Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexa-hydro-quinoline derivative: tert-butyl 4-([1,1'-biphen-yl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate

Sema Öztürk Yıldırım; Mehmet Akkurt; Gökalp Çetin; Rahime Şimşek; Ray J Butcher; Ajaya Bhattarai

doi:10.1107/S2056989022007022

Synthesis, characterization, crystal structure and Hirshfeld surface analysis of a hexa-hydro-quinoline derivative: tert-butyl 4-([1,1'-biphen-yl]-4-yl)-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexa-hydro-quinoline-3-carboxyl-ate

Acta Crystallogr E Crystallogr Commun. 2022 Jul 14;78(Pt 8):798-803. doi: 10.1107/S2056989022007022. eCollection 2022 Aug 1.

Authors

Sema Öztürk Yıldırım^{1

2}, Mehmet Akkurt², Gökalp Çetin^{3

4}, Rahime Şimşek⁴, Ray J Butcher⁵, Ajaya Bhattarai⁶

Affiliations

¹ Department of Physics, Faculty of Science, Eskisehir Technical University, Yunus Emre Campus 26470 Eskisehir, Turkey.
² Department of Physics, Faculty of Science, Erciyes University, 38039 Kayseri, Turkey.
³ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Erzincan Binali Yıldırım University, 24100 Erzincan, Turkey.
⁴ Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, 06100 Sıhhiye-Ankara, Turkey.
⁵ Department of Chemistry, Howard University, Washington DC 20059, USA.
⁶ Department of Chemistry, M.M.A.M.C (Tribhuvan University), Biratnagar, Nepal.

Abstract

The title compound, C₂₉H₃₃NO₃, crystallizes with three mol-ecules (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-di-hydro-pyridine ring. In all three mol-ecules, the 1,4-di-hydro-pyridine ring adopts a distorted boat conformation. The cyclo-hexene ring has an envelope conformation in mol-ecules A and B, while it exhibits a distorted half-chair conformation for both the major and minor components in the disordered mol-ecule C. In the crystal, mol-ecules are linked by C-H⋯O and N-H⋯O hydrogen bonds, forming layers parallel to (100) defining R ¹ ₄(6) and C(7) graph-set motifs. Additional C-H⋯π inter-actions consolidate the layered structure. Between the layers, van der Waals inter-actions 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) inter-actions.

Keywords: 1,4-dihydropyridine ring; Hirshfeld surface analysis; crystal structure; cyclohexene ring; disorder; quinoline ring system; van der Waals interactions.

Grants and funding

RJB is grateful for funding from NSF (award 1205608) and the Partnership for Reduced Dimensional Materials for partial funding of this research, and the NSF–MRI program (grant No. CHE0619278) for funds to purchase the X-ray diffractometer. This study was supported by Hacettepe University Scientific Research Unit (Project No. THD-2020–18806).