[Journal logo]

Volume 69 
Part 4 
Page o596  
April 2013  

Received 18 January 2013
Accepted 15 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.104
Data-to-parameter ratio = 15.7
Details
Open access

Bis(4-sulfamoylanilinium) sulfate

aDepartment of Physics, Devanga Arts College, Aruppukottai 626 101, India, and bDepartment of Physics, University College of Engineering Nagercoil, Anna University Chennai, Nagercoil 629 004, India
Correspondence e-mail: athi81s@yahoo.co.in

In the title salt, 2C6H9N2O2S+·SO42-, the sulfate S atom is situated on a crystallographic twofold axis (the symmetry of the anion is 2). The anion exerts intense libration, which is manifested by shortening of the observed sulfate S-O bonds, as well as by features in the electron-density map. The crystal structure is stabilized through a three-dimensional hydrogen-bonding network formed by strong N-H...O hydrogen bonds.

Related literature

For information about folate synthesis, see: Kent (2000[Kent, M. (2000). Advanced Biology, p. 46. New York: Oxford University Press Inc.]). For related structures, see: Pandiarajan et al. (2011[Pandiarajan, S., Balasubramanian, S., Ravikumar, B. & Athimoolam, S. (2011). Acta Cryst. E67, o2788.]); Zaouali Zgolli et al. (2010[Zaouali Zgolli, D., Boughzala, H. & Driss, A. (2010). Acta Cryst. E66, o1488.]). For correction of the S-O distances in the sulfate anion due to libration movement, see: Nardelli (1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]). For TLS approximation, see: Schomaker & Trueblood (1968[Schomaker, V. & Trueblood, K. N. (1968). Acta Cryst. B24, 63-76.]). For graph-set motifs, see: Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]). For the categorization of hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, p. 13. International Union of Crystallography and Oxford Science Publications.]).

[Scheme 1]

Experimental

Crystal data
  • 2C6H9N2O2S+·SO42-

  • Mr = 442.48

  • Orthorhombic, P b c n

  • a = 9.6543 (6) Å

  • b = 9.7591 (11) Å

  • c = 18.579 (3) Å

  • V = 1750.5 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.48 mm-1

  • T = 293 K

  • 0.24 × 0.22 × 0.19 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 18054 measured reflections

  • 2054 independent reflections

  • 1950 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.104

  • S = 1.05

  • 2054 reflections

  • 131 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.69 e Å-3

  • [Delta][rho]min = -0.51 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O22i 0.84 (2) 1.93 (2) 2.743 (3) 164 (3)
N1-H2N...O21ii 0.86 (2) 1.99 (2) 2.849 (3) 168 (3)
N2-H2B...O2iii 0.89 2.30 3.043 (3) 141
N2-H2B...O1iv 0.89 2.57 3.146 (2) 123
N2-H2A...O22v 0.89 1.90 2.787 (3) 177
N2-H2C...O21vi 0.89 2.06 2.900 (3) 158
Symmetry codes: (i) [-x+1, y, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (iii) -x, -y+1, -z+1; (iv) [x, -y+1, z-{\script{1\over 2}}]; (v) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]; (vi) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL/PC and JANA2006 (Petricek et al., 2006[Petricek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics of the Czech Academy of Sciences, Prague, Czech Republic.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and JANA2006; software used to prepare material for publication: SHELXTL/PC.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2278 ).


Acknowledgements

SPR and BRK thank the management of the Devanga Arts College for their support and encouragement and also extend their thanks to the University Grants Commission for the financial support of this work in the form of a Minor Research Project.

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology, p. 13. International Union of Crystallography and Oxford Science Publications.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [ISI] [details]
Kent, M. (2000). Advanced Biology, p. 46. New York: Oxford University Press Inc.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Pandiarajan, S., Balasubramanian, S., Ravikumar, B. & Athimoolam, S. (2011). Acta Cryst. E67, o2788.  [CrossRef] [details]
Petricek, V., Dusek, M. & Palatinus, L. (2006). JANA2006. Institute of Physics of the Czech Academy of Sciences, Prague, Czech Republic.
Schomaker, V. & Trueblood, K. N. (1968). Acta Cryst. B24, 63-76.  [CrossRef] [ChemPort] [details] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Zaouali Zgolli, D., Boughzala, H. & Driss, A. (2010). Acta Cryst. E66, o1488.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o596  [ doi:10.1107/S1600536813007216 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.