organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-(p-Tol­yl­oxy)pyrimidine

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: seikweng@um.edu.my

(Received 7 July 2009; accepted 8 July 2009; online 15 July 2009)

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[Shah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10N2O

  • Mr = 186.21

  • Orthorhombic, P b c a

  • 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)

  • Rint = 0.025

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 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[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supporting information


Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C11H10N2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
2-(o-Tolyloxy)pyrimidine top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
1789 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 27.5°, θmin = 1.8°
ω scansh = 1413
12308 measured reflectionsk = 99
2189 independent reflectionsl = 3030
Refinement top
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 = 1.02 w = 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
Crystal data top
C11H10N2OV = 1904.48 (6) Å3
Mr = 186.21Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.2918 (2) ŵ = 0.09 mm1
b = 7.2275 (1) ÅT = 153 K
c = 23.3359 (5) Å0.35 × 0.35 × 0.35 mm
Data collection top
Bruker SMART APEX
diffractometer
1789 reflections with I > 2σ(I)
12308 measured reflectionsRint = 0.025
2189 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.109H-atom parameters constrained
S = 1.02Δρmax = 0.19 e Å3
2189 reflectionsΔρmin = 0.20 e Å3
128 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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)
H90.56770.09460.31150.041*
C100.43334 (11)0.01911 (18)0.35755 (5)0.0318 (3)
H100.40180.09400.37160.038*
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) top
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, º) top
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—N20.4 (2)C1—O1—C5—C671.51 (14)
C2—N1—C1—O1179.29 (11)C10—C5—C6—C70.44 (18)
C4—N2—C1—N10.13 (19)O1—C5—C6—C7174.79 (10)
C4—N2—C1—O1178.78 (10)C5—C6—C7—C80.27 (19)
C5—O1—C1—N112.16 (16)C6—C7—C8—C90.69 (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—C40.3 (2)C11—C8—C9—C10179.37 (12)
C1—N2—C4—C30.51 (18)C6—C5—C10—C90.70 (18)
C2—C3—C4—N20.3 (2)O1—C5—C10—C9174.60 (10)
C1—O1—C5—C10113.10 (12)C8—C9—C10—C50.26 (19)

Experimental details

Crystal data
Chemical formulaC11H10N2O
Mr186.21
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)153
a, b, c (Å)11.2918 (2), 7.2275 (1), 23.3359 (5)
V3)1904.48 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.35 × 0.35 × 0.35
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12308, 2189, 1789
Rint0.025
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.109, 1.02
No. of reflections2189
No. of parameters128
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.20

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS Google Scholar
First citationBruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationShah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWestrip, S. P. (2009). publCIF. In preparation.  Google Scholar

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ISSN: 2056-9890
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