2. Structural commentary
Compounds I, III, and V each crystallize in orthorhombic space groups, with I and III in P212121 and V in Pbcn. Compounds II and IV crystallize in the monoclinic space groups P21/n and P21 respectively (Fig. 1). With the exception of V, which has one half molecule per asymmetric unit, each compound crystallizes with one molecule per asymmetric unit. The dihedral angle between the aryl susbstituent and the pyridine ring ranges between 56.35 (8) and 80.89 (5)°. In V, the rings of the biphenyl system are rotated by 27.30 (5)° from each other.
| Figure 1 The molecular structures of (a) I, (b) II, (c) III, (d) IV, and (e) V. Displacement ellipsoids are shown at the 50% probability level. |
3. Supramolecular features and Hirshfeld surface analysis
In the crystal structures of each compound, the packing is consolidated by various C—H⋯F and C—F⋯π interactions (Tables 1–5). In II, the packing is aided by C—H⋯π and C—Br⋯N interactions, the latter of which lead to the formation of chains in the [10] direction. Compound III also shows C—H⋯N hydrogen bonding. Further, in IV, C—H⋯π and C—Br⋯π interactions also contribute to the packing. Finally, in I, III, and IV, the packing is aided by halogen bonds of the type C—F⋯F—C or C—F⋯Br—C. In I, the C2—F2⋯F3 distance is 2.8156 (15) Å, with an angle of 119.54 (8)° (symmetry code: 1 − x, + y, − z). For III, the C2—F2⋯F3 distance is 2.766 (15) Å, with an angle of 146.28 (10)° (symmetry code: 1 − x, + y, − z). The bromine atom participates in the halogen bonding of IV, with the C11—Br1⋯F2 distance being 3.095 (5) Å and the angle 164.46 (14)° (symmetry code: 2 − x, − + y, 1 − z). All the observed halogen-bonding geometries fall within typically observed values (Cavallo et al., 2016).
X—Y⋯A | X—Y | Y⋯A | X⋯A | X—Y⋯A | C11—H11⋯F1i | 0.95 | 2.46 | 3.4049 (19) | 170.3 | C1—F1⋯Cg1ii | 1.3404 (18) | 3.6822 (13) | 4.8632 (17) | 147.20 (9) | Symmetry codes: (i) −x + 2, y − , −z + ; (ii) 2 − x, + x, − z. | |
X—Y⋯A | X—Y | Y⋯A | X⋯A | X—Y⋯A | C10—H10⋯F3i | 0.95 | 2.39 | 3.2214 (19) | 145.9 | C11—H11⋯Cg2i | 0.95 | 2.90 | 3.668 (2) | 139 | C1—F1⋯Cg1ii | 1.3395 (19) | 3.1531 (14) | 4.068 (2) | 124.76 (10) | C5—F4⋯Cg1iii | 1.3401 (19) | 3.1094 (13) | 3.6241 (18) | 101.55 (9) | C9—Br1⋯N1iv | 1.8952 (17) | 3.2639 (16) | 5.104 (3) | 162.65 (7) | Symmetry codes: (i) −x + , y + , −z + ; (ii) −x + , y + , −z + ; (iii) −x + 1, −y + 1, −z + 2; (iv) + x, − y, − + z. | |
X—Y⋯A | X—Y | Y⋯A | X⋯A | X—Y⋯A | C7—H7⋯F3i | 0.95 | 2.50 | 3.4366 (19) | 169.6 | C15—H15⋯N1ii | 0.95 | 2.59 | 3.455 (2) | 152.1 | C1—F1⋯Cg2iii | 1.334 (2) | 3.2922 (15) | 3.5581 (19) | 90.28 (10) | C5—F4⋯Cg1iv | 1.343 (2) | 3.2790 (14) | 4.2804 (18) | 130.88 (11) | Symmetry codes: (i) x + 1, y, z; (ii) −x, y + , −z + ; (iii) 1 − x, − + y, − z; (iv) − x, − + y, − z. | |
X—Y⋯A | X—Y | Y⋯A | X⋯A | X—Y⋯A | C15—H15⋯F3ii | 0.95 | 2.43 | 3.105 (5) | 127.5 | C9—H9⋯Cg3i | 0.95 | 2.83 | 3.519 (5) | 130 | C11—Br1⋯Cg1iii | 1.901 (4) | 3.6283 (19) | 4.923 (5) | 122.74 (13) | C11—Br1⋯Cg2iv | 1.901 (4) | 3.735 (2) | 5.037 (4) | 123.34 (12) | C4—F3⋯Cg1v | 1.344 (6) | 3.082 (3) | 3.936 (5) | 120.3 (3) | Symmetry codes: (i) −x + 1, y + , −z + 1; (ii) x + 1, y, z; (iii) −x + 1, y − , −z + 1; (iv) −x + 2, y − , −z + 1; (v) −x, y − , −z. | |
X—Y⋯A | X—Y | Y⋯A | X⋯A | X—Y⋯A | C11—H11⋯F3i | 0.95 | 2.63 | 3.2361 (13) | 121.8 | C11—H11⋯F3ii | 0.95 | 2.60 | 3.2711 (12) | 127.8 | C11—H11⋯O1i | 0.95 | 2.61 | 3.3446 (13) | 134.3 | C5—F4⋯Cg1iii | 1.3382 (12) | 3.4138 (9) | 4.3778 (12) | 128.77 (6) | Symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) x, −y + 1, z − ; (iii) x, 1 − y, + z. | |
Hirshfeld surface analysis was used to further investigate the intermolecular interactions in the crystal structures. The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009) was generated by CrystalExplorer17.5 (Turner et al., 2017), and was comprised of dnorm surface plots. The plots of the Hirshfeld surface are mapped over dnorm using standard surface resolution with a fixed colour scale of −0.1300 (red) to 1.2500 (blue). The characteristic bright-red spots near F1 and H11 in the Hirshfeld surface of I (Fig. 2a) confirm the previously mentioned C11—H11⋯F1 (symmetry code: −x + 2, y − , −z + ) inter-atomic contacts. As expected, the same bright-red spots are observed for the C10—H10⋯F3 (symmetry code: −x + , y + , −z + ) in II (Fig. 2b), C7—H7⋯F3 (symmetry code: x + 1, y, z) in III (Fig. 2c), C15—H15⋯F3 (symmetry code: −x + 1, y + , −z + 1) in IV (Fig. 2d), and both C11—H11⋯F3i and C11—H11⋯F3ii [symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) x, −y + 1, z − ] inter-atomic contacts in V (Fig. 2e). The contributions of the various intermolecular interactions in each of the title compounds are shown in Tables 6–10. With the exception of IV, the packing is dominated by ⋯H/H⋯F interactions, accounting for as high as 36.9% of the packing forces in I. In IV, the largest contribution is made by C⋯H/H⋯C interactions (19.1%), followed closely by F⋯H/H⋯F (18.8%).
Contact | Percentage contribution | F⋯H/H⋯F | 36.9 | C⋯H/H⋯C | 14.8 | F⋯F | 12.1 | H⋯H | 9.6 | N⋯H/H⋯N | 4.8 | F⋯C/C⋯F | 4.7 | F⋯O/O⋯F | 4.2 | C⋯C | 4.1 | N⋯C/C⋯N | 3.2 | O⋯C/C⋯O | 2.2 | O⋯N/N⋯O | 2.0 | F⋯N/N⋯F | 1.3 | O⋯H/H⋯O | 0.1 | | |
Contact | Percentage contribution | F⋯H/H⋯F | 18.7 | F⋯C/C⋯F | 11.8 | C⋯H/H⋯C | 11.7 | F⋯F | 10.8 | Br⋯F/F⋯Br | 8.3 | Br⋯H/H⋯Br | 7.7 | H⋯H | 6.9 | F⋯N/N⋯F | 6.1 | O⋯H/H⋯O | 4.6 | Br⋯N/N⋯Br | 3.5 | C⋯C | 3.4 | Br⋯C/C⋯Br | 2.2 | Br⋯O/O⋯Br | 1.8 | N⋯C/C⋯N | 0.9 | F⋯O/O⋯F | 0.8 | O⋯C/C⋯O | 0.6 | N⋯H/H⋯N | 0.2 | | |
Contact | Percentage contribution | F⋯H/H⋯F | 30.4 | C⋯H/H⋯C | 22.8 | H⋯H | 14.0 | F⋯C/C⋯F | 10.0 | F⋯F | 6.6 | N⋯H/H⋯N | 4.2 | O⋯C/C⋯O | 2.9 | F⋯O/O⋯F | 2.3 | F⋯N/N⋯F | 2.0 | O⋯H/H⋯O | 0.3 | O⋯N/N⋯O | 1.6 | C⋯C | 1.5 | N⋯C/C⋯N | 1.4 | | |
Contact | Percentage contribution | C⋯H/H⋯C | 19.1 | F⋯H/H⋯F | 18.8 | F⋯C/C⋯F | 9.4 | H⋯H | 9.1 | Br⋯H/H⋯Br | 8.7 | F⋯F | 7.7 | Br⋯C/C⋯Br | 7.2 | F⋯O/O⋯F | 4.5 | Br⋯F/F⋯Br | 3.9 | F⋯N/N⋯F | 3.7 | N⋯H/H⋯N | 2.6 | C⋯C | 1.5 | N⋯C/C⋯N | 1.1 | O⋯N/N⋯O | 0.9 | Br⋯N/N⋯Br | 0.8 | O⋯C/C⋯O | 0.6 | O⋯H/H⋯O | 0.3 | | |
Contact | Percentage contribution | F⋯H/H⋯F | 32.3 | F⋯C/C⋯F | 19.0 | H⋯H | 11.6 | F⋯F | 11.3 | N⋯H/H⋯N | 7.1 | F⋯N/N⋯F | 6.3 | C⋯H/H⋯C | 4.8 | O⋯H/H⋯O | 4.5 | F⋯O/O⋯F | 1.8 | C⋯C | 1.3 | | |
| Figure 2 Hirshfeld surface of (a) I, (b) II, (c) III, (d) IV, and (e) V mapped with dnorm. |
Owing to the presence of nitrogen, oxygen and bromine atoms in the various structures, several other contact types are confirmed by the Hirshfeld surface maps. In II, the C9—Br1⋯N1 (symmetry code: − x, − y, − + z) halogen bond is clearly visible. The analogous halogen bond is not observed in IV. Only in III does a C—H⋯N interaction significantly contribute to the packing, with the C15—H15⋯N1 (symmetry code: −x, y + , −z + ] visible in the dnorm surface plot.
4. Database survey
A search of the November 2019 release of the Cambridge Structure Database (Groom et al., 2016), with updates through May 2019, was performed using the program ConQuest (Bruno et al., 2002). The search was limited to organic structures with R ≤ 0.1. A search for perfluoropyridines bearing a ether-linked substituents in the 4-position returned six results: 2,3,5,6-tetrafluoropyridin-4-ol (UDUXEY; Sen et al., 2009); benzophenone O-(2,3,5,6-tetrafluoro-4-pyridyl)oxime (HICBAW; Banks et al., 1995); methyl N,O-bis(2,3,5,6-tetrafluoropyridin-4-yl)threoninate (GOFCIP; Webster et al., 2014); 2,3,5,6-tetrafluoro-4-(4-nitrophenoxy)pyridine and 4,4′-[(1,1′-binaphthalene)-2,2′diylbis(oxy)]bis(tetrafluoropyridine) (FISJUP and FISJOJ; Brittain & Cobb, 2019). In the binaphthalene-derived compound (FISJOJ), analogous to V, the naphthalene ring systems are rotated by 38.91 (5)° from each other.
5. Synthesis and crystallization
2,3,5,6-Tetrafluoro-4-phenoxypyridine (I): To a stirred solution of potassium carbonate (1 M, 147.5 ml), phenol (5.58 g, 59.0 mmol), pentafluoropyridine (6.5 ml, 59 mmol), and DMF (150 ml) were added. The resulting solution was allowed to stir at room temperature for 24 h. Dichloromethane (75 ml) and saturated aqueous ammonium chloride (100 ml) were added and the biphasic solution stirred vigorously for an additional 24 h. The organic layer was separated, washed with water (5 × 200 ml), dried over MgSO4, and solvent removed via rotary evaporation. The resulting pale-brown solid was dissolved in refluxing EtOH (75 ml) and cooled to 278 K for 12 h. Vacuum filtration, washing with cold EtOH (20 ml) and vacuum drying afforded the target compound as a white, crystalline solid (14.3 g, 99%). Colourless needles were obtained from a saturated EtOH solution by cooling to 298 K. 1H NMR (400 MHz, CDCl3): 6.92 (d, 2H, J = 8.0 Hz), 7.08 (d, 1H, J = 8.4 Hz), 7.24 (t, 2H, J = 8.0 Hz). 19F NMR (376 MHz, CDCl3): −88.9, −154.4.
4-(4-Bromophenoxy)-2,3,5,6-tetrafluoropyridine (II): To a stirred solution of potassium carbonate (1 M, 22.8 ml), 4-bromophenol (1.58 g, 9.11 mmol), pentafluoropyridine (1.00 ml, 9.11 mmol), and DMF (25 ml) were added. The resulting solution was allowed to stir at room temperature for 24 h. Diethyl ether (50 ml) and saturated aqueous ammonium chloride (50 ml) were added and the biphasic solution stirred vigorously for an additional 24 h. The organic layer was separated, washed with water (5 × 100 ml), dried over MgSO4, and solvent removed via rotary evaporation. The resulting pale brown solid was dissolved in refluxing EtOH (15 ml) and cooled to 278 K for 12 h. Vacuum filtration, washing with cold EtOH (20 ml) and vacuum drying afforded the target compound as a white, crystalline solid (2.12 g, 73%). Colourless rectangular prisms were obtained from a saturated EtOH solution by cooling to 298 K. 1H NMR (400 MHz, CDCl3): 7.50 (d, 2H, J = 7.5 Hz), 6.96 (d, 2H, J = 7.5 Hz). 19F NMR (376 MHz, CDCl3): −87.9, −154.0.
2,3,5,6-Tetrafluoro-4-[(naphthalen-2-yl)oxy]pyridine (III): To a stirred solution of potassium carbonate (1 M, 90 ml), naphthalen-2-ol (4.98 g, 34.5 mmol), pentafluoropyridine (3.8 ml, 34.5 mmol), and DMF (100 ml) were added. The resulting solution was allowed to stir at room temperature for 24 h. Dichloromethane (50 ml) and saturated aqueous ammonium chloride (100 ml) were added and the biphasic solution stirred vigorously for an additional 24 h. The organic layer was separated, washed with water (5 × 200 ml), dried over MgSO4, and solvent removed via rotary evaporation. The resulting pale brown solid was dissolved in refluxing EtOH (50 ml) and cooled to 298 K for 12 h. Vacuum filtration, washing with cold EtOH (20 ml) and vacuum drying afforded the target compound as a white, crystalline solid (5.90 g, 58%). Colourless rectangular prisms were obtained from a saturated EtOH solution by cooling to 298 K. 1H NMR (500 MHz, CDCl3): 7.90-7.86 (m, 2H), 7.76 (d, 1H, J = 8 Hz), 7.54-7.47 (m, 2H), 7.35–7.31 (m, 2H). 19F NMR (471 MHz, CDCl3): −88.3, −154.0.
2,3,5,6-Tetrafluoro-4-[(6-bromonaphthalen-2-yl)oxy]pyridine (IV): To a stirred solution of potassium carbonate (1 M, 60 ml), 6-bromo-2-naphthol (5.00 g, 22.4 mmol), pentafluoropyridine (2.45 ml, 22.4 mmol), and DMF (60 ml) were added. The resulting solution was allowed to stir at room temperature for 24 h. Diethyl ether (50 ml) and saturated aqueous ammonium chloride (100 ml) were added and the biphasic solution stirred vigorously for an additional 2 h. The organic layer was separated, washed with water (5 × 200 ml), dried over MgSO4, and solvent removed via rotary evaporation. The resulting off-white solid was dissolved in refluxing EtOH (40 ml) and cooled to 298 K for 12 h. Vacuum filtration, washing with cold EtOH (20 ml) and vacuum drying afforded the target compound as a white, crystalline solid (6.46 g, 78%). Colourless plates were obtained from a saturated EtOH solution by cooling to 298 K. 1H NMR (500 MHz, CDCl3): 8.00 (s, 1H), 7.81–7.75 (m, 1H), 7.63–7.55 (m, 2H), 7.35–7.27 (m, 2H). 19F NMR (471 MHz, CDCl3): −87.9, −153.8.
2,2′-Bis[(2,3,5,6-tetrafluoropyridin-4-yl)oxy]-1,1′-biphenyl (V): To a stirred solution of potassium carbonate (1 M, 30 ml), 2,2′-biphenol (1.02 g, 5.37 mmol), pentafluoropyridine (1.2 ml, 11 mmol), and DMF (30 ml) were added. The resulting solution was allowed to stir at room temperature for 24 h. Diethyl ether (50 ml) and saturated aqueous ammonium chloride (100 ml) were added and the biphasic solution stirred vigorously for an additional 2 h. The organic layer was separated, washed with water (5 × 200 ml), dried over MgSO4, and solvent removed via rotary evaporation. The resulting off-white solid was dissolved in refluxing EtOH (10 ml) and cooled to 298 K for 12 h. Vacuum filtration, washing with cold EtOH (20 ml) and vacuum drying afforded the target compound as a white solid (2.57 g, 97%). Colourless rectangular prisms were obtained from a saturated EtOH solution by cooling to 298 K. 1H NMR (500 MHz, CDCl3): 7.45–7.24 (m, 6H), 6.99 (t, 2H, J = 7.5 Hz). 19F NMR (471 MHz, CDCl3): −88.9, −155.0.
6. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 11. H atoms were positioned geometrically and refined using a riding model with C—H = 0.95 Å and Uiso(H) = 1.2Ueq(C). The absolute structures of I and III were intermediate in the present refinement. Compound IV was refined as an inversion twin.
| I | II | III | IV | V | Crystal data | Chemical formula | C11H5F4NO | C11H4BrF4NO | C15H7F4NO | C15H6BrF4NO | C22H8F8N2O2 | Mr | 243.16 | 322.06 | 293.22 | 372.12 | 484.30 | Crystal system, space group | Orthorhombic, P212121 | Monoclinic, P21/n | Orthorhombic, P212121 | Monoclinic, P21 | Orthorhombic, Pbcn | Temperature (K) | 100 | 100 | 100 | 100 | 100 | a, b, c (Å) | 5.4199 (5), 10.3293 (9), 17.4076 (15) | 13.3530 (5), 5.8584 (2), 14.8863 (6) | 5.4703 (5), 9.2548 (9), 24.109 (2) | 6.0135 (3), 7.4994 (4), 14.6318 (7) | 18.8516 (6), 10.6512 (3), 9.2196 (3) | α, β, γ (°) | 90, 90, 90 | 90, 113.585 (2), 90 | 90, 90, 90 | 90, 101.401 (2), 90 | 90, 90, 90 | V (Å3) | 974.54 (15) | 1067.24 (7) | 1220.6 (2) | 646.84 (6) | 1851.22 (10) | Z | 4 | 4 | 4 | 2 | 4 | Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα | Mo Kα | μ (mm−1) | 0.16 | 3.89 | 0.14 | 3.23 | 0.17 | Crystal size (mm) | 0.25 × 0.11 × 0.09 | 0.15 × 0.10 × 0.09 | 0.54 × 0.36 × 0.29 | 0.30 × 0.14 × 0.04 | 0.33 × 0.27 × 0.26 | | Data collection | Diffractometer | Bruker SMART APEX CCD | Bruker SMART APEX CCD | Bruker SMART APEX CCD | Bruker SMART APEX CCD | Bruker SMART APEX CCD | Absorption correction | Multi-scan (SADABS; Bruker, 2017) | Multi-scan (SADABS; Bruker, 2017) | Multi-scan (SADABS; Bruker, 2017) | Multi-scan (SADABS; Bruker, 2017) | Multi-scan (SADABS; Bruker, 2017) | Tmin, Tmax | 0.93, 0.99 | 0.21, 0.72 | 0.83, 0.96 | 0.63, 0.89 | 0.87, 0.96 | No. of measured, independent and observed [I > 2σ(I)] reflections | 13236, 2603, 2520 | 19174, 3544, 3013 | 26820, 3296, 3149 | 12954, 2775, 2566 | 36854, 2830, 2554 | Rint | 0.021 | 0.040 | 0.025 | 0.040 | 0.028 | (sin θ/λ)max (Å−1) | 0.684 | 0.735 | 0.684 | 0.641 | 0.714 | | Refinement | R[F2 > 2σ(F2)], wR(F2), S | 0.028, 0.073, 1.05 | 0.031, 0.083, 1.06 | 0.031, 0.078, 1.07 | 0.031, 0.058, 1.14 | 0.036, 0.098, 1.06 | No. of reflections | 2603 | 3544 | 3296 | 2775 | 2830 | No. of parameters | 154 | 163 | 190 | 200 | 154 | No. of restraints | 0 | 0 | 0 | 1 | 0 | H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | Δρmax, Δρmin (e Å−3) | 0.26, −0.15 | 0.84, −0.77 | 0.27, −0.15 | 0.70, −0.47 | 0.54, −0.24 | Absolute structure | Flack x determined using 1019 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013) | – | Flack x determined using 1255 quotients [(I+)−(I−)]/[(I+)+(I−)] (Parsons et al., 2013) | Refined as an inversion twin | – | Absolute structure parameter | −0.20 (13) | – | −0.08 (14) | 0.171 (12) | – | Computer programs: APEX3 and SAINT (Bruker, 2017), SHELXT (Sheldrick, 2015a), SHELXL2016/6 (Sheldrick, 2015b), Mercury (Macrae et al., 2008), Olex2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010). | |
Supporting information
For all structures, data collection: APEX3 (Bruker, 2017); cell refinement: SAINT (Bruker, 2017); data reduction: SAINT (Bruker, 2017); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2008). Software used to prepare material for publication: Olex2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010) for (I); publCIF (Westrip, 2010) for (II), (III), (IV), (V).
2,3,5,6-Tetrafluoro-4-phenoxypyridine (I)
top Crystal data top C11H5F4NO | Dx = 1.657 Mg m−3 |
Mr = 243.16 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 7895 reflections |
a = 5.4199 (5) Å | θ = 2.3–29.5° |
b = 10.3293 (9) Å | µ = 0.16 mm−1 |
c = 17.4076 (15) Å | T = 100 K |
V = 974.54 (15) Å3 | Needle, colourless |
Z = 4 | 0.25 × 0.11 × 0.09 mm |
F(000) = 488 | |
Data collection top Bruker SMART APEX CCD diffractometer | 2603 independent reflections |
Radiation source: fine focus sealed tube | 2520 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.1°, θmin = 2.3° |
ω Scans scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | k = −14→14 |
Tmin = 0.93, Tmax = 0.99 | l = −23→23 |
13236 measured reflections | |
Refinement top Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.028 | w = 1/[σ2(Fo2) + (0.0371P)2 + 0.2471P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.073 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.26 e Å−3 |
2603 reflections | Δρmin = −0.15 e Å−3 |
154 parameters | Absolute structure: Flack x determined using 1019 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: −0.20 (13) |
Primary atom site location: structure-invariant direct methods | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | 1.0458 (2) | 0.96948 (10) | 0.27358 (6) | 0.0304 (2) | |
F2 | 0.64334 (19) | 0.87849 (9) | 0.34737 (5) | 0.0247 (2) | |
F3 | 0.4522 (2) | 0.64159 (11) | 0.12257 (6) | 0.0339 (3) | |
F4 | 0.8628 (2) | 0.74537 (11) | 0.05818 (6) | 0.0354 (3) | |
O1 | 0.3304 (2) | 0.70337 (11) | 0.27133 (6) | 0.0220 (2) | |
N1 | 0.9535 (3) | 0.85667 (14) | 0.16598 (8) | 0.0232 (3) | |
C1 | 0.8951 (3) | 0.88735 (15) | 0.23682 (9) | 0.0214 (3) | |
C2 | 0.6915 (3) | 0.84050 (14) | 0.27546 (8) | 0.0185 (3) | |
C3 | 0.5371 (3) | 0.75320 (15) | 0.23844 (9) | 0.0182 (3) | |
C4 | 0.5954 (3) | 0.72270 (15) | 0.16263 (9) | 0.0223 (3) | |
C5 | 0.8047 (3) | 0.77713 (16) | 0.13038 (9) | 0.0240 (3) | |
C6 | 0.3557 (3) | 0.65167 (14) | 0.34628 (8) | 0.0179 (3) | |
C7 | 0.1718 (3) | 0.68151 (16) | 0.39875 (9) | 0.0212 (3) | |
H7 | 0.041504 | 0.738816 | 0.385477 | 0.025* | |
C8 | 0.1829 (3) | 0.62530 (16) | 0.47149 (9) | 0.0227 (3) | |
H8 | 0.058655 | 0.644261 | 0.508309 | 0.027* | |
C9 | 0.3749 (3) | 0.54150 (15) | 0.49061 (9) | 0.0214 (3) | |
H9 | 0.380741 | 0.503169 | 0.540181 | 0.026* | |
C10 | 0.5583 (3) | 0.51402 (15) | 0.43697 (9) | 0.0210 (3) | |
H10 | 0.689859 | 0.4575 | 0.450189 | 0.025* | |
C11 | 0.5492 (3) | 0.56943 (15) | 0.36367 (9) | 0.0194 (3) | |
H11 | 0.673132 | 0.550979 | 0.326676 | 0.023* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0275 (5) | 0.0317 (5) | 0.0320 (5) | −0.0123 (4) | −0.0031 (4) | 0.0032 (4) |
F2 | 0.0311 (5) | 0.0254 (5) | 0.0177 (4) | −0.0052 (4) | 0.0026 (4) | −0.0038 (4) |
F3 | 0.0478 (7) | 0.0312 (5) | 0.0228 (5) | −0.0132 (5) | −0.0036 (5) | −0.0051 (4) |
F4 | 0.0497 (7) | 0.0354 (6) | 0.0210 (5) | 0.0030 (5) | 0.0127 (5) | −0.0014 (4) |
O1 | 0.0185 (5) | 0.0281 (6) | 0.0193 (5) | −0.0037 (5) | −0.0018 (4) | 0.0049 (4) |
N1 | 0.0218 (6) | 0.0234 (6) | 0.0242 (6) | 0.0035 (5) | 0.0047 (5) | 0.0067 (5) |
C1 | 0.0201 (7) | 0.0196 (7) | 0.0245 (7) | −0.0010 (6) | −0.0025 (6) | 0.0044 (6) |
C2 | 0.0208 (7) | 0.0184 (6) | 0.0163 (6) | 0.0007 (6) | −0.0006 (5) | 0.0013 (5) |
C3 | 0.0178 (6) | 0.0177 (6) | 0.0191 (6) | 0.0008 (5) | −0.0012 (5) | 0.0029 (5) |
C4 | 0.0295 (8) | 0.0184 (7) | 0.0190 (7) | −0.0002 (6) | −0.0018 (6) | 0.0005 (5) |
C5 | 0.0316 (8) | 0.0222 (7) | 0.0182 (7) | 0.0061 (7) | 0.0058 (6) | 0.0029 (6) |
C6 | 0.0178 (6) | 0.0185 (6) | 0.0175 (6) | −0.0035 (5) | −0.0013 (5) | 0.0009 (5) |
C7 | 0.0160 (6) | 0.0235 (7) | 0.0240 (7) | 0.0018 (6) | 0.0000 (6) | −0.0006 (6) |
C8 | 0.0199 (7) | 0.0270 (7) | 0.0214 (7) | −0.0002 (6) | 0.0041 (6) | −0.0017 (6) |
C9 | 0.0238 (7) | 0.0216 (7) | 0.0188 (7) | −0.0013 (6) | 0.0010 (6) | 0.0019 (5) |
C10 | 0.0199 (7) | 0.0186 (7) | 0.0245 (7) | 0.0013 (6) | 0.0005 (6) | 0.0022 (6) |
C11 | 0.0183 (6) | 0.0186 (7) | 0.0212 (7) | −0.0002 (5) | 0.0035 (6) | 0.0000 (5) |
Geometric parameters (Å, º) top F1—C1 | 1.3404 (18) | C6—C11 | 1.383 (2) |
F2—C2 | 1.3375 (17) | C6—C7 | 1.387 (2) |
F3—C4 | 1.3382 (19) | C7—C8 | 1.394 (2) |
F4—C5 | 1.3366 (18) | C7—H7 | 0.9500 |
O1—C3 | 1.3594 (18) | C8—C9 | 1.394 (2) |
O1—C6 | 1.4164 (18) | C8—H8 | 0.9500 |
N1—C5 | 1.307 (2) | C9—C10 | 1.393 (2) |
N1—C1 | 1.312 (2) | C9—H9 | 0.9500 |
C1—C2 | 1.380 (2) | C10—C11 | 1.399 (2) |
C2—C3 | 1.389 (2) | C10—H10 | 0.9500 |
C3—C4 | 1.393 (2) | C11—H11 | 0.9500 |
C4—C5 | 1.385 (2) | | |
| | | |
C3—O1—C6 | 116.81 (12) | C11—C6—O1 | 120.43 (13) |
C5—N1—C1 | 116.66 (14) | C7—C6—O1 | 116.98 (13) |
N1—C1—F1 | 117.05 (14) | C6—C7—C8 | 118.34 (15) |
N1—C1—C2 | 124.49 (15) | C6—C7—H7 | 120.8 |
F1—C1—C2 | 118.46 (14) | C8—C7—H7 | 120.8 |
F2—C2—C1 | 120.62 (14) | C9—C8—C7 | 120.50 (15) |
F2—C2—C3 | 120.48 (14) | C9—C8—H8 | 119.8 |
C1—C2—C3 | 118.90 (14) | C7—C8—H8 | 119.8 |
O1—C3—C2 | 123.16 (13) | C10—C9—C8 | 119.95 (14) |
O1—C3—C4 | 120.02 (14) | C10—C9—H9 | 120.0 |
C2—C3—C4 | 116.73 (14) | C8—C9—H9 | 120.0 |
F3—C4—C5 | 121.20 (15) | C9—C10—C11 | 120.18 (15) |
F3—C4—C3 | 120.24 (15) | C9—C10—H10 | 119.9 |
C5—C4—C3 | 118.56 (15) | C11—C10—H10 | 119.9 |
N1—C5—F4 | 117.04 (15) | C6—C11—C10 | 118.52 (14) |
N1—C5—C4 | 124.62 (15) | C6—C11—H11 | 120.7 |
F4—C5—C4 | 118.33 (16) | C10—C11—H11 | 120.7 |
C11—C6—C7 | 122.50 (14) | | |
| | | |
C5—N1—C1—F1 | −179.60 (14) | C1—N1—C5—F4 | 180.00 (14) |
C5—N1—C1—C2 | 0.7 (2) | C1—N1—C5—C4 | −1.1 (2) |
N1—C1—C2—F2 | −178.92 (14) | F3—C4—C5—N1 | −179.80 (15) |
F1—C1—C2—F2 | 1.4 (2) | C3—C4—C5—N1 | −0.4 (2) |
N1—C1—C2—C3 | 1.1 (2) | F3—C4—C5—F4 | −0.9 (2) |
F1—C1—C2—C3 | −178.63 (13) | C3—C4—C5—F4 | 178.56 (14) |
C6—O1—C3—C2 | −49.3 (2) | C3—O1—C6—C11 | −46.61 (19) |
C6—O1—C3—C4 | 134.31 (15) | C3—O1—C6—C7 | 136.93 (15) |
F2—C2—C3—O1 | 1.0 (2) | C11—C6—C7—C8 | −0.5 (2) |
C1—C2—C3—O1 | −178.94 (14) | O1—C6—C7—C8 | 175.90 (14) |
F2—C2—C3—C4 | 177.58 (14) | C6—C7—C8—C9 | 0.1 (2) |
C1—C2—C3—C4 | −2.4 (2) | C7—C8—C9—C10 | 0.4 (2) |
O1—C3—C4—F3 | −1.8 (2) | C8—C9—C10—C11 | −0.6 (2) |
C2—C3—C4—F3 | −178.48 (14) | C7—C6—C11—C10 | 0.3 (2) |
O1—C3—C4—C5 | 178.73 (14) | O1—C6—C11—C10 | −175.95 (14) |
C2—C3—C4—C5 | 2.1 (2) | C9—C10—C11—C6 | 0.2 (2) |
4-(4-Bromophenoxy)-2,3,5,6-tetrafluoropyridine (II)
top Crystal data top C11H4BrF4NO | F(000) = 624 |
Mr = 322.06 | Dx = 2.004 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.3530 (5) Å | Cell parameters from 7652 reflections |
b = 5.8584 (2) Å | θ = 2.6–31.9° |
c = 14.8863 (6) Å | µ = 3.89 mm−1 |
β = 113.585 (2)° | T = 100 K |
V = 1067.24 (7) Å3 | Rectangular prism, colourless |
Z = 4 | 0.15 × 0.10 × 0.09 mm |
Data collection top Bruker SMART APEX CCD diffractometer | 3544 independent reflections |
Radiation source: fine focus sealed tube | 3013 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 31.5°, θmin = 1.7° |
ω Scans scans | h = −19→19 |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | k = −8→8 |
Tmin = 0.21, Tmax = 0.72 | l = −21→21 |
19174 measured reflections | |
Refinement top Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.050P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.002 |
3544 reflections | Δρmax = 0.84 e Å−3 |
163 parameters | Δρmin = −0.77 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 0.69708 (2) | 0.16236 (3) | 0.49318 (2) | 0.01909 (7) | |
F1 | 0.26006 (9) | 0.89335 (18) | 0.84433 (9) | 0.0217 (2) | |
F2 | 0.38676 (8) | 1.02091 (16) | 0.74927 (8) | 0.0180 (2) | |
F3 | 0.57954 (9) | 0.32539 (15) | 0.85557 (9) | 0.0198 (2) | |
F4 | 0.44206 (9) | 0.22697 (18) | 0.94178 (8) | 0.0204 (2) | |
O1 | 0.55019 (9) | 0.75025 (19) | 0.75137 (9) | 0.0171 (3) | |
N1 | 0.35097 (12) | 0.5592 (2) | 0.89200 (11) | 0.0165 (3) | |
C1 | 0.33969 (13) | 0.7540 (3) | 0.84459 (13) | 0.0158 (3) | |
C2 | 0.40295 (14) | 0.8195 (2) | 0.79609 (13) | 0.0138 (3) | |
C3 | 0.48559 (14) | 0.6752 (3) | 0.79564 (13) | 0.0139 (3) | |
C4 | 0.49951 (13) | 0.4716 (3) | 0.84799 (12) | 0.0146 (3) | |
C5 | 0.42904 (14) | 0.4238 (3) | 0.89247 (12) | 0.0151 (3) | |
C6 | 0.57942 (13) | 0.6035 (3) | 0.69117 (12) | 0.0140 (3) | |
C7 | 0.52283 (14) | 0.4050 (3) | 0.65069 (13) | 0.0161 (3) | |
H7 | 0.460999 | 0.360861 | 0.662945 | 0.019* | |
C8 | 0.55832 (14) | 0.2716 (3) | 0.59177 (13) | 0.0167 (3) | |
H8 | 0.522146 | 0.13251 | 0.564996 | 0.02* | |
C9 | 0.64660 (14) | 0.3426 (3) | 0.57230 (13) | 0.0147 (3) | |
C10 | 0.70034 (14) | 0.5462 (3) | 0.61029 (13) | 0.0162 (3) | |
H10 | 0.759498 | 0.595176 | 0.594964 | 0.019* | |
C11 | 0.66669 (14) | 0.6774 (3) | 0.67088 (13) | 0.0153 (3) | |
H11 | 0.703098 | 0.816021 | 0.698056 | 0.018* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.02336 (11) | 0.01936 (10) | 0.01944 (11) | 0.00095 (6) | 0.01371 (8) | −0.00288 (6) |
F1 | 0.0176 (5) | 0.0205 (5) | 0.0311 (7) | 0.0047 (4) | 0.0139 (5) | −0.0027 (4) |
F2 | 0.0211 (5) | 0.0126 (4) | 0.0200 (5) | 0.0021 (4) | 0.0079 (4) | 0.0014 (4) |
F3 | 0.0176 (5) | 0.0176 (5) | 0.0239 (6) | 0.0066 (4) | 0.0081 (4) | 0.0008 (4) |
F4 | 0.0280 (6) | 0.0157 (5) | 0.0170 (5) | −0.0011 (4) | 0.0082 (4) | 0.0035 (4) |
O1 | 0.0209 (6) | 0.0151 (6) | 0.0210 (7) | −0.0036 (5) | 0.0145 (5) | −0.0047 (5) |
N1 | 0.0169 (7) | 0.0177 (6) | 0.0166 (7) | −0.0019 (5) | 0.0086 (6) | −0.0027 (5) |
C1 | 0.0138 (7) | 0.0155 (7) | 0.0182 (9) | 0.0004 (6) | 0.0065 (6) | −0.0041 (6) |
C2 | 0.0158 (7) | 0.0110 (7) | 0.0134 (8) | −0.0011 (5) | 0.0047 (6) | −0.0020 (5) |
C3 | 0.0136 (7) | 0.0155 (7) | 0.0137 (8) | −0.0031 (5) | 0.0064 (6) | −0.0037 (5) |
C4 | 0.0132 (7) | 0.0149 (7) | 0.0143 (8) | 0.0018 (6) | 0.0040 (6) | −0.0020 (5) |
C5 | 0.0196 (8) | 0.0136 (7) | 0.0107 (8) | −0.0006 (6) | 0.0047 (6) | 0.0006 (5) |
C6 | 0.0147 (7) | 0.0142 (7) | 0.0142 (8) | 0.0006 (6) | 0.0068 (6) | −0.0016 (6) |
C7 | 0.0151 (7) | 0.0176 (7) | 0.0181 (8) | −0.0044 (6) | 0.0094 (6) | −0.0042 (6) |
C8 | 0.0189 (8) | 0.0156 (7) | 0.0172 (9) | −0.0040 (6) | 0.0091 (7) | −0.0045 (6) |
C9 | 0.0153 (7) | 0.0167 (7) | 0.0132 (8) | 0.0016 (6) | 0.0068 (6) | −0.0003 (5) |
C10 | 0.0143 (7) | 0.0186 (7) | 0.0174 (8) | −0.0022 (6) | 0.0080 (6) | −0.0009 (6) |
C11 | 0.0151 (7) | 0.0166 (7) | 0.0155 (8) | −0.0041 (6) | 0.0076 (7) | −0.0014 (6) |
Geometric parameters (Å, º) top Br1—C9 | 1.8952 (17) | C4—C5 | 1.379 (2) |
F1—C1 | 1.3395 (19) | C6—C11 | 1.385 (2) |
F2—C2 | 1.3430 (18) | C6—C7 | 1.386 (2) |
F3—C4 | 1.3386 (18) | C7—C8 | 1.392 (2) |
F4—C5 | 1.3401 (19) | C7—H7 | 0.95 |
O1—C3 | 1.352 (2) | C8—C9 | 1.385 (2) |
O1—C6 | 1.4050 (19) | C8—H8 | 0.95 |
N1—C5 | 1.308 (2) | C9—C10 | 1.390 (2) |
N1—C1 | 1.318 (2) | C10—C11 | 1.389 (2) |
C1—C2 | 1.368 (2) | C10—H10 | 0.95 |
C2—C3 | 1.392 (2) | C11—H11 | 0.95 |
C3—C4 | 1.396 (2) | | |
| | | |
C3—O1—C6 | 120.41 (13) | C11—C6—O1 | 114.89 (14) |
C5—N1—C1 | 116.63 (15) | C7—C6—O1 | 123.25 (15) |
N1—C1—F1 | 116.72 (15) | C6—C7—C8 | 118.76 (16) |
N1—C1—C2 | 124.29 (15) | C6—C7—H7 | 120.6 |
F1—C1—C2 | 118.99 (16) | C8—C7—H7 | 120.6 |
F2—C2—C1 | 121.02 (15) | C9—C8—C7 | 119.74 (16) |
F2—C2—C3 | 119.63 (15) | C9—C8—H8 | 120.1 |
C1—C2—C3 | 119.34 (15) | C7—C8—H8 | 120.1 |
O1—C3—C2 | 117.79 (14) | C8—C9—C10 | 121.07 (16) |
O1—C3—C4 | 125.59 (15) | C8—C9—Br1 | 120.46 (12) |
C2—C3—C4 | 116.43 (15) | C10—C9—Br1 | 118.47 (13) |
F3—C4—C5 | 120.31 (15) | C11—C10—C9 | 119.35 (16) |
F3—C4—C3 | 121.15 (15) | C11—C10—H10 | 120.3 |
C5—C4—C3 | 118.54 (15) | C9—C10—H10 | 120.3 |
N1—C5—F4 | 116.96 (15) | C6—C11—C10 | 119.20 (15) |
N1—C5—C4 | 124.73 (16) | C6—C11—H11 | 120.4 |
F4—C5—C4 | 118.29 (15) | C10—C11—H11 | 120.4 |
C11—C6—C7 | 121.80 (16) | | |
| | | |
C5—N1—C1—F1 | −179.75 (15) | C1—N1—C5—C4 | 0.5 (3) |
C5—N1—C1—C2 | 0.7 (3) | F3—C4—C5—N1 | 177.56 (15) |
N1—C1—C2—F2 | −179.99 (15) | C3—C4—C5—N1 | −2.2 (3) |
F1—C1—C2—F2 | 0.5 (2) | F3—C4—C5—F4 | −0.9 (2) |
N1—C1—C2—C3 | −0.2 (3) | C3—C4—C5—F4 | 179.31 (14) |
F1—C1—C2—C3 | −179.71 (15) | C3—O1—C6—C11 | −163.96 (15) |
C6—O1—C3—C2 | −137.39 (15) | C3—O1—C6—C7 | 19.0 (2) |
C6—O1—C3—C4 | 47.9 (2) | C11—C6—C7—C8 | 3.0 (3) |
F2—C2—C3—O1 | 3.2 (2) | O1—C6—C7—C8 | 179.83 (16) |
C1—C2—C3—O1 | −176.63 (15) | C6—C7—C8—C9 | −2.0 (3) |
F2—C2—C3—C4 | 178.33 (14) | C7—C8—C9—C10 | −0.4 (3) |
C1—C2—C3—C4 | −1.5 (2) | C7—C8—C9—Br1 | 179.46 (13) |
O1—C3—C4—F3 | −2.5 (3) | C8—C9—C10—C11 | 1.7 (3) |
C2—C3—C4—F3 | −177.21 (15) | Br1—C9—C10—C11 | −178.07 (13) |
O1—C3—C4—C5 | 177.29 (16) | C7—C6—C11—C10 | −1.7 (3) |
C2—C3—C4—C5 | 2.5 (2) | O1—C6—C11—C10 | −178.70 (15) |
C1—N1—C5—F4 | 179.03 (14) | C9—C10—C11—C6 | −0.8 (3) |
2,3,5,6-Tetrafluoro-4-[(naphthalen-2-yl)oxy]pyridine (III)
top Crystal data top C15H7F4NO | Dx = 1.596 Mg m−3 |
Mr = 293.22 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 9963 reflections |
a = 5.4703 (5) Å | θ = 2.4–29.2° |
b = 9.2548 (9) Å | µ = 0.14 mm−1 |
c = 24.109 (2) Å | T = 100 K |
V = 1220.6 (2) Å3 | Rectangular prism, colourless |
Z = 4 | 0.54 × 0.36 × 0.29 mm |
F(000) = 592 | |
Data collection top Bruker SMART APEX CCD diffractometer | 3296 independent reflections |
Radiation source: fine focus sealed tube | 3149 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 29.1°, θmin = 2.4° |
ω Scans scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | k = −12→12 |
Tmin = 0.83, Tmax = 0.96 | l = −32→33 |
26820 measured reflections | |
Refinement top Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0385P)2 + 0.2387P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.078 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.27 e Å−3 |
3296 reflections | Δρmin = −0.15 e Å−3 |
190 parameters | Absolute structure: Flack x determined using 1255 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: −0.08 (14) |
Primary atom site location: structure-invariant direct methods | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | 0.1901 (3) | 0.27940 (14) | 0.13034 (5) | 0.0479 (3) | |
F2 | 0.5809 (2) | 0.39295 (12) | 0.18393 (4) | 0.0389 (3) | |
F3 | 0.2850 (2) | 0.16943 (11) | 0.34729 (4) | 0.0312 (2) | |
F4 | −0.0860 (2) | 0.06445 (13) | 0.28603 (6) | 0.0493 (3) | |
O1 | 0.6420 (2) | 0.34634 (14) | 0.29382 (5) | 0.0277 (3) | |
N1 | 0.0540 (3) | 0.17233 (17) | 0.20838 (7) | 0.0356 (3) | |
C1 | 0.2194 (4) | 0.25229 (19) | 0.18427 (7) | 0.0320 (4) | |
C2 | 0.4193 (3) | 0.31157 (17) | 0.21119 (6) | 0.0265 (3) | |
C3 | 0.4454 (3) | 0.28847 (16) | 0.26793 (6) | 0.0222 (3) | |
C4 | 0.2711 (3) | 0.20160 (17) | 0.29324 (6) | 0.0246 (3) | |
C5 | 0.0823 (3) | 0.14819 (18) | 0.26127 (8) | 0.0320 (4) | |
C6 | 0.6094 (3) | 0.40005 (17) | 0.34853 (6) | 0.0228 (3) | |
C7 | 0.7792 (3) | 0.36372 (17) | 0.38711 (6) | 0.0241 (3) | |
H7 | 0.908206 | 0.299232 | 0.377994 | 0.029* | |
C8 | 0.7619 (3) | 0.42322 (17) | 0.44129 (6) | 0.0226 (3) | |
C9 | 0.9344 (3) | 0.3885 (2) | 0.48337 (7) | 0.0285 (3) | |
H9 | 1.064542 | 0.323683 | 0.475557 | 0.034* | |
C10 | 0.9133 (3) | 0.4482 (2) | 0.53513 (7) | 0.0320 (4) | |
H10 | 1.030211 | 0.425143 | 0.562892 | 0.038* | |
C11 | 0.7196 (4) | 0.5437 (2) | 0.54765 (7) | 0.0326 (4) | |
H11 | 0.707125 | 0.584129 | 0.583766 | 0.039* | |
C12 | 0.5492 (4) | 0.57864 (19) | 0.50802 (7) | 0.0294 (3) | |
H12 | 0.419415 | 0.642863 | 0.516865 | 0.035* | |
C13 | 0.5662 (3) | 0.51895 (17) | 0.45372 (6) | 0.0233 (3) | |
C14 | 0.3926 (3) | 0.55230 (17) | 0.41174 (7) | 0.0250 (3) | |
H14 | 0.260636 | 0.615515 | 0.419906 | 0.03* | |
C15 | 0.4135 (3) | 0.49422 (17) | 0.35952 (6) | 0.0242 (3) | |
H15 | 0.298037 | 0.51716 | 0.331426 | 0.029* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0678 (8) | 0.0484 (7) | 0.0276 (5) | 0.0196 (6) | −0.0202 (6) | −0.0095 (5) |
F2 | 0.0582 (7) | 0.0356 (5) | 0.0229 (4) | −0.0087 (5) | 0.0076 (5) | 0.0027 (4) |
F3 | 0.0379 (6) | 0.0285 (5) | 0.0271 (5) | −0.0018 (4) | 0.0053 (4) | 0.0050 (4) |
F4 | 0.0365 (6) | 0.0367 (6) | 0.0748 (9) | −0.0157 (5) | 0.0055 (6) | −0.0067 (6) |
O1 | 0.0237 (5) | 0.0394 (6) | 0.0199 (5) | −0.0060 (5) | 0.0015 (4) | −0.0052 (5) |
N1 | 0.0318 (7) | 0.0300 (7) | 0.0449 (8) | 0.0049 (6) | −0.0128 (7) | −0.0146 (6) |
C1 | 0.0416 (10) | 0.0272 (8) | 0.0271 (8) | 0.0118 (7) | −0.0106 (7) | −0.0084 (6) |
C2 | 0.0358 (8) | 0.0221 (7) | 0.0216 (7) | 0.0024 (7) | −0.0004 (6) | −0.0010 (5) |
C3 | 0.0234 (7) | 0.0210 (6) | 0.0221 (7) | 0.0008 (6) | −0.0015 (6) | −0.0011 (5) |
C4 | 0.0267 (7) | 0.0212 (6) | 0.0260 (7) | 0.0015 (6) | 0.0005 (6) | 0.0001 (6) |
C5 | 0.0261 (8) | 0.0224 (7) | 0.0474 (10) | −0.0016 (6) | −0.0013 (7) | −0.0064 (7) |
C6 | 0.0228 (7) | 0.0273 (7) | 0.0182 (6) | −0.0047 (6) | 0.0010 (5) | −0.0003 (6) |
C7 | 0.0192 (6) | 0.0293 (7) | 0.0237 (6) | −0.0001 (6) | 0.0012 (5) | −0.0001 (6) |
C8 | 0.0200 (7) | 0.0264 (7) | 0.0215 (6) | −0.0026 (6) | −0.0010 (6) | 0.0033 (5) |
C9 | 0.0230 (7) | 0.0378 (9) | 0.0248 (7) | 0.0001 (7) | −0.0019 (6) | 0.0061 (6) |
C10 | 0.0306 (8) | 0.0429 (10) | 0.0227 (7) | −0.0051 (8) | −0.0055 (7) | 0.0062 (7) |
C11 | 0.0396 (9) | 0.0379 (9) | 0.0204 (7) | −0.0058 (8) | −0.0011 (7) | −0.0016 (6) |
C12 | 0.0333 (8) | 0.0298 (8) | 0.0251 (7) | −0.0003 (7) | 0.0009 (7) | −0.0028 (6) |
C13 | 0.0246 (7) | 0.0231 (7) | 0.0222 (7) | −0.0034 (6) | −0.0001 (6) | 0.0015 (5) |
C14 | 0.0250 (7) | 0.0234 (7) | 0.0264 (7) | 0.0018 (6) | −0.0010 (6) | 0.0003 (6) |
C15 | 0.0237 (7) | 0.0259 (7) | 0.0231 (7) | −0.0016 (6) | −0.0041 (6) | 0.0025 (5) |
Geometric parameters (Å, º) top F1—C1 | 1.334 (2) | C7—H7 | 0.95 |
F2—C2 | 1.334 (2) | C8—C13 | 1.421 (2) |
F3—C4 | 1.3389 (18) | C8—C9 | 1.422 (2) |
F4—C5 | 1.343 (2) | C9—C10 | 1.369 (2) |
O1—C3 | 1.3538 (19) | C9—H9 | 0.95 |
O1—C6 | 1.4209 (18) | C10—C11 | 1.413 (3) |
N1—C5 | 1.304 (3) | C10—H10 | 0.95 |
N1—C1 | 1.305 (3) | C11—C12 | 1.374 (2) |
C1—C2 | 1.385 (3) | C11—H11 | 0.95 |
C2—C3 | 1.392 (2) | C12—C13 | 1.424 (2) |
C3—C4 | 1.389 (2) | C12—H12 | 0.95 |
C4—C5 | 1.380 (2) | C13—C14 | 1.421 (2) |
C6—C7 | 1.357 (2) | C14—C15 | 1.374 (2) |
C6—C15 | 1.407 (2) | C14—H14 | 0.95 |
C7—C8 | 1.421 (2) | C15—H15 | 0.95 |
| | | |
C3—O1—C6 | 117.82 (12) | C7—C8—C9 | 121.61 (15) |
C5—N1—C1 | 116.78 (16) | C13—C8—C9 | 119.34 (14) |
N1—C1—F1 | 117.23 (17) | C10—C9—C8 | 120.20 (16) |
N1—C1—C2 | 124.26 (16) | C10—C9—H9 | 119.9 |
F1—C1—C2 | 118.50 (18) | C8—C9—H9 | 119.9 |
F2—C2—C1 | 121.05 (15) | C9—C10—C11 | 120.68 (15) |
F2—C2—C3 | 120.19 (16) | C9—C10—H10 | 119.7 |
C1—C2—C3 | 118.73 (16) | C11—C10—H10 | 119.7 |
O1—C3—C4 | 124.90 (14) | C12—C11—C10 | 120.51 (15) |
O1—C3—C2 | 118.27 (15) | C12—C11—H11 | 119.7 |
C4—C3—C2 | 116.76 (15) | C10—C11—H11 | 119.7 |
F3—C4—C5 | 120.43 (15) | C11—C12—C13 | 120.26 (16) |
F3—C4—C3 | 121.15 (14) | C11—C12—H12 | 119.9 |
C5—C4—C3 | 118.42 (15) | C13—C12—H12 | 119.9 |
N1—C5—F4 | 116.90 (17) | C14—C13—C8 | 119.22 (13) |
N1—C5—C4 | 125.00 (17) | C14—C13—C12 | 121.77 (15) |
F4—C5—C4 | 118.11 (17) | C8—C13—C12 | 119.00 (14) |
C7—C6—C15 | 123.10 (14) | C15—C14—C13 | 120.81 (15) |
C7—C6—O1 | 117.64 (14) | C15—C14—H14 | 119.6 |
C15—C6—O1 | 119.15 (13) | C13—C14—H14 | 119.6 |
C6—C7—C8 | 119.25 (14) | C14—C15—C6 | 118.57 (14) |
C6—C7—H7 | 120.4 | C14—C15—H15 | 120.7 |
C8—C7—H7 | 120.4 | C6—C15—H15 | 120.7 |
C7—C8—C13 | 119.05 (13) | | |
| | | |
C5—N1—C1—F1 | −179.02 (15) | C3—O1—C6—C7 | 134.10 (15) |
C5—N1—C1—C2 | 0.1 (3) | C3—O1—C6—C15 | −49.6 (2) |
N1—C1—C2—F2 | −179.70 (15) | C15—C6—C7—C8 | −0.4 (2) |
F1—C1—C2—F2 | −0.6 (2) | O1—C6—C7—C8 | 175.80 (13) |
N1—C1—C2—C3 | −1.6 (3) | C6—C7—C8—C13 | 0.3 (2) |
F1—C1—C2—C3 | 177.43 (14) | C6—C7—C8—C9 | 179.80 (15) |
C6—O1—C3—C4 | −39.6 (2) | C7—C8—C9—C10 | 179.68 (15) |
C6—O1—C3—C2 | 143.33 (15) | C13—C8—C9—C10 | −0.8 (2) |
F2—C2—C3—O1 | −2.2 (2) | C8—C9—C10—C11 | 0.6 (3) |
C1—C2—C3—O1 | 179.72 (14) | C9—C10—C11—C12 | −0.2 (3) |
F2—C2—C3—C4 | −179.48 (15) | C10—C11—C12—C13 | −0.1 (3) |
C1—C2—C3—C4 | 2.4 (2) | C7—C8—C13—C14 | 0.2 (2) |
O1—C3—C4—F3 | 0.8 (2) | C9—C8—C13—C14 | −179.35 (15) |
C2—C3—C4—F3 | 177.89 (14) | C7—C8—C13—C12 | −179.93 (15) |
O1—C3—C4—C5 | −178.91 (15) | C9—C8—C13—C12 | 0.5 (2) |
C2—C3—C4—C5 | −1.8 (2) | C11—C12—C13—C14 | 179.78 (16) |
C1—N1—C5—F4 | −179.19 (15) | C11—C12—C13—C8 | −0.1 (2) |
C1—N1—C5—C4 | 0.6 (3) | C8—C13—C14—C15 | −0.6 (2) |
F3—C4—C5—N1 | −179.41 (16) | C12—C13—C14—C15 | 179.57 (16) |
C3—C4—C5—N1 | 0.3 (3) | C13—C14—C15—C6 | 0.5 (2) |
F3—C4—C5—F4 | 0.4 (2) | C7—C6—C15—C14 | 0.0 (2) |
C3—C4—C5—F4 | −179.88 (14) | O1—C6—C15—C14 | −176.10 (14) |
4-[(6-Bromonaphthalen-2-yl)oxy]-2,3,5,6-tetrafluoropyridine (IV)
top Crystal data top C15H6BrF4NO | F(000) = 364 |
Mr = 372.12 | Dx = 1.911 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.0135 (3) Å | Cell parameters from 7392 reflections |
b = 7.4994 (4) Å | θ = 3.1–27.4° |
c = 14.6318 (7) Å | µ = 3.23 mm−1 |
β = 101.401 (2)° | T = 100 K |
V = 646.84 (6) Å3 | Plate, colourless |
Z = 2 | 0.30 × 0.14 × 0.04 mm |
Data collection top Bruker SMART APEX CCD diffractometer | 2775 independent reflections |
Radiation source: fine focus sealed tube | 2566 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 27.1°, θmin = 1.4° |
ω Scans scans | h = −7→7 |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | k = −9→9 |
Tmin = 0.63, Tmax = 0.89 | l = −18→18 |
12954 measured reflections | |
Refinement top Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.031 | w = 1/[σ2(Fo2) + (0.0174P)2 + 0.147P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.058 | (Δ/σ)max = 0.001 |
S = 1.14 | Δρmax = 0.70 e Å−3 |
2775 reflections | Δρmin = −0.46 e Å−3 |
200 parameters | Absolute structure: Refined as an inversion twin |
1 restraint | Absolute structure parameter: 0.171 (12) |
Primary atom site location: structure-invariant direct methods | |
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. Refined as a 2-component inversion twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Br1 | 1.11387 (6) | 0.12723 (7) | 0.65331 (3) | 0.02027 (12) | |
F1 | 0.1437 (5) | 0.8959 (4) | 0.1693 (2) | 0.0341 (8) | |
F2 | 0.4300 (3) | 0.6186 (6) | 0.20499 (14) | 0.0245 (5) | |
F3 | −0.1671 (5) | 0.2537 (4) | 0.04981 (19) | 0.0325 (7) | |
F4 | −0.4284 (4) | 0.5505 (4) | 0.0217 (2) | 0.0430 (9) | |
O1 | 0.2637 (6) | 0.2724 (4) | 0.1423 (2) | 0.0258 (8) | |
N1 | −0.1424 (7) | 0.7231 (7) | 0.0963 (3) | 0.0276 (11) | |
C1 | 0.0692 (8) | 0.7344 (7) | 0.1415 (3) | 0.0242 (11) | |
C2 | 0.2157 (7) | 0.5921 (6) | 0.1599 (3) | 0.0163 (12) | |
C3 | 0.1384 (8) | 0.4227 (8) | 0.1316 (3) | 0.0187 (11) | |
C4 | −0.0837 (8) | 0.4126 (7) | 0.0826 (3) | 0.0227 (11) | |
C5 | −0.2127 (9) | 0.5642 (8) | 0.0680 (4) | 0.0277 (15) | |
C6 | 0.4160 (7) | 0.2377 (6) | 0.2262 (3) | 0.0196 (10) | |
C7 | 0.3753 (7) | 0.2843 (6) | 0.3113 (3) | 0.0186 (10) | |
H7 | 0.238946 | 0.343679 | 0.31662 | 0.022* | |
C8 | 0.5417 (7) | 0.2423 (5) | 0.3922 (3) | 0.0148 (9) | |
C9 | 0.5119 (7) | 0.2886 (6) | 0.4829 (3) | 0.0164 (9) | |
H9 | 0.375158 | 0.344584 | 0.490712 | 0.02* | |
C10 | 0.6783 (7) | 0.2534 (6) | 0.5599 (3) | 0.0165 (9) | |
H10 | 0.657322 | 0.284878 | 0.620469 | 0.02* | |
C11 | 0.8803 (7) | 0.1702 (5) | 0.5475 (3) | 0.0157 (11) | |
C12 | 0.9146 (6) | 0.1211 (10) | 0.4619 (2) | 0.0165 (7) | |
H12 | 1.052023 | 0.064184 | 0.45575 | 0.02* | |
C13 | 0.7438 (6) | 0.1551 (7) | 0.3814 (3) | 0.0150 (11) | |
C14 | 0.7724 (7) | 0.1040 (8) | 0.2918 (3) | 0.0199 (11) | |
H14 | 0.90638 | 0.042866 | 0.284841 | 0.024* | |
C15 | 0.6108 (6) | 0.1412 (10) | 0.2154 (3) | 0.0208 (9) | |
H15 | 0.628527 | 0.10273 | 0.155347 | 0.025* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.01749 (18) | 0.0207 (2) | 0.0211 (2) | 0.0017 (3) | 0.00019 (13) | 0.0006 (3) |
F1 | 0.047 (2) | 0.021 (2) | 0.036 (2) | 0.0032 (15) | 0.0129 (16) | 0.0016 (15) |
F2 | 0.0190 (10) | 0.0269 (13) | 0.0241 (12) | −0.0047 (19) | −0.0044 (9) | −0.003 (2) |
F3 | 0.0324 (15) | 0.0414 (19) | 0.0232 (15) | −0.0209 (14) | 0.0041 (12) | −0.0085 (13) |
F4 | 0.0148 (13) | 0.082 (3) | 0.0296 (16) | 0.0036 (13) | −0.0019 (12) | 0.0034 (15) |
O1 | 0.037 (2) | 0.0213 (19) | 0.0158 (17) | 0.0043 (15) | −0.0035 (14) | −0.0020 (14) |
N1 | 0.022 (3) | 0.039 (3) | 0.022 (3) | 0.010 (2) | 0.005 (2) | 0.007 (2) |
C1 | 0.036 (3) | 0.020 (3) | 0.019 (3) | 0.004 (2) | 0.011 (2) | 0.001 (2) |
C2 | 0.0181 (19) | 0.018 (4) | 0.0127 (19) | −0.0040 (19) | 0.0015 (15) | 0.0025 (18) |
C3 | 0.022 (3) | 0.023 (3) | 0.011 (2) | −0.001 (2) | 0.0038 (19) | 0.004 (2) |
C4 | 0.022 (2) | 0.035 (3) | 0.012 (2) | −0.010 (2) | 0.0045 (18) | −0.002 (2) |
C5 | 0.015 (3) | 0.051 (4) | 0.017 (3) | 0.001 (2) | 0.001 (2) | 0.004 (2) |
C6 | 0.026 (2) | 0.014 (2) | 0.017 (2) | −0.0022 (19) | −0.0007 (18) | −0.0005 (19) |
C7 | 0.018 (2) | 0.016 (2) | 0.021 (2) | 0.0012 (17) | 0.0039 (18) | 0.0000 (19) |
C8 | 0.018 (2) | 0.008 (2) | 0.019 (2) | −0.0034 (16) | 0.0052 (17) | −0.0006 (17) |
C9 | 0.016 (2) | 0.013 (2) | 0.021 (2) | 0.0029 (17) | 0.0047 (18) | −0.0009 (18) |
C10 | 0.019 (2) | 0.014 (2) | 0.017 (2) | −0.0024 (18) | 0.0045 (18) | −0.0025 (18) |
C11 | 0.0161 (19) | 0.009 (3) | 0.021 (2) | −0.0012 (15) | 0.0009 (16) | 0.0038 (16) |
C12 | 0.0174 (17) | 0.0099 (18) | 0.0233 (19) | 0.000 (3) | 0.0069 (14) | 0.000 (3) |
C13 | 0.0178 (18) | 0.009 (3) | 0.020 (2) | −0.0012 (17) | 0.0077 (15) | 0.0013 (19) |
C14 | 0.0220 (19) | 0.016 (3) | 0.024 (2) | 0.000 (2) | 0.0118 (16) | −0.004 (2) |
C15 | 0.028 (2) | 0.020 (3) | 0.0167 (19) | −0.003 (3) | 0.0091 (15) | 0.001 (3) |
Geometric parameters (Å, º) top Br1—C11 | 1.901 (4) | C7—C8 | 1.427 (6) |
F1—C1 | 1.328 (6) | C7—H7 | 0.95 |
F2—C2 | 1.342 (4) | C8—C13 | 1.416 (6) |
F3—C4 | 1.344 (6) | C8—C9 | 1.417 (6) |
F4—C5 | 1.344 (6) | C9—C10 | 1.376 (6) |
O1—C3 | 1.348 (6) | C9—H9 | 0.95 |
O1—C6 | 1.403 (5) | C10—C11 | 1.408 (6) |
N1—C5 | 1.304 (7) | C10—H10 | 0.95 |
N1—C1 | 1.316 (6) | C11—C12 | 1.360 (6) |
C1—C2 | 1.376 (6) | C12—C13 | 1.424 (5) |
C2—C3 | 1.387 (7) | C12—H12 | 0.95 |
C3—C4 | 1.388 (6) | C13—C14 | 1.408 (6) |
C4—C5 | 1.369 (7) | C14—C15 | 1.358 (6) |
C6—C7 | 1.361 (6) | C14—H14 | 0.95 |
C6—C15 | 1.412 (7) | C15—H15 | 0.95 |
| | | |
C3—O1—C6 | 120.7 (4) | C13—C8—C7 | 119.1 (4) |
C5—N1—C1 | 116.0 (5) | C9—C8—C7 | 121.7 (4) |
N1—C1—F1 | 116.6 (5) | C10—C9—C8 | 120.9 (4) |
N1—C1—C2 | 124.5 (5) | C10—C9—H9 | 119.6 |
F1—C1—C2 | 118.9 (4) | C8—C9—H9 | 119.6 |
F2—C2—C1 | 119.8 (4) | C9—C10—C11 | 119.1 (4) |
F2—C2—C3 | 121.0 (4) | C9—C10—H10 | 120.5 |
C1—C2—C3 | 119.2 (5) | C11—C10—H10 | 120.5 |
O1—C3—C2 | 125.8 (4) | C12—C11—C10 | 122.0 (4) |
O1—C3—C4 | 118.2 (5) | C12—C11—Br1 | 118.8 (3) |
C2—C3—C4 | 115.8 (5) | C10—C11—Br1 | 119.2 (3) |
F3—C4—C5 | 121.4 (4) | C11—C12—C13 | 119.8 (4) |
F3—C4—C3 | 119.1 (5) | C11—C12—H12 | 120.1 |
C5—C4—C3 | 119.5 (5) | C13—C12—H12 | 120.1 |
N1—C5—F4 | 116.7 (4) | C14—C13—C8 | 119.7 (4) |
N1—C5—C4 | 124.8 (5) | C14—C13—C12 | 121.3 (4) |
F4—C5—C4 | 118.4 (5) | C8—C13—C12 | 119.0 (4) |
C7—C6—O1 | 123.3 (4) | C15—C14—C13 | 120.8 (4) |
C7—C6—C15 | 122.5 (4) | C15—C14—H14 | 119.6 |
O1—C6—C15 | 114.2 (4) | C13—C14—H14 | 119.6 |
C6—C7—C8 | 118.7 (4) | C14—C15—C6 | 119.2 (4) |
C6—C7—H7 | 120.7 | C14—C15—H15 | 120.4 |
C8—C7—H7 | 120.7 | C6—C15—H15 | 120.4 |
C13—C8—C9 | 119.2 (4) | | |
| | | |
C5—N1—C1—F1 | 179.0 (5) | C3—O1—C6—C15 | −147.8 (5) |
C5—N1—C1—C2 | 0.0 (8) | O1—C6—C7—C8 | 179.9 (4) |
N1—C1—C2—F2 | 178.6 (4) | C15—C6—C7—C8 | 3.4 (7) |
F1—C1—C2—F2 | −0.3 (6) | C6—C7—C8—C13 | 0.5 (6) |
N1—C1—C2—C3 | −1.5 (7) | C6—C7—C8—C9 | 179.3 (4) |
F1—C1—C2—C3 | 179.5 (4) | C13—C8—C9—C10 | 1.5 (6) |
C6—O1—C3—C2 | 42.9 (7) | C7—C8—C9—C10 | −177.3 (4) |
C6—O1—C3—C4 | −141.8 (4) | C8—C9—C10—C11 | 0.0 (6) |
F2—C2—C3—O1 | −2.3 (7) | C9—C10—C11—C12 | −1.0 (7) |
C1—C2—C3—O1 | 177.8 (4) | C9—C10—C11—Br1 | 178.3 (3) |
F2—C2—C3—C4 | −177.7 (4) | C10—C11—C12—C13 | 0.6 (8) |
C1—C2—C3—C4 | 2.4 (7) | Br1—C11—C12—C13 | −178.8 (4) |
O1—C3—C4—F3 | 1.6 (7) | C9—C8—C13—C14 | 178.2 (5) |
C2—C3—C4—F3 | 177.4 (4) | C7—C8—C13—C14 | −3.0 (7) |
O1—C3—C4—C5 | −177.8 (4) | C9—C8—C13—C12 | −1.9 (7) |
C2—C3—C4—C5 | −2.0 (7) | C7—C8—C13—C12 | 176.9 (4) |
C1—N1—C5—F4 | 180.0 (4) | C11—C12—C13—C14 | −179.2 (5) |
C1—N1—C5—C4 | 0.5 (9) | C11—C12—C13—C8 | 0.9 (8) |
F3—C4—C5—N1 | −178.8 (5) | C8—C13—C14—C15 | 1.6 (8) |
C3—C4—C5—N1 | 0.6 (9) | C12—C13—C14—C15 | −178.3 (6) |
F3—C4—C5—F4 | 1.7 (7) | C13—C14—C15—C6 | 2.2 (9) |
C3—C4—C5—F4 | −178.9 (4) | C7—C6—C15—C14 | −4.9 (9) |
C3—O1—C6—C7 | 35.4 (6) | O1—C6—C15—C14 | 178.4 (5) |
2,2'-Bis[(2,3,5,6-tetrafluoropyridin-4-yl)oxy]-1,1'-biphenyl (V)
top Crystal data top C22H8F8N2O2 | Dx = 1.738 Mg m−3 |
Mr = 484.30 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbcn | Cell parameters from 9894 reflections |
a = 18.8516 (6) Å | θ = 3.1–31.0° |
b = 10.6512 (3) Å | µ = 0.17 mm−1 |
c = 9.2196 (3) Å | T = 100 K |
V = 1851.22 (10) Å3 | Rectangular prism, colourless |
Z = 4 | 0.33 × 0.27 × 0.26 mm |
F(000) = 968 | |
Data collection top Bruker SMART APEX CCD diffractometer | 2830 independent reflections |
Radiation source: fine focus sealed tube | 2554 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 8.3333 pixels mm-1 | θmax = 30.5°, θmin = 2.2° |
ω Scans scans | h = −26→26 |
Absorption correction: multi-scan (SADABS; Bruker, 2017) | k = −15→15 |
Tmin = 0.87, Tmax = 0.96 | l = −13→13 |
36854 measured reflections | |
Refinement top Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.098 | w = 1/[σ2(Fo2) + (0.0477P)2 + 1.0353P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2830 reflections | Δρmax = 0.54 e Å−3 |
154 parameters | Δρmin = −0.24 e Å−3 |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F1 | 0.23289 (4) | 0.82100 (7) | 0.58850 (9) | 0.02742 (18) | |
F2 | 0.36863 (4) | 0.80572 (6) | 0.50165 (8) | 0.02166 (16) | |
F3 | 0.39175 (4) | 0.45355 (6) | 0.81381 (8) | 0.02052 (15) | |
F4 | 0.25208 (4) | 0.47778 (7) | 0.87330 (8) | 0.02652 (17) | |
O1 | 0.45506 (4) | 0.60742 (7) | 0.62192 (8) | 0.01451 (15) | |
N1 | 0.24272 (5) | 0.64972 (10) | 0.73110 (11) | 0.0206 (2) | |
C1 | 0.27334 (6) | 0.72890 (11) | 0.64163 (12) | 0.0190 (2) | |
C2 | 0.34353 (5) | 0.72303 (10) | 0.59814 (11) | 0.01551 (19) | |
C3 | 0.38644 (5) | 0.62907 (9) | 0.65624 (11) | 0.01334 (18) | |
C4 | 0.35408 (5) | 0.54608 (9) | 0.75268 (11) | 0.01526 (19) | |
C5 | 0.28294 (6) | 0.56017 (11) | 0.78372 (12) | 0.0184 (2) | |
C6 | 0.49905 (5) | 0.70787 (9) | 0.57843 (11) | 0.01314 (18) | |
C7 | 0.51479 (5) | 0.80445 (9) | 0.67541 (11) | 0.01353 (19) | |
C8 | 0.56072 (6) | 0.89900 (10) | 0.62696 (11) | 0.0168 (2) | |
H8 | 0.571595 | 0.967538 | 0.689043 | 0.02* | |
C9 | 0.59065 (6) | 0.89380 (10) | 0.48901 (12) | 0.0184 (2) | |
H9 | 0.621893 | 0.958404 | 0.457927 | 0.022* | |
C10 | 0.57499 (6) | 0.79449 (11) | 0.39657 (12) | 0.0176 (2) | |
H10 | 0.59608 | 0.790723 | 0.30309 | 0.021* | |
C11 | 0.52840 (5) | 0.70047 (10) | 0.44090 (11) | 0.01560 (19) | |
H11 | 0.516981 | 0.632684 | 0.378125 | 0.019* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0200 (3) | 0.0288 (4) | 0.0334 (4) | 0.0094 (3) | −0.0009 (3) | 0.0074 (3) |
F2 | 0.0203 (3) | 0.0201 (3) | 0.0246 (3) | −0.0002 (2) | 0.0006 (3) | 0.0094 (3) |
F3 | 0.0197 (3) | 0.0198 (3) | 0.0220 (3) | 0.0033 (2) | 0.0021 (2) | 0.0073 (3) |
F4 | 0.0211 (3) | 0.0304 (4) | 0.0280 (4) | −0.0027 (3) | 0.0089 (3) | 0.0090 (3) |
O1 | 0.0122 (3) | 0.0132 (3) | 0.0181 (3) | −0.0012 (2) | 0.0020 (3) | 0.0001 (3) |
N1 | 0.0146 (4) | 0.0256 (5) | 0.0217 (4) | 0.0017 (3) | 0.0019 (3) | 0.0007 (4) |
C1 | 0.0160 (4) | 0.0206 (5) | 0.0203 (5) | 0.0038 (4) | −0.0018 (4) | 0.0006 (4) |
C2 | 0.0156 (4) | 0.0152 (4) | 0.0157 (4) | −0.0001 (3) | −0.0008 (3) | 0.0016 (3) |
C3 | 0.0129 (4) | 0.0141 (4) | 0.0130 (4) | −0.0007 (3) | 0.0000 (3) | −0.0016 (3) |
C4 | 0.0151 (4) | 0.0155 (4) | 0.0152 (4) | 0.0006 (3) | 0.0003 (3) | 0.0012 (4) |
C5 | 0.0160 (4) | 0.0217 (5) | 0.0174 (5) | −0.0025 (4) | 0.0030 (4) | 0.0018 (4) |
C6 | 0.0120 (4) | 0.0126 (4) | 0.0148 (4) | −0.0011 (3) | 0.0001 (3) | 0.0010 (3) |
C7 | 0.0141 (4) | 0.0135 (4) | 0.0130 (4) | 0.0008 (3) | −0.0003 (3) | 0.0008 (3) |
C8 | 0.0188 (5) | 0.0145 (4) | 0.0170 (5) | −0.0029 (4) | −0.0011 (4) | 0.0002 (3) |
C9 | 0.0185 (5) | 0.0173 (5) | 0.0196 (5) | −0.0037 (4) | 0.0009 (4) | 0.0030 (4) |
C10 | 0.0163 (4) | 0.0210 (5) | 0.0153 (4) | −0.0015 (4) | 0.0020 (3) | 0.0018 (4) |
C11 | 0.0153 (4) | 0.0172 (4) | 0.0143 (4) | −0.0008 (3) | 0.0001 (3) | −0.0014 (3) |
Geometric parameters (Å, º) top F1—C1 | 1.3356 (13) | C6—C11 | 1.3856 (14) |
F2—C2 | 1.3383 (12) | C6—C7 | 1.3949 (14) |
F3—C4 | 1.3390 (12) | C7—C8 | 1.4012 (14) |
F4—C5 | 1.3382 (12) | C7—C7i | 1.4842 (19) |
O1—C3 | 1.3517 (12) | C8—C9 | 1.3925 (15) |
O1—C6 | 1.4118 (12) | C8—H8 | 0.95 |
N1—C5 | 1.3114 (14) | C9—C10 | 1.3900 (15) |
N1—C1 | 1.3134 (15) | C9—H9 | 0.95 |
C1—C2 | 1.3840 (15) | C10—C11 | 1.3934 (14) |
C2—C3 | 1.3938 (14) | C10—H10 | 0.95 |
C3—C4 | 1.3942 (14) | C11—H11 | 0.95 |
C4—C5 | 1.3795 (14) | | |
| | | |
C3—O1—C6 | 119.96 (8) | C11—C6—O1 | 116.82 (9) |
C5—N1—C1 | 116.44 (10) | C7—C6—O1 | 120.12 (9) |
N1—C1—F1 | 116.81 (10) | C6—C7—C8 | 117.20 (9) |
N1—C1—C2 | 124.97 (10) | C6—C7—C7i | 120.93 (7) |
F1—C1—C2 | 118.22 (10) | C8—C7—C7i | 121.85 (8) |
F2—C2—C1 | 120.06 (9) | C9—C8—C7 | 120.86 (10) |
F2—C2—C3 | 121.52 (9) | C9—C8—H8 | 119.6 |
C1—C2—C3 | 118.42 (10) | C7—C8—H8 | 119.6 |
O1—C3—C2 | 126.01 (9) | C10—C9—C8 | 120.28 (10) |
O1—C3—C4 | 117.37 (9) | C10—C9—H9 | 119.9 |
C2—C3—C4 | 116.52 (9) | C8—C9—H9 | 119.9 |
F3—C4—C5 | 120.55 (9) | C9—C10—C11 | 120.06 (10) |
F3—C4—C3 | 120.20 (9) | C9—C10—H10 | 120.0 |
C5—C4—C3 | 119.25 (10) | C11—C10—H10 | 120.0 |
N1—C5—F4 | 117.00 (9) | C6—C11—C10 | 118.63 (10) |
N1—C5—C4 | 124.36 (10) | C6—C11—H11 | 120.7 |
F4—C5—C4 | 118.64 (10) | C10—C11—H11 | 120.7 |
C11—C6—C7 | 122.93 (9) | | |
| | | |
C5—N1—C1—F1 | −179.46 (10) | F3—C4—C5—N1 | 178.43 (10) |
C5—N1—C1—C2 | 1.11 (17) | C3—C4—C5—N1 | −1.84 (17) |
N1—C1—C2—F2 | 177.24 (10) | F3—C4—C5—F4 | −1.58 (16) |
F1—C1—C2—F2 | −2.18 (16) | C3—C4—C5—F4 | 178.15 (9) |
N1—C1—C2—C3 | −2.24 (17) | C3—O1—C6—C11 | −119.50 (10) |
F1—C1—C2—C3 | 178.34 (10) | C3—O1—C6—C7 | 64.48 (12) |
C6—O1—C3—C2 | 30.14 (14) | C11—C6—C7—C8 | 2.07 (15) |
C6—O1—C3—C4 | −153.56 (9) | O1—C6—C7—C8 | 177.84 (9) |
F2—C2—C3—O1 | −1.91 (16) | C11—C6—C7—C7i | −176.48 (10) |
C1—C2—C3—O1 | 177.56 (10) | O1—C6—C7—C7i | −0.71 (15) |
F2—C2—C3—C4 | −178.24 (9) | C6—C7—C8—C9 | −1.77 (15) |
C1—C2—C3—C4 | 1.24 (15) | C7i—C7—C8—C9 | 176.77 (10) |
O1—C3—C4—F3 | 3.69 (14) | C7—C8—C9—C10 | 0.33 (16) |
C2—C3—C4—F3 | −179.66 (9) | C8—C9—C10—C11 | 0.92 (17) |
O1—C3—C4—C5 | −176.05 (9) | C7—C6—C11—C10 | −0.88 (16) |
C2—C3—C4—C5 | 0.61 (15) | O1—C6—C11—C10 | −176.78 (9) |
C1—N1—C5—F4 | −179.01 (10) | C9—C10—C11—C6 | −0.66 (16) |
C1—N1—C5—C4 | 0.98 (17) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Contact geometry (Å ,°) for I topCg1 is the centroid of the N1/C1–C5 ring. |
X—Y···A | X—Y | Y···A | X···A | X—Y···A |
C11—H11···F1i | 0.95 | 2.46 | 3.4049 (19) | 170.3 |
C1—F1···Cg1ii | 1.3404 (18) | 3.6822 (13) | 4.8632 (17) | 147.20 (9) |
Symmetry codes: (i) -x + 2, y - 1/2, -z + 1/2; (ii) 2 - x, 1/2 + x, 1/2 - z. |
Contact geometry (Å, °) for II topCg1 and Cg2 are the centroids of the N1/C1–C4 and C6–C11 rings, respectively. |
X—Y···A | X—Y | Y···A | X···A | X—Y···A |
C10—H10···F3i | 0.95 | 2.39 | 3.2214 (19) | 145.9 |
C11—H11···Cg2i | 0.95 | 2.90 | 3.668 (2) | 139 |
C1—F1···Cg1ii | 1.3395 (19) | 3.1531 (14) | 4.068 (2) | 124.76 (10) |
C5—F4···Cg1iii | 1.3401 (19) | 3.1094 (13) | 3.6241 (18) | 101.55 (9) |
C9—Br1···N1iv | 1.8952 (17) | 3.2639 (16) | 5.104 (3) | 162.65 (7) |
Symmetry codes: (i) -x + 3/2, y + 1/2, -z + 3/2; (ii) -x + 1/2, y + 1/2, -z + 3/2; (iii) -x + 1, -y + 1, -z + 2; (iv) 1/2 + x, 1/2 - y, -1/2 + z. |
Contact geometry (Å, °) for III topCg1 and Cg2 are the centroids of the N1/C1–C5 and C6–C15 rings respectively. |
X—Y···A | X—Y | Y···A | X···A | X—Y···A |
C7—H7···F3i | 0.95 | 2.50 | 3.4366 (19) | 169.6 |
C15—H15···N1ii | 0.95 | 2.59 | 3.455 (2) | 152.1 |
C1—F1···Cg2iii | 1.334 (2) | 3.2922 (15) | 3.5581 (19) | 90.28 (10) |
C5—F4···Cg1iv | 1.343 (2) | 3.2790 (14) | 4.2804 (18) | 130.88 (11) |
Symmetry codes: (i) x + 1, y, z; (ii) -x, y + 1/2, -z + 1/2; (iii) 1 - x, -1/2 + y, 1/2 - z; (iv) - x, -1/2 + y, 1/2 - z. |
Contact geometry (Å, °) for IV topCg1, Cg2, and Cg3 are the centroids of the N1/C1–C5, C6–C15, and C8–C13 rings, respectively. |
X—Y···A | X—Y | Y···A | X···A | X—Y···A |
C15—H15···F3ii | 0.95 | 2.43 | 3.105 (5) | 127.5 |
C9—H9···Cg3i | 0.95 | 2.83 | 3.519 (5) | 130 |
C11—Br1···Cg1iii | 1.901 (4) | 3.6283 (19) | 4.923 (5) | 122.74 (13) |
C11—Br1···Cg2iv | 1.901 (4) | 3.735 (2) | 5.037 (4) | 123.34 (12) |
C4—F3···Cg1v | 1.344 (6) | 3.082 (3) | 3.936 (5) | 120.3 (3) |
Symmetry codes: (i) -x + 1, y + 1/2, -z + 1; (ii) x + 1, y, z; (iii) -x + 1, y - 1/2, -z + 1; (iv) -x + 2, y - 1/2, -z + 1; (v) -x, y - 1/2, -z. |
Contact geometry (Å, °) for V topCg1 is the centroid of the N1/C1–C5 ring. |
X—Y···A | X—Y | Y···A | X···A | X—Y···A |
C11—H11···F3i | 0.95 | 2.63 | 3.2361 (13) | 121.8 |
C11—H11···F3ii | 0.95 | 2.60 | 3.2711 (12) | 127.8 |
C11—H11···O1i | 0.95 | 2.61 | 3.3446 (13) | 134.3 |
C5—F4···Cg1iii | 1.3382 (12) | 3.4138 (9) | 4.3778 (12) | 128.77 (6) |
Symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) x, -y + 1, z - 1/2; (iii) x, 1 - y, 1/2 + z. |
Percentage contributions of inter-atomic contacts to the Hirshfeld surface for I topContact | Percentage contribution |
F···H/H···F | 36.9 |
C···H/H···C | 14.8 |
F···F | 12.1 |
H···H | 9.6 |
N···H/H···N | 4.8 |
F···C/C···F | 4.7 |
F···O/O···F | 4.2 |
C···C | 4.1 |
N···C/C···N | 3.2 |
O···C/C···O | 2.2 |
O···N/N···O | 2.0 |
F···N/N···F | 1.3 |
O···H/H···O | 0.1 |
Percentage contributions of inter-atomic contacts to the Hirshfeld surface for II topContact | Percentage contribution |
F···H/H···F | 18.7 |
F···C/C···F | 11.8 |
C···H/H···C | 11.7 |
F···F | 10.8 |
Br···F/F···Br | 8.3 |
Br···H/H···Br | 7.7 |
H···H | 6.9 |
F···N/N···F | 6.1 |
O···H/H···O | 4.6 |
Br···N/N···Br | 3.5 |
C···C | 3.4 |
Br···C/C···Br | 2.2 |
Br···O/O···Br | 1.8 |
N···C/C···N | 0.9 |
F···O/O···F | 0.8 |
O···C/C···O | 0.6 |
N···H/H···N | 0.2 |
Percentage contributions of inter-atomic contacts to the Hirshfeld surface for III topContact | Percentage contribution |
F···H/H···F | 30.4 |
C···H/H···C | 22.8 |
H···H | 14.0 |
F···C/C···F | 10.0 |
F···F | 6.6 |
N···H/H···N | 4.2 |
O···C/C···O | 2.9 |
F···O/O···F | 2.3 |
F···N/N···F | 2.0 |
O···H/H···O | 0.3 |
O···N/N···O | 1.6 |
C···C | 1.5 |
N···C/C···N | 1.4 |
Percentage contributions of inter-atomic contacts to the Hirshfeld surface for IV topContact | Percentage contribution |
C···H/H···C | 19.1 |
F···H/H···F | 18.8 |
F···C/C···F | 9.4 |
H···H | 9.1 |
Br···H/H···Br | 8.7 |
F···F | 7.7 |
Br···C/C···Br | 7.2 |
F···O/O···F | 4.5 |
Br···F/F···Br | 3.9 |
F···N/N···F | 3.7 |
N···H/H···N | 2.6 |
C···C | 1.5 |
N···C/C···N | 1.1 |
O···N/N···O | 0.9 |
Br···N/N···Br | 0.8 |
O···C/C···O | 0.6 |
O···H/H···O | 0.3 |
Percentage contributions of inter-atomic contacts to the Hirshfeld surface for V topContact | Percentage contribution |
F···H/H···F | 32.3 |
F···C/C···F | 19.0 |
H···H | 11.6 |
F···F | 11.3 |
N···H/H···N | 7.1 |
F···N/N···F | 6.3 |
C···H/H···C | 4.8 |
O···H/H···O | 4.5 |
F···O/O···F | 1.8 |
C···C | 1.3 |
Funding information
Funding for this research was provided by: Air Force Office of Scientific Research.
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