Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680402392X/wn6282sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680402392X/wn6282Isup2.hkl |
CCDC reference: 231991
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.015 Å
- R factor = 0.057
- wR factor = 0.147
- Data-to-parameter ratio = 17.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.78 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.18 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 15 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. Cl4 .. 3.44 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.180 Tmax scaled 0.180 Tmin scaled 0.065
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 in WinGX (Farrugia, 1999); program(s) used to solve structure: SIR92 in WinGX; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 in WinGX; software used to prepare material for publication: SHELXL97.
C6H2BrCl2I | F(000) = 1280 |
Mr = 351.79 | Dx = 2.616 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.630 (6) Å | Cell parameters from 25 reflections |
b = 10.020 (4) Å | θ = 10–15° |
c = 16.30 (1) Å | µ = 8.58 mm−1 |
β = 109.84 (4)° | T = 293 K |
V = 1786.6 (15) Å3 | Block, colourless |
Z = 8 | 0.3 × 0.2 × 0.2 mm |
Enraf-Nonius CAD-4 diffractometer | 1730 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
ω/2θ scans | h = 0→13 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→11 |
Tmin = 0.361, Tmax = 1.000 | l = −19→18 |
3287 measured reflections | 2 standard reflections every 60 min |
3125 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.0856P)2] where P = (Fo2 + 2Fc2)/3 |
3125 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 1.16 e Å−3 |
0 restraints | Δρmin = −1.71 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8819 (9) | 0.4265 (11) | 0.0461 (6) | 0.041 (2) | |
C2 | 0.7979 (10) | 0.4264 (11) | −0.0398 (7) | 0.046 (3) | |
C3 | 0.7926 (9) | 0.3288 (12) | −0.1006 (6) | 0.045 (3) | |
H3 | 0.7352 | 0.3322 | −0.1565 | 0.054* | |
C4 | 0.8744 (10) | 0.2277 (11) | −0.0756 (6) | 0.044 (3) | |
C5 | 0.9634 (10) | 0.2177 (11) | 0.0108 (6) | 0.046 (3) | |
H5 | 1.0187 | 0.1474 | 0.0272 | 0.055* | |
C6 | 0.9614 (9) | 0.3206 (11) | 0.0689 (6) | 0.040 (2) | |
C7 | 0.6534 (10) | 0.1141 (11) | 0.0394 (6) | 0.044 (3) | |
C8 | 0.5940 (10) | 0.2355 (11) | 0.0348 (6) | 0.043 (3) | |
C9 | 0.5155 (9) | 0.2916 (11) | −0.0437 (6) | 0.046 (3) | |
H9 | 0.4771 | 0.3734 | −0.0451 | 0.055* | |
C10 | 0.4989 (9) | 0.2165 (12) | −0.1196 (6) | 0.046 (3) | |
C11 | 0.5557 (10) | 0.0959 (10) | −0.1175 (6) | 0.046 (3) | |
H11 | 0.5417 | 0.0476 | −0.1687 | 0.055* | |
C12 | 0.6336 (9) | 0.0462 (12) | −0.0393 (7) | 0.050 (3) | |
Cl1 | 0.6927 (3) | 0.5573 (3) | −0.0744 (2) | 0.0691 (9) | |
Cl2 | 1.0719 (3) | 0.3062 (4) | 0.17239 (17) | 0.0725 (10) | |
Cl3 | 0.6131 (3) | 0.3298 (4) | 0.12813 (17) | 0.0712 (10) | |
Cl4 | 0.7030 (3) | −0.1032 (3) | −0.0396 (2) | 0.0707 (9) | |
Br1 | 0.87679 (14) | 0.09778 (14) | −0.15729 (8) | 0.0699 (4) | |
Br2 | 0.39898 (13) | 0.28920 (16) | −0.22700 (7) | 0.0710 (4) | |
I1 | 0.88694 (9) | 0.57855 (9) | 0.13488 (5) | 0.0670 (3) | |
I2 | 0.77746 (8) | 0.04638 (10) | 0.15695 (5) | 0.0660 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.028 (5) | 0.046 (7) | 0.054 (5) | 0.004 (6) | 0.020 (4) | 0.004 (5) |
C2 | 0.041 (6) | 0.046 (7) | 0.058 (6) | −0.006 (6) | 0.026 (5) | 0.012 (5) |
C3 | 0.039 (6) | 0.055 (8) | 0.043 (5) | −0.002 (6) | 0.016 (4) | 0.000 (5) |
C4 | 0.041 (6) | 0.046 (7) | 0.054 (5) | −0.009 (6) | 0.028 (5) | −0.007 (5) |
C5 | 0.042 (6) | 0.042 (7) | 0.053 (5) | 0.006 (6) | 0.017 (5) | 0.006 (5) |
C6 | 0.036 (6) | 0.038 (7) | 0.047 (5) | −0.012 (6) | 0.015 (4) | 0.003 (5) |
C7 | 0.046 (6) | 0.043 (7) | 0.048 (5) | −0.020 (6) | 0.021 (4) | −0.004 (5) |
C8 | 0.039 (6) | 0.049 (7) | 0.045 (5) | 0.003 (6) | 0.020 (4) | −0.002 (5) |
C9 | 0.031 (6) | 0.045 (7) | 0.059 (6) | 0.003 (6) | 0.013 (4) | 0.001 (5) |
C10 | 0.029 (5) | 0.062 (8) | 0.043 (5) | −0.002 (6) | 0.008 (4) | 0.005 (5) |
C11 | 0.063 (7) | 0.026 (6) | 0.052 (5) | 0.000 (6) | 0.024 (5) | −0.002 (5) |
C12 | 0.033 (6) | 0.052 (8) | 0.070 (6) | −0.017 (6) | 0.026 (5) | −0.002 (6) |
Cl1 | 0.061 (2) | 0.054 (2) | 0.092 (2) | 0.0225 (19) | 0.0263 (16) | 0.0166 (16) |
Cl2 | 0.065 (2) | 0.083 (3) | 0.0545 (14) | −0.006 (2) | 0.0016 (13) | 0.0019 (15) |
Cl3 | 0.068 (2) | 0.088 (3) | 0.0533 (14) | 0.012 (2) | 0.0147 (14) | −0.0186 (16) |
Cl4 | 0.074 (2) | 0.049 (2) | 0.092 (2) | 0.012 (2) | 0.0319 (17) | 0.0021 (16) |
Br1 | 0.0833 (10) | 0.0660 (9) | 0.0656 (7) | 0.0118 (8) | 0.0322 (6) | −0.0118 (6) |
Br2 | 0.0664 (8) | 0.0870 (11) | 0.0512 (6) | 0.0069 (8) | 0.0088 (5) | 0.0082 (6) |
I1 | 0.0860 (7) | 0.0553 (5) | 0.0739 (5) | −0.0146 (5) | 0.0457 (4) | −0.0143 (4) |
I2 | 0.0525 (5) | 0.0813 (7) | 0.0586 (4) | 0.0069 (5) | 0.0116 (3) | 0.0170 (4) |
C1—C6 | 1.373 (14) | C7—C8 | 1.387 (15) |
C1—C2 | 1.408 (14) | C7—C12 | 1.401 (14) |
C1—I1 | 2.089 (10) | C7—I2 | 2.082 (10) |
C2—C3 | 1.379 (15) | C8—C9 | 1.412 (14) |
C2—Cl1 | 1.751 (11) | C8—Cl3 | 1.740 (10) |
C3—C4 | 1.354 (15) | C9—C10 | 1.404 (14) |
C3—H3 | 0.9300 | C9—H9 | 0.9300 |
C4—C5 | 1.440 (14) | C10—C11 | 1.371 (15) |
C4—Br1 | 1.869 (10) | C10—Br2 | 1.889 (9) |
C5—C6 | 1.406 (14) | C11—C12 | 1.382 (15) |
C5—H5 | 0.9300 | C11—H11 | 0.9300 |
C6—Cl2 | 1.745 (9) | C12—Cl4 | 1.702 (12) |
C6—C1—C2 | 116.4 (9) | C8—C7—C12 | 116.9 (9) |
C6—C1—I1 | 121.2 (7) | C8—C7—I2 | 120.8 (7) |
C2—C1—I1 | 122.4 (8) | C12—C7—I2 | 122.1 (9) |
C3—C2—C1 | 124.1 (11) | C7—C8—C9 | 123.7 (9) |
C3—C2—Cl1 | 116.4 (8) | C7—C8—Cl3 | 121.0 (7) |
C1—C2—Cl1 | 119.5 (9) | C9—C8—Cl3 | 115.3 (8) |
C4—C3—C2 | 117.3 (9) | C10—C9—C8 | 115.9 (10) |
C4—C3—H3 | 121.3 | C10—C9—H9 | 122.0 |
C2—C3—H3 | 121.3 | C8—C9—H9 | 122.0 |
C3—C4—C5 | 123.0 (9) | C11—C10—C9 | 122.0 (9) |
C3—C4—Br1 | 119.0 (8) | C11—C10—Br2 | 120.2 (8) |
C5—C4—Br1 | 118.0 (8) | C9—C10—Br2 | 117.8 (9) |
C6—C5—C4 | 115.9 (10) | C10—C11—C12 | 120.0 (10) |
C6—C5—H5 | 122.0 | C10—C11—H11 | 120.0 |
C4—C5—H5 | 122.0 | C12—C11—H11 | 120.0 |
C1—C6—C5 | 123.2 (9) | C11—C12—C7 | 121.5 (11) |
C1—C6—Cl2 | 122.2 (8) | C11—C12—Cl4 | 118.5 (9) |
C5—C6—Cl2 | 114.6 (8) | C7—C12—Cl4 | 120.0 (9) |
C6—C1—C2—C3 | −0.8 (15) | C12—C7—C8—C9 | 0.7 (15) |
I1—C1—C2—C3 | 179.2 (8) | I2—C7—C8—C9 | 175.4 (8) |
C6—C1—C2—Cl1 | 179.8 (7) | C12—C7—C8—Cl3 | −179.2 (8) |
I1—C1—C2—Cl1 | −0.3 (12) | I2—C7—C8—Cl3 | −4.4 (12) |
C1—C2—C3—C4 | −0.5 (16) | C7—C8—C9—C10 | 0.3 (16) |
Cl1—C2—C3—C4 | 179.0 (8) | Cl3—C8—C9—C10 | −179.8 (8) |
C2—C3—C4—C5 | 1.0 (15) | C8—C9—C10—C11 | 0.0 (16) |
C2—C3—C4—Br1 | −176.7 (7) | C8—C9—C10—Br2 | −178.0 (7) |
C3—C4—C5—C6 | −0.3 (15) | C9—C10—C11—C12 | −1.2 (16) |
Br1—C4—C5—C6 | 177.4 (7) | Br2—C10—C11—C12 | 176.7 (8) |
C2—C1—C6—C5 | 1.5 (14) | C10—C11—C12—C7 | 2.3 (16) |
I1—C1—C6—C5 | −178.4 (8) | C10—C11—C12—Cl4 | −179.6 (8) |
C2—C1—C6—Cl2 | 179.5 (7) | C8—C7—C12—C11 | −2.0 (15) |
I1—C1—C6—Cl2 | −0.4 (12) | I2—C7—C12—C11 | −176.6 (7) |
C4—C5—C6—C1 | −1.0 (15) | C8—C7—C12—Cl4 | 179.9 (8) |
C4—C5—C6—Cl2 | −179.2 (7) | I2—C7—C12—Cl4 | 5.2 (12) |