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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 [sigma](C-C) = 0.004 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 12.8
Details
Open access

Ammonium 4-methoxybenzenesulfonate

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[Desiraju, G. R. P. (2007). Angew. Chem. Int. Ed. 46, 8342-8356.]). For related structures, see: Fewings et al. (2001[Fewings, K. R., Junk, P. C., Georganopoulou, D., Prince, P. D. & Steed, J. W. (2001). Polyhedron, 20, 643-649.]); Wang et al. (2007[Wang, K.-W., Feng, W.-J., Li, H.-Y., Ma, L.-L. & Jin, Z.-M. (2007). Acta Cryst. E63, o3481.]). For the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For the synthesis, see: Porcheddu et al. (2009[Porcheddu, A., De Luca, L. & Giacomelli, G. (2009). Synlett, 13, 2149-2153.]).

[Scheme 1]

Experimental

Crystal data
  • NH4+·C7H7O4S-

  • Mr = 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[alpha] radiation

  • [mu] = 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.]) Tmin = 0.958, Tmax = 0.965

  • 4265 measured reflections

  • 1732 independent reflections

  • 1548 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 637 Friedel pairs

  • Flack parameter: -0.11 (14)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.88 (2) 1.99 (2) 2.851 (3) 170 (3)
N1-H4N...O2ii 0.86 (2) 1.98 (2) 2.797 (3) 160 (3)
N1-H2N...O3iii 0.88 (2) 1.98 (2) 2.824 (3) 162 (3)
N1-H3N...O3 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[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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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: 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[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

References

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


Acta Cryst (2012). E68, o2228-o2229   [ doi:10.1107/S1600536812028103 ]

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