11-[(E)-Benzylidene]-14-hydroxy-8-phenyl-3,13-diazaheptacyclo[13.7.1.19,13.02,9.02,14.03,7.019,23]tetracosa-1(22),15,17,19(23),20-pentaen-10-one

In the title compound, C35H30N2O2, the piperidine ring adopts a chair conformation and the pyrrolidine ring adopts an envelope conformation. The naphthalene ring makes dihedral angles of 24.56 (3) and 36.13 (4)° with the terminal phenyl rings. The dihedral angle between the two terminal phenyl rings is 55.27 (5)°. One of the C atoms in the pyrrolidine ring is disordered over two sites, with a refined occupany ratio of 0.670 (3):0.330 (3). An intramolecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal structure, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R 2 2(18) loops within sheets of molecules lying parallel to the bc plane.

In the title compound, C 35 H 30 N 2 O 2 , the piperidine ring adopts a chair conformation and the pyrrolidine ring adopts an envelope conformation. The naphthalene ring makes dihedral angles of 24.56 (3) and 36.13 (4) with the terminal phenyl rings. The dihedral angle between the two terminal phenyl rings is 55.27 (5) . One of the C atoms in the pyrrolidine ring is disordered over two sites, with a refined occupany ratio of 0.670 (3):0.330 (3). An intramolecular O-HÁ Á ÁN hydrogen bond generates an S(6) ring. In the crystal structure, inversion dimers linked by pairs of C-HÁ Á ÁO hydrogen bonds generate R 2 2 (18) loops within sheets of molecules lying parallel to the bc plane.

Comment
The intermolecular [3+2]-cycloaddition of azomethine ylides with olefinic dipolarophiles affords a number of novel heterocyclic scaffolds which are useful for the creation of diverse chemical libraries of drug-like molecules for biological screening (Padwa, 1984;Grigg & Sridharan, 1993). Functionalized pyrrolizidines are the central skeleton for numerous alkaloids and constitute classes of compounds with significant biological activity (Monlineux, 1987). In view of the biological significance of pyrrolizidines, the crystal structure determination of the title compound was carried out and the results are presented here.
The molecular structure of the title compound is shown in Fig In the crystal packing (Fig. 2), adjacent molecules are connected by intramolecular O2-H1O2···N2 and intermolecular C35-H35A···O2 (Table 1) hydrogen bonds, forming dimers lying on sheets parallel to the bc plane.

Experimental
A mixture of 3,5-bis[(E)-phenylmethylidene]tetrahydro-4(1H)-pyridinone (0.100 g, 0.363 mmol), acenaphthenequinone (0.066 g, 0.363 mmol) and proline (0.042 g, 0.363 mmol) were dissolved in methanol (5 ml) and refluxed for 30 min. 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 afford the product which was recrystallised from ethyl acetate to reveal the title compound as colourless plates.

Refinement
The hydroxyl H atom H1O2 was located from a difference Fourier map and refined freely. The remaining H atoms were positioned geometrically [C-H = 0.93-0.97 Å] and were refined using a riding model, with U iso (H) = 1.2U eq (C). One of the C atom (C26) of the pyrrolidine ring and the associated H atoms H25A, H25B, H26A, H26B, H27A and H27B disordered over two sites with a refined occupancy ratio of 0.670 (3):0.330 (3). Fig. 1. The asymmetric unit of the title compound, showing 30% probability displacement ellipsoids (H atoms are omitted for clarity). Dotted lines represents the disorder component.    (2)