Abstract
Five new crystal structures of perfluoro-pyridine substituted in the 4-position with phen-oxy, 4-bromo-phen-oxy, naphthalen-2-yl-oxy, 6-bromo-naphthalen-2-yl-oxy, and 4,4'-biphen-oxy are reported, viz. 2,3,5,6-tetra-fluoro-4-phen-oxy-pyridine, C11H5F4NO (I), 4-(4-bromo-phen-oxy)-2,3,5,6-tetra-fluoro-pyridine, C11H4BrF4NO (II), 2,3,5,6-tetra-fluoro-4-[(naphthalen-2-yl)-oxy]pyridine, C15H7F4NO (III), 4-[(6-bromo-naphthalen-2-yl)-oxy]-2,3,5,6-tetra-fluoropyridine, C15H6BrF4NO (IV), and 2,2'-bis-[(perfluoro-pyridin-4-yl)-oxy]-1,1'-biphenyl, C22H8F8N2O2 (V). The dihedral angles between the aromatic ring systems in I-IV are 78.74 (8), 56.35 (8), 74.30 (7), and 64.34 (19)°, respectively. The complete mol-ecule of V is generated by a crystallographic twofold axis: the dihedral angle between the pyridine ring and adjacent phenyl ring is 80.89 (5)° and the equivalent angle between the biphenyl rings is 27.30 (5)°. In each crystal, the packing is driven by C-H⋯F inter-actions, along with a variety of C-F⋯π, C-H⋯π, C-Br⋯N, C-H⋯N, and C-Br⋯π contacts. Hirshfeld surface analysis was conducted to aid in the visualization of these various influences on the packing.
Highlights
Pentafluoropyridine, or perfluoropyridine (C5F5N) is one of the most important perfluoroheteroaromatic compounds
In an effort to further understand the intermolecular interactions in the solid state of these fluorinated compounds, five new crystal structures of pentafluoropyridine derivatives are reported as well as their syntheses
Compounds II and IV crystallize in the monoclinic space groups P21/n and P21 respectively (Fig. 1)
Summary
Pentafluoropyridine, or perfluoropyridine (C5F5N) is one of the most important perfluoroheteroaromatic compounds. As a result of the presence of five fluorine atoms, in addition to the nitrogen atom of the pyridine ring, these systems are highly electrophilic and undergo substitution reactions readily in a predictable pattern (Baker & Muir, 2010; Chambers et al, 1988). This chemistry has already been used in the design of several drugs (Bhambra et al, 2016) and in peptide modification (Gimenez et al, 2017). In an effort to further understand the intermolecular interactions in the solid state of these fluorinated compounds, five new crystal structures of pentafluoropyridine derivatives are reported as well as their syntheses
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