5-p-Tolyl-1H-tetra­zole

Hu, D.-Y.; Chu, X.-W.; Qu, Z.-R.

doi:10.1107/S1600536809036411

Volume 65
Part 10
Page o2463
October 2009

Received 31 July 2009
Accepted 9 September 2009
Online 12 September 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.048
wR = 0.115
Data-to-parameter ratio = 14.3
Details

5-p-Tolyl-1H-tetrazole

Dong-Yue Hu,^a Xiao-Wei Chu ^a and Zhi-Rong Qu ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical, Engineering, Southeast University, Nanjing 210096, People's Republic of China
Correspondence e-mail: quzr@seu.edu.cn

The title compound, C₈H₈N₄, possesses crystallographic mirror symmetry, with four C atoms lying on the reflecting plane, which bisects the phenyl and tetrazole rings. It is composed of a planar r.m.s. deviation (0.0012 Å) tetrazole ring which is nearly coplanar with the benzene ring, the dihedral angle being 2.67 (9)°. In the crystal, symmetry-related molecules are linked by intermolecular N-HN hydrogen bonds. The molecules stack along [100] with a [pi] [pi] interaction involving the phenyl and tetrazole rings of adjacent molecules [centroid-centroid distance = 3.5639 (15) Å]. The H atom of the N-H group is disordered over two sites of equal occupancy. The methyl H atoms were modelled as disordered over two sets of sites of equal occupancy rotated by 60° with respect to each other.

Related literature

For related manganese(II) complexes, see: Hu et al. (2007); Lü (2008). For applications of tetrazoles in coordination chemistry, medicinal chemistry and materials science, see: Xiong et al. (2002); Xue et al. (2002); Wang et al. (2005); Dunica et al. (1991); Wittenberger et al. (1993).

Experimental

Crystal data

C₈H₈N₄
M_r = 160.18
Orthorhombic, P b c m
a = 4.5370 (15) Å
b = 17.729 (5) Å
c = 9.778 (2) Å
V = 786.5 (4) Å³
Z = 4
Mo K radiation
= 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 = 0.981, T_max = 0.983
7310 measured reflections
946 independent reflections
792 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.115
S = 1.12
946 reflections
66 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.17 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1ⁱ	0.87 (3)	1.94 (3)	2.806 (2)	171 (3)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, -z+1]$ .

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 (Sheldrick, 2008); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2134 ).

Acknowledgements

This work was supported by a start-up grant from Southeast University to ZRQ.

References

Dunica, J. V., Pierce, M. E. & Santella, J. B. III (1991). J. Org. Chem. 56, 2395-2400.
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada.
Hu, B., Xu, X.-B., Li, Y.-X. & Ye, H.-Y. (2007). Acta Cryst. E63, m2698.
Lü, Y. (2008). Acta Cryst. E64, m1255.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, X. S., Tang, Y. Z., Huang, X. F., Qu, Z. R., Che, C. M., Chan, C. W. H. & Xiong, R. G. (2005). Inorg. Chem. 44, 5278-5285.
Wittenberger, S. J. & Donner, B. G. (1993). J. Org. Chem. 58, 4139-4141.
Xiong, R. G., Xue, X., Zhao, H., You, X. Z., Abrahams, B. F. & Xue, Z. L. (2002). Angew. Chem. Int. Ed. 41. 3800-3803.
Xue, X., Wang, X. S., Wang, L. Z., Xiong, R. G., Abrahams, B. F., You, X. Z., Xue, Z. L. & Che, C.-M. (2002). Inorg. Chem. 41, 3800-3803.

organic compounds