Abstract
Orange, yellow, and colorless crystals were obtained for the title compound. The orange crystals are triclinic, space groupP¯1,a=9.181(2),b=10.734(2),c=15.245(3) Å,α=73.06(2),β=79.21(2), χ=67.83(2)°,V=1325.9(5) Å3,Z=4. Two different symmetry-independent molecules (moleculeA andB) were determined in the crystal unit. The conformation ofA is stabilized by an intramolecular H bond from the amino NH to the keto and phenolic O atoms [1.89(2) and 2.38(2) Å, respectively]. The conformation ofB is stabilized by only one intramolecular H bond, from the amino NH to the keto O atom [1.925(2) Å]. The colorless crystals (moleculeC) are monoclinic, space groupP21/n,a=11.883(3),b=11.004(3),c=10.053(3) Å,β=95.93(3)°,V=1307.5(6) Å3,Z=4. This conformation is stabilized by one intramolecular H bond, the same as in B, with N-H⋯O, 1.84(3) Å. An intermolecular H bond is observed forA,B, and C, O-H⋯O, 2.634(2), 2.640(2), and 2.697(2) Å, respectively. The yellow crystals are adducts with ethanol (1H NMR, infrared and GC measurements).
Similar content being viewed by others
References
Brown, N. M. D., and Nonhebel, D. C. (1968)Tetrahedron 24, 5655–5664.
Dudek, G. O., and Holm, R. H. (1962)J. Am. Chem. Soc. 84, 2691–2696.
International Tables for X-Ray Crystallography (1974), Vol. IV (Kynoch Press, Birmingham, England).
Sheldrick, G. M. (1986)SHELXS-86. Program for the solution of crystal structures (University of Göttingen, Germany).
SYNTEX XTL/XTLE Structure Determination System (1976) Syntex Analytical Instruments (Cuppertino, Calif.).
Sobczak, J. M., Głowiak, T., and Ziółkowski, J. J. (1990)Trans. Met. Chem. 15, 208–11.
Singh, R. V., and Tandon, J. P. (1978)Ind. J. Chem. A 16, 84–6; 1062–65.
Sawka-Dobrowolska, W., Siatecki, Z., and Sobczak, J. M. (1990)Acta Crystallogr. C 46, 1691–3.
Sawka-Dobrowolska, W., Siatecki, Z., and Sobczak, J. M. (1992)Acta Crystallogr. In press.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Głowiak, T., Sobczak, J.M. Crystal and molecular structure of 1-phenyl-3-(2-hydroxyphenylamino)-2-buten-1-one, C16H15NO2 . Journal of Crystallographic and Spectroscopic Research 22, 673–678 (1992). https://doi.org/10.1007/BF01160984
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01160984