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In the title compound, C20H22N2O2, the central pyridine ring forms a dihedral angle of 76.32 (8)° with the pseudo-axial benzene ring. The cyclo­octane ring adopts a twisted boat chair conformation. In the crystal, weak inter­molecular C—H...π inter­actions between inversion-related mol­ecules result in the formation of linear double chains along the b-axis direction.

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In the title compound, C19H19FN2O, the cyclo­octene ring adopts a twisted boat-chair conformation. The dihedral angle between the plane of the fluorophenyl substituent and that of the pyridine ring is 76.39 (8)°. The F and ortho-H atoms of the fluoro­benzene ring are disordered, with occupancy factors of 0.226 (5) and 0.774 (5). In the crystal, no significant inter­actions are observed between the mol­ecules beyond van der Waals contacts.

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In the title compound, C24H14BrN3S, the dihedral angles between the planes of the pyridine ring and the pendant thio­phene ring, the indole ring system (r.m.s. deviation = 0.022 Å) and the bromo­benzene ring are 9.37 (17), 21.90 (12) and 69.01 (15)°, respectively. The approximate coplanarity of the central ring and the indole ring system is supported by two intra­molecular C—H...N inter­actions. In the crystal, inversion dimers linked by pairs of N—H...N hydrogen bonds generate R22(16) loops and the dimers are linked by C—H...π and aromatic π–π stacking [shortest centroid–centroid separation = 3.729 (3) Å] into a three-dimensional network.

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In the title compound, C26H16ClN3, the dihedral angles between the central pyridine ring and the pendant phenyl, chloro­benzene and indole rings are 18.52 (12), 48.97 (11) and 21.20 (10)°, respectively. An intra­molecular C—H...Nc (c = cyanide) hydrogen bond occurs. In the crystal, inversion dimers linked by pairs of N—H...Nc hydrogen bonds generate R22(16) loops.

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In the title compound, C27H19N3O, the dihedral angles between the plane of the pyridine ring and those of the indole (r.m.s. deviation = 0.018 Å), phenyl and meth­oxy­benzene substituents are 33.60 (6), 25.28 (7) and 49.31 (7)°, respectively. The N atom of the carbo­nitrile group is significantly displaced [0.288 (2) Å] from the plane of the pyridine ring, perhaps due to steric crowding. In the crystal, inversion dimers linked by pairs of N—H...Nn (n = nitrile) hydrogen bonds generate R22(16) loops. Aromatic π–π stacking [centroid–centroid separation = 3.6906 (7) Å] and very weak C—H...π inter­actions are also observed".
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