(3a S,4 R,5 R,6 S,7a R)-4,5-Di-bromo-2-[4-(tri-fluoro-meth-yl)phen-yl]-2,3,3a,4,5,6,7,7a-octa-hydro-3a,6-ep-oxy-1 H-isoindol-1-one: crystal structure and Hirshfeld surface analysis

Dmitriy F Mertsalov; Kseniia A Alekseeva; Magrycheva S Daria; Maxim E Cheshigin; Sevim Türktekin Çelikesir; Mehmet Akkurt; Mikhail S Grigoriev; Sixberth Mlowe

doi:10.1107/S2056989021003200

(3a S,4 R,5 R,6 S,7a R)-4,5-Di-bromo-2-[4-(tri-fluoro-meth-yl)phen-yl]-2,3,3a,4,5,6,7,7a-octa-hydro-3a,6-ep-oxy-1 H-isoindol-1-one: crystal structure and Hirshfeld surface analysis

Acta Crystallogr E Crystallogr Commun. 2021 Apr 9;77(Pt 5):466-472. doi: 10.1107/S2056989021003200. eCollection 2021 May 1.

Authors

Dmitriy F Mertsalov¹, Kseniia A Alekseeva¹, Magrycheva S Daria¹, Maxim E Cheshigin¹, Sevim Türktekin Çelikesir², Mehmet Akkurt², Mikhail S Grigoriev³, Sixberth Mlowe⁴

Affiliations

¹ Department of Organic Chemistry, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklaya St., 117198, Moscow, Russian Federation.
² Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey.
³ Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskiy prospect 31-4, Moscow 119071, Russian Federation.
⁴ University of Dar es Salaam, Dar es Salaam University College of Education, Department of Chemistry, PO Box 2329, Dar es Salaam, Tanzania.

Abstract

The asymmetric unit of the title compound, C₁₅H₁₂Br₂F₃NO₂, consists of two crystallographically independent mol-ecules. In both mol-ecules, the pyrrolidine and tetra-hydro-furan rings adopt an envelope conformation. In the crystal, mol-ecule pairs generate centrosymmetric rings with R ² ₂(8) motifs linked by C-H⋯O hydrogen bonds. These pairs of mol-ecules form a tetra-meric supra-molecular motif, leading to mol-ecular layers parallel to the (100) plane by C-H⋯π and C-Br⋯π inter-actions. Inter-layer van der Waals and inter-halogen inter-actions stabilize mol-ecular packing. The F atoms of the CF₃ groups of both mol-ecules are disordered over two sets of sites with refined site occupancies of 0.60 (3)/0.40 (3) and 0.640 (15)/0.360 (15). The most important contributions to the surface contacts of both mol-ecules are from H⋯H (23.8 and 22.4%), Br⋯H/H⋯Br (18.3 and 12.3%), O⋯H/H⋯O (14.3 and 9.7%) and F⋯H/H⋯F (10.4 and 19.1%) inter-actions, as concluded from a Hirshfeld surface analysis.

Keywords: Hirshfeld surface analysis; crystal structure; epoxyisoindole group; halogen bond; hydrogen bond; non-covalent interactions.

Grants and funding

This work was funded by Ministry of Education and Science of the Russian Federation grant 075–03-2020–223 (FSSF-2020–0017).