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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 [sigma](C-C) = 0.006 Å
R = 0.071
wR = 0.173
Data-to-parameter ratio = 13.5
Details
Open access

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

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-H...O(carboxylic acid) bond. In the crystal, the cation forms a single N+-H...Osulfonate hydrogen bond with the anion. These cation-anion pairs interact through duplex anion carboxylic acid O-H...Osulfonate 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, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1997). J. Chem. Crystallogr. 27, 307-317.]); Smith & Wermuth (2010[Smith, G. & Wermuth, U. D. (2010). Acta Cryst. E66, o1173.]). For examples of the structures of salts of 5-sulfosalicylic acid, see: Raj et al. (2003[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.]); Smith et al. (2004[Smith, G., Wermuth, U. D. & White, J. M. (2004). Acta Cryst. C60, o575-o581.]). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11N2O2+·C7H5O6S-

  • Mr = 432.41

  • Monoclinic, P 21 /c

  • a = 7.4154 (7) Å

  • b = 12.8896 (10) Å

  • c = 19.649 (2) Å

  • [beta] = 92.848 (9)°

  • V = 1875.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]) Tmin = 0.916, Tmax = 0.980

  • 14534 measured reflections

  • 3671 independent reflections

  • 2631 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.071

  • wR(F2) = 0.173

  • S = 1.21

  • 3671 reflections

  • 272 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O51A 0.86 1.88 2.732 (5) 172
O2A-H2A...O12A 0.95 1.70 2.613 (5) 159
O11A-H11A...O53Ai 0.94 1.65 2.583 (4) 172
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) within WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [CrossRef] [ISI] [details]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
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.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1997). J. Chem. Crystallogr. 27, 307-317.  [CrossRef] [ChemPort] [ISI]
Smith, G. & Wermuth, U. D. (2010). Acta Cryst. E66, o1173.  [CSD] [CrossRef] [details]
Smith, G., Wermuth, U. D. & White, J. M. (2004). Acta Cryst. C60, o575-o581.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o206  [ doi:10.1107/S1600536813000093 ]

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