Crystal structure of ( E )-3-(benzylideneamino)- 2-phenylthiazolidin-4-one, C 16 H 14 N 2 OS

C 16 H 14 N 2 OS, monoclinic, P 2 1 / n (no. 14), a = 13.8369(4) Å, b =15.8967(4) Å, c =13.8600(4) Å, β =109.983(1) ° , V =2865.11(14) Å 3 , Z = 8, R gt ( F ) = 0.0439, w R ref ( F 2 ) = 0.1091, T = 296.15 K.


Source of material
All reagents were purchased from Merck and used as obtained.The target compound was synthesized in two synthetic steps where the intermediate (1E,2E)-1,2-dibenzylidenehydrazine was obtained according to Brown with slight modification [5].In the first step, benzaldehyde (19.6 mmol) and acetic acid (0.5 mL) were added to a round bottom flask containing 10 mL of absolute ethanol.To this mixture, 2 mol equivalence of hydrazine monohydrate was added dropwise and stirred at room temperature for 3 h.Thereafter, the precipitate was filtered and dried under vacuum.To synthesize (E )-3-(benzylideneamino)-2-phenylthiazolidin-4-one, a procedure by Ravichandran [6] was employed with slight modification.A mixture of (1E,2E)-1,2-dibenzylidenehydrazine (1 mmol), thioglycolic acid (1 mmol) and a catalytic amount of ZnCl 2 was refluxed at 100 °C overnight.After the completion of the reaction, as monitored by TLC, the solvent was removed under reduced pressure and the remaining residue was dissolved in ethyl acetate.The organic layer was then successively washed with water, 10 % NaHCO 3 and brine solution.Subsequently, the organic layer was dried over anhydrous Na 2 SO 4 , filtered and concentrated under reduced pressure to afford the crude product.Slow evaporation of an ethanolic solution of the crude afforded colourless block crystals of the target compound.The crystals were collected by vacuum filtration and dried in vacuo.Yield = 67 %, 1

Experimental details
Using OLEX2 [2], the structure was solved with the SHELXT [3] structure solution program using intrinsic phasing and refined with the olex2.refine[4] refinement package.
3 Comment Thiazolidinones are widely recognized for their remarkable biological properties, including anticancer [7] and antidiabetic effects [8,9].The electron-rich thiazole component of the pharmacophore makes it an ideal ligand for binding to enzymes and receptors [10].As a result, medicinal chemists find thiazolidinones to be an intriguing subject of study [11].
In this work, we report a crystal structure of a novel thiazolidinone derivative.

Table  :
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å  ).