NDLI: 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

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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

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Year: 2013 Volume: 69 Issue: Part 2

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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

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Brzezinski, Krzysztof Lazny, Ryszard Nodzewska, Aneta Sidorowicz, Katarzyna
Description	Country affiliation: Poland Author Affiliation: Brzezinski K ( Institute of Chemistry, University of Bialystok, Hurtowa 1, 15-399 Bialystok, Poland. k.brzezinski@uwb.edu.pl)
Abstract	The title compounds, C $_{21}H$ $_{22}BrNO$ $_{2},$ are isomeric 8-benzyl-2-[(4-bromophenyl)(hydroxy)methyl]-8-azabicyclo[3.2.1]octan-3-ones. Compound (I), the (±)- exo, syn-(1 RS,2 SR,5 SR,9 SR) isomer, crystallizes in the hexagonal space group R , while compounds (II) [the (+)- exo, anti-(1 R,2 S,5 S,9 R) isomer] and (III) [the (±)- exo, anti-(1 RS,2 SR,5 SR,9 RS) isomer] crystallize in the orthorhombic space groups P2 $_{1}2$ $_{1}2$ $_{1}$ and Pna2 $_{1},$ 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 formed via intermolecular O-H O interactions. Additionally, face-to-edge - interactions are present in the crystal structures of (I) and (II). In all three structures, the piperidinone rings adopt chair conformations and the N-benzyl substituents occupy the equatorial positions.
File Format	HTM / HTML
e-ISSN	20532296
Journal	Acta Crystallographica Section C Crystal Structure Communications
Issue Number	Pt 3
Volume Number	69
Language	English
Publisher	IUCr/Wiley
Publisher Date	2013-03-01
Publisher Place	United States
Access Restriction	Open
Subject Keyword	Discipline Analytical Chemistry Discipline Crystallography Aza Compounds Chemistry Bicyclo Compounds, Heterocyclic Ketones Crystallography, X-ray Hydrogen Bonding Isomerism Molecular Conformation Molecular Structure Research Support, Non-u.s. Gov't
Content Type	Text
Resource Type	Article

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