Tetra­ethyl­ammonium toluene-4-sulfon­ate

Brus, D.M.; Czyrko, J.; Brzezinski, K.

doi:10.1107/S1600536813002961

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 (C-C) = 0.005 Å
Disorder in main residue
R = 0.076
wR = 0.163
Data-to-parameter ratio = 15.5
Details

Tetraethylammonium toluene-4-sulfonate

Diana Malgorzata Brus,^a Justyna Czyrko ^a and Krzysztof Brzezinski ^a ^*

^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-HO hydrogen bonds, forming ribbons along [10-1]. The ribbons are linked via C-HO 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). For its application as a phase-transfer catalyst, see: Cerveau et al. (2002) or as the supporting electrolyte, see: Adachi et al. (1979); Wynne & Street (1985); Yoshida et al. (1986); Wong & Moeller (1993); Ben et al. (2011).

Experimental

Crystal data

C₈H₂₀N⁺·C₇H₇O₃S^-
M_r = 301.21
Monoclinic, P 2₁ /n
a = 16.8771 (3) Å
b = 7.53713 (16) Å
c = 26.2404 (6) Å
= 97.2938 (18)°
V = 3310.90 (12) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.771, T_max = 1.000
6276 measured reflections
6276 independent reflections
5477 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.076
wR(F²) = 0.163
S = 1.19
6276 reflections
406 parameters
82 restraints
H-atom parameters constrained
_max = 0.46 e Å^-3
_min = -0.50 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6B-H6BO23	0.95	2.57	3.351 (6)	140
C31-H31BO3Bⁱ	0.99	2.49	3.344 (4)	145
C33-H33AO2B	0.99	2.47	3.354 (4)	148
C35-H35AO22ⁱⁱ	0.99	2.42	3.228 (4)	138
C36-H36CO3Bⁱⁱⁱ	0.98	2.58	3.544 (4)	169
C43-H43BO22	0.99	2.44	3.269 (4)	141
C45-H45AO2B	0.99	2.53	3.367 (4)	142
C47-H47AO3Bⁱ	0.99	2.57	3.440 (4)	147
C48-H48BO22^iv	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); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXD (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); 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.
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Baizer, M. M. (1964). J. Electrochem. Soc. 111, 215-222.
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.
Cerveau, G., Chappellet, S., Corriu, R. J. P., Dabiens, B. & Le Bideau, J. (2002). Organometallics, 21, 1560-1564.
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wong, P. L. & Moeller, D. K. (1993). J. Am. Chem. Soc. 115, 11434-11445.
Wynne, K. J. & Street, G. B. (1985). Macromolecules, 18, 2361-2368.
Yoshida, J., Muraki, K., Funahashi, H. & Kawabata, N. (1986). J. Org. Chem. 51, 3996-4000.

organic compounds