1-(3,3-Dichloro-all-yloxy)-4-methyl-2-nitro-benzene.

In the title compound, C(10)H(9)Cl(2)NO(3), the dihedral angle between the benzene ring and the plane of the nitro group is 39.1 (1)°, while that between the benzene ring and the plane through the three C and two Cl atoms of the dichloro-all-yloxy unit is 40.1 (1)°. In the crystal, C-H⋯O hydrogen bonds to the nitro groups form chains along the b axis. These chains are linked by inversion-related pairs of Cl⋯O inter-actions at a distance of 3.060 (3) Å, forming sheets approximately parallel to [-201] and generating R(2) (2)(18) rings. π-π contacts between benzene rings in adjacent sheets, with centroid-centroid distances of 3.671 (2) Å, stack mol-ecules along c.

Related literature

For background to the applications of the title compound, see: Kolosov et al. (2002 ▶). For its synthesis, see: Walker et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C10H9Cl2NO3

M = 262.08

Triclinic,

a = 7.5430 (15) Å

b = 7.7630 (16) Å

c = 10.713 (2) Å

α = 83.69 (3)°

β = 88.78 (3)°

γ = 67.23 (3)°

V = 574.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.56 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 = 0.851, T max = 0.947

2277 measured reflections

2103 independent reflections

1638 reflections with I > 2σ(I)

R int = 0.021

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.156

S = 1.01

2103 reflections

145 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.28 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: 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/S1600536812023057/sj5235sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023057/sj5235Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812023057/sj5235Isup3.cml

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

C10H9Cl2NO3	Z = 2
Mr = 262.08	F(000) = 268
Triclinic, P1	Dx = 1.514 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5430 (15) Å	Cell parameters from 25 reflections
b = 7.7630 (16) Å	θ = 10–13°
c = 10.713 (2) Å	µ = 0.56 mm−1
α = 83.69 (3)°	T = 293 K
β = 88.78 (3)°	Block, colourless
γ = 67.23 (3)°	0.30 × 0.20 × 0.10 mm
V = 574.8 (2) Å3

Enraf–Nonius CAD-4 diffractometer	1638 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
Graphite monochromator	θmax = 25.4°, θmin = 1.9°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = −8→9
Tmin = 0.851, Tmax = 0.947	l = −12→12
2277 measured reflections	3 standard reflections every 200 reflections
2103 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1P)2 + 0.130P] where P = (Fo2 + 2Fc2)/3
2103 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.28 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
Cl1	0.35049 (14)	0.31042 (13)	0.40617 (7)	0.0723 (3)
Cl2	0.20254 (13)	0.53282 (12)	0.60994 (8)	0.0713 (3)
O1	0.8637 (4)	−0.2999 (3)	0.8304 (2)	0.0767 (8)
O2	0.7766 (4)	−0.4263 (3)	0.9976 (2)	0.0731 (7)
O3	0.6554 (3)	0.0677 (3)	0.82149 (17)	0.0542 (5)
N	0.8110 (4)	−0.2976 (3)	0.9385 (2)	0.0534 (6)
C1	0.6985 (4)	0.1898 (4)	1.0130 (3)	0.0506 (7)
H1A	0.6478	0.3133	0.9755	0.061*
C2	0.7574 (4)	0.1533 (4)	1.1372 (3)	0.0511 (7)
H2A	0.7446	0.2537	1.1816	0.061*
C3	0.8352 (4)	−0.0276 (4)	1.1987 (2)	0.0461 (6)
C4	0.8481 (4)	−0.1727 (4)	1.1298 (2)	0.0457 (6)
H4A	0.8972	−0.2958	1.1681	0.055*
C5	0.7892 (4)	−0.1372 (4)	1.0055 (2)	0.0411 (6)
C6	0.7139 (4)	0.0451 (4)	0.9434 (2)	0.0417 (6)
C7	0.9018 (5)	−0.0623 (5)	1.3344 (3)	0.0661 (9)
H7A	0.8808	0.0554	1.3652	0.099*
H7B	1.0364	−0.1409	1.3409	0.099*
H7C	0.8306	−0.1235	1.3835	0.099*
C8	0.5768 (5)	0.2544 (4)	0.7592 (3)	0.0515 (7)
H8A	0.6681	0.3142	0.7612	0.062*
H8B	0.4597	0.3296	0.7989	0.062*
C9	0.5358 (5)	0.2340 (4)	0.6279 (3)	0.0537 (7)
H9A	0.6257	0.1337	0.5915	0.064*
C10	0.3856 (5)	0.3433 (4)	0.5586 (3)	0.0517 (7)

	U11	U22	U33	U12	U13	U23
Cl1	0.0946 (7)	0.0785 (6)	0.0430 (4)	−0.0320 (5)	−0.0101 (4)	−0.0062 (4)
Cl2	0.0730 (6)	0.0587 (5)	0.0630 (5)	−0.0040 (4)	−0.0091 (4)	−0.0066 (4)
O1	0.112 (2)	0.0556 (14)	0.0473 (13)	−0.0128 (13)	−0.0062 (13)	−0.0175 (10)
O2	0.0858 (17)	0.0430 (12)	0.0966 (18)	−0.0307 (12)	0.0023 (14)	−0.0107 (12)
O3	0.0765 (14)	0.0393 (10)	0.0438 (11)	−0.0199 (10)	−0.0116 (10)	0.0006 (8)
N	0.0584 (15)	0.0364 (12)	0.0599 (16)	−0.0107 (11)	−0.0099 (12)	−0.0090 (11)
C1	0.0641 (18)	0.0350 (14)	0.0531 (16)	−0.0199 (13)	−0.0054 (13)	−0.0024 (12)
C2	0.0625 (18)	0.0450 (15)	0.0504 (16)	−0.0239 (13)	0.0007 (13)	−0.0127 (12)
C3	0.0460 (15)	0.0525 (16)	0.0410 (14)	−0.0199 (12)	0.0037 (11)	−0.0078 (12)
C4	0.0489 (15)	0.0438 (14)	0.0412 (14)	−0.0166 (12)	0.0006 (11)	0.0027 (11)
C5	0.0426 (14)	0.0373 (13)	0.0453 (14)	−0.0170 (11)	0.0030 (11)	−0.0065 (11)
C6	0.0453 (14)	0.0415 (14)	0.0376 (13)	−0.0165 (11)	−0.0009 (11)	−0.0020 (11)
C7	0.076 (2)	0.076 (2)	0.0444 (16)	−0.0263 (18)	−0.0025 (15)	−0.0086 (15)
C8	0.0635 (18)	0.0411 (14)	0.0446 (15)	−0.0158 (13)	−0.0059 (13)	0.0023 (12)
C9	0.0617 (18)	0.0477 (16)	0.0449 (15)	−0.0139 (14)	0.0011 (13)	−0.0051 (12)
C10	0.0648 (18)	0.0487 (16)	0.0413 (15)	−0.0218 (14)	−0.0014 (13)	−0.0033 (12)

Cl1—C10	1.721 (3)	C3—C7	1.510 (4)
Cl2—C10	1.717 (3)	C4—C5	1.378 (4)
O1—N	1.216 (3)	C4—H4A	0.9300
O2—N	1.233 (3)	C5—C6	1.398 (4)
O3—C6	1.358 (3)	C7—H7A	0.9600
O3—C8	1.427 (3)	C7—H7B	0.9600
N—C5	1.458 (3)	C7—H7C	0.9600
C1—C2	1.375 (4)	C8—C9	1.484 (4)
C1—C6	1.383 (4)	C8—H8A	0.9700
C1—H1A	0.9300	C8—H8B	0.9700
C2—C3	1.388 (4)	C9—C10	1.307 (4)
C2—H2A	0.9300	C9—H9A	0.9300
C3—C4	1.384 (4)
C6—O3—C8	117.7 (2)	O3—C6—C5	118.1 (2)
O1—N—O2	123.7 (2)	C1—C6—C5	116.9 (2)
O1—N—C5	119.6 (3)	C3—C7—H7A	109.5
O2—N—C5	116.6 (2)	C3—C7—H7B	109.5
C2—C1—C6	120.8 (3)	H7A—C7—H7B	109.5
C2—C1—H1A	119.6	C3—C7—H7C	109.5
C6—C1—H1A	119.6	H7A—C7—H7C	109.5
C1—C2—C3	122.5 (3)	H7B—C7—H7C	109.5
C1—C2—H2A	118.7	O3—C8—C9	105.5 (2)
C3—C2—H2A	118.7	O3—C8—H8A	110.6
C4—C3—C2	116.9 (2)	C9—C8—H8A	110.6
C4—C3—C7	122.2 (3)	O3—C8—H8B	110.6
C2—C3—C7	120.9 (3)	C9—C8—H8B	110.6
C5—C4—C3	120.9 (3)	H8A—C8—H8B	108.8
C5—C4—H4A	119.5	C10—C9—C8	126.3 (3)
C3—C4—H4A	119.5	C10—C9—H9A	116.9
C4—C5—C6	122.0 (3)	C8—C9—H9A	116.9
C4—C5—N	117.7 (2)	C9—C10—Cl2	123.7 (2)
C6—C5—N	120.3 (2)	C9—C10—Cl1	123.2 (2)
O3—C6—C1	124.9 (2)	Cl2—C10—Cl1	113.06 (18)
C6—C1—C2—C3	0.3 (5)	C8—O3—C6—C5	179.3 (2)
C1—C2—C3—C4	−1.3 (4)	C2—C1—C6—O3	178.3 (3)
C1—C2—C3—C7	178.8 (3)	C2—C1—C6—C5	0.7 (4)
C2—C3—C4—C5	1.2 (4)	C4—C5—C6—O3	−178.6 (2)
C7—C3—C4—C5	−178.9 (3)	N—C5—C6—O3	2.5 (4)
C3—C4—C5—C6	−0.2 (4)	C4—C5—C6—C1	−0.8 (4)
C3—C4—C5—N	178.7 (3)	N—C5—C6—C1	−179.7 (3)
O1—N—C5—C4	−140.1 (3)	C6—O3—C8—C9	177.3 (2)
O2—N—C5—C4	38.8 (4)	O3—C8—C9—C10	140.5 (3)
O1—N—C5—C6	38.9 (4)	C8—C9—C10—Cl2	−1.1 (5)
O2—N—C5—C6	−142.3 (3)	C8—C9—C10—Cl1	179.4 (2)
C8—O3—C6—C1	1.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2i	0.93	2.59	3.241 (4)	127

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2i	0.93	2.59	3.241 (4)	127

Symmetry code: (i) .