(1S,8R,15S,19R)-17-Benzyl-17-azapentacyclo[6.6.5.02,7.09,14.015,19]nonadeca-2(7),3,5,9(14),10,12-hexaene chloroform monosolvate

In the title compound, C25H23N·CHCl3, the dihydroanthracene unit is bent with a dihedral angle between the benzene rings of 57.82 (8)°. The N atom of the pyrrolidine heterocycle, which has an envelope conformation with the N atom as the flap, exhibits a pronounced pyramidalization [Σ(C—N—C) = 328.07°], indicating an accentuated N-donor character. In the crystal, this behaviour is evident by the C—H⋯N hydrogen bond involving a solvent molecule and the N atom. The absolute configuration at the C-atom fused positions of the pyrrolidine group were crystallographically confirmed to be S and R.

In the title compound, C 25 H 23 NÁCHCl 3 , the dihydroanthracene unit is bent with a dihedral angle between the benzene rings of 57.82 (8) . The N atom of the pyrrolidine heterocycle, which has an envelope conformation with the N atom as the flap, exhibits a pronounced pyramidalization [AE(C-N-C) = 328.07 ], indicating an accentuated N-donor character. In the crystal, this behaviour is evident by the C-HÁ Á ÁN hydrogen bond involving a solvent molecule and the N atom. The absolute configuration at the C-atom fused positions of the pyrrolidine group were crystallographically confirmed to be S and R.
The molecular structure of the title compound is shown in Fig. 1. The 9,10-dihydroanthracenyl is bent with a dihedral angle between the benzene rings of 57.82 (8)°. The pyrrolidine heterocycle has an envelope conformation with atom N1 as the flap. It is displaced from the mean plane of the four C-atoms, C15-C18 [maximum deviation = 0.0025 (15) Å] by 0.6313 (14) Å. This mean plane forms a dihedral angle of 50.78 (10)° with the C20-C25 benzyl ring. In contrast to analogous dicarboximide compounds, a pronounced pyramidalization of the atom N1 is observed with Σ C-N1-C = 328.07°, which signifies an accentuated N-donor character.
In the crystal, this N-donor behaviour is evident by the C-H···N intermolecular hydrogen bond involving a chloroform solvate molecule (Table 1 and Fig. 2).
The absolute configuration of atoms C15 and C16 was crystallographically confirmed to be S and R, respectively ( Fig.   1).

Experimental
The title compound was prepared by the reduction of the corresponding 9,10-dihydroanthracene-succinimide following the reported procedure (Sanhes et al., 2008). To a solution of the succinimide (920 mg, 2.52 mmol) in 50 ml of THF at 273 K, LiAlH 4 (1.43 g, 37.7 mmol) was added in small portions and the mixture was then refluxed for 72 h. The reaction mixture was cooled to 273 K, then diethylether (30 ml) and an aqueous saturated solution of Na 2 SO 4 were sequentially added. The precipitate that formed was filtered off and the filtrate washed three times with water. The combined organic layers were dried over anhydrous Na 2 SO 4 , filtered and the solvent evaporated under vacuum. Crystals of the title compound were obtained by slow evaporation of a solution in CHCl 3 . The title compound was characterized by high-