
HA53B0.60640.35180.27500.054*0.523 (5)
C54A0.4982 (11)0.3477 (8)0.4039 (6)0.0405 (19)0.523 (5)
HA54A0.56820.29120.43950.049*0.523 (5)
HA54B0.53520.42870.41020.049*0.523 (5)
C52B0.398 (2)0.377 (2)0.2549 (13)0.038 (3)0.477 (5)
C53B0.4895 (7)0.4495 (5)0.3180 (4)0.0389 (14)0.477 (5)
HB53A0.59590.45850.29320.047*0.477 (5)
HB53B0.44050.52970.31970.047*0.477 (5)
C54B0.4957 (11)0.3904 (7)0.4148 (7)0.0355 (19)0.477 (5)
HB54A0.52540.44910.45810.043*0.477 (5)
HB54B0.57550.32550.41730.043*0.477 (5)
C550.3091 (3)0.3160 (2)0.53997 (19)0.0365 (6)
C560.1604 (3)0.2858 (2)0.56897 (18)0.0345 (5)
C570.0357 (3)0.2893 (2)0.50902 (19)0.0342 (5)
C580.0645 (3)0.3129 (2)0.41409 (19)0.0366 (6)
C590.2153 (3)0.3346 (3)0.3839 (2)0.0437 (6)
C600.3370 (3)0.3390 (3)0.4452 (2)0.0441 (7)
C61A0.3660 (7)0.5140 (5)0.2516 (4)0.0457 (14)0.523 (5)
HA61A0.30730.54960.19900.069*0.523 (5)
HA61B0.47150.54290.24840.069*0.523 (5)
HA61C0.31590.53600.30910.069*0.523 (5)
C62A0.3814 (7)0.3441 (6)0.1501 (4)0.0449 (14)0.523 (5)
HA62A0.38590.25730.15100.067*0.523 (5)
HA62B0.47490.37590.12010.067*0.523 (5)
HA62C0.29040.37520.11600.067*0.523 (5)
C61B0.4591 (8)0.2526 (6)0.2504 (5)0.0485 (16)0.477 (5)
HB61A0.56490.25340.22560.073*0.477 (5)
HB61B0.39360.21040.21030.073*0.477 (5)
HB61C0.45890.21230.31240.073*0.477 (5)
C62B0.3773 (8)0.4428 (7)0.1606 (4)0.0498 (17)0.477 (5)
HB62A0.33230.52230.16810.075*0.477 (5)
HB62B0.30820.39890.12370.075*0.477 (5)
HB62C0.47790.44980.12920.075*0.477 (5)
C630.4369 (3)0.3278 (2)0.60830 (19)0.0404 (6)
H63A0.49800.39690.58870.061*
H63B0.50370.25600.61090.061*
H63C0.39160.33800.66940.061*
O640.1302 (2)0.25883 (15)0.66386 (12)0.0352 (4)
C650.1279 (3)0.2750 (2)0.5431 (2)0.0383 (6)
H65A0.18960.34670.52420.058*
H65B0.12910.26270.61040.058*
H65C0.17170.20630.51670.058*
C660.0684 (3)0.3201 (3)0.3479 (2)0.0418 (6)
H66A0.12930.24860.35800.063*
H66B0.02820.32610.28450.063*
H66C0.13400.39020.35830.063*
C670.1988 (3)0.1507 (2)0.70335 (19)0.0370 (6)
H67A0.28180.12180.66130.044*
C680.0754 (3)0.0573 (2)0.71880 (18)0.0358 (5)
H68A0.12410.01770.74740.043*
C690.0498 (3)0.1007 (2)0.78254 (19)0.0368 (6)
H69A0.10180.17410.75330.044*
C700.0221 (3)0.1284 (2)0.87262 (19)0.0360 (6)
H70A0.06220.05350.90610.043*
C710.1532 (3)0.2149 (2)0.85451 (18)0.0359 (6)
H71A0.11000.29390.83000.043*
C720.2424 (3)0.2292 (2)0.9411 (2)0.0404 (6)
H72A0.17610.27120.98510.049*
H72B0.27130.14990.97050.049*
O730.2619 (2)0.16994 (16)0.78913 (12)0.0373 (4)
O740.0062 (2)0.03338 (16)0.63368 (13)0.0390 (4)
C750.0909 (3)0.0373 (2)0.5785 (2)0.0402 (6)
O760.2155 (2)0.07916 (18)0.60091 (15)0.0470 (5)
C770.0086 (4)0.0553 (3)0.4925 (2)0.0510 (7)
H77A0.07920.09360.44970.077*
H77B0.02800.02170.46420.077*
H77C0.07970.10580.50660.077*
O780.1617 (2)0.01101 (16)0.80209 (13)0.0386 (4)
C790.3014 (3)0.0277 (3)0.7598 (2)0.0439 (6)
O800.3347 (2)0.1129 (2)0.71021 (16)0.0539 (6)
C810.4040 (4)0.0740 (3)0.7847 (3)0.0565 (8)
H81A0.50760.04360.80010.085*
H81B0.36160.12180.83800.085*
H81C0.40980.12340.73230.085*
O820.0937 (2)0.18503 (15)0.92817 (13)0.0384 (4)
C830.1639 (3)0.1161 (2)0.9962 (2)0.0396 (6)
C840.2941 (4)0.1831 (3)1.0383 (2)0.0542 (8)
H84A0.27270.26791.03340.081*
H84B0.30570.15521.10340.081*
H84C0.38980.17011.00580.081*
O850.1246 (3)0.01617 (18)1.01807 (15)0.0516 (5)
O860.3803 (2)0.2954 (2)0.92082 (15)0.0484 (5)
C870.3644 (4)0.4134 (3)0.9065 (2)0.0524 (8)
C880.5135 (5)0.4673 (5)0.8774 (3)0.0841 (14)
H88A0.49790.55340.86600.126*
H88B0.55140.43360.82090.126*
H88C0.58950.45040.92630.126*
O890.2423 (3)0.4656 (2)0.91500 (18)0.0616 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O010.0416 (11)0.0643 (14)0.0400 (12)0.0051 (10)0.0039 (9)0.0009 (10)
C02A0.038 (2)0.040 (3)0.039 (2)0.0009 (18)0.0043 (16)0.0008 (19)
C03A0.0435 (17)0.0315 (15)0.0412 (18)0.0003 (13)0.0014 (13)0.0001 (13)
C04A0.042 (2)0.033 (2)0.047 (2)0.0019 (15)0.0032 (15)0.0004 (17)
C02B0.057 (17)0.030 (13)0.066 (16)0.002 (12)0.010 (13)0.005 (12)
C03B0.085 (13)0.051 (11)0.053 (12)0.023 (11)0.001 (11)0.009 (10)
C04B0.041 (11)0.077 (16)0.024 (10)0.000 (12)0.009 (8)0.011 (11)
C050.0466 (15)0.0285 (12)0.0431 (16)0.0058 (11)0.0021 (12)0.0003 (11)
C060.0421 (14)0.0265 (12)0.0371 (14)0.0025 (10)0.0029 (11)0.0007 (10)
C070.0447 (14)0.0275 (12)0.0380 (14)0.0052 (10)0.0005 (11)0.0021 (10)
C080.0497 (16)0.0302 (13)0.0375 (15)0.0053 (11)0.0005 (12)0.0001 (11)
C090.0454 (15)0.0340 (13)0.0403 (16)0.0042 (11)0.0002 (12)0.0005 (11)
C100.0426 (14)0.0377 (14)0.0440 (16)0.0010 (11)0.0049 (12)0.0010 (12)
C11A0.055 (2)0.0369 (17)0.052 (2)0.0079 (15)0.0018 (16)0.0083 (15)
C12A0.0456 (19)0.051 (2)0.045 (2)0.0000 (16)0.0002 (15)0.0025 (16)
C11B0.065 (14)0.054 (13)0.031 (10)0.025 (10)0.007 (9)0.006 (9)
C12B0.042 (11)0.086 (18)0.056 (14)0.011 (12)0.005 (10)0.015 (13)
C130.0491 (16)0.0374 (15)0.0459 (17)0.0032 (12)0.0016 (13)0.0006 (12)
O140.0472 (10)0.0316 (9)0.0348 (10)0.0071 (8)0.0001 (8)0.0004 (8)
C150.0444 (15)0.0362 (14)0.0404 (15)0.0043 (11)0.0011 (11)0.0023 (11)
C160.0495 (16)0.0403 (15)0.0428 (16)0.0012 (12)0.0008 (12)0.0034 (12)
C170.0456 (15)0.0307 (13)0.0330 (14)0.0055 (11)0.0003 (11)0.0019 (10)
C180.0435 (14)0.0319 (13)0.0359 (14)0.0055 (11)0.0020 (11)0.0025 (11)
C190.0430 (14)0.0287 (12)0.0410 (15)0.0021 (11)0.0035 (11)0.0008 (11)
C200.0449 (15)0.0286 (13)0.0371 (14)0.0070 (11)0.0059 (11)0.0019 (10)
C210.0412 (14)0.0336 (13)0.0360 (14)0.0042 (11)0.0011 (11)0.0009 (11)
C220.0487 (16)0.0344 (14)0.0402 (15)0.0017 (12)0.0022 (12)0.0022 (11)
O230.0419 (10)0.0358 (10)0.0361 (10)0.0060 (8)0.0008 (8)0.0039 (8)
O240.0487 (11)0.0308 (9)0.0398 (11)0.0077 (8)0.0009 (8)0.0065 (8)
C250.0525 (16)0.0282 (13)0.0427 (16)0.0037 (12)0.0019 (12)0.0056 (11)
O260.0496 (12)0.0398 (11)0.0516 (13)0.0096 (9)0.0027 (9)0.0066 (9)
C270.068 (2)0.0439 (17)0.0453 (17)0.0103 (15)0.0048 (15)0.0139 (13)
O280.0440 (10)0.0308 (9)0.0439 (11)0.0009 (8)0.0013 (8)0.0001 (8)
C290.0472 (15)0.0375 (15)0.0421 (16)0.0078 (12)0.0043 (12)0.0062 (12)
O300.0516 (12)0.0491 (12)0.0587 (14)0.0070 (10)0.0070 (10)0.0045 (10)
C310.0489 (17)0.0507 (18)0.062 (2)0.0046 (14)0.0029 (14)0.0087 (15)
O320.0483 (11)0.0307 (9)0.0423 (11)0.0031 (8)0.0080 (8)0.0026 (8)
C330.0524 (16)0.0374 (15)0.0408 (15)0.0018 (12)0.0064 (12)0.0027 (12)
C340.060 (2)0.0548 (19)0.071 (2)0.0059 (16)0.0217 (17)0.0072 (17)
O350.0635 (14)0.0443 (12)0.0470 (13)0.0027 (10)0.0102 (10)0.0049 (10)
O360.0431 (10)0.0422 (11)0.0478 (12)0.0019 (9)0.0010 (8)0.0047 (9)
C370.0570 (18)0.0419 (16)0.0381 (16)0.0010 (14)0.0017 (13)0.0007 (12)
C380.065 (2)0.060 (2)0.055 (2)0.0152 (17)0.0055 (16)0.0012 (16)
O390.0559 (13)0.0428 (12)0.0616 (15)0.0070 (10)0.0014 (10)0.0045 (10)
O510.0351 (11)0.112 (2)0.0362 (12)0.0017 (12)0.0016 (9)0.0153 (12)
C52A0.031 (7)0.029 (4)0.051 (5)0.000 (4)0.005 (4)0.003 (3)
C53A0.041 (3)0.057 (4)0.036 (3)0.005 (3)0.003 (2)0.000 (3)
C54A0.040 (4)0.042 (5)0.039 (4)0.007 (4)0.002 (3)0.002 (3)
C52B0.027 (6)0.050 (6)0.037 (6)0.009 (4)0.010 (4)0.001 (4)
C53B0.038 (3)0.034 (3)0.044 (3)0.010 (2)0.000 (2)0.000 (2)
C54B0.032 (3)0.032 (4)0.042 (4)0.004 (3)0.001 (3)0.003 (3)
C550.0381 (13)0.0325 (13)0.0382 (15)0.0011 (10)0.0034 (11)0.0033 (11)
C560.0429 (14)0.0275 (12)0.0325 (14)0.0001 (10)0.0016 (11)0.0018 (10)
C570.0375 (13)0.0279 (12)0.0366 (14)0.0020 (10)0.0017 (10)0.0023 (10)
C580.0370 (14)0.0347 (13)0.0376 (15)0.0029 (11)0.0001 (10)0.0020 (11)
C590.0416 (14)0.0523 (17)0.0353 (15)0.0005 (13)0.0034 (11)0.0088 (12)
C600.0378 (14)0.0516 (17)0.0410 (16)0.0032 (12)0.0001 (11)0.0100 (13)
C61A0.053 (3)0.039 (3)0.046 (3)0.017 (2)0.003 (3)0.003 (2)
C62A0.041 (3)0.061 (4)0.033 (3)0.009 (3)0.001 (2)0.004 (3)
C61B0.053 (4)0.044 (3)0.050 (4)0.003 (3)0.003 (3)0.012 (3)
C62B0.055 (4)0.057 (4)0.038 (3)0.018 (3)0.001 (3)0.001 (3)
C630.0436 (15)0.0379 (14)0.0394 (15)0.0039 (12)0.0051 (11)0.0004 (11)
O640.0412 (10)0.0301 (9)0.0337 (10)0.0015 (7)0.0003 (7)0.0004 (7)
C650.0382 (13)0.0368 (14)0.0396 (15)0.0026 (11)0.0019 (11)0.0002 (11)
C660.0377 (14)0.0443 (15)0.0429 (16)0.0021 (12)0.0041 (11)0.0015 (12)
C670.0443 (15)0.0299 (13)0.0362 (14)0.0023 (11)0.0001 (11)0.0001 (11)
C680.0440 (14)0.0302 (12)0.0328 (14)0.0004 (10)0.0004 (11)0.0005 (10)
C690.0436 (14)0.0277 (12)0.0386 (15)0.0018 (10)0.0046 (11)0.0009 (10)
C700.0408 (14)0.0288 (12)0.0378 (14)0.0025 (10)0.0061 (11)0.0025 (10)
C710.0400 (14)0.0298 (13)0.0377 (15)0.0006 (11)0.0028 (11)0.0030 (10)
C720.0474 (15)0.0350 (14)0.0386 (15)0.0035 (12)0.0005 (12)0.0001 (11)
O730.0394 (10)0.0377 (10)0.0345 (10)0.0022 (8)0.0005 (8)0.0023 (8)
O740.0472 (10)0.0335 (9)0.0364 (10)0.0013 (8)0.0014 (8)0.0056 (8)
C750.0511 (17)0.0276 (13)0.0419 (16)0.0015 (12)0.0079 (12)0.0037 (11)
O760.0495 (12)0.0390 (11)0.0528 (13)0.0044 (9)0.0010 (9)0.0087 (9)
C770.064 (2)0.0446 (16)0.0454 (18)0.0022 (14)0.0022 (14)0.0091 (14)
O780.0425 (10)0.0315 (9)0.0415 (11)0.0038 (8)0.0005 (8)0.0009 (8)
C790.0415 (15)0.0460 (16)0.0438 (16)0.0025 (12)0.0012 (12)0.0000 (13)
O800.0455 (12)0.0523 (13)0.0617 (14)0.0003 (10)0.0047 (10)0.0104 (11)
C810.0499 (17)0.0492 (18)0.070 (2)0.0116 (15)0.0026 (15)0.0007 (16)
O820.0431 (10)0.0305 (9)0.0413 (11)0.0005 (8)0.0068 (8)0.0023 (8)
C830.0434 (14)0.0361 (14)0.0395 (15)0.0072 (12)0.0023 (11)0.0032 (11)
C840.0579 (19)0.0458 (17)0.058 (2)0.0022 (14)0.0196 (15)0.0041 (14)
O850.0649 (14)0.0396 (11)0.0483 (13)0.0003 (10)0.0079 (10)0.0064 (9)
O860.0447 (11)0.0559 (13)0.0455 (12)0.0094 (10)0.0035 (9)0.0048 (10)
C870.058 (2)0.057 (2)0.0420 (17)0.0141 (16)0.0108 (14)0.0056 (14)
C880.075 (3)0.113 (4)0.063 (3)0.049 (3)0.016 (2)0.019 (2)
O890.0707 (17)0.0452 (13)0.0693 (17)0.0071 (12)0.0181 (12)0.0014 (11)
Geometric parameters (Å, º) top
O01—C02B1.26 (4)O51—C52A1.36 (2)
O01—C091.390 (4)O51—C591.383 (4)
O01—C02A1.465 (7)O51—C52B1.53 (2)
C02A—C12A1.504 (6)C52A—C61A1.499 (19)
C02A—C03A1.518 (6)C52A—C62A1.53 (2)
C02A—C11A1.524 (7)C52A—C53A1.541 (15)
C03A—C04A1.521 (6)C53A—C54A1.529 (9)
C03A—HA03A0.9900C53A—HA53A0.9900
C03A—HA03B0.9900C53A—HA53B0.9900
C04A—C101.517 (5)C54A—C601.515 (9)
C04A—HA04A0.9900C54A—HA54A0.9900
C04A—HA04B0.9900C54A—HA54B0.9900
C02B—C11B1.526 (19)C52B—C61B1.49 (2)
C02B—C03B1.526 (19)C52B—C53B1.521 (16)
C02B—C12B1.535 (19)C52B—C62B1.52 (2)
C03B—C04B1.532 (17)C53B—C54B1.514 (11)
C03B—HB03A0.9900C53B—HB53A0.9900
C03B—HB03B0.9900C53B—HB53B0.9900
C04B—C101.525 (17)C54B—C601.554 (10)
C04B—HB04A0.9900C54B—HB54A0.9900
C04B—HB04B0.9900C54B—HB54B0.9900
C05—C061.391 (4)C55—C561.394 (4)
C05—C101.417 (4)C55—C601.403 (4)
C05—C131.504 (4)C55—C631.514 (4)
C06—O141.410 (3)C56—C571.396 (4)
C06—C071.407 (4)C56—O641.414 (3)
C07—C081.400 (4)C57—C581.407 (4)
C07—C151.506 (4)C57—C651.504 (4)
C08—C091.394 (4)C58—C591.395 (4)
C08—C161.508 (4)C58—C661.508 (4)
C09—C101.389 (4)C59—C601.396 (4)
C11A—HA11A0.9800C61A—HA61A0.9800
C11A—HA11B0.9800C61A—HA61B0.9800
C11A—HA11C0.9800C61A—HA61C0.9800
C12A—HA12A0.9800C62A—HA62A0.9800
C12A—HA12B0.9800C62A—HA62B0.9800
C12A—HA12C0.9800C62A—HA62C0.9800
C11B—HB11A0.9800C61B—HB61A0.9800
C11B—HB11B0.9800C61B—HB61B0.9800
C11B—HB11C0.9800C61B—HB61C0.9800
C12B—HB12A0.9800C62B—HB62A0.9800
C12B—HB12B0.9800C62B—HB62B0.9800
C12B—HB12C0.9800C62B—HB62C0.9800
C13—H13A0.9800C63—H63A0.9800
C13—H13B0.9800C63—H63B0.9800
C13—H13C0.9800C63—H63C0.9800
O14—C171.422 (3)O64—C671.426 (3)
C15—H15A0.9800C65—H65A0.9800
C15—H15B0.9800C65—H65B0.9800
C15—H15C0.9800C65—H65C0.9800
C16—H16A0.9800C66—H66A0.9800
C16—H16B0.9800C66—H66B0.9800
C16—H16C0.9800C66—H66C0.9800
C17—O231.407 (3)C67—O731.404 (3)
C17—C181.530 (4)C67—C681.529 (4)
C17—H17A1.0000C67—H67A1.0000
C18—O241.440 (3)C68—O741.432 (3)
C18—C191.510 (4)C68—C691.510 (3)
C18—H18A1.0000C68—H68A1.0000
C19—O281.447 (3)C69—O781.435 (3)
C19—C201.516 (4)C69—C701.517 (4)
C19—H19A1.0000C69—H69A1.0000
C20—O321.451 (3)C70—O821.442 (3)
C20—C211.526 (4)C70—C711.530 (4)
C20—H20A1.0000C70—H70A1.0000
C21—O231.433 (3)C71—O731.436 (3)
C21—C221.508 (4)C71—C721.509 (4)
C21—H21A1.0000C71—H71A1.0000
C22—O361.435 (4)C72—O861.445 (4)
C22—H22A0.9900C72—H72A0.9900
C22—H22B0.9900C72—H72B0.9900
O24—C251.354 (3)O74—C751.364 (3)
C25—O261.196 (3)C75—O761.204 (4)
C25—C271.491 (4)C75—C771.480 (4)
C27—H27A0.9800C77—H77A0.9800
C27—H27B0.9800C77—H77B0.9800
C27—H27C0.9800C77—H77C0.9800
O28—C291.359 (4)O78—C791.367 (3)
C29—O301.193 (3)C79—O801.190 (4)
C29—C311.499 (4)C79—C811.495 (4)
C31—H31A0.9800C81—H81A0.9800
C31—H31B0.9800C81—H81B0.9800
C31—H31C0.9800C81—H81C0.9800
O32—C331.358 (4)O82—C831.361 (3)
C33—O351.181 (4)C83—O851.190 (4)
C33—C341.496 (5)C83—C841.488 (4)
C34—H34A0.9800C84—H84A0.9800
C34—H34B0.9800C84—H84B0.9800
C34—H34C0.9800C84—H84C0.9800
O36—C371.342 (4)O86—C871.337 (4)
C37—O391.211 (4)C87—O891.204 (4)
C37—C381.490 (5)C87—C881.488 (5)
C38—H38A0.9800C88—H88A0.9800
C38—H38B0.9800C88—H88B0.9800
C38—H38C0.9800C88—H88C0.9800
C02B—O01—C09123.9 (11)C52A—O51—C59122.0 (7)
C02B—O01—C02A6.8 (12)C52A—O51—C52B7.3 (13)
C09—O01—C02A118.2 (3)C59—O51—C52B115.5 (6)
O01—C02A—C12A105.5 (4)O51—C52A—C61A102.3 (13)
O01—C02A—C03A109.1 (4)O51—C52A—C62A111.0 (10)
C12A—C02A—C03A111.8 (4)C61A—C52A—C62A111.4 (14)
O01—C02A—C11A106.9 (4)O51—C52A—C53A112.0 (14)
C12A—C02A—C11A111.0 (4)C61A—C52A—C53A112.7 (10)
C03A—C02A—C11A112.1 (4)C62A—C52A—C53A107.5 (13)
C02A—C03A—C04A112.0 (3)C54A—C53A—C52A110.2 (9)
C02A—C03A—HA03A109.2C54A—C53A—HA53A109.6
C04A—C03A—HA03A109.2C52A—C53A—HA53A109.6
C02A—C03A—HA03B109.2C54A—C53A—HA53B109.6
C04A—C03A—HA03B109.2C52A—C53A—HA53B109.6
HA03A—C03A—HA03B107.9HA53A—C53A—HA53B108.1
C10—C04A—C03A110.8 (3)C60—C54A—C53A114.0 (6)
C10—C04A—HA04A109.5C60—C54A—HA54A108.8
C03A—C04A—HA04A109.5C53A—C54A—HA54A108.8
C10—C04A—HA04B109.5C60—C54A—HA54B108.8
C03A—C04A—HA04B109.5C53A—C54A—HA54B108.8
HA04A—C04A—HA04B108.1HA54A—C54A—HA54B107.6
O01—C02B—C11B92.6 (19)C61B—C52B—O5199.3 (13)
O01—C02B—C03B114 (2)C61B—C52B—C53B113.7 (12)
C11B—C02B—C03B110 (2)O51—C52B—C53B114.0 (14)
O01—C02B—C12B119 (2)C61B—C52B—C62B113.4 (13)
C11B—C02B—C12B110 (2)O51—C52B—C62B104.6 (11)
C03B—C02B—C12B110 (2)C53B—C52B—C62B111.0 (14)
C02B—C03B—C04B113.4 (18)C54B—C53B—C52B111.1 (9)
C02B—C03B—HB03A108.9C54B—C53B—HB53A109.4
C04B—C03B—HB03A108.9C52B—C53B—HB53A109.4
C02B—C03B—HB03B108.9C54B—C53B—HB53B109.4
C04B—C03B—HB03B108.9C52B—C53B—HB53B109.4
HB03A—C03B—HB03B107.7HB53A—C53B—HB53B108.0
C10—C04B—C03B111.4 (16)C53B—C54B—C60111.2 (7)
C10—C04B—HB04A109.3C53B—C54B—HB54A109.4
C03B—C04B—HB04A109.3C60—C54B—HB54A109.4
C10—C04B—HB04B109.3C53B—C54B—HB54B109.4
C03B—C04B—HB04B109.3C60—C54B—HB54B109.4
HB04A—C04B—HB04B108.0HB54A—C54B—HB54B108.0
C06—C05—C10118.3 (3)C56—C55—C60118.2 (2)
C06—C05—C13121.3 (3)C56—C55—C63121.5 (2)
C10—C05—C13120.3 (3)C60—C55—C63120.3 (2)
C05—C06—O14120.6 (2)C55—C56—C57122.8 (2)
C05—C06—C07122.2 (3)C55—C56—O64119.3 (2)
O14—C06—C07117.1 (2)C57—C56—O64117.7 (2)
C08—C07—C06119.0 (3)C56—C57—C58118.4 (2)
C08—C07—C15119.0 (2)C56—C57—C65122.2 (2)
C06—C07—C15121.9 (2)C58—C57—C65119.3 (2)
C09—C08—C07118.7 (3)C59—C58—C57118.9 (2)
C09—C08—C16120.8 (3)C59—C58—C66121.4 (3)
C07—C08—C16120.5 (3)C57—C58—C66119.6 (2)
O01—C09—C10122.6 (3)O51—C59—C58114.8 (2)
O01—C09—C08114.7 (2)O51—C59—C60123.2 (3)
C10—C09—C08122.6 (3)C58—C59—C60122.0 (3)
C09—C10—C05119.0 (3)C59—C60—C55119.3 (3)
C09—C10—C04A120.8 (3)C59—C60—C54A117.0 (4)
C05—C10—C04A120.1 (3)C55—C60—C54A122.8 (4)
C09—C10—C04B115.9 (9)C59—C60—C54B122.1 (4)
C05—C10—C04B121.7 (10)C55—C60—C54B117.6 (4)
C04A—C10—C04B20.7 (12)C54A—C60—C54B19.4 (3)
C02A—C11A—HA11A109.5C52A—C61A—HA61A109.5
C02A—C11A—HA11B109.5C52A—C61A—HA61B109.5
HA11A—C11A—HA11B109.5HA61A—C61A—HA61B109.5
C02A—C11A—HA11C109.5C52A—C61A—HA61C109.5
HA11A—C11A—HA11C109.5HA61A—C61A—HA61C109.5
HA11B—C11A—HA11C109.5HA61B—C61A—HA61C109.5
C02A—C12A—HA12A109.5C52A—C62A—HA62A109.5
C02A—C12A—HA12B109.5C52A—C62A—HA62B109.5
HA12A—C12A—HA12B109.5HA62A—C62A—HA62B109.5
C02A—C12A—HA12C109.5C52A—C62A—HA62C109.5
HA12A—C12A—HA12C109.5HA62A—C62A—HA62C109.5
HA12B—C12A—HA12C109.5HA62B—C62A—HA62C109.5
C02B—C11B—HB11A109.5C52B—C61B—HB61A109.5
C02B—C11B—HB11B109.5C52B—C61B—HB61B109.5
HB11A—C11B—HB11B109.5HB61A—C61B—HB61B109.5
C02B—C11B—HB11C109.5C52B—C61B—HB61C109.5
HB11A—C11B—HB11C109.5HB61A—C61B—HB61C109.5
HB11B—C11B—HB11C109.5HB61B—C61B—HB61C109.5
C02B—C12B—HB12A109.5C52B—C62B—HB62A109.5
C02B—C12B—HB12B109.5C52B—C62B—HB62B109.5
HB12A—C12B—HB12B109.5HB62A—C62B—HB62B109.5
C02B—C12B—HB12C109.5C52B—C62B—HB62C109.5
HB12A—C12B—HB12C109.5HB62A—C62B—HB62C109.5
HB12B—C12B—HB12C109.5HB62B—C62B—HB62C109.5
C05—C13—H13A109.5C55—C63—H63A109.5
C05—C13—H13B109.5C55—C63—H63B109.5
H13A—C13—H13B109.5H63A—C63—H63B109.5
C05—C13—H13C109.5C55—C63—H63C109.5
H13A—C13—H13C109.5H63A—C63—H63C109.5
H13B—C13—H13C109.5H63B—C63—H63C109.5
C06—O14—C17116.4 (2)C56—O64—C67116.09 (18)
C07—C15—H15A109.5C57—C65—H65A109.5
C07—C15—H15B109.5C57—C65—H65B109.5
H15A—C15—H15B109.5H65A—C65—H65B109.5
C07—C15—H15C109.5C57—C65—H65C109.5
H15A—C15—H15C109.5H65A—C65—H65C109.5
H15B—C15—H15C109.5H65B—C65—H65C109.5
C08—C16—H16A109.5C58—C66—H66A109.5
C08—C16—H16B109.5C58—C66—H66B109.5
H16A—C16—H16B109.5H66A—C66—H66B109.5
C08—C16—H16C109.5C58—C66—H66C109.5
H16A—C16—H16C109.5H66A—C66—H66C109.5
H16B—C16—H16C109.5H66B—C66—H66C109.5
O23—C17—O14109.6 (2)O73—C67—O64109.6 (2)
O23—C17—C18107.5 (2)O73—C67—C68108.2 (2)
O14—C17—C18110.4 (2)O64—C67—C68109.7 (2)
O23—C17—H17A109.8O73—C67—H67A109.8
O14—C17—H17A109.8O64—C67—H67A109.8
C18—C17—H17A109.8C68—C67—H67A109.8
O24—C18—C19107.6 (2)O74—C68—C69108.4 (2)
O24—C18—C17110.7 (2)O74—C68—C67111.1 (2)
C19—C18—C17109.9 (2)C69—C68—C67109.9 (2)
O24—C18—H18A109.5O74—C68—H68A109.1
C19—C18—H18A109.5C69—C68—H68A109.1
C17—C18—H18A109.5C67—C68—H68A109.1
O28—C19—C18109.2 (2)O78—C69—C68110.5 (2)
O28—C19—C20108.5 (2)O78—C69—C70108.4 (2)
C18—C19—C20109.3 (2)C68—C69—C70109.1 (2)
O28—C19—H19A109.9O78—C69—H69A109.6
C18—C19—H19A109.9C68—C69—H69A109.6
C20—C19—H19A109.9C70—C69—H69A109.6
O32—C20—C19107.5 (2)O82—C70—C69108.8 (2)
O32—C20—C21106.5 (2)O82—C70—C71107.7 (2)
C19—C20—C21110.7 (2)C69—C70—C71110.4 (2)
O32—C20—H20A110.7O82—C70—H70A110.0
C19—C20—H20A110.7C69—C70—H70A110.0
C21—C20—H20A110.7C71—C70—H70A110.0
O23—C21—C22106.2 (2)O73—C71—C72106.5 (2)
O23—C21—C20109.8 (2)O73—C71—C70110.1 (2)
C22—C21—C20111.7 (2)C72—C71—C70111.3 (2)
O23—C21—H21A109.7O73—C71—H71A109.6
C22—C21—H21A109.7C72—C71—H71A109.6
C20—C21—H21A109.7C70—C71—H71A109.6
O36—C22—C21111.0 (2)O86—C72—C71111.0 (2)
O36—C22—H22A109.4O86—C72—H72A109.4
C21—C22—H22A109.4C71—C72—H72A109.4
O36—C22—H22B109.4O86—C72—H72B109.4
C21—C22—H22B109.4C71—C72—H72B109.4
H22A—C22—H22B108.0H72A—C72—H72B108.0
C17—O23—C21114.2 (2)C67—O73—C71114.6 (2)
C25—O24—C18115.6 (2)C75—O74—C68116.2 (2)
O26—C25—O24123.3 (3)O76—C75—O74121.9 (3)
O26—C25—C27125.7 (3)O76—C75—C77126.6 (3)
O24—C25—C27111.1 (3)O74—C75—C77111.5 (3)
C25—C27—H27A109.5C75—C77—H77A109.5
C25—C27—H27B109.5C75—C77—H77B109.5
H27A—C27—H27B109.5H77A—C77—H77B109.5
C25—C27—H27C109.5C75—C77—H77C109.5
H27A—C27—H27C109.5H77A—C77—H77C109.5
H27B—C27—H27C109.5H77B—C77—H77C109.5
C29—O28—C19116.9 (2)C79—O78—C69117.1 (2)
O30—C29—O28124.1 (3)O80—C79—O78123.5 (3)
O30—C29—C31124.9 (3)O80—C79—C81125.5 (3)
O28—C29—C31111.1 (2)O78—C79—C81111.0 (2)
C29—C31—H31A109.5C79—C81—H81A109.5
C29—C31—H31B109.5C79—C81—H81B109.5
H31A—C31—H31B109.5H81A—C81—H81B109.5
C29—C31—H31C109.5C79—C81—H81C109.5
H31A—C31—H31C109.5H81A—C81—H81C109.5
H31B—C31—H31C109.5H81B—C81—H81C109.5
C33—O32—C20118.1 (2)C83—O82—C70117.3 (2)
O35—C33—O32123.9 (3)O85—C83—O82123.9 (3)
O35—C33—C34125.9 (3)O85—C83—C84125.5 (3)
O32—C33—C34110.2 (3)O82—C83—C84110.6 (2)
C33—C34—H34A109.5C83—C84—H84A109.5
C33—C34—H34B109.5C83—C84—H84B109.5
H34A—C34—H34B109.5H84A—C84—H84B109.5
C33—C34—H34C109.5C83—C84—H84C109.5
H34A—C34—H34C109.5H84A—C84—H84C109.5
H34B—C34—H34C109.5H84B—C84—H84C109.5
C37—O36—C22117.4 (2)C87—O86—C72117.7 (3)
O39—C37—O36122.8 (3)O89—C87—O86122.5 (3)
O39—C37—C38126.3 (3)O89—C87—C88126.2 (4)
O36—C37—C38110.9 (3)O86—C87—C88111.2 (4)
C37—C38—H38A109.5C87—C88—H88A109.5
C37—C38—H38B109.5C87—C88—H88B109.5
H38A—C38—H38B109.5H88A—C88—H88B109.5
C37—C38—H38C109.5C87—C88—H88C109.5
H38A—C38—H38C109.5H88A—C88—H88C109.5
H38B—C38—H38C109.5H88B—C88—H88C109.5
C02B—O01—C02A—C12A48 (11)C59—O51—C52A—C61A85.3 (10)
C09—O01—C02A—C12A162.9 (3)C52B—O51—C52A—C61A114 (12)
C02B—O01—C02A—C03A169 (12)C59—O51—C52A—C62A155.7 (7)
C09—O01—C02A—C03A42.6 (5)C52B—O51—C52A—C62A127 (12)
C02B—O01—C02A—C11A70 (11)C59—O51—C52A—C53A35.6 (15)
C09—O01—C02A—C11A78.9 (4)C52B—O51—C52A—C53A7 (11)
O01—C02A—C03A—C04A59.6 (5)O51—C52A—C53A—C54A53.6 (13)
C12A—C02A—C03A—C04A175.9 (4)C61A—C52A—C53A—C54A61.1 (17)
C11A—C02A—C03A—C04A58.6 (5)C62A—C52A—C53A—C54A175.7 (9)
C02A—C03A—C04A—C1045.5 (5)C52A—C53A—C54A—C6042.3 (12)
C09—O01—C02B—C11B95.5 (14)C52A—O51—C52B—C61B120 (12)
C02A—O01—C02B—C11B62 (11)C59—O51—C52B—C61B86.5 (9)
C09—O01—C02B—C03B18 (3)C52A—O51—C52B—C53B118 (12)
C02A—O01—C02B—C03B52 (10)C59—O51—C52B—C53B34.8 (16)
C09—O01—C02B—C12B150.1 (16)C52A—O51—C52B—C62B3 (11)
C02A—O01—C02B—C12B176 (13)C59—O51—C52B—C62B156.2 (7)
O01—C02B—C03B—C04B46 (3)C61B—C52B—C53B—C54B56.8 (17)
C11B—C02B—C03B—C04B56 (3)O51—C52B—C53B—C54B56.1 (16)
C12B—C02B—C03B—C04B178 (2)C62B—C52B—C53B—C54B173.9 (11)
C02B—C03B—C04B—C1040 (3)C52B—C53B—C54B—C6041.4 (12)
C10—C05—C06—O14179.9 (2)C60—C55—C56—C576.7 (4)
C13—C05—C06—O142.2 (4)C63—C55—C56—C57171.5 (2)
C10—C05—C06—C073.9 (4)C60—C55—C56—O64178.2 (2)
C13—C05—C06—C07173.9 (2)C63—C55—C56—O643.7 (4)
C05—C06—C07—C084.5 (4)C55—C56—C57—C586.4 (4)
O14—C06—C07—C08179.3 (2)O64—C56—C57—C58178.4 (2)
C05—C06—C07—C15172.1 (2)C55—C56—C57—C65170.3 (2)
O14—C06—C07—C154.1 (3)O64—C56—C57—C654.9 (4)
C06—C07—C08—C091.2 (4)C56—C57—C58—C591.4 (4)
C15—C07—C08—C09175.5 (2)C65—C57—C58—C59175.4 (3)
C06—C07—C08—C16179.7 (2)C56—C57—C58—C66178.5 (2)
C15—C07—C08—C163.5 (4)C65—C57—C58—C661.7 (4)
C02B—O01—C09—C1016.6 (15)C52A—O51—C59—C58175.5 (9)
C02A—O01—C09—C1012.4 (4)C52B—O51—C59—C58179.4 (9)
C02B—O01—C09—C08166.3 (15)C52A—O51—C59—C604.2 (10)
C02A—O01—C09—C08170.5 (3)C52B—O51—C59—C600.3 (10)
C07—C08—C09—O01179.7 (2)C57—C58—C59—O51177.2 (3)
C16—C08—C09—O010.7 (4)C66—C58—C59—O515.7 (4)
C07—C08—C09—C102.7 (4)C57—C58—C59—C603.1 (4)
C16—C08—C09—C10176.4 (3)C66—C58—C59—C60174.0 (3)
O01—C09—C10—C05179.9 (2)O51—C59—C60—C55177.5 (3)
C08—C09—C10—C053.3 (4)C58—C59—C60—C552.8 (5)
O01—C09—C10—C04A2.4 (4)O51—C59—C60—C54A7.9 (6)
C08—C09—C10—C04A174.5 (3)C58—C59—C60—C54A172.5 (5)
O01—C09—C10—C04B20.6 (15)O51—C59—C60—C54B13.7 (6)
C08—C09—C10—C04B162.6 (15)C58—C59—C60—C54B165.9 (4)
C06—C05—C10—C090.0 (4)C56—C55—C60—C591.9 (4)
C13—C05—C10—C09177.8 (3)C63—C55—C60—C59176.2 (3)
C06—C05—C10—C04A177.8 (3)C56—C55—C60—C54A167.1 (4)
C13—C05—C10—C04A0.0 (4)C63—C55—C60—C54A14.7 (6)
C06—C05—C10—C04B158.1 (15)C56—C55—C60—C54B171.2 (4)
C13—C05—C10—C04B24.2 (15)C63—C55—C60—C54B6.9 (5)
C03A—C04A—C10—C0914.9 (5)C53A—C54A—C60—C5913.4 (8)
C03A—C04A—C10—C05162.8 (3)C53A—C54A—C60—C55155.9 (5)
C03A—C04A—C10—C04B97 (3)C53A—C54A—C60—C54B124 (2)
C03B—C04B—C10—C099 (3)C53B—C54B—C60—C598.7 (8)
C03B—C04B—C10—C05150.0 (15)C53B—C54B—C60—C55160.2 (4)
C03B—C04B—C10—C04A118 (4)C53B—C54B—C60—C54A89 (2)
C05—C06—O14—C1768.2 (3)C55—C56—O64—C6769.3 (3)
C07—C06—O14—C17115.6 (3)C57—C56—O64—C67115.3 (3)
C06—O14—C17—O23137.0 (2)C56—O64—C67—O73136.3 (2)
C06—O14—C17—C18104.8 (3)C56—O64—C67—C68105.0 (2)
O23—C17—C18—O24179.22 (19)O73—C67—C68—O74179.99 (19)
O14—C17—C18—O2459.8 (3)O64—C67—C68—O7460.5 (3)
O23—C17—C18—C1960.5 (3)O73—C67—C68—C6960.0 (3)
O14—C17—C18—C1959.0 (3)O64—C67—C68—C6959.4 (3)
O24—C18—C19—O2864.1 (3)O74—C68—C69—O7861.9 (3)
C17—C18—C19—O28175.3 (2)C67—C68—C69—O78176.5 (2)
O24—C18—C19—C20177.3 (2)O74—C68—C69—C70179.1 (2)
C17—C18—C19—C2056.7 (3)C67—C68—C69—C7057.5 (3)
O28—C19—C20—O3271.9 (2)O78—C69—C70—O8267.5 (3)
C18—C19—C20—O32169.06 (19)C68—C69—C70—O82172.2 (2)
O28—C19—C20—C21172.1 (2)O78—C69—C70—C71174.6 (2)
C18—C19—C20—C2153.1 (3)C68—C69—C70—C7154.2 (3)
O32—C20—C21—O23169.9 (2)O82—C70—C71—O73172.12 (19)
C19—C20—C21—O2353.3 (3)C69—C70—C71—O7353.4 (3)
O32—C20—C21—C2272.6 (3)O82—C70—C71—C7270.1 (3)
C19—C20—C21—C22170.8 (2)C69—C70—C71—C72171.3 (2)
O23—C21—C22—O3657.8 (3)O73—C71—C72—O8650.8 (3)
C20—C21—C22—O36177.5 (2)C70—C71—C72—O86170.7 (2)
O14—C17—O23—C2156.5 (3)O64—C67—O73—C7157.8 (3)
C18—C17—O23—C2163.5 (3)C68—C67—O73—C7161.8 (3)
C22—C21—O23—C17178.6 (2)C72—C71—O73—C67180.0 (2)
C20—C21—O23—C1760.5 (3)C70—C71—O73—C6759.1 (3)
C19—C18—O24—C25160.4 (2)C69—C68—O74—C75161.9 (2)
C17—C18—O24—C2579.4 (3)C67—C68—O74—C7577.3 (3)
C18—O24—C25—O264.1 (4)C68—O74—C75—O761.4 (4)
C18—O24—C25—C27176.4 (2)C68—O74—C75—C77179.6 (2)
C18—C19—O28—C29112.1 (3)C68—C69—O78—C79105.6 (3)
C20—C19—O28—C29128.8 (2)C70—C69—O78—C79134.9 (2)
C19—O28—C29—O300.0 (4)C69—O78—C79—O801.7 (4)
C19—O28—C29—C31178.9 (2)C69—O78—C79—C81178.5 (2)
C19—C20—O32—C33103.3 (3)C69—C70—O82—C8399.7 (3)
C21—C20—O32—C33138.0 (2)C71—C70—O82—C83140.7 (2)
C20—O32—C33—O356.1 (4)C70—O82—C83—O857.9 (4)
C20—O32—C33—C34174.2 (3)C70—O82—C83—C84172.3 (2)
C21—C22—O36—C3779.0 (3)C71—C72—O86—C8778.2 (3)
C22—O36—C37—O392.3 (4)C72—O86—C87—O894.3 (4)
C22—O36—C37—C38176.6 (2)C72—O86—C87—C88174.4 (3)

Experimental details

Crystal data
Chemical formulaC28H38O11
Mr550.58
Crystal system, space groupTriclinic, P1
Temperature (K)100
a, b, c (Å)8.66 (1), 11.30 (1), 14.55 (1)
α, β, γ (°)85.74 (5), 89.13 (5), 88.16 (5)
V3)1419 (2)
Z2
Radiation typeSynchrotron, λ = 0.59040 Å
µ (mm1)0.06
Crystal size (mm)0.25 × 0.15 × 0.09
Data collection
DiffractometerMar Research MAR315 CCD
diffractometer
Absorption correctionMulti-scan
(SCALEPACK; Otwinowski et al., 2003)
Tmin, Tmax0.985, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
8538, 5956, 5260
Rint0.023
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.118, 0.99
No. of reflections5956
No. of parameters795
No. of restraints752
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.21, 0.23

Computer programs: NECAT APS beamline software, HKL-2000 (Otwinowski & Minor, 1997), SHELXD (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and pyMOL (DeLano, 2002).

 

Acknowledgements

This work was in part supported by the Intra­mural Research Program of the NIH, National Cancer Institute, Center for Cancer Research. X-ray data were collected at the NECAT 24ID-C beamline of the Advanced Photon Source, Argonne National Laboratory. Use of the APS was supported by the US Department of Energy under contract No. W-31–109-Eng-38.

References

First citationAzzi, A. & Stoker, A. (2000). Progr. Lipid Res. 39, 231–255.  Web of Science CrossRef CAS Google Scholar
First citationDeLano, W. L. (2002). The pyMOL Molecular Graphics System. DeLano Scientific, San Carlos, CA, USA.  Google Scholar
First citationDubbs, M. D. & Gupta, R. B. (1998). J. Chem. Eng. Data, 43, 590–591.  Web of Science CrossRef CAS Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationOtwinowski, Z., Borek, D., Majewski, W. & Minor, W. (2003). Acta Cryst. A59, 228–234.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationOtwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTraber, M. G. & Atkinson, J. (2007). Free Rad. Biol. Med. 43, 4–15.  Web of Science CrossRef PubMed CAS Google Scholar
First citationWitkowski, S. & Walejko, P. (2002). Z. Naturforsch. Teil B, 57, 571–578.  CAS Google Scholar

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