2-(10-Bromoanthracen-9-yl)-N-phenylaniline

The N—H group of the title compound does not form a hydrogen bond due to steric hindrance.

In the title compound, C 26 H 18 BrN, the central benzene ring makes dihedral angles with its adjacent anthracene ring system and pendant benzene ring of 87.49 (13) and 62.01 (17) � , respectively.The N-H moiety is sterically blocked from forming a hydrogen bond, but weak C-H� � �� interactions occur in the extended structure.

Structure description
Anthracene derivatives are candidates for two-dimensional molecular crystals, which can show interesting properties with applications in electronics, biomedicine, and sensors (Yan et al., 2023).As part of our studies of anthracene derivatives, we now report the synthesis and crystal structure of the title compound, C 26 H 18 BrN, (I).
The molecular structure of (I) is illustrated in Fig. 1.As expected, the anthracene (C1-C14) ring system is almost planar, with a maximum deviation of 0.039 (4) A ˚for atom C1.The central benzene (C15-C20) ring makes dihedral angles of 87.49 (13) and 62.01 (17) � with the anthracene ring system and the terminal C21-C26 phenyl ring, respectively.The dihedral angle between the phenyl ring and anthracene ring system is 87.92 (14) � .
In the extended structure, the N-H grouping in (I) is presumably blocked from forming a hydrogen bond due to steric reasons but two weak C-H� � �� interactions are observed (Table 1).The packing is illustrated in Fig. 2.
Related structures reported in the Cambridge Structural Database (CSD, Version 5.41, updated November 2019; Groom et al., 2016)

Synthesis and crystallization
Following the method of Justin Thomas et al. (2005), a mixture of diphenylamine (1.69 g, 10.0 mmol), sodium tert-butoxide (1.15 g, 12.0 mmol) and Pd 2 (dba) 3 (dba = dibenzylideneacetone; 23 mg, 0.10 mmol) was dissolved in dry toluene (50 ml), and 9,10-dibromoanthracene (3.33 g, 10.0 mmol) and 1,1 0 -ferrocenediyl-bis(diphenylphosphine) (0.277 g, 0.5 mmol) were added sequentially.The mixture was heated to reflux, stirred for 24 h and then cooled and 5 ml of water were added.The solution was extracted with dichloromethane/water.The organic layer was dried over anhydrous sodium sulfate, filtered, and dried.The residue was chromatographed through silica gel using a mixture of dichloromethane and hexane as the eluent to give the pure product as yellow crystals.

Refinement
Crystal data, data collection and structure refinement details are summarized in Table 2.

Figure 1
The molecular structure of (I) showing displacement ellipsoids at the 50% probability level (H atoms are omitted for clarity).

Special details
Geometry.All esds (except the esd in the dihedral angle between two l.s.planes) are estimated using the full covariance matrix.The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry.An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s.planes.

data reports data-2
IUCrData (2024).9, x240475 Refinement.The N-bound hydrogen atom was located in a difference map and its position was freely refined.The remaining hydrogen atoms were positioned geometrically [C-H = 0.93 Å] and were refined using a riding model, with U iso (H) = 1.2 or 1.5U eq (C).

Table 2
Experimental details.