Crystal structure of 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate

• Main Authors: Imtiaz Khan, Aliya Ibrar, Shahid Hameed, Jonathan M. White, Jim Simpson
• Format: Article
• Language: English
• Published: International Union of Crystallography 2014-11-01
• Series: Acta Crystallographica Section E
• Subjects: crystal structure; 2-(4-chlorophenyl)-2-oxoethyl 3-bromobenzoate; synthesis; π–π interactions; inversion dimers
• Online Access: http://scripts.iucr.org/cgi-bin/paper?S1600536814021643

2-(4-Chlorophenyl)-2-oxoethyl 3-bromobenzoate, C15H10BrClO3, was synthesized in a single-step reaction by condensation of 3-bromobenzoic acid with 2-bromo-1-(4-chlorophenyl)ethanone in dimethylformamide in the presence of triethylamine as a catalyst. The structure consists of an aryl ketone moiety linked to an aryl ester unit by a methylene group. Both units are reasonably planar (r.m.s. deviations of 0.119 and 0.010 Å for the aryl ketone and aryl ester units, respectively) and are almost orthogonal, with an angle of 88.60 (3)° between them. In the crystal, molecules form five separate sets of inversion dimers. Three of these are generated by two C—H...O interactions and a C—H...Br contact, and form chains along c and along the ab cell diagonal. In addition, two inversion-related π–π stacking interactions between like aryl rings again form chains of molecules but in this instance along the bc diagonal. These contacts generate infinite layers of molecules parallel to (011) and stack the molecules along the a-axis direction.