In the title compound, C24H25N3O5, the eth­oxy group is disordered over two orientations in a 0.853 (14):0.147 (14) ratio. The benzimadazole ring system (r.m.s. deviation = 0.016 Å) makes a dihedral angle of 35.47 (7)° with the attached benzene ring. The pyrrolidine ring adopts an envelope conformation with a methyl­ene C atom as the flap. In the crystal, inversion dimers linked by pairs of O—H⋯N hydrogen bonds generate R 2 2(16) loops. C—H⋯O inter­actions link the dimers into a three-dimensional network.

In the title compound, C26H18N2O3, the maximum deviations from planarity for the tetra­hydro-1H-naphtho­[2,3-c]pyrrole and indoline rings systems are 0.091 (1) and 0.012 (2) Å, respectively. These ring systems make a dihedral angle of 89.95 (6)° with each other and they make dihedral angles of 73.42 (8) and 71.28 (9)°, respectively, with the benzene ring. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops and C—H⋯O inter­actions connect the dimers into corrugated sheets lying parallel to the bc plane.

In the title compound, C23H20N2O3·CH3OH, the hexa­hydro-1H-benzo[f]isoindole and indoline rings are planar, with maximum deviations of 0.092 (1) and −0.095 (1) Å, respectively. The dihedral angle between these two rings is 88.03 (4)°. An O—H⋯N inter­action links the main mol­ecule and the methanol solvent mol­ecule. An intra­molecular C—H⋯O inter­action forms an S(6) ring motif. In the crystal, the mol­ecules form two-dimensional layers parallel to the bc plane through N—H⋯O and C—H⋯O inter­actions.

In the title compound, C15H14N2O4, the dihedral angle between the benzene rings is 40.59 (4)° and an intra­molecular O—H⋯N hydrogen bond generates an S(6) ring. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O inter­actions link the mol­ecules into a three-dimensional network.

In the title mol­ecular salt, C18H24N4 2+·2PF6 −, the complete dication is generated by a crystallographic inversion centre. The central benzene ring makes a dihedral angle of 77.19 (9)° with each of the imidazole rings. In the crystal, C—H⋯F inter­actions link the cations and anions into layers lying parallel to the bc plane. The hexa­fluoro­phosphate anion is disordered over two sets of sites in a 0.520 (11):0.480 (11) ratio.

In the title compound, [PdBr(C27H23N3OPS)]·C3H6O, the coordination geometry about the PdII atom is distorted square-planar, arising from the attached Br, S, P and N atoms (N and Br are trans), the maximum deviation from the plane being 0.2053 (4) Å for the N atom. The three benzene rings attached to the P atom make dihedral angles of 69.78 (7), 87.05 (7) and 77.50 (7)° with each other. An intra­molecular C—H⋯N hydrogen bond forms an S(6) ring motif. In the crystal, the complex mol­ecules form infinite chains along the a-axis direction through C—H⋯Br inter­actions, and a C—H⋯O inter­action links the main mol­ecule with the acetone solvent mol­ecule.

In the title compound, C20H28N4 2+·2PF6 −, the dihedral angles between the benzene ring and the imidazole rings are 70.18 (11) and 69.83 (11)°, while the imidazole rings form a dihedral angle of 40.52 (12)°. In the crystal, weak C—H⋯F inter­actions link the mol­ecules into a two-dimensional network parallel to (001). A π–π inter­action with a centroid–centroid distance of 3.601 (1) Å is also observed in the crystal structure.

In the title compound, C14H11N3O3, the chromene ring is almost planar, with a maximum deviation of 0.065 (2) Å from the mean plane for one of the C atoms. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate R 2 2(8) loops. The dimers are linked by C—H⋯N and C—H⋯O inter­actions into a three-dimensional network. An aromatic π–π stacking inter­action, with a centroid–centroid distance of 3.562 (10) Å, is also observed.

In the title compound, C15H14N2O3, the dihedral angle between the benzene rings is 66.56 (5)°. In the crystal, N—H⋯O, O—H⋯O and C—H⋯O inter­actions link the mol­ecules into a three-dimensional network. A π–π inter­action, with a centroid–centroid distance of 3.628 (6) Å, helps to establish the packing.

In the title compound, C32H36N4 2+·2PF6 −, the cation and the anions each have crystallographic twofold rotation symmetry. The benzimidazole ring is almost planar [r.m.s. deviation = 0.0161 (1) Å] and makes a dihedral angle of 5.77 (4)° with its symmetry-related component and a dihedral angle of 80.96 (5)° with the central benzene ring. The cyclo­pentyl ring adopts a half-chair conformation. In the crystal, mol­ecules are linked into a three-dimensional network through C—H⋯F hydrogen bonds. A C—H⋯π inter­action is also observed.

In the title compound, C26H28N4 2+·2PF6 −, the complete cation is generated by a crystallographic twofold axis. The benz­imidazole ring is almost planar (r.m.s. deviation = 0.0207 Å) and makes dihedral angles of 50.12 (2)° with its symmetry-related component and 65.81 (2)° with the central benzene ring. In the crystal, mol­ecules are linked into a three-dimensional network by C—H⋯F inter­actions. A π–π inter­action with a centroid–centroid distance of 3.530 (1) Å is observed. Four F atoms of the hexa­fluoro­phosphate anion are disordered over two sets of sites in a 0.889 (6):0.111 (6) ratio.

In the title compound, C19H21N2O2 +·C2H3O2 −, the 1H-indole ring system is essentially planar [maximum deviation = 0.0257 (14) Å] and forms a dihedral angle of 87.92 (7) Å with the benzene ring attached to the tetra­hydro­pyridinium fragment. The tetra­hydro­pyridinium ring adopts a half-chair conformation. In the crystal, cations and anions are linked by inter­ionic N—H⋯O, C—H⋯O and C—H⋯N hydrogen bonds into chains along the a axis.

In the title compound, [Pd(C21H24N2O4)], the complete mol­ecule is generated by crystallographic mirror symmetry with the Pd and three C atoms lying on the mirror plane. The Pd—O and Pd—N distances are 1.9932 (6) and 2.0029 (7) Å, respectively. The dihedral angle between two benzene rings of the ligand is 79.21 (4)°. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into layers parallel to the ab plane. These planes are further connected by C—H⋯O inter­actions, forming a three-dimensional network.

The asymmetric unit of the title compound, (C13H17N2O)2[ZnCl4]·2H2O, contains two tetra­hydro­harmine cations, one tetra­chloro­zincate(II) anion and two water mol­ecules. In the cations, the two 1H-indole ring systems are essentially planar, with maximum deviations of 0.016 (2) and 0.018 (2) Å, and both tetra­hydro­pyridinium rings show a half-chair conformation. The ZnII complex anion has a distorted tetra­hedral geometry. In the crystal, inter­molecular N—H⋯O, N—H⋯Cl, O—H⋯O, O—H⋯Cl and C—H⋯O hydrogen bonds link the components into a three-dimensional network. A π–π inter­action with a centroid–centroid distance of 3.542 (14) Å is also observed.

In the title compound, C18H13F2NO5S2, the complete mol­ecule is generated by a crystallographic inversion centre, and the O atom and the N—H group attached to the central ring are statistically disordered. The dihedral angle between the central and terminal benzene rings is 64.03 (6)°. In the crystal, N—H⋯O, C—H⋯F and C—H⋯O inter­actions link the mol­ecules into a three-dimensional network.

The complete mol­ecule of the title compound, C20H19NO5S2, is generated by a crystallographic twofold axis and the O atom and N—H group attached to the central benzene ring are statistically disordered. The dihedral angle between the central and terminal benzene rings is 56.91 (5)° and that between the terminal benzene rings is 29.80 (5)°. In the crystal, N—H⋯O hydrogen bonding links the mol­ecules into sheets lying parallel to the ab plane.

In the title compound, [Cr(C18H12F3P)2(CO)4], the Cr atom is octa­hedrally coordinated by four carbonyl ligands and the two tertiary phosphanes, which are trans to each other. The three benzene rings in one phosphane ligand make dihedral angles of 53.50 (9), 75.51 (10) and 80.63 (10)° with each other, while in the other ligand these angles are 51.92 (10), 78.56 (11) and 86.80 (10)°. C—H⋯O and C—H⋯F inter­actions link the mol­ecules into a three-dimensional network. Each of the F atoms is disordered over two positions with refined occupancies of 0.944 (3):0.056 (3), 0.702 (4):0.298 (4), 0.829 (4):0.171 (4), 0.567 (4):0.433 (4), 0.545 (4):0.455 (4) and 0.920 (4):0.080 (4).

In the title compound, C38H30N2O2, the acenaphthyl­ene ring is close to being planar [maximum deviation = 0.1047 (11) Å]. The dihedral angles between the three benzene rings and the acenaphthyl­ene system are 39.47 (3), 37.65 (3) and 44.47 (3)°. An intra­molecular O—H⋯N inter­action forms an S(5) hydrogen-bond ring motif. In the crystal, mol­ecules are linked into [101] chains by a set of C—H⋯O inter­actions.

In the title compound, [Cr(C26H24As2)(CO)4], the Cr atom is octa­hedrally coordinated by four carbonyl ligands and one bidentate 1,2-bis­(diphenyl­arsan­yl)ethane ligand, which chelates in a cis manner with an As—Cr—As bite angle of 82.513 (9)°. The dihedral angles between the pairs of benzene rings attached to each As atom are 84.63 (9) and 77.15 (8)°. In the crystal, mol­ecules are linked by C—H⋯O inter­actions, forming infinite chains along the a axis. The crystal structure is further stabilized by C—H⋯π inter­actions.

In the title compound, [Cr(C18H12F3P)2(CO)4], the Cr atom is octa­hedrally coordinated by four carbonyl ligands and the two tertiary phosphanes that are trans to each other. The Cr atom and two carbonyl groups are on a twofold axis. The benzene rings attached to the phospho­rus atom make dihedral angles of 80.32 (5), 52.91 (5) and 83.80 (5)° with each other. In the crystal, C—H⋯O and C—H⋯F inter­molecular inter­actions form an infinite three-dimensional network.

In the title compound, C19H18, the anthracene system is almost planar, with a maximum deviation of −0.039 (1) Å. The structure is stabilized by C—H⋯π inter­actions. The pentene moiety is not planar and is twisted away from the attached anthracene system with a maximum torsion angle of 91.2 (1)°.

In the title compound, C17H11F3O2, the dihydro­indene ring is approximately planar with a maximum deviation of 0.024 (2) Å and makes a dihedral angle of 3.17 (8) Å with the adjacent benzene ring. In the crystal, mol­ecules are inter­connected by C—H⋯O inter­actions, forming an infinite chain along the c axis.

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).

The asymmetric unit of the title compound, C21H26O4S, consists of two independent mol­ecules. In both mol­ecules, intra­molecular O—H⋯O hydrogen bonds stabilize the mol­ecular structure. In the crystal, each mol­ecule and its symmetry-related mol­ecule by twofold rotation form a dimer through a pair of inter­molecular C—H⋯O hydrogen bonds. In one of the mol­ecules, the thio­phene group is disordered over two sets of sites with occupancies of 0.735 (3) and 0.265 (3).

The asymmetric unit of the title compound, C26H32N4O4, consists of two independent mol­ecules. In both mol­ecules, the eth­oxy groups are each disordered over two sets of sites with occupancies of 0.695 (4):0.305 (4) and 0.877 (2):0.123 (2). The dihedral angles between the benzimidazole ring system and the adjacent benzene ring in the two mol­ecules are 41.41 (5) and 31.46 (5)°. In the crystal, mol­ecules are linked by C—H⋯O and C—H⋯N inter­actions.