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Volume 68 
Part 3 
Page o758  
March 2012  

Received 12 February 2012
Accepted 12 February 2012
Online 17 February 2012

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Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.007 Å
R = 0.082
wR = 0.147
Data-to-parameter ratio = 17.2
Details
Open access

6-Methoxy-2-phenyl-4,4a,6,7,8,8a-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diyl bis(4-methylbenzene-1-sulfonate)

James L. Wardella+ and Edward R. T. Tiekinkb*

aCentro de Desenvolvimento Tecnológico em Saúde (CDTS), Fundação Oswaldo Cruz (FIOCRUZ), Casa Amarela, Campus de Manguinhos, Avenida Brasil 4365, 21040-900, Rio de Janeiro, RJ, Brazil, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

In the title [alpha]-D-glucopyranoside derivative, C28H30O10S2, each heterocyclic ring adopts a chair conformation. In the trisubstituted ring, the methoxy and one sulfonate group occupy axial positions, whereas the second sulfonate group occupies an axial position. The phenyl group on the other ring is in an equatorial position. In the crystal, supramolecular chains propagating along [100] are formed through C-H...O and C-H...[pi] interactions.

Related literature

For the synthesis of the title compound, see: Brown et al. (1995[Brown, M. A., Cox, P. J., Howie, R. A., Melvin, O. A., Taylor, O. J. & Wardell, J. L. (1995). J. Organomet. Chem. 498, 275-282.]); Whistler (1962[Whistler, R. (1962). Methods in Carbohydrate Chemistry, Vol. 1, pp. 308-351. New York: Academic Press.]). For the 13C NMR spectrum, see: Sugiyama et al. (1978[Sugiyama, H., Yamasaki, T., Senda, Y., Ishiyama, J., Matsuda, K. & Seto, S. (1978). Bull. Chem. Soc. Jpn, 51, 3659-3660.]).

[Scheme 1]

Experimental

Crystal data

  • C28H30O10S2

  • Mr = 590.64

  • Orthorhombic, P 21 21 21

  • a = 5.7031 (16) Å

  • b = 17.020 (5) Å

  • c = 28.084 (8) Å

  • V = 2726.0 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 100 K

  • 0.20 × 0.01 × 0.01 mm
Data collection

  • Rigaku Saturn724+ diffractometer

  • Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011[Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.747, Tmax = 1.000

  • 25991 measured reflections

  • 6262 independent reflections

  • 5326 reflections with I > 2[sigma](I)

  • Rint = 0.103
Refinement

  • R[F2 > 2[sigma](F2)] = 0.082

  • wR(F2) = 0.147

  • S = 1.18

  • 6262 reflections

  • 364 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 2656 Friedel pairs

  • Flack parameter: 0.21 (11)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C23-C28 phenyl ring.
D-H...A D-H H...A D...A D-H...A
C2-H2...O7i 1.00 2.59 3.548 (5) 162
C8-H8B...O1i 0.98 2.50 3.325 (6) 142
C10-H10...O7i 0.95 2.47 3.023 (6) 117
C20-H20...Cg1i 0.95 2.79 3.479 (5) 130
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear-SM Expert (Rigaku, 2011[Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6633 ).

Acknowledgements

The use of the EPSRC X-ray crystallographic service at the University of Southampton, England, and the valuable assistance of the staff there are gratefully acknowledged. JLW acknowledges support from CAPES (Brazil). We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research Scheme (grant No. UM.C/HIR/MOHE/SC/12).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Brown, M. A., Cox, P. J., Howie, R. A., Melvin, O. A., Taylor, O. J. & Wardell, J. L. (1995). J. Organomet. Chem. 498, 275-282.  [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Rigaku (2011). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sugiyama, H., Yamasaki, T., Senda, Y., Ishiyama, J., Matsuda, K. & Seto, S. (1978). Bull. Chem. Soc. Jpn, 51, 3659-3660.  [CrossRef] [ChemPort] [ISI]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Whistler, R. (1962). Methods in Carbohydrate Chemistry, Vol. 1, pp. 308-351. New York: Academic Press.

Acta Cryst (2012). E68, o758  [ doi:10.1107/S1600536812006186 ]

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