Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate
The bis(anil) molecule of the title compound, C47H32N2O2·C6H4Cl2, contains two anil fragments in the enol–enol form, exhibiting intramolecular O—H...N hydrogen bonds. The two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)° between them, and...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2020-10-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989020012104 |
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| author | Ayalew Wodajo Alexander G. Tskhovrebov Tuan Anh Le Alexey S. Kubasov Maria M. Grishina Oleg N. Krutius Victor N. Khrustalev |
| author_facet | Ayalew Wodajo Alexander G. Tskhovrebov Tuan Anh Le Alexey S. Kubasov Maria M. Grishina Oleg N. Krutius Victor N. Khrustalev |
| author_sort | Ayalew Wodajo |
| collection | DOAJ |
| description | The bis(anil) molecule of the title compound, C47H32N2O2·C6H4Cl2, contains two anil fragments in the enol–enol form, exhibiting intramolecular O—H...N hydrogen bonds. The two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)° between them, and each ring system makes a large dihedral angle [55.11 (11) and 48.50 (10)°] with the adjacent benzene ring. In the crystal, the bis(anil) molecules form an inversion dimer by a pair of weak C—H...O interactions. The dimers arrange in a one-dimensional column along the b axis via another C—H...O interaction and a π–π stacking interaction between the hydroxynaphthalene ring system with a centroid–centroid distance of 3.6562 (16) Å. The solvent 1,2-dichlorobenzene molecules are located between the dimers and bind neighbouring columns by weak C—H...Cl interactions. Theoretical prediction of potential biological activities was performed, which suggested that the title anil compound can exhibit histone deacetylase SIRT2, histone deacetylase class III and histone deacetylase SIRT1 activities, and will act as inhibitor to aspulvinone dimethylallyltransferase, dehydro-l-gulonate decarboxylase and glutathione thiolesterase. |
| first_indexed | 2024-04-11T16:30:42Z |
| format | Article |
| id | doaj.art-bf3a1b94ba2d414b946b56983185e887 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T16:30:42Z |
| publishDate | 2020-10-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-bf3a1b94ba2d414b946b56983185e8872022-12-22T04:14:02ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902020-10-0176101579158110.1107/S2056989020012104is5554Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvateAyalew Wodajo0Alexander G. Tskhovrebov1Tuan Anh Le2Alexey S. Kubasov3Maria M. Grishina4Oleg N. Krutius5Victor N. Khrustalev6College of Natural and Computational Sciences, University of Gondar, 196 Gondar, EthiopiaN. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Ul. Kosygina 4, Moscow, Russian FederationFaculty of Chemistry, VNU University of Science, 334 Nguyen Trai, Thanh Xuan, Hanoi, VietnamKurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninsky Prosp. 31, Moscow, Russian FederationPeoples Friendship University of Russia, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian FederationN. N. Semenov Federal Research Center for Chemical Physics, Russian Academy of Sciences, Ul. Kosygina 4, Moscow, Russian FederationPeoples Friendship University of Russia, 6 Miklukho-Maklaya Street, Moscow, 117198, Russian FederationThe bis(anil) molecule of the title compound, C47H32N2O2·C6H4Cl2, contains two anil fragments in the enol–enol form, exhibiting intramolecular O—H...N hydrogen bonds. The two hydroxynaphthalene ring systems are approximately parallel to each other with a dihedral angle of 4.67 (8)° between them, and each ring system makes a large dihedral angle [55.11 (11) and 48.50 (10)°] with the adjacent benzene ring. In the crystal, the bis(anil) molecules form an inversion dimer by a pair of weak C—H...O interactions. The dimers arrange in a one-dimensional column along the b axis via another C—H...O interaction and a π–π stacking interaction between the hydroxynaphthalene ring system with a centroid–centroid distance of 3.6562 (16) Å. The solvent 1,2-dichlorobenzene molecules are located between the dimers and bind neighbouring columns by weak C—H...Cl interactions. Theoretical prediction of potential biological activities was performed, which suggested that the title anil compound can exhibit histone deacetylase SIRT2, histone deacetylase class III and histone deacetylase SIRT1 activities, and will act as inhibitor to aspulvinone dimethylallyltransferase, dehydro-l-gulonate decarboxylase and glutathione thiolesterase.http://scripts.iucr.org/cgi-bin/paper?S2056989020012104azomethinesimineshydrogen bondingweak interactionsexcited-state intramolecular proton transfercrystal structure |
| spellingShingle | Ayalew Wodajo Alexander G. Tskhovrebov Tuan Anh Le Alexey S. Kubasov Maria M. Grishina Oleg N. Krutius Victor N. Khrustalev Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate Acta Crystallographica Section E: Crystallographic Communications azomethines imines hydrogen bonding weak interactions excited-state intramolecular proton transfer crystal structure |
| title | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
| title_full | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
| title_fullStr | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
| title_full_unstemmed | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
| title_short | Crystal structure of 1,1′-{(1E,1′E)-[4,4′-(9H-fluorene-9,9-diyl)bis(4,1-phenylene)]bis(azanylylidene)bis(methanylylidene)}bis(naphthalen-2-ol) dichlorobenzene monosolvate |
| title_sort | crystal structure of 1 1 1e 1 e 4 4 9h fluorene 9 9 diyl bis 4 1 phenylene bis azanylylidene bis methanylylidene bis naphthalen 2 ol dichlorobenzene monosolvate |
| topic | azomethines imines hydrogen bonding weak interactions excited-state intramolecular proton transfer crystal structure |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989020012104 |
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