2,5-Bis[2-(2-methoxy­ethoxy)phen­yl]-1,3,4-oxadiazole

Xia Tian; Xiao-Li Zhen; Jian-Rong Han; Chang-Xin Ming; Shou-Xin Liu

doi:10.1107/S1600536809028931

. 2009 Jul 29;65(Pt 8):o2010. doi: 10.1107/S1600536809028931

2,5-Bis[2-(2-methoxyethoxy)phenyl]-1,3,4-oxadiazole

Xia Tian ^a, Xiao-Li Zhen ^a, Jian-Rong Han ^a,^*, Chang-Xin Ming ^a, Shou-Xin Liu ^b,^‡

PMCID: PMC2977367 PMID: 21583681

Abstract

In the title compound, C₂₀H₂₂N₂O₅, the central 1,3,4-oxadiazole ring is essentially planar [r.m.s. deviation from the best plane of 0.0011 Å] and makes dihedral angles of 4.10 (3) and 13.32 (4)° with the two benzene rings. In the crystal structure, the packing is stabilized by weak non-classical intermolecular C—H⋯N hydrogen bonds, which link the molecules into an extended network.

Related literature

For the optical and electronic properties of 1,3,4-oxadizole and its dericatives, see: Emi & Toru (2006 ▶). Liu et al. (1997 ▶); Peng et al. (2006 ▶); Satoshi et al. (2000 ▶). For reference geometrical data: see: Tian et al. (2009 ▶). For related structures, see: Orgzall et al. (2005 ▶).

Experimental

Crystal data

C₂₀H₂₂N₂O₅
M _r = 370.40
Monoclinic,
a = 7.7264 (15) Å
b = 13.886 (3) Å
c = 16.911 (3) Å
β = 96.42 (3)°
V = 1803.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.16 × 0.14 × 0.10 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.984, T _max = 0.990
13017 measured reflections
4290 independent reflections
3635 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.110
S = 1.04
4290 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.23 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/S1600536809028931/pv2184sup1.cif

e-65-o2010-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028931/pv2184Isup2.hkl

e-65-o2010-Isup2.hkl^{(210.2KB, 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
C5—H5⋯N2ⁱ	0.93	2.62	3.385 (2)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Foundation of Hebei University of Science & Technology (No. XL200746).

supplementary crystallographic information

Comment

The optical and electronic properties of 1,3,4-oxadizole have received great attention in the field of electroluminescence (Emi et al., 2006). A well known derivative of 1,3,4-oxadiazole, 2-(4-biphenyl)-5-(tert-butylphenyl)-1,3,4-oxadiazole (PBD), has been used as electron-injection material to improve the balance of charge carrier and to increase the photon/electron quantum efficiency (Liu et al., 1997) and the electron-transporting material in organic electroluminescence device (Satoshi et al., 2000). It has been demonstrated that modifying the side chains or inserting other heterocycles in 1,3,4-oxadizole system could result in good electroluminescent molecules as organic electroluminescence materials (Peng et al., 2006). As part of an investigation on potential electroluminescent molecules by modifying the side chains of 2,5-diaryl-1,3,4-oxadizole, we reporte here the synthesis and structure of the title compound, (I).

The molecular structure of (I) is presented in Fig. 1. The oxadizole ring (O3/C10/N1/N2/C11) is essentially planar, with an r.m.s. deviation for fitted atoms of 0.0011 Å. It makes dihedral angles of, 13.32 (4) and 4.10 (3)°, respectively, with the benzene rings (C4—C9) and (C12—C17). The crystal packing is stabilized by weak non-classical intermolecular C—H···N hydrogen bonds which link the molecules into an infinite network. The bond lengths and angles in (I) are within their normal ranges (Tian et al. 2009). The crystal structure of a 2,5-diaryl-1,3,4-oxadiazole derivative have been reported (Orgzall et al., 2005).

Experimental

2,5-Di(o-hydroxyphenyl)-1,3,4-oxadiazole (0.8 g, 3.0 mmol), NaH (0.5 g, 20 mmol) and 1-chloro-2-methoxyethane (0.75 g, 8 mmol) were added and dissolved in 50 ml of THF, the mixture was stirred refluxing for 10 h. giving a colourless precipitate. The product was isolated, recrystallized from ethyl acetate then dried in a vacuum to give the pure compound in 81% yield. colourless single crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of ethyl acetate solution at room temperature.