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The crystal structure of 1,2,3,3,4,4,5,5,6,6-decafluorocyclohex-1-ene (decafluorocyclohex-1-ene, C6F10) was solved in direct space from neutron powder diffraction data previously collected at 4.2 K [Pawley, G. S. (1981). J. Appl. Cryst. 14, 357–361] and refined by energy minimization in the solid state. To optimize the positions of the 64 atoms in the monoclinic computational cell the PBESOL and hybrid PBE0 functionals were used. The crystal structure of the title compound, which is liquid at room temperature, is built of antiparallel pairs of molecules assembled into molecular columns stacked along the a axis. Dominating the crystal-building forces are weak intermolecular dispersion interactions. Bonding conditions in the structure were analysed by theoretical molecular calculations of representative next-neighbor molecular dimers carried out using dispersion-corrected density functional theory (DFT) functionals and the SCS-MP2 wavefunction method. The largest interaction energy is of the order of ∼ 21 kJ mol−1, above the interaction energy of a benzene dimer (11.3 kJ mol−1) and close to that of a water dimer (20.9 kJ mol−1). The interaction energy for the second most stable dimer can be compared with either that of a benzene dimer or of a C—H...π hydrogen bond. The remaining five weakly interacting dimers (∼ 4.2–8.4 kJ mol−1) can be characterized as having stronger interactions than those of methane dimers (−2.2 kJ mol−1), but weaker than those of benzene molecule pairs or weak C—H...C interactions for instance.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052519213013365/eb5026sup1.cif
Contains datablocks allCIF, c6f10justsolved, c6f10pbesol, c6f10pbe0

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213013365/eb5026c6f10justsolvedsup2.hkl
Contains datablock C6F10justsolved

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052519213013365/eb5026c6f10justsolvedsup3.rtv
Contains datablock C6F10justsolved

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213013365/eb5026c6f10pbesolsup4.hkl
Contains datablock C6F10PBESOL

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052519213013365/eb5026c6f10pbe0sup5.hkl
Contains datablock C6F10PBE0

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052519213013365/eb5026c6f10pbesolsup6.rtv
Contains datablock C6F10PBESOL

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S2052519213013365/eb5026c6f10pbe0sup7.rtv
Contains datablock C6F10PBE0

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052519213013365/eb5026sup8.pdf
Table of interaction energies

CCDC references: 958008; 958009; 958010

Computing details top

Program(s) used to solve structure: ESPOIR for c6f10justsolved.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(c6f10justsolved) decafluorocyclohex-1-ene top
Crystal data top
C6F10β = 113.34 (1)°
Mr = 262.06V = 766.1 (3) Å3
Monoclinic, P21/nZ = 4
Hall symbol: -P 2ynConstant Wavelength Neutron Diffraction radiation, λ = 1.90900 Å
a = 11.915 (3) ÅT = 4 K
b = 7.247 (2) Å × × mm
c = 9.663 (2) Å
Data collection top
Diffractometerk = ??
h = ??l = ??
Refinement top
Crystal data top
C6F10β = 113.34 (1)°
Mr = 262.06V = 766.1 (3) Å3
Monoclinic, P21/nZ = 4
a = 11.915 (3) ÅConstant Wavelength Neutron Diffraction radiation, λ = 1.90900 Å
b = 7.247 (2) ÅT = 4 K
c = 9.663 (2) Å × × mm
Data collection top
Diffractometer
Refinement top
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzBiso*/Beq
C10.728450.679370.03636
C20.794590.509810.04909
C30.649350.631240.19967
C40.703620.362220.04943
C50.576980.457800.21471
C60.602030.335460.10224
F10.657300.749700.03118
F20.809470.812570.03165
F30.868150.554500.19251
F40.867870.441930.01641
F50.723720.609680.27536
F60.575860.777120.26519
F70.764950.202320.10331
F80.654840.413240.14964
F90.483210.422570.34763
F100.532130.182330.12617
(c6f10pbesol) decafluorocyclohex-1-ene top
Crystal data top
C6F10β = 113.34°
Mr = 262.06V = 766.1 Å3
Monoclinic, P21/nZ = 4
Hall symbol: -P 2yn? radiation, λ = ? Å
a = 11.915 ÅT = 4 K
b = 7.247 Å × × mm
c = 9.663 Å
Data collection top
h = ??l = ??
k = ??
Refinement top
Crystal data top
C6F10β = 113.34°
Mr = 262.06V = 766.1 Å3
Monoclinic, P21/nZ = 4
a = 11.915 Å? radiation, λ = ? Å
b = 7.247 ÅT = 4 K
c = 9.663 Å × × mm
Data collection top
Refinement top
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzBiso*/Beq
C50.2711100.3171480.531559
C40.2089180.4883790.437933
C60.3450030.3664690.699616
C30.3026870.6423780.450680
C10.4138700.5434150.718735
C20.3943820.6667710.608431
F5a0.3489740.2445290.474536
F5b0.1854370.1896060.521239
F4a0.1493860.4407310.292039
F4b0.1267330.5545790.490813
F6b0.2656720.3776110.770516
F6a0.4236100.2259460.765769
F3b0.2410450.8029610.400265
F3a0.3604900.5998420.357026
F10.4967720.5732700.857262
F20.4573930.8233880.633012
(c6f10pbe0) decafluorocyclohex-1-ene top
Crystal data top
C6F10c = 9.6630 Å
Mr = 262.06β = 113.3400°
Monoclinic, P21/nV = ? Å3
Hall symbol: -P 2ynZ = 4
a = 11.9150 Å? radiation, λ = ? Å
b = 7.2470 Å × × mm
Data collection top
h = ??l = ??
k = ??
Refinement top
Crystal data top
C6F10β = 113.3400°
Mr = 262.06V = ? Å3
Monoclinic, P21/nZ = 4
a = 11.9150 Å? radiation, λ = ? Å
b = 7.2470 Å × × mm
c = 9.6630 Å
Data collection top
Refinement top
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzBiso*/Beq
C50.2712760.3176140.531404
C40.2091310.4884340.438172
C60.3449380.3667780.698972
C30.3026300.6418490.450999
C10.4137380.5437550.717998
C20.3942150.6660740.608830
F5a0.3484600.2454370.474781
F5b0.1862120.1910380.520883
F4a0.1499290.4411500.293383
F4b0.1275330.5540340.490576
F6b0.2665630.3783840.769460
F6a0.4229370.2275200.764519
F3b0.2415160.8010980.400947
F3a0.3603310.5996840.358682
F10.4959850.5730230.855899
F20.4566040.8220940.632901

Experimental details

(c6f10justsolved)(c6f10pbesol)(c6f10pbe0)
Crystal data
Chemical formulaC6F10C6F10C6F10
Mr262.06262.06262.06
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)44?
a, b, c (Å)11.915 (3), 7.247 (2), 9.663 (2)11.915, 7.247, 9.66311.9150, 7.2470, 9.6630
β (°) 113.34 (1) 113.34 113.3400
V3)766.1 (3)766.1?
Z444
Radiation typeConstant Wavelength Neutron Diffraction, λ = 1.90900 Å?, λ = ? Å?, λ = ? Å
µ (mm1)???
Crystal size (mm) × × × × × ×
Data collection
DiffractometerDiffractometer??
Absorption correction???
No. of measured, independent and
observed (?) reflections
?, ?, ? ?, ?, ? ?, ?, ?
Rint???
Refinement
R[F2 > 2σ(F2)], wR(F2), S ?, ?, ? ?, ?, ? ?, ?, ?
No. of reflections???
No. of parameters???
No. of restraints???
Δρmax, Δρmin (e Å3)?, ??, ??, ?

Computer programs: ESPOIR.

 

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