9-Benzyl-9H-carbazole

The asymmetric unit of the title compound, C19H15N, contains two crystallographically independent molecules. In both molecules, the planar carbazole moieties [maximum deviations = 0.037 (4) and 0.042 (3) Å] are oriented with respect to the adjacent benzene rings, at dihedral angles of 85.29 (8) and 89.89 (7)°, respectively. In the crystal structure, weak C—H⋯π interactions are observed involving the carbazole rings.

The asymmetric unit of the title compound, C 19 H 15 N, contains two crystallographically independent molecules. In both molecules, the planar carbazole moieties [maximum deviations = 0.037 (4) and 0.042 (3) Å ] are oriented with respect to the adjacent benzene rings, at dihedral angles of 85.29 (8) and 89.89 (7) , respectively. In the crystal structure, weak C-HÁ Á Á interactions are observed involving the carbazole rings.
The title compound consists of a carbazole skeleton with a benzyl group. Its asymmetric unit, (Fig. 1), contains two crystallographically independent molecules, where the bond lengths (Allen et al., 1987) and angles are within normal ranges, and generally agree with those in compounds (II)-(X). In all structures atom N9 is substituted.
An examination of the deviations from the least-squares planes through individual rings shows that rings A (C1-C4/ In the crystal structure, three weak C-H···π interactions (Table 1) involving the carbazole rings are observed.

Experimental
For the preparation of the title compound, (I), sodium hydride (2.38 g, 59.85 mmol) was added to a solution of carbazole (5.00 g, 29.92 mmol) in dry tetrahydrofuran (200 ml) in several portions, and stirred at room temperature for 1 h under argon atmosphere. Then, benzylchloride (5.68 g, 44.88 mmol) was added and stirred at 343 K for 6 h. The reaction mixture was supplementary materials sup-2 cooled in an ice bath, and hydrochloric acid (10%, 200 ml) was added. After the extraction with dichloromethane (300 ml), the organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by column chromatograpy using silica gel and dichloromethane-petroleum ether (1:1), and the product was recrystallized from diethyl ether and cyclohexane mixture (1:1) (yield; 4.00 g, 80%, m.p. 388 K).

Refinement
H3 and H7' atoms were positioned geometrically, with C-H = 0.93 Å for aromatic H atoms and constrained to ride on their parent atoms, with U iso (H) = 1.2U eq (C). The remaining H atoms were located in difference synthesis and refined isotropically. Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 50% probability level.

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.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating Rfactors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.