N-(5-Sulfanyl­idene-4,5-dihydro-1,3,4-thia­diazol-2-yl)acetamide dimethyl sulfoxide disolvate

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

doi:10.1107/S1600536811054298

Volume 68
Part 1
Page o224
January 2012

Received 7 December 2011
Accepted 16 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.039
wR = 0.117
Data-to-parameter ratio = 13.4
Details

N-(5-Sulfanylidene-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide dimethyl sulfoxide disolvate

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, C₄H₅N₃OS₂·2C₂H₆OS, the five-membered heterocyclic ring and the N-(C=O)-C plane of the acetamide group are essentially co-planar, with a dihedral angle of 1.25 (3)°. Intermolecular N-HO hydrogen bonds between the acetamide compound and the dimethyl sulfoxide molecules stabilize the crystal structure. The two dimethyl sulfoxide molecules are each disordered over two positions with occupancy ratios of 0.605 (2):0.395 (2) and 0.8629 (18):0.1371 (18).

Related literature

For the synthesis and biological activity of thiadiazole compounds, see: Hildebrandt et al. (2011); Cho et al. (1993). For the structures of thiadiazole derivatives, see: Zhan et al. (2007, 2009).

Experimental

Crystal data

C₄H₅N₃OS₂·2C₂H₆OS
M_r = 331.49
Triclinic, $[P \overline 1]$
a = 7.090 (2) Å
b = 9.982 (3) Å
c = 11.513 (3) Å
= 100.872 (6)°
= 96.827 (4)°
= 91.359 (4)°
V = 793.6 (4) Å³
Z = 2
Mo K radiation
= 0.60 mm^-1
T = 296 K
0.28 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.894, T_max = 0.916
24389 measured reflections
3292 independent reflections
2625 reflections with I > 2(I)
R_int = 0.180

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.117
S = 1.06
3292 reflections
245 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.22 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N5-H5O16	0.88 (2)	1.91 (2)	2.783 (3)	170 (3)
N7-H7O12	0.86 (2)	1.89 (2)	2.734 (8)	166 (2)

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: IS5026 ).

References

Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Cho, N. S., Kim, G. N. & Parkanyi, C. (1993). J. Heterocycl. Chem. 30, 397-401.
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.
Zhan, P., Liu, X., Fang, Z., Li, Z., Pannecouque, C. & De Clercq, E. (2009). Eur. J. Med. Chem. 44, 4648-4653.
Zhan, J.-Y., Xiong, D.-J., Wang, Y.-G. & Li, H.-B. (2007). Acta Cryst. E63, o2184-o2185.

organic compounds