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The inter­nal C-Ge-C bond angle in the germacyclo­pentene ring of the title compound, C20H18F6Ge or [Ge(C6H10)(C7H4F3)2], is 93.17 (9)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015024/fl2113sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015024/fl2113Isup2.hkl
Contains datablock I

CCDC reference: 647208

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • Disorder in main residue
  • R factor = 0.040
  • wR factor = 0.109
  • Data-to-parameter ratio = 24.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C17 PLAT431_ALERT_2_B Short Inter HL..A Contact F1A .. F1A .. 2.49 Ang.
Alert level C PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 11 PLAT213_ALERT_2_C Atom F2 has ADP max/min Ratio ............. 3.10 prola PLAT213_ALERT_2_C Atom C17 has ADP max/min Ratio ............. 3.20 oblat PLAT213_ALERT_2_C Atom F1A has ADP max/min Ratio ............. 3.30 prola PLAT213_ALERT_2_C Atom F2A has ADP max/min Ratio ............. 4.00 prola PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17A PLAT301_ALERT_3_C Main Residue Disorder ......................... 13.00 Perc. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C5
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEXII (Bruker, 2006); cell refinement: APEXII; data reduction: SAINT (Sheldrick, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXTL (Sheldrick, 2000).

3,4-Dimethyl-1,1-bis[4-(trifluoromethyl)phenyl]-2,5-dihydro-1H-germole top
Crystal data top
[Ge(C6H10)(C7H4F3)2]F(000) = 896
Mr = 444.93Dx = 1.572 Mg m3
Monoclinic, P21/cMelting point: 59.2 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 6.535 (2) ÅCell parameters from 6132 reflections
b = 18.367 (6) Åθ = 2.6–31.7°
c = 15.674 (5) ŵ = 1.69 mm1
β = 91.726 (6)°T = 173 K
V = 1880.4 (10) Å3Block, colorless
Z = 40.20 × 0.20 × 0.08 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
8127 independent reflections
Radiation source: fine-focus sealed tube5493 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
φ and ω scansθmax = 36.3°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1997)
h = 610
Tmin = 0.733, Tmax = 0.87k = 3030
43214 measured reflectionsl = 2526
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.052P)2 + 0.3451P]
where P = (Fo2 + 2Fc2)/3
8127 reflections(Δ/σ)max = 0.002
326 parametersΔρmax = 0.55 e Å3
42 restraintsΔρmin = 0.41 e Å3
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
xyzUiso*/UeqOcc. (<1)
Ge10.37011 (3)0.29082 (9)0.27900 (11)0.02359 (6)
C10.5709 (3)0.36294 (10)0.31801 (13)0.0311 (4)
C20.5364 (3)0.42557 (9)0.25664 (12)0.0293 (4)
C30.3746 (3)0.42372 (10)0.20158 (12)0.0303 (4)
C40.2302 (3)0.35918 (10)0.20200 (13)0.0310 (4)
C50.3211 (4)0.48218 (12)0.13742 (16)0.0476 (6)
H5A0.19660.46830.10500.071*
H5B0.43400.48810.09830.071*
H5C0.29770.52820.16720.071*
C60.6927 (4)0.48576 (12)0.26242 (16)0.0430 (5)
H6A0.79520.47430.30730.065*
H6B0.62460.53170.27600.065*
H6C0.76000.49050.20760.065*
C110.4981 (3)0.21205 (9)0.21705 (11)0.0248 (3)
C120.6861 (3)0.18282 (11)0.24504 (12)0.0310 (4)
C130.7825 (3)0.12910 (11)0.19858 (12)0.0324 (4)
C140.6913 (3)0.10339 (10)0.12395 (11)0.0279 (3)
C150.5035 (3)0.13044 (11)0.09538 (12)0.0310 (4)
C160.4084 (3)0.18444 (11)0.14197 (12)0.0288 (4)
C210.1977 (3)0.24657 (9)0.36455 (11)0.0243 (3)
C220.1934 (3)0.17081 (10)0.37464 (12)0.0280 (3)
C230.0633 (3)0.13757 (10)0.43115 (12)0.0296 (4)
C240.0662 (3)0.18031 (10)0.47865 (11)0.0275 (3)
C250.0612 (3)0.25561 (11)0.47116 (12)0.0318 (4)
H250.14800.28480.50470.039 (7)*
C260.0699 (3)0.28833 (10)0.41494 (12)0.0295 (4)
C270.2178 (3)0.14580 (12)0.53562 (13)0.0359 (4)
F40.1760 (2)0.07622 (7)0.55366 (9)0.0511 (4)
F50.2273 (2)0.18006 (8)0.61090 (8)0.0491 (3)
F60.4071 (2)0.14691 (11)0.50101 (11)0.0665 (5)
H10.706 (4)0.3464 (12)0.3143 (14)0.033 (6)*
H20.552 (4)0.3785 (16)0.3778 (19)0.058 (8)*
H90.209 (3)0.3386 (12)0.1459 (15)0.029 (5)*
H100.101 (4)0.3736 (14)0.2242 (15)0.039 (7)*
H120.753 (4)0.1997 (13)0.2989 (18)0.044 (7)*
H130.904 (4)0.1081 (14)0.2175 (15)0.041 (7)*
H150.447 (4)0.1119 (14)0.0440 (16)0.042 (7)*
H160.291 (4)0.2024 (12)0.1224 (16)0.033 (6)*
H220.283 (4)0.1376 (14)0.3410 (17)0.047 (7)*
H230.060 (4)0.0847 (15)0.4343 (17)0.049 (7)*
H260.068 (4)0.3358 (14)0.4071 (15)0.037 (6)*
C170.7972 (14)0.0437 (6)0.0731 (6)0.0268 (18)0.54 (2)
F10.9993 (11)0.0649 (5)0.0656 (7)0.071 (2)0.54 (2)
F20.804 (2)0.0169 (5)0.1067 (8)0.084 (4)0.54 (2)
F30.7367 (16)0.0450 (6)0.0063 (3)0.073 (3)0.54 (2)
C17A0.804 (2)0.0523 (9)0.0751 (8)0.043 (3)0.46 (2)
F1A0.6828 (17)0.0168 (8)0.0123 (11)0.100 (4)0.46 (2)
F2A0.9663 (19)0.0694 (4)0.0436 (8)0.080 (4)0.46 (2)
F3A0.847 (2)0.0109 (6)0.1189 (9)0.075 (3)0.46 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ge10.02359 (10)0.02219 (8)0.02501 (9)0.00257 (7)0.00095 (6)0.00087 (7)
C10.0319 (10)0.0286 (8)0.0325 (9)0.0013 (7)0.0033 (7)0.0013 (7)
C20.0327 (10)0.0223 (7)0.0333 (9)0.0022 (7)0.0071 (7)0.0026 (6)
C30.0356 (10)0.0247 (8)0.0308 (9)0.0071 (7)0.0051 (7)0.0007 (7)
C40.0312 (10)0.0300 (9)0.0317 (9)0.0065 (7)0.0024 (7)0.0011 (7)
C50.0641 (16)0.0347 (11)0.0440 (12)0.0085 (10)0.0004 (11)0.0114 (9)
C60.0470 (13)0.0310 (10)0.0514 (13)0.0079 (9)0.0073 (10)0.0018 (9)
C110.0250 (8)0.0248 (7)0.0248 (7)0.0018 (6)0.0042 (6)0.0011 (6)
C120.0317 (9)0.0332 (9)0.0279 (8)0.0076 (8)0.0024 (7)0.0016 (7)
C130.0292 (9)0.0372 (10)0.0307 (9)0.0106 (8)0.0003 (7)0.0003 (7)
C140.0299 (9)0.0267 (8)0.0276 (8)0.0040 (7)0.0089 (7)0.0002 (6)
C150.0308 (9)0.0334 (9)0.0289 (8)0.0027 (7)0.0006 (7)0.0059 (7)
C160.0235 (9)0.0315 (8)0.0311 (9)0.0042 (7)0.0011 (7)0.0047 (7)
C210.0242 (8)0.0239 (7)0.0247 (7)0.0022 (6)0.0010 (6)0.0020 (6)
C220.0290 (9)0.0252 (8)0.0301 (8)0.0039 (7)0.0037 (7)0.0031 (6)
C230.0313 (9)0.0247 (8)0.0328 (9)0.0013 (7)0.0025 (7)0.0012 (7)
C240.0265 (9)0.0316 (9)0.0244 (8)0.0007 (7)0.0005 (6)0.0005 (6)
C250.0326 (10)0.0312 (9)0.0318 (9)0.0046 (7)0.0070 (7)0.0058 (7)
C260.0334 (10)0.0227 (7)0.0325 (9)0.0038 (7)0.0038 (7)0.0032 (7)
C270.0321 (10)0.0429 (11)0.0327 (9)0.0015 (8)0.0038 (8)0.0012 (8)
F40.0624 (9)0.0389 (7)0.0532 (8)0.0045 (6)0.0222 (7)0.0077 (6)
F50.0557 (9)0.0543 (8)0.0386 (7)0.0022 (7)0.0224 (6)0.0054 (6)
F60.0298 (7)0.1050 (14)0.0641 (10)0.0166 (8)0.0059 (7)0.0263 (9)
C170.027 (3)0.024 (2)0.031 (3)0.0072 (19)0.017 (2)0.010 (2)
F10.032 (2)0.078 (4)0.104 (4)0.0056 (19)0.020 (3)0.038 (3)
F20.144 (7)0.0232 (19)0.089 (6)0.000 (3)0.083 (6)0.005 (2)
F30.091 (5)0.102 (5)0.0271 (19)0.063 (4)0.0064 (19)0.019 (2)
C17A0.062 (7)0.033 (4)0.033 (5)0.001 (3)0.012 (4)0.011 (3)
F1A0.065 (4)0.103 (7)0.129 (8)0.034 (4)0.025 (5)0.093 (6)
F2A0.109 (7)0.025 (2)0.111 (6)0.001 (3)0.097 (6)0.005 (3)
F3A0.123 (6)0.043 (4)0.062 (3)0.051 (5)0.032 (4)0.011 (3)
Geometric parameters (Å, º) top
Ge1—C111.9455 (17)C14—C17A1.430 (13)
Ge1—C11.950 (2)C14—C171.534 (7)
Ge1—C41.9500 (19)C15—C161.389 (3)
Ge1—C211.9541 (18)C15—H150.94 (3)
C1—C21.512 (3)C16—H160.88 (2)
C1—H10.94 (2)C21—C261.397 (2)
C1—H20.99 (3)C21—C221.401 (3)
C2—C31.345 (3)C22—C231.388 (3)
C2—C61.506 (3)C22—H221.00 (3)
C3—C51.505 (3)C23—C241.387 (3)
C3—C41.515 (3)C23—H230.97 (3)
C4—H90.96 (2)C24—C251.388 (3)
C4—H100.96 (2)C24—C271.495 (3)
C5—H5A0.9800C25—C261.385 (3)
C5—H5B0.9800C25—H250.9500
C5—H5C0.9800C26—H260.88 (3)
C6—H6A0.9800C27—F41.335 (3)
C6—H6B0.9800C27—F61.336 (3)
C6—H6C0.9800C27—F51.340 (2)
C11—C161.394 (3)C17—F21.232 (13)
C11—C121.399 (3)C17—F31.295 (12)
C12—C131.389 (3)C17—F11.385 (12)
C12—H120.99 (3)C17A—F2A1.223 (17)
C13—C141.380 (3)C17A—F3A1.375 (16)
C13—H130.92 (3)C17A—F1A1.406 (17)
C14—C151.386 (3)
C11—Ge1—C1111.49 (9)C13—C14—C17A117.5 (6)
C11—Ge1—C4111.75 (8)C15—C14—C17A121.9 (6)
C1—Ge1—C493.17 (9)C13—C14—C17119.7 (4)
C11—Ge1—C21107.36 (7)C15—C14—C17119.9 (4)
C1—Ge1—C21117.64 (8)C14—C15—C16119.47 (18)
C4—Ge1—C21115.04 (8)C14—C15—H15117.9 (15)
C2—C1—Ge1103.36 (13)C16—C15—H15122.6 (15)
C2—C1—H1109.2 (14)C15—C16—C11121.32 (18)
Ge1—C1—H1112.8 (14)C15—C16—H16118.9 (16)
C2—C1—H2111.2 (17)C11—C16—H16119.8 (16)
Ge1—C1—H2112.8 (17)C26—C21—C22117.86 (16)
H1—C1—H2107 (2)C26—C21—Ge1121.78 (13)
C3—C2—C6125.15 (18)C22—C21—Ge1120.31 (12)
C3—C2—C1119.25 (17)C23—C22—C21121.59 (16)
C6—C2—C1115.60 (18)C23—C22—H22116.4 (15)
C2—C3—C5124.98 (19)C21—C22—H22122.0 (15)
C2—C3—C4119.64 (17)C24—C23—C22119.27 (17)
C5—C3—C4115.38 (18)C24—C23—H23121.4 (16)
C3—C4—Ge1103.05 (13)C22—C23—H23119.2 (16)
C3—C4—H9112.1 (13)C23—C24—C25120.14 (17)
Ge1—C4—H9111.4 (13)C23—C24—C27120.44 (18)
C3—C4—H10109.8 (15)C25—C24—C27119.37 (17)
Ge1—C4—H10110.7 (14)C26—C25—C24120.17 (17)
H9—C4—H10109.6 (19)C26—C25—H25119.9
C3—C5—H5A109.5C24—C25—H25119.9
C3—C5—H5B109.5C25—C26—C21120.92 (17)
H5A—C5—H5B109.5C25—C26—H26120.8 (16)
C3—C5—H5C109.5C21—C26—H26118.1 (17)
H5A—C5—H5C109.5F4—C27—F6106.35 (19)
H5B—C5—H5C109.5F4—C27—F5106.11 (17)
C2—C6—H6A109.5F6—C27—F5106.47 (18)
C2—C6—H6B109.5F4—C27—C24113.41 (17)
H6A—C6—H6B109.5F6—C27—C24111.93 (17)
C2—C6—H6C109.5F5—C27—C24112.08 (17)
H6A—C6—H6C109.5F2—C17—F3115.8 (11)
H6B—C6—H6C109.5F2—C17—F1105.4 (9)
C16—C11—C12117.91 (16)F3—C17—F1100.3 (7)
C16—C11—Ge1121.04 (14)F2—C17—C14115.8 (7)
C12—C11—Ge1121.02 (14)F3—C17—C14110.9 (7)
C13—C12—C11121.06 (18)F1—C17—C14106.8 (8)
C13—C12—H12118.4 (15)F2A—C17A—F3A104.6 (11)
C11—C12—H12120.5 (15)F2A—C17A—F1A108.3 (11)
C14—C13—C12119.77 (18)F3A—C17A—F1A93.5 (14)
C14—C13—H13118.3 (15)F2A—C17A—C14121.0 (14)
C12—C13—H13121.8 (15)F3A—C17A—C14112.8 (10)
C13—C14—C15120.46 (17)F1A—C17A—C14113.0 (10)
C11—Ge1—C1—C2104.19 (13)C11—Ge1—C21—C223.27 (17)
C4—Ge1—C1—C210.68 (14)C1—Ge1—C21—C22123.38 (15)
C21—Ge1—C1—C2131.19 (12)C4—Ge1—C21—C22128.34 (15)
Ge1—C1—C2—C38.4 (2)C26—C21—C22—C231.6 (3)
Ge1—C1—C2—C6170.95 (14)Ge1—C21—C22—C23175.99 (15)
C6—C2—C3—C51.0 (3)C21—C22—C23—C240.2 (3)
C1—C2—C3—C5179.72 (19)C22—C23—C24—C251.7 (3)
C6—C2—C3—C4179.30 (18)C22—C23—C24—C27175.89 (18)
C1—C2—C3—C40.1 (3)C23—C24—C25—C261.4 (3)
C2—C3—C4—Ge18.4 (2)C27—C24—C25—C26176.22 (19)
C5—C3—C4—Ge1171.87 (15)C24—C25—C26—C210.5 (3)
C11—Ge1—C4—C3104.00 (13)C22—C21—C26—C251.9 (3)
C1—Ge1—C4—C310.66 (14)Ge1—C21—C26—C25175.64 (15)
C21—Ge1—C4—C3133.26 (12)C23—C24—C27—F417.8 (3)
C1—Ge1—C11—C16137.17 (15)C25—C24—C27—F4164.65 (18)
C4—Ge1—C11—C1634.40 (18)C23—C24—C27—F6102.5 (2)
C21—Ge1—C11—C1692.63 (16)C25—C24—C27—F675.0 (2)
C1—Ge1—C11—C1240.87 (17)C23—C24—C27—F5137.91 (19)
C4—Ge1—C11—C12143.65 (15)C25—C24—C27—F544.5 (3)
C21—Ge1—C11—C1289.32 (16)C13—C14—C17—F269.1 (12)
C16—C11—C12—C131.3 (3)C15—C14—C17—F2110.0 (11)
Ge1—C11—C12—C13176.76 (16)C13—C14—C17—F3156.3 (9)
C11—C12—C13—C140.6 (3)C15—C14—C17—F324.6 (12)
C12—C13—C14—C150.5 (3)C17A—C14—C17—F390 (10)
C12—C13—C14—C17A175.1 (7)C13—C14—C17—F148.0 (9)
C12—C13—C14—C17179.6 (5)C15—C14—C17—F1132.9 (7)
C13—C14—C15—C160.8 (3)C17A—C14—C17—F118 (10)
C17A—C14—C15—C16174.6 (8)C13—C14—C17A—F2A63.4 (14)
C17—C14—C15—C16179.9 (5)C15—C14—C17A—F2A112.2 (14)
C14—C15—C16—C110.0 (3)C13—C14—C17A—F3A61.5 (15)
C12—C11—C16—C151.0 (3)C15—C14—C17A—F3A123.0 (11)
Ge1—C11—C16—C15177.08 (15)C17—C14—C17A—F3A55 (10)
C11—Ge1—C21—C26174.20 (15)C13—C14—C17A—F1A165.9 (13)
C1—Ge1—C21—C2659.15 (18)C15—C14—C17A—F1A18.5 (18)
C4—Ge1—C21—C2649.13 (18)C17—C14—C17A—F1A49 (10)
 

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