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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o704.
Published online 2009 March 6. doi:  10.1107/S1600536809007697
PMCID: PMC2968901

3-Nitro­phenyl pyrimidin-2-yl ether

Abstract

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.

Related literature

For the structure of phenyl pyrimidin-2-yl ether, see: Shah Bakhtiar et al. (2009 [triangle]).

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Object name is e-65-0o704-scheme1.jpg

Experimental

Crystal data

  • C10H7N3O3
  • M r = 217.19
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o704-efi1.jpg
  • a = 18.1360 (3) Å
  • b = 7.3355 (1) Å
  • c = 14.5986 (3) Å
  • V = 1942.15 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 118 K
  • 0.40 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: none
  • 12785 measured reflections
  • 2242 independent reflections
  • 1890 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.102
  • S = 1.02
  • 2242 reflections
  • 145 parameters
  • H-atom parameters constrained
  • Δρmax = 0.27 e Å−3
  • Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007697/hb2922sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007697/hb2922Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank the University of Malaya for supporting this study (FS358/2008 A).

supplementary crystallographic information

Experimental

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.

Refinement

The H-atoms were placed in calculated positions (C—H 0.95 Å) and refined as riding with U(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) with displacement ellipsoids drawn at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C10H7N3O3F(000) = 896
Mr = 217.19Dx = 1.486 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 4130 reflections
a = 18.1360 (3) Åθ = 2.8–28.2°
b = 7.3355 (1) ŵ = 0.11 mm1
c = 14.5986 (3) ÅT = 118 K
V = 1942.15 (6) Å3Block, faint brown
Z = 80.40 × 0.20 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer1890 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
graphiteθmax = 27.5°, θmin = 2.3°
ω scansh = −23→23
12785 measured reflectionsk = −9→9
2242 independent reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0556P)2 + 0.7122P] where P = (Fo2 + 2Fc2)/3
2242 reflections(Δ/σ)max = 0.001
145 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.29 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.46423 (5)0.52259 (12)0.36904 (6)0.0222 (2)
O20.34305 (5)0.73218 (14)0.08352 (6)0.0291 (2)
O30.22956 (6)0.7828 (2)0.12079 (7)0.0467 (3)
N10.42087 (6)0.22878 (14)0.35641 (8)0.0228 (2)
N20.54579 (6)0.29874 (15)0.39501 (8)0.0234 (3)
N30.29278 (6)0.73707 (16)0.13953 (7)0.0238 (3)
C10.43734 (8)0.05109 (18)0.36142 (10)0.0280 (3)
H10.3994−0.03550.35020.034*
C20.50707 (8)−0.01134 (18)0.38219 (10)0.0284 (3)
H20.5182−0.13780.38500.034*
C30.56002 (7)0.12058 (19)0.39866 (10)0.0267 (3)
H30.60870.08240.41320.032*
C40.47660 (7)0.33980 (16)0.37377 (8)0.0180 (3)
C50.39288 (6)0.58007 (15)0.34572 (8)0.0179 (3)
C60.34150 (7)0.60883 (16)0.41443 (8)0.0205 (3)
H60.35320.58200.47640.025*
C70.27269 (7)0.67742 (17)0.39132 (9)0.0218 (3)
H70.23690.69650.43780.026*
C80.25564 (7)0.71852 (17)0.30078 (8)0.0202 (3)
H80.20860.76550.28450.024*
C90.30919 (7)0.68896 (16)0.23527 (8)0.0181 (3)
C100.37846 (6)0.61910 (15)0.25487 (8)0.0180 (2)
H100.41410.59910.20830.022*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0150 (4)0.0171 (4)0.0344 (5)−0.0013 (3)−0.0053 (4)0.0031 (4)
O20.0272 (5)0.0406 (6)0.0196 (5)−0.0023 (4)0.0039 (4)0.0012 (4)
O30.0262 (6)0.0873 (10)0.0266 (6)0.0152 (6)−0.0062 (4)0.0083 (6)
N10.0197 (5)0.0192 (5)0.0295 (6)−0.0015 (4)−0.0035 (4)−0.0006 (4)
N20.0175 (5)0.0233 (6)0.0294 (6)0.0008 (4)−0.0015 (4)0.0036 (4)
N30.0215 (5)0.0300 (6)0.0199 (5)0.0000 (4)−0.0019 (4)0.0000 (4)
C10.0278 (7)0.0187 (6)0.0375 (8)−0.0030 (5)−0.0046 (6)−0.0024 (5)
C20.0300 (7)0.0199 (6)0.0352 (7)0.0038 (5)−0.0011 (6)−0.0005 (5)
C30.0209 (6)0.0265 (7)0.0326 (7)0.0050 (5)−0.0013 (5)0.0033 (5)
C40.0183 (6)0.0186 (6)0.0173 (6)−0.0010 (4)0.0003 (4)0.0019 (4)
C50.0150 (5)0.0133 (5)0.0255 (6)−0.0016 (4)−0.0025 (5)0.0005 (4)
C60.0237 (6)0.0193 (6)0.0186 (6)−0.0031 (5)−0.0010 (5)0.0015 (4)
C70.0215 (6)0.0224 (6)0.0214 (6)0.0007 (5)0.0046 (5)−0.0013 (5)
C80.0154 (5)0.0213 (6)0.0240 (6)0.0022 (4)0.0007 (5)−0.0010 (5)
C90.0185 (6)0.0182 (5)0.0175 (6)−0.0013 (4)−0.0012 (4)−0.0005 (4)
C100.0152 (5)0.0173 (5)0.0214 (6)−0.0010 (4)0.0023 (4)−0.0021 (4)

Geometric parameters (Å, °)

O1—C41.3613 (15)C2—H20.9500
O1—C51.4029 (14)C3—H30.9500
O2—N31.2252 (14)C5—C101.3819 (17)
O3—N31.2256 (15)C5—C61.3852 (17)
N1—C41.3225 (16)C6—C71.3872 (18)
N1—C11.3392 (17)C6—H60.9500
N2—C41.3273 (16)C7—C81.3907 (18)
N2—C31.3332 (17)C7—H70.9500
N3—C91.4720 (16)C8—C91.3801 (17)
C1—C21.379 (2)C8—H80.9500
C1—H10.9500C9—C101.3867 (17)
C2—C31.384 (2)C10—H100.9500
C4—O1—C5117.41 (9)C10—C5—C6122.42 (11)
C4—N1—C1114.73 (11)C10—C5—O1118.01 (10)
C4—N2—C3114.50 (11)C6—C5—O1119.37 (11)
O2—N3—O3123.73 (11)C5—C6—C7118.97 (11)
O2—N3—C9118.44 (11)C5—C6—H6120.5
O3—N3—C9117.82 (11)C7—C6—H6120.5
N1—C1—C2122.68 (13)C6—C7—C8120.65 (11)
N1—C1—H1118.7C6—C7—H7119.7
C2—C1—H1118.7C8—C7—H7119.7
C1—C2—C3116.25 (12)C9—C8—C7117.91 (11)
C1—C2—H2121.9C9—C8—H8121.0
C3—C2—H2121.9C7—C8—H8121.0
N2—C3—C2122.96 (12)C8—C9—C10123.55 (11)
N2—C3—H3118.5C8—C9—N3118.55 (11)
C2—C3—H3118.5C10—C9—N3117.88 (11)
N1—C4—N2128.87 (12)C5—C10—C9116.49 (11)
N1—C4—O1118.10 (11)C5—C10—H10121.8
N2—C4—O1113.03 (10)C9—C10—H10121.8
C4—N1—C1—C2−0.6 (2)O1—C5—C6—C7175.68 (10)
N1—C1—C2—C30.5 (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—N20.0 (2)C7—C8—C9—C100.66 (18)
C1—N1—C4—N20.2 (2)C7—C8—C9—N3−178.15 (11)
C1—N1—C4—O1179.32 (11)O2—N3—C9—C8171.09 (11)
C3—N2—C4—N10.3 (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—C10173.41 (13)
C5—O1—C4—N2179.13 (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—C689.88 (13)C8—C9—C10—C5−0.57 (18)
C10—C5—C6—C70.74 (18)N3—C9—C10—C5178.25 (10)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2922).

References

  • 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. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography