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

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

In the title compound, C 10 H 12 N 2 OS 2 , the thione and S-methyl groups are syn. An intramolecular bifurcated O-HÁ Á Á(S,N) hydrogen bond occurs.

Experimental
Hence, the crystal structure of the ligand has been described.

Experimental
The title compound was isolated by following four steps synthetic procedure: Step1. Synthesis of N-methyl-S-methyldithiocarbamate: Potassium hydroxide (11.5 g) was dissolved in 60 ml of 90% ethanol and the mixture was cooled down to 273 K in an ice bath. To this, methylhydrazine (11.1 ml) was added slowly with mechanical stirring. A solution of carbondisulfide (12 ml) was added dropwise from a burette with constant stirring over a period of an hour. During the addition of carbondisulfide, the temperature of the reaction mixture was not allowed to rise above 279 K. A yellow colored solution was obtained. After adding carbondisulfide, methyl iodide (12.5 ml) was added from a burette dropwise with vigorous mechanical stirring. After the complete addition, the mixture was stirred for further 15 minutes, whereupon well formed shining crystals appeared. The product was separated by filtration and washed with water and recrystallized from ethanol and dried in a vacuum desiccator over silica gel. Yield: 15.25 g, M.pt.: 361-363 K.
Step 2. Synthesis of methyl-N-(2-hydroxybenzyledine)-N-methyl hydrazinecarbodithionate, L (1): A hot solution of salicyladehyde (1.04 ml, 10 mmol) in absolute ethanol (40 ml) was mixed with hot solution of N-methyl-S-methyldithiocarbamate (1.36 g, 10 mmol) in the same solvent. The mixture was refluxed for 6 h. on a water bath. After reducing the volume, a yellowish white product appeared which was filtered off. This product was washed with ethanol several times (3 x 2 ml) and dried in a vacuum desiccator over silica gel. Yield: 1.65 g. M.pt.: 399-401 K.
Step 3. Attempted preparation of the oxovanadium(IV) complex with (I): Vanadyl acetylacetonate [VO2(acac)2] (2.65 g, 10 mmol) was dissolved in dry ethanol, in which a hot solution of L (2.4 g, 10 mmol) in dry ethanol was added. The mixture was refluxed for 6 h. on water bath. After reducing the volume and standing over night a light greenish yellow product appeared, which was washed with ethanol for several times and dried in a vacuum desiccator over silica gel.
Melting point of product was 443-445 K. Step 4. Crystallization: The product was dissolved in ethanol to which half volume of petroleum ether was added (10/5 ml v/v). The solution was left for several days after which the title compound, (I), was deposited as crystals.

Refinement
Methyl groups were idealized (C-H = 0.96 A °) and allowed to ride. In all cases, H-atom displacement parameters were taken as U iso (H) = 1.5Ueq(C) for methyl groups or 1.2Ueq(C,O) otherwise.

Figure 1
The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Figure 2
Cristal packing for the title compound viewed along c.

Methyl 3-(2-hydroxybenzylidene)-2-methyldithiocarbazate
Crystal data Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.