The asymmetric unit of the title compound, C27H32N4O4·H2O, contains two independent benzimidazole-5-carboxyl­ate mol­ecules and two water mol­ecules. In both main mol­ecules, the pyrrolidine rings are in an envelope conformation with a methyl­ene C atom as the flap. The morpholine rings adopt chair conformations. Both benzimidazole rings are essentially planar, with maximum deviations of 0.008 (1) Å, and form dihedral angles of 37.65 (6) and 45.44 (6)° with the benzene rings. In one mol­ecule, an intra­molecular C—H⋯O hydrogen bond forms an S(7) ring motif. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds connect pairs of main mol­ecules and pairs of water mol­ecules into two independent centrosymmetric four-compoment aggregates. These aggregates are connect by C—H⋯O hydrogen bonds leading to the formation of a three-dimensional network, which is stabilized by C—H⋯π interactions.

In the title compound, C27H20BrNO3, two intra­molecular C—H⋯O hydrogen bonds both form S(6) rings. The pyrrolidine ring adopts a twisted conformation about the C—C bond bearing the indane ring systems. The other two five-membered rings within the indane systems are in shallow envelope conformations, with the spiro C atoms as the flap atoms. The mean plane of the pyrrolidine ring [maximum deviation = 0.275 (1) Å] makes dihedral angles of 65.25 (7), 78.33 (6) and 75.25 (6)° with the bromo-substituted benzene ring and the mean planes of the mono- and dioxo-substituted indane rings, respectively. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into a three-dimensional network. In addition, C—H⋯π inter­actions are observed.

In the title compound, C23H17F3N2O3, an intra­molecular C—H⋯F hydrogen bond generates an S(6) ring motif. The essentially planar 1H-benzimidazole ring system [maximum deviation = 0.021 (2) Å] forms dihedral angles of 25.00 (10) and 62.53 (11)° with the trifluoro­meth­oxy-substituted benzene and phenyl rings, respectively. The twist of the ethyl acetate group from the least-squares plane of the 1H-benzimidazole ring system is defined by a C(=O)—O—C—C torsion angle of 79.5 (3)°. In the crystal, mol­ecules are linked into a two-dimensional network parallel to the bc plane by weak C—H⋯N and C—H⋯O hydrogen bonds. Weak C—H⋯π inter­actions also observed.

In the title compound, C22H17ClN2O2, the essentially planar benzimidazole ring system [maximum deviation = 0.012 (2) Å] forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23 (8)°. In the crystal, mol­ecules are linked into a zigzag chain along the a axis by inter­molecular C—H⋯O hydrogen bonds. C—H⋯π inter­actions are also present.

The asymmetric unit of the title compound, C23H17F3N2O2, contains two mol­ecules. In one of the mol­ecules, the phenyl and triflouromethyl-substituted benzene rings form dihedral angles of 52.05 (8) and 33.70 (8)°, respectively, with the benzimidazole ring system, while the dihedral angle between them is 58.24 (10)°. The corresponding values in the other mol­ecule are 58.40 (8), 25.90 (8) and 60.83 (10)°, respectively. In the crystal, mol­ecules are linked into chains along [100] by C—H⋯O and C—H⋯N hydrogen bonds. Aromatic π–π stacking inter­actions [centroid–centroid distance = 3.6700 (12) Å] also occur.

In the title compound, C22H17BrN2O2, the benzimidazole ring system is essentially planar, with a maximum deviation of 0.017 (1) Å, and forms dihedral angles of 27.79 (6) and 64.43 (6)° with the phenyl and bromo-substituted benzene rings, respectively. In the crystal, mol­ecules are linked into one-dimensional chains along the a axis by weak C—H⋯O hydrogen bonds. Weak inter­molecular C—H⋯π inter­actions are also present.

In the title compound, C30H22BrNO2, the cyclo­pentane ring of the dihydro­acenaphthyl­ene group and the pyrrolidine ring are both in envelope conformations with the spiro C atom and N atom, respectively, as the flap atom. The cyclo­pentane ring of the indane group adopts a half-chair conformation. A weak intra­molecular C—H⋯O hydrogen bond forms an S(8) ring motif. The naphthalene ring system of the dihydro­acenaphthyl­ene group forms dihedral angles of 41.76 (6) and 42.17 (6)° with the benzene ring of the bromo­phenyl group and the benzene ring of the indane group, respectively. The dihedral angle between the two benzene rings is 83.92 (7)°. In the crystal, mol­ecules are linked by weak C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. Weak C—H⋯π inter­actions are also observed.

In the title compound, C31H22F3NO2, the pyrrolidine and cyclo­pentane rings within the dihydro­indene ring system are in envelope conformations, with the N atom and the spiro-C atom at the flap, respectively. An intra­molecular C—H⋯O hydrogen bond forms an S(8) ring motif. The mean plane through the pyrrolidine ring [r.m.s. deviation = 0.179 (2) Å] makes dihedral angles of 86.30 (13), 88.99 (10) and 79.69 (11)° with the benzene ring, the dihydro­acenaphthyl­ene ring and the mean plane of the indane system, respectively. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N hydrogen bonds into a two-dimensional network parallel to the ac plane. C—H⋯π inter­actions further stabilize the crystal structure.

In the title compound, C31H23NO2S, the pyrrolidine ring adopts an envelope conformation (with the spiro C atom as the flap), while the thia­zolidine ring and the two cyclo­pentane rings adopt twisted conformations. The mean plane through the hexa­hydro­pyrrolo­[1,2-c]thia­zole ring [r.m.s deviation = 0.400 (1) Å] forms dihedral angles of 76.83 (4), 80.70 (5) and 79.00 (4)° with the benzene ring and the mean planes of the dihydro­acenaphthyl­ene and the dihydro­indene rings, respectively. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into sheets lying parallel to the bc plane. One of the ketone O atoms accepts three such bonds. Weak C—H⋯π inter­actions are also observed.

In the title compound, C30H25NO5S, all the five-membered rings are in envelope conformations with the spiro and methylene C atoms as the flap atoms. Intra­molecular C—H⋯O inter­actions stabilize the mol­ecular structure and form S(6) and S(7) ring motifs. The mean plane through the hexa­hydro­pyrrolo­[1,2-c]thia­zole ring [r.m.s deviation of 0.0393 (1) Å] makes dihedral angles of 60.92 (5), 88.33 (4) and 84.12 (4)° with the terminal benzene ring and the mean planes of the mono and di-oxo substituted indan rings, respectively. Mol­ecules are linked by inter­molecular C—H⋯O inter­actions into a three-dimensional network. In addition, C—H⋯π and π–π inter­actions [centroid-to-centroid distance = 3.4084 (8) Å] further stabilize the crystal structure.

In the title mol­ecule, C17H11F3O, the indan ring system and the trifluoro­methyl-substituted benzene ring are approximately individually planar and form a dihedral angle of 1.81 (5)° with each other. In the crystal, mol­ecules are linked by pairs of weak bifurcated (C—H)2⋯O hydrogen bonds to form centrosymmetric dimers, generating R 2 1(6) and R 2 2(10) ring motifs. These dimers are connected by further weak C—H⋯O hydrogen bonds into one-dimensional chains along the b axis. Weak C—H⋯π inter­actions are also present.

In the title compound, C23H25N3O3, the benzimidazole ring system is essentially planar [maximum deviation = 0.0240 (18) Å]. The mean plane through this ring system forms a dihedral angle of 42.23 (7)° with the benzene ring. The pyrrolidine ring is in an envelope conformation with the flap atom disordered over two sites with occupancies of 0.813 (11) and 0.187 (11). In the crystal, weak C—H⋯O hydrogen bonds form R 2 2(10) ring motifs, which are connected by further C—H⋯O inter­actions, forming ribbons along the b axis. The crystal structure is further stabilized by weak π–π inter­actions involving the imidazole and benzene rings of the benzimidazole ring system [centroid–centroid distances = 3.6788 (11) and 3.6316 (10) Å] and weak C—H⋯π inter­actions.

The asymmetric unit of the title compound, C24H27N3O4, contains two mol­ecules, A and B. The benzimidazole rings are essentially planar [maximum deviations = 0.0144 (10) and 0.0311 (8) Å in A and B, respectively]. The dihedral angle between the benzimidazole mean plane and its attached benzene ring is 36.90 (5) ° for mol­ecule A and 51.40 (5) ° for mol­ecule B. In both mol­ecules, the pyrrolidine ring adopts an envelope conformation with a C atom as the flap. In molecule B, the flap C atom is disordered over two positions in a 0.711 (6):0.289 (6) ratio. In the crystal, C—H⋯O inter­actions link the mol­ecules, generating [100] chains. The crystal packing also features weak π–π inter­actions between the imidazole and benzene rings [centroid–centroid distances = 3.8007 (7) and 3.8086 (7) Å] and between the benzene rings [centroid–centroid distance = 3.7001 (7) Å] and C—H⋯π inter­actions involving the benzene rings.

In the title compound, C23H22N4O4, the essentially planar [maximum deviation = 0.022 (1) Å] benzimidazole ring system forms dihedral angles of 86.16 (7) and 37.38 (6)°, respectively, with the imidazole and benzene rings. The dioxolane ring adopts an envelope conformation with the methyl­ene C atom at the flap. In the crystal, C—H⋯O and C—H⋯N inter­actions link the mol­ecules into a ribbon along the a axis. The crystal packing is further stabilized by weak π–π stacking inter­actions [centroid–centroid distances = 3.5954 (8) and 3.7134 (8) Å] and C—H⋯π inter­actions.

In the title compound, C23H24N4O5, the essentially planar benzimidazole ring system [maximum deviation = 0.008 (2) Å] forms a dihedral angle of 39.22 (7)° with the attached nitro­benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with a C atom as the flap. In the crystal, mol­ecules are connected by C—H⋯O inter­actions, forming sheets propagating in (011). The crystal packing also features weak π–π stacking inter­actions [centroid–centroid = 3.6746 (12) Å].

In the title compound, C24H27N3O5·H2O, the essentially planar benzimidazole ring system [maximum deviation = 0.020 (1) Å] forms dihedral angles of 54.10 (11) and 67.79 (6)°, respectively, with the mean plane of pyrrolidin-2-one ring and the benzene ring. The pyrrolidin-2-one ring adopts an envelope conformation with one of the methylene C atoms at the flap. An intra­molecular C—H⋯π inter­action is observed. In the crystal, O—H⋯O and O—H⋯N hydrogen bonds link the two components into a double-tape structure along the a axis. The crystal packing is further stabilized by weak π–π stacking [centroid–centroid distance = 3.6632 (9) Å] and C—H⋯O inter­actions.

The asymmetric unit of the title compound, C28H21NO3S, contains two mol­ecules with similar geometries. The thia­zolidine rings adopt half-chair conformations while the pyrrolidine and the diketo-substituted five-membered carbocyclic rings are in envelope conformations with the spiro C atoms at the flaps. In one mol­ecule, the phenyl ring forms dihedral angles of 57.76 (12) and 71.79 (12)° with the fused benzene rings and the fused benzene rings form a dihedral angle of 57.75 (13)°. The corresponding dihedral angles in the other mol­ecule are 60.04 (12), 72.93 (12) and 54.51 (13)°. The mol­ecular structure is stabilized by intra­molecular C—H⋯O hydrogen bonds, which generate S(6) ring motifs. In the crystal, mol­ecules are linked via C—H⋯O and C—H⋯N hydrogen bonds into layers lying parallel to the ab plane.

In the title compound, C22H21BrN4O2·H2O, the two pyrazole rings are essentially planar [maximum deviations 0.002 (1) and 0.002 (1) Å], and form a dihedral angle of 73.46 (9)°. The dihedral angle between the benzene rings is 29.33 (7)°. In the crystal, mol­ecules are connected via C—H⋯O and O—H⋯N hydrogen bonds, forming layers in the ab plane.

In the title compound, C28H20F3NO3, the pyrrolidine ring adopts a half-chair conformation. The other five-membered rings adopt envelope conformations with the spiro and methylene C atoms as the flap atoms. In the crystal, mol­ecules are connected via weak C—H⋯O hydrogen bonds, forming sheets parallel to the bc plane.

In the title compound, C15H18N4O4, the 1H-imidazole ring forms a dihedral angle of 67.12 (8)° with the benzene ring. An S(6) ring motif is formed via an intra­molecular N—H⋯O hydrogen bond. In the crystal, neighbouring mol­ecules are linked by a pair of inter­molecular N—H⋯N hydrogen bonds, forming an inversion dimer. The dimers are further linked by a pair of C—H⋯O hydrogen bonds, leading to the formation of chain along [021]. A C—H⋯π inter­action involving the centroid of the benzene ring is also observed between the chains.

In the title compound, C27H25NO, the piperidine ring adopts an envelope conformation with the N atom at the flap position. The two benzylidene-benzene rings are oriented at a dihedral angle of 8.5 (1)°. In the crystal, the mol­ecules are linked into centrosymmetric dimers by pairs of inter­molecular C—H⋯O hydrogen bonds. The dimers are connected via C—H⋯π inter­actions involving the phenyl rings.

The conformation of the title compound, C27H21NO3, is stabilized by a weak intra­molecular C—H⋯O hydrogen bond, which generates an S(6) ring motif. The pyrrolidine ring adopts a half-chair conformation. Both of the other five-membered rings are in envelope conformations. No significant inter­molecular hydrogen bonds are observed.

In the title compound, C16H11BrO, the dihydro­indene ring system is approximately planar, with a maximum deviation of 0.008 (2) Å. The mean plane of this ring system forms a dihedral angle of 3.73 (11)°, with the bromo-substituted benzene ring. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into sheets parallel to the ab plane and further stabilization is provided by weak C—H⋯π inter­actions involving the bromo-substituted benzene rings.

In the title compound, C16H11ClO, the dihedral angle between the almost planar dihydro­indene ring system (r.m.s. deviation = 0.009 Å) and the chloro­benzene ring is 3.51 (14)°. In the crystal, mol­ecules are connected by C—H⋯O and weak C—H⋯Cl inter­actions, forming infinite layers parallel to (101).

In the title compound, C18H17NO, the dihydro­indene ring system is approximately planar, with a maximum deviation of 0.041 (2) Å. This ring system is almost coplanar with the benzene ring, making a dihedral angle of 5.22 (9)°. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into chains along the b axis.