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Smith, Graham, Wermuth, Urs, & Young, David(2010)Bis[2-(2,4-dinitrobenzyl)pyridinium] biphenyl-4,4’-disulfonate trihydrate.Acta Crystallographica Section E: Crystallographic Communications,66(5), o1184-o1185.

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Smith, Graham and Wermuth, Urs D. and Young, David J. (2010) Bis[2-(2,4-dinitrobenzyl)pyridinium] biphenyl-4,4'-disulfonate. Acta Crystallographica E : Structure Reports Online, 66. o1184-o1185.

Copyright 2010 International Union of Crystallography

electronic reprintActa Crystallographica Section E

Structure ReportsOnline

ISSN 1600-5368

Editors: W.T.A. Harrison, J. Simpson andM. Weil

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

Graham Smith, Urs D. Wermuth and David J. Young

Acta Cryst. (2010). E66, o1184–o1185

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Acta Cryst. (2010). E66, o1184–o1185 Smith et al. · 2C12H10N3O4+·C12H8O6S2

2−·3H2O

Bis[2-(2,4-dinitrobenzyl)pyridinium]biphenyl-4,4000-disulfonate trihydrate

Graham Smith,a* Urs D. Wermutha and David J. Youngb

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

Received 22 April 2010; accepted 22 April 2010

Key indicators: single-crystal X-ray study; T = 173 K; mean �(C–C) = 0.003 A;

disorder in solvent or counterion; R factor = 0.042; wR factor = 0.104; data-to-

parameter ratio = 13.0.

In the structure of the title salt, 2C12H10N3O4+�C12H8O6S2

2��-3H2O, determined at 173 K, the biphenyl-4,40-disulfonatedianions lie across crystallographic inversion centres with

the sulfonate groups interacting head-to-head through centro-

symmetric cyclic bis(water)-bridged hydrogen-bonding asso-

ciations [graph set R44(11)], forming chains. The 2-(2,4-

dinitrobenzyl)pyridinium cations are linked to these chains

through pyridinium–water N—H� � �O 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 �–� aromatic ring interactions

[minimum ring centroid separation = 3.8441 (13) A].

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-4,40-disul-fonate 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��3H2OMr = 886.83Triclinic, P1a = 8.3897 (3) Ab = 10.6455 (4) Ac = 11.7405 (5) A� = 97.879 (3)�

� = 96.926 (3)�

� = 112.066 (4)�

V = 945.53 (7) A3

Z = 1Mo K� radiation� = 0.23 mm�1

T = 173 K0.30 � 0.25 � 0.15 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer

Absorption correction: multi-scan(SADABS; Sheldrick, 1996)Tmin = 0.98, Tmax = 0.99

8964 measured reflections3844 independent reflections3441 reflections with I > 2�(I)Rint = 0.020

Refinement

R[F 2 > 2�(F 2)] = 0.042wR(F 2) = 0.104S = 1.033844 reflections296 parameters

H atoms treated by a mixture ofindependent and constrainedrefinement

��max = 0.35 e A�3

��min = �0.30 e A�3

Table 1Hydrogen-bond geometry (A, �).

D—H� � �A D—H H� � �A D� � �A D—H� � �A

N1—H1� � �O1W 0.95 (3) 1.71 (3) 2.655 (3) 175 (3)O1W—H11W� � �O43Ai 0.88 (4) 1.84 (4) 2.716 (2) 175 (3)O1W—H12W� � �O41A 0.80 (3) 2.01 (3) 2.806 (2) 172 (3)O2W—H21W� � �O43A 0.82 (4) 1.99 (4) 2.761 (4) 155 (4)O2W—H22W� � �O21ii 0.87 (3) 2.32 (3) 2.867 (2) 124 (3)

Symmetry codes: (i) �xþ 1;�yþ 1;�zþ 2; (ii) x; yþ 1; z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell

refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduc-

tion: 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.

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.

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

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. (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.

organic compounds

o1184 Smith et al. doi:10.1107/S1600536810014819 Acta Cryst. (2010). E66, o1184–o1185

Acta Crystallographica Section E

Structure ReportsOnline

ISSN 1600-5368

electronic reprint

Naumov, P., Sekine, A., Uekusa, H. & Ohashi, Y. (2002). J. Am. Chem. Soc.124, 8540–8541.

Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. OxfordDiffraction 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 Gottingen, 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

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