2-(4-Meth-oxy-phen-oxy)-3-nitro-pyridine.

In the title mol-ecule, C(12)H(10)N(2)O(4), the pyridine and benzene rings are almost orthogonal [dihedral angle = 86.69 (11)°], with the pyridine N atom directed towards the centre of the benzene ring. The -NO(2) [O-N-C-C = -26.1 (3)°] and -OMe [C-O-C-C = 166.5 (2)°] substituents are not coplanar with their respective aromatic rings. In the crystal, supra-molecular layers in the ab plane are formed via C-H⋯π inter-actions involving methyl H atoms and the pyridine and benzene rings. Short N-O⋯π contacts (where the π-system is derived from the pyridine ring) occur between layers in the c-axis direction.

Related literature

For background to fluorescence properties of compounds related to the title compound, see: Kawai et al. (2001 ▶); Abdullah (2005 ▶). For a related structure, see: Nasir et al. (2010 ▶).

Experimental

Crystal data

C12H10N2O4

M = 246.22

Orthorhombic,

a = 7.4737 (10) Å

b = 12.8128 (17) Å

c = 24.529 (3) Å

V = 2348.8 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.28 × 0.07 mm

Data collection

Bruker SMART APEX CCD diffractometer

16986 measured reflections

2066 independent reflections

1364 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.123

S = 1.03

2066 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT; 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/S1600536810034057/hb5614sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810034057/hb5614Isup2.hkl

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

C12H10N2O4	F(000) = 1024
Mr = 246.22	Dx = 1.393 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2051 reflections
a = 7.4737 (10) Å	θ = 3.2–20.1°
b = 12.8128 (17) Å	µ = 0.11 mm−1
c = 24.529 (3) Å	T = 293 K
V = 2348.8 (5) Å3	Block, colourless
Z = 8	0.30 × 0.28 × 0.07 mm

Bruker SMART APEX CCD diffractometer	1364 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.060
graphite	θmax = 25.0°, θmin = 1.7°
ω scans	h = −8→8
16986 measured reflections	k = −15→15
2066 independent reflections	l = −27→29

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0589P)2 + 0.4422P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
2066 reflections	Δρmax = 0.19 e Å−3
165 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0042 (9)

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.

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 > σ(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	0.6185 (3)	0.61280 (14)	0.47253 (8)	0.0772 (6)
O2	0.4138 (3)	0.73025 (14)	0.47339 (9)	0.0986 (7)
O3	0.56918 (18)	0.47091 (11)	0.39640 (7)	0.0603 (5)
O4	0.8030 (2)	0.16173 (11)	0.25569 (7)	0.0659 (5)
N1	0.2758 (2)	0.42013 (14)	0.38381 (8)	0.0536 (5)
N2	0.4665 (3)	0.64262 (14)	0.46264 (8)	0.0553 (5)
C1	0.3912 (3)	0.48503 (15)	0.40591 (9)	0.0440 (5)
C2	0.3378 (3)	0.57022 (15)	0.43811 (8)	0.0450 (5)
C3	0.1573 (3)	0.58629 (19)	0.44736 (9)	0.0578 (6)
H3	0.1181	0.6424	0.4682	0.069*
C4	0.0362 (3)	0.5166 (2)	0.42471 (11)	0.0654 (7)
H4	−0.0861	0.5245	0.4303	0.078*
C5	0.1010 (3)	0.4359 (2)	0.39382 (10)	0.0607 (6)
H5	0.0192	0.3892	0.3789	0.073*
C6	0.6196 (3)	0.39115 (16)	0.35921 (10)	0.0473 (6)
C7	0.6735 (3)	0.29624 (17)	0.37948 (9)	0.0518 (6)
H7	0.6684	0.2826	0.4167	0.062*
C8	0.7358 (3)	0.22109 (16)	0.34344 (9)	0.0521 (6)
H8	0.7739	0.1567	0.3566	0.063*
C9	0.7416 (3)	0.24148 (15)	0.28798 (9)	0.0478 (6)
C10	0.6896 (3)	0.33849 (16)	0.26848 (10)	0.0557 (6)
H10	0.6960	0.3531	0.2314	0.067*
C11	0.6281 (3)	0.41331 (16)	0.30457 (10)	0.0556 (6)
H11	0.5926	0.4784	0.2918	0.067*
C12	0.7750 (4)	0.1697 (2)	0.19822 (10)	0.0708 (8)
H12A	0.8173	0.1074	0.1807	0.106*
H12B	0.8393	0.2289	0.1843	0.106*
H12C	0.6496	0.1783	0.1910	0.106*

	U11	U22	U33	U12	U13	U23
O1	0.0679 (12)	0.0787 (13)	0.0851 (14)	0.0010 (10)	−0.0152 (10)	−0.0238 (10)
O2	0.1079 (17)	0.0574 (11)	0.1304 (18)	0.0146 (11)	−0.0116 (14)	−0.0361 (11)
O3	0.0388 (9)	0.0600 (9)	0.0822 (12)	−0.0012 (7)	0.0057 (8)	−0.0320 (8)
O4	0.0852 (14)	0.0505 (9)	0.0620 (11)	0.0161 (8)	0.0111 (9)	−0.0123 (8)
N1	0.0424 (11)	0.0514 (11)	0.0669 (13)	−0.0061 (9)	0.0038 (9)	−0.0059 (9)
N2	0.0690 (14)	0.0490 (11)	0.0478 (12)	0.0041 (10)	0.0011 (10)	−0.0068 (9)
C1	0.0413 (12)	0.0424 (11)	0.0483 (13)	0.0008 (9)	0.0061 (10)	−0.0011 (9)
C2	0.0500 (13)	0.0437 (11)	0.0414 (12)	0.0054 (10)	0.0039 (10)	0.0027 (9)
C3	0.0606 (16)	0.0626 (14)	0.0503 (14)	0.0187 (13)	0.0118 (12)	0.0007 (11)
C4	0.0432 (14)	0.0796 (18)	0.0733 (18)	0.0092 (13)	0.0110 (13)	0.0079 (14)
C5	0.0426 (13)	0.0678 (15)	0.0717 (17)	−0.0073 (12)	0.0027 (12)	0.0039 (13)
C6	0.0353 (11)	0.0450 (12)	0.0616 (15)	−0.0023 (9)	0.0046 (10)	−0.0141 (10)
C7	0.0469 (13)	0.0571 (13)	0.0514 (14)	−0.0012 (10)	0.0048 (11)	−0.0043 (11)
C8	0.0534 (14)	0.0427 (11)	0.0604 (15)	0.0064 (10)	0.0017 (12)	0.0002 (11)
C9	0.0470 (13)	0.0431 (11)	0.0533 (14)	0.0015 (10)	0.0057 (11)	−0.0051 (10)
C10	0.0661 (16)	0.0468 (12)	0.0540 (15)	0.0027 (11)	0.0072 (12)	0.0020 (10)
C11	0.0587 (15)	0.0386 (11)	0.0694 (17)	0.0041 (10)	0.0021 (13)	−0.0019 (11)
C12	0.0761 (19)	0.0777 (17)	0.0585 (17)	0.0018 (14)	0.0073 (14)	−0.0230 (13)

O1—N2	1.223 (2)	C5—H5	0.9300
O2—N2	1.219 (2)	C6—C11	1.371 (3)
O3—C1	1.363 (3)	C6—C7	1.374 (3)
O3—C6	1.421 (2)	C7—C8	1.388 (3)
O4—C9	1.372 (2)	C7—H7	0.9300
O4—C12	1.429 (3)	C8—C9	1.386 (3)
N1—C1	1.315 (3)	C8—H8	0.9300
N1—C5	1.345 (3)	C9—C10	1.387 (3)
N2—C2	1.466 (3)	C10—C11	1.384 (3)
C1—C2	1.405 (3)	C10—H10	0.9300
C2—C3	1.383 (3)	C11—H11	0.9300
C3—C4	1.387 (3)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.371 (3)	C12—H12C	0.9600
C4—H4	0.9300
C1—O3—C6	117.66 (15)	C7—C6—O3	118.8 (2)
C9—O4—C12	117.84 (18)	C6—C7—C8	118.8 (2)
C1—N1—C5	117.85 (19)	C6—C7—H7	120.6
O2—N2—O1	123.0 (2)	C8—C7—H7	120.6
O2—N2—C2	117.4 (2)	C7—C8—C9	120.3 (2)
O1—N2—C2	119.57 (18)	C7—C8—H8	119.8
N1—C1—O3	119.05 (18)	C9—C8—H8	119.8
N1—C1—C2	122.5 (2)	O4—C9—C10	124.2 (2)
O3—C1—C2	118.47 (18)	O4—C9—C8	115.89 (19)
C3—C2—C1	119.0 (2)	C10—C9—C8	119.90 (19)
C3—C2—N2	118.59 (19)	C11—C10—C9	119.6 (2)
C1—C2—N2	122.40 (19)	C11—C10—H10	120.2
C2—C3—C4	118.3 (2)	C9—C10—H10	120.2
C2—C3—H3	120.8	C6—C11—C10	119.8 (2)
C4—C3—H3	120.8	C6—C11—H11	120.1
C5—C4—C3	118.5 (2)	C10—C11—H11	120.1
C5—C4—H4	120.8	O4—C12—H12A	109.5
C3—C4—H4	120.8	O4—C12—H12B	109.5
N1—C5—C4	123.9 (2)	H12A—C12—H12B	109.5
N1—C5—H5	118.1	O4—C12—H12C	109.5
C4—C5—H5	118.1	H12A—C12—H12C	109.5
C11—C6—C7	121.54 (19)	H12B—C12—H12C	109.5
C11—C6—O3	119.39 (19)
C5—N1—C1—O3	−180.0 (2)	C3—C4—C5—N1	−0.3 (4)
C5—N1—C1—C2	−1.4 (3)	C1—O3—C6—C11	86.8 (2)
C6—O3—C1—N1	5.0 (3)	C1—O3—C6—C7	−98.8 (2)
C6—O3—C1—C2	−173.55 (19)	C11—C6—C7—C8	−0.8 (3)
N1—C1—C2—C3	0.5 (3)	O3—C6—C7—C8	−175.10 (18)
O3—C1—C2—C3	179.02 (19)	C6—C7—C8—C9	−0.6 (3)
N1—C1—C2—N2	−179.89 (19)	C12—O4—C9—C10	−14.5 (3)
O3—C1—C2—N2	−1.4 (3)	C12—O4—C9—C8	166.5 (2)
O2—N2—C2—C3	−24.8 (3)	C7—C8—C9—O4	−179.2 (2)
O1—N2—C2—C3	153.5 (2)	C7—C8—C9—C10	1.8 (3)
O2—N2—C2—C1	155.6 (2)	O4—C9—C10—C11	179.4 (2)
O1—N2—C2—C1	−26.1 (3)	C8—C9—C10—C11	−1.6 (3)
C1—C2—C3—C4	0.6 (3)	C7—C6—C11—C10	1.0 (3)
N2—C2—C3—C4	−179.1 (2)	O3—C6—C11—C10	175.26 (19)
C2—C3—C4—C5	−0.6 (4)	C9—C10—C11—C6	0.2 (4)
C1—N1—C5—C4	1.4 (4)

Cg1 and Cg2 are the centroids of the N1,C1–C5 and C6–C11 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12a···Cg1i	0.96	2.73	3.521 (3)	140
C12—H12b···Cg2ii	0.96	2.80	3.616 (3)	143
N2—O1···Cg1iii	1.223 (2)	3.350 (2)	4.240 (2)	129.93 (15)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1,C1–C5 and C6–C11 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12a⋯Cg1i	0.96	2.73	3.521 (3)	140
C12—H12b⋯Cg2ii	0.96	2.80	3.616 (3)	143
N2—O1⋯Cg1iii	1.22 (1)	3.35 (1)	4.240 (2)	130 (1)

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