Abstract
In the title compound [systematic name: rac-1-benzyl-5-bromo-3-hydroxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one ethanol monosolvate], C19H17BrN4O3·C2H5OH, which crystallized as a racemate (RR and SS), the isatin ring is almost planar, with an r.m.s. deviations from the mean plane of 0.0276 (14) Å. The phenyl ring of the benzyl group makes a dihedral angle with the mean plane of the isatin ring of 87.40 (5)° and the dihedral angle between the imidazole and isatin rings is 58.56 (7)°. In the crystal, molecules are linked into two-dimensional pleated-sheet networks in the ac plane formed by O—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds; within these sheets there are R 4 4(10) rings that involve three molecules of the title compound and a single ethanol solvent molecule. In addition, there are π–π interactions between inversion-related benzyl groups, with an interplanar spacing of 3.444 (3) Å.
Highlights
In the title compound [systematic name: rac-1-benzyl-5bromo-3-hydroxy-3-(2-imino-3-methyl-5-oxoimidazolidin4-yl)-2,3-dihydro-1H-indol-2-one ethanol monosolvate], C19H17BrN4O3C2H5OH, which crystallized as a racemate (RR and SS), the isatin ring is almost planar, with an r.m.s
The phenyl ring of the benzyl group makes a dihedral angle with the mean plane of the isatin ring of 87.40 (5) and the dihedral angle between the imidazole and isatin rings is 58.56 (7)
Background information on the biological importance of isatins has been given by Pandeya et al (2005), and by Vine et al (2007)
Summary
Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA Key indicators: single-crystal X-ray study; T = 90 K; mean (C–C) = 0.003 Å; R factor = 0.029; wR factor = 0.074; data-to-parameter ratio = 16.9.
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