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Volume 69 
Part 11 
Page o1725  
November 2013  

Received 21 September 2013
Accepted 25 October 2013
Online 31 October 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.110
Data-to-parameter ratio = 22.0
Details
Open access

Uronium 3-carb­oxy-4-hy­droxy­benzene­sulfonate

aDepartment of Physics, Presidency College, Chennai 600 005, India,bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and cKunthavai Naacchiyaar Govt. Arts College (W), Thanjavur 613 007, India
Correspondence e-mail: chakkaravarthi_2005@yahoo.com, kan_uma6@yahoo.com

In the title compound, CH5N2O+·C7H5O6S-, the dihedral angle between the benzene ring and the mean plane of the uronium cation is 76.02 (8)°. The carboxyl group in the anion is twisted by 1.47 (9)° from the benzene ring. In the crystal, the cation is linked to the anion by weak O-H...O and N-H...O hydrogen bonds and [pi]-[pi] inter­actions [centroid-centroid distance = 3.8859 (8) Å], forming a three-dimensional network.

Related literature

For the biological activity of urea derivatives, see: Sliskovic et al. (1999[Sliskovic, D. R., Krause, B. R. & Bocan, T. M. A. (1999). Annu. Rep. Med. Chem. 34, 101-110.]); Furlong et al. (2000[Furlong, E. T., Burkhardt, M. R., Gates, P. M., Werner, S. L. & Battaglin, W. A. (2000). Sci. Total Environ. 248, 135-146.]); Houghton et al. (1995[Houghton, P. J., Sosinski, J., Thakar, J. H., Border, G. B. & Grindey, G. B. (1995). Biochem. Pharmacol. 49, 661-668.]). For related structures, see: Krishnakumar et al. (2012[Krishnakumar, M., Sudhahar, S., Silambarasan, A., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3268.]); Sudhahar et al. (2013[Sudhahar, S., Krishnakumar, M., Sornamurthy, B. M., Chakkaravarthi, G. & Mohankumar, R. (2013). Acta Cryst. E69, o279.]); Worsham & Busing (1969[Worsham, J. E. & Busing, W. R. (1969). Acta Cryst. B25, 572-578.]); Nelyubina et al. (2007[Nelyubina, Y. V., Lyssenko, K. A., Golovanov, D. G. & Antipin, Yu. A. (2007). CrystEngComm. 9, 991-996.]).

[Scheme 1]

Experimental

Crystal data
  • CH5N2O+·C7H5O6S-

  • Mr = 278.24

  • Triclinic, [P \overline 1]

  • a = 7.2248 (4) Å

  • b = 8.7718 (5) Å

  • c = 10.1549 (5) Å

  • [alpha] = 85.504 (3)°

  • [beta] = 71.087 (2)°

  • [gamma] = 68.659 (2)°

  • V = 566.50 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 295 K

  • 0.30 × 0.24 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.911, Tmax = 0.939

  • 14246 measured reflections

  • 4079 independent reflections

  • 3432 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.110

  • S = 1.05

  • 4079 reflections

  • 185 parameters

  • 7 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O2 0.82 (1) 1.83 (1) 2.5966 (14) 154 (18)
O7-H7...O6 0.82 (1) 1.85 (1) 2.6629 (14) 169 (18)
N1-H1A...O4 0.84 (1) 1.96 (1) 2.7979 (16) 175 (16)
O1-H1...O5i 0.83 (1) 1.84 (1) 2.6511 (12) 167 (18)
N1-H1B...O5ii 0.85 (1) 1.95 (1) 2.7976 (16) 178 (15)
N2-H2B...O6ii 0.86 (1) 2.22 (1) 3.0712 (16) 172 (15)
N2-H2A...O3iii 0.85 (1) 2.19 (1) 3.0347 (16) 173 (15)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) x, y, z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2485 ).


Acknowledgements

The authors thank the SAIF, IIT Madras, for the data collection. MKK thanks the Council of Scientific and Industrial Research, New Delhi, India, for providing financial support [project No. 03 (1200)/11/EMR-II].

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Furlong, E. T., Burkhardt, M. R., Gates, P. M., Werner, S. L. & Battaglin, W. A. (2000). Sci. Total Environ. 248, 135-146.  [CrossRef] [PubMed] [ChemPort]
Houghton, P. J., Sosinski, J., Thakar, J. H., Border, G. B. & Grindey, G. B. (1995). Biochem. Pharmacol. 49, 661-668.  [CrossRef] [ChemPort] [PubMed]
Krishnakumar, M., Sudhahar, S., Silambarasan, A., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3268.  [CSD] [CrossRef] [IUCr Journals]
Nelyubina, Y. V., Lyssenko, K. A., Golovanov, D. G. & Antipin, Yu. A. (2007). CrystEngComm. 9, 991-996.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sliskovic, D. R., Krause, B. R. & Bocan, T. M. A. (1999). Annu. Rep. Med. Chem. 34, 101-110.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sudhahar, S., Krishnakumar, M., Sornamurthy, B. M., Chakkaravarthi, G. & Mohankumar, R. (2013). Acta Cryst. E69, o279.  [CSD] [CrossRef] [IUCr Journals]
Worsham, J. E. & Busing, W. R. (1969). Acta Cryst. B25, 572-578.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1725  [ doi:10.1107/S1600536813029474 ]

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