2-Bromo-3-hydroxy-6-methylpyridine

In the title compound, C6H6BrNO, the Br atom is displaced from the pyridine ring mean plane by 0.0948 (3) Å, while the hydroxyl O atom and the methyl C atom are displaced by 0.0173 (19) and 0.015 (3) Å, respectively. In the crystal, molecules are linked via O—H⋯N hydrogen bonds, forming chains propagating along the a-axis direction. These chains are linked by C—H⋯Br hydrogen bonds, forming corrugated two-dimensional networks lying parallel to the ac plane.

In the title compound, C 6 H 6 BrNO, the Br atom is displaced from the pyridine ring mean plane by 0.0948 (3) Å , while the hydroxyl O atom and the methyl C atom are displaced by 0.0173 (19) and 0.015 (3) Å , respectively. In the crystal, molecules are linked via O-HÁ Á ÁN hydrogen bonds, forming chains propagating along the a-axis direction. These chains are linked by C-HÁ Á ÁBr hydrogen bonds, forming corrugated two-dimensional networks lying parallel to the ac plane.

Comment
3-Hydroxypyridine is an integral part of Nikkomycin Z (NZ), a potent fungicide, insecticide, miticide, and inhibitor of fungal and insect chitin synthetase (Tetsu et al., 1990). Various biaryl derivative compounds, derived originally from 3hydroxypyridine, are PDE4 inhibitors useful for the treatment and prevention of strokes, myocardial infarction and cardiovascular inflammatory diseases and disorders. Herein we describe the crystal structure of the 2-bromo derivative of 3-hydroxy-6-methylpyridine, previously synthesized by (Kjell et al., 1969).
The molecular structure of the title molecule is illustrated in Fig. 1. The bond lengths and angles are normal.
In the crystal, molecules are linked via O-H···N hydrogen bonds forming chains propagating along the a axis direction ( Fig. 2 and Table 1). These chains are linked by weak C-H···Br hydrogen bonds forming corrugated two-dimensional networks lying parallel to the ac plane ( Fig. 2 and Table 1).

Experimental
The title compound was synthesized following the published procedure (Kjell et al., 1969). Colourless crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of a solution of the title compound in ethanol [m.p. =

Computing details
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and X-SEED (Barbour, 2001 Table 1 for details; a axis vertical; c axis horizontal). 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 esds 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