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Acta Cryst. (2009). E65, o114    [ doi:10.1107/S1600536808041196 ]

2-Phenoxypyrimidine

N. Shah Bakhtiar, Z. Abdullah and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. 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.
2-Phenoxypyrimidine top
Crystal data top
C10H8N2OF(000) = 720
Mr = 172.18Dx = 1.339 Mg m−3
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 mm−1
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 top
Bruker SMART APEX
diffractometer		3026 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 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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 1.03 w = 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 Å−3
0 restraintsΔρmin = −0.22 e Å−3
Crystal data top
C10H8N2OV = 1707.8 (3) Å3
Mr = 172.18Z = 8
Monoclinic, P21/cMo Kα radiation
a = 10.859 (1) ŵ = 0.09 mm−1
b = 20.181 (2) ÅT = 100 K
c = 8.1339 (8) Å0.25 × 0.20 × 0.15 mm
β = 106.637 (2)°
Data collection top
Bruker SMART APEX
diffractometer		3026 reflections with I > 2σ(I)
9752 measured reflectionsRint = 0.024
3901 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.102Δρmax = 0.18 e Å−3
S = 1.03Δρmin = −0.22 e Å−3
3901 reflectionsAbsolute structure: ?
235 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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)
Acknowledgements top

We thank the University of Malaya for supporting this study (FS358/2008 A).

references
References top

Abdullah, Z. & Ng, S. W. (2008). Acta Cryst. E64, o2165.

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.

Idris, A., Afiffin, A., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o7–?.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2009). publCIF. In preparation.