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

Yangfeng Peng; Sohrab Rohani; Paul D Boyle; Quan He

doi:10.1107/S1600536814023204

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

Acta Crystallogr Sect E Struct Rep Online. 2014 Nov 5;70(Pt 12):o1223-4. doi: 10.1107/S1600536814023204. eCollection 2014 Dec 1.

Authors

Yangfeng Peng¹, Sohrab Rohani², Paul D Boyle², Quan He³

Affiliations

¹ School of Chemical Engineering, East China University of Science and Technology, Shanghai, 200237, People's Republic of China.
² Department of Chemical and Biochemical Engineering, Western University, London, Ontario, N6A 5B9, Canada.
³ Department of Engineering, Faculty of Agriculture, Dalhousie University, Truro, NovaScotia, B2N 5E3, Canada.

Abstract

The absolute configuration of the title mol-ecular salt, C15H18N(+)·C8H6ClO3 (-), has been confirmed by resonant scattering. In the (R)-N-benzyl-1-phenyl-ethyl-ammonium cation, the phenyl rings are inclined to one another by 44.65 (7)°. In the crystal, the (R)-4-chloro-mandelate 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 inter-actions and a short Cl⋯Cl inter-action [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: 4-chloromandelate; Cl⋯Cl interaction; Crystal structure; C—H⋯π interactions; absolute structure; diastereomeric salt; hydrogen bonding; resolution; resonant scattering.