Crystal structure of 3,3′-[2,2′-(1,2-ethylenedioxy)dibenzylmethylimino] bis(acetophenone oxime), C32H30N4O4

Abstract

Source of materialTo ah ot ethanol solution (7 ml) of 3-amino-acetophenone (818.2 mg, 6.00 mmol) was added amixture of ahot ethanol solution (10 ml) of hydroxylamine hydrochloride (423.5 mg, 6.00 mmol) and ahot ethanol solution (5 ml) of sodiumacetate. After the solution had been stirred at 55°C for 12 h, the mixture wasconcentrated. Then 30 ml distilled waterwas added. After refrigeratingat-6°Cfor 24 h, thesolutiongavethe yellow solid3-amino-acetophenone oxime, whichwas filtered andwashedsuccessivelywithdistilledwater andethanol/ hexane (1:4). Theisolatedcompoundwas dried under vacuum and gave 551.0 mg of yellow crystalline solid (yield 60.9 %; m. p. 135 -137°C). Thetitle compound 3,3'-[2,2'-(1,2-ethylenedioxy)dibenzylmethylimino]bis(acetophenone oxime) was prepared in as imilar way from 3-amino-acetophenone oximea nd 2,2'-(1,2-ethylenedioxy)dibenzaldehyde. The title compound was dried under vacuum and gave 302.2 mg of light pink solid (yield 76.4 %; m. p. 199 -200°C). Block-shaped colorless single crystals of the title compound suitable for X-ray diffraction studies could be obtained by slow evaporation of an ethanol solution at room temperature. In the crystal structure, the molecules are held together by two pairs of intermolecular C12-H12×××O1 hydrogen bonds between the oxime-oxygen atom and -C12H12 group of the aromatic ring with the distance d(C12-O1) =3 .518(2) Å. In addition, the adjacent rings (C10-C15)a re further linked by aw eak intermolecular p×××p stacking interaction (centroid-centroid distance of 4.106 Å). Thus, every molecule is linked with four other molecules into al ayer supramolecular structure via intermolecular C-H×××Ohydrogen bonds and p×××p stacking interactions.