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Volume 69 
Part 8 
Page o1236  
August 2013  

Received 8 June 2013
Accepted 29 June 2013
Online 10 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.022
wR = 0.061
Data-to-parameter ratio = 14.3
Details
Open access

4-Sulfamoylanilinium perchlorate

aDepartment of Physics, Regional centre of Anna University, Tirunelveli Region, Tirunelveli 627 007, India,bDepartment of Physics, University College of Engineering, Nagercoil, Anna University, Tirunelveli Region, Nagercoil 629 004, India, and cLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 607, India
Correspondence e-mail: physics.autt@gmail.com

In the crystal of the title salt, C6H9N2O2S+·ClO4-, the components are linked by N-H...O hydrogen bonds, forming a three-dimensional network. The cations are connected along a and b axes, leading to linear and zigzag C(3) and C(8) chain motifs, respectively. A cation-anion interaction along the c axis leads to a C22(12) chain motif. R33(18) and R33(20) ring motifs are observed as cation-anion-type interactions. These hydrogen-bonding ring and chain motifs are localized at z = 0 or 1, leading to alternate hydrophilic and hydrophobic regions along the c axis as a result of the stacking of anions and the aromatic cationic parts.

Related literature

For the first use of sulfanilamide, see: Buttle et al. (1936[Buttle, G. A. H., Grey, W. H. & Stephenson, D. (1936). Lancet, 1, 1286-1290.]). For related structures, see: Ravikumar et al. (2013[Ravikumar, B., Pandiarajan, S. & Athimoolam, S. (2013). Acta Cryst. E69, o596.]); Pandiarajan et al. (2011[Pandiarajan, S., Balasubramanian, S., Ravikumar, B. & Athimoolam, S. (2011). Acta Cryst. E67, o2788.]); Topacli & Kesimli (2001[Topacli, A. & Kesimli, B. (2001). Sepctrosc. Lett. 34, 513-526.]). For graph-set motifs, see Etter et al. (1990[Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9N2O2S+·ClO4-

  • Mr = 272.66

  • Monoclinic, P 21

  • a = 4.9158 (10) Å

  • b = 10.514 (2) Å

  • c = 9.814 (2) Å

  • [beta] = 93.716 (3)°

  • V = 506.15 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.60 mm-1

  • T = 293 K

  • 0.24 × 0.16 × 0.12 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 5796 measured reflections

  • 2367 independent reflections

  • 2361 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.061

  • S = 1.08

  • 2367 reflections

  • 166 parameters

  • 5 restraints

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

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1287 Friedel pairs

  • Flack parameter: 0.00 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.88 (1) 2.12 (1) 2.953 (2) 160 (3)
N1-H1B...O6ii 0.88 (3) 2.30 (3) 3.086 (2) 149 (2)
N2-H2A...O5i 0.88 (1) 2.19 (1) 3.044 (2) 164 (3)
N2-H2B...O2iii 0.88 (1) 2.16 (2) 2.876 (2) 139 (2)
N2-H2C...O4iv 0.88 (1) 2.30 (2) 2.858 (2) 122 (2)
N2-H2C...O5 0.88 (1) 2.37 (2) 3.058 (2) 136 (2)
Symmetry codes: (i) x+1, y, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) [-x+2, y+{\script{1\over 2}}, -z+1]; (iv) [-x+1, y+{\script{1\over 2}}, -z].

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; molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL/PC.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG5332 ).


Acknowledgements

SA is grateful to the Department of Science and Technology, SERB, for the financial support of this work in the form of the Fast-track Research Project scheme.

References

Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Buttle, G. A. H., Grey, W. H. & Stephenson, D. (1936). Lancet, 1, 1286-1290.  [CrossRef]
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.  [CrossRef] [Web of Science] [IUCr Journals]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [IUCr Journals]
Pandiarajan, S., Balasubramanian, S., Ravikumar, B. & Athimoolam, S. (2011). Acta Cryst. E67, o2788.  [CSD] [CrossRef] [IUCr Journals]
Ravikumar, B., Pandiarajan, S. & Athimoolam, S. (2013). Acta Cryst. E69, o596.  [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Topacli, A. & Kesimli, B. (2001). Sepctrosc. Lett. 34, 513-526.  [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1236  [ doi:10.1107/S1600536813017972 ]

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