Crystal structures of two bi-cyclo-[5.1.0]octa-nes: potassium trans-bi-cyclo-[5.1.0]octane-4-carboxyl-ate monohydrate and cis-bi-cyclo-[5.1.0]octan-4-yl 4-bromo-benzene-sulfonate

Peter W R Corfield; Richard A Kershaw

doi:10.1107/S2056989017011756

Crystal structures of two bi-cyclo-[5.1.0]octa-nes: potassium trans-bi-cyclo-[5.1.0]octane-4-carboxyl-ate monohydrate and cis-bi-cyclo-[5.1.0]octan-4-yl 4-bromo-benzene-sulfonate

Acta Crystallogr E Crystallogr Commun. 2017 Aug 21;73(Pt 9):1357-1362. doi: 10.1107/S2056989017011756. eCollection 2017 Sep 1.

Authors

Peter W R Corfield¹, Richard A Kershaw²

Affiliations

¹ Department of Chemistry, Fordham University, 441 East Fordham Road, Bronx, NY 10458, USA.
² Department of Chemistry, The Ohio State University, Columbus, Ohio 43210, USA.

Abstract

The crystal structures of the trans-fused compound potassium trans-bi-cyclo-[5.1.0]octane-4-carboxyl-ate monohydrate, K⁺·C₉H₁₃O₂^-·H₂O, (I), and of cis-bi-cyclo-[5.1.0]octan-4-yl 4-bromo-benzene-sulfonate, C₁₄H₁₇BrO₃S, (II), have been determined. Compound (I) represents the smallest trans-fused cyclo-propane structure known to date, and features the expected shortening of the bridging C-C bond relative to the other cyclo-propane bond lengths, in contrast to the cis-fused system, (II), where all of the cyclo-propane bond lengths are the same. The bicyclic ring system of (I) is disordered across a crystallographic mirror plane. The geometries of the cis-fused and trans-fused ring systems are compared.

Keywords: bicyclic; cis-fused; crystal structure; octane; trans-fused.