Bis[2-(2,4-dinitro­benz­yl)pyridinium] biphenyl-4,4′-disulfonate trihydrate

Smith, G.; Wermuth, U.D.; Young, D.J.

doi:10.1107/S1600536810014819

Volume 66
Part 5
Pages o1184-o1185
May 2010

Received 22 April 2010
Accepted 22 April 2010
Online 28 April 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
Disorder in solvent or counterion
R = 0.042
wR = 0.104
Data-to-parameter ratio = 13.0
Details

Bis[2-(2,4-dinitrobenzyl)pyridinium] biphenyl-4,4'-disulfonate trihydrate

Graham Smith,^a ^* Urs D. Wermuth ^a and David J. Young ^b

^aFaculty of Science and Technology, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia, and ^bSchool of Biomolecular and Physical Sciences, Griffith University, Nathan, Queensland 4111, Australia
Correspondence e-mail: g.smith@qut.edu.au

In the structure of the title salt, 2C₁₂H₁₀N₃O₄⁺·C₁₂H₈O₆S₂^2-·3H₂O, determined at 173 K, the biphenyl-4,4'-disulfonate dianions lie across crystallographic inversion centres with the sulfonate groups interacting head-to-head through centrosymmetric cyclic bis(water)-bridged hydrogen-bonding associations [graph set R₄⁴(11)], forming chains. The 2-(2,4-dinitrobenzyl)pyridinium cations are linked to these chains through pyridinium-water N-HO hydrogen bonds and a two-dimensional network is formed through water bridges between sulfonate and 2-nitro O atoms, while the structure also has weak cation-anion [pi] - [pi] aromatic ring interactions [minimum ring centroid separation = 3.8441 (13) Å].

Related literature

For structural data on 2-(2,4-dinitrobenzyl)pyridine and related compounds, see Seff & Trueblood (1968); Scherl et al. (1996); Naumov et al. (2002, 2005). For bipyridine-4,4'-disulfonate compounds, see: Swift et al. (1998); Swift & Ward (1998); Holman & Ward (2000); Liao et al. (2001). For graph-set notation, see: Etter et al. (1990).

Experimental

Crystal data

2C₁₂H₁₀N₃O₄⁺·C₁₂H₈O₆S₂^2-·3H₂O
M_r = 886.83
Triclinic, $[P \overline 1]$
a = 8.3897 (3) Å
b = 10.6455 (4) Å
c = 11.7405 (5) Å
= 97.879 (3)°
= 96.926 (3)°
= 112.066 (4)°
V = 945.53 (7) Å³
Z = 1
Mo K radiation
= 0.23 mm^-1
T = 173 K
0.30 × 0.25 × 0.15 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.98, T_max = 0.99
8964 measured reflections
3844 independent reflections
3441 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.104
S = 1.03
3844 reflections
296 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.35 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1W	0.95 (3)	1.71 (3)	2.655 (3)	175 (3)
O1W-H11WO43Aⁱ	0.88 (4)	1.84 (4)	2.716 (2)	175 (3)
O1W-H12WO41A	0.80 (3)	2.01 (3)	2.806 (2)	172 (3)
O2W-H21WO43A	0.82 (4)	1.99 (4)	2.761 (4)	155 (4)
O2W-H22WO21ⁱⁱ	0.87 (3)	2.32 (3)	2.867 (2)	124 (3)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y+1, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2763 ).

Acknowledgements

The authors acknowledge financial support from the Australian Research Council, the Faculty of Science and Technology, Queensland University of Technology, and the School of Biomolecular and Physical Sciences, Griffith University.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Holman, K. T. & Ward, M. D. (2000). Angew Chem. Int. Ed. 39, 1653-1655.
Liao, C.-Z., Feng, X.-L., Yao, J.-H. & Cai, J.-W. (2001). Acta Cryst. C57, 1215-1216.
Naumov, P., Sakurai, K., Ishikawa, T., Takahashi, J., Koshihawa, S. & Ohashi, Y. (2005). J. Phys. Chem. A, 109, 7264-7275.
Naumov, P., Sekine, A., Uekusa, H. & Ohashi, Y. (2002). J. Am. Chem. Soc. 124, 8540-8541.
Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Scherl, M., Haarer, D., Fischer, J., DeCian, A., Lehn, J.-M. & Eichen, Y. (1996). J. Phys. Chem. 100, 16175-16186.
Seff, K. & Trueblood, K. N. (1968). Acta Cryst. B24, 1406-1415.
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.
Swift, J. A., Reynolds, A. M. & Ward, M. D. (1998). Chem. Mater. 10, 4159-4168.
Swift, J. A. & Ward, M. D. (1998). Chem. Mater. 10, 1501-1504.

organic compounds