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Volume 70 
Part 1 
Pages o57-o58  
January 2014  

Received 8 December 2013
Accepted 11 December 2013
Online 14 December 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.120
Data-to-parameter ratio = 15.0
Details
Open access

4-[(E)-(4-Chloro­benzyl­idene)amino]-3-methyl-1H-1,2,4-triazole-5(4H)-thione

aDepartment of Chemistry, P.A. College of Engineering, Nadupadavu 574 153, D.K., Mangalore, India,bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India,cDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India, and dDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C10H9ClN4S, the dihedral angle between the mean planes of the phenyl and 1H-1,2,4-triazole-5(4H)-thione rings is 25.3 (9)°. The latter ring is essentially planar, with maximum deviations of 0.010 and -0.010 Å for the ring N atom in the 4-position and ring C atom bearing the methyl group, respectively. An intra­molecular C-H...S contact occurs. In the crystal, pairs of weak N-H...S inter­actions link the mol­ecules into inversion dimers in the ac plane, forming R22(8) graph-set motifs. In addition, weak [pi]-[pi] inter­actions [centroid-centroid distances = 3.3463 (14) and 3.6127 (13)Å] are observed.

Related literature

For the chemistry of 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.]). For the use of Schiff bases containing different donor atoms in analytical applications and metal coordination, see: Galic et al. (2001[Galic, N., Peric, B., Prodic, K. B. & Cimerman, Z. (2001). J. Med. Chem. 559, 187-194.]); Wyrzykiewicz & Prukah (1998[Wyrzykiewicz, E. & Prukah, D. (1998). J. Heterocycl. Chem. 35, 381-387.]); Reddy & Lirgappa (1994[Reddy, H. & Lirgappa, Y. (1994). Indian J. Heterocycl. Chem. 33, 919-923.]). Many compounds containing S and N atoms are anti­hypertensive (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.]), analgesic (Thieme et al., 1973a[Thieme, P., Konig, H. & Amann, A. (1973a). BASF, Ger. Patent 2228259.],b[Thieme, P., Konig, H. & Amann, A. (1973b). Chem. Abstr. 80, 83034q.]), anti­inflammatory (Dornow et al., 1964[Dornow, A., Menzel, H. & Marx, P. (1964). Chem. Ber. 97, 2173-2178.]), sedative (Barrera et al.,1985[Barrera, H., Vinas, J. M., Font-Altaba, M. & Solans, X. (1985). Polyhedron, 4, 2027-2030.]), or fungicidal (Malik et al., 2011[Malik, S., Ghosh, S. & Mitu, L. (2011). J. Serb. Chem. Soc. 76, 1387-1394.]). For the crystal structures of related Schiff bases, see: Jeyaseelan et al. (2012[Jeyaseelan, S., Devarajegowda, H. C., Sathishkumar, R., D'souza, A. S. & D'souza, A. (2012). Acta Cryst. E68, o1407.]); Devarajegowda et al. (2012[Devarajegowda, H. C., Jeyaseelan, S., Sathishkumar, R., D'souza, A. S. & D'souza, A. (2012). Acta Cryst. E68, o1607.]); Vinduvahini et al. (2011[Vinduvahini, M., Roopashree, K. R., Bhattacharya, S., Krishna, K. M. & Devaru, V. B. (2011). Acta Cryst. E67, o2535-o2536.]); Almutairi et al. (2012[Almutairi, M. S., Al-Shehri, M. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o656.]); Kubicki et al. (2012[Kubicki, M., Dutkiewicz, G., Praveen, A. S., Mayekar, A. N., Narayana, B. & Yathirajan, H. S. (2012). J. Chem. Crystallogr. 42, 432-437.]); Praveen et al. (2012[Praveen, A. S., Jasinski, J. P., Keeley, A. C., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o3435.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Sapnakumari, M., Sarojini, B. K. & Narayana, B. (2012). Acta Cryst. E68, o2193.]); Ding et al. (2009[Ding, Q.-C., Huang, Y.-L., Jin, J.-Y., Zhang, L.-X., Zhou, C.-F. & Hu, M.-L. (2009). Z. Kristallogr. New Cryst. Struct. 224, 105-106.]). For the crystal structures of Schiff bases reported by our group, see: Sarojini et al. (2007a[Sarojini, B. K., Yathirajan, H. S., Narayana, B., Sunil, K. & Bolte, M. (2007a). Acta Cryst. E63, o3521.],b[Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007b). Acta Cryst. E63, o3551.]). For standard bond lengths, 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 [pi]-[pi] stacking, see: Grimme (2008[Grimme, S. (2008). Angew. Chem. Int. Ed. 47, 3430-3434.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9ClN4S

  • Mr = 252.72

  • Triclinic, [P \overline 1]

  • a = 7.0718 (8) Å

  • b = 7.2901 (8) Å

  • c = 11.8434 (7) Å

  • [alpha] = 92.778 (7)°

  • [beta] = 94.986 (7)°

  • [gamma] = 109.752 (10)°

  • V = 570.50 (10) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 4.49 mm-1

  • T = 173 K

  • 0.42 × 0.08 × 0.06 mm

Data collection
  • Agilent Gemini EOS diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.544, Tmax = 1.000

  • 3413 measured reflections

  • 2195 independent reflections

  • 1860 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.120

  • S = 1.02

  • 2195 reflections

  • 146 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...S1i 0.86 2.43 3.2926 (19) 176
C1-H1...S1 0.93 2.62 3.199 (2) 121
Symmetry code: (i) -x-1, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: OLEX2 (Dolomanov et al., 2009[Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.]); software used to prepare material for publication: OLEX2.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: QM2102 ).


Acknowledgements

BKS and PSM gratefully acknowledge the Department of Chemistry, P. A. College of Engineering, for providing research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
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.  [CrossRef]
Almutairi, M. S., Al-Shehri, M. M., El-Emam, A. A., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o656.  [CSD] [CrossRef] [IUCr Journals]
Barrera, H., Vinas, J. M., Font-Altaba, M. & Solans, X. (1985). Polyhedron, 4, 2027-2030.  [CSD] [CrossRef] [ChemPort] [Web of Science]
Devarajegowda, H. C., Jeyaseelan, S., Sathishkumar, R., D'souza, A. S. & D'souza, A. (2012). Acta Cryst. E68, o1607.  [CSD] [CrossRef] [IUCr Journals]
Ding, Q.-C., Huang, Y.-L., Jin, J.-Y., Zhang, L.-X., Zhou, C.-F. & Hu, M.-L. (2009). Z. Kristallogr. New Cryst. Struct. 224, 105-106.  [ChemPort]
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339-341.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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.  [CrossRef] [ChemPort]
Galic, N., Peric, B., Prodic, K. B. & Cimerman, Z. (2001). J. Med. Chem. 559, 187-194.  [ChemPort]
Grimme, S. (2008). Angew. Chem. Int. Ed. 47, 3430-3434.  [Web of Science] [CrossRef] [ChemPort]
Jeyaseelan, S., Devarajegowda, H. C., Sathishkumar, R., D'souza, A. S. & D'souza, A. (2012). Acta Cryst. E68, o1407.  [CSD] [CrossRef] [IUCr Journals]
Kant, R., Gupta, V. K., Kapoor, K., Sapnakumari, M., Sarojini, B. K. & Narayana, B. (2012). Acta Cryst. E68, o2193.  [CSD] [CrossRef] [IUCr Journals]
Kubicki, M., Dutkiewicz, G., Praveen, A. S., Mayekar, A. N., Narayana, B. & Yathirajan, H. S. (2012). J. Chem. Crystallogr. 42, 432-437.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Malik, S., Ghosh, S. & Mitu, L. (2011). J. Serb. Chem. Soc. 76, 1387-1394.  [Web of Science] [CrossRef] [ChemPort]
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Praveen, A. S., Jasinski, J. P., Keeley, A. C., Yathirajan, H. S. & Narayana, B. (2012). Acta Cryst. E68, o3435.  [CSD] [CrossRef] [IUCr Journals]
Reddy, H. & Lirgappa, Y. (1994). Indian J. Heterocycl. Chem. 33, 919-923.
Sarojini, B. K., Narayana, B., Sunil, K., Yathirajan, H. S. & Bolte, M. (2007b). Acta Cryst. E63, o3551.  [CSD] [CrossRef] [IUCr Journals]
Sarojini, B. K., Yathirajan, H. S., Narayana, B., Sunil, K. & Bolte, M. (2007a). Acta Cryst. E63, o3521.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Thieme, P., Konig, H. & Amann, A. (1973a). BASF, Ger. Patent 2228259.
Thieme, P., Konig, H. & Amann, A. (1973b). Chem. Abstr. 80, 83034q.
Vinduvahini, M., Roopashree, K. R., Bhattacharya, S., Krishna, K. M. & Devaru, V. B. (2011). Acta Cryst. E67, o2535-o2536.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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.
Wyrzykiewicz, E. & Prukah, D. (1998). J. Heterocycl. Chem. 35, 381-387.  [CrossRef] [ChemPort]
Yadav, S., Srivastava, S. & Pandey, O. P. (1994). Synth. React. Inorg. Met. Org. Chem. 24, 925-939.  [CrossRef] [ChemPort]


Acta Cryst (2014). E70, o57-o58   [ doi:10.1107/S1600536813033527 ]

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