2000
DOI: 10.1107/s0108270100006739
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(M)- and (P)-8-[(1S,2R)-2-hydroxy-1-methyl-2-phenylethyl]-8-methyl-8,9-dihydro-7H-dinaphth[2,1-c:1′,2′-e]azepinium bromide solvates

Abstract: The title compounds are diastereoisomers with antipodean axial chirality. The M isomer crystallizes as a (1/3) acetone solvate, C(32)H(30)NO(+).Br(-).3C(3)H(6)O, while the P isomer crystallizes as a (1/1) dichloromethane solvate, C(32)H(30)NO(+).Br(-).CH(2)Cl(2). In each structure, O-H.Br hydrogen bonds link the cations and anions to give ion pairs. The seven-membered azepinium ring adopts the usual twisted-boat conformation and its ring strain causes a slight curvature of the plane of each naphthyl ring.

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“…fused with both naphthyl moieties, as reported for azepinium bromide structures [10] and dinaphthazepines P,N-ligands [11]. As commonly observed in structures containing diphenylphosphinate groups [12], P(1) is a slightly distorted tetrahedron: bond angles values indicate that electrostatic repulsion between the lone pair of O(2) and bond pairs enlarges the angles involving O(2) and narrows those at the tetrahedral basis.…”
mentioning
confidence: 78%
“…fused with both naphthyl moieties, as reported for azepinium bromide structures [10] and dinaphthazepines P,N-ligands [11]. As commonly observed in structures containing diphenylphosphinate groups [12], P(1) is a slightly distorted tetrahedron: bond angles values indicate that electrostatic repulsion between the lone pair of O(2) and bond pairs enlarges the angles involving O(2) and narrows those at the tetrahedral basis.…”
mentioning
confidence: 78%