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Volume 68 
Part 1 
Page o90  
January 2012  

Received 2 December 2011
Accepted 7 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.109
Data-to-parameter ratio = 19.0
Details
Open access

Bis(trimethylammonium) naphthalene-1,5-disulfonate

aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
Correspondence e-mail: jinyunihao@yahoo.cn

The asymmetric unit of the title compound, 2C3H10N+·C10H6S2O62-, contains a half-anion, which is completed by inversion symmetry, and one cation. The cations and anions are associated via strong N-H...O(sulfonate) hydrogen-bonding interactions, forming cation-anion-cation groups. Secondary interactions such as C-H(ammonium)...O(sulfonate) and van der Waals interactions link the cations and anions together in a three-dimensional crystal structure, with zigzag rows of cations lying between layers of anions.

Related literature

The title compound was investigated as part of our search for simple ferroelectric compounds. For general background to ferroelectric metal-organic frameworks, see: Ye et al. (2006[Ye, Q., Song, Y.-M., Wang, G.-X., Chen, K., Fu, D.-W., Hong Chan, P. W., Zhu, J.-S., Huang, S. D. & Xiong, R.-G. (2006). J. Am. Chem. Soc. 128, 6554-6555.]); Zhang et al. (2008[Zhang, W., Xiong, R.-G. & Huang, S. D. (2008). J. Am. Chem. Soc. 130, 10468-10469.], 2009[Zhang, W., Chen, L.-Z., Xiong, R.-G., Nakamura, T. & Huang, S. D. (2009). J. Am. Chem. Soc. 131, 12544-12545.], 2010[Zhang, W., Ye, H.-Y., Cai, H.-L., Ge, J.-Z., Xiong, R.-G. & Huang, S. D. (2010). J. Am. Chem. Soc. 132, 7300-7302.]); Fu et al. (2009[Fu, D.-W., Ge, J.-Z., Dai, J., Ye, H.-Y. & Qu, Z.-R. (2009). Inorg. Chem. Commun. 12, 994-997.]). For a related structure, see: Wang & Yang (2011[Wang, C. & Yang, S. L. (2011). Acta Cryst. E67, o1847.]).

[Scheme 1]

Experimental

Crystal data
  • 2C3H10N+·C10H6O6S22-

  • Mr = 406.51

  • Monoclinic, P 21 /c

  • a = 8.3428 (17) Å

  • b = 10.502 (2) Å

  • c = 11.742 (2) Å

  • [beta] = 105.81 (3)°

  • V = 989.8 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 293 K

  • 0.3 × 0.3 × 0.2 mm

Data collection
  • Rigaku Mercury CCD diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.489, Tmax = 1.000

  • 10031 measured reflections

  • 2265 independent reflections

  • 2016 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.109

  • S = 1.10

  • 2265 reflections

  • 119 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1E...O2i 0.91 1.81 2.718 (2) 173
C1-H1C...O1 0.96 2.43 3.372 (3) 166
C2-H2B...O3ii 0.96 2.31 3.232 (4) 162
Symmetry codes: (i) x+1, y, z; (ii) [x+1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2404 ).


Acknowledgements

The author thanks the Ordered Matter Science Research Center, Southeast University, for its excellent experimental conditions and its generous financial support.

References

Fu, D.-W., Ge, J.-Z., Dai, J., Ye, H.-Y. & Qu, Z.-R. (2009). Inorg. Chem. Commun. 12, 994-997.  [ISI] [CSD] [CrossRef] [ChemPort]
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, C. & Yang, S. L. (2011). Acta Cryst. E67, o1847.  [CSD] [CrossRef] [details]
Ye, Q., Song, Y.-M., Wang, G.-X., Chen, K., Fu, D.-W., Hong Chan, P. W., Zhu, J.-S., Huang, S. D. & Xiong, R.-G. (2006). J. Am. Chem. Soc. 128, 6554-6555.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhang, W., Chen, L.-Z., Xiong, R.-G., Nakamura, T. & Huang, S. D. (2009). J. Am. Chem. Soc. 131, 12544-12545.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhang, W., Xiong, R.-G. & Huang, S. D. (2008). J. Am. Chem. Soc. 130, 10468-10469.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhang, W., Ye, H.-Y., Cai, H.-L., Ge, J.-Z., Xiong, R.-G. & Huang, S. D. (2010). J. Am. Chem. Soc. 132, 7300-7302.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o90  [ doi:10.1107/S1600536811052718 ]

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