Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetrahydroisoquinoline-4-carbonitrile
In the title compound, C28H21N3O, the 1,2-dihydropyridine ring of the 1,2,7,8-tetrahydroisoquinoline ring system is planar as expected, while the cyclohexa-1,3-diene ring has a twist-boat conformation, with Cremer–Pople parameters QT = 0.367 (2) A, θ = 117.3 (3)° and φ = 327.3 (4)°. The dihedral ang...
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| Format: | Article |
| Language: | English |
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International Union of Crystallography
2021-02-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989021000785 |
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| author | Farid N. Naghiyev Maria M. Grishina Victor N. Khrustalev Ali N. Khalilov Mehmet Akkurt Anzurat A. Akobirshoeva İbrahim G. Mamedov |
| author_facet | Farid N. Naghiyev Maria M. Grishina Victor N. Khrustalev Ali N. Khalilov Mehmet Akkurt Anzurat A. Akobirshoeva İbrahim G. Mamedov |
| author_sort | Farid N. Naghiyev |
| collection | DOAJ |
| description | In the title compound, C28H21N3O, the 1,2-dihydropyridine ring of the 1,2,7,8-tetrahydroisoquinoline ring system is planar as expected, while the cyclohexa-1,3-diene ring has a twist-boat conformation, with Cremer–Pople parameters QT = 0.367 (2) A, θ = 117.3 (3)° and φ = 327.3 (4)°. The dihedral angles between the best planes through the isoquinoline ring system and the three phenyl rings are 81.69 (12), 82.45 (11) and 47.36 (10)°. In the crystal, molecules are linked via N—H...O and C—H...N hydrogen bonds, forming a three-dimensional network. Furthermore, the crystal packing is dominated by C—H...π bonds with a strong interaction involving the phenyl H atoms. The role of the intermolecular interactions in the crystal packing was clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (46.0%), C...H/H...C (35.1%) and N...H/H...N (10.5%) contacts. |
| first_indexed | 2024-04-11T19:46:22Z |
| format | Article |
| id | doaj.art-cd049d61e3234749905b99ba6724e667 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-04-11T19:46:22Z |
| publishDate | 2021-02-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-cd049d61e3234749905b99ba6724e6672022-12-22T04:06:29ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902021-02-0177219519910.1107/S2056989021000785vm2245Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetrahydroisoquinoline-4-carbonitrileFarid N. Naghiyev0Maria M. Grishina1Victor N. Khrustalev2Ali N. Khalilov3Mehmet Akkurt4Anzurat A. Akobirshoeva5İbrahim G. Mamedov6Department of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148 Baku, AzerbaijanPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St.6, Moscow, 117198 , Russian FederationPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St.6, Moscow, 117198 , Russian FederationDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148 Baku, AzerbaijanDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, TurkeyAcad. Sci. Republ. Tadzhikistan, Kh. Yu. Yusufbekov Pamir Biol. Inst., 1 Kholdorova St, Khorog 736002, Gbao, TajikistanDepartment of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148 Baku, AzerbaijanIn the title compound, C28H21N3O, the 1,2-dihydropyridine ring of the 1,2,7,8-tetrahydroisoquinoline ring system is planar as expected, while the cyclohexa-1,3-diene ring has a twist-boat conformation, with Cremer–Pople parameters QT = 0.367 (2) A, θ = 117.3 (3)° and φ = 327.3 (4)°. The dihedral angles between the best planes through the isoquinoline ring system and the three phenyl rings are 81.69 (12), 82.45 (11) and 47.36 (10)°. In the crystal, molecules are linked via N—H...O and C—H...N hydrogen bonds, forming a three-dimensional network. Furthermore, the crystal packing is dominated by C—H...π bonds with a strong interaction involving the phenyl H atoms. The role of the intermolecular interactions in the crystal packing was clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (46.0%), C...H/H...C (35.1%) and N...H/H...N (10.5%) contacts.http://scripts.iucr.org/cgi-bin/paper?S2056989021000785crystal structurecyclocondensation product1,2,7,8-tetrahydroisoquinoline ring systemhirshfeld surface analysis |
| spellingShingle | Farid N. Naghiyev Maria M. Grishina Victor N. Khrustalev Ali N. Khalilov Mehmet Akkurt Anzurat A. Akobirshoeva İbrahim G. Mamedov Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetrahydroisoquinoline-4-carbonitrile Acta Crystallographica Section E: Crystallographic Communications crystal structure cyclocondensation product 1,2,7,8-tetrahydroisoquinoline ring system hirshfeld surface analysis |
| title | Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetrahydroisoquinoline-4-carbonitrile |
| title_full | Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetrahydroisoquinoline-4-carbonitrile |
| title_fullStr | Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetrahydroisoquinoline-4-carbonitrile |
| title_full_unstemmed | Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetrahydroisoquinoline-4-carbonitrile |
| title_short | Crystal structure and Hirshfeld surface analysis of 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetrahydroisoquinoline-4-carbonitrile |
| title_sort | crystal structure and hirshfeld surface analysis of 3 amino 1 oxo 2 6 8 triphenyl 1 2 7 8 tetrahydroisoquinoline 4 carbonitrile |
| topic | crystal structure cyclocondensation product 1,2,7,8-tetrahydroisoquinoline ring system hirshfeld surface analysis |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989021000785 |
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