Dipyridinium 2,2′-dithio­dinicotinate

Yehye, W.A.; Ariffin, A.; Rahman, N.A.; Ng, S.W.

doi:10.1107/S1600536809013543

Volume 65
Part 5
Page o1068
May 2009

Received 7 April 2009
Accepted 10 April 2009
Online 18 April 2009

Key indicators
Single-crystal X-ray study
T = 123 K
Mean (C-C) = 0.009 Å
R = 0.092
wR = 0.269
Data-to-parameter ratio = 12.7
Details

Dipyridinium 2,2'-dithiodinicotinate

Wagee A. Yehye,^a Azhar Ariffin,^a Noorsaadah Abdul Rahman ^a and Seik Weng Ng ^a ^*

^aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The dianion of the title salt, 2C₅H₆N⁺·C₁₂H₆N₂O₄S₂^2-, lies on a special position of 2 site symmetry that relates one thionicotinate part to the other, and the dihedral angle between the niotinate planes is 89.2 (2)°. The pyridinium cations are hydrogen bonded to the carboxylate group by way of N-HO links.

Related literature

The structure is a non-merohedral twin; for the program to model twinned crystal structures, see: Spek (2003). For 1,1'-dithio-2,2'-dinicotinic acid, see: Zhu et al. (2002). For the methyl, ethyl and n-butyl esters, see: Cindric et al. (2001); Toma et al. (2004).

Experimental

Crystal data

2C₅H₆N⁺·C₁₂H₆N₂O₄S₂^2-
M_r = 466.52
Monoclinic, C 2/c
a = 7.9621 (3) Å
b = 12.3354 (4) Å
c = 21.5057 (8) Å
= 95.917 (2)°
V = 2100.9 (1) Å³
Z = 4
Mo K radiation
= 0.29 mm^-1
T = 123 K
0.28 × 0.16 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.923, T_max = 0.977
6726 measured reflections
1855 independent reflections
1496 reflections with I > 2(I)
R_int = 0.101

Refinement

R[F² > 2(F²)] = 0.092
wR(F²) = 0.269
S = 1.59
1855 reflections
146 parameters
H-atom parameters constrained
_max = 0.47 e Å^-3
_min = -0.57 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O2	0.88	1.71	2.586 (7)	174

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: SI2170 ).

Acknowledgements

We thank 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.
Cindric, M., Strukan, N., Kaifez, T., Giester, G. & Kamenar, B. (2001). Z. Anorg. Allg. Chem. 627, 2604-2608.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Toma, M., Sanchez, A., Castellano, E. E. & Ellena, J. (2004). Rev. Chim. (Bucharest), 55, 719-723.
Westrip, S. P. (2009). publCIF. In preparation.
Zhu, J.-X., Zhao, Y.-J., Hong, M.-C., Sun, D.-F., Shi, Q. & Cao, R. (2002). Chem. Lett. pp. 484-485.

organic compounds