 | Acta Crystallographica Section E Acta Crystallographica Section E CRYSTALLOGRAPHIC COMMUNICATIONS |
journal menu
organic compounds
| CRYSTALLOGRAPHIC COMMUNICATIONS |
access2-(2-Fluoro-4-nitrophenoxy)-3-nitropyridine
aDepartment of Chemistry and Chemical Engineering, Changchun University of Science and Technology, Changchun 130022, People's Republic of China
*Correspondence e-mail: cuilili1127@gmail.com
In the title compound, C11H6FN3O5, the dihedral angle between the aromatic rings is 72.4 (3)°. The NO2 groups form dihedral angles of 40.8 (2) and 4.8 (2)°, respectively, with the attached pyridine and benzene rings. The features π–π stacking between centrosymmetrically related pairs of pyridine rings [centroid–centroid separation = 3.800 (3) Å].
CCDC reference: 977994
Related literature
For applications and the biological activity of 2-phenoxypyridine, see: Chao et al. (2013![[Chao, H., Turdi, H., Herpin, T. F., Roberge, J. Y., Liu, Y., Schnur, D. M., Poss, M. A., Rehfuss, R., Hua, J., Wu, Q., Price, L. A., Abell, L. M., Schumacher, W. A., Bostwick, J. S., Steinbacher, T. E., Stewart, A. B., Ogletree, M. L., Huang, C. S., Chang, M., Cacace, A. M., Arcuri, M. J., Celani, D., Wexler, R. R. & Lawrence, R. M. (2013). J. Med. Chem. 56, 1704-1714.]](../../../../../../logos/arrows/e_arr.gif "Chao, H., Turdi, H., Herpin, T. F., Roberge, J. Y., Liu, Y., Schnur, D. M., Poss, M. A., Rehfuss, R., Hua, J., Wu, Q., Price, L. A., Abell, L. M., Schumacher, W. A., Bostwick, J. S., Steinbacher, T. E., Stewart, A. B., Ogletree, M. L., Huang, C. S., Chang, M., Cacace, A. M., Arcuri, M. J., Celani, D., Wexler, R. R. & Lawrence, R. M. (2013). J. Med. Chem. 56, 1704-1714.")
).
![[Scheme 1]](pk2504scheme1.gif)
Experimental
Crystal data
|
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
CCDC reference: 977994
contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536813034181/pk2504sup1.cif
Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536813034181/pk2504Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536813034181/pk2504Isup3.cml
To a solution of 2-chloro-3-nitropyridine (1.0 g, 6.3 mmol) and 2-fluoro-4-nitrophenol (1.48 g, 9.45 mmol) in toluene (35 ml) was added N,N-diisopropylethylamine (3.3 ml, 18.9 mmol). The reaction mixture was stirred for 48 h under reflux. The reaction mixture was concentrated in vacuo, diluted with water, and extracted with EtOAc. The organic phase was washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo to yield the crude product as a solid. Purification by recrystallization from methanol gave the desired product, 2-(2-fluoro-4-nitrophenoxy)-3- nitropyridine (yellow solid, 0.80 g, 46%, 97.1–98.4 oC). 1H NMR (DMSO-d6, 300 Hz), 8.70 (dd, J = 8.1, 1.8 Hz, 1H), 8.47 (dd, J = 4.8, 1.8 Hz, 1H), 8.41 (dd, J = 10.2, 2.7 Hz, 1H), 8.25–8.20 (m, 1H), 7.80–7.74 (m 1H), 7.54–7.50 (m, 1H); ES–MS: 279.8 [(M + H+)]. Crystals of the title compound for X-ray diffraction were obtained by slow evaporation of MeOH/CH2Cl2 solution.
All hydrogen atoms were fixed at calculated positions and refined by using a riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C).
2-Phenoxypyridines have been shown to be small molecule P2Y1 antagonists (Chao et al. 2013). Here, the of 2-(2-fluoro-4-nitrophenoxy)- 3-nitropyridine is reported.
For applications and the biological activity of 2-phenoxypyridine, see: Chao et al. (2013).
Data collection: RAPID-AUTO (Rigaku, 1998); cell RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./pk2504fig1thm.gif) | Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level. |
| C11H6FN3O5 | F(000) = 568 |
| Mr = 279.19 | Dx = 1.606 Mg m−3 |
| Monoclinic, P21/c | Melting point = 370.1–371.4 K |
| Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
| a = 7.5275 (15) Å | Cell parameters from 7455 reflections |
| b = 21.804 (4) Å | θ = 3.1–27.7° |
| c = 7.1681 (14) Å | µ = 0.14 mm−1 |
| β = 101.07 (3)° | T = 293 K |
| V = 1154.6 (4) Å3 | Block, colourless |
| Z = 4 | 0.41 × 0.36 × 0.22 mm |
| Rigaku R-AXIS RAPID IP diffractometer | 2611 independent reflections |
| Radiation source: fine-focus sealed tube | 1351 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.083 |
| Detector resolution: 0.1 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
| oscillation scans | h = −9→9 |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −28→28 |
| Tmin = 0.945, Tmax = 0.970 | l = −9→8 |
| 10606 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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.140 | H-atom parameters constrained |
| S = 0.94 | w = 1/[σ2(Fo2) + (0.0498P)2] where P = (Fo2 + 2Fc2)/3 |
| 2611 reflections | (Δ/σ)max < 0.001 |
| 181 parameters | Δρmax = 0.21 e Å−3 |
| 0 restraints | Δρmin = −0.26 e Å−3 |
| C11H6FN3O5 | V = 1154.6 (4) Å3 |
| Mr = 279.19 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 7.5275 (15) Å | µ = 0.14 mm−1 |
| b = 21.804 (4) Å | T = 293 K |
| c = 7.1681 (14) Å | 0.41 × 0.36 × 0.22 mm |
| β = 101.07 (3)° |
| Rigaku R-AXIS RAPID IP diffractometer | 2611 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1351 reflections with I > 2σ(I) |
| Tmin = 0.945, Tmax = 0.970 | Rint = 0.083 |
| 10606 measured reflections |
| R[F2 > 2σ(F2)] = 0.062 | 0 restraints |
| wR(F2) = 0.140 | H-atom parameters constrained |
| S = 0.94 | Δρmax = 0.21 e Å−3 |
| 2611 reflections | Δρmin = −0.26 e Å−3 |
| 181 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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. |
| x | y | z | Uiso*/Ueq | ||
| C5 | 0.7119 (3) | 0.37835 (11) | 0.5574 (3) | 0.0470 (6) | |
| C4 | 0.8649 (3) | 0.34302 (12) | 0.6136 (3) | 0.0453 (6) | |
| C1 | 0.5475 (3) | 0.29000 (12) | 0.4494 (3) | 0.0492 (6) | |
| C3 | 0.8592 (3) | 0.28155 (12) | 0.5825 (3) | 0.0535 (7) | |
| H3 | 0.9634 | 0.2580 | 0.6169 | 0.064* | |
| C6 | 0.5501 (3) | 0.35242 (12) | 0.4752 (3) | 0.0516 (7) | |
| H6 | 0.4464 | 0.3761 | 0.4385 | 0.062* | |
| C2 | 0.6968 (3) | 0.25381 (13) | 0.4988 (4) | 0.0554 (7) | |
| H2 | 0.6904 | 0.2117 | 0.4772 | 0.066* | |
| C7 | 1.0406 (3) | 0.39397 (11) | 0.8728 (3) | 0.0430 (6) | |
| C8 | 1.1950 (3) | 0.42593 (11) | 0.9561 (3) | 0.0446 (6) | |
| C9 | 1.2093 (3) | 0.44800 (12) | 1.1372 (3) | 0.0524 (6) | |
| H9 | 1.3124 | 0.4691 | 1.1956 | 0.063* | |
| C10 | 1.0688 (4) | 0.43849 (13) | 1.2313 (3) | 0.0598 (7) | |
| H10 | 1.0732 | 0.4535 | 1.3536 | 0.072* | |
| C11 | 0.9221 (4) | 0.40613 (13) | 1.1387 (3) | 0.0580 (7) | |
| H11 | 0.8268 | 0.3995 | 1.2018 | 0.070* | |
| F1 | 0.7237 (2) | 0.43888 (7) | 0.5831 (2) | 0.0720 (5) | |
| O1 | 1.0278 (2) | 0.37145 (9) | 0.6923 (2) | 0.0550 (5) | |
| O4 | 1.3069 (3) | 0.45113 (12) | 0.6873 (3) | 0.0846 (7) | |
| O5 | 1.4970 (2) | 0.43310 (12) | 0.9461 (4) | 0.0937 (8) | |
| O2 | 0.3673 (3) | 0.20648 (13) | 0.3537 (5) | 0.1251 (11) | |
| O3 | 0.2448 (3) | 0.29424 (13) | 0.3109 (4) | 0.1255 (12) | |
| N3 | 0.9075 (3) | 0.38343 (10) | 0.9628 (3) | 0.0508 (5) | |
| N2 | 1.3435 (3) | 0.43708 (10) | 0.8543 (4) | 0.0593 (6) | |
| N1 | 0.3735 (3) | 0.26136 (14) | 0.3662 (4) | 0.0716 (7) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| C5 | 0.0507 (13) | 0.0405 (14) | 0.0488 (12) | −0.0032 (11) | 0.0074 (11) | −0.0045 (10) |
| C4 | 0.0391 (12) | 0.0565 (16) | 0.0385 (11) | −0.0039 (11) | 0.0029 (10) | −0.0049 (10) |
| C1 | 0.0444 (13) | 0.0523 (16) | 0.0473 (13) | −0.0054 (11) | −0.0005 (11) | −0.0089 (11) |
| C3 | 0.0452 (13) | 0.0559 (17) | 0.0568 (14) | 0.0103 (11) | 0.0034 (12) | −0.0036 (12) |
| C6 | 0.0428 (13) | 0.0531 (17) | 0.0541 (14) | 0.0053 (11) | −0.0028 (11) | −0.0027 (11) |
| C2 | 0.0579 (15) | 0.0461 (16) | 0.0600 (15) | 0.0013 (12) | 0.0060 (13) | −0.0083 (11) |
| C7 | 0.0374 (12) | 0.0461 (14) | 0.0429 (11) | −0.0031 (10) | 0.0009 (10) | −0.0003 (10) |
| C8 | 0.0356 (11) | 0.0426 (14) | 0.0526 (13) | −0.0010 (10) | 0.0008 (11) | 0.0020 (10) |
| C9 | 0.0477 (13) | 0.0484 (15) | 0.0546 (14) | −0.0047 (11) | −0.0060 (12) | −0.0031 (11) |
| C10 | 0.0678 (17) | 0.0625 (18) | 0.0448 (13) | −0.0060 (14) | 0.0003 (13) | −0.0058 (12) |
| C11 | 0.0575 (15) | 0.0730 (19) | 0.0447 (13) | −0.0122 (14) | 0.0126 (12) | −0.0008 (12) |
| F1 | 0.0736 (10) | 0.0425 (9) | 0.0955 (11) | −0.0038 (7) | 0.0051 (9) | −0.0074 (8) |
| O1 | 0.0392 (9) | 0.0785 (13) | 0.0472 (9) | −0.0119 (8) | 0.0080 (7) | −0.0158 (8) |
| O4 | 0.0682 (13) | 0.116 (2) | 0.0747 (13) | −0.0145 (13) | 0.0261 (11) | 0.0135 (13) |
| O5 | 0.0355 (10) | 0.121 (2) | 0.1207 (18) | −0.0093 (11) | 0.0043 (11) | −0.0072 (15) |
| O2 | 0.0874 (18) | 0.0756 (19) | 0.202 (3) | −0.0328 (14) | 0.0027 (18) | −0.0372 (19) |
| O3 | 0.0584 (14) | 0.109 (2) | 0.183 (3) | −0.0043 (14) | −0.0421 (17) | −0.0136 (19) |
| N3 | 0.0449 (11) | 0.0617 (14) | 0.0457 (10) | −0.0105 (10) | 0.0086 (9) | −0.0026 (9) |
| N2 | 0.0392 (11) | 0.0564 (15) | 0.0805 (16) | −0.0078 (10) | 0.0073 (11) | −0.0048 (12) |
| N1 | 0.0568 (15) | 0.0735 (19) | 0.0797 (16) | −0.0166 (13) | 0.0011 (13) | −0.0196 (14) |
| C5—F1 | 1.333 (3) | C7—C8 | 1.388 (3) |
| C5—C6 | 1.369 (3) | C8—C9 | 1.369 (3) |
| C5—C4 | 1.380 (3) | C8—N2 | 1.468 (3) |
| C4—C3 | 1.358 (3) | C9—C10 | 1.375 (4) |
| C4—O1 | 1.393 (3) | C9—H9 | 0.9300 |
| C1—C2 | 1.363 (3) | C10—C11 | 1.370 (3) |
| C1—C6 | 1.373 (3) | C10—H10 | 0.9300 |
| C1—N1 | 1.470 (3) | C11—N3 | 1.339 (3) |
| C3—C2 | 1.392 (3) | C11—H11 | 0.9300 |
| C3—H3 | 0.9300 | O4—N2 | 1.215 (3) |
| C6—H6 | 0.9300 | O5—N2 | 1.218 (2) |
| C2—H2 | 0.9300 | O2—N1 | 1.200 (3) |
| C7—N3 | 1.312 (3) | O3—N1 | 1.209 (3) |
| C7—O1 | 1.370 (3) | ||
| F1—C5—C6 | 119.9 (2) | C9—C8—C7 | 119.4 (2) |
| F1—C5—C4 | 118.9 (2) | C9—C8—N2 | 118.9 (2) |
| C6—C5—C4 | 121.3 (2) | C7—C8—N2 | 121.6 (2) |
| C3—C4—C5 | 120.3 (2) | C8—C9—C10 | 119.0 (2) |
| C3—C4—O1 | 120.3 (2) | C8—C9—H9 | 120.5 |
| C5—C4—O1 | 119.3 (2) | C10—C9—H9 | 120.5 |
| C2—C1—C6 | 123.3 (2) | C11—C10—C9 | 117.6 (2) |
| C2—C1—N1 | 119.0 (2) | C11—C10—H10 | 121.2 |
| C6—C1—N1 | 117.7 (2) | C9—C10—H10 | 121.2 |
| C4—C3—C2 | 119.8 (2) | N3—C11—C10 | 124.0 (3) |
| C4—C3—H3 | 120.1 | N3—C11—H11 | 118.0 |
| C2—C3—H3 | 120.1 | C10—C11—H11 | 118.0 |
| C5—C6—C1 | 117.1 (2) | C7—O1—C4 | 116.05 (18) |
| C5—C6—H6 | 121.4 | C7—N3—C11 | 117.8 (2) |
| C1—C6—H6 | 121.4 | O4—N2—O5 | 124.2 (2) |
| C1—C2—C3 | 118.2 (3) | O4—N2—C8 | 118.75 (19) |
| C1—C2—H2 | 120.9 | O5—N2—C8 | 117.0 (2) |
| C3—C2—H2 | 120.9 | O2—N1—O3 | 123.3 (3) |
| N3—C7—O1 | 118.66 (19) | O2—N1—C1 | 118.2 (3) |
| N3—C7—C8 | 122.1 (2) | O3—N1—C1 | 118.4 (3) |
| O1—C7—C8 | 119.2 (2) |
Experimental details
| Crystal data | |
| Chemical formula | C11H6FN3O5 |
| Mr | 279.19 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 293 |
| a, b, c (Å) | 7.5275 (15), 21.804 (4), 7.1681 (14) |
| β (°) | 101.07 (3) |
| V (Å3) | 1154.6 (4) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.14 |
| Crystal size (mm) | 0.41 × 0.36 × 0.22 |
| Data collection | |
| Diffractometer | Rigaku R-AXIS RAPID IP |
| Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
| Tmin, Tmax | 0.945, 0.970 |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 10606, 2611, 1351 |
| Rint | 0.083 |
| (sin θ/λ)max (Å−1) | 0.649 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.062, 0.140, 0.94 |
| No. of reflections | 2611 |
| No. of parameters | 181 |
| H-atom treatment | H-atom parameters constrained |
| Δρmax, Δρmin (e Å−3) | 0.21, −0.26 |
Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Acknowledgements
The project was sponsored by the Natural Science Foundation of China (No. 21273024) and the Natural Science Foundation of Jilin Province, China (No. 201215135).
References
Chao, H., Turdi, H., Herpin, T. F., Roberge, J. Y., Liu, Y., Schnur, D. M., Poss, M. A., Rehfuss, R., Hua, J., Wu, Q., Price, L. A., Abell, L. M., Schumacher, W. A., Bostwick, J. S., Steinbacher, T. E., Stewart, A. B., Ogletree, M. L., Huang, C. S., Chang, M., Cacace, A. M., Arcuri, M. J., Celani, D., Wexler, R. R. & Lawrence, R. M. (2013). J. Med. Chem. 56, 1704–1714. Web of Science CrossRef CAS PubMed Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
| CRYSTALLOGRAPHIC COMMUNICATIONS |
2-Phenoxypyridines have been shown to be small molecule P2Y1 antagonists (Chao et al. 2013). Here, the crystal structure of 2-(2-fluoro-4-nitrophenoxy)- 3-nitropyridine is reported.