Crystal structure of 15-(2-chlorophenyl)-6b-hydroxy-17-methyl-6b,7,16,17-tetrahydro-7,14a-methanonaphtho[1′,8′:1,2,3]pyrrolo[3′,2′:8,8a]azuleno[5,6-b]quinolin-14(15H)-one

In the title compound, C34H25ClN2O2, the fused pyrrolidine ring adopts an envelope conformation with the N atom as the flap. The two adjacent cyclopentane rings also adopt envelope conformations. The mean plane of the pyrrolidine ring makes dihedral angles of 40.53 (10) and 80.23 (10)° with the mean planes of the cyclopentane rings. The dihedral angle between the mean planes of the cyclopentane rings is 46.71 (9)°. An intramolecular O—H⋯N hydrogen bond is observed. In the crystal, molecules are linked by C—H⋯O, C—H⋯N and C—H⋯π interactions, forming a layer parallel to (10-2).

In the title molecule, one cyclopentane ring I (C10-C12/C22/C23) is fused with the other cyclopentane ring II (C22-C24/C29/C30) of the acenaphthylene ring system (C22-C33). The pyrrolidine ring (C12/C14/C21/N2/C22) is fused with the cyclopentane ring I, and adopts an envelope conformation with atom N2 as the flap atom deviating by 0.5765 (2) Å from the mean plane defined by the other atoms (C12/C14/C21/C22). The two cyclopentane rings I and II adopt envelope conformations with atoms C11 and C22 as the flap atoms, respectively, deviating by 0.7033 and 0.1765 Å from the mean plane. The mean plane of the pyrrolidine ring makes dihedral angles of 40.53 (10) and 80.23 (10)° with the mean planes of the cyclopentane rings I and II, respectively. The mean plane of the pyrrolidine ring makes dihedral angles of 82.04 (8) and 68.25 (9)° with the mean plane of the acenapthylene and phenyl (C8-C13) ring systems, respectively. The mean plane of the cyclopentane ring I makes a dihedral angle of 46.71 (9)° with the mean plane of the cyclopentane ring II. The mean plane of the cyclopentane ring makes dihedral angles of 47.85 (7) and 87.06 (9)° with the mean plane of the acenaphthylene ring system and the phenyl ring, respectively.
In the crystal, a pair of C-H···N interactions (Table 1) show an R 2 2 (14) ring (Fig. 2). In addition, a C-H···O hydrogen bond links the symmetry-related molecules, forming a helical chain running along the b axis (Fig. 3). The two molecules are also held together by a C-H···π interaction (Fig. 4).

S2. Experimental
A mixture of (E)-2-(2-chlorobenzylidene)-3,4-dihydroacridin-1(2H)-one (1 mmol), acenaphthoquinone (1 mmol) and sarcosine (1.5 mmol) was heated to reflux in toluene (3 ml) for 10 h. After completion of the reaction as evident from TLC, the reaction mixture was extracted with ethyl acetate (2 × 20 ml), washed with water (2 × 10 ml), dried over supporting information anhydrous Na 2 SO 4 and concentrated under reduced pressure, subjected to column chromatography using petroleum ether-AcOEt (5:1 v/v) as eluent to obtain pure product. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethanol at room temperature.

S3. Refinement
The hydrogen atoms were placed in calculated positions with C-H = 0.93-0.98 Å and O-H = 0.82 Å, and were refined in a riding model with U iso (H) = 1.5U eq (C methyl , O) or 1.2U eq (C).

Figure 1
The molecular structure of the title compound, showing the atomic numbering and displacement ellipsoids drawn at 20% probability level.    Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.