Abstract
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.
Related literature
For a related structure, see: Siddle et al. (2010 ▶).
Experimental
Crystal data
C11H7F2N
M r = 191.18
Orthorhombic,
a = 20.365 (2) Å
b = 3.8303 (3) Å
c = 11.4835 (14) Å
V = 895.74 (16) Å3
Z = 4
Mo Kα radiation
μ = 0.11 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
3601 measured reflections
1489 independent reflections
1162 reflections with I > 2σ(I)
R int = 0.020
Refinement
R[F 2 > 2σ(F 2)] = 0.030
wR(F 2) = 0.072
S = 1.03
1489 reflections
128 parameters
1 restraint
H-atom parameters constrained
Δρmax = 0.11 e Å−3
Δρmin = −0.09 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/S1600536812025160/hb6833sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025160/hb6833Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812025160/hb6833Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report
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
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.
Experimental
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).
Refinement
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 absolute structure of the crystal used in this experiment was indeterminate.
Figures
Fig. 1.
View of the title compound with displacement ellipsoids are drawn at the 50% probability level.
Crystal data
| 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 |
Data collection
| 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
| 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 |
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 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)
| 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* |
Atomic displacement parameters (Å2)
| 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) |
Geometric parameters (Å, º)
| 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) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6833).
References
- Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
- Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
- Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
- Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- Siddle, J. S., Batsanov, A. S., Caldwell, S. T., Cooke, G. & Bryce, M. R. (2010). Tetrahedron, 66, 6138–6149.
- Spek, A. L. (2009). Acta Cryst. D65, 148–155. [DOI] [PMC free article] [PubMed]
Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025160/hb6833sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025160/hb6833Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812025160/hb6833Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report