2,2′-[2,3,5,6-Tetra­methyl-p-phenyl­ene­bis(methyl­enethio)]bis­(pyridine N-oxide)

Ravindran Durai Nayagam, B.; Jebas, S.R.; Grace, S.; Schollmeyer, D.

doi:10.1107/S1600536807068766

Volume 64
Part 2
Page o409
February 2008

Received 15 December 2007
Accepted 29 December 2007
Online 9 January 2008

Key indicators
Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.006 Å
R = 0.057
wR = 0.170
Data-to-parameter ratio = 14.1
Details

2,2'-[2,3,5,6-Tetramethyl-p-phenylenebis(methylenethio)]bis(pyridine N-oxide)

B. Ravindran Durai Nayagam,^a ^* Samuel Robinson Jebas,^b Selvarathi Grace ^a and Dieter Schollmeyer ^c

^aDepartment of Chemistry, Popes College, Sawyerpuram, Tamilnadu, India,^bDepartment of Physics, Karunya University, Coimbatore 641114, India, and ^cInstitut für Organische Chemie, Universität Mainz, Duesbergweg 10-14, 55099 Mainz, Germany
Correspondence e-mail: b_ravidurai@yahoo.com

Molecules of the title compound, C₂₂H₂₄N₂O₂S₂, lie across centres of inversion. The two thiopyridine N-oxide groups adopt a stepped trans configuration with respect to the benzene ring, by virtue of the symmetry. The oxopyridinium ring forms a dihedral angle of 79.9 (2)° with the benzene ring. The crystal structure is stabilized by a strong [pi] - [pi] interaction between the pyridinium rings of adjacent molecules [ring centroid-centroid distance = 3.464 (3) Å].

Related literature

For bond-length data, see: Allen et al. (1987). For biological activities of N-oxide derivatives, see: Bovin et al. (1992); Katsuyuki et al. (1991); Leonard et al. (1955); Lobana & Bhatia (1989); Symons & West (1985). For a related structure, see: Hartung et al. (1996).

Experimental

Crystal data

C₂₂H₂₄N₂O₂S₂
M_r = 412.55
Monoclinic, P 2₁ /c
a = 11.8431 (13) Å
b = 9.0108 (9) Å
c = 9.7551 (10) Å
= 112.611 (9)°
V = 961.01 (17) Å³
Z = 2
Cu K radiation
= 2.68 mm^-1
T = 193 (2) K
0.10 × 0.10 × 0.05 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.80, T_max = 0.87
1929 measured reflections
1813 independent reflections
1200 reflections with I > 2(I)
R_int = 0.077
3 standard reflections frequency: 60 min intensity decay: 3%

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.170
S = 0.99
1813 reflections
129 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.41 e Å^-3

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2548 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bovin, D. H. R., Crepon, E. & Zard, S. Z. (1992). Bull. Soc. Chim. Fr. 129, 145-150.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Hartung, J., Svoboda, I. & Fuess, H. (1996). Acta Cryst. C52, 2841-2844.
Katsuyuki, N., Carter, B. J., Xu, J. & Hetch, S. M. (1991). J. Am. Chem. Soc. 113, 5099-5100.
Leonard, F., Barklay, F. A., Brown, E. V., Anderson, F. E. & Green, D. M. (1955). Antibiot. Chemother. pp. 261-264.
Lobana, T. S. & Bhatia, P. K. (1989). J. Sci. Ind. Res. 48, 394-401.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Symons, M. C. R. & West, D.-X. (1985). J. Chem. Soc. Daltan Trans., pp. 379-381.

organic compounds