2-(2-Naphth-yloxy)pyrimidine.

In the title compound, C(14)H(10)N(2)O, 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 = 222.24

Orthorhombic,

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[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

Δρmax = 0.19 e Å−3

Δρmin = −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 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809026592/bt2997sup1.cif

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

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

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

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 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

	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*

	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)

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)