1,2,3-Triiodo­benzene

In the asymmetric unit of the title compound, C₆H₃I₃, there are two independent mol­ecules. The mol­ecules are stacked along the a axis. The mol­ecular geometry shows evidence of I...I intra­molecular steric repulsion.

Key indicators

• Single-crystal X-ray study
• T = 223 K
• Mean [sigma](C-C)= 0.007 Å
• R factor = 0.034
• wR factor = 0.086
• Data-to-parameter ratio = 30.7

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

1,2,3-Triiodobenzene

Crystal data

C6H3I3	Z = 4
Mr = 455.78	F(000) = 792
Triclinic, P1	Dx = 3.410 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2439 (5) Å	Cell parameters from 7891 reflections
b = 10.4665 (7) Å	θ = 2.6–30.0°
c = 11.7952 (8) Å	µ = 10.48 mm^−1
α = 90.45 (5)°	T = 223 K
β = 96.869 (5)°	Plate, colorless
γ = 90.84 (5)°	0.30 × 0.18 × 0.10 mm
V = 887.74 (10) Å^3

Data collection

Bruker SMART CCD area detector diffractometer	5119 independent reflections
Radiation source: fine-focus sealed tube	4554 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.120, Tmax = 0.349	k = −14→14
13551 measured reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H-atom parameters constrained
wR(F^2) = 0.086	w = 1/[σ^2(Fo^2) + (0.0467P)^2 + 0.5033P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
5119 reflections	Δρmax = 1.10 e Å^−3
167 parameters	Δρmin = −1.13 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00151 (17)

Special details

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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
I1	0.64920 (5)	0.72362 (3)	−0.08999 (3)	0.04346 (10)
I2	0.72769 (4)	0.98243 (3)	0.11419 (3)	0.03702 (9)
I3	1.17283 (5)	0.98908 (3)	0.29385 (3)	0.04151 (9)
C1	0.9060 (6)	0.7559 (4)	0.0098 (4)	0.0322 (8)
C2	0.9354 (6)	0.8502 (4)	0.0940 (3)	0.0285 (8)
C3	1.1068 (6)	0.8562 (4)	0.1617 (4)	0.0307 (8)
C4	1.2465 (6)	0.7698 (5)	0.1438 (4)	0.0375 (9)
H4	1.3623	0.7751	0.1891	0.045*
C5	1.2150 (7)	0.6777 (5)	0.0603 (5)	0.0410 (10)
H5	1.3085	0.6192	0.0495	0.049*
C6	1.0448 (7)	0.6704 (4)	−0.0083 (4)	0.0382 (10)
H6	1.0239	0.6081	−0.0664	0.046*
I4	0.76538 (5)	0.24251 (3)	0.34303 (3)	0.04907 (10)
I5	0.71569 (5)	0.56257 (3)	0.23095 (2)	0.04069 (9)
I6	0.69954 (6)	0.81772 (3)	0.43319 (3)	0.04732 (10)
C7	0.7574 (6)	0.4029 (4)	0.4486 (4)	0.0307 (8)
C8	0.7354 (6)	0.5270 (4)	0.4055 (3)	0.0299 (8)
C9	0.7304 (6)	0.6277 (4)	0.4839 (4)	0.0297 (8)
C10	0.7458 (6)	0.6058 (5)	0.6005 (4)	0.0347 (9)
H10	0.7397	0.6743	0.6519	0.042*
C11	0.7700 (6)	0.4837 (5)	0.6405 (4)	0.0364 (9)
H11	0.7831	0.4692	0.7196	0.044*
C12	0.7754 (6)	0.3814 (4)	0.5659 (4)	0.0347 (9)
H12	0.7911	0.2981	0.5941	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
I1	0.04006 (17)	0.0545 (2)	0.03477 (16)	−0.00491 (14)	0.00163 (12)	−0.01109 (13)
I2	0.03662 (16)	0.03594 (15)	0.03730 (16)	0.01214 (11)	−0.00175 (11)	−0.00320 (11)
I3	0.04194 (18)	0.03199 (15)	0.04728 (18)	0.00100 (12)	−0.00800 (13)	−0.00511 (12)
C1	0.035 (2)	0.034 (2)	0.0286 (19)	0.0018 (16)	0.0082 (16)	−0.0006 (16)
C2	0.0291 (19)	0.0266 (18)	0.0298 (19)	0.0030 (15)	0.0035 (15)	0.0009 (15)
C3	0.029 (2)	0.0265 (18)	0.036 (2)	0.0008 (15)	0.0021 (16)	0.0021 (15)
C4	0.030 (2)	0.039 (2)	0.043 (2)	0.0076 (17)	0.0027 (18)	0.0048 (19)
C5	0.038 (2)	0.037 (2)	0.050 (3)	0.0075 (19)	0.014 (2)	0.003 (2)
C6	0.046 (3)	0.032 (2)	0.039 (2)	0.0017 (18)	0.0147 (19)	−0.0040 (18)
I4	0.0513 (2)	0.03937 (18)	0.0535 (2)	0.00964 (14)	−0.00597 (15)	−0.01474 (15)
I5	0.04512 (18)	0.05194 (19)	0.02464 (13)	0.00657 (14)	0.00213 (11)	−0.00211 (12)
I6	0.0661 (2)	0.03354 (16)	0.04039 (17)	0.00140 (14)	−0.00176 (15)	0.00075 (12)
C7	0.0235 (18)	0.037 (2)	0.0305 (19)	0.0017 (15)	−0.0010 (14)	−0.0039 (16)
C8	0.0235 (18)	0.039 (2)	0.0259 (18)	0.0011 (15)	−0.0010 (14)	−0.0020 (15)
C9	0.0272 (19)	0.0304 (19)	0.0306 (19)	0.0012 (15)	−0.0004 (15)	−0.0002 (15)
C10	0.034 (2)	0.042 (2)	0.0287 (19)	0.0023 (18)	0.0052 (16)	−0.0041 (17)
C11	0.032 (2)	0.050 (3)	0.0268 (19)	0.0005 (18)	0.0026 (16)	0.0050 (18)
C12	0.032 (2)	0.036 (2)	0.036 (2)	0.0028 (17)	0.0021 (17)	0.0046 (17)

Geometric parameters (Å, º)

I1—C1	2.101 (5)	I4—C7	2.088 (4)
I2—C2	2.092 (4)	I5—C8	2.083 (4)
I3—C3	2.089 (4)	I6—C9	2.088 (4)
C1—C6	1.390 (6)	C7—C12	1.394 (6)
C1—C2	1.390 (6)	C7—C8	1.403 (6)
C2—C3	1.394 (6)	C8—C9	1.401 (6)
C3—C4	1.400 (6)	C9—C10	1.388 (6)
C4—C5	1.370 (7)	C10—C11	1.372 (7)
C4—H4	0.9400	C10—H10	0.9400
C5—C6	1.392 (7)	C11—C12	1.384 (7)
C5—H5	0.9400	C11—H11	0.9400
C6—H6	0.9400	C12—H12	0.9400
C6—C1—C2	121.1 (4)	C12—C7—C8	120.8 (4)
C6—C1—I1	115.4 (3)	C12—C7—I4	116.7 (3)
C2—C1—I1	123.4 (3)	C8—C7—I4	122.5 (3)
C1—C2—C3	118.5 (4)	C9—C8—C7	117.8 (4)
C1—C2—I2	120.1 (3)	C9—C8—I5	120.5 (3)
C3—C2—I2	121.3 (3)	C7—C8—I5	121.6 (3)
C2—C3—C4	120.4 (4)	C10—C9—C8	121.2 (4)
C2—C3—I3	123.6 (3)	C10—C9—I6	116.3 (3)
C4—C3—I3	116.0 (3)	C8—C9—I6	122.4 (3)
C5—C4—C3	120.2 (4)	C11—C10—C9	119.7 (4)
C5—C4—H4	119.9	C11—C10—H10	120.1
C3—C4—H4	119.9	C9—C10—H10	120.1
C4—C5—C6	120.2 (4)	C10—C11—C12	120.8 (4)
C4—C5—H5	119.8	C10—C11—H11	119.6
C6—C5—H5	120.0	C12—C11—H11	119.6
C1—C6—C5	119.5 (4)	C11—C12—C7	119.6 (4)
C1—C6—H6	120.2	C11—C12—H12	120.2
C5—C6—H6	120.2	C7—C12—H12	120.2