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Syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide

The first title benzoyl amide, C(17)H(20)ClNO(5) (3a), crystallizes in the monoclinic space group P2(1)/c with Z = 4 and the second, C(19)H(24)ClNO(5) (3b), also crystallizes in P2(1)/c with Z = 8 (Z′ = 2), thus there are two independent mol­ecules in the asymmetric unit. In 3a, the phenyl ring make...

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Autores principales: Anderson, Alan J., Butcher, Ray J., Ollie, Edward
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2021
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8061103/
https://www.ncbi.nlm.nih.gov/pubmed/33953958
http://dx.doi.org/10.1107/S2056989021001778
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author Anderson, Alan J.
Butcher, Ray J.
Ollie, Edward
author_facet Anderson, Alan J.
Butcher, Ray J.
Ollie, Edward
author_sort Anderson, Alan J.
collection PubMed
description The first title benzoyl amide, C(17)H(20)ClNO(5) (3a), crystallizes in the monoclinic space group P2(1)/c with Z = 4 and the second, C(19)H(24)ClNO(5) (3b), also crystallizes in P2(1)/c with Z = 8 (Z′ = 2), thus there are two independent mol­ecules in the asymmetric unit. In 3a, the phenyl ring makes a dihedral angle of 50.8 (3)° with the amide moiety with the C=O group on the same side of the mol­ecule as the C—Cl group. One meth­oxy group is almost in the plane of the benzene ring, while the eth­oxy and other meth­oxy substituent are arranged on opposite sides of the ring with the eth­oxy group occupying the same side of the ring as the C=O group in the amide moiety. For one of the two mol­ecules in 3b, both the amide and 5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl moieties are disordered over two sets of sites with occupancies of 0.551 (2)/0.449 (2) with the major difference between the two conformers being due to the conformation adopted by the cyclo­hex-2-en-1-one ring. The three mol­ecules in 3b (i.e., the undisordered mol­ecule and the two disorder components) differ in the arrangement of the subsituents on the phenyl ring and the conformation adopted by their 5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl moieties. In the crystal of 3a, N—H⋯O hydrogen bonds link the mol­ecules into a zigzag chain propagating in the [001] direction. For 3b a combination of C—H⋯O and N—H⋯O inter­molecular inter­actions link the mol­ecules into a zigzag ribbon propagating in the [001] direction.
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spelling pubmed-80611032021-05-04 Syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide Anderson, Alan J. Butcher, Ray J. Ollie, Edward Acta Crystallogr E Crystallogr Commun Research Communications The first title benzoyl amide, C(17)H(20)ClNO(5) (3a), crystallizes in the monoclinic space group P2(1)/c with Z = 4 and the second, C(19)H(24)ClNO(5) (3b), also crystallizes in P2(1)/c with Z = 8 (Z′ = 2), thus there are two independent mol­ecules in the asymmetric unit. In 3a, the phenyl ring makes a dihedral angle of 50.8 (3)° with the amide moiety with the C=O group on the same side of the mol­ecule as the C—Cl group. One meth­oxy group is almost in the plane of the benzene ring, while the eth­oxy and other meth­oxy substituent are arranged on opposite sides of the ring with the eth­oxy group occupying the same side of the ring as the C=O group in the amide moiety. For one of the two mol­ecules in 3b, both the amide and 5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl moieties are disordered over two sets of sites with occupancies of 0.551 (2)/0.449 (2) with the major difference between the two conformers being due to the conformation adopted by the cyclo­hex-2-en-1-one ring. The three mol­ecules in 3b (i.e., the undisordered mol­ecule and the two disorder components) differ in the arrangement of the subsituents on the phenyl ring and the conformation adopted by their 5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl moieties. In the crystal of 3a, N—H⋯O hydrogen bonds link the mol­ecules into a zigzag chain propagating in the [001] direction. For 3b a combination of C—H⋯O and N—H⋯O inter­molecular inter­actions link the mol­ecules into a zigzag ribbon propagating in the [001] direction. International Union of Crystallography 2021-02-26 /pmc/articles/PMC8061103/ /pubmed/33953958 http://dx.doi.org/10.1107/S2056989021001778 Text en © Anderson et al. 2021 https://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.
spellingShingle Research Communications
Anderson, Alan J.
Butcher, Ray J.
Ollie, Edward
Syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide
title Syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide
title_full Syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide
title_fullStr Syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide
title_full_unstemmed Syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide
title_short Syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-N-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-N-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide
title_sort syntheses and structures of two benzoyl amides: 2-chloro-4-eth­oxy-3,5-dimeth­oxy-n-(3-oxo­cyclo­hex-1-en-1-yl)benzamide and 2-chloro-n-(5,5-dimethyl-3-oxo­cyclo­hex-1-en-1-yl)-4-eth­oxy-3,5-di­meth­oxy­benzamide
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8061103/
https://www.ncbi.nlm.nih.gov/pubmed/33953958
http://dx.doi.org/10.1107/S2056989021001778
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