Abstract
In the title pyrrolizidine derivative, C33H26F2N2O2, both pyrrolidine rings of the pyrrolizidine moiety adopt an envelope conformation. The di-fluoro-phenyl group is oriented at an angle of 54.3 (1)° with respect to the oxindole moiety. The crystal packing features an N-H⋯O hydrogen bond, which forms an R 2 (2)(8) motif, and a C-H⋯O inter-action, which generates a C(8) chain along [010]. In addition, this chain structure is stabilized by C-H⋯π inter-actions. In one of the pyrrolidine rings, the methyl-ene group forming the flap of an envelope and the H atoms of the adjacent methyl-ene groups are disordered over two sets of sites, with site-occupancy factors of 0.571 (4) and 0.429 (4).
Highlights
In the title pyrrolizidine derivative, C33H26F2N2O2, both pyrrolidine rings of the pyrrolizidine moiety adopt an envelope conformation
The difluorophenyl group is oriented at an angle of 54.3 (1) with respect to the oxindole moiety
In one of the pyrrolidine rings, the methylene group forming the flap of an envelope and the H atoms of the adjacent methylene groups are disordered over two sets of sites, with site-occupancy factors of 0.571 (4) and 0.429 (4)
Summary
Isatin (1H-indole-2,3-dione) has been exploited extensively as a key intermediate in organic multicomponent reactions due to its antibacterial (Sridhar et al, 2001), antifungal (Amal Raj et al, 2003; Dandia et al, 2006), antiviral (Quenelle et al., 2006), anti-HIV (Sriram et al, 2006; Pandeya et al, 2000), antimycobacterial (Feng et al, 2010), anticancer (Gursoy & Karali, 2003), anti-inflammatory (Sridhar & Ramesh, 2001) and anticonvulsant (Verma et al, 2004) activities. The versatile reactivity of isatin has led to the synthesis of a number of isatin-based spiro compounds. Chalcones are precursors and valuable intermediates for the synthesis of many biologically important heterocyclic compounds. The combination of chalcone with isatin and secondary amino acids provides spirooxindolopyrrolizidine derivatives with enhanced biological activities. In view of the many interesting applications of pyrrolizidine derivatives, we synthesized the title compound and report its crystal structure. The molecular structure of the title compound, showing the atom labelling.
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