2-(2-Naphth­yloxy)pyrimidine

Abstract

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 = 13.0119 (3) Å

• b = 22.4944 (5) Å

• c = 7.5355 (2) Å

• V = 2205.60 (9) ų

• 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[F ² > 2σ(F ²)] = 0.029

• wR(F ²) = 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 ▶).

Supplementary Material

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

supplementary crystallographic information

Experimental

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.

Refinement

H-atoms were placed in calculated positions (C—H 0.95 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

In the absence of anomalous scatterers, 1111 Friedel pairs were merged and the absolute structure was arbitrarily set.

Figures

Fig. 1.

Anisotropic displacement ellipsoid plot (Barbour, 2001) of C14H10N2O at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Crystal data

C14H10N2O	F(000) = 928
Mr = 222.24	Dx = 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

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

Refinement

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(Fo2) + (0.0476P)2 + 0.7203P] where P = (Fo2 + 2Fc2)/3
1366 reflections	(Δ/σ)max = 0.001
154 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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)