4-Methyl­anilinium p-toluene­sulfonate

Rui-jun Xu

doi:10.1107/S1600536810021537

. 2010 Jun 26;66(Pt 7):o1794. doi: 10.1107/S1600536810021537

4-Methylanilinium p-toluenesulfonate

Rui-jun Xu ^a,^*

PMCID: PMC3006818 PMID: 21588004

Abstract

The crystal structure of the title compound, C₇H₁₀N⁺·C₇H₇O₃S⁻, displays strong N—H⋯O and N—H⋯S hydrogen bonding between the ammonium group and the p-toluenesulfonate anion, linking the cations and anions into chains along the b axis.

Related literature

For background to dielectric–ferroelectric materials, see: Hang et al. (2009 ▶); Li et al. (2008 ▶).

Experimental

Crystal data

C₇H₁₀N⁺·C₇H₇O₃S⁻
M _r = 279.35
Monoclinic,
a = 5.775 (4) Å
b = 9.026 (5) Å
c = 13.350 (8) Å
β = 96.344 (9)°
V = 691.6 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.929, T _max = 1.000
6641 measured reflections
3136 independent reflections
2876 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.093
S = 0.99
3136 reflections
174 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.23 e Å⁻³
Absolute structure: Flack (1983 ▶), 1448 Friedel pairs
Flack parameter: 0.05 (8)

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: PRPKAPPA (Ferguson, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021537/fj2307sup1.cif

e-66-o1794-sup1.cif^{(17.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021537/fj2307Isup2.hkl

e-66-o1794-Isup2.hkl^{(153.9KB, hkl)}

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
N1—H1D⋯O1ⁱ	0.89	2.31	3.170 (3)	164
N1—H1D⋯O2ⁱ	0.89	2.33	2.824 (3)	115
N1—H1D⋯S1ⁱ	0.89	2.81	3.570 (3)	144
N1—H1E⋯O1ⁱⁱ	0.89	1.96	2.829 (3)	165
N1—H1F⋯O3ⁱⁱⁱ	0.89	2.02	2.785 (3)	143

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

Acknowledgments

The author thanks Southeast University for financial support of this research and is grateful for the guidance of Professor Wen Zhang.

supplementary crystallographic information

Comment

Dielectric-ferroelectric as an interesting class of materials, there are organic ligands (Li et al., 2008), metal-organic coordination compounds (Hang et al., 2009) and organic-inorganic hybrid. In this article, the preparation and crystal structure of the title compound have been presented. It should be not a real ferroelectrics or there may be no distinct phase transition occurred within the measured temperature range. Similarly, below the melting point (477 K) of the compound, the dielectric constant as a function of temperature also goes smoothly, and there is no dielectric anomaly observed.

The asymmetric unit of the title compound contains a (CH₃—C₆H₄—NH₃⁺) cation and an (CH₃—C₆H₄—SO₃^-) anion (Fig.1). The strong N—H···S, N—H···O hydrogen bonds involving H1D and H1E (N1···S1 3.570 (3) Å and N1···O1 2.829 (3) Å) are beneficial to the stability of the crystal structure and link the cations and anions to chains along the b axis (Fig. 2 and Tab. 1).

Experimental

The title compound was obtained by the addition of p-toluenesulfonic acid (3.78 g, 0.022 mol) to a solution of 4-methylaniline (2.14 g, 0.02 mol) in ethanol, in the stoichiometric ratio 1.1:1. After two weeks, good quality single crystals were obtained by slow evaporation.