Abstract
The title compound, C14H13Cl2NO3, was obtained as the product of an attempted synthesis of herbicidally active compounds containing oxime ether and cyclohexenone groups. In the crystal structure, the molecule adopts an endocyclic enol tautomeric form and the cyclohexene ring adopts a distorted envelope form. The oxime ether group has an E configuration, with the methoxy group anti to the ortho-chloro substitutent. Intramolecular O—H⋯O and intermolecular C—H⋯O hydrogen bonds are found in the crystal structure.
Highlights
The title compound, C14H13Cl2NO3, was obtained as the product of an attempted synthesis of herbicidally active compounds containing oxime ether and cyclohexenone groups
Intramolecular O—HÁ Á ÁO and intermolecular C—HÁ Á ÁO hydrogen bonds are found in the crystal structure
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2144)
Summary
Key indicators: single-crystal X-ray study; T = 298 K; mean (C–C) = 0.004 A; R factor = 0.049; wR factor = 0.144; data-to-parameter ratio = 13.9. The title compound, C14H13Cl2NO3, was obtained as the product of an attempted synthesis of herbicidally active compounds containing oxime ether and cyclohexenone groups. The molecule adopts an endocyclic enol tautomeric form and the cyclohexene ring adopts a distorted envelope form. Intramolecular O—HÁ Á ÁO and intermolecular C—HÁ Á ÁO hydrogen bonds are found in the crystal structure. Related literature For the structure of 5-chloro-2-methylthio-3H-indole-3-one 3oxime O-methyl ether, see: Beddoes et al (1992). For theoretical studies on the tautomerism of benzoylcyclohexane-1,3dione and its derivatives, see: Huang et al (2002). For the potential herbicidal property of the title compound and related compounds, see: Knudsen (1988). For the chemistry of 2-acylcycloalkane-1,3-diones, see: Rubinov et al (1999)
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