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Volume 70 
Part 1 
Page o37  
January 2014  

Received 5 December 2013
Accepted 5 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 200 K
Mean [sigma](C-C) = 0.005 Å
R = 0.061
wR = 0.161
Data-to-parameter ratio = 14.4
Details
Open access

4-(4-Amino­phenyl­sulfon­yl)anilinium toluene-4-sulfonate

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 p-toluene­sulfonate salt of the drug dapsone, C12H13N2O2S+·C7H7O3S-, the dihedral angle between the two aromatic rings of the dapsone monocation is 70.19 (17)° and those between these rings and that of the p-toluene­sulfonate anion are 72.34 (17) and 46.43 (17)°. All amine and aminium H atoms are involved in inter­molecular N-H...O hydrogen-bonding associations with sulfonyl O-atom acceptors as well as one of the sulfone O atoms, giving a three-dimensional structure.

Related literature

For drug applications of dapsone, see: Wilson et al. (1991[Wilson, J. D., Braunwald, E., Isselbacher, K. J., Petersdorf, R. G., Martin, J. B., Fauci, A. S. & Root, R. K. (1991). Harrison's Principles of Internal Medicine 12th ed., pp. 320, 647-648, 787. New York: McGraw-Hill.]). For the structures of dapsone solvates, see: Kus'mina et al. (1981[Kus'mina, L. G., Struchkov, Yu. T., Novozhilova, N. V. & Tudorovskaya, G. L. (1981). Kristallografiya, 26, 690-694.]); Lemmer et al. (2012[Lemmer, H., Stieger, N., Liebenberg, W. & Caira, M. R. (2012). Cryst. Growth Des. 12, 1683-1692.]). For the structures of adducts and a salt of dapsone, see: Smith & Wermuth (2012a[Smith, G. & Wermuth, U. D. (2012a). Acta Cryst. E68, o494.],b[Smith, G. & Wermuth, U. D. (2012b). Acta Cryst. E68, o669.], 2013[Smith, G. & Wermuth, U. D. (2013). J. Chem. Crystallogr. 43, 664-670.]).

[Scheme 1]

Experimental

Crystal data
  • C12H13N2O2S+·C7H7O3S-

  • Mr = 420.49

  • Monoclinic, P 21 /n

  • a = 5.9516 (9) Å

  • b = 25.147 (3) Å

  • c = 12.4506 (15) Å

  • [beta] = 94.908 (11)°

  • V = 1856.6 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 200 K

  • 0.25 × 0.12 × 0.12 mm

Data collection
  • Oxford Diffraction Gemini-S CCD-detector diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Tehnologies Ltd, Yarnton, Oxfordshire, England.]) Tmin = 0.935, Tmax = 0.980

  • 6908 measured reflections

  • 3650 independent reflections

  • 2653 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.161

  • S = 1.02

  • 3650 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H41...O13Ai 0.86 1.91 2.759 (4) 165
N4-H42...O11ii 0.83 2.24 3.008 (4) 153
N4-H43...O11Aiii 0.86 1.89 2.718 (4) 160
N41-H411...O12A 0.90 2.18 3.012 (4) 152
N41-H412...O13Aiv 0.97 2.46 3.369 (4) 155
Symmetry codes: (i) -x+1, -y, -z+1; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iii) -x, -y, -z+1; (iv) -x, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2013[Agilent (2013). CrysAlis PRO. Agilent Tehnologies Ltd, Yarnton, Oxfordshire, 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.]); 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: SJ5377 ).


Acknowledgements

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

References

Agilent (2013). CrysAlis PRO. Agilent Tehnologies Ltd, Yarnton, Oxfordshire, England.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Kus'mina, L. G., Struchkov, Yu. T., Novozhilova, N. V. & Tudorovskaya, G. L. (1981). Kristallografiya, 26, 690-694.
Lemmer, H., Stieger, N., Liebenberg, W. & Caira, M. R. (2012). Cryst. Growth Des. 12, 1683-1692.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Smith, G. & Wermuth, U. D. (2012a). Acta Cryst. E68, o494.  [CSD] [CrossRef] [IUCr Journals]
Smith, G. & Wermuth, U. D. (2012b). Acta Cryst. E68, o669.  [CSD] [CrossRef] [IUCr Journals]
Smith, G. & Wermuth, U. D. (2013). J. Chem. Crystallogr. 43, 664-670.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Wilson, J. D., Braunwald, E., Isselbacher, K. J., Petersdorf, R. G., Martin, J. B., Fauci, A. S. & Root, R. K. (1991). Harrison's Principles of Internal Medicine 12th ed., pp. 320, 647-648, 787. New York: McGraw-Hill.


Acta Cryst (2014). E70, o37  [ doi:10.1107/S1600536813033023 ]

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