Crystal and molecular structures of two antiarrythmic alpha-[(diarylmethoxy)methyl]-1-piperidineethanols

The crystal structures of two antiarrythmic piperidineethanols, alpha-{[(2- methylphenyl)phenyl methoxy]methyl}-2,6-dimethyl-1-piperidineethanol (1) an d alpha-[(bis(2,6-dimethylphenyl)methoxy)methyl]-2,6-dimethyl-1-piperidinee thanol (2) have been determined by X-ray structure analysis of single cryst als. The piperidine rings are close to ideal chair conformations, the methy l substituents are in equatorial positions. Overall shapes of the molecules differ significantly: in compound I the oxygen atoms are in anti position, while in 2 their mutual disposition is gauche. Dihedral angles between the phenyl rings and C-O-C plane are close to 90 degrees for the mono- or di-s ubstituted phenyl rings, while for the unsubstituted phenyl ring in I this value is smaller, equals 27.8(3)degrees. The bond angles in phenyl rings ar e influenced by the presence of methyl substituents. In both crystal struct ures the molecules make centrosymmetric dimers connected by strong O-(HN)-N -... hydrogen bonds (piperidine nitrogen atoms act as acceptors).