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Acta Crystallogr Sect E Struct Rep Online. 2009 January 1; 65(Pt 1): o114.
Published online 2008 December 13. doi:  10.1107/S1600536808041196
PMCID: PMC2968036

2-Phenoxy­pyrimidine

Abstract

There are two molecules in the asymmetric unit of, C10H8N2O, with dihedral angles between the aromatic ring planes of 75.9 (1) and 79.3 (1)°.

Related literature

For other phen­oxy-substituted N-heterocycles, see: Abdullah & Ng (2008 [triangle]); Hassan et al. (2008 [triangle]); Idris et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o114-scheme1.jpg

Experimental

Crystal data

  • C10H8N2O
  • M r = 172.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o114-efi1.jpg
  • a = 10.859 (1) Å
  • b = 20.181 (2) Å
  • c = 8.1339 (8) Å
  • β = 106.637 (2)°
  • V = 1707.8 (3) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 100 (2) K
  • 0.25 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 9752 measured reflections
  • 3901 independent reflections
  • 3026 reflections with I > 2σ(I)
  • R int = 0.024

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.102
  • S = 1.03
  • 3901 reflections
  • 235 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.22 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/S1600536808041196/tk2342sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041196/tk2342Isup2.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

Phenol (1.88 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 ether. The ether phase was dried over sodium sulfate; the evaporation of the solvent gave well shaped colorless crystals along with some unidentified brown material.

Refinement

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

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of the two independent molecules of C10H8N2O at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C10H8N2OF(000) = 720
Mr = 172.18Dx = 1.339 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2782 reflections
a = 10.859 (1) Åθ = 2.2–28.2°
b = 20.181 (2) ŵ = 0.09 mm1
c = 8.1339 (8) ÅT = 100 K
β = 106.637 (2)°Block, colorless
V = 1707.8 (3) Å30.25 × 0.20 × 0.15 mm
Z = 8

Data collection

Bruker SMART APEX diffractometer3026 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.024
graphiteθmax = 27.5°, θmin = 2.0°
ω scansh = −11→14
9752 measured reflectionsk = −26→26
3901 independent reflectionsl = −10→10

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 = 1.03w = 1/[σ2(Fo2) + (0.0497P)2 + 0.2571P] where P = (Fo2 + 2Fc2)/3
3901 reflections(Δ/σ)max = 0.001
235 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.22 e Å3

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

xyzUiso*/Ueq
O10.69295 (8)0.58216 (5)0.51546 (11)0.0274 (2)
O20.97744 (9)0.67233 (5)0.77250 (11)0.0281 (2)
N10.59037 (10)0.60351 (5)0.72195 (13)0.0245 (2)
N20.77301 (10)0.53229 (5)0.76936 (14)0.0253 (2)
N31.05326 (11)0.62385 (5)1.03911 (13)0.0264 (3)
N40.87443 (10)0.69812 (5)0.96601 (13)0.0247 (2)
C10.59965 (12)0.62116 (6)0.40077 (16)0.0213 (3)
C20.48239 (12)0.59386 (6)0.31580 (17)0.0256 (3)
H20.46170.55000.34080.031*
C30.39513 (13)0.63124 (7)0.19343 (18)0.0297 (3)
H30.31360.61330.13460.036*
C40.42700 (14)0.69480 (7)0.15706 (17)0.0311 (3)
H40.36710.72040.07290.037*
C50.54526 (14)0.72141 (6)0.24218 (18)0.0314 (3)
H15A0.56660.76500.21610.038*
C60.63298 (13)0.68443 (6)0.36592 (17)0.0263 (3)
H6B0.71440.70240.42540.032*
C70.68331 (12)0.57302 (6)0.67684 (16)0.0208 (3)
C80.58755 (14)0.59106 (7)0.88258 (17)0.0303 (3)
H80.52270.61150.92250.036*
C90.67458 (14)0.54993 (7)0.99239 (17)0.0295 (3)
H90.67110.54161.10590.035*
C100.76711 (13)0.52151 (6)0.92888 (17)0.0267 (3)
H100.82910.49311.00150.032*
C111.07433 (12)0.63814 (6)0.72453 (15)0.0235 (3)
C121.05906 (12)0.57148 (6)0.68472 (15)0.0235 (3)
H120.98590.54800.69540.028*
C131.15275 (12)0.53963 (6)0.62894 (15)0.0239 (3)
H131.14390.49390.60070.029*
C141.25931 (13)0.57413 (7)0.61407 (16)0.0258 (3)
H141.32390.55180.57730.031*
C151.27177 (13)0.64082 (7)0.65256 (18)0.0298 (3)
H151.34450.66440.64090.036*
C161.17853 (13)0.67363 (6)0.70825 (17)0.0284 (3)
H161.18650.71960.73450.034*
C170.96950 (12)0.66360 (6)0.93451 (15)0.0214 (3)
C181.03893 (14)0.61819 (7)1.19692 (17)0.0302 (3)
H181.09570.59001.27740.036*
C190.94557 (14)0.65152 (7)1.24657 (16)0.0293 (3)
H190.93680.64721.35900.035*
C200.86503 (13)0.69161 (6)1.12499 (17)0.0271 (3)
H200.79990.71571.15600.033*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0224 (5)0.0355 (5)0.0264 (5)0.0089 (4)0.0102 (4)0.0033 (4)
O20.0304 (5)0.0329 (5)0.0221 (5)0.0140 (4)0.0092 (4)0.0064 (4)
N10.0230 (6)0.0253 (5)0.0255 (6)0.0043 (4)0.0075 (5)−0.0019 (4)
N20.0205 (6)0.0237 (5)0.0302 (6)0.0025 (4)0.0050 (5)−0.0001 (4)
N30.0246 (6)0.0298 (6)0.0219 (5)0.0066 (5)0.0018 (4)0.0021 (4)
N40.0242 (6)0.0241 (5)0.0261 (6)0.0051 (4)0.0079 (5)0.0030 (4)
C10.0202 (6)0.0238 (6)0.0221 (6)0.0030 (5)0.0097 (5)−0.0010 (5)
C20.0237 (7)0.0206 (6)0.0340 (7)−0.0018 (5)0.0107 (6)0.0004 (5)
C30.0232 (7)0.0314 (7)0.0326 (7)0.0008 (5)0.0052 (6)−0.0040 (6)
C40.0389 (8)0.0280 (7)0.0260 (7)0.0102 (6)0.0084 (6)0.0020 (5)
C50.0441 (9)0.0198 (6)0.0346 (7)−0.0002 (6)0.0181 (7)0.0007 (5)
C60.0262 (7)0.0263 (6)0.0291 (7)−0.0069 (5)0.0121 (6)−0.0077 (5)
C70.0192 (6)0.0181 (5)0.0248 (6)−0.0026 (5)0.0059 (5)−0.0031 (5)
C80.0297 (7)0.0349 (7)0.0285 (7)0.0062 (6)0.0118 (6)−0.0031 (6)
C90.0321 (8)0.0323 (7)0.0231 (6)0.0014 (6)0.0059 (6)0.0008 (5)
C100.0239 (7)0.0236 (6)0.0288 (7)0.0007 (5)0.0015 (5)0.0012 (5)
C110.0232 (7)0.0282 (6)0.0175 (6)0.0075 (5)0.0034 (5)0.0034 (5)
C120.0213 (6)0.0276 (6)0.0209 (6)0.0000 (5)0.0052 (5)0.0034 (5)
C130.0246 (7)0.0248 (6)0.0205 (6)0.0010 (5)0.0037 (5)−0.0004 (5)
C140.0218 (7)0.0313 (7)0.0240 (6)0.0039 (5)0.0064 (5)0.0011 (5)
C150.0226 (7)0.0320 (7)0.0345 (7)−0.0030 (6)0.0077 (6)0.0028 (6)
C160.0298 (7)0.0234 (6)0.0292 (7)0.0006 (5)0.0039 (6)0.0005 (5)
C170.0218 (6)0.0202 (6)0.0204 (6)0.0007 (5)0.0031 (5)0.0000 (5)
C180.0308 (8)0.0343 (7)0.0210 (6)0.0057 (6)0.0001 (6)0.0038 (5)
C190.0357 (8)0.0316 (7)0.0200 (6)0.0016 (6)0.0069 (6)0.0015 (5)
C200.0275 (7)0.0268 (6)0.0291 (7)0.0024 (5)0.0113 (6)0.0007 (5)

Geometric parameters (Å, °)

O1—C71.3590 (15)C6—H6B0.9500
O1—C11.4053 (15)C8—C91.3771 (19)
O2—C171.3565 (14)C8—H80.9500
O2—C111.4037 (15)C9—C101.3793 (19)
N1—C71.3205 (16)C9—H90.9500
N1—C81.3394 (17)C10—H100.9500
N2—C71.3307 (16)C11—C161.3772 (19)
N2—C101.3352 (17)C11—C121.3824 (18)
N3—C171.3235 (16)C12—C131.3850 (17)
N3—C181.3414 (17)C12—H120.9500
N4—C171.3297 (16)C13—C141.3851 (18)
N4—C201.3324 (16)C13—H130.9500
C1—C21.3780 (18)C14—C151.3797 (18)
C1—C61.3785 (17)C14—H140.9500
C2—C31.3848 (19)C15—C161.3897 (19)
C2—H20.9500C15—H150.9500
C3—C41.3824 (19)C16—H160.9500
C3—H30.9500C18—C191.3703 (19)
C4—C51.381 (2)C18—H180.9500
C4—H40.9500C19—C201.3792 (18)
C5—C61.389 (2)C19—H190.9500
C5—H15A0.9500C20—H200.9500
C7—O1—C1118.48 (9)N2—C10—C9122.61 (12)
C17—O2—C11117.86 (9)N2—C10—H10118.7
C7—N1—C8114.61 (11)C9—C10—H10118.7
C7—N2—C10114.78 (11)C16—C11—C12122.03 (12)
C17—N3—C18114.85 (11)C16—C11—O2118.22 (11)
C17—N4—C20114.51 (11)C12—C11—O2119.62 (12)
C2—C1—C6121.77 (12)C11—C12—C13118.57 (12)
C2—C1—O1119.74 (11)C11—C12—H12120.7
C6—C1—O1118.26 (11)C13—C12—H12120.7
C1—C2—C3119.11 (12)C12—C13—C14120.38 (12)
C1—C2—H2120.4C12—C13—H13119.8
C3—C2—H2120.4C14—C13—H13119.8
C4—C3—C2119.85 (13)C15—C14—C13120.04 (12)
C4—C3—H3120.1C15—C14—H14120.0
C2—C3—H3120.1C13—C14—H14120.0
C5—C4—C3120.48 (13)C14—C15—C16120.37 (12)
C5—C4—H4119.8C14—C15—H15119.8
C3—C4—H4119.8C16—C15—H15119.8
C4—C5—C6120.05 (12)C11—C16—C15118.61 (12)
C4—C5—H15A120.0C11—C16—H16120.7
C6—C5—H15A120.0C15—C16—H16120.7
C1—C6—C5118.74 (12)N3—C17—N4128.48 (11)
C1—C6—H6B120.6N3—C17—O2118.70 (11)
C5—C6—H6B120.6N4—C17—O2112.82 (10)
N1—C7—N2128.65 (11)N3—C18—C19122.58 (12)
N1—C7—O1118.78 (11)N3—C18—H18118.7
N2—C7—O1112.56 (10)C19—C18—H18118.7
N1—C8—C9122.86 (12)C18—C19—C20116.58 (12)
N1—C8—H8118.6C18—C19—H19121.7
C9—C8—H8118.6C20—C19—H19121.7
C8—C9—C10116.48 (12)N4—C20—C19123.00 (12)
C8—C9—H9121.8N4—C20—H20118.5
C10—C9—H9121.8C19—C20—H20118.5
C7—O1—C1—C2−80.80 (14)C17—O2—C11—C16−106.60 (13)
C7—O1—C1—C6104.66 (13)C17—O2—C11—C1277.48 (15)
C6—C1—C2—C3−0.72 (19)C16—C11—C12—C130.84 (19)
O1—C1—C2—C3−175.06 (11)O2—C11—C12—C13176.60 (10)
C1—C2—C3—C40.64 (19)C11—C12—C13—C140.14 (18)
C2—C3—C4—C5−0.1 (2)C12—C13—C14—C15−0.92 (19)
C3—C4—C5—C6−0.3 (2)C13—C14—C15—C160.7 (2)
C2—C1—C6—C50.28 (18)C12—C11—C16—C15−1.03 (19)
O1—C1—C6—C5174.70 (11)O2—C11—C16—C15−176.84 (11)
C4—C5—C6—C10.24 (19)C14—C15—C16—C110.23 (19)
C8—N1—C7—N2−0.11 (19)C18—N3—C17—N40.05 (19)
C8—N1—C7—O1179.36 (11)C18—N3—C17—O2179.77 (11)
C10—N2—C7—N1−0.22 (19)C20—N4—C17—N30.79 (19)
C10—N2—C7—O1−179.71 (10)C20—N4—C17—O2−178.94 (11)
C1—O1—C7—N1−3.06 (16)C11—O2—C17—N30.36 (17)
C1—O1—C7—N2176.49 (10)C11—O2—C17—N4−179.88 (10)
C7—N1—C8—C90.14 (19)C17—N3—C18—C19−0.63 (19)
N1—C8—C9—C100.1 (2)N3—C18—C19—C200.3 (2)
C7—N2—C10—C90.52 (18)C17—N4—C20—C19−1.10 (19)
C8—C9—C10—N2−0.5 (2)C18—C19—C20—N40.6 (2)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2342).

References

  • Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2165. [PMC free article] [PubMed]
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2007). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Hassan, N. D., Tajuddin, H. A., Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o1820. [PMC free article] [PubMed]
  • Idris, A., Afiffin, A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o7. [PMC free article] [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2009). publCIF In preparation.

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