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N,N′-Bis(pyridin-3-ylmethyl)ethanediamide monohydrate: crystal structure, Hirshfeld surface analysis and computational study
The molecular structure of the title bis-pyridyl substituted diamide hydrate, C(14)H(14)N(4)O(2)·H(2)O, features a central C(2)N(2)O(2) residue (r.m.s. deviation = 0.0205 Å) linked at each end to 3-pyridyl rings through methylene groups. The pyridyl rings lie to the same side of the plane, i.e. h...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2020
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6944093/ https://www.ncbi.nlm.nih.gov/pubmed/31921447 http://dx.doi.org/10.1107/S2056989019016153 |
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author | Tan, Sang Loon Tiekink, Edward R. T. |
author_facet | Tan, Sang Loon Tiekink, Edward R. T. |
author_sort | Tan, Sang Loon |
collection | PubMed |
description | The molecular structure of the title bis-pyridyl substituted diamide hydrate, C(14)H(14)N(4)O(2)·H(2)O, features a central C(2)N(2)O(2) residue (r.m.s. deviation = 0.0205 Å) linked at each end to 3-pyridyl rings through methylene groups. The pyridyl rings lie to the same side of the plane, i.e. have a syn-periplanar relationship, and form dihedral angles of 59.71 (6) and 68.42 (6)° with the central plane. An almost orthogonal relationship between the pyridyl rings is indicated by the dihedral angle between them [87.86 (5)°]. Owing to an anti disposition between the carbonyl-O atoms in the core, two intramolecular amide-N—H⋯O(carbonyl) hydrogen bonds are formed, each closing an S(5) loop. Supramolecular tapes are formed in the crystal via amide-N—H⋯O(carbonyl) hydrogen bonds and ten-membered {⋯HNC(2)O}(2) synthons. Two symmetry-related tapes are linked by a helical chain of hydrogen-bonded water molecules via water-O—H⋯N(pyridyl) hydrogen bonds. The resulting aggregate is parallel to the b-axis direction. Links between these, via methylene-C—H⋯O(water) and methylene-C—H⋯π(pyridyl) interactions, give rise to a layer parallel to (10[Image: see text]); the layers stack without directional interactions between them. The analysis of the Hirshfeld surfaces point to the importance of the specified hydrogen-bonding interactions, and to the significant influence of the water molecule of crystallization upon the molecular packing. The analysis also indicates the contribution of methylene-C—H⋯O(carbonyl) and pyridyl-C—H⋯C(carbonyl) contacts to the stability of the inter-layer region. The calculated interaction energies are consistent with importance of significant electrostatic attractions in the crystal. |
format | Online Article Text |
id | pubmed-6944093 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-69440932020-01-09 N,N′-Bis(pyridin-3-ylmethyl)ethanediamide monohydrate: crystal structure, Hirshfeld surface analysis and computational study Tan, Sang Loon Tiekink, Edward R. T. Acta Crystallogr E Crystallogr Commun Research Communications The molecular structure of the title bis-pyridyl substituted diamide hydrate, C(14)H(14)N(4)O(2)·H(2)O, features a central C(2)N(2)O(2) residue (r.m.s. deviation = 0.0205 Å) linked at each end to 3-pyridyl rings through methylene groups. The pyridyl rings lie to the same side of the plane, i.e. have a syn-periplanar relationship, and form dihedral angles of 59.71 (6) and 68.42 (6)° with the central plane. An almost orthogonal relationship between the pyridyl rings is indicated by the dihedral angle between them [87.86 (5)°]. Owing to an anti disposition between the carbonyl-O atoms in the core, two intramolecular amide-N—H⋯O(carbonyl) hydrogen bonds are formed, each closing an S(5) loop. Supramolecular tapes are formed in the crystal via amide-N—H⋯O(carbonyl) hydrogen bonds and ten-membered {⋯HNC(2)O}(2) synthons. Two symmetry-related tapes are linked by a helical chain of hydrogen-bonded water molecules via water-O—H⋯N(pyridyl) hydrogen bonds. The resulting aggregate is parallel to the b-axis direction. Links between these, via methylene-C—H⋯O(water) and methylene-C—H⋯π(pyridyl) interactions, give rise to a layer parallel to (10[Image: see text]); the layers stack without directional interactions between them. The analysis of the Hirshfeld surfaces point to the importance of the specified hydrogen-bonding interactions, and to the significant influence of the water molecule of crystallization upon the molecular packing. The analysis also indicates the contribution of methylene-C—H⋯O(carbonyl) and pyridyl-C—H⋯C(carbonyl) contacts to the stability of the inter-layer region. The calculated interaction energies are consistent with importance of significant electrostatic attractions in the crystal. International Union of Crystallography 2020-01-01 /pmc/articles/PMC6944093/ /pubmed/31921447 http://dx.doi.org/10.1107/S2056989019016153 Text en © Tan and Tiekink 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 Tan, Sang Loon Tiekink, Edward R. T. N,N′-Bis(pyridin-3-ylmethyl)ethanediamide monohydrate: crystal structure, Hirshfeld surface analysis and computational study |
title |
N,N′-Bis(pyridin-3-ylmethyl)ethanediamide monohydrate: crystal structure, Hirshfeld surface analysis and computational study |
title_full |
N,N′-Bis(pyridin-3-ylmethyl)ethanediamide monohydrate: crystal structure, Hirshfeld surface analysis and computational study |
title_fullStr |
N,N′-Bis(pyridin-3-ylmethyl)ethanediamide monohydrate: crystal structure, Hirshfeld surface analysis and computational study |
title_full_unstemmed |
N,N′-Bis(pyridin-3-ylmethyl)ethanediamide monohydrate: crystal structure, Hirshfeld surface analysis and computational study |
title_short |
N,N′-Bis(pyridin-3-ylmethyl)ethanediamide monohydrate: crystal structure, Hirshfeld surface analysis and computational study |
title_sort | n,n′-bis(pyridin-3-ylmethyl)ethanediamide monohydrate: crystal structure, hirshfeld surface analysis and computational study |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6944093/ https://www.ncbi.nlm.nih.gov/pubmed/31921447 http://dx.doi.org/10.1107/S2056989019016153 |
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