Abstract
X-ray crystallographic studies of the two title compounds have shown that the molecules crystallize in the same triclinic space group,\(P\bar 1\), with very similar cell dimensions. For C21H21BrO4,a=12.056(5),b=13.206(5),c=7.595(3)Å, α=90.38(3), β=106.07(3) and γ=124.42(3)° and for C21H23BrO3,a=12.076(6),b=13.090(5),c=7.490(3)Å, α=92.65(5), β=104.90(5) and γ=124.55(5)°. Both compounds possess the oxabicyclo[3.2.1]octane bridged ring system and differ only at the carbon α to the ring oxygen where the Csp3 in the ether is replaced by Csp2=O in the lactone. Both cyclohexane rings adopt distorted chair conformations and the lactone and ether rings approximate closely to the envelope conformation. The bromine substituent at C(4) results in distortion of the naphthalene ring. Both molecules pack with the naphthalene rings parallel to each other with interplanar spacings of 3.71 Å in the ether and 3.66Å in the lactone.
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Cox, P.J. Crystal and molecular structure of: 5-(1-oxoethyl)-1-methyl-2-(5-bromo-6-methoxy-2-naphthyl)-6-oxabicyclo[3.2.1]octan-7-one and 5-(1-oxoethyl)-1-methyl-2-(5-bromo-6-methoxy-2-naphthyl)-6-oxabicyclo[3.2.1]octane. J Chem Crystallogr 25, 671–675 (1995). https://doi.org/10.1007/BF01665974
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DOI: https://doi.org/10.1007/BF01665974