Molecular conformations. Part VIII. The bicyclo[2,2,2]octane system: X-ray analysis of 1-p-bromobenzenesulphonyloxymethylbicyclo[2,2,2]-octane
- 1 January 1968
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society B: Physical Organic
- p. 1249-1255
- https://doi.org/10.1039/j29680001249
Abstract
The conformation of a 1-p-bromobenzenesulphonyloxymethyl derivative of bicyclo[2,2,2]octane has been determined by a single-crystal X-ray analysis. The crystals are monoclinic, space group P21/c, with four molecules of C15H19SO3Br in a unit cell of dimensions a 18·99, b 6·65, c 12·56 Å, β 96·0°. The structure was solved by the heavy-atom method and refined by least-squares methods. R is 0·104 for 1715 data. The bicyclo[2,2,2]octyl system closely conforms to symmetry D3, with the group of atoms C(2)C(7)C(6) rotated 3° about the C(1) C(4) axis with respect to the C(3)C(5)C(8) group. This has the effect of increasing the torsional angles at C(2)–C(3), C(5)–C(6), and C(7)–C(8) to 5°, whereas with an eclipsed D3h model a zero value would hold.Keywords
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