5-(4-Chloro­phen­yl)-2-fluoro­pyridine

Adeel, M.; Elahi, F.; Tahir, M.N.; Khan, A.; Langer, P.

doi:10.1107/S1600536812025378

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2043

https://doi.org/10.1107/S1600536812025378

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5-(4-Chlorophenyl)-2-fluoropyridine

Muhammad Adeel,^a Fazal Elahi,^a M. Nawaz Tahir,^b ^* Azim Khan ^a and Peter Langer ^c

^aDepartment of Chemistry, Gomal University, Dera Ismail Khan, K.P.K, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cUniversität Rostock, Institut für Chemie, Abteilung für Organische Chemie, Albert-Einstein-Strasse 3a, 18059 Rostock Department of Chemistry, Germany
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 4 June 2012; accepted 4 June 2012; online 13 June 2012)

In the title compound, C₁₁H₇ClFN, the chlorobenzene and 2-fluoropyridine rings are oriented at a dihedral angle of 38.83 (5)°. In the crystal, there are no hydrogen-bonding interactions.

Related literature

For a related structure, see: Elahi et al. (2012 ).

Experimental

Crystal data

C₁₁H₇ClFN
M_r = 207.63
Orthorhombic, P c a 2₁
a = 21.1252 (14) Å
b = 3.8763 (3) Å
c = 11.7009 (8) Å
V = 958.16 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.37 mm⁻¹
T = 296 K
0.26 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.932, T_max = 0.950
4142 measured reflections
1619 independent reflections
1255 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.073
S = 1.08
1619 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.11 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ), 735 Friedel pairs
Flack parameter: −0.09 (8)

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/S1600536812025378/bq2365sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025378/bq2365Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025378/bq2365Isup3.cml

checkCIF report

Comment top

The title compound (I), (Fig. 1) is prepared as a precursor and for the study of biological activities.

We have reported the crystal structure of 5-(4-fluorophenyl)-2-fluoropyridine previously (Elahi et al., 2012) which is related to (I). In (I) the chlorobenzene A (C1–C6/CL1) and the 2-fluoropyridine B (C7—C11/N1/F1) are planar with r.m.s. deviations of 0.0093 Å and 0.0064 Å. The dihedral angle between A/B is 38.82 (5)°. There does not exist any kind of π-interactions and the molecules must be stabilized due to van Der Wall forces.

Related literature top

For a related structure, see: Elahi et al. (2012).

Experimental top

To a 5 ml solution of 5-bromo-2-fluoropyridine (0.1 g, 0.568 mmol), 4-chlorophenylboronic acid (0.097 g, 0.624 mmol) in dioxane and K₃PO₄ (0.132 g, 0.624 mmol) 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 to the reaction mixture. The aqueous layer was extracted three times with CH₂Cl₂(3 × 15 ml). The organic layer was evaporated in vacuo and the title compound (I) was obtained as a colorless crystalline solid. Yield: 0.106 g, 91 %. M.p. 344–347 K. Crystallization from a saturated CHCl₃ /CH₃OH solution gave colorless crystals.

Structure description top

The title compound (I), (Fig. 1) is prepared as a precursor and for the study of biological activities.

For a related structure, see: 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 the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level.

5-(4-Chlorophenyl)-2-fluoropyridine top

Crystal data top

C₁₁H₇ClFN	F(000) = 424
M_r = 207.63	D_x = 1.439 Mg m⁻³
Orthorhombic, Pca2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 1255 reflections
a = 21.1252 (14) Å	θ = 2.6–26.0°
b = 3.8763 (3) Å	µ = 0.37 mm⁻¹
c = 11.7009 (8) Å	T = 296 K
V = 958.16 (12) Å³	Prism, colorless
Z = 4	0.26 × 0.20 × 0.18 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1619 independent reflections
Radiation source: fine-focus sealed tube	1255 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
Detector resolution: 8.10 pixels mm^-1	θ_max = 26.0°, θ_min = 2.6°
ω scans	h = −18→26
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −3→4
T_min = 0.932, T_max = 0.950	l = −14→10
4142 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.0344P)²] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
1619 reflections	Δρ_max = 0.11 e Å⁻³
127 parameters	Δρ_min = −0.13 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 735 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (8)

Crystal data top

C₁₁H₇ClFN	V = 958.16 (12) Å³
M_r = 207.63	Z = 4
Orthorhombic, Pca2₁	Mo Kα radiation
a = 21.1252 (14) Å	µ = 0.37 mm⁻¹
b = 3.8763 (3) Å	T = 296 K
c = 11.7009 (8) Å	0.26 × 0.20 × 0.18 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	1619 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1255 reflections with I > 2σ(I)
T_min = 0.932, T_max = 0.950	R_int = 0.021
4142 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.073	Δρ_max = 0.11 e Å⁻³
S = 1.08	Δρ_min = −0.13 e Å⁻³
1619 reflections	Absolute structure: Flack (1983), 735 Friedel pairs
127 parameters	Absolute structure parameter: −0.09 (8)
0 restraints

Special details top

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 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
C1	0.25579 (12)	0.5138 (6)	0.1995 (3)	0.0593 (8)
C2	0.24833 (12)	0.3704 (7)	0.3061 (3)	0.0634 (7)
H2	0.2834	0.3347	0.3528	0.076*
C3	0.18888 (12)	0.2798 (7)	0.3435 (2)	0.0571 (7)
H3	0.1840	0.1830	0.4157	0.068*
C4	0.13552 (11)	0.3311 (6)	0.2745 (2)	0.0460 (5)
C5	0.14486 (11)	0.4731 (6)	0.1677 (2)	0.0531 (6)
H5	0.1102	0.5058	0.1199	0.064*
C6	0.20444 (12)	0.5682 (6)	0.1297 (2)	0.0591 (7)
H6	0.2096	0.6673	0.0579	0.071*
C7	0.07137 (11)	0.2343 (6)	0.31377 (19)	0.0464 (6)
C8	0.05152 (13)	0.2866 (7)	0.4246 (2)	0.0607 (7)
H8	0.0804	0.3817	0.4756	0.073*
C9	−0.04479 (14)	0.0724 (8)	0.3900 (3)	0.0646 (8)
C10	0.02695 (11)	0.0942 (6)	0.2397 (2)	0.0521 (6)
H10	0.0374	0.0584	0.1635	0.062*
C11	−0.03221 (12)	0.0085 (7)	0.2783 (3)	0.0595 (7)
H11	−0.0623	−0.0890	0.2301	0.071*
Cl1	0.33061 (3)	0.6376 (2)	0.15406 (9)	0.0880 (3)
F1	−0.10306 (8)	−0.0034 (5)	0.43168 (15)	0.0899 (6)
N1	−0.00621 (11)	0.2107 (6)	0.4643 (2)	0.0696 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0572 (16)	0.0525 (15)	0.068 (2)	0.0040 (12)	0.0070 (13)	−0.0211 (14)
C2	0.0583 (17)	0.0676 (17)	0.064 (2)	0.0100 (14)	−0.0131 (13)	−0.0165 (17)
C3	0.0652 (16)	0.0590 (16)	0.0470 (15)	0.0066 (13)	−0.0051 (12)	−0.0039 (14)
C4	0.0594 (14)	0.0404 (12)	0.0383 (14)	0.0086 (10)	−0.0039 (11)	−0.0043 (11)
C5	0.0569 (13)	0.0544 (14)	0.0479 (16)	0.0071 (11)	−0.0051 (13)	−0.0076 (15)
C6	0.0756 (18)	0.0536 (15)	0.0480 (17)	0.0056 (12)	0.0076 (13)	−0.0061 (13)
C7	0.0550 (14)	0.0421 (13)	0.0423 (16)	0.0082 (11)	−0.0046 (11)	−0.0004 (11)
C8	0.0730 (18)	0.0689 (18)	0.0402 (16)	−0.0056 (14)	−0.0050 (12)	−0.0040 (14)
C9	0.0650 (19)	0.0668 (18)	0.062 (2)	−0.0003 (14)	0.0088 (15)	0.0067 (16)
C10	0.0597 (16)	0.0539 (16)	0.0426 (15)	0.0108 (12)	−0.0054 (12)	−0.0059 (12)
C11	0.0539 (15)	0.0619 (17)	0.063 (2)	0.0036 (13)	−0.0089 (13)	−0.0048 (14)
Cl1	0.0620 (4)	0.0905 (5)	0.1114 (6)	−0.0092 (4)	0.0216 (5)	−0.0273 (6)
F1	0.0695 (10)	0.1191 (15)	0.0811 (12)	−0.0215 (10)	0.0192 (10)	0.0066 (10)
N1	0.0768 (16)	0.0824 (17)	0.0495 (15)	−0.0109 (13)	0.0091 (13)	−0.0003 (13)

Geometric parameters (Å, º) top

C1—C2	1.374 (4)	C6—H6	0.9300
C1—C6	1.375 (3)	C7—C8	1.378 (3)
C1—Cl1	1.735 (3)	C7—C10	1.388 (3)
C2—C3	1.376 (4)	C8—N1	1.338 (3)
C2—H2	0.9300	C8—H8	0.9300
C3—C4	1.400 (3)	C9—N1	1.306 (3)
C3—H3	0.9300	C9—F1	1.356 (3)
C4—C5	1.380 (3)	C9—C11	1.357 (4)
C4—C7	1.479 (3)	C10—C11	1.369 (3)
C5—C6	1.385 (3)	C10—H10	0.9300
C5—H5	0.9300	C11—H11	0.9300

C2—C1—C6	120.8 (2)	C5—C6—H6	120.5
C2—C1—Cl1	119.6 (2)	C8—C7—C10	116.1 (2)
C6—C1—Cl1	119.6 (2)	C8—C7—C4	122.2 (2)
C1—C2—C3	119.8 (2)	C10—C7—C4	121.7 (2)
C1—C2—H2	120.1	N1—C8—C7	124.9 (2)
C3—C2—H2	120.1	N1—C8—H8	117.6
C2—C3—C4	121.0 (3)	C7—C8—H8	117.6
C2—C3—H3	119.5	N1—C9—F1	114.6 (3)
C4—C3—H3	119.5	N1—C9—C11	126.4 (3)
C5—C4—C3	117.6 (2)	F1—C9—C11	119.0 (3)
C5—C4—C7	120.9 (2)	C11—C10—C7	120.4 (2)
C3—C4—C7	121.5 (2)	C11—C10—H10	119.8
C4—C5—C6	121.8 (2)	C7—C10—H10	119.8
C4—C5—H5	119.1	C9—C11—C10	116.8 (2)
C6—C5—H5	119.1	C9—C11—H11	121.6
C1—C6—C5	119.0 (3)	C10—C11—H11	121.6
C1—C6—H6	120.5	C9—N1—C8	115.3 (2)

C6—C1—C2—C3	0.0 (4)	C5—C4—C7—C10	37.1 (3)
Cl1—C1—C2—C3	178.4 (2)	C3—C4—C7—C10	−142.3 (2)
C1—C2—C3—C4	0.1 (4)	C10—C7—C8—N1	0.4 (4)
C2—C3—C4—C5	0.5 (4)	C4—C7—C8—N1	178.6 (2)
C2—C3—C4—C7	179.9 (2)	C8—C7—C10—C11	−1.5 (3)
C3—C4—C5—C6	−1.1 (3)	C4—C7—C10—C11	−179.7 (2)
C7—C4—C5—C6	179.5 (2)	N1—C9—C11—C10	0.7 (4)
C2—C1—C6—C5	−0.6 (4)	F1—C9—C11—C10	179.0 (2)
Cl1—C1—C6—C5	−179.00 (17)	C7—C10—C11—C9	1.0 (3)
C4—C5—C6—C1	1.2 (3)	F1—C9—N1—C8	179.9 (2)
C5—C4—C7—C8	−140.9 (3)	C11—C9—N1—C8	−1.7 (4)
C3—C4—C7—C8	39.6 (3)	C7—C8—N1—C9	1.1 (4)

Experimental details

Crystal data
Chemical formula	C₁₁H₇ClFN
M_r	207.63
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	296
a, b, c (Å)	21.1252 (14), 3.8763 (3), 11.7009 (8)
V (Å³)	958.16 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.37
Crystal size (mm)	0.26 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.932, 0.950
No. of measured, independent and observed [I > 2σ(I)] reflections	4142, 1619, 1255
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.073, 1.08
No. of reflections	1619
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.13
Absolute structure	Flack (1983), 735 Friedel pairs
Absolute structure parameter	−0.09 (8)

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).

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 theWorld University Service, Germany, for an equipment grant and the Higher Education Commission, Pakistan, for a resource grant.

References

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