Syntheses, crystal structures and Hirshfeld surface analyses of (3aR,4S,7R,7aS)-2-(perfluoropyridin-4-yl)-3a,4,7,7a-tetrahydro-4,7-methanoisoindole-1,3-dione and (3aR,4S,7R,7aS)-2-[(perfluoropyridin-4-yl)oxy]-3a,4,7,7a-tetrahydro-4,7-methanoisoindole-1,3-dione

Abstract

The syntheses and crystal structures of the title compounds, C14H8F4N2O2 and C14H8F4N2O3, are reported. In each crystal, the packing is driven by C—H...F intertactions, along with a variety of C—H...O, C—O...π, and C—F...π contacts. Hirshfeld surface analysis was conducted to aid in the visualization of these various influences on the packing: they showed that the largest contributions to the surface contacts arise from H...F/F...H interactions, followed by H...H and O...H/H...O.