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Methyl (Z)-2-chloro-3-(2-methoxy-carbonyl-phen-yl)prop-2-enoate.

ABSTRACT: 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 ? systems of the aromatic ring and chloro-propenoate substituent are not coplanar; the corresponding dihedral angle is 51.5?(1)°. The noncoplanarity is likely due to steric inter-actions between the propenoate H atom and the ortho-methoxy-carbonyl 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).

SUBMITTER: Fadgen CJ

PROVIDER: S-EPMC2979665 | biostudies-literature | 2010 Jan

REPOSITORIES: biostudies-literature

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Methyl (Z)-2-chloro-3-(2-methoxy-carbonyl-phen-yl)prop-2-enoate.

Fadgen Casey J CJ Groy Thomas L TL Rose Seth D SD

Acta crystallographica. Section E, Structure reports online 20100116 Pt 2

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 chloro-propenoate substituent are not coplanar; the corresponding dihedral angle is 51.5 (1)°. The noncoplanarity is likely due to steric inter-actions between the propenoate H atom and the ortho-methoxy-carbonyl group ...[more]

PMID: 21579798

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