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

Hazari, S.K.S.; Suarez, S.; Ganguly, B.; Doctorovich, F.; Goy, T.

doi:10.1107/S160053681201731X

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 (C-C) = 0.004 Å
R = 0.053
wR = 0.171
Data-to-parameter ratio = 19.7
Details

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

S. K. S. Hazari,^a Sebastian Suarez,^b Biplab Ganguly,^a Fabio Doctorovich ^b and Tapashi G. Roy ^a ^*

^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); Ali & Livingstone (1974); Ali et al. (1995); Hazari et al. (1999, 2002). For the synthesis and characterization of sulfur-nitrogen-containing ligands, see: Hazari et al. (2002, 2006). For a related structure, see: Hazari et al. (2012).

Experimental

Crystal data

C₁₀H₁₂N₂OS₂
M_r = 240.34
Monoclinic, P 2₁ /c
a = 11.3561 (16) Å
b = 8.9033 (13) Å
c = 11.5045 (16) Å
= 91.411 (13)°
V = 1162.8 (3) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.859, T_max = 0.917
16680 measured reflections
2833 independent reflections
2039 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(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
_max = 0.42 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1OS2	0.91 (5)	2.67 (5)	3.453 (2)	145 (4)
O1-H1ON1	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

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.
Ali, M. A. & Livingstone, S. E. (1974). Coord. Chem. Rev. 13, 101-132.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
French, F. A. & Blang, E. J. (1965). Cancer Res. 25, 1454-58.
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.
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds