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

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Yildirim S. O., AKKURT M., ÇETİN G., ŞİMŞEK R., Butcher R. J., Bhattarai A.

ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, vol.78, pp.798-821, 2022 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 78
  • Publication Date: 2022
  • Doi Number: 10.1107/s2056989022007022
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.798-821
  • Keywords: crystal structure, 1,4-dihydropyridine ring, cyclohexene ring, quinoline ring system, van der Waals interactions, Hirshfeld surface analysis, disorder, CELLS
  • Hacettepe University Affiliated: Yes


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 1,10-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 center dot center dot center dot O and N-H center dot center dot center dot O hydrogen bonds, forming layers parallel to (100) defining R-4(1)(6) and C(7) graph-set motifs. Additional C-H center dot center dot center dot pi interactions consolidate the layered structure. Between the layers, van derWaals interactions stabilize the packing, as revealed by Hirshfeld surface analysis. The greatest contributions to the crystal packing are from H center dot center dot center dot H (69.6% in A, 69.9% in B, 70.1% in C), C center dot center dot center dot H/H center dot center dot center dot C (20.3% in A, 20.6% in B, 20.3% in C) and O center dot center dot center dot H/H center dot center dot center dot O (8.6% in A, 8.6% in B, 8.4% in C) interactions.