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Volume 69 
Part 11 
Page o1609  
November 2013  

Received 22 September 2013
Accepted 29 September 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.038
wR = 0.107
Data-to-parameter ratio = 15.4
Details
Open access

4-Nitro­anilinium 3-carb­oxy-4-hy­droxy­benzene­sulfonate monohydrate

aDepartment of Physics, M. N. M. Jain Engineering College, Chennai 600 097, India,bDepartment of Physics, Presidency College, Chennai 600 005, India, and cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
Correspondence e-mail: chakkaravarthi_2005@yahoo.com, srkanagadurai@yahoo.co.in

In the title hydrated salt, C6H7N2O2+·C7H5O6S-·H2O, the benzene ring of the cation makes a dihedral angle of 1.32 (19)° with the attached nitro group. In the anion, an intra­molecular O-H...O hydrogen bond with an S(6) ring motif is formed between the carb­oxyl and hy­droxy groups; the dihedral angle between the carb­oxyl group and the benzene ring is 8.76 (8)°. The crystal structure exhibits inter­molecular N-H...O, O-H...O, C-H...O, and [pi]-[pi] [centroid-centroid distances = 3.6634 (9) and 3.7426 (9) Å] inter­actions to form a three-dimensional network.

Related literature

For mol­ecular compounds with nonlinear optical properties, see: Nalwa & Miyata (1997[Nalwa, H. S. & Miyata, S. (1997). In Nonlinear Optics of Organic Molecules and Polymers. Boca Raton: CRC Press.]). For related structures, see: Asiri et al. (2010[Asiri, A. M., Khan, S. A., Tan, K. W. & Ng, S. W. (2010). Acta Cryst. E66, o1765.]); Krishnakumar et al. (2012[Krishnakumar, M., Sudhahar, S., Silambarasan, A., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3268.]); Sudhahar et al. (2013[Sudhahar, S., Krishnakumar, M., Sornamurthy, B. M., Chakkaravarthi, G. & Mohankumar, R. (2013). Acta Cryst. E69, o279.]).

[Scheme 1]

Experimental

Crystal data
  • C6H7N2O2+·C7H5O6S-·H2O

  • Mr = 374.32

  • Orthorhombic, P b c a

  • a = 13.2676 (3) Å

  • b = 13.5572 (3) Å

  • c = 17.1246 (4) Å

  • V = 3080.23 (12) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.27 mm-1

  • T = 295 K

  • 0.26 × 0.24 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.934, Tmax = 0.949

  • 15578 measured reflections

  • 3640 independent reflections

  • 3062 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.107

  • S = 1.03

  • 3640 reflections

  • 236 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O9 0.89 1.99 2.841 (2) 160
N1-H1B...O1 0.89 1.95 2.8357 (18) 171
O4-H4A...O5 0.82 1.88 2.6028 (18) 146
C9-H9...O9 0.93 2.57 3.141 (3) 121
N1-H1A...O7i 0.89 2.40 2.836 (2) 111
N1-H1C...O2ii 0.89 1.93 2.8069 (18) 168
O4-H4A...O2iii 0.82 2.38 2.9494 (16) 128
O6-H6...O3iv 0.82 1.86 2.6595 (17) 164
O9-H9A...O2v 0.82 (1) 2.33 (3) 3.005 (2) 139 (4)
O9-H9A...O3v 0.82 (1) 2.48 (3) 3.151 (2) 140 (4)
O9-H9B...O4vi 0.82 (1) 2.56 (3) 3.283 (2) 149 (4)
Symmetry codes: (i) [-x+{\script{1\over 2}}, -y, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+1; (iii) [x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]; (iv) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (v) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]; (vi) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5308 ).


Acknowledgements

The authors thank SAIF, IIT, Madras, for the data collection. MKK thanks the Council of Scientific and Industrial Research, New Delhi, India, for providing financial support [project No.03 (1200)/11/EMR-II].

References

Asiri, A. M., Khan, S. A., Tan, K. W. & Ng, S. W. (2010). Acta Cryst. E66, o1765.  [CSD] [CrossRef] [IUCr Journals]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Krishnakumar, M., Sudhahar, S., Silambarasan, A., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3268.  [CSD] [CrossRef] [IUCr Journals]
Nalwa, H. S. & Miyata, S. (1997). In Nonlinear Optics of Organic Molecules and Polymers. Boca Raton: CRC Press.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
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]
Sudhahar, S., Krishnakumar, M., Sornamurthy, B. M., Chakkaravarthi, G. & Mohankumar, R. (2013). Acta Cryst. E69, o279.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1609  [ doi:10.1107/S1600536813026779 ]

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