4-(2-Fluoro­pyridin-5-yl)phenol

Elahi, F.; Adeel, M.; Tahir, M.N.

doi:10.1107/S1600536812026499

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2124

https://doi.org/10.1107/S1600536812026499

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

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

^aDepartment of Chemistry, Gomal University, Dera Ismail Khan, K.P.K., Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 10 June 2012; accepted 11 June 2012; online 16 June 2012)

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, P b c a
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[F² > 2σ(F²)] = 0.051
wR(F²) = 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

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
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812026499/hb6846sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812026499/hb6846Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812026499/hb6846Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Structure description top

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).

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

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing, which shows that molecules form C(9) chains extending along [001].

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

Crystal data top

C₁₁H₈FNO	F(000) = 784
M_r = 189.18	D_x = 1.425 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 869 reflections
a = 12.275 (3) Å	θ = 2.1–26.0°
b = 7.4343 (11) Å	µ = 0.11 mm⁻¹
c = 19.328 (3) Å	T = 296 K
V = 1763.8 (6) Å³	Plate, light brown
Z = 8	0.28 × 0.22 × 0.18 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1732 independent reflections
Radiation source: fine-focus sealed tube	896 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.064
Detector resolution: 8.00 pixels mm^-1	θ_max = 26.0°, θ_min = 2.1°
ω scans	h = −15→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −9→9
T_min = 0.975, T_max = 0.985	l = −17→23
7508 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0483P)²] where P = (F_o² + 2F_c²)/3
1732 reflections	(Δ/σ)_max < 0.001
128 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

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

Data collection top

Bruker Kappa APEXII CCD diffractometer	1732 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	896 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.985	R_int = 0.064
7508 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
1732 reflections	Δρ_min = −0.18 e Å⁻³
128 parameters

Special details top

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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 (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.16138 (14)	0.0574 (2)	0.57218 (6)	0.0807 (7)
O1	0.44529 (15)	0.4234 (3)	0.12632 (8)	0.0611 (8)
N1	0.3071 (2)	0.1137 (3)	0.50603 (9)	0.0532 (9)
C1	0.3319 (2)	0.2565 (3)	0.31870 (11)	0.0361 (9)
C2	0.4308 (2)	0.3444 (3)	0.31099 (12)	0.0414 (9)
C3	0.4687 (2)	0.3971 (3)	0.24670 (12)	0.0439 (10)
C4	0.4071 (2)	0.3622 (3)	0.18829 (12)	0.0416 (9)
C5	0.3108 (2)	0.2682 (3)	0.19463 (11)	0.0449 (10)
C6	0.2736 (2)	0.2170 (3)	0.25895 (10)	0.0419 (9)
C7	0.2856 (2)	0.2081 (3)	0.38699 (11)	0.0367 (9)
C8	0.1738 (2)	0.2085 (3)	0.39711 (12)	0.0462 (10)
C9	0.1293 (2)	0.1575 (3)	0.45939 (12)	0.0520 (11)
C10	0.2008 (3)	0.1116 (3)	0.51007 (12)	0.0524 (10)
C11	0.3492 (2)	0.1610 (3)	0.44353 (11)	0.0470 (10)
H1	0.39877	0.40831	0.09643	0.0916*
H2	0.47273	0.36848	0.34999	0.0497*
H3	0.53530	0.45572	0.24276	0.0527*
H5	0.27072	0.23925	0.15533	0.0540*
H6	0.20815	0.15470	0.26247	0.0503*
H8	0.12817	0.24378	0.36118	0.0555*
H9	0.05436	0.15458	0.46643	0.0624*
H11	0.42453	0.16170	0.43841	0.0565*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0964 (16)	0.1031 (13)	0.0427 (9)	−0.0147 (11)	0.0132 (9)	0.0107 (8)
O1	0.0498 (15)	0.0910 (14)	0.0424 (10)	−0.0135 (11)	0.0072 (9)	0.0057 (10)
N1	0.066 (2)	0.0596 (15)	0.0339 (13)	0.0057 (14)	0.0004 (12)	−0.0012 (10)
C1	0.0395 (18)	0.0352 (13)	0.0335 (14)	0.0013 (12)	0.0020 (12)	−0.0030 (10)
C2	0.0406 (18)	0.0456 (14)	0.0380 (14)	0.0002 (13)	−0.0052 (12)	−0.0044 (10)
C3	0.0363 (18)	0.0471 (16)	0.0484 (16)	−0.0038 (13)	0.0056 (13)	−0.0035 (11)
C4	0.0421 (19)	0.0493 (15)	0.0335 (15)	0.0028 (14)	0.0063 (13)	−0.0012 (11)
C5	0.045 (2)	0.0555 (16)	0.0341 (15)	−0.0048 (14)	−0.0050 (12)	−0.0024 (11)
C6	0.0418 (18)	0.0457 (15)	0.0382 (15)	−0.0071 (13)	0.0006 (13)	−0.0018 (11)
C7	0.0412 (19)	0.0336 (13)	0.0354 (14)	0.0023 (12)	−0.0028 (13)	−0.0028 (10)
C8	0.049 (2)	0.0521 (16)	0.0376 (16)	0.0036 (14)	−0.0005 (14)	0.0011 (11)
C9	0.048 (2)	0.0627 (18)	0.0453 (17)	−0.0060 (15)	0.0049 (15)	−0.0046 (12)
C10	0.069 (2)	0.0544 (17)	0.0339 (17)	−0.0055 (17)	0.0102 (17)	−0.0002 (12)
C11	0.050 (2)	0.0504 (16)	0.0405 (16)	0.0029 (14)	0.0015 (14)	−0.0054 (11)

Geometric parameters (Å, º) top

F1—C10	1.356 (3)	C7—C8	1.386 (3)
O1—C4	1.364 (3)	C7—C11	1.388 (3)
O1—H1	0.8200	C8—C9	1.375 (3)
N1—C11	1.360 (3)	C9—C10	1.359 (4)
N1—C10	1.307 (4)	C2—H2	0.9300
C1—C2	1.387 (3)	C3—H3	0.9300
C1—C7	1.481 (3)	C5—H5	0.9300
C1—C6	1.390 (3)	C6—H6	0.9300
C2—C3	1.384 (3)	C8—H8	0.9300
C3—C4	1.383 (3)	C9—H9	0.9300
C4—C5	1.379 (3)	C11—H11	0.9300
C5—C6	1.378 (3)

C4—O1—H1	109.00	N1—C10—C9	126.8 (2)
C10—N1—C11	115.8 (2)	F1—C10—C9	118.9 (3)
C2—C1—C6	117.5 (2)	N1—C11—C7	123.4 (2)
C6—C1—C7	119.4 (2)	C1—C2—H2	119.00
C2—C1—C7	123.1 (2)	C3—C2—H2	119.00
C1—C2—C3	121.6 (2)	C2—C3—H3	120.00
C2—C3—C4	119.7 (2)	C4—C3—H3	120.00
O1—C4—C5	122.8 (2)	C4—C5—H5	120.00
C3—C4—C5	119.4 (2)	C6—C5—H5	120.00
O1—C4—C3	117.8 (2)	C1—C6—H6	119.00
C4—C5—C6	120.3 (2)	C5—C6—H6	119.00
C1—C6—C5	121.4 (2)	C7—C8—H8	119.00
C1—C7—C8	120.3 (2)	C9—C8—H8	119.00
C1—C7—C11	123.2 (2)	C8—C9—H9	122.00
C8—C7—C11	116.5 (2)	C10—C9—H9	122.00
C7—C8—C9	121.1 (2)	N1—C11—H11	118.00
C8—C9—C10	116.3 (2)	C7—C11—H11	118.00
F1—C10—N1	114.4 (2)

C11—N1—C10—F1	177.63 (19)	C2—C3—C4—O1	177.2 (2)
C11—N1—C10—C9	−2.5 (4)	C2—C3—C4—C5	−2.8 (3)
C10—N1—C11—C7	1.2 (3)	O1—C4—C5—C6	−176.9 (2)
C6—C1—C2—C3	2.3 (3)	C3—C4—C5—C6	3.1 (3)
C7—C1—C2—C3	−176.1 (2)	C4—C5—C6—C1	−0.7 (4)
C2—C1—C6—C5	−2.0 (3)	C1—C7—C8—C9	177.6 (2)
C7—C1—C6—C5	176.5 (2)	C11—C7—C8—C9	−2.6 (3)
C2—C1—C7—C8	146.8 (2)	C1—C7—C11—N1	−178.9 (2)
C2—C1—C7—C11	−33.1 (3)	C8—C7—C11—N1	1.2 (3)
C6—C1—C7—C8	−31.6 (3)	C7—C8—C9—C10	1.5 (3)
C6—C1—C7—C11	148.5 (2)	C8—C9—C10—F1	−178.9 (2)
C1—C2—C3—C4	0.1 (3)	C8—C9—C10—N1	1.2 (4)

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₈FNO
M_r	189.18
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.275 (3), 7.4343 (11), 19.328 (3)
V (Å³)	1763.8 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.28 × 0.22 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.975, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	7508, 1732, 896
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.123, 1.00
No. of reflections	1732
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.18

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Symmetry code: (i) x, −y+1/2, z−1/2.

Acknowledgements

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.

References

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