Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 3 (March 2013)

organic compounds

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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