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access2-Fluoro-5-(4-fluorophenyl)pyridine
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
In the title compound, C11H7F2N, the fluorobenzene and the 2-fluoropyridine rings are oriented at a dihedral angle of 37.93 (5)°. In the crystal, only van der Waals interactions occur.
![[Scheme 1]](hb6833scheme1.gif)
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2007![[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]](../../../../../../logos/arrows/e_arr.gif "Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.")
); cell 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
contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812025160/hb6833sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025160/hb6833Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812025160/hb6833Isup3.cml
To a 6 ml solution of 5-bromo-2-fluoropyridine (0.2 g, 1.136 mmol), 4-fluorophenylboronic 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 a colourless solid. Yield: 0.185 g, 85%. M.p. 350–352 K. Crystallization from a saturated CHCl3 /CH3OH solution gave colorless rods of (I).
The H-atoms were positioned geometrically (C–H = 0.93 Å) and refined as riding with Uiso(H) = xUeq(C), where x = 1.2 for all H-atoms. The of the crystal used in this experiment was indeterminate.
The title compound (I), (Fig. 1) is prepared as a precursor and for the study of biological activities.
The of 6-fluoro-3-(4-methoxyphenyl)pyridin-2-ol (Siddle et al., 2010) has been published which is related to (I).
In (I) the fluorophenyl A (C1–C6/F1) and the 2-fluoropyridine B (C7—C11/N1/F2) are almost planar with r. m. s. deviations of 0.0025 Å and 0.0071 Å, rspectively. The dihedral angle between A/B is 37.93 (5)°. There does not exist any kind of π-interactions and the molecules must interact due to van Der Waals forces.
For a related structure, see: Siddle et al. (2010).
Data collection: APEX2 (Bruker, 2007); cell 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).
![[Figure 1]](./hb6833fig1thm.gif) | Fig. 1. View of the title compound with displacement ellipsoids are drawn at the 50% probability level. |
| C11H7F2N | F(000) = 392 |
| Mr = 191.18 | Dx = 1.418 Mg m−3 |
| Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2c -2ac | Cell parameters from 1162 reflections |
| a = 20.365 (2) Å | θ = 2.0–25.3° |
| b = 3.8303 (3) Å | µ = 0.11 mm−1 |
| c = 11.4835 (14) Å | T = 296 K |
| V = 895.74 (16) Å3 | Rod, colorless |
| Z = 4 | 0.26 × 0.20 × 0.18 mm |
| Bruker Kappa APEXII CCD diffractometer | 1489 independent reflections |
| Radiation source: fine-focus sealed tube | 1162 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.020 |
| Detector resolution: 8.10 pixels mm-1 | θmax = 25.5°, θmin = 2.0° |
| ω scans | h = −21→24 |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −2→4 |
| Tmin = 0.932, Tmax = 0.950 | l = −13→13 |
| 3601 measured reflections |
| 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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.072 | H-atom parameters constrained |
| S = 1.03 | w = 1/[σ2(Fo2) + (0.0344P)2] where P = (Fo2 + 2Fc2)/3 |
| 1489 reflections | (Δ/σ)max < 0.001 |
| 128 parameters | Δρmax = 0.11 e Å−3 |
| 1 restraint | Δρmin = −0.09 e Å−3 |
| C11H7F2N | V = 895.74 (16) Å3 |
| Mr = 191.18 | Z = 4 |
| Orthorhombic, Pca21 | Mo Kα radiation |
| a = 20.365 (2) Å | µ = 0.11 mm−1 |
| b = 3.8303 (3) Å | T = 296 K |
| c = 11.4835 (14) Å | 0.26 × 0.20 × 0.18 mm |
| Bruker Kappa APEXII CCD diffractometer | 1489 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | 1162 reflections with I > 2σ(I) |
| Tmin = 0.932, Tmax = 0.950 | Rint = 0.020 |
| 3601 measured reflections |
| R[F2 > 2σ(F2)] = 0.030 | 1 restraint |
| wR(F2) = 0.072 | H-atom parameters constrained |
| S = 1.03 | Δρmax = 0.11 e Å−3 |
| 1489 reflections | Δρmin = −0.09 e Å−3 |
| 128 parameters |
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. |
| x | y | z | Uiso*/Ueq | ||
| F1 | 0.16885 (7) | −0.0787 (5) | 0.32200 (16) | 0.1219 (8) | |
| F2 | 0.60621 (6) | 0.4445 (4) | 0.58901 (13) | 0.0984 (6) | |
| N1 | 0.50519 (9) | 0.2455 (5) | 0.62465 (14) | 0.0695 (7) | |
| C1 | 0.35628 (9) | 0.1391 (5) | 0.43374 (16) | 0.0497 (7) | |
| C2 | 0.30232 (10) | 0.2088 (6) | 0.50519 (18) | 0.0635 (9) | |
| C3 | 0.23904 (11) | 0.1346 (7) | 0.4674 (2) | 0.0767 (10) | |
| C4 | 0.23116 (11) | −0.0048 (7) | 0.3597 (2) | 0.0785 (11) | |
| C5 | 0.28211 (11) | −0.0803 (6) | 0.28686 (19) | 0.0713 (9) | |
| C6 | 0.34494 (10) | −0.0045 (5) | 0.32527 (18) | 0.0586 (8) | |
| C7 | 0.42374 (9) | 0.2219 (5) | 0.47208 (15) | 0.0468 (7) | |
| C8 | 0.47047 (9) | 0.3501 (6) | 0.39465 (17) | 0.0560 (8) | |
| C9 | 0.53273 (10) | 0.4268 (5) | 0.43285 (19) | 0.0609 (8) | |
| C10 | 0.54517 (11) | 0.3685 (6) | 0.54736 (19) | 0.0636 (9) | |
| C11 | 0.44444 (10) | 0.1735 (5) | 0.58562 (18) | 0.0603 (8) | |
| H2 | 0.30881 | 0.30545 | 0.57858 | 0.0761* | |
| H3 | 0.20297 | 0.17943 | 0.51471 | 0.0918* | |
| H5 | 0.27490 | −0.17911 | 0.21400 | 0.0855* | |
| H6 | 0.38044 | −0.05144 | 0.27678 | 0.0703* | |
| H8 | 0.45950 | 0.38384 | 0.31684 | 0.0672* | |
| H9 | 0.56470 | 0.51406 | 0.38289 | 0.0731* | |
| H11 | 0.41423 | 0.08497 | 0.63868 | 0.0723* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| F1 | 0.0663 (9) | 0.1613 (16) | 0.1380 (14) | −0.0246 (9) | −0.0268 (10) | 0.0455 (14) |
| F2 | 0.0764 (9) | 0.1291 (14) | 0.0898 (10) | −0.0286 (8) | −0.0211 (9) | 0.0164 (9) |
| N1 | 0.0759 (13) | 0.0821 (15) | 0.0506 (10) | −0.0147 (10) | −0.0079 (10) | 0.0035 (9) |
| C1 | 0.0565 (12) | 0.0413 (12) | 0.0512 (11) | 0.0046 (9) | 0.0032 (9) | 0.0085 (9) |
| C2 | 0.0662 (15) | 0.0613 (17) | 0.0629 (13) | 0.0067 (11) | 0.0106 (11) | 0.0089 (10) |
| C3 | 0.0576 (15) | 0.086 (2) | 0.0864 (18) | 0.0097 (12) | 0.0101 (13) | 0.0230 (16) |
| C4 | 0.0586 (16) | 0.082 (2) | 0.095 (2) | −0.0085 (11) | −0.0191 (14) | 0.0332 (15) |
| C5 | 0.0751 (16) | 0.0737 (18) | 0.0650 (14) | −0.0054 (12) | −0.0149 (12) | 0.0147 (12) |
| C6 | 0.0617 (13) | 0.0589 (15) | 0.0551 (12) | 0.0015 (10) | −0.0007 (10) | 0.0079 (10) |
| C7 | 0.0552 (12) | 0.0393 (12) | 0.0459 (10) | 0.0062 (8) | 0.0027 (9) | 0.0011 (8) |
| C8 | 0.0600 (14) | 0.0609 (14) | 0.0471 (11) | 0.0077 (10) | 0.0020 (10) | 0.0078 (9) |
| C9 | 0.0595 (14) | 0.0634 (16) | 0.0599 (14) | −0.0003 (10) | 0.0094 (10) | 0.0089 (10) |
| C10 | 0.0596 (15) | 0.0635 (16) | 0.0678 (14) | −0.0058 (10) | −0.0088 (11) | 0.0024 (12) |
| C11 | 0.0667 (14) | 0.0627 (15) | 0.0514 (12) | −0.0080 (10) | 0.0065 (10) | 0.0050 (10) |
| F1—C4 | 1.370 (3) | C7—C8 | 1.392 (3) |
| F2—C10 | 1.363 (3) | C7—C11 | 1.383 (3) |
| N1—C10 | 1.293 (3) | C8—C9 | 1.374 (3) |
| N1—C11 | 1.344 (3) | C9—C10 | 1.358 (3) |
| C1—C2 | 1.397 (3) | C2—H2 | 0.9300 |
| C1—C6 | 1.381 (3) | C3—H3 | 0.9300 |
| C1—C7 | 1.477 (3) | C5—H5 | 0.9300 |
| C2—C3 | 1.389 (3) | C6—H6 | 0.9300 |
| C3—C4 | 1.357 (3) | C8—H8 | 0.9300 |
| C4—C5 | 1.364 (3) | C9—H9 | 0.9300 |
| C5—C6 | 1.384 (3) | C11—H11 | 0.9300 |
| C10—N1—C11 | 115.17 (18) | F2—C10—C9 | 118.35 (19) |
| C2—C1—C6 | 118.31 (18) | N1—C10—C9 | 127.4 (2) |
| C2—C1—C7 | 121.03 (17) | N1—C11—C7 | 124.57 (18) |
| C6—C1—C7 | 120.66 (17) | C1—C2—H2 | 120.00 |
| C1—C2—C3 | 120.47 (19) | C3—C2—H2 | 120.00 |
| C2—C3—C4 | 118.4 (2) | C2—C3—H3 | 121.00 |
| F1—C4—C3 | 118.6 (2) | C4—C3—H3 | 121.00 |
| F1—C4—C5 | 117.8 (2) | C4—C5—H5 | 121.00 |
| C3—C4—C5 | 123.6 (2) | C6—C5—H5 | 121.00 |
| C4—C5—C6 | 117.6 (2) | C1—C6—H6 | 119.00 |
| C1—C6—C5 | 121.70 (19) | C5—C6—H6 | 119.00 |
| C1—C7—C8 | 121.42 (16) | C7—C8—H8 | 120.00 |
| C1—C7—C11 | 122.40 (17) | C9—C8—H8 | 120.00 |
| C8—C7—C11 | 116.18 (17) | C8—C9—H9 | 122.00 |
| C7—C8—C9 | 120.17 (18) | C10—C9—H9 | 122.00 |
| C8—C9—C10 | 116.52 (19) | N1—C11—H11 | 118.00 |
| F2—C10—N1 | 114.27 (19) | C7—C11—H11 | 118.00 |
| C11—N1—C10—F2 | 179.11 (18) | C2—C3—C4—F1 | 180.0 (2) |
| C11—N1—C10—C9 | −1.0 (3) | C2—C3—C4—C5 | 0.8 (4) |
| C10—N1—C11—C7 | 0.1 (3) | F1—C4—C5—C6 | 179.9 (2) |
| C6—C1—C2—C3 | 0.0 (3) | C3—C4—C5—C6 | −1.0 (4) |
| C7—C1—C2—C3 | 179.0 (2) | C4—C5—C6—C1 | 0.7 (3) |
| C2—C1—C6—C5 | −0.2 (3) | C1—C7—C8—C9 | 179.62 (19) |
| C7—C1—C6—C5 | −179.19 (19) | C11—C7—C8—C9 | −1.1 (3) |
| C2—C1—C7—C8 | −142.1 (2) | C1—C7—C11—N1 | −179.87 (18) |
| C2—C1—C7—C11 | 38.7 (3) | C8—C7—C11—N1 | 0.9 (3) |
| C6—C1—C7—C8 | 36.9 (3) | C7—C8—C9—C10 | 0.4 (3) |
| C6—C1—C7—C11 | −142.3 (2) | C8—C9—C10—F2 | −179.37 (19) |
| C1—C2—C3—C4 | −0.3 (4) | C8—C9—C10—N1 | 0.7 (3) |
Experimental details
| Crystal data | |
| Chemical formula | C11H7F2N |
| Mr | 191.18 |
| Crystal system, space group | Orthorhombic, Pca21 |
| Temperature (K) | 296 |
| a, b, c (Å) | 20.365 (2), 3.8303 (3), 11.4835 (14) |
| V (Å3) | 895.74 (16) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.11 |
| Crystal size (mm) | 0.26 × 0.20 × 0.18 |
| Data collection | |
| Diffractometer | Bruker Kappa APEXII CCD |
| Absorption correction | Multi-scan (SADABS; Bruker, 2005) |
| Tmin, Tmax | 0.932, 0.950 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 3601, 1489, 1162 |
| Rint | 0.020 |
| (sin θ/λ)max (Å−1) | 0.606 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.072, 1.03 |
| No. of reflections | 1489 |
| No. of parameters | 128 |
| No. of restraints | 1 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.11, −0.09 |
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 the World University Service, Germany, for an equipment grant and the Higher Education Commission, Pakistan, for a resource grant.
References
Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siddle, J. S., Batsanov, A. S., Caldwell, S. T., Cooke, G. & Bryce, M. R. (2010). Tetrahedron, 66, 6138–6149. Web of Science CSD CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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| CRYSTALLOGRAPHIC COMMUNICATIONS |
The title compound (I), (Fig. 1) is prepared as a precursor and for the study of biological activities.
The crystal structure of 6-fluoro-3-(4-methoxyphenyl)pyridin-2-ol (Siddle et al., 2010) has been published which is related to (I).
In (I) the fluorophenyl A (C1–C6/F1) and the 2-fluoropyridine B (C7—C11/N1/F2) are almost planar with r. m. s. deviations of 0.0025 Å and 0.0071 Å, rspectively. The dihedral angle between A/B is 37.93 (5)°. There does not exist any kind of π-interactions and the molecules must interact due to van Der Waals forces.