2,6-Dichloro-3-nitro-pyridine.

The asymmetric unit of the title compound, C(5)H(2)Cl(2)N(2)O(2), consists of two crystallographically independent mol-ecules. The pyridine ring in each mol-ecule is essentially planar, with maximum deviations of 0.004 (4) and 0.007 (4) Å. Short Cl⋯O [3.09 (3) and 3.13 (4) Å] and Cl⋯Cl [3.38 (12) Å] contacts were observed. No significant inter-molecular inter-actions were observed in the crystal packing.

Related literature

For the role of the nitro­pyridine nucleus in the development of medicinal agents and in the field of agrochemicals, see: Davis et al. (1996 ▶). For the properties and use of pyridine derivatives, see: Vacher et al. (1998 ▶); Olah et al. (1980 ▶); Bare et al. (1989 ▶). For standard bond lengths, see: Allen et al. (1987 ▶). For the melting point, see: Johnson et al. (1967 ▶).

Experimental

Crystal data

C5H2Cl2N2O2

M = 192.99

Monoclinic,

a = 7.9021 (8) Å

b = 19.166 (2) Å

c = 11.0987 (9) Å

β = 122.072 (5)°

V = 1424.4 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.85 mm−1

T = 296 K

0.40 × 0.27 × 0.24 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.727, T max = 0.821

16845 measured reflections

4817 independent reflections

2323 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.180

S = 1.08

4817 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023683/ng5183sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023683/ng5183Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811023683/ng5183Isup3.cml

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

C5H2Cl2N2O2	F(000) = 768
Mr = 192.99	Dx = 1.800 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3419 reflections
a = 7.9021 (8) Å	θ = 2.4–31.7°
b = 19.166 (2) Å	µ = 0.85 mm−1
c = 11.0987 (9) Å	T = 296 K
β = 122.072 (5)°	Block, yellow
V = 1424.4 (2) Å3	0.40 × 0.27 × 0.24 mm
Z = 8

Bruker SMART APEXII DUO CCD area-detector diffractometer	4817 independent reflections
Radiation source: fine-focus sealed tube	2323 reflections with I > 2σ(I)
graphite	Rint = 0.060
φ and ω scans	θmax = 31.8°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.727, Tmax = 0.821	k = −28→28
16845 measured reflections	l = −16→16

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0527P)2 + 1.2999P] where P = (Fo2 + 2Fc2)/3
4817 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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
Cl1A	0.51344 (18)	0.68002 (5)	0.26085 (12)	0.0667 (3)
Cl2A	0.49627 (16)	0.91466 (4)	0.03753 (9)	0.0540 (3)
O1A	0.6135 (4)	1.00995 (14)	0.4256 (3)	0.0656 (8)
O2A	0.4472 (5)	1.01996 (13)	0.1975 (3)	0.0641 (8)
N1A	0.5042 (4)	0.80475 (13)	0.1709 (3)	0.0411 (6)
N2A	0.5284 (4)	0.98557 (14)	0.3053 (3)	0.0433 (6)
C1A	0.5404 (5)	0.87035 (18)	0.4058 (3)	0.0445 (8)
H1A	0.5538	0.8926	0.4848	0.053*
C2A	0.5356 (5)	0.79924 (18)	0.3979 (4)	0.0463 (8)
H2A	0.5436	0.7720	0.4701	0.056*
C3A	0.5182 (5)	0.76941 (15)	0.2786 (3)	0.0397 (7)
C4A	0.5072 (5)	0.87406 (15)	0.1788 (3)	0.0359 (7)
C5A	0.5251 (5)	0.90936 (15)	0.2945 (3)	0.0351 (7)
Cl1B	1.01800 (19)	0.67408 (5)	0.25606 (12)	0.0673 (3)
Cl2B	0.98563 (15)	0.91167 (5)	0.03234 (9)	0.0532 (3)
O1B	0.9156 (5)	1.00415 (15)	0.3366 (3)	0.0731 (9)
O2B	1.1216 (5)	1.01192 (14)	0.2658 (3)	0.0663 (8)
N1B	1.0071 (4)	0.79906 (13)	0.1667 (3)	0.0403 (6)
N2B	1.0196 (5)	0.97918 (15)	0.2975 (3)	0.0470 (7)
C1B	1.0342 (5)	0.86410 (18)	0.4000 (3)	0.0450 (8)
H1B	1.0422	0.8863	0.4773	0.054*
C2B	1.0342 (5)	0.79259 (19)	0.3928 (4)	0.0481 (8)
H2B	1.0421	0.7650	0.4646	0.058*
C3B	1.0218 (5)	0.76313 (16)	0.2741 (3)	0.0427 (8)
C4B	1.0086 (5)	0.86795 (16)	0.1754 (3)	0.0356 (7)
C5B	1.0219 (5)	0.90270 (16)	0.2895 (3)	0.0376 (7)

	U11	U22	U33	U12	U13	U23
Cl1A	0.0972 (8)	0.0347 (4)	0.0768 (7)	0.0060 (5)	0.0521 (7)	0.0129 (4)
Cl2A	0.0868 (7)	0.0430 (4)	0.0416 (5)	−0.0036 (4)	0.0405 (5)	0.0053 (3)
O1A	0.085 (2)	0.0609 (17)	0.0551 (16)	−0.0130 (15)	0.0404 (16)	−0.0206 (13)
O2A	0.093 (2)	0.0406 (13)	0.0633 (17)	0.0096 (13)	0.0444 (17)	0.0094 (12)
N1A	0.0520 (18)	0.0343 (12)	0.0418 (15)	0.0003 (12)	0.0281 (14)	0.0016 (11)
N2A	0.0494 (17)	0.0377 (13)	0.0509 (17)	−0.0023 (12)	0.0321 (15)	−0.0046 (12)
C1A	0.049 (2)	0.056 (2)	0.0346 (17)	0.0028 (16)	0.0257 (17)	0.0035 (14)
C2A	0.050 (2)	0.055 (2)	0.0391 (18)	0.0067 (16)	0.0274 (17)	0.0137 (15)
C3A	0.0457 (19)	0.0331 (14)	0.0429 (18)	0.0047 (13)	0.0252 (17)	0.0086 (13)
C4A	0.0435 (19)	0.0332 (14)	0.0329 (16)	0.0010 (13)	0.0215 (15)	0.0025 (11)
C5A	0.0392 (18)	0.0337 (14)	0.0353 (16)	0.0015 (13)	0.0218 (14)	0.0012 (12)
Cl1B	0.0970 (9)	0.0390 (5)	0.0691 (7)	0.0050 (5)	0.0463 (6)	0.0105 (4)
Cl2B	0.0762 (7)	0.0501 (5)	0.0381 (4)	−0.0015 (4)	0.0335 (5)	0.0079 (3)
O1B	0.084 (2)	0.0648 (18)	0.093 (2)	0.0032 (15)	0.062 (2)	−0.0159 (16)
O2B	0.093 (2)	0.0517 (15)	0.0721 (18)	−0.0135 (15)	0.0556 (18)	−0.0038 (13)
N1B	0.0452 (16)	0.0392 (14)	0.0387 (15)	0.0028 (12)	0.0238 (13)	0.0050 (11)
N2B	0.0530 (18)	0.0447 (15)	0.0421 (16)	−0.0030 (14)	0.0244 (15)	−0.0050 (12)
C1B	0.051 (2)	0.0542 (19)	0.0355 (17)	−0.0033 (16)	0.0268 (17)	−0.0007 (14)
C2B	0.052 (2)	0.059 (2)	0.0369 (18)	−0.0006 (17)	0.0255 (17)	0.0104 (15)
C3B	0.046 (2)	0.0391 (16)	0.0417 (19)	0.0036 (14)	0.0224 (17)	0.0085 (14)
C4B	0.0360 (18)	0.0426 (16)	0.0296 (15)	0.0014 (13)	0.0183 (14)	0.0045 (12)
C5B	0.0385 (18)	0.0420 (16)	0.0358 (16)	−0.0011 (14)	0.0221 (15)	0.0013 (13)

Cl1A—C3A	1.723 (3)	Cl1B—C3B	1.717 (3)
Cl2A—C4A	1.711 (3)	Cl2B—C4B	1.717 (3)
O1A—N2A	1.224 (3)	O1B—N2B	1.214 (4)
O2A—N2A	1.209 (4)	O2B—N2B	1.211 (4)
N1A—C4A	1.331 (4)	N1B—C4B	1.323 (4)
N1A—C3A	1.326 (4)	N1B—C3B	1.327 (4)
N2A—C5A	1.465 (4)	N2B—C5B	1.469 (4)
C1A—C2A	1.365 (5)	C1B—C2B	1.373 (5)
C1A—C5A	1.393 (4)	C1B—C5B	1.391 (4)
C1A—H1A	0.9300	C1B—H1B	0.9300
C2A—C3A	1.381 (5)	C2B—C3B	1.389 (5)
C2A—H2A	0.9300	C2B—H2B	0.9300
C4A—C5A	1.391 (4)	C4B—C5B	1.385 (4)
C4A—N1A—C3A	117.4 (3)	C4B—N1B—C3B	117.3 (3)
O2A—N2A—O1A	124.5 (3)	O2B—N2B—O1B	125.5 (3)
O2A—N2A—C5A	119.0 (3)	O2B—N2B—C5B	117.9 (3)
O1A—N2A—C5A	116.5 (3)	O1B—N2B—C5B	116.6 (3)
C2A—C1A—C5A	119.5 (3)	C2B—C1B—C5B	118.8 (3)
C2A—C1A—H1A	120.2	C2B—C1B—H1B	120.6
C5A—C1A—H1A	120.2	C5B—C1B—H1B	120.6
C1A—C2A—C3A	117.4 (3)	C1B—C2B—C3B	117.3 (3)
C1A—C2A—H2A	121.3	C1B—C2B—H2B	121.4
C3A—C2A—H2A	121.3	C3B—C2B—H2B	121.4
N1A—C3A—C2A	124.8 (3)	N1B—C3B—C2B	124.7 (3)
N1A—C3A—Cl1A	114.8 (2)	N1B—C3B—Cl1B	115.0 (3)
C2A—C3A—Cl1A	120.4 (2)	C2B—C3B—Cl1B	120.2 (3)
N1A—C4A—C5A	122.4 (3)	N1B—C4B—C5B	122.7 (3)
N1A—C4A—Cl2A	113.8 (2)	N1B—C4B—Cl2B	115.3 (2)
C5A—C4A—Cl2A	123.8 (2)	C5B—C4B—Cl2B	122.0 (2)
C1A—C5A—C4A	118.4 (3)	C4B—C5B—C1B	119.1 (3)
C1A—C5A—N2A	118.2 (3)	C4B—C5B—N2B	122.5 (3)
C4A—C5A—N2A	123.3 (3)	C1B—C5B—N2B	118.4 (3)
C5A—C1A—C2A—C3A	0.9 (5)	C5B—C1B—C2B—C3B	0.0 (5)
C4A—N1A—C3A—C2A	0.0 (5)	C4B—N1B—C3B—C2B	1.5 (5)
C4A—N1A—C3A—Cl1A	−180.0 (3)	C4B—N1B—C3B—Cl1B	179.7 (2)
C1A—C2A—C3A—N1A	−0.6 (6)	C1B—C2B—C3B—N1B	−1.1 (6)
C1A—C2A—C3A—Cl1A	179.4 (3)	C1B—C2B—C3B—Cl1B	−179.2 (3)
C3A—N1A—C4A—C5A	0.3 (5)	C3B—N1B—C4B—C5B	−0.9 (5)
C3A—N1A—C4A—Cl2A	178.0 (2)	C3B—N1B—C4B—Cl2B	−179.1 (2)
C2A—C1A—C5A—C4A	−0.6 (5)	N1B—C4B—C5B—C1B	0.0 (5)
C2A—C1A—C5A—N2A	179.3 (3)	Cl2B—C4B—C5B—C1B	178.1 (3)
N1A—C4A—C5A—C1A	0.0 (5)	N1B—C4B—C5B—N2B	−178.8 (3)
Cl2A—C4A—C5A—C1A	−177.5 (3)	Cl2B—C4B—C5B—N2B	−0.7 (5)
N1A—C4A—C5A—N2A	−179.9 (3)	C2B—C1B—C5B—C4B	0.5 (5)
Cl2A—C4A—C5A—N2A	2.6 (5)	C2B—C1B—C5B—N2B	179.3 (3)
O2A—N2A—C5A—C1A	−153.8 (3)	O2B—N2B—C5B—C4B	−44.8 (5)
O1A—N2A—C5A—C1A	25.6 (4)	O1B—N2B—C5B—C4B	135.7 (4)
O2A—N2A—C5A—C4A	26.1 (5)	O2B—N2B—C5B—C1B	136.4 (3)
O1A—N2A—C5A—C4A	−154.5 (3)	O1B—N2B—C5B—C1B	−43.0 (5)