1-Naphthyl quinoxalin-2-yl ether.

In the crystal structure of the title compound, C(18)H(12)N(2)O, the dihedral angle between the two fused-ring systems is 84.3 (1) °; the C-O-C angle at the ether O atom is 117.31 (18)°.

Related literature

For the crystal structure of the two forms of quinoxalinyl 2-phenyl ether, see: Abdullah & Ng (2008 ▶); Hassan et al. (2008 ▶).

Experimental

Crystal data

C18H12N2O

M = 272.30

Orthorhombic,

a = 18.2758 (6) Å

b = 18.5123 (6) Å

c = 7.7947 (3) Å

V = 2637.2 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 118 K

0.12 × 0.04 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

12370 measured reflections

1626 independent reflections

1316 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.087

S = 1.02

1626 reflections

190 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.24 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/S1600536809007867/tk2386sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007867/tk2386Isup2.hkl

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

C18H12N2O	F(000) = 1136
Mr = 272.30	Dx = 1.372 Mg m−3
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: A 2 -2ac	Cell parameters from 1495 reflections
a = 18.2758 (6) Å	θ = 2.2–21.2°
b = 18.5123 (6) Å	µ = 0.09 mm−1
c = 7.7947 (3) Å	T = 118 K
V = 2637.2 (2) Å3	Prism, colorless
Z = 8	0.12 × 0.04 × 0.02 mm

Bruker SMART APEX diffractometer	1316 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.071
graphite	θmax = 27.5°, θmin = 2.2°
ω scans	h = −22→23
12370 measured reflections	k = −24→23
1626 independent reflections	l = −10→10

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) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.046P)2 + 0.5804P] where P = (Fo2 + 2Fc2)/3
1626 reflections	(Δ/σ)max = 0.001
190 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	0.19391 (9)	0.24366 (9)	0.5000 (2)	0.0217 (4)
N1	0.15328 (11)	0.34927 (11)	0.3713 (3)	0.0192 (5)
N2	0.30285 (11)	0.38838 (11)	0.3387 (3)	0.0218 (5)
C1	0.12235 (13)	0.21546 (12)	0.4887 (4)	0.0192 (5)
C2	0.07744 (14)	0.22066 (13)	0.6269 (4)	0.0222 (6)
H2	0.0930	0.2454	0.7273	0.027*
C3	0.00734 (14)	0.18873 (13)	0.6196 (3)	0.0234 (6)
H3	−0.0246	0.1922	0.7155	0.028*
C4	−0.01480 (14)	0.15306 (13)	0.4762 (3)	0.0231 (6)
H4	−0.0619	0.1314	0.4737	0.028*
C5	0.03121 (13)	0.14761 (12)	0.3301 (3)	0.0198 (5)
C6	0.00887 (15)	0.11230 (14)	0.1784 (4)	0.0269 (6)
H6	−0.0381	0.0903	0.1737	0.032*
C7	0.05358 (16)	0.10925 (15)	0.0388 (4)	0.0301 (7)
H7	0.0375	0.0857	−0.0627	0.036*
C8	0.12373 (16)	0.14110 (15)	0.0448 (4)	0.0278 (6)
H8	0.1546	0.1388	−0.0531	0.033*
C9	0.14764 (14)	0.17502 (13)	0.1890 (4)	0.0219 (6)
H9	0.1952	0.1957	0.1917	0.026*
C10	0.10190 (13)	0.17973 (13)	0.3355 (3)	0.0180 (5)
C11	0.20655 (14)	0.30943 (13)	0.4253 (3)	0.0189 (5)
C12	0.28187 (14)	0.32836 (13)	0.4113 (3)	0.0213 (6)
H12	0.3178	0.2964	0.4560	0.026*
C13	0.24804 (15)	0.43279 (12)	0.2773 (3)	0.0190 (5)
C14	0.26686 (14)	0.49812 (13)	0.1965 (4)	0.0232 (6)
H14	0.3168	0.5114	0.1841	0.028*
C15	0.21262 (15)	0.54275 (14)	0.1356 (4)	0.0247 (6)
H15	0.2253	0.5866	0.0798	0.030*
C16	0.13869 (15)	0.52397 (13)	0.1552 (4)	0.0231 (6)
H16	0.1017	0.5552	0.1123	0.028*
C17	0.11934 (14)	0.46108 (13)	0.2357 (3)	0.0212 (6)
H17	0.0691	0.4494	0.2501	0.025*
C18	0.17350 (13)	0.41378 (13)	0.2971 (3)	0.0190 (5)

	U11	U22	U33	U12	U13	U23
O1	0.0185 (9)	0.0192 (9)	0.0275 (10)	−0.0015 (7)	−0.0032 (8)	0.0043 (8)
N1	0.0177 (11)	0.0189 (10)	0.0211 (12)	−0.0005 (8)	−0.0005 (8)	0.0002 (9)
N2	0.0202 (11)	0.0228 (11)	0.0223 (11)	−0.0011 (8)	−0.0006 (10)	−0.0001 (10)
C1	0.0154 (13)	0.0156 (11)	0.0266 (14)	0.0005 (9)	−0.0035 (12)	0.0063 (11)
C2	0.0246 (14)	0.0183 (12)	0.0237 (14)	0.0038 (10)	−0.0013 (12)	0.0002 (11)
C3	0.0228 (14)	0.0215 (13)	0.0259 (15)	0.0046 (10)	0.0077 (12)	0.0030 (12)
C4	0.0164 (13)	0.0212 (12)	0.0316 (16)	0.0026 (9)	0.0011 (12)	0.0054 (12)
C5	0.0179 (13)	0.0159 (12)	0.0255 (14)	0.0015 (10)	−0.0038 (11)	0.0057 (11)
C6	0.0244 (14)	0.0236 (13)	0.0326 (16)	−0.0003 (11)	−0.0065 (13)	−0.0009 (13)
C7	0.0321 (16)	0.0316 (15)	0.0266 (16)	0.0045 (12)	−0.0094 (13)	−0.0040 (13)
C8	0.0325 (15)	0.0312 (15)	0.0198 (14)	0.0087 (12)	0.0021 (12)	0.0017 (12)
C9	0.0206 (13)	0.0194 (12)	0.0257 (14)	0.0031 (10)	0.0009 (11)	0.0065 (12)
C10	0.0184 (12)	0.0152 (11)	0.0205 (13)	0.0019 (9)	−0.0007 (11)	0.0045 (10)
C11	0.0225 (14)	0.0169 (12)	0.0172 (12)	−0.0021 (10)	−0.0020 (11)	−0.0011 (10)
C12	0.0193 (14)	0.0229 (13)	0.0217 (13)	0.0016 (10)	−0.0012 (11)	−0.0018 (11)
C13	0.0191 (12)	0.0193 (11)	0.0184 (13)	0.0000 (10)	−0.0003 (10)	−0.0023 (10)
C14	0.0226 (14)	0.0226 (12)	0.0243 (14)	−0.0037 (10)	0.0031 (12)	−0.0002 (12)
C15	0.0312 (15)	0.0203 (12)	0.0225 (14)	−0.0016 (11)	0.0019 (12)	0.0017 (11)
C16	0.0243 (14)	0.0199 (12)	0.0252 (14)	0.0032 (10)	−0.0034 (12)	−0.0006 (11)
C17	0.0192 (13)	0.0199 (12)	0.0245 (14)	−0.0004 (10)	−0.0005 (11)	−0.0023 (11)
C18	0.0205 (13)	0.0160 (11)	0.0204 (13)	−0.0010 (10)	0.0000 (11)	−0.0043 (11)

O1—C11	1.369 (3)	C7—C8	1.412 (4)
O1—C1	1.411 (3)	C7—H7	0.9500
N1—C11	1.292 (3)	C8—C9	1.360 (4)
N1—C18	1.378 (3)	C8—H8	0.9500
N2—C12	1.304 (3)	C9—C10	1.418 (3)
N2—C13	1.382 (3)	C9—H9	0.9500
C1—C2	1.358 (4)	C11—C12	1.425 (3)
C1—C10	1.415 (3)	C12—H12	0.9500
C2—C3	1.412 (4)	C13—C14	1.406 (3)
C2—H2	0.9500	C13—C18	1.415 (4)
C3—C4	1.360 (4)	C14—C15	1.375 (4)
C3—H3	0.9500	C14—H14	0.9500
C4—C5	1.419 (4)	C15—C16	1.404 (4)
C4—H4	0.9500	C15—H15	0.9500
C5—C6	1.411 (4)	C16—C17	1.369 (4)
C5—C10	1.423 (3)	C16—H16	0.9500
C6—C7	1.362 (4)	C17—C18	1.405 (3)
C6—H6	0.9500	C17—H17	0.9500
C11—O1—C1	117.31 (18)	C10—C9—H9	119.8
C11—N1—C18	115.4 (2)	C1—C10—C9	123.5 (2)
C12—N2—C13	116.4 (2)	C1—C10—C5	117.4 (2)
C2—C1—O1	119.0 (2)	C9—C10—C5	119.1 (2)
C2—C1—C10	122.9 (2)	N1—C11—O1	121.3 (2)
O1—C1—C10	118.1 (2)	N1—C11—C12	124.2 (2)
C1—C2—C3	119.1 (2)	O1—C11—C12	114.5 (2)
C1—C2—H2	120.5	N2—C12—C11	121.8 (2)
C3—C2—H2	120.5	N2—C12—H12	119.1
C4—C3—C2	120.4 (2)	C11—C12—H12	119.1
C4—C3—H3	119.8	N2—C13—C14	119.3 (2)
C2—C3—H3	119.8	N2—C13—C18	120.8 (2)
C3—C4—C5	121.2 (2)	C14—C13—C18	119.9 (2)
C3—C4—H4	119.4	C15—C14—C13	119.7 (2)
C5—C4—H4	119.4	C15—C14—H14	120.2
C6—C5—C4	122.3 (2)	C13—C14—H14	120.2
C6—C5—C10	118.8 (2)	C14—C15—C16	120.5 (2)
C4—C5—C10	119.0 (2)	C14—C15—H15	119.7
C7—C6—C5	121.0 (2)	C16—C15—H15	119.7
C7—C6—H6	119.5	C17—C16—C15	120.6 (2)
C5—C6—H6	119.5	C17—C16—H16	119.7
C6—C7—C8	120.0 (3)	C15—C16—H16	119.7
C6—C7—H7	120.0	C16—C17—C18	120.3 (2)
C8—C7—H7	120.0	C16—C17—H17	119.9
C9—C8—C7	120.8 (3)	C18—C17—H17	119.9
C9—C8—H8	119.6	N1—C18—C17	119.6 (2)
C7—C8—H8	119.6	N1—C18—C13	121.3 (2)
C8—C9—C10	120.3 (2)	C17—C18—C13	119.1 (2)
C8—C9—H9	119.8
C11—O1—C1—C2	−101.4 (3)	C18—N1—C11—O1	−179.3 (2)
C11—O1—C1—C10	81.6 (3)	C18—N1—C11—C12	−0.3 (4)
O1—C1—C2—C3	−176.3 (2)	C1—O1—C11—N1	10.9 (3)
C10—C1—C2—C3	0.5 (3)	C1—O1—C11—C12	−168.2 (2)
C1—C2—C3—C4	0.2 (3)	C13—N2—C12—C11	0.4 (4)
C2—C3—C4—C5	−0.7 (4)	N1—C11—C12—N2	−1.0 (4)
C3—C4—C5—C6	−178.6 (2)	O1—C11—C12—N2	178.1 (2)
C3—C4—C5—C10	0.5 (3)	C12—N2—C13—C14	−179.6 (2)
C4—C5—C6—C7	178.6 (2)	C12—N2—C13—C18	1.4 (4)
C10—C5—C6—C7	−0.5 (4)	N2—C13—C14—C15	−179.7 (2)
C5—C6—C7—C8	0.6 (4)	C18—C13—C14—C15	−0.7 (4)
C6—C7—C8—C9	0.1 (4)	C13—C14—C15—C16	0.7 (4)
C7—C8—C9—C10	−0.8 (4)	C14—C15—C16—C17	0.2 (4)
C2—C1—C10—C9	178.8 (2)	C15—C16—C17—C18	−1.2 (4)
O1—C1—C10—C9	−4.4 (3)	C11—N1—C18—C17	−179.5 (2)
C2—C1—C10—C5	−0.7 (3)	C11—N1—C18—C13	2.1 (3)
O1—C1—C10—C5	176.1 (2)	C16—C17—C18—N1	−177.3 (2)
C8—C9—C10—C1	−178.6 (2)	C16—C17—C18—C13	1.2 (4)
C8—C9—C10—C5	0.9 (4)	N2—C13—C18—N1	−2.8 (4)
C6—C5—C10—C1	179.3 (2)	C14—C13—C18—N1	178.2 (2)
C4—C5—C10—C1	0.2 (3)	N2—C13—C18—C17	178.8 (2)
C6—C5—C10—C9	−0.2 (3)	C14—C13—C18—C17	−0.3 (4)
C4—C5—C10—C9	−179.3 (2)