Ammonium 4-meth­oxy­benzene­sulfonate

Suarez, S.; Doctorovich, F.; Baggio, R.

doi:10.1107/S1600536812028103

Volume 68
Part 7
Pages o2228-o2229
July 2012

Received 14 June 2012
Accepted 20 June 2012
Online 27 June 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 12.8
Details

Ammonium 4-methoxybenzenesulfonate

Sebastián Suarez,^a ^* Fabio Doctorovich ^a ⁺ and Ricardo Baggio ^b

^aDepartamento de Química Inorgánica, Analítica y Química, Física/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Buenos Aires, Argentina, and ^bGerencia de Investigación y Aplicaciones, Centro Atómico Constituyentes, Comisión Nacional de Energía Atómica, Buenos Aires, Argentina
Correspondence e-mail: seba@qi.fcen.uba.ar

The molecular structure of the title compound, NH₄⁺·C₇H₇O₄S^-, is featureless [the methoxy C atom deviating 0.173 (6) Å from the phenyl mean plane] with interatomic distances and angles in the expected ranges. The main feature of interest is the packing mode. Hydrophilic (SO₃ and NH₄) and hydrophobic (PhOCH₃) parts in the structure segregate, the former interacting through a dense hydrogen-bonding scheme, leading to a well connected two-dimensional structure parallel to (100) and the latter hydrophobic groups acting as spacers for an interplanar separation of c/2 = 10.205 (2) Å. In spite of being aligned along [110], the benzene rings stack in a far from parallel fashion [viz. consecutive ring centers determine a broken line with a 164.72 (12)° zigzag angle], thus preventing any possible [pi] - [pi] interaction.

Related literature

For literature on the role of weak interactions in supramolecular structures, see: Desiraju (2007). For related structures, see: Fewings et al. (2001); Wang et al. (2007). For the Cambridge Structural Database, see: Allen (2002). For the synthesis, see: Porcheddu et al. (2009).

Experimental

Crystal data

NH₄⁺·C₇H₇O₄S^-
M_r = 205.23
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.2664 (12) Å
b = 7.1342 (12) Å
c = 20.410 (2) Å
V = 912.4 (2) Å³
Z = 4
Mo K radiation
= 0.34 mm^-1
T = 298 K
0.20 × 0.10 × 0.10 mm

Data collection

Oxford Diffraction Gemini CCD S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.958, T_max = 0.965
4265 measured reflections
1732 independent reflections
1548 reflections with I > 2(I)
R_int = 0.050

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.119
S = 1.04
1732 reflections
135 parameters
21 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.47 e Å^-3
_min = -0.36 e Å^-3
Absolute structure: Flack (1983), 637 Friedel pairs
Flack parameter: -0.11 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.88 (2)	1.99 (2)	2.851 (3)	170 (3)
N1-H4NO2ⁱⁱ	0.86 (2)	1.98 (2)	2.797 (3)	160 (3)
N1-H2NO3ⁱⁱⁱ	0.88 (2)	1.98 (2)	2.824 (3)	162 (3)
N1-H3NO3	0.87 (2)	2.04 (2)	2.890 (3)	164 (3)
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2074 ).

Acknowledgements

The authors acknowledge ANPCyT (project No. PME 2006-01113) for the purchase of the Oxford Gemini CCD diffractometer and the Spanish Research Council (CSIC) for the provision of a free-of-charge licence to the Cambridge Structural Database (Allen, 2002).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Desiraju, G. R. P. (2007). Angew. Chem. Int. Ed. 46, 8342-8356.
Fewings, K. R., Junk, P. C., Georganopoulou, D., Prince, P. D. & Steed, J. W. (2001). Polyhedron, 20, 643-649.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.
Porcheddu, A., De Luca, L. & Giacomelli, G. (2009). Synlett, 13, 2149-2153.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wang, K.-W., Feng, W.-J., Li, H.-Y., Ma, L.-L. & Jin, Z.-M. (2007). Acta Cryst. E63, o3481.

organic compounds