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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 [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.039
wR = 0.117
Data-to-parameter ratio = 13.4
Details
Open access

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

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-H...O 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[Hildebrandt, A., Schaarschmidt, D., van As, L., Swarts, J. C. & Lang, H. (2011). Inorg. Chim. Acta, 374, 112-118.]); Cho et al. (1993[Cho, N. S., Kim, G. N. & Parkanyi, C. (1993). J. Heterocycl. Chem. 30, 397-401.]). For the structures of thiadiazole derivatives, see: Zhan et al. (2007[Zhan, J.-Y., Xiong, D.-J., Wang, Y.-G. & Li, H.-B. (2007). Acta Cryst. E63, o2184-o2185.], 2009[Zhan, P., Liu, X., Fang, Z., Li, Z., Pannecouque, C. & De Clercq, E. (2009). Eur. J. Med. Chem. 44, 4648-4653.]).

[Scheme 1]

Experimental

Crystal data
  • C4H5N3OS2·2C2H6OS

  • Mr = 331.49

  • Triclinic, [P \overline 1]

  • a = 7.090 (2) Å

  • b = 9.982 (3) Å

  • c = 11.513 (3) Å

  • [alpha] = 100.872 (6)°

  • [beta] = 96.827 (4)°

  • [gamma] = 91.359 (4)°

  • V = 793.6 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.894, Tmax = 0.916

  • 24389 measured reflections

  • 3292 independent reflections

  • 2625 reflections with I > 2[sigma](I)

  • Rint = 0.180

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N5-H5...O16 0.88 (2) 1.91 (2) 2.783 (3) 170 (3)
N7-H7...O12 0.86 (2) 1.89 (2) 2.734 (8) 166 (2)

Data collection: SMART (Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


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.  [CrossRef] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Hildebrandt, A., Schaarschmidt, D., van As, L., Swarts, J. C. & Lang, H. (2011). Inorg. Chim. Acta, 374, 112-118.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhan, P., Liu, X., Fang, Z., Li, Z., Pannecouque, C. & De Clercq, E. (2009). Eur. J. Med. Chem. 44, 4648-4653.  [ISI] [CrossRef] [PubMed] [ChemPort]
Zhan, J.-Y., Xiong, D.-J., Wang, Y.-G. & Li, H.-B. (2007). Acta Cryst. E63, o2184-o2185.  [CrossRef] [details]


Acta Cryst (2012). E68, o224  [ doi:10.1107/S1600536811054298 ]

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