2-(o-Tol­yloxy)pyrimidine

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

doi:10.1107/S1600536809026609

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1880

doi:10.1107/S1600536809026609

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2-(o-Tolyloxy)pyrimidine

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 7 July 2009; accepted 8 July 2009; online 18 July 2009)

The title compound, C₁₁H₁₀N₂O, crystallizes with two molecules in the asymmetric unit. The angle at the ether O atom is widened to 118.13 (15)° [117.89 (16)° for the second molecule in the asymmetric unit]; the six-membered rings subtend a dihedral angle of 84.3 (1)° [87.4 (1)° in the second molecule].

Related literature

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

Experimental

Crystal data

C₁₁H₁₀N₂O
M_r = 186.21
Orthorhombic, P c a 2₁
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[F² > 2σ(F²)] = 0.033
wR(F²) = 0.088
S = 1.02
2317 reflections
255 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −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 ).

Supporting information

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

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

checkCIF report

Related literature top

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

Experimental top

o-Cresol (2.16 g, 20 mmol) and sodium hydroxide (0.80 g, 20 mmol) were dissolved in water (50 ml) and to the solution was added 2-chloropyridimidine (2.30 g, 20 mmol) dissolved in THF (50 ml). The mixture was heated for 4 h. Water was added and the organic phase extracted with chloroform. The chloroform solution was dried over sodium sulfate; slow evaporation led to the formation of colorless crystals.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₁H₁₀N₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

2-(o-Tolyloxy)pyrimidine top

Crystal data top

C₁₁H₁₀N₂O	F(000) = 784
M_r = 186.21	D_x = 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

Data collection top

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

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0474P)² + 0.3519P] where P = (F_o² + 2F_c²)/3
2317 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₁H₁₀N₂O	V = 1956.16 (8) Å³
M_r = 186.21	Z = 8
Orthorhombic, Pca2₁	Mo Kα radiation
a = 7.5197 (2) Å	µ = 0.08 mm⁻¹
b = 12.7997 (3) Å	T = 153 K
c = 20.3238 (4) Å	0.35 × 0.25 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	2030 reflections with I > 2σ(I)
12792 measured reflections	R_int = 0.028
2317 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	1 restraint
wR(F²) = 0.088	H-atom parameters constrained
S = 1.02	Δρ_max = 0.16 e Å⁻³
2317 reflections	Δρ_min = −0.19 e Å⁻³
255 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₂O
M_r	186.21
Crystal system, space group	Orthorhombic, Pca2₁
Temperature (K)	153
a, b, c (Å)	7.5197 (2), 12.7997 (3), 20.3238 (4)
V (Å³)	1956.16 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12792, 2317, 2030
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.088, 1.02
No. of reflections	2317
No. of parameters	255
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

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

Acknowledgements

We thank the University of Malaya (FP047/2008 C, RG027/09AFR) for supporting this study.

References

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