2-Hydroxy-5-[(E)-2-methylbenzylidene]-8-(2-methylphenyl)-9-phenyl-3,10-diazahexacyclo[10.7.1.13,7.02,11.07,11.016,20]henicosa-1(20),12,14,16,18-pentaen-6-one

In the title compound, C40H34N2O2, the central piperidine ring adopts a half-chair conformation and the fused pyrrolidine rings adopt twisted envelope (with the C atom bearing the methylphenyl ring as the flap atom) and envelope (with the C atom bound to the N atom, common to the pyridinone and pyrrolidine rings being the flap atom) conformations. The molecular structure features weak intramolecular N—H⋯O and C—H⋯O interactions. In the crystal, O—H⋯O hydrogen bonds generate a C(7) chain along the b-axis direction. C—H⋯O interactions also occur.

In the title compound, C 40 H 34 N 2 O 2 , the central piperidine ring adopts a half-chair conformation and the fused pyrrolidine rings adopt twisted envelope (with the C atom bearing the methylphenyl ring as the flap atom) and envelope (with the C atom bound to the N atom, common to the pyridinone and pyrrolidine rings being the flap atom) conformations. The molecular structure features weak intramolecular N-HÁ Á ÁO and C-HÁ Á ÁO interactions. In the crystal, O-HÁ Á ÁO hydrogen bonds generate a C(7) chain along the b-axis direction. C-HÁ Á ÁO interactions also occur.

Suresh Comment
The pyrrolidine ring system has been the subject of research for more than three decades. Many natural and synthetic compounds with pyrrolidine moieties have received much attention because of their remarkable biological properties (Shorvon, 2001;Watson et al., 2001;Asano et al., 2000;Winchester et al., 1992). Recognizing the importance of such compounds in drug discovery and as a part of our ongoing research in the construction of novel heterocycles, has prompted us to investigate the 1,3-dipolar cycloaddition of bisarylmethylidene pyridinones with azomethine ylide generated in situ from acenaphthenequinone and proline, we and report the crystal structure of the resulting pyrrolidine cyclo-adduct in this paper.
In the structure, the aryl ring C22-C27 is not coplanar with the mean plane of the piperidone ring [torsion angle C1-C2 -C21-C22 is 5.77 (3)] °, which is due to non-bonded interactions between one of the ortho H atoms in the aryl ring and the equatorial H atom at the 2-position of the piperidone ring (H12A/H1A or H1B).

Experimental
A mixture of 3,5-bis[(E)-(2-methylphenyl)methylidene]tetrahydro-4(1H)-pyridinone (1 mmol), acenaphthenequinone (1 mmol), and phenylglycine (1 mmol) were dissolved in methanol (5 ml) and refluxed in a water bath for 1 h. After completion of the reaction as evident from TLC, the mixture was poured into water (50 ml). The precipitated solid was filtered and washed with water to obtain the product which was further purified by recrystallization from ethyl acetate. Refinement H atoms were placed at calculated positions and allowed to ride on their carrier atoms with C-H = 0.93-0.97 Å and O-H = 0.82 Å. U iso = 1.2U eq (C) for CH CH 2 groups and U iso = 1.5U eq (C) for OH and CH 3 groups.

Figure 1
The molecular structure of (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme.     Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.