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Methyl (Z)-2-chloro-3-(2-methoxy­carbonyl­phen­yl)prop-2-enoate

In the title compound, C(12)H(11)ClO(4), the propenoate C=C bond is in the Z configuration. The propenoate C=O and C=C groups are essentially coplanar [C=C—C=O torsion angle = 172.4 (3)°] with the O atom synperiplanar to the Cl atom. However, the π systems of the aromatic ring and chloro­propenoate...

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Detalles Bibliográficos
Autores principales: Fadgen, Casey J., Groy, Thomas L., Rose, Seth D.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2010
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979665/
https://www.ncbi.nlm.nih.gov/pubmed/21579798
http://dx.doi.org/10.1107/S160053681000084X
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author Fadgen, Casey J.
Groy, Thomas L.
Rose, Seth D.
author_facet Fadgen, Casey J.
Groy, Thomas L.
Rose, Seth D.
author_sort Fadgen, Casey J.
collection PubMed
description In the title compound, C(12)H(11)ClO(4), the propenoate C=C bond is in the Z configuration. The propenoate C=O and C=C groups are essentially coplanar [C=C—C=O torsion angle = 172.4 (3)°] with the O atom synperiplanar to the Cl atom. However, the π systems of the aromatic ring and chloro­propenoate substituent are not coplanar; the corresponding dihedral angle is 51.5 (1)°. The noncoplanarity is likely due to steric inter­actions between the propenoate H atom and the ortho-methoxy­carbonyl group on the aromatic ring. Even in the observed noncoplanar conformation, the ortho C=O to H distance (2.40 Å) is less than the sum of the van der Waals radii of O and H (2.65 Å).
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spelling pubmed-29796652010-12-30 Methyl (Z)-2-chloro-3-(2-methoxy­carbonyl­phen­yl)prop-2-enoate Fadgen, Casey J. Groy, Thomas L. Rose, Seth D. Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(12)H(11)ClO(4), the propenoate C=C bond is in the Z configuration. The propenoate C=O and C=C groups are essentially coplanar [C=C—C=O torsion angle = 172.4 (3)°] with the O atom synperiplanar to the Cl atom. However, the π systems of the aromatic ring and chloro­propenoate substituent are not coplanar; the corresponding dihedral angle is 51.5 (1)°. The noncoplanarity is likely due to steric inter­actions between the propenoate H atom and the ortho-methoxy­carbonyl group on the aromatic ring. Even in the observed noncoplanar conformation, the ortho C=O to H distance (2.40 Å) is less than the sum of the van der Waals radii of O and H (2.65 Å). International Union of Crystallography 2010-01-16 /pmc/articles/PMC2979665/ /pubmed/21579798 http://dx.doi.org/10.1107/S160053681000084X Text en © Fadgen et al. 2010 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Fadgen, Casey J.
Groy, Thomas L.
Rose, Seth D.
Methyl (Z)-2-chloro-3-(2-methoxy­carbonyl­phen­yl)prop-2-enoate
title Methyl (Z)-2-chloro-3-(2-methoxy­carbonyl­phen­yl)prop-2-enoate
title_full Methyl (Z)-2-chloro-3-(2-methoxy­carbonyl­phen­yl)prop-2-enoate
title_fullStr Methyl (Z)-2-chloro-3-(2-methoxy­carbonyl­phen­yl)prop-2-enoate
title_full_unstemmed Methyl (Z)-2-chloro-3-(2-methoxy­carbonyl­phen­yl)prop-2-enoate
title_short Methyl (Z)-2-chloro-3-(2-methoxy­carbonyl­phen­yl)prop-2-enoate
title_sort methyl (z)-2-chloro-3-(2-methoxy­carbonyl­phen­yl)prop-2-enoate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2979665/
https://www.ncbi.nlm.nih.gov/pubmed/21579798
http://dx.doi.org/10.1107/S160053681000084X
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