4-Fluorobenzyl (Z)-2-(2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate

The crystal structure of a new fluorinated dithiocarbazate imine containing the isatin moiety, 4-fluorobenzyl (Z)-2-(2-oxoindolin-3-ylidene)hydrazine-1-carbodithioate, is described.

The title compound, C 16 H 12 FN 3 OS, a fluorinated dithiocarbazate imine derivative, was synthesized by the one-pot, multi-component condensation reaction of hydrazine hydrate, carbon disulfide, 4-fluorobenzyl chloride and isatin.The compound demonstrates near-planarity across much of the molecule in the solid state and a Z configuration for the azomethine C N bond.The Z form is further stabilized by the presence of an intramolecular N-H� � �O hydrogen bond.In the extended structure, molecules are linked into dimers by N-H� � �O hydrogen bonds and further connected into chains along either [210] or [100] by weak C-H� � �S and C-H� � �F hydrogen bonds, which further link into corrugated sheets and in combination form the overall three-dimensional network.

Structure description
Various sulfur-containing molecules isolated from natural sources have been reported to exhibit a broad spectrum of biological activities (Wang et al., 2020;Chen & Li, 2023).Some synthetic sulfur-containing drugs inspired by natural products include the antibiotics dalfopristin and quinupristin, and the anticancer agents phthalascidin and ixabepilone (Mustafa & Winum, 2022;Hai et al., 2021).The ubiquitous role of fluorine in the design of bioactive molecules is expending rapidly, as a better understanding of the unique properties of this element is gained.The introduction of a fluorinated substituent atom can influence pK a , basicity, dipole moment, conformation, intrinsic potency, membrane permeability, metabolic stability and pharmacokinetic properties (Richardson, 2021;Ali & Zhou, 2023).The literature reveals that various fluorine-and sulfur-containing drugs have been approved by the US Food and Drug Administration to combat diseases.Some examples are the recently reported lenacapavir for the treatment of HIV-1 infection (Paik, 2022;Han & Lu, 2023) and belzutifan for the treatment of kidney cancer (Deeks, 2021;Fallah et al., 2022).As part of our ongoing studies in this area, we now describe the synthesis and structure of the title compound.

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.Refinement.Refined as a 2-component twin.

Figure 3
Figure 3View of the hydrogen-bonded chains along [100] (top to bottom) formed from a combination of weak C-H� � �S and C-H� � �F hydrogen bonds with R 1 2 (6) and R 2 2 (8) motifs, respectively.

Table 2
Experimental details.