2-Chloro-4-(3,3-dichloro-all-yloxy)-1-nitro-benzene.

In the crystal structure of the title compound, C(9)H(6)Cl(3)NO(3), mol-ecules are connected by C-H⋯O hydrogen bonds, forming chains along the b axis. The dihedral angle between the benzene ring and the plane of the nitro group is 16.2 (1)° and that between the benzene ring and the plane of the dichloro-allyl group is 10.2 (1)°.

Related literature

For background to the applications of the title compound, see: Kolosov et al. (2002 ▶). For the synthesis, see: Walker et al. (2005 ▶).

Experimental

Crystal data

C9H6Cl3NO3

M = 282.50

Monoclinic,

a = 12.476 (3) Å

b = 12.775 (3) Å

c = 7.2230 (14) Å

β = 92.32 (3)°

V = 1150.3 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.79 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.799, T max = 0.926

2300 measured reflections

2118 independent reflections

1414 reflections with I > 2σ(I)

R int = 0.023

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.183

S = 1.00

2118 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (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/S160053681201865X/vm2169sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201865X/vm2169Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681201865X/vm2169Isup3.cml

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

C9H6Cl3NO3	F(000) = 568
Mr = 282.50	Dx = 1.631 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 12.476 (3) Å	θ = 10–13°
b = 12.775 (3) Å	µ = 0.79 mm−1
c = 7.2230 (14) Å	T = 293 K
β = 92.32 (3)°	Block, colourless
V = 1150.3 (4) Å3	0.30 × 0.20 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1414 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Graphite monochromator	θmax = 25.4°, θmin = 1.6°
ω/2θ scans	h = −15→15
Absorption correction: ψ scan (North et al., 1968)	k = −15→0
Tmin = 0.799, Tmax = 0.926	l = 0→8
2300 measured reflections	3 standard reflections every 200 reflections
2118 independent reflections	intensity decay: 1%

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.183	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.7P] where P = (Fo2 + 2Fc2)/3
2118 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.52 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
N	0.0625 (4)	1.3968 (3)	0.1971 (7)	0.0603 (12)
Cl1	0.31002 (11)	1.42882 (9)	0.1250 (2)	0.0643 (4)
C1	0.2996 (4)	1.2216 (4)	0.1245 (7)	0.0468 (11)
H1A	0.3724	1.2256	0.1021	0.056*
O1	0.3184 (3)	1.0417 (2)	0.1211 (5)	0.0560 (9)
Cl2	0.45065 (11)	0.67097 (10)	0.1106 (2)	0.0685 (5)
C2	0.2415 (4)	1.3117 (3)	0.1436 (7)	0.0452 (11)
O2	0.1009 (4)	1.4802 (3)	0.2323 (8)	0.1053 (18)
Cl3	0.22239 (11)	0.70364 (10)	0.1046 (2)	0.0679 (5)
C3	0.1325 (3)	1.3051 (3)	0.1756 (7)	0.0441 (11)
O3	−0.0309 (3)	1.3841 (4)	0.1923 (12)	0.157 (3)
C4	0.0837 (4)	1.2084 (4)	0.1880 (7)	0.0505 (12)
H4A	0.0105	1.2044	0.2073	0.061*
C5	0.1433 (4)	1.1170 (4)	0.1718 (7)	0.0496 (12)
H5A	0.1106	1.0520	0.1837	0.060*
C6	0.2501 (4)	1.1231 (3)	0.1384 (6)	0.0432 (11)
C7	0.2718 (4)	0.9380 (3)	0.1296 (8)	0.0585 (14)
H7A	0.2213	0.9272	0.0256	0.070*
H7B	0.2340	0.9297	0.2434	0.070*
C8	0.3611 (4)	0.8612 (4)	0.1230 (7)	0.0542 (13)
H8A	0.4310	0.8865	0.1258	0.065*
C9	0.3467 (4)	0.7601 (4)	0.1137 (7)	0.0493 (12)

	U11	U22	U33	U12	U13	U23
N	0.055 (3)	0.040 (2)	0.087 (3)	0.0090 (19)	0.005 (2)	−0.007 (2)
Cl1	0.0614 (8)	0.0331 (6)	0.0991 (11)	−0.0085 (5)	0.0112 (7)	−0.0018 (6)
C1	0.042 (2)	0.037 (2)	0.062 (3)	0.0005 (19)	0.013 (2)	0.005 (2)
O1	0.0505 (18)	0.0324 (16)	0.086 (2)	−0.0030 (14)	0.0182 (17)	0.0000 (17)
Cl2	0.0583 (8)	0.0419 (7)	0.1055 (12)	0.0096 (6)	0.0065 (7)	−0.0031 (7)
C2	0.052 (3)	0.026 (2)	0.058 (3)	−0.0048 (19)	0.005 (2)	−0.001 (2)
O2	0.081 (3)	0.042 (2)	0.194 (6)	0.011 (2)	0.022 (3)	−0.013 (3)
Cl3	0.0563 (8)	0.0419 (7)	0.1063 (12)	−0.0047 (6)	0.0121 (7)	−0.0094 (7)
C3	0.044 (2)	0.031 (2)	0.058 (3)	0.0050 (19)	0.002 (2)	0.000 (2)
O3	0.037 (2)	0.069 (3)	0.366 (10)	0.009 (2)	0.019 (4)	−0.050 (5)
C4	0.041 (2)	0.046 (3)	0.065 (3)	−0.004 (2)	0.010 (2)	−0.001 (2)
C5	0.054 (3)	0.030 (2)	0.066 (3)	−0.005 (2)	0.011 (2)	0.003 (2)
C6	0.051 (3)	0.029 (2)	0.050 (3)	0.0001 (19)	0.010 (2)	0.001 (2)
C7	0.048 (3)	0.032 (2)	0.096 (4)	−0.006 (2)	0.010 (3)	−0.002 (3)
C8	0.052 (3)	0.037 (3)	0.074 (3)	−0.005 (2)	0.006 (2)	−0.002 (2)
C9	0.052 (3)	0.037 (3)	0.059 (3)	0.004 (2)	0.008 (2)	0.006 (2)

N—O3	1.176 (6)	Cl3—C9	1.709 (5)
N—O2	1.192 (6)	C3—C4	1.382 (6)
N—C3	1.472 (6)	C4—C5	1.392 (6)
Cl1—C2	1.731 (4)	C4—H4A	0.9300
C1—C2	1.370 (6)	C5—C6	1.367 (6)
C1—C6	1.406 (6)	C5—H5A	0.9300
C1—H1A	0.9300	C7—C8	1.487 (6)
O1—C6	1.353 (5)	C7—H7A	0.9700
O1—C7	1.449 (5)	C7—H7B	0.9700
Cl2—C9	1.727 (5)	C8—C9	1.304 (7)
C2—C3	1.392 (6)	C8—H8A	0.9300
O3—N—O2	121.2 (5)	C6—C5—H5A	120.2
O3—N—C3	118.6 (4)	C4—C5—H5A	120.2
O2—N—C3	119.9 (4)	O1—C6—C5	126.4 (4)
C2—C1—C6	120.6 (4)	O1—C6—C1	113.6 (4)
C2—C1—H1A	119.7	C5—C6—C1	119.9 (4)
C6—C1—H1A	119.7	O1—C7—C8	107.5 (4)
C6—O1—C7	116.4 (4)	O1—C7—H7A	110.2
C1—C2—C3	119.4 (4)	C8—C7—H7A	110.2
C1—C2—Cl1	117.0 (4)	O1—C7—H7B	110.2
C3—C2—Cl1	123.6 (3)	C8—C7—H7B	110.2
C4—C3—C2	120.1 (4)	H7A—C7—H7B	108.5
C4—C3—N	116.1 (4)	C9—C8—C7	123.6 (5)
C2—C3—N	123.9 (4)	C9—C8—H8A	118.2
C3—C4—C5	120.4 (4)	C7—C8—H8A	118.2
C3—C4—H4A	119.8	C8—C9—Cl3	122.9 (4)
C5—C4—H4A	119.8	C8—C9—Cl2	123.4 (4)
C6—C5—C4	119.7 (4)	Cl3—C9—Cl2	113.7 (3)
C6—C1—C2—C3	−0.5 (7)	C3—C4—C5—C6	−1.8 (7)
C6—C1—C2—Cl1	179.8 (4)	C7—O1—C6—C5	3.3 (7)
C1—C2—C3—C4	0.0 (7)	C7—O1—C6—C1	−178.5 (4)
Cl1—C2—C3—C4	179.8 (4)	C4—C5—C6—O1	179.4 (5)
C1—C2—C3—N	−179.6 (5)	C4—C5—C6—C1	1.3 (7)
Cl1—C2—C3—N	0.1 (7)	C2—C1—C6—O1	−178.4 (4)
O3—N—C3—C4	−12.3 (8)	C2—C1—C6—C5	−0.2 (7)
O2—N—C3—C4	162.1 (5)	C6—O1—C7—C8	−175.5 (4)
O3—N—C3—C2	167.3 (6)	O1—C7—C8—C9	−174.5 (5)
O2—N—C3—C2	−18.2 (8)	C7—C8—C9—Cl3	0.9 (8)
C2—C3—C4—C5	1.1 (7)	C7—C8—C9—Cl2	−178.7 (4)
N—C3—C4—C5	−179.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O3i	0.93	2.54	3.449 (7)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O3i	0.93	2.54	3.449 (7)	165

Symmetry code: (i) .