3,4-Bis(2-pyrid­yl)-5-(3-pyrid­yl)-4H-1,2,4-triazole

Jing-Min Wu; Wei Guo; Cheng-Peng Li

doi:10.1107/S1600536811014140

. 2011 Apr 22;67(Pt 5):o1189. doi: 10.1107/S1600536811014140

3,4-Bis(2-pyridyl)-5-(3-pyridyl)-4H-1,2,4-triazole

Jing-Min Wu ^a, Wei Guo ^a, Cheng-Peng Li ^a,^*

PMCID: PMC3089253 PMID: 21754491

Abstract

In the title molecule, C₁₇H₁₂N₆, the 2-pyridyl rings in the 3- and 4-positions and the 3-pyridyl ring in the 5-position make dihedral angles of 29.78 (16), 67.06 (16) and 32.97 (16)°, respectively, with the triazole group. The dihedral angle between the two 2-pyridyl rings is 65.72 (15)°. The dihedral angles between the 3-pyridyl ring and the two 2-pyridyl rings in the 3- and 4-positions are 61.28 (15) and 63.11 (15)°, respectively. In the crystal, C—H⋯π and π–π interactions [centroid-centroid distance = 3.6248 (19) Å] link the molecules, forming a two-dimensional network.

Related literature

For the synthesis of the title compound, see: Klingele & Brooker (2004 ▶). For related structures and background references, see: Guo et al. (2010 ▶); Yang et al. (2010 ▶).

Experimental

Crystal data

C₁₇H₁₂N₆
M _r = 300.33
Monoclinic,
a = 5.7621 (9) Å
b = 15.250 (3) Å
c = 16.640 (3) Å
β = 105.023 (5)°
V = 1412.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.975, T _max = 0.982
6865 measured reflections
2496 independent reflections
1407 reflections with I > 2σ(I)
R _int = 0.046

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.129
S = 1.08
2496 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 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: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811014140/su2269sup1.cif

e-67-o1189-sup1.cif^{(18.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014140/su2269Isup2.hkl

e-67-o1189-Isup2.hkl^{(122.7KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 and Cg4 are the centroids of the N1/C8–C12 and N6/C13–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg2ⁱ	0.93	2.94	3.765 (4)	149
C4—H4⋯Cg4	0.93	2.92	3.616 (3)	133

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported financially by Tianjin Normal University (52X09004).

supplementary crystallographic information

Comment

In continuation of our work on tripyridine-substituted triazole derivatives (Guo et al., 2010; Yang et al., 2010), we now describe the synthesis and crystal structure of the title compound. It consists of two 2-pyridyl groups and one 3-pyridyl ring attached to a triazole ring (Fig. 1).

The three pyridyl rings in the 3-, 4-, and 5-positions deviate from the triazole ring by 29.78 (16)°, 67.06 (16)°, and 32.97 (16)°, respectively. The dihedral angle between the two 2-pyridyl groups is 65.72 (15)°. In addition, the dihedral angles between the 3-pyridyl ring and the two 2-pyridyl rings in the 3- and 4-positions are 61.28 (15)° and 63.11 (15)°, respectively.

In the crystal, there exists a π–π interaction involving the 2-pyridyl rings in 3-positions of molecules related by an inversion center [centroid-centroid distance = 3.6248 (19) Å]. The molecular packing is also stabilized by two types of C—H···π interactions; the intramolecular C4—H4···Cg4 [Cg4 is the centroid of pyridine ring (N6/C13-C17)] and the intermolecular C3—H3···Cg2ⁱ [Cg2 is the centroid of pyridine ring (N1/C8-C12)] interactions (see Table 1 and Fig. 2 for details). This leads to the formation of a two-dimensional network.

Experimental

The title compound was prepared from a mixture of N-(pyridin-2-yl)pyridine-2-carbothioamide and pyridine-3-carbohydrazide using the method described by Klingele et al. (2004).