1,1-Bis[4-(trifluoro­meth­yl)phen­yl]germetane

Huck, L.A.; Potter, G.D.; Jenkins, H.A.; Britten, J.F.; Leigh, W.J.

doi:10.1107/S1600536809015268

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m602

doi:10.1107/S1600536809015268

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1,1-Bis[4-(trifluoromethyl)phenyl]germetane

Lawrence A. Huck,^a Gregory D. Potter,^a Hilary A. Jenkins,^a James F. Britten ^a and William J. Leigh ^a ^*

^aDepartment of Chemistry, McMaster University, Hamilton, ON, Canada L8S 4M1
^*Correspondence e-mail: leigh@mcmaster.ca

(Received 19 March 2009; accepted 23 April 2009; online 30 April 2009)

The internal C—Ge—C bond angle in the germacyclobutane ring of the title compound, C₁₇H₁₄F₆Ge or [Ge(C₃H₆)(C₇H₄F₃)₂], is 77.8 (3)°. The –CF₃ groups display rotational disorder [occupancies 0.604 (14):0.396 (14) and 0.410 (6):0.411 (6):0.179 (3)] and the germacyclobutane ring also shows disorder [occupancies 0.604 (14):0.396 (14)].

Related literature

For the synthesis of the title compound, see: Leigh et al. (2008 ). For related compounds see: Tokitoh et al. (1995 ); Eichler et al. (1999 ); Meiners et al. (2002 ); Tajima et al. (2005 ). For 1,1-bis[3,5-bis(trifluoromethyl)phenyl]germetane, which exhibits similar structural features, see: Potter et al. (2009 ).

Experimental

Crystal data

[Ge(C₃H₆)(C₇H₄F₃)₂]
M_r = 404.87
Monoclinic, P 2₁ /n
a = 13.596 (6) Å
b = 6.412 (3) Å
c = 20.243 (9) Å
β = 107.081 (7)°
V = 1687 (1) Å³
Z = 4
Mo Kα radiation
μ = 1.87 mm⁻¹
T = 173 K
0.40 × 0.38 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan SADABS (Bruker, 1997 ) T_min = 0.484, T_max = 0.688
14478 measured reflections
3867 independent reflections
2378 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.097
S = 0.99
3867 reflections
258 parameters
19 restraints
H-atom parameters constrained
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015268/im2108sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809015268/im2108Isup2.hkl

checkCIF report

Comment top

Photolysis of 1,1-diarylgermetanes results in two competing modes of cycloreversion: (2 + 2) to yield the corresponding 1,1-diarylgermene (R₂Ge=CH₂) and ethylene, and (3 + 1) to yield the corresponding diarylgermylene (R₂Ge) and cyclopropane (Leigh et al., 2008). While the quantum yield for decomposition of the germetane remains roughly constant regardless of aromatic substitutent (Φ ca 0.10), decreasing the electron density at germanium by aromatic ring substitution favors formation of the germylene and cyclopropane (Leigh et al., 2008). The molecular structure of (I) is shown in Figure 1. The internal C—Ge—C bond angle is 77.8 (3)°.

To our knowledge, there are no other reported crystal structures of germacyclobutanes (i.e. those in which the three carbon atoms of the four membered ring are all saturated) with which to compare these data. There are, however, several reported crystal structures of germacyclobutenes to which limited comparisons can be made (Tokitoh et al., 1995; Eichler et al., 1999; Meiners et al., 2002; Tajima et al., 2005). The endocyclic Ge—C bond distances are quite similar, despite the carbon-carbon double bond within the ring, and the endocyclic C—Ge—C angle is slightly smaller in these germacyclobutene molecules, which is to be expected. The 4-membered germacyclobutane ring of the title compound is not planar. The angle between the plane made by the carbon atoms in the ring (C15—C17) and the plane containing the germanium and two adjacent carbon atoms in the ring (C15, C17) is 24 (2)°. The aromatic rings are nearly perpendicular, with an angle of 85.8 (1)° between them.

The trifluoromethyl groups are disordered and have been refined as such (see refinement details). The two CF₃ groups interact with each other and the germacyclobutane ring of neighbouring molecules (see the packing diagram - Figure 2). The non-planarity of the germacyclobutane ring results in disorder that has been refined over two occupancy sites.

The crystal structure of an analogue of (I) in which the aromatic rings are substituted at the 3 and 5 positions with CF₃ groups [i.e. 1,1-bis(3,5-bis(trifluoromethyl)phenyl)germetane] exhibits similar structural features (Potter, et al., 2009).

Related literature top

For the synthesis of the title compound, see: Leigh et al. (2008). For related compounds see: Tokitoh et al. (1995); Eichler et al. (1999); Meiners et al. (2002); Tajima et al. (2005). For 1,1-bis(3,5-bis(trifluoromethyl)phenyl)germetane], which exhibits similar structural features, see: Potter et al. (2009).

Experimental top

Compound (I) was synthesized as described elsewhere (Leigh et al., 2008). Single crystals for x-ray diffraction were obtained via repeated recrystallizations from methanol.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structures of (I) drawn with 50% probability ellipsoids. H atoms not shown. Both trifluoromethyl groups and the (CH₂)₃ group are disordered but the disorder is not shown for clarity.
	Fig. 2. Packing diagram of (I) in the space group P 2₁/n.

1,1-Bis[4-(trifluoromethyl)phenyl]germetane top

Crystal data top

[Ge(C₃H₆)(C₇H₄F₃)₂]	F(000) = 808
M_r = 404.87	D_x = 1.594 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 319 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 13.596 (6) Å	Cell parameters from 5916 reflections
b = 6.412 (3) Å	θ = 3.5–26.6°
c = 20.243 (9) Å	µ = 1.87 mm⁻¹
β = 107.081 (7)°	T = 173 K
V = 1687 (1) Å³	Block, colourless
Z = 4	0.40 × 0.38 × 0.20 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3867 independent reflections
Radiation source: fine-focus sealed tube	2378 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.6°
Absorption correction: multi-scan SADABS	h = −17→17
T_min = 0.484, T_max = 0.688	k = −8→8
14478 measured reflections	l = −26→25

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0275P)² + 2.3419P] where P = (F_o² + 2F_c²)/3
3867 reflections	(Δ/σ)_max = 0.022
258 parameters	Δρ_max = 0.68 e Å⁻³
19 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Ge(C₃H₆)(C₇H₄F₃)₂]	V = 1687 (1) Å³
M_r = 404.87	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.596 (6) Å	µ = 1.87 mm⁻¹
b = 6.412 (3) Å	T = 173 K
c = 20.243 (9) Å	0.40 × 0.38 × 0.20 mm
β = 107.081 (7)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3867 independent reflections
Absorption correction: multi-scan SADABS	2378 reflections with I > 2σ(I)
T_min = 0.484, T_max = 0.688	R_int = 0.053
14478 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	19 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 0.99	Δρ_max = 0.68 e Å⁻³
3867 reflections	Δρ_min = −0.61 e Å⁻³
258 parameters

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ge1A	0.88719 (3)	0.20119 (6)	0.19017 (2)	0.03626 (13)	0.396 (14)
C15A	0.7582 (7)	0.347 (4)	0.1861 (18)	0.049 (3)	0.396 (14)
H15C	0.7483	0.3738	0.2319	0.058*	0.396 (14)
H15D	0.7466	0.4755	0.1576	0.058*	0.396 (14)
C16A	0.6994 (5)	0.152 (3)	0.1482 (9)	0.058 (3)	0.396 (14)
H16C	0.6402	0.1931	0.1086	0.070*	0.396 (14)
H16D	0.6745	0.0638	0.1801	0.070*	0.396 (14)
C17A	0.7845 (7)	0.034 (4)	0.1227 (15)	0.0493 (15)	0.396 (14)
H17C	0.7811	0.0624	0.0740	0.059*	0.396 (14)
H17D	0.7889	−0.1177	0.1325	0.059*	0.396 (14)
Ge1	0.88719 (3)	0.20119 (6)	0.19017 (2)	0.03626 (13)	0.604 (14)
C15	0.7486 (5)	0.302 (3)	0.1857 (11)	0.049 (3)	0.604 (14)
H15A	0.7232	0.2525	0.2240	0.058*	0.604 (14)
H15B	0.7400	0.4551	0.1796	0.058*	0.604 (14)
C16	0.7073 (5)	0.1749 (18)	0.1173 (6)	0.058 (3)	0.604 (14)
H16A	0.6958	0.2660	0.0763	0.070*	0.604 (14)
H16B	0.6424	0.1022	0.1156	0.070*	0.604 (14)
C17	0.7979 (11)	0.013 (6)	0.122 (2)	0.0493 (15)	0.604 (14)
H17A	0.8172	−0.0008	0.0786	0.059*	0.604 (14)
H17B	0.7874	−0.1249	0.1407	0.059*	0.604 (14)
C1	0.9675 (3)	0.0705 (5)	0.27568 (18)	0.0341 (8)
C2	1.0113 (3)	−0.1241 (6)	0.2752 (2)	0.0445 (9)
H2A	1.0030	−0.1936	0.2324	0.053*
C3	1.0670 (3)	−0.2189 (6)	0.3359 (2)	0.0485 (10)
H3A	1.0965	−0.3526	0.3346	0.058*
C4	1.0799 (3)	−0.1212 (6)	0.39821 (19)	0.0407 (9)
C5	1.0369 (3)	0.0734 (6)	0.3998 (2)	0.0471 (10)
H5A	1.0456	0.1424	0.4427	0.056*
C6	0.9812 (3)	0.1671 (5)	0.3389 (2)	0.0444 (9)
H6A	0.9517	0.3006	0.3404	0.053*
C8	0.9769 (3)	0.3844 (5)	0.15718 (18)	0.0379 (8)
C9	1.0823 (3)	0.3923 (6)	0.1889 (2)	0.0470 (10)
H9A	1.1126	0.3007	0.2262	0.056*
C10	1.1437 (3)	0.5314 (6)	0.1669 (2)	0.0510 (10)
H10A	1.2158	0.5345	0.1889	0.061*
C11	1.1000 (3)	0.6659 (6)	0.1130 (2)	0.0448 (9)
C12	0.9955 (3)	0.6588 (6)	0.0806 (2)	0.0512 (10)
H12A	0.9653	0.7506	0.0433	0.061*
C13	0.9352 (3)	0.5183 (6)	0.1024 (2)	0.0471 (10)
H13A	0.8635	0.5130	0.0795	0.057*
C7	1.1400 (4)	−0.2268 (7)	0.4628 (2)	0.0561 (11)	0.604 (14)
F1	1.1175 (11)	−0.4307 (12)	0.4626 (7)	0.083 (3)	0.604 (14)
F2	1.1343 (13)	−0.146 (2)	0.5219 (6)	0.078 (4)	0.604 (14)
F3	1.2396 (5)	−0.227 (3)	0.4671 (8)	0.072 (3)	0.604 (14)
C7A	1.1400 (4)	−0.2268 (7)	0.4628 (2)	0.0561 (11)	0.396 (14)
F1A	1.0871 (16)	−0.380 (3)	0.4803 (12)	0.106 (7)	0.396 (14)
F2A	1.1506 (18)	−0.091 (3)	0.5158 (8)	0.070 (5)	0.396 (14)
F3A	1.2337 (11)	−0.281 (4)	0.4667 (12)	0.091 (8)	0.396 (14)
C14	1.1663 (3)	0.8216 (7)	0.0908 (2)	0.0589 (11)	0.410 (6)
F4	1.1154 (5)	1.0064 (10)	0.0742 (5)	0.0613 (7)*	0.410 (6)
F5	1.1939 (6)	0.7630 (11)	0.0372 (4)	0.0613 (7)*	0.410 (6)
F6	1.2236 (6)	0.9328 (12)	0.1444 (3)	0.0613 (7)*	0.410 (6)
C14'	1.1663 (3)	0.8216 (7)	0.0908 (2)	0.0589 (11)	0.411 (6)
F4'	1.1110 (5)	0.9575 (12)	0.0424 (5)	0.0613 (7)*	0.411 (6)
F5'	1.2282 (6)	0.7196 (11)	0.0569 (4)	0.0613 (7)*	0.411 (6)
F6'	1.2569 (6)	0.8560 (12)	0.1386 (4)	0.0613 (7)*	0.411 (6)
C14A	1.1663 (3)	0.8216 (7)	0.0908 (2)	0.0589 (11)	0.179 (3)
F4A	1.1322 (12)	0.867 (2)	0.0240 (6)	0.0613 (7)*	0.179 (3)
F5A	1.2639 (10)	0.769 (2)	0.1061 (9)	0.0613 (7)*	0.179 (3)
F6A	1.1623 (13)	1.0042 (19)	0.1205 (9)	0.0613 (7)*	0.179 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ge1A	0.0323 (2)	0.03686 (19)	0.0365 (2)	0.00216 (19)	0.00519 (16)	0.0002 (2)
C15A	0.042 (3)	0.046 (7)	0.062 (3)	0.005 (3)	0.021 (3)	0.017 (4)
C16A	0.032 (3)	0.065 (4)	0.072 (7)	−0.005 (3)	0.006 (4)	0.022 (6)
C17A	0.042 (3)	0.052 (5)	0.045 (3)	−0.009 (4)	−0.002 (4)	0.003 (3)
Ge1	0.0323 (2)	0.03686 (19)	0.0365 (2)	0.00216 (19)	0.00519 (16)	0.0002 (2)
C15	0.042 (3)	0.046 (7)	0.062 (3)	0.005 (3)	0.021 (3)	0.017 (4)
C16	0.032 (3)	0.065 (4)	0.072 (7)	−0.005 (3)	0.006 (4)	0.022 (6)
C17	0.042 (3)	0.052 (5)	0.045 (3)	−0.009 (4)	−0.002 (4)	0.003 (3)
C1	0.0292 (19)	0.0364 (17)	0.034 (2)	−0.0018 (15)	0.0055 (16)	−0.0001 (16)
C2	0.048 (2)	0.045 (2)	0.037 (2)	0.0075 (18)	0.0078 (19)	−0.0067 (17)
C3	0.051 (2)	0.0427 (19)	0.047 (2)	0.0167 (19)	0.007 (2)	0.0012 (19)
C4	0.036 (2)	0.0454 (19)	0.039 (2)	0.0012 (17)	0.0077 (18)	0.0022 (18)
C5	0.049 (2)	0.051 (2)	0.035 (2)	0.0023 (19)	0.0048 (19)	−0.0080 (19)
C6	0.043 (2)	0.037 (2)	0.047 (2)	0.0069 (17)	0.0042 (19)	−0.0044 (18)
C8	0.037 (2)	0.0359 (17)	0.035 (2)	0.0027 (16)	0.0030 (17)	−0.0011 (16)
C9	0.039 (2)	0.048 (2)	0.050 (2)	0.0036 (18)	0.006 (2)	0.0091 (19)
C10	0.034 (2)	0.056 (2)	0.059 (3)	0.0020 (19)	0.007 (2)	0.006 (2)
C11	0.044 (2)	0.046 (2)	0.045 (2)	−0.0039 (18)	0.0148 (19)	−0.0005 (18)
C12	0.048 (2)	0.055 (3)	0.045 (2)	−0.004 (2)	0.006 (2)	0.0112 (19)
C13	0.035 (2)	0.057 (2)	0.041 (2)	−0.0023 (19)	−0.0019 (18)	0.0086 (19)
C7	0.058 (3)	0.063 (3)	0.041 (2)	0.009 (3)	0.004 (2)	0.006 (2)
F1	0.110 (8)	0.054 (3)	0.061 (6)	−0.009 (4)	−0.013 (4)	0.019 (3)
F2	0.110 (8)	0.089 (7)	0.042 (4)	0.048 (6)	0.034 (4)	0.022 (4)
F3	0.044 (5)	0.093 (6)	0.062 (5)	0.014 (4)	−0.011 (4)	0.014 (4)
C7A	0.058 (3)	0.063 (3)	0.041 (2)	0.009 (3)	0.004 (2)	0.006 (2)
F1A	0.110 (12)	0.108 (12)	0.075 (12)	−0.022 (10)	−0.012 (7)	0.050 (9)
F2A	0.078 (7)	0.099 (11)	0.023 (5)	0.012 (7)	0.001 (5)	0.015 (6)
F3A	0.103 (13)	0.122 (17)	0.053 (8)	0.080 (12)	0.029 (8)	0.013 (8)
C14	0.055 (3)	0.062 (3)	0.059 (3)	0.005 (2)	0.015 (2)	0.006 (2)
C14'	0.055 (3)	0.062 (3)	0.059 (3)	0.005 (2)	0.015 (2)	0.006 (2)
C14A	0.055 (3)	0.062 (3)	0.059 (3)	0.005 (2)	0.015 (2)	0.006 (2)

Geometric parameters (Å, º) top

Ge1A—C1	1.944 (3)	C3—C4	1.372 (5)
Ge1A—C8	1.947 (4)	C3—H3A	0.9500
Ge1A—C17A	1.961 (4)	C4—C5	1.382 (5)
Ge1A—C15A	1.969 (5)	C4—C7	1.486 (5)
Ge1A—C16A	2.463 (6)	C5—C6	1.381 (5)
C15A—C16A	1.562 (11)	C5—H5A	0.9500
C15A—H15C	0.9900	C6—H6A	0.9500
C15A—H15D	0.9900	C8—C13	1.384 (5)
C16A—C17A	1.591 (13)	C8—C9	1.389 (5)
C16A—H16C	0.9900	C9—C10	1.381 (5)
C16A—H16D	0.9900	C9—H9A	0.9500
C17A—H17C	0.9900	C10—C11	1.382 (5)
C17A—H17D	0.9900	C10—H10A	0.9500
C15—C16	1.563 (11)	C11—C12	1.379 (5)
C15—H15A	0.9900	C11—C14	1.500 (6)
C15—H15B	0.9900	C12—C13	1.376 (5)
C16—C17	1.591 (13)	C12—H12A	0.9500
C16—H16A	0.9900	C13—H13A	0.9500
C16—H16B	0.9900	C7—F2	1.326 (9)
C17—H17A	0.9900	C7—F3	1.331 (9)
C17—H17B	0.9900	C7—F1	1.342 (9)
C1—C6	1.383 (5)	C14—F5	1.302 (8)
C1—C2	1.385 (5)	C14—F6	1.340 (7)
C2—C3	1.381 (5)	C14—F4	1.363 (7)
C2—H2A	0.9500

C1—Ge1A—C8	108.72 (15)	C3—C2—C1	121.0 (3)
C1—Ge1A—C17A	118.9 (11)	C3—C2—H2A	119.5
C8—Ge1A—C17A	118.7 (11)	C1—C2—H2A	119.5
C1—Ge1A—C15A	120.2 (12)	C4—C3—C2	120.4 (3)
C8—Ge1A—C15A	109.8 (11)	C4—C3—H3A	119.8
C17A—Ge1A—C15A	77.8 (3)	C2—C3—H3A	119.8
C1—Ge1A—C16A	120.4 (4)	C3—C4—C5	119.5 (3)
C8—Ge1A—C16A	130.5 (4)	C3—C4—C7	119.3 (3)
C16A—C15A—Ge1A	87.7 (4)	C5—C4—C7	121.2 (4)
C16A—C15A—H15C	114.0	C6—C5—C4	119.8 (3)
Ge1A—C15A—H15C	114.0	C6—C5—H5A	120.1
C16A—C15A—H15D	114.0	C4—C5—H5A	120.1
Ge1A—C15A—H15D	114.0	C5—C6—C1	121.4 (3)
H15C—C15A—H15D	111.2	C5—C6—H6A	119.3
C15A—C16A—C17A	103.0 (8)	C1—C6—H6A	119.3
C15A—C16A—Ge1A	53.0 (3)	C13—C8—C9	118.1 (4)
C17A—C16A—Ge1A	52.7 (2)	C13—C8—Ge1A	119.9 (3)
C15A—C16A—H16C	111.2	C9—C8—Ge1A	121.9 (3)
C17A—C16A—H16C	111.2	C10—C9—C8	120.9 (4)
Ge1A—C16A—H16C	139.4	C10—C9—H9A	119.5
C15A—C16A—H16D	111.2	C8—C9—H9A	119.5
C17A—C16A—H16D	111.2	C9—C10—C11	119.9 (4)
Ge1A—C16A—H16D	111.5	C9—C10—H10A	120.1
H16C—C16A—H16D	109.1	C11—C10—H10A	120.1
C16A—C17A—Ge1A	87.1 (5)	C12—C11—C10	119.8 (4)
C16A—C17A—H17C	114.1	C12—C11—C14	120.4 (4)
Ge1A—C17A—H17C	114.1	C10—C11—C14	119.8 (4)
C16A—C17A—H17D	114.1	C13—C12—C11	119.8 (4)
Ge1A—C17A—H17D	114.1	C13—C12—H12A	120.1
H17C—C17A—H17D	111.3	C11—C12—H12A	120.1
C16—C15—H15A	114.1	C12—C13—C8	121.4 (4)
C16—C15—H15B	114.1	C12—C13—H13A	119.3
H15A—C15—H15B	111.2	C8—C13—H13A	119.3
C15—C16—C17	102.6 (8)	F2—C7—F3	105.6 (9)
C15—C16—H16A	111.2	F2—C7—F1	108.0 (9)
C17—C16—H16A	111.2	F3—C7—F1	103.0 (9)
C15—C16—H16B	111.2	F2—C7—C4	117.0 (7)
C17—C16—H16B	111.2	F3—C7—C4	110.1 (8)
H16A—C16—H16B	109.2	F1—C7—C4	112.0 (7)
C16—C17—H17A	114.1	F5—C14—F6	125.9 (6)
C16—C17—H17B	114.1	F5—C14—F4	107.2 (5)
H17A—C17—H17B	111.3	F6—C14—F4	82.5 (6)
C6—C1—C2	117.9 (3)	F5—C14—C11	113.7 (5)
C6—C1—Ge1A	121.2 (3)	F6—C14—C11	111.6 (4)
C2—C1—Ge1A	120.8 (3)	F4—C14—C11	110.2 (4)

C1—Ge1A—C15A—C16A	−102.4 (14)	Ge1A—C1—C6—C5	179.0 (3)
C8—Ge1A—C15A—C16A	130.5 (14)	C1—Ge1A—C8—C13	−170.8 (3)
C17A—Ge1A—C15A—C16A	14 (2)	C17A—Ge1A—C8—C13	49.1 (6)
Ge1A—C15A—C16A—C17A	−18 (2)	C15A—Ge1A—C8—C13	−37.5 (9)
C1—Ge1A—C16A—C15A	102 (2)	C16A—Ge1A—C8—C13	1.8 (7)
C8—Ge1A—C16A—C15A	−70 (2)	C1—Ge1A—C8—C9	6.4 (4)
C17A—Ge1A—C16A—C15A	−158 (3)	C17A—Ge1A—C8—C9	−133.7 (6)
C1—Ge1A—C16A—C17A	−100.0 (19)	C15A—Ge1A—C8—C9	139.7 (9)
C8—Ge1A—C16A—C17A	88.2 (19)	C16A—Ge1A—C8—C9	179.0 (7)
C15A—Ge1A—C16A—C17A	158 (3)	C13—C8—C9—C10	0.7 (6)
C15A—C16A—C17A—Ge1A	18 (2)	Ge1A—C8—C9—C10	−176.5 (3)
C1—Ge1A—C17A—C16A	104.0 (13)	C8—C9—C10—C11	0.4 (6)
C8—Ge1A—C17A—C16A	−119.9 (14)	C9—C10—C11—C12	−0.9 (6)
C15A—Ge1A—C17A—C16A	−13.9 (19)	C9—C10—C11—C14	178.0 (4)
C8—Ge1A—C1—C6	86.7 (3)	C10—C11—C12—C13	0.3 (6)
C17A—Ge1A—C1—C6	−133.3 (7)	C14—C11—C12—C13	−178.6 (4)
C15A—Ge1A—C1—C6	−40.9 (8)	C11—C12—C13—C8	0.9 (6)
C16A—Ge1A—C1—C6	−86.8 (6)	C9—C8—C13—C12	−1.4 (6)
C8—Ge1A—C1—C2	−94.4 (3)	Ge1A—C8—C13—C12	175.9 (3)
C17A—Ge1A—C1—C2	45.6 (7)	C3—C4—C7—F2	−167.6 (9)
C15A—Ge1A—C1—C2	138.0 (8)	C5—C4—C7—F2	12.3 (10)
C16A—Ge1A—C1—C2	92.1 (6)	C3—C4—C7—F3	71.9 (9)
C6—C1—C2—C3	0.0 (6)	C5—C4—C7—F3	−108.2 (9)
Ge1A—C1—C2—C3	−178.9 (3)	C3—C4—C7—F1	−42.2 (8)
C1—C2—C3—C4	0.0 (6)	C5—C4—C7—F1	137.8 (7)
C2—C3—C4—C5	−0.1 (6)	C12—C11—C14—F5	−82.7 (6)
C2—C3—C4—C7	179.9 (4)	C10—C11—C14—F5	98.4 (6)
C3—C4—C5—C6	0.2 (6)	C12—C11—C14—F6	127.5 (6)
C7—C4—C5—C6	−179.8 (4)	C10—C11—C14—F6	−51.4 (7)
C4—C5—C6—C1	−0.2 (6)	C12—C11—C14—F4	37.7 (7)
C2—C1—C6—C5	0.1 (6)	C10—C11—C14—F4	−141.2 (6)

Experimental details

Crystal data
Chemical formula	[Ge(C₃H₆)(C₇H₄F₃)₂]
M_r	404.87
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	13.596 (6), 6.412 (3), 20.243 (9)
β (°)	107.081 (7)
V (Å³)	1687 (1)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.87
Crystal size (mm)	0.40 × 0.38 × 0.20

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan SADABS
T_min, T_max	0.484, 0.688
No. of measured, independent and observed [I > 2σ(I)] reflections	14478, 3867, 2378
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.097, 0.99
No. of reflections	3867
No. of parameters	258
No. of restraints	19
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.68, −0.61

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

We thank the Natural Sciences and Engineering Research Council (NSERC) of Canada for financial support and for a postgraduate scholarship to LAH.

References

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