Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006823/sj6052sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006823/sj6052Isup2.hkl |
CCDC reference: 270523
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.007 Å
- R factor = 0.021
- wR factor = 0.055
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level A DIFF020_ALERT_1_A _diffrn_standards_interval_count and _diffrn_standards_interval_time are missing. Number of measurements between standards or time (min) between standards. DIFF022_ALERT_1_A _diffrn_standards_decay_% is missing Percentage decrease in standards intensity.
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT432_ALERT_2_C Short Inter X...Y Contact I2 .. C10 .. 3.43 Ang. PLAT432_ALERT_2_C Short Inter X...Y Contact I2 .. C4 .. 3.45 Ang. PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.04
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 1903 Count of symmetry unique reflns 969 Completeness (_total/calc) 196.39% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 934 Fraction of Friedel pairs measured 0.964 Are heavy atom types Z>Si present yes
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXTL.
C10H6I2 | F(000) = 688 |
Mr = 379.95 | Dx = 2.563 Mg m−3 |
Monoclinic, Cc | Melting point: 102 K |
Hall symbol: C -2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.487 (3) Å | Cell parameters from 3884 reflections |
b = 23.287 (9) Å | θ = 2.9–26.0° |
c = 5.675 (2) Å | µ = 6.33 mm−1 |
β = 95.579 (7)° | T = 100 K |
V = 984.7 (6) Å3 | Block, black |
Z = 4 | 0.25 × 0.11 × 0.06 mm |
Bruker APEX diffractometer | 1903 independent reflections |
Radiation source: fine-focus sealed tube | 1896 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
ω scans | θmax = 26.0°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −9→9 |
Tmin = 0.301, Tmax = 0.703 | k = −25→28 |
5207 measured reflections | l = −6→6 |
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)] = 0.021 | H-atom parameters constrained |
wR(F2) = 0.055 | w = 1/[σ2(Fo2) + (0.044P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
1903 reflections | Δρmax = 0.89 e Å−3 |
109 parameters | Δρmin = −0.57 e Å−3 |
2 restraints | Absolute structure: Flack (1983), with 935 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (4) |
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. The planar molecule sits obliquely in the unit cell. With the C centering and c-glide systematic absences, the fact that Z = 4, and the fact that the molecule sits obliquely in the unit cell, the best choice for the space group is Cc. |
x | y | z | Uiso*/Ueq | ||
I1 | 0.74063 (5) | 0.555141 (13) | 0.02278 (6) | 0.01970 (10) | |
I2 | 0.76879 (5) | 0.744021 (13) | 0.78887 (6) | 0.02440 (11) | |
C1 | 0.6640 (6) | 0.6083 (2) | 0.2890 (8) | 0.0184 (10) | |
C2 | 0.7655 (7) | 0.6534 (3) | 0.3929 (10) | 0.0221 (10) | |
H2 | 0.8789 | 0.6657 | 0.3499 | 0.026* | |
C3 | 0.6734 (7) | 0.6775 (2) | 0.5699 (9) | 0.0182 (9) | |
C4 | 0.3829 (7) | 0.6590 (2) | 0.7390 (9) | 0.0211 (10) | |
H4 | 0.4096 | 0.6901 | 0.8452 | 0.025* | |
C5 | 0.2200 (8) | 0.6310 (2) | 0.7632 (11) | 0.0248 (12) | |
H5 | 0.1540 | 0.6444 | 0.8871 | 0.030* | |
C6 | 0.1431 (7) | 0.5858 (2) | 0.6268 (10) | 0.0252 (11) | |
H6 | 0.0278 | 0.5742 | 0.6652 | 0.030* | |
C7 | 0.2083 (9) | 0.5556 (2) | 0.4457 (11) | 0.0204 (13) | |
H7 | 0.1344 | 0.5250 | 0.3833 | 0.025* | |
C8 | 0.3682 (7) | 0.5634 (2) | 0.3396 (9) | 0.0181 (10) | |
H8 | 0.3853 | 0.5384 | 0.2115 | 0.022* | |
C9 | 0.5041 (7) | 0.6026 (2) | 0.3964 (9) | 0.0175 (8) | |
C10 | 0.5113 (7) | 0.6483 (2) | 0.5835 (8) | 0.0171 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
I1 | 0.02039 (16) | 0.02110 (17) | 0.01883 (17) | 0.00258 (13) | 0.00811 (12) | 0.00052 (12) |
I2 | 0.0309 (2) | 0.02089 (17) | 0.02124 (18) | −0.00535 (15) | 0.00181 (14) | −0.00196 (15) |
C1 | 0.019 (2) | 0.019 (2) | 0.018 (2) | 0.0048 (19) | 0.0059 (18) | 0.0030 (18) |
C2 | 0.015 (2) | 0.027 (3) | 0.025 (3) | −0.0006 (19) | 0.004 (2) | 0.006 (2) |
C3 | 0.021 (2) | 0.016 (2) | 0.017 (2) | −0.0034 (19) | −0.0031 (18) | 0.0023 (18) |
C4 | 0.025 (3) | 0.019 (3) | 0.020 (2) | 0.003 (2) | 0.004 (2) | 0.0048 (19) |
C5 | 0.020 (3) | 0.026 (3) | 0.030 (3) | 0.006 (2) | 0.012 (2) | 0.008 (2) |
C6 | 0.020 (3) | 0.030 (3) | 0.027 (3) | 0.005 (2) | 0.009 (2) | 0.003 (2) |
C7 | 0.022 (3) | 0.015 (3) | 0.024 (3) | −0.0001 (19) | 0.001 (2) | −0.0006 (18) |
C8 | 0.020 (3) | 0.016 (2) | 0.018 (2) | 0.0012 (18) | 0.003 (2) | 0.0018 (18) |
C9 | 0.0158 (19) | 0.019 (2) | 0.018 (2) | 0.0048 (16) | 0.0015 (16) | 0.0017 (16) |
C10 | 0.023 (2) | 0.014 (2) | 0.014 (2) | 0.0035 (18) | −0.001 (2) | 0.0033 (16) |
I1—C1 | 2.076 (5) | C5—C6 | 1.397 (8) |
I2—C3 | 2.069 (5) | C5—H5 | 0.9500 |
C1—C2 | 1.395 (8) | C6—C7 | 1.374 (8) |
C1—C9 | 1.401 (7) | C6—H6 | 0.9500 |
C2—C3 | 1.390 (8) | C7—C8 | 1.403 (8) |
C2—H2 | 0.9500 | C7—H7 | 0.9500 |
C3—C10 | 1.400 (7) | C8—C9 | 1.381 (7) |
C4—C10 | 1.389 (7) | C8—H8 | 0.9500 |
C4—C5 | 1.401 (8) | C9—C10 | 1.501 (7) |
C4—H4 | 0.9500 | ||
C2—C1—C9 | 109.9 (4) | C7—C6—C5 | 130.0 (5) |
C2—C1—I1 | 125.4 (4) | C7—C6—H6 | 115.0 |
C9—C1—I1 | 124.6 (4) | C5—C6—H6 | 115.0 |
C3—C2—C1 | 108.8 (4) | C6—C7—C8 | 129.4 (5) |
C3—C2—H2 | 125.6 | C6—C7—H7 | 115.3 |
C1—C2—H2 | 125.6 | C8—C7—H7 | 115.3 |
C2—C3—C10 | 109.7 (4) | C9—C8—C7 | 128.7 (5) |
C2—C3—I2 | 124.7 (4) | C9—C8—H8 | 115.7 |
C10—C3—I2 | 125.5 (4) | C7—C8—H8 | 115.7 |
C10—C4—C5 | 129.9 (5) | C8—C9—C1 | 127.0 (5) |
C10—C4—H4 | 115.1 | C8—C9—C10 | 127.5 (5) |
C5—C4—H4 | 115.1 | C1—C9—C10 | 105.5 (5) |
C6—C5—C4 | 127.7 (6) | C4—C10—C3 | 127.2 (5) |
C6—C5—H5 | 116.1 | C4—C10—C9 | 126.7 (5) |
C4—C5—H5 | 116.1 | C3—C10—C9 | 106.1 (4) |
C9—C1—C2—C3 | 0.3 (6) | C2—C1—C9—C10 | −0.6 (6) |
I1—C1—C2—C3 | −177.7 (4) | I1—C1—C9—C10 | 177.5 (3) |
C1—C2—C3—C10 | 0.1 (6) | C5—C4—C10—C3 | −179.1 (5) |
C1—C2—C3—I2 | 177.5 (3) | C5—C4—C10—C9 | 0.5 (9) |
C10—C4—C5—C6 | −2.7 (10) | C2—C3—C10—C4 | 179.3 (5) |
C4—C5—C6—C7 | 3.6 (10) | I2—C3—C10—C4 | 1.9 (7) |
C5—C6—C7—C8 | −3.1 (10) | C2—C3—C10—C9 | −0.4 (6) |
C6—C7—C8—C9 | 2.4 (10) | I2—C3—C10—C9 | −177.8 (3) |
C7—C8—C9—C1 | 178.6 (5) | C8—C9—C10—C4 | 1.4 (8) |
C7—C8—C9—C10 | −2.1 (9) | C1—C9—C10—C4 | −179.1 (5) |
C2—C1—C9—C8 | 178.9 (5) | C8—C9—C10—C3 | −178.9 (5) |
I1—C1—C9—C8 | −3.0 (8) | C1—C9—C10—C3 | 0.6 (5) |