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Volume 69 
Part 8 
Page o1277  
August 2013  

Received 19 June 2013
Accepted 5 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.122
Data-to-parameter ratio = 23.3
Details
Open access

3-Hydroxyanilinium p-toluenesulfonate

aDepartment of Physics, Anna University, Chennai 600 025, India
Correspondence e-mail: krgkrishnan@annauniv.edu

The asymmetric unit of the title salt, C6H8NO+·C7H7O3S-, contains two cations and two anions. In the crystal, the cations and anions are linked through extensive N-H...O and O-H...O hydrogen-bonding interactions, which result in R44(18) and R21(4) ring motifs, forming a three-dimensional network.

Related literature

For related structures of 4-toluenesulfonate salts, see: Koshima et al. (2004[Koshima, H., Miyamoto, H., Yagi, I. & Uosaki, K. (2004). Cryst. Growth Des. 4,807-811.]); Biradha & Mahata (2005[Biradha, K. & Mahata, G. (2005). Cryst. Growth Des. 5, 49-51.]); Sivakumar et al. (2012[Sivakumar, P. K., Krishnakumar, M., Kanagadurai, R., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3059.]).

[Scheme 1]

Experimental

Crystal data
  • C6H8NO+·C7H7O3S-

  • Mr = 281.32

  • Triclinic, [P \overline 1]

  • a = 9.5775 (3) Å

  • b = 10.8224 (3) Å

  • c = 14.1445 (4) Å

  • [alpha] = 96.787 (2)°

  • [beta] = 109.701 (1)°

  • [gamma] = 91.324 (2)°

  • V = 1367.50 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.910, Tmax = 0.953

  • 32207 measured reflections

  • 8651 independent reflections

  • 6679 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.122

  • S = 1.03

  • 8651 reflections

  • 372 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.33 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O7-H7...O6i 0.82 1.95 2.7657 (16) 173 (2)
N2-H2C...O4i 0.89 (1) 2.06 (1) 2.9441 (18) 170 (2)
N2-H2B...O3i 0.89 (1) 2.31 (2) 2.9020 (17) 124 (2)
N2-H2A...O3ii 0.90 (1) 1.89 (1) 2.7784 (18) 170 (2)
N2-H2B...O5ii 0.89 (1) 2.20 (2) 2.9395 (19) 141 (2)
N1-H1B...O5iii 0.89 (1) 2.15 (2) 2.9406 (19) 147 (2)
N1-H1B...O6iii 0.89 (1) 2.32 (2) 3.1087 (19) 147 (2)
N1-H1C...O2iv 0.89 (1) 1.86 (1) 2.7410 (18) 177 (2)
O8-H8...O1 0.82 1.94 2.7216 (17) 160
N1-H1A...O1 0.90 (1) 1.95 (1) 2.8007 (17) 158 (2)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) -x+2, -y+1, -z+1; (iv) -x+2, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2454 ).


Acknowledgements

The authors thank thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, Chennai, India, for the data collection.

References

Biradha, K. & Mahata, G. (2005). Cryst. Growth Des. 5, 49-51.  [CSD] [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Koshima, H., Miyamoto, H., Yagi, I. & Uosaki, K. (2004). Cryst. Growth Des. 4,807-811.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sivakumar, P. K., Krishnakumar, M., Kanagadurai, R., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3059.  [CSD] [CrossRef] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1277  [ doi:10.1107/S1600536813018692 ]

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