Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene]naphthalen-2(1H)-one
The title compound, C16H11N2OF, is a member of the azo dye family. The dihedral angle subtended by the benzene ring and the naphthalene ring system measures 18.75 (7)°, indicating that the compound is not perfectly planar. An intramolecular N—H...O hydrogen bond occurs between the imino and carbonyl...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2024-02-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989024000227 |
| _version_ | 1797323993367183360 |
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| author | Hibet Errahmane Meroua Akkache Noudjoud Hamdouni Ali Boudjada Mohamed larbi Medjroubi Assia Mili Olivier Jeannin |
| author_facet | Hibet Errahmane Meroua Akkache Noudjoud Hamdouni Ali Boudjada Mohamed larbi Medjroubi Assia Mili Olivier Jeannin |
| author_sort | Hibet Errahmane Meroua Akkache |
| collection | DOAJ |
| description | The title compound, C16H11N2OF, is a member of the azo dye family. The dihedral angle subtended by the benzene ring and the naphthalene ring system measures 18.75 (7)°, indicating that the compound is not perfectly planar. An intramolecular N—H...O hydrogen bond occurs between the imino and carbonyl groups. In the crystal, the molecules are linked into inversion dimers by C—H...O interactions. Aromatic π–π stacking between the naphthalene ring systems lead to the formation of chains along [001]. A Hirshfeld surface analysis was undertaken to investigate and quantify the intermolecular interactions. In addition, energy frameworks were used to examine the cooperative effect of these intermolecular interactions across the crystal, showing dispersion energy to be the most influential factor in the crystal organization of the compound. |
| first_indexed | 2024-03-08T05:36:03Z |
| format | Article |
| id | doaj.art-903168f14fbb4424b17a5f438bb7a9ea |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-03-08T05:36:03Z |
| publishDate | 2024-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-903168f14fbb4424b17a5f438bb7a9ea2024-02-05T17:27:26ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902024-02-0180213714210.1107/S2056989024000227ee2002Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene]naphthalen-2(1H)-oneHibet Errahmane Meroua Akkache0Noudjoud Hamdouni1Ali Boudjada2Mohamed larbi Medjroubi3Assia Mili4Olivier Jeannin5Laboratoire de Cristallographie, Département de Physique, Université Mentouri-Constantine, 25000 Constantine, AlgeriaLaboratoire de Cristallographie, Département de Physique, Université Mentouri-Constantine, 25000 Constantine, AlgeriaLaboratoire de Cristallographie, Département de Physique, Université Mentouri-Constantine, 25000 Constantine, AlgeriaLaboratoire de Cristallographie, Département de Physique, Université Mentouri-Constantine, 25000 Constantine, AlgeriaUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, Faculté du Sciences Exactes, Université de Constantine 1, 25000 Constantine, AlgeriaUMR 6226 CNRS–Université Rennes 1, `Sciences Chimiques de Rennes', Equipe `Matière Condensée et Systèmes Electroactifs', Bâtiment 10C Campus de Beaulieu, 263 Avenue du Général Leclerc, F-35042 Rennes, FranceThe title compound, C16H11N2OF, is a member of the azo dye family. The dihedral angle subtended by the benzene ring and the naphthalene ring system measures 18.75 (7)°, indicating that the compound is not perfectly planar. An intramolecular N—H...O hydrogen bond occurs between the imino and carbonyl groups. In the crystal, the molecules are linked into inversion dimers by C—H...O interactions. Aromatic π–π stacking between the naphthalene ring systems lead to the formation of chains along [001]. A Hirshfeld surface analysis was undertaken to investigate and quantify the intermolecular interactions. In addition, energy frameworks were used to examine the cooperative effect of these intermolecular interactions across the crystal, showing dispersion energy to be the most influential factor in the crystal organization of the compound.http://scripts.iucr.org/cgi-bin/paper?S2056989024000227azo compounds2-naphtholscrystal structurehirshfeld surface calculationstwo-dimensional fingerprint plotenergy frameworks |
| spellingShingle | Hibet Errahmane Meroua Akkache Noudjoud Hamdouni Ali Boudjada Mohamed larbi Medjroubi Assia Mili Olivier Jeannin Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene]naphthalen-2(1H)-one Acta Crystallographica Section E: Crystallographic Communications azo compounds 2-naphthols crystal structure hirshfeld surface calculations two-dimensional fingerprint plot energy frameworks |
| title | Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene]naphthalen-2(1H)-one |
| title_full | Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene]naphthalen-2(1H)-one |
| title_fullStr | Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene]naphthalen-2(1H)-one |
| title_full_unstemmed | Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene]naphthalen-2(1H)-one |
| title_short | Crystal structure, Hirshfeld surface analysis and energy frameworks of 1-[(E)-2-(2-fluorophenyl)diazan-1-ylidene]naphthalen-2(1H)-one |
| title_sort | crystal structure hirshfeld surface analysis and energy frameworks of 1 e 2 2 fluorophenyl diazan 1 ylidene naphthalen 2 1h one |
| topic | azo compounds 2-naphthols crystal structure hirshfeld surface calculations two-dimensional fingerprint plot energy frameworks |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989024000227 |
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