2,4-Diiodo-3-nitro-anisole.

IN THE TITLE COMPOUND (SYSTEMATIC NAME: 1,3-diiodo-4-meth-oxy-2-nitro-benzene), C(7)H(5)I(2)NO(3), the dihedral angle between the benzene ring and the nitro group is 88.0 (3)°, and the methyl group lies almost in the same plane as the ring [deviation = 0.034 (6) Å]. In the crystal, aromatic π-π stacking occurs between inversion-related rings [centroid-centroid separation = 3.865 (3) Å and slippage = 0.642 Å]. A possible weak C-I⋯π inter-action occurs [I⋯π = 3.701 (2) Å and C-I⋯π = 130.18 (13)°], but there are no significant inter-molecular I⋯I contacts.

Related literature

For the crystal structures of isomers of the title compound, see: Garden et al. (2002 ▶, 2004 ▶).

Experimental

Crystal data

C7H5I2NO3

M = 404.92

Monoclinic,

a = 9.264 (2) Å

b = 8.756 (2) Å

c = 13.549 (3) Å

β = 108.835 (2)°

V = 1040.2 (4) Å3

Z = 4

Mo Kα radiation

μ = 6.02 mm−1

T = 296 K

0.36 × 0.33 × 0.14 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.220, T max = 0.486

7459 measured reflections

1937 independent reflections

1712 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.065

S = 1.00

2689 reflections

172 parameters

H-atom parameters constrained

Δρmax = 1.06 e Å−3

Δρmin = −1.25 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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) global, I. DOI: 10.1107/S160053681200952X/hb6662sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681200952X/hb6662Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681200952X/hb6662Isup3.cml

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

C7H5I2NO3	F(000) = 736
Mr = 404.92	Dx = 2.586 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.264 (2) Å	Cell parameters from 3452 reflections
b = 8.756 (2) Å	θ = 2.8–27.0°
c = 13.549 (3) Å	µ = 6.02 mm−1
β = 108.835 (2)°	T = 296 K
V = 1040.2 (4) Å3	Block, yellow
Z = 4	0.36 × 0.33 × 0.14 mm

Bruker SMART CCD diffractometer	1937 independent reflections
Radiation source: fine-focus sealed tube	1712 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
phi and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
Tmin = 0.220, Tmax = 0.486	k = −10→10
7459 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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0264P)2 + 3.0364P] where P = (Fo2 + 2Fc2)/3
2689 reflections	(Δ/σ)max = 0.001
172 parameters	Δρmax = 1.06 e Å−3
0 restraints	Δρmin = −1.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.3646 (5)	0.8010 (5)	0.0510 (3)	0.0431 (10)
C2	0.4466 (5)	0.8963 (5)	0.1324 (3)	0.0391 (9)
C3	0.6036 (5)	0.9031 (5)	0.1575 (3)	0.0405 (9)
C4	0.6821 (5)	0.8208 (6)	0.1041 (3)	0.0465 (11)
C5	0.5990 (6)	0.7285 (6)	0.0233 (3)	0.0519 (12)
H5	0.6490	0.6724	−0.0141	0.062*
C6	0.4412 (6)	0.7182 (6)	−0.0030 (3)	0.0488 (11)
H6	0.3870	0.6549	−0.0574	0.059*
C7	0.1252 (6)	0.7011 (7)	−0.0503 (4)	0.0659 (15)
H7A	0.1457	0.7238	−0.1138	0.099*
H7B	0.0185	0.7152	−0.0607	0.099*
H7C	0.1529	0.5971	−0.0306	0.099*
N1	0.6918 (5)	1.0000 (5)	0.2475 (3)	0.0507 (10)
O1	0.7319 (6)	0.9427 (5)	0.3316 (3)	0.0860 (14)
O2	0.7193 (5)	1.1291 (5)	0.2286 (3)	0.0831 (13)
O3	0.2116 (4)	0.8002 (4)	0.0299 (2)	0.0571 (9)
I1	0.33063 (4)	1.02858 (4)	0.21050 (3)	0.05654 (12)
I2	0.91883 (4)	0.82973 (6)	0.14145 (3)	0.08415 (18)

	U11	U22	U33	U12	U13	U23
C1	0.048 (2)	0.046 (2)	0.034 (2)	−0.002 (2)	0.0103 (18)	0.0012 (19)
C2	0.047 (2)	0.037 (2)	0.034 (2)	0.0034 (19)	0.0143 (18)	0.0028 (18)
C3	0.048 (2)	0.039 (2)	0.032 (2)	−0.0018 (19)	0.0096 (18)	0.0047 (18)
C4	0.044 (2)	0.056 (3)	0.041 (2)	0.007 (2)	0.0163 (19)	0.009 (2)
C5	0.067 (3)	0.054 (3)	0.040 (2)	0.009 (2)	0.024 (2)	−0.002 (2)
C6	0.062 (3)	0.049 (3)	0.033 (2)	0.000 (2)	0.011 (2)	−0.0057 (19)
C7	0.054 (3)	0.093 (4)	0.046 (3)	−0.021 (3)	0.009 (2)	−0.017 (3)
N1	0.050 (2)	0.056 (3)	0.043 (2)	−0.0101 (19)	0.0105 (18)	0.0048 (18)
O1	0.119 (4)	0.081 (3)	0.039 (2)	−0.024 (3)	−0.001 (2)	0.005 (2)
O2	0.105 (3)	0.064 (3)	0.065 (2)	−0.034 (2)	0.007 (2)	0.000 (2)
O3	0.0453 (18)	0.070 (2)	0.0505 (19)	−0.0050 (16)	0.0083 (15)	−0.0121 (17)
I1	0.0635 (2)	0.0536 (2)	0.0582 (2)	0.00317 (16)	0.02756 (16)	−0.01141 (15)
I2	0.0470 (2)	0.1373 (4)	0.0684 (3)	0.0114 (2)	0.01898 (18)	−0.0001 (2)

C1—O3	1.353 (5)	C5—C6	1.391 (7)
C1—C6	1.378 (6)	C5—H5	0.9300
C1—C2	1.396 (6)	C6—H6	0.9300
C2—C3	1.384 (6)	C7—O3	1.419 (6)
C2—I1	2.086 (4)	C7—H7A	0.9600
C3—C4	1.382 (6)	C7—H7B	0.9600
C3—N1	1.493 (6)	C7—H7C	0.9600
C4—C5	1.379 (7)	N1—O1	1.189 (5)
C4—I2	2.087 (5)	N1—O2	1.205 (5)
O3—C1—C6	124.7 (4)	C6—C5—H5	119.6
O3—C1—C2	115.9 (4)	C1—C6—C5	120.6 (4)
C6—C1—C2	119.4 (4)	C1—C6—H6	119.7
C3—C2—C1	118.7 (4)	C5—C6—H6	119.7
C3—C2—I1	121.6 (3)	O3—C7—H7A	109.5
C1—C2—I1	119.6 (3)	O3—C7—H7B	109.5
C4—C3—C2	122.5 (4)	H7A—C7—H7B	109.5
C4—C3—N1	118.9 (4)	O3—C7—H7C	109.5
C2—C3—N1	118.6 (4)	H7A—C7—H7C	109.5
C5—C4—C3	117.9 (4)	H7B—C7—H7C	109.5
C5—C4—I2	119.2 (3)	O1—N1—O2	125.2 (4)
C3—C4—I2	122.9 (3)	O1—N1—C3	117.6 (4)
C4—C5—C6	120.8 (4)	O2—N1—C3	117.2 (4)
C4—C5—H5	119.6	C1—O3—C7	117.3 (4)
O3—C1—C2—C3	−179.6 (4)	C3—C4—C5—C6	−0.4 (7)
C6—C1—C2—C3	−1.0 (6)	I2—C4—C5—C6	179.2 (4)
O3—C1—C2—I1	−1.1 (5)	O3—C1—C6—C5	178.8 (4)
C6—C1—C2—I1	177.5 (3)	C2—C1—C6—C5	0.3 (7)
C1—C2—C3—C4	1.0 (6)	C4—C5—C6—C1	0.4 (7)
I1—C2—C3—C4	−177.5 (3)	C4—C3—N1—O1	−90.3 (6)
C1—C2—C3—N1	−177.4 (4)	C2—C3—N1—O1	88.1 (6)
I1—C2—C3—N1	4.2 (5)	C4—C3—N1—O2	88.1 (6)
C2—C3—C4—C5	−0.3 (7)	C2—C3—N1—O2	−93.5 (5)
N1—C3—C4—C5	178.0 (4)	C6—C1—O3—C7	3.3 (7)
C2—C3—C4—I2	−179.9 (3)	C2—C1—O3—C7	−178.2 (4)
N1—C3—C4—I2	−1.5 (6)