2-Benzoyl-3-hydroxy-1-naphthylamino-3-phenyl-2-propen-1-one

Abstract

In the title compound, C 26 H 19 NO 3 , the phenyl rings form a dihedral angle of 46.8 (1)° and they make dihedral angles of 79.6 (1) and 67.7 (1)° with the naphthalene ring. The hydroxy groups involve in O-H···O intramolecular H-bonds. CommentNaphthylamine moiety is found to be extremely carcinogenic (Sigma Chemical Company, 1994). Naphthylamine is employed as a disinfectant or insecticide (moth balls) and for the preparation of hydronaphthalenes, phthalic acid and anthronilic acid, but mainly for the manufacture of great many derivatives, which are employed in the colour industry (Tedder & Nechvatal, 1967;Kipping & Kipping, 1961). C 26 H 19 NO 3 existence to tautomerizes in liquid phase (Tezcan, 1990). The intramolecular distance in this structure [H3O···O1 2.416 (4) Å], indicates the presence of hydrogen bonding which occur in the tautomeric enol form. The similar structure dibenzoylacetic acid-N-carboxymethylamide (Fabian et al., 1992) is keto form. The crystal structure determination of the title compound was undertaken in order to elucidate the molecular conformation and hydrogen bonding. The structure has the enolic form in solid phase.The bond lengths and angles in this structure are normal and comparable to those observed in dibenzoylacetic acid-Ncarboxymethylamine (Fabian et al., 1992) and 3-endo-(1-naphthylamino)camphor (Yagi, Ohashi, Ishige & Maeda, 1989).The naphthalene ring is planar with a maximum deviation of 0.040 (4) Å for C6. The phenyl ring planes form a dihedral angle of 46.8 (1)° between them. The naphthalene ring make dihedral angles of 79.6 (1)° and 67.7 (1)°, respectively with the two phenyl rings. The hydroxy group involve in O-H···O intramolecular hydrogen bond with the carbonyl oxygen. The detail of the hydrogen bond is O3-H3O 1.11 (5), O3···O1 2.416 (4), H3O···O1 1.35 (5)Å and O3-H3O···O1 157 (5)°. ExperimentalTo a solution of dibenzoyl-L-acetic acid-N-carboxymethyamide (0.325 g m) was added 1-naphthylamine (0.150 g m) and toluene (25 ml). The mixture was boiled under reflux for 3 h.(C=O), δ=172.32-105.95 p.p.m. (olefenic carbon). RefinementThe temperature of the crystal was maintained at 173 (2) K by using the Watlow control systems. The data collection was covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different φ angle (0,