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Crystal structures of N (2),N (3),N (5),N (6)-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide and N (2),N (3),N (5),N (6)-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide
The title compounds, C(32)H(28)N(10)O(4)· unknown solvent, (I), and C(32)H(28)N(10)O(4), (II), are pyrazine-2,3,5,6-tetracarboxamide derivatives. In (I), the substituents are (pyridin-2-ylmethyl)carboxamide, while in (II), the substituents are (pyridin-4-ylmethyl)carboxamide. Both compounds cryst...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5290586/ https://www.ncbi.nlm.nih.gov/pubmed/28217363 http://dx.doi.org/10.1107/S205698901700127X |
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author | Cati, Dilovan S. Stoeckli-Evans, Helen |
author_facet | Cati, Dilovan S. Stoeckli-Evans, Helen |
author_sort | Cati, Dilovan S. |
collection | PubMed |
description | The title compounds, C(32)H(28)N(10)O(4)· unknown solvent, (I), and C(32)H(28)N(10)O(4), (II), are pyrazine-2,3,5,6-tetracarboxamide derivatives. In (I), the substituents are (pyridin-2-ylmethyl)carboxamide, while in (II), the substituents are (pyridin-4-ylmethyl)carboxamide. Both compounds crystallize in the monoclinic space group P2(1)/n, with Z′ = 1 for (I), and Z′ = 0.5 for (II). The whole molecule of (II) is generated by inversion symmetry, the pyrazine ring being situated about a center of inversion. In (I), the four pyridine rings are inclined to the pyrazine ring by 83.9 (2), 82.16 (18), 82.73 (19) and 17.65 (19)°. This last dihedral angle involves a pyridine ring that is linked to the adjacent carboxamide O atom by an intramolecular C—H⋯O hydrogen bond. In compound (II), the unique pyridine rings are inclined to the pyrazine ring by 33.3 (3) and 81.71 (10)°. There are two symmetrical intramolecular C—H⋯O hydrogen bonds present in (II). In the crystal of (I), molecules are linked by N—H⋯O and N—H⋯N hydrogen bonds, forming layers parallel to (10-1). The layers are linked by C—H⋯O and C—H⋯N hydrogen bonds, forming a three-dimensional framework. In the crystal of (II), molecules are linked by N—H⋯N hydrogen bonds, forming chains propagating along the [010] direction. The chains are linked by a weaker N—H⋯N hydrogen bond, forming layers parallel to the (101) plane, which are in turn linked by C—H⋯O hydrogen bonds, forming a three-dimensional structure. In the crystal of compound (I), a region of disordered electron density was treated with the SQUEEZE routine in PLATON [Spek (2015 ▸). Acta Cryst. C71, 9–18]. Their contribution was not taken into account during refinement. In compound (II), one of the pyridine rings is positionally disordered, and the refined occupancy ratio for the disordered C(ar)—C(ar)—N(py) atoms is 0.58 (3):0.42 (3). |
format | Online Article Text |
id | pubmed-5290586 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-52905862017-02-17 Crystal structures of N (2),N (3),N (5),N (6)-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide and N (2),N (3),N (5),N (6)-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide Cati, Dilovan S. Stoeckli-Evans, Helen Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, C(32)H(28)N(10)O(4)· unknown solvent, (I), and C(32)H(28)N(10)O(4), (II), are pyrazine-2,3,5,6-tetracarboxamide derivatives. In (I), the substituents are (pyridin-2-ylmethyl)carboxamide, while in (II), the substituents are (pyridin-4-ylmethyl)carboxamide. Both compounds crystallize in the monoclinic space group P2(1)/n, with Z′ = 1 for (I), and Z′ = 0.5 for (II). The whole molecule of (II) is generated by inversion symmetry, the pyrazine ring being situated about a center of inversion. In (I), the four pyridine rings are inclined to the pyrazine ring by 83.9 (2), 82.16 (18), 82.73 (19) and 17.65 (19)°. This last dihedral angle involves a pyridine ring that is linked to the adjacent carboxamide O atom by an intramolecular C—H⋯O hydrogen bond. In compound (II), the unique pyridine rings are inclined to the pyrazine ring by 33.3 (3) and 81.71 (10)°. There are two symmetrical intramolecular C—H⋯O hydrogen bonds present in (II). In the crystal of (I), molecules are linked by N—H⋯O and N—H⋯N hydrogen bonds, forming layers parallel to (10-1). The layers are linked by C—H⋯O and C—H⋯N hydrogen bonds, forming a three-dimensional framework. In the crystal of (II), molecules are linked by N—H⋯N hydrogen bonds, forming chains propagating along the [010] direction. The chains are linked by a weaker N—H⋯N hydrogen bond, forming layers parallel to the (101) plane, which are in turn linked by C—H⋯O hydrogen bonds, forming a three-dimensional structure. In the crystal of compound (I), a region of disordered electron density was treated with the SQUEEZE routine in PLATON [Spek (2015 ▸). Acta Cryst. C71, 9–18]. Their contribution was not taken into account during refinement. In compound (II), one of the pyridine rings is positionally disordered, and the refined occupancy ratio for the disordered C(ar)—C(ar)—N(py) atoms is 0.58 (3):0.42 (3). International Union of Crystallography 2017-01-31 /pmc/articles/PMC5290586/ /pubmed/28217363 http://dx.doi.org/10.1107/S205698901700127X Text en © Cati and Stoeckli-Evans 2017 http://creativecommons.org/licenses/by/2.0/uk/ 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/2.0/uk/ |
spellingShingle | Research Communications Cati, Dilovan S. Stoeckli-Evans, Helen Crystal structures of N (2),N (3),N (5),N (6)-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide and N (2),N (3),N (5),N (6)-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide |
title | Crystal structures of N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide and N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide |
title_full | Crystal structures of N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide and N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide |
title_fullStr | Crystal structures of N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide and N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide |
title_full_unstemmed | Crystal structures of N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide and N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide |
title_short | Crystal structures of N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide and N
(2),N
(3),N
(5),N
(6)-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide |
title_sort | crystal structures of n
(2),n
(3),n
(5),n
(6)-tetrakis(pyridin-2-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide and n
(2),n
(3),n
(5),n
(6)-tetrakis(pyridin-4-ylmethyl)pyrazine-2,3,5,6-tetracarboxamide |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5290586/ https://www.ncbi.nlm.nih.gov/pubmed/28217363 http://dx.doi.org/10.1107/S205698901700127X |
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