A. Danilovski, M. Vinković, D. Filić
Aug 15, 1999
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Acta Crystallographica Section C-crystal Structure Communications
Abstract
Crystallographic experiments performed on single crystals of m-nitroglutethimide [3-ethyl-3-(3'-nitrophenyl)piperidine-2,6-dione, C 13 H 14 N 2 O 4 ], (I), and o,p-dinitroglutethimide [3-ethyl-3-(2',4'-dinitrophenyl)-piperidine-2,6-dione, C 13 H 13 N 3 O 6 ], (II), have unambiguously confirmed the molecular structures. From HPLC data it has been found that both of the title compounds are by-products in the nitration of glutethimide. The six-membered glutarimide rings of (I) and (II) have an envelope conformation with the C4 atom out of the plane, i.e. with C4-exo puckering in (I), but with C4-endo puckering in (II). Steric hindrances are, most likely, responsible for the observed conformational dissimilarity. The molecular structure of compound (I), unlike compound (II), is very similar to that of aminoglutethimide. Enantiomeric molecules in both compounds are linked together through pairs of symmetric R 2 2 (8) intermolecular hydrogen bonds forming centrosymmetric racemic dimers.