(2S,NS)-N-Allyl-N-benzyl-1-hydroxy-3-(4-hydroxyphenyl)-N-methylpropan-2-aminium bromide

Hua-Fang Wu,Xin-Fu Pan,Guo-Lin Zhang,Kai-Bei Yu,Ying-Gang Luo

doi:10.1107/s1600536808023210

Abstract

The title compound, C20H26NO2 +·Br−, is an N-chiral quaternary ammonium salt synthesized from (2S*)-N-benzyl-N-methyltyrosine methyl ester. The dihedral angle between the phenyl ring and the benzene ring is 11.61 (19)°. In the crystal structure, the allyl group is disordered over two positions with site occupancy factors of ca 0.8 and 0.2. The bromide anion links to the quaternary ammonium cations via O—H⋯Br hydrogen bonding. An intramolecular O—H⋯Br hydrogen bond is also observed.

Highlights

The title compound, C20H26NO2+Br, is an N-chiral quaternary ammonium salt synthesized from (2S*)-Nbenzyl-N-methyltyrosine methyl ester
The allyl group is disordered over two positions with site occupancy factors of ca 0.8 and 0.2
The title compound is a Nchiral quaternary ammonium salt (N-CQAS), we present here its structure

Summary

Data collection

Tmin = 0.406, Tmax = 0.433 a Department of Chemistry, State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000, People’s Republic of China, bChengdu. Republic of China, and cChengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, People’s Republic of China. Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.011 Å; disorder in main residue; R factor = 0.055; wR factor = 0.211; data-to-parameter ratio = 20.1. The title compound, C20H26NO2+Br, is an N-chiral quaternary ammonium salt synthesized from (2S*)-Nbenzyl-N-methyltyrosine methyl ester. The allyl group is disordered over two positions with site occupancy factors of ca 0.8 and 0.2. The bromide anion links to the quaternary ammonium cations via. An intramolecular O—H Br hydrogen bond is observed. Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL

Graphite monochromator ω scans

Special details