Title of article :
Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide
Author/Authors :
Tien, Cong Nguyen Faculty of Chemistry - Ho Chi Minh City University of Education, Vietnam , Quoc, Trung Vu Faculty of Chemistry - Hanoi National University of Education, Vietnam , Dang, Dat Nguyen Faculty of Chemistry - Hanoi National University of Education, Vietnam , Duc, Giang Le School of Natural Sciences Education - Vinh University, Vietnam , Meervelt, Luc Van Department of Chemistry - KU Leuven - Biomolecular Architecture, Belgium
Abstract :
The title compound N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide, C24H21NO4, was prepared from reaction of N-(4-methoxyphenyl)-2-chloroacetamide and (E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one, which was obtained from the reaction of 4-hydroxybenzaldehyde and acetophenone. The structure of the title compound was determined by IR, 1H-NMR, 13C-NMR and HR–MS spectroscopic data and further characterized by single-crystal X-ray diffraction. The asymmetric unit contains four molecules, each displaying an E-configuration of the C=C bond. The dihedral angle between the phenyl rings in each molecule varies between 14.9 (2) and 45.8 (2)°. In the crystal, C—H⋯O hydrogen-bonding interactions link the molecules into chains running along the [001] direction. In addition, C—H⋯π interactions further stabilize the crystal packing. A Hirshfeld analysis indicates that the most important contributions to the surface contacts are from H⋯H (43.6%), C⋯H/H⋯C (32.1%) and O⋯H/H⋯O (18.1%) interactions.
Keywords :
crystal structure , chalcones , Hirshfeld analysis , C—H⋯π interactions , hydrogen bonding
Journal title :
Acta Crystallographica Section E: Crystallographic Communications