(3-Pyrid­yl)methanaminium 4-nitro­phenolate 4-nitro­phenol solvate

Yuan Zhang; Meng Ting Han

doi:10.1107/S1600536810021902

. 2010 Jun 16;66(Pt 7):o1649. doi: 10.1107/S1600536810021902

(3-Pyridyl)methanaminium 4-nitrophenolate 4-nitrophenol solvate

Yuan Zhang ^a,^*, Meng Ting Han ^a

PMCID: PMC3006836 PMID: 21587877

Abstract

In the crystal structure of the title compound, C₆H₉N₂ ⁺·C₆H₄NO₃ ⁻·C₆H₅NO₃, ions and molecules are connected via intermolecular N—H⋯O, N—H⋯N, O—H⋯O and C—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For background to the development of ferroelectric pure organic or inorganic compounds, see: Haertling et al. (1999 ▶); Homes et al. (2001 ▶). For our recent reports on the synthesis of a variety of compounds which have potential piezoelectric and ferroelectric properties, see: Fu et al. (2009 ▶); Hang et al. (2009 ▶).

Experimental

Crystal data

C₆H₉N₂ ⁺·C₆H₄NO₃ ⁻·C₆H₅NO₃
M _r = 386.36
Triclinic,
a = 6.3666 (13) Å
b = 7.4451 (15) Å
c = 21.262 (4) Å
α = 92.41 (3)°
β = 95.56 (3)°
γ = 113.99 (3)°
V = 912.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.825, T _max = 1.000
9547 measured reflections
4182 independent reflections
2896 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.140
S = 1.05
4182 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 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 datablocks I, global. DOI: 10.1107/S1600536810021902/jh2162sup1.cif

e-66-o1649-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810021902/jh2162Isup2.hkl

e-66-o1649-Isup2.hkl^{(204.9KB, 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—H1A⋯O2ⁱ	0.89	2.09	2.952 (2)	162
N1—H1B⋯O3ⁱⁱ	0.89	1.87	2.753 (2)	169
N1—H1C⋯N2ⁱⁱⁱ	0.89	2.16	2.866 (2)	136
O4—H4A⋯O3	0.96	1.58	2.5385 (19)	173
C1—H1D⋯O5^iv	0.93	2.52	3.229 (3)	133
C2—H2A⋯O6^v	0.93	2.58	3.327 (3)	138
C8—H10A⋯O4ⁱⁱⁱ	0.93	2.54	3.462 (3)	169

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

Acknowledgments

The authors are grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

supplementary crystallographic information

Comment

At present, much attention in ferroelectric material field is focused on developing ferroelectric pure organic or inorganic compounds (Haertling et al. 1999; Homes et al. 2001). Recently we have reported the synthesis of a variety of compounds (Fu et al., 2009; Hang et al., 2009), which have potential piezoelectric and ferroelectric properties. In order to find more dielectric ferroelectric materials, we investigate the physical properties of the title compound(Fig. 1). The dielectric constant of the title compound as a function of temperature indicates that the permittivity is basically temperature-independent (dielectric constant equaling to 2.8 to 4.6), suggesting that this compound 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 (399 K) of the compound, the dielectric constant as a function of temperature also goes smoothly, and there is no dielectric anomaly observed (dielectric constant equaling to 2.8 to 4.6).Herein, we report the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. There are one 4-nitrophenolate anion, an substituted ammonium cation and a neutral 4-nitrophenol molecule in the asymmetric unit. Molecules of the title compound have normal geometric parameters. The bond lengths and angles are within their normal ranges. All pyridine rings are, of course, planar. As can be seen from the packing diagram (Fig. 2), molecules are connected via intermolecular C—H···O and O—H···N hydrogen bonds to form a three dimensional network. Dipole–dipole and van der Waals interactions are effective in the molecular packing.

Experimental

4-nitrophenol (2.085 g, 0.015 mol) was added slowly to a solution of pyridin-3-ylmethanamine (1.62 g, 0.015 mol) in methanol.After several days, the title compound was formed and recrystallized from solution to afford colourless prismatic crystals suitable for X-ray analysis.