2-(3-Nitro-phen-oxy)quinoxaline.

In the title mol-ecule, C(14)H(9)N(3)O(3), the dihedral angle between the quinoxaline and benzene rings is 77.13 (9)°. The mol-ecule is twisted about the ether-benzene O-C bond, with a C-O-C-C torsion angle of -102.8 (2)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming layers in the ab plane, with one nitro O atom accepting two such inter-actions. The layers stack along the c-axis direction via weak C-H⋯π inter-actions.

Related literature

For background to the fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶). For the structures of the polymorphic phenyl quinoxalin-2-yl ether compound, see: Hassan et al. (2008 ▶); Abdullah & Ng (2008 ▶).

Experimental

Crystal data

C14H9N3O3

M = 267.24

Monoclinic,

a = 6.0643 (6) Å

b = 5.3676 (5) Å

c = 18.2443 (17) Å

β = 91.780 (1)°

V = 593.58 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

5637 measured reflections

1502 independent reflections

1403 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.093

S = 1.04

1501 reflections

181 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810034100/hb5615sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034100/hb5615Isup2.hkl

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

C14H9N3O3	F(000) = 276
Mr = 267.24	Dx = 1.495 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2560 reflections
a = 6.0643 (6) Å	θ = 2.2–28.3°
b = 5.3676 (5) Å	µ = 0.11 mm−1
c = 18.2443 (17) Å	T = 100 K
β = 91.780 (1)°	Prism, red
V = 593.58 (10) Å3	0.35 × 0.25 × 0.15 mm
Z = 2

Bruker SMART APEX CCD diffractometer	1403 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 27.5°, θmin = 1.1°
ω scans	h = −7→7
5637 measured reflections	k = −6→6
1502 independent reflections	l = −23→23

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.093	w = 1/[σ2(Fo2) + (0.0584P)2 + 0.098P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
1501 reflections	Δρmax = 0.24 e Å−3
181 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: nd
Primary atom site location: structure-invariant direct methods

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	1.2692 (2)	0.5001 (3)	0.29144 (7)	0.0241 (3)
O2	0.4391 (2)	0.8540 (4)	0.41409 (8)	0.0309 (4)
O3	0.5748 (2)	0.9758 (3)	0.31197 (9)	0.0309 (4)
N1	1.1038 (2)	0.1916 (4)	0.22012 (8)	0.0203 (4)
N2	1.4817 (3)	0.2107 (4)	0.13226 (9)	0.0242 (4)
N3	0.5762 (3)	0.8419 (4)	0.36598 (9)	0.0224 (4)
C1	1.2685 (3)	0.3411 (4)	0.23292 (10)	0.0201 (4)
C2	1.4591 (3)	0.3556 (4)	0.18864 (11)	0.0229 (4)
H2	1.5713	0.4735	0.2007	0.028*
C3	1.3147 (3)	0.0427 (4)	0.11749 (10)	0.0212 (4)
C4	1.3319 (3)	−0.1261 (5)	0.05877 (11)	0.0261 (5)
H4	1.4576	−0.1216	0.0290	0.031*
C5	1.1678 (3)	−0.2970 (5)	0.04435 (11)	0.0281 (5)
H5	1.1817	−0.4113	0.0050	0.034*
C6	0.9785 (3)	−0.3042 (5)	0.08741 (11)	0.0268 (5)
H6	0.8666	−0.4243	0.0774	0.032*
C7	0.9563 (3)	−0.1377 (5)	0.14384 (10)	0.0227 (4)
H7	0.8263	−0.1393	0.1716	0.027*
C8	1.1248 (3)	0.0355 (4)	0.16091 (10)	0.0194 (4)
C9	1.0867 (3)	0.4856 (4)	0.33663 (10)	0.0198 (4)
C10	1.0743 (3)	0.2998 (4)	0.38865 (11)	0.0228 (4)
H10	1.1866	0.1769	0.3930	0.027*
C11	0.8952 (3)	0.2945 (4)	0.43471 (11)	0.0229 (4)
H11	0.8867	0.1690	0.4712	0.027*
C12	0.7295 (3)	0.4715 (4)	0.42751 (10)	0.0200 (4)
H12	0.6051	0.4671	0.4579	0.024*
C13	0.7504 (3)	0.6547 (4)	0.37477 (10)	0.0181 (4)
C14	0.9282 (3)	0.6693 (4)	0.32869 (10)	0.0193 (4)
H14	0.9402	0.7989	0.2936	0.023*

	U11	U22	U33	U12	U13	U23
O1	0.0166 (6)	0.0277 (8)	0.0286 (7)	−0.0011 (6)	0.0085 (5)	−0.0071 (7)
O2	0.0254 (7)	0.0371 (9)	0.0307 (8)	0.0124 (7)	0.0081 (6)	−0.0029 (7)
O3	0.0265 (7)	0.0290 (9)	0.0372 (8)	0.0069 (7)	0.0003 (6)	0.0113 (7)
N1	0.0184 (7)	0.0230 (9)	0.0198 (7)	0.0034 (7)	0.0028 (6)	0.0005 (7)
N2	0.0211 (8)	0.0274 (10)	0.0244 (8)	0.0027 (7)	0.0074 (6)	0.0035 (8)
N3	0.0192 (7)	0.0220 (9)	0.0260 (8)	0.0050 (7)	0.0011 (6)	−0.0017 (8)
C1	0.0166 (8)	0.0204 (10)	0.0233 (9)	0.0038 (8)	0.0033 (7)	0.0004 (9)
C2	0.0188 (9)	0.0241 (11)	0.0262 (10)	0.0003 (9)	0.0056 (7)	0.0011 (9)
C3	0.0222 (9)	0.0231 (11)	0.0183 (9)	0.0061 (8)	0.0035 (7)	0.0025 (8)
C4	0.0285 (10)	0.0294 (12)	0.0208 (9)	0.0081 (10)	0.0062 (7)	0.0013 (9)
C5	0.0327 (11)	0.0308 (12)	0.0210 (9)	0.0080 (10)	0.0006 (8)	−0.0042 (9)
C6	0.0286 (10)	0.0272 (12)	0.0245 (10)	0.0019 (9)	−0.0024 (8)	−0.0005 (10)
C7	0.0227 (9)	0.0262 (11)	0.0193 (9)	0.0010 (9)	0.0017 (7)	0.0013 (9)
C8	0.0196 (8)	0.0211 (11)	0.0177 (8)	0.0045 (8)	0.0018 (6)	0.0026 (8)
C9	0.0134 (8)	0.0234 (10)	0.0228 (9)	−0.0010 (8)	0.0041 (6)	−0.0058 (9)
C10	0.0182 (9)	0.0205 (11)	0.0296 (10)	0.0048 (8)	−0.0001 (7)	−0.0018 (8)
C11	0.0244 (9)	0.0202 (11)	0.0240 (10)	0.0004 (8)	0.0016 (7)	0.0023 (8)
C12	0.0176 (8)	0.0228 (11)	0.0198 (9)	0.0003 (8)	0.0032 (6)	−0.0015 (8)
C13	0.0167 (8)	0.0181 (10)	0.0196 (8)	0.0025 (7)	0.0003 (6)	−0.0032 (8)
C14	0.0193 (9)	0.0202 (10)	0.0186 (8)	−0.0001 (8)	0.0014 (6)	−0.0007 (8)

O1—C1	1.367 (2)	C5—H5	0.9500
O1—C9	1.402 (2)	C6—C7	1.373 (3)
O2—N3	1.229 (2)	C6—H6	0.9500
O3—N3	1.219 (2)	C7—C8	1.410 (3)
N1—C1	1.297 (3)	C7—H7	0.9500
N1—C8	1.376 (3)	C9—C10	1.380 (3)
N2—C2	1.300 (3)	C9—C14	1.382 (3)
N2—C3	1.376 (3)	C10—C11	1.394 (3)
N3—C13	1.463 (2)	C10—H10	0.9500
C1—C2	1.433 (2)	C11—C12	1.386 (3)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.409 (3)	C12—C13	1.384 (3)
C3—C8	1.419 (2)	C12—H12	0.9500
C4—C5	1.373 (3)	C13—C14	1.390 (3)
C4—H4	0.9500	C14—H14	0.9500
C5—C6	1.411 (3)
C1—O1—C9	116.22 (15)	C6—C7—C8	120.51 (18)
C1—N1—C8	115.37 (16)	C6—C7—H7	119.7
C2—N2—C3	116.86 (16)	C8—C7—H7	119.7
O3—N3—O2	123.90 (18)	N1—C8—C7	119.41 (16)
O3—N3—C13	118.70 (16)	N1—C8—C3	121.23 (17)
O2—N3—C13	117.40 (17)	C7—C8—C3	119.35 (18)
N1—C1—O1	120.68 (16)	C10—C9—C14	122.35 (16)
N1—C1—C2	124.22 (18)	C10—C9—O1	120.34 (17)
O1—C1—C2	115.10 (17)	C14—C9—O1	117.25 (18)
N2—C2—C1	121.36 (19)	C9—C10—C11	119.30 (18)
N2—C2—H2	119.3	C9—C10—H10	120.3
C1—C2—H2	119.3	C11—C10—H10	120.3
N2—C3—C4	119.93 (17)	C12—C11—C10	120.34 (19)
N2—C3—C8	120.91 (17)	C12—C11—H11	119.8
C4—C3—C8	119.17 (18)	C10—C11—H11	119.8
C5—C4—C3	120.34 (18)	C13—C12—C11	118.07 (17)
C5—C4—H4	119.8	C13—C12—H12	121.0
C3—C4—H4	119.8	C11—C12—H12	121.0
C4—C5—C6	120.6 (2)	C12—C13—C14	123.39 (18)
C4—C5—H5	119.7	C12—C13—N3	118.84 (16)
C6—C5—H5	119.7	C14—C13—N3	117.76 (18)
C7—C6—C5	120.0 (2)	C9—C14—C13	116.51 (18)
C7—C6—H6	120.0	C9—C14—H14	121.7
C5—C6—H6	120.0	C13—C14—H14	121.7
C8—N1—C1—O1	−178.20 (17)	C4—C3—C8—N1	178.05 (18)
C8—N1—C1—C2	2.1 (3)	N2—C3—C8—C7	179.52 (18)
C9—O1—C1—N1	1.7 (3)	C4—C3—C8—C7	−0.8 (3)
C9—O1—C1—C2	−178.60 (17)	C1—O1—C9—C10	79.9 (2)
C3—N2—C2—C1	−0.3 (3)	C1—O1—C9—C14	−102.8 (2)
N1—C1—C2—N2	−1.8 (3)	C14—C9—C10—C11	0.5 (3)
O1—C1—C2—N2	178.42 (18)	O1—C9—C10—C11	177.72 (17)
C2—N2—C3—C4	−177.78 (19)	C9—C10—C11—C12	1.1 (3)
C2—N2—C3—C8	1.9 (3)	C10—C11—C12—C13	−1.5 (3)
N2—C3—C4—C5	178.96 (19)	C11—C12—C13—C14	0.3 (3)
C8—C3—C4—C5	−0.7 (3)	C11—C12—C13—N3	179.51 (17)
C3—C4—C5—C6	0.8 (3)	O3—N3—C13—C12	−167.50 (18)
C4—C5—C6—C7	0.7 (3)	O2—N3—C13—C12	12.5 (3)
C5—C6—C7—C8	−2.2 (3)	O3—N3—C13—C14	11.8 (3)
C1—N1—C8—C7	178.47 (18)	O2—N3—C13—C14	−168.20 (18)
C1—N1—C8—C3	−0.4 (3)	C10—C9—C14—C13	−1.7 (3)
C6—C7—C8—N1	−176.59 (19)	O1—C9—C14—C13	−178.92 (16)
C6—C7—C8—C3	2.3 (3)	C12—C13—C14—C9	1.3 (3)
N2—C3—C8—N1	−1.6 (3)	N3—C13—C14—C9	−177.99 (16)

Cg1 is the centroid of the C3–C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2i	0.95	2.34	3.282 (3)	173
C12—H12···O2ii	0.95	2.44	3.159 (2)	133
C5—H5···Cg1iii	0.95	2.99	3.696 (2)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C3–C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2i	0.95	2.34	3.282 (3)	173
C12—H12⋯O2ii	0.95	2.44	3.159 (2)	133
C5—H5⋯Cg1iii	0.95	2.99	3.696 (2)	133

Symmetry codes: (i) ; (ii) ; (iii) .