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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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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2010
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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). |
format | Text |
id | pubmed-2979665 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2010 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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