2-(2,4-Difluoro-phen-yl)-5-nitro-pyridine.

In the title mol-ecule, C(11)H(6)F(2)N(2)O(2), the benzene and pyridine rings form a dihedral angle of 32.57 (6)°. The nitro group is tilted with respect to the pyridine ring by 12.26 (9)°. An intra-molecular C-H⋯F hydrogen bond is present. In the crystal, mol-ecules inter-act through π-π stacking inter-actions [centroid-centroid distances = 3.7457 (14) Å], forming columnar arrangements along the b axis. The crystal packing is further enforced by inter-molecular C-H⋯O and C-H⋯N hydrogen bonds.

Related literature

For general background to organic light-emitting diodes (OLEDs), see: Baldo et al. (2000 ▶); Flamigni et al. (2007 ▶); Yang et al. (2007 ▶); Yersin (2008 ▶). For luminescent IrIII complexes containing 2-phenyl­pyridine or its derivatives, see: Nazeeruddin et al. (2003 ▶); Dedeian et al. (2007 ▶); Chin et al. (2007 ▶); Shen et al. (2011 ▶).

Experimental

Crystal data

C11H6F2N2O2

M = 236.18

Orthorhombic,

a = 22.185 (4) Å

b = 3.7457 (6) Å

c = 11.894 (2) Å

V = 988.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.14 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.989

6331 measured reflections

1750 independent reflections

1450 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.081

S = 1.06

1750 reflections

155 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812024713/rz2765sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812024713/rz2765Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812024713/rz2765Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812024713/rz2765Isup4.cml

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

C11H6F2N2O2	F(000) = 480
Mr = 236.18	Dx = 1.587 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 24 reflections
a = 22.185 (4) Å	θ = 1.9–26.7°
b = 3.7457 (6) Å	µ = 0.14 mm−1
c = 11.894 (2) Å	T = 296 K
V = 988.4 (3) Å3	Block, colourless
Z = 4	0.14 × 0.12 × 0.08 mm

Bruker APEXII CCD diffractometer	1750 independent reflections
Radiation source: fine-focus sealed tube	1450 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→26
Tmin = 0.981, Tmax = 0.989	k = −4→4
6331 measured reflections	l = −14→14

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.034	w = 1/[σ2(Fo2) + (0.0417P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.081	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.14 e Å−3
1750 reflections	Δρmin = −0.12 e Å−3
155 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.020 (2)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 823 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 1.3 (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
F1	0.43717 (7)	0.8814 (4)	0.19399 (11)	0.0706 (5)
F2	0.64096 (6)	0.8761 (5)	0.29027 (14)	0.0783 (5)
N1	0.39001 (8)	0.6832 (5)	0.52314 (14)	0.0468 (5)
N2	0.23174 (9)	0.3925 (7)	0.5480 (2)	0.0604 (6)
C1	0.33559 (10)	0.6124 (6)	0.56308 (18)	0.0487 (6)
H1A	0.3278	0.6546	0.6388	0.058*
C2	0.29008 (9)	0.4788 (6)	0.4966 (2)	0.0461 (5)
C3	0.29993 (10)	0.4202 (6)	0.38367 (19)	0.0499 (6)
H3A	0.2696	0.3316	0.3376	0.060*
C4	0.35623 (9)	0.4973 (6)	0.34139 (19)	0.0480 (6)
H4A	0.3644	0.4647	0.2654	0.058*
C5	0.40050 (9)	0.6236 (5)	0.41293 (17)	0.0392 (5)
C6	0.46353 (9)	0.6929 (5)	0.37757 (17)	0.0406 (5)
C7	0.48022 (10)	0.8139 (6)	0.27144 (19)	0.0457 (6)
C8	0.53882 (12)	0.8781 (6)	0.2407 (2)	0.0529 (6)
H8A	0.5485	0.9618	0.1693	0.064*
C9	0.58240 (10)	0.8137 (6)	0.3194 (2)	0.0524 (6)
C10	0.57000 (11)	0.6967 (7)	0.4255 (2)	0.0552 (7)
H10A	0.6007	0.6581	0.4773	0.066*
C11	0.51028 (9)	0.6372 (6)	0.45341 (19)	0.0468 (6)
H11A	0.5011	0.5571	0.5254	0.056*
O1	0.19644 (9)	0.2185 (6)	0.49287 (19)	0.0910 (7)
O2	0.22205 (9)	0.4973 (7)	0.6427 (2)	0.1016 (8)

	U11	U22	U33	U12	U13	U23
F1	0.0672 (10)	0.0979 (13)	0.0468 (8)	0.0059 (9)	−0.0017 (7)	0.0135 (8)
F2	0.0529 (8)	0.1004 (11)	0.0818 (11)	−0.0123 (8)	0.0206 (8)	−0.0020 (9)
N1	0.0453 (11)	0.0560 (12)	0.0390 (11)	−0.0035 (9)	0.0008 (8)	−0.0029 (9)
N2	0.0466 (13)	0.0676 (13)	0.0671 (16)	−0.0070 (11)	0.0044 (12)	0.0016 (11)
C1	0.0491 (13)	0.0584 (14)	0.0387 (13)	−0.0033 (12)	0.0016 (10)	−0.0016 (10)
C2	0.0423 (12)	0.0445 (12)	0.0514 (15)	0.0006 (10)	0.0018 (11)	0.0024 (11)
C3	0.0468 (13)	0.0535 (13)	0.0494 (14)	−0.0034 (11)	−0.0103 (11)	−0.0086 (12)
C4	0.0531 (14)	0.0548 (14)	0.0360 (12)	0.0004 (11)	−0.0040 (11)	−0.0040 (11)
C5	0.0446 (12)	0.0343 (11)	0.0386 (11)	0.0014 (10)	−0.0010 (9)	0.0006 (9)
C6	0.0492 (14)	0.0339 (11)	0.0387 (12)	0.0036 (9)	0.0022 (11)	−0.0021 (10)
C7	0.0543 (15)	0.0437 (13)	0.0392 (12)	0.0042 (11)	0.0012 (11)	0.0027 (11)
C8	0.0614 (16)	0.0494 (16)	0.0480 (13)	−0.0010 (12)	0.0133 (12)	0.0017 (11)
C9	0.0449 (14)	0.0506 (14)	0.0617 (16)	−0.0035 (11)	0.0146 (13)	−0.0053 (12)
C10	0.0486 (15)	0.0605 (16)	0.0564 (16)	0.0036 (11)	0.0012 (12)	0.0028 (13)
C11	0.0443 (13)	0.0487 (14)	0.0474 (13)	0.0022 (10)	0.0016 (11)	0.0038 (11)
O1	0.0561 (11)	0.1191 (18)	0.0978 (18)	−0.0343 (12)	−0.0064 (12)	−0.0072 (13)
O2	0.0777 (15)	0.151 (2)	0.0764 (15)	−0.0335 (14)	0.0293 (12)	−0.0233 (16)

F1—C7	1.351 (3)	C4—C5	1.383 (3)
F2—C9	1.365 (2)	C4—H4A	0.9300
N1—C1	1.324 (3)	C5—C6	1.483 (3)
N1—C5	1.350 (3)	C6—C11	1.390 (3)
N2—O1	1.212 (3)	C6—C7	1.391 (3)
N2—O2	1.213 (3)	C7—C8	1.372 (3)
N2—C2	1.467 (3)	C8—C9	1.367 (4)
C1—C2	1.377 (3)	C8—H8A	0.9300
C1—H1A	0.9300	C9—C10	1.364 (4)
C2—C3	1.378 (3)	C10—C11	1.384 (3)
C3—C4	1.377 (3)	C10—H10A	0.9300
C3—H3A	0.9300	C11—H11A	0.9300
C1—N1—C5	118.19 (19)	C11—C6—C7	116.04 (19)
O1—N2—O2	124.2 (2)	C11—C6—C5	119.54 (19)
O1—N2—C2	117.6 (2)	C7—C6—C5	124.4 (2)
O2—N2—C2	118.2 (2)	F1—C7—C8	117.1 (2)
N1—C1—C2	122.4 (2)	F1—C7—C6	119.44 (19)
N1—C1—H1A	118.8	C8—C7—C6	123.5 (2)
C2—C1—H1A	118.8	C9—C8—C7	117.1 (2)
C1—C2—C3	120.1 (2)	C9—C8—H8A	121.4
C1—C2—N2	119.2 (2)	C7—C8—H8A	121.4
C3—C2—N2	120.7 (2)	C10—C9—F2	118.8 (2)
C4—C3—C2	117.8 (2)	C10—C9—C8	123.2 (2)
C4—C3—H3A	121.1	F2—C9—C8	118.0 (2)
C2—C3—H3A	121.1	C9—C10—C11	117.8 (2)
C3—C4—C5	119.4 (2)	C9—C10—H10A	121.1
C3—C4—H4A	120.3	C11—C10—H10A	121.1
C5—C4—H4A	120.3	C10—C11—C6	122.3 (2)
N1—C5—C4	122.1 (2)	C10—C11—H11A	118.9
N1—C5—C6	114.14 (19)	C6—C11—H11A	118.9
C4—C5—C6	123.72 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.93	2.56	3.306 (3)	138
C8—H8A···N1ii	0.93	2.58	3.448 (3)	156
C4—H4A···F1	0.93	2.40	2.893 (3)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1i	0.93	2.56	3.306 (3)	138
C8—H8A⋯N1ii	0.93	2.58	3.448 (3)	156
C4—H4A⋯F1	0.93	2.40	2.893 (3)	113

Symmetry codes: (i) ; (ii) .