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

Wu, J.-M.; Guo, W.; Li, C.-P.

doi:10.1107/S1600536811014140

Volume 67
Part 5
Page o1189
May 2011

Received 13 April 2011
Accepted 15 April 2011
Online 22 April 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.005 Å
R = 0.050
wR = 0.129
Data-to-parameter ratio = 11.9
Details

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

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

^aCollege of Chemistry, Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Tianjin Normal University, Tianjin 300387, People's Republic of China
Correspondence e-mail: tjnulicp@gmail.com

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 [pi] and [pi] - [pi] 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, P 2₁ /c
a = 5.7621 (9) Å
b = 15.250 (3) Å
c = 16.640 (3) Å
= 105.023 (5)°
V = 1412.2 (4) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.129
S = 1.08
2496 reflections
209 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C3-H3Cg2ⁱ	0.93	2.94	3.765 (4)	149
C4-H4Cg4	0.93	2.92	3.616 (3)	133
Symmetry code: (i) $[x-1, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: SU2269 ).

Acknowledgements

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

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Guo, W., Yang, Y.-Y. & Du, M. (2010). Inorg. Chem. Commun. 13 863-866.
Klingele, M. H. & Brooker, S. (2004). Eur. J. Org. Chem. pp. 3422-3434.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, Y.-Y., Guo, W. & Du, M. (2010). Inorg. Chem. Commun. 13 1195-1198.

organic compounds