Crystal structure and Hirshfeld surface analysis of (22 RS,23 SR,25 RS,26 SR)-23,25,5-trimethyl-21-(2,2,2-tri-fluoro-acet-yl)-5-aza-2(2,6)-piperidina-1,3(2,5)-di-furana-cyclo-hexa-phan-24-one

Sema Öztürk Yıldırım; Mehmet Akkurt; Anastasia A Ershova; Mikhail S Grigoriev; Bruno G M Rocha; Ajaya Bhattarai

doi:10.1107/S2056989023001986

Crystal structure and Hirshfeld surface analysis of (2² RS,2³ SR,2⁵ RS,2⁶ SR)-2³,2⁵,5-trimethyl-2¹-(2,2,2-tri-fluoro-acet-yl)-5-aza-2(2,6)-piperidina-1,3(2,5)-di-furana-cyclo-hexa-phan-2⁴-one

Acta Crystallogr E Crystallogr Commun. 2023 Mar 10;79(Pt 4):292-296. doi: 10.1107/S2056989023001986. eCollection 2023 Mar 1.

Authors

Sema Öztürk Yıldırım^{1

2}, Mehmet Akkurt², Anastasia A Ershova³, Mikhail S Grigoriev⁴, Bruno G M Rocha⁵, Ajaya Bhattarai⁶

Affiliations

¹ Department of Physics, Faculty of Science, Eskisehir Technical University, Yunus Emre Campus 26470 Eskisehir, Türkiye.
² Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye.
³ Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., Moscow, 117198, Russian Federation.
⁴ Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences (IPCE RAS), 31 Bldg 4, Leninsky prosp., Moscow, 119071, Russian Federation.
⁵ Centro de Química Estrutural, Institute of Molecular Sciences, Instituto Superior Técnico, Universidade de Lisboa, Av. Rovisco Pais, 1049-001 Lisboa, Portugal.
⁶ Department of Chemistry, M.M.A.M.C (Tribhuvan University), Biratnagar, Nepal.

Abstract

The title compound, C₂₀H₂₁F₃N₂O₄, features a main twelve-membered difuryl ring with which the furan rings make dihedral angles of 76.14 (5) and 33.81 (5)°. The dihedral angle between the furan rings is 42.55 (7)°. The six-membered nitro-gen heterocycle has a twist-boat conformation. In the crystal, pairs of mol-ecules are connected by inter-molecular C-H⋯O inter-actions, generating an R ² ₂(14) ring motif. These pairs of mol-ecules form zigzag chains along the a-axis direction by means of C-H⋯F inter-actions. Furthermore, C-H⋯π and C-F⋯π inter-actions link the mol-ecules into chains along the b-axis direction, forming sheets parallel to the (001) plane. These sheets are also connected by van der Waals inter-actions.

Keywords: Hirshfeld surface analysis; Mannich reaction; alkylation; crystal structure; furan; piperidon; twelve-membered heterocycles.