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Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate
The title compound, C(22)H(16)N(4)O(2), contains two pyridine rings and one methoxycarbonylphenyl group attached to a pyridazine ring which deviates very slightly from planarity. In the crystal, ribbons consisting of inversion-related chains of molecules extending along the a-axis direction are...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829718/ https://www.ncbi.nlm.nih.gov/pubmed/31709088 http://dx.doi.org/10.1107/S2056989019013732 |
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author | Filali, Mouad El Ghayati, Lhoussaine Hökelek, Tuncer Mague, Joel T. Ben-Tama, Abdessalam El Hadrami, El Mestafa Sebbar, Nada Kheira |
author_facet | Filali, Mouad El Ghayati, Lhoussaine Hökelek, Tuncer Mague, Joel T. Ben-Tama, Abdessalam El Hadrami, El Mestafa Sebbar, Nada Kheira |
author_sort | Filali, Mouad |
collection | PubMed |
description | The title compound, C(22)H(16)N(4)O(2), contains two pyridine rings and one methoxycarbonylphenyl group attached to a pyridazine ring which deviates very slightly from planarity. In the crystal, ribbons consisting of inversion-related chains of molecules extending along the a-axis direction are formed by C—H(Mthy)⋯O(Carbx) (Mthy = methyl and Carbx = carboxylate) hydrogen bonds. The ribbons are connected into layers parallel to the bc plane by C—H(Bnz)⋯π(ring) (Bnz = benzene) interactions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (39.7%), H⋯C/C⋯H (27.5%), H⋯N/N⋯H (15.5%) and O⋯H/H⋯O (11.1%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—H(Mthy)⋯O(Carbx) hydrogen-bond energies are 62.0 and 34.3 kJ mol(−1), respectively. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap. |
format | Online Article Text |
id | pubmed-6829718 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-68297182019-11-08 Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate Filali, Mouad El Ghayati, Lhoussaine Hökelek, Tuncer Mague, Joel T. Ben-Tama, Abdessalam El Hadrami, El Mestafa Sebbar, Nada Kheira Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(22)H(16)N(4)O(2), contains two pyridine rings and one methoxycarbonylphenyl group attached to a pyridazine ring which deviates very slightly from planarity. In the crystal, ribbons consisting of inversion-related chains of molecules extending along the a-axis direction are formed by C—H(Mthy)⋯O(Carbx) (Mthy = methyl and Carbx = carboxylate) hydrogen bonds. The ribbons are connected into layers parallel to the bc plane by C—H(Bnz)⋯π(ring) (Bnz = benzene) interactions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (39.7%), H⋯C/C⋯H (27.5%), H⋯N/N⋯H (15.5%) and O⋯H/H⋯O (11.1%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—H(Mthy)⋯O(Carbx) hydrogen-bond energies are 62.0 and 34.3 kJ mol(−1), respectively. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap. International Union of Crystallography 2019-10-22 /pmc/articles/PMC6829718/ /pubmed/31709088 http://dx.doi.org/10.1107/S2056989019013732 Text en © Filali 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 Filali, Mouad El Ghayati, Lhoussaine Hökelek, Tuncer Mague, Joel T. Ben-Tama, Abdessalam El Hadrami, El Mestafa Sebbar, Nada Kheira Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate |
title | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate |
title_full | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate |
title_fullStr | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate |
title_full_unstemmed | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate |
title_short | Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate |
title_sort | crystal structure, hirshfeld surface analysis and interaction energy and dft studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6829718/ https://www.ncbi.nlm.nih.gov/pubmed/31709088 http://dx.doi.org/10.1107/S2056989019013732 |
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