Crystal structure of a 1,1,2,2-tetrachloroethane-solvated hydrazinecarbothioamide compound

The crystal structure of the title compound, which contains azomethine groups, is reported; its keto and enol tautomeric forms are investigated.


Figure 4
View of the packing in (I) along the a-axis direction, showing the hydrogen-bonded system.
hydrogen atom (clearly identified in the X-ray analysis) and forms an intramolecular hydrogen bond N8-H8NÁ Á ÁO1.
The structure of the product was substantiated via spectroscopic data. For example, 1 H NMR spectra of compounds 3 revealed two singlet signals at = 2.35 and 10.28 ppm, attributed to the methyl group adjacent to hydrazone (CH 3 -C N-NH) (de Oliveira et al., 2014) and NH of the hydrazone group (C N-NH), respectively; there are also two signals ( = 8.11 and 8.43 ppm) for the NH 2 group. A singlet signal at = 10.70 ppm is due to the OH group whereas the C OÁ Á ÁHN appears at = 12.53 ppm, see Fig. 3.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2. The non-hydrogen atoms were refined with anisotropic thermal parameters. Hydrogen atoms on the O and N atoms were located in difference maps and were refined with distance constraints viz O-H distances were set to 0.82 (2) (Sheldrick, 2015); molecular graphics: ORTEP (Johnson, 1976;Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and WinGX (Farrugia, 2012).

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.