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

In the title compound, C(12)H(10)N(2)O(4), the pyridine and benzene rings are almost orthogonal, forming a dihedral angle of 86.63 (6)°. Each of the nitro [O-N-C-C torsion angle = -6.45 (19)°] and meth-oxy [C-O-C-C torsion angle = 179.69 (11)°] groups is almost coplanar with the ring to which it is connected. Mol-ecules are consolidated in the crystal structure via C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For the structure of a related nitro-pyridine derivative, see: Nasir et al. (2010 ▶).

Experimental

Crystal data

C12H10N2O4

M = 246.22

Monoclinic,

a = 7.5017 (7) Å

b = 7.1542 (6) Å

c = 20.6369 (18) Å

β = 91.878 (1)°

V = 1106.96 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.35 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.961, T max = 0.978

10026 measured reflections

2551 independent reflections

2103 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.103

S = 1.03

2551 reflections

164 parameters

H-atom parameters constrained

Δρmax = 0.25 e Å−3

Δρmin = −0.25 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 datablock(s) global, I. DOI: 10.1107/S1600536811045247/hb6471sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811045247/hb6471Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811045247/hb6471Isup3.cml

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

C12H10N2O4	F(000) = 512
Mr = 246.22	Dx = 1.477 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3556 reflections
a = 7.5017 (7) Å	θ = 2.9–28.2°
b = 7.1542 (6) Å	µ = 0.11 mm−1
c = 20.6369 (18) Å	T = 100 K
β = 91.878 (1)°	Block, colourless
V = 1106.96 (17) Å3	0.35 × 0.30 × 0.20 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2551 independent reflections
Radiation source: fine-focus sealed tube	2103 reflections with I > 2σ(I)
graphite	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.961, Tmax = 0.978	k = −9→9
10026 measured reflections	l = −23→26

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.053P)2 + 0.3772P] where P = (Fo2 + 2Fc2)/3
2551 reflections	(Δ/σ)max < 0.001
164 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

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	0.36667 (12)	0.22735 (12)	0.12197 (4)	0.0182 (2)
O2	0.71311 (12)	0.13613 (14)	0.12236 (4)	0.0206 (2)
O3	0.20311 (15)	0.16998 (15)	0.01073 (5)	0.0316 (3)
O4	0.12030 (15)	0.40621 (16)	−0.04768 (5)	0.0323 (3)
N1	0.47657 (14)	0.52273 (15)	0.13850 (5)	0.0190 (2)
N2	0.20013 (15)	0.33758 (17)	−0.00044 (5)	0.0207 (3)
C1	0.38285 (16)	0.40572 (17)	0.10136 (6)	0.0150 (3)
C2	0.29836 (16)	0.46433 (18)	0.04319 (6)	0.0171 (3)
C3	0.30952 (18)	0.6508 (2)	0.02541 (7)	0.0235 (3)
H3	0.2519	0.6939	−0.0135	0.028*
C4	0.4052 (2)	0.7729 (2)	0.06477 (7)	0.0262 (3)
H4	0.4140	0.9017	0.0541	0.031*
C5	0.48791 (18)	0.70151 (19)	0.12028 (7)	0.0236 (3)
H5	0.5568	0.7842	0.1470	0.028*
C6	0.45474 (17)	0.18151 (17)	0.18111 (6)	0.0165 (3)
C7	0.35938 (17)	0.17835 (18)	0.23680 (6)	0.0198 (3)
H7	0.2382	0.2170	0.2360	0.024*
C8	0.44250 (18)	0.11778 (19)	0.29441 (7)	0.0217 (3)
H8	0.3787	0.1162	0.3334	0.026*
C9	0.61791 (18)	0.06017 (18)	0.29447 (6)	0.0196 (3)
H9	0.6736	0.0169	0.3337	0.024*
C10	0.71438 (17)	0.06438 (17)	0.23835 (6)	0.0179 (3)
H10	0.8354	0.0250	0.2392	0.022*
C11	0.63311 (17)	0.12668 (17)	0.18063 (6)	0.0160 (3)
C12	0.89664 (19)	0.0810 (2)	0.12152 (7)	0.0250 (3)
H12A	0.9384	0.0882	0.0771	0.038*
H12B	0.9088	−0.0477	0.1374	0.038*
H12C	0.9683	0.1646	0.1495	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0237 (5)	0.0134 (4)	0.0169 (5)	−0.0025 (4)	−0.0074 (4)	0.0026 (3)
O2	0.0236 (5)	0.0230 (5)	0.0152 (5)	0.0025 (4)	−0.0015 (4)	0.0007 (4)
O3	0.0442 (6)	0.0264 (6)	0.0235 (6)	−0.0106 (5)	−0.0096 (5)	0.0015 (4)
O4	0.0353 (6)	0.0440 (7)	0.0170 (5)	0.0105 (5)	−0.0087 (4)	0.0004 (5)
N1	0.0201 (5)	0.0141 (5)	0.0226 (6)	−0.0003 (4)	−0.0027 (4)	−0.0002 (4)
N2	0.0199 (5)	0.0292 (7)	0.0129 (5)	0.0011 (5)	−0.0003 (4)	0.0006 (5)
C1	0.0153 (6)	0.0132 (6)	0.0165 (6)	0.0011 (4)	0.0009 (5)	0.0009 (5)
C2	0.0167 (6)	0.0196 (7)	0.0149 (6)	0.0013 (5)	0.0006 (5)	0.0009 (5)
C3	0.0247 (7)	0.0230 (7)	0.0230 (7)	0.0054 (5)	0.0025 (5)	0.0084 (6)
C4	0.0311 (7)	0.0146 (6)	0.0332 (8)	0.0021 (5)	0.0042 (6)	0.0075 (6)
C5	0.0244 (7)	0.0144 (6)	0.0318 (8)	−0.0016 (5)	−0.0009 (6)	−0.0009 (6)
C6	0.0222 (6)	0.0105 (6)	0.0162 (6)	−0.0025 (5)	−0.0060 (5)	0.0009 (5)
C7	0.0194 (6)	0.0181 (6)	0.0216 (7)	−0.0023 (5)	−0.0020 (5)	0.0006 (5)
C8	0.0253 (7)	0.0216 (7)	0.0182 (7)	−0.0050 (5)	0.0004 (5)	0.0020 (5)
C9	0.0272 (7)	0.0156 (6)	0.0156 (6)	−0.0040 (5)	−0.0055 (5)	0.0027 (5)
C10	0.0219 (6)	0.0126 (6)	0.0189 (7)	−0.0003 (5)	−0.0041 (5)	0.0004 (5)
C11	0.0233 (6)	0.0096 (6)	0.0151 (6)	−0.0019 (5)	−0.0018 (5)	0.0002 (5)
C12	0.0243 (7)	0.0282 (8)	0.0226 (7)	0.0043 (6)	0.0004 (5)	0.0000 (6)

O1—C1	1.3518 (15)	C5—H5	0.9500
O1—C6	1.4075 (14)	C6—C7	1.3735 (18)
O2—C11	1.3630 (15)	C6—C11	1.3947 (18)
O2—C12	1.4329 (16)	C7—C8	1.3934 (18)
O3—N2	1.2211 (16)	C7—H7	0.9500
O4—N2	1.2295 (14)	C8—C9	1.3788 (19)
N1—C1	1.3217 (16)	C8—H8	0.9500
N1—C5	1.3367 (17)	C9—C10	1.3860 (19)
N2—C2	1.4604 (17)	C9—H9	0.9500
C1—C2	1.4031 (17)	C10—C11	1.3935 (17)
C2—C3	1.3871 (19)	C10—H10	0.9500
C3—C4	1.378 (2)	C12—H12A	0.9800
C3—H3	0.9500	C12—H12B	0.9800
C4—C5	1.383 (2)	C12—H12C	0.9800
C4—H4	0.9500
C1—O1—C6	116.64 (9)	C11—C6—O1	118.84 (11)
C11—O2—C12	116.62 (10)	C6—C7—C8	119.22 (12)
C1—N1—C5	118.72 (12)	C6—C7—H7	120.4
O3—N2—O4	123.18 (12)	C8—C7—H7	120.4
O3—N2—C2	119.18 (11)	C9—C8—C7	119.61 (12)
O4—N2—C2	117.63 (12)	C9—C8—H8	120.2
N1—C1—O1	117.84 (11)	C7—C8—H8	120.2
N1—C1—C2	121.57 (12)	C8—C9—C10	121.14 (12)
O1—C1—C2	120.57 (11)	C8—C9—H9	119.4
C3—C2—C1	118.97 (12)	C10—C9—H9	119.4
C3—C2—N2	117.89 (11)	C9—C10—C11	119.70 (12)
C1—C2—N2	123.14 (11)	C9—C10—H10	120.1
C4—C3—C2	119.24 (13)	C11—C10—H10	120.1
C4—C3—H3	120.4	O2—C11—C10	125.24 (12)
C2—C3—H3	120.4	O2—C11—C6	116.28 (11)
C3—C4—C5	117.71 (13)	C10—C11—C6	118.47 (12)
C3—C4—H4	121.1	O2—C12—H12A	109.5
C5—C4—H4	121.1	O2—C12—H12B	109.5
N1—C5—C4	123.76 (13)	H12A—C12—H12B	109.5
N1—C5—H5	118.1	O2—C12—H12C	109.5
C4—C5—H5	118.1	H12A—C12—H12C	109.5
C7—C6—C11	121.84 (11)	H12B—C12—H12C	109.5
C7—C6—O1	119.13 (11)
C5—N1—C1—O1	−177.26 (11)	C3—C4—C5—N1	−1.7 (2)
C5—N1—C1—C2	1.09 (19)	C1—O1—C6—C7	98.47 (13)
C6—O1—C1—N1	−1.12 (16)	C1—O1—C6—C11	−86.40 (14)
C6—O1—C1—C2	−179.48 (11)	C11—C6—C7—C8	−0.36 (19)
N1—C1—C2—C3	−1.92 (19)	O1—C6—C7—C8	174.62 (11)
O1—C1—C2—C3	176.38 (11)	C6—C7—C8—C9	−0.73 (19)
N1—C1—C2—N2	177.31 (11)	C7—C8—C9—C10	1.1 (2)
O1—C1—C2—N2	−4.40 (18)	C8—C9—C10—C11	−0.40 (19)
O3—N2—C2—C3	172.79 (12)	C12—O2—C11—C10	−1.44 (18)
O4—N2—C2—C3	−6.00 (17)	C12—O2—C11—C6	179.69 (11)
O3—N2—C2—C1	−6.45 (19)	C9—C10—C11—O2	−179.52 (11)
O4—N2—C2—C1	174.76 (12)	C9—C10—C11—C6	−0.68 (18)
C1—C2—C3—C4	0.92 (19)	C7—C6—C11—O2	−179.99 (11)
N2—C2—C3—C4	−178.35 (12)	O1—C6—C11—O2	5.02 (16)
C2—C3—C4—C5	0.8 (2)	C7—C6—C11—C10	1.06 (18)
C1—N1—C5—C4	0.8 (2)	O1—C6—C11—C10	−173.93 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.58	3.4085 (17)	146
C9—H9···O4ii	0.95	2.55	3.2659 (16)	132
C12—H12a···O3iii	0.98	2.52	3.3560 (18)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.58	3.4085 (17)	146
C9—H9⋯O4ii	0.95	2.55	3.2659 (16)	132
C12—H12a⋯O3iii	0.98	2.52	3.3560 (18)	143

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