2-(4-Methyl-phen-oxy)-5-nitro-pyridine.

The title mol-ecule, C(12)H(10)N(2)O(3), is twisted, the dihedral angle between the rings being 61.16 (13)°. The nitro group is approximately coplanar with the pyridine ring to which it is attached [O-N-C-C torsion angle = -178.1 (3)°]. Supra-molecular chains along [010] and mediated by C-H⋯O and π-π [centroid(pyrid-yl)-(benzene) distance = 3.8259 (18) Å] contacts feature in the crystal packing.

Related literature

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

Experimental

Crystal data

C12H10N2O3

M = 230.22

Orthorhombic,

a = 7.2818 (18) Å

b = 11.977 (2) Å

c = 25.362 (5) Å

V = 2211.9 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.20 × 0.18 × 0.07 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.670, T max = 0.746

15887 measured reflections

1951 independent reflections

1089 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.147

S = 1.02

1951 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.13 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/S1600536811044047/hg5116sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044047/hg5116Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811044047/hg5116Isup3.cml

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

C12H10N2O3	F(000) = 960
Mr = 230.22	Dx = 1.383 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1038 reflections
a = 7.2818 (18) Å	θ = 3.2–19.7°
b = 11.977 (2) Å	µ = 0.10 mm−1
c = 25.362 (5) Å	T = 293 K
V = 2211.9 (8) Å3	Block, colourless
Z = 8	0.20 × 0.18 × 0.07 mm

Bruker SMART APEX diffractometer	1951 independent reflections
Radiation source: fine-focus sealed tube	1089 reflections with I > 2σ(I)
graphite	Rint = 0.074
ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.670, Tmax = 0.746	k = −14→14
15887 measured reflections	l = −30→30

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.147	w = 1/[σ2(Fo2) + (0.0643P)2 + 0.2807P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
1951 reflections	Δρmax = 0.15 e Å−3
156 parameters	Δρmin = −0.13 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: 0.0060 (13)

	x	y	z	Uiso*/Ueq
O1	0.5542 (3)	0.41426 (14)	0.32750 (7)	0.0725 (6)
O2	0.8217 (3)	0.59307 (19)	0.54024 (9)	0.1039 (8)
O3	0.7135 (4)	0.74378 (19)	0.50863 (8)	0.1135 (9)
N1	0.6779 (3)	0.41528 (17)	0.41124 (9)	0.0699 (7)
N2	0.7486 (4)	0.6456 (2)	0.50490 (10)	0.0758 (7)
C1	0.6005 (4)	0.4707 (2)	0.37191 (11)	0.0595 (7)
C2	0.5682 (3)	0.5841 (2)	0.37215 (10)	0.0613 (7)
H2	0.5145	0.6191	0.3433	0.074*
C3	0.6168 (4)	0.6439 (2)	0.41563 (10)	0.0648 (7)
H3	0.5978	0.7206	0.4173	0.078*
C4	0.6950 (4)	0.5868 (2)	0.45701 (10)	0.0576 (7)
C5	0.7247 (4)	0.4751 (2)	0.45359 (11)	0.0675 (8)
H5	0.7798	0.4389	0.4819	0.081*
C6	0.5381 (4)	0.2976 (2)	0.32825 (10)	0.0588 (7)
C7	0.6205 (4)	0.2394 (2)	0.28825 (9)	0.0625 (7)
H7	0.6943	0.2759	0.2638	0.075*
C8	0.5920 (4)	0.1252 (2)	0.28494 (10)	0.0639 (7)
H8	0.6459	0.0857	0.2574	0.077*
C9	0.4864 (4)	0.0685 (2)	0.32118 (10)	0.0601 (7)
C10	0.4088 (4)	0.1301 (2)	0.36136 (11)	0.0675 (8)
H10	0.3393	0.0936	0.3868	0.081*
C11	0.4313 (4)	0.2442 (2)	0.36485 (10)	0.0685 (8)
H11	0.3747	0.2844	0.3917	0.082*
C12	0.4559 (4)	−0.0556 (2)	0.31771 (12)	0.0854 (9)
H12A	0.4765	−0.0888	0.3517	0.128*
H12B	0.5397	−0.0871	0.2926	0.128*
H12C	0.3320	−0.0700	0.3067	0.128*

	U11	U22	U33	U12	U13	U23
O1	0.0976 (16)	0.0589 (12)	0.0612 (11)	0.0000 (10)	−0.0111 (11)	0.0016 (9)
O2	0.142 (2)	0.0885 (16)	0.0806 (14)	0.0159 (14)	−0.0259 (15)	−0.0119 (13)
O3	0.210 (3)	0.0523 (12)	0.0784 (14)	−0.0020 (15)	0.0069 (16)	−0.0057 (11)
N1	0.0881 (17)	0.0516 (13)	0.0699 (14)	0.0073 (11)	−0.0110 (14)	−0.0033 (12)
N2	0.104 (2)	0.0597 (16)	0.0639 (15)	−0.0023 (14)	0.0124 (14)	−0.0004 (13)
C1	0.0622 (17)	0.0557 (16)	0.0607 (16)	0.0015 (13)	0.0020 (14)	0.0036 (14)
C2	0.0640 (18)	0.0586 (17)	0.0615 (16)	0.0076 (13)	0.0040 (14)	0.0104 (14)
C3	0.0754 (19)	0.0496 (15)	0.0695 (17)	0.0059 (14)	0.0120 (16)	0.0042 (14)
C4	0.0645 (17)	0.0508 (16)	0.0574 (15)	−0.0002 (13)	0.0085 (14)	−0.0002 (13)
C5	0.081 (2)	0.0566 (17)	0.0650 (17)	0.0056 (15)	−0.0076 (15)	0.0019 (14)
C6	0.0642 (18)	0.0568 (17)	0.0555 (16)	0.0006 (13)	−0.0087 (14)	−0.0002 (13)
C7	0.0632 (17)	0.0729 (18)	0.0513 (15)	−0.0010 (14)	−0.0007 (13)	0.0029 (14)
C8	0.0646 (17)	0.0730 (19)	0.0541 (15)	0.0055 (15)	−0.0050 (14)	−0.0100 (14)
C9	0.0536 (16)	0.0654 (18)	0.0614 (16)	−0.0024 (14)	−0.0105 (14)	−0.0089 (14)
C10	0.0596 (17)	0.075 (2)	0.0683 (18)	−0.0082 (14)	0.0032 (15)	0.0007 (15)
C11	0.0697 (19)	0.0705 (19)	0.0651 (17)	0.0041 (15)	0.0042 (15)	−0.0086 (15)
C12	0.088 (2)	0.071 (2)	0.098 (2)	−0.0109 (16)	−0.0140 (19)	−0.0137 (17)

O1—C1	1.356 (3)	C6—C11	1.369 (3)
O1—C6	1.403 (3)	C6—C7	1.369 (3)
O2—N2	1.217 (3)	C7—C8	1.386 (4)
O3—N2	1.208 (3)	C7—H7	0.9300
N1—C1	1.324 (3)	C8—C9	1.377 (3)
N1—C5	1.336 (3)	C8—H8	0.9300
N2—C4	1.457 (3)	C9—C10	1.379 (3)
C1—C2	1.379 (3)	C9—C12	1.505 (3)
C2—C3	1.361 (3)	C10—C11	1.380 (3)
C2—H2	0.9300	C10—H10	0.9300
C3—C4	1.376 (3)	C11—H11	0.9300
C3—H3	0.9300	C12—H12A	0.9600
C4—C5	1.358 (3)	C12—H12B	0.9600
C5—H5	0.9300	C12—H12C	0.9600
C1—O1—C6	120.4 (2)	C7—C6—O1	117.4 (2)
C1—N1—C5	116.4 (2)	C6—C7—C8	118.8 (3)
O3—N2—O2	122.5 (3)	C6—C7—H7	120.6
O3—N2—C4	118.6 (3)	C8—C7—H7	120.6
O2—N2—C4	118.8 (2)	C9—C8—C7	122.0 (2)
N1—C1—O1	118.8 (2)	C9—C8—H8	119.0
N1—C1—C2	124.3 (3)	C7—C8—H8	119.0
O1—C1—C2	116.9 (2)	C8—C9—C10	117.3 (2)
C3—C2—C1	118.5 (2)	C8—C9—C12	122.0 (2)
C3—C2—H2	120.7	C10—C9—C12	120.7 (3)
C1—C2—H2	120.7	C9—C10—C11	121.9 (3)
C2—C3—C4	117.7 (2)	C9—C10—H10	119.0
C2—C3—H3	121.2	C11—C10—H10	119.0
C4—C3—H3	121.2	C6—C11—C10	119.1 (3)
C5—C4—C3	120.4 (3)	C6—C11—H11	120.4
C5—C4—N2	119.1 (3)	C10—C11—H11	120.4
C3—C4—N2	120.5 (2)	C9—C12—H12A	109.5
N1—C5—C4	122.7 (3)	C9—C12—H12B	109.5
N1—C5—H5	118.7	H12A—C12—H12B	109.5
C4—C5—H5	118.7	C9—C12—H12C	109.5
C11—C6—C7	120.9 (2)	H12A—C12—H12C	109.5
C11—C6—O1	121.5 (2)	H12B—C12—H12C	109.5
C5—N1—C1—O1	178.5 (2)	C3—C4—C5—N1	−1.2 (4)
C5—N1—C1—C2	0.7 (4)	N2—C4—C5—N1	179.4 (2)
C6—O1—C1—N1	18.3 (4)	C1—O1—C6—C11	52.0 (3)
C6—O1—C1—C2	−163.8 (2)	C1—O1—C6—C7	−133.5 (2)
N1—C1—C2—C3	−0.7 (4)	C11—C6—C7—C8	0.9 (4)
O1—C1—C2—C3	−178.6 (2)	O1—C6—C7—C8	−173.7 (2)
C1—C2—C3—C4	−0.2 (4)	C6—C7—C8—C9	−1.2 (4)
C2—C3—C4—C5	1.1 (4)	C7—C8—C9—C10	0.0 (4)
C2—C3—C4—N2	−179.4 (2)	C7—C8—C9—C12	−179.8 (2)
O3—N2—C4—C5	−176.4 (3)	C8—C9—C10—C11	1.6 (4)
O2—N2—C4—C5	1.3 (4)	C12—C9—C10—C11	−178.6 (3)
O3—N2—C4—C3	4.1 (4)	C7—C6—C11—C10	0.7 (4)
O2—N2—C4—C3	−178.1 (3)	O1—C6—C11—C10	175.0 (2)
C1—N1—C5—C4	0.2 (4)	C9—C10—C11—C6	−1.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O(3)i	0.93	2.43	3.135 (3)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O(3)i	0.93	2.43	3.135 (3)	132

Symmetry code: (i) .