2-[4-(4-Methoxy­phen­yl)-5-(2-pyrid­yl)-4H-1,2,4-triazol-3-yl]phenol

Mei-An Zhu; Zhao-Di Liu; Shu-Ping Zhang; Ying Wei; Si-Chang Shao

doi:10.1107/S1600536809022223

. 2009 Jun 27;65(Pt 7):o1690. doi: 10.1107/S1600536809022223

2-[4-(4-Methoxyphenyl)-5-(2-pyridyl)-4H-1,2,4-triazol-3-yl]phenol

Mei-An Zhu ^a, Zhao-Di Liu ^a, Shu-Ping Zhang ^a, Ying Wei ^a, Si-Chang Shao ^a,^*

PMCID: PMC2969267 PMID: 21582946

Abstract

In the title compound, C₂₀H₁₆N₄O₂, the benzene rings of the 2-hydroxyphenyl and 4-methoxylphenyl groups form dihedral angles of 64.02 (8) and 77.39 (7)°, respectively, with the mean plane of the triazole ring. The dihedral angle between the triazole ring mean plane and the pyridyl ring is 9.61 (8)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into zigzag chains propagating in [010].

Related literature

For the potential antifungal and antibacterial properties of 1,2,4-triazoles, see: Collin, et al. (2003 ▶); Papakonstantinou-Garoufalias, et al. (2002 ▶). For the synthesis of the title compound, see: Zhang et al. (2004 ▶). For related structures, see: Zhang et al. (2004 ▶); Zhang, Liu, Ma et al. (2005 ▶); Zhang, Liu, Yang et al. (2005 ▶); Zhu et al. (2000 ▶).

Experimental

Crystal data

C₂₀H₁₆N₄O₂
M _r = 344.37
Monoclinic,
a = 10.0842 (9) Å
b = 10.4903 (9) Å
c = 16.7214 (14) Å
β = 94.658 (2)°
V = 1763.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.10 × 0.10 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.991, T _max = 0.993
8997 measured reflections
3278 independent reflections
2734 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.110
S = 1.04
3278 reflections
238 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); 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/S1600536809022223/su2120sup1.cif

e-65-o1690-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022223/su2120Isup2.hkl

e-65-o1690-Isup2.hkl^{(160.8KB, 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
O1—H1O⋯N1ⁱ	0.938 (18)	1.759 (19)	2.6937 (16)	174.2 (16)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Education Office of Anhui Province, People’s Republic of China, for research grant No. KJ2009A047Z.

supplementary crystallographic information

Comment

Molecules containing a 1,2,4-triazole moiety have elicited considerable interest among medicinal chemists because they display a wide range of antifungal (Collin et al., 2003) and antibacterial (Papakonstantinou-Garoufalias et al., 2002) activities. We have synthesed and reported the crystal structures of various 1,2,4-triazole ligands and their metal complexes (Zhang et al., 2004; Zhang, Liu, Ma et al., 2005; Zhang, Liu, Yang et al., 2005; Zhu et al., 2000). As an extension of our work on the structural characterization of triazole derivatives, we report herein on the crystal structure of the title compound.

In the title compound the pyridyl ring and the benzene rings lie in a propeller arrangement around the central 1,2,4-triazole ring (Fig. 1), thereby minimizing the steric effects among these rings. The benzene rings of the 2-hydroxyphenyl and 4-methoxylphenyl groups are inclined to the mean plane of the triazole ring by 64.02 (8) and 77.39 (7)°, respectively. In contrast the pyridyl ring is inclined to the triazole ring by 9.61 (8)°.

In the crystal structure intermolecular O–H···N hydrogen bonds, involving hydroxyl O1-H1O and a triazole N-atom, N1, link the molecules into zigzag chains propagating in the [010] direction (Fig. 2 and Table 1).

Experimental

The title compound was synthesized according to a literature method (Zhang et al., 2004). Equivalent amounts of p-methoxylphenylphosphazoanilide and N-(2-pyridoyl)-N'-(2-Hydroxyphenyl)hydrazine were reacted in N,N'-dimethylaniline for 3 h at 463 K, with stirring. Colourless block-shaped crystals were obtained by slow evaporation of an acetone solution. The crystals were collected and dried in a vacuum desiccator using anhydrous CaCl₂ (yield 52%).