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Volume 69 
Part 5 
Page o725  
May 2013  

Received 8 March 2013
Accepted 7 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.030
wR = 0.091
Data-to-parameter ratio = 13.1
Details
Open access

4-Methylanilinium 4-hydroxybenzenesulfonate

aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and bDepartment of Physics, Loyola college, Chennai-34, Tamilnadu, India
Correspondence e-mail: guqmc@yahoo.com

In the crystal of the title molecular salt, C7H10N+·C6H5O4S-, the benzenesulfonate units are linked through phenol-sulfonate O-H...O hydrogen bonds, forming chains along the c-axis direction. These chains are linked via N-H...O hydrogen bonds involving two of the three H atoms of the ammonium group of the 4-methylanilium cation, giving rise to two-dimensional networks parallel to the bc plane which are further connected through an additional N-H...O interaction in which the third ammonium H atom is involved, generating a three-dimensional network.

Related literature

For the biological activity of related compounds, see: Fukami et al. (2000[Fukami, H., Imajo, S., Ito, A., Kakutani, S., Shibata, H., Sumida, M., Tanaka, T., Niwata, S., Saitoh, M., Kiso, Y., Miyazaki, M., Okunishi, H., Urata, H. & Arakawa, K. (2000). Drug Des. Discov. 17, 69-84.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Waston, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C7H10N+·C6H5O4S-

  • Mr = 281.32

  • Monoclinic, P 21 /c

  • a = 11.6450 (2) Å

  • b = 7.1670 (1) Å

  • c = 16.3080 (3) Å

  • [beta] = 107.654 (1)°

  • V = 1296.96 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.926, Tmax = 0.950

  • 11047 measured reflections

  • 2285 independent reflections

  • 2045 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.091

  • S = 1.06

  • 2285 reflections

  • 175 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1C...O1i 0.89 1.96 2.8367 (19) 169
N1-H1B...O4ii 0.89 1.96 2.839 (2) 170
N1-H1A...O2iii 0.89 1.94 2.8091 (19) 166
O4-H4...O3iii 0.82 1.82 2.6343 (17) 173
Symmetry codes: (i) [x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y, -z; (iii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: 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: LR2102 ).


Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data collection and computer facilities.

References

Allen, F. H., Kennard, O., Waston, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fukami, H., Imajo, S., Ito, A., Kakutani, S., Shibata, H., Sumida, M., Tanaka, T., Niwata, S., Saitoh, M., Kiso, Y., Miyazaki, M., Okunishi, H., Urata, H. & Arakawa, K. (2000). Drug Des. Discov. 17, 69-84.  [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o725  [ doi:10.1107/S1600536813009410 ]

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