4-Chloro-1-iodo-2-nitro-benzene.

In the mol-ecule of the title compound, C(6)H(3)ClINO(2), the nitro group is disordered over two sites with occupancies of 0.506 (6) and 0.494 (6). The dihedral angles between the benzene ring and the two disordered components of the nitro group are 29.0 (2) and 51.0 (3)°. The disordering avoids short O⋯O inter-molecular contacts in the crystal.

Related literature

For background, see: Arshad et al. (2008 ▶, 2009 ▶). For related structures, see: Meriles et al. (1999 ▶).

Experimental

Crystal data

C6H3ClINO2

M = 283.44

Monoclinic,

a = 4.1583 (2) Å

b = 14.5213 (7) Å

c = 13.7990 (6) Å

β = 93.361 (2)°

V = 831.81 (7) Å3

Z = 4

Mo Kα radiation

μ = 4.12 mm−1

T = 296 K

0.26 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.554, T max = 0.664

9922 measured reflections

2157 independent reflections

1684 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.023

wR(F 2) = 0.051

S = 1.02

2157 reflections

128 parameters

Only H-atom coordinates refined

Δρmax = 0.66 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004930/hb2905sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004930/hb2905Isup2.hkl

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

C6H3ClINO2	F(000) = 528
Mr = 283.44	Dx = 2.263 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2157 reflections
a = 4.1583 (2) Å	θ = 2.8–28.7°
b = 14.5213 (7) Å	µ = 4.12 mm−1
c = 13.7990 (6) Å	T = 296 K
β = 93.361 (2)°	Needle, yellow
V = 831.81 (7) Å3	0.26 × 0.12 × 0.10 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	2157 independent reflections
Radiation source: fine-focus sealed tube	1684 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 7.40 pixels mm-1	θmax = 28.7°, θmin = 2.8°
ω scans	h = −5→3
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −18→19
Tmin = 0.554, Tmax = 0.664	l = −18→18
9922 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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051	Only H-atom coordinates refined
S = 1.01	w = 1/[σ2(Fo2) + (0.0177P)2 + 0.626P] where P = (Fo2 + 2Fc2)/3
2157 reflections	(Δ/σ)max = 0.002
128 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
I1	−0.08606 (5)	0.03022 (1)	0.36564 (1)	0.0520 (1)
Cl1	0.5423 (2)	0.29672 (6)	0.03919 (7)	0.0739 (3)
O1A	0.1842 (14)	−0.0814 (3)	0.2012 (4)	0.0693 (19)	0.506 (6)
O2A	0.1343 (15)	−0.0393 (3)	0.0522 (4)	0.077 (2)	0.506 (6)
N1	0.1689 (7)	−0.02093 (18)	0.14257 (19)	0.0521 (9)
C1	0.2016 (6)	0.07685 (18)	0.16917 (19)	0.0395 (8)
C2	0.1064 (6)	0.10984 (18)	0.25738 (18)	0.0394 (8)
C3	0.1504 (8)	0.2032 (2)	0.2764 (2)	0.0525 (10)
C4	0.2833 (8)	0.2599 (2)	0.2098 (3)	0.0554 (11)
C5	0.3754 (7)	0.2250 (2)	0.1233 (2)	0.0487 (9)
C6	0.3366 (7)	0.1329 (2)	0.1020 (2)	0.0460 (9)
O1B	−0.0923 (15)	−0.0561 (3)	0.1528 (4)	0.0721 (19)	0.494 (6)
O2B	0.4074 (16)	−0.0577 (3)	0.1171 (4)	0.082 (3)	0.494 (6)
H6	0.392 (7)	0.109 (2)	0.045 (2)	0.0552*
H3	0.086 (8)	0.228 (2)	0.336 (2)	0.0630*
H4	0.325 (8)	0.321 (2)	0.223 (2)	0.0666*

	U11	U22	U33	U12	U13	U23
I1	0.0531 (1)	0.0648 (1)	0.0392 (1)	0.0006 (1)	0.0124 (1)	0.0053 (1)
Cl1	0.0847 (6)	0.0649 (5)	0.0724 (6)	−0.0142 (5)	0.0073 (5)	0.0265 (4)
O1A	0.098 (4)	0.038 (3)	0.074 (3)	0.000 (2)	0.024 (3)	0.007 (2)
O2A	0.109 (5)	0.074 (3)	0.050 (3)	−0.023 (3)	0.013 (3)	−0.024 (2)
N1	0.0660 (16)	0.0438 (15)	0.0478 (15)	−0.0018 (12)	0.0137 (13)	−0.0032 (12)
C1	0.0427 (13)	0.0359 (14)	0.0398 (14)	0.0018 (11)	0.0015 (11)	−0.0004 (11)
C2	0.0406 (13)	0.0450 (15)	0.0325 (13)	0.0061 (11)	0.0010 (10)	0.0014 (11)
C3	0.0650 (18)	0.0492 (18)	0.0432 (16)	0.0097 (14)	0.0029 (14)	−0.0066 (14)
C4	0.070 (2)	0.0375 (16)	0.058 (2)	0.0011 (14)	−0.0022 (16)	−0.0001 (15)
C5	0.0504 (15)	0.0462 (17)	0.0490 (17)	−0.0004 (12)	−0.0010 (13)	0.0131 (14)
C6	0.0508 (15)	0.0496 (17)	0.0382 (15)	0.0019 (12)	0.0072 (12)	0.0004 (13)
O1B	0.096 (4)	0.057 (3)	0.066 (3)	−0.027 (3)	0.027 (3)	−0.012 (2)
O2B	0.100 (5)	0.055 (3)	0.095 (5)	0.019 (3)	0.037 (4)	−0.017 (3)

I1—C2	2.086 (3)	C1—C2	1.387 (4)
Cl1—C5	1.734 (3)	C2—C3	1.391 (4)
O1A—N1	1.193 (6)	C3—C4	1.374 (5)
O1B—N1	1.216 (7)	C4—C5	1.372 (5)
O2A—N1	1.275 (6)	C5—C6	1.377 (4)
O2B—N1	1.197 (7)	C3—H3	0.95 (3)
N1—C1	1.471 (4)	C4—H4	0.92 (3)
C1—C6	1.378 (4)	C6—H6	0.90 (3)
O2B···O1Bi	2.110 (9)
O1A—N1—O2A	120.5 (4)	C2—C3—C4	120.8 (3)
O1A—N1—C1	122.7 (3)	C3—C4—C5	120.3 (3)
O2A—N1—C1	116.7 (3)	Cl1—C5—C4	120.2 (2)
O1B—N1—C1	116.5 (3)	Cl1—C5—C6	119.1 (2)
O2B—N1—C1	116.0 (3)	C4—C5—C6	120.6 (3)
O1B—N1—O2B	127.4 (4)	C1—C6—C5	118.5 (3)
N1—C1—C2	121.7 (2)	C2—C3—H3	119.5 (18)
N1—C1—C6	116.0 (2)	C4—C3—H3	119.8 (18)
C2—C1—C6	122.3 (2)	C3—C4—H4	121.6 (18)
I1—C2—C1	125.33 (19)	C5—C4—H4	118.0 (18)
I1—C2—C3	117.19 (19)	C1—C6—H6	119.6 (19)
C1—C2—C3	117.5 (2)	C5—C6—H6	121.8 (19)
O1A—N1—C1—C2	−30.2 (5)	C2—C1—C6—C5	−0.5 (4)
O1A—N1—C1—C6	148.8 (4)	I1—C2—C3—C4	178.4 (2)
O2A—N1—C1—C2	152.2 (4)	C1—C2—C3—C4	0.0 (4)
O2A—N1—C1—C6	−28.8 (5)	C2—C3—C4—C5	−0.1 (5)
N1—C1—C2—I1	1.0 (4)	C3—C4—C5—Cl1	179.9 (3)
N1—C1—C2—C3	179.3 (3)	C3—C4—C5—C6	−0.1 (5)
C6—C1—C2—I1	−177.9 (2)	Cl1—C5—C6—C1	−179.5 (2)
C6—C1—C2—C3	0.3 (4)	C4—C5—C6—C1	0.4 (4)
N1—C1—C6—C5	−179.5 (3)