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Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl-perfluoro-pyridines.

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??, C-H??, C-Br?N, C-H?N, and C-Br?? contacts. Hirshfeld surface analysis was conducted to aid in the visualization of these various influences on the packing.

SUBMITTER: Peloquin AJ

PROVIDER: S-EPMC6690456 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature

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Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl-perfluoro-pyridines.

Peloquin Andrew J AJ Corley Cynthia A CA Adas Sonya K SK Balaich Gary J GJ Iacono Scott T ST

Acta crystallographica. Section E, Crystallographic communications 20190704 Pt 8

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, C15H7F ...[more]

PMID: 31417773

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Project description:The crystal structures of two ammonium salts of 2-amino-4-nitro-benzoic acid are described, namely di-methyl-aza-nium 2-amino-4-nitro-benzoate, C2H8N+·C7H5N2O4-, (I), and di-butyl-aza-nium 2-amino-4-nitro-benzoate, C8H20N+·C7H5N2O4-, (II). The asymmetric unit of (I) comprises a single cation and a single anion. In the anion, small twists are noted for the carboxyl-ate and nitro groups from the ring to which they are connected, as indicated by the dihedral angles of 11.45?(13) and 3.71?(15)°, respectively; the dihedral angle between the substituents is 7.9?(2)°. The asymmetric unit of (II) comprises two independent pairs of cations and anions. In the cations, different conformations are noted in the side chains in that three chains have an all-trans [(+)-anti-periplanar] conformation, while one has a distinctive kink resulting in a (+)-synclinal conformation. The anions, again, exhibit twists with the dihedral angles between the carboxyl-ate and nitro groups and the ring being 12.73?(6) and 4.30?(10)°, respectively, for the first anion and 8.1?(4) and 12.6?(3)°, respectively, for the second. The difference between anions in (I) and (II) is that in the anions of (II), the terminal groups are conrotatory, forming dihedral angles of 17.02?(8) and 19.0?(5)°, respectively. In each independent anion of (I) and (II), an intra-molecular amino-N-H?O(carboxyl-ate) hydrogen bond is formed. In the crystal of (I), anions are linked into a jagged supra-molecular chain by charge-assisted amine-N-H?O(carboxyl-ate) hydrogen bonds and these are connected into layers via charge-assisted ammonium-N-H?O(carboxyl-ate) hydrogen bonds. The resulting layers stack along the a axis, being connected by nitro-N-O??(arene) and methyl-C-H?O(nitro) inter-actions. In the crystal of (II), the anions are connected into four-ion aggregates by charge-assisted amino-N-H?O(carboxyl-ate) hydrogen bonding. The formation of ammonium-N-H?O(carboxyl-ate) hydrogen bonds, involving all ammonium-N-H and carboxyl-ate O atoms leads to a three-dimensional architecture; additional C-H?O(nitro) inter-actions contribute to the packing. The Hirshfeld surface analysis confirms the importance of the hydrogen bonding in both crystal structures. Indeed, O?H/H?O inter-actions contribute nearly 50% to the entire Hirshfeld surface in (I).

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Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl-perfluoro-pyridines.

Publications

Crystal structures and Hirshfeld surface analysis of a series of 4-<i>O</i>-aryl-perfluoro-pyridines.

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