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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...

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Autores principales: Assoumatine, Tokouré, Stoeckli-Evans, Helen
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
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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.
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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
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