2-[(E)-2-Hy­droxy-3-methoxy­benzyl­idene]-N-methyl­hydrazinecarbothio­amide

Shankara, B.S.; Shashidhar, N.; Patil, Y.P.; Krishna, P.M.; Nethaji, M.

doi:10.1107/S1600536812049847

Volume 69
Part 1
Page o61
January 2013

Received 30 August 2012
Accepted 5 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R = 0.064
wR = 0.180
Data-to-parameter ratio = 13.9
Details

2-[(E)-2-Hydroxy-3-methoxybenzylidene]-N-methylhydrazinecarbothioamide

B. S. Shankara,^a N. Shashidhar,^b Yogesh Prakash Patil,^c P. Murali Krishna ^d ^* and Munirathinam Nethaji ^c

^aDepartment of Chemistry, Sri Krishna Institute of Technology, Bangalore 560 090, India,^bDepartment of Chemistry, S. D. M. College of Engineering and Technology, Dharwad 580 002, India,^cDepartment of Inorganic and Physical Chemistry, Indian Institute of Science, Bangalore 560 012, India, and ^dDepartment of Chemistry, M. S. Ramaiah Institute of Technology, Bangalore 560 054, Karnataka, India
Correspondence e-mail: muralikp21@gmail.com

In the crystal structure of the title compound, C₁₁H₁₅N₃O₂S, molecules are linked by pairs of N-HO and O-HS hydrogen, forming inversion dimers. These dimers are linked by N-HS hydrogen bonds, forming double-stranded chains propagating along the b-axis direction. The two C atoms of the end chain of the molecule are disordered over two sets os sites [occupancy ratio 0.574 (9):0.426 (9)].

Related literature

For related structures, see: Joseph et al. (2006); Ren-Gao Zhao et al.(2008). For the biological activity of thiosemicarbazone Schiff bases, see: Kasuga et al. (2003); Murali et al. (2008, 2009); Paterson & Donnelly (2011).

Experimental

Crystal data

C₁₁H₁₅N₃O₂S
M_r = 253.32
Monoclinic, P 2₁ /c
a = 13.251 (6) Å
b = 6.185 (3) Å
c = 16.380 (8) Å
= 113.153 (7)°
V = 1234.4 (11) Å³
Z = 4
Mo K radiation
= 0.26 mm^-1
T = 293 K
0.26 × 0.09 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006) T_min = 0.936, T_max = 0.987
7373 measured reflections
2433 independent reflections
1666 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.064
wR(F²) = 0.180
S = 1.06
2433 reflections
175 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.46 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1S1ⁱ	0.87 (4)	2.42 (4)	3.169 (3)	145 (3)
N2-H2O1ⁱ	0.82 (3)	2.29 (4)	3.010 (4)	147 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2126 ).

Acknowledgements

The work was financed by a grant (project No: VTU/Aca./2010-11/A-9/11341) from Visvesvaraya Technological University. YPP thanks the CSIR, India, for a fellowship.

References

Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Joseph, M., Kuriakose, M., Kurup, M. R. P., Suresh, E., Kishore, A. & Bhat, S. G. (2006). Polyhedron, 25, 61-70.
Kasuga, N. C., Sekino, K., Ishikawa, M., Honda, A., Yokoyama, M., Nakano, S., Shimada, N., Koumo, C. & Nomiya, K. (2003). J. Inorg. Biochem. 96, 298-310.
Murali Krishna, P. & Hussain Reddy, K. (2009). Inorg. Chim. Acta, 362, 4185-4190.
Murali Krishna, P., Hussain Reddy, K., Pandey, J. P. & Dayananda, S. (2008). Transition Met. Chem. 33, 661-668.
Paterson, B. M. & Donnelly, P. S. (2011). Chem. Soc. Rev. 40, 3005-3018.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Zhao, R.-G., Zhang, W., Li, J.-K. & Zhang, L.-Y. (2008). Acta Cryst. E64, o1113.

organic compounds