2-(o-Tol-yloxy)pyrimidine.

The title compound, C(11)H(10)N(2)O, crystallizes with two mol-ecules in the asymmetric unit. The angle at the ether O atom is widened to 118.13 (15)° [117.89 (16)° for the second mol-ecule in the asymmetric unit]; the six-membered rings subtend a dihedral angle of 84.3 (1)° [87.4 (1)° in the second mol-ecule].

Related literature

For 2-phenoxy­pyrimidine, see: Shah Bakhtiar et al. (2009 ▶).

Experimental

Crystal data

C11H10N2O

M = 186.21

Orthorhombic,

a = 7.5197 (2) Å

b = 12.7997 (3) Å

c = 20.3238 (4) Å

V = 1956.16 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 153 K

0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

12792 measured reflections

2317 independent reflections

2030 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.088

S = 1.02

2317 reflections

255 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026609/bt2995sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026609/bt2995Isup2.hkl

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

C11H10N2O	F(000) = 784
Mr = 186.21	Dx = 1.265 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3906 reflections
a = 7.5197 (2) Å	θ = 2.6–27.9°
b = 12.7997 (3) Å	µ = 0.08 mm−1
c = 20.3238 (4) Å	T = 153 K
V = 1956.16 (8) Å3	Block, colorless
Z = 8	0.35 × 0.25 × 0.15 mm

Bruker SMART APEX diffractometer	2030 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 27.5°, θmin = 1.6°
ω scans	h = −9→9
12792 measured reflections	k = −16→16
2317 independent reflections	l = −26→26

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0474P)2 + 0.3519P] where P = (Fo2 + 2Fc2)/3
2317 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.19 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.09137 (18)	0.69839 (11)	0.50102 (8)	0.0294 (3)
O2	0.3463 (2)	0.79763 (11)	0.83583 (8)	0.0288 (3)
N1	0.3704 (2)	0.76815 (13)	0.51731 (9)	0.0290 (4)
N2	0.3222 (2)	0.59497 (13)	0.47797 (10)	0.0346 (4)
N3	0.0668 (3)	0.73277 (14)	0.81493 (10)	0.0311 (4)
N4	0.1165 (3)	0.90210 (14)	0.85951 (10)	0.0342 (4)
C1	0.2716 (3)	0.68835 (14)	0.49926 (10)	0.0240 (4)
C2	0.5457 (3)	0.75182 (17)	0.51316 (13)	0.0346 (5)
H2	0.6241	0.8068	0.5252	0.041*
C3	0.6173 (3)	0.65849 (18)	0.49217 (13)	0.0369 (5)
H3	0.7421	0.6478	0.4895	0.044*
C4	0.4976 (3)	0.58168 (19)	0.47530 (14)	0.0393 (6)
H4	0.5424	0.5160	0.4611	0.047*
C5	0.0193 (3)	0.78821 (16)	0.53078 (11)	0.0260 (4)
C6	−0.0168 (3)	0.87417 (16)	0.49211 (12)	0.0302 (5)
H6	0.0168	0.8751	0.4471	0.036*
C7	−0.1029 (3)	0.95922 (17)	0.51989 (13)	0.0369 (5)
H7	−0.1291	1.0191	0.4940	0.044*
C8	−0.1500 (3)	0.95613 (18)	0.58534 (14)	0.0400 (6)
H8	−0.2097	1.0140	0.6046	0.048*
C9	−0.1111 (3)	0.8691 (2)	0.62345 (13)	0.0419 (6)
H9	−0.1435	0.8687	0.6686	0.050*
C10	−0.0255 (3)	0.78224 (18)	0.59682 (11)	0.0318 (5)
C11	0.0132 (4)	0.6853 (2)	0.63601 (14)	0.0484 (7)
H11A	0.1420	0.6738	0.6377	0.073*
H11B	−0.0442	0.6251	0.6151	0.073*
H11C	−0.0328	0.6936	0.6808	0.073*
C12	0.1667 (3)	0.81024 (15)	0.83622 (10)	0.0239 (4)
C13	−0.1090 (3)	0.75137 (18)	0.81651 (12)	0.0362 (5)
H13	−0.1879	0.6982	0.8019	0.043*
C14	−0.1789 (3)	0.84386 (17)	0.83828 (12)	0.0360 (5)
H14	−0.3034	0.8565	0.8383	0.043*
C15	−0.0596 (3)	0.91746 (18)	0.86010 (14)	0.0392 (6)
H15	−0.1039	0.9820	0.8763	0.047*
C16	0.4168 (3)	0.71305 (15)	0.79991 (10)	0.0254 (4)
C17	0.4576 (3)	0.62233 (17)	0.83289 (13)	0.0337 (5)
H17	0.4291	0.6148	0.8782	0.040*
C18	0.5409 (3)	0.54212 (18)	0.79914 (15)	0.0417 (6)
H18	0.5700	0.4789	0.8211	0.050*
C19	0.5813 (3)	0.5547 (2)	0.73329 (15)	0.0445 (6)
H19	0.6388	0.4999	0.7100	0.053*
C20	0.5387 (3)	0.6461 (2)	0.70137 (13)	0.0433 (6)
H20	0.5663	0.6530	0.6560	0.052*
C21	0.4562 (3)	0.72886 (19)	0.73387 (12)	0.0328 (5)
C22	0.4127 (4)	0.8309 (2)	0.70067 (14)	0.0513 (7)
H22A	0.4773	0.8877	0.7225	0.077*
H22B	0.2845	0.8439	0.7036	0.077*
H22C	0.4481	0.8275	0.6543	0.077*

	U11	U22	U33	U12	U13	U23
O1	0.0202 (8)	0.0232 (7)	0.0447 (9)	−0.0012 (6)	−0.0002 (6)	−0.0071 (6)
O2	0.0207 (8)	0.0268 (7)	0.0389 (8)	0.0008 (6)	−0.0035 (6)	−0.0081 (6)
N1	0.0227 (9)	0.0239 (8)	0.0404 (10)	−0.0021 (7)	−0.0004 (8)	−0.0044 (8)
N2	0.0261 (10)	0.0239 (9)	0.0540 (12)	0.0003 (7)	−0.0015 (9)	−0.0096 (8)
N3	0.0246 (10)	0.0255 (9)	0.0433 (11)	−0.0027 (7)	0.0012 (8)	−0.0061 (8)
N4	0.0274 (11)	0.0249 (9)	0.0503 (11)	0.0003 (7)	−0.0039 (9)	−0.0087 (9)
C1	0.0213 (10)	0.0214 (9)	0.0292 (10)	−0.0003 (7)	−0.0012 (8)	0.0014 (8)
C2	0.0232 (12)	0.0315 (12)	0.0490 (14)	−0.0067 (9)	−0.0006 (10)	−0.0074 (11)
C3	0.0199 (11)	0.0410 (13)	0.0499 (13)	0.0042 (9)	−0.0008 (10)	−0.0085 (11)
C4	0.0296 (12)	0.0316 (12)	0.0567 (15)	0.0092 (9)	−0.0024 (11)	−0.0134 (11)
C5	0.0183 (10)	0.0241 (10)	0.0357 (11)	−0.0007 (7)	−0.0015 (8)	−0.0041 (8)
C6	0.0259 (11)	0.0275 (10)	0.0373 (11)	−0.0023 (8)	0.0013 (9)	−0.0001 (9)
C7	0.0269 (12)	0.0251 (10)	0.0587 (15)	−0.0006 (8)	−0.0047 (11)	−0.0002 (10)
C8	0.0259 (12)	0.0328 (12)	0.0614 (15)	0.0031 (9)	−0.0020 (11)	−0.0210 (11)
C9	0.0304 (13)	0.0549 (15)	0.0403 (13)	−0.0003 (11)	0.0010 (10)	−0.0152 (12)
C10	0.0232 (11)	0.0375 (12)	0.0346 (12)	−0.0014 (9)	−0.0031 (8)	−0.0004 (10)
C11	0.0465 (16)	0.0536 (16)	0.0450 (14)	0.0039 (12)	−0.0021 (12)	0.0111 (12)
C12	0.0229 (11)	0.0226 (9)	0.0260 (9)	−0.0012 (8)	−0.0022 (8)	0.0010 (8)
C13	0.0246 (12)	0.0349 (12)	0.0492 (13)	−0.0044 (9)	0.0013 (10)	−0.0113 (11)
C14	0.0226 (12)	0.0401 (12)	0.0453 (12)	0.0021 (9)	−0.0006 (10)	−0.0090 (11)
C15	0.0315 (13)	0.0321 (12)	0.0541 (14)	0.0064 (9)	−0.0028 (11)	−0.0128 (11)
C16	0.0175 (10)	0.0240 (10)	0.0346 (11)	−0.0008 (8)	−0.0011 (8)	−0.0047 (8)
C17	0.0271 (12)	0.0289 (11)	0.0452 (13)	−0.0003 (9)	0.0037 (10)	0.0030 (10)
C18	0.0302 (13)	0.0240 (11)	0.0709 (17)	0.0006 (9)	0.0035 (12)	−0.0010 (11)
C19	0.0294 (13)	0.0401 (13)	0.0640 (16)	0.0009 (10)	0.0028 (12)	−0.0244 (12)
C20	0.0332 (14)	0.0600 (17)	0.0368 (12)	0.0010 (12)	0.0037 (10)	−0.0129 (12)
C21	0.0255 (12)	0.0375 (12)	0.0353 (11)	−0.0013 (9)	−0.0024 (9)	−0.0001 (10)
C22	0.0511 (17)	0.0592 (18)	0.0435 (14)	0.0078 (14)	0.0015 (13)	0.0192 (13)

O1—C1	1.362 (2)	C9—C10	1.394 (3)
O1—C5	1.408 (2)	C9—H9	0.9500
O2—C12	1.360 (2)	C10—C11	1.503 (4)
O2—C16	1.409 (2)	C11—H11A	0.9800
N1—C1	1.315 (3)	C11—H11B	0.9800
N1—C2	1.337 (3)	C11—H11C	0.9800
N2—C4	1.332 (3)	C13—C14	1.369 (3)
N2—C1	1.327 (2)	C13—H13	0.9500
N3—C12	1.317 (3)	C14—C15	1.375 (3)
N3—C13	1.343 (3)	C14—H14	0.9500
N4—C12	1.323 (3)	C15—H15	0.9500
N4—C15	1.339 (3)	C16—C17	1.375 (3)
C2—C3	1.378 (3)	C16—C21	1.389 (3)
C2—H2	0.9500	C17—C18	1.384 (3)
C3—C4	1.376 (3)	C17—H17	0.9500
C3—H3	0.9500	C18—C19	1.382 (4)
C4—H4	0.9500	C18—H18	0.9500
C5—C6	1.379 (3)	C19—C20	1.376 (4)
C5—C10	1.386 (3)	C19—H19	0.9500
C6—C7	1.387 (3)	C20—C21	1.394 (3)
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.377 (4)	C21—C22	1.506 (3)
C7—H7	0.9500	C22—H22A	0.9800
C8—C9	1.388 (4)	C22—H22B	0.9800
C8—H8	0.9500	C22—H22C	0.9800
C1—O1—C5	118.13 (15)	C10—C11—H11C	109.5
C12—O2—C16	117.89 (16)	H11A—C11—H11C	109.5
C1—N1—C2	114.70 (18)	H11B—C11—H11C	109.5
C4—N2—C1	114.36 (19)	N3—C12—N4	128.6 (2)
C12—N3—C13	114.84 (19)	N3—C12—O2	118.38 (18)
C12—N4—C15	114.59 (19)	N4—C12—O2	113.02 (17)
N1—C1—N2	128.94 (19)	N3—C13—C14	122.6 (2)
N1—C1—O1	118.79 (17)	N3—C13—H13	118.7
N2—C1—O1	112.27 (17)	C14—C13—H13	118.7
N1—C2—C3	122.7 (2)	C13—C14—C15	116.5 (2)
N1—C2—H2	118.6	C13—C14—H14	121.8
C3—C2—H2	118.6	C15—C14—H14	121.8
C2—C3—C4	116.2 (2)	N4—C15—C14	122.8 (2)
C2—C3—H3	121.9	N4—C15—H15	118.6
C4—C3—H3	121.9	C14—C15—H15	118.6
N2—C4—C3	123.1 (2)	C17—C16—C21	123.1 (2)
N2—C4—H4	118.4	C17—C16—O2	118.68 (19)
C3—C4—H4	118.4	C21—C16—O2	117.95 (19)
C6—C5—C10	123.2 (2)	C16—C17—C18	119.0 (2)
C6—C5—O1	118.85 (19)	C16—C17—H17	120.5
C10—C5—O1	117.69 (19)	C18—C17—H17	120.5
C5—C6—C7	119.1 (2)	C17—C18—C19	119.6 (2)
C5—C6—H6	120.4	C17—C18—H18	120.2
C7—C6—H6	120.4	C19—C18—H18	120.2
C8—C7—C6	119.4 (2)	C20—C19—C18	120.3 (2)
C8—C7—H7	120.3	C20—C19—H19	119.9
C6—C7—H7	120.3	C18—C19—H19	119.9
C7—C8—C9	120.5 (2)	C19—C20—C21	121.8 (2)
C7—C8—H8	119.7	C19—C20—H20	119.1
C9—C8—H8	119.7	C21—C20—H20	119.1
C8—C9—C10	121.4 (2)	C16—C21—C20	116.2 (2)
C8—C9—H9	119.3	C16—C21—C22	120.9 (2)
C10—C9—H9	119.3	C20—C21—C22	122.9 (2)
C5—C10—C9	116.4 (2)	C21—C22—H22A	109.5
C5—C10—C11	120.8 (2)	C21—C22—H22B	109.5
C9—C10—C11	122.8 (2)	H22A—C22—H22B	109.5
C10—C11—H11A	109.5	C21—C22—H22C	109.5
C10—C11—H11B	109.5	H22A—C22—H22C	109.5
H11A—C11—H11B	109.5	H22B—C22—H22C	109.5
C2—N1—C1—N2	0.2 (3)	C13—N3—C12—N4	1.1 (3)
C2—N1—C1—O1	−179.1 (2)	C13—N3—C12—O2	−179.6 (2)
C4—N2—C1—N1	0.5 (4)	C15—N4—C12—N3	−1.2 (3)
C4—N2—C1—O1	179.9 (2)	C15—N4—C12—O2	179.5 (2)
C5—O1—C1—N1	−8.8 (3)	C16—O2—C12—N3	13.5 (3)
C5—O1—C1—N2	171.72 (19)	C16—O2—C12—N4	−167.07 (18)
C1—N1—C2—C3	−0.5 (4)	C12—N3—C13—C14	0.3 (3)
N1—C2—C3—C4	0.1 (4)	N3—C13—C14—C15	−1.3 (4)
C1—N2—C4—C3	−0.9 (4)	C12—N4—C15—C14	0.0 (4)
C2—C3—C4—N2	0.7 (4)	C13—C14—C15—N4	1.1 (4)
C1—O1—C5—C6	92.2 (2)	C12—O2—C16—C17	−97.0 (2)
C1—O1—C5—C10	−93.2 (2)	C12—O2—C16—C21	88.6 (2)
C10—C5—C6—C7	−0.3 (3)	C21—C16—C17—C18	−0.4 (3)
O1—C5—C6—C7	174.07 (18)	O2—C16—C17—C18	−174.54 (19)
C5—C6—C7—C8	0.1 (3)	C16—C17—C18—C19	0.0 (3)
C6—C7—C8—C9	0.4 (3)	C17—C18—C19—C20	−0.2 (4)
C7—C8—C9—C10	−0.7 (4)	C18—C19—C20—C21	0.7 (4)
C6—C5—C10—C9	0.0 (3)	C17—C16—C21—C20	0.9 (3)
O1—C5—C10—C9	−174.42 (19)	O2—C16—C21—C20	175.07 (19)
C6—C5—C10—C11	178.4 (2)	C17—C16—C21—C22	−178.4 (2)
O1—C5—C10—C11	4.0 (3)	O2—C16—C21—C22	−4.2 (3)
C8—C9—C10—C5	0.5 (3)	C19—C20—C21—C16	−1.1 (4)
C8—C9—C10—C11	−177.9 (2)	C19—C20—C21—C22	178.2 (2)