Bis(trimethyl­ammonium) naphthalene-1,5-disulfonate

Jin, Y.

doi:10.1107/S1600536811052718

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 (C-C) = 0.002 Å
R = 0.041
wR = 0.109
Data-to-parameter ratio = 19.0
Details

Bis(trimethylammonium) naphthalene-1,5-disulfonate

Yu Jin ^a ^*

^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⁺·C₁₀H₆S₂O₆^2-, contains a half-anion, which is completed by inversion symmetry, and one cation. The cations and anions are associated via strong N-HO(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); Zhang et al. (2008, 2009, 2010); Fu et al. (2009). For a related structure, see: Wang & Yang (2011).

Experimental

Crystal data

2C₃H₁₀N⁺·C₁₀H₆O₆S₂^2-
M_r = 406.51
Monoclinic, P 2₁ /c
a = 8.3428 (17) Å
b = 10.502 (2) Å
c = 11.742 (2) Å
= 105.81 (3)°
V = 989.8 (3) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.489, T_max = 1.000
10031 measured reflections
2265 independent reflections
2016 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.109
S = 1.10
2265 reflections
119 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.36 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1EO2ⁱ	0.91	1.81	2.718 (2)	173
C1-H1CO1	0.96	2.43	3.372 (3)	166
C2-H2BO3ⁱⁱ	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); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, C. & Yang, S. L. (2011). Acta Cryst. E67, o1847.
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, W., Chen, L.-Z., Xiong, R.-G., Nakamura, T. & Huang, S. D. (2009). J. Am. Chem. Soc. 131, 12544-12545.
Zhang, W., Xiong, R.-G. & Huang, S. D. (2008). J. Am. Chem. Soc. 130, 10468-10469.
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.

organic compounds