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Volume 69 
Part 3 
Page o324  
March 2013  

Received 24 January 2013
Accepted 29 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.076
wR = 0.163
Data-to-parameter ratio = 15.5
Details
Open access

Tetraethylammonium toluene-4-sulfonate

aInstitute of Chemistry, University of Bialystok, Hurtowa 1, 15-399 Bialystok, Poland
Correspondence e-mail: k.brzezinski@uwb.edu.pl

There are two tetraethylammonium cations and two toluene-4-sulfate anions in the asymmetric unit of the title salt, C8H20N+·C7H7O3S-. One of the anions is disordered over two positions, with refined occupancies of 0.447 (3) and 0.553 (3). In the crystal, the cations and anions are linked by C-H...O hydrogen bonds, forming ribbons along [10-1]. The ribbons are linked via C-H...O hydrogen bonds, forming a two-dimensional network lying parallel to (10-1).

Related literature

For the preparation of tetraethylammonium toluene-4-sulfonate from ethyl 4-toluenesulfonate and triethylamine, see: Baizer (1964[Baizer, M. M. (1964). J. Electrochem. Soc. 111, 215-222.]). For its application as a phase-transfer catalyst, see: Cerveau et al. (2002[Cerveau, G., Chappellet, S., Corriu, R. J. P., Dabiens, B. & Le Bideau, J. (2002). Organometallics, 21, 1560-1564.]) or as the supporting electrolyte, see: Adachi et al. (1979[Adachi, T., Iwasaki, T., Inoue, I. & Miyoshi, M. (1979). J. Org. Chem. 44, 1404-1409.]); Wynne & Street (1985[Wynne, K. J. & Street, G. B. (1985). Macromolecules, 18, 2361-2368.]); Yoshida et al. (1986[Yoshida, J., Muraki, K., Funahashi, H. & Kawabata, N. (1986). J. Org. Chem. 51, 3996-4000.]); Wong & Moeller (1993[Wong, P. L. & Moeller, D. K. (1993). J. Am. Chem. Soc. 115, 11434-11445.]); Ben et al. (2011[Ben, T., Shi, K., Cui, Y., Pei, C., Zuo, Y., Guo, H., Zhang, D., Xu, J., Deng, F., Tian, Z. & Qiu, S. (2011). J. Mater. Chem. 21, 18208-18214.]).

[Scheme 1]

Experimental

Crystal data
  • C8H20N+·C7H7O3S-

  • Mr = 301.21

  • Monoclinic, P 21 /n

  • a = 16.8771 (3) Å

  • b = 7.53713 (16) Å

  • c = 26.2404 (6) Å

  • [beta] = 97.2938 (18)°

  • V = 3310.90 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 100 K

  • 0.8 × 0.6 × 0.3 mm

Data collection
  • Agilent SuperNova (Dual, Cu at zero, Atlas) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.771, Tmax = 1.000

  • 6276 measured reflections

  • 6276 independent reflections

  • 5477 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.076

  • wR(F2) = 0.163

  • S = 1.19

  • 6276 reflections

  • 406 parameters

  • 82 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.50 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6B-H6B...O23 0.95 2.57 3.351 (6) 140
C31-H31B...O3Bi 0.99 2.49 3.344 (4) 145
C33-H33A...O2B 0.99 2.47 3.354 (4) 148
C35-H35A...O22ii 0.99 2.42 3.228 (4) 138
C36-H36C...O3Biii 0.98 2.58 3.544 (4) 169
C43-H43B...O22 0.99 2.44 3.269 (4) 141
C45-H45A...O2B 0.99 2.53 3.367 (4) 142
C47-H47A...O3Bi 0.99 2.57 3.440 (4) 147
C48-H48B...O22iv 0.98 2.58 3.562 (4) 175
Symmetry codes: (i) x, y+1, z; (ii) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iv) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXD (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: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KP2445 ).


Acknowledgements

The X-ray diffractometer was funded by the EFRD as part of the Operational Programme Development of Eastern Poland 2007-2013, project POPW.01.03.00-20-034/09-00.

References

Adachi, T., Iwasaki, T., Inoue, I. & Miyoshi, M. (1979). J. Org. Chem. 44, 1404-1409.  [CrossRef] [ChemPort]
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Baizer, M. M. (1964). J. Electrochem. Soc. 111, 215-222.  [CrossRef] [ChemPort] [ISI]
Ben, T., Shi, K., Cui, Y., Pei, C., Zuo, Y., Guo, H., Zhang, D., Xu, J., Deng, F., Tian, Z. & Qiu, S. (2011). J. Mater. Chem. 21, 18208-18214.  [ISI] [CrossRef] [ChemPort]
Cerveau, G., Chappellet, S., Corriu, R. J. P., Dabiens, B. & Le Bideau, J. (2002). Organometallics, 21, 1560-1564.  [CrossRef] [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wong, P. L. & Moeller, D. K. (1993). J. Am. Chem. Soc. 115, 11434-11445.  [CrossRef] [ChemPort] [ISI]
Wynne, K. J. & Street, G. B. (1985). Macromolecules, 18, 2361-2368.  [CrossRef] [ChemPort] [ISI]
Yoshida, J., Muraki, K., Funahashi, H. & Kawabata, N. (1986). J. Org. Chem. 51, 3996-4000.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o324  [ doi:10.1107/S1600536813002961 ]

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