p-Tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzyl­idene-1-thio-α-l-idopyran­oside

Gainsford, G.J.; Tyler, P.C.; Zubkova, O.V.

doi:10.1107/S1600536810020970

Volume 66
Part 7
Pages o1598-o1599
July 2010

Received 25 May 2010
Accepted 1 June 2010
Online 9 June 2010

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.009 Å
Disorder in main residue
R = 0.068
wR = 0.201
Data-to-parameter ratio = 14.2
Details

p-Tolyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-1-thio--L-idopyranoside

Graeme J. Gainsford,^a ^* Peter C. Tyler ^a and Olga V. Zubkova ^a

^aCarbohydrate Chemistry Team, Industrial Research Limited, PO Box 31-310, Lower Hutt, New Zealand 5040
Correspondence e-mail: g.gainsford@irl.cri.nz

The title compound, C₃₄H₃₂O₆S, is an ido-configured thioglycoside building block for heparan sulfate fragments. It contains disordered tolyl and O-benzyl groups with occupancy ratios of 0.539 (13):0.461 (13) and 0.613 (13):0.387 (13), respectively, as determined from a weakly diffracting crystal. The fused rings adopt chair conformations with the molecules packing into a three-dimensional network via C-HO and three C-H [pi] interactions. The former interactions, occuring between molecules related by a twofold axis, define an R₂²(26) motif.

Related literature

For the synthesis, see: Barroca & Jacquinet (2000); Polat & Wong (2007). For a related structure, see: Zhou et al. (2006). For ring conformations, see: Cremer & Pople (1975) and for hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₃₄H₃₂O₆S
M_r = 568.66
Monoclinic, C 2
a = 19.296 (4) Å
b = 8.2060 (16) Å
c = 19.045 (4) Å
= 101.27 (3)°
V = 2957.5 (10) Å³
Z = 4
Cu K radiation
= 1.34 mm^-1
T = 123 K
0.60 × 0.11 × 0.11 mm

Data collection

Rigaku Spider diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.754, T_max = 1.0
10947 measured reflections
4882 independent reflections
2352 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.068
wR(F²) = 0.201
S = 1.03
4882 reflections
343 parameters
1 restraint
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.31 e Å^-3
Absolute structure: Flack (1983), 1939 Friedel pairs
Flack parameter: 0.01 (4)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C2,C9-C13, C14A-C19A and C22-C27 phenyl rings, respectively.

D-HA	D-H	HA	DA	D-HA
C11-H11O4ⁱ	0.95	2.50	3.359 (8)	150
C1-H1O2ⁱⁱ	1.00	2.62	3.592 (7)	164
C3-H3ACg1ⁱⁱ	0.99	2.60	3.506 (7)	152
C28A-H28BCg3ⁱⁱⁱ	0.99	2.60	3.572 (11)	165
C31A-H31ACg2ⁱⁱⁱ	0.95	2.87	3.526 (13)	127
C31B-H31BCg2ⁱⁱⁱ	0.93	2.81	3.68 (2)	157
Symmetry codes: (i) -x+1, y, -z; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z]$ ; (iii) x, y-1, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: FSProcess (Rigaku, 1998); data reduction: FSProcess; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP in WinGX (Farrugia, 1999) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2277 ).

Acknowledgements

We thank the MacDiarmid Institute for Advanced Materials and Nanotechnology for funding of the diffractometer equipment and Dr Shane Telfer (Massey University, Palmerston North) for his assistance. This work was supported by the New Zealand Foundation for Research, Science & Technology, project C08X0601, `New Synthesis Methods'.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Barroca, N. & Jacquinet, J.-C. (2000). Carbohydr. Res. 329, 667-679.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.
Polat, T. & Wong, C.-H. (2007). J. Am. Chem. Soc. 129, 12795-12800.
Rigaku (1998). FSProcess. Rigaku Corporation, Tokyo, Japan.
Rigaku (2005). CrystalClear. Rigaku Americas Corporation, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Zhou, F.-Y., Zhou, F.-Y. & Zhong, J.-H. (2006). Acta Cryst. E62, o266-o267.

organic compounds