Buy article online - an online subscription or single-article purchase is required to access this article.
The crystal structure of 1,2,3,3,4,4,5,5,6,6-decafluorocyclohex-1-ene (decafluorocyclohex-1-ene, C
6F
10) 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
CCDC references: 958008; 958009; 958010
Program(s) used to solve structure: ESPOIR for c6f10justsolved.
(c6f10justsolved) decafluorocyclohex-1-ene
top
Crystal data top
C6F10 | β = 113.34 (1)° |
Mr = 262.06 | V = 766.1 (3) Å3 |
Monoclinic, P21/n | Z = 4 |
Hall symbol: -P 2yn | Constant Wavelength Neutron Diffraction radiation, λ = 1.90900 Å |
a = 11.915 (3) Å | T = 4 K |
b = 7.247 (2) Å | × × mm |
c = 9.663 (2) Å | |
Data collection top
Diffractometer | k = ?→? |
h = ?→? | l = ?→? |
Crystal data top
C6F10 | β = 113.34 (1)° |
Mr = 262.06 | V = 766.1 (3) Å3 |
Monoclinic, P21/n | Z = 4 |
a = 11.915 (3) Å | Constant Wavelength Neutron Diffraction radiation, λ = 1.90900 Å |
b = 7.247 (2) Å | T = 4 K |
c = 9.663 (2) Å | × × mm |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Biso*/Beq | |
C1 | 0.72845 | 0.67937 | −0.03636 | | |
C2 | 0.79459 | 0.50981 | 0.04909 | | |
C3 | 0.64935 | 0.63124 | −0.19967 | | |
C4 | 0.70362 | 0.36222 | 0.04943 | | |
C5 | 0.57698 | 0.45780 | −0.21471 | | |
C6 | 0.60203 | 0.33546 | −0.10224 | | |
F1 | 0.65730 | 0.74970 | 0.03118 | | |
F2 | 0.80947 | 0.81257 | −0.03165 | | |
F3 | 0.86815 | 0.55450 | 0.19251 | | |
F4 | 0.86787 | 0.44193 | −0.01641 | | |
F5 | 0.72372 | 0.60968 | −0.27536 | | |
F6 | 0.57586 | 0.77712 | −0.26519 | | |
F7 | 0.76495 | 0.20232 | 0.10331 | | |
F8 | 0.65484 | 0.41324 | 0.14964 | | |
F9 | 0.48321 | 0.42257 | −0.34763 | | |
F10 | 0.53213 | 0.18233 | −0.12617 | | |
(c6f10pbesol) decafluorocyclohex-1-ene
top
Crystal data top
C6F10 | β = 113.34° |
Mr = 262.06 | V = 766.1 Å3 |
Monoclinic, P21/n | Z = 4 |
Hall symbol: -P 2yn | ? radiation, λ = ? Å |
a = 11.915 Å | T = 4 K |
b = 7.247 Å | × × mm |
c = 9.663 Å | |
Crystal data top
C6F10 | β = 113.34° |
Mr = 262.06 | V = 766.1 Å3 |
Monoclinic, P21/n | Z = 4 |
a = 11.915 Å | ? radiation, λ = ? Å |
b = 7.247 Å | T = 4 K |
c = 9.663 Å | × × mm |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Biso*/Beq | |
C5 | 0.271110 | 0.317148 | 0.531559 | | |
C4 | 0.208918 | 0.488379 | 0.437933 | | |
C6 | 0.345003 | 0.366469 | 0.699616 | | |
C3 | 0.302687 | 0.642378 | 0.450680 | | |
C1 | 0.413870 | 0.543415 | 0.718735 | | |
C2 | 0.394382 | 0.666771 | 0.608431 | | |
F5a | 0.348974 | 0.244529 | 0.474536 | | |
F5b | 0.185437 | 0.189606 | 0.521239 | | |
F4a | 0.149386 | 0.440731 | 0.292039 | | |
F4b | 0.126733 | 0.554579 | 0.490813 | | |
F6b | 0.265672 | 0.377611 | 0.770516 | | |
F6a | 0.423610 | 0.225946 | 0.765769 | | |
F3b | 0.241045 | 0.802961 | 0.400265 | | |
F3a | 0.360490 | 0.599842 | 0.357026 | | |
F1 | 0.496772 | 0.573270 | 0.857262 | | |
F2 | 0.457393 | 0.823388 | 0.633012 | | |
(c6f10pbe0) decafluorocyclohex-1-ene
top
Crystal data top
C6F10 | c = 9.6630 Å |
Mr = 262.06 | β = 113.3400° |
Monoclinic, P21/n | V = ? Å3 |
Hall symbol: -P 2yn | Z = 4 |
a = 11.9150 Å | ? radiation, λ = ? Å |
b = 7.2470 Å | × × mm |
Crystal data top
C6F10 | β = 113.3400° |
Mr = 262.06 | V = ? Å3 |
Monoclinic, P21/n | Z = 4 |
a = 11.9150 Å | ? radiation, λ = ? Å |
b = 7.2470 Å | × × mm |
c = 9.6630 Å | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Biso*/Beq | |
C5 | 0.271276 | 0.317614 | 0.531404 | | |
C4 | 0.209131 | 0.488434 | 0.438172 | | |
C6 | 0.344938 | 0.366778 | 0.698972 | | |
C3 | 0.302630 | 0.641849 | 0.450999 | | |
C1 | 0.413738 | 0.543755 | 0.717998 | | |
C2 | 0.394215 | 0.666074 | 0.608830 | | |
F5a | 0.348460 | 0.245437 | 0.474781 | | |
F5b | 0.186212 | 0.191038 | 0.520883 | | |
F4a | 0.149929 | 0.441150 | 0.293383 | | |
F4b | 0.127533 | 0.554034 | 0.490576 | | |
F6b | 0.266563 | 0.378384 | 0.769460 | | |
F6a | 0.422937 | 0.227520 | 0.764519 | | |
F3b | 0.241516 | 0.801098 | 0.400947 | | |
F3a | 0.360331 | 0.599684 | 0.358682 | | |
F1 | 0.495985 | 0.573023 | 0.855899 | | |
F2 | 0.456604 | 0.822094 | 0.632901 | | |
Experimental details
| (c6f10justsolved) | (c6f10pbesol) | (c6f10pbe0) |
Crystal data |
Chemical formula | C6F10 | C6F10 | C6F10 |
Mr | 262.06 | 262.06 | 262.06 |
Crystal system, space group | Monoclinic, P21/n | Monoclinic, P21/n | Monoclinic, P21/n |
Temperature (K) | 4 | 4 | ? |
a, b, c (Å) | 11.915 (3), 7.247 (2), 9.663 (2) | 11.915, 7.247, 9.663 | 11.9150, 7.2470, 9.6630 |
β (°) | 113.34 (1) | 113.34 | 113.3400 |
V (Å3) | 766.1 (3) | 766.1 | ? |
Z | 4 | 4 | 4 |
Radiation type | Constant Wavelength Neutron Diffraction, λ = 1.90900 Å | ?, λ = ? Å | ?, λ = ? Å |
µ (mm−1) | ? | ? | ? |
Crystal size (mm) | × × | × × | × × |
|
Data collection |
Diffractometer | Diffractometer | ? | ? |
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 Å−3) | ?, ? | ?, ? | ?, ? |
Subscribe to Acta Crystallographica Section B: Structural Science, Crystal Engineering and Materials
The full text of this article is available to subscribers to the journal.
If you have already registered and are using a computer listed in your registration details, please email
support@iucr.org for assistance.