Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105017374/av5039sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105017374/av50391dcmsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105017374/av50392dcmsup3.hkl |
CCDC references: 286332; 286333
For both compounds, data collection: CrysAlis (Oxford Diffraction, 2004); cell refinement: CrysAlis (Oxford Diffraction, 2004); data reduction: CrysAlis (Oxford Diffraction, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
CH_{2}Cl_{2} | D_{x} = 1.920 Mg m^{−}^{3} |
M_{r} = 84.93 | Melting point: 176 K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 1459 reflections |
a = 3.984 (1) Å | θ = 5–30° |
b = 7.863 (2) Å | µ = 1.86 mm^{−}^{1} |
c = 9.357 (2) Å | T = 293 K |
V = 293.12 (12) Å^{3} | Cylinder, colourless |
Z = 4 | 0.42 × 0.42 × 0.15 × 0.21 (radius) mm |
F(000) = 168 |
Kuma KM4CCD κ geometry diffractometer | 219 independent reflections |
Radiation source: fine-focus sealed tube | 188 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.096 |
ω scans | θ_{max} = 29.6°, θ_{min} = 5.2° |
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} = 0.50, T_{max} = 0.85 | k = −10→10 |
2203 measured reflections | l = −5→5 |
Refinement on F^{2} | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F^{2} > 2σ(F^{2})] = 0.061 | H atoms treated by a mixture of independent and constrained refinement |
wR(F^{2}) = 0.190 | w = 1/[σ^{2}(F_{o}^{2}) + (0.1099P)^{2} + 0.0415P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
S = 1.28 | (Δ/σ)_{max} < 0.001 |
219 reflections | Δρ_{max} = 0.30 e Å^{−}^{3} |
20 parameters | Δρ_{min} = −0.29 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: 0.11 (4) |
CH_{2}Cl_{2} | V = 293.12 (12) Å^{3} |
M_{r} = 84.93 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 3.984 (1) Å | µ = 1.86 mm^{−}^{1} |
b = 7.863 (2) Å | T = 293 K |
c = 9.357 (2) Å | 0.42 × 0.42 × 0.15 × 0.21 (radius) mm |
Kuma KM4CCD κ geometry diffractometer | 219 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 | 188 reflections with I > 2σ(I) |
T_{min} = 0.50, T_{max} = 0.85 | R_{int} = 0.096 |
2203 measured reflections |
R[F^{2} > 2σ(F^{2})] = 0.061 | 0 restraints |
wR(F^{2}) = 0.190 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.28 | Δρ_{max} = 0.30 e Å^{−}^{3} |
219 reflections | Δρ_{min} = −0.29 e Å^{−}^{3} |
20 parameters |
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 | 0.1889 (4) | 0.14840 (17) | 0.1165 (2) | 0.0499 (16) | |
C1 | 0.0000 | 0.0223 (8) | 0.2500 | 0.037 (4) | |
H1 | 0.184 (19) | −0.061 (11) | 0.275 (18) | 0.09 (3)* |
U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} | |
Cl1 | 0.0594 (12) | 0.0515 (11) | 0.039 (5) | −0.0122 (4) | −0.0052 (6) | 0.0038 (8) |
C1 | 0.050 (3) | 0.040 (3) | 0.020 (14) | 0.000 | 0.002 (3) | 0.000 |
Cl1—C1 | 1.765 (4) | C1—H1 | 1.01 (10) |
Cl1^{i}—C1—Cl1 | 111.6 (3) | Cl1—C1—H1 | 103 (7) |
Cl1^{i}—C1—H1 | 121 (9) |
Symmetry code: (i) −x, y, −z+1/2. |
CH_{2}Cl_{2} | D_{x} = 1.972 Mg m^{−}^{3} |
M_{r} = 84.93 | Melting point: 176 K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 1495 reflections |
a = 3.924 (1) Å | θ = 5–30° |
b = 7.793 (2) Å | µ = 1.91 mm^{−}^{1} |
c = 9.335 (2) Å | T = 293 K |
V = 285.46 (12) Å^{3} | Cylinder, colourless |
Z = 4 | 0.42 × 0.42 × 0.14 × 0.21 (radius) mm |
F(000) = 168 |
Kuma KM4CCD κ geometry diffractometer | 174 independent reflections |
Radiation source: fine-focus sealed tube | 157 reflections with I > 2σ(I) |
Graphite monochromator | R_{int} = 0.068 |
ω scans | θ_{max} = 29.9°, θ_{min} = 5.2° |
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} = 0.46, T_{max} = 0.86 | k = −10→10 |
2063 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})] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F^{2}) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.25 | w = 1/[σ^{2}(F_{o}^{2}) + (0.0601P)^{2} + 0.5145P] where P = (F_{o}^{2} + 2F_{c}^{2})/3 |
174 reflections | (Δ/σ)_{max} < 0.001 |
19 parameters | Δρ_{max} = 0.29 e Å^{−}^{3} |
0 restraints | Δρ_{min} = −0.28 e Å^{−}^{3} |
CH_{2}Cl_{2} | V = 285.46 (12) Å^{3} |
M_{r} = 84.93 | Z = 4 |
Orthorhombic, Pbcn | Mo Kα radiation |
a = 3.924 (1) Å | µ = 1.91 mm^{−}^{1} |
b = 7.793 (2) Å | T = 293 K |
c = 9.335 (2) Å | 0.42 × 0.42 × 0.14 × 0.21 (radius) mm |
Kuma KM4CCD κ geometry diffractometer | 174 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 | 157 reflections with I > 2σ(I) |
T_{min} = 0.46, T_{max} = 0.86 | R_{int} = 0.068 |
2063 measured reflections |
R[F^{2} > 2σ(F^{2})] = 0.055 | 0 restraints |
wR(F^{2}) = 0.135 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.25 | Δρ_{max} = 0.29 e Å^{−}^{3} |
174 reflections | Δρ_{min} = −0.28 e Å^{−}^{3} |
19 parameters |
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 | 0.1903 (4) | 0.14808 (17) | 0.1156 (4) | 0.0404 (19) | |
C1 | 0.0000 | 0.0202 (8) | 0.2500 | 0.028 (9) | |
H1 | 0.181 (19) | −0.071 (9) | 0.31 (2) | 0.08 (3)* |
U^{11} | U^{22} | U^{33} | U^{12} | U^{13} | U^{23} | |
Cl1 | 0.0467 (9) | 0.0424 (8) | 0.032 (6) | −0.0098 (4) | −0.0013 (11) | 0.0025 (9) |
C1 | 0.049 (4) | 0.029 (3) | 0.01 (3) | 0.000 | −0.005 (7) | 0.000 |
Cl1—C1 | 1.769 (4) | C1—H1 | 1.13 (12) |
Cl1^{i}—C1—Cl1 | 111.4 (4) | Cl1—C1—H1 | 115 (7) |
Cl1^{i}—C1—H1 | 107 (9) |
Symmetry code: (i) −x, y, −z+1/2. |
Experimental details
(1dcm) | (2dcm) | |
Crystal data | ||
Chemical formula | CH_{2}Cl_{2} | CH_{2}Cl_{2} |
M_{r} | 84.93 | 84.93 |
Crystal system, space group | Orthorhombic, Pbcn | Orthorhombic, Pbcn |
Temperature (K) | 293 | 293 |
a, b, c (Å) | 3.984 (1), 7.863 (2), 9.357 (2) | 3.924 (1), 7.793 (2), 9.335 (2) |
V (Å^{3}) | 293.12 (12) | 285.46 (12) |
Z | 4 | 4 |
Radiation type | Mo Kα | Mo Kα |
µ (mm^{−}^{1}) | 1.86 | 1.91 |
Crystal size (mm) | 0.42 × 0.42 × 0.15 × 0.21 (radius) | 0.42 × 0.42 × 0.14 × 0.21 (radius) |
Data collection | ||
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 |
T_{min}, T_{max} | 0.50, 0.85 | 0.46, 0.86 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2203, 219, 188 | 2063, 174, 157 |
R_{int} | 0.096 | 0.068 |
(sin θ/λ)_{max} (Å^{−}^{1}) | 0.695 | 0.700 |
Refinement | ||
R[F^{2} > 2σ(F^{2})], wR(F^{2}), S | 0.061, 0.190, 1.28 | 0.055, 0.135, 1.25 |
No. of reflections | 219 | 174 |
No. of parameters | 20 | 19 |
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 |
Δρ_{max}, Δρ_{min} (e Å^{−}^{3}) | 0.30, −0.29 | 0.29, −0.28 |
Computer programs: CrysAlis (Oxford Diffraction, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1990).