Relative configuration, absolute configuration and absolute structure of three isomeric 8-benzyl-2-[(4-bromophenyl)(hydroxy)methyl]-8-azabicyclo[3.2.1]octan-3-ones
| Autor: | Aneta Nodzewska, Katarzyna Sidorowicz, Krzysztof Brzezinski, Ryszard Lazny |
|---|---|
| Rok vydání: | 2013 |
| Předmět: |
Aza Compounds
Molecular Structure Bicyclic molecule Stereochemistry Chemistry Hydrogen bond Molecular Conformation Absolute configuration Space group Hydrogen Bonding General Medicine Crystal structure Ketones Bridged Bicyclo Compounds Heterocyclic Crystallography X-Ray General Biochemistry Genetics and Molecular Biology Crystal Crystallography Isomerism Group (periodic table) Atom |
| Zdroj: | Acta Crystallographica Section C Crystal Structure Communications. 69:303-306 |
| ISSN: | 0108-2701 |
| DOI: | 10.1107/s0108270113002503 |
| Popis: | The title compounds, C21H22BrNO2, are isomeric 8-benzyl-2-[(4-bromophenyl)(hydroxy)methyl]-8-azabicyclo[3.2.1]octan-3-ones. Compound (I), the (±)-exo,syn-(1RS,2SR,5SR,9SR) isomer, crystallizes in the hexagonal space groupR\overline{3}, while compounds (II) [the (+)-exo,anti-(1R,2S,5S,9R) isomer] and (III) [the (±)-exo,anti-(1RS,2SR,5SR,9RS) isomer] crystallize in the orthorhombic space groupsP212121andPna21, respectively. The absolute configuration was determined for enantiomerically pure (II). For the noncentrosymmetric crystal of (III), its absolute structure was established. In the crystal structures of (I) and (II), an intramolecular hydrogen bond is formed between the hydroxy group and the heterocyclic N atom. In the crystal structure of racemic (III), hydrogen-bonded chains of molecules are formedviaintermolecular O—H...O interactions. Additionally, face-to-edge π–π interactions are present in the crystal structures of (I) and (II). In all three structures, the piperidinone rings adopt chair conformations and theN-benzyl substituents occupy the equatorial positions. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text