{4-[5-(4-tert-Butyl­phen­yl)-1,3,4-oxa­diazol-2-yl]phen­yl}methanol

Yu-Ling Zhao; Zhe Lv; Bin Tian; Zhe Hou; Zhong-Rong Geng

doi:10.1107/S1600536810052967

. 2011 Jan 8;67(Pt 2):o251. doi: 10.1107/S1600536810052967

{4-[5-(4-tert-Butylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}methanol

Yu-Ling Zhao ^a,^*, Zhe Lv ^a, Bin Tian ^a, Zhe Hou ^a, Zhong-Rong Geng ^b

PMCID: PMC3051771 PMID: 21522945

Abstract

In the title compound, C₁₉H₂₀N₂O₂, the 1,3,4-oxadiazole ring is almost coplanar with the two neighboring benzene rings [dihedral angles = 3.76 (4) and 5.49 (4)°]. In the crystal, molecules are connected by strong intermolecular O—H⋯N hydrogen bonds, forming chains parallel to the c axis.

Related literature

For the properties and applications of 1,3,4-oxadiazole derivatives, see: Hughes & Bryce (2005 ▶); Kim & Lee (2007 ▶); Kulkarni et al. (2004 ▶); Liang et al. (2003 ▶); Liou et al. (2006 ▶); Strukelj et al. (1995 ▶). For the biological activity of compounds containing the 1,3,4-oxadiazole moiety, see: Cacic et al. (2006 ▶); Mansour et al. (2003 ▶); Yar et al. (2007 ▶); Zhang et al. (2007 ▶). For synthesis of the intermediate, see Mashraqui et al. (2007 ▶).

Experimental

Crystal data

C₁₉H₂₀N₂O₂
M _r = 308.37
Monoclinic,
a = 16.3958 (18) Å
b = 6.0654 (7) Å
c = 16.7206 (19) Å
β = 102.289 (2)°
V = 1624.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 185 K
0.32 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.974, T _max = 0.993
8995 measured reflections
2886 independent reflections
1805 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.122
S = 0.98
2886 reflections
212 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 global, I. DOI: 10.1107/S1600536810052967/pk2290sup1.cif

e-67-0o251-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052967/pk2290Isup2.hkl

e-67-0o251-Isup2.hkl^{(141.7KB, 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
O1—H1⋯N2ⁱ	0.84	2.07	2.906 (3)	179

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by the Natural Science Foundation of Gansu Province (096RJZA086) and the project of students’ science and technology innovation funds (DXS2010–041) of Lanzhou Jiaotong University.

supplementary crystallographic information

Comment

It is well known that 1,3,4-oxadiazole derivatives have strong electron affinity and possess electron-transporting characteristics. They have been widely used as electroluminescent materials and as electron-transport materials in organic light-emitting diodes (OLEDs) (Strukelj et al., 1995; Kulkarni et al., 2004; Hughes & Bryce 2005). Due to its excellent electron transporting properties, the 1,3,4-oxadiazole unit has been embedded in larger compounds to improve the quantum efficiencies of OLEDs (Liang et al., 2003; Liou et al., 2006; Kim & Lee 2007). Moreover, the compounds containing 1,3,4-oxadiazole also exhibit beneficial biological activity, such as anti-inflammatory, antibacterial, anticancer, plant growth regulation, weed and worm killing, anti-HIV and other activities (Cacic et al., 2006; Mansour et al., 2003; Zhang et al., 2007; Yar et al., 2007).

The molecular structure of the title compound is shown in Fig.1. Bond lengths and angles in the molecule are within normal ranges. The 1,3,4-oxadiazole ring is almost coplanar with two neighboring benzene rings (dihedral angles between the 1,3,4-oxadiazole ring and two benzene rings are 3.76 (4)° and 5.49 (4)°. The crystal structure is stabilized by intermolecular O—H···N hydrogen bonds (Fig. 2), to form chains parallel to the c axis.

Experimental

The title compound was obtained by reacting 2-[4-(bromomethyl)phenyl]-5-(4-tert-butylphenyl)-1,3,4-oxadiazole and potassium hydroxide in N,N-dimethyllformamide. The intermediate, 2-[4-(bromomethyl)phenyl]-5-(4-tert-butylphenyl)-1,3,4-oxadiazole, was synthesized according to the method described by Mashraqui et al. (Mashraqui et al., 2007).

After dispersing potassium hydroxide (3.62 mmol) in N,N-dimethylformamide (30 ml) for 10 min, 2-[4-(bromomethyl)phenyl]-5-(4-tert-butylphenyl)- 1,3,4-oxadiazole (3.62 mmol) was added. The reaction vessel was refluxed for one day. Neutralization with saturated aqueous ammonium chloride (100 ml) followed by extraction with dichloromethane (100 ml) was performed, and the organic layer was dried over anhydrous magnesium sulfate. The concentrated crude product was purified with silica column chromatography to afford the title compound. m.p. 381–383 K. ¹H-NMR (500 MHz, CDCl₃): 8.12–8.05 (m, 4H, Ar—H), 7.56–7.52 (m, 4H, Ar—H), 4.81 (s, 2H, –CH₂–), 2.31 (s, 1H, –OH), 1.41 (s, 9H, –CH₃).

Colourless single crystals were obtained by slow evaporation of a methanolic solution at room temperature.