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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2019
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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. |
format | Online Article Text |
id | pubmed-6690456 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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