2,9-Bis(3-nitrophenyl)-1-azaadamantan-4-one

Abstract

The title compound, 2,9-bis(3-nitrophenyl)-1-azatricyclo[3.3.1.1(3,7)]decan-4-one, C21H19N3O5, has a tricyclic structure. The torsion angles may be used to describe the relationship of the carbonyl group to the adjacent faces, whereby it is seen that the angles on the face of the arylpiperidinone side [122.0 (3) and -122.0 (3) degrees ] are greater than those on the cyclohexanone side [-119.8 (4) and 119.9 (4) degrees ]. Although these differences may explain a facial selectivity during nucleophilic addition to the carbonyl group, the presence of the aryl rings is probably also important.

Assessable Consequences of Through‐Bond Donor–Acceptor Interactions in β‐Aminoketones

“…We have chosen instead to discuss and analyze bond lengths (Figure 5 and Table 2) and angles (Figure 6 and Table 3) in the context of related aza‐ and deaza‐adamantane crystal structures (with crystallographic R factors <0.05) 23. Included in Table 2 is the average bond length data for 6 and 7 , along side data for analogous structures available in the literature (the di‐ (CSD code KOLSIN24) and mono‐ (OCAYEW25) ketones 23 and 24 , respectively) and a saturated aza‐adamantane 25 (EJIQUJ26). 27 Also shown are average bond lengths for three adamantanediones (DESVIG ( 26 ),28 LIXFIH ( 27 ),29 and LIXFUT ( 28 )29), a selected adamantanone (FITPED ( 29 )30), and variously substituted adamantanes ( AD ).…”