(2Z)-2-(5-Fluoro-1-methyl-2-oxoindolin-3-ylidene)-N-(3-fluorophenyl)hydrazine-1-carbothioamide

Abstract

In the title compound, C16H12F2N4OS, the whole molecule is essentially planar (r.m.s deviation = 0.003 Å), with only the H atoms of the methyl group lying out of the molecular plane. A planar indole fused-ring system (r.m.s deviation = 0.004 Å) is linked through a hydrazine–carbothioamide bridge to a fluorobenzene ring, with the indole ring system and inclined to the fluorobenzene ring by 4.26 (14)°. The planarity of the molecule is strengthened by three intramolecular N—H...N, N—H...O and C—H...S hydrogen bonds that generateS(5),S(6) andS(6) ring motifs, respectively. In the crystal, π–π stacking interactions combine with C—H...·F hydrogen bonds to link the molecules into layers parallel to the (10-1) plane.

5‐Fluoro/(trifluoromethoxy)‐2‐indolinone derivatives with anti‐interleukin‐1 activity

“…1‐(Non)substituted 5‐fluoro/(trifluoromethoxy)−1 H ‐indole‐2,3‐dione 3‐(4‐phenylthiosemicarbazones) (compounds 47–116 ) were obtained by condensation of the compounds 1–8 with the compounds 28–46 . [ 30,39,42–45 ] The compounds 47–82 and 99 have been previously described by Güzel et al, [ 30 ] Karalı et al, [ 34,46 ] Sevinçli et al, [ 39,42 ] Soylu‐Eter et al, [ 43 ] Ahmad et al, [ 44 ] and Pervez et al [ 45 ] in literature (Experimental information for these molecules was given in the Supplementary Material). Structures of the synthesized new compounds 83–116 were confirmed by spectral (IR, 1 H NMR, 13 C NMR, HSQC‐2D, HMBC‐2D, and MS) and analytical data (Scheme 1, Section 4, and Supporting Information).…”

“…The isomeric structures of compounds 72 and 99 were determined by X‐ray single‐crystal diffraction analysis, and the stable isomers were found to be in Z configuration. [ 42,43 ]…”

“…The isomeric structures of compounds 72 and 99 were determined by X-ray single-crystal diffraction analysis, and the stable isomers were found to be in Z configuration. [42,43] The new compounds' solid phase (KBr) IR spectra showed in 3134-3361 cm −1 region resulting from the NH stretching bands of the thioamide groups. Furthermore, C═S stretching bands observing 1138-1273 cm −1 region proved the presence of thioamide groups.…”

“…(compounds 47-116) were obtained by condensation of the compounds 1-8 with the compounds 28-46. [30,39,[42][43][44][45] The compounds 47-82 and 99 have been previously described by Güzel et al, [30] Karalı et al, [34,46] Sevinçli et al, [39,42] Soylu-Eter et al, [43] Ahmad et al, [44] and Pervez et al [45] in literature (Experimental information for these molecules was given in the Supplementary Material). Structures of the synthesized new QPlogBB: Blood-brain barrier partition coefficient, CNS: central nervous system activity.…”

Molecular and crystal structure of 1-methyl 5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone]

“…The N-N-C S and N-N-C(S)-N torsion angles were -170.76(19) and 8.0 (3)°, respectively. All bond lengths and angles were within normal ranges and were in agreement with those reported for 2-(5-fluoro-1-methyl-2-oxoindolin-3-ylidene)-N-[4-(methylsulfanyl) phenyl]hydrazine-1-carbothioamide (Atioğlu, et al, 2017a), (Z)-2-(6-fluoro-3-methyl-2-oxo-2,3-dihydro-1H-inden-1-ylidene)-N-(3-fluorophenyl)hydrazine-1-carbothioamide (Atioğlu, Sevinçli, Karalı, Akkurt, & Ersanlı, 2017b), (3E)-3-[(4-butylphenyl)imino]-1,3-dihydro-2H-indol-2-one (Akkurt, Öztürk, Erçağ, Özgür, & Heinemann, 2003), N'-[(2Z)-3-allyl-4-oxo-1,3thiazolidin-2-ylidene]-5-fluoro-3-phenyl-1H-indole-2-carbohydrazide (Akkurt, Karaca, Cihan, Çapan, & Büyükgüngör, 2009) and 5-trifluoromethoxy-1H-indole-2,3-dione 3-thiosemicarbazone derivatives (Kaynak et al, 2013).…”