4-(2-Fluoro­pyridin-5-yl)phenol

Fazal Elahi; Muhammad Adeel; M Nawaz Tahir

doi:10.1107/S1600536812026499

. 2012 Jun 16;68(Pt 7):o2124. doi: 10.1107/S1600536812026499

4-(2-Fluoropyridin-5-yl)phenol

Fazal Elahi ^a, Muhammad Adeel ^a, M Nawaz Tahir ^b,^*

PMCID: PMC3393935 PMID: 22798800

Abstract

In the title compound, C₁₁H₈FNO, the aromatic rings are oriented at a dihedral angle of 31.93 (6)°. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming C(9) chains propagating along the c-axis direction. There are aromatic π–π stacking interactions between the pyridine rings [centroid–centroid separation = 3.7238 (16) Å].

Related literature

For related structures, see: Adeel et al. (2012 ▶); Elahi et al. (2012 ▶).

Experimental

Crystal data

C₁₁H₈FNO
M _r = 189.18
Orthorhombic,
a = 12.275 (3) Å
b = 7.4343 (11) Å
c = 19.328 (3) Å
V = 1763.8 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.975, T _max = 0.985
7508 measured reflections
1732 independent reflections
896 reflections with I > 2σ(I)
R _int = 0.064

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.123
S = 1.00
1732 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026499/hb6846sup1.cif

e-68-o2124-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026499/hb6846Isup2.hkl

e-68-o2124-Isup2.hkl^{(83.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812026499/hb6846Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.82	2.08	2.891 (3)	168

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. MA also acknowledges financial support from the World University Service, Germany, for an equipment grant and the Higher Education Commission, Pakistan, for a resource grant.

supplementary crystallographic information

Comment

We have reported the crystal structure of 5-(4-fluorophenyl)-2-fluoropyridine (Elahi et al., 2012) and 5-(4-chlorophenyl)-2-fluoropyridine (Adeel et al., 2012) which are related to (I).

In (I) the 4-hydroxybenzene A (C1–C6/O1) and the 2-fluoropyridine B (C7—C11/N1/F1) are planar with r.m.s. deviations of 0.0222 Å and 0.0154 Å. The dihedral angle between A/B is 31.93 (6)°. There molecules are stabilized in the form of one-dimensional C(9) chains along the c-axis due to H-bondings of O—H···N type between hydroxy and pyridine groups (Table 1, Fig. 2). There exist π–π interaction between Cg1···Cg1ⁱ [i = 1/2 - x, -1/2 + y, z] and Cg1···Cg1ⁱⁱ [ii = 1/2 - x, 1/2 + y, z] at a distance of 3.7238 (16) Å, where Cg1 is the centroid of pyridine ring.

Experimental

To a 6 ml solution of 5-bromo-2-fluoropyridine (0.2 g, 1.136 mmol), 4-hydroxyphenylboronic acid (0.190 g, 1.36 mmol) in dioxane and K₃PO₄ (0.361 g, 1.5 mmol, in 1 ml H₂O) was added Pd(PPh₃)₄ (1.5 mole %) at 373 K under N₂ atmosphere. The reaction mixture was refluxed for 8 h. Then 20 ml of distilled water was added. The aqueous layer was extracted three times with EtOAc(3×15 ml). The organic layer was evaporated in vacuo and title compound was obtained as light brown solid. Yield: 0.191 g, 89%. M.p. 350–352 K. Crystallization from a saturated solution of CHCl₃ /CH₃OH gave light brown plates.