Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107037263/av5090sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107037263/av5090dichloroacetic_acid_1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107037263/av5090dichloroacetic_acid_2sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107037263/av5090dichloroacetic_acid_3sup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768107037263/av5090dichloroacetic_acid_4sup5.hkl |
CCDC references: 671595; 671596; 671597; 671598
For all compounds, data collection: CrysAlis (Oxford Diffraction, 2003); cell refinement: CrysAlis (Oxford Diffraction, 2003); data reduction: CrysAlis (Oxford Diffraction, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C_{2}H_{2}O_{2}Cl_{2} | D_{x} = 1.822 Mg m^{−}^{3} |
M_{r} = 128.94 | Melting point: 283 K |
Monoclinic, P2_{1}/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.914 (2) Å | Cell parameters from 1197 reflections |
b = 11.384 (7) Å | θ = 3.0–29.3° |
c = 8.418 (5) Å | µ = 1.23 mm^{−}^{1} |
β = 93.45 (6)° | T = 293 K |
V = 470.1 (5) Å^{3} | Disc, colourless |
Z = 4 | 0.44 × 0.40 × 0.18 mm |
F(000) = 256 |
Kuma KM4CCD κ geometry diffractometer | 508 independent reflections |
Radiation source: fine-focus sealed tube | 413 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.080 |
ω scans | θ_{max} = 29.3°, θ_{min} = 3.0° |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | h = −6→6 |
T_{min} = 0.43, T_{max} = 0.89 | k = −14→14 |
3383 measured reflections | l = −5→6 |
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.117 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.191 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.37 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0327P)^{2} + 1.9238P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
508 reflections | (Δ/σ)_{max} < 0.001 |
59 parameters | Δρ_{max} = 0.24 e Å^{−}^{3} |
0 restraints | Δρ_{min} = −0.31 e Å^{−}^{3} |
C_{2}H_{2}O_{2}Cl_{2} | V = 470.1 (5) Å^{3} |
M_{r} = 128.94 | Z = 4 |
Monoclinic, P2_{1}/n | Mo Kα radiation |
a = 4.914 (2) Å | µ = 1.23 mm^{−}^{1} |
b = 11.384 (7) Å | T = 293 K |
c = 8.418 (5) Å | 0.44 × 0.40 × 0.18 mm |
β = 93.45 (6)° |
Kuma KM4CCD κ geometry diffractometer | 508 independent reflections |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | 413 reflections with I > 2σ(I) |
T_{min} = 0.43, T_{max} = 0.89 | R_{int} = 0.080 |
3383 measured reflections |
R[F^{2} > 2σ(F^{2})] = 0.117 | 0 restraints |
wR(F^{2}) = 0.191 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.37 | Δρ_{max} = 0.24 e Å^{−}^{3} |
508 reflections | Δρ_{min} = −0.31 e Å^{−}^{3} |
59 parameters |
Experimental. High-pressure measurement at 0.1 GPa. |
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 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} > σ(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 | U_{iso}*/U_{eq} | ||
Cl1 | 0.2403 (7) | 0.1223 (2) | 0.4428 (6) | 0.0694 (18) | |
Cl2 | 0.2874 (7) | 0.3278 (2) | 0.2459 (5) | 0.0772 (18) | |
O1 | 0.6725 (13) | 0.0452 (6) | 0.1850 (13) | 0.063 (4) | |
H1 | 0.6828 | 0.0008 | 0.1089 | 0.095* | |
O2 | 0.3004 (15) | 0.1118 (5) | 0.0498 (14) | 0.057 (4) | |
C1 | 0.4645 (19) | 0.1134 (7) | 0.161 (2) | 0.045 (6) | |
C2 | 0.439 (2) | 0.1947 (9) | 0.308 (2) | 0.041 (6) | |
H2 | 0.582 (18) | 0.216 (7) | 0.330 (15) | 0.03 (3)* |
U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} | |
Cl1 | 0.094 (2) | 0.071 (2) | 0.045 (6) | −0.0060 (15) | 0.014 (2) | 0.0005 (16) |
Cl2 | 0.127 (3) | 0.049 (2) | 0.056 (6) | 0.0314 (16) | 0.011 (3) | −0.0035 (15) |
O1 | 0.056 (4) | 0.063 (5) | 0.070 (15) | 0.021 (3) | −0.007 (5) | −0.020 (4) |
O2 | 0.059 (4) | 0.055 (5) | 0.056 (15) | 0.021 (3) | −0.006 (6) | −0.012 (4) |
C1 | 0.032 (4) | 0.040 (7) | 0.06 (2) | −0.009 (4) | 0.004 (7) | 0.003 (6) |
C2 | 0.051 (6) | 0.046 (7) | 0.03 (2) | 0.001 (5) | 0.011 (8) | −0.007 (5) |
Cl1—C2 | 1.750 (15) | O2—C1 | 1.197 (17) |
Cl2—C2 | 1.753 (12) | C1—C2 | 1.55 (2) |
O1—C1 | 1.290 (12) | ||
O2—C1—O1 | 127.2 (13) | C1—C2—Cl1 | 108.2 (8) |
O2—C1—C2 | 123.1 (9) | C1—C2—Cl2 | 109.4 (12) |
O1—C1—C2 | 109.5 (13) | Cl1—C2—Cl2 | 110.9 (6) |
O2—C1—C2—Cl1 | 86.8 (15) | O2—C1—C2—Cl2 | −34.1 (16) |
O1—C1—C2—Cl1 | −88.5 (9) | O1—C1—C2—Cl2 | 150.6 (8) |
C_{2}H_{2}O_{2}Cl_{2} | D_{x} = 2.000 Mg m^{−}^{3} |
M_{r} = 128.94 | Melting point: 283 K |
Monoclinic, P2_{1}/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.6404 (18) Å | Cell parameters from 1729 reflections |
b = 11.134 (7) Å | θ = 3.1–29.8° |
c = 8.299 (5) Å | µ = 1.35 mm^{−}^{1} |
β = 92.89 (5)° | T = 293 K |
V = 428.2 (4) Å^{3} | Disc, colourless |
Z = 4 | 0.36 × 0.34 × 0.18 mm |
F(000) = 256 |
Kuma KM4CCD κ geometry diffractometer | 468 independent reflections |
Radiation source: fine-focus sealed tube | 409 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.051 |
ω scans | θ_{max} = 29.8°, θ_{min} = 3.1° |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | h = −6→6 |
T_{min} = 0.45, T_{max} = 0.88 | k = −13→13 |
2443 measured reflections | l = −7→7 |
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.30 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0244P)^{2} + 0.4612P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
468 reflections | (Δ/σ)_{max} < 0.001 |
63 parameters | Δρ_{max} = 0.19 e Å^{−}^{3} |
0 restraints | Δρ_{min} = −0.16 e Å^{−}^{3} |
C_{2}H_{2}O_{2}Cl_{2} | V = 428.2 (4) Å^{3} |
M_{r} = 128.94 | Z = 4 |
Monoclinic, P2_{1}/n | Mo Kα radiation |
a = 4.6404 (18) Å | µ = 1.35 mm^{−}^{1} |
b = 11.134 (7) Å | T = 293 K |
c = 8.299 (5) Å | 0.36 × 0.34 × 0.18 mm |
β = 92.89 (5)° |
Kuma KM4CCD κ geometry diffractometer | 468 independent reflections |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | 409 reflections with I > 2σ(I) |
T_{min} = 0.45, T_{max} = 0.88 | R_{int} = 0.051 |
2443 measured reflections |
R[F^{2} > 2σ(F^{2})] = 0.053 | 0 restraints |
wR(F^{2}) = 0.091 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.30 | Δρ_{max} = 0.19 e Å^{−}^{3} |
468 reflections | Δρ_{min} = −0.16 e Å^{−}^{3} |
63 parameters |
Experimental. High-pressure measurement at 0.7 GPa. |
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 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} > σ(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 | U_{iso}*/U_{eq} | ||
Cl1 | 0.2364 (3) | 0.11950 (12) | 0.4541 (2) | 0.0437 (5) | |
Cl2 | 0.2725 (3) | 0.33161 (11) | 0.2558 (2) | 0.0491 (5) | |
O1 | 0.6874 (7) | 0.0453 (4) | 0.1859 (7) | 0.0398 (13) | |
O2 | 0.2918 (7) | 0.1138 (3) | 0.0527 (5) | 0.0347 (11) | |
C1 | 0.4660 (10) | 0.1146 (4) | 0.1661 (9) | 0.0274 (17) | |
C2 | 0.4397 (10) | 0.1962 (5) | 0.3120 (9) | 0.0276 (16) | |
H2 | 0.592 (9) | 0.216 (4) | 0.362 (7) | 0.019 (12)* | |
H1 | 0.690 (11) | −0.012 (6) | 0.128 (11) | 0.05 (2)* |
U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} | |
Cl1 | 0.0554 (8) | 0.0473 (12) | 0.0288 (19) | −0.0025 (6) | 0.0073 (7) | 0.0034 (5) |
Cl2 | 0.0754 (9) | 0.0264 (10) | 0.0463 (18) | 0.0162 (6) | 0.0108 (8) | 0.0001 (5) |
O1 | 0.0352 (18) | 0.039 (3) | 0.044 (5) | 0.0119 (15) | −0.0051 (19) | −0.0148 (18) |
O2 | 0.0395 (17) | 0.038 (3) | 0.027 (5) | 0.0087 (14) | −0.003 (2) | −0.0051 (14) |
C1 | 0.027 (2) | 0.018 (4) | 0.038 (8) | −0.0013 (19) | 0.009 (3) | 0.0003 (18) |
C2 | 0.028 (2) | 0.029 (4) | 0.025 (7) | 0.002 (2) | −0.002 (3) | −0.0022 (18) |
Cl1—C2 | 1.767 (7) | O2—C1 | 1.210 (7) |
Cl2—C2 | 1.748 (6) | C1—C2 | 1.524 (8) |
O1—C1 | 1.288 (6) | ||
O2—C1—O1 | 126.3 (5) | C1—C2—Cl2 | 110.8 (6) |
O2—C1—C2 | 123.0 (5) | C1—C2—Cl1 | 108.0 (4) |
O1—C1—C2 | 110.5 (6) | Cl2—C2—Cl1 | 110.5 (3) |
O2—C1—C2—Cl2 | −31.9 (7) | O2—C1—C2—Cl1 | 89.2 (7) |
O1—C1—C2—Cl2 | 151.0 (4) | O1—C1—C2—Cl1 | −87.8 (4) |
C_{2}H_{2}O_{2}Cl_{2} | D_{x} = 2.008 Mg m^{−}^{3} |
M_{r} = 128.94 | Melting point: 283 K |
Monoclinic, P2_{1}/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.6589 (9) Å | Cell parameters from 2076 reflections |
b = 11.174 (2) Å | θ = 4.4–25.1° |
c = 8.2013 (16) Å | µ = 1.36 mm^{−}^{1} |
β = 92.88 (3)° | T = 293 K |
V = 426.42 (14) Å^{3} | Disc, colourless |
Z = 4 | 0.46 × 0.44 × 0.18 mm |
F(000) = 256 |
Kuma KM4CCD κ geometry diffractometer | 176 independent reflections |
Radiation source: fine-focus sealed tube | 166 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.041 |
ω scans | θ_{max} = 25.1°, θ_{min} = 4.4° |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | h = −5→5 |
T_{min} = 0.71, T_{max} = 0.97 | k = −11→11 |
1184 measured reflections | l = −4→4 |
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0232P)^{2} + 0.6301P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
176 reflections | (Δ/σ)_{max} < 0.001 |
58 parameters | Δρ_{max} = 0.10 e Å^{−}^{3} |
0 restraints | Δρ_{min} = −0.12 e Å^{−}^{3} |
C_{2}H_{2}O_{2}Cl_{2} | V = 426.42 (14) Å^{3} |
M_{r} = 128.94 | Z = 4 |
Monoclinic, P2_{1}/n | Mo Kα radiation |
a = 4.6589 (9) Å | µ = 1.36 mm^{−}^{1} |
b = 11.174 (2) Å | T = 293 K |
c = 8.2013 (16) Å | 0.46 × 0.44 × 0.18 mm |
β = 92.88 (3)° |
Kuma KM4CCD κ geometry diffractometer | 176 independent reflections |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | 166 reflections with I > 2σ(I) |
T_{min} = 0.71, T_{max} = 0.97 | R_{int} = 0.041 |
1184 measured reflections |
R[F^{2} > 2σ(F^{2})] = 0.025 | 0 restraints |
wR(F^{2}) = 0.057 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρ_{max} = 0.10 e Å^{−}^{3} |
176 reflections | Δρ_{min} = −0.12 e Å^{−}^{3} |
58 parameters |
Experimental. High-pressure measurement at 0.9 GPa. |
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 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} > σ(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 | U_{iso}*/U_{eq} | ||
Cl1 | 0.2358 (3) | 0.11942 (13) | 0.4557 (3) | 0.0400 (18) | |
Cl2 | 0.2723 (3) | 0.33199 (13) | 0.2568 (3) | 0.0460 (15) | |
O1 | 0.6891 (7) | 0.0453 (4) | 0.1862 (9) | 0.038 (4) | |
O2 | 0.2923 (9) | 0.1129 (4) | 0.0540 (10) | 0.028 (4) | |
C1 | 0.4648 (12) | 0.1142 (5) | 0.1671 (13) | 0.027 (5) | |
C2 | 0.4416 (12) | 0.1967 (5) | 0.3121 (13) | 0.0247 (16)* | |
H2 | 0.613 (10) | 0.210 (4) | 0.366 (10) | 0.025 (14)* | |
H1 | 0.666 (18) | −0.022 (9) | 0.14 (3) | 0.11 (4)* |
U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} | |
Cl1 | 0.0531 (9) | 0.046 (2) | 0.022 (7) | −0.0025 (6) | 0.0102 (12) | 0.0022 (7) |
Cl2 | 0.0710 (10) | 0.0277 (18) | 0.040 (6) | 0.0161 (6) | 0.0113 (13) | 0.0001 (7) |
O1 | 0.0331 (18) | 0.031 (6) | 0.048 (16) | 0.0118 (17) | −0.004 (3) | −0.011 (2) |
O2 | 0.0359 (19) | 0.033 (4) | 0.014 (16) | 0.0060 (16) | −0.006 (3) | −0.009 (2) |
C1 | 0.027 (3) | 0.013 (6) | 0.04 (2) | −0.002 (2) | 0.005 (5) | −0.002 (3) |
Cl1—C2 | 1.779 (9) | O2—C1 | 1.196 (9) |
Cl2—C2 | 1.754 (7) | C1—C2 | 1.513 (11) |
O1—C1 | 1.301 (7) | ||
O2—C1—O1 | 126.2 (7) | C1—C2—Cl2 | 111.8 (8) |
O2—C1—C2 | 123.0 (6) | C1—C2—Cl1 | 106.6 (5) |
O1—C1—C2 | 110.8 (8) | Cl2—C2—Cl1 | 109.8 (3) |
O2—C1—C2—Cl2 | −30.9 (10) | O2—C1—C2—Cl1 | 89.1 (9) |
O1—C1—C2—Cl2 | 150.8 (5) | O1—C1—C2—Cl1 | −89.2 (5) |
C_{2}H_{2}O_{2}Cl_{2} | D_{x} = 2.116 Mg m^{−}^{3} |
M_{r} = 128.94 | Melting point: 283 K |
Monoclinic, P2_{1}/n | Mo Kα radiation, λ = 0.71073 Å |
a = 4.563 (2) Å | Cell parameters from 1711 reflections |
b = 10.978 (8) Å | θ = 3.1–24.0° |
c = 8.087 (6) Å | µ = 1.43 mm^{−}^{1} |
β = 92.60 (6)° | T = 293 K |
V = 404.7 (4) Å^{3} | Disc, colourless |
Z = 4 | 0.44 × 0.42 × 0.18 mm |
F(000) = 256 |
Kuma KM4CCD κ geometry diffractometer | 146 independent reflections |
Radiation source: fine-focus sealed tube | 141 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.038 |
ω scans | θ_{max} = 24.0°, θ_{min} = 3.1° |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | h = −5→5 |
T_{min} = 0.73, T_{max} = 0.97 | k = −9→9 |
936 measured reflections | l = −5→5 |
Refinement on F^{2} | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F^{2} > 2σ(F^{2})] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.22 | w = 1/[σ^{2}(F_{o}^{2}) + (0.046P)^{2} + 0.3851P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
146 reflections | (Δ/σ)_{max} < 0.001 |
57 parameters | Δρ_{max} = 0.16 e Å^{−}^{3} |
0 restraints | Δρ_{min} = −0.15 e Å^{−}^{3} |
C_{2}H_{2}O_{2}Cl_{2} | V = 404.7 (4) Å^{3} |
M_{r} = 128.94 | Z = 4 |
Monoclinic, P2_{1}/n | Mo Kα radiation |
a = 4.563 (2) Å | µ = 1.43 mm^{−}^{1} |
b = 10.978 (8) Å | T = 293 K |
c = 8.087 (6) Å | 0.44 × 0.42 × 0.18 mm |
β = 92.60 (6)° |
Kuma KM4CCD κ geometry diffractometer | 146 independent reflections |
Absorption correction: analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | 141 reflections with I > 2σ(I) |
T_{min} = 0.73, T_{max} = 0.97 | R_{int} = 0.038 |
936 measured reflections | θ_{max} = 24.0° |
R[F^{2} > 2σ(F^{2})] = 0.030 | 0 restraints |
wR(F^{2}) = 0.073 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.22 | Δρ_{max} = 0.16 e Å^{−}^{3} |
146 reflections | Δρ_{min} = −0.15 e Å^{−}^{3} |
57 parameters |
Experimental. High-pressure measurement at 1.4 GPa. |
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 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} > σ(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 | U_{iso}*/U_{eq} | ||
Cl1 | 0.2335 (4) | 0.1185 (2) | 0.4604 (4) | 0.0340 (14) | |
Cl2 | 0.2664 (4) | 0.3341 (3) | 0.2609 (3) | 0.0385 (14) | |
O1 | 0.6962 (10) | 0.0434 (9) | 0.1900 (13) | 0.026 (4) | |
O2 | 0.2870 (12) | 0.1145 (6) | 0.0543 (11) | 0.025 (3) | |
C1 | 0.4643 (18) | 0.1152 (11) | 0.167 (2) | 0.021 (4) | |
C2 | 0.4409 (19) | 0.1976 (11) | 0.316 (2) | 0.025 (2)* | |
H2 | 0.602 (15) | 0.217 (7) | 0.345 (12) | 0.030* | |
H1 | 0.699 (19) | 0.010 (12) | 0.06 (2) | 0.07 (4)* |
U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} | |
Cl1 | 0.0440 (13) | 0.047 (5) | 0.012 (7) | −0.0026 (9) | 0.0059 (14) | 0.0031 (11) |
Cl2 | 0.0589 (14) | 0.019 (5) | 0.038 (8) | 0.0099 (10) | 0.0080 (14) | −0.0002 (9) |
O1 | 0.024 (2) | 0.045 (13) | 0.01 (2) | 0.012 (2) | −0.003 (4) | −0.009 (3) |
O2 | 0.026 (3) | 0.036 (12) | 0.013 (16) | −0.001 (2) | −0.004 (4) | −0.008 (3) |
C1 | 0.025 (4) | 0.023 (13) | 0.01 (2) | −0.006 (4) | 0.011 (6) | −0.004 (4) |
Cl1—C2 | 1.764 (16) | O2—C1 | 1.189 (14) |
Cl2—C2 | 1.746 (14) | C1—C2 | 1.518 (15) |
O1—C1 | 1.327 (14) | ||
O2—C1—O1 | 128.0 (9) | C1—C2—Cl2 | 110.8 (15) |
O2—C1—C2 | 122.9 (10) | C1—C2—Cl1 | 107.0 (11) |
O1—C1—C2 | 108.9 (14) | Cl2—C2—Cl1 | 109.9 (4) |
O2—C1—C2—Cl2 | −31 (2) | O2—C1—C2—Cl1 | 88 (2) |
O1—C1—C2—Cl2 | 152.4 (7) | O1—C1—C2—Cl1 | −87.9 (8) |
Experimental details
(dichloroacetic_acid_1) | (dichloroacetic_acid_2) | (dichloroacetic_acid_3) | (dichloroacetic_acid_4) | |
Crystal data | ||||
Chemical formula | C_{2}H_{2}O_{2}Cl_{2} | C_{2}H_{2}O_{2}Cl_{2} | C_{2}H_{2}O_{2}Cl_{2} | C_{2}H_{2}O_{2}Cl_{2} |
M_{r} | 128.94 | 128.94 | 128.94 | 128.94 |
Crystal system, space group | Monoclinic, P2_{1}/n | Monoclinic, P2_{1}/n | Monoclinic, P2_{1}/n | Monoclinic, P2_{1}/n |
Temperature (K) | 293 | 293 | 293 | 293 |
a, b, c (Å) | 4.914 (2), 11.384 (7), 8.418 (5) | 4.6404 (18), 11.134 (7), 8.299 (5) | 4.6589 (9), 11.174 (2), 8.2013 (16) | 4.563 (2), 10.978 (8), 8.087 (6) |
β (°) | 93.45 (6) | 92.89 (5) | 92.88 (3) | 92.60 (6) |
V (Å^{3}) | 470.1 (5) | 428.2 (4) | 426.42 (14) | 404.7 (4) |
Z | 4 | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm^{−}^{1}) | 1.23 | 1.35 | 1.36 | 1.43 |
Crystal size (mm) | 0.44 × 0.40 × 0.18 | 0.36 × 0.34 × 0.18 | 0.46 × 0.44 × 0.18 | 0.44 × 0.42 × 0.18 |
Data collection | ||||
Diffractometer | Kuma KM4CCD κ geometry diffractometer | Kuma KM4CCD κ geometry diffractometer | Kuma KM4CCD κ geometry diffractometer | Kuma KM4CCD κ geometry diffractometer |
Absorption correction | Analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | Analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | Analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 | Analytical Katrusiak, A. (2003). REDSHADE - Program for correcting reflections intensities for DAC absorption, gasket shadowing and sample crystal absorption. Adam Mickiewicz University, Poznań. Katrusiak, A. (2004). Z. Kristallogr. 219, 461-467 |
T_{min}, T_{max} | 0.43, 0.89 | 0.45, 0.88 | 0.71, 0.97 | 0.73, 0.97 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3383, 508, 413 | 2443, 468, 409 | 1184, 176, 166 | 936, 146, 141 |
R_{int} | 0.080 | 0.051 | 0.041 | 0.038 |
θ_{max} (°) | 29.3 | 29.8 | 25.1 | 24.0 |
(sin θ/λ)_{max} (Å^{−}^{1}) | 0.688 | 0.698 | 0.597 | 0.573 |
Refinement | ||||
R[F^{2} > 2σ(F^{2})], wR(F^{2}), S | 0.117, 0.191, 1.37 | 0.053, 0.091, 1.30 | 0.025, 0.057, 1.10 | 0.030, 0.073, 1.22 |
No. of reflections | 508 | 468 | 176 | 146 |
No. of parameters | 59 | 63 | 58 | 57 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρ_{max}, Δρ_{min} (e Å^{−}^{3}) | 0.24, −0.31 | 0.19, −0.16 | 0.10, −0.12 | 0.16, −0.15 |
Computer programs: CrysAlis (Oxford Diffraction, 2003), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1990).