3-(2-Pyrid­yl)-5-(4-pyrid­yl)-4-(p-tol­yl)-1H-1,2,4-triazole

Lu-Tong Yuan; Hai Zhang; Zuo-Xiang Wang; Zhi-Rong Qu

doi:10.1107/S1600536809016432

. 2009 May 7;65(Pt 6):o1225. doi: 10.1107/S1600536809016432

3-(2-Pyridyl)-5-(4-pyridyl)-4-(p-tolyl)-1H-1,2,4-triazole

Lu-Tong Yuan ^a, Hai Zhang ^b, Zuo-Xiang Wang ^b, Zhi-Rong Qu ^b,^*

PMCID: PMC2969765 PMID: 21583093

Abstract

In the molecule of the title compound, C₁₉H₁₅N₅, the dihedral angles formed by the plane of the triazole ring with those of the 2-pyridyl, 4-pyridyl and p-tolyl rings are 28.12 (10), 34.62 (10) and 71.43 (9)°, respectively. The crystal structure is consolidated by C—H⋯π hydrogen-bonding interactions and by π–π stacking interactions, with a centroid–centroid distance of 3.794 (4) Å.

Related literature

For the pharmaceutical and agricultural applications of triazoles, see: Grénman et al. (2003 ▶). For general background on the coordination chemistry of triazoles, see: Haasnoot (2000 ▶); Klingele & Brooker (2003 ▶); Beckmann & Brooker (2003 ▶). For the synthesis of the title compound, see: Erwin (1958 ▶).

Experimental

Crystal data

C₁₉H₁₅N₅
M _r = 313.36
Monoclinic,
a = 5.6104 (11) Å
b = 16.312 (3) Å
c = 16.902 (4) Å
β = 105.07 (3)°
V = 1493.6 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.982, T _max = 0.983
13896 measured reflections
2918 independent reflections
1734 reflections with I > 2σ(I)
R _int = 0.105

Refinement

R[F ² > 2σ(F ²)] = 0.071
wR(F ²) = 0.159
S = 1.07
2918 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.26 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/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809016432/rz2317sup1.cif

e-65-o1225-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016432/rz2317Isup2.hkl

e-65-o1225-Isup2.hkl^{(143.2KB, 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
C11—H11A⋯Cg1ⁱ	0.93	2.79	3.630 (4)	150
C12—H12A⋯Cg3	0.93	2.90	3.532 (4)	126
C14—H14A⋯Cg1ⁱⁱ	0.93	2.76	3.628 (4)	156
C18—H18A⋯Cg2ⁱⁱⁱ	0.93	2.78	3.615 (4)	149
C19—H19C⋯Cg3^iv	0.96	3.08	3.698 (4)	124

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1, Cg2 and Cg3 are the centroids of the N1–N3/C1,C2, N4/C3–C7 and N5/C8–C12 rings, respectively.

Table 2. π–π Stacking interaction geometry.

Group 1	Group 2	α (°)	DCC (Å)	τ (°)
Cg2	Cg2ⁱ	0.0	3.794 (3)	31.30

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Symmetry code: (i) 3 − x, 1 − y, 2 − z. α is the dihedral angle between the planes, DCC is the length of the centroid–centroid vector, τ is the angle subtended by the plane normal to CC and Cg2 is the centroid of ring N5/C8–C12.

Acknowledgments

This work was supported by the Technical Fund Financing Projects (grant Nos. 9207042464 and 9207041482) from Southeast University to ZRQ.

supplementary crystallographic information

Comment

The main interest in triazoles lies in their pharmaceutical and agricultural applications (Grénman et al., 2003). The utilization of 1,2,4-triazole derivatives as bridging ligands in transition-metal complexes is currently of considerable interest because of the fact that it represents a hybrid of pyrazole and imidazole with regard to the arrangement of its heteroatoms, thus promising a rich and versatile coordination chemistry (Haasnoot, 2000; Klingele & Brooker, 2003; Beckmann & Brooker, 2003). We report here the crystal structure of the title compound, which is a substituted 1,2,4-triazole synthesized by the reaction of 4,4'-dimethylphenylphosphazoanilide with N-(2-pyridyl)-N'-(4-pyridyl)hydrazine in o-dichlorobenzene (Erwin, 1958).

The structure of the title compound (Fig. 1) features a dihedral angle of 28.12 (10)° between the 2-pyridyl and triazole rings, a dihedral angle of 34.62 (10)° between the 4-pyridyl and triazole rings, and a dihedral angle of 71.43 (9) ° between the p-tolyl and the triazole rings. The crystal structure is stabilized by C—H···π hydrogen interactions (Table 1) and π–π stacking interactions (Table 2).

Experimental

A mixture of 4,4'-dimethylphenylphosphazoanilide (3.60 g, 14.9 mmol) and N-(2-pyridyl)-N'-(4-pyridyl)hydrazine (3.00 g, 12.4 mmol) in o-dichlorobenzene (30 ml) was refluxed for 3 h, then conc. HCl (5 ml) and H₂O (5 ml) were added to the system after the removal of the solvent under reduced pressure. After refluxing for 1 h, the mixture was filtered and the fietrate was neutralized with K₂CO₃ to pH 8–9 to achieve a white solid. Colourless crystals of the title compound suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.