Crystal structure and Hirshfeld surface analysis of 4-bromo-2-[3-methyl-5-(2,4,6-trimethylbenzyl)oxazolidin-2-yl]phenol

Abstract

The title compound, C20H24BrNO2, is chiral at the carbon atoms on either side of the oxygen atom of the oxazolidine ring and crystallizes as a racemate. The 1,3-oxazolidine ring adopts an envelope conformation with the N atom in an endo position. The mean plane of the oxazolidine ring makes dihedral angles of 77.74 (10) and 45.50 (11)°, respectively, with the 4-bromophenol and 1,3,5-trimethylbenzene rings. In the crystal, adjacent molecules are connected via C—H...O hydrogen bonds and C—H...π interactions into layers parallel to the (200) plane. The packing is strengthened by van der Waals interactions between parallel molecular layers. A Hirshfeld surface analysis shows that H...H (58.2%), C...H/H...C (18.9%), and Br...H/H...Br (11.5%) interactions are the most abundant in the crystal packing.