Synthesis and Structure Elucidation of Novel Spirooxindole Linked to Ferrocene and Triazole Systems via [3+2] Cycloaddition Reaction

In the present work, a novel heterocyclic hybrid of a spirooxindole system was synthesized via the attachment of ferrocene and triazole motifs into an azomethine ylide by [3 + 2] cycloaddition reaction protocol. The X-ray structure of the heterocyclic hybrid (1 '' R,2 '' S,3R)-2 ''-(1-(3-chloro-4-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-carbonyl)-5-methyl-1 ''-(ferrocin-2-yl)-1 '',2 '',5 '',6 '',7 '',7a ''-hexahydrospiro[indoline-3,3 ''-pyrrolizin]-2-one revealed very well the expected structure, by using different analytical tools (FTIR and NMR spectroscopy). It crystallized in the triclinic-crystal system and the P-1-space group. The unit cell parameters are a = 9.1442(2) angstrom, b = 12.0872(3) angstrom, c = 14.1223(4) angstrom, alpha = 102.1700(10)degrees, beta = 97.4190(10)degrees, gamma = 99.1600(10)degrees, and V = 1484.81(7) angstrom(3). There are two molecules per unit cell and one formula unit per asymmetric unit. Hirshfeld analysis was used to study the molecular packing of the heterocyclic hybrid. H center dot center dot center dot H (50.8%), H center dot center dot center dot C (14.2%), Cl center dot center dot center dot H (8.9%), O center dot center dot center dot H (7.3%), and N center dot center dot center dot H (5.1%) are the most dominant intermolecular contacts in the crystal structure. O center dot center dot center dot H, N center dot center dot center dot H, H center dot center dot center dot C, F center dot center dot center dot H, F center dot center dot center dot C, and O center dot center dot center dot O are the only contacts that have the characteristic features of short and significant interactions. AIM study indicated predominant covalent characters for the Fe-C interactions. Also, the electron density (rho(r)) at the bond critical point correlated inversely with the Fe-C distances.

Automated summary

In this study, a novel heterocyclic hybrid of a spirooxindole system was synthesized by attaching ferrocene and triazole motifs into an azomethine ylide through a [3 + 2] cycloaddition reaction. The X-ray structure analysis revealed the expected structure of the heterocyclic hybrid and its crystallization in the triclinic-crystal system. Hirshfeld analysis provided insights into the molecular packing and identified the dominant intermolecular contacts in the crystal structure. AIM study indicated covalent characteristics for the Fe-C interactions.