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

Karczmarzyk, Z.; Pitucha, M.; Wysocki, W.; Fruziński, A.; Olender, E.

doi:10.1107/S1600536812044716

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 (C-C) = 0.005 Å
R = 0.062
wR = 0.198
Data-to-parameter ratio = 23.1
Details

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

Zbigniew Karczmarzyk,^a ^* Monika Pitucha,^b Waldemar Wysocki,^a Andrzej Fruzinski ^c and Ewa Olender ^a

^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-HS, C-HN and C-HO hydrogen bonds into chains parallel to [100].

Related literature

For background information on the title compound, see: Saadeh et al. (2010); Akhtar et al. (2008); Al-Omar et al. (2010). For the biological activity of 1,2,4-triazoline-thiones, see: Pitucha et al. (2010). For their synthesis, see: Bany & Dobosz (1972). For related structures, see: Kruszynski et al. (2007); Siwek et al. (2008). For graph-set motifs, see: Bernstein et al. (1995).

Experimental

Crystal data

C₇H₁₁N₃O₂S
M_r = 201.25
Monoclinic, P 2₁ /c
a = 6.4438 (19) Å
b = 15.2328 (15) Å
c = 9.9672 (8) Å
= 98.416 (19)°
V = 967.8 (3) Å³
Z = 4
Mo K radiation
= 0.31 mm^-1
T = 293 K
0.60 × 0.30 × 0.30 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.754, T_max = 0.869
2979 measured reflections
2837 independent reflections
1571 reflections with I > 2(I)
R_int = 0.069
2 standard reflections every 100 reflections intensity decay: 8.9%

Refinement

R[F² > 2(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
_max = 0.64 e Å^-3
_min = -0.48 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1S6ⁱ	0.79 (4)	2.56 (4)	3.339 (3)	170 (4)
C8-H8BN2ⁱⁱ	0.97	2.50	3.407 (3)	155
C13-H13AO10ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2601 ).

References

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Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Pitucha, M., Polak, B., Swatko-Ossor, M., Popiolek, L. & Ginalska, G. (2010). Croat. Chem. Acta, 83, 299-306.
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Siwek, A., Wujec, M., Wawrzycka-Gorczyca, I., Dobosz, M. & Paneth, P. (2008). Heteroat. Chem. 19, 337-344.

organic compounds