Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 3 (March 2013)

organic compounds

gz3222 scheme

Acta Cryst. (2013). C69, 303-306    [ doi:10.1107/S0108270113002503 ]

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

K. Brzezinski, R. Lazny, A. Nodzewska and K. Sidorowicz

Abstract: 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 group R\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 groups P212121 and Pna21, 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 [pi]-[pi] 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.

Formula: Three isomers of C21H22BrNO2

hkldisplay filedownload file

Structure factor file (CIF format) (239.6 kbytes)
[ doi:10.1107/S0108270113002503/gz3222Isup2.hkl ]
Contains datablock I

hkldisplay filedownload file

Structure factor file (CIF format) (262.4 kbytes)
[ doi:10.1107/S0108270113002503/gz3222IIsup3.hkl ]
Contains datablock II

hkldisplay filedownload file

Structure factor file (CIF format) (212.0 kbytes)
[ doi:10.1107/S0108270113002503/gz3222IIIsup4.hkl ]
Contains datablock III


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