(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.
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.
Schneider
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M
Institute of Organic Chemistry, University of Zurich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland.
Linden
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Rippert
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D001381:Azepines / Q000737:chemistry*; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D008968:Molecular Conformation; D009281:Naphthalenes / Q000737:chemistry*; D013237:Stereoisomerism
C413874:8-(2-hydroxy-1-methyl-2-phenylethyl)-8-methyl-8,9-dihydro-7H-dinaphth(2,1-c-1',2'-e)azepinium; D001381:Azepines; D009281:Naphthalenes