The ( Z)-4,4,4-trifluoro-3-(2-hydroxyethylamino)-1-(2-hydroxyphenyl)-2-buten-1-one (C12H12F3NO3) compound was thoroughly studied by IR, Raman, UV-visible, and C-13 and F-19 NMR spectroscopies. The solid-state molecular structure was determined by X-ray diffraction methods. It crystallizes in the P2(1)/c space group with a = 12.1420(4) angstrom, b = 7.8210(3) angstrom, c := 13.8970(5) angstrom, beta = 116.162(2)degrees, and Z = 4 molecules per unit cell. The molecule shows a nearly planar molecular skeleton, favored by intramolecular OH center dot center dot center dot 0 and NH center dot center dot center dot 0 bonds, which are arranged in the lattice as an OH center dot center dot center dot 0 bonded polymer coiled around crystallographic 2-fold screw-axes. The three postulated tautomers were evaluated using quantum chemical calculations. The lowest energy tautomer (I) calculated with density functional theory methods agrees with the observed crystal structure. The structural and conformational properties are discussed considering the effect of the intra- and intermolecular hydrogen bond interactions.