Abstract
The title compound N-(4-meth-oxy-phen-yl)-2-[4-(3-oxo-3-phenyl-prop-1-en-1-yl)phen-oxy]acetamide, C24H21NO4, was prepared from reaction of N-(4-meth-oxy-phen-yl)-2-chloro-acetamide and (E)-3-(4-hy-droxy-phen-yl)-1-phenyl-prop-2-en-1-one, which was obtained from the reaction of 4-hy-droxy-benzaldehyde and aceto-phenone. 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 mol-ecules, each displaying an E-configuration of the C=C bond. The dihedral angle between the phenyl rings in each mol-ecule varies between 14.9 (2) and 45.8 (2)°. In the crystal, C-H⋯O hydrogen-bonding inter-actions link the mol-ecules into chains running along the [001] direction. In addition, C-H⋯π inter-actions 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%) inter-actions.
Highlights
Cong Nguyen Tien,a* Trung Vu Quoc,b Dat Nguyen Dang,b Giang Le Ducc and Luc Van Meerveltd*
The title compound N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1yl)phenoxy]acetamide, C24H21NO4, was prepared from reaction of N-(4methoxyphenyl)-2-chloroacetamide and (E)-3-(4-hydroxyphenyl)-1-phenylprop-2-en-1-one, which was obtained from the reaction of 4-hydroxybenzaldehyde and acetophenone
A Hirshfeld analysis indicates that the most important contributions to the surface contacts are from HÁ Á ÁH (43.6%), CÁ Á ÁH/HÁ Á ÁC (32.1%) and OÁ Á ÁH/HÁ Á ÁO (18.1%) interactions
Summary
Chalcones are important intermediates in the biosynthesis of flavonoids, but are valuable starting materials for the synthesis of biologically important heterocycles such as pyrazolines, isoxazolines, benzodiazepines and benzothiazepines (Zhuang et al, 2017; Ovonramwen et al, 2019). With the presence of the N—HÁ Á ÁO hydrogen bond, one would assume the central and the methoxy-substituted phenyl rings to be almost coplanar This is not the case, with dihedral angles between the least-squares planes through the two rings being 17.27 (19), 45.8 (2), 38.91 (19) and 14.9 (2) for molecules A–D, respectively. The terminal methyl group is oriented differently for molecule C
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