4-(4-Nitro­benz­yl)pyridinium 3-carb­oxy-4-hy­droxy­benzene­sulfonate

Smith, G.; Wermuth, U.D.

doi:10.1107/S1600536813000093

Volume 69
Part 2
Page o206
February 2013

Received 20 December 2012
Accepted 2 January 2013
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.006 Å
R = 0.071
wR = 0.173
Data-to-parameter ratio = 13.5
Details

4-(4-Nitrobenzyl)pyridinium 3-carboxy-4-hydroxybenzenesulfonate

Graham Smith ^a ^* and Urs D. Wermuth ^a

^aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
Correspondence e-mail: g.smith@qut.edu.au

In the title salt, C₁₂H₁₁N₂O₂⁺·C₇H₅O₆S^-, the dihedral angle between the benzene and pyridine rings in the 4-(4-nitrobenzyl)pyridinium cation is 82.7 (2)°. Within the anion there is an intramolecular hydroxy-O-HO(carboxylic acid) bond. In the crystal, the cation forms a single N⁺-HO_sulfonate hydrogen bond with the anion. These cation-anion pairs interact through duplex anion carboxylic acid O-HO_sulfonate hydrogen bonds, giving a centrosymmetric cyclic association [graph set R₂²(16)]. The crystals studied were non-merohedrally twinned.

Related literature

For data on 4-(4-nitrobenzyl)pyridine adduct and salt structures, see: Smith et al. (1997); Smith & Wermuth (2010). For examples of the structures of salts of 5-sulfosalicylic acid, see: Raj et al. (2003); Smith et al. (2004). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990).

Experimental

Crystal data

C₁₂H₁₁N₂O₂⁺·C₇H₅O₆S^-
M_r = 432.41
Monoclinic, P 2₁ /c
a = 7.4154 (7) Å
b = 12.8896 (10) Å
c = 19.649 (2) Å
= 92.848 (9)°
V = 1875.8 (3) Å³
Z = 4
Mo K radiation
= 0.23 mm^-1
T = 200 K
0.25 × 0.20 × 0.15 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.916, T_max = 0.980
14534 measured reflections
3671 independent reflections
2631 reflections with I > 2(I)
R_int = 0.049

Refinement

R[F² > 2(F²)] = 0.071
wR(F²) = 0.173
S = 1.21
3671 reflections
272 parameters
H-atom parameters constrained
_max = 0.39 e Å^-3
_min = -0.54 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O51A	0.86	1.88	2.732 (5)	172
O2A-H2AO12A	0.95	1.70	2.613 (5)	159
O11A-H11AO53Aⁱ	0.94	1.65	2.583 (4)	172
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 2012); 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: BH2470 ).

Acknowledgements

The authors acknowledge financial support from the Australian Research Council, the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Raj, S. B., Sethuraman, V., Francis, S., Hemamalini, M., Muthiah, P. T., Bocelli, G., Cantoni, A., Rychlewska, U. & Warzajtis, B. (2003). CrysEngComm, 5, 70-76.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1997). J. Chem. Crystallogr. 27, 307-317.
Smith, G. & Wermuth, U. D. (2010). Acta Cryst. E66, o1173.
Smith, G., Wermuth, U. D. & White, J. M. (2004). Acta Cryst. C60, o575-o581.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds