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Volume 69 
Part 2 
Pages o155-o156  
February 2013  

Received 6 November 2012
Accepted 19 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.047
wR = 0.156
Data-to-parameter ratio = 17.6
Details
Open access

3-Benzyl-4-ethyl-1H-1,2,4-triazole-5(4H)-thione

aDepartment of Chemistry, Siedlce University, ul. 3 Maja 54, 08-110 Siedlce, Poland, and bDepartment of Organic Chemistry, Faculty of Pharmacy with Division of Medical Analytics, Medical University, ul. Chodzki 4A, 20-093 Lublin, Poland
Correspondence e-mail: kar@uph.edu.pl

The title compound, C11H13N3S, exists in the 5-thioxo tautomeric form. The benzene ring exhibits disorder with a refined ratio of 0.77 (2):0.23 (2) for components A and B with a common bridgehead C atom. The 1,2,4-triazole ring is essentially planar, with a maximum deviation of 0.002 (3) Å for the benzyl-substituted C atom, and forms dihedral angles of 88.94 (18) and 86.56 (49)° with the benzene rings of components A and B, respectively. The angle between the plane of the ethyl chain and the mean plane of 1,2,4-triazole ring is 88.55 (15)° and this conformation is stabilized by an intramolecular C-H...S contact. In the crystal, pairs of N-H...S hydrogen bonds link molecules into inversion dimers. [pi]-[pi] interactions are observed between the triazole and benzene rings, with centroid-centroid separations of 3.547 (4) and 3.544 (12) Å for components A and B, and slippages of 0.49 (6) and 0.58 (15) Å, respectively.

Related literature

For background information on 1,2,4-triazole-5-thiones, see: Saadeh et al. (2010[Saadeh, H. A., Mosleh, I. M., Al-Bakri, A. G. & Mubarak, M. I. (2010). Monatsh. Chem. 141, 471-478.]); Akhtar et al. (2008[Akhtar, T., Hameede, S., Khan, K. M. & Choudhary, M. I. (2008). Med. Chem. 4, 539-543.]); Al-Omar et al. (2010[Al-Omar, M. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Molecules, 15, 2526-2550.]). For their biological activity, see: Pitucha et al. (2010[Pitucha, M., Polak, B., Swatko-Ossor, M., Popiolek, L. & Ginalska, G. (2010). Croat. Chem. Acta, 83, 299-306.]). For the synthesis, see: Dobosz & Pachuta-Stec (1996[Dobosz, M. & Pachuta-Stec, A. (1996). Acta Pol. Pharm. 53, 123-131.]). For related structures, see: Karczmarzyk et al. (2012[Karczmarzyk, Z., Pitucha, M., Wysocki, W., Fruzinski, A. & Olender, E. (2012). Acta Cryst. E68, o3264-o3265.]); Kruszynski et al. (2007[Kruszynski, R., Trzesowska, A., Przybycin, M., Gil, K. & Dobosz, M. (2007). Acta Cryst. E63, o4378.]); Siwek et al. (2008[Siwek, A., Wujec, M., Wawrzycka-Gorczyca, I., Dobosz, M. & Paneth, P. (2008). Heteroat. Chem. 19, 337-344.]). For 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
  • C11H13N3S

  • Mr = 219.30

  • Monoclinic, P 21 /c

  • a = 7.3731 (5) Å

  • b = 8.9408 (19) Å

  • c = 16.9936 (8) Å

  • [beta] = 91.892 (4)°

  • V = 1119.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 296 K

  • 0.55 × 0.20 × 0.20 mm

Data collection
  • Kuma KM-4 four-circle diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.834, Tmax = 0.852

  • 3392 measured reflections

  • 3289 independent reflections

  • 1385 reflections with I > 2[sigma](I)

  • Rint = 0.039

  • 2 standard reflections every 100 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.156

  • S = 0.98

  • 3289 reflections

  • 187 parameters

  • 6 restraints

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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7B...S6 0.97 2.85 3.204 (3) 103
N1-H1...S6i 0.86 (3) 2.46 (3) 3.303 (3) 167 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: KM4B8 (Galdecki et al., 1996[Galdecki, Z., Kowalski, A., Kucharczyk, D. & Uszynski, L. (1996). KM4B8. Kuma Diffraction, Wroclaw, Poland.]); cell refinement: KM4B8; data reduction: DATAPROC (Galdecki et al., 1995[Galdecki, Z., Kowalski, A. & Uszynski, L. (1995). DATAPROC. Kuma Diffraction, Wroclaw, Poland.]); 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.]); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2077 ).


References

Akhtar, T., Hameede, S., Khan, K. M. & Choudhary, M. I. (2008). Med. Chem. 4, 539-543.  [CrossRef] [PubMed] [ChemPort]
Al-Omar, M. A., Al-Abdullah, E. S., Shehata, I. A., Habib, E. E., Ibrahim, T. M. & El-Emam, A. A. (2010). Molecules, 15, 2526-2550.  [ChemPort] [PubMed]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Dobosz, M. & Pachuta-Stec, A. (1996). Acta Pol. Pharm. 53, 123-131.  [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Galdecki, Z., Kowalski, A., Kucharczyk, D. & Uszynski, L. (1996). KM4B8. Kuma Diffraction, Wroclaw, Poland.
Galdecki, Z., Kowalski, A. & Uszynski, L. (1995). DATAPROC. Kuma Diffraction, Wroclaw, Poland.
Karczmarzyk, Z., Pitucha, M., Wysocki, W., Fruzinski, A. & Olender, E. (2012). Acta Cryst. E68, o3264-o3265.  [CSD] [CrossRef] [details]
Kruszynski, R., Trzesowska, A., Przybycin, M., Gil, K. & Dobosz, M. (2007). Acta Cryst. E63, o4378.  [CSD] [CrossRef] [details]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Pitucha, M., Polak, B., Swatko-Ossor, M., Popiolek, L. & Ginalska, G. (2010). Croat. Chem. Acta, 83, 299-306.  [ChemPort]
Saadeh, H. A., Mosleh, I. M., Al-Bakri, A. G. & Mubarak, M. I. (2010). Monatsh. Chem. 141, 471-478.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siwek, A., Wujec, M., Wawrzycka-Gorczyca, I., Dobosz, M. & Paneth, P. (2008). Heteroat. Chem. 19, 337-344.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o155-o156   [ doi:10.1107/S1600536812051276 ]

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