2-Naphthyl quinoxalin-2-yl ether.

In the crystal structure of the title compound, C(18)H(12)N(2)O, the two fused rings are aligned at 64.2 (1)°; the C-O-C angle is 118.73 (12)°.

Related literature

For the crystal structure of 1-naphthyl quinoxalinyl ether, see: Hassan et al. (2009 ▶).

Experimental

Crystal data

C18H12N2O

M = 272.30

Monoclinic,

a = 6.808 (1) Å

b = 7.609 (1) Å

c = 26.234 (3) Å

β = 92.522 (2)°

V = 1357.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.45 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

7510 measured reflections

3094 independent reflections

1950 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.127

S = 1.04

3094 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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/S1600536809007855/tk2387sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007855/tk2387Isup2.hkl

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

C18H12N2O	F(000) = 568
Mr = 272.30	Dx = 1.332 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1541 reflections
a = 6.808 (1) Å	θ = 2.7–28.2°
b = 7.609 (1) Å	µ = 0.08 mm−1
c = 26.234 (3) Å	T = 295 K
β = 92.522 (2)°	Block, colorless
V = 1357.5 (3) Å3	0.45 × 0.15 × 0.10 mm
Z = 4

Bruker SMART APEX diffractometer	1950 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.032
graphite	θmax = 27.5°, θmin = 2.8°
ω scans	h = −6→8
7510 measured reflections	k = −9→8
3094 independent reflections	l = −28→34

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0544P)2 + 0.1253P] where P = (Fo2 + 2Fc2)/3
3094 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.11303 (15)	0.36756 (17)	0.59259 (4)	0.0477 (3)
N1	−0.13352 (19)	0.2389 (2)	0.47654 (5)	0.0459 (4)
N2	0.25074 (18)	0.24104 (18)	0.52218 (5)	0.0379 (3)
C1	0.2995 (2)	0.3759 (2)	0.61786 (6)	0.0392 (4)
C2	0.4441 (2)	0.4866 (2)	0.59948 (6)	0.0447 (4)
H2	0.4210	0.5499	0.5695	0.054*
C3	0.6192 (2)	0.5003 (2)	0.62616 (6)	0.0435 (4)
H3	0.7168	0.5723	0.6138	0.052*
C4	0.6559 (2)	0.4077 (2)	0.67216 (6)	0.0371 (4)
C5	0.5053 (2)	0.3003 (2)	0.69082 (6)	0.0394 (4)
C6	0.3253 (2)	0.2858 (2)	0.66207 (6)	0.0412 (4)
H6	0.2253	0.2147	0.6735	0.049*
C7	0.8364 (2)	0.4201 (3)	0.70077 (6)	0.0483 (5)
H7	0.9372	0.4892	0.6888	0.058*
C8	0.8642 (3)	0.3322 (3)	0.74553 (7)	0.0618 (6)
H8	0.9839	0.3414	0.7638	0.074*
C9	0.7154 (3)	0.2285 (3)	0.76428 (7)	0.0694 (6)
H9	0.7355	0.1704	0.7953	0.083*
C10	0.5402 (3)	0.2116 (3)	0.73751 (7)	0.0593 (5)
H10	0.4424	0.1406	0.7502	0.071*
C11	0.0985 (2)	0.3003 (2)	0.54445 (6)	0.0375 (4)
C12	−0.0954 (2)	0.2999 (2)	0.52209 (6)	0.0439 (4)
H12	−0.1976	0.3445	0.5406	0.053*
C13	0.0233 (2)	0.1738 (2)	0.45104 (6)	0.0389 (4)
C14	−0.0076 (3)	0.1015 (3)	0.40208 (6)	0.0520 (5)
H14	−0.1333	0.1008	0.3867	0.062*
C15	0.1453 (3)	0.0325 (3)	0.37707 (7)	0.0561 (5)
H15	0.1237	−0.0157	0.3447	0.067*
C16	0.3351 (3)	0.0340 (2)	0.39983 (7)	0.0524 (5)
H16	0.4385	−0.0139	0.3824	0.063*
C17	0.3705 (2)	0.1044 (2)	0.44705 (6)	0.0430 (4)
H17	0.4977	0.1063	0.4615	0.052*
C18	0.2149 (2)	0.1739 (2)	0.47388 (5)	0.0348 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0342 (6)	0.0636 (9)	0.0449 (6)	0.0032 (5)	−0.0035 (5)	−0.0096 (6)
N1	0.0344 (8)	0.0508 (10)	0.0517 (8)	−0.0015 (6)	−0.0080 (6)	0.0037 (7)
N2	0.0336 (7)	0.0387 (8)	0.0409 (7)	−0.0003 (6)	−0.0048 (5)	0.0016 (6)
C1	0.0348 (9)	0.0424 (11)	0.0402 (9)	0.0010 (7)	−0.0013 (7)	−0.0076 (7)
C2	0.0497 (10)	0.0453 (11)	0.0389 (9)	−0.0025 (8)	−0.0017 (7)	0.0046 (8)
C3	0.0441 (9)	0.0424 (11)	0.0441 (9)	−0.0095 (8)	0.0033 (7)	0.0009 (8)
C4	0.0376 (8)	0.0339 (10)	0.0398 (8)	0.0010 (7)	0.0004 (6)	−0.0055 (7)
C5	0.0420 (9)	0.0356 (10)	0.0404 (9)	0.0010 (7)	0.0010 (7)	0.0008 (7)
C6	0.0392 (9)	0.0390 (11)	0.0457 (9)	−0.0056 (7)	0.0052 (7)	−0.0005 (8)
C7	0.0382 (9)	0.0534 (13)	0.0529 (10)	−0.0002 (8)	−0.0015 (7)	−0.0099 (9)
C8	0.0510 (12)	0.0723 (16)	0.0603 (12)	0.0077 (10)	−0.0177 (9)	−0.0017 (10)
C9	0.0681 (15)	0.0816 (17)	0.0571 (12)	0.0052 (12)	−0.0130 (10)	0.0210 (11)
C10	0.0594 (12)	0.0617 (15)	0.0566 (11)	−0.0039 (10)	−0.0004 (9)	0.0194 (10)
C11	0.0366 (9)	0.0351 (10)	0.0404 (8)	−0.0013 (7)	−0.0033 (7)	0.0026 (7)
C12	0.0332 (8)	0.0476 (11)	0.0506 (10)	0.0030 (8)	−0.0019 (7)	0.0007 (8)
C13	0.0387 (9)	0.0341 (10)	0.0431 (9)	−0.0050 (7)	−0.0058 (7)	0.0045 (7)
C14	0.0502 (11)	0.0557 (13)	0.0486 (10)	−0.0079 (9)	−0.0138 (8)	−0.0009 (9)
C15	0.0689 (13)	0.0558 (14)	0.0431 (10)	−0.0075 (10)	−0.0046 (9)	−0.0087 (9)
C16	0.0559 (11)	0.0509 (13)	0.0507 (10)	0.0038 (9)	0.0047 (8)	−0.0040 (9)
C17	0.0401 (9)	0.0415 (11)	0.0473 (9)	0.0018 (7)	−0.0013 (7)	0.0025 (8)
C18	0.0360 (8)	0.0295 (9)	0.0386 (8)	−0.0029 (7)	−0.0036 (6)	0.0060 (7)

O1—C11	1.3622 (18)	C7—H7	0.9300
O1—C1	1.4073 (18)	C8—C9	1.391 (3)
N1—C12	1.297 (2)	C8—H8	0.9300
N1—C13	1.377 (2)	C9—C10	1.363 (3)
N2—C11	1.2928 (19)	C9—H9	0.9300
N2—C18	1.3778 (19)	C10—H10	0.9300
C1—C6	1.352 (2)	C11—C12	1.421 (2)
C1—C2	1.398 (2)	C12—H12	0.9300
C2—C3	1.359 (2)	C13—C14	1.405 (2)
C2—H2	0.9300	C13—C18	1.411 (2)
C3—C4	1.410 (2)	C14—C15	1.360 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.415 (2)	C15—C16	1.399 (2)
C4—C7	1.415 (2)	C15—H15	0.9300
C5—C10	1.410 (2)	C16—C17	1.361 (2)
C5—C6	1.414 (2)	C16—H16	0.9300
C6—H6	0.9300	C17—C18	1.401 (2)
C7—C8	1.357 (2)	C17—H17	0.9300
C11—O1—C1	118.73 (12)	C8—C9—H9	119.8
C12—N1—C13	116.62 (13)	C9—C10—C5	120.83 (19)
C11—N2—C18	115.58 (13)	C9—C10—H10	119.6
C6—C1—C2	122.30 (15)	C5—C10—H10	119.6
C6—C1—O1	117.50 (15)	N2—C11—O1	121.55 (13)
C2—C1—O1	119.95 (14)	N2—C11—C12	124.14 (15)
C3—C2—C1	118.92 (15)	O1—C11—C12	114.31 (14)
C3—C2—H2	120.5	N1—C12—C11	121.72 (15)
C1—C2—H2	120.5	N1—C12—H12	119.1
C2—C3—C4	121.39 (16)	C11—C12—H12	119.1
C2—C3—H3	119.3	N1—C13—C14	119.82 (15)
C4—C3—H3	119.3	N1—C13—C18	121.02 (14)
C3—C4—C5	118.72 (14)	C14—C13—C18	119.14 (15)
C3—C4—C7	122.55 (16)	C15—C14—C13	120.36 (16)
C5—C4—C7	118.72 (15)	C15—C14—H14	119.8
C10—C5—C4	118.70 (15)	C13—C14—H14	119.8
C10—C5—C6	122.33 (16)	C14—C15—C16	120.19 (16)
C4—C5—C6	118.97 (14)	C14—C15—H15	119.9
C1—C6—C5	119.65 (15)	C16—C15—H15	119.9
C1—C6—H6	120.2	C17—C16—C15	120.98 (17)
C5—C6—H6	120.2	C17—C16—H16	119.5
C8—C7—C4	120.72 (17)	C15—C16—H16	119.5
C8—C7—H7	119.6	C16—C17—C18	119.89 (16)
C4—C7—H7	119.6	C16—C17—H17	120.1
C7—C8—C9	120.65 (17)	C18—C17—H17	120.1
C7—C8—H8	119.7	N2—C18—C17	119.67 (14)
C9—C8—H8	119.7	N2—C18—C13	120.91 (14)
C10—C9—C8	120.38 (18)	C17—C18—C13	119.43 (14)
C10—C9—H9	119.8
C11—O1—C1—C6	−119.60 (16)	C18—N2—C11—O1	178.93 (14)
C11—O1—C1—C2	65.9 (2)	C18—N2—C11—C12	−0.3 (2)
C6—C1—C2—C3	2.0 (3)	C1—O1—C11—N2	1.5 (2)
O1—C1—C2—C3	176.20 (15)	C1—O1—C11—C12	−179.20 (15)
C1—C2—C3—C4	−1.1 (3)	C13—N1—C12—C11	0.3 (2)
C2—C3—C4—C5	−0.7 (2)	N2—C11—C12—N1	−0.2 (3)
C2—C3—C4—C7	−179.77 (16)	O1—C11—C12—N1	−179.53 (15)
C3—C4—C5—C10	−178.29 (16)	C12—N1—C13—C14	178.37 (16)
C7—C4—C5—C10	0.8 (2)	C12—N1—C13—C18	0.1 (2)
C3—C4—C5—C6	1.7 (2)	N1—C13—C14—C15	−178.25 (17)
C7—C4—C5—C6	−179.25 (15)	C18—C13—C14—C15	0.0 (3)
C2—C1—C6—C5	−1.1 (3)	C13—C14—C15—C16	−0.4 (3)
O1—C1—C6—C5	−175.37 (14)	C14—C15—C16—C17	−0.2 (3)
C10—C5—C6—C1	179.15 (16)	C15—C16—C17—C18	1.1 (3)
C4—C5—C6—C1	−0.8 (2)	C11—N2—C18—C17	−179.07 (14)
C3—C4—C7—C8	178.35 (17)	C11—N2—C18—C13	0.8 (2)
C5—C4—C7—C8	−0.7 (3)	C16—C17—C18—N2	178.38 (15)
C4—C7—C8—C9	−0.2 (3)	C16—C17—C18—C13	−1.5 (2)
C7—C8—C9—C10	1.0 (3)	N1—C13—C18—N2	−0.7 (2)
C8—C9—C10—C5	−0.9 (3)	C14—C13—C18—N2	−178.94 (15)
C4—C5—C10—C9	0.0 (3)	N1—C13—C18—C17	179.13 (15)
C6—C5—C10—C9	−179.97 (18)	C14—C13—C18—C17	0.9 (2)