2-Phenoxy­pyrimidine

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

doi:10.1107/S1600536808041196

organic compounds

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ISSN: 2056-9890

Volume 65| Part 1| January 2009| Page o114

doi:10.1107/S1600536808041196

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2-Phenoxypyrimidine

Nasir Shah Bakhtiar,^a Zanariah Abdullah ^a and Seik Weng Ng ^a ^*

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

(Received 4 December 2008; accepted 5 December 2008; online 13 December 2008)

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 ); Hassan et al. (2008 ); Idris et al. (2009 ).

Experimental

Crystal data

C₁₀H₈N₂O
M_r = 172.18
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.037
wR(F²) = 0.102
S = 1.03
3901 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041196/tk2342sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808041196/tk2342Isup2.hkl

checkCIF report

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.

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

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

C₁₀H₈N₂O	F(000) = 720
M_r = 172.18	D_x = 1.339 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2782 reflections
a = 10.859 (1) Å	θ = 2.2–28.2°
b = 20.181 (2) Å	µ = 0.09 mm⁻¹
c = 8.1339 (8) Å	T = 100 K
β = 106.637 (2)°	Block, colorless
V = 1707.8 (3) Å³	0.25 × 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 tube	R_int = 0.024
Graphite monochromator	θ_max = 27.5°, θ_min = 2.0°
ω scans	h = −11→14
9752 measured reflections	k = −26→26
3901 independent reflections	l = −10→10

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0497P)² + 0.2571P] where P = (F_o² + 2F_c²)/3
3901 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₀H₈N₂O	V = 1707.8 (3) Å³
M_r = 172.18	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.859 (1) Å	µ = 0.09 mm⁻¹
b = 20.181 (2) Å	T = 100 K
c = 8.1339 (8) Å	0.25 × 0.20 × 0.15 mm
β = 106.637 (2)°

Data collection top

Bruker SMART APEX diffractometer	3026 reflections with I > 2σ(I)
9752 measured reflections	R_int = 0.024
3901 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.102	H-atom parameters constrained
S = 1.03	Δρ_max = 0.18 e Å⁻³
3901 reflections	Δρ_min = −0.22 e Å⁻³
235 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.69295 (8)	0.58216 (5)	0.51546 (11)	0.0274 (2)
O2	0.97744 (9)	0.67233 (5)	0.77250 (11)	0.0281 (2)
N1	0.59037 (10)	0.60351 (5)	0.72195 (13)	0.0245 (2)
N2	0.77301 (10)	0.53229 (5)	0.76936 (14)	0.0253 (2)
N3	1.05326 (11)	0.62385 (5)	1.03911 (13)	0.0264 (3)
N4	0.87443 (10)	0.69812 (5)	0.96601 (13)	0.0247 (2)
C1	0.59965 (12)	0.62116 (6)	0.40077 (16)	0.0213 (3)
C2	0.48239 (12)	0.59386 (6)	0.31580 (17)	0.0256 (3)
H2	0.4617	0.5500	0.3408	0.031*
C3	0.39513 (13)	0.63124 (7)	0.19343 (18)	0.0297 (3)
H3	0.3136	0.6133	0.1346	0.036*
C4	0.42700 (14)	0.69480 (7)	0.15706 (17)	0.0311 (3)
H4	0.3671	0.7204	0.0729	0.037*
C5	0.54526 (14)	0.72141 (6)	0.24218 (18)	0.0314 (3)
H15A	0.5666	0.7650	0.2161	0.038*
C6	0.63298 (13)	0.68443 (6)	0.36592 (17)	0.0263 (3)
H6B	0.7144	0.7024	0.4254	0.032*
C7	0.68331 (12)	0.57302 (6)	0.67684 (16)	0.0208 (3)
C8	0.58755 (14)	0.59106 (7)	0.88258 (17)	0.0303 (3)
H8	0.5227	0.6115	0.9225	0.036*
C9	0.67458 (14)	0.54993 (7)	0.99239 (17)	0.0295 (3)
H9	0.6711	0.5416	1.1059	0.035*
C10	0.76711 (13)	0.52151 (6)	0.92888 (17)	0.0267 (3)
H10	0.8291	0.4931	1.0015	0.032*
C11	1.07433 (12)	0.63814 (6)	0.72453 (15)	0.0235 (3)
C12	1.05906 (12)	0.57148 (6)	0.68472 (15)	0.0235 (3)
H12	0.9859	0.5480	0.6954	0.028*
C13	1.15275 (12)	0.53963 (6)	0.62894 (15)	0.0239 (3)
H13	1.1439	0.4939	0.6007	0.029*
C14	1.25931 (13)	0.57413 (7)	0.61407 (16)	0.0258 (3)
H14	1.3239	0.5518	0.5773	0.031*
C15	1.27177 (13)	0.64082 (7)	0.65256 (18)	0.0298 (3)
H15	1.3445	0.6644	0.6409	0.036*
C16	1.17853 (13)	0.67363 (6)	0.70825 (17)	0.0284 (3)
H16	1.1865	0.7196	0.7345	0.034*
C17	0.96950 (12)	0.66360 (6)	0.93451 (15)	0.0214 (3)
C18	1.03893 (14)	0.61819 (7)	1.19692 (17)	0.0302 (3)
H18	1.0957	0.5900	1.2774	0.036*
C19	0.94557 (14)	0.65152 (7)	1.24657 (16)	0.0293 (3)
H19	0.9368	0.6472	1.3590	0.035*
C20	0.86503 (13)	0.69161 (6)	1.12499 (17)	0.0271 (3)
H20	0.7999	0.7157	1.1560	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0224 (5)	0.0355 (5)	0.0264 (5)	0.0089 (4)	0.0102 (4)	0.0033 (4)
O2	0.0304 (5)	0.0329 (5)	0.0221 (5)	0.0140 (4)	0.0092 (4)	0.0064 (4)
N1	0.0230 (6)	0.0253 (5)	0.0255 (6)	0.0043 (4)	0.0075 (5)	−0.0019 (4)
N2	0.0205 (6)	0.0237 (5)	0.0302 (6)	0.0025 (4)	0.0050 (5)	−0.0001 (4)
N3	0.0246 (6)	0.0298 (6)	0.0219 (5)	0.0066 (5)	0.0018 (4)	0.0021 (4)
N4	0.0242 (6)	0.0241 (5)	0.0261 (6)	0.0051 (4)	0.0079 (5)	0.0030 (4)
C1	0.0202 (6)	0.0238 (6)	0.0221 (6)	0.0030 (5)	0.0097 (5)	−0.0010 (5)
C2	0.0237 (7)	0.0206 (6)	0.0340 (7)	−0.0018 (5)	0.0107 (6)	0.0004 (5)
C3	0.0232 (7)	0.0314 (7)	0.0326 (7)	0.0008 (5)	0.0052 (6)	−0.0040 (6)
C4	0.0389 (8)	0.0280 (7)	0.0260 (7)	0.0102 (6)	0.0084 (6)	0.0020 (5)
C5	0.0441 (9)	0.0198 (6)	0.0346 (7)	−0.0002 (6)	0.0181 (7)	0.0007 (5)
C6	0.0262 (7)	0.0263 (6)	0.0291 (7)	−0.0069 (5)	0.0121 (6)	−0.0077 (5)
C7	0.0192 (6)	0.0181 (5)	0.0248 (6)	−0.0026 (5)	0.0059 (5)	−0.0031 (5)
C8	0.0297 (7)	0.0349 (7)	0.0285 (7)	0.0062 (6)	0.0118 (6)	−0.0031 (6)
C9	0.0321 (8)	0.0323 (7)	0.0231 (6)	0.0014 (6)	0.0059 (6)	0.0008 (5)
C10	0.0239 (7)	0.0236 (6)	0.0288 (7)	0.0007 (5)	0.0015 (5)	0.0012 (5)
C11	0.0232 (7)	0.0282 (6)	0.0175 (6)	0.0075 (5)	0.0034 (5)	0.0034 (5)
C12	0.0213 (6)	0.0276 (6)	0.0209 (6)	0.0000 (5)	0.0052 (5)	0.0034 (5)
C13	0.0246 (7)	0.0248 (6)	0.0205 (6)	0.0010 (5)	0.0037 (5)	−0.0004 (5)
C14	0.0218 (7)	0.0313 (7)	0.0240 (6)	0.0039 (5)	0.0064 (5)	0.0011 (5)
C15	0.0226 (7)	0.0320 (7)	0.0345 (7)	−0.0030 (6)	0.0077 (6)	0.0028 (6)
C16	0.0298 (7)	0.0234 (6)	0.0292 (7)	0.0006 (5)	0.0039 (6)	0.0005 (5)
C17	0.0218 (6)	0.0202 (6)	0.0204 (6)	0.0007 (5)	0.0031 (5)	0.0000 (5)
C18	0.0308 (8)	0.0343 (7)	0.0210 (6)	0.0057 (6)	0.0001 (6)	0.0038 (5)
C19	0.0357 (8)	0.0316 (7)	0.0200 (6)	0.0016 (6)	0.0069 (6)	0.0015 (5)
C20	0.0275 (7)	0.0268 (6)	0.0291 (7)	0.0024 (5)	0.0113 (6)	0.0007 (5)

Geometric parameters (Å, º) top

O1—C7	1.3590 (15)	C6—H6B	0.9500
O1—C1	1.4053 (15)	C8—C9	1.3771 (19)
O2—C17	1.3565 (14)	C8—H8	0.9500
O2—C11	1.4037 (15)	C9—C10	1.3793 (19)
N1—C7	1.3205 (16)	C9—H9	0.9500
N1—C8	1.3394 (17)	C10—H10	0.9500
N2—C7	1.3307 (16)	C11—C16	1.3772 (19)
N2—C10	1.3352 (17)	C11—C12	1.3824 (18)
N3—C17	1.3235 (16)	C12—C13	1.3850 (17)
N3—C18	1.3414 (17)	C12—H12	0.9500
N4—C17	1.3297 (16)	C13—C14	1.3851 (18)
N4—C20	1.3324 (16)	C13—H13	0.9500
C1—C2	1.3780 (18)	C14—C15	1.3797 (18)
C1—C6	1.3785 (17)	C14—H14	0.9500
C2—C3	1.3848 (19)	C15—C16	1.3897 (19)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.3824 (19)	C16—H16	0.9500
C3—H3	0.9500	C18—C19	1.3703 (19)
C4—C5	1.381 (2)	C18—H18	0.9500
C4—H4	0.9500	C19—C20	1.3792 (18)
C5—C6	1.389 (2)	C19—H19	0.9500
C5—H15A	0.9500	C20—H20	0.9500

C7—O1—C1	118.48 (9)	N2—C10—C9	122.61 (12)
C17—O2—C11	117.86 (9)	N2—C10—H10	118.7
C7—N1—C8	114.61 (11)	C9—C10—H10	118.7
C7—N2—C10	114.78 (11)	C16—C11—C12	122.03 (12)
C17—N3—C18	114.85 (11)	C16—C11—O2	118.22 (11)
C17—N4—C20	114.51 (11)	C12—C11—O2	119.62 (12)
C2—C1—C6	121.77 (12)	C11—C12—C13	118.57 (12)
C2—C1—O1	119.74 (11)	C11—C12—H12	120.7
C6—C1—O1	118.26 (11)	C13—C12—H12	120.7
C1—C2—C3	119.11 (12)	C12—C13—C14	120.38 (12)
C1—C2—H2	120.4	C12—C13—H13	119.8
C3—C2—H2	120.4	C14—C13—H13	119.8
C4—C3—C2	119.85 (13)	C15—C14—C13	120.04 (12)
C4—C3—H3	120.1	C15—C14—H14	120.0
C2—C3—H3	120.1	C13—C14—H14	120.0
C5—C4—C3	120.48 (13)	C14—C15—C16	120.37 (12)
C5—C4—H4	119.8	C14—C15—H15	119.8
C3—C4—H4	119.8	C16—C15—H15	119.8
C4—C5—C6	120.05 (12)	C11—C16—C15	118.61 (12)
C4—C5—H15A	120.0	C11—C16—H16	120.7
C6—C5—H15A	120.0	C15—C16—H16	120.7
C1—C6—C5	118.74 (12)	N3—C17—N4	128.48 (11)
C1—C6—H6B	120.6	N3—C17—O2	118.70 (11)
C5—C6—H6B	120.6	N4—C17—O2	112.82 (10)
N1—C7—N2	128.65 (11)	N3—C18—C19	122.58 (12)
N1—C7—O1	118.78 (11)	N3—C18—H18	118.7
N2—C7—O1	112.56 (10)	C19—C18—H18	118.7
N1—C8—C9	122.86 (12)	C18—C19—C20	116.58 (12)
N1—C8—H8	118.6	C18—C19—H19	121.7
C9—C8—H8	118.6	C20—C19—H19	121.7
C8—C9—C10	116.48 (12)	N4—C20—C19	123.00 (12)
C8—C9—H9	121.8	N4—C20—H20	118.5
C10—C9—H9	121.8	C19—C20—H20	118.5

C7—O1—C1—C2	−80.80 (14)	C17—O2—C11—C16	−106.60 (13)
C7—O1—C1—C6	104.66 (13)	C17—O2—C11—C12	77.48 (15)
C6—C1—C2—C3	−0.72 (19)	C16—C11—C12—C13	0.84 (19)
O1—C1—C2—C3	−175.06 (11)	O2—C11—C12—C13	176.60 (10)
C1—C2—C3—C4	0.64 (19)	C11—C12—C13—C14	0.14 (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—C16	0.7 (2)
C2—C1—C6—C5	0.28 (18)	C12—C11—C16—C15	−1.03 (19)
O1—C1—C6—C5	174.70 (11)	O2—C11—C16—C15	−176.84 (11)
C4—C5—C6—C1	0.24 (19)	C14—C15—C16—C11	0.23 (19)
C8—N1—C7—N2	−0.11 (19)	C18—N3—C17—N4	0.05 (19)
C8—N1—C7—O1	179.36 (11)	C18—N3—C17—O2	179.77 (11)
C10—N2—C7—N1	−0.22 (19)	C20—N4—C17—N3	0.79 (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—N3	0.36 (17)
C1—O1—C7—N2	176.49 (10)	C11—O2—C17—N4	−179.88 (10)
C7—N1—C8—C9	0.14 (19)	C17—N3—C18—C19	−0.63 (19)
N1—C8—C9—C10	0.1 (2)	N3—C18—C19—C20	0.3 (2)
C7—N2—C10—C9	0.52 (18)	C17—N4—C20—C19	−1.10 (19)
C8—C9—C10—N2	−0.5 (2)	C18—C19—C20—N4	0.6 (2)

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂O
M_r	172.18
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	10.859 (1), 20.181 (2), 8.1339 (8)
β (°)	106.637 (2)
V (Å³)	1707.8 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	9752, 3901, 3026
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.102, 1.03
No. of reflections	3901
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

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

References

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