Abstract
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,
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[F 2 > 2σ(F 2)] = 0.032
wR(F 2) = 0.073
S = 1.08
1619 reflections
127 parameters
H-atom parameters constrained
Δρmax = 0.11 e Å−3
Δρmin = −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.
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812025378/bq2365sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025378/bq2365Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812025378/bq2365Isup3.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 theWorld 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.
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.
Experimental
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.
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.
Figures
Fig. 1.
View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level.
Crystal data
| C11H7ClFN | F(000) = 424 |
| Mr = 207.63 | Dx = 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
| Bruker Kappa APEXII CCD diffractometer | 1619 independent reflections |
| Radiation source: fine-focus sealed tube | 1255 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.021 |
| Detector resolution: 8.10 pixels mm-1 | θmax = 26.0°, θmin = 2.6° |
| ω scans | h = −18→26 |
| Absorption correction: multi-scan (SADABS; Bruker, 2005) | k = −3→4 |
| Tmin = 0.932, Tmax = 0.950 | l = −14→10 |
| 4142 measured reflections |
Refinement
| 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(Fo2) + (0.0344P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max < 0.001 |
| 1619 reflections | Δρmax = 0.11 e Å−3 |
| 127 parameters | Δρmin = −0.13 e Å−3 |
| 0 restraints | Absolute structure: Flack (1983), 735 Friedel pairs |
| Primary atom site location: structure-invariant direct methods | Flack parameter: −0.09 (8) |
Special details
| 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)
| x | y | z | Uiso*/Ueq | ||
| 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)
| 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)
| 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) |
Footnotes
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2365).
References
- Bruker (2005). SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
- Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
- Elahi, F., Adeel, M., Tahir, M. N., Langer, P. & Ahmad, S. (2012). Acta Cryst. E68, o2070. [DOI] [PMC free article] [PubMed]
- Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
- Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.
- Flack, H. D. (1983). Acta Cryst. A39, 876–881.
- Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
- 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/S1600536812025378/bq2365sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025378/bq2365Isup2.hkl
Supplementary material file. DOI: 10.1107/S1600536812025378/bq2365Isup3.cml
Additional supplementary materials: crystallographic information; 3D view; checkCIF report