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Volume 69 
Part 5 
Pages o718-o719  
May 2013  

Received 3 April 2013
Accepted 9 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.032
wR = 0.088
Data-to-parameter ratio = 15.7
Details
Open access

3-Methyl-4-{(E)-[4-(methylsulfanyl)benzylidene]amino}-1H-1,2,4-triazole-5(4H)-thione

aDepartment of Chemistry, PA College of Engineering, Nadupadavu 574 153, D.K. Mangalore, India,bFaculty of Industrial Science and Technology, University Malaysia Pahang, LebuhrayaTunRazak, 2630 0Gambang, 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, C11H12N4S2, the dihedral angle between the triazole and benzene rings is 21.31 (5)°. A weak intramolecular C-H...S hydrogen bond generates an S(6) ring motif. In the crystal, pairs of N-H...S hydrogen bonds form inversion dimers. In addition, [pi]-[pi] interactions are observed between the benzene rings, with a centroid-centroid separation of 3.7599 (11) Å.

Related literature

For background to Schiff base compounds, see: Dubey & Vaid (1991[Dubey, S. N. & Vaid, B. K. (1991). Synth. React. Inorg. Met. Org. Chem. 21, 1299-1311.]); Yadav et al. (1994[Yadav, S., Srivastava, S. & Pandey, O. P. (1994). Synth. React. Inorg. Met. Org. Chem. 24, 925-939.]); Galic et al. (2001[Galic, N., Peric, B., Prodic, K. B. & Cimerman, Z. (2001). J. Med. Chem. 559, 187-194.]). For biological applications of sulfur- and nitrogen-containing compounds, see: Wei et al. (1981[Wei, P. H. L. & Bell, C. S. (1981). Chem. Abstr. 96, 104227.], 1982[Wei, P. H. L. & Bell, C. S. (1982). American Home Products Corporation, US Patent No. 4302585.]); Thieme et al. (1973a[Thieme, P., König, H. & Amann, A. (1973a). BASF, German Patent 2228259.],b[Thieme, P., König, H. & Amann, A. (1973b). Chem. Abstr. 80, 83034q.]); Dornow et al. (1964[Dornow, A., Menzel, H. & Marx, P. (1964). Chem. Ber. 97, 2173-2178.]); Barrera et al. (1985[Barrera, H., Vinas, J. M., Font-Altaba, M. & Solans, X. (1985). Polyhedron, 4, 2027-2030.]); Malik et al., (2011[Malik, S., Ghosh, S. & Mitu, L. (2011). J. Serb. Chem. Soc. 76, 1387-1394.]). For related structures, see: Devarajegowda et al. (2012[Devarajegowda, H. C., Jeyaseelan, S., Sathishkumar, R., D'souza, A. S. & D'souza, A. (2012). Acta Cryst. E68, o1607.]); Fun et al. (2008[Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S., Kalluraya, B., Muralidharan, A. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o1509.]); Wang et al. (2008[Wang, M., Cao, M., Hu, B., Cheng, C. X. & Song, X. G. (2008). Acta Cryst. E64, o374.]). 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.]). For hydrogen-bond graph-set motifs, see: Bernstein et al.(1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12N4S2

  • Mr = 264.37

  • Triclinic, [P \overline 1]

  • a = 7.7873 (2) Å

  • b = 9.5982 (2) Å

  • c = 9.6041 (2) Å

  • [alpha] = 76.608 (2)°

  • [beta] = 70.602 (2)°

  • [gamma] = 68.570 (2)°

  • V = 625.30 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.41 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 and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.866, Tmax = 1.000

  • 30316 measured reflections

  • 2449 independent reflections

  • 2121 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.088

  • S = 1.03

  • 2449 reflections

  • 156 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C8-H8...S1 0.93 2.57 3.212 (2) 126
N2-H2...S1i 0.86 2.48 3.328 (2) 169
Symmetry code: (i) -x, -y+1, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and 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: LH5604 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for the sanction of the single-crystal X-ray diffractometer as a National Facility under 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.
Barrera, H., Vinas, J. M., Font-Altaba, M. & Solans, X. (1985). Polyhedron, 4, 2027-2030.  [CrossRef] [ChemPort] [ISI]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Devarajegowda, H. C., Jeyaseelan, S., Sathishkumar, R., D'souza, A. S. & D'souza, A. (2012). Acta Cryst. E68, o1607.  [CSD] [CrossRef] [details]
Dornow, A., Menzel, H. & Marx, P. (1964). Chem. Ber. 97, 2173-2178.  [CrossRef] [ChemPort]
Dubey, S. N. & Vaid, B. K. (1991). Synth. React. Inorg. Met. Org. Chem. 21, 1299-1311.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S., Kalluraya, B., Muralidharan, A. & Dharmaprakash, S. M. (2008). Acta Cryst. E64, o1509.  [CSD] [CrossRef] [details]
Galic, N., Peric, B., Prodic, K. B. & Cimerman, Z. (2001). J. Med. Chem. 559, 187-194.  [ChemPort]
Malik, S., Ghosh, S. & Mitu, L. (2011). J. Serb. Chem. Soc. 76, 1387-1394.  [ISI] [CrossRef] [ChemPort]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. 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]
Thieme, P., König, H. & Amann, A. (1973a). BASF, German Patent 2228259.
Thieme, P., König, H. & Amann, A. (1973b). Chem. Abstr. 80, 83034q.
Wang, M., Cao, M., Hu, B., Cheng, C. X. & Song, X. G. (2008). Acta Cryst. E64, o374.  [CSD] [CrossRef] [details]
Wei, P. H. L. & Bell, C. S. (1981). Chem. Abstr. 96, 104227.
Wei, P. H. L. & Bell, C. S. (1982). American Home Products Corporation, US Patent No. 4302585.
Yadav, S., Srivastava, S. & Pandey, O. P. (1994). Synth. React. Inorg. Met. Org. Chem. 24, 925-939.  [ChemPort]


Acta Cryst (2013). E69, o718-o719   [ doi:10.1107/S1600536813009690 ]

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