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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 [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.111
Data-to-parameter ratio = 16.7
Details
Open access

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

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-H...N 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[Paulvannan, K., Hale, R., Sedehi, D. & Chen, T. (2001). Tetrahedron, 57, 9677-9682.]); El-Sagheer & Brown (2011[El-Sagheer, A. H. & Brown, T. (2011). Chem. Commun. 47, 12057-12058.]).

[Scheme 1]

Experimental

Crystal data
  • C9H10N4S

  • Mr = 206.27

  • Monoclinic, P 21 /c

  • a = 9.870 (2) Å

  • b = 9.6370 (19) Å

  • c = 10.398 (2) Å

  • [beta] = 90.18 (3)°

  • V = 989.0 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.897, Tmax = 0.970

  • 9367 measured reflections

  • 2267 independent reflections

  • 1372 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H41...N1i 0.89 (1) 2.20 (2) 3.044 (3) 158 (3)
N2-H21...N3ii 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[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ChemPort]
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Paulvannan, K., Hale, R., Sedehi, D. & Chen, T. (2001). Tetrahedron, 57, 9677-9682.  [ISI] [CrossRef] [ChemPort]
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.  [CrossRef] [details]


Acta Cryst (2012). E68, o83  [ doi:10.1107/S1600536811052159 ]

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