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ISSN: 2056-9890

2-(o-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 18 July 2009)

The title compound, C11H10N2O, crystallizes with two mol­ecules in the asymmetric unit. The angle at the ether O atom is widened to 118.13 (15)° [117.89 (16)° for the second mol­ecule in the asymmetric unit]; the six-membered rings subtend a dihedral angle of 84.3 (1)° [87.4 (1)° in the second mol­ecule].

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 c a 21

  • a = 7.5197 (2) Å

  • b = 12.7997 (3) Å

  • c = 20.3238 (4) Å

  • V = 1956.16 (8) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.08 mm−1

  • T = 153 K

  • 0.35 × 0.25 × 0.15 mm

Data collection
  • Bruker SMART APEX diffractometer

  • Absorption correction: none

  • 12792 measured reflections

  • 2317 independent reflections

  • 2030 reflections with I > 2σ(I)

  • Rint = 0.028

Refinement
  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.088

  • S = 1.02

  • 2317 reflections

  • 255 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.19 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

o-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 extracted with chloroform. The chloroform solution was dried over sodium sulfate; slow evaporation led to the formation of colorless crystals.

Refinement top

Carbon-bound 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).

In the absence of anomalous scatterers, 2119 Friedel pairs were merged. The absolute structure was arbitrarily set.

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 = 1.265 Mg m3
Orthorhombic, Pca21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2acCell parameters from 3906 reflections
a = 7.5197 (2) Åθ = 2.6–27.9°
b = 12.7997 (3) ŵ = 0.08 mm1
c = 20.3238 (4) ÅT = 153 K
V = 1956.16 (8) Å3Block, colorless
Z = 80.35 × 0.25 × 0.15 mm
Data collection top
Bruker SMART APEX
diffractometer
2030 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.028
Graphite monochromatorθmax = 27.5°, θmin = 1.6°
ω scansh = 99
12792 measured reflectionsk = 1616
2317 independent reflectionsl = 2626
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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0474P)2 + 0.3519P]
where P = (Fo2 + 2Fc2)/3
2317 reflections(Δ/σ)max = 0.001
255 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = 0.19 e Å3
Crystal data top
C11H10N2OV = 1956.16 (8) Å3
Mr = 186.21Z = 8
Orthorhombic, Pca21Mo Kα radiation
a = 7.5197 (2) ŵ = 0.08 mm1
b = 12.7997 (3) ÅT = 153 K
c = 20.3238 (4) Å0.35 × 0.25 × 0.15 mm
Data collection top
Bruker SMART APEX
diffractometer
2030 reflections with I > 2σ(I)
12792 measured reflectionsRint = 0.028
2317 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0331 restraint
wR(F2) = 0.088H-atom parameters constrained
S = 1.02Δρmax = 0.16 e Å3
2317 reflectionsΔρmin = 0.19 e Å3
255 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.09137 (18)0.69839 (11)0.50102 (8)0.0294 (3)
O20.3463 (2)0.79763 (11)0.83583 (8)0.0288 (3)
N10.3704 (2)0.76815 (13)0.51731 (9)0.0290 (4)
N20.3222 (2)0.59497 (13)0.47797 (10)0.0346 (4)
N30.0668 (3)0.73277 (14)0.81493 (10)0.0311 (4)
N40.1165 (3)0.90210 (14)0.85951 (10)0.0342 (4)
C10.2716 (3)0.68835 (14)0.49926 (10)0.0240 (4)
C20.5457 (3)0.75182 (17)0.51316 (13)0.0346 (5)
H20.62410.80680.52520.041*
C30.6173 (3)0.65849 (18)0.49217 (13)0.0369 (5)
H30.74210.64780.48950.044*
C40.4976 (3)0.58168 (19)0.47530 (14)0.0393 (6)
H40.54240.51600.46110.047*
C50.0193 (3)0.78821 (16)0.53078 (11)0.0260 (4)
C60.0168 (3)0.87417 (16)0.49211 (12)0.0302 (5)
H60.01680.87510.44710.036*
C70.1029 (3)0.95922 (17)0.51989 (13)0.0369 (5)
H70.12911.01910.49400.044*
C80.1500 (3)0.95613 (18)0.58534 (14)0.0400 (6)
H80.20971.01400.60460.048*
C90.1111 (3)0.8691 (2)0.62345 (13)0.0419 (6)
H90.14350.86870.66860.050*
C100.0255 (3)0.78224 (18)0.59682 (11)0.0318 (5)
C110.0132 (4)0.6853 (2)0.63601 (14)0.0484 (7)
H11A0.14200.67380.63770.073*
H11B0.04420.62510.61510.073*
H11C0.03280.69360.68080.073*
C120.1667 (3)0.81024 (15)0.83622 (10)0.0239 (4)
C130.1090 (3)0.75137 (18)0.81651 (12)0.0362 (5)
H130.18790.69820.80190.043*
C140.1789 (3)0.84386 (17)0.83828 (12)0.0360 (5)
H140.30340.85650.83830.043*
C150.0596 (3)0.91746 (18)0.86010 (14)0.0392 (6)
H150.10390.98200.87630.047*
C160.4168 (3)0.71305 (15)0.79991 (10)0.0254 (4)
C170.4576 (3)0.62233 (17)0.83289 (13)0.0337 (5)
H170.42910.61480.87820.040*
C180.5409 (3)0.54212 (18)0.79914 (15)0.0417 (6)
H180.57000.47890.82110.050*
C190.5813 (3)0.5547 (2)0.73329 (15)0.0445 (6)
H190.63880.49990.71000.053*
C200.5387 (3)0.6461 (2)0.70137 (13)0.0433 (6)
H200.56630.65300.65600.052*
C210.4562 (3)0.72886 (19)0.73387 (12)0.0328 (5)
C220.4127 (4)0.8309 (2)0.70067 (14)0.0513 (7)
H22A0.47730.88770.72250.077*
H22B0.28450.84390.70360.077*
H22C0.44810.82750.65430.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0202 (8)0.0232 (7)0.0447 (9)0.0012 (6)0.0002 (6)0.0071 (6)
O20.0207 (8)0.0268 (7)0.0389 (8)0.0008 (6)0.0035 (6)0.0081 (6)
N10.0227 (9)0.0239 (8)0.0404 (10)0.0021 (7)0.0004 (8)0.0044 (8)
N20.0261 (10)0.0239 (9)0.0540 (12)0.0003 (7)0.0015 (9)0.0096 (8)
N30.0246 (10)0.0255 (9)0.0433 (11)0.0027 (7)0.0012 (8)0.0061 (8)
N40.0274 (11)0.0249 (9)0.0503 (11)0.0003 (7)0.0039 (9)0.0087 (9)
C10.0213 (10)0.0214 (9)0.0292 (10)0.0003 (7)0.0012 (8)0.0014 (8)
C20.0232 (12)0.0315 (12)0.0490 (14)0.0067 (9)0.0006 (10)0.0074 (11)
C30.0199 (11)0.0410 (13)0.0499 (13)0.0042 (9)0.0008 (10)0.0085 (11)
C40.0296 (12)0.0316 (12)0.0567 (15)0.0092 (9)0.0024 (11)0.0134 (11)
C50.0183 (10)0.0241 (10)0.0357 (11)0.0007 (7)0.0015 (8)0.0041 (8)
C60.0259 (11)0.0275 (10)0.0373 (11)0.0023 (8)0.0013 (9)0.0001 (9)
C70.0269 (12)0.0251 (10)0.0587 (15)0.0006 (8)0.0047 (11)0.0002 (10)
C80.0259 (12)0.0328 (12)0.0614 (15)0.0031 (9)0.0020 (11)0.0210 (11)
C90.0304 (13)0.0549 (15)0.0403 (13)0.0003 (11)0.0010 (10)0.0152 (12)
C100.0232 (11)0.0375 (12)0.0346 (12)0.0014 (9)0.0031 (8)0.0004 (10)
C110.0465 (16)0.0536 (16)0.0450 (14)0.0039 (12)0.0021 (12)0.0111 (12)
C120.0229 (11)0.0226 (9)0.0260 (9)0.0012 (8)0.0022 (8)0.0010 (8)
C130.0246 (12)0.0349 (12)0.0492 (13)0.0044 (9)0.0013 (10)0.0113 (11)
C140.0226 (12)0.0401 (12)0.0453 (12)0.0021 (9)0.0006 (10)0.0090 (11)
C150.0315 (13)0.0321 (12)0.0541 (14)0.0064 (9)0.0028 (11)0.0128 (11)
C160.0175 (10)0.0240 (10)0.0346 (11)0.0008 (8)0.0011 (8)0.0047 (8)
C170.0271 (12)0.0289 (11)0.0452 (13)0.0003 (9)0.0037 (10)0.0030 (10)
C180.0302 (13)0.0240 (11)0.0709 (17)0.0006 (9)0.0035 (12)0.0010 (11)
C190.0294 (13)0.0401 (13)0.0640 (16)0.0009 (10)0.0028 (12)0.0244 (12)
C200.0332 (14)0.0600 (17)0.0368 (12)0.0010 (12)0.0037 (10)0.0129 (12)
C210.0255 (12)0.0375 (12)0.0353 (11)0.0013 (9)0.0024 (9)0.0001 (10)
C220.0511 (17)0.0592 (18)0.0435 (14)0.0078 (14)0.0015 (13)0.0192 (13)
Geometric parameters (Å, º) top
O1—C11.362 (2)C9—C101.394 (3)
O1—C51.408 (2)C9—H90.9500
O2—C121.360 (2)C10—C111.503 (4)
O2—C161.409 (2)C11—H11A0.9800
N1—C11.315 (3)C11—H11B0.9800
N1—C21.337 (3)C11—H11C0.9800
N2—C41.332 (3)C13—C141.369 (3)
N2—C11.327 (2)C13—H130.9500
N3—C121.317 (3)C14—C151.375 (3)
N3—C131.343 (3)C14—H140.9500
N4—C121.323 (3)C15—H150.9500
N4—C151.339 (3)C16—C171.375 (3)
C2—C31.378 (3)C16—C211.389 (3)
C2—H20.9500C17—C181.384 (3)
C3—C41.376 (3)C17—H170.9500
C3—H30.9500C18—C191.382 (4)
C4—H40.9500C18—H180.9500
C5—C61.379 (3)C19—C201.376 (4)
C5—C101.386 (3)C19—H190.9500
C6—C71.387 (3)C20—C211.394 (3)
C6—H60.9500C20—H200.9500
C7—C81.377 (4)C21—C221.506 (3)
C7—H70.9500C22—H22A0.9800
C8—C91.388 (4)C22—H22B0.9800
C8—H80.9500C22—H22C0.9800
C1—O1—C5118.13 (15)C10—C11—H11C109.5
C12—O2—C16117.89 (16)H11A—C11—H11C109.5
C1—N1—C2114.70 (18)H11B—C11—H11C109.5
C4—N2—C1114.36 (19)N3—C12—N4128.6 (2)
C12—N3—C13114.84 (19)N3—C12—O2118.38 (18)
C12—N4—C15114.59 (19)N4—C12—O2113.02 (17)
N1—C1—N2128.94 (19)N3—C13—C14122.6 (2)
N1—C1—O1118.79 (17)N3—C13—H13118.7
N2—C1—O1112.27 (17)C14—C13—H13118.7
N1—C2—C3122.7 (2)C13—C14—C15116.5 (2)
N1—C2—H2118.6C13—C14—H14121.8
C3—C2—H2118.6C15—C14—H14121.8
C2—C3—C4116.2 (2)N4—C15—C14122.8 (2)
C2—C3—H3121.9N4—C15—H15118.6
C4—C3—H3121.9C14—C15—H15118.6
N2—C4—C3123.1 (2)C17—C16—C21123.1 (2)
N2—C4—H4118.4C17—C16—O2118.68 (19)
C3—C4—H4118.4C21—C16—O2117.95 (19)
C6—C5—C10123.2 (2)C16—C17—C18119.0 (2)
C6—C5—O1118.85 (19)C16—C17—H17120.5
C10—C5—O1117.69 (19)C18—C17—H17120.5
C5—C6—C7119.1 (2)C17—C18—C19119.6 (2)
C5—C6—H6120.4C17—C18—H18120.2
C7—C6—H6120.4C19—C18—H18120.2
C8—C7—C6119.4 (2)C20—C19—C18120.3 (2)
C8—C7—H7120.3C20—C19—H19119.9
C6—C7—H7120.3C18—C19—H19119.9
C7—C8—C9120.5 (2)C19—C20—C21121.8 (2)
C7—C8—H8119.7C19—C20—H20119.1
C9—C8—H8119.7C21—C20—H20119.1
C8—C9—C10121.4 (2)C16—C21—C20116.2 (2)
C8—C9—H9119.3C16—C21—C22120.9 (2)
C10—C9—H9119.3C20—C21—C22122.9 (2)
C5—C10—C9116.4 (2)C21—C22—H22A109.5
C5—C10—C11120.8 (2)C21—C22—H22B109.5
C9—C10—C11122.8 (2)H22A—C22—H22B109.5
C10—C11—H11A109.5C21—C22—H22C109.5
C10—C11—H11B109.5H22A—C22—H22C109.5
H11A—C11—H11B109.5H22B—C22—H22C109.5
C2—N1—C1—N20.2 (3)C13—N3—C12—N41.1 (3)
C2—N1—C1—O1179.1 (2)C13—N3—C12—O2179.6 (2)
C4—N2—C1—N10.5 (4)C15—N4—C12—N31.2 (3)
C4—N2—C1—O1179.9 (2)C15—N4—C12—O2179.5 (2)
C5—O1—C1—N18.8 (3)C16—O2—C12—N313.5 (3)
C5—O1—C1—N2171.72 (19)C16—O2—C12—N4167.07 (18)
C1—N1—C2—C30.5 (4)C12—N3—C13—C140.3 (3)
N1—C2—C3—C40.1 (4)N3—C13—C14—C151.3 (4)
C1—N2—C4—C30.9 (4)C12—N4—C15—C140.0 (4)
C2—C3—C4—N20.7 (4)C13—C14—C15—N41.1 (4)
C1—O1—C5—C692.2 (2)C12—O2—C16—C1797.0 (2)
C1—O1—C5—C1093.2 (2)C12—O2—C16—C2188.6 (2)
C10—C5—C6—C70.3 (3)C21—C16—C17—C180.4 (3)
O1—C5—C6—C7174.07 (18)O2—C16—C17—C18174.54 (19)
C5—C6—C7—C80.1 (3)C16—C17—C18—C190.0 (3)
C6—C7—C8—C90.4 (3)C17—C18—C19—C200.2 (4)
C7—C8—C9—C100.7 (4)C18—C19—C20—C210.7 (4)
C6—C5—C10—C90.0 (3)C17—C16—C21—C200.9 (3)
O1—C5—C10—C9174.42 (19)O2—C16—C21—C20175.07 (19)
C6—C5—C10—C11178.4 (2)C17—C16—C21—C22178.4 (2)
O1—C5—C10—C114.0 (3)O2—C16—C21—C224.2 (3)
C8—C9—C10—C50.5 (3)C19—C20—C21—C161.1 (4)
C8—C9—C10—C11177.9 (2)C19—C20—C21—C22178.2 (2)

Experimental details

Crystal data
Chemical formulaC11H10N2O
Mr186.21
Crystal system, space groupOrthorhombic, Pca21
Temperature (K)153
a, b, c (Å)7.5197 (2), 12.7997 (3), 20.3238 (4)
V3)1956.16 (8)
Z8
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.35 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
12792, 2317, 2030
Rint0.028
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.088, 1.02
No. of reflections2317
No. of parameters255
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.19

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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