Received 11 December 2012
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-HO, N-HO and O-HN hydrogen bonds; within these sheets there are R44(10) rings that involve three molecules of the title compound and a single ethanol solvent molecule. In addition, there are - interactions between inversion-related benzyl groups, with an interplanar spacing of 3.444 (3) Å.
Background information on the biological importance of isatins has been given by Pandeya et al. (2005), and by Vine et al. (2007). For similar structures, see: Tang et al. (2009); Penthala et al. (2009a,b).
Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 and local procedures.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5279 ).
This investigation was supported by NIH/National Cancer Institute grant PO1 CA140409. We thank Dr S. Parkin, University of Kentucky, for X-ray crystallographic services.
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