{[(E)-(1,3-Benzodioxol-5-yl)methylidene]amino}thiourea

The synthesis and crystallographic analysis of [(E)-1,3-benzodioxol-5-ylmethylideneamino]thiourea is reported, offering a comprehensive exploration of its structural features and supramolecular arrangements within the crystal.

The synthesis and crystallographic analysis of the title compound, C 9 H 9 N 3 O 2 S, are reported.The compound crystallizes in the monoclinic space group P2 1 /c, revealing characteristic bond lengths and angles typical of thiosemicarbazone groups.The supramolecular organization primarily arises from hydrogen bonding and �-� stacking interactions, leading to distinctive dimeric formations.

Chemical context
The group of thiosemicarbazone Schiff bases, capable of coordinating with metal centers through nitrogen and sulfur atoms, has garnered significant recent attention (Corte ´s et al., 2011;Singh et al., 2016) due to the exhibited biological and pharmacological properties, such as antibacterial and antiviral activities (Hu et al., 2006).This study focuses on describing the synthesis and the analysis of the crystal structure of the title molecule.

Structural commentary
The target compound (I) crystallizes in the monoclinic space group P2 1 /c with one molecule in the asymmetric unit (Z = 4).A view of the molecule is shown in Fig. 1.Selected bond lengths and angles for the product are listed in Table 1.All bond lengths exhibit typical values (Dias et al., 2017).

Supramolecular features
The supramolecular arrangements of I primarily result from classical and non-classical hydrogen bonds and �-� stacking interactions.These contacts were recognized by Mercury 2022 (Macrae et al., 2020; sum of van der Waals radii plus 0.1 A ˚).The hydrogen-bonding geometry is listed in Table 2, and the packing of molecules viewed down along the c axis is shown in Fig. 2. Together, the hydrogen-bonding interactions lead to the formation of a two-dimensional network parallel to (100).The molecules at (x, y, z) and (2 À x, À y, 1 À z) are components of dimers centered at (1, 0, 1 2 ), while the separation between the aryl ring centroids is 3.778 (2) A ˚, indicating �-� stacking interactions between the aromatic ring systems.

Database Survey
Six crystal structures, authored by different researchers and featuring the [(E)-1,3-benzodioxol-5-ylmethylideneamino]thiourea fragment (piperonal, thiosemicarbazone), have been documented in the Cambridge Structural Database (CSD, WebCSD search December 2023; Groom et al., 2016).The crystal structure here under discussion can be considered the parent compound among those reported in the CSD.These other structures show substitutions in the imine hydrogen with methyl (de Oliveira et al., 2013Oliveira et al., , 2015a,b) ,b) or nitro group (Dias et al., 2017), and in the amidic hydrogen with methyl (de Oliveira et al., 2015b), ethyl (Dias et al. 2017;de Oliveira et al., 2015a), and phenyl (Dias et al. 2017) radicals.Some of these structures crystallize in the triclinic space group P1, while others in the monoclinic space group P2 1 /c.Finally, Beckford et al. (2011), provide detailed information on the crystal structure of [(� 6 -p-cymene)Ru(pPhTSC)Cl]Cl, which crystallizes in the monoclinic space group P2 1 /n.All of the structures reveal co-planar arrangements of the piperonal thio-semicarbazone portion along with �-� and hydrogen-bonding interactions.

Synthesis and crystallization
The synthesis of the Schiff base ligand (1,3-benzodioxol-5ylformaldehyde) thiosemicarbazone was performed according to a previously published procedure (Casas et al., 2015).

Refinement details
Crystal data, data collection and structure refinement details are summarized in Table 3.The H atoms were all located in difference maps, but those attached to carbon atoms were repositioned geometrically.The H atoms were initially refined with soft restraints on the bond lengths and angles to regularize their geometry (C-H in the range 0.93-0.98A ˚, N-H = 0.86 A ˚, O-H = 0.82 A ˚) and U iso (H) (in the range 1.2-1.5 times U eq of the parent atom), after which the positions were refined with riding constraints.

Table 3
Experimental details.