4-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]pyridinium benzoate

Meng Ting Han; Yuan Zhang

doi:10.1107/S1600536811001358

. 2011 Jan 22;67(Pt 2):o447. doi: 10.1107/S1600536811001358

4-[5-(Pyridin-4-yl)-1,3,4-oxadiazol-2-yl]pyridinium benzoate

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

PMCID: PMC3051668 PMID: 21523110

Abstract

In the title compound, C₁₂H₉N₄O⁺·C₇H₅O₂ ⁻, π–π stacking interactions [centroid–centroid distance = 3.6275 (14) Å] stabilize the crystal structure. The dihedral angles between the central ring and the terminal rings are 3.27 (12) and 10.30 (13)°.

Related literature

For background to the development of ferroelectric compounds, see: Haertling et al. (1999 ▶); Homes et al. (2001 ▶). For the synthesis of a variety of compounds with potential piezoelectric and ferroelectric properties, see: Ye et al. (2006 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C₁₂H₉N₄O⁺·C₇H₅O₂ ⁻
M _r = 346.34
Monoclinic,
a = 20.459 (4) Å
b = 7.1958 (14) Å
c = 11.249 (2) Å
β = 90.53 (3)°
V = 1656.0 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 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 = 0.854, T _max = 1.000
16725 measured reflections
3808 independent reflections
2248 reflections with I > 2σ(I)
R _int = 0.064

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.171
S = 1.02
3808 reflections
236 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 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/S1600536811001358/jh2244sup1.cif

e-67-0o447-sup1.cif^{(19.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001358/jh2244Isup2.hkl

e-67-0o447-Isup2.hkl^{(186.7KB, 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	0.86	1.79	2.648 (2)	174
C8—H8⋯O1ⁱⁱ	0.93	2.48	3.371 (3)	161

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

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 (Ye et al., 2006; Zhang et al., 2008), 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 3.6 to 4.7), 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 (374 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 3.0 to 4.2).Herein, we report the synthesis and crystal structure of the title compound.

The asymmetric unit of (I) consists of one bpo cation and one benzoate anions. The π—π packing interaction of adjacent rings with Cg(1)—Cg(4), 3.6275 (14) A °; Cg(3)—Cg(3), 4.1148 (16) A °; [Cg(1), Cg(3) and Cg(4) are the centroids of rings, where Cg(1): O3/C13/N2/N3/C14; Cg(3): N4/C15–C19; Cg(4): C2–C7;],make great contribution to the stability of the crystal structure.

Experimental

A mix of 2,5-bis(4-pyridyl)-1,3,4-oxadiazole (2.24 g, 0.01 mol) and benzoate acid (2.44 g,0.02 mol) in methanol (20 ml) was stirred until clear. After several days, the title compound was formed and recrystallized from solution to afford colourlesss prismatic crystals suitable for X-ray analysis.