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Volume 68 
Part 1 
Page o184  
January 2012  

Received 3 November 2011
Accepted 13 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 26.3
Details
Open access

(E)-2-[(E)-3-(Hydroxyimino)butan-2-ylidene]-N-methylhydrazinecarbothioamide

aSchool of Chemical Sciences, Universiti Sains Malaysia, Minden, Penang, Malaysia,bFaculty of Science, Sabha University, Libya,cDepartment of Chemistry, International University of Africa, Khartoum, Sudan, and dX-ray Crystallography Unit, School of Physics,Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: sgteoh@usm.my

In the title compound, C6H12N4OS, an intramolecular N-H...N hydrogen-bond is present giving rise to an S(5) ring motif. In the crystal, double-stranded chains propagating along [10[\overline{1}]] are formed via pairs of O-H...S and N-H...S hydrogen bonds. The chains are further stabilized by C-H...S interactions.

Related literature

For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For related structures, see: Choi et al. (2008[Choi, K.-Y., Yang, S.-M., Lee, K.-C., Ryu, H., Lee, C. H., Seo, J. & Suh, M. (2008). Transition Met. Chem. 33, 99-105.]). For the biological activity and pharmacological properties of thiosemicarbazones and their metal complexes, see: Cowley et al. (2002[Cowley, A. R., Dilworth, J. R., Donnelly, P. S., Labisbal, E. & Sousa, A. (2002). J. Am. Chem. Soc. 124, 5270-5271.]); Ming (2003[Ming, L.-J. (2003). Med. Res. Rev. 23, 697-762.]); Lobana et al. (2004[Lobana T. S., Rekha & Butcher, R. J. (2004). Transition Met. Chem. 29, 291-295.], 2007[Lobana T. S., Rekha, Pannu A.P.S., Hundal G., Butcher R. J. & Castineiras A. (2007). Polyhedron, 26, 2621-2628.]).

[Scheme 1]

Experimental

Crystal data
  • C6H12N4OS

  • Mr = 188.26

  • Triclinic, [P \overline 1]

  • a = 5.5205 (1) Å

  • b = 8.6077 (2) Å

  • c = 9.5650 (2) Å

  • [alpha] = 79.750 (1)°

  • [beta] = 89.509 (1)°

  • [gamma] = 85.083 (1)°

  • V = 445.61 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 100 K

  • 0.51 × 0.25 × 0.07 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.854, Tmax = 0.978

  • 12035 measured reflections

  • 3256 independent reflections

  • 2920 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.081

  • S = 1.08

  • 3256 reflections

  • 124 parameters

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

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H1N3...S1i 0.877 (16) 2.781 (16) 3.6519 (9) 172.0 (14)
N4-H1N4...N2 0.848 (16) 2.155 (16) 2.5932 (11) 111.9 (13)
O1-H1O1...S1ii 0.857 (19) 2.437 (19) 3.2930 (8) 178.3 (17)
C4-H4A...S1i 0.98 2.69 3.3991 (12) 129
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x-1, y, z+1; (iii) x+1, y, z; (iv) -x, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: MW2038 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia for the RU research Grant (1001/PKIMIA/815067). NEE thanks Universiti Sains Malaysia for a post-doctoral fellowship and the International University of Africa (Sudan) for providing research leave. HAF and AQA each thank the Ministry of Higher Education and the University of Sabha (Libya) for a scholarship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, K.-Y., Yang, S.-M., Lee, K.-C., Ryu, H., Lee, C. H., Seo, J. & Suh, M. (2008). Transition Met. Chem. 33, 99-105.  [ISI] [CSD] [CrossRef] [ChemPort]
Cowley, A. R., Dilworth, J. R., Donnelly, P. S., Labisbal, E. & Sousa, A. (2002). J. Am. Chem. Soc. 124, 5270-5271.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Lobana T. S., Rekha & Butcher, R. J. (2004). Transition Met. Chem. 29, 291-295.
Lobana T. S., Rekha, Pannu A.P.S., Hundal G., Butcher R. J. & Castineiras A. (2007). Polyhedron, 26, 2621-2628.
Ming, L.-J. (2003). Med. Res. Rev. 23, 697-762.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o184  [ doi:10.1107/S1600536811053621 ]

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