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The competing effects of squeezed OH...O bonds, destabilizing the H-atom position, and of displaced hydrogen donor and acceptor groups, favouring the ordered H-atom sites, have been tuned by pressure in the pressure-frozen dichloroacetic acid. Its structure has been determined at 0.1, 0.7, 0.9 and 1.4 GPa: in this pressure range the crystals are stable in the monoclinic space group P21/n. The molecules are O—H...O hydrogen bonded into dimers, which in turn interact via a unique pattern of halogen...halogen contacts. Between 0.1 and 1.4 GPa the OH...O bond is squeezed from 2.674 (13) to 2.632 (9) Å. Within the pressure range investigated the hydrogen bonds are squeezed and the shear displacement of the molecules compensate, and the H atoms remain ordered.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107037263/av5090sup1.cif
Contains datablocks dichloroacetic_acid_1, dichloroacetic_acid_2, dichloroacetic_acid_3, dichloroacetic_acid_4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107037263/av5090dichloroacetic_acid_1sup2.hkl
Contains datablock dichloroacetic_acid_1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107037263/av5090dichloroacetic_acid_2sup3.hkl
Contains datablock dichloroacetic_acid_2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107037263/av5090dichloroacetic_acid_3sup4.hkl
Contains datablock dichloroacetic_acid_3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107037263/av5090dichloroacetic_acid_4sup5.hkl
Contains datablock dichloroacetic_acid_4

CCDC references: 671595; 671596; 671597; 671598

Computing details top

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).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(dichloroacetic_acid_1) dichloroacetic acid top
Crystal data top
C2H2O2Cl2Dx = 1.822 Mg m3
Mr = 128.94Melting point: 283 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.914 (2) ÅCell parameters from 1197 reflections
b = 11.384 (7) Åθ = 3.0–29.3°
c = 8.418 (5) ŵ = 1.23 mm1
β = 93.45 (6)°T = 293 K
V = 470.1 (5) Å3Disc, colourless
Z = 40.44 × 0.40 × 0.18 mm
F(000) = 256
Data collection top
Kuma KM4CCD κ geometry
diffractometer
508 independent reflections
Radiation source: fine-focus sealed tube413 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.080
ω scansθmax = 29.3°, θmin = 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 = 66
Tmin = 0.43, Tmax = 0.89k = 1414
3383 measured reflectionsl = 56
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.117Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.191H atoms treated by a mixture of independent and constrained refinement
S = 1.37 w = 1/[σ2(Fo2) + (0.0327P)2 + 1.9238P]
where P = (Fo2 + 2Fc2)/3
508 reflections(Δ/σ)max < 0.001
59 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.31 e Å3
Crystal data top
C2H2O2Cl2V = 470.1 (5) Å3
Mr = 128.94Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.914 (2) ŵ = 1.23 mm1
b = 11.384 (7) ÅT = 293 K
c = 8.418 (5) Å0.44 × 0.40 × 0.18 mm
β = 93.45 (6)°
Data collection top
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)
Tmin = 0.43, Tmax = 0.89Rint = 0.080
3383 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.1170 restraints
wR(F2) = 0.191H atoms treated by a mixture of independent and constrained refinement
S = 1.37Δρmax = 0.24 e Å3
508 reflectionsΔρmin = 0.31 e Å3
59 parameters
Special details top

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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2403 (7)0.1223 (2)0.4428 (6)0.0694 (18)
Cl20.2874 (7)0.3278 (2)0.2459 (5)0.0772 (18)
O10.6725 (13)0.0452 (6)0.1850 (13)0.063 (4)
H10.68280.00080.10890.095*
O20.3004 (15)0.1118 (5)0.0498 (14)0.057 (4)
C10.4645 (19)0.1134 (7)0.161 (2)0.045 (6)
C20.439 (2)0.1947 (9)0.308 (2)0.041 (6)
H20.582 (18)0.216 (7)0.330 (15)0.03 (3)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.094 (2)0.071 (2)0.045 (6)0.0060 (15)0.014 (2)0.0005 (16)
Cl20.127 (3)0.049 (2)0.056 (6)0.0314 (16)0.011 (3)0.0035 (15)
O10.056 (4)0.063 (5)0.070 (15)0.021 (3)0.007 (5)0.020 (4)
O20.059 (4)0.055 (5)0.056 (15)0.021 (3)0.006 (6)0.012 (4)
C10.032 (4)0.040 (7)0.06 (2)0.009 (4)0.004 (7)0.003 (6)
C20.051 (6)0.046 (7)0.03 (2)0.001 (5)0.011 (8)0.007 (5)
Geometric parameters (Å, º) top
Cl1—C21.750 (15)O2—C11.197 (17)
Cl2—C21.753 (12)C1—C21.55 (2)
O1—C11.290 (12)
O2—C1—O1127.2 (13)C1—C2—Cl1108.2 (8)
O2—C1—C2123.1 (9)C1—C2—Cl2109.4 (12)
O1—C1—C2109.5 (13)Cl1—C2—Cl2110.9 (6)
O2—C1—C2—Cl186.8 (15)O2—C1—C2—Cl234.1 (16)
O1—C1—C2—Cl188.5 (9)O1—C1—C2—Cl2150.6 (8)
(dichloroacetic_acid_2) dichloroacetic acid top
Crystal data top
C2H2O2Cl2Dx = 2.000 Mg m3
Mr = 128.94Melting point: 283 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.6404 (18) ÅCell parameters from 1729 reflections
b = 11.134 (7) Åθ = 3.1–29.8°
c = 8.299 (5) ŵ = 1.35 mm1
β = 92.89 (5)°T = 293 K
V = 428.2 (4) Å3Disc, colourless
Z = 40.36 × 0.34 × 0.18 mm
F(000) = 256
Data collection top
Kuma KM4CCD κ geometry
diffractometer
468 independent reflections
Radiation source: fine-focus sealed tube409 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ω scansθmax = 29.8°, θmin = 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 = 66
Tmin = 0.45, Tmax = 0.88k = 1313
2443 measured reflectionsl = 77
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.30 w = 1/[σ2(Fo2) + (0.0244P)2 + 0.4612P]
where P = (Fo2 + 2Fc2)/3
468 reflections(Δ/σ)max < 0.001
63 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C2H2O2Cl2V = 428.2 (4) Å3
Mr = 128.94Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.6404 (18) ŵ = 1.35 mm1
b = 11.134 (7) ÅT = 293 K
c = 8.299 (5) Å0.36 × 0.34 × 0.18 mm
β = 92.89 (5)°
Data collection top
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)
Tmin = 0.45, Tmax = 0.88Rint = 0.051
2443 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.091H atoms treated by a mixture of independent and constrained refinement
S = 1.30Δρmax = 0.19 e Å3
468 reflectionsΔρmin = 0.16 e Å3
63 parameters
Special details top

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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2364 (3)0.11950 (12)0.4541 (2)0.0437 (5)
Cl20.2725 (3)0.33161 (11)0.2558 (2)0.0491 (5)
O10.6874 (7)0.0453 (4)0.1859 (7)0.0398 (13)
O20.2918 (7)0.1138 (3)0.0527 (5)0.0347 (11)
C10.4660 (10)0.1146 (4)0.1661 (9)0.0274 (17)
C20.4397 (10)0.1962 (5)0.3120 (9)0.0276 (16)
H20.592 (9)0.216 (4)0.362 (7)0.019 (12)*
H10.690 (11)0.012 (6)0.128 (11)0.05 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0554 (8)0.0473 (12)0.0288 (19)0.0025 (6)0.0073 (7)0.0034 (5)
Cl20.0754 (9)0.0264 (10)0.0463 (18)0.0162 (6)0.0108 (8)0.0001 (5)
O10.0352 (18)0.039 (3)0.044 (5)0.0119 (15)0.0051 (19)0.0148 (18)
O20.0395 (17)0.038 (3)0.027 (5)0.0087 (14)0.003 (2)0.0051 (14)
C10.027 (2)0.018 (4)0.038 (8)0.0013 (19)0.009 (3)0.0003 (18)
C20.028 (2)0.029 (4)0.025 (7)0.002 (2)0.002 (3)0.0022 (18)
Geometric parameters (Å, º) top
Cl1—C21.767 (7)O2—C11.210 (7)
Cl2—C21.748 (6)C1—C21.524 (8)
O1—C11.288 (6)
O2—C1—O1126.3 (5)C1—C2—Cl2110.8 (6)
O2—C1—C2123.0 (5)C1—C2—Cl1108.0 (4)
O1—C1—C2110.5 (6)Cl2—C2—Cl1110.5 (3)
O2—C1—C2—Cl231.9 (7)O2—C1—C2—Cl189.2 (7)
O1—C1—C2—Cl2151.0 (4)O1—C1—C2—Cl187.8 (4)
(dichloroacetic_acid_3) dichloroacetic acid top
Crystal data top
C2H2O2Cl2Dx = 2.008 Mg m3
Mr = 128.94Melting point: 283 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.6589 (9) ÅCell parameters from 2076 reflections
b = 11.174 (2) Åθ = 4.4–25.1°
c = 8.2013 (16) ŵ = 1.36 mm1
β = 92.88 (3)°T = 293 K
V = 426.42 (14) Å3Disc, colourless
Z = 40.46 × 0.44 × 0.18 mm
F(000) = 256
Data collection top
Kuma KM4CCD κ geometry
diffractometer
176 independent reflections
Radiation source: fine-focus sealed tube166 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
ω scansθmax = 25.1°, θmin = 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 = 55
Tmin = 0.71, Tmax = 0.97k = 1111
1184 measured reflectionsl = 44
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0232P)2 + 0.6301P]
where P = (Fo2 + 2Fc2)/3
176 reflections(Δ/σ)max < 0.001
58 parametersΔρmax = 0.10 e Å3
0 restraintsΔρmin = 0.12 e Å3
Crystal data top
C2H2O2Cl2V = 426.42 (14) Å3
Mr = 128.94Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.6589 (9) ŵ = 1.36 mm1
b = 11.174 (2) ÅT = 293 K
c = 8.2013 (16) Å0.46 × 0.44 × 0.18 mm
β = 92.88 (3)°
Data collection top
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)
Tmin = 0.71, Tmax = 0.97Rint = 0.041
1184 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.057H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.10 e Å3
176 reflectionsΔρmin = 0.12 e Å3
58 parameters
Special details top

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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2358 (3)0.11942 (13)0.4557 (3)0.0400 (18)
Cl20.2723 (3)0.33199 (13)0.2568 (3)0.0460 (15)
O10.6891 (7)0.0453 (4)0.1862 (9)0.038 (4)
O20.2923 (9)0.1129 (4)0.0540 (10)0.028 (4)
C10.4648 (12)0.1142 (5)0.1671 (13)0.027 (5)
C20.4416 (12)0.1967 (5)0.3121 (13)0.0247 (16)*
H20.613 (10)0.210 (4)0.366 (10)0.025 (14)*
H10.666 (18)0.022 (9)0.14 (3)0.11 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0531 (9)0.046 (2)0.022 (7)0.0025 (6)0.0102 (12)0.0022 (7)
Cl20.0710 (10)0.0277 (18)0.040 (6)0.0161 (6)0.0113 (13)0.0001 (7)
O10.0331 (18)0.031 (6)0.048 (16)0.0118 (17)0.004 (3)0.011 (2)
O20.0359 (19)0.033 (4)0.014 (16)0.0060 (16)0.006 (3)0.009 (2)
C10.027 (3)0.013 (6)0.04 (2)0.002 (2)0.005 (5)0.002 (3)
Geometric parameters (Å, º) top
Cl1—C21.779 (9)O2—C11.196 (9)
Cl2—C21.754 (7)C1—C21.513 (11)
O1—C11.301 (7)
O2—C1—O1126.2 (7)C1—C2—Cl2111.8 (8)
O2—C1—C2123.0 (6)C1—C2—Cl1106.6 (5)
O1—C1—C2110.8 (8)Cl2—C2—Cl1109.8 (3)
O2—C1—C2—Cl230.9 (10)O2—C1—C2—Cl189.1 (9)
O1—C1—C2—Cl2150.8 (5)O1—C1—C2—Cl189.2 (5)
(dichloroacetic_acid_4) top
Crystal data top
C2H2O2Cl2Dx = 2.116 Mg m3
Mr = 128.94Melting point: 283 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.563 (2) ÅCell parameters from 1711 reflections
b = 10.978 (8) Åθ = 3.1–24.0°
c = 8.087 (6) ŵ = 1.43 mm1
β = 92.60 (6)°T = 293 K
V = 404.7 (4) Å3Disc, colourless
Z = 40.44 × 0.42 × 0.18 mm
F(000) = 256
Data collection top
Kuma KM4CCD κ geometry
diffractometer
146 independent reflections
Radiation source: fine-focus sealed tube141 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 24.0°, θmin = 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 = 55
Tmin = 0.73, Tmax = 0.97k = 99
936 measured reflectionsl = 55
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.22 w = 1/[σ2(Fo2) + (0.046P)2 + 0.3851P]
where P = (Fo2 + 2Fc2)/3
146 reflections(Δ/σ)max < 0.001
57 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C2H2O2Cl2V = 404.7 (4) Å3
Mr = 128.94Z = 4
Monoclinic, P21/nMo Kα radiation
a = 4.563 (2) ŵ = 1.43 mm1
b = 10.978 (8) ÅT = 293 K
c = 8.087 (6) Å0.44 × 0.42 × 0.18 mm
β = 92.60 (6)°
Data collection top
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)
Tmin = 0.73, Tmax = 0.97Rint = 0.038
936 measured reflectionsθmax = 24.0°
Refinement top
R[F2 > 2σ(F2)] = 0.0300 restraints
wR(F2) = 0.073H atoms treated by a mixture of independent and constrained refinement
S = 1.22Δρmax = 0.16 e Å3
146 reflectionsΔρmin = 0.15 e Å3
57 parameters
Special details top

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 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.2335 (4)0.1185 (2)0.4604 (4)0.0340 (14)
Cl20.2664 (4)0.3341 (3)0.2609 (3)0.0385 (14)
O10.6962 (10)0.0434 (9)0.1900 (13)0.026 (4)
O20.2870 (12)0.1145 (6)0.0543 (11)0.025 (3)
C10.4643 (18)0.1152 (11)0.167 (2)0.021 (4)
C20.4409 (19)0.1976 (11)0.316 (2)0.025 (2)*
H20.602 (15)0.217 (7)0.345 (12)0.030*
H10.699 (19)0.010 (12)0.06 (2)0.07 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0440 (13)0.047 (5)0.012 (7)0.0026 (9)0.0059 (14)0.0031 (11)
Cl20.0589 (14)0.019 (5)0.038 (8)0.0099 (10)0.0080 (14)0.0002 (9)
O10.024 (2)0.045 (13)0.01 (2)0.012 (2)0.003 (4)0.009 (3)
O20.026 (3)0.036 (12)0.013 (16)0.001 (2)0.004 (4)0.008 (3)
C10.025 (4)0.023 (13)0.01 (2)0.006 (4)0.011 (6)0.004 (4)
Geometric parameters (Å, º) top
Cl1—C21.764 (16)O2—C11.189 (14)
Cl2—C21.746 (14)C1—C21.518 (15)
O1—C11.327 (14)
O2—C1—O1128.0 (9)C1—C2—Cl2110.8 (15)
O2—C1—C2122.9 (10)C1—C2—Cl1107.0 (11)
O1—C1—C2108.9 (14)Cl2—C2—Cl1109.9 (4)
O2—C1—C2—Cl231 (2)O2—C1—C2—Cl188 (2)
O1—C1—C2—Cl2152.4 (7)O1—C1—C2—Cl187.9 (8)

Experimental details

(dichloroacetic_acid_1)(dichloroacetic_acid_2)(dichloroacetic_acid_3)(dichloroacetic_acid_4)
Crystal data
Chemical formulaC2H2O2Cl2C2H2O2Cl2C2H2O2Cl2C2H2O2Cl2
Mr128.94128.94128.94128.94
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)293293293293
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)
V3)470.1 (5)428.2 (4)426.42 (14)404.7 (4)
Z4444
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)1.231.351.361.43
Crystal size (mm)0.44 × 0.40 × 0.180.36 × 0.34 × 0.180.46 × 0.44 × 0.180.44 × 0.42 × 0.18
Data collection
DiffractometerKuma KM4CCD κ geometry
diffractometer
Kuma KM4CCD κ geometry
diffractometer
Kuma KM4CCD κ geometry
diffractometer
Kuma KM4CCD κ geometry
diffractometer
Absorption correctionAnalytical
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

Tmin, Tmax0.43, 0.890.45, 0.880.71, 0.970.73, 0.97
No. of measured, independent and
observed [I > 2σ(I)] reflections
3383, 508, 413 2443, 468, 409 1184, 176, 166 936, 146, 141
Rint0.0800.0510.0410.038
θmax (°)29.329.825.124.0
(sin θ/λ)max1)0.6880.6980.5970.573
Refinement
R[F2 > 2σ(F2)], wR(F2), 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 reflections508468176146
No. of parameters59635857
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.24, 0.310.19, 0.160.10, 0.120.16, 0.15

Computer programs: CrysAlis (Oxford Diffraction, 2003), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1990).

 

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