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Volume 68 
Part 1 
Page o212  
January 2012  

Received 9 November 2011
Accepted 9 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.054
wR = 0.156
Data-to-parameter ratio = 17.7
Details
Open access

Bis(3-hydroxypropanaminium) naphthalene-1,5-disulfonate

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

In the title molecular salt, 2C3H10NO+·C10H6O6S22-, the cations and anions are associated via N-H...O and O-H...O hydrogen-bonding interactions, giving rise to a three-dimensional structure with zigzag rows of cations lying between rows of anions. The asymmetric unit contains one cation and one half-anion, which is related to the remainder of the molecule by an inversion center.

Related literature

The title compound was studied as part of a 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. (2006). J. Am. Chem. Soc. 128, 6554-6555.]); Zhang et al. (2008[Zhang, W., Xiong, R.-G. & Huang, S.-P. D. (2008). J. Am. Chem. Soc. 130, 10468-10469.], 2009[Zhang, W., Li, Z.-C., Xiong, R.-G., Nakamura, T. & Huang, S.-P. (2009). J. Am. Chem. Soc. 131, 12544-12545.], 2010[Zhang, W., Ye, H.-Y., Cai, H.-L., Ge, J.-Z. & Xiong, R.-G. (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.]).

[Scheme 1]

Experimental

Crystal data
  • 2C3H10NO+·C10H6O6S22-

  • Mr = 438.51

  • Monoclinic, P 21 /c

  • a = 10.004 (2) Å

  • b = 8.8311 (18) Å

  • c = 11.183 (2) Å

  • [beta] = 92.79 (3)°

  • V = 986.8 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.32 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

  • 9820 measured reflections

  • 2268 independent reflections

  • 2135 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.156

  • S = 1.08

  • 2268 reflections

  • 128 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.58 e Å-3

  • [Delta][rho]min = -0.63 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O4-H4A...O1i 0.82 1.95 2.772 (3) 177
N1-H1D...O3ii 0.89 1.93 2.768 (3) 157
N1-H1C...O4iii 0.89 2.07 2.854 (3) 147
Symmetry codes: (i) x-1, y, z; (ii) [-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -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: EZ2272 ).


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]
Ye, Q., Song, Y.-M., Wang, G.-X., Chen, K. & Fu, D.-W. (2006). J. Am. Chem. Soc. 128, 6554-6555.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhang, W., Li, Z.-C., Xiong, R.-G., Nakamura, T. & Huang, S.-P. (2009). J. Am. Chem. Soc. 131, 12544-12545.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Zhang, W., Xiong, R.-G. & Huang, S.-P. 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. (2010). J. Am. Chem. Soc. 132, 7300-7302.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2012). E68, o212  [ doi:10.1107/S1600536811053141 ]

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