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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-tetra­...

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Autores principales: Peloquin, Andrew J., Corley, Cynthia A., Adas, Sonya K., Balaich, Gary J., Iacono, Scott T.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6690456/
https://www.ncbi.nlm.nih.gov/pubmed/31417773
http://dx.doi.org/10.1107/S2056989019009344
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author Peloquin, Andrew J.
Corley, Cynthia A.
Adas, Sonya K.
Balaich, Gary J.
Iacono, Scott T.
author_facet Peloquin, Andrew J.
Corley, Cynthia A.
Adas, Sonya K.
Balaich, Gary J.
Iacono, Scott T.
author_sort Peloquin, Andrew J.
collection PubMed
description 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.
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spelling pubmed-66904562019-08-15 Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl­perfluoro­pyridines Peloquin, Andrew J. Corley, Cynthia A. Adas, Sonya K. Balaich, Gary J. Iacono, Scott T. Acta Crystallogr E Crystallogr Commun Research Communications 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. International Union of Crystallography 2019-07-04 /pmc/articles/PMC6690456/ /pubmed/31417773 http://dx.doi.org/10.1107/S2056989019009344 Text en © Peloquin et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Peloquin, Andrew J.
Corley, Cynthia A.
Adas, Sonya K.
Balaich, Gary J.
Iacono, Scott T.
Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl­perfluoro­pyridines
title Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl­perfluoro­pyridines
title_full Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl­perfluoro­pyridines
title_fullStr Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl­perfluoro­pyridines
title_full_unstemmed Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl­perfluoro­pyridines
title_short Crystal structures and Hirshfeld surface analysis of a series of 4-O-aryl­perfluoro­pyridines
title_sort crystal structures and hirshfeld surface analysis of a series of 4-o-aryl­perfluoro­pyridines
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6690456/
https://www.ncbi.nlm.nih.gov/pubmed/31417773
http://dx.doi.org/10.1107/S2056989019009344
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