2,4-Diiodo-aniline.

The structure of the title compound, C(6)H(5)I(2)N, shows a weak inter-molecular amine-amine N-H⋯N hydrogen-bonding inter-action, giving a helical chain which extends along the a axis. An intra-molecular N-H⋯I hydrogen bond is also observed.

Related literature

For related structures, see: Garden et al. (2002 ▶). For the synthesis, see: Dains et al. (1935 ▶); Hodgson & Marsden (1937 ▶); O’Neil (2001 ▶). For graph-set analysis of hydrogen bonding, see: Etter et al. (1990 ▶).

Experimental

Crystal data

C6H5I2N

M = 344.91

Orthorhombic,

a = 4.3870 (1) Å

b = 10.9626 (3) Å

c = 16.9778 (4) Å

V = 816.51 (3) Å3

Z = 4

Mo Kα radiation

μ = 7.62 mm−1

T = 200 K

0.30 × 0.18 × 0.18 mm

Data collection

Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer

Absorption correction: multi-scan (; Sheldrick, 1996 ▶) T min = 0.146, T max = 0.250

6739 measured reflections

1873 independent reflections

1790 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.038

S = 1.05

1873 reflections

90 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.47 e Å−3

Absolute structure: Flack (1983 ▶), 737 Friedel pairs

Flack parameter: −0.03 (4)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) within WinGX (Farrugia, 1999 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809030438/is2440sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030438/is2440Isup2.hkl

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

C6H5I2N	Dx = 2.806 Mg m−3
Mr = 344.91	Melting point = 368–369 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5620 reflections
a = 4.3870 (1) Å	θ = 3.0–32.2°
b = 10.9626 (3) Å	µ = 7.62 mm−1
c = 16.9778 (4) Å	T = 200 K
V = 816.51 (3) Å3	Needle, colourless
Z = 4	0.30 × 0.18 × 0.18 mm
F(000) = 616

Oxford Diffraction Gemini-S Ultra CCD-detector diffractometer	1873 independent reflections
Radiation source: Enhance (Mo) X-ray tube	1790 reflections with I > 2σ(I)
graphite	Rint = 0.024
ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→5
Tmin = 0.146, Tmax = 0.250	k = −13→14
6739 measured reflections	l = −22→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.018	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.038	w = 1/[σ2(Fo2) + (0.0207P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.003
1873 reflections	Δρmax = 0.38 e Å−3
90 parameters	Δρmin = −0.47 e Å−3
0 restraints	Absolute structure: Flack (1983), 737 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.03 (4)

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
I2	0.57888 (5)	0.42657 (2)	1.08868 (1)	0.0293 (1)
I4	0.48489 (5)	0.28546 (2)	0.75021 (1)	0.0330 (1)
N1	0.1721 (9)	0.6552 (3)	1.0212 (2)	0.0291 (11)
C1	0.2299 (7)	0.5690 (3)	0.9630 (2)	0.0218 (9)
C2	0.4096 (8)	0.4658 (3)	0.97570 (19)	0.0221 (9)
C3	0.4807 (8)	0.3859 (3)	0.9156 (2)	0.0247 (9)
C4	0.3689 (8)	0.4074 (3)	0.8407 (2)	0.0235 (10)
C5	0.1876 (8)	0.5075 (3)	0.8256 (2)	0.0260 (11)
C6	0.1216 (9)	0.5877 (3)	0.8865 (2)	0.0278 (11)
H3	0.60280	0.31820	0.92530	0.0300*
H5	0.11070	0.52100	0.77530	0.0310*
H6	0.00190	0.65580	0.87610	0.0330*
H11	0.190 (8)	0.626 (3)	1.062 (2)	0.038 (9)*
H12	0.043 (8)	0.704 (4)	1.010 (2)	0.040 (9)*

	U11	U22	U33	U12	U13	U23
I2	0.0335 (1)	0.0341 (1)	0.0202 (1)	0.0009 (1)	−0.0038 (1)	0.0021 (1)
I4	0.0383 (1)	0.0389 (1)	0.0219 (1)	0.0022 (1)	0.0017 (1)	−0.0069 (1)
N1	0.037 (2)	0.0222 (16)	0.028 (2)	0.0055 (15)	−0.0021 (16)	0.0013 (15)
C1	0.0214 (15)	0.0191 (16)	0.0248 (18)	−0.0039 (15)	0.0014 (14)	0.0021 (14)
C2	0.0251 (16)	0.0226 (16)	0.0186 (17)	−0.0034 (15)	−0.0009 (14)	0.0032 (11)
C3	0.0289 (18)	0.0218 (14)	0.0234 (17)	−0.0007 (11)	−0.0010 (16)	0.0015 (12)
C4	0.0252 (17)	0.0226 (18)	0.0228 (18)	−0.0031 (13)	0.0028 (14)	−0.0029 (13)
C5	0.027 (2)	0.0313 (19)	0.0197 (19)	−0.0028 (14)	−0.0018 (15)	0.0044 (14)
C6	0.0323 (19)	0.0236 (18)	0.0276 (19)	0.0028 (15)	0.0007 (15)	0.0051 (13)

I2—C2	2.101 (3)	C2—C3	1.381 (5)
I4—C4	2.099 (3)	C3—C4	1.383 (5)
N1—C1	1.391 (5)	C4—C5	1.379 (5)
N1—H12	0.80 (4)	C5—C6	1.388 (5)
N1—H11	0.77 (3)	C3—H3	0.9300
C1—C6	1.398 (5)	C5—H5	0.9300
C1—C2	1.396 (5)	C6—H6	0.9300
H11—N1—H12	124 (4)	I4—C4—C3	118.6 (2)
C1—N1—H11	110 (3)	C3—C4—C5	120.7 (3)
C1—N1—H12	114 (3)	C4—C5—C6	119.1 (3)
N1—C1—C6	119.9 (3)	C1—C6—C5	121.9 (3)
N1—C1—C2	123.0 (3)	C2—C3—H3	120.00
C2—C1—C6	117.0 (3)	C4—C3—H3	120.00
I2—C2—C1	120.4 (2)	C4—C5—H5	120.00
I2—C2—C3	117.7 (2)	C6—C5—H5	121.00
C1—C2—C3	121.9 (3)	C1—C6—H6	119.00
C2—C3—C4	119.4 (3)	C5—C6—H6	119.00
I4—C4—C5	120.7 (2)
N1—C1—C2—I2	5.0 (5)	C1—C2—C3—C4	−0.7 (5)
N1—C1—C2—C3	−175.5 (3)	C2—C3—C4—I4	179.3 (3)
C6—C1—C2—I2	−178.9 (2)	C2—C3—C4—C5	0.0 (5)
C6—C1—C2—C3	0.6 (5)	I4—C4—C5—C6	−178.5 (3)
N1—C1—C6—C5	176.5 (3)	C3—C4—C5—C6	0.9 (5)
C2—C1—C6—C5	0.3 (5)	C4—C5—C6—C1	−1.0 (5)
I2—C2—C3—C4	178.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H11···I2	0.77 (3)	2.81 (3)	3.283 (4)	122 (3)
N1—H12···N1i	0.80 (4)	2.30 (4)	3.106 (5)	180 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H11⋯I2	0.77 (3)	2.81 (3)	3.283 (4)	122 (3)
N1—H12⋯N1i	0.80 (4)	2.30 (4)	3.106 (5)	180 (5)

Symmetry code: (i) .