(4,9-Dimethyl-9H-carbazol-3-yl)methanol

In the title compound, C15H15NO, the carbazole skeleton includes a methanol group at the 3-position. The indole ring system is almost planar [maximum deviation = 0.045 (2) Å]. In the crystal, O—H⋯O hydrogen bonds link the molecules into zigzag chains along the b-axis direction. There are weak C—H⋯π interactions within the chains and linking neighbouring chains forming sheets lying parallel to (001).

The molecule of the title compound contains a carbazole skeleton with a methanol group at the 3 position, Fig. 1. The bond lengths are close to standard values (Allen et al., 1987) and generally agree with those in previously reported compounds (Hökelek et al., 1994;Patır et al., 1997;Öncüoğlu et al., 2014). In all structures atom N9 is substituted.
In the crystal, O-H···O hydrogen bonds link the molecules into zigzag chains along the b-axis direction (Table 1 and Fig. 2). There are weak C-H···π interactions within the chains and linking neighbouring chains forming two-dimensional networks lying parallel to (001); see Table 1.

Experimental
The title compound was synthesized according to the literature method (Karmakar et al., 1991). A solution of ethyl 4,9dimethyl-9H-carbazole-3 -carboxylate (4.00 g, 15 mmol) in anhydrous tetrahydrofurane (50 ml) was added drop wise to a stirred solution of lithium aluminium hydride (1.20 g, 31 mmol) in tetrahydrofurane at room temperature. The reaction mixture was refluxed for 5 h under a nitrogen atmosphere, and then cooled and the excess of lithium aluminium hydride was destroyed with water and extracted with ethyl acetate. The organic phase was dried with anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was recrystallized from ether (Yield; 95%, M.p. 475 K), giving block-like colourless crystals suitable for X-ray diffraction analysis.

Refinement
Atom H1A (for OH) was located in a difference Fourier map and freely refined. The C-bound H-atoms were positioned geometrically with C-H = 0.93, 0.97 and 0.96 Å, for aromatic, methylene and methyl H-atoms, respectively, and constrained to ride on their parent atoms with U iso (H) = 1.5U eq (C-methyl) and = 1.2U eq (C) for other H-atoms.

Figure 1
The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A view of the crystal packing of the title compound with the O-H···O hydrogen bonds shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been 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. 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 > 2sigma(F 2 ) is used only for calculating R-factors(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.