3-Benzyl-7-methyl-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexahydro-1H-pyrrolo[3,4-b]quinoline

In the title compound, C32H32N2O2S, the pyrrolidine ring adopts a twist conformation while the tetrahydropyridine ring is in a distorted half-chair conformation. The two rings are trans-fused. The dihedral angle between the sulfonyl and benzyl phenyl rings is 72.54 (14)°. The molecular structure is stabilized by C—H⋯O hydrogen bonds, and N—H⋯π interactions involving the benzyl phenyl ring. The screw-related molecules are linked into chains along the b axis by C—H⋯O hydrogen bonds and C—H⋯π interactions. Adjacent inversion-related chains interact via C—H⋯π interactions, forming a two-dimensional network parallel to the bc plane.

In the title compound, C 32 H 32 N 2 O 2 S, the pyrrolidine ring adopts a twist conformation while the tetrahydropyridine ring is in a distorted half-chair conformation. The two rings are trans-fused. The dihedral angle between the sulfonyl and benzyl phenyl rings is 72.54 (14) . The molecular structure is stabilized by C-HÁ Á ÁO hydrogen bonds, and N-HÁ Á Á interactions involving the benzyl phenyl ring. The screwrelated molecules are linked into chains along the b axis by C-HÁ Á ÁO hydrogen bonds and C-HÁ Á Á interactions. Adjacent inversion-related chains interact via C-HÁ Á Á interactions, forming a two-dimensional network parallel to the bc plane.

Comment
Pyrroloquinoline derivatives have been synthesized and investigated as potential anticancer drugs (Ferlin et al., 2005;Gasparotto et al., 2007). Some of them have been found to exhibit photochemotherapeutic activity (Barraja et al., 2003). As part of our studies on pyrroloquinoline derivatives, we report here the crystal structure of the title compound (I).
In the solid state, screw-related molecules are linked into chains along the b axis by C-H···O hydrogen bonds and C-H···π interactions involving the C26-C31 ring (Table 1). Adjacent inversion-related chains interact via C-H···π interactions involving the C4-C9 and C12-C17 rings to form a two-dimensional network parallel to the bc plane ( Fig.3).
A comparison of crystal packing in (I) and (II) shows that the presence of the methyl group at 7-position completely changes the packing mode. Without the methyl group, the molecules are linked into a chain along the a axis by intermolecular C-H···π interactions. But the presence of the methyl group resulted in a two-dimensional network parallel to the bc plane, as discussed above.

Experimental
InCl 3 (20 mol%) was added to a mixture of 2-(N-cinnamyl-N-tosylamino)-3-phenyl propanal (1 mmol) and p-methyl aniline (1 mmol) in acetonitrile (20 ml). The reaction mixture was stirred at room temperature for 1 min. On completion of the reaction, as indicated by TLC, the mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over Na 2 SO 4 . The solvent was evaporated in vacuo and the crude product was chromatographed on silica gel using a hexane-ethyl acetate (8.5:1.5 v/v) mixture to obtain the title compound. The compound was recrystallized from ethyl acetate solution by slow evaporation. positioned geometrically (C-H = 0.93-0.98 Å) and allowed to ride on their parent atoms, with U iso (H) = 1.2U eq (C) or 1.5U eq (C methyl ). A rotating group model was used for methyl groups. Reflection 002 was partially obscured by the beam stop and was omitted.   3-Benzyl-7-methyl-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexahydro-1H-pyrrolo [3,4-b]quinoline as those based on F, and R-factors based on ALL data will be even larger.