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ISSN: 2056-9890

2-(3-Meth­­oxy­phen­­oxy)pyrimidine

aDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
*Correspondence e-mail: edward.tiekink@gmail.com

(Received 28 July 2010; accepted 29 July 2010; online 31 July 2010)

In the title compound, C11H10N2O2, the benzene ring faces towards one of the pyrimidine N atoms, and is almost orthogonal to the plane through the pyrimidine ring [dihedral angle = 84.40 (14)°]. In the crystal, the presence of C—H⋯π and ππ [centroid–centroid separation = 3.7658 (18) Å] inter­actions leads to a supra­molecular array in the ac plane. The layers thus formed inter­digitate along the b axis.

Related literature

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001[Kawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23-32.]); Abdullah (2005[Abdullah, Z. (2005). Int. J. Chem. Sci. 3, 9-15.]).

[Scheme 1]

Experimental

Crystal data
  • C11H10N2O2

  • Mr = 202.21

  • Monoclinic, C c

  • a = 8.8120 (16) Å

  • b = 18.215 (3) Å

  • c = 7.2094 (10) Å

  • β = 119.380 (2)°

  • V = 1008.4 (3) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 293 K

  • 0.40 × 0.30 × 0.08 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.889, Tmax = 1.000

  • 4725 measured reflections

  • 1165 independent reflections

  • 897 reflections with I > 2σ(I)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.086

  • S = 1.02

  • 1165 reflections

  • 138 parameters

  • 2 restraints

  • H-atom parameters constrained

  • Δρmax = 0.10 e Å−3

  • Δρmin = −0.10 e Å−3

  • Absolute structure: nd

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C5–C10 ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C4—H4⋯Cg2i 0.93 2.89 3.710 (4) 148
Symmetry code: (i) [x-1, -y, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information


Comment top

Interest in the title compound stems from interesting fluorescence properties of related compounds (Kawai et al. 2001; Abdullah, 2005). In (I), the least-squares plane through the pyrimidine ring bisects the plane through the benzene ring with the C5 and C8 atoms of the latter lying in the plane; the dihedral angle between the planes is 84.40 (14) °. The benzene ring lies to one side of the pyrimidine ring, being proximate to the N1 atom. The methoxy group is almost co-planar with the benzene ring to which is bonded as seen in the value of the C11–O2–C7–C6 torsion angle of 171.7 (2) °.

In the crystal, the presence of C–H···π interactions, formed between pyrimidine-H atoms and benzene rings, and ππ interactions [centroid-centroid separation = 3.7658 (18)Å], formed between pyrimidine rings, leads to the formation of layers in the ac plane, Fig. 2 and Table 1. Layers comprise alternating rows of pyrimidine and benzene molecules, and inter-digitate along the b axis as shown in Fig. 3.

Related literature top

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001); Abdullah (2005).

Experimental top

3-Methoxyphenol (2.2 ml, 20 mmol) was mixed with sodium hydroxide (0.8 g, 20 mmol) in several drops of water. The water was then evaporated. The paste was heated with 2-chloropyrimidine (2.3 g, 20 mmol) at 423–433 K for 5 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 colourless prisms of (I).

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.96 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Uequiv(C). In the absence of significant anomalous scattering effects, 985 Friedel pairs were averaged in the final refinement.

Structure description top

Interest in the title compound stems from interesting fluorescence properties of related compounds (Kawai et al. 2001; Abdullah, 2005). In (I), the least-squares plane through the pyrimidine ring bisects the plane through the benzene ring with the C5 and C8 atoms of the latter lying in the plane; the dihedral angle between the planes is 84.40 (14) °. The benzene ring lies to one side of the pyrimidine ring, being proximate to the N1 atom. The methoxy group is almost co-planar with the benzene ring to which is bonded as seen in the value of the C11–O2–C7–C6 torsion angle of 171.7 (2) °.

In the crystal, the presence of C–H···π interactions, formed between pyrimidine-H atoms and benzene rings, and ππ interactions [centroid-centroid separation = 3.7658 (18)Å], formed between pyrimidine rings, leads to the formation of layers in the ac plane, Fig. 2 and Table 1. Layers comprise alternating rows of pyrimidine and benzene molecules, and inter-digitate along the b axis as shown in Fig. 3.

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001); Abdullah (2005).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.
[Figure 2] Fig. 2. Supramolecular layer in (I) mediated by C–H···π and ππ interactions, shown as orange and purple dashed lines, respectively.
[Figure 3] Fig. 3. Unit-cell contents shown in projection down the c axis in (I), highlighting the stacking of layers. The C–H···π and ππ interactions are shown as orange and purple dashed lines, respectively.
2-(3-Methoxyphenoxy)pyrimidine top
Crystal data top
C11H10N2O2F(000) = 424
Mr = 202.21Dx = 1.332 Mg m3
Monoclinic, CcMo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 1361 reflections
a = 8.8120 (16) Åθ = 2.2–21.9°
b = 18.215 (3) ŵ = 0.09 mm1
c = 7.2094 (10) ÅT = 293 K
β = 119.380 (2)°Prism, colourless
V = 1008.4 (3) Å30.40 × 0.30 × 0.08 mm
Z = 4
Data collection top
Bruker SMART APEX CCD
diffractometer
1165 independent reflections
Radiation source: fine-focus sealed tube897 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1111
Tmin = 0.889, Tmax = 1.000k = 2323
4725 measured reflectionsl = 99
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0443P)2 + 0.0614P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.10 e Å3
1165 reflectionsΔρmin = 0.10 e Å3
138 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
2 restraintsExtinction coefficient: 0.016 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: nd
Secondary atom site location: difference Fourier map
Crystal data top
C11H10N2O2V = 1008.4 (3) Å3
Mr = 202.21Z = 4
Monoclinic, CcMo Kα radiation
a = 8.8120 (16) ŵ = 0.09 mm1
b = 18.215 (3) ÅT = 293 K
c = 7.2094 (10) Å0.40 × 0.30 × 0.08 mm
β = 119.380 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer
1165 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
897 reflections with I > 2σ(I)
Tmin = 0.889, Tmax = 1.000Rint = 0.033
4725 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0322 restraints
wR(F2) = 0.086H-atom parameters constrained
S = 1.02Δρmax = 0.10 e Å3
1165 reflectionsΔρmin = 0.10 e Å3
138 parametersAbsolute structure: nd
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5000 (2)0.02433 (8)0.5000 (3)0.0629 (5)
O20.7604 (2)0.21319 (8)0.3071 (3)0.0628 (5)
N10.2553 (3)0.09456 (10)0.4018 (3)0.0595 (5)
N20.2520 (3)0.03621 (10)0.4056 (4)0.0655 (6)
C10.3265 (3)0.02912 (11)0.4325 (4)0.0510 (5)
C20.0840 (4)0.09409 (16)0.3359 (5)0.0756 (8)
H20.02620.13870.31290.091*
C30.0084 (4)0.03096 (19)0.3015 (5)0.0828 (9)
H30.12720.03140.25550.099*
C40.0819 (4)0.03306 (17)0.3379 (5)0.0789 (8)
H40.02130.07700.31410.095*
C50.5948 (3)0.09030 (11)0.5548 (4)0.0531 (6)
C60.6335 (3)0.12134 (10)0.4098 (4)0.0484 (5)
H60.59540.09950.27760.058*
C70.7304 (3)0.18570 (11)0.4623 (3)0.0488 (5)
C80.7882 (3)0.21731 (13)0.6603 (4)0.0624 (6)
H80.85270.26050.69700.075*
C90.7481 (4)0.18335 (17)0.8027 (4)0.0771 (8)
H90.78700.20450.93590.093*
C100.6533 (3)0.11978 (16)0.7543 (4)0.0697 (7)
H100.62920.09730.85290.084*
C110.8382 (4)0.28395 (15)0.3411 (5)0.0868 (9)
H11A0.84430.29860.21690.130*
H11B0.95350.28230.46150.130*
H11C0.76920.31870.36760.130*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0614 (11)0.0435 (8)0.0919 (13)0.0088 (7)0.0438 (11)0.0096 (8)
O20.0722 (11)0.0520 (9)0.0643 (10)0.0123 (8)0.0335 (8)0.0019 (8)
N10.0551 (11)0.0530 (11)0.0691 (12)0.0075 (9)0.0294 (10)0.0016 (10)
N20.0773 (15)0.0501 (12)0.0735 (14)0.0070 (10)0.0403 (12)0.0005 (10)
C10.0553 (14)0.0481 (12)0.0565 (14)0.0034 (10)0.0329 (12)0.0045 (10)
C20.0570 (16)0.0763 (17)0.087 (2)0.0111 (14)0.0299 (15)0.0078 (15)
C30.0562 (17)0.101 (2)0.087 (2)0.0074 (16)0.0322 (15)0.0199 (17)
C40.076 (2)0.0799 (19)0.084 (2)0.0262 (17)0.0412 (16)0.0136 (15)
C50.0468 (12)0.0451 (12)0.0666 (14)0.0094 (9)0.0273 (11)0.0057 (10)
C60.0480 (12)0.0415 (10)0.0535 (12)0.0036 (9)0.0231 (10)0.0013 (9)
C70.0427 (11)0.0464 (10)0.0546 (13)0.0040 (9)0.0219 (10)0.0008 (10)
C80.0555 (13)0.0619 (13)0.0614 (15)0.0069 (11)0.0223 (12)0.0156 (12)
C90.0779 (19)0.097 (2)0.0549 (15)0.0069 (16)0.0315 (14)0.0186 (15)
C100.0733 (17)0.0811 (18)0.0651 (17)0.0059 (14)0.0419 (14)0.0032 (14)
C110.103 (2)0.0589 (16)0.088 (2)0.0223 (14)0.0389 (19)0.0037 (14)
Geometric parameters (Å, º) top
O1—C11.361 (3)C5—C61.372 (3)
O1—C51.405 (3)C5—C101.377 (3)
O2—C71.365 (3)C6—C71.389 (3)
O2—C111.424 (3)C6—H60.9300
N1—C11.314 (3)C7—C81.384 (3)
N1—C21.342 (3)C8—C91.384 (4)
N2—C11.327 (3)C8—H80.9300
N2—C41.330 (4)C9—C101.369 (4)
C2—C31.360 (4)C9—H90.9300
C2—H20.9300C10—H100.9300
C3—C41.363 (4)C11—H11A0.9600
C3—H30.9300C11—H11B0.9600
C4—H40.9300C11—H11C0.9600
C1—O1—C5117.01 (16)C5—C6—H6120.3
C7—O2—C11117.50 (19)C7—C6—H6120.3
C1—N1—C2114.5 (2)O2—C7—C8124.9 (2)
C1—N2—C4113.7 (2)O2—C7—C6115.23 (18)
N1—C1—N2128.9 (2)C8—C7—C6119.9 (2)
N1—C1—O1118.57 (19)C7—C8—C9118.7 (2)
N2—C1—O1112.54 (19)C7—C8—H8120.7
N1—C2—C3122.6 (3)C9—C8—H8120.7
N1—C2—H2118.7C10—C9—C8122.4 (3)
C3—C2—H2118.7C10—C9—H9118.8
C2—C3—C4116.6 (3)C8—C9—H9118.8
C2—C3—H3121.7C9—C10—C5117.7 (2)
C4—C3—H3121.7C9—C10—H10121.2
N2—C4—C3123.6 (3)C5—C10—H10121.2
N2—C4—H4118.2O2—C11—H11A109.5
C3—C4—H4118.2O2—C11—H11B109.5
C6—C5—C10122.0 (2)H11A—C11—H11B109.5
C6—C5—O1118.3 (2)O2—C11—H11C109.5
C10—C5—O1119.6 (2)H11A—C11—H11C109.5
C5—C6—C7119.3 (2)H11B—C11—H11C109.5
C2—N1—C1—N20.6 (4)C10—C5—C6—C72.0 (3)
C2—N1—C1—O1179.8 (2)O1—C5—C6—C7178.59 (19)
C4—N2—C1—N10.1 (4)C11—O2—C7—C88.0 (3)
C4—N2—C1—O1179.5 (2)C11—O2—C7—C6171.7 (2)
C5—O1—C1—N16.9 (3)C5—C6—C7—O2179.02 (19)
C5—O1—C1—N2173.5 (2)C5—C6—C7—C80.7 (3)
C1—N1—C2—C30.7 (4)O2—C7—C8—C9180.0 (2)
N1—C2—C3—C40.2 (5)C6—C7—C8—C90.3 (3)
C1—N2—C4—C30.8 (4)C7—C8—C9—C100.1 (4)
C2—C3—C4—N20.6 (5)C8—C9—C10—C51.1 (4)
C1—O1—C5—C6100.4 (2)C6—C5—C10—C92.1 (4)
C1—O1—C5—C1082.8 (3)O1—C5—C10—C9178.7 (2)
Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C5–C10 ring.
D—H···AD—HH···AD···AD—H···A
C4—H4···Cg2i0.932.893.710 (4)148
Symmetry code: (i) x1, y, z1/2.

Experimental details

Crystal data
Chemical formulaC11H10N2O2
Mr202.21
Crystal system, space groupMonoclinic, Cc
Temperature (K)293
a, b, c (Å)8.8120 (16), 18.215 (3), 7.2094 (10)
β (°) 119.380 (2)
V3)1008.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.40 × 0.30 × 0.08
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.889, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
4725, 1165, 897
Rint0.033
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.086, 1.02
No. of reflections1165
No. of parameters138
No. of restraints2
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.10, 0.10
Absolute structureNd

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
Cg2 is the centroid of the C5–C10 ring.
D—H···AD—HH···AD···AD—H···A
C4—H4···Cg2i0.932.893.710 (4)148
Symmetry code: (i) x1, y, z1/2.
 

Footnotes

Additional correspondence author, e-mail: zana@um.edu.my.

Acknowledgements

AZ thanks the Ministry of Higher Education, Malaysia, for research grants (PS341/2010, FP047/2008 C and RG027/09AFR). The authors are also grateful to the University of Malaya for support of the crystallographic facility.

References

First citationAbdullah, Z. (2005). Int. J. Chem. Sci. 3, 9–15.  CAS Google Scholar
First citationBrandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationKawai, M., Lee, M. J., Evans, K. O. & Norlund, T. (2001). J. Fluoresc. 11, 23–32.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  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. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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