2-(2-Naphth­yloxy)pyrimidine

Shah Bakhtiar, N.; Bakar, M.A.A.; Abdullah, Z.; Ng, S.W.

doi:10.1107/S1600536809026592

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o1881

doi:10.1107/S1600536809026592

Open

access

2-(2-Naphthyloxy)pyrimidine

Nasir Shah Bakhtiar,^a Maizathul Akmam A. Bakar,^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)

In the title compound, C₁₄H₁₀N₂O, the organic rings are inclined at an angle of 86.1 (1)°. The angle at the ether O atom is widened to 117.18 (14)°.

Related literature

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

Experimental

Crystal data

C₁₄H₁₀N₂O
M_r = 222.24
Orthorhombic, A b a 2
a = 13.0119 (3) Å
b = 22.4944 (5) Å
c = 7.5355 (2) Å
V = 2205.60 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 120 K
0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
7375 measured reflections
1366 independent reflections
1271 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.081
S = 1.03
1366 reflections
154 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 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/S1600536809026592/bt2997sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026592/bt2997Isup2.hkl

checkCIF report

Related literature top

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

Experimental top

2-Naphthol (2.88 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 (2.60 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 C₁₄H₁₀N₂O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

2-(2-Naphthyloxy)pyrimidine top

Crystal data top

C₁₄H₁₀N₂O	F(000) = 928
M_r = 222.24	D_x = 1.339 Mg m⁻³
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 3105 reflections
a = 13.0119 (3) Å	θ = 2.4–28.0°
b = 22.4944 (5) Å	µ = 0.09 mm⁻¹
c = 7.5355 (2) Å	T = 120 K
V = 2205.60 (9) Å³	Block, colorless
Z = 8	0.35 × 0.25 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	1271 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 27.5°, θ_min = 1.8°
ω scans	h = −16→16
7375 measured reflections	k = −29→29
1366 independent reflections	l = −9→9

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0476P)² + 0.7203P] where P = (F_o² + 2F_c²)/3
1366 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₄H₁₀N₂O	V = 2205.60 (9) Å³
M_r = 222.24	Z = 8
Orthorhombic, Aba2	Mo Kα radiation
a = 13.0119 (3) Å	µ = 0.09 mm⁻¹
b = 22.4944 (5) Å	T = 120 K
c = 7.5355 (2) Å	0.35 × 0.25 × 0.15 mm

Data collection top

Bruker SMART APEX diffractometer	1271 reflections with I > 2σ(I)
7375 measured reflections	R_int = 0.026
1366 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	1 restraint
wR(F²) = 0.081	H-atom parameters constrained
S = 1.03	Δρ_max = 0.19 e Å⁻³
1366 reflections	Δρ_min = −0.18 e Å⁻³
154 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.05750 (10)	0.07574 (6)	0.49878 (19)	0.0292 (3)
N1	0.15301 (12)	0.04684 (7)	0.7306 (2)	0.0289 (4)
N2	−0.00893 (12)	0.09426 (7)	0.7772 (2)	0.0282 (3)
C1	0.06580 (13)	0.07234 (7)	0.6787 (2)	0.0225 (4)
C2	0.16628 (15)	0.04528 (9)	0.9060 (3)	0.0343 (5)
H2	0.2275	0.0280	0.9513	0.041*
C3	0.09591 (17)	0.06737 (10)	1.0241 (3)	0.0394 (5)
H3	0.1074	0.0663	1.1486	0.047*
C4	0.00719 (16)	0.09122 (10)	0.9522 (3)	0.0362 (5)
H4	−0.0442	0.1060	1.0302	0.043*
C5	−0.02862 (13)	0.10606 (8)	0.4298 (2)	0.0247 (4)
C6	−0.01790 (13)	0.16416 (8)	0.3824 (3)	0.0246 (4)
H6	0.0460	0.1839	0.3985	0.030*
C7	−0.10287 (13)	0.19501 (7)	0.3090 (2)	0.0233 (4)
C8	−0.09853 (15)	0.25595 (8)	0.2640 (3)	0.0306 (4)
H8	−0.0356	0.2770	0.2763	0.037*
C9	−0.18366 (15)	0.28497 (8)	0.2030 (3)	0.0326 (4)
H9	−0.1795	0.3260	0.1747	0.039*
C10	−0.27770 (14)	0.25454 (8)	0.1818 (3)	0.0292 (4)
H10	−0.3367	0.2753	0.1407	0.035*
C11	−0.28390 (13)	0.19533 (8)	0.2202 (3)	0.0266 (4)
H11	−0.3471	0.1749	0.2032	0.032*
C12	−0.19730 (13)	0.16397 (7)	0.2850 (2)	0.0226 (3)
C13	−0.20239 (14)	0.10272 (8)	0.3295 (3)	0.0271 (4)
H13	−0.2641	0.0813	0.3086	0.033*
C14	−0.11979 (14)	0.07416 (7)	0.4021 (3)	0.0277 (4)
H14	−0.1241	0.0333	0.4333	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0250 (6)	0.0400 (7)	0.0225 (6)	0.0093 (5)	0.0003 (5)	−0.0022 (6)
N1	0.0250 (7)	0.0328 (8)	0.0290 (9)	0.0070 (6)	−0.0002 (6)	−0.0046 (7)
N2	0.0237 (7)	0.0350 (8)	0.0260 (8)	0.0053 (6)	0.0005 (7)	−0.0019 (7)
C1	0.0219 (8)	0.0222 (7)	0.0235 (9)	−0.0017 (6)	−0.0003 (7)	−0.0034 (7)
C2	0.0309 (10)	0.0381 (10)	0.0339 (12)	0.0091 (8)	−0.0079 (9)	−0.0034 (8)
C3	0.0435 (12)	0.0513 (13)	0.0234 (11)	0.0129 (10)	−0.0051 (9)	−0.0014 (9)
C4	0.0331 (10)	0.0500 (12)	0.0255 (11)	0.0115 (9)	0.0047 (9)	−0.0026 (9)
C5	0.0227 (8)	0.0335 (9)	0.0180 (8)	0.0034 (7)	0.0001 (7)	−0.0016 (7)
C6	0.0198 (8)	0.0323 (8)	0.0218 (9)	−0.0040 (6)	0.0013 (7)	−0.0037 (7)
C7	0.0245 (8)	0.0275 (8)	0.0177 (8)	−0.0040 (7)	0.0020 (7)	−0.0029 (7)
C8	0.0296 (9)	0.0299 (9)	0.0322 (10)	−0.0082 (7)	0.0042 (8)	−0.0005 (8)
C9	0.0380 (10)	0.0240 (8)	0.0358 (11)	−0.0032 (7)	0.0041 (10)	0.0029 (8)
C10	0.0300 (9)	0.0314 (8)	0.0263 (10)	0.0050 (7)	−0.0013 (8)	0.0007 (8)
C11	0.0236 (8)	0.0318 (8)	0.0243 (9)	−0.0029 (6)	−0.0013 (7)	−0.0005 (7)
C12	0.0231 (8)	0.0261 (8)	0.0186 (8)	−0.0032 (6)	0.0007 (7)	−0.0011 (7)
C13	0.0254 (8)	0.0275 (8)	0.0285 (10)	−0.0066 (7)	−0.0034 (8)	0.0012 (7)
C14	0.0293 (9)	0.0236 (8)	0.0303 (11)	−0.0007 (7)	0.0006 (9)	0.0009 (7)

Geometric parameters (Å, º) top

O1—C1	1.362 (2)	C7—C8	1.413 (2)
O1—C5	1.411 (2)	C7—C12	1.425 (2)
N1—C1	1.330 (2)	C8—C9	1.365 (3)
N1—C2	1.334 (3)	C8—H8	0.9500
N2—C1	1.319 (2)	C9—C10	1.411 (3)
N2—C4	1.337 (3)	C9—H9	0.9500
C2—C3	1.370 (3)	C10—C11	1.365 (3)
C2—H2	0.9500	C10—H10	0.9500
C3—C4	1.383 (3)	C11—C12	1.416 (2)
C3—H3	0.9500	C11—H11	0.9500
C4—H4	0.9500	C12—C13	1.420 (2)
C5—C6	1.362 (2)	C13—C14	1.366 (3)
C5—C14	1.402 (2)	C13—H13	0.9500
C6—C7	1.418 (2)	C14—H14	0.9500
C6—H6	0.9500

C1—O1—C5	117.18 (14)	C6—C7—C12	118.81 (14)
C1—N1—C2	114.41 (16)	C9—C8—C7	120.79 (16)
C1—N2—C4	114.86 (16)	C9—C8—H8	119.6
N2—C1—N1	128.65 (17)	C7—C8—H8	119.6
N2—C1—O1	118.73 (15)	C8—C9—C10	120.66 (16)
N1—C1—O1	112.61 (15)	C8—C9—H9	119.7
N1—C2—C3	123.22 (19)	C10—C9—H9	119.7
N1—C2—H2	118.4	C11—C10—C9	120.02 (17)
C3—C2—H2	118.4	C11—C10—H10	120.0
C2—C3—C4	116.4 (2)	C9—C10—H10	120.0
C2—C3—H3	121.8	C10—C11—C12	120.80 (16)
C4—C3—H3	121.8	C10—C11—H11	119.6
N2—C4—C3	122.46 (19)	C12—C11—H11	119.6
N2—C4—H4	118.8	C11—C12—C13	121.86 (16)
C3—C4—H4	118.8	C11—C12—C7	119.05 (14)
C6—C5—C14	122.60 (16)	C13—C12—C7	119.08 (16)
C6—C5—O1	118.62 (16)	C14—C13—C12	120.94 (16)
C14—C5—O1	118.65 (15)	C14—C13—H13	119.5
C5—C6—C7	119.48 (15)	C12—C13—H13	119.5
C5—C6—H6	120.3	C13—C14—C5	118.99 (15)
C7—C6—H6	120.3	C13—C14—H14	120.5
C8—C7—C6	122.49 (15)	C5—C14—H14	120.5
C8—C7—C12	118.66 (16)

C4—N2—C1—N1	1.5 (3)	C6—C7—C8—C9	−176.20 (19)
C4—N2—C1—O1	−177.46 (18)	C12—C7—C8—C9	1.6 (3)
C2—N1—C1—N2	−2.1 (3)	C7—C8—C9—C10	−0.7 (3)
C2—N1—C1—O1	176.91 (17)	C8—C9—C10—C11	−0.8 (3)
C5—O1—C1—N2	3.8 (2)	C9—C10—C11—C12	1.3 (3)
C5—O1—C1—N1	−175.36 (14)	C10—C11—C12—C13	178.62 (19)
C1—N1—C2—C3	0.7 (3)	C10—C11—C12—C7	−0.3 (3)
N1—C2—C3—C4	1.0 (3)	C8—C7—C12—C11	−1.1 (3)
C1—N2—C4—C3	0.5 (3)	C6—C7—C12—C11	176.80 (17)
C2—C3—C4—N2	−1.7 (4)	C8—C7—C12—C13	179.90 (17)
C1—O1—C5—C6	96.5 (2)	C6—C7—C12—C13	−2.2 (3)
C1—O1—C5—C14	−87.6 (2)	C11—C12—C13—C14	−175.94 (19)
C14—C5—C6—C7	2.8 (3)	C7—C12—C13—C14	3.0 (3)
O1—C5—C6—C7	178.52 (16)	C12—C13—C14—C5	−1.0 (3)
C5—C6—C7—C8	177.22 (18)	C6—C5—C14—C13	−2.0 (3)
C5—C6—C7—C12	−0.6 (3)	O1—C5—C14—C13	−177.73 (17)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O
M_r	222.24
Crystal system, space group	Orthorhombic, Aba2
Temperature (K)	120
a, b, c (Å)	13.0119 (3), 22.4944 (5), 7.5355 (2)
V (Å³)	2205.60 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
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	7375, 1366, 1271
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.081, 1.03
No. of reflections	1366
No. of parameters	154
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

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