5-(Pyridin-2-yl)-3,3′-bi(1H-1,2,4-triazole)

Xu, Z.; Zhao, X.; Wang, Q.

doi:10.1107/S1600536811027449

Volume 67
Part 8
Page o2037
August 2011

Received 5 July 2011
Accepted 8 July 2011
Online 13 July 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.050
wR = 0.156
Data-to-parameter ratio = 11.9
Details

5-(Pyridin-2-yl)-3,3'-bi(1H-1,2,4-triazole)

Zhouqing Xu,^a Xinping Zhao ^b and Qiang Wang ^a ^*

^aThe Department of Physics-Chemistry, Henan Polytechnic University, Jiao Zuo, 454000, People's Republic of China, and ^bThe Hospital of Henan Polytechnic University, Jiao Zuo, 454000, People's Republic of China
Correspondence e-mail: wangqiang@hpu.edu.cn

In the title molecule, C₉H₇N₇, the two triazole rings are twisted by an angle of 3.8 (5)°; the central triazole ring is twisted by 32.3 (6)° with respect to the pyridyl ring. The crystal packing consists of layers generated by intermolecular N-HN hydrogen bonds.

Related literature

For related structures, see: Mai et al. (2009); Zhang et al. (2010). For the synthesis, see: Potts (1960); Wiley & Hart (1953).

Experimental

Crystal data

C₉H₇N₇
M_r = 213.22
Monoclinic, P 2₁ /c
a = 12.372 (3) Å
b = 7.5361 (15) Å
c = 10.007 (2) Å
= 93.670 (4)°
V = 931.1 (3) Å³
Z = 4
Mo K radiation
= 0.11 mm^-1
T = 296 K
0.24 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.975, T_max = 0.979
5150 measured reflections
1832 independent reflections
1072 reflections with I > 2(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.156
S = 0.94
1832 reflections
154 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N6-H1N4ⁱ	0.98 (4)	1.93 (4)	2.891 (3)	165 (3)
N2-H2N3ⁱⁱ	0.99 (3)	1.90 (4)	2.878 (3)	167 (3)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); 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 data and figures for this paper are available from the IUCr electronic archives (Reference: NG5195 ).

Acknowledgements

This work was supported by the Natural Science Research Program of the Education Department of Henan Province (2011 A150015), the Henan Polytechnic University Foundation for Youths (P051102) and the Henan Polytechnic University Foundation for Doctor Teachers (B2010-65). The authors thank Dr D. Zhao for help with the diffraction analysis.

References

Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Mai, X., Xia, H.-Y., Cao, Y.-S., Lu, X.-S. & Liao, Y.-J. (2009). Z. Kristallogr. New Cryst. Struct. 224, 547-548.
Potts, K. T. (1960). Chem. Rev. 61, 87-127.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wiley, R. H. & Hart, A. J. (1953). J. Org. Chem. 18, 1368-1371.
Zhang, C.-H., Zhang, J.-J., Li, W. & Liu, B.-H. (2010). Z. Kristallogr. New Cryst. Struct. 225, 599-600.

organic compounds