Abstract
The title compound, C50H36N2, synthesized by the condensation reaction of 2-methyl-4,6-diphenylaniline and acenaphthylene-1,2-dione, crystallizes with two independent molecules (AandB) in the asymmetric unit. The two molecules differ essentially in the orientation of the phenyl ring at position 3′ of the terphenyl group with respect to the central ring of this unit. In moleculeAthis dihedral angle is 16.68 (14)°, while in moleculeBthe corresponding angle is 33.10 (16)°. The three-fused-ring 1,2-dihydroacenaphthylene units are planar in each molecule; r.m.s. deviation of 0.025 Å in moleculeAand 0.017 Å in moleculeB. The central rings of the terphenyl groups are almost normal to the mean plane of the three-fused-ring units with dihedral angles of 79.43 (12) and 82.66 (13)° in moleculeAand 88.99 (13) and 87.98 (12)° in moleculeB. In the crystal, the two molecules are linkedviaa C—H...N hydrogen bond. TheseA–Bunits are linked by a pair of C—H...π interactions, forming a four-molecule unit located about an inversion center. These four-molecule units are linked by weak π–π interactions [most significant intercentroid distance = 3.794 (2) Å], forming columns along direction [010]. A region of disordered electron density was corrected for using the SQUEEZE routine inPLATON[Spek (2015).Acta Cryst. C71, 9–18]. The formula mass and unit-cell characteristics of this unknown solvent were not be taken into account during the refinement.
Highlights
The title compound, C50H36N2, synthesized by the condensation reaction of 2-methyl-4,6-diphenylaniline and acenaphthylene-1,2-dione, crystallizes with two independent molecules (A and B) in the asymmetric unit
The two molecules are linked via a C—HÁ Á ÁN hydrogen bond
These A– B units are linked by a pair of C—HÁ Á Á interactions, forming a four-molecule unit located about an inversion center
Summary
The solution was placed in a round-bottomed flask and stirred at room temperature for 12 h. The solution was eluted with ethyl acetate/petroleum ether (v/v = 1:15) through a column, giving compound (1) as a colourless liquid (yield: 0.75 g, 79%). Synthesis of the title compound: Formic acid (0.5 ml) was added to a stirred solution of acenaphthylene-1,2-dione (2) [0.18 g, 1.00 mmol] and compound (1) [0.57 g, 2.2 mmol) in ethanol Crystals suitable for X–ray structure analysis were grown from a cyclohexane/ dichloromethane (v/v = 1:2) solution by slow evaporation. The formula mass and unit-cell characteristics of this unknown solvent were not taken into account during the refinement
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