Crystal and molecular structure of 1-phenyl-3-(2-hydroxyphenylamino)-2-buten-1-one, C16H15NO2

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) A,α=73.06(2),β=79.21(2), χ=67.83(2)°,V=1325.9(5) A3,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) A, respectively]. The conformation ofB is stabilized by only one intramolecular H bond, from the amino NH to the keto O atom [1.925(2) A]. The colorless crystals (moleculeC) are monoclinic, space groupP21/n,a=11.883(3),b=11.004(3),c=10.053(3) A,β=95.93(3)°,V=1307.5(6) A3,Z=4. This conformation is stabilized by one intramolecular H bond, the same as in B, with N-H⋯O, 1.84(3) A. An intermolecular H bond is observed forA,B, and C, O-H⋯O, 2.634(2), 2.640(2), and 2.697(2) A, respectively. The yellow crystals are adducts with ethanol (1H NMR, infrared and GC measurements).