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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1859.
Published online 2009 July 15. doi:  10.1107/S1600536809026610
PMCID: PMC2977406

2-(p-Tol­yloxy)pyrimidine

Abstract

In the title compound, C11H10N2O, the aromatic rings make a dihedral angle of 76.3 (1)°. The C—O—C angle at the ether atom is widened to 117.79 (9)°.

Related literature

For 2-phenoxy­pyrimidine, see: Shah Bakhtiar et al. (2009 [triangle]).

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Object name is e-65-o1859-scheme1.jpg

Experimental

Crystal data

  • C11H10N2O
  • M r = 186.21
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1859-efi1.jpg
  • a = 11.2918 (2) Å
  • b = 7.2275 (1) Å
  • c = 23.3359 (5) Å
  • V = 1904.48 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 153 K
  • 0.35 × 0.35 × 0.35 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 12308 measured reflections
  • 2189 independent reflections
  • 1789 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.109
  • S = 1.02
  • 2189 reflections
  • 128 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [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/S1600536809026610/bt2996sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026610/bt2996Isup2.hkl

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

Acknowledgments

We thank the University of Malaya (FP047/2008 C, RG027/09AFR) for supporting this study.

supplementary crystallographic information

Experimental

p-Cresol (2.16 g, 20 mmol) and sodium hydroxide (0.80 g, 20 mmol) were dissolved in water (50 ml) and to the solution was added 2-chloropyridimidine (2.30 g, 20 mmol) dissolved in THF (50 ml). The mixture was heated for 4 h. Water was added and the organic phase was extracted with chloroform. The chloroform solution was dried over sodium sulfate; slow evaporation led to the formation of colorless crystals.

Refinement

H-atoms were placed in calculated positions (C—H 0.95–0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of C11H10N2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C11H10N2OF(000) = 784
Mr = 186.21Dx = 1.299 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 3922 reflections
a = 11.2918 (2) Åθ = 2.8–28.2°
b = 7.2275 (1) ŵ = 0.09 mm1
c = 23.3359 (5) ÅT = 153 K
V = 1904.48 (6) Å3Irregular, colorless
Z = 80.35 × 0.35 × 0.35 mm

Data collection

Bruker SMART APEX diffractometer1789 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
graphiteθmax = 27.5°, θmin = 1.8°
ω scansh = −14→13
12308 measured reflectionsk = −9→9
2189 independent reflectionsl = −30→30

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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0517P)2 + 0.6197P] where P = (Fo2 + 2Fc2)/3
2189 reflections(Δ/σ)max = 0.001
128 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.20 e Å3

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

xyzUiso*/Ueq
O10.27705 (7)0.18284 (13)0.40394 (4)0.0310 (2)
N10.38531 (9)0.28051 (15)0.48203 (4)0.0294 (2)
N20.17358 (8)0.27108 (15)0.48092 (4)0.0303 (3)
C10.28062 (9)0.24949 (16)0.45862 (5)0.0253 (3)
C20.38117 (11)0.34394 (19)0.53603 (5)0.0330 (3)
H20.45340.37030.55520.040*
C30.27601 (11)0.37220 (19)0.56462 (5)0.0334 (3)
H30.27430.41660.60290.040*
C40.17305 (11)0.33291 (18)0.53495 (5)0.0332 (3)
H40.09920.35050.55360.040*
C50.38237 (10)0.18523 (17)0.37209 (5)0.0272 (3)
C60.42753 (11)0.35123 (18)0.35269 (5)0.0319 (3)
H60.39160.46500.36330.038*
C70.52621 (11)0.34878 (18)0.31740 (5)0.0335 (3)
H70.55800.46250.30400.040*
C80.57990 (11)0.18345 (18)0.30110 (5)0.0305 (3)
C90.53213 (11)0.01971 (18)0.32187 (5)0.0339 (3)
H90.5677−0.09460.31150.041*
C100.43334 (11)0.01911 (18)0.35755 (5)0.0318 (3)
H100.4018−0.09400.37160.038*
C110.68626 (13)0.1829 (2)0.26196 (6)0.0416 (3)
H11A0.75850.19850.28470.062*
H11B0.67960.28480.23440.062*
H11C0.68980.06500.24130.062*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0222 (4)0.0426 (5)0.0281 (4)−0.0027 (4)−0.0013 (3)−0.0065 (4)
N10.0229 (5)0.0361 (6)0.0291 (5)−0.0004 (4)−0.0016 (4)−0.0035 (4)
N20.0215 (5)0.0360 (6)0.0335 (5)−0.0015 (4)0.0020 (4)0.0026 (4)
C10.0239 (6)0.0248 (6)0.0271 (6)0.0001 (4)−0.0007 (4)0.0011 (4)
C20.0296 (6)0.0397 (7)0.0298 (6)−0.0048 (5)−0.0025 (5)−0.0034 (5)
C30.0369 (7)0.0353 (7)0.0279 (6)−0.0040 (5)0.0048 (5)−0.0026 (5)
C40.0281 (6)0.0374 (7)0.0343 (6)−0.0006 (5)0.0085 (5)0.0017 (5)
C50.0219 (5)0.0369 (7)0.0227 (5)−0.0008 (5)−0.0028 (4)−0.0028 (5)
C60.0326 (6)0.0305 (6)0.0327 (6)0.0034 (5)−0.0003 (5)−0.0022 (5)
C70.0354 (7)0.0317 (6)0.0333 (6)−0.0033 (5)0.0002 (5)0.0032 (5)
C80.0287 (6)0.0371 (7)0.0256 (6)−0.0010 (5)−0.0008 (5)−0.0018 (5)
C90.0356 (7)0.0309 (6)0.0352 (7)0.0024 (5)0.0045 (5)−0.0038 (5)
C100.0336 (6)0.0305 (6)0.0313 (6)−0.0039 (5)0.0017 (5)−0.0016 (5)
C110.0368 (7)0.0461 (8)0.0420 (8)−0.0015 (6)0.0096 (6)−0.0012 (6)

Geometric parameters (Å, °)

O1—C11.3644 (14)C6—C71.3856 (18)
O1—C51.4026 (14)C6—H60.9500
N1—C11.3215 (14)C7—C81.3928 (18)
N1—C21.3419 (16)C7—H70.9500
N2—C11.3252 (15)C8—C91.3880 (18)
N2—C41.3376 (17)C8—C111.5090 (17)
C2—C31.3773 (18)C9—C101.3919 (17)
C2—H20.9500C9—H90.9500
C3—C41.3826 (18)C10—H100.9500
C3—H30.9500C11—H11A0.9800
C4—H40.9500C11—H11B0.9800
C5—C101.3740 (17)C11—H11C0.9800
C5—C61.3801 (17)
C1—O1—C5117.79 (9)C7—C6—H6120.6
C1—N1—C2114.53 (10)C6—C7—C8121.55 (12)
C1—N2—C4114.44 (10)C6—C7—H7119.2
N1—C1—N2129.31 (11)C8—C7—H7119.2
N1—C1—O1118.23 (10)C9—C8—C7117.84 (11)
N2—C1—O1112.45 (10)C9—C8—C11121.23 (12)
N1—C2—C3122.38 (11)C7—C8—C11120.94 (12)
N1—C2—H2118.8C8—C9—C10121.53 (12)
C3—C2—H2118.8C8—C9—H9119.2
C2—C3—C4116.87 (12)C10—C9—H9119.2
C2—C3—H3121.6C5—C10—C9118.73 (12)
C4—C3—H3121.6C5—C10—H10120.6
N2—C4—C3122.47 (11)C9—C10—H10120.6
N2—C4—H4118.8C8—C11—H11A109.5
C3—C4—H4118.8C8—C11—H11B109.5
C10—C5—C6121.59 (11)H11A—C11—H11B109.5
C10—C5—O1118.38 (11)C8—C11—H11C109.5
C6—C5—O1119.86 (11)H11A—C11—H11C109.5
C5—C6—C7118.75 (12)H11B—C11—H11C109.5
C5—C6—H6120.6
C2—N1—C1—N2−0.4 (2)C1—O1—C5—C6−71.51 (14)
C2—N1—C1—O1−179.29 (11)C10—C5—C6—C70.44 (18)
C4—N2—C1—N1−0.13 (19)O1—C5—C6—C7−174.79 (10)
C4—N2—C1—O1178.78 (10)C5—C6—C7—C80.27 (19)
C5—O1—C1—N1−12.16 (16)C6—C7—C8—C9−0.69 (19)
C5—O1—C1—N2168.79 (10)C6—C7—C8—C11179.10 (12)
C1—N1—C2—C30.64 (19)C7—C8—C9—C100.42 (19)
N1—C2—C3—C4−0.3 (2)C11—C8—C9—C10−179.37 (12)
C1—N2—C4—C30.51 (18)C6—C5—C10—C9−0.70 (18)
C2—C3—C4—N2−0.3 (2)O1—C5—C10—C9174.60 (10)
C1—O1—C5—C10113.10 (12)C8—C9—C10—C50.26 (19)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2996).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). 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