Abstract
The X-ray crystal structure of the drug N-(2,6-dioxo-3-piperidyl)pthalimide (thalidomide), C13H10N2O4, obtained from 1∶1 dimethyformamide-ethanol solution, is reported. This species is monoclinic, space groupC2/c, witha=20.679(5),b=8.042(2),c=14.162(5) Å, β=102.86(3)°,Z=8,R=0.051 for 1674 unique reflections. crystal packing is determined by intermolecular N−H... O hydrogen bonding which is more extensive than that reported in the literature for a racemate of thalidomide crystallizing in space groupP21/n. Comparison of the melting behavior and X-ray powder diffractograms of the two racemic polymorphs shows that they are distinctly different, allowing easy identification of these species. By comparing experimental X-ray powder patterns with those calculated from single crystal data, it was concluded that neither of these polymorphs undergoes a phase change on trituration.
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Caira, M.R., Botha, S.A. & Flanagan, D.R. Polymorphism of N-(2,6-dioxo-3-piperidyl)pthalimide (thalidomide): Structural characterization of a second monoclinic racemic modification. J Chem Crystallogr 24, 95–99 (1994). https://doi.org/10.1007/BF01665353
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DOI: https://doi.org/10.1007/BF01665353