2,3,4,6-Tetra-O-acetyl-β-d-galacto­pyranosyl 2-(2,4-dichloro­anilino)-4,4-dimethyl-6-oxocyclo­hex-1-enecarbo­dithio­ate

El Ashry, E.S.H.; Amer, M.R.; Shah, M.R.; Ng, S.W.

doi:10.1107/S1600536809014743

Volume 65
Part 5
Page o1106
May 2009

Received 17 April 2009
Accepted 21 April 2009
Online 25 April 2009

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.011 Å
R = 0.092
wR = 0.263
Data-to-parameter ratio = 18.1
Details

2,3,4,6-Tetra-O-acetyl--D-galactopyranosyl 2-(2,4-dichloroanilino)-4,4-dimethyl-6-oxocyclohex-1-enecarbodithioate

El Sayed H. El Ashry,^a Mohammed R. Amer,^a M. Raza Shah ^a and Seik Weng Ng ^b ^*

^aHEJ Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The cyclohexene ring in the title compound, C₂₉H₃₃Cl₂NO₁₀S₂, adopts an envelope conformation, with the C atom bearing the two methyl groups representing the flap. This atom deviates by 0.63 (1) Å from the plane through the other five ring atoms (r.m.s. deviation = 0.11 Å). The molecular conformation is stabilized by an intramolecular N-HS hydrogen bond. The crystal studied was a non-merohedral twin, with a minor twin component of 29%.

Related literature

For background to thioglycosides, see: El Ashry et al. (2006, 2008), Haikel et al. (2003). For the deconvolution of non-merohedrally twinned diffraction data, see: Spek (2009).

Experimental

Crystal data

C₂₉H₃₃Cl₂NO₁₀S₂
M_r = 690.58
Monoclinic, P 2₁
a = 13.8257 (4) Å
b = 8.7697 (3) Å
c = 14.0690 (4) Å
= 106.486 (2)°
V = 1635.70 (9) Å³
Z = 2
Mo K radiation
= 0.38 mm^-1
T = 100 K
0.35 × 0.15 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.852, T_max = 0.992
15059 measured reflections
7402 independent reflections
5732 reflections with I > 2(I)
R_int = 0.065

Refinement

R[F² > 2(F²)] = 0.092
wR(F²) = 0.263
S = 1.09
7402 reflections
408 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 1.06 e Å^-3
_min = -0.99 e Å^-3
Absolute structure: Flack (1983), 3420 Friedel pairs
Flack parameter: 0.1 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1S2	0.88 (1)	2.07 (5)	2.882 (6)	152 (9)

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2430 ).

Acknowledgements

We thank the Higher Education Commission of Pakistan and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
El Ashry, E. S. H., Awad, L. F. & Atta, A. I. (2006). Tetrahedron, 62, 2943-2998.
El Ashry, E. S. H., Rashed, N., Awad, L. F., Ramadan, E. S., Abdel-Maggeed, S. M. & Rezki, N. (2008). J. Carbohydr. Chem. 27, 70-85.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Haikel, A. Z., El Ashry, E. S. H. & Banoub, J. (2003). Carbohydr. Res. 338, 2291-2299.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2009). publCIF. In preparation.

organic compounds