2-(p-Tol­yloxy)pyrimidine

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

doi:10.1107/S1600536809026610

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1859

doi:10.1107/S1600536809026610

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2-(p-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 15 July 2009)

In the title compound, C₁₁H₁₀N₂O, 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_r = 186.21
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.109
S = 1.02
2189 reflections
128 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026610/bt2996sup1.cif

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

checkCIF report

Related literature top

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

Experimental top

p-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 was 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 = 1.299 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

Data collection top

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

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0517P)² + 0.6197P] where P = (F_o² + 2F_c²)/3
2189 reflections	(Δ/σ)_max = 0.001
128 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₁H₁₀N₂O	V = 1904.48 (6) Å³
M_r = 186.21	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.2918 (2) Å	µ = 0.09 mm⁻¹
b = 7.2275 (1) Å	T = 153 K
c = 23.3359 (5) Å	0.35 × 0.35 × 0.35 mm

Data collection top

Bruker SMART APEX diffractometer	1789 reflections with I > 2σ(I)
12308 measured reflections	R_int = 0.025
2189 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.02	Δρ_max = 0.19 e Å⁻³
2189 reflections	Δρ_min = −0.20 e Å⁻³
128 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀N₂O
M_r	186.21
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	153
a, b, c (Å)	11.2918 (2), 7.2275 (1), 23.3359 (5)
V (Å³)	1904.48 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.35 × 0.35 × 0.35

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12308, 2189, 1789
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.109, 1.02
No. of reflections	2189
No. of parameters	128
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

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

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shah Bakhtiar, N., Abdullah, Z. & Ng, S. W. (2009). Acta Cryst. E65, o114. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar