4-Meth­oxy­anilinium hexa­fluoro­phosphate monohydrate

Yong-le Yang; Xue-qun Fu

doi:10.1107/S1600536810022348

. 2010 Jun 23;66(Pt 7):o1726. doi: 10.1107/S1600536810022348

4-Methoxyanilinium hexafluorophosphate monohydrate

Yong-le Yang ^a, Xue-qun Fu ^a,^*

PMCID: PMC3006782 PMID: 21587943

Abstract

In the structure of the title compound, C₇H₁₀NO⁺·PF₆ ⁻·H₂O, the protonated 4-methoxyanilinium cations and hexafluorophosphate anions are bridged by the water molecule via N—H⋯O and O—H⋯F hydrogen bonds. The resulting zigzag chains extend along the c axis. In addition, C—H⋯π interactions are observed in the crystal packing.

Related literature

The title compound was studied as part of our search for ferroelectric compounds, which usually have a phase transition. For background to phase-transition materials, see: Li et al. (2008 ▶); Zhang et al. (2009 ▶); Fu (2009 ▶).

Experimental

Crystal data

C₇H₁₀NO⁺·PF₆ ⁻·H₂O
M _r = 287.15
Monoclinic,
a = 15.152 (3) Å
b = 5.079 (1) Å
c = 14.758 (3) Å
β = 94.26 (3)°
V = 1132.6 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 298 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.939, T _max = 0.939
11166 measured reflections
2602 independent reflections
2083 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.145
S = 1.06
2602 reflections
199 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.43 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: PRPKAPPA (Ferguson, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810022348/im2206sup1.cif

e-66-o1726-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022348/im2206Isup2.hkl

e-66-o1726-Isup2.hkl^{(127.8KB, 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—H1C⋯O1W	0.84 (3)	2.06 (3)	2.896 (3)	172 (3)
N1—H1A⋯O1Wⁱ	0.92 (3)	2.00 (3)	2.917 (3)	172 (3)
N1—H1B⋯F3ⁱⁱ	0.87 (3)	2.32 (3)	3.056 (5)	142 (2)
N1—H1B⋯F1ⁱⁱⁱ	0.87 (3)	2.49 (3)	3.049 (5)	123 (2)
O1W—H1WB⋯F6^iv	0.85 (2)	2.21 (4)	2.91 (2)	139 (3)
O1W—H1WB⋯F4^v	0.85 (2)	2.57 (4)	3.04 (3)	116 (3)
C7—H7B⋯Cg1^vi	0.96	3.18	4.013 (5)	146

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

Acknowledgments

The authors are grateful to the Starter Fund of Southeast University for financial support in purchasing the X-ray diffractometer.

supplementary crystallographic information

Comment

As a continuation of our study of dielectric-ferroelectric materials, including organic ligands (Li et al., 2008), metal-organic coordination compounds (Zhang et al., 2009) and organic-inorganic hybrid materials, we studied the dielectric properties of the title compound. Unfortunately, there was no distinct anomaly observed from 93 K to 350 K, suggesting that this compound should be not a real ferroelectric material or there may be no distinct phase transition occurred within the measured temperature range. The crystal structure of 4-methoxyanilinium bromide is known (Fu, 2009). In this article, the crystal structure of the title compound is presented.

The asymmetric unit of the title compound consists of an almost planar 4-methoxyanilinium cation with a mean deviation from the plan of 0.0512 Å, a disordered hexafluorophosphate anion and a water molecule (Fig.1). N—H···F, N—H···O and O—H···F hydrogen bonds link the cations, anions and water molecules to chains along c axis (Fig.2). The C—H···π interactions with a C7···Cg1 distance of 4.013 (5) Å are also observed in the crystal packing.

Experimental

1.23 g (10 mmol) 4-Methoxyaniline was dissolved in 10 ml e thanol, to which hexafluorophosphoric acid in aqueous solution (70% w/w) was then added under stirring until the pH of the solution was ca 6. Ethanol was added until all suspended substrates disappeared. Single crystals of the title compound were prepared by slow evaporation of the acidic solution at room temperature of the acidic solution after 3 days giving a yield of 85%.