Crystal structure and Hirshfeld surface analysis of 1-[6-bromo-2-(3-bromo-phen-yl)-1,2,3,4-tetra-hydro-quinolin-4-yl]pyrrolidin-2-one

Anastasia A Pronina; Alexandra G Kutasevich; Mikhail S Grigoriev; Khudayar I Hasanov; Nurlana D Sadikhova; Tahir A Javadzade; Mehmet Akkurt; Ajaya Bhattarai

doi:10.1107/S2056989024008144

Crystal structure and Hirshfeld surface analysis of 1-[6-bromo-2-(3-bromo-phen-yl)-1,2,3,4-tetra-hydro-quinolin-4-yl]pyrrolidin-2-one

Acta Crystallogr E Crystallogr Commun. 2024 Aug 30;80(Pt 9):967-972. doi: 10.1107/S2056989024008144. eCollection 2024 Sep 1.

Authors

Anastasia A Pronina¹, Alexandra G Kutasevich¹, Mikhail S Grigoriev², Khudayar I Hasanov^{3

4}, Nurlana D Sadikhova⁵, Tahir A Javadzade⁶, Mehmet Akkurt⁷, Ajaya Bhattarai⁸

Affiliations

¹ RUDN University, 6 Miklukho-Maklaya St, Moscow, 117198, Russian Federation.
² Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninskiy prospect 31-4, Moscow 119071, Russian Federation.
³ Western Caspian University, Istiqlaliyyat Street 31, AZ1001, Baku, Azerbaijan.
⁴ Azerbaijan Medical University, Scientific Research Centre (SRC), A. Kasumzade St. 14. AZ 1022, Baku, Azerbaijan.
⁵ Department of Chemistry, Baku State University, Z. Xalilov Str. 23, Az 1148 Baku, Azerbaijan.
⁶ Department of Chemistry and Chemical Engineering, Khazar University, Mahsati St. 41, AZ 1096, Baku, Azerbaijan.
⁷ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye.
⁸ Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal.

Abstract

This study presents the synthesis, characterization and Hirshfeld surface analysis of 1-[6-bromo-2-(3-bromo-phen-yl)-1,2,3,4-tetra-hydro-quinolin-4-yl]pyrrolidin-2-one, C₁₉H₁₈Br₂N₂O. In the title compound, the pyrrolidine ring adopts a distorted envelope configuration. In the crystal, mol-ecules are linked by inter-molecular N-H⋯O, C-H⋯O and C-H⋯Br hydrogen bonds, forming a three-dimensional network. In addition, pairs of mol-ecules along the c axis are connected by C-H⋯π inter-actions. According to a Hirshfeld surface study, H⋯H (36.9%), Br⋯H/H⋯Br (28.2%) and C⋯H/H⋯C (24.3%) inter-actions are the most significant contributors to the crystal packing.

Keywords: Hirshfeld surface analysis; crystal structure; hydrogen bonds; tetrahydroquinoline; the Povarov method.

Grants and funding

This work was funded by Western Caspian University ; Azerbaijan Medical University ; Baku State University ; RUDN University Scientific Projects Grant System grant 021408--2-000.