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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054535/is2125sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054535/is2125Isup2.hkl
Contains datablock I

CCDC reference: 636706

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

No syntax errors found


No errors found in this datablock

Computing details top

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 top
Crystal data top
C6H3I3Z = 4
Mr = 455.78F(000) = 792
Triclinic, P1Dx = 3.410 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2439 (5) ÅCell parameters from 7891 reflections
b = 10.4665 (7) Åθ = 2.6–30.0°
c = 11.7952 (8) ŵ = 10.48 mm1
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) Å3
Data collection top
Bruker SMART CCD area detector
diffractometer
5119 independent reflections
Radiation source: fine-focus sealed tube4554 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ω scansθmax = 30.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.120, Tmax = 0.349k = 1414
13551 measured reflectionsl = 1616
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0467P)2 + 0.5033P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
5119 reflectionsΔρmax = 1.10 e Å3
167 parametersΔρmin = 1.13 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00151 (17)
Special details top

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 (Å2) top
xyzUiso*/Ueq
I10.64920 (5)0.72362 (3)0.08999 (3)0.04346 (10)
I20.72769 (4)0.98243 (3)0.11419 (3)0.03702 (9)
I31.17283 (5)0.98908 (3)0.29385 (3)0.04151 (9)
C10.9060 (6)0.7559 (4)0.0098 (4)0.0322 (8)
C20.9354 (6)0.8502 (4)0.0940 (3)0.0285 (8)
C31.1068 (6)0.8562 (4)0.1617 (4)0.0307 (8)
C41.2465 (6)0.7698 (5)0.1438 (4)0.0375 (9)
H41.36230.77510.18910.045*
C51.2150 (7)0.6777 (5)0.0603 (5)0.0410 (10)
H51.30850.61920.04950.049*
C61.0448 (7)0.6704 (4)0.0083 (4)0.0382 (10)
H61.02390.60810.06640.046*
I40.76538 (5)0.24251 (3)0.34303 (3)0.04907 (10)
I50.71569 (5)0.56257 (3)0.23095 (2)0.04069 (9)
I60.69954 (6)0.81772 (3)0.43319 (3)0.04732 (10)
C70.7574 (6)0.4029 (4)0.4486 (4)0.0307 (8)
C80.7354 (6)0.5270 (4)0.4055 (3)0.0299 (8)
C90.7304 (6)0.6277 (4)0.4839 (4)0.0297 (8)
C100.7458 (6)0.6058 (5)0.6005 (4)0.0347 (9)
H100.73970.67430.65190.042*
C110.7700 (6)0.4837 (5)0.6405 (4)0.0364 (9)
H110.78310.46920.71960.044*
C120.7754 (6)0.3814 (4)0.5659 (4)0.0347 (9)
H120.79110.29810.59410.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.04006 (17)0.0545 (2)0.03477 (16)0.00491 (14)0.00163 (12)0.01109 (13)
I20.03662 (16)0.03594 (15)0.03730 (16)0.01214 (11)0.00175 (11)0.00320 (11)
I30.04194 (18)0.03199 (15)0.04728 (18)0.00100 (12)0.00800 (13)0.00511 (12)
C10.035 (2)0.034 (2)0.0286 (19)0.0018 (16)0.0082 (16)0.0006 (16)
C20.0291 (19)0.0266 (18)0.0298 (19)0.0030 (15)0.0035 (15)0.0009 (15)
C30.029 (2)0.0265 (18)0.036 (2)0.0008 (15)0.0021 (16)0.0021 (15)
C40.030 (2)0.039 (2)0.043 (2)0.0076 (17)0.0027 (18)0.0048 (19)
C50.038 (2)0.037 (2)0.050 (3)0.0075 (19)0.014 (2)0.003 (2)
C60.046 (3)0.032 (2)0.039 (2)0.0017 (18)0.0147 (19)0.0040 (18)
I40.0513 (2)0.03937 (18)0.0535 (2)0.00964 (14)0.00597 (15)0.01474 (15)
I50.04512 (18)0.05194 (19)0.02464 (13)0.00657 (14)0.00213 (11)0.00211 (12)
I60.0661 (2)0.03354 (16)0.04039 (17)0.00140 (14)0.00176 (15)0.00075 (12)
C70.0235 (18)0.037 (2)0.0305 (19)0.0017 (15)0.0010 (14)0.0039 (16)
C80.0235 (18)0.039 (2)0.0259 (18)0.0011 (15)0.0010 (14)0.0020 (15)
C90.0272 (19)0.0304 (19)0.0306 (19)0.0012 (15)0.0004 (15)0.0002 (15)
C100.034 (2)0.042 (2)0.0287 (19)0.0023 (18)0.0052 (16)0.0041 (17)
C110.032 (2)0.050 (3)0.0268 (19)0.0005 (18)0.0026 (16)0.0050 (18)
C120.032 (2)0.036 (2)0.036 (2)0.0028 (17)0.0021 (17)0.0046 (17)
Geometric parameters (Å, º) top
I1—C12.101 (5)I4—C72.088 (4)
I2—C22.092 (4)I5—C82.083 (4)
I3—C32.089 (4)I6—C92.088 (4)
C1—C61.390 (6)C7—C121.394 (6)
C1—C21.390 (6)C7—C81.403 (6)
C2—C31.394 (6)C8—C91.401 (6)
C3—C41.400 (6)C9—C101.388 (6)
C4—C51.370 (7)C10—C111.372 (7)
C4—H40.9400C10—H100.9400
C5—C61.392 (7)C11—C121.384 (7)
C5—H50.9400C11—H110.9400
C6—H60.9400C12—H120.9400
C6—C1—C2121.1 (4)C12—C7—C8120.8 (4)
C6—C1—I1115.4 (3)C12—C7—I4116.7 (3)
C2—C1—I1123.4 (3)C8—C7—I4122.5 (3)
C1—C2—C3118.5 (4)C9—C8—C7117.8 (4)
C1—C2—I2120.1 (3)C9—C8—I5120.5 (3)
C3—C2—I2121.3 (3)C7—C8—I5121.6 (3)
C2—C3—C4120.4 (4)C10—C9—C8121.2 (4)
C2—C3—I3123.6 (3)C10—C9—I6116.3 (3)
C4—C3—I3116.0 (3)C8—C9—I6122.4 (3)
C5—C4—C3120.2 (4)C11—C10—C9119.7 (4)
C5—C4—H4119.9C11—C10—H10120.1
C3—C4—H4119.9C9—C10—H10120.1
C4—C5—C6120.2 (4)C10—C11—C12120.8 (4)
C4—C5—H5119.8C10—C11—H11119.6
C6—C5—H5120.0C12—C11—H11119.6
C1—C6—C5119.5 (4)C11—C12—C7119.6 (4)
C1—C6—H6120.2C11—C12—H12120.2
C5—C6—H6120.2C7—C12—H12120.2
Average molecular geometries (Å, °) of some iodobenzenes top
MoleculeC—IC—C—CI···I
iodobenzene2.09 (1)121 (1)none
1,3,5-triiodobenzene2.095 (5)121.7 (6)none
1,2,3-triiodobenzene2.09 (1)118.0 (4)3.60 (2)
hexaiodobenzene2.09 (4)119.8 (8)3.51 (1)
C—C—C and I···I correspond to the endocyclic angles at carbons with vicinal iodines and non-bonding intermolecular distances, respectively.
 

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