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The title compound, C6H2I4, has crystallographically exact Ci and approximate D2h molecular symmetry. Two half-mol­ecules comprise the asymmetric unit. The mol­ecules are stacked along the c axis and neigbouring stacks are connected via weak I...I inter­molecular inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806048823/kp2054sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806048823/kp2054Isup2.hkl
Contains datablock I

CCDC reference: 630039

Key indicators

  • Single-crystal X-ray study
  • T = 223 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.045
  • wR factor = 0.110
  • Data-to-parameter ratio = 32.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.20 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

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

1,2,4,5-tetraiodobenzene top
Crystal data top
C6H2I4F(000) = 1000
Mr = 581.68Dx = 3.739 Mg m3
Monoclinic, P2/cMo Kα radiation, λ = 0.71073 Å
a = 17.8144 (8) ÅCell parameters from 8192 reflections
b = 7.4999 (8) Åθ = 2.1–25.0°
c = 7.9125 (8) ŵ = 12.00 mm1
β = 102.203 (2)°T = 223 K
V = 1033.27 (15) Å3Plate, cut, colourless
Z = 40.40 × 0.10 × 0.08 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
3006 independent reflections
Radiation source: fine-focus sealed tube2485 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
φ and ω scansθmax = 30.0°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1825
Tmin = 0.129, Tmax = 0.381k = 810
8332 measured reflectionsl = 1111
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)] = 0.045H-atom parameters constrained
wR(F2) = 0.110 w = 1/[σ2(Fo2) + (0.0526P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
3006 reflectionsΔρmax = 1.47 e Å3
92 parametersΔρmin = 1.84 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0040 (3)
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
I10.12124 (3)0.15513 (7)0.68451 (7)0.03190 (10)
I20.18047 (3)0.62698 (7)0.73215 (7)0.03116 (10)
I40.38087 (3)0.65031 (6)0.56686 (7)0.03375 (10)
I60.67999 (3)0.88392 (7)0.42765 (6)0.02877 (10)
C10.0505 (4)0.3659 (5)0.5740 (5)0.0230 (8)
C20.0724 (4)0.5458 (5)0.5946 (5)0.0222 (8)
C30.0216 (4)0.6777 (5)0.5214 (5)0.0235 (8)
H30.03610.79810.53650.028*
C40.4505 (4)0.8634 (5)0.5255 (5)0.0223 (8)
C50.5232 (4)0.8238 (5)0.4957 (5)0.0237 (8)
H50.53900.70440.49270.028*
C60.5719 (4)0.9594 (5)0.4707 (5)0.0218 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0279 (3)0.0260 (3)0.0419 (3)0.00650 (9)0.0077 (2)0.00415 (18)
I20.0202 (3)0.0346 (3)0.0365 (3)0.00720 (9)0.00099 (9)0.00335 (18)
I40.0320 (3)0.0242 (3)0.0484 (3)0.0067 (2)0.0160 (2)0.00051 (19)
I60.0200 (3)0.0334 (3)0.0345 (3)0.00754 (9)0.00949 (8)0.00348 (18)
C10.022 (3)0.018 (3)0.031 (3)0.002 (3)0.011 (3)0.002 (2)
C20.018 (3)0.029 (3)0.020 (3)0.007 (3)0.004 (2)0.003 (2)
C30.020 (3)0.020 (3)0.034 (4)0.001 (3)0.012 (3)0.003 (3)
C40.016 (3)0.024 (3)0.028 (3)0.002 (3)0.008 (3)0.002 (2)
C50.025 (4)0.018 (3)0.028 (3)0.003 (3)0.003 (3)0.002 (2)
C60.019 (3)0.024 (3)0.023 (3)0.005 (3)0.007 (2)0.001 (2)
Geometric parameters (Å, º) top
I1—C12.094 (7)C3—C1i1.384 (7)
I2—C22.092 (6)C3—H30.9400
I4—C42.091 (7)C4—C6ii1.390 (7)
I6—C62.102 (7)C4—C51.397 (7)
C1—C3i1.384 (7)C5—C61.378 (7)
C1—C21.404 (7)C5—H50.9400
C2—C31.383 (7)C6—C4ii1.390 (7)
C3i—C1—C2119.6 (6)C6ii—C4—C5119.2 (6)
C3i—C1—I1117.1 (5)C6ii—C4—I4123.0 (5)
C2—C1—I1123.3 (5)C5—C4—I4117.8 (5)
C3—C2—C1119.8 (6)C6—C5—C4120.1 (6)
C3—C2—I2117.3 (5)C6—C5—H5119.9
C1—C2—I2122.9 (5)C4—C5—H5120.0
C2—C3—C1i120.6 (6)C5—C6—C4ii120.7 (6)
C2—C3—H3119.7C5—C6—I6116.8 (5)
C1i—C3—H3119.7C4ii—C6—I6122.5 (5)
Symmetry codes: (i) x, y+1, z+1; (ii) x+1, y+2, z+1.
 

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