Download citation
Download citation
link to html
The structure of 1,2,3-trichloropropane, ClCH2CHClCH2Cl, in-situ crystallized in a diamond–anvil cell, has been determined by single-crystal X-ray diffraction at 0.28 and 0.35 GPa. A melting point at 295 K and 0.22 GPa has been determined. The molecular conformation of aliphatic chain and terminal Cl atoms is approximately C2 symmetric. Of the intermolecular contacts, the tightest are the Cl...Cl and then the Cl...H contacts, whereas the H...H distances are considerably longer than the sum of the van der Waals radii and leave narrow voids in the structure. The elevated pressure reduces the H...H separations but hardly affects the Cl...Cl distances. The crystal growth rates, compression and types of intermolecular interactions in the structures can be correlated with the directions of the Cl...Cl contacts, which can be considered the main motif responsible for the molecular arrangement in the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106030229/av5065sup1.cif
Contains datablocks 1tcp, 2tcp

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106030229/av5065sup2.hkl
Contains datablock 1tcp

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106030229/av5065sup3.hkl
Contains datablock 2tcp

CCDC references: 629804; 629805

Computing details top

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, 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]
(1tcp) 1,2,3-trichloropropane top
Crystal data top
C3H5Cl3Dx = 1.706 Mg m3
Mr = 147.42Melting point: 259 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 5.1404 (10) ÅCell parameters from 3519 reflections
b = 11.363 (2) Åθ = 3–30°
c = 9.885 (2) ŵ = 1.44 mm1
β = 96.21 (3)°T = 295 K
V = 574.0 (2) Å3Cylinder, colourless
Z = 40.46 × 0.41 × 0.26 mm
F(000) = 296
Data collection top
Kuma KM4CCD κ geometry
diffractometer
679 independent reflections
Radiation source: fine-focus sealed tube520 reflections with > 4σ(I)
Graphite monochromatorRint = 0.082
ω scansθmax = 30.1°, θmin = 2.7°
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 = 67
Tmin = 0.20, Tmax = 0.61k = 66
4431 measured reflectionsl = 1313
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.1174P)2]
where P = (Fo2 + 2Fc2)/3
679 reflections(Δ/σ)max < 0.001
77 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C3H5Cl3V = 574.0 (2) Å3
Mr = 147.42Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.1404 (10) ŵ = 1.44 mm1
b = 11.363 (2) ÅT = 295 K
c = 9.885 (2) Å0.46 × 0.41 × 0.26 mm
β = 96.21 (3)°
Data collection top
Kuma KM4CCD κ geometry
diffractometer
679 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
520 reflections with > 4σ(I)
Tmin = 0.20, Tmax = 0.61Rint = 0.082
4431 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.167H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.32 e Å3
679 reflectionsΔρmin = 0.34 e Å3
77 parameters
Special details top

Experimental. High-pressure experiment at 0.28 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
Cl30.25665 (19)0.0386 (2)0.85740 (13)0.0608 (14)
Cl10.2553 (2)0.1045 (2)0.52854 (10)0.0575 (13)
Cl20.27487 (19)0.3235 (3)0.74680 (10)0.0518 (14)
C20.0000 (7)0.2277 (9)0.7403 (4)0.033 (4)
H2A0.159 (6)0.253 (7)0.769 (3)0.020 (8)*
C30.0271 (8)0.1301 (9)0.8416 (4)0.048 (4)
H3A0.176 (11)0.052 (9)0.823 (5)0.066 (16)*
H3B0.032 (7)0.179 (8)0.924 (4)0.039 (11)*
C10.0201 (8)0.1870 (10)0.5959 (4)0.048 (4)
H1A0.167 (10)0.139 (10)0.586 (4)0.054 (14)*
H1B0.039 (9)0.260 (11)0.539 (5)0.057 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl30.0493 (6)0.053 (5)0.0782 (9)0.0134 (10)0.0036 (5)0.0111 (10)
Cl10.0621 (7)0.054 (4)0.0535 (7)0.0042 (10)0.0076 (4)0.0087 (8)
Cl20.0564 (7)0.034 (4)0.0655 (7)0.0119 (9)0.0095 (5)0.0011 (7)
C20.0378 (17)0.006 (13)0.055 (2)0.005 (3)0.0010 (14)0.000 (3)
C30.050 (2)0.053 (14)0.042 (2)0.004 (4)0.0067 (15)0.006 (3)
C10.046 (2)0.051 (13)0.048 (2)0.010 (4)0.0079 (15)0.001 (3)
Geometric parameters (Å, º) top
Cl3—C31.784 (7)C2—H2A0.88 (4)
Cl1—C11.766 (7)C3—H3A1.17 (8)
Cl2—C21.791 (7)C3—H3B0.99 (6)
C2—C31.510 (10)C1—H1A0.95 (8)
C2—C11.515 (7)C1—H1B1.01 (10)
C3—C2—C1114.9 (8)C2—C3—H3B99 (5)
C3—C2—Cl2107.1 (3)Cl3—C3—H3B110 (3)
C1—C2—Cl2110.7 (4)H3A—C3—H3B119 (5)
C3—C2—H2A100 (4)C2—C1—Cl1112.6 (3)
C1—C2—H2A104 (2)C2—C1—H1A114 (3)
Cl2—C2—H2A120 (4)Cl1—C1—H1A106 (5)
C2—C3—Cl3110.7 (3)C2—C1—H1B107 (5)
C2—C3—H3A124 (3)Cl1—C1—H1B110 (3)
Cl3—C3—H3A95 (4)H1A—C1—H1B107 (6)
C1—C2—C3—Cl363.2 (5)C3—C2—C1—Cl159.2 (6)
Cl2—C2—C3—Cl3173.4 (3)Cl2—C2—C1—Cl162.2 (8)
(2tcp) top
Crystal data top
C3H5Cl3Dx = 1.712 Mg m3
Mr = 147.42Melting point: 259 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 5.1285 (10) ÅCell parameters from 3388 reflections
b = 11.377 (2) Åθ = 4–29°
c = 9.859 (2) ŵ = 1.45 mm1
β = 96.13 (3)°T = 295 K
V = 572.0 (2) Å3Cylinder, colourless
Z = 40.45 × 0.40 × 0.18 mm
F(000) = 296
Data collection top
Kuma KM4CCD κ geometry
diffractometer
538 independent reflections
Radiation source: fine-focus sealed tube438 reflections with > 4σ(I)
Graphite monochromatorRint = 0.112
ω scansθmax = 29.7°, θmin = 4.2°
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 = 77
Tmin = 0.27, Tmax = 0.69k = 44
4612 measured reflectionsl = 1313
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)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.123P)2]
where P = (Fo2 + 2Fc2)/3
538 reflections(Δ/σ)max < 0.001
77 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C3H5Cl3V = 572.0 (2) Å3
Mr = 147.42Z = 4
Monoclinic, P21/nMo Kα radiation
a = 5.1285 (10) ŵ = 1.45 mm1
b = 11.377 (2) ÅT = 295 K
c = 9.859 (2) Å0.45 × 0.40 × 0.18 mm
β = 96.13 (3)°
Data collection top
Kuma KM4CCD κ geometry
diffractometer
538 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
438 reflections with > 4σ(I)
Tmin = 0.27, Tmax = 0.69Rint = 0.112
4612 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.28 e Å3
538 reflectionsΔρmin = 0.25 e Å3
77 parameters
Special details top

Experimental. High-pressure experiment at 0.35 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
Cl30.2569 (2)0.0380 (3)0.85765 (13)0.061 (3)
Cl10.2556 (2)0.1043 (3)0.52835 (11)0.063 (3)
Cl20.2749 (2)0.3236 (4)0.74693 (11)0.057 (2)
C20.0030 (7)0.2309 (11)0.7396 (4)0.041 (7)
H2A0.180 (5)0.275 (7)0.771 (3)0.003 (6)*
C30.0268 (8)0.1287 (11)0.8420 (4)0.044 (7)
H3A0.213 (11)0.049 (11)0.846 (5)0.067 (19)*
H3B0.047 (8)0.137 (13)0.931 (5)0.053 (13)*
C10.0229 (9)0.1851 (13)0.5959 (5)0.044 (6)
H1A0.189 (11)0.126 (11)0.577 (5)0.051 (13)*
H1B0.042 (11)0.242 (17)0.547 (7)0.07 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl30.0506 (7)0.057 (8)0.0751 (8)0.0153 (12)0.0023 (5)0.0107 (12)
Cl10.0614 (7)0.070 (8)0.0539 (7)0.0031 (13)0.0066 (5)0.0111 (10)
Cl20.0554 (7)0.049 (7)0.0671 (8)0.0088 (12)0.0101 (5)0.0048 (11)
C20.0362 (18)0.04 (2)0.050 (2)0.003 (4)0.0021 (14)0.000 (4)
C30.051 (2)0.04 (2)0.047 (2)0.001 (4)0.0092 (15)0.005 (4)
C10.050 (2)0.03 (2)0.049 (2)0.001 (4)0.0098 (17)0.003 (4)
Geometric parameters (Å, º) top
Cl3—C31.776 (9)C2—H2A1.08 (4)
Cl1—C11.768 (9)C3—H3A1.32 (10)
Cl2—C21.756 (9)C3—H3B0.90 (5)
C2—C11.529 (9)C1—H1A1.12 (9)
C2—C31.554 (14)C1—H1B0.82 (16)
C1—C2—C3111.5 (10)C2—C3—H3B126 (9)
C1—C2—Cl2113.0 (4)Cl3—C3—H3B99 (5)
C3—C2—Cl2107.8 (3)H3A—C3—H3B83 (7)
C1—C2—H2A105.5 (17)C2—C1—Cl1112.3 (4)
C3—C2—H2A107 (3)C2—C1—H1A120 (2)
Cl2—C2—H2A112 (4)Cl1—C1—H1A103 (4)
C2—C3—Cl3111.8 (3)C2—C1—H1B108 (10)
C2—C3—H3A130 (3)Cl1—C1—H1B109 (6)
Cl3—C3—H3A101 (4)H1A—C1—H1B104 (9)
C1—C2—C3—Cl362.0 (5)C3—C2—C1—Cl162.3 (7)
Cl2—C2—C3—Cl3173.4 (4)Cl2—C2—C1—Cl159.4 (11)

Experimental details

(1tcp)(2tcp)
Crystal data
Chemical formulaC3H5Cl3C3H5Cl3
Mr147.42147.42
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)295295
a, b, c (Å)5.1404 (10), 11.363 (2), 9.885 (2)5.1285 (10), 11.377 (2), 9.859 (2)
β (°) 96.21 (3) 96.13 (3)
V3)574.0 (2)572.0 (2)
Z44
Radiation typeMo KαMo Kα
µ (mm1)1.441.45
Crystal size (mm)0.46 × 0.41 × 0.260.45 × 0.40 × 0.18
Data collection
DiffractometerKuma 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
Tmin, Tmax0.20, 0.610.27, 0.69
No. of measured, independent and
observed [ > 4σ(I)] reflections
4431, 679, 520 4612, 538, 438
Rint0.0820.112
(sin θ/λ)max1)0.7060.696
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.167, 1.03 0.061, 0.162, 1.02
No. of reflections679538
No. of parameters7777
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.340.28, 0.25

Computer programs: CrysAlis (Oxford Diffraction, 2004), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1990).

 

Follow Acta Cryst. B
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds