Crystal structure of 5''-benzyl-idene-1'-methyl-4'-phenyl-tri-spiro-[ace-naphthyl-ene-1,2'-pyrrolidine-3',1''-cyclo-hexane-3'',2'''-[1,3]dioxane]-2,6''-dione.

Kuppan Chandralekha,Deivasigamani Gavaskar,Adukamparai Rajukrishnan Sureshbabu,Srinivasakannan Lakshmi

doi:10.1107/s2056989016002875

Kuppan Chandralekha, Deivasigamani Gavaskar + Show 2 more

Open Access

https://doi.org/10.1107/s2056989016002875

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Abstract

In the title compound, C36H31NO4, two spiro links connect the methyl-substituted pyrrolidine ring to the ace-naphthyl-ene and cyclo-hexa-none rings. The cyclo-hexa-none ring is further connected to the dioxalane ring by a third spiro junction. The five-membered ring of the ace-naphthylen-1-one ring system adopts a flattened envelope conformation with the ketonic C atom as flap, whereas the dioxalane and pyrrolidine rings each have a twist conformation. The cyclo-hexa-none ring assumes a boat conformation. Three intra-molecular C-H⋯O hydrogen bonds involving both ketonic O atoms as acceptors are present. In the crystal, C-H⋯O hydrogen bonds connect centrosymmetrically related mol-ecule into chains parallel to the b axis, forming rings of R 2 (2)(10)and R 2 (2)(8) graph-set motifs.

Highlights

In the title compound, C36H31NO4, two spiro links connect the methylsubstituted pyrrolidine ring to the acenaphthylene and cyclohexanone rings
The cyclohexanone ring is further connected to the dioxalane ring by a third spiro junction
The biological properties of spiro compounds containing cyclic structures are evident from their presence in many natural products (Molvi et al, 2014)

Summary

Chemical context

The biological properties of spiro compounds containing cyclic structures are evident from their presence in many natural products (Molvi et al, 2014). Spiro pyrrolidines act as inhibitors of human NK-I receptor activity (Kumar, Perumal, Manju et al, 2009). They are exhibit antimicrobial (Sureshbabu et al, 2008), anticonvulsant and neurotoxic properties (Obniska et al, 2006) and antiproliferative activities (Almansour et al, 2014). A rare dispiroheterocyclic compound was synthesized through 1,3dipolar cycloaddition of azomethine ylide for the purpose of designing a new class of complex dispiroheterocycles with potential biological activities. In continuation of our work in this field, the crystal structure of title trispiropyrrolidine is reported on

Structural commentary

Supramolecular features

Synthesis and crystallization

Refinement