(E)-2-[(E)-3-(Hydroxyimino)butan-2-ylidene]-N-methylhydrazinecarbothioamide

In the title compound, C6H12N4OS, an intramolecular N—H⋯N hydrogen-bond is present giving rise to an S(5) ring motif. In the crystal, double-stranded chains propagating along [10] are formed via pairs of O—H⋯S and N—H⋯S hydrogen bonds. The chains are further stabilized by C—H⋯S interactions.

In the title compound, C 6 H 12 N 4 OS, an intramolecular N-HÁ Á ÁN hydrogen-bond is present giving rise to an S(5) ring motif. In the crystal, double-stranded chains propagating along [101] are formed via pairs of O-HÁ Á ÁS and N-HÁ Á ÁS hydrogen bonds. The chains are further stabilized by C-HÁ Á ÁS interactions.

Experimental
To a hot stirred solution of 2,3-butanedione monoxime (1.01 g, 10 mmole) in ethanol (20 ml) containing a few drops of glacial acetic acid was added 4-methyl-3-thiosemicarbazide (1.05 g, 10 mmole) dissolved in ethanol (20 ml). The reaction mixture was then heated under reflux for 3 h. The mixture was filtered and left to cool, the resulting white solid was collected by suction filtration and washed with cold EtOH. The white crystals were grown from ethanol soultion by slow evaporation at room temperature, yield, 78.8%, m.p., 487.5-490 K.

Refinement
N and O bound H atoms were located in a difference Fourier map and were refined freely. The remaining H atoms were positioned geometrically and refined using a riding model with C-H = 0.98 and U iso (H) = 1.5U eq (C) for methyl groups.
The highest residual electron density peak is located 0.63 Å from C2 and the deepest hole is located 0.68 Å from C4.
supplementary materials sup-2 Figures   Fig. 1. The molecular structure of the title compound with 50% probability displacement ellipsoids and the atom-numbering scheme. 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 Rfactors(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.