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In the title compound, C25H27NO4S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH3 groups on the azepine ring is trans. The seven-membered azepin ring has a chair-like conformation. The planar aromatic rings of the benzyl and tosylate moiety are inclined to the planar 3-benzazepine ring by 78.39 (15) and 77.03 (14)°, respectively, and to each another by 13.82 (15)°. In the crystal, molecules are linked via O—H...O and C—H...O hydrogen bonds, forming double-stranded chains along the a-axis direction. The chains are linked via C—H...π interactions, forming a three-dimensional architecture.

The title compounds, C22H29NO2 (3) and C22H29NO2 (4) [systematic names: (1S*,2R*)-7-methoxy-2-methyl-3-(4-phenylbutyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol and (1R*,2R*)-7-methoxy-2-methyl-3-(4-phenylbutyl)-2,3,4,5-tetrahydro-1H-3-benzazepin-1-ol, are diastereomers with the relative configuration of the adjacent hydroxyl and methyl groups at the seven-membered azepine ring being trans in (3) and cis in (4). In the crystals the orientation of these groups is −anti-periplanar (3) and +syn-clinal (4). In both cases, the crystals studied proved to be of a racemic mixture, with relative configurations (R*,S*)-3 and (R*,R*)-4. In both compounds, the seven-membered azepine ring has a chair-like conformation, and the 4-phenylbutyl side chain adopts a extended conformation in (R*,S*)-3, but a twisted conformation in (R*,R*)-4. In the crystal of (S*,R*)-3, molecules are linked via C—H...O hydrogen bonds, forming slabs parallel to the ac plane. In the crystal of (R*,R*)-4, molecules are linked via O—H...N hydrogen bonds, forming chains propagating along the c-axis direction. The chains are linked by C—H...O hydrogen bonds, forming slabs parallel to the ac plane.

The title compounds, C22H29NO2 (3) and C22H29NO2 (4) [systematic names: (1S*,2R*)-7-meth-oxy-2-methyl-3-(4-phenyl-but-yl)-2,3,4,5-tetra-hydro-1H-3-benzazepin-1-ol and (1R*,2R*)-7-meth-oxy-2-methyl-3-(4-phenyl-but-yl)-2,3,4,5-tetra-hydro-1H-3-benzazepin-1-ol, are diastereomers with the relative configuration of the adjacent hydroxyl and methyl groups at the seven-membered azepine ring being trans in (3) and cis in (4). In the crystals the orientation of these groups is -anti-periplanar (3) and +syn-clinal (4). In both cases, the crystals studied proved to be of a racemic mixture, with relative configurations (R*,S*)-3 and (R*,R*)-4. In both compounds, the seven-membered azepine ring has a chair-like conformation, and the 4-phenyl-butyl side chain adopts a extended conformation in (R*,S*)-3, but a twisted conformation in (R*,R*)-4. In the crystal of (S*,R*)-3, mol-ecules are linked via C-H⋯O hydrogen bonds, forming slabs parallel to the ac plane. In the crystal of (R*,R*)-4, mol-ecules are linked via O-H⋯N hydrogen bonds, forming chains propagating along the c-axis direction. The chains are linked by C-H⋯O hydrogen bonds, forming slabs parallel to the ac plane.

In the title compound, C25H27NO4S, which crystallized as a racemate, the relative configuration of the adjacent OH and CH3 groups on the azepine ring is trans. The seven-membered azepin ring has a chair-like conformation. The planar aromatic rings of the benzyl and tosyl-ate moiety are inclined to the planar 3-benzazepine ring by 78.39 (15) and 77.03 (14)°, respectively, and to each another by 13.82 (15)°. In the crystal, mol-ecules are linked via O-H⋯O and C-H⋯O hydrogen bonds, forming double-stranded chains along the a-axis direction. The chains are linked via C-H⋯π inter-actions, forming a three-dimensional architecture.