Cargando…
The crystal structures, Hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane
The title thiapyrazinophanes, 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane, C(16)H(24)N(2)S(6), (I), and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane, C(16)H(24)N(2)S(6), (II), are regioisomers; m-bis L1 and p-bis L1, respectively. Both compounds have a central tetra-2,3,5,6-me...
Autores principales: | , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7336784/ https://www.ncbi.nlm.nih.gov/pubmed/32695437 http://dx.doi.org/10.1107/S2056989020007057 |
_version_ | 1783554389881913344 |
---|---|
author | Assoumatine, Tokouré Stoeckli-Evans, Helen |
author_facet | Assoumatine, Tokouré Stoeckli-Evans, Helen |
author_sort | Assoumatine, Tokouré |
collection | PubMed |
description | The title thiapyrazinophanes, 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane, C(16)H(24)N(2)S(6), (I), and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane, C(16)H(24)N(2)S(6), (II), are regioisomers; m-bis L1 and p-bis L1, respectively. Both compounds have a central tetra-2,3,5,6-methylenepyrazine unit with two –S—CH(2)—CH(2)—S—CH(2)—CH(2)—S– chains, linking the methylene C atoms at positions 2 and 6 and 3 and 5 on the pyrazine ring of I, but linking the methylene C atoms at positions 2 and 5 and 3 and 6 on the pyrazine ring of II. Both compounds crystallize with half a molecule in the asymmetric unit. The whole molecule of I is generated by inversion symmetry, with the pyrazine ring being located about a center of symmetry. The whole molecule of II is generated by twofold rotation symmetry, with the pyrazine N atoms being located on the twofold rotation axis. In compound I, there are pairs of intramolecular C—H⋯S contacts present, but none in compound II. In the crystal of I, there are no significant intermolecular interactions present, while in the crystal of II, molecules are linked by pairs of C—H⋯S hydrogen bonds, forming corrugated layers lying parallel the ac plane. The Hirshfeld surfaces and the energy frameworks of the two regioisomers indicate little difference in the interatomic contacts, which are dominated by dispersion forces. |
format | Online Article Text |
id | pubmed-7336784 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-73367842020-07-20 The crystal structures, Hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane Assoumatine, Tokouré Stoeckli-Evans, Helen Acta Crystallogr E Crystallogr Commun Research Communications The title thiapyrazinophanes, 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane, C(16)H(24)N(2)S(6), (I), and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane, C(16)H(24)N(2)S(6), (II), are regioisomers; m-bis L1 and p-bis L1, respectively. Both compounds have a central tetra-2,3,5,6-methylenepyrazine unit with two –S—CH(2)—CH(2)—S—CH(2)—CH(2)—S– chains, linking the methylene C atoms at positions 2 and 6 and 3 and 5 on the pyrazine ring of I, but linking the methylene C atoms at positions 2 and 5 and 3 and 6 on the pyrazine ring of II. Both compounds crystallize with half a molecule in the asymmetric unit. The whole molecule of I is generated by inversion symmetry, with the pyrazine ring being located about a center of symmetry. The whole molecule of II is generated by twofold rotation symmetry, with the pyrazine N atoms being located on the twofold rotation axis. In compound I, there are pairs of intramolecular C—H⋯S contacts present, but none in compound II. In the crystal of I, there are no significant intermolecular interactions present, while in the crystal of II, molecules are linked by pairs of C—H⋯S hydrogen bonds, forming corrugated layers lying parallel the ac plane. The Hirshfeld surfaces and the energy frameworks of the two regioisomers indicate little difference in the interatomic contacts, which are dominated by dispersion forces. International Union of Crystallography 2020-06-02 /pmc/articles/PMC7336784/ /pubmed/32695437 http://dx.doi.org/10.1107/S2056989020007057 Text en © Assoumatine and Stoeckli-Evans 2020 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 Assoumatine, Tokouré Stoeckli-Evans, Helen The crystal structures, Hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane |
title | The crystal structures, Hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane |
title_full | The crystal structures, Hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane |
title_fullStr | The crystal structures, Hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane |
title_full_unstemmed | The crystal structures, Hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane |
title_short | The crystal structures, Hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane |
title_sort | crystal structures, hirshfeld surface analyses and energy frameworks of two hexathiapyrazinophane regioisomers; 2,5,8,11,14,17-hexathia-[9.9](2,6,3,5)-pyrazinophane and 2,5,8,11,14,17-hexathia-[9.9](2,5,3,6)-pyrazinophane |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7336784/ https://www.ncbi.nlm.nih.gov/pubmed/32695437 http://dx.doi.org/10.1107/S2056989020007057 |
work_keys_str_mv | AT assoumatinetokoure thecrystalstructureshirshfeldsurfaceanalysesandenergyframeworksoftwohexathiapyrazinophaneregioisomers258111417hexathia992635pyrazinophaneand258111417hexathia992536pyrazinophane AT stoecklievanshelen thecrystalstructureshirshfeldsurfaceanalysesandenergyframeworksoftwohexathiapyrazinophaneregioisomers258111417hexathia992635pyrazinophaneand258111417hexathia992536pyrazinophane AT assoumatinetokoure crystalstructureshirshfeldsurfaceanalysesandenergyframeworksoftwohexathiapyrazinophaneregioisomers258111417hexathia992635pyrazinophaneand258111417hexathia992536pyrazinophane AT stoecklievanshelen crystalstructureshirshfeldsurfaceanalysesandenergyframeworksoftwohexathiapyrazinophaneregioisomers258111417hexathia992635pyrazinophaneand258111417hexathia992536pyrazinophane |