Supramolecular structures of four (Z)-5-arylmethylene-2-thioxothiazolidin-4-ones: hydrogen-bonded dimers, chains of rings and sheets

Abstract

In each of the four title compounds, namely (Z)-5-benzylidene-2-thioxothiazolidin-4-one, C10H7NOS2, (I), which crystallizes with Z' = 2 in space group P2(1)/n, (Z)-5-(4-methylbenzylidene)-2-thioxothiazolidin-4-one, C11H9NOS2, (II), (Z)-2-thioxo-5-[4-(trifluoromethyl)benzylidene]thiazolidin-4-one, C11H6F3NOS2, (III), and (Z)-5-(4-methoxybenzylidene)-2-thioxothiazolidin-4-one, C11H9NO2S2, (IV), there is a very wide C-C-C angle (ca 130 degrees ) at the methine C atom linking the two rings. Pairs of N-H...O hydrogen bonds link the two independent molecules in (I) into a cyclic dimeric unit, and these units are further linked into complex sheets by three independent C-H...pi(arene) hydrogen bonds. The molecules of (II) are linked by paired N-H...O hydrogen bonds into centrosymmetric R(2)(2)(8) dimers; the molecules of (III) and (IV) are linked into chains of rings, which are constructed from a combination of N-H...S and C-H...O hydrogen bonds in (III), and from a combination of N-H...O and C-H...S hydrogen bonds in (IV).

2-Methoxy-4-[(5-oxo-2-phenyl-4,5-dihydro-1,3-oxazol-4-ylidene)methyl]phenyl 4-methylbenzenesulfonate

“…The C15ÐC16 bond is signi®cantly shorter than the C11ÐC15 bond. Because of the steric hindrance of the oxazolone and aromatic rings, atom C15 has a distorted trigonal geometry, with the angle deviating signi®cantly from the ideal trigonal value, as found also in previously reported analogues (Delgado et al, 2005(Delgado et al, , 2006. The S atom has a distorted tetrahedral geometry.…”

Three substituted (Z)-5-benzylidene-2-thioxothiazolidin-4-ones: hydrogen-bonded dimers that can be effectively isolated or linked into chains either by aromatic π–π stacking interactions or by dipolar carbonyl–carbonyl interactions

“…1 and 2), and (Z)-5-(3,4,5-trimethoxybenzylidene)-2-thioxothiazolidin-4-one, (III) (Fig. 3), and we brie¯y compare these with the structures of the four analogues (IV)± (VII) (see scheme), which have been reported recently (Delgado et al, 2005). As for compounds (IV)±(VII), compounds (I)±(III) have been prepared by condensation of 2-thioxothiazolidin-4-one (rhodanine) with a substituted benzaldehyde using microwave radiation in a solvent-free system.…”

“…We note very brie¯y the different patterns of supramolecular aggregation in the analogues (IV)±(VII) (Delgado et al, 2005). In (IV), which crystallizes with Z H = 2 in the space group P2 1 /n, the two independent molecules are linked by NÐ HÁ Á ÁO bonds into a dimer, as in (III), but these dimers are not isolated; instead they are linked by CÐHÁ Á Á%(arene) hydrogen bonds into sheets.…”

Chemistry of polyhalogenated nitrobutadienes, 14: Efficient synthesis of functionalized (Z)-2-allylidenethiazolidin-4-ones

“…Thus, the 5-arylmethylidenethiazolidin-4-ones 22 – 26 were obtained in 68–94% yield. The presence of only one signal for the benzylidene proton at 7.83–7.98 ppm in the 1 H NMR spectra of 22 – 26 suggested the formation of a single isomer, which was assigned to the Z -configuration according to the literature for similar compounds [47–48]. Interestingly, close analogues of these structures, i.e., the 5-arylmethylidene rhodanines, possess photosynthesis-inhibiting and antialgal properties [49], show anticancer activity [50–51], and are inhibitors of bacterial enzyme synthetase MurD with E. coli [52].…”