Supporting information
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520618012295/xk5047sup2.pdf | |
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520618012295/xk5047sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520618012295/xk50471234TCB_270Ksup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520618012295/xk50471234TCB_90Ksup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520618012295/xk50471235TCB_270Ksup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520618012295/xk50471235TCB_90Ksup6.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520618012295/xk50471234TCB_270Ksup7.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520618012295/xk50471234TCB_90Ksup8.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520618012295/xk50471235TCB_270Ksup9.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2052520618012295/xk50471235TCB_90Ksup10.cml |
CCDC references: 1857059; 1857060; 1857061; 1857062
For all structures, data collection: CrysAlis CCD ver. 1.171.33.57 (Oxford Diffraction Ltd., 2010); cell refinement: CrysAlis PRO ver. 1.171.39.15e (Rigaku Oxford Diffraction, 2015); data reduction: CrysAlis PRO ver. 1.171.39.15e (Rigaku Oxford Diffraction, 2015); program(s) used to solve structure: SHELXS97 (G.M.Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (G.M.Sheldrick, 2008, 2015); molecular graphics: Mercury (C.F.Macrae at al., 2008); software used to prepare material for publication: SHELXL97 (G.M.Sheldrick, 2008, 2015).
C6H2Cl4 | Dx = 1.837 Mg m−3 |
Mr = 215.88 | Melting point: 320.7 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 3.8682 (3) Å | Cell parameters from 2263 reflections |
b = 14.9766 (9) Å | θ = 3.3–28.4° |
c = 13.4758 (9) Å | µ = 1.43 mm−1 |
β = 90.378 (6)° | T = 270 K |
V = 780.67 (9) Å3 | Tabular, colourless |
Z = 4 | 0.46 × 0.35 × 0.26 mm |
F(000) = 424 |
Xcalibur diffractometer | 1520 independent reflections |
Radiation source: fine-focus sealed tube | 1252 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω–scan | θmax = 26.0°, θmin = 3.0° |
Absorption correction: multi-scan CrysAlisPro ver. 1.171.39.15e (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −4→4 |
Tmin = 0.906, Tmax = 1.000 | k = −15→18 |
5063 measured reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | H-atom parameters constrained |
wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.0378P)2 + 3.6776P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max < 0.001 |
1520 reflections | Δρmax = 0.57 e Å−3 |
92 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.019 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.1255 (15) | 0.2526 (4) | 0.1690 (4) | 0.0465 (13) | |
Cl1 | −0.0467 (5) | 0.17466 (11) | 0.08858 (14) | 0.0678 (6) | |
C2 | 0.1635 (15) | 0.3405 (4) | 0.1405 (4) | 0.0442 (13) | |
Cl2 | 0.0361 (5) | 0.37454 (12) | 0.02399 (11) | 0.0652 (5) | |
C3 | 0.3085 (15) | 0.4016 (4) | 0.2066 (4) | 0.0452 (12) | |
Cl3 | 0.3591 (5) | 0.51143 (11) | 0.17090 (15) | 0.0717 (6) | |
C4 | 0.4055 (15) | 0.3748 (4) | 0.3011 (4) | 0.0457 (13) | |
Cl4 | 0.5782 (5) | 0.45067 (13) | 0.38398 (13) | 0.0686 (6) | |
C5 | 0.3675 (17) | 0.2864 (4) | 0.3293 (4) | 0.0558 (15) | |
H5 | 0.4347 | 0.2679 | 0.3924 | 0.067* | |
C6 | 0.2285 (17) | 0.2259 (4) | 0.2625 (5) | 0.0584 (16) | |
H6 | 0.2042 | 0.1664 | 0.2809 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.044 (3) | 0.043 (3) | 0.053 (3) | 0.004 (2) | 0.010 (2) | −0.006 (2) |
Cl1 | 0.0696 (11) | 0.0536 (9) | 0.0803 (12) | −0.0056 (8) | −0.0022 (9) | −0.0189 (8) |
C2 | 0.045 (3) | 0.048 (3) | 0.040 (3) | 0.004 (2) | 0.004 (2) | −0.001 (2) |
Cl2 | 0.0831 (12) | 0.0678 (11) | 0.0448 (8) | 0.0067 (9) | −0.0101 (8) | 0.0051 (7) |
C3 | 0.044 (3) | 0.043 (3) | 0.049 (3) | 0.004 (2) | 0.001 (2) | −0.001 (2) |
Cl3 | 0.0909 (13) | 0.0417 (9) | 0.0825 (12) | −0.0050 (8) | −0.0106 (10) | 0.0090 (8) |
C4 | 0.044 (3) | 0.051 (3) | 0.042 (3) | 0.004 (3) | 0.002 (2) | −0.005 (2) |
Cl4 | 0.0689 (11) | 0.0777 (12) | 0.0591 (10) | 0.0033 (9) | −0.0092 (8) | −0.0215 (8) |
C5 | 0.061 (4) | 0.065 (4) | 0.041 (3) | 0.007 (3) | −0.001 (3) | 0.012 (3) |
C6 | 0.065 (4) | 0.042 (3) | 0.069 (4) | 0.001 (3) | 0.003 (3) | 0.017 (3) |
C1—C6 | 1.378 (8) | C3—Cl3 | 1.725 (6) |
C1—C2 | 1.380 (8) | C4—C5 | 1.387 (8) |
C1—Cl1 | 1.724 (6) | C4—Cl4 | 1.725 (6) |
C2—C3 | 1.393 (8) | C5—C6 | 1.384 (9) |
C2—Cl2 | 1.720 (6) | C5—H5 | 0.9300 |
C3—C4 | 1.384 (8) | C6—H6 | 0.9300 |
C6—C1—C2 | 120.1 (5) | C3—C4—C5 | 120.1 (5) |
C6—C1—Cl1 | 119.1 (5) | C3—C4—Cl4 | 120.4 (5) |
C2—C1—Cl1 | 120.8 (5) | C5—C4—Cl4 | 119.5 (4) |
C1—C2—C3 | 119.5 (5) | C6—C5—C4 | 119.2 (5) |
C1—C2—Cl2 | 120.4 (4) | C6—C5—H5 | 120.4 |
C3—C2—Cl2 | 120.1 (4) | C4—C5—H5 | 120.4 |
C4—C3—C2 | 120.2 (5) | C1—C6—C5 | 120.9 (5) |
C4—C3—Cl3 | 120.2 (4) | C1—C6—H6 | 119.6 |
C2—C3—Cl3 | 119.6 (4) | C5—C6—H6 | 119.6 |
C6—C1—C2—C3 | 0.4 (8) | Cl3—C3—C4—C5 | −179.4 (5) |
Cl1—C1—C2—C3 | −179.0 (4) | C2—C3—C4—Cl4 | −178.9 (4) |
C6—C1—C2—Cl2 | 180.0 (5) | Cl3—C3—C4—Cl4 | −0.1 (7) |
Cl1—C1—C2—Cl2 | 0.6 (7) | C3—C4—C5—C6 | −0.7 (9) |
C1—C2—C3—C4 | −1.7 (8) | Cl4—C4—C5—C6 | 179.9 (5) |
Cl2—C2—C3—C4 | 178.8 (4) | C2—C1—C6—C5 | 0.7 (9) |
C1—C2—C3—Cl3 | 179.6 (4) | Cl1—C1—C6—C5 | −179.9 (5) |
Cl2—C2—C3—Cl3 | 0.0 (7) | C4—C5—C6—C1 | −0.5 (10) |
C2—C3—C4—C5 | 1.8 (9) |
C6H2Cl4 | Dx = 1.905 Mg m−3 |
Mr = 215.88 | Melting point: 320.7 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 3.79937 (12) Å | Cell parameters from 3724 reflections |
b = 14.8635 (4) Å | θ = 3.1–29.4° |
c = 13.3272 (4) Å | µ = 1.48 mm−1 |
β = 89.674 (3)° | T = 90 K |
V = 752.60 (4) Å3 | Tabular, colourless |
Z = 4 | 0.46 × 0.35 × 0.26 mm |
F(000) = 424 |
Xcalibur diffractometer | 1469 independent reflections |
Radiation source: fine-focus sealed tube | 1343 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
ω–scan | θmax = 26.0°, θmin = 3.1° |
Absorption correction: multi-scan CrysAlisPro ver. 1.171.39.15e (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −4→4 |
Tmin = 0.953, Tmax = 1.000 | k = −15→18 |
4993 measured reflections | l = −16→16 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | H-atom parameters constrained |
wR(F2) = 0.131 | w = 1/[σ^2^(Fo^2^) + (0.P)^2^ + 6.5793P] where P = (Fo^2^ + 2Fc^2^)/3 |
S = 1.36 | (Δ/σ)max < 0.001 |
1469 reflections | Δρmax = 0.61 e Å−3 |
92 parameters | Δρmin = −0.51 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc^*^=kFc[1+0.001xFc^2^λ^3^/sin(2θ)]^-1/4^ |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0059 (14) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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 | 0.1177 (14) | 0.2518 (4) | 0.1684 (4) | 0.0151 (11) | |
Cl1 | −0.0570 (4) | 0.17365 (9) | 0.08651 (11) | 0.0204 (4) | |
C2 | 0.1575 (15) | 0.3414 (4) | 0.1394 (4) | 0.0153 (11) | |
Cl2 | 0.0294 (4) | 0.37671 (10) | 0.02238 (10) | 0.0195 (4) | |
C3 | 0.3025 (15) | 0.4025 (4) | 0.2074 (4) | 0.0160 (11) | |
Cl3 | 0.3591 (4) | 0.51373 (9) | 0.17186 (11) | 0.0215 (4) | |
C4 | 0.4009 (14) | 0.3745 (4) | 0.3023 (4) | 0.0138 (11) | |
Cl4 | 0.5782 (4) | 0.45046 (10) | 0.38660 (11) | 0.0203 (4) | |
C5 | 0.3590 (15) | 0.2846 (4) | 0.3309 (4) | 0.0177 (12) | |
H5 | 0.4260 | 0.2656 | 0.3945 | 0.021* | |
C6 | 0.2162 (15) | 0.2241 (4) | 0.2632 (4) | 0.0180 (12) | |
H6 | 0.1864 | 0.1642 | 0.2817 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.011 (3) | 0.015 (3) | 0.019 (3) | −0.001 (2) | 0.003 (2) | −0.006 (2) |
Cl1 | 0.0205 (7) | 0.0160 (7) | 0.0246 (8) | −0.0017 (5) | −0.0013 (6) | −0.0057 (6) |
C2 | 0.013 (3) | 0.019 (3) | 0.013 (3) | 0.001 (2) | 0.000 (2) | −0.001 (2) |
Cl2 | 0.0241 (8) | 0.0202 (7) | 0.0141 (7) | 0.0012 (6) | −0.0028 (5) | 0.0018 (5) |
C3 | 0.013 (3) | 0.015 (3) | 0.020 (3) | 0.000 (2) | 0.002 (2) | 0.002 (2) |
Cl3 | 0.0261 (8) | 0.0134 (7) | 0.0250 (8) | −0.0017 (6) | −0.0032 (6) | 0.0028 (6) |
C4 | 0.011 (3) | 0.017 (3) | 0.014 (3) | 0.000 (2) | 0.000 (2) | −0.002 (2) |
Cl4 | 0.0204 (7) | 0.0230 (7) | 0.0176 (7) | 0.0004 (6) | −0.0028 (5) | −0.0061 (6) |
C5 | 0.015 (3) | 0.025 (3) | 0.013 (3) | 0.002 (2) | 0.000 (2) | 0.002 (2) |
C6 | 0.018 (3) | 0.014 (3) | 0.022 (3) | 0.000 (2) | 0.003 (2) | 0.005 (2) |
C1—C6 | 1.382 (8) | C3—Cl3 | 1.732 (6) |
C1—C2 | 1.395 (8) | C4—C5 | 1.398 (8) |
C1—Cl1 | 1.729 (6) | C4—Cl4 | 1.732 (6) |
C2—C3 | 1.399 (8) | C5—C6 | 1.386 (8) |
C2—Cl2 | 1.718 (6) | C5—H5 | 0.9300 |
C3—C4 | 1.385 (8) | C6—H6 | 0.9300 |
C6—C1—C2 | 120.6 (5) | C3—C4—C5 | 120.3 (5) |
C6—C1—Cl1 | 118.9 (4) | C3—C4—Cl4 | 120.3 (4) |
C2—C1—Cl1 | 120.5 (4) | C5—C4—Cl4 | 119.4 (4) |
C1—C2—C3 | 118.8 (5) | C6—C5—C4 | 119.2 (5) |
C1—C2—Cl2 | 120.9 (4) | C6—C5—H5 | 120.4 |
C3—C2—Cl2 | 120.3 (4) | C4—C5—H5 | 120.4 |
C4—C3—C2 | 120.4 (5) | C1—C6—C5 | 120.7 (5) |
C4—C3—Cl3 | 120.2 (4) | C1—C6—H6 | 119.7 |
C2—C3—Cl3 | 119.4 (4) | C5—C6—H6 | 119.7 |
C6—C1—C2—C3 | 0.7 (8) | Cl3—C3—C4—C5 | −179.3 (4) |
Cl1—C1—C2—C3 | −179.5 (4) | C2—C3—C4—Cl4 | −179.7 (4) |
C6—C1—C2—Cl2 | −179.0 (4) | Cl3—C3—C4—Cl4 | 0.5 (7) |
Cl1—C1—C2—Cl2 | 0.8 (7) | C3—C4—C5—C6 | −0.3 (8) |
C1—C2—C3—C4 | −0.7 (8) | Cl4—C4—C5—C6 | 179.9 (4) |
Cl2—C2—C3—C4 | 179.0 (4) | C2—C1—C6—C5 | −0.5 (8) |
C1—C2—C3—Cl3 | 179.2 (4) | Cl1—C1—C6—C5 | 179.7 (4) |
Cl2—C2—C3—Cl3 | −1.1 (7) | C4—C5—C6—C1 | 0.3 (8) |
C2—C3—C4—C5 | 0.5 (8) |
C6H2Cl4 | Dx = 1.818 Mg m−3 |
Mr = 215.88 | Melting point: 327.7 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 3.83433 (11) Å | Cell parameters from 5103 reflections |
b = 23.9377 (6) Å | θ = 3.4–28.8° |
c = 17.2355 (4) Å | µ = 1.41 mm−1 |
β = 94.293 (3)° | T = 270 K |
V = 1577.52 (7) Å3 | Pillar, colourless |
Z = 8 | 0.40 × 0.26 × 0.25 mm |
F(000) = 848 |
Xcalibur diffractometer | 3097 independent reflections |
Radiation source: fine-focus sealed tube | 2317 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω–scan | θmax = 26.0°, θmin = 3.4° |
Absorption correction: multi-scan CrysAlisPro ver. 1.171.39.15e (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −2→4 |
Tmin = 0.981, Tmax = 1.000 | k = −29→29 |
10692 measured reflections | l = −21→21 |
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)] = 0.025 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.060 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ^2^(Fo^2^) + (0.032P)^2^] where P = (Fo^2^ + 2Fc^2^)/3 |
3097 reflections | (Δ/σ)max = 0.001 |
181 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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 | 0.1928 (4) | −0.03197 (7) | 0.36377 (10) | 0.0391 (4) | |
Cl1 | 0.36535 (14) | −0.07516 (2) | 0.43755 (3) | 0.05800 (15) | |
C2 | 0.1674 (4) | −0.05067 (7) | 0.28738 (10) | 0.0358 (4) | |
Cl2 | 0.30717 (13) | −0.116412 (18) | 0.26445 (3) | 0.05096 (14) | |
C3 | 0.0261 (4) | −0.01461 (7) | 0.22987 (10) | 0.0378 (4) | |
Cl3 | −0.00755 (15) | −0.03547 (2) | 0.13382 (3) | 0.05990 (16) | |
C4 | −0.0867 (4) | 0.03816 (7) | 0.24784 (10) | 0.0393 (4) | |
H4 | −0.1807 | 0.0619 | 0.2090 | 0.047* | |
C5 | −0.0577 (4) | 0.05504 (7) | 0.32425 (10) | 0.0409 (4) | |
Cl5 | −0.19961 (14) | 0.121523 (19) | 0.34728 (3) | 0.06024 (15) | |
C6 | 0.0818 (5) | 0.02079 (7) | 0.38276 (11) | 0.0439 (4) | |
H6 | 0.1010 | 0.0330 | 0.4341 | 0.053* | |
C7 | 0.4340 (5) | 0.35148 (7) | 0.51498 (10) | 0.0391 (4) | |
Cl7 | 0.55033 (15) | 0.41901 (2) | 0.54078 (3) | 0.05906 (15) | |
C8 | 0.3166 (5) | 0.31475 (7) | 0.57000 (10) | 0.0404 (4) | |
Cl8 | 0.28425 (16) | 0.33537 (2) | 0.66451 (3) | 0.06430 (17) | |
C9 | 0.2287 (5) | 0.26081 (7) | 0.54648 (11) | 0.0428 (4) | |
Cl9 | 0.08067 (14) | 0.21350 (2) | 0.61234 (3) | 0.06384 (16) | |
C10 | 0.2565 (5) | 0.24360 (7) | 0.47127 (12) | 0.0478 (5) | |
H10 | 0.1979 | 0.2072 | 0.4564 | 0.057* | |
C11 | 0.3731 (5) | 0.28108 (8) | 0.41788 (10) | 0.0452 (5) | |
Cl11 | 0.41105 (19) | 0.25968 (2) | 0.32310 (3) | 0.07385 (19) | |
C12 | 0.4624 (5) | 0.33506 (7) | 0.43896 (10) | 0.0410 (4) | |
H12 | 0.5403 | 0.3600 | 0.4026 | 0.049* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0382 (10) | 0.0376 (10) | 0.0408 (10) | −0.0026 (8) | −0.0003 (8) | 0.0058 (8) |
Cl1 | 0.0705 (3) | 0.0537 (3) | 0.0479 (3) | 0.0054 (3) | −0.0086 (2) | 0.0102 (2) |
C2 | 0.0345 (9) | 0.0296 (9) | 0.0436 (10) | −0.0024 (7) | 0.0046 (8) | 0.0016 (8) |
Cl2 | 0.0626 (3) | 0.0361 (3) | 0.0553 (3) | 0.0078 (2) | 0.0115 (2) | 0.0011 (2) |
C3 | 0.0380 (10) | 0.0386 (10) | 0.0368 (9) | −0.0052 (8) | 0.0028 (8) | −0.0022 (8) |
Cl3 | 0.0887 (4) | 0.0521 (3) | 0.0382 (3) | 0.0086 (3) | 0.0004 (3) | −0.0031 (2) |
C4 | 0.0396 (10) | 0.0327 (9) | 0.0451 (10) | −0.0018 (8) | −0.0008 (8) | 0.0044 (8) |
C5 | 0.0397 (10) | 0.0307 (9) | 0.0523 (11) | −0.0016 (8) | 0.0029 (9) | −0.0048 (8) |
Cl5 | 0.0733 (4) | 0.0363 (3) | 0.0706 (3) | 0.0068 (2) | 0.0022 (3) | −0.0115 (2) |
C6 | 0.0485 (11) | 0.0439 (11) | 0.0390 (10) | −0.0044 (9) | 0.0003 (9) | −0.0050 (8) |
C7 | 0.0434 (10) | 0.0318 (9) | 0.0410 (10) | −0.0008 (8) | −0.0033 (8) | 0.0009 (8) |
Cl7 | 0.0893 (4) | 0.0382 (3) | 0.0487 (3) | −0.0132 (3) | −0.0019 (3) | −0.0037 (2) |
C8 | 0.0419 (10) | 0.0432 (10) | 0.0354 (9) | 0.0049 (9) | −0.0010 (8) | 0.0044 (8) |
Cl8 | 0.0914 (4) | 0.0638 (3) | 0.0385 (3) | 0.0025 (3) | 0.0098 (3) | 0.0019 (2) |
C9 | 0.0389 (11) | 0.0397 (10) | 0.0492 (11) | 0.0014 (8) | −0.0005 (9) | 0.0133 (9) |
Cl9 | 0.0662 (3) | 0.0546 (3) | 0.0708 (4) | −0.0081 (3) | 0.0059 (3) | 0.0269 (3) |
C10 | 0.0548 (12) | 0.0323 (10) | 0.0551 (12) | −0.0032 (9) | −0.0039 (10) | −0.0003 (9) |
C11 | 0.0540 (12) | 0.0406 (10) | 0.0407 (10) | 0.0016 (9) | 0.0010 (9) | −0.0041 (8) |
Cl11 | 0.1174 (5) | 0.0561 (3) | 0.0489 (3) | −0.0062 (3) | 0.0128 (3) | −0.0152 (2) |
C12 | 0.0486 (11) | 0.0360 (10) | 0.0386 (10) | −0.0007 (8) | 0.0034 (9) | 0.0059 (8) |
C1—C6 | 1.380 (2) | C7—C12 | 1.380 (2) |
C1—C2 | 1.387 (2) | C7—C8 | 1.393 (2) |
C1—Cl1 | 1.7314 (17) | C7—Cl7 | 1.7263 (17) |
C2—C3 | 1.393 (2) | C8—C9 | 1.387 (2) |
C2—Cl2 | 1.7179 (17) | C8—Cl8 | 1.7153 (18) |
C3—C4 | 1.378 (2) | C9—C10 | 1.372 (3) |
C3—Cl3 | 1.7248 (17) | C9—Cl9 | 1.7291 (18) |
C4—C5 | 1.374 (2) | C10—C11 | 1.383 (3) |
C4—H4 | 0.9300 | C10—H10 | 0.9300 |
C5—C6 | 1.376 (2) | C11—C12 | 1.378 (2) |
C5—Cl5 | 1.7374 (18) | C11—Cl11 | 1.7286 (18) |
C6—H6 | 0.9300 | C12—H12 | 0.9300 |
C6—C1—C2 | 121.30 (16) | C12—C7—C8 | 121.28 (16) |
C6—C1—Cl1 | 118.68 (14) | C12—C7—Cl7 | 118.31 (13) |
C2—C1—Cl1 | 120.02 (13) | C8—C7—Cl7 | 120.41 (14) |
C1—C2—C3 | 118.11 (15) | C9—C8—C7 | 118.19 (16) |
C1—C2—Cl2 | 120.87 (13) | C9—C8—Cl8 | 120.81 (14) |
C3—C2—Cl2 | 121.02 (13) | C7—C8—Cl8 | 121.00 (14) |
C4—C3—C2 | 121.34 (16) | C10—C9—C8 | 121.42 (17) |
C4—C3—Cl3 | 118.61 (14) | C10—C9—Cl9 | 118.43 (14) |
C2—C3—Cl3 | 120.05 (13) | C8—C9—Cl9 | 120.15 (15) |
C5—C4—C3 | 118.73 (16) | C9—C10—C11 | 119.05 (17) |
C5—C4—H4 | 120.6 | C9—C10—H10 | 120.5 |
C3—C4—H4 | 120.6 | C11—C10—H10 | 120.5 |
C4—C5—C6 | 121.74 (16) | C12—C11—C10 | 121.26 (17) |
C4—C5—Cl5 | 118.95 (14) | C12—C11—Cl11 | 119.34 (14) |
C6—C5—Cl5 | 119.31 (14) | C10—C11—Cl11 | 119.39 (14) |
C5—C6—C1 | 118.77 (17) | C11—C12—C7 | 118.79 (16) |
C5—C6—H6 | 120.6 | C11—C12—H12 | 120.6 |
C1—C6—H6 | 120.6 | C7—C12—H12 | 120.6 |
C6—C1—C2—C3 | 0.0 (3) | C12—C7—C8—C9 | 0.1 (3) |
Cl1—C1—C2—C3 | 179.83 (12) | Cl7—C7—C8—C9 | −179.55 (14) |
C6—C1—C2—Cl2 | 179.89 (13) | C12—C7—C8—Cl8 | 179.66 (14) |
Cl1—C1—C2—Cl2 | −0.3 (2) | Cl7—C7—C8—Cl8 | 0.0 (2) |
C1—C2—C3—C4 | −0.2 (2) | C7—C8—C9—C10 | 0.2 (3) |
Cl2—C2—C3—C4 | 179.96 (14) | Cl8—C8—C9—C10 | −179.35 (15) |
C1—C2—C3—Cl3 | 179.36 (13) | C7—C8—C9—Cl9 | −179.89 (13) |
Cl2—C2—C3—Cl3 | −0.5 (2) | Cl8—C8—C9—Cl9 | 0.6 (2) |
C2—C3—C4—C5 | 0.0 (3) | C8—C9—C10—C11 | −0.4 (3) |
Cl3—C3—C4—C5 | −179.51 (13) | Cl9—C9—C10—C11 | 179.71 (15) |
C3—C4—C5—C6 | 0.3 (3) | C9—C10—C11—C12 | 0.2 (3) |
C3—C4—C5—Cl5 | −179.99 (13) | C9—C10—C11—Cl11 | 179.69 (15) |
C4—C5—C6—C1 | −0.5 (3) | C10—C11—C12—C7 | 0.0 (3) |
Cl5—C5—C6—C1 | 179.84 (13) | Cl11—C11—C12—C7 | −179.39 (14) |
C2—C1—C6—C5 | 0.3 (3) | C8—C7—C12—C11 | −0.2 (3) |
Cl1—C1—C6—C5 | −179.54 (13) | Cl7—C7—C12—C11 | 179.45 (14) |
C6H2Cl4 | Dx = 1.884 Mg m−3 |
Mr = 215.88 | Melting point: 327.7 K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 3.76927 (10) Å | Cell parameters from 7572 reflections |
b = 23.6053 (6) Å | θ = 3.4–29.5° |
c = 17.1740 (4) Å | µ = 1.46 mm−1 |
β = 94.902 (2)° | T = 90 K |
V = 1522.46 (7) Å3 | Pillar, colourless |
Z = 8 | 0.40 × 0.26 × 0.25 mm |
F(000) = 848 |
Xcalibur diffractometer | 2994 independent reflections |
Radiation source: fine-focus sealed tube | 2634 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ω–scan | θmax = 26.0°, θmin = 3.5° |
Absorption correction: multi-scan CrysAlisPro ver. 1.171.39.15e (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −2→4 |
Tmin = 0.970, Tmax = 1.000 | k = −29→29 |
10291 measured reflections | l = −21→21 |
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)] = 0.018 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.047 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ^2^(Fo^2^) + (0.0266P)^2^ + 0.0934P] where P = (Fo^2^ + 2Fc^2^)/3 |
2994 reflections | (Δ/σ)max = 0.001 |
181 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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 | 0.1923 (4) | −0.03345 (6) | 0.36523 (8) | 0.0138 (3) | |
Cl1 | 0.36967 (10) | −0.077100 (16) | 0.44003 (2) | 0.01819 (9) | |
C2 | 0.1734 (4) | −0.05217 (6) | 0.28804 (8) | 0.0125 (3) | |
Cl2 | 0.32340 (10) | −0.118568 (14) | 0.26517 (2) | 0.01590 (9) | |
C3 | 0.0297 (4) | −0.01565 (6) | 0.22961 (8) | 0.0125 (3) | |
Cl3 | 0.00618 (10) | −0.036308 (15) | 0.13281 (2) | 0.01842 (9) | |
C4 | −0.0932 (4) | 0.03784 (6) | 0.24733 (9) | 0.0134 (3) | |
H4 | −0.1894 | 0.0618 | 0.2081 | 0.016* | |
C5 | −0.0694 (4) | 0.05469 (6) | 0.32478 (9) | 0.0141 (3) | |
Cl5 | −0.22052 (10) | 0.121814 (15) | 0.34747 (2) | 0.01856 (9) | |
C6 | 0.0732 (4) | 0.01995 (6) | 0.38434 (9) | 0.0147 (3) | |
H6 | 0.0889 | 0.0321 | 0.4360 | 0.018* | |
C7 | 0.4363 (4) | 0.35277 (6) | 0.51414 (8) | 0.0131 (3) | |
Cl7 | 0.56850 (10) | 0.420938 (15) | 0.53986 (2) | 0.01757 (9) | |
C8 | 0.3156 (4) | 0.31611 (6) | 0.57008 (8) | 0.0132 (3) | |
Cl8 | 0.29511 (10) | 0.337546 (16) | 0.66543 (2) | 0.01921 (9) | |
C9 | 0.2152 (4) | 0.26137 (6) | 0.54699 (9) | 0.0143 (3) | |
Cl9 | 0.06403 (10) | 0.214333 (15) | 0.61401 (2) | 0.01882 (9) | |
C10 | 0.2348 (4) | 0.24324 (6) | 0.47094 (9) | 0.0149 (3) | |
H10 | 0.1687 | 0.2065 | 0.4563 | 0.018* | |
C11 | 0.3547 (4) | 0.28079 (6) | 0.41680 (8) | 0.0149 (3) | |
Cl11 | 0.38266 (11) | 0.258378 (16) | 0.32143 (2) | 0.02154 (10) | |
C12 | 0.4551 (4) | 0.33561 (6) | 0.43748 (8) | 0.0135 (3) | |
H12 | 0.5335 | 0.3604 | 0.4005 | 0.016* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0118 (7) | 0.0136 (7) | 0.0158 (8) | −0.0008 (6) | 0.0000 (6) | 0.0034 (6) |
Cl1 | 0.02215 (19) | 0.01674 (19) | 0.01499 (18) | 0.00191 (15) | −0.00248 (15) | 0.00325 (14) |
C2 | 0.0108 (7) | 0.0096 (7) | 0.0173 (7) | −0.0002 (6) | 0.0016 (6) | −0.0003 (6) |
Cl2 | 0.01909 (19) | 0.01119 (18) | 0.01773 (19) | 0.00284 (14) | 0.00335 (15) | 0.00040 (14) |
C3 | 0.0119 (7) | 0.0145 (7) | 0.0112 (7) | −0.0028 (6) | 0.0013 (6) | −0.0017 (6) |
Cl3 | 0.0266 (2) | 0.01678 (19) | 0.01175 (18) | 0.00343 (15) | 0.00066 (15) | −0.00115 (14) |
C4 | 0.0124 (7) | 0.0123 (7) | 0.0154 (7) | −0.0012 (6) | −0.0002 (6) | 0.0023 (6) |
C5 | 0.0123 (7) | 0.0097 (7) | 0.0203 (8) | −0.0006 (6) | 0.0024 (6) | −0.0023 (6) |
Cl5 | 0.0224 (2) | 0.01135 (18) | 0.0217 (2) | 0.00232 (14) | 0.00063 (15) | −0.00351 (14) |
C6 | 0.0152 (7) | 0.0158 (8) | 0.0130 (7) | −0.0026 (6) | 0.0005 (6) | −0.0025 (6) |
C7 | 0.0125 (7) | 0.0102 (7) | 0.0162 (7) | −0.0009 (6) | −0.0010 (6) | −0.0008 (6) |
Cl7 | 0.0252 (2) | 0.01169 (18) | 0.01561 (18) | −0.00436 (15) | 0.00036 (15) | −0.00117 (14) |
C8 | 0.0117 (7) | 0.0153 (7) | 0.0123 (7) | 0.0023 (6) | −0.0003 (6) | 0.0003 (6) |
Cl8 | 0.0268 (2) | 0.0190 (2) | 0.01208 (18) | −0.00095 (16) | 0.00295 (15) | −0.00027 (14) |
C9 | 0.0115 (7) | 0.0146 (8) | 0.0168 (8) | 0.0005 (6) | 0.0003 (6) | 0.0050 (6) |
Cl9 | 0.02011 (19) | 0.01587 (19) | 0.02052 (19) | −0.00263 (15) | 0.00195 (15) | 0.00699 (15) |
C10 | 0.0154 (8) | 0.0096 (7) | 0.0191 (8) | −0.0007 (6) | −0.0019 (6) | −0.0004 (6) |
C11 | 0.0150 (7) | 0.0173 (8) | 0.0124 (7) | 0.0028 (6) | 0.0001 (6) | −0.0022 (6) |
Cl11 | 0.0324 (2) | 0.0175 (2) | 0.01504 (19) | −0.00236 (16) | 0.00424 (16) | −0.00473 (15) |
C12 | 0.0132 (7) | 0.0136 (7) | 0.0137 (7) | −0.0003 (6) | 0.0005 (6) | 0.0031 (6) |
C1—C6 | 1.387 (2) | C7—C12 | 1.385 (2) |
C1—C2 | 1.393 (2) | C7—C8 | 1.398 (2) |
C1—Cl1 | 1.7355 (14) | C7—Cl7 | 1.7307 (14) |
C2—C3 | 1.3967 (19) | C8—C9 | 1.394 (2) |
C2—Cl2 | 1.7229 (14) | C8—Cl8 | 1.7219 (15) |
C3—C4 | 1.388 (2) | C9—C10 | 1.382 (2) |
C3—Cl3 | 1.7275 (14) | C9—Cl9 | 1.7304 (15) |
C4—C5 | 1.384 (2) | C10—C11 | 1.388 (2) |
C4—H4 | 0.9300 | C10—H10 | 0.9300 |
C5—C6 | 1.383 (2) | C11—C12 | 1.386 (2) |
C5—Cl5 | 1.7392 (15) | C11—Cl11 | 1.7330 (15) |
C6—H6 | 0.9300 | C12—H12 | 0.9300 |
C6—C1—C2 | 121.47 (13) | C12—C7—C8 | 121.22 (13) |
C6—C1—Cl1 | 118.46 (11) | C12—C7—Cl7 | 118.53 (11) |
C2—C1—Cl1 | 120.07 (11) | C8—C7—Cl7 | 120.25 (11) |
C1—C2—C3 | 118.23 (13) | C9—C8—C7 | 118.34 (13) |
C1—C2—Cl2 | 120.95 (11) | C9—C8—Cl8 | 120.63 (11) |
C3—C2—Cl2 | 120.82 (11) | C7—C8—Cl8 | 121.03 (11) |
C4—C3—C2 | 121.35 (13) | C10—C9—C8 | 121.36 (13) |
C4—C3—Cl3 | 118.51 (11) | C10—C9—Cl9 | 118.49 (11) |
C2—C3—Cl3 | 120.14 (11) | C8—C9—Cl9 | 120.15 (11) |
C5—C4—C3 | 118.48 (13) | C9—C10—C11 | 118.81 (13) |
C5—C4—H4 | 120.8 | C9—C10—H10 | 120.6 |
C3—C4—H4 | 120.8 | C11—C10—H10 | 120.6 |
C6—C5—C4 | 121.97 (13) | C12—C11—C10 | 121.47 (14) |
C6—C5—Cl5 | 119.24 (11) | C12—C11—Cl11 | 119.33 (11) |
C4—C5—Cl5 | 118.79 (11) | C10—C11—Cl11 | 119.19 (11) |
C5—C6—C1 | 118.50 (13) | C7—C12—C11 | 118.79 (13) |
C5—C6—H6 | 120.8 | C7—C12—H12 | 120.6 |
C1—C6—H6 | 120.8 | C11—C12—H12 | 120.6 |
C6—C1—C2—C3 | −0.1 (2) | C12—C7—C8—C9 | 0.3 (2) |
Cl1—C1—C2—C3 | −179.83 (11) | Cl7—C7—C8—C9 | −179.36 (11) |
C6—C1—C2—Cl2 | 179.85 (11) | C12—C7—C8—Cl8 | 179.65 (11) |
Cl1—C1—C2—Cl2 | 0.16 (17) | Cl7—C7—C8—Cl8 | 0.00 (17) |
C1—C2—C3—C4 | −0.3 (2) | C7—C8—C9—C10 | 0.3 (2) |
Cl2—C2—C3—C4 | 179.75 (11) | Cl8—C8—C9—C10 | −179.08 (11) |
C1—C2—C3—Cl3 | 179.03 (11) | C7—C8—C9—Cl9 | 179.97 (11) |
Cl2—C2—C3—Cl3 | −0.96 (17) | Cl8—C8—C9—Cl9 | 0.61 (18) |
C2—C3—C4—C5 | 0.3 (2) | C8—C9—C10—C11 | −0.5 (2) |
Cl3—C3—C4—C5 | −179.05 (11) | Cl9—C9—C10—C11 | 179.81 (11) |
C3—C4—C5—C6 | 0.2 (2) | C9—C10—C11—C12 | 0.1 (2) |
C3—C4—C5—Cl5 | 179.64 (11) | C9—C10—C11—Cl11 | 179.65 (11) |
C4—C5—C6—C1 | −0.6 (2) | C8—C7—C12—C11 | −0.6 (2) |
Cl5—C5—C6—C1 | 179.97 (11) | Cl7—C7—C12—C11 | 179.03 (11) |
C2—C1—C6—C5 | 0.5 (2) | C10—C11—C12—C7 | 0.4 (2) |
Cl1—C1—C6—C5 | −179.76 (11) | Cl11—C11—C12—C7 | −179.10 (11) |