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

Yu-feng Wang

doi:10.1107/S1600536812019149

. 2012 May 5;68(Pt 6):o1619. doi: 10.1107/S1600536812019149

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

Yu-feng Wang ^a,^*

PMCID: PMC3379225 PMID: 22719423

Abstract

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—H⋯O and O—H⋯O 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,
a = 7.1301 (14) Å
b = 8.1773 (16) Å
c = 9.970 (2) Å
α = 75.58 (3)°
β = 75.10 (3)°
γ = 80.34 (3)°
V = 540.7 (2) Å³
Z = 1
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.059

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.107
S = 0.94
2475 reflections
154 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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 Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812019149/yk2053sup1.cif

e-68-o1619-sup1.cif^{(14.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019149/yk2053Isup2.hkl

e-68-o1619-Isup2.hkl^{(124KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812019149/yk2053Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4C⋯O2ⁱ	0.82 (2)	1.95 (2)	2.754 (3)	167 (3)
O4—H4B⋯O2ⁱⁱ	0.82 (2)	1.92 (2)	2.730 (3)	166 (3)
N1—H1D⋯O1ⁱⁱⁱ	0.86	2.00	2.768 (3)	149
N2—H2B⋯O4	0.86	1.78	2.628 (3)	169

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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

supplementary crystallographic information

Comment

The compounds exhibiting the dielectric-ferroelectric phase transition constitute an interesting class of materials, comprising organic and metal-organic coordination compounds, organic-inorganic hybrids and organic salts (Ye et al., 2009; Zhang et al., 2009). Unfortunately, the temperature dependence of dielectric constant of the title compound indicates that the permittivity is temperature-independent below the melting point (388 - 389 K) of the compound. Herein we descibe the crystal structure of this compound.

The asymmetric unit of the title compound consists of a 2-methylimidazolium cation, a half of naphthalene-1,5-disulfonate anion and a water molecule (Fig. 1). The cations, anions and water molecules are connected by N—H···O and O—H···O hydrogen bonds, which form the layers parallel to the (1 1 1) plane (Fig. 2 and Table 1).

Experimental

The title compound was obtained by the addition of naphthalene-1,5-disulfonic acid (2.88 g, 0.01 mol) to a solution of 2-methylimidazole (1.6 g, 0.02 mol) in water. Good quality single crystals were obtained by slow evaporation after two days (the chemical yield is 45%).