Phenyl quinoxalin-2-yl ether.

The aromatic ring systems in the title compound, C(14)H(10)N(2)O, form a dihedral angle of 63.8 (1)°, resulting in an opening up of the ether-O atom angle to 118.2 (1)°.

Related literature

The title compound exhibits fluorescence; see: Abdullah (2005 ▶); Kawai et al. (2001 ▶); Mohd Salleh et al. (2007 ▶). For the only previously reported structural example of a quinoxalin­oxy compound, see: Csikós et al. (1999 ▶).

Experimental

Crystal data

C14H10N2O

M = 222.24

Monoclinic,

a = 18.175 (2) Å

b = 6.6589 (8) Å

c = 19.488 (2) Å

β = 112.937 (2)°

V = 2172.1 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 (2) K

0.30 × 0.20 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: none

6018 measured reflections

2478 independent reflections

1909 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.104

S = 1.07

2478 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.27 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, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808026809/tk2297sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026809/tk2297Isup2.hkl

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

C14H10N2O	F000 = 928
Mr = 222.24	Dx = 1.359 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1614 reflections
a = 18.175 (2) Å	θ = 2.4–28.2º
b = 6.6589 (8) Å	µ = 0.09 mm−1
c = 19.488 (2) Å	T = 100 (2) K
β = 112.937 (2)º	Prism, colorless
V = 2172.1 (5) Å3	0.30 × 0.20 × 0.05 mm
Z = 8

Bruker SMART APEX diffractometer	1909 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Monochromator: graphite	θmax = 27.5º
T = 100(2) K	θmin = 2.3º
ω scans	h = −23→16
Absorption correction: None	k = −8→8
6018 measured reflections	l = −23→25
2478 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0479P)2 + 0.7132P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
2478 reflections	Δρmax = 0.27 e Å−3
154 parameters	Δρmin = −0.27 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
O1	0.68658 (5)	0.68613 (14)	0.55215 (5)	0.0196 (2)
N1	0.59181 (6)	0.76551 (15)	0.59977 (6)	0.0166 (2)
N2	0.47638 (6)	0.72591 (16)	0.45219 (6)	0.0176 (2)
C1	0.74734 (7)	0.7128 (2)	0.62327 (7)	0.0178 (3)
C2	0.75301 (8)	0.5866 (2)	0.68141 (8)	0.0242 (3)
H2	0.7143	0.4846	0.6749	0.029*
C3	0.81628 (9)	0.6118 (2)	0.74933 (8)	0.0291 (4)
H3	0.8209	0.5269	0.7900	0.035*
C4	0.87301 (9)	0.7599 (2)	0.75850 (8)	0.0293 (4)
H4	0.9163	0.7763	0.8053	0.035*
C5	0.86637 (8)	0.8838 (2)	0.69930 (8)	0.0267 (3)
H5	0.9053	0.9849	0.7055	0.032*
C6	0.80290 (8)	0.8608 (2)	0.63088 (7)	0.0208 (3)
H6	0.7980	0.9456	0.5901	0.025*
C7	0.60973 (7)	0.71759 (18)	0.54400 (7)	0.0167 (3)
C8	0.55218 (8)	0.69640 (19)	0.46909 (7)	0.0180 (3)
H8	0.5698	0.6599	0.4309	0.022*
C9	0.45400 (7)	0.77709 (18)	0.50983 (7)	0.0156 (3)
C10	0.37309 (8)	0.81243 (19)	0.49536 (7)	0.0184 (3)
H10	0.3341	0.8006	0.4460	0.022*
C11	0.35029 (8)	0.86377 (19)	0.55218 (7)	0.0202 (3)
H11	0.2955	0.8882	0.5420	0.024*
C12	0.40760 (8)	0.8806 (2)	0.62563 (7)	0.0204 (3)
H12	0.3912	0.9162	0.6647	0.025*
C13	0.48681 (8)	0.8460 (2)	0.64120 (7)	0.0189 (3)
H13	0.5249	0.8564	0.6910	0.023*
C14	0.51180 (7)	0.79510 (18)	0.58369 (7)	0.0157 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0157 (5)	0.0261 (5)	0.0182 (5)	0.0021 (4)	0.0079 (4)	−0.0013 (4)
N1	0.0167 (6)	0.0160 (5)	0.0179 (5)	−0.0007 (4)	0.0077 (4)	−0.0009 (4)
N2	0.0214 (6)	0.0154 (5)	0.0166 (5)	−0.0008 (4)	0.0079 (4)	−0.0009 (4)
C1	0.0158 (6)	0.0218 (6)	0.0172 (6)	0.0052 (5)	0.0079 (5)	−0.0004 (5)
C2	0.0238 (7)	0.0257 (7)	0.0295 (7)	0.0071 (6)	0.0174 (6)	0.0064 (6)
C3	0.0297 (8)	0.0404 (9)	0.0233 (7)	0.0181 (7)	0.0169 (6)	0.0118 (6)
C4	0.0222 (7)	0.0439 (9)	0.0184 (7)	0.0127 (7)	0.0045 (6)	−0.0019 (6)
C5	0.0208 (7)	0.0291 (7)	0.0277 (7)	0.0011 (6)	0.0067 (6)	−0.0045 (6)
C6	0.0196 (7)	0.0228 (7)	0.0215 (7)	0.0036 (5)	0.0097 (6)	0.0029 (5)
C7	0.0161 (6)	0.0148 (6)	0.0208 (6)	−0.0003 (5)	0.0090 (5)	0.0005 (5)
C8	0.0221 (7)	0.0164 (6)	0.0176 (6)	−0.0006 (5)	0.0102 (5)	−0.0007 (5)
C9	0.0182 (6)	0.0120 (6)	0.0170 (6)	−0.0008 (5)	0.0074 (5)	−0.0006 (5)
C10	0.0177 (7)	0.0159 (6)	0.0185 (6)	−0.0008 (5)	0.0037 (5)	0.0000 (5)
C11	0.0149 (6)	0.0189 (6)	0.0270 (7)	0.0001 (5)	0.0084 (5)	0.0006 (5)
C12	0.0220 (7)	0.0213 (6)	0.0215 (6)	−0.0001 (5)	0.0123 (6)	−0.0019 (5)
C13	0.0196 (7)	0.0205 (6)	0.0168 (6)	−0.0005 (5)	0.0072 (5)	−0.0009 (5)
C14	0.0152 (6)	0.0133 (6)	0.0184 (6)	−0.0006 (5)	0.0062 (5)	0.0003 (5)

O1—C7	1.3591 (15)	C5—H5	0.9500
O1—C1	1.4068 (15)	C6—H6	0.9500
N1—C7	1.2904 (17)	C7—C8	1.4335 (17)
N1—C14	1.3771 (16)	C8—H8	0.9500
N2—C8	1.3006 (17)	C9—C10	1.4051 (18)
N2—C9	1.3782 (17)	C9—C14	1.4182 (17)
C1—C6	1.3769 (19)	C10—C11	1.3685 (19)
C1—C2	1.3821 (18)	C10—H10	0.9500
C2—C3	1.384 (2)	C11—C12	1.4086 (18)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.387 (2)	C12—C13	1.3703 (18)
C3—H3	0.9500	C12—H12	0.9500
C4—C5	1.385 (2)	C13—C14	1.4048 (18)
C4—H4	0.9500	C13—H13	0.9500
C5—C6	1.3903 (18)
C7—O1—C1	118.16 (10)	O1—C7—C8	114.37 (11)
C7—N1—C14	115.75 (11)	N2—C8—C7	121.57 (12)
C8—N2—C9	116.80 (11)	N2—C8—H8	119.2
C6—C1—C2	121.99 (12)	C7—C8—H8	119.2
C6—C1—O1	117.24 (11)	N2—C9—C10	119.73 (11)
C2—C1—O1	120.65 (12)	N2—C9—C14	120.73 (12)
C1—C2—C3	118.61 (14)	C10—C9—C14	119.54 (12)
C1—C2—H2	120.7	C11—C10—C9	120.18 (12)
C3—C2—H2	120.7	C11—C10—H10	119.9
C2—C3—C4	120.54 (13)	C9—C10—H10	119.9
C2—C3—H3	119.7	C10—C11—C12	120.33 (12)
C4—C3—H3	119.7	C10—C11—H11	119.8
C5—C4—C3	119.82 (13)	C12—C11—H11	119.8
C5—C4—H4	120.1	C13—C12—C11	120.57 (12)
C3—C4—H4	120.1	C13—C12—H12	119.7
C4—C5—C6	120.25 (14)	C11—C12—H12	119.7
C4—C5—H5	119.9	C12—C13—C14	120.16 (12)
C6—C5—H5	119.9	C12—C13—H13	119.9
C1—C6—C5	118.80 (13)	C14—C13—H13	119.9
C1—C6—H6	120.6	N1—C14—C13	119.60 (11)
C5—C6—H6	120.6	N1—C14—C9	121.18 (12)
N1—C7—O1	121.67 (11)	C13—C14—C9	119.22 (12)
N1—C7—C8	123.96 (12)
C7—O1—C1—C6	−117.62 (13)	O1—C7—C8—N2	−178.58 (11)
C7—O1—C1—C2	66.18 (16)	C8—N2—C9—C10	179.57 (11)
C6—C1—C2—C3	0.5 (2)	C8—N2—C9—C14	−0.26 (17)
O1—C1—C2—C3	176.56 (12)	N2—C9—C10—C11	−179.85 (12)
C1—C2—C3—C4	−0.4 (2)	C14—C9—C10—C11	−0.03 (19)
C2—C3—C4—C5	0.0 (2)	C9—C10—C11—C12	−0.3 (2)
C3—C4—C5—C6	0.3 (2)	C10—C11—C12—C13	0.0 (2)
C2—C1—C6—C5	−0.2 (2)	C11—C12—C13—C14	0.6 (2)
O1—C1—C6—C5	−176.37 (11)	C7—N1—C14—C13	179.44 (12)
C4—C5—C6—C1	−0.2 (2)	C7—N1—C14—C9	−1.19 (17)
C14—N1—C7—O1	179.35 (11)	C12—C13—C14—N1	178.41 (11)
C14—N1—C7—C8	0.49 (18)	C12—C13—C14—C9	−0.98 (19)
C1—O1—C7—N1	−1.81 (18)	N2—C9—C14—N1	1.12 (18)
C1—O1—C7—C8	177.15 (10)	C10—C9—C14—N1	−178.70 (11)
C9—N2—C8—C7	−0.45 (18)	N2—C9—C14—C13	−179.50 (12)
N1—C7—C8—N2	0.3 (2)	C10—C9—C14—C13	0.68 (18)