Bis(2-methyl-1H-imidazol-3-ium) naphthalene-1,5-disulfonate dihydrate

Wang, Y.

doi:10.1107/S1600536812019149

Volume 68
Part 6
Page o1619
June 2012

Received 11 April 2012
Accepted 28 April 2012
Online 5 May 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.055
wR = 0.107
Data-to-parameter ratio = 16.1
Details

Bis(2-methyl-1H-imidazol-3-ium) naphthalene-1,5-disulfonate dihydrate

Yu-feng Wang ^a ^*

^aOrdered Matter Science Research Center, Southeast University, Nanjing 211189, People's Republic of China
Correspondence e-mail: seuwei@126.com

The asymmetric unit of the title organic salt, 2C₄H₇N₂⁺·C₁₀H₆O₆S₂^2-·2H₂O, consists of a 2-methylimidazolium cation, a half of a naphthalene-1,5-disulfonate anion, which lies about a center of symmetry, and a water molecule. In the crystal, N-HO and O-HO hydrogen bonds link the cations, anions and water molecules into the layers parallel to (111).

Related literature

For general background to dielectric-ferroelectric phase transitions, see: Ye et al. (2009); Zhang et al. (2009). For the structures of naphthalene-1,5-disulfonate salts with N-heterocyclic cations, see: Janczak & Perpétuo (2008); Wang et al. (2008).

Experimental

Crystal data

2C₄H₇N₂⁺·C₁₀H₆O₆S₂^2-·2H₂O
M_r = 488.53
Triclinic, $[P \overline 1]$
a = 7.1301 (14) Å
b = 8.1773 (16) Å
c = 9.970 (2) Å
= 75.58 (3)°
= 75.10 (3)°
= 80.34 (3)°
V = 540.7 (2) Å³
Z = 1
Mo K radiation
= 0.30 mm^-1
T = 293 K
0.23 × 0.22 × 0.18 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T_min = 0.933, T_max = 0.947
5695 measured reflections
2475 independent reflections
1490 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.107
S = 0.94
2475 reflections
154 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4CO2ⁱ	0.82 (2)	1.95 (2)	2.754 (3)	167 (3)
O4-H4BO2ⁱⁱ	0.82 (2)	1.92 (2)	2.730 (3)	166 (3)
N1-H1DO1ⁱⁱⁱ	0.86	2.00	2.768 (3)	149
N2-H2BO4	0.86	1.78	2.628 (3)	169
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y-1, z; (iii) -x, -y+1, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2053 ).

Acknowledgements

The author is grateful to the starter fund of Southeast University for the purchase of the diffractometer.

References

Janczak, J. & Perpétuo, G. J. (2008). Acta Cryst. C64, o91-o94.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, Z.-L., Jin, L.-Y. & Wei, L.-H. (2008). Acta Cryst. E64, o674.
Ye, H. Y., Fu, D. W., Zhang, Y., Zhang, W., Xiong, R. G. & Huang, S. P. (2009). J. Am. Chem. Soc. 131, 42-43.
Zhang, W., Cheng, L. Z., Xiong, R. G., Nakamura, T. & Huang, S. P. (2009). J. Am. Chem. Soc. 131, 12544-12545.

organic compounds

Bis(2-methyl-1H-imidazol-3-ium) naphthalene-1,5-disulfonate dihydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References