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Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide
The title compound N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide, C(24)H(21)NO(4), 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-hydroxybenza...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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International Union of Crystallography
2021
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7869538/ https://www.ncbi.nlm.nih.gov/pubmed/33614151 http://dx.doi.org/10.1107/S2056989021000864 |
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author | Nguyen Tien, Cong Vu Quoc, Trung Nguyen Dang, Dat Le Duc, Giang Van Meervelt, Luc |
author_facet | Nguyen Tien, Cong Vu Quoc, Trung Nguyen Dang, Dat Le Duc, Giang Van Meervelt, Luc |
author_sort | Nguyen Tien, Cong |
collection | PubMed |
description | The title compound N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide, C(24)H(21)NO(4), 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, (1)H-NMR, (13)C-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. |
format | Online Article Text |
id | pubmed-7869538 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-78695382021-02-19 Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide Nguyen Tien, Cong Vu Quoc, Trung Nguyen Dang, Dat Le Duc, Giang Van Meervelt, Luc Acta Crystallogr E Crystallogr Commun Research Communications The title compound N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide, C(24)H(21)NO(4), 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, (1)H-NMR, (13)C-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. International Union of Crystallography 2021-01-29 /pmc/articles/PMC7869538/ /pubmed/33614151 http://dx.doi.org/10.1107/S2056989021000864 Text en © Nguyen Tien et al. 2021 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Nguyen Tien, Cong Vu Quoc, Trung Nguyen Dang, Dat Le Duc, Giang Van Meervelt, Luc Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide |
title | Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide |
title_full | Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide |
title_fullStr | Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide |
title_full_unstemmed | Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide |
title_short | Synthesis and structure of (E)-N-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide |
title_sort | synthesis and structure of (e)-n-(4-methoxyphenyl)-2-[4-(3-oxo-3-phenylprop-1-en-1-yl)phenoxy]acetamide |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7869538/ https://www.ncbi.nlm.nih.gov/pubmed/33614151 http://dx.doi.org/10.1107/S2056989021000864 |
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