Crystal structure of (R)-N-benzyl-1-phenylethanaminium (R)-4-chloromandelate

Abstract

The absolute configuration of the title molecular salt, C15H18N+·C8H6ClO3−, has been confirmed by resonant scattering. In the (R)-N-benzyl-1-phenyl-ethylammonium cation, the phenyl rings are inclined to one another by 44.65 (7)°. In the crystal, the (R)-4-chloromandelate anions are linked via O—H...O hydrogen bonds and bridged by N—H...O hydrogen bonds involving the cations, forming chains along [010]. There are C—H...O hydrogen bonds present within the chains, which are linked via C—H...π interactions and a short Cl...Cl interaction [3.193 (1) Å] forming a three-dimensional framework. The structure was refined as a two-component inversion twin giving a Flack parameter of 0.05 (4).

Keywords

• Crystal structure
• 4-chloromandelate
• diastereomeric salt
• resolution
• absolute structure
• resonant scattering
• hydrogen bonding
• C—H...π interactions
• Cl...Cl interaction