9-(4-Methoxyphenyl)-9H-carbazole

In the title carbazole derivative, the dihedral angle between the carbazole ring system and the pendant phenyl ring is 56.78 (8)°.

In the title compound, C 19 H 15 NO, the dihedral angle between the benzene rings of the carbazole moiety is 1.73 (12) � and the methoxy-substituted phenyl ring deviates from the mean plane of the carbazole grouping (r.m.s.deviation = 0.020 A ˚) by 56.78 (8) � .In the crystal, weak C-H� � �� interactions link the molecules.The two-dimensional fingerprint plots derived from the Hirshfeld surface indicate that H� � �H (51.2%) and C� � �H/H� � �C (39.9%) contacts dominate the packing.

Structure description
Carbazole and its derivatives have attracted attention in the development of electrical and electronic materials because of their conjugated �-electron systems (Taranekar et al., 2007).The N-heterocyclic carbazole molecule has also been employed as a promising candidate in the treatment of cancer (Patil et al., 2022).As part of our studies in this area, we now describe the synthesis and structure of the title compound.

Synthesis and crystallization
A 100 ml round-bottom flask was charged with 4-iodoanisole 1.78 g (7.6 mmol, 1 equiv), 9H-carbazole 1.143 g (6.8 mmol, 1.1 equiv), which were uniformly dispersed in 35 ml of dimethylformamide (DMF) and the mixture was dissolved homogeneously under an N 2 atm.To the mixture, K 2 CO 3 (5.25 g, 38 mmol, 5 equiv), CuI (0.144 g, 0.76 mmol, 0.1 equiv) and 1,10-phenanthroline (0.137 g, 0.76 mmol, 0.1 equiv) was added and the mixture was refluxed for 12 h under N 2 .The progress of the reaction was monitored by TLC.After the completion of the reaction, the reaction was quenched in icewater and the solid product was dissolved in ethyl acetate and washed with brine solution.The obtained solvent was removed under reduced pressure and the obtained residue

Figure 3
Crystal packing viewed along the a-axis direction.

Figure 4
A view of the three-dimensional Hirshfeld surface of the title compound mapped over d norm in the range À 0.05 to 1.63 a.u.

Figure 1
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.was further purified using column chromatography (100-200 mesh silica gel) to afford the title compound as shown in Fig. 6.Single crystals in the form of colourless needles were grown from dichloromethane solution at room temperature.

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.

Figure 2 A
Figure 2A view of the C-H� � �� interactions in the title compound.Cg1 is the centroid of the pyrrole ring of the carbazole molecule (symmetry code: 1 À x, À 1 2 + y, 3 2 À z) and Cg3 is the centroid of the phenyl ring of the carbazole molecule (symmetry code: x, 1 + y, z).

Table 1
Experimental details.