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Volume 68 
Part 12 
Pages o3264-o3265  
December 2012  

Received 9 October 2012
Accepted 29 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.062
wR = 0.198
Data-to-parameter ratio = 23.1
Details
Open access

Ethyl 2-(3-methyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-4-yl)acetate

aDepartment of Chemistry, Siedlce University, ul. 3 Maja 54, 08-110 Siedlce, Poland,bDepartment of Organic Chemistry, Faculty of Pharmacy with Division of Medical Analytics, Medical University, ul. Chodzki 4A, 20-093 Lublin, Poland, and cDepartment of General and Ecological Chemistry, Technical University, ul. Zeromskiego 115, 90-924 Lódz, Poland
Correspondence e-mail: kar@uph.edu.pl

The title compound, C7H11N3O2S, exists in the 5-thioxo tautomeric form. The 1,2,4-triazoline ring is essentially planar, with a maximum deviation of 0.010 (2) Å for the substituted N atom. The ethyl acetate substituent is almost planar, with a maximum deviation of 0.061 (4) Å for the methylene C atom of the ethoxy group. The angle between the mean plane of this substituent and the mean plane of the 1,2,4-triazoline ring is 89.74 (8)°. In the crystal, molecules are linked by a combination of N-H...S, C-H...N and C-H...O hydrogen bonds into chains parallel to [100].

Related literature

For background information on the title compound, 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., Hameed, 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 the biological activity of 1,2,4-triazoline-thiones, see: Pitucha et al. (2010[Pitucha, M., Polak, B., Swatko-Ossor, M., Popiolek, L. & Ginalska, G. (2010). Croat. Chem. Acta, 83, 299-306.]). For their synthesis, see: Bany & Dobosz (1972[Bany, T. & Dobosz, M. (1972). Ann. Univ. Mariae Curie-Sklodowska Sect AA, 26/27, 23-32.]). For related structures, see: 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
  • C7H11N3O2S

  • Mr = 201.25

  • Monoclinic, P 21 /c

  • a = 6.4438 (19) Å

  • b = 15.2328 (15) Å

  • c = 9.9672 (8) Å

  • [beta] = 98.416 (19)°

  • V = 967.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.31 mm-1

  • T = 293 K

  • 0.60 × 0.30 × 0.30 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 = 0.754, Tmax = 0.869

  • 2979 measured reflections

  • 2837 independent reflections

  • 1571 reflections with I > 2[sigma](I)

  • Rint = 0.069

  • 2 standard reflections every 100 reflections intensity decay: 8.9%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.198

  • S = 0.93

  • 2837 reflections

  • 123 parameters

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

  • [Delta][rho]max = 0.64 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...S6i 0.79 (4) 2.56 (4) 3.339 (3) 170 (4)
C8-H8B...N2ii 0.97 2.50 3.407 (3) 155
C13-H13A...O10ii 0.96 2.57 3.482 (5) 159
Symmetry codes: (i) -x, -y, -z+1; (ii) x+1, y, z.

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: FJ2601 ).


References

Akhtar, T., Hameed, 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]
Bany, T. & Dobosz, M. (1972). Ann. Univ. Mariae Curie-Sklodowska Sect AA, 26/27, 23-32.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
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.
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 (2012). E68, o3264-o3265   [ doi:10.1107/S1600536812044716 ]

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