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Structure ReportsOnline
ISSN 1600-5368
Editors: W.T.A. Harrison, J. Simpson and M.Weil
2,2,5,7,8-Pentamethylchroman-6-yl2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside from synchrotrondata
Krzysztof Brzezinski, Piotr Wałejko, Aneta Baj, Stanisław Witkowski andZbigniew Dauter
Acta Cryst. (2011). E67, o718
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Inorganic compounds
Metal-organic compounds
Organic compounds
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Acta Cryst. (2011). E67, o718 Brzezinski et al. · C28H38O11
2,2,5,7,8-Pentamethylchroman-6-yl2,3,4,6-tetra-O-acetyl-a-D-glucopyran-oside from synchrotron data
Krzysztof Brzezinski,a* Piotr Wałejko,b Aneta Baj,b
Stanisław Witkowskib and Zbigniew Dautera
aSynchrotron Radiation Research Section, MCL, National Cancer Institute, Argonne
National Laboratory, Biosciences Division, Bldg 202, Argonne, IL 60439, USA, andbInstitute 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
Key indicators: single-crystal synchrotron study; T = 100 K; mean �(C–C) = 0.004 A;
disorder in main residue; R factor = 0.045; wR factor = 0.118; data-to-parameter
ratio = 7.5.
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 conforma-
tions. 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 �-tocopherol [systematic
name 2,7,8-trimethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-
chromen-6-ol] and its derivatives and their applications, see:
Dubbs & Gupta (1998); Azzi & Stoker (2000); Traber &
Atkinson (2007). For the preparation, see: Witkowski &
Walejko (2002).
Experimental
Crystal data
C28H38O11
Mr = 550.58Triclinic, P1a = 8.66 (1) Ab = 11.30 (1) Ac = 14.55 (1) A� = 85.74 (5)�
� = 89.13 (5)�
� = 88.16 (5)�
V = 1419 (2) A3
Z = 2Synchrotron radiation� = 0.59040 A� = 0.06 mm�1
T = 100 K0.25 � 0.15 � 0.09 mm
Data collection
Mar Research MAR315 CCDdiffractometer
Absorption correction: multi-scan(SCALEPACK; Otwinowski &Minor, 2003)Tmin = 0.985, Tmax = 0.995
8538 measured reflections5956 independent reflections5260 reflections with I > 2�(I)Rint = 0.023
Refinement
R[F 2 > 2�(F 2)] = 0.045wR(F 2) = 0.118S = 0.995956 reflections795 parameters
752 restraintsH-atom parameters constrained��max = 0.21 e A�3
��min = �0.23 e A�3
Data collection: NECAT APS beamline software (unpublished);
cell refinement: HKL-2000 (Otwinowski & Minor, 1997); data
reduction: HKL-2000; 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.
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.
Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: GK2341).
References
Azzi, A. & Stoker, A. (2000). Progr. Lipid Res. 39, 231–255.DeLano, W. L. (2002). The pyMOL Molecular Graphics System. DeLano
Scientific, San Carlos, CA, USA.Dubbs, M. D. & Gupta, R. B. (1998). J. Chem. Eng. Data, 43, 590–591.Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.Otwinowski, Z., Borek, D., Majewski, W. & Minor, W. (2003). Acta Cryst. A59,
228–234.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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Traber, M. G. & Atkinson, J. (2007). Free Rad. Biol. Med. 43, 4–15.Witkowski, S. & Walejko, P. (2002). Z. Naturforsch. Teil B, 57, 571–578.
organic compounds
o718 Brzezinski et al. doi:10.1107/S160053681100626X Acta Cryst. (2011). E67, o718
Acta Crystallographica Section E
Structure ReportsOnline
ISSN 1600-5368
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