Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate
The title compound, C29H33NO3, crystallizes with three molecules (A, B and C) in the asymmetric unit. They differ in the twist of the phenyl and benzene rings of the 1,1′-biphenyl ring with respect to the plane of the 1,4-dihydropyridine ring. In all three molecules, the 1,4-dihydropyridine ring ado...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
International Union of Crystallography
2022-08-01
|
| Series: | Acta Crystallographica Section E: Crystallographic Communications |
| Subjects: | |
| Online Access: | http://scripts.iucr.org/cgi-bin/paper?S2056989022007022 |
| _version_ | 1828443452355903488 |
|---|---|
| author | Sema Öztürk Yıldırım Mehmet Akkurt Gökalp Çetin Rahime Şimşek Ray J. Butcher Ajaya Bhattarai |
| author_facet | Sema Öztürk Yıldırım Mehmet Akkurt Gökalp Çetin Rahime Şimşek Ray J. Butcher Ajaya Bhattarai |
| author_sort | Sema Öztürk Yıldırım |
| collection | DOAJ |
| description | The title compound, C29H33NO3, crystallizes with three molecules (A, B and C) in the asymmetric unit. They differ in the twist of the phenyl and benzene rings of the 1,1′-biphenyl ring with respect to the plane of the 1,4-dihydropyridine ring. In all three molecules, the 1,4-dihydropyridine ring adopts a distorted boat conformation. The cyclohexene ring has an envelope conformation in molecules A and B, while it exhibits a distorted half-chair conformation for both the major and minor components in the disordered molecule C. In the crystal, molecules are linked by C—H...O and N—H...O hydrogen bonds, forming layers parallel to (100) defining R14(6) and C(7) graph-set motifs. Additional C—H...π interactions consolidate the layered structure. Between the layers, van der Waals interactions stabilize the packing, as revealed by Hirshfeld surface analysis. The greatest contributions to the crystal packing are from H...H (69.6% in A, 69.9% in B, 70.1% in C), C...H/H...C (20.3% in A, 20.6% in B, 20.3% in C) and O...H/H...O (8.6% in A, 8.6% in B, 8.4% in C) interactions. |
| first_indexed | 2024-12-10T21:28:32Z |
| format | Article |
| id | doaj.art-e0002e71f80644049f7d27f8f32b1670 |
| institution | Directory Open Access Journal |
| issn | 2056-9890 |
| language | English |
| last_indexed | 2024-12-10T21:28:32Z |
| publishDate | 2022-08-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj.art-e0002e71f80644049f7d27f8f32b16702022-12-22T01:32:54ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902022-08-0178879880310.1107/S2056989022007022wm5652Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylateSema Öztürk Yıldırım0Mehmet Akkurt1Gökalp Çetin2Rahime Şimşek3Ray J. Butcher4Ajaya Bhattarai5Department of Physics, Faculty of Science, Eskisehir Technical University, Yunus Emre Campus 26470 Eskisehir, TurkeyDepartment of Physics, Faculty of Science, Erciyes University, 38039 Kayseri, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Erzincan Binali Yıldırım University, 24100 Erzincan, TurkeyDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, 06100 Sıhhiye-Ankara, TurkeyDepartment of Chemistry, Howard University, Washington DC 20059, USADepartment of Chemistry, M.M.A.M.C (Tribhuvan University), Biratnagar, NepalThe title compound, C29H33NO3, crystallizes with three molecules (A, B and C) in the asymmetric unit. They differ in the twist of the phenyl and benzene rings of the 1,1′-biphenyl ring with respect to the plane of the 1,4-dihydropyridine ring. In all three molecules, the 1,4-dihydropyridine ring adopts a distorted boat conformation. The cyclohexene ring has an envelope conformation in molecules A and B, while it exhibits a distorted half-chair conformation for both the major and minor components in the disordered molecule C. In the crystal, molecules are linked by C—H...O and N—H...O hydrogen bonds, forming layers parallel to (100) defining R14(6) and C(7) graph-set motifs. Additional C—H...π interactions consolidate the layered structure. Between the layers, van der Waals interactions stabilize the packing, as revealed by Hirshfeld surface analysis. The greatest contributions to the crystal packing are from H...H (69.6% in A, 69.9% in B, 70.1% in C), C...H/H...C (20.3% in A, 20.6% in B, 20.3% in C) and O...H/H...O (8.6% in A, 8.6% in B, 8.4% in C) interactions.http://scripts.iucr.org/cgi-bin/paper?S2056989022007022crystal structure1,4-dihydropyridine ringcyclohexene ringquinoline ring systemvan der waals interactionshirshfeld surface analysisdisorder |
| spellingShingle | Sema Öztürk Yıldırım Mehmet Akkurt Gökalp Çetin Rahime Şimşek Ray J. Butcher Ajaya Bhattarai Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate Acta Crystallographica Section E: Crystallographic Communications crystal structure 1,4-dihydropyridine ring cyclohexene ring quinoline ring system van der waals interactions hirshfeld surface analysis disorder |
| title | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
| title_full | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
| title_fullStr | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
| title_full_unstemmed | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
| title_short | Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexahydroquinoline derivative: tert-butyl 4-([1,1′-biphenyl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate |
| title_sort | synthesis characterization crystal structure and hirshfeld surface analysis of a hexahydroquinoline derivative tert butyl 4 1 1 biphenyl 4 yl 2 6 6 trimethyl 5 oxo 1 4 5 6 7 8 hexahydroquinoline 3 carboxylate |
| topic | crystal structure 1,4-dihydropyridine ring cyclohexene ring quinoline ring system van der waals interactions hirshfeld surface analysis disorder |
| url | http://scripts.iucr.org/cgi-bin/paper?S2056989022007022 |
| work_keys_str_mv | AT semaozturkyıldırım synthesischaracterizationcrystalstructureandhirshfeldsurfaceanalysisofahexahydroquinolinederivativetertbutyl411biphenyl4yl266trimethyl5oxo145678hexahydroquinoline3carboxylate AT mehmetakkurt synthesischaracterizationcrystalstructureandhirshfeldsurfaceanalysisofahexahydroquinolinederivativetertbutyl411biphenyl4yl266trimethyl5oxo145678hexahydroquinoline3carboxylate AT gokalpcetin synthesischaracterizationcrystalstructureandhirshfeldsurfaceanalysisofahexahydroquinolinederivativetertbutyl411biphenyl4yl266trimethyl5oxo145678hexahydroquinoline3carboxylate AT rahimesimsek synthesischaracterizationcrystalstructureandhirshfeldsurfaceanalysisofahexahydroquinolinederivativetertbutyl411biphenyl4yl266trimethyl5oxo145678hexahydroquinoline3carboxylate AT rayjbutcher synthesischaracterizationcrystalstructureandhirshfeldsurfaceanalysisofahexahydroquinolinederivativetertbutyl411biphenyl4yl266trimethyl5oxo145678hexahydroquinoline3carboxylate AT ajayabhattarai synthesischaracterizationcrystalstructureandhirshfeldsurfaceanalysisofahexahydroquinolinederivativetertbutyl411biphenyl4yl266trimethyl5oxo145678hexahydroquinoline3carboxylate |