Crystal structure and Hirshfeld surface analysis of 2,5-di-imino-8a-methyl-4,9-bis-(4-methyl-phen-yl)-7-oxo-6-phenyl-deca-hydro-2 H-3,8-methano-pyrano[3,2- c]pyridine-3,4a-dicarbo-nitrile N, N-di-methyl-formamide monosolvate

Farid N Naghiyev; Victor N Khrustalev; Anton P Novikov; Mehmet Akkurt; Ali N Khalilov; Ajaya Bhattarai; İbrahim G Mamedov

doi:10.1107/S2056989023001718

Crystal structure and Hirshfeld surface analysis of 2,5-di-imino-8a-methyl-4,9-bis-(4-methyl-phen-yl)-7-oxo-6-phenyl-deca-hydro-2 H-3,8-methano-pyrano[3,2- c]pyridine-3,4a-dicarbo-nitrile N, N-di-methyl-formamide monosolvate

Acta Crystallogr E Crystallogr Commun. 2023 Mar 2;79(Pt 4):254-258. doi: 10.1107/S2056989023001718. eCollection 2023 Mar 1.

Authors

Farid N Naghiyev¹, Victor N Khrustalev^{2

3}, Anton P Novikov², Mehmet Akkurt⁴, Ali N Khalilov^{5

1}, Ajaya Bhattarai⁶, İbrahim G Mamedov¹

Affiliations

¹ Department of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148, Baku, Azerbaijan.
² Peoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St.6, Moscow, 117198, Russian Federation.
³ N. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation.
⁴ Department of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye.
⁵ "Composite Materials" Scientific Research Center, Azerbaijan State Economic University (UNEC), H. Aliyev str. 135, Az 1063, Baku, Azerbaijan.
⁶ Department of Chemistry, M.M.A.M.C (Tribhuvan University) Biratnagar, Nepal.

Abstract

In the title compound, C₃₂H₂₉N₅O₂·C₃H₇NO, the bi-cyclo[3.3.1]nonane ring sys-tem adopts a half-chair/twist-boat conformation, with the phenyl rings in equatorial orientations with respect to the piperidine ring. The two oxane rings of the 2-oxabi-cyclo-[2.2.2]octane ring system exhibit a distorted boat conformation. Inter-molecular C-H⋯O and C-H⋯N hydrogen bonds connect the mol-ecules in the crystal, generating layers extending parallel to (100). These layers are connected by C-H⋯π inter-actions. A Hirshfeld surface analysis was per-formed to qu-antify the contributions of the different inter-molecular inter-actions, indicating that the most important contributions to the crystal packing are from H⋯H (52.5%), N⋯H/H⋯N (19.2%), C⋯H/H⋯C (18.8%) and O⋯H/H⋯O (8.3%) inter-actions.

Keywords: C—H⋯π interactions; Hirshfeld surface analysis; bicyclo [3.3.1]nonane ring system; crystal structure; hydrogen-bonding.

Grants and funding

This paper was supported by Baku State University and the Ministry of Science and Higher Education of the Russian Federation [award No. 075–03–2020-223 (FSSF-2020–0017)].