Received 11 December 2012
The title compound, C19H18N4O3 [systematic name: (RS)-1-benzyl-3-hydroxy-3-(2-imino-3-methyl-5-oxoimidazolidin-4-yl)-2,3-dihydro-1H-indol-2-one], was prepared as a racemate (RR and SS) by the aldol condensation of N-benzylisatin with creatinine in the presence of sodium acetate in acetic acid. The r.m.s. deviation of the isatin ring system is 0.033 Å. The benzyl group is disordered over two orientations, with refined occupancies of 0.847 (7) and 0.153 (7). The dihedral angles between the isatin ring system and the benzene ring (major disorder component) and the imidazole ring are 82.82 (7) and 51.31 (3)°, respectively, In the crystal, molecules are linked into (001) sheets by N-HO and O-HN hydrogen bonds, which incorporate R22(9) ring motifs. The crystal was grown from mixed solvents (ethanol, methanol and possibly also ethyl acetate). These solvents are disordered in the crystal and the resulting electron density was found to be uninterpretable. The solvent contribution to the scattering was removed with the SQUEEZE routine in PLATON [Spek (2009). Acta Cryst. D65, 148-155]. The formula mass and density do not take account of the solvent.
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; 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: SHELX97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7013 ).
This investigation was supported by NIH/National Cancer Institute grant RO1 CA140409.
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