2-(p-Tol-yloxy)pyrimidine.

In the title compound, C(11)H(10)N(2)O, the aromatic rings make a dihedral angle of 76.3 (1)°. The C-O-C angle at the ether atom is widened to 117.79 (9)°.

Related literature

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

Experimental

Crystal data

C11H10N2O

M = 186.21

Orthorhombic,

a = 11.2918 (2) Å

b = 7.2275 (1) Å

c = 23.3359 (5) Å

V = 1904.48 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 153 K

0.35 × 0.35 × 0.35 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

12308 measured reflections

2189 independent reflections

1789 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.109

S = 1.02

2189 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.20 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/S1600536809026610/bt2996sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026610/bt2996Isup2.hkl

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

C11H10N2O	F(000) = 784
Mr = 186.21	Dx = 1.299 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3922 reflections
a = 11.2918 (2) Å	θ = 2.8–28.2°
b = 7.2275 (1) Å	µ = 0.09 mm−1
c = 23.3359 (5) Å	T = 153 K
V = 1904.48 (6) Å3	Irregular, colorless
Z = 8	0.35 × 0.35 × 0.35 mm

Bruker SMART APEX diffractometer	1789 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.025
graphite	θmax = 27.5°, θmin = 1.8°
ω scans	h = −14→13
12308 measured reflections	k = −9→9
2189 independent reflections	l = −30→30

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0517P)2 + 0.6197P] where P = (Fo2 + 2Fc2)/3
2189 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.27705 (7)	0.18284 (13)	0.40394 (4)	0.0310 (2)
N1	0.38531 (9)	0.28051 (15)	0.48203 (4)	0.0294 (2)
N2	0.17358 (8)	0.27108 (15)	0.48092 (4)	0.0303 (3)
C1	0.28062 (9)	0.24949 (16)	0.45862 (5)	0.0253 (3)
C2	0.38117 (11)	0.34394 (19)	0.53603 (5)	0.0330 (3)
H2	0.4534	0.3703	0.5552	0.040*
C3	0.27601 (11)	0.37220 (19)	0.56462 (5)	0.0334 (3)
H3	0.2743	0.4166	0.6029	0.040*
C4	0.17305 (11)	0.33291 (18)	0.53495 (5)	0.0332 (3)
H4	0.0992	0.3505	0.5536	0.040*
C5	0.38237 (10)	0.18523 (17)	0.37209 (5)	0.0272 (3)
C6	0.42753 (11)	0.35123 (18)	0.35269 (5)	0.0319 (3)
H6	0.3916	0.4650	0.3633	0.038*
C7	0.52621 (11)	0.34878 (18)	0.31740 (5)	0.0335 (3)
H7	0.5580	0.4625	0.3040	0.040*
C8	0.57990 (11)	0.18345 (18)	0.30110 (5)	0.0305 (3)
C9	0.53213 (11)	0.01971 (18)	0.32187 (5)	0.0339 (3)
H9	0.5677	−0.0946	0.3115	0.041*
C10	0.43334 (11)	0.01911 (18)	0.35755 (5)	0.0318 (3)
H10	0.4018	−0.0940	0.3716	0.038*
C11	0.68626 (13)	0.1829 (2)	0.26196 (6)	0.0416 (3)
H11A	0.7585	0.1985	0.2847	0.062*
H11B	0.6796	0.2848	0.2344	0.062*
H11C	0.6898	0.0650	0.2413	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0222 (4)	0.0426 (5)	0.0281 (4)	−0.0027 (4)	−0.0013 (3)	−0.0065 (4)
N1	0.0229 (5)	0.0361 (6)	0.0291 (5)	−0.0004 (4)	−0.0016 (4)	−0.0035 (4)
N2	0.0215 (5)	0.0360 (6)	0.0335 (5)	−0.0015 (4)	0.0020 (4)	0.0026 (4)
C1	0.0239 (6)	0.0248 (6)	0.0271 (6)	0.0001 (4)	−0.0007 (4)	0.0011 (4)
C2	0.0296 (6)	0.0397 (7)	0.0298 (6)	−0.0048 (5)	−0.0025 (5)	−0.0034 (5)
C3	0.0369 (7)	0.0353 (7)	0.0279 (6)	−0.0040 (5)	0.0048 (5)	−0.0026 (5)
C4	0.0281 (6)	0.0374 (7)	0.0343 (6)	−0.0006 (5)	0.0085 (5)	0.0017 (5)
C5	0.0219 (5)	0.0369 (7)	0.0227 (5)	−0.0008 (5)	−0.0028 (4)	−0.0028 (5)
C6	0.0326 (6)	0.0305 (6)	0.0327 (6)	0.0034 (5)	−0.0003 (5)	−0.0022 (5)
C7	0.0354 (7)	0.0317 (6)	0.0333 (6)	−0.0033 (5)	0.0002 (5)	0.0032 (5)
C8	0.0287 (6)	0.0371 (7)	0.0256 (6)	−0.0010 (5)	−0.0008 (5)	−0.0018 (5)
C9	0.0356 (7)	0.0309 (6)	0.0352 (7)	0.0024 (5)	0.0045 (5)	−0.0038 (5)
C10	0.0336 (6)	0.0305 (6)	0.0313 (6)	−0.0039 (5)	0.0017 (5)	−0.0016 (5)
C11	0.0368 (7)	0.0461 (8)	0.0420 (8)	−0.0015 (6)	0.0096 (6)	−0.0012 (6)

O1—C1	1.3644 (14)	C6—C7	1.3856 (18)
O1—C5	1.4026 (14)	C6—H6	0.9500
N1—C1	1.3215 (14)	C7—C8	1.3928 (18)
N1—C2	1.3419 (16)	C7—H7	0.9500
N2—C1	1.3252 (15)	C8—C9	1.3880 (18)
N2—C4	1.3376 (17)	C8—C11	1.5090 (17)
C2—C3	1.3773 (18)	C9—C10	1.3919 (17)
C2—H2	0.9500	C9—H9	0.9500
C3—C4	1.3826 (18)	C10—H10	0.9500
C3—H3	0.9500	C11—H11A	0.9800
C4—H4	0.9500	C11—H11B	0.9800
C5—C10	1.3740 (17)	C11—H11C	0.9800
C5—C6	1.3801 (17)
C1—O1—C5	117.79 (9)	C7—C6—H6	120.6
C1—N1—C2	114.53 (10)	C6—C7—C8	121.55 (12)
C1—N2—C4	114.44 (10)	C6—C7—H7	119.2
N1—C1—N2	129.31 (11)	C8—C7—H7	119.2
N1—C1—O1	118.23 (10)	C9—C8—C7	117.84 (11)
N2—C1—O1	112.45 (10)	C9—C8—C11	121.23 (12)
N1—C2—C3	122.38 (11)	C7—C8—C11	120.94 (12)
N1—C2—H2	118.8	C8—C9—C10	121.53 (12)
C3—C2—H2	118.8	C8—C9—H9	119.2
C2—C3—C4	116.87 (12)	C10—C9—H9	119.2
C2—C3—H3	121.6	C5—C10—C9	118.73 (12)
C4—C3—H3	121.6	C5—C10—H10	120.6
N2—C4—C3	122.47 (11)	C9—C10—H10	120.6
N2—C4—H4	118.8	C8—C11—H11A	109.5
C3—C4—H4	118.8	C8—C11—H11B	109.5
C10—C5—C6	121.59 (11)	H11A—C11—H11B	109.5
C10—C5—O1	118.38 (11)	C8—C11—H11C	109.5
C6—C5—O1	119.86 (11)	H11A—C11—H11C	109.5
C5—C6—C7	118.75 (12)	H11B—C11—H11C	109.5
C5—C6—H6	120.6
C2—N1—C1—N2	−0.4 (2)	C1—O1—C5—C6	−71.51 (14)
C2—N1—C1—O1	−179.29 (11)	C10—C5—C6—C7	0.44 (18)
C4—N2—C1—N1	−0.13 (19)	O1—C5—C6—C7	−174.79 (10)
C4—N2—C1—O1	178.78 (10)	C5—C6—C7—C8	0.27 (19)
C5—O1—C1—N1	−12.16 (16)	C6—C7—C8—C9	−0.69 (19)
C5—O1—C1—N2	168.79 (10)	C6—C7—C8—C11	179.10 (12)
C1—N1—C2—C3	0.64 (19)	C7—C8—C9—C10	0.42 (19)
N1—C2—C3—C4	−0.3 (2)	C11—C8—C9—C10	−179.37 (12)
C1—N2—C4—C3	0.51 (18)	C6—C5—C10—C9	−0.70 (18)
C2—C3—C4—N2	−0.3 (2)	O1—C5—C10—C9	174.60 (10)
C1—O1—C5—C10	113.10 (12)	C8—C9—C10—C5	0.26 (19)