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Bromochloromethane, CH2BrCl, has been temperature-frozen and in situ pressure-frozen and the structure determined by X-ray diffraction at low temperatures of 170 and 100 K at ambient pressure (0.10 MPa), and at high pressures of 1.04 and 1.72 GPa at room temperature (295 K). CH2BrCl exhibits a remarkable polymorphism: at low temperature it crystallizes in the monoclinic space group C2/c (phase I), isostructural to the crystals of CH2Br2. The pressure-frozen crystal of CH2BrCl is orthorhombic, space group Pbcn, and is isostructural to the crystal of CH2Cl2. In both phases I and II the Br and Cl atoms are substitutionally disordered. The freezing temperatures and pressures of simple dihalomethanes have been correlated to their molecular weight and halogen... halogen distances. Calculated electrostatic potential surfaces have been related to the different crystal packing of dihalomethanes investigated.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107044618/av5094sup1.cif
Contains datablocks global, cbm_170K, cbm_100K, cbm_1.04GPa, cbm_1.72GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107044618/av5094cbm_170Ksup2.hkl
Contains datablock cbm_170K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107044618/av5094cbm_100Ksup3.hkl
Contains datablock cbm_100K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107044618/av5094cbm_1.04GPasup4.hkl
Contains datablock cbm_1.04GPa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107044618/av5094cbm_1.72GPasup5.hkl
Contains datablock cbm_1.72GPa

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S0108768107044618/av5094sup6.pdf
Supplementary material

CCDC references: 671599; 671600; 671601; 671602

Computing details top

For all compounds, data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004). Data reduction: CrysAlis RED (Oxford Diffraction, 2004) for cbm_170K, cbm_100K; CrysAlis RED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003) for cbm_1.04GPa, cbm_1.72GPa. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for cbm_170K, cbm_100K; SHELXS–97 (Sheldrick, 1997) for cbm_1.04GPa, cbm_1.72GPa. Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for cbm_170K, cbm_100K; SHELXL–97 (Sheldrick, 1997) for cbm_1.04GPa, cbm_1.72GPa. For all compounds, molecular graphics: X-SEED 2.0; software used to prepare material for publication: SHELXL–97 (Sheldrick, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(cbm_170K) bromochloromethane top
Crystal data top
CH2BrClDx = 2.357 Mg m3
Mr = 129.39Melting point: 185 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 11.959 (2) ÅCell parameters from 1010 reflections
b = 4.4531 (9) Åθ = 3.0–29.1°
c = 14.873 (3) ŵ = 11.73 mm1
β = 112.96 (3)°T = 170 K
V = 729.3 (3) Å3Irregular, colourless
Z = 80.12 × 0.12 × 0.10 mm
F(000) = 480
Data collection top
KM-4 CCD
diffractometer
909 independent reflections
Radiation source: fine-focus sealed tube643 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.109
ω–scansθmax = 29.1°, θmin = 3.0°
Absorption correction: multi-scan
Correction for absorption was made using XEMP (SHELXTL, Sheldrick (1990)).
h = 1516
Tmin = 0.22, Tmax = 0.32k = 45
2422 measured reflectionsl = 2019
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.172 w = 1/[σ2(Fo2) + (0.0777P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max = 0.009
909 reflectionsΔρmax = 0.83 e Å3
36 parametersΔρmin = 0.66 e Å3
6 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.036 (4)
Crystal data top
CH2BrClV = 729.3 (3) Å3
Mr = 129.39Z = 8
Monoclinic, C2/cMo Kα radiation
a = 11.959 (2) ŵ = 11.73 mm1
b = 4.4531 (9) ÅT = 170 K
c = 14.873 (3) Å0.12 × 0.12 × 0.10 mm
β = 112.96 (3)°
Data collection top
KM-4 CCD
diffractometer
909 independent reflections
Absorption correction: multi-scan
Correction for absorption was made using XEMP (SHELXTL, Sheldrick (1990)).
643 reflections with I > 2σ(I)
Tmin = 0.22, Tmax = 0.32Rint = 0.109
2422 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0666 restraints
wR(F2) = 0.172H atoms treated by a mixture of independent and constrained refinement
S = 1.15Δρmax = 0.83 e Å3
909 reflectionsΔρmin = 0.66 e Å3
36 parameters
Special details top

Experimental. Data were collected at ambient pressure (100 kPa) and 170 K with the crystal obtained by the in situ low-temperature crystallization technique.

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*/UeqOcc. (<1)
Br10.09023 (3)0.6643 (2)0.13228 (7)0.0531 (5)0.508 (3)
Cl10.09023 (3)0.6643 (2)0.13228 (7)0.0531 (5)0.492 (3)
Br20.34640 (3)0.6410 (2)0.13258 (7)0.0495 (5)0.492 (3)
Cl20.34640 (3)0.6410 (2)0.13258 (7)0.0495 (5)0.508 (3)
C10.2014 (6)0.43217 (10)0.1066 (2)0.057 (2)
H10.16979 (17)0.3694 (12)0.0388 (4)0.069*
H20.22013 (17)0.2511 (2)0.1460 (3)0.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0468 (7)0.0539 (7)0.0632 (8)0.0041 (4)0.0265 (5)0.0092 (4)
Cl10.0468 (7)0.0539 (7)0.0632 (8)0.0041 (4)0.0265 (5)0.0092 (4)
Br20.0369 (6)0.0517 (7)0.0577 (8)0.0020 (4)0.0159 (5)0.0027 (4)
Cl20.0369 (6)0.0517 (7)0.0577 (8)0.0020 (4)0.0159 (5)0.0027 (4)
C10.066 (5)0.026 (3)0.085 (5)0.003 (3)0.034 (4)0.007 (3)
Geometric parameters (Å, º) top
Br1—C11.837 (6)Br2—C11.871 (6)
Cl1—C11.837 (6)Cl2—C11.871 (6)
Cl1—C1—Br10.00 (5)Cl1—C1—Br2111.41 (8)
Cl1—C1—Cl2111.41 (8)Br1—C1—Br2111.41 (8)
Br1—C1—Cl2111.41 (8)Cl2—C1—Br20.00 (8)
(cbm_100K) bromochloromethane top
Crystal data top
CH2BrClDx = 2.422 Mg m3
Mr = 129.39Melting point: 185 K
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 11.874 (2) ÅCell parameters from 1948 reflections
b = 4.4224 (9) Åθ = 3.0–29.7°
c = 14.582 (3) ŵ = 12.05 mm1
β = 112.04 (3)°T = 100 K
V = 709.8 (2) Å3Irregular, colourless
Z = 80.12 × 0.12 × 0.10 mm
F(000) = 480
Data collection top
KM-4 CCD
diffractometer
923 independent reflections
Radiation source: fine-focus sealed tube784 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.078
ω–scansθmax = 29.7°, θmin = 3.0°
Absorption correction: multi-scan
Correction for absorption was made using XEMP (SHELXTL, Sheldrick (1990)).
h = 1615
Tmin = 0.22, Tmax = 0.32k = 46
3122 measured reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.0553P)2 + 4.5134P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max < 0.001
923 reflectionsΔρmax = 1.51 e Å3
36 parametersΔρmin = 0.72 e Å3
6 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0023 (9)
Crystal data top
CH2BrClV = 709.8 (2) Å3
Mr = 129.39Z = 8
Monoclinic, C2/cMo Kα radiation
a = 11.874 (2) ŵ = 12.05 mm1
b = 4.4224 (9) ÅT = 100 K
c = 14.582 (3) Å0.12 × 0.12 × 0.10 mm
β = 112.04 (3)°
Data collection top
KM-4 CCD
diffractometer
923 independent reflections
Absorption correction: multi-scan
Correction for absorption was made using XEMP (SHELXTL, Sheldrick (1990)).
784 reflections with I > 2σ(I)
Tmin = 0.22, Tmax = 0.32Rint = 0.078
3122 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0516 restraints
wR(F2) = 0.128H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 1.51 e Å3
923 reflectionsΔρmin = 0.72 e Å3
36 parameters
Special details top

Experimental. Data were collected at ambient pressure (100 kPa) and 100 K with the crystal obtained by the in situ low-temperature crystallization technique.

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*/UeqOcc. (<1)
Br10.08668 (3)0.67376 (15)0.13130 (5)0.0279 (3)0.475 (3)
Cl10.08668 (3)0.67376 (15)0.13130 (5)0.0279 (3)0.525 (3)
Br20.34594 (3)0.65355 (15)0.13301 (5)0.0279 (3)0.525 (3)
Cl20.34594 (3)0.65355 (15)0.13301 (5)0.0279 (3)0.475 (3)
C10.2026 (4)0.43547 (16)0.10799 (15)0.0295 (11)
H10.17142 (11)0.3738 (7)0.0391 (2)0.035*
H20.22127 (11)0.26233 (19)0.1520 (2)0.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0256 (5)0.0271 (4)0.0337 (5)0.0027 (3)0.0141 (3)0.0051 (3)
Cl10.0256 (5)0.0271 (4)0.0337 (5)0.0027 (3)0.0141 (3)0.0051 (3)
Br20.0215 (4)0.0282 (4)0.0329 (5)0.0008 (2)0.0089 (3)0.0019 (3)
Cl20.0215 (4)0.0282 (4)0.0329 (5)0.0008 (2)0.0089 (3)0.0019 (3)
C10.030 (3)0.018 (2)0.036 (3)0.0000 (19)0.007 (2)0.005 (2)
Geometric parameters (Å, º) top
Br1—C11.863 (4)Br2—C11.870 (4)
Cl1—C11.863 (4)Cl2—C11.870 (4)
Cl1—C1—Br10.00 (4)Cl1—C1—Br2110.70 (6)
Cl1—C1—Cl2110.70 (6)Br1—C1—Br2110.70 (6)
Br1—C1—Cl2110.70 (6)Cl2—C1—Br20.00 (6)
(cbm_1.04GPa) bromochloromethane top
Crystal data top
CH2BrClDx = 2.655 Mg m3
Mr = 129.39Melting point: 185 K
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
a = 4.1126 (8) ÅCell parameters from 1476 reflections
b = 8.0685 (16) Åθ = 5.1–29.9°
c = 9.755 (2) ŵ = 13.21 mm1
V = 323.69 (11) Å3T = 295 K
Z = 4Cylinder, colourless
F(000) = 2400.31 × 0.31 × 0.05 mm
Data collection top
KM-4 CCD
diffractometer
160 independent reflections
Radiation source: fine-focus sealed tube126 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
ϕ– and ω–scansθmax = 29.9°, θmin = 5.1°
Absorption correction: numerical
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 = 55
Tmin = 0.18, Tmax = 0.42k = 1110
2144 measured reflectionsl = 33
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.058 w = 1/[σ2(Fo2) + (0.0301P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
160 reflectionsΔρmax = 0.18 e Å3
25 parametersΔρmin = 0.23 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (5)
Crystal data top
CH2BrClV = 323.69 (11) Å3
Mr = 129.39Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 4.1126 (8) ŵ = 13.21 mm1
b = 8.0685 (16) ÅT = 295 K
c = 9.755 (2) Å0.31 × 0.31 × 0.05 mm
Data collection top
KM-4 CCD
diffractometer
160 independent reflections
Absorption correction: numerical
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).
126 reflections with I > 2σ(I)
Tmin = 0.18, Tmax = 0.42Rint = 0.083
2144 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0302 restraints
wR(F2) = 0.058H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.18 e Å3
160 reflectionsΔρmin = 0.23 e Å3
25 parameters
Special details top

Experimental. Data were collected at room temperature and pressure of 1.04 (5) GPa 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.19106 (12)0.84807 (8)0.3854 (2)0.059 (18)0.50
Br10.19106 (12)0.84807 (8)0.3854 (2)0.052 (7)0.50
C10.00000.97434 (8)0.25000.048 (10)
H10.158 (3)1.0499 (16)0.2892 (2)0.057*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.074 (7)0.033 (3)0.07 (5)0.000 (3)0.008 (12)0.005 (12)
Br10.053 (2)0.063 (2)0.04 (2)0.0197 (14)0.008 (4)0.008 (5)
C10.066 (4)0.028 (3)0.05 (3)0.0000.006 (8)0.000
Geometric parameters (Å, º) top
Cl1—C11.8436 (15)C1—Cl1i1.8436 (15)
Br1—C11.8436 (15)C1—H10.9700 (1)
C1—Br1i1.8436 (15)
Br1i—C1—Cl1i0.00 (3)Cl1—C1—Br10.00 (9)
Br1i—C1—Cl1112.91 (8)Br1i—C1—H1110.1 (9)
Cl1i—C1—Cl1112.91 (8)Cl1i—C1—H1110.1 (9)
Br1i—C1—Br1112.91 (8)Cl1—C1—H1110.52 (11)
Cl1i—C1—Br1112.91 (8)Br1—C1—H1110.52 (11)
Symmetry code: (i) x, y, z+1/2.
(cbm_1.72GPa) bromochloromethane top
Crystal data top
CH2BrClDx = 2.802 Mg m3
Mr = 129.39Melting point: 185 K
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
a = 3.9929 (8) ÅCell parameters from 1548 reflections
b = 7.9351 (16) Åθ = 5.1–29.6°
c = 9.6808 (19) ŵ = 13.94 mm1
V = 306.73 (11) Å3T = 295 K
Z = 4Cylinder, colourless
F(000) = 2400.38 × 0.38 × 0.08 mm
Data collection top
KM-4 CCD
diffractometer
295 independent reflections
Radiation source: fine-focus sealed tube271 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
ϕ– and ω–scansθmax = 29.6°, θmin = 5.1°
Absorption correction: numerical
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 = 33
Tmin = 0.13, Tmax = 0.31k = 1010
2283 measured reflectionsl = 1212
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.065 w = 1/[σ2(Fo2) + (0.031P)2 + 0.0922P]
where P = (Fo2 + 2Fc2)/3
S = 1.20(Δ/σ)max < 0.001
295 reflectionsΔρmax = 0.35 e Å3
25 parametersΔρmin = 0.34 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.005 (2)
Crystal data top
CH2BrClV = 306.73 (11) Å3
Mr = 129.39Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 3.9929 (8) ŵ = 13.94 mm1
b = 7.9351 (16) ÅT = 295 K
c = 9.6808 (19) Å0.38 × 0.38 × 0.08 mm
Data collection top
KM-4 CCD
diffractometer
295 independent reflections
Absorption correction: numerical
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).
271 reflections with I > 2σ(I)
Tmin = 0.13, Tmax = 0.31Rint = 0.057
2283 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0292 restraints
wR(F2) = 0.065H atoms treated by a mixture of independent and constrained refinement
S = 1.20Δρmax = 0.35 e Å3
295 reflectionsΔρmin = 0.34 e Å3
25 parameters
Special details top

Experimental. Data were collected at room temperature and pressure of 1.72 (5) GPa 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl10.19596 (12)0.84967 (6)0.38649 (5)0.034 (3)0.50
Br10.19596 (12)0.84967 (6)0.38649 (5)0.0377 (17)0.50
C10.00000.98034 (8)0.25000.0353 (14)
H10.166 (3)1.0547 (16)0.2907 (3)0.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.048 (9)0.027 (4)0.027 (4)0.002 (3)0.016 (4)0.004 (3)
Br10.038 (4)0.044 (2)0.032 (2)0.0114 (16)0.0010 (17)0.0061 (13)
C10.036 (5)0.028 (2)0.042 (2)0.0000.003 (2)0.000
Geometric parameters (Å, º) top
Cl1—C11.8529 (6)C1—Cl1i1.8529 (6)
Br1—C11.8529 (6)C1—H10.9700 (1)
C1—Br1i1.8529 (6)
Br1i—C1—Cl1i0.00 (3)Cl1—C1—Br10.00 (3)
Br1i—C1—Cl1111.94 (5)Br1i—C1—H1110.0 (9)
Cl1i—C1—Cl1111.94 (5)Cl1i—C1—H1110.0 (9)
Br1i—C1—Br1111.94 (5)Cl1—C1—H1109.82 (4)
Cl1i—C1—Br1111.94 (5)Br1—C1—H1109.82 (4)
Symmetry code: (i) x, y, z+1/2.

Experimental details

(cbm_170K)(cbm_100K)(cbm_1.04GPa)(cbm_1.72GPa)
Crystal data
Chemical formulaCH2BrClCH2BrClCH2BrClCH2BrCl
Mr129.39129.39129.39129.39
Crystal system, space groupMonoclinic, C2/cMonoclinic, C2/cOrthorhombic, PbcnOrthorhombic, Pbcn
Temperature (K)170100295295
a, b, c (Å)11.959 (2), 4.4531 (9), 14.873 (3)11.874 (2), 4.4224 (9), 14.582 (3)4.1126 (8), 8.0685 (16), 9.755 (2)3.9929 (8), 7.9351 (16), 9.6808 (19)
α, β, γ (°)90, 112.96 (3), 9090, 112.04 (3), 9090, 90, 9090, 90, 90
V3)729.3 (3)709.8 (2)323.69 (11)306.73 (11)
Z8844
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)11.7312.0513.2113.94
Crystal size (mm)0.12 × 0.12 × 0.100.12 × 0.12 × 0.100.31 × 0.31 × 0.050.38 × 0.38 × 0.08
Data collection
DiffractometerKM-4 CCD
diffractometer
KM-4 CCD
diffractometer
KM-4 CCD
diffractometer
KM-4 CCD
diffractometer
Absorption correctionMulti-scan
Correction for absorption was made using XEMP (SHELXTL, Sheldrick (1990)).
Multi-scan
Correction for absorption was made using XEMP (SHELXTL, Sheldrick (1990)).
Numerical
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).
Numerical
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, Tmax0.22, 0.320.22, 0.320.18, 0.420.13, 0.31
No. of measured, independent and
observed [I > 2σ(I)] reflections
2422, 909, 643 3122, 923, 784 2144, 160, 126 2283, 295, 271
Rint0.1090.0780.0830.057
(sin θ/λ)max1)0.6840.6960.7020.696
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.172, 1.15 0.051, 0.128, 1.12 0.030, 0.058, 1.05 0.029, 0.065, 1.20
No. of reflections909923160295
No. of parameters36362525
No. of restraints6622
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)0.83, 0.661.51, 0.720.18, 0.230.35, 0.34

Computer programs: CrysAlis CCD (Oxford Diffraction, 2004), CrysAlis RED (Oxford Diffraction, 2004); REDSHABS (Katrusiak, A. 2003), SHELXS97 (Sheldrick, 1990), SHELXS–97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXL–97 (Sheldrick, 1997), X-SEED 2.0.

 

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