electronic reprintActa Crystallographica Section E

Structure ReportsOnline

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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

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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

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