Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 4-(prop-2-en-1-yl-oxy)meth-yl-3,6-bis-(pyridin-2-yl)pyridazine

Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 4-(prop-2-en-1-yl-oxy)meth-yl-3,6-bis-(pyridin-2-yl)pyridazine

The title compound, C18H16N4O, consists of a 3,6-bis-(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl-oxy)meth-yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-HPyrd⋯NPy...

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Veröffentlicht in:Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2019-09, Vol.75 (Pt 9), p.1321
Hauptverfasser: Filali, Mouad, Sebbar, Nada Kheira, Hökelek, Tuncer, Mague, Joel T, Chakroune, Said, Ben-Tama, Abdessalam, El Hadrami, El Mestafa
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container_title Acta crystallographica. Section E, Crystallographic communications
container_volume 75
creator Filali, Mouad
Sebbar, Nada Kheira
Hökelek, Tuncer
Mague, Joel T
Chakroune, Said
Ben-Tama, Abdessalam
El Hadrami, El Mestafa
description The title compound, C18H16N4O, consists of a 3,6-bis-(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl-oxy)meth-yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-HPrp-oxy⋯π (Prp-oxy = prop-2-en-1-yl-oxy) inter-actions link the mol-ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter-actions being the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.The title compound, C18H16N4O, consists of a 3,6-bis-(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl-oxy)meth-yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-HPrp-oxy⋯π (Prp-oxy = prop-2-en-1-yl-oxy) inter-actions link the mol-ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter-actions being the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.
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The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-HPrp-oxy⋯π (Prp-oxy = prop-2-en-1-yl-oxy) inter-actions link the mol-ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter-actions being the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.The title compound, C18H16N4O, consists of a 3,6-bis-(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl-oxy)meth-yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-HPrp-oxy⋯π (Prp-oxy = prop-2-en-1-yl-oxy) inter-actions link the mol-ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter-actions being the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.</description><identifier>ISSN: 2056-9890</identifier><identifier>EISSN: 2056-9890</identifier><identifier>DOI: 10.1107/S2056989019011186</identifier><language>eng</language><ispartof>Acta crystallographica. 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Section E, Crystallographic communications</title><description>The title compound, C18H16N4O, consists of a 3,6-bis-(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl-oxy)meth-yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-HPrp-oxy⋯π (Prp-oxy = prop-2-en-1-yl-oxy) inter-actions link the mol-ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter-actions being the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.The title compound, C18H16N4O, consists of a 3,6-bis-(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl-oxy)meth-yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-HPrp-oxy⋯π (Prp-oxy = prop-2-en-1-yl-oxy) inter-actions link the mol-ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter-actions being the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. 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Section E, Crystallographic communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Filali, Mouad</au><au>Sebbar, Nada Kheira</au><au>Hökelek, Tuncer</au><au>Mague, Joel T</au><au>Chakroune, Said</au><au>Ben-Tama, Abdessalam</au><au>El Hadrami, El Mestafa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 4-(prop-2-en-1-yl-oxy)meth-yl-3,6-bis-(pyridin-2-yl)pyridazine</atitle><jtitle>Acta crystallographica. Section E, Crystallographic communications</jtitle><date>2019-09-01</date><risdate>2019</risdate><volume>75</volume><issue>Pt 9</issue><spage>1321</spage><pages>1321-</pages><issn>2056-9890</issn><eissn>2056-9890</eissn><abstract>The title compound, C18H16N4O, consists of a 3,6-bis-(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl-oxy)meth-yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-HPrp-oxy⋯π (Prp-oxy = prop-2-en-1-yl-oxy) inter-actions link the mol-ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter-actions being the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.The title compound, C18H16N4O, consists of a 3,6-bis-(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yl-oxy)meth-yl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C-HPyrd⋯NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C-HPrp-oxy⋯π (Prp-oxy = prop-2-en-1-yl-oxy) inter-actions link the mol-ecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H⋯H (48.5%), H⋯C/C⋯H (26.0%) and H⋯N/N⋯H (17.1%) contacts, hydrogen bonding and van der Waals inter-actions being the dominant inter-actions in the crystal packing. Computational chemistry indicates that in the crystal, the C-HPyrd⋯NPyrdz hydrogen-bond energy is 64.3 kJ mol-1. Density functional theory (DFT) optimized structures at the B3LYP/6-311 G(d,p) level are compared with the experimentally determined mol-ecular structure in the solid state. The HOMO-LUMO behaviour was elucidated to determine the energy gap.</abstract><doi>10.1107/S2056989019011186</doi></addata></record>
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title Crystal structure, Hirshfeld surface analysis and inter-action energy and DFT studies of 4-(prop-2-en-1-yl-oxy)meth-yl-3,6-bis-(pyridin-2-yl)pyridazine
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