Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl­perfluoro­pyridines

Five new crystal structures of perfluoro­pyridine substituted in the 4-position with phen­oxy, 4-bromo­phen­oxy, naphthalen-2-yl­oxy, 6-bromo­naphthalen-2-yl­oxy, and 4,4′-biphen­oxy are reported, viz. 2,3,5,6-tetra­fluoro-4-phen­oxy­pyridine, C(11)H(5)F(4)NO (I), 4-(4-bromo­phen­oxy)-2,3,5,6-tetra­fluoro­pyridine, C(11)H(4)BrF(4)NO (II), 2,3,5,6-tetra­fluoro-4-[(naphthalen-2-yl)­oxy]pyridine, C(15)H(7)F(4)NO (III), 4-[(6-bromo­naphthalen-2-yl)­oxy]-2,3,5,6-tetra­fluoropyridine, C(15)H(6)BrF(4)NO (IV), and 2,2′-bis­[(perfluoro­pyridin-4-yl)­oxy]-1,1′-biphenyl, C(22)H(8)F(8)N(2)O(2) (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 mol­ecule 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 inter­actions, 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.