(E)-2-(2-Hydroxy-3-methylbenzylidene)-N-methylhydrazine-1-carbothioamide: supramolecular assemblies in two-dimensions mediated by N—H⋯S and C—H⋯π interactions

The character of the methylhydrazine carbothioamide moiety in the title compound is a thiosemicarbazone Schiff base was confirmed by its bond lengths and bond angles. In the crystal, molecules of the title compound are mediated into sheets parallel to the ab plane by N—H⋯S hydrogen bonds and C—H⋯π interactions.

In the title compound, C 10 H 13 N 3 OS, the azomethine C N double bond has an E configuration. The phenyl ring and methylhydrazine carbothioamide moiety [maximum deviation = 0.008 (2) Å ] are twisted slightly with a dihedral angle of 14.88 (10) . In the crystal, molecules are linked into sheets parallel to the ab plane via N-HÁ Á ÁS hydrogen bonds and C-HÁ Á Á interactions.

Chemical context
Schiff base compounds are very important and can be used for multidisciplinary applications. They are widely used in the food and dye industries and exhibit many types of biological activity (Gaur, 2000) such as antibacterial, antifungal, and antimalarial (Annapoorani & Krishnan, 2013). The azomethine C N group of Schiff bases plays an important role in the biological activity. Metal complexes of thiosemicarbazones have also received much attention. The metal chelation typically improves the lipophilicity of the ligand and facilitates the penetration of the complexes into bacterial membranes (Lobana et al., 2009;Rogolino et al., 2017). Thiosemicarbazones have multi-donor characteristics because of the presence of nitrogen and sulfur atoms in their molecular backbone. This results in a variety of coordination modes and many different physiochemical properties (Sharma et al., 2016). As part of our ongoing studies on thiosemicarbazone Schiff bases (Arafath et al., 2018a), we report herein the synthesis and structural determination of the title compound.

Figure 3
(a) A view of a dimer of C 10 H 13 N 3 OS with N2-H1N2Á Á ÁS1 hydrogen bonds shown as cyan dotted lines. (b) A view of a dimeric sheet with C10-H10AÁ Á ÁCg1 interactions shown as green dotted lines. Hydrogen atoms not involved in with these interactions are omitted for clarity.

Figure 1
The atom labelling scheme and displacement ellipsoids of the molecular structure at the 50% probability level.

Synthesis and crystallization
2-Hydroxy-3-methylbenzaldehyde (0.68 g, 5.00 mmol) was dissolved in 20.0 mL of methanol. 0.20 mL of glacial acetic acid was added and the mixture was refluxed for 30 minutes. A solution of 0.52 g (5.00 mmol) of N-methyl hydrazinecarbothioamide in 20.0 mL of methanol was added dropwise with stirring to the aldehyde solution (Fig. 4). The resulting colourless solution was heated under reflux for 4 h with stirring. The crude product was washed with 5.0 mL of n-hexane.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 3. C-bound H atoms were positioned geometrically (C-H = 0.93-0.96 Å ) and refined using a riding model with U iso (H) = 1.2 or 1.5 U eq (C). All N-and O-bound H atoms were located from a difference-Fourier map and freely refined. Reaction scheme for the synthesis of C 10 H 13 N 3 OS.  program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXL2013 (Sheldrick, 2015) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015) and PLATON (Spek, 2009).

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.