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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 [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.064
wR = 0.180
Data-to-parameter ratio = 13.9
Details
Open access

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

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-H...O and O-H...S hydrogen, forming inversion dimers. These dimers are linked by N-H...S 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[Joseph, M., Kuriakose, M., Kurup, M. R. P., Suresh, E., Kishore, A. & Bhat, S. G. (2006). Polyhedron, 25, 61-70.]); Ren-Gao Zhao et al.(2008[Zhao, R.-G., Zhang, W., Li, J.-K. & Zhang, L.-Y. (2008). Acta Cryst. E64, o1113.]). For the biological activity of thiosemicarbazone Schiff bases, see: Kasuga et al. (2003[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 et al. (2008[Murali Krishna, P., Hussain Reddy, K., Pandey, J. P. & Dayananda, S. (2008). Transition Met. Chem. 33, 661-668.], 2009[Murali Krishna, P. & Hussain Reddy, K. (2009). Inorg. Chim. Acta, 362, 4185-4190.]); Paterson & Donnelly (2011[Paterson, B. M. & Donnelly, P. S. (2011). Chem. Soc. Rev. 40, 3005-3018.]).

[Scheme 1]

Experimental

Crystal data
  • C11H15N3O2S

  • Mr = 253.32

  • Monoclinic, P 21 /c

  • a = 13.251 (6) Å

  • b = 6.185 (3) Å

  • c = 16.380 (8) Å

  • [beta] = 113.153 (7)°

  • V = 1234.4 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]) Tmin = 0.936, Tmax = 0.987

  • 7373 measured reflections

  • 2433 independent reflections

  • 1666 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...S1i 0.87 (4) 2.42 (4) 3.169 (3) 145 (3)
N2-H2...O1i 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[Bruker (2006). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2, SAINT and SADABS. 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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.  [ISI] [CrossRef] [ChemPort] [details]
Joseph, M., Kuriakose, M., Kurup, M. R. P., Suresh, E., Kishore, A. & Bhat, S. G. (2006). Polyhedron, 25, 61-70.  [ISI] [CSD] [CrossRef] [ChemPort]
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.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef]
Paterson, B. M. & Donnelly, P. S. (2011). Chem. Soc. Rev. 40, 3005-3018.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhao, R.-G., Zhang, W., Li, J.-K. & Zhang, L.-Y. (2008). Acta Cryst. E64, o1113.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o61  [ doi:10.1107/S1600536812049847 ]

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