2,4-Di-chloro-1-iodo-6-nitro-benzene.

In the crystal structure of the title compound, C6H2Cl2INO2, there are weak C-H⋯Cl inter-actions and I⋯O [3.387 (4) Å] close contacts. These inter-actions form sheets in the ac plane, with the closest contact between adjacent planes occurring between inversion-related nitro O atoms [3.025 (8) Å]. The molecule possesses mirror symmetry, with the halogen, N and C atoms all lying in the mirror plane. Hence, the dihedral angle between the benzene ring and the nitro group is 90°.

Related literature

For crystal structures of similar substituted nitro­benzenes, see: Li et al. (2012 ▶); Tahir et al. (2009 ▶). For information about polychlorinated bi­phenyls (PCBs) and their synthesis, see: Joshi et al. (2011 ▶); Lehmler et al. (2010 ▶); Lehmler & Robertson (2001 ▶). For the synthesis of the title compound, see: Sohn et al. (2003 ▶).

Experimental

Crystal data

C6H2Cl2INO2

M = 317.89

Orthorhombic,

a = 8.7760 (5) Å

b = 6.8989 (4) Å

c = 14.3518 (8) Å

V = 868.93 (9) Å3

Z = 4

Cu Kα radiation

μ = 34.30 mm−1

T = 90 K

0.13 × 0.10 × 0.04 mm

Data collection

Bruker X8 Proteum diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008b ▶) T min = 0.052, T max = 0.216

9625 measured reflections

862 independent reflections

827 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.12

862 reflections

71 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.68 e Å−3

Data collection: APEX2 (Bruker, 2006) ▶; cell refinement: SAINT (Bruker, 2006) ▶; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008a ▶); molecular graphics: XP in (Sheldrick, 2008a ▶); software used to prepare material for publication: SHELXTL and CIFFIX (Parkin, 2013 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814008733/lh5698sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008733/lh5698Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814008733/lh5698Isup3.cml

CCDC reference: 997807

Additional supporting information: crystallographic information; 3D view; checkCIF report

C6H2Cl2INO2	Dx = 2.430 Mg m−3
Mr = 317.89	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pnma	Cell parameters from 6956 reflections
a = 8.7760 (5) Å	θ = 5.9–67.7°
b = 6.8989 (4) Å	µ = 34.30 mm−1
c = 14.3518 (8) Å	T = 90 K
V = 868.93 (9) Å3	Rounded block, pale yellow
Z = 4	0.13 × 0.10 × 0.04 mm
F(000) = 592

Bruker X8 Proteum diffractometer	862 independent reflections
Radiation source: fine-focus rotating anode	827 reflections with I > 2σ(I)
Detector resolution: 5.6 pixels mm-1	Rint = 0.082
φ and ω scans	θmax = 68.0°, θmin = 5.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008b)	h = −10→7
Tmin = 0.052, Tmax = 0.216	k = −8→8
9625 measured reflections	l = −13→17

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0668P)2 + 0.2013P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max = 0.001
862 reflections	Δρmax = 0.67 e Å−3
71 parameters	Δρmin = −0.68 e Å−3
0 restraints	Extinction correction: SHELXL2013 (Sheldrick, 2008a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0021 (4)

Experimental. Diffraction data were collected with the crystal at 90 K, which is standard practice in this laboratory for the majority of flash-cooled crystals.A correction for radiation damage was included in the SADABS (Sheldrick, 2008b) run. This seems to have resulted in all the atomic displacement parameter ellipsoids looking more spherical than usual.

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.

	x	y	z	Uiso*/Ueq
I1	0.10397 (4)	0.2500	0.70325 (2)	0.0776 (3)
Cl1	−0.18714 (15)	0.2500	0.54761 (10)	0.0783 (4)
Cl2	0.16156 (18)	0.2500	0.24439 (10)	0.0807 (4)
N1	0.4037 (5)	0.2500	0.5700 (4)	0.0797 (14)
O1	0.4576 (4)	0.4066 (6)	0.5918 (2)	0.0946 (9)
C1	0.1230 (7)	0.2500	0.5590 (5)	0.0739 (13)
C2	−0.0053 (7)	0.2500	0.5003 (5)	0.0753 (13)
C3	0.0065 (7)	0.2500	0.4060 (4)	0.0754 (13)
H3	−0.0828	0.2500	0.3686	0.090*
C4	0.1510 (8)	0.2500	0.3637 (5)	0.0740 (13)
C5	0.2811 (7)	0.2500	0.4179 (5)	0.0765 (13)
H5	0.3796	0.2500	0.3904	0.092*
C6	0.2624 (7)	0.2500	0.5133 (4)	0.0757 (13)

	U11	U22	U33	U12	U13	U23
I1	0.0812 (4)	0.0798 (4)	0.0718 (4)	0.000	0.00182 (13)	0.000
Cl1	0.0753 (8)	0.0786 (8)	0.0810 (8)	0.000	0.0026 (6)	0.000
Cl2	0.0828 (9)	0.0878 (9)	0.0715 (8)	0.000	0.0000 (6)	0.000
N1	0.079 (3)	0.091 (4)	0.070 (3)	0.000	0.003 (2)	0.000
O1	0.0929 (19)	0.097 (2)	0.0936 (18)	−0.0143 (17)	−0.0113 (16)	−0.0056 (17)
C1	0.081 (3)	0.071 (3)	0.069 (3)	0.000	−0.001 (2)	0.000
C2	0.074 (3)	0.067 (3)	0.084 (3)	0.000	0.002 (3)	0.000
C3	0.084 (3)	0.065 (3)	0.077 (3)	0.000	−0.004 (3)	0.000
C4	0.079 (3)	0.069 (3)	0.074 (3)	0.000	−0.004 (3)	0.000
C5	0.076 (3)	0.073 (3)	0.081 (3)	0.000	0.005 (3)	0.000
C6	0.076 (3)	0.073 (3)	0.078 (3)	0.000	−0.003 (3)	0.000

I1—C1	2.077 (7)	C1—C2	1.406 (9)
Cl1—C2	1.734 (7)	C2—C3	1.358 (9)
Cl2—C4	1.715 (7)	C3—C4	1.406 (10)
N1—O1	1.220 (4)	C3—H3	0.9500
N1—O1i	1.220 (4)	C4—C5	1.381 (9)
N1—C6	1.484 (8)	C5—C6	1.379 (9)
C1—C6	1.388 (9)	C5—H5	0.9500
O1—N1—O1i	124.6 (6)	C4—C3—H3	120.0
O1—N1—C6	117.7 (3)	C5—C4—C3	120.2 (6)
O1i—N1—C6	117.7 (3)	C5—C4—Cl2	121.1 (5)
C6—C1—C2	114.9 (6)	C3—C4—Cl2	118.7 (5)
C6—C1—I1	122.9 (5)	C6—C5—C4	117.4 (6)
C2—C1—I1	122.2 (5)	C6—C5—H5	121.3
C3—C2—C1	122.4 (6)	C4—C5—H5	121.3
C3—C2—Cl1	117.4 (5)	C5—C6—C1	125.1 (6)
C1—C2—Cl1	120.2 (5)	C5—C6—N1	116.5 (5)
C2—C3—C4	119.9 (6)	C1—C6—N1	118.4 (5)
C2—C3—H3	120.0
C6—C1—C2—C3	0.000 (2)	C4—C5—C6—C1	0.000 (2)
I1—C1—C2—C3	180.000 (1)	C4—C5—C6—N1	180.000 (1)
C6—C1—C2—Cl1	180.000 (1)	C2—C1—C6—C5	0.000 (2)
I1—C1—C2—Cl1	0.000 (1)	I1—C1—C6—C5	180.000 (1)
C1—C2—C3—C4	0.000 (2)	C2—C1—C6—N1	180.000 (1)
Cl1—C2—C3—C4	180.000 (1)	I1—C1—C6—N1	0.000 (2)
C2—C3—C4—C5	0.000 (2)	O1—N1—C6—C5	90.0 (5)
C2—C3—C4—Cl2	180.000 (1)	O1i—N1—C6—C5	−90.0 (5)
C3—C4—C5—C6	0.000 (1)	O1—N1—C6—C1	−90.0 (5)
Cl2—C4—C5—C6	180.000 (1)	O1i—N1—C6—C1	90.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cl2ii	0.95	2.77	3.718 (7)	179

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cl2i	0.95	2.77	3.718 (7)	179

Symmetry code: (i) .