5-Eth­oxy-1,3,4-thia­diazole-2(3H)-thione

Kang, S.K.; Cho, N.S.; Jang, S.

doi:10.1107/S1600536812002024

Volume 68
Part 2
Page o503
February 2012

Received 15 January 2012
Accepted 17 January 2012
Online 21 January 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.035
wR = 0.106
Data-to-parameter ratio = 15.5
Details

5-Ethoxy-1,3,4-thiadiazole-2(3H)-thione

Sung Kwon Kang,^a ^* Nam Sook Cho ^a and Siyoung Jang ^a

^aDepartment of Chemistry, Chungnam National University, Daejeon 305-764, Republic of Korea
Correspondence e-mail: skkang@cnu.ac.kr

In the title compound, C₄H₆N₂OS₂, the dihedral angle between the five-membered heterocyclic ring and the plane of the ethoxy group is 4.9 (2)°. The 1,3,4-thiadiazole-2-thione unit is planar, with an r.m.s. deviation of 0.011 Å from the corresponding squares plane defined by the seven constituent atoms. In the crystal, pairs of N-HS hydrogen bonds link the molecules into inversion dimers.

Related literature

For the synthesis and reactivity of thiadiazole derivatives, see: Hildebrandt et al. (2011); Zhan et al. (2009); Cho et al. (1998); Squillacote & Felippis (1994); Antolini et al. (1993).

Experimental

Crystal data

C₄H₆N₂OS₂
M_r = 162.23
Triclinic, $[P \overline 1]$
a = 6.0308 (12) Å
b = 8.1171 (16) Å
c = 8.7616 (18) Å
= 116.55 (4)°
= 93.70 (3)°
= 106.10 (3)°
V = 359.7 (2) Å³
Z = 2
Mo K radiation
= 0.66 mm^-1
T = 296 K
0.16 × 0.12 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.905, T_max = 0.951
10973 measured reflections
1329 independent reflections
1020 reflections with I > 2(I)
R_int = 0.078

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.106
S = 1.03
1329 reflections
86 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.34 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3S6ⁱ	0.76 (2)	2.57 (2)	3.317 (3)	170 (3)
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5053 ).

References

Antolini, L., Cornia, A., Fabretti, A. C. & Schenetti, L. (1993). J. Chem. Soc. Perkin Trans. 2, pp. 417-420.
Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Cho, N. S., Park, C. K., Kim, H. S., Choi, E. S. & Kang, S. K. (1998). Bull. Korean Chem. Soc. 19, 103-106.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Hildebrandt, A., Schaarschmidt, D., van As, L., Swarts, J. C. & Lang, H. (2011). Inorg. Chim. Acta, 374, 112-118.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Squillacote, M. & Felippis, J. D. (1994). J. Org. Chem. 59, 3564-3571.
Zhan, P., Liu, X., Fang, Z., Li, Z., Pannecouque, C. & De Clercq, E. (2009). Eur. J. Med. Chem. 44, 4648-4653.

organic compounds