In the crystal structure of the title compound, a di­spiro­[indoline-3,2′-pyrrolidine-3′,6′′-iso­quinoline]-2,5′′-dione, C—H⋯O hydrogen bonding predominates, linking mol­ecules to form chains propagating along [100].

The title compounds, C32H35NO2, (I), and C30H29Br2NO2, (II), differ by the presence of a bromine atom instead of a methyl atom in the para position of two benzene rings of compound (II). The two compounds have a structural overlap r.m.s. deviation of 0.27 Å. The pyran and seven-membered cycloheptene rings in both structures adopt boat and boat-sofa conformations, respectively. Intra- and intermolecular C—H...O hydrogen bonds are responsible for the consolidation of the crystal packing of both molecules. In addition to this, weak C—H...π interactions are also observed. The intermolecular interactions were quantified and analysed using Hirshfeld surface analysis.

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In the title compound, C21H18N2O, the non-aromatic six-membered ring adopts a distorted envelope conformation with one of the methylene-C atoms being the flap atom. The dihedral angle between the phenyl and 4-tolyl rings is 75.3 (1)°. The 1,2-diazole ring forms dihedral angles of 41.9 (1) and 65.5 (1)° with the phenyl and 4-tolyl rings, respectively. In the crystal, stabilizing C—H...O, C—H...π and π–π interactions are evident. The calculated Hirshfeld surfaces highlight the prominent role of C—H...O interactions (8.6%), along with H...H (51.7%) and C...H/H...C (29.2%) surface contacts.

In the title compound, C20H15ClN2O, the non-aromatic six-membered ring adopts a distorted envelope conformation with methylene-C atom nearest to the five-membered ring being the flap atom. The dihedral angle between the phenyl and chlorobenzene rings is 74.5 (1)°. The heterocyclic ring forms dihedral angles of 37.9 (1) and 64.3 (1)° with the phenyl and chlorobenzene rings, respectively. In the crystal, weak C—H...O interactions feature predominantly within the three-dimensional architecture. The intermolecular interactions are further analysed with the calculation of the Hirshfeld surfaces highlighting the prominent role of C—H...O interactions, along with H...H (36.8%) and C...H/H...C (26.5%) contacts.