supplementary materials
3-Nitrophenyl pyrimidin-2-yl ether
In the title compound, C10H7N3O3, the dihedral angle between the two aromatic rings is 87.5 (1) Å; their ipso-C atoms subtend an angle of 117.4 (1)° at the ether O atom.
3-Nitrophenol (2.78 g, 20 mmol) was mixed with sodium hydroxide (0.08 g, 20 mmol) in several drops of water. The water was then evaporated. The paste was
heated with 2-chloropyrimidine (2.30 g, 20 mmol) at 423–433 K for 6 h. The
product was dissolved in water and the solution extracted with chloroform. The
chloroform phase was dried over sodium sulfate; the evaporation of the solvent
gave well shaped very pale brown
blocks of (I) 40% yield along with some unidentified
brown material.
The H-atoms were placed in calculated positions (C—H 0.95 Å) and
refined as riding with U(H) = 1.2Ueq(C).
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).
3-Nitrophenyl pyrimidin-2-yl ether
top
Crystal data top
| C10H7N3O3 | F(000) = 896 |
| Mr = 217.19 | Dx = 1.486 Mg m−3 |
| Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2n 2ab | Cell parameters from 4130 reflections |
| a = 18.1360 (3) Å | θ = 2.8–28.2° |
| b = 7.3355 (1) Å | µ = 0.11 mm−1 |
| c = 14.5986 (3) Å | T = 118 K |
| V = 1942.15 (6) Å3 | Block, faint brown |
| Z = 8 | 0.40 × 0.20 × 0.15 mm |
Data collection top
Bruker SMART APEX CCD
diffractometer | 1890 reflections with I > 2σ(I) |
| Radiation source: fine-focus sealed tube | Rint = 0.029 |
| graphite | θmax = 27.5°, θmin = 2.3° |
| ω scans | h = −23→23 |
| 12785 measured reflections | k = −9→9 |
| 2242 independent reflections | l = −18→18 |
Refinement top
| 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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.102 | H-atom parameters constrained |
| S = 1.02 | w = 1/[σ2(Fo2) + (0.0556P)2 + 0.7122P]
where P = (Fo2 + 2Fc2)/3 |
| 2242 reflections | (Δ/σ)max = 0.001 |
| 145 parameters | Δρmax = 0.27 e Å−3 |
| 0 restraints | Δρmin = −0.29 e Å−3 |
Crystal data top
| C10H7N3O3 | V = 1942.15 (6) Å3 |
| Mr = 217.19 | Z = 8 |
| Orthorhombic, Pbcn | Mo Kα radiation |
| a = 18.1360 (3) Å | µ = 0.11 mm−1 |
| b = 7.3355 (1) Å | T = 118 K |
| c = 14.5986 (3) Å | 0.40 × 0.20 × 0.15 mm |
Data collection top
Bruker SMART APEX CCD
diffractometer | 1890 reflections with I > 2σ(I) |
| 12785 measured reflections | Rint = 0.029 |
| 2242 independent reflections | θmax = 27.5° |
Refinement top
| R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
| wR(F2) = 0.102 | Δρmax = 0.27 e Å−3 |
| S = 1.02 | Δρmin = −0.29 e Å−3 |
| 2242 reflections | Absolute structure: ? |
| 145 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top| | x | y | z | Uiso*/Ueq | |
| O1 | 0.46423 (5) | 0.52259 (12) | 0.36904 (6) | 0.0222 (2) | |
| O2 | 0.34305 (5) | 0.73218 (14) | 0.08352 (6) | 0.0291 (2) | |
| O3 | 0.22956 (6) | 0.7828 (2) | 0.12079 (7) | 0.0467 (3) | |
| N1 | 0.42087 (6) | 0.22878 (14) | 0.35641 (8) | 0.0228 (2) | |
| N2 | 0.54579 (6) | 0.29874 (15) | 0.39501 (8) | 0.0234 (3) | |
| N3 | 0.29278 (6) | 0.73707 (16) | 0.13953 (7) | 0.0238 (3) | |
| C1 | 0.43734 (8) | 0.05109 (18) | 0.36142 (10) | 0.0280 (3) | |
| H1 | 0.3994 | −0.0355 | 0.3502 | 0.034* | |
| C2 | 0.50707 (8) | −0.01134 (18) | 0.38219 (10) | 0.0284 (3) | |
| H2 | 0.5182 | −0.1378 | 0.3850 | 0.034* | |
| C3 | 0.56002 (7) | 0.12058 (19) | 0.39866 (10) | 0.0267 (3) | |
| H3 | 0.6087 | 0.0824 | 0.4132 | 0.032* | |
| C4 | 0.47660 (7) | 0.33980 (16) | 0.37377 (8) | 0.0180 (3) | |
| C5 | 0.39288 (6) | 0.58007 (15) | 0.34572 (8) | 0.0179 (3) | |
| C6 | 0.34150 (7) | 0.60883 (16) | 0.41443 (8) | 0.0205 (3) | |
| H6 | 0.3532 | 0.5820 | 0.4764 | 0.025* | |
| C7 | 0.27269 (7) | 0.67742 (17) | 0.39132 (9) | 0.0218 (3) | |
| H7 | 0.2369 | 0.6965 | 0.4378 | 0.026* | |
| C8 | 0.25564 (7) | 0.71852 (17) | 0.30078 (8) | 0.0202 (3) | |
| H8 | 0.2086 | 0.7655 | 0.2845 | 0.024* | |
| C9 | 0.30919 (7) | 0.68896 (16) | 0.23527 (8) | 0.0181 (3) | |
| C10 | 0.37846 (6) | 0.61910 (15) | 0.25487 (8) | 0.0180 (2) | |
| H10 | 0.4141 | 0.5991 | 0.2083 | 0.022* | |
Atomic displacement parameters (Å2) top| | U11 | U22 | U33 | U12 | U13 | U23 |
| O1 | 0.0150 (4) | 0.0171 (4) | 0.0344 (5) | −0.0013 (3) | −0.0053 (4) | 0.0031 (4) |
| O2 | 0.0272 (5) | 0.0406 (6) | 0.0196 (5) | −0.0023 (4) | 0.0039 (4) | 0.0012 (4) |
| O3 | 0.0262 (6) | 0.0873 (10) | 0.0266 (6) | 0.0152 (6) | −0.0062 (4) | 0.0083 (6) |
| N1 | 0.0197 (5) | 0.0192 (5) | 0.0295 (6) | −0.0015 (4) | −0.0035 (4) | −0.0006 (4) |
| N2 | 0.0175 (5) | 0.0233 (6) | 0.0294 (6) | 0.0008 (4) | −0.0015 (4) | 0.0036 (4) |
| N3 | 0.0215 (5) | 0.0300 (6) | 0.0199 (5) | 0.0000 (4) | −0.0019 (4) | 0.0000 (4) |
| C1 | 0.0278 (7) | 0.0187 (6) | 0.0375 (8) | −0.0030 (5) | −0.0046 (6) | −0.0024 (5) |
| C2 | 0.0300 (7) | 0.0199 (6) | 0.0352 (7) | 0.0038 (5) | −0.0011 (6) | −0.0005 (5) |
| C3 | 0.0209 (6) | 0.0265 (7) | 0.0326 (7) | 0.0050 (5) | −0.0013 (5) | 0.0033 (5) |
| C4 | 0.0183 (6) | 0.0186 (6) | 0.0173 (6) | −0.0010 (4) | 0.0003 (4) | 0.0019 (4) |
| C5 | 0.0150 (5) | 0.0133 (5) | 0.0255 (6) | −0.0016 (4) | −0.0025 (5) | 0.0005 (4) |
| C6 | 0.0237 (6) | 0.0193 (6) | 0.0186 (6) | −0.0031 (5) | −0.0010 (5) | 0.0015 (4) |
| C7 | 0.0215 (6) | 0.0224 (6) | 0.0214 (6) | 0.0007 (5) | 0.0046 (5) | −0.0013 (5) |
| C8 | 0.0154 (5) | 0.0213 (6) | 0.0240 (6) | 0.0022 (4) | 0.0007 (5) | −0.0010 (5) |
| C9 | 0.0185 (6) | 0.0182 (5) | 0.0175 (6) | −0.0013 (4) | −0.0012 (4) | −0.0005 (4) |
| C10 | 0.0152 (5) | 0.0173 (5) | 0.0214 (6) | −0.0010 (4) | 0.0023 (4) | −0.0021 (4) |
Geometric parameters (Å, °) top
| O1—C4 | 1.3613 (15) | C2—H2 | 0.9500 |
| O1—C5 | 1.4029 (14) | C3—H3 | 0.9500 |
| O2—N3 | 1.2252 (14) | C5—C10 | 1.3819 (17) |
| O3—N3 | 1.2256 (15) | C5—C6 | 1.3852 (17) |
| N1—C4 | 1.3225 (16) | C6—C7 | 1.3872 (18) |
| N1—C1 | 1.3392 (17) | C6—H6 | 0.9500 |
| N2—C4 | 1.3273 (16) | C7—C8 | 1.3907 (18) |
| N2—C3 | 1.3332 (17) | C7—H7 | 0.9500 |
| N3—C9 | 1.4720 (16) | C8—C9 | 1.3801 (17) |
| C1—C2 | 1.379 (2) | C8—H8 | 0.9500 |
| C1—H1 | 0.9500 | C9—C10 | 1.3867 (17) |
| C2—C3 | 1.384 (2) | C10—H10 | 0.9500 |
| | | |
| C4—O1—C5 | 117.41 (9) | C10—C5—C6 | 122.42 (11) |
| C4—N1—C1 | 114.73 (11) | C10—C5—O1 | 118.01 (10) |
| C4—N2—C3 | 114.50 (11) | C6—C5—O1 | 119.37 (11) |
| O2—N3—O3 | 123.73 (11) | C5—C6—C7 | 118.97 (11) |
| O2—N3—C9 | 118.44 (11) | C5—C6—H6 | 120.5 |
| O3—N3—C9 | 117.82 (11) | C7—C6—H6 | 120.5 |
| N1—C1—C2 | 122.68 (13) | C6—C7—C8 | 120.65 (11) |
| N1—C1—H1 | 118.7 | C6—C7—H7 | 119.7 |
| C2—C1—H1 | 118.7 | C8—C7—H7 | 119.7 |
| C1—C2—C3 | 116.25 (12) | C9—C8—C7 | 117.91 (11) |
| C1—C2—H2 | 121.9 | C9—C8—H8 | 121.0 |
| C3—C2—H2 | 121.9 | C7—C8—H8 | 121.0 |
| N2—C3—C2 | 122.96 (12) | C8—C9—C10 | 123.55 (11) |
| N2—C3—H3 | 118.5 | C8—C9—N3 | 118.55 (11) |
| C2—C3—H3 | 118.5 | C10—C9—N3 | 117.88 (11) |
| N1—C4—N2 | 128.87 (12) | C5—C10—C9 | 116.49 (11) |
| N1—C4—O1 | 118.10 (11) | C5—C10—H10 | 121.8 |
| N2—C4—O1 | 113.03 (10) | C9—C10—H10 | 121.8 |
| | | |
| C4—N1—C1—C2 | −0.6 (2) | O1—C5—C6—C7 | 175.68 (10) |
| N1—C1—C2—C3 | 0.5 (2) | C5—C6—C7—C8 | −0.65 (18) |
| C4—N2—C3—C2 | −0.3 (2) | C6—C7—C8—C9 | −0.02 (18) |
| C1—C2—C3—N2 | 0.0 (2) | C7—C8—C9—C10 | 0.66 (18) |
| C1—N1—C4—N2 | 0.2 (2) | C7—C8—C9—N3 | −178.15 (11) |
| C1—N1—C4—O1 | 179.32 (11) | O2—N3—C9—C8 | 171.09 (11) |
| C3—N2—C4—N1 | 0.3 (2) | O3—N3—C9—C8 | −7.71 (18) |
| C3—N2—C4—O1 | −178.92 (11) | O2—N3—C9—C10 | −7.78 (17) |
| C5—O1—C4—N1 | −0.16 (16) | O3—N3—C9—C10 | 173.41 (13) |
| C5—O1—C4—N2 | 179.13 (10) | C6—C5—C10—C9 | −0.15 (17) |
| C4—O1—C5—C10 | −94.96 (13) | O1—C5—C10—C9 | −175.15 (10) |
| C4—O1—C5—C6 | 89.88 (13) | C8—C9—C10—C5 | −0.57 (18) |
| C10—C5—C6—C7 | 0.74 (18) | N3—C9—C10—C5 | 178.25 (10) |
We thank the University of Malaya for supporting this study (FS358/2008 A).
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Shah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2009). publCIF. In preparation.
![[Figure 1]](./hb2922fig1thm.gif)
