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The crystal structures of four cyclo­alkane­spiro‐4′‐imidazolidine‐2′,5′‐dithiones, namely cyclo­pentane­spiro‐4′‐imidazolidine‐2′,5′‐dithione {systematic name: 1,3‐diaza­spiro­[4.4]­nonane‐2,4‐dithione}, C7H10N2S2, cyclo­hexane­spiro‐4′‐imidazolidine‐2′,5′‐dithione {systematic name: 1,3‐diaza­spiro­[4.5]decane‐2,4‐dithione}, C8H12N2S2, cyclo­heptane­spiro‐4′‐imidazolidine‐2′,5′‐dithione {systematic name: 1,3‐diaza­spiro­[4.6]undecane‐2,4‐dithione}, C9H14N2S2, and cyclo­octane­spiro‐4′‐imidazolidine‐2′,5′‐dithione {systematic name: 1,3‐di­aza­spiro­[4.7]dodecane‐2,4‐dithione}, C10H16N2S2, have been determined. The three‐dimensional packing in all of the structures is based on closely similar chains, in which hydantoin moieties are linked through N—H⋯S hydrogen bonding. The size of the cyclo­alkane moiety influences the degree of its deformation. In the cyclo­octane compound, the cyclo­octane ring assumes both boat–chair and boat–boat conformations.

This work describes a method for synthesis, as well as in vitro antiproliferative and antibacterial investigation of 3-methyl-9'-fluorenespiro-5-hydantoin. The structure of the substituted fluorenylspirohydantoin derivative was verified by UV-Vis, FT-IR, Raman, 1 H NMR and 13 C NMR spectroscopy, and by using a combination of 2D NMR experiments, which included 1 H-1 H COSY, HMQC and HMBC sequences. The geometry of the compound was optimized by the B3LYP density functional with 6-31G(d) basis set and the 1 H and 13 C NMR spectra were predicted with the HF/6-31G(d) calculations at the optimized geometry. The anticancer activity of the 3-methyl-9'-fluorenespiro-5-hydantoin was determined in suspension cell lines originating from tumors in humans (WERI-Rb-1). The cytotoxic effect was evaluated by WST-assay (Roche Applied Science). The antimicrobial effect of the compound against Gram-negative, Gram-positive bacteria and the yeast Candida albicans was investigated.

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The synthesis, structure and spectral properties of a new cinnamoyl derivative of 2-acetyl-1,3-indandione (2AID), p-fluoro-cinnamoyl-1,3-indandione, LH and its metal(II) complexes with Cu(II), Zn(II) and Cd(II), are described. In order to verify the molecular structure of the free ligand and its metal complexes, model geometries based on the spectroscopic data were optimized using quantum chemical methods. The experimental spectroscopic data (IR and NMR) of the ligand, LH, complemented by the calculated ones, show that it exists in the exocyclic enolic form in the gas phase, solution and solid state. Good quality single crystals of Cd(II) complex were obtained from a DMSO solution and were studied by means of single-crystal X-ray diffraction. The data show bidentate coordination of the ligand and two DMSO molecules coordinated to the metal centre, thus forming a complex with octahedral geometry. On the contrary, the spectroscopic data on the amorphous samples indicate a square planar geometry of the Cu(II) complex and distorted octahedral geometry for Zn(II) and Cd(II) complexes with two water molecules coordinated to the metal centre. The used quantum chemical method for structure optimization of the transition metal complexes, B3LYP/LANL2DZ, shows very good agreement with the crystallographic data and, therefore, was also employed for structural determination for the non-crystalline complexes.