5-Fluoroindoline-2,3-dione

Abstract

In the title compound (5‐fluoro­isatin), C8H4FNO2, the N atom of one mol­ecule is linked to the amido‐O atom of an adjacent mol­ecule across a center of symmetry by a cyclic hydrogen bond [N⃛O = 2.888 (4) Å].

Synthesis and theoretical study of 5-methoxyisatin-3-(N-cyclohexyl)thiosemicarbazone and its Ni(II) and Zn(II) complexes

“…Previously 5-methoxyisatin-3-(N-phenyl) thiosemicarbazone, 5-methoxyisatin-3-(N-benzyl)thiosemicarbazone and 5-methoxyisatin-3-(N-(4-chlorophenyl))thiosemicarbazone [9], and zinc(II) complex of 5-fluoroisatin-3-(N-benzyl)thiosemicarbazone [10] were synthesized and characterized. The crystal structure of 5-fluoro-1-(morpholin-4-ylmethyl)-1H-indole-2,3-dione-3-(Nallylthiosemicarbazone), 5-fluoro-1-(piperidin-1-ylmethyl)-1H-indole-2,3-dione-3-(N-allylthiosemicarbazone) [4], isatin 3-semicarbazone and 1-methyl-isatin 3-semicarbazone [11], 5-fluoroindoline-2,3-dione [12] had been reported.…”

Discovery of three polymorphs of 7-fluoroisatin reveals challenges in using computational crystal structure prediction as a complement to experimental screening

“…A manual crystallisation screen of 7-fluoroisatin led to the discovery of three polymorphs, whereas a similar screen on the isomer 5-fluoroisatin gave only the previously known crystal structure. The experimental stability ordering of the polymorphs of 1, with the thermodynamically most stable form displaying a Z 0 ¼ 2 R 4 4 (18) hydrogen bonding motif, clearly shows that this polymorphic system will provide a stringent test for the development of computational polymorph prediction methods. In contrast, the crystal structure of the isomer, 2, was readily predicted, and we can only hypothesise as to why metastable polymorphs with different hydrogen bonding motifs were not found.…”

“…Form II crystallises in the triclinic space group P1 with two independent molecules in the asymmetric unit (Table 1). In contrast to forms I and III which have structures based on the R 2 2 (8) dimer, the crystal structure of form II is characterised by an expanded tetrameric R 4 4 (18) ring motif. Only one oxygen of each symmetry independent molecule is utilised as a hydrogen bond acceptor; O2 for molecule 1 and O1 in molecule 2.…”

N′-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene)benzenesulfonohydrazide

“…For the crystal structures of related 3-indole benzenesulfonylhydrazones, see: Ali et al (2007a,b,c). For the crystal structure of 5-fluoro-1H-indole-2,3-dione, see: Naumov et al (2000).…”

“…The studies continue with the benzenesulfonohydrazide that is obtained by condensing benzenesulfonohydrazine with a substituted 1H-indol-2,3-dione, 5-fluroisatin. This compound exists as a hydrogen-bonded dimer (Naumov et al, 2000).…”