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

Experimental

Crystal data

• C₁₀H₈N₂O

• M _r = 172.18

• Monoclinic,

• a = 10.859 (1) Å

• b = 20.181 (2) Å

• c = 8.1339 (8) Å

• β = 106.637 (2)°

• V = 1707.8 (3) ų

• 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

• 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 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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 1.2U_eq(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

C10H8N2O	F(000) = 720
Mr = 172.18	Dx = 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

Bruker SMART APEX diffractometer	3026 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
graphite	θmax = 27.5°, θmin = 2.0°
ω scans	h = −11→14
9752 measured reflections	k = −26→26
3901 independent reflections	l = −10→10

Refinement

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(Fo2) + (0.0497P)2 + 0.2571P] where P = (Fo2 + 2Fc2)/3
3901 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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)