Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106046684/so5006sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768106046684/so5006oDCBsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768106046684/so5006mDCBsup3.hkl |
CCDC references: 637751; 637752
For both compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003); program(s) used to solve structure: SHELXS–97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL–97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1990); software used to prepare material for publication: SHELXL–97 (Sheldrick, 1997).
C6H4Cl2 | F(000) = 296 |
Mr = 146.99 | Dx = 1.558 Mg m−3 |
Monoclinic, P21/n | Melting point: 256.4 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 3.9274 (4) Å | Cell parameters from 1765 reflections |
b = 10.5678 (10) Å | θ = 2.3–25.7° |
c = 15.199 (9) Å | µ = 0.91 mm−1 |
β = 96.70 (2)° | T = 295 K |
V = 626.5 (4) Å3 | Column, colourless |
Z = 4 | 0.44 × 0.30 × 0.12 mm |
KM-4 CCD diffractometer | 431 independent reflections |
Radiation source: fine-focus sealed tube | 133 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.069 |
ϕ– and ω–scans | θmax = 25.0°, θmin = 3.9° |
Absorption correction: analytical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | h = −4→4 |
Tmin = 0.43, Tmax = 0.79 | k = −12→12 |
3835 measured reflections | l = −6→6 |
Refinement on F2 | Primary atom site location: Patterson |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.037 | H-atom parameters constrained |
S = 0.63 | w = 1/[σ2(Fo2) + (0.0138P)2] where P = (Fo2 + 2Fc2)/3 |
431 reflections | (Δ/σ)max < 0.001 |
73 parameters | Δρmax = 0.21 e Å−3 |
111 restraints | Δρmin = −0.22 e Å−3 |
C6H4Cl2 | V = 626.5 (4) Å3 |
Mr = 146.99 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 3.9274 (4) Å | µ = 0.91 mm−1 |
b = 10.5678 (10) Å | T = 295 K |
c = 15.199 (9) Å | 0.44 × 0.30 × 0.12 mm |
β = 96.70 (2)° |
KM-4 CCD diffractometer | 431 independent reflections |
Absorption correction: analytical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | 133 reflections with I > 2σ(I) |
Tmin = 0.43, Tmax = 0.79 | Rint = 0.069 |
3835 measured reflections |
R[F2 > 2σ(F2)] = 0.031 | 111 restraints |
wR(F2) = 0.037 | H-atom parameters constrained |
S = 0.63 | Δρmax = 0.21 e Å−3 |
431 reflections | Δρmin = −0.22 e Å−3 |
73 parameters |
Experimental. Data were collected at pressure of 0.18 GPa (180000 kPa) with the crystal obtained by the in situ high-pressure crystallization technique Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. |
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 DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.0111 (6) | 0.80323 (19) | 0.7942 (5) | 0.100 (4) | |
Cl2 | −0.2769 (4) | 0.99043 (12) | 0.6415 (3) | 0.0646 (19) | |
C1 | 0.0274 (16) | 0.7634 (7) | 0.6869 (15) | 0.051 (4) | |
C2 | −0.103 (3) | 0.8469 (7) | 0.6220 (11) | 0.054 (5) | |
C3 | −0.073 (2) | 0.8126 (8) | 0.5341 (13) | 0.060 (5) | |
H3 | −0.1529 | 0.8670 | 0.4882 | 0.072* | |
C4 | 0.0759 (13) | 0.6978 (6) | 0.5150 (10) | 0.068 (4) | |
H4 | 0.0961 | 0.6751 | 0.4567 | 0.082* | |
C5 | 0.191 (2) | 0.6195 (7) | 0.5830 (10) | 0.065 (5) | |
H5 | 0.2894 | 0.5425 | 0.5705 | 0.078* | |
C6 | 0.166 (2) | 0.6512 (6) | 0.6701 (11) | 0.058 (5) | |
H6 | 0.2438 | 0.5963 | 0.7159 | 0.070* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.1007 (15) | 0.0817 (13) | 0.121 (14) | −0.0101 (12) | 0.024 (3) | −0.002 (3) |
Cl2 | 0.0658 (7) | 0.0566 (8) | 0.071 (6) | 0.0029 (9) | 0.0039 (11) | 0.004 (2) |
C1 | 0.044 (3) | 0.060 (3) | 0.047 (13) | −0.003 (3) | −0.002 (8) | −0.011 (6) |
C2 | 0.050 (3) | 0.051 (3) | 0.063 (15) | −0.003 (3) | 0.017 (8) | 0.005 (6) |
C3 | 0.052 (4) | 0.070 (3) | 0.054 (13) | −0.006 (3) | −0.009 (9) | 0.004 (7) |
C4 | 0.065 (4) | 0.082 (3) | 0.061 (13) | −0.014 (3) | 0.024 (7) | −0.016 (6) |
C5 | 0.056 (4) | 0.061 (4) | 0.079 (14) | 0.002 (4) | 0.018 (8) | −0.020 (5) |
C6 | 0.055 (4) | 0.051 (3) | 0.068 (13) | 0.000 (3) | 0.008 (10) | −0.002 (5) |
Cl1—C1 | 1.71 (2) | C4—C5 | 1.359 (16) |
C1—C2 | 1.376 (18) | C5—C6 | 1.379 (17) |
C1—C6 | 1.342 (10) | C3—H3 | 0.9300 |
Cl2—C2 | 1.704 (9) | C4—H4 | 0.9300 |
C2—C3 | 1.403 (19) | C5—H5 | 0.9300 |
C3—C4 | 1.391 (11) | C6—H6 | 0.9300 |
C1—C2—Cl2 | 124.7 (13) | C6—C1—C2 | 123.7 (17) |
C1—C2—C3 | 116.8 (11) | C1—C6—H6 | 120.9 |
C1—C6—C5 | 118.2 (14) | C2—C3—H3 | 119.7 |
C2—C1—Cl1 | 117.3 (9) | C3—C4—H4 | 120.6 |
C3—C2—Cl2 | 118.4 (9) | C4—C3—H3 | 119.7 |
C4—C3—C2 | 120.6 (14) | C4—C5—H5 | 119.1 |
C4—C5—C6 | 121.8 (9) | C5—C4—H4 | 120.6 |
C5—C4—C3 | 118.8 (14) | C5—C6—H6 | 120.9 |
C6—C1—Cl1 | 118.9 (14) | C6—C5—H5 | 119.1 |
C1—C2—C3—C4 | 1.3 (17) | C6—C1—C2—Cl2 | −179.4 (7) |
C2—C1—C6—C5 | 2.3 (15) | Cl1—C1—C2—C3 | −179.4 (10) |
C2—C3—C4—C5 | 0.1 (16) | Cl1—C1—C6—C5 | 179.1 (8) |
C3—C4—C5—C6 | −0.4 (17) | Cl1—C1—C2—Cl2 | 3.9 (10) |
C4—C5—C6—C1 | −0.8 (18) | Cl2—C2—C3—C4 | 178.3 (4) |
C6—C1—C2—C3 | −2.6 (14) |
C6H4Cl2 | F(000) = 592 |
Mr = 146.99 | Dx = 1.541 Mg m−3 |
Monoclinic, P21/c | Melting point: 248.3 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 3.9163 (6) Å | Cell parameters from 2167 reflections |
b = 12.532 (5) Å | θ = 2.3–22.6° |
c = 25.849 (5) Å | µ = 0.90 mm−1 |
β = 93.098 (14)° | T = 295 K |
V = 1266.8 (6) Å3 | Column, colourless |
Z = 8 | 0.40 × 0.25 × 0.12 mm |
KM-4 CCD diffractometer | 800 independent reflections |
Radiation source: fine-focus sealed tube | 627 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.091 |
ϕ– and ω–scans | θmax = 25.0°, θmin = 2.9° |
Absorption correction: analytical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | h = −4→4 |
Tmin = 0.40, Tmax = 0.82 | k = −9→7 |
4205 measured reflections | l = −27→27 |
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)] = 0.109 | H-atom parameters constrained |
wR(F2) = 0.129 | w = 1/[σ2(Fo2) + (0.023P)2 + 1.956P] where P = (Fo2 + 2Fc2)/3 |
S = 1.47 | (Δ/σ)max < 0.001 |
800 reflections | Δρmax = 0.18 e Å−3 |
146 parameters | Δρmin = −0.19 e Å−3 |
222 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: Patterson | Extinction coefficient: 0.018 (2) |
C6H4Cl2 | V = 1266.8 (6) Å3 |
Mr = 146.99 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 3.9163 (6) Å | µ = 0.90 mm−1 |
b = 12.532 (5) Å | T = 295 K |
c = 25.849 (5) Å | 0.40 × 0.25 × 0.12 mm |
β = 93.098 (14)° |
KM-4 CCD diffractometer | 800 independent reflections |
Absorption correction: analytical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | 627 reflections with I > 2σ(I) |
Tmin = 0.40, Tmax = 0.82 | Rint = 0.091 |
4205 measured reflections |
R[F2 > 2σ(F2)] = 0.109 | 222 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.47 | Δρmax = 0.18 e Å−3 |
800 reflections | Δρmin = −0.19 e Å−3 |
146 parameters |
Experimental. Data were collected at pressure of 0.17 GPa (170000 kPa) with the crystal obtained by the in situ high-pressure crystallization technique Pressure was determined by monitoring the shift of the ruby R1-fluorescence line. |
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 DAC imposes severe restrictions on which reflections can be collected, resulting in a low data:parameter ratio. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.2856 (7) | 0.5602 (4) | 0.09131 (11) | 0.076 (2) | |
Cl2 | −0.2206 (7) | 0.2061 (4) | 0.17370 (10) | 0.0707 (19) | |
Cl3 | 0.4221 (7) | 1.0049 (4) | 0.25859 (9) | 0.076 (2) | |
Cl4 | 0.3740 (7) | 0.9352 (4) | 0.05431 (10) | 0.0797 (19) | |
C1 | 0.153 (2) | 0.4284 (15) | 0.0842 (4) | 0.050 (4) | |
C2 | 0.030 (2) | 0.3750 (13) | 0.1259 (4) | 0.045 (4) | |
H2 | 0.0177 | 0.4096 | 0.1576 | 0.054* | |
C3 | −0.074 (2) | 0.2716 (13) | 0.1208 (4) | 0.045 (4) | |
C4 | −0.050 (2) | 0.2198 (12) | 0.0746 (4) | 0.057 (4) | |
H4 | −0.1155 | 0.1487 | 0.0710 | 0.069* | |
C5 | 0.074 (3) | 0.2752 (13) | 0.0334 (4) | 0.063 (4) | |
H5 | 0.0860 | 0.2406 | 0.0017 | 0.076* | |
C6 | 0.180 (3) | 0.3784 (14) | 0.0373 (4) | 0.061 (4) | |
H6 | 0.2684 | 0.4137 | 0.0093 | 0.074* | |
C7 | 0.510 (2) | 0.9219 (13) | 0.2060 (4) | 0.048 (4) | |
C8 | 0.410 (2) | 0.9590 (13) | 0.1571 (3) | 0.047 (4) | |
H8 | 0.2969 | 1.0235 | 0.1516 | 0.057* | |
C9 | 0.493 (2) | 0.8925 (13) | 0.1168 (4) | 0.048 (4) | |
C10 | 0.664 (3) | 0.7977 (13) | 0.1237 (4) | 0.058 (4) | |
H10 | 0.7198 | 0.7566 | 0.0954 | 0.069* | |
C11 | 0.752 (3) | 0.7650 (13) | 0.1732 (4) | 0.062 (4) | |
H11 | 0.8634 | 0.7001 | 0.1788 | 0.074* | |
C12 | 0.677 (3) | 0.8283 (13) | 0.2149 (4) | 0.057 (4) | |
H12 | 0.7392 | 0.8070 | 0.2486 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.074 (2) | 0.067 (8) | 0.088 (3) | −0.010 (3) | 0.0043 (15) | 0.008 (2) |
Cl2 | 0.0676 (18) | 0.070 (7) | 0.075 (2) | −0.014 (2) | 0.0054 (15) | 0.014 (2) |
Cl3 | 0.083 (2) | 0.090 (7) | 0.055 (2) | 0.001 (2) | 0.0121 (14) | −0.015 (2) |
Cl4 | 0.101 (2) | 0.086 (7) | 0.052 (2) | −0.017 (3) | −0.0003 (15) | −0.0020 (19) |
C1 | 0.041 (5) | 0.057 (12) | 0.053 (6) | −0.012 (7) | 0.002 (5) | 0.003 (6) |
C2 | 0.036 (6) | 0.054 (12) | 0.045 (5) | −0.011 (7) | 0.000 (4) | −0.004 (6) |
C3 | 0.033 (6) | 0.053 (12) | 0.049 (5) | −0.011 (7) | −0.003 (5) | 0.002 (6) |
C4 | 0.056 (6) | 0.055 (12) | 0.062 (7) | −0.002 (7) | 0.010 (5) | −0.013 (6) |
C5 | 0.064 (7) | 0.068 (12) | 0.058 (6) | −0.003 (8) | 0.012 (5) | −0.012 (7) |
C6 | 0.062 (7) | 0.071 (12) | 0.052 (6) | −0.010 (8) | 0.011 (5) | 0.004 (7) |
C7 | 0.048 (6) | 0.050 (12) | 0.047 (5) | −0.003 (7) | 0.017 (5) | −0.001 (6) |
C8 | 0.052 (5) | 0.038 (12) | 0.053 (6) | −0.006 (6) | 0.010 (5) | 0.003 (5) |
C9 | 0.049 (6) | 0.046 (12) | 0.051 (6) | −0.012 (7) | 0.010 (5) | −0.005 (6) |
C10 | 0.063 (7) | 0.044 (12) | 0.067 (6) | −0.011 (7) | 0.020 (6) | −0.007 (7) |
C11 | 0.055 (6) | 0.049 (12) | 0.084 (7) | 0.008 (7) | 0.020 (6) | 0.007 (6) |
C12 | 0.056 (6) | 0.057 (13) | 0.060 (6) | 0.002 (7) | 0.006 (5) | 0.010 (6) |
Cl1—C1 | 1.739 (17) | Cl3—C7 | 1.761 (13) |
C1—C2 | 1.380 (13) | C7—C8 | 1.383 (11) |
C1—C6 | 1.373 (13) | C7—C12 | 1.357 (15) |
Cl2—C3 | 1.719 (12) | Cl4—C9 | 1.741 (11) |
C2—C3 | 1.362 (15) | C8—C9 | 1.384 (13) |
C3—C4 | 1.368 (12) | C9—C10 | 1.372 (15) |
C4—C5 | 1.382 (13) | C10—C11 | 1.369 (11) |
C5—C6 | 1.360 (16) | C11—C12 | 1.383 (13) |
C2—H2 | 0.9300 | C8—H8 | 0.9300 |
C4—H4 | 0.9300 | C10—H10 | 0.9300 |
C5—H5 | 0.9300 | C11—H11 | 0.9300 |
C6—H6 | 0.9300 | C12—H12 | 0.9300 |
C2—C3—Cl2 | 119.2 (9) | C8—C9—Cl4 | 116.8 (11) |
C3—C2—C1 | 120.1 (12) | C7—C8—C9 | 114.8 (12) |
C5—C6—C1 | 117.5 (13) | C7—C12—C11 | 119.0 (12) |
C2—C1—Cl1 | 119.5 (10) | C8—C7—Cl3 | 116.8 (11) |
C4—C3—Cl2 | 120.6 (11) | C10—C9—Cl4 | 119.4 (9) |
C2—C3—C4 | 120.1 (11) | C10—C9—C8 | 123.8 (12) |
C6—C5—C4 | 122.7 (13) | C10—C11—C12 | 120.2 (14) |
C3—C4—C5 | 118.6 (14) | C11—C10—C9 | 118.5 (12) |
C6—C1—Cl1 | 119.4 (10) | C12—C7—Cl3 | 119.5 (9) |
C6—C1—C2 | 121.1 (15) | C12—C7—C8 | 123.7 (12) |
C1—C2—H2 | 120.0 | C7—C8—H8 | 122.6 |
C1—C6—H6 | 121.3 | C7—C12—H12 | 120.5 |
C3—C2—H2 | 120.0 | C9—C8—H8 | 122.6 |
C3—C4—H4 | 120.7 | C9—C10—H10 | 120.7 |
C4—C5—H5 | 118.7 | C10—C11—H11 | 119.9 |
C5—C4—H4 | 120.7 | C11—C10—H10 | 120.7 |
C5—C6—H6 | 121.3 | C11—C12—H12 | 120.5 |
C6—C5—H5 | 118.7 | C12—C11—H11 | 119.9 |
C1—C2—C3—C4 | 1.5 (17) | C8—C9—C10—C11 | 1.7 (19) |
C1—C2—C3—Cl2 | 179.0 (7) | C9—C10—C11—C12 | −1.7 (18) |
C2—C1—C6—C5 | 1.5 (18) | C10—C11—C12—C7 | 1.1 (17) |
C2—C3—C4—C5 | −1.5 (17) | Cl1—C1—C2—C3 | −179.9 (10) |
C3—C4—C5—C6 | 1.5 (18) | Cl1—C1—C6—C5 | 179.9 (11) |
C4—C5—C6—C1 | −2 (2) | Cl2—C3—C4—C5 | −178.9 (8) |
C6—C1—C2—C3 | −1.5 (16) | C12—C7—C8—C9 | 0.3 (16) |
C7—C8—C9—C10 | −1.0 (17) | Cl3—C7—C8—C9 | 178.2 (8) |
C7—C8—C9—Cl4 | 180.0 (8) | Cl3—C7—C12—C11 | −178.2 (8) |
C8—C7—C12—C11 | −0.4 (19) | Cl4—C9—C10—C11 | −179.3 (8) |
Experimental details
(oDCB) | (mDCB) | |
Crystal data | ||
Chemical formula | C6H4Cl2 | C6H4Cl2 |
Mr | 146.99 | 146.99 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/c |
Temperature (K) | 295 | 295 |
a, b, c (Å) | 3.9274 (4), 10.5678 (10), 15.199 (9) | 3.9163 (6), 12.532 (5), 25.849 (5) |
β (°) | 96.70 (2) | 93.098 (14) |
V (Å3) | 626.5 (4) | 1266.8 (6) |
Z | 4 | 8 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.91 | 0.90 |
Crystal size (mm) | 0.44 × 0.30 × 0.12 | 0.40 × 0.25 × 0.12 |
Data collection | ||
Diffractometer | KM-4 CCD diffractometer | KM-4 CCD diffractometer |
Absorption correction | Analytical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). | Analytical Correction for absorption of the diamond-anvil cell and the sample were made using program REDSHABS (Katrusiak, A. (2003) REDSHABS. Adam Mickiewicz University Poznań; Katrusiak, A. (2004) Z. Kristallogr. 219, 461-467). |
Tmin, Tmax | 0.43, 0.79 | 0.40, 0.82 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3835, 431, 133 | 4205, 800, 627 |
Rint | 0.069 | 0.091 |
(sin θ/λ)max (Å−1) | 0.594 | 0.594 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.037, 0.63 | 0.109, 0.129, 1.47 |
No. of reflections | 431 | 800 |
No. of parameters | 73 | 146 |
No. of restraints | 111 | 222 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.22 | 0.18, −0.19 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003), SHELXS–97 (Sheldrick, 1997), SHELXL–97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1990).
Cl1—C1 | 1.71 (2) | C2—C3 | 1.403 (19) |
C1—C2 | 1.376 (18) | C3—C4 | 1.391 (11) |
C1—C6 | 1.342 (10) | C4—C5 | 1.359 (16) |
Cl2—C2 | 1.704 (9) | C5—C6 | 1.379 (17) |
C1—C2—Cl2 | 124.7 (13) | C4—C3—C2 | 120.6 (14) |
C1—C2—C3 | 116.8 (11) | C4—C5—C6 | 121.8 (9) |
C1—C6—C5 | 118.2 (14) | C5—C4—C3 | 118.8 (14) |
C2—C1—Cl1 | 117.3 (9) | C6—C1—Cl1 | 118.9 (14) |
C3—C2—Cl2 | 118.4 (9) | C6—C1—C2 | 123.7 (17) |
Cl1—C1 | 1.739 (17) | Cl3—C7 | 1.761 (13) |
C1—C2 | 1.380 (13) | C7—C8 | 1.383 (11) |
C1—C6 | 1.373 (13) | C7—C12 | 1.357 (15) |
Cl2—C3 | 1.719 (12) | Cl4—C9 | 1.741 (11) |
C2—C3 | 1.362 (15) | C8—C9 | 1.384 (13) |
C3—C4 | 1.368 (12) | C9—C10 | 1.372 (15) |
C4—C5 | 1.382 (13) | C10—C11 | 1.369 (11) |
C5—C6 | 1.360 (16) | C11—C12 | 1.383 (13) |
C2—C3—Cl2 | 119.2 (9) | C8—C9—Cl4 | 116.8 (11) |
C3—C2—C1 | 120.1 (12) | C7—C8—C9 | 114.8 (12) |
C5—C6—C1 | 117.5 (13) | C7—C12—C11 | 119.0 (12) |
C2—C1—Cl1 | 119.5 (10) | C8—C7—Cl3 | 116.8 (11) |
C4—C3—Cl2 | 120.6 (11) | C10—C9—Cl4 | 119.4 (9) |
C2—C3—C4 | 120.1 (11) | C10—C9—C8 | 123.8 (12) |
C6—C5—C4 | 122.7 (13) | C10—C11—C12 | 120.2 (14) |
C3—C4—C5 | 118.6 (14) | C11—C10—C9 | 118.5 (12) |
C6—C1—Cl1 | 119.4 (10) | C12—C7—Cl3 | 119.5 (9) |
C6—C1—C2 | 121.1 (15) | C12—C7—C8 | 123.7 (12) |
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