3-Benzyl­sulfanyl-1H-1,2,4-triazol-5-amine

Zhang, S.; Liu, P.-J.; Ma, D.-S.; Hou, G.-F.

doi:10.1107/S1600536811052159

Volume 68
Part 1
Page o83
January 2012

Received 29 November 2011
Accepted 3 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.111
Data-to-parameter ratio = 16.7
Details

3-Benzylsulfanyl-1H-1,2,4-triazol-5-amine

Shuai Zhang,^a Pei-Jiang Liu,^a Dong-Sheng Ma ^a ^* and Guang-Feng Hou ^a

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
Correspondence e-mail: hgf1000@163.com

In the title molecule, C₉H₁₀N₄S, the dihedral angle between the benzene and triazole rings is 81.05 (5)°. In the crystal, N-HN hydrogen bonds link the molecules into infinite zigzag chains along [010].

Related literature

For the biological properties of 1,2,4-triazoles derivatives, see: Paulvannan et al. (2001); El-Sagheer & Brown (2011).

Experimental

Crystal data

C₉H₁₀N₄S
M_r = 206.27
Monoclinic, P 2₁ /c
a = 9.870 (2) Å
b = 9.6370 (19) Å
c = 10.398 (2) Å
= 90.18 (3)°
V = 989.0 (3) Å³
Z = 4
Mo K radiation
= 0.29 mm^-1
T = 293 K
0.38 × 0.26 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.897, T_max = 0.970
9367 measured reflections
2267 independent reflections
1372 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.111
S = 1.04
2267 reflections
136 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N4-H41N1ⁱ	0.89 (1)	2.20 (2)	3.044 (3)	158 (3)
N2-H21N3ⁱⁱ	0.90 (1)	2.03 (2)	2.873 (2)	155 (2)
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002); 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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5211 ).

Acknowledgements

The authors thank Heilongjiang University for supporting this work.

References

El-Sagheer, A. H. & Brown, T. (2011). Chem. Commun. 47, 12057-12058.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Paulvannan, K., Hale, R., Sedehi, D. & Chen, T. (2001). Tetrahedron, 57, 9677-9682.
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds