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.

Graphical abstractCrystal structures and Hirshfeld surfaces illustrate 1, 3 and 2, 4 are isostructural owing to similar packing and comparable intermolecular interactions.Figure optionsDownload full-size imageDownload as PowerPoint slide