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Volume 69 
Part 5 
Page o728  
May 2013  

Received 4 April 2013
Accepted 10 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.088
Data-to-parameter ratio = 13.8
Details
Open access

4-Amino-3-(3-methoxybenzyl)-1H-1,2,4-triazole-5(4H)-thione

aDepartment of Chemistry, P A College of Engineering, Nadupadavu 574 153, D.K. Mangalore, India,bFaculty of Industrial Science and Technology, University Malaysia Pahang, LebuhrayaTunRazak, 26300 Gambang, Kuantan, Pahang Darul Makmur, Malaysia, and cX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
Correspondence e-mail: rkvk.paper11@gmail.com

In the title molecule, C10H12N4SO, the triazole ring forms a dihedral angle of 73.0 (5)° with the benzene ring. The methoxy group is approximtely coplanar with the benzene ring with a C[pdbond]C-O-Cmethyl torsion angle of 4.7 (3)°. In the crystal, N-H...S hydrogen bonds connect pairs of inversion-related molecules, which are in turn connected by N-H...N hydrogen bonds into chains of rings along [010]. Weak C-H...O hydrogen bonds connect these chains into a two-dimensional network parallel to (-102).

Related literature

For background to the chemistry of triazoles, see: Holla et al. (2001[Holla, B. S., Sarojini, B. K., Rao, B. S., Akberali, P. M. & Suchetha Kumari, N. (2001). Il Farmaco, 56, 565-570.], 2006[Holla, B. S., Rao, B. S., Sarojini, B. K., Akberali, P. M. & Suchetha Kumari, N. (2006). Euro. J. Med. Chem. 41, 657-663.]). For the biological activity of 1,2,4-triazole derivatives, see: Cansiz et al. (2001[Cansiz, A., Servi, S., Koparir, M., Altintas, M. & Digrak, M. (2001). J. Chem. Soc. Pak. 23, 237-239.]); Jones et al. (1965[Jones, D. H., Slack, R., Squires, S. & Wooldridge, K. R. H. (1965). J. Med. Chem. 8, 676-680.]); Kane et al. (1988[Kane, J. M., Dudley, M. W., Sorensen, S. M. & Miller, F. P. (1988). J. Med. Chem. 31, 1253-1258.]); Mullican et al. (1993[Mullican, M. D., Wilson, M. W., Connor, D. T., Kostlan, C. R., Schrier, D. J. & Dyer, R. D. (1993). J. Med. Chem. 36, 1090-1099.]). For related structures, see: Chen et al. (2007[Chen, X.-A., Huang, X.-B. & Wu, H.-Y. (2007). Acta Cryst. E63, o3191.]); Gao et al. (2011[Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794.]); Karczmarzyk et al. (2012[Karczmarzyk, Z., Pitucha, M., Wysocki, W., Fruzinski, A. & Olender, E. (2012). Acta Cryst. E68, o3264-o3265.]). For standard bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C10H12N4OS

  • Mr = 236.30

  • Monoclinic, P 21 /n

  • a = 7.4580 (3) Å

  • b = 5.8006 (2) Å

  • c = 25.2817 (10) Å

  • [beta] = 94.513 (4)°

  • V = 1090.32 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.28 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.1 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.946, Tmax = 1.000

  • 15190 measured reflections

  • 2130 independent reflections

  • 1748 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.088

  • S = 1.03

  • 2130 reflections

  • 154 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7A...O1i 0.97 2.46 3.308 (2) 146
N6-H62...N1ii 0.90 (2) 2.30 (2) 3.190 (2) 174
N2-H2...S1iii 0.86 2.60 3.377 (1) 151
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) x, y+1, z; (iii) -x+2, -y+2, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5605 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for the sanction of the single-crystal X-ray diffractometer as a National Facility under a mega research project No. SR/S2/ CMP-47/2003.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Cansiz, A., Servi, S., Koparir, M., Altintas, M. & Digrak, M. (2001). J. Chem. Soc. Pak. 23, 237-239.  [ChemPort]
Chen, X.-A., Huang, X.-B. & Wu, H.-Y. (2007). Acta Cryst. E63, o3191.  [CSD] [CrossRef] [details]
Gao, Y., Zhang, L. & Wang, H. (2011). Acta Cryst. E67, o1794.  [CSD] [CrossRef] [details]
Holla, B. S., Rao, B. S., Sarojini, B. K., Akberali, P. M. & Suchetha Kumari, N. (2006). Euro. J. Med. Chem. 41, 657-663.  [ChemPort]
Holla, B. S., Sarojini, B. K., Rao, B. S., Akberali, P. M. & Suchetha Kumari, N. (2001). Il Farmaco, 56, 565-570.  [CrossRef] [PubMed] [ChemPort]
Jones, D. H., Slack, R., Squires, S. & Wooldridge, K. R. H. (1965). J. Med. Chem. 8, 676-680.  [CrossRef] [ChemPort] [ISI]
Kane, J. M., Dudley, M. W., Sorensen, S. M. & Miller, F. P. (1988). J. Med. Chem. 31, 1253-1258.  [CrossRef] [ChemPort] [PubMed] [ISI]
Karczmarzyk, Z., Pitucha, M., Wysocki, W., Fruzinski, A. & Olender, E. (2012). Acta Cryst. E68, o3264-o3265.  [CSD] [CrossRef] [ChemPort] [details]
Mullican, M. D., Wilson, M. W., Connor, D. T., Kostlan, C. R., Schrier, D. J. & Dyer, R. D. (1993). J. Med. Chem. 36, 1090-1099.  [CrossRef] [ChemPort] [PubMed] [ISI]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o728  [ doi:10.1107/S1600536813009859 ]

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