Crystal structure of (Z)-4-benzyl-N'-(4-chloro-2-oxoindolin-3-ylidene)- piperazine-1-carbothiohydrazide, C_(20)H_(20)ClN_5OS

摘要

(Equation presentation) (Table presentation) Source of material A mixture of the 4-chloroindoline-2,3-dione (0.18 g, 1.0 mmol) and 4-benzylpiperazine-1- carbothiohydrazide (0.25 g, 1.0mmol) in absolutemethanol (20 mL) was stirred at room temperature for 3 days. Thin layer chromatography (TLC) of the solution indicated the end of the reaction (Rf = 0.40, dichloromethane/methanol = 95:5, v/v). The precipitates were collected by filtration and dried in air, which was purified by recrystallization from ethanol to give the title compound (yield 40%; m.p. 497-498 K). Yellow single crystals suitable for X-ray diffraction were grown from a mixture of dichloromethane and methanol (5:1, v/v) by slow evaporation at room temperature. Experimental details Accidentally only 94.5% data completeness was achieved. Discussion Substituted indolin-2-ones have been identified as a versatile scaffold which exhibit diverse chemotherapeutic activities such as anticancer, antiviral and many others properties [1-3]. Among them, 1H-indole-2,3-dioxo-3-thiosemicarbazones have in general been reported to possess antitumour activities [3, 4].Our previous studies have revealed the promising cytotoxic properties of various piperazine-1-carbothiohydrazide-based derivatives of indolin-2-one [5].With the effort to obtain new and more potential antitumor agents, we synthesized the title compound. The dihedral angles between the indol-2-one ring and the benzene ring is 39.08(3)°, while the bridging piperazine ring links to the indol- 2-one via C9-N3-N2 atoms and to the benzene ring via a methylene group, and adopts a chair conformation. The double bond lengths between C7 and N2 (1.301(3) ?) are in agreement with those analog reported [6, 7]. Furthermore, there are two N- H...O hydrogen bonds (D...A = 2.742(3) ?,