Crystal structures and Hirshfeld surface analysis of a series of 4-O-arylperfluoropyridines
Abstract
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, C11H5F4NO (I), 4-(4-bromophenoxy)-2,3,5,6-tetrafluoropyridine, C11H4BrF4NO (II), 2,3,5,6-tetrafluoro-4-[(naphthalen-2-yl)oxy]pyridine, C15H7F4NO (III), 4-[(6-bromonaphthalen-2-yl)oxy]-2,3,5,6-tetrafluoropyridine, C15H6BrF4NO (IV), and 2,2′-bis[(perfluoropyridin-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 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.
Document Details
- Document Type
- Pub Defense Publication
- Publication Date
- Jul 04, 2019
- Source ID
- 10.1107/s2056989019009344
Entities
People
- Andrew J Peloquin
- Cynthia A. Corley
- Gary J Balaich
- Scott T Iacono
- Sonya K. Adas
Organizations
- Air Force Office of Scientific Research