Quantitative crystal structure analysis of fluorinated porphyrins

• We report the crystal structures of fluorinated porphyrins.
• Two isostructural pairs of porphyrins were identified.
• Quantitative analysis of intermolecular interactions by crystal explorer.

Herein, we report a series of fluorinated porphyrins, 5,10,15,20-tetrakis(2′,6′-difluorophenyl)porphyrin, MT(2′,6′-DFP)P where M = 2H, 1; Co(II)·(MeOH)2, 2; Cu(II), 3; Zn(II)·(MeOH)2, 4 and Zn(II)·(THF)3, 5 have been structurally characterized by single crystal X-ray diffraction analysis. All the compounds are crystallized in monoclinic crystal system and the crystal structures of 2, 4 and 5 features octahedral geometry whereas 3 exhibits square planar geometry. The compounds 1, 3 and 2, 4 are isostructural, show similar molecular crystal packing and comparable intermolecular interactions. The supramolecular self assembly of compounds 1–5 is dominated by a variety of intermolecular interactions such as CH⋯F, CH⋯π, CF⋯π and F⋯F. Furthermore, the role of weak intermolecular interactions in the crystal packing has been analysed and quantified using Hirshfeld surface analysis.

Crystal structures and Hirshfeld surfaces illustrate 1, 3 and 2, 4 are isostructural owing to similar packing and comparable intermolecular interactions.Figure optionsDownload as PowerPoint slide