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In the title compound, C39H38N4O8, the quinoxaline and indene subunits are essentially planar, with maximum deviations of 0.071 (2) and 0.009 (2) Å, respectively. The indeno­quinoxaline system forms a dihedral angle of 72.81 (3)° with the chromenopyrrolizine system. The two dioxolane rings, as well as the pyran ring of the chromeno group and the terminal pyrrolizine, each adopt an envelope conformation with O and C as flap atoms. The central pyrrolizine ring adopts a twisted conformation. Intra­molecular C—H...O and C—H...N hydrogen bonds occur. The crystal structure exhibits C—H...O hydrogen bonds, and is further stablized by C—H...π inter­actions, forming a two-dimensional network along the bc plane.

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The title compounds, (I) and (II), are di­spiro-indole-pyrrolidine-benzo­thio­phene derivatives, with (II) having a chlorine substituent on the oxo­indole unit. As a result, the conformation of the two mol­ecules differs in the angle of inclination of the indole moiety with respect to the benzo­thio­phene ring system, with a dihedral angle of 71.59 (5) in (I) and 82.27 (7)° in (II).

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In the title indole derivative, C22H21NO4, the dihedral angle between the benzene and pyrrole rings of indole moiety is 1.8 (1)°. The plane of the 4-meth­oxy­phenyl ring is oriented with a dihedral angle of 60.7 (1)° with respect to the plane of the indole moiety. The mol­ecular packing is stabilized by C—H...O hydrogen bonds which form a V-shaped chain arrangement along the bc plane of the unit cell. In addition to this, C—H...π and π–π inter­actions [centroid–centroid distances = 3.8102 (11) and 3.8803(12) Å], which run along the b-axis direction, stabilize the mol­ecular packing.
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