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Volume 68 
Part 5 
Page o1533  
May 2012  

Received 17 April 2012
Accepted 18 April 2012
Online 25 April 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.053
wR = 0.171
Data-to-parameter ratio = 19.7
Details
Open access

Methyl 3-(2-hydroxybenzylidene)-2-methyldithiocarbazate

aUniversity of Chittagong, Chittagong 4331, Bangladesh, and bDepartamento de Química Inorgánica, Analítica y Química, Física/INQUIMAE-CONICET, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Argentina
Correspondence e-mail: tapashir57@gmail.com

In the title compound, C10H12N2OS2, the thione and S-methyl groups are syn. An intramolecular bifurcated O-H...(S,N) hydrogen bond occurs.

Related literature

For the biological activity of sulfur-ligand compounds, see: French & Blang (1965[French, F. A. & Blang, E. J. (1965). Cancer Res. 25, 1454-58.]); Ali & Livingstone (1974[Ali, M. A. & Livingstone, S. E. (1974). Coord. Chem. Rev. 13, 101-132.]); Ali et al. (1995[Ali, M. A., Fernando, K. R., Palit, D. & Nazimuddin, M. (1995). Transition Met. Chem. 20, 19-22.]); Hazari et al. (1999[Hazari, S. K. S., Dey, B. K., Palit, D., Roy, T. G., Ali, M. A. & Sen, K. (1999). J. Bang. Chem. Soc. 12, 83-91.], 2002[Hazari, S. K. S., Dey, B. K., Palit, D., Ganguli, B. & Sen, K. (2002). Ceylon J. Sci. Phys. Sci. 9, 23-30.]). For the synthesis and characterization of sulfur-nitrogen-containing ligands, see: Hazari et al. (2002[Hazari, S. K. S., Dey, B. K., Palit, D., Ganguli, B. & Sen, K. (2002). Ceylon J. Sci. Phys. Sci. 9, 23-30.], 2006[Hazari, S. K. S., Dey, B. K., Palit, D., Roy, T. G. & Alam, K. M. D. (2006). Ceylon J. Sci. Phys. Sci. 11, 23-31.]). For a related structure, see: Hazari et al. (2012[Hazari, S. K. S., Dey, B. K., Roy, T. G., Ganguly, B., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1216.]).

[Scheme 1]

Experimental

Crystal data
  • C10H12N2OS2

  • Mr = 240.34

  • Monoclinic, P 21 /c

  • a = 11.3561 (16) Å

  • b = 8.9033 (13) Å

  • c = 11.5045 (16) Å

  • [beta] = 91.411 (13)°

  • V = 1162.8 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.43 mm-1

  • T = 298 K

  • 0.35 × 0.30 × 0.22 mm

Data collection
  • Oxford Diffraction Gemini CCD S Ultra diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.859, Tmax = 0.917

  • 16680 measured reflections

  • 2833 independent reflections

  • 2039 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.171

  • S = 1.05

  • 2833 reflections

  • 144 parameters

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

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...S2 0.91 (5) 2.67 (5) 3.453 (2) 145 (4)
O1-H1O...N1 0.91 (5) 1.88 (5) 2.678 (3) 145 (4)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS86 (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 for Windows (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]); 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: QM2064 ).


Acknowledgements

The authors acknowledge the UGC, Bangladesh, for the award of a fellowship to BG and thank the TWAS, Trieste, Italy, for awarding a TWAS-UNESCO Associateship to TGR. They are also grateful to ANPCyT for a grant (PME-2006- 01113) and to R. Baggio for his helpful suggestions.

References

Ali, M. A., Fernando, K. R., Palit, D. & Nazimuddin, M. (1995). Transition Met. Chem. 20, 19-22.  [CrossRef] [ChemPort]
Ali, M. A. & Livingstone, S. E. (1974). Coord. Chem. Rev. 13, 101-132.  [CrossRef] [ChemPort]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
French, F. A. & Blang, E. J. (1965). Cancer Res. 25, 1454-58.  [ChemPort] [PubMed]
Hazari, S. K. S., Dey, B. K., Palit, D., Ganguli, B. & Sen, K. (2002). Ceylon J. Sci. Phys. Sci. 9, 23-30.
Hazari, S. K. S., Dey, B. K., Palit, D., Roy, T. G. & Alam, K. M. D. (2006). Ceylon J. Sci. Phys. Sci. 11, 23-31.
Hazari, S. K. S., Dey, B. K., Palit, D., Roy, T. G., Ali, M. A. & Sen, K. (1999). J. Bang. Chem. Soc. 12, 83-91.
Hazari, S. K. S., Dey, B. K., Roy, T. G., Ganguly, B., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o1216.  [CrossRef] [details]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o1533  [ doi:10.1107/S160053681201731X ]

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