Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038426/at2119sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038426/at2119Isup2.hkl |
CCDC reference: 623979
Key indicators
- Single-crystal X-ray study
- T = 190 K
- Mean () = 0.000 Å
- Disorder in main residue
- R factor = 0.034
- wR factor = 0.089
- Data-to-parameter ratio = 12.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT301_ALERT_3_B Main Residue Disorder ......................... 33.00 Perc. PLAT431_ALERT_2_B Short Inter HL..A Contact I1' .. Cl3' .. 3.31 Ang. PLAT431_ALERT_2_B Short Inter HL..A Contact I1' .. Cl6 .. 3.39 Ang.
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 27.45 From the CIF: _reflns_number_total 1946 Count of symmetry unique reflns 1022 Completeness (_total/calc) 190.41% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 924 Fraction of Friedel pairs measured 0.904 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: COLLECT (Nonius, 2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C6H2Cl3I | F(000) = 568 |
Mr = 307.33 | Dx = 2.391 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2c -2ac | Cell parameters from 3770 reflections |
a = 16.4873 (16) Å | θ = 1.0–27.5° |
b = 4.0530 (4) Å | µ = 4.61 mm−1 |
c = 12.7746 (13) Å | T = 190 K |
V = 853.64 (15) Å3 | Blade, colourless |
Z = 4 | 0.24 × 0.09 × 0.05 mm |
Nonius KappaCCD diffractometer | 1946 independent reflections |
Radiation source: fine-focus sealed tube | 1678 reflections with I > 2u(I) |
Graphite monochromator | Rint = 0.027 |
Detector resolution: 9 pixels mm-1 | θmax = 27.5°, θmin = 3.0° |
φ and ω scans | h = −21→21 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −5→5 |
Tmin = 0.404, Tmax = 0.802 | l = −16→16 |
20082 measured reflections |
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)] = 0.034 | H-atom parameters constrained |
wR(F2) = 0.089 | w = 1/[σ2(Fo2) + (0.0486P)2 + 0.953P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.008 |
1946 reflections | Δρmax = 0.74 e Å−3 |
155 parameters | Δρmin = −0.50 e Å−3 |
102 restraints | Absolute structure: Flack (1983), 924 Freidel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.30 (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 molecule was disordered over three orientations. The second orientation ('ed labels) is approximated by a twofold rotation about an axis passing through the midpoint of the C1—C2 and C4—C5 bonds of main orientation. The third orientation ("ed labels)is approximated by a twofold rotation about the C1—I1 bond direction. The relative occupancies refined to 0.625 (5):0.339 (3):0.036 (3) and were restrained to sum to 1.0. The molecular conformations were restrained to be the same. 'Partial' atom occupying the same general site (e.g, I1, Cl2', and I1") were constrained to have the same anisotropic thermal parameters except Cl3" (Uiso(Cl3")=1.2*Uiso-equiv(C3"). Additionally, the crystal was a racemic mix (0.70 (4):0.30 (4)) as determined by twin refinement. The three orientations were restrained to be flat. An anti-bumping restraint was imposed on Cl3" ···. Cl6"i (i=-0.5 + x, -y, z). 925 Friedel pairs were collected. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.6506 (8) | 0.145 (2) | 0.5776 (9) | 0.0384 (16) | 0.625 (5) |
I1 | 0.60838 (9) | −0.0672 (2) | 0.7202 (2) | 0.0550 (3) | 0.625 (5) |
C2 | 0.5952 (7) | 0.268 (2) | 0.5039 (10) | 0.0402 (17) | 0.625 (5) |
Cl2 | 0.4935 (7) | 0.2459 (15) | 0.5292 (9) | 0.0627 (8) | 0.625 (5) |
C3 | 0.6232 (7) | 0.415 (2) | 0.4143 (9) | 0.0367 (17) | 0.625 (5) |
Cl3 | 0.5587 (3) | 0.5682 (10) | 0.3206 (4) | 0.0490 (9) | 0.625 (5) |
C4 | 0.7074 (7) | 0.440 (2) | 0.3947 (8) | 0.0366 (18) | 0.625 (5) |
H4 | 0.7266 | 0.5433 | 0.3326 | 0.044* | 0.625 (5) |
C5 | 0.7601 (7) | 0.317 (2) | 0.4652 (9) | 0.0411 (18) | 0.625 (5) |
H5 | 0.8166 | 0.3286 | 0.4514 | 0.049* | 0.625 (5) |
C6 | 0.7333 (8) | 0.174 (2) | 0.5576 (9) | 0.0397 (17) | 0.625 (5) |
Cl6 | 0.8023 (4) | 0.0157 (14) | 0.6448 (6) | 0.0522 (7) | 0.625 (5) |
C1' | 0.6090 (8) | 0.253 (3) | 0.5145 (12) | 0.0402 (17) | 0.339 (3) |
I1' | 0.4810 (3) | 0.2064 (7) | 0.5342 (5) | 0.0627 (8) | 0.339 (3) |
C2' | 0.6628 (9) | 0.129 (3) | 0.5896 (11) | 0.0384 (16) | 0.339 (3) |
Cl2' | 0.6263 (7) | −0.043 (2) | 0.7022 (8) | 0.0550 (3) | 0.339 (3) |
C3' | 0.7449 (9) | 0.151 (3) | 0.5729 (11) | 0.0397 (17) | 0.339 (3) |
Cl3' | 0.8139 (7) | 0.000 (3) | 0.6614 (10) | 0.0522 (7) | 0.339 (3) |
C4' | 0.7759 (7) | 0.294 (3) | 0.4803 (11) | 0.0411 (18) | 0.339 (3) |
H4' | 0.8328 | 0.3052 | 0.4686 | 0.049* | 0.339 (3) |
C5' | 0.7237 (8) | 0.415 (3) | 0.4090 (11) | 0.0366 (18) | 0.339 (3) |
H5' | 0.7443 | 0.5142 | 0.3471 | 0.044* | 0.339 (3) |
C6' | 0.6407 (8) | 0.397 (3) | 0.4242 (11) | 0.0367 (17) | 0.339 (3) |
Cl6' | 0.5761 (7) | 0.563 (2) | 0.3329 (8) | 0.0490 (9) | 0.339 (3) |
C1" | 0.6365 (19) | 0.126 (4) | 0.5961 (17) | 0.0384 (16) | 0.036 (3) |
I1" | 0.599 (2) | −0.093 (4) | 0.7399 (15) | 0.0550 (3) | 0.036 (3) |
C2" | 0.7192 (19) | 0.156 (4) | 0.5716 (18) | 0.0397 (17) | 0.036 (3) |
Cl2" | 0.7904 (19) | 0.013 (4) | 0.657 (2) | 0.0522 (7) | 0.036 (3) |
C3" | 0.7420 (19) | 0.300 (4) | 0.4790 (18) | 0.0411 (18) | 0.036 (3) |
Cl3" | 0.8420 (19) | 0.345 (5) | 0.444 (2) | 0.049* | 0.036 (3) |
C4" | 0.683 (2) | 0.418 (4) | 0.4077 (17) | 0.0366 (18) | 0.036 (3) |
H4" | 0.6992 | 0.5177 | 0.3437 | 0.044* | 0.036 (3) |
C5" | 0.604 (2) | 0.388 (4) | 0.4319 (17) | 0.0367 (17) | 0.036 (3) |
H5" | 0.5643 | 0.4672 | 0.3843 | 0.044* | 0.036 (3) |
C6" | 0.5794 (19) | 0.244 (4) | 0.5250 (17) | 0.0402 (17) | 0.036 (3) |
Cl6" | 0.4779 (18) | 0.209 (4) | 0.5529 (18) | 0.0627 (8) | 0.036 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.059 (4) | 0.027 (2) | 0.030 (3) | −0.001 (3) | 0.003 (3) | 0.000 (2) |
I1 | 0.0729 (9) | 0.0407 (3) | 0.0515 (7) | −0.0027 (4) | 0.0191 (5) | 0.0052 (4) |
C2 | 0.040 (4) | 0.032 (3) | 0.048 (4) | −0.004 (2) | 0.002 (3) | −0.005 (2) |
Cl2 | 0.0535 (17) | 0.0607 (9) | 0.0739 (8) | −0.0079 (9) | 0.0101 (10) | −0.0087 (8) |
C3 | 0.041 (5) | 0.033 (3) | 0.036 (3) | 0.004 (3) | −0.008 (3) | −0.004 (2) |
Cl3 | 0.046 (3) | 0.0580 (9) | 0.0433 (14) | 0.0022 (11) | −0.0230 (12) | 0.0048 (8) |
C4 | 0.042 (5) | 0.045 (3) | 0.023 (3) | −0.005 (3) | −0.007 (3) | −0.003 (2) |
C5 | 0.036 (5) | 0.050 (3) | 0.037 (4) | −0.005 (3) | −0.009 (3) | −0.004 (3) |
C6 | 0.053 (4) | 0.033 (3) | 0.033 (4) | 0.005 (3) | −0.008 (3) | −0.008 (2) |
Cl6 | 0.057 (2) | 0.0649 (10) | 0.035 (2) | 0.0128 (10) | −0.0177 (11) | −0.0044 (11) |
C1' | 0.040 (4) | 0.032 (3) | 0.048 (4) | −0.004 (2) | 0.002 (3) | −0.005 (2) |
I1' | 0.0535 (17) | 0.0607 (9) | 0.0739 (8) | −0.0079 (9) | 0.0101 (10) | −0.0087 (8) |
C2' | 0.059 (4) | 0.027 (2) | 0.030 (3) | −0.001 (3) | 0.003 (3) | 0.000 (2) |
Cl2' | 0.0729 (9) | 0.0407 (3) | 0.0515 (7) | −0.0027 (4) | 0.0191 (5) | 0.0052 (4) |
C3' | 0.053 (4) | 0.033 (3) | 0.033 (4) | 0.005 (3) | −0.008 (3) | −0.008 (2) |
Cl3' | 0.057 (2) | 0.0649 (10) | 0.035 (2) | 0.0128 (10) | −0.0177 (11) | −0.0044 (11) |
C4' | 0.036 (5) | 0.050 (3) | 0.037 (4) | −0.005 (3) | −0.009 (3) | −0.004 (3) |
C5' | 0.042 (5) | 0.045 (3) | 0.023 (3) | −0.005 (3) | −0.007 (3) | −0.003 (2) |
C6' | 0.041 (5) | 0.033 (3) | 0.036 (3) | 0.004 (3) | −0.008 (3) | −0.004 (2) |
Cl6' | 0.046 (3) | 0.0580 (9) | 0.0433 (14) | 0.0022 (11) | −0.0230 (12) | 0.0048 (8) |
C1" | 0.059 (4) | 0.027 (2) | 0.030 (3) | −0.001 (3) | 0.003 (3) | 0.000 (2) |
I1" | 0.0729 (9) | 0.0407 (3) | 0.0515 (7) | −0.0027 (4) | 0.0191 (5) | 0.0052 (4) |
C2" | 0.053 (4) | 0.033 (3) | 0.033 (4) | 0.005 (3) | −0.008 (3) | −0.008 (2) |
Cl2" | 0.057 (2) | 0.0649 (10) | 0.035 (2) | 0.0128 (10) | −0.0177 (11) | −0.0044 (11) |
C3" | 0.036 (5) | 0.050 (3) | 0.037 (4) | −0.005 (3) | −0.009 (3) | −0.004 (3) |
C4" | 0.042 (5) | 0.045 (3) | 0.023 (3) | −0.005 (3) | −0.007 (3) | −0.003 (2) |
C5" | 0.041 (5) | 0.033 (3) | 0.036 (3) | 0.004 (3) | −0.008 (3) | −0.004 (2) |
C6" | 0.040 (4) | 0.032 (3) | 0.048 (4) | −0.004 (2) | 0.002 (3) | −0.005 (2) |
Cl6" | 0.0535 (17) | 0.0607 (9) | 0.0739 (8) | −0.0079 (9) | 0.0101 (10) | −0.0087 (8) |
C1—C6 | 1.392 (18) | C3'—Cl3' | 1.716 (11) |
C1—C2 | 1.405 (9) | C4'—C5' | 1.345 (10) |
C1—I1 | 2.131 (12) | C4'—H4' | 0.9500 |
C2—C3 | 1.370 (18) | C5'—C6' | 1.385 (17) |
C2—Cl2 | 1.710 (15) | C5'—H5' | 0.9500 |
C3—C4 | 1.414 (16) | C6'—Cl6' | 1.715 (11) |
C3—Cl3 | 1.718 (10) | C1"—C6" | 1.393 (19) |
C4—C5 | 1.346 (9) | C1"—C2" | 1.403 (9) |
C4—H4 | 0.9500 | C1"—I1" | 2.132 (13) |
C5—C6 | 1.387 (16) | C2"—C3" | 1.372 (18) |
C5—H5 | 0.9500 | C2"—Cl2" | 1.709 (16) |
C6—Cl6 | 1.719 (11) | C3"—C4" | 1.415 (16) |
C1'—C6' | 1.394 (19) | C3"—Cl3" | 1.718 (11) |
C1'—C2' | 1.401 (9) | C4"—C5" | 1.345 (10) |
C1'—I1' | 2.133 (13) | C4"—H4" | 0.9500 |
C2'—C3' | 1.373 (19) | C5"—C6" | 1.386 (16) |
C2'—Cl2' | 1.709 (15) | C5"—H5" | 0.9500 |
C3'—C4' | 1.414 (17) | C6"—Cl6" | 1.717 (11) |
C6—C1—C2 | 118.9 (13) | C5'—C4'—C3' | 119.0 (13) |
C6—C1—I1 | 120.8 (8) | C5'—C4'—H4' | 120.5 |
C2—C1—I1 | 120.3 (12) | C3'—C4'—H4' | 120.5 |
C3—C2—C1 | 119.7 (13) | C4'—C5'—C6' | 121.3 (13) |
C3—C2—Cl2 | 120.8 (10) | C4'—C5'—H5' | 119.4 |
C1—C2—Cl2 | 119.5 (13) | C6'—C5'—H5' | 119.4 |
C2—C3—C4 | 120.7 (9) | C5'—C6'—C1' | 120.5 (10) |
C2—C3—Cl3 | 122.0 (9) | C5'—C6'—Cl6' | 119.9 (10) |
C4—C3—Cl3 | 117.3 (9) | C1'—C6'—Cl6' | 119.6 (10) |
C5—C4—C3 | 119.2 (12) | C6"—C1"—C2" | 118.8 (13) |
C5—C4—H4 | 120.4 | C6"—C1"—I1" | 120.5 (9) |
C3—C4—H4 | 120.4 | C2"—C1"—I1" | 120.7 (13) |
C4—C5—C6 | 121.2 (12) | C3"—C2"—C1" | 119.7 (14) |
C4—C5—H5 | 119.4 | C3"—C2"—Cl2" | 120.6 (10) |
C6—C5—H5 | 119.4 | C1"—C2"—Cl2" | 119.7 (14) |
C5—C6—C1 | 120.3 (9) | C2"—C3"—C4" | 120.7 (10) |
C5—C6—Cl6 | 119.8 (9) | C2"—C3"—Cl3" | 122.1 (10) |
C1—C6—Cl6 | 119.8 (9) | C4"—C3"—Cl3" | 117.2 (10) |
C6'—C1'—C2' | 118.7 (13) | C5"—C4"—C3" | 119.1 (13) |
C6'—C1'—I1' | 120.3 (9) | C5"—C4"—H4" | 120.4 |
C2'—C1'—I1' | 120.9 (13) | C3"—C4"—H4" | 120.4 |
C3'—C2'—C1' | 119.7 (14) | C4"—C5"—C6" | 121.3 (13) |
C3'—C2'—Cl2' | 120.3 (10) | C4"—C5"—H5" | 119.4 |
C1'—C2'—Cl2' | 120.0 (14) | C6"—C5"—H5" | 119.4 |
C2'—C3'—C4' | 120.8 (10) | C5"—C6"—C1" | 120.4 (10) |
C2'—C3'—Cl3' | 121.9 (10) | C5"—C6"—Cl6" | 119.9 (10) |
C4'—C3'—Cl3' | 117.3 (10) | C1"—C6"—Cl6" | 119.7 (10) |
C6—C1—C2—C3 | −0.1 (12) | Cl3'—C3'—C4'—C5' | 179.9 (10) |
I1—C1—C2—C3 | 177.6 (6) | C3'—C4'—C5'—C6' | −0.8 (17) |
C6—C1—C2—Cl2 | −177.9 (6) | C4'—C5'—C6'—C1' | 0.2 (18) |
I1—C1—C2—Cl2 | −0.2 (9) | C4'—C5'—C6'—Cl6' | 178.4 (10) |
C1—C2—C3—C4 | 0.6 (12) | C2'—C1'—C6'—C5' | 0.3 (17) |
Cl2—C2—C3—C4 | 178.4 (6) | I1'—C1'—C6'—C5' | −177.1 (9) |
C1—C2—C3—Cl3 | 179.5 (6) | C2'—C1'—C6'—Cl6' | −178.0 (9) |
Cl2—C2—C3—Cl3 | −2.7 (10) | I1'—C1'—C6'—Cl6' | 4.6 (14) |
C2—C3—C4—C5 | 0.3 (12) | C6"—C1"—C2"—C3" | 0.0 (18) |
Cl3—C3—C4—C5 | −178.7 (6) | I1"—C1"—C2"—C3" | −179.5 (10) |
C3—C4—C5—C6 | −1.7 (12) | C6"—C1"—C2"—Cl2" | −179.9 (11) |
C4—C5—C6—C1 | 2.3 (12) | I1"—C1"—C2"—Cl2" | 0.5 (16) |
C4—C5—C6—Cl6 | 179.2 (7) | C1"—C2"—C3"—C4" | 0.1 (19) |
C2—C1—C6—C5 | −1.4 (12) | Cl2"—C2"—C3"—C4" | 180.0 (11) |
I1—C1—C6—C5 | −179.0 (6) | C1"—C2"—C3"—Cl3" | 179.8 (11) |
C2—C1—C6—Cl6 | −178.3 (6) | Cl2"—C2"—C3"—Cl3" | −0.3 (17) |
I1—C1—C6—Cl6 | 4.1 (9) | C2"—C3"—C4"—C5" | −0.1 (19) |
C6'—C1'—C2'—C3' | 0.0 (17) | Cl3"—C3"—C4"—C5" | −179.8 (11) |
I1'—C1'—C2'—C3' | 177.3 (9) | C3"—C4"—C5"—C6" | 0.0 (19) |
C6'—C1'—C2'—Cl2' | 179.0 (9) | C4"—C5"—C6"—C1" | 0.0 (19) |
I1'—C1'—C2'—Cl2' | −3.6 (14) | C4"—C5"—C6"—Cl6" | −179.8 (11) |
C1'—C2'—C3'—C4' | −0.6 (17) | C2"—C1"—C6"—C5" | 0.0 (18) |
Cl2'—C2'—C3'—C4' | −179.7 (9) | I1"—C1"—C6"—C5" | 179.5 (10) |
C1'—C2'—C3'—Cl3' | −179.4 (10) | C2"—C1"—C6"—Cl6" | 179.8 (11) |
Cl2'—C2'—C3'—Cl3' | 1.5 (15) | I1"—C1"—C6"—Cl6" | −0.7 (16) |
C2'—C3'—C4'—C5' | 1.1 (17) |