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

Abduelftah, H.S.; Ali, A.Q.; Eltayeb, N.E.; Teoh, S.G.; Fun, H.-K.

doi:10.1107/S1600536811053621

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 (C-C) = 0.001 Å
R = 0.031
wR = 0.081
Data-to-parameter ratio = 26.3
Details

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

Halema Shaban Abduelftah,^a,^b Amna Qasem Ali,^a,^b Naser Eltaher Eltayeb,^a,^c ⁺ Siang Guan Teoh ^a ^* and Hoong-Kun Fun ^d ⁺⁺

^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-HN 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-HS and N-HS hydrogen bonds. The chains are further stabilized by C-HS interactions.

Related literature

For standard bond lengths, see: Allen et al. (1987). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995). For related structures, see: Choi et al. (2008). For the biological activity and pharmacological properties of thiosemicarbazones and their metal complexes, see: Cowley et al. (2002); Ming (2003); Lobana et al. (2004, 2007).

Experimental

Crystal data

C₆H₁₂N₄OS
M_r = 188.26
Triclinic, $[P \overline 1]$
a = 5.5205 (1) Å
b = 8.6077 (2) Å
c = 9.5650 (2) Å
= 79.750 (1)°
= 89.509 (1)°
= 85.083 (1)°
V = 445.61 (2) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.854, T_max = 0.978
12035 measured reflections
3256 independent reflections
2920 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(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
_max = 0.40 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H1N3S1ⁱ	0.877 (16)	2.781 (16)	3.6519 (9)	172.0 (14)
N4-H1N4N2	0.848 (16)	2.155 (16)	2.5932 (11)	111.9 (13)
O1-H1O1S1ⁱⁱ	0.857 (19)	2.437 (19)	3.2930 (8)	178.3 (17)
C4-H4AS1ⁱ	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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

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.
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.
Cowley, A. R., Dilworth, J. R., Donnelly, P. S., Labisbal, E. & Sousa, A. (2002). J. Am. Chem. Soc. 124, 5270-5271.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds