1,6-Dibromonaphthalen-2-ol methanol monosolvate

The naphthol-containing molecule of the title compound, C10H6Br2O·CH3OH, crystallized as a methanol monosolvate and is planar to within 0.069 (1) Å for all non-H atoms. In the crystal, molecules are linked by two pairs of O—H⋯O hydrogen bonds, involving the methanol molecule, forming dimer-like arrangements. The crystal structure is further stabilized by π–π stacking [centroid–centroid distance = 3.676 (2) Å] and Br⋯Br interactions [3.480 (4) and 3.786 (1) Å], forming a three-dimensional structure.

The molecule of the title compound is planar to within 0.069 (1) Å for all non-H atoms ( Fig. 1).
In the crystal, molecules are linked by two pairs of O-H···O hydrogen bonds, involving the methanol molecule, forming dimer-like arrangements (Table 1 and Fig. 2).

Experimental
Approximately 100 mg of 1,6-dibromo-2-napthol (Sigma-Aldrich) was dissolved in a 2 ml 50% methanol: 50% hexanes solution. On slow evaporation over the course of two weeks colourless plate-like crystals were obtained. The crystals decomposed rapidly when removed from the mother liquor.

Refinement
The OH and C-bound H atoms were included in calculate positions and treated as riding atoms: O-H = 0.84 Å, C-H = 0.95 and 0.98 Å for CH and CH 3 H atoms, respectively, with U iso (H) = 1.5U eq (O,C-methyl) and = 1.2U eq (C) for other H atoms. A residual density peak of 1.31 e/Å 3 was located near atom C10. Twinning was not found and no disorder could be modeled.

Figure 2
A view along the a axis of the crystal packing of the title compound. The tetramer of Br···Br contacts, the π stacking of the naphthol rings, and the O-H···O hydrogen bonds (Table 1)  where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.002 Δρ max = 1.31 e Å −3 Δρ min = −0.60 e Å −3 Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles 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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq