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organic compounds
In the title centrosymmetric molecule, C16H8F4N2, the dihedral angle between the pyridine and benzene rings is 50.47 (5)°, which is intermediate between those observed when the central ring is benzene and when it is an anthracene. The crystal structure consists of layers of molecules parallel to (20
).
).Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806025402/ci2088sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S1600536806025402/ci2088Isup2.hkl |
CCDC reference: 618158
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean
![[sigma]](//journals.iucr.org/logos/entities/sigma_rmgif.gif)
(C-C)= 0.002 Å - R factor = 0.059
- wR factor = 0.137
- Data-to-parameter ratio = 16.8
![[sigma]](http://journals.iucr.org/logos/entities/sigma_rmgif.gif){kind=small}
(C-C)= 0.002 ÅcheckCIF/PLATON results
No syntax errors found No errors found in this datablock
Computing details top
Data collection: MARXDS (Klein, 2000); cell refinement: AUTOMAR (Klein & Bartels, 2000); data reduction: MARSCALE (Klein, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 2003); software used to prepare material for publication: PLATON (Spek, 2003).
2,3–5,6-Tetrafluoro-1,4-di-4-pyridylbenzene top
Crystal data top
| C16H8F4N2 | F(000) = 616 |
| Mr = 304.24 | Dx = 1.639 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -C 2yc | Cell parameters from 147 reflections |
| a = 17.126 (10) Å | θ = 6.3–21.6° |
| b = 5.919 (5) Å | µ = 0.14 mm−1 |
| c = 12.376 (8) Å | T = 294 K |
| β = 100.56 (3)° | Prism, white |
| V = 1233.3 (15) Å3 | 0.3 × 0.2 × 0.1 mm |
| Z = 4 |
Data collection top
| MAR345 image-plate diffractometer | 1473 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.026 |
| Graphite monochromator | θmax = 30.0°, θmin = 2.4° |
| φ scans | h = −23→22 |
| 6143 measured reflections | k = 0→7 |
| 1693 independent reflections | l = 0→17 |
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)] = 0.059 | H-atom parameters constrained |
| wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0816P)2 + 0.0195P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.21 | (Δ/σ)max = 0.001 |
| 1693 reflections | Δρmax = 0.49 e Å−3 |
| 101 parameters | Δρmin = −0.42 e Å−3 |
| 0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.014 (3) |
Special details top
Experimental. Data collection in MAR345 diffractometer was carried out with fixed the image-plate detector at a distance of 84 mm. In total 60 Images were collected with 3°/image and 420 s of exposition per image. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| N | 0.20933 (7) | 0.50516 (17) | 0.41828 (9) | 0.0519 (3) | |
| F1 | −0.00231 (4) | 0.14631 (9) | 0.13829 (5) | 0.0458 (2) | |
| F2 | −0.10191 (4) | 0.14893 (10) | −0.05090 (5) | 0.0461 (2) | |
| C1 | 0.15711 (7) | 0.31785 (17) | 0.24699 (10) | 0.0433 (3) | |
| H1 | 0.1573 | 0.1914 | 0.2024 | 0.052* | |
| C2 | 0.20533 (7) | 0.32728 (19) | 0.35079 (10) | 0.0497 (3) | |
| H2 | 0.2366 | 0.2021 | 0.3745 | 0.060* | |
| C3 | 0.16328 (8) | 0.68117 (19) | 0.38226 (9) | 0.0475 (3) | |
| H3 | 0.1654 | 0.8070 | 0.4277 | 0.057* | |
| C4 | 0.11220 (7) | 0.68866 (17) | 0.28090 (9) | 0.0413 (3) | |
| H4 | 0.0811 | 0.8155 | 0.2598 | 0.050* | |
| C5 | 0.10880 (6) | 0.50163 (16) | 0.21184 (8) | 0.0360 (2) | |
| C6 | 0.05390 (5) | 0.49946 (14) | 0.10312 (7) | 0.0345 (2) | |
| C7 | 0.00131 (6) | 0.32302 (15) | 0.07101 (7) | 0.0348 (3) | |
| C8 | −0.05135 (6) | 0.32455 (15) | −0.02883 (8) | 0.0358 (3) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N | 0.0497 (5) | 0.0572 (6) | 0.0417 (5) | −0.0049 (4) | −0.0100 (4) | 0.0028 (4) |
| F1 | 0.0562 (4) | 0.0415 (4) | 0.0367 (4) | −0.0036 (2) | 0.0005 (3) | 0.0077 (2) |
| F2 | 0.0501 (4) | 0.0420 (4) | 0.0424 (4) | −0.0108 (2) | −0.0015 (3) | −0.0006 (2) |
| C1 | 0.0438 (6) | 0.0407 (5) | 0.0417 (6) | 0.0034 (4) | −0.0019 (4) | −0.0006 (4) |
| C2 | 0.0468 (6) | 0.0481 (6) | 0.0471 (6) | 0.0028 (4) | −0.0099 (5) | 0.0063 (4) |
| C3 | 0.0531 (6) | 0.0489 (6) | 0.0358 (5) | −0.0063 (4) | −0.0040 (4) | −0.0043 (4) |
| C4 | 0.0447 (6) | 0.0416 (5) | 0.0345 (5) | 0.0011 (4) | −0.0010 (4) | −0.0014 (3) |
| C5 | 0.0352 (5) | 0.0404 (5) | 0.0305 (5) | −0.0012 (3) | 0.0012 (3) | 0.0005 (3) |
| C6 | 0.0364 (5) | 0.0367 (5) | 0.0290 (5) | 0.0029 (3) | 0.0020 (4) | −0.0012 (3) |
| C7 | 0.0391 (5) | 0.0346 (5) | 0.0291 (5) | 0.0019 (3) | 0.0021 (4) | 0.0012 (3) |
| C8 | 0.0379 (5) | 0.0344 (5) | 0.0335 (5) | −0.0034 (3) | 0.0021 (4) | −0.0022 (3) |
Geometric parameters (Å, º) top
| N—C3 | 1.3331 (17) | C3—H3 | 0.93 |
| N—C2 | 1.3379 (17) | C4—C5 | 1.3933 (16) |
| F1—C7 | 1.3454 (13) | C4—H4 | 0.93 |
| F2—C8 | 1.3485 (13) | C5—C6 | 1.4936 (16) |
| C1—C5 | 1.3875 (16) | C6—C8i | 1.3848 (15) |
| C1—C2 | 1.3952 (16) | C6—C7 | 1.3887 (14) |
| C1—H1 | 0.93 | C7—C8 | 1.3899 (15) |
| C2—H2 | 0.93 | C8—C6i | 1.3848 (15) |
| C3—C4 | 1.3923 (16) | ||
| C3—N—C2 | 116.53 (11) | C1—C5—C4 | 118.36 (10) |
| C5—C1—C2 | 118.40 (10) | C1—C5—C6 | 121.09 (9) |
| C5—C1—H1 | 120.8 | C4—C5—C6 | 120.54 (9) |
| C2—C1—H1 | 120.8 | C8i—C6—C7 | 115.84 (10) |
| N—C2—C1 | 124.08 (10) | C8i—C6—C5 | 121.98 (9) |
| N—C2—H2 | 118.0 | C7—C6—C5 | 122.17 (8) |
| C1—C2—H2 | 118.0 | F1—C7—C6 | 120.57 (9) |
| N—C3—C4 | 124.17 (10) | F1—C7—C8 | 117.34 (8) |
| N—C3—H3 | 117.9 | C6—C7—C8 | 122.05 (8) |
| C4—C3—H3 | 117.9 | F2—C8—C6i | 120.30 (9) |
| C3—C4—C5 | 118.43 (10) | F2—C8—C7 | 117.58 (8) |
| C3—C4—H4 | 120.8 | C6i—C8—C7 | 122.11 (9) |
| C5—C4—H4 | 120.8 |
| Symmetry code: (i) −x, −y+1, −z. |
