1-Iodo-4-meth-oxy-2-nitro-benzene.

In the title compound, C(7)H(6)INO(3), the 12 non-H atoms are planar, with an r.m.s. deviation of 0.016 Å. A close intra-molecular I⋯O inter-action [3.0295 (13) Å] is present. Inter-molecular I⋯O inter-actions [3.3448 (13) Å] lead to the formation of zigzag chains along the b axis. These are assembled into layers by weak π-π inter-actions [centroid-centroid distance = 3.8416 (9) Å], and the layers stack along the a axis, being connected by C-H⋯O contacts.

Related literature

For general background to halogen bonding, see: Metrangolo et al. (2008 ▶); Pennington et al. (2008 ▶). For previous structural studies probing iodo–nitro inter­actions, see: Glidewell et al. (2002 ▶, 2004 ▶); Garden et al. (2002 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

C7H6INO3

M = 279.03

Orthorhombic,

a = 18.6370 (13) Å

b = 11.6257 (5) Å

c = 7.4740 (3) Å

V = 1619.38 (15) Å3

Z = 8

Mo Kα radiation

μ = 3.92 mm−1

T = 100 K

0.13 × 0.09 × 0.01 mm

Data collection

Rigaku Saturn724+ (2 × 2 bin mode) diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011 ▶) T min = 0.755, T max = 1.000

8053 measured reflections

1841 independent reflections

1615 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.014

wR(F 2) = 0.039

S = 1.04

1841 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku, 2011 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006484/hg5176sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006484/hg5176Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006484/hg5176Isup3.cml

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

C7H6INO3	F(000) = 1056
Mr = 279.03	Dx = 2.289 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 6840 reflections
a = 18.6370 (13) Å	θ = 3.4–27.4°
b = 11.6257 (5) Å	µ = 3.92 mm−1
c = 7.4740 (3) Å	T = 100 K
V = 1619.38 (15) Å3	Plate, dark-orange
Z = 8	0.13 × 0.09 × 0.01 mm

Rigaku Saturn724+ (2x2 bin mode) diffractometer	1841 independent reflections
Radiation source: Rotating Anode	1615 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.017
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.4°
profile data from ω–scans	h = −15→24
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2011)	k = −14→14
Tmin = 0.755, Tmax = 1.000	l = −9→8
8053 measured reflections

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)] = 0.014	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.039	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0188P)2 + 0.9351P] where P = (Fo2 + 2Fc2)/3
1841 reflections	(Δ/σ)max = 0.002
110 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
I1	0.697282 (5)	0.925416 (9)	−0.003362 (13)	0.01546 (5)
O1	0.70514 (6)	0.66598 (11)	−0.03589 (18)	0.0231 (3)
O2	0.62939 (7)	0.52986 (10)	0.01236 (15)	0.0214 (3)
O3	0.41118 (6)	0.68759 (8)	0.23820 (15)	0.0148 (2)
N1	0.64607 (7)	0.63180 (12)	0.01188 (16)	0.0133 (3)
C1	0.60441 (8)	0.83551 (12)	0.0734 (2)	0.0119 (3)
C2	0.59202 (8)	0.71660 (12)	0.0719 (2)	0.0116 (3)
C3	0.52698 (8)	0.67047 (12)	0.12652 (19)	0.0122 (3)
H3	0.5199	0.5896	0.1236	0.015*
C4	0.47214 (8)	0.74173 (12)	0.1854 (2)	0.0115 (3)
C5	0.48273 (8)	0.86045 (12)	0.1870 (2)	0.0128 (3)
H5	0.4455	0.9104	0.2254	0.015*
C6	0.54812 (8)	0.90498 (12)	0.1319 (2)	0.0131 (3)
H6	0.5548	0.9860	0.1342	0.016*
C7	0.35196 (8)	0.75849 (13)	0.2943 (2)	0.0157 (3)
H7A	0.3658	0.8025	0.4007	0.024*
H7B	0.3107	0.7096	0.3228	0.024*
H7C	0.3391	0.8116	0.1977	0.024*

	U11	U22	U33	U12	U13	U23
I1	0.01244 (8)	0.01476 (8)	0.01918 (8)	−0.00280 (4)	0.00198 (3)	0.00187 (4)
O1	0.0129 (6)	0.0209 (6)	0.0354 (7)	0.0015 (5)	0.0054 (5)	−0.0037 (5)
O2	0.0223 (7)	0.0104 (5)	0.0315 (7)	0.0033 (5)	0.0035 (5)	−0.0004 (4)
O3	0.0109 (5)	0.0121 (5)	0.0214 (6)	−0.0013 (4)	0.0029 (4)	−0.0001 (4)
N1	0.0128 (6)	0.0149 (6)	0.0124 (6)	0.0025 (5)	−0.0020 (4)	−0.0002 (5)
C1	0.0108 (7)	0.0137 (7)	0.0113 (7)	−0.0019 (6)	−0.0011 (5)	0.0018 (5)
C2	0.0122 (7)	0.0115 (6)	0.0111 (7)	0.0038 (6)	−0.0016 (5)	−0.0007 (5)
C3	0.0146 (7)	0.0091 (6)	0.0130 (7)	0.0003 (5)	−0.0024 (5)	0.0004 (5)
C4	0.0101 (6)	0.0135 (7)	0.0109 (7)	−0.0013 (5)	−0.0014 (5)	0.0007 (5)
C5	0.0116 (7)	0.0121 (6)	0.0148 (7)	0.0027 (6)	−0.0009 (5)	−0.0010 (5)
C6	0.0154 (7)	0.0097 (6)	0.0143 (7)	−0.0006 (6)	−0.0014 (6)	0.0003 (6)
C7	0.0110 (7)	0.0170 (7)	0.0191 (8)	0.0009 (6)	0.0019 (6)	0.0001 (6)

I1—C1	2.1017 (14)	C3—C4	1.387 (2)
O1—N1	1.2238 (18)	C3—H3	0.9500
O2—N1	1.225 (2)	C4—C5	1.394 (2)
O3—C4	1.3574 (18)	C5—C6	1.386 (2)
O3—C7	1.4398 (18)	C5—H5	0.9500
N1—C2	1.4791 (19)	C6—H6	0.9500
C1—C6	1.395 (2)	C7—H7A	0.9800
C1—C2	1.4017 (19)	C7—H7B	0.9800
C2—C3	1.387 (2)	C7—H7C	0.9800
C4—O3—C7	117.44 (11)	O3—C4—C5	125.10 (13)
O1—N1—O2	122.90 (14)	C3—C4—C5	119.30 (13)
O1—N1—C2	119.00 (13)	C6—C5—C4	119.44 (13)
O2—N1—C2	118.10 (13)	C6—C5—H5	120.3
C6—C1—C2	116.72 (13)	C4—C5—H5	120.3
C6—C1—I1	114.66 (10)	C5—C6—C1	122.56 (13)
C2—C1—I1	128.62 (11)	C5—C6—H6	118.7
C3—C2—C1	121.54 (13)	C1—C6—H6	118.7
C3—C2—N1	115.27 (12)	O3—C7—H7A	109.5
C1—C2—N1	123.19 (13)	O3—C7—H7B	109.5
C2—C3—C4	120.42 (13)	H7A—C7—H7B	109.5
C2—C3—H3	119.8	O3—C7—H7C	109.5
C4—C3—H3	119.8	H7A—C7—H7C	109.5
O3—C4—C3	115.59 (12)	H7B—C7—H7C	109.5
C6—C1—C2—C3	−0.2 (2)	C7—O3—C4—C3	−177.84 (13)
I1—C1—C2—C3	−179.68 (11)	C7—O3—C4—C5	2.3 (2)
C6—C1—C2—N1	179.41 (13)	C2—C3—C4—O3	−179.07 (13)
I1—C1—C2—N1	−0.1 (2)	C2—C3—C4—C5	0.8 (2)
O1—N1—C2—C3	−178.97 (13)	O3—C4—C5—C6	179.05 (14)
O2—N1—C2—C3	1.04 (19)	C3—C4—C5—C6	−0.9 (2)
O1—N1—C2—C1	1.5 (2)	C4—C5—C6—C1	0.4 (2)
O2—N1—C2—C1	−178.54 (14)	C2—C1—C6—C5	0.1 (2)
C1—C2—C3—C4	−0.3 (2)	I1—C1—C6—C5	179.73 (12)
N1—C2—C3—C4	−179.93 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7B···O1i	0.98	2.58	3.4503 (19)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7B⋯O1i	0.98	2.58	3.4503 (19)	148

Symmetry code: (i) .