2-(5-{6-[5-(Pyrazin-2-yl)-1H-1,2,4-triazol-3-yl]pyridin-2-yl}-1H-1,2,4-triazol-3-yl)pyrazine

Zhouqing Xu; Yanchun Sun; Qiang Wang

doi:10.1107/S1600536811034520

. 2011 Aug 27;67(Pt 9):o2457. doi: 10.1107/S1600536811034520

2-(5-{6-[5-(Pyrazin-2-yl)-1H-1,2,4-triazol-3-yl]pyridin-2-yl}-1H-1,2,4-triazol-3-yl)pyrazine

Zhouqing Xu ^a, Yanchun Sun ^b, Qiang Wang ^a,^*

PMCID: PMC3200783 PMID: 22064978

Abstract

In the title molecule, C₁₇H₁₁N₁₁, the five rings are almost coplanar [maxium deviation 0.1949 (1) Å]. The dihedral angles between the two pyrazine rings and the two triazole rings are 1.52 (4) and 2.51 (5)°, respectively. The central pyridine ring forms dihedral angles of 5.57 (1) and 1.71 (1)° with the two triazole rings. The crystal packing consists of a three-dimensional network structure generated by intermolecular N—H⋯N hydrogen bonds. The crystal structure is further consolidated by π–π stacking [centroid-to-centroid distances 3.599 (10) and 4.769 (13) Å].

Related literature

For the applications of compounds containing triazole subunits, see: Zhang et al. (2010 ▶); Fischer (2007 ▶); Ouellette et al. (2007 ▶). For a recent study, see: Xu et al. (2011 ▶). For the synthesis, see: Browne (1975 ▶); Klingele & Brooker (2004 ▶).

Experimental

Crystal data

C₁₇H₁₁N₁₁
M _r = 369.37
Monoclinic,
a = 10.751 (2) Å
b = 13.721 (3) Å
c = 11.385 (2) Å
β = 102.57 (3)°
V = 1639.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T _min = 0.905, T _max = 1.000
17628 measured reflections
3204 independent reflections
2896 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.125
S = 1.22
3204 reflections
259 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 datablock(s) I, global. DOI: 10.1107/S1600536811034520/ng5216sup1.cif

e-67-o2457-sup1.cif^{(17.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034520/ng5216Isup2.hkl

e-67-o2457-Isup2.hkl^{(157.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034520/ng5216Isup3.cml

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
N8—H34⋯N12ⁱ	0.96 (2)	1.92 (2)	2.817 (3)	155 (2)
N4—H35⋯N13ⁱⁱ	0.92 (2)	2.21 (2)	3.113 (3)	167 (2)

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

This work was supported by the Natural Science Research Programme of the Education Department of Henan Province (grant No. 2011 A150015), the Henan Polytechnic University Foundation for Youth (grant No. P051102) and the Henan Polytechnic University Foundation for Doctoral Teachers (grant No. B2010-65). The authors thank Dr D. Zhao for assistance with the data analysis.

supplementary crystallographic information

Comment

Compounds containing triazole subunits have been intensively studied owing to diverse biological properties and also to the ease of complexation (Zhang et al., 2010; Fischer, 2007; Ouellette et al., 2007). In continuation with a recent study (Xu et al., 2011), we report the title compound (Scheme I), 2-(5-(6-(5-(pyrazin-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-yl)-1H-1,2,4-triazol-3-yl)pyrazine.

The five rings are almost coplanar (maxium deviation = 0.1949 (1) Å). The dihedral angles between the two pyrazine rings and the two triazole rings are 1.52 (4) and 2.51 (5)°, respectively. The central pyridine ring forms dihedral angles of 5.57 (1) and 1.71 (1)° with the two triazole rings (Fig. 1). The crystal packing consists of a three-dimensional net structure generated by intermolecular N—H···N hydrogen bonds. The crystal structure is further consolidated by π–π stacking [centroid–centroid distances = 3.599 (10) and 4.769 (13) Å].

Experimental

2-(5-(6-(5-(pyrazin-2-yl)-1H-1,2,4-triazol-3-yl)pyridin-2-yl)-1H-1,2,4-triazol-3-yl)pyrazine was prepared according to Browne (1975) and Klingele & Brooker (2004). The crystals suitable for crystallographic analysis were grown by recrystallization from DMF and ethanol solution as colorless prism.