Dimeth­yl(4-methyl­phen­yl)ammonium naphthalene-1,5-disulfonate dihydrate

Bin Wei

doi:10.1107/S1600536811037068

. 2011 Sep 17;67(Pt 10):o2678. doi: 10.1107/S1600536811037068

Dimethyl(4-methylphenyl)ammonium naphthalene-1,5-disulfonate dihydrate

Bin Wei ^a,^*

PMCID: PMC3201563 PMID: 22065142

Abstract

The asymmetric unit of the organic–inorganic hybrid salt, 2C₉H₁₄N⁺·C₁₀H₆O₆S₂ ²⁻·2H₂O, consists of one dimethyl(4-methylphenyl)ammonium cation, one half of a naphthalene-1,5-disulfonate anion lying on a crystallographic centre of inversion, and one water molecule. In the crystal, O—H⋯O(S) and N—H⋯OH₂ hydrogen bonds link the cations and anions forming ring motifs.

Related literature

The title compound was obtained during attempts to obtain dielectric-ferroelectric materials. For general background to ferroelectric metal-organic frameworks, see: Wu et al. (2011 ▶); Fu et al. (2009 ▶); Ye et al. (2006 ▶); Zhang et al. (2008 ▶); Zhang et al. (2010 ▶).

Experimental

Crystal data

2C₉H₁₄N⁺·C₁₀H₆O₆S₂ ²⁻·2H₂O
M _r = 594.74
Triclinic,
a = 9.2660 (19) Å
b = 9.882 (2) Å
c = 10.260 (2) Å
α = 109.59 (3)°
β = 115.79 (3)°
γ = 98.39 (3)°
V = 748.3 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.955, T _max = 0.955
7762 measured reflections
3421 independent reflections
2951 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.115
S = 1.06
3421 reflections
197 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.34 e Å⁻³

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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811037068/jh2329sup1.cif

e-67-o2678-sup1.cif^{(16.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037068/jh2329Isup2.hkl

e-67-o2678-Isup2.hkl^{(167.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037068/jh2329Isup3.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—H4B⋯O3ⁱ	0.85 (3)	1.93 (3)	2.778 (3)	176 (3)
O4—H4B⋯S1ⁱ	0.85 (3)	2.96 (3)	3.753 (3)	157 (2)
N1—H10⋯O4ⁱⁱ	0.89 (2)	1.84 (2)	2.723 (2)	174.2 (19)
O4—H4A⋯O1ⁱⁱⁱ	0.84 (3)	2.01 (3)	2.846 (2)	171 (2)
O4—H4A⋯S1ⁱⁱⁱ	0.84 (3)	2.87 (3)	3.6569 (18)	156 (2)

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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

Dielectric-ferroelectric constitute an interesting class of materials, comprising organic ligands, metal-organic coordination compounds and organic-inorganic hybrids(Fu et al., 2009; Zhang et al., 2010; Zhang et al., 2008; Ye et al., 2006). Unfortunately,the dielectric constant of the title compound as a function of temperature indicates that the permittivity is basically temperature-independent, below the melting point (385k-387k) of the compound, we have found that cyclohexylammonium 4-methoxy-benzoate has no dielectric disuniform from 80 K to 405 K. Herein we descibe the crystal structure of this compound.

Regarding its crystal structure,the asymmetric unit of the title compound consists of a dimethyl(4-methylphenyl)ammonium cation, a half of naphthalene-1,5-disulfonate anion and a water molecule(Fig. 1). The free water molecules connected cations and anions by intermolecular hydrogen bonds involving O—H···S, O—H···O and N—H···O which makes great contribution to the stability of the crystal structure,and these hydrogen bonds link the cations, water molecules and anions into a chains along the c axis(Fig. 2 and Tab. 1).

Experimental

The title compound was obtained by the addition of naphthalene-1,5-disulfonate acid (3.62 g, 0.01 mol) to a solution of dimethyl(4-methylphenyl)amine (2.72 g, 0.02 mol) in water, in the stoichiometric ratio 1: 2. Good quality single crystals were obtained by slow evaporation after two days(the chemical yield is 35%).