Ethyl (2Z)-3-(4-chlorophenyl)-2-cyano-3-(methoxyamino)prop-2-enoate was prepared by reacting the lithium salt of ethyl cyanoacetate with (Z)-O-methyl-4-chloroben-zohydroximoyl fluoride. This compound crystallizes in space group Pbca,with lattice constants a=7.5740(15) Å, b=11.337(2) Å, and c=30.424(5) Å at 110 K. Characterizations include spectrometric identifications employing IR, UV, and 1H and 13C NMR. The compound exists in the solid as the enamine tautomer, with the cyano group cis to the 4-chlorophenyl group (the Z configuration). The C=C and C–N bond distances are 1.3930(16) Å and 1.3278(16) Å, respectively. The N–H group forms a bifurcated hydrogen bond with acceptors C=O (intramolecular) and C≡N (intermolecular).
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The Minority Biomedical Research Support Program of the National Institutes of Health (NIH-MBRS Grant GM08256), the Robert A. Welch Foundation and the Texas Woman's University Research Enhancement Program supported this work. The purchase of the diffractometer was made possible by grant No. LEQSF (1999-2000)-ENH-TR-13, administrated by the Louisiana Board of Regents.
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CCDC-289444 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, by e-mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; Fax: +44(0)1223-336033.
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Johnson, J.E., Canseco, D.C., Dolliver, D.D. et al. Synthesis, characterization, and structural analysis of ethyl (2Z)-3-(4-chlorophenyl)-2-cyano-3-(methoxyamino)prop-2-enoate. J Chem Crystallogr 36, 667–672 (2006). https://doi.org/10.1007/s10870-006-9115-3
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DOI: https://doi.org/10.1007/s10870-006-9115-3