Synthesis, characterization, crystal structure and Hirshfeld surface analysis of isobutyl 4-[4-(difluoromethoxy)phenyl]-2,6,6-trimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate

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Yıldırım S. Ö., AKKURT M., ÇETİN G., ŞİMŞEK R., Butcher R. J., Bhattarai A.

Acta Crystallographica Section E: Crystallographic Communications, vol.79, no.Pt 12, pp.1132-1136, 2023 (ESCI) identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 79 Issue: Pt 12
  • Publication Date: 2023
  • Doi Number: 10.1107/s2056989023009623
  • Journal Name: Acta Crystallographica Section E: Crystallographic Communications
  • Journal Indexes: Emerging Sources Citation Index (ESCI), Scopus
  • Page Numbers: pp.1132-1136
  • Keywords: 1,4-dihydropyridine ring, crystal structure, cyclohexene ring, Hirshfeld surface analysis, quinoline ring system, van der Waals interactions
  • Erciyes University Affiliated: Yes

Abstract

In the title compound, C24H29F2NO4, which crystallizes in the orthorhombic Pca21 space group with Z = 4, the 1,4-dihydropyridine ring adopts a distorted boat conformation, while the cyclohexene ring is in a distorted half-chair conformation. In the crystal, the molecules are linked by N—H· · ·O and C—H· · ·O interactions, forming supramolecular chains parallel to the a axis. These chains pack with C—H· · ·π interactions between them, forming layers parallel to the (010) plane. The cohesion of the crystal structure is ensured by van der Waals interactions between these layers. Hirshfeld surface analysis shows the major contributions to the crystal packing are from H· · ·H (56.9%), F· · ·H/H· · ·F (15.7%), O· · ·H/H· · ·O (13.7%) and C· · ·H/H· · ·C (9.5%) contacts.