Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052676/sa2026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052676/sa2026Isup2.hkl |
CCDC reference: 633987
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.025
- wR factor = 0.045
- Data-to-parameter ratio = 36.8
checkCIF/PLATON results
No syntax errors found
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 34.90 From the CIF: _reflns_number_total 5705 Count of symmetry unique reflns 3615 Completeness (_total/calc) 157.81% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2090 Fraction of Friedel pairs measured 0.578 Are heavy atom types Z>Si present yes PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 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 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: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C9H4Cl8 | Dx = 1.895 Mg m−3 |
Mr = 395.72 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P41212 | Cell parameters from 5705 reflections |
Hall symbol: P 4abw 2nw | θ = 2.8–34.9° |
a = 8.518 (1) Å | µ = 1.60 mm−1 |
c = 38.236 (5) Å | T = 100 K |
V = 2774.3 (6) Å3 | Fragment, light brown |
Z = 8 | 0.25 × 0.25 × 0.20 mm |
F(000) = 1552 |
Nonius KappaCCD area-detector (with Oxford Cryosystems Cryostream cooler) diffractometer | 5705 independent reflections |
Radiation source: fine-focus sealed tube | 4162 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω scans with κ offsets | θmax = 34.9°, θmin = 2.8° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −13→13 |
Tmin = 0.670, Tmax = 0.726 | k = −13→13 |
17778 measured reflections | l = −60→61 |
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.045 | w = 1/[σ2(Fo2) + (0.0061P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
5705 reflections | Δρmax = 0.36 e Å−3 |
155 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Absolute structure: Flack (1983), with 2143 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.08 (5) |
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 | ||
Cl1 | 0.55671 (4) | 0.72690 (4) | 0.441321 (11) | 0.02205 (9) | |
Cl2 | 0.20529 (4) | 0.88527 (4) | 0.443585 (11) | 0.02423 (9) | |
Cl3 | 0.24361 (4) | 1.28645 (4) | 0.456728 (10) | 0.02419 (9) | |
Cl4 | 0.62439 (4) | 1.35899 (4) | 0.469742 (11) | 0.02337 (9) | |
Cl5 | 0.83466 (4) | 1.01300 (4) | 0.462257 (11) | 0.02133 (8) | |
Cl6 | 0.57495 (4) | 0.99423 (4) | 0.509250 (10) | 0.01972 (7) | |
Cl7 | 0.50885 (4) | 1.42200 (4) | 0.378523 (11) | 0.02482 (9) | |
Cl8 | 0.43778 (4) | 0.86978 (4) | 0.351024 (11) | 0.02208 (8) | |
C1 | 0.61347 (15) | 1.16112 (16) | 0.41082 (4) | 0.0155 (3) | |
C2 | 0.59621 (14) | 1.00798 (16) | 0.40402 (4) | 0.0146 (3) | |
C3 | 0.53563 (15) | 0.93119 (15) | 0.43791 (4) | 0.0155 (3) | |
C4 | 0.37025 (15) | 0.99624 (16) | 0.44508 (4) | 0.0159 (3) | |
C5 | 0.38655 (15) | 1.14844 (16) | 0.45090 (4) | 0.0160 (3) | |
C6 | 0.56269 (16) | 1.18572 (15) | 0.44913 (4) | 0.0155 (3) | |
C7 | 0.62791 (15) | 1.03078 (15) | 0.46532 (4) | 0.0146 (3) | |
C8 | 0.66817 (15) | 1.28972 (15) | 0.38796 (4) | 0.0186 (3) | |
H8A | 0.7096 | 1.2456 | 0.3659 | 0.022* | |
H8B | 0.7541 | 1.3477 | 0.3997 | 0.022* | |
C9 | 0.62377 (15) | 0.92120 (16) | 0.37107 (4) | 0.0181 (3) | |
H9A | 0.6846 | 0.8246 | 0.3760 | 0.022* | |
H9B | 0.6857 | 0.9871 | 0.3548 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.02804 (18) | 0.01220 (15) | 0.0259 (2) | 0.00162 (13) | 0.00206 (17) | 0.00103 (16) |
Cl2 | 0.01651 (16) | 0.02924 (19) | 0.0270 (2) | −0.00516 (14) | 0.00107 (16) | −0.00010 (18) |
Cl3 | 0.02731 (18) | 0.02834 (19) | 0.0169 (2) | 0.01500 (15) | 0.00034 (16) | −0.00161 (16) |
Cl4 | 0.0349 (2) | 0.01520 (16) | 0.0200 (2) | −0.00240 (14) | −0.00534 (17) | −0.00315 (16) |
Cl5 | 0.01456 (15) | 0.02819 (18) | 0.0212 (2) | 0.00184 (13) | −0.00178 (15) | 0.00313 (17) |
Cl6 | 0.02407 (16) | 0.02194 (16) | 0.01314 (18) | 0.00235 (14) | 0.00050 (16) | 0.00246 (16) |
Cl7 | 0.02602 (18) | 0.02125 (16) | 0.0272 (2) | 0.00319 (15) | −0.00145 (18) | 0.00747 (17) |
Cl8 | 0.02019 (16) | 0.02524 (18) | 0.0208 (2) | −0.00052 (14) | −0.00230 (16) | −0.00533 (16) |
C1 | 0.0145 (6) | 0.0180 (6) | 0.0139 (8) | 0.0003 (5) | −0.0022 (6) | 0.0011 (6) |
C2 | 0.0131 (6) | 0.0171 (6) | 0.0138 (8) | 0.0026 (5) | 0.0000 (6) | −0.0003 (6) |
C3 | 0.0171 (7) | 0.0115 (6) | 0.0179 (8) | 0.0013 (5) | 0.0017 (6) | 0.0011 (6) |
C4 | 0.0144 (6) | 0.0190 (6) | 0.0145 (8) | −0.0009 (6) | −0.0013 (6) | 0.0024 (6) |
C5 | 0.0173 (6) | 0.0209 (7) | 0.0099 (7) | 0.0068 (5) | 0.0013 (6) | 0.0008 (6) |
C6 | 0.0200 (6) | 0.0117 (6) | 0.0149 (8) | 0.0003 (5) | −0.0029 (6) | −0.0020 (6) |
C7 | 0.0144 (6) | 0.0165 (6) | 0.0130 (8) | 0.0013 (5) | 0.0013 (6) | 0.0019 (6) |
C8 | 0.0185 (7) | 0.0187 (7) | 0.0186 (9) | 0.0014 (5) | 0.0000 (6) | 0.0018 (6) |
C9 | 0.0150 (6) | 0.0218 (7) | 0.0175 (8) | 0.0009 (5) | 0.0005 (6) | −0.0017 (7) |
Cl1—C3 | 1.7543 (13) | C2—C9 | 1.479 (2) |
Cl2—C4 | 1.6945 (14) | C2—C3 | 1.541 (2) |
Cl3—C5 | 1.7071 (13) | C3—C4 | 1.5384 (18) |
Cl4—C6 | 1.7538 (14) | C3—C7 | 1.561 (2) |
Cl5—C7 | 1.7715 (14) | C4—C5 | 1.3227 (19) |
Cl6—C7 | 1.7667 (15) | C5—C6 | 1.535 (2) |
Cl7—C8 | 1.8004 (13) | C6—C7 | 1.5601 (19) |
Cl8—C9 | 1.8137 (14) | C8—H8A | 0.9900 |
C1—C2 | 1.3382 (19) | C8—H8B | 0.9900 |
C1—C8 | 1.4768 (19) | C9—H9A | 0.9900 |
C1—C6 | 1.542 (2) | C9—H9B | 0.9900 |
C2—C1—C8 | 129.99 (14) | C5—C6—Cl4 | 116.56 (10) |
C2—C1—C6 | 106.64 (12) | C1—C6—Cl4 | 117.21 (10) |
C8—C1—C6 | 123.37 (12) | C7—C6—Cl4 | 115.27 (10) |
C1—C2—C9 | 129.43 (14) | C6—C7—C3 | 90.79 (11) |
C1—C2—C3 | 106.69 (13) | C6—C7—Cl6 | 115.82 (10) |
C9—C2—C3 | 123.87 (12) | C3—C7—Cl6 | 114.46 (9) |
C4—C3—C2 | 107.68 (11) | C6—C7—Cl5 | 113.58 (9) |
C4—C3—C7 | 98.38 (11) | C3—C7—Cl5 | 114.19 (10) |
C2—C3—C7 | 99.53 (10) | Cl6—C7—Cl5 | 107.56 (8) |
C4—C3—Cl1 | 115.96 (9) | C1—C8—Cl7 | 110.18 (9) |
C2—C3—Cl1 | 116.70 (10) | C1—C8—H8A | 109.6 |
C7—C3—Cl1 | 115.95 (10) | Cl7—C8—H8A | 109.6 |
C5—C4—C3 | 106.67 (12) | C1—C8—H8B | 109.6 |
C5—C4—Cl2 | 129.75 (11) | Cl7—C8—H8B | 109.6 |
C3—C4—Cl2 | 123.53 (10) | H8A—C8—H8B | 108.1 |
C4—C5—C6 | 107.33 (11) | C2—C9—Cl8 | 110.00 (9) |
C4—C5—Cl3 | 128.47 (11) | C2—C9—H9A | 109.7 |
C6—C5—Cl3 | 124.08 (10) | Cl8—C9—H9A | 109.7 |
C5—C6—C1 | 106.75 (12) | C2—C9—H9B | 109.7 |
C5—C6—C7 | 98.94 (11) | Cl8—C9—H9B | 109.7 |
C1—C6—C7 | 99.34 (11) | H9A—C9—H9B | 108.2 |
C8—C1—C2—C9 | −1.4 (2) | C8—C1—C6—C5 | 114.33 (13) |
C6—C1—C2—C9 | 178.19 (12) | C2—C1—C6—C7 | 37.02 (13) |
C8—C1—C2—C3 | 179.82 (13) | C8—C1—C6—C7 | −143.31 (12) |
C6—C1—C2—C3 | −0.54 (14) | C2—C1—C6—Cl4 | 161.84 (10) |
C1—C2—C3—C4 | 65.92 (14) | C8—C1—C6—Cl4 | −18.50 (17) |
C9—C2—C3—C4 | −112.90 (13) | C5—C6—C7—C3 | 54.25 (12) |
C1—C2—C3—C7 | −36.12 (13) | C1—C6—C7—C3 | −54.50 (11) |
C9—C2—C3—C7 | 145.06 (12) | Cl4—C6—C7—C3 | 179.34 (10) |
C1—C2—C3—Cl1 | −161.65 (10) | C5—C6—C7—Cl6 | −63.57 (13) |
C9—C2—C3—Cl1 | 19.53 (16) | C1—C6—C7—Cl6 | −172.33 (9) |
C2—C3—C4—C5 | −64.24 (15) | Cl4—C6—C7—Cl6 | 61.51 (13) |
C7—C3—C4—C5 | 38.62 (15) | C5—C6—C7—Cl5 | 171.20 (10) |
Cl1—C3—C4—C5 | 162.93 (12) | C1—C6—C7—Cl5 | 62.44 (12) |
C2—C3—C4—Cl2 | 113.65 (13) | Cl4—C6—C7—Cl5 | −63.72 (14) |
C7—C3—C4—Cl2 | −143.49 (11) | C4—C3—C7—C6 | −55.37 (11) |
Cl1—C3—C4—Cl2 | −19.18 (18) | C2—C3—C7—C6 | 54.26 (11) |
C3—C4—C5—C6 | −2.14 (17) | Cl1—C3—C7—C6 | −179.70 (10) |
Cl2—C4—C5—C6 | −179.85 (13) | C4—C3—C7—Cl6 | 63.63 (12) |
C3—C4—C5—Cl3 | 174.01 (12) | C2—C3—C7—Cl6 | 173.25 (8) |
Cl2—C4—C5—Cl3 | −3.7 (2) | Cl1—C3—C7—Cl6 | −60.70 (12) |
C4—C5—C6—C1 | 67.51 (15) | C4—C3—C7—Cl5 | −171.78 (9) |
Cl3—C5—C6—C1 | −108.85 (13) | C2—C3—C7—Cl5 | −62.15 (11) |
C4—C5—C6—C7 | −35.13 (15) | Cl1—C3—C7—Cl5 | 63.90 (13) |
Cl3—C5—C6—C7 | 148.51 (12) | C2—C1—C8—Cl7 | 111.76 (15) |
C4—C5—C6—Cl4 | −159.31 (12) | C6—C1—C8—Cl7 | −67.82 (15) |
Cl3—C5—C6—Cl4 | 24.33 (18) | C1—C2—C9—Cl8 | −105.69 (15) |
C2—C1—C6—C5 | −65.33 (14) | C3—C2—C9—Cl8 | 72.85 (14) |
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