Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270104030963/fr1515sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104030963/fr1515Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104030963/fr1515IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270104030963/fr1515IIIsup4.hkl |
CCDC references: 212509; 212510; 263032
Compounds (I), (II) and (III) were synthesized following the literature methods described by Choudhary et al. (2001). Suitable crystals were isolated for X-ray analyses by dissolving the respective compound (0.5 g) in chloroform (5.0 ml), to which a few drops of acetone were added. Slow evaporation of the solvent at room temperature over a period of several days yielded fine crystals, which were subsequently washed with acetone. For (I), IR (cm−1): υ 3100–3500 (b, OH), 1699 (s, CO), 563 (w, GeC); 1H NMR (p.p.m.): 2.75 (s, 2H, CH2), 1.47(s, 6H, CH3), 10.81 (s, 1H, OH); 13C NMR (p.p.m.): 46.58 (CH2), 45.48 (C), 25.83 (CH3). For (II), IR (cm−1): υ 3000–3410 (b, OH), 1695 (s, CO), 621 (w, Ge—C); 1H NMR (p.p.m.): 2.55 (s, 2H, CH2), 1.35 (s, 6H, CH3), 7.25–7.81 (m, 15H, C6H5); 13C NMR (p.p.m.): 48.72 (CH2), 42.61 (C), 27.20 (CH3), 136.21, 135.98, 128.13, 131.42 (C6H5Ge). For (III), IR (cm−1): υ 3100–3480 (b, OH), 1711 (s, CO), 629 (w, Ge—C); 1H NMR (p.p.m.): 2.64 (s, 2H, CH2), 1.45 (s, 6H, CH3), 1.18 (d, 9H, J =6.9 Hz, p-CH3C6H4); 13C NMR (p.p.m.): 38.51 (CH2), 34.10 (C), 29.57 (CH3), 21.71 (p-CH3C6H4), 139.45, 134.08, 128.90, 133.86 (C6H4Ge).
In all structures, H-atoms were located from difference Fourier syntheses and were included in the refinements at geometrically idealized positions, with O—H distances of 0.84 Å, C—H distances of 0.95, 0.98 and 0.99 Å, and Uiso(H) values of 1.5 (hydroxyl and methyl) and 1.2 (aromatic and CH2) times Ueq of the parent atoms. The final difference map was free of any chemically significant features.
For all compounds, data collection: COLLECT (Hooft, 1998); cell refinement: HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976). Software used to prepare material for publication: SHELXL97 for (I), (II); SHELXL97 (Sheldrick, 1997) for (III).
[Ge(C5H9O2)Cl3] | F(000) = 1104 |
Mr = 280.06 | Dx = 1.778 Mg m−3 |
Monoclinic, P21/c | Melting point = 351–353 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 15.526 (4) Å | Cell parameters from 4514 reflections |
b = 11.521 (4) Å | θ = 2.6–27.5° |
c = 11.828 (6) Å | µ = 3.65 mm−1 |
β = 98.423 (15)° | T = 173 K |
V = 2092.9 (14) Å3 | Block, colorless |
Z = 8 | 0.22 × 0.18 × 0.15 mm |
Nonius KappaCCD diffractometer | 4760 independent reflections |
Radiation source: fine-focus sealed tube | 3200 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.037 |
ω and ϕ scans | θmax = 27.6°, θmin = 2.6° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −20→20 |
Tmin = 0.501, Tmax = 0.611 | k = −13→14 |
8438 measured reflections | l = −15→15 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.028P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3 |
4760 reflections | (Δ/σ)max = 0.001 |
201 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.50 e Å−3 |
[Ge(C5H9O2)Cl3] | V = 2092.9 (14) Å3 |
Mr = 280.06 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 15.526 (4) Å | µ = 3.65 mm−1 |
b = 11.521 (4) Å | T = 173 K |
c = 11.828 (6) Å | 0.22 × 0.18 × 0.15 mm |
β = 98.423 (15)° |
Nonius KappaCCD diffractometer | 4760 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 3200 reflections with I > 2.0σ(I) |
Tmin = 0.501, Tmax = 0.611 | Rint = 0.037 |
8438 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.35 e Å−3 |
4760 reflections | Δρmin = −0.50 e Å−3 |
201 parameters |
x | y | z | Uiso*/Ueq | ||
Ge1 | 0.08846 (2) | 0.33115 (3) | 0.63993 (3) | 0.02912 (10) | |
Cl1 | −0.04901 (5) | 0.30496 (8) | 0.59573 (8) | 0.0518 (2) | |
Cl2 | 0.13806 (5) | 0.15776 (6) | 0.66369 (7) | 0.0395 (2) | |
Cl3 | 0.12262 (5) | 0.39513 (7) | 0.48295 (7) | 0.0434 (2) | |
O1 | 0.27348 (12) | 0.37351 (19) | 0.69626 (18) | 0.0360 (5) | |
O2 | 0.34530 (13) | 0.3554 (2) | 0.87359 (17) | 0.0392 (5) | |
H2 | 0.3889 | 0.3550 | 0.8391 | 0.059* | |
C1 | 0.27483 (19) | 0.3726 (2) | 0.8002 (3) | 0.0302 (7) | |
C2 | 0.19506 (19) | 0.3873 (3) | 0.8552 (3) | 0.0367 (8) | |
H2A | 0.2084 | 0.4424 | 0.9197 | 0.044* | |
H2B | 0.1809 | 0.3116 | 0.8876 | 0.044* | |
C3 | 0.11390 (18) | 0.4313 (3) | 0.7766 (2) | 0.0333 (7) | |
C4 | 0.1259 (2) | 0.5556 (3) | 0.7351 (3) | 0.0504 (10) | |
H4A | 0.0742 | 0.5789 | 0.6822 | 0.076* | |
H4B | 0.1772 | 0.5590 | 0.6959 | 0.076* | |
H4C | 0.1338 | 0.6084 | 0.8008 | 0.076* | |
C5 | 0.0361 (2) | 0.4243 (4) | 0.8420 (3) | 0.0520 (10) | |
H5A | 0.0482 | 0.4699 | 0.9125 | 0.078* | |
H5B | 0.0259 | 0.3431 | 0.8611 | 0.078* | |
H5C | −0.0158 | 0.4552 | 0.7944 | 0.078* | |
Ge2 | 0.66060 (2) | 0.34054 (3) | 0.83457 (3) | 0.03169 (11) | |
Cl4 | 0.79756 (6) | 0.34223 (9) | 0.89944 (9) | 0.0578 (3) | |
Cl5 | 0.63167 (6) | 0.15935 (7) | 0.81354 (7) | 0.0415 (2) | |
Cl6 | 0.60825 (6) | 0.40656 (8) | 0.97867 (7) | 0.0505 (2) | |
O3 | 0.48214 (13) | 0.35157 (19) | 0.76144 (17) | 0.0385 (5) | |
O4 | 0.41019 (12) | 0.3788 (2) | 0.58617 (17) | 0.0369 (5) | |
H4 | 0.3669 | 0.3802 | 0.6213 | 0.055* | |
C6 | 0.48130 (19) | 0.3694 (3) | 0.6595 (3) | 0.0320 (7) | |
C7 | 0.56345 (18) | 0.3789 (3) | 0.6088 (2) | 0.0310 (7) | |
H7A | 0.5526 | 0.4288 | 0.5401 | 0.037* | |
H7B | 0.5795 | 0.3008 | 0.5839 | 0.037* | |
C8 | 0.64081 (18) | 0.4291 (3) | 0.6905 (2) | 0.0298 (7) | |
C9 | 0.6242 (2) | 0.5563 (3) | 0.7205 (3) | 0.0415 (8) | |
H9A | 0.6724 | 0.5845 | 0.7765 | 0.062* | |
H9B | 0.5697 | 0.5617 | 0.7529 | 0.062* | |
H9C | 0.6197 | 0.6039 | 0.6511 | 0.062* | |
C10 | 0.72331 (19) | 0.4183 (3) | 0.6340 (3) | 0.0461 (9) | |
H10A | 0.7137 | 0.4559 | 0.5588 | 0.069* | |
H10B | 0.7369 | 0.3360 | 0.6248 | 0.069* | |
H10C | 0.7721 | 0.4560 | 0.6822 | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ge1 | 0.02675 (18) | 0.02630 (18) | 0.03443 (19) | −0.00131 (14) | 0.00490 (14) | 0.00387 (14) |
Cl1 | 0.0277 (4) | 0.0543 (6) | 0.0698 (6) | −0.0052 (4) | −0.0044 (4) | 0.0099 (5) |
Cl2 | 0.0433 (5) | 0.0274 (4) | 0.0466 (5) | 0.0028 (4) | 0.0025 (4) | 0.0027 (4) |
Cl3 | 0.0509 (5) | 0.0429 (5) | 0.0373 (5) | −0.0023 (4) | 0.0095 (4) | 0.0091 (4) |
O1 | 0.0241 (11) | 0.0488 (14) | 0.0349 (13) | −0.0001 (10) | 0.0032 (9) | −0.0027 (10) |
O2 | 0.0291 (12) | 0.0539 (15) | 0.0342 (12) | 0.0004 (11) | 0.0036 (10) | −0.0036 (11) |
C1 | 0.0292 (17) | 0.0230 (15) | 0.0382 (19) | −0.0019 (13) | 0.0045 (14) | −0.0024 (14) |
C2 | 0.0328 (17) | 0.0427 (19) | 0.0355 (18) | −0.0019 (16) | 0.0084 (14) | −0.0025 (15) |
C3 | 0.0284 (16) | 0.0356 (18) | 0.0375 (18) | 0.0036 (14) | 0.0102 (14) | −0.0044 (14) |
C4 | 0.053 (2) | 0.0322 (19) | 0.065 (2) | 0.0050 (17) | 0.0041 (19) | −0.0073 (18) |
C5 | 0.0352 (19) | 0.070 (3) | 0.054 (2) | 0.0112 (19) | 0.0173 (17) | −0.001 (2) |
Ge2 | 0.0357 (2) | 0.02722 (18) | 0.03096 (19) | 0.00098 (15) | 0.00092 (15) | 0.00222 (14) |
Cl4 | 0.0405 (5) | 0.0616 (6) | 0.0638 (6) | −0.0008 (5) | −0.0173 (4) | 0.0123 (5) |
Cl5 | 0.0515 (5) | 0.0276 (4) | 0.0454 (5) | 0.0011 (4) | 0.0065 (4) | 0.0008 (4) |
Cl6 | 0.0749 (6) | 0.0434 (5) | 0.0344 (5) | 0.0011 (5) | 0.0118 (4) | −0.0057 (4) |
O3 | 0.0268 (12) | 0.0586 (15) | 0.0300 (13) | 0.0031 (11) | 0.0037 (9) | 0.0095 (11) |
O4 | 0.0218 (11) | 0.0558 (14) | 0.0324 (12) | −0.0014 (11) | 0.0016 (9) | 0.0023 (11) |
C6 | 0.0281 (17) | 0.0292 (17) | 0.0382 (19) | 0.0008 (14) | 0.0035 (14) | 0.0003 (14) |
C7 | 0.0270 (16) | 0.0370 (17) | 0.0293 (16) | 0.0012 (14) | 0.0047 (13) | −0.0001 (14) |
C8 | 0.0258 (16) | 0.0303 (16) | 0.0334 (17) | −0.0022 (14) | 0.0047 (13) | 0.0067 (14) |
C9 | 0.046 (2) | 0.0306 (18) | 0.046 (2) | −0.0027 (16) | −0.0007 (16) | 0.0076 (16) |
C10 | 0.0306 (18) | 0.066 (2) | 0.043 (2) | −0.0051 (18) | 0.0089 (15) | 0.0095 (18) |
Ge1—C3 | 1.978 (3) | Ge2—C8 | 1.971 (3) |
Ge1—Cl3 | 2.1356 (12) | Ge2—Cl6 | 2.1330 (12) |
Ge1—Cl1 | 2.1431 (10) | Ge2—Cl5 | 2.1422 (11) |
Ge1—Cl2 | 2.1446 (10) | Ge2—Cl4 | 2.1525 (10) |
O1—C1 | 1.227 (4) | O3—C6 | 1.222 (3) |
O2—C1 | 1.308 (3) | O4—C6 | 1.305 (3) |
O2—H2 | 0.8400 | O4—H4 | 0.8400 |
C1—C2 | 1.491 (4) | C6—C7 | 1.490 (4) |
C2—C3 | 1.539 (4) | C7—C8 | 1.540 (4) |
C2—H2A | 0.9900 | C7—H7A | 0.9900 |
C2—H2B | 0.9900 | C7—H7B | 0.9900 |
C3—C5 | 1.530 (4) | C8—C10 | 1.535 (4) |
C3—C4 | 1.534 (5) | C8—C9 | 1.539 (4) |
C4—H4A | 0.9800 | C9—H9A | 0.9800 |
C4—H4B | 0.9800 | C9—H9B | 0.9800 |
C4—H4C | 0.9800 | C9—H9C | 0.9800 |
C5—H5A | 0.9800 | C10—H10A | 0.9800 |
C5—H5B | 0.9800 | C10—H10B | 0.9800 |
C5—H5C | 0.9800 | C10—H10C | 0.9800 |
C3—Ge1—Cl3 | 117.63 (10) | C8—Ge2—Cl6 | 118.47 (10) |
C3—Ge1—Cl1 | 110.73 (9) | C8—Ge2—Cl5 | 113.62 (9) |
Cl3—Ge1—Cl1 | 101.64 (4) | Cl6—Ge2—Cl5 | 110.02 (4) |
C3—Ge1—Cl2 | 114.30 (10) | C8—Ge2—Cl4 | 108.92 (9) |
Cl3—Ge1—Cl2 | 107.77 (4) | Cl6—Ge2—Cl4 | 100.61 (5) |
Cl1—Ge1—Cl2 | 103.09 (4) | Cl5—Ge2—Cl4 | 103.27 (4) |
C1—O2—H2 | 109.5 | C6—O4—H4 | 109.5 |
O1—C1—O2 | 123.8 (3) | O3—C6—O4 | 123.8 (3) |
O1—C1—C2 | 122.9 (3) | O3—C6—C7 | 121.5 (3) |
O2—C1—C2 | 113.3 (3) | O4—C6—C7 | 114.7 (3) |
C1—C2—C3 | 115.6 (3) | C6—C7—C8 | 114.2 (3) |
C1—C2—H2A | 108.4 | C6—C7—H7A | 108.7 |
C3—C2—H2A | 108.4 | C8—C7—H7A | 108.7 |
C1—C2—H2B | 108.4 | C6—C7—H7B | 108.7 |
C3—C2—H2B | 108.4 | C8—C7—H7B | 108.7 |
H2A—C2—H2B | 107.4 | H7A—C7—H7B | 107.6 |
C5—C3—C4 | 110.7 (3) | C10—C8—C9 | 110.9 (3) |
C5—C3—C2 | 108.3 (3) | C10—C8—C7 | 108.7 (3) |
C4—C3—C2 | 112.0 (3) | C9—C8—C7 | 111.1 (2) |
C5—C3—Ge1 | 107.7 (2) | C10—C8—Ge2 | 107.5 (2) |
C4—C3—Ge1 | 107.6 (2) | C9—C8—Ge2 | 107.7 (2) |
C2—C3—Ge1 | 110.5 (2) | C7—C8—Ge2 | 110.88 (19) |
C3—C4—H4A | 109.5 | C8—C9—H9A | 109.5 |
C3—C4—H4B | 109.5 | C8—C9—H9B | 109.5 |
H4A—C4—H4B | 109.5 | H9A—C9—H9B | 109.5 |
C3—C4—H4C | 109.5 | C8—C9—H9C | 109.5 |
H4A—C4—H4C | 109.5 | H9A—C9—H9C | 109.5 |
H4B—C4—H4C | 109.5 | H9B—C9—H9C | 109.5 |
C3—C5—H5A | 109.5 | C8—C10—H10A | 109.5 |
C3—C5—H5B | 109.5 | C8—C10—H10B | 109.5 |
H5A—C5—H5B | 109.5 | H10A—C10—H10B | 109.5 |
C3—C5—H5C | 109.5 | C8—C10—H10C | 109.5 |
H5A—C5—H5C | 109.5 | H10A—C10—H10C | 109.5 |
H5B—C5—H5C | 109.5 | H10B—C10—H10C | 109.5 |
O1—C1—C2—C3 | −13.4 (4) | O3—C6—C7—C8 | −31.1 (4) |
O2—C1—C2—C3 | 168.4 (3) | O4—C6—C7—C8 | 150.5 (3) |
C1—C2—C3—C5 | 171.9 (3) | C6—C7—C8—C10 | 172.2 (3) |
C1—C2—C3—C4 | −65.8 (4) | C6—C7—C8—C9 | −65.5 (3) |
C1—C2—C3—Ge1 | 54.1 (3) | C6—C7—C8—Ge2 | 54.3 (3) |
Cl3—Ge1—C3—C5 | 138.5 (2) | Cl6—Ge2—C8—C10 | 143.52 (19) |
Cl1—Ge1—C3—C5 | 22.3 (2) | Cl5—Ge2—C8—C10 | −85.0 (2) |
Cl2—Ge1—C3—C5 | −93.6 (2) | Cl4—Ge2—C8—C10 | 29.5 (2) |
Cl3—Ge1—C3—C4 | 19.2 (2) | Cl6—Ge2—C8—C9 | 24.0 (2) |
Cl1—Ge1—C3—C4 | −97.1 (2) | Cl5—Ge2—C8—C9 | 155.42 (17) |
Cl2—Ge1—C3—C4 | 147.06 (18) | Cl4—Ge2—C8—C9 | −90.08 (19) |
Cl3—Ge1—C3—C2 | −103.4 (2) | Cl6—Ge2—C8—C7 | −97.8 (2) |
Cl1—Ge1—C3—C2 | 140.44 (18) | Cl5—Ge2—C8—C7 | 33.6 (2) |
Cl2—Ge1—C3—C2 | 24.6 (2) | Cl4—Ge2—C8—C7 | 148.13 (18) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 | 1.83 | 2.665 (3) | 179 |
O4—H4···O1 | 0.84 | 1.81 | 2.649 (3) | 176 |
[Ge(C6H5)3(C5H9O2)] | F(000) = 1680 |
Mr = 405.01 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/c | Melting point = 387–388 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.785 (1) Å | Cell parameters from 16723 reflections |
b = 15.678 (2) Å | θ = 1.4–27.5° |
c = 32.703 (5) Å | µ = 1.56 mm−1 |
β = 96.668 (5)° | T = 173 K |
V = 3964.5 (9) Å3 | Block, colorless |
Z = 8 | 0.16 × 0.14 × 0.12 mm |
Nonius KappaCCD diffractometer | 9032 independent reflections |
Radiation source: fine-focus sealed tube | 6226 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.043 |
ω and ϕ scans | θmax = 27.5°, θmin = 1.4° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −10→10 |
Tmin = 0.789, Tmax = 0.835 | k = −20→19 |
16723 measured reflections | l = −42→42 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0344P)2 + 1.542P] where P = (Fo2 + 2Fc2)/3 |
9032 reflections | (Δ/σ)max = 0.003 |
475 parameters | Δρmax = 0.59 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
[Ge(C6H5)3(C5H9O2)] | V = 3964.5 (9) Å3 |
Mr = 405.01 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.785 (1) Å | µ = 1.56 mm−1 |
b = 15.678 (2) Å | T = 173 K |
c = 32.703 (5) Å | 0.16 × 0.14 × 0.12 mm |
β = 96.668 (5)° |
Nonius KappaCCD diffractometer | 9032 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 6226 reflections with I > 2.0σ(I) |
Tmin = 0.789, Tmax = 0.835 | Rint = 0.043 |
16723 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.59 e Å−3 |
9032 reflections | Δρmin = −0.39 e Å−3 |
475 parameters |
x | y | z | Uiso*/Ueq | ||
Ge1 | 0.16992 (4) | 0.747093 (17) | 0.503243 (8) | 0.02481 (8) | |
O1 | 0.2593 (3) | 0.60634 (14) | 0.37012 (6) | 0.0483 (6) | |
O2 | 0.5170 (3) | 0.59827 (16) | 0.40683 (7) | 0.0581 (7) | |
H2 | 0.5316 | 0.5607 | 0.3892 | 0.087* | |
C1 | 0.3620 (4) | 0.62929 (18) | 0.39952 (9) | 0.0364 (7) | |
C2 | 0.3137 (4) | 0.69377 (18) | 0.42989 (8) | 0.0370 (7) | |
H2A | 0.2140 | 0.7273 | 0.4170 | 0.044* | |
H2B | 0.4117 | 0.7336 | 0.4364 | 0.044* | |
C3 | 0.2661 (4) | 0.65469 (17) | 0.47050 (8) | 0.0319 (7) | |
C4 | 0.4280 (5) | 0.6177 (2) | 0.49529 (10) | 0.0592 (11) | |
H4A | 0.4784 | 0.5739 | 0.4789 | 0.089* | |
H4B | 0.3965 | 0.5921 | 0.5207 | 0.089* | |
H4C | 0.5125 | 0.6633 | 0.5021 | 0.089* | |
C5 | 0.1276 (5) | 0.5843 (2) | 0.46146 (11) | 0.0595 (10) | |
H5A | 0.0298 | 0.6070 | 0.4431 | 0.089* | |
H5B | 0.0873 | 0.5657 | 0.4873 | 0.089* | |
H5C | 0.1779 | 0.5357 | 0.4482 | 0.089* | |
C6 | 0.0501 (4) | 0.69526 (17) | 0.54624 (8) | 0.0278 (6) | |
C7 | 0.1394 (4) | 0.64374 (17) | 0.57689 (8) | 0.0317 (7) | |
H7 | 0.2611 | 0.6372 | 0.5777 | 0.038* | |
C8 | 0.0532 (4) | 0.60247 (18) | 0.60576 (8) | 0.0352 (7) | |
H8 | 0.1159 | 0.5676 | 0.6261 | 0.042* | |
C9 | −0.1224 (4) | 0.61144 (18) | 0.60536 (8) | 0.0356 (7) | |
H9 | −0.1814 | 0.5827 | 0.6252 | 0.043* | |
C10 | −0.2123 (4) | 0.66246 (19) | 0.57603 (8) | 0.0391 (7) | |
H10 | −0.3338 | 0.6690 | 0.5756 | 0.047* | |
C11 | −0.1263 (4) | 0.70445 (18) | 0.54708 (8) | 0.0329 (7) | |
H11 | −0.1899 | 0.7403 | 0.5274 | 0.040* | |
C12 | 0.3549 (3) | 0.82041 (16) | 0.52902 (8) | 0.0264 (6) | |
C13 | 0.3724 (4) | 0.83658 (17) | 0.57104 (8) | 0.0341 (7) | |
H13 | 0.2927 | 0.8119 | 0.5875 | 0.041* | |
C14 | 0.5047 (4) | 0.88828 (18) | 0.58946 (9) | 0.0432 (8) | |
H14 | 0.5151 | 0.8981 | 0.6183 | 0.052* | |
C15 | 0.6207 (4) | 0.92528 (19) | 0.56607 (10) | 0.0428 (8) | |
H15 | 0.7107 | 0.9608 | 0.5786 | 0.051* | |
C16 | 0.6050 (4) | 0.91030 (19) | 0.52403 (10) | 0.0418 (8) | |
H16 | 0.6847 | 0.9354 | 0.5077 | 0.050* | |
C17 | 0.4731 (4) | 0.85884 (17) | 0.50586 (9) | 0.0335 (7) | |
H17 | 0.4629 | 0.8495 | 0.4770 | 0.040* | |
C18 | 0.0095 (4) | 0.81772 (17) | 0.46745 (7) | 0.0273 (6) | |
C19 | 0.0323 (4) | 0.90580 (17) | 0.46563 (8) | 0.0292 (6) | |
H19 | 0.1262 | 0.9314 | 0.4824 | 0.035* | |
C20 | −0.0786 (4) | 0.95680 (19) | 0.44002 (8) | 0.0372 (7) | |
H20 | −0.0604 | 1.0167 | 0.4394 | 0.045* | |
C21 | −0.2155 (4) | 0.9209 (2) | 0.41532 (9) | 0.0418 (8) | |
H21 | −0.2913 | 0.9558 | 0.3977 | 0.050* | |
C22 | −0.2417 (4) | 0.8337 (2) | 0.41636 (9) | 0.0417 (8) | |
H22 | −0.3350 | 0.8088 | 0.3991 | 0.050* | |
C23 | −0.1324 (4) | 0.78246 (19) | 0.44245 (8) | 0.0353 (7) | |
H23 | −0.1537 | 0.7229 | 0.4435 | 0.042* | |
Ge2 | 0.54844 (4) | 0.233204 (17) | 0.254755 (8) | 0.02547 (9) | |
O3 | 0.5596 (3) | 0.46509 (13) | 0.35939 (6) | 0.0443 (5) | |
O4 | 0.3541 (3) | 0.50860 (12) | 0.31103 (6) | 0.0384 (5) | |
H4 | 0.3356 | 0.5428 | 0.3298 | 0.058* | |
C24 | 0.4861 (4) | 0.46122 (17) | 0.32348 (8) | 0.0308 (6) | |
C25 | 0.5435 (4) | 0.40019 (17) | 0.29293 (8) | 0.0308 (6) | |
H25A | 0.6655 | 0.3843 | 0.3015 | 0.037* | |
H25B | 0.5383 | 0.4288 | 0.2658 | 0.037* | |
C26 | 0.4318 (3) | 0.31782 (16) | 0.28833 (8) | 0.0270 (6) | |
C27 | 0.2478 (4) | 0.33682 (19) | 0.26746 (9) | 0.0389 (7) | |
H27A | 0.1891 | 0.3753 | 0.2849 | 0.058* | |
H27B | 0.1826 | 0.2834 | 0.2635 | 0.058* | |
H27C | 0.2548 | 0.3638 | 0.2407 | 0.058* | |
C28 | 0.4185 (4) | 0.27681 (18) | 0.33069 (8) | 0.0370 (7) | |
H28A | 0.5348 | 0.2685 | 0.3451 | 0.055* | |
H28B | 0.3600 | 0.2216 | 0.3269 | 0.055* | |
H28C | 0.3523 | 0.3143 | 0.3470 | 0.055* | |
C29 | 0.6579 (4) | 0.28937 (17) | 0.21092 (7) | 0.0270 (6) | |
C30 | 0.5744 (4) | 0.35288 (19) | 0.18587 (8) | 0.0388 (7) | |
H30 | 0.4609 | 0.3701 | 0.1902 | 0.047* | |
C31 | 0.6539 (4) | 0.3910 (2) | 0.15501 (9) | 0.0434 (8) | |
H31 | 0.5954 | 0.4344 | 0.1386 | 0.052* | |
C32 | 0.8188 (4) | 0.36608 (19) | 0.14787 (8) | 0.0381 (7) | |
H32 | 0.8731 | 0.3916 | 0.1263 | 0.046* | |
C33 | 0.9021 (4) | 0.3045 (2) | 0.17216 (9) | 0.0412 (7) | |
H33 | 1.0156 | 0.2876 | 0.1677 | 0.049* | |
C34 | 0.8226 (4) | 0.26659 (18) | 0.20323 (8) | 0.0350 (7) | |
H34 | 0.8829 | 0.2238 | 0.2197 | 0.042* | |
C35 | 0.3682 (4) | 0.15458 (17) | 0.23134 (8) | 0.0304 (6) | |
C36 | 0.3066 (4) | 0.15754 (19) | 0.18962 (9) | 0.0402 (7) | |
H36 | 0.3603 | 0.1946 | 0.1719 | 0.048* | |
C37 | 0.1695 (5) | 0.1078 (2) | 0.17353 (11) | 0.0529 (9) | |
H37 | 0.1282 | 0.1113 | 0.1451 | 0.063* | |
C38 | 0.0916 (4) | 0.0524 (2) | 0.19896 (12) | 0.0557 (10) | |
H38 | −0.0033 | 0.0182 | 0.1879 | 0.067* | |
C39 | 0.1516 (4) | 0.0473 (2) | 0.23991 (11) | 0.0514 (9) | |
H39 | 0.0994 | 0.0089 | 0.2573 | 0.062* | |
C40 | 0.2894 (4) | 0.09837 (19) | 0.25608 (10) | 0.0420 (8) | |
H40 | 0.3301 | 0.0946 | 0.2846 | 0.050* | |
C41 | 0.7248 (4) | 0.17112 (17) | 0.29045 (7) | 0.0280 (6) | |
C42 | 0.7278 (4) | 0.08265 (18) | 0.29178 (8) | 0.0357 (7) | |
H42 | 0.6450 | 0.0513 | 0.2742 | 0.043* | |
C43 | 0.8493 (4) | 0.03923 (19) | 0.31833 (9) | 0.0428 (8) | |
H43 | 0.8488 | −0.0214 | 0.3188 | 0.051* | |
C44 | 0.9706 (4) | 0.0833 (2) | 0.34406 (9) | 0.0417 (8) | |
H44 | 1.0534 | 0.0534 | 0.3623 | 0.050* | |
C45 | 0.9713 (4) | 0.1712 (2) | 0.34319 (9) | 0.0401 (7) | |
H45 | 1.0543 | 0.2020 | 0.3610 | 0.048* | |
C46 | 0.8516 (4) | 0.21457 (19) | 0.31653 (8) | 0.0341 (7) | |
H46 | 0.8550 | 0.2751 | 0.3158 | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ge1 | 0.02730 (17) | 0.02277 (15) | 0.02401 (14) | −0.00081 (12) | 0.00141 (11) | 0.00060 (11) |
O1 | 0.0507 (15) | 0.0572 (15) | 0.0357 (12) | 0.0132 (12) | −0.0008 (10) | −0.0110 (10) |
O2 | 0.0446 (15) | 0.0745 (18) | 0.0544 (15) | 0.0138 (13) | 0.0023 (11) | −0.0339 (12) |
C1 | 0.041 (2) | 0.0331 (17) | 0.0355 (16) | 0.0037 (15) | 0.0071 (14) | −0.0016 (13) |
C2 | 0.048 (2) | 0.0281 (16) | 0.0368 (16) | 0.0021 (14) | 0.0123 (14) | −0.0040 (12) |
C3 | 0.0409 (18) | 0.0233 (15) | 0.0318 (14) | 0.0025 (13) | 0.0057 (12) | −0.0023 (12) |
C4 | 0.077 (3) | 0.053 (2) | 0.046 (2) | 0.038 (2) | 0.0016 (18) | −0.0034 (16) |
C5 | 0.085 (3) | 0.0337 (19) | 0.065 (2) | −0.0184 (19) | 0.032 (2) | −0.0164 (16) |
C6 | 0.0317 (17) | 0.0256 (15) | 0.0260 (13) | −0.0039 (12) | 0.0025 (11) | −0.0011 (11) |
C7 | 0.0300 (17) | 0.0338 (16) | 0.0307 (14) | 0.0004 (13) | 0.0015 (12) | 0.0018 (12) |
C8 | 0.045 (2) | 0.0288 (16) | 0.0315 (15) | 0.0007 (14) | 0.0034 (13) | 0.0064 (12) |
C9 | 0.042 (2) | 0.0336 (17) | 0.0334 (15) | −0.0052 (14) | 0.0131 (13) | −0.0014 (12) |
C10 | 0.0339 (18) | 0.051 (2) | 0.0330 (16) | −0.0006 (15) | 0.0074 (13) | −0.0028 (14) |
C11 | 0.0337 (18) | 0.0385 (17) | 0.0264 (14) | 0.0048 (14) | 0.0027 (12) | 0.0034 (12) |
C12 | 0.0266 (16) | 0.0213 (14) | 0.0306 (14) | 0.0040 (12) | 0.0003 (11) | −0.0002 (11) |
C13 | 0.0423 (19) | 0.0299 (16) | 0.0292 (15) | −0.0033 (14) | 0.0003 (13) | 0.0030 (12) |
C14 | 0.060 (2) | 0.0322 (17) | 0.0341 (16) | −0.0050 (16) | −0.0100 (15) | −0.0027 (13) |
C15 | 0.0370 (19) | 0.0327 (17) | 0.054 (2) | −0.0035 (15) | −0.0132 (15) | −0.0034 (15) |
C16 | 0.0325 (19) | 0.0362 (18) | 0.057 (2) | −0.0055 (15) | 0.0073 (15) | −0.0036 (15) |
C17 | 0.0324 (18) | 0.0316 (16) | 0.0372 (15) | −0.0037 (14) | 0.0065 (12) | −0.0050 (13) |
C18 | 0.0313 (16) | 0.0283 (15) | 0.0227 (13) | 0.0034 (13) | 0.0052 (11) | 0.0019 (11) |
C19 | 0.0324 (17) | 0.0271 (16) | 0.0284 (14) | 0.0022 (13) | 0.0044 (12) | −0.0001 (11) |
C20 | 0.042 (2) | 0.0307 (17) | 0.0395 (16) | 0.0061 (14) | 0.0089 (14) | 0.0051 (13) |
C21 | 0.0379 (19) | 0.052 (2) | 0.0365 (16) | 0.0145 (16) | 0.0063 (14) | 0.0166 (15) |
C22 | 0.0323 (18) | 0.058 (2) | 0.0330 (16) | −0.0006 (16) | −0.0043 (13) | 0.0011 (15) |
C23 | 0.0343 (18) | 0.0364 (17) | 0.0342 (15) | −0.0010 (14) | −0.0002 (13) | 0.0028 (13) |
Ge2 | 0.02674 (17) | 0.02554 (16) | 0.02383 (14) | 0.00045 (13) | 0.00161 (11) | −0.00099 (11) |
O3 | 0.0455 (14) | 0.0474 (13) | 0.0376 (11) | 0.0137 (11) | −0.0058 (10) | −0.0096 (10) |
O4 | 0.0433 (13) | 0.0329 (12) | 0.0381 (11) | 0.0108 (10) | 0.0014 (9) | −0.0060 (9) |
C24 | 0.0299 (17) | 0.0237 (15) | 0.0385 (16) | −0.0019 (13) | 0.0033 (13) | 0.0015 (12) |
C25 | 0.0301 (17) | 0.0285 (16) | 0.0339 (15) | 0.0003 (13) | 0.0046 (12) | −0.0022 (12) |
C26 | 0.0240 (15) | 0.0259 (15) | 0.0314 (14) | 0.0000 (12) | 0.0041 (11) | −0.0029 (11) |
C27 | 0.0297 (18) | 0.0368 (18) | 0.0492 (18) | 0.0011 (14) | 0.0008 (14) | −0.0072 (14) |
C28 | 0.047 (2) | 0.0318 (16) | 0.0343 (15) | −0.0027 (14) | 0.0151 (13) | 0.0010 (12) |
C29 | 0.0312 (16) | 0.0273 (15) | 0.0222 (13) | −0.0018 (12) | 0.0024 (11) | −0.0021 (11) |
C30 | 0.0345 (18) | 0.0455 (19) | 0.0364 (16) | 0.0065 (15) | 0.0040 (13) | 0.0084 (14) |
C31 | 0.051 (2) | 0.0412 (19) | 0.0355 (17) | −0.0008 (16) | −0.0036 (15) | 0.0133 (14) |
C32 | 0.045 (2) | 0.0407 (18) | 0.0300 (15) | −0.0143 (15) | 0.0079 (13) | −0.0003 (13) |
C33 | 0.0350 (19) | 0.047 (2) | 0.0436 (17) | −0.0001 (15) | 0.0129 (14) | −0.0008 (15) |
C34 | 0.0379 (18) | 0.0329 (17) | 0.0348 (15) | 0.0047 (14) | 0.0070 (13) | 0.0034 (12) |
C35 | 0.0279 (16) | 0.0254 (15) | 0.0377 (15) | 0.0020 (13) | 0.0026 (12) | −0.0091 (12) |
C36 | 0.0381 (19) | 0.0358 (18) | 0.0438 (17) | 0.0040 (15) | −0.0068 (14) | −0.0083 (14) |
C37 | 0.049 (2) | 0.047 (2) | 0.056 (2) | 0.0088 (18) | −0.0211 (17) | −0.0150 (17) |
C38 | 0.028 (2) | 0.051 (2) | 0.085 (3) | 0.0032 (17) | −0.0074 (18) | −0.029 (2) |
C39 | 0.042 (2) | 0.0389 (19) | 0.077 (2) | −0.0080 (16) | 0.0217 (18) | −0.0188 (17) |
C40 | 0.043 (2) | 0.0367 (18) | 0.0475 (18) | −0.0081 (15) | 0.0104 (15) | −0.0117 (14) |
C41 | 0.0305 (16) | 0.0292 (15) | 0.0245 (13) | 0.0042 (13) | 0.0041 (11) | 0.0013 (11) |
C42 | 0.0420 (19) | 0.0281 (16) | 0.0349 (16) | −0.0029 (14) | −0.0044 (13) | −0.0045 (12) |
C43 | 0.056 (2) | 0.0253 (16) | 0.0441 (18) | 0.0034 (15) | −0.0081 (15) | 0.0062 (13) |
C44 | 0.047 (2) | 0.0409 (19) | 0.0350 (16) | 0.0066 (16) | −0.0054 (14) | 0.0092 (14) |
C45 | 0.0365 (19) | 0.045 (2) | 0.0367 (16) | −0.0056 (15) | −0.0032 (13) | −0.0036 (14) |
C46 | 0.0305 (17) | 0.0296 (16) | 0.0406 (16) | −0.0004 (13) | −0.0024 (13) | 0.0005 (13) |
Ge1—C6 | 1.953 (3) | Ge2—C41 | 1.955 (3) |
Ge1—C18 | 1.954 (3) | Ge2—C35 | 1.956 (3) |
Ge1—C12 | 1.955 (3) | Ge2—C29 | 1.960 (3) |
Ge1—C3 | 1.998 (3) | Ge2—C26 | 2.005 (3) |
O1—C1 | 1.231 (3) | O3—C24 | 1.246 (3) |
O2—C1 | 1.297 (3) | O4—C24 | 1.295 (3) |
O2—H2 | 0.8400 | O4—H4 | 0.8400 |
C1—C2 | 1.496 (4) | C24—C25 | 1.489 (4) |
C2—C3 | 1.546 (4) | C25—C26 | 1.555 (4) |
C2—H2A | 0.9900 | C25—H25A | 0.9900 |
C2—H2B | 0.9900 | C25—H25B | 0.9900 |
C3—C4 | 1.532 (4) | C26—C28 | 1.542 (4) |
C3—C5 | 1.547 (4) | C26—C27 | 1.543 (4) |
C4—H4A | 0.9800 | C27—H27A | 0.9800 |
C4—H4B | 0.9800 | C27—H27B | 0.9800 |
C4—H4C | 0.9800 | C27—H27C | 0.9800 |
C5—H5A | 0.9800 | C28—H28A | 0.9800 |
C5—H5B | 0.9800 | C28—H28B | 0.9800 |
C5—H5C | 0.9800 | C28—H28C | 0.9800 |
C6—C11 | 1.384 (4) | C29—C34 | 1.382 (4) |
C6—C7 | 1.407 (4) | C29—C30 | 1.401 (4) |
C7—C8 | 1.382 (4) | C30—C31 | 1.379 (4) |
C7—H7 | 0.9500 | C30—H30 | 0.9500 |
C8—C9 | 1.373 (4) | C31—C32 | 1.388 (4) |
C8—H8 | 0.9500 | C31—H31 | 0.9500 |
C9—C10 | 1.376 (4) | C32—C33 | 1.365 (4) |
C9—H9 | 0.9500 | C32—H32 | 0.9500 |
C10—C11 | 1.387 (4) | C33—C34 | 1.384 (4) |
C10—H10 | 0.9500 | C33—H33 | 0.9500 |
C11—H11 | 0.9500 | C34—H34 | 0.9500 |
C12—C13 | 1.389 (3) | C35—C40 | 1.387 (4) |
C12—C17 | 1.395 (4) | C35—C36 | 1.393 (4) |
C13—C14 | 1.392 (4) | C36—C37 | 1.376 (4) |
C13—H13 | 0.9500 | C36—H36 | 0.9500 |
C14—C15 | 1.377 (4) | C37—C38 | 1.389 (5) |
C14—H14 | 0.9500 | C37—H37 | 0.9500 |
C15—C16 | 1.386 (4) | C38—C39 | 1.368 (5) |
C15—H15 | 0.9500 | C38—H38 | 0.9500 |
C16—C17 | 1.384 (4) | C39—C40 | 1.393 (4) |
C16—H16 | 0.9500 | C39—H39 | 0.9500 |
C17—H17 | 0.9500 | C40—H40 | 0.9500 |
C18—C19 | 1.394 (4) | C41—C42 | 1.388 (4) |
C18—C23 | 1.409 (4) | C41—C46 | 1.404 (4) |
C19—C20 | 1.385 (4) | C42—C43 | 1.386 (4) |
C19—H19 | 0.9500 | C42—H42 | 0.9500 |
C20—C21 | 1.380 (4) | C43—C44 | 1.376 (4) |
C20—H20 | 0.9500 | C43—H43 | 0.9500 |
C21—C22 | 1.382 (4) | C44—C45 | 1.379 (4) |
C21—H21 | 0.9500 | C44—H44 | 0.9500 |
C22—C23 | 1.389 (4) | C45—C46 | 1.379 (4) |
C22—H22 | 0.9500 | C45—H45 | 0.9500 |
C23—H23 | 0.9500 | C46—H46 | 0.9500 |
C6—Ge1—C18 | 109.98 (11) | C41—Ge2—C35 | 110.01 (12) |
C6—Ge1—C12 | 108.89 (11) | C41—Ge2—C29 | 109.00 (11) |
C18—Ge1—C12 | 108.22 (11) | C35—Ge2—C29 | 110.49 (11) |
C6—Ge1—C3 | 108.92 (11) | C41—Ge2—C26 | 109.49 (10) |
C18—Ge1—C3 | 110.07 (11) | C35—Ge2—C26 | 106.35 (11) |
C12—Ge1—C3 | 110.75 (11) | C29—Ge2—C26 | 111.48 (11) |
C1—O2—H2 | 109.5 | C24—O4—H4 | 109.5 |
O1—C1—O2 | 122.7 (3) | O3—C24—O4 | 121.9 (3) |
O1—C1—C2 | 121.7 (3) | O3—C24—C25 | 121.5 (3) |
O2—C1—C2 | 115.6 (3) | O4—C24—C25 | 116.5 (2) |
C1—C2—C3 | 114.0 (2) | C24—C25—C26 | 113.0 (2) |
C1—C2—H2A | 108.8 | C24—C25—H25A | 109.0 |
C3—C2—H2A | 108.8 | C26—C25—H25A | 109.0 |
C1—C2—H2B | 108.8 | C24—C25—H25B | 109.0 |
C3—C2—H2B | 108.8 | C26—C25—H25B | 109.0 |
H2A—C2—H2B | 107.7 | H25A—C25—H25B | 107.8 |
C4—C3—C2 | 109.9 (3) | C28—C26—C27 | 108.8 (2) |
C4—C3—C5 | 110.1 (3) | C28—C26—C25 | 110.8 (2) |
C2—C3—C5 | 110.5 (2) | C27—C26—C25 | 111.3 (2) |
C4—C3—Ge1 | 109.12 (19) | C28—C26—Ge2 | 107.34 (18) |
C2—C3—Ge1 | 108.37 (17) | C27—C26—Ge2 | 109.99 (17) |
C5—C3—Ge1 | 108.9 (2) | C25—C26—Ge2 | 108.59 (17) |
C3—C4—H4A | 109.5 | C26—C27—H27A | 109.5 |
C3—C4—H4B | 109.5 | C26—C27—H27B | 109.5 |
H4A—C4—H4B | 109.5 | H27A—C27—H27B | 109.5 |
C3—C4—H4C | 109.5 | C26—C27—H27C | 109.5 |
H4A—C4—H4C | 109.5 | H27A—C27—H27C | 109.5 |
H4B—C4—H4C | 109.5 | H27B—C27—H27C | 109.5 |
C3—C5—H5A | 109.5 | C26—C28—H28A | 109.5 |
C3—C5—H5B | 109.5 | C26—C28—H28B | 109.5 |
H5A—C5—H5B | 109.5 | H28A—C28—H28B | 109.5 |
C3—C5—H5C | 109.5 | C26—C28—H28C | 109.5 |
H5A—C5—H5C | 109.5 | H28A—C28—H28C | 109.5 |
H5B—C5—H5C | 109.5 | H28B—C28—H28C | 109.5 |
C11—C6—C7 | 117.1 (2) | C34—C29—C30 | 117.1 (2) |
C11—C6—Ge1 | 121.9 (2) | C34—C29—Ge2 | 120.6 (2) |
C7—C6—Ge1 | 120.9 (2) | C30—C29—Ge2 | 122.4 (2) |
C8—C7—C6 | 121.1 (3) | C31—C30—C29 | 121.2 (3) |
C8—C7—H7 | 119.4 | C31—C30—H30 | 119.4 |
C6—C7—H7 | 119.4 | C29—C30—H30 | 119.4 |
C9—C8—C7 | 120.5 (3) | C30—C31—C32 | 120.3 (3) |
C9—C8—H8 | 119.7 | C30—C31—H31 | 119.9 |
C7—C8—H8 | 119.7 | C32—C31—H31 | 119.9 |
C8—C9—C10 | 119.4 (3) | C33—C32—C31 | 119.1 (3) |
C8—C9—H9 | 120.3 | C33—C32—H32 | 120.4 |
C10—C9—H9 | 120.3 | C31—C32—H32 | 120.4 |
C9—C10—C11 | 120.3 (3) | C32—C33—C34 | 120.6 (3) |
C9—C10—H10 | 119.8 | C32—C33—H33 | 119.7 |
C11—C10—H10 | 119.8 | C34—C33—H33 | 119.7 |
C6—C11—C10 | 121.5 (3) | C29—C34—C33 | 121.7 (3) |
C6—C11—H11 | 119.3 | C29—C34—H34 | 119.1 |
C10—C11—H11 | 119.2 | C33—C34—H34 | 119.1 |
C13—C12—C17 | 117.6 (3) | C40—C35—C36 | 117.8 (3) |
C13—C12—Ge1 | 121.1 (2) | C40—C35—Ge2 | 121.2 (2) |
C17—C12—Ge1 | 121.3 (2) | C36—C35—Ge2 | 120.8 (2) |
C12—C13—C14 | 121.2 (3) | C37—C36—C35 | 121.3 (3) |
C12—C13—H13 | 119.4 | C37—C36—H36 | 119.4 |
C14—C13—H13 | 119.4 | C35—C36—H36 | 119.4 |
C15—C14—C13 | 120.3 (3) | C36—C37—C38 | 119.9 (3) |
C15—C14—H14 | 119.8 | C36—C37—H37 | 120.1 |
C13—C14—H14 | 119.8 | C38—C37—H37 | 120.1 |
C14—C15—C16 | 119.4 (3) | C39—C38—C37 | 120.0 (3) |
C14—C15—H15 | 120.3 | C39—C38—H38 | 120.0 |
C16—C15—H15 | 120.3 | C37—C38—H38 | 120.0 |
C17—C16—C15 | 120.0 (3) | C38—C39—C40 | 119.8 (3) |
C17—C16—H16 | 120.0 | C38—C39—H39 | 120.1 |
C15—C16—H16 | 120.0 | C40—C39—H39 | 120.1 |
C16—C17—C12 | 121.5 (3) | C35—C40—C39 | 121.2 (3) |
C16—C17—H17 | 119.3 | C35—C40—H40 | 119.4 |
C12—C17—H17 | 119.3 | C39—C40—H40 | 119.4 |
C19—C18—C23 | 117.3 (2) | C42—C41—C46 | 117.3 (2) |
C19—C18—Ge1 | 120.7 (2) | C42—C41—Ge2 | 121.6 (2) |
C23—C18—Ge1 | 121.9 (2) | C46—C41—Ge2 | 121.1 (2) |
C20—C19—C18 | 121.6 (3) | C43—C42—C41 | 121.2 (3) |
C20—C19—H19 | 119.2 | C43—C42—H42 | 119.4 |
C18—C19—H19 | 119.2 | C41—C42—H42 | 119.4 |
C21—C20—C19 | 120.2 (3) | C44—C43—C42 | 120.4 (3) |
C21—C20—H20 | 119.9 | C44—C43—H43 | 119.8 |
C19—C20—H20 | 119.9 | C42—C43—H43 | 119.8 |
C20—C21—C22 | 119.7 (3) | C43—C44—C45 | 119.6 (3) |
C20—C21—H21 | 120.2 | C43—C44—H44 | 120.2 |
C22—C21—H21 | 120.2 | C45—C44—H44 | 120.2 |
C21—C22—C23 | 120.3 (3) | C46—C45—C44 | 120.1 (3) |
C21—C22—H22 | 119.8 | C46—C45—H45 | 119.9 |
C23—C22—H22 | 119.8 | C44—C45—H45 | 119.9 |
C22—C23—C18 | 120.8 (3) | C45—C46—C41 | 121.4 (3) |
C22—C23—H23 | 119.6 | C45—C46—H46 | 119.3 |
C18—C23—H23 | 119.6 | C41—C46—H46 | 119.3 |
O1—C1—C2—C3 | 100.6 (3) | O3—C24—C25—C26 | 98.7 (3) |
O2—C1—C2—C3 | −78.0 (4) | O4—C24—C25—C26 | −80.0 (3) |
C1—C2—C3—C4 | 69.7 (3) | C24—C25—C26—C28 | −52.0 (3) |
C1—C2—C3—C5 | −52.0 (4) | C24—C25—C26—C27 | 69.2 (3) |
C1—C2—C3—Ge1 | −171.1 (2) | C24—C25—C26—Ge2 | −169.61 (19) |
C6—Ge1—C3—C4 | −76.2 (2) | C41—Ge2—C26—C28 | −36.0 (2) |
C18—Ge1—C3—C4 | 163.1 (2) | C35—Ge2—C26—C28 | 82.8 (2) |
C12—Ge1—C3—C4 | 43.5 (2) | C29—Ge2—C26—C28 | −156.71 (18) |
C6—Ge1—C3—C2 | 164.12 (19) | C41—Ge2—C26—C27 | −154.24 (18) |
C18—Ge1—C3—C2 | 43.5 (2) | C35—Ge2—C26—C27 | −35.4 (2) |
C12—Ge1—C3—C2 | −76.2 (2) | C29—Ge2—C26—C27 | 85.1 (2) |
C6—Ge1—C3—C5 | 43.9 (2) | C41—Ge2—C26—C25 | 83.78 (19) |
C18—Ge1—C3—C5 | −76.7 (2) | C35—Ge2—C26—C25 | −157.40 (17) |
C12—Ge1—C3—C5 | 163.6 (2) | C29—Ge2—C26—C25 | −36.9 (2) |
C18—Ge1—C6—C11 | 4.9 (3) | C41—Ge2—C29—C34 | 14.7 (2) |
C12—Ge1—C6—C11 | 123.4 (2) | C35—Ge2—C29—C34 | −106.3 (2) |
C3—Ge1—C6—C11 | −115.8 (2) | C26—Ge2—C29—C34 | 135.7 (2) |
C18—Ge1—C6—C7 | −177.7 (2) | C41—Ge2—C29—C30 | −166.0 (2) |
C12—Ge1—C6—C7 | −59.3 (2) | C35—Ge2—C29—C30 | 73.0 (2) |
C3—Ge1—C6—C7 | 61.6 (2) | C26—Ge2—C29—C30 | −45.1 (2) |
C11—C6—C7—C8 | 1.7 (4) | C34—C29—C30—C31 | −0.2 (4) |
Ge1—C6—C7—C8 | −175.7 (2) | Ge2—C29—C30—C31 | −179.5 (2) |
C6—C7—C8—C9 | −0.5 (4) | C29—C30—C31—C32 | 0.8 (5) |
C7—C8—C9—C10 | −0.4 (4) | C30—C31—C32—C33 | −1.0 (4) |
C8—C9—C10—C11 | 0.0 (4) | C31—C32—C33—C34 | 0.7 (4) |
C7—C6—C11—C10 | −2.1 (4) | C30—C29—C34—C33 | −0.1 (4) |
Ge1—C6—C11—C10 | 175.3 (2) | Ge2—C29—C34—C33 | 179.2 (2) |
C9—C10—C11—C6 | 1.3 (4) | C32—C33—C34—C29 | −0.2 (5) |
C6—Ge1—C12—C13 | −7.1 (2) | C41—Ge2—C35—C40 | 50.2 (3) |
C18—Ge1—C12—C13 | 112.4 (2) | C29—Ge2—C35—C40 | 170.6 (2) |
C3—Ge1—C12—C13 | −126.8 (2) | C26—Ge2—C35—C40 | −68.3 (3) |
C6—Ge1—C12—C17 | 173.4 (2) | C41—Ge2—C35—C36 | −134.3 (2) |
C18—Ge1—C12—C17 | −67.1 (2) | C29—Ge2—C35—C36 | −13.9 (3) |
C3—Ge1—C12—C17 | 53.7 (2) | C26—Ge2—C35—C36 | 107.2 (2) |
C17—C12—C13—C14 | −0.9 (4) | C40—C35—C36—C37 | 1.4 (4) |
Ge1—C12—C13—C14 | 179.6 (2) | Ge2—C35—C36—C37 | −174.2 (2) |
C12—C13—C14—C15 | 0.6 (4) | C35—C36—C37—C38 | −0.9 (5) |
C13—C14—C15—C16 | −0.3 (5) | C36—C37—C38—C39 | −0.2 (5) |
C14—C15—C16—C17 | 0.3 (5) | C37—C38—C39—C40 | 0.8 (5) |
C15—C16—C17—C12 | −0.6 (4) | C36—C35—C40—C39 | −0.9 (4) |
C13—C12—C17—C16 | 0.9 (4) | Ge2—C35—C40—C39 | 174.8 (2) |
Ge1—C12—C17—C16 | −179.5 (2) | C38—C39—C40—C35 | −0.2 (5) |
C6—Ge1—C18—C19 | 115.1 (2) | C35—Ge2—C41—C42 | 9.8 (3) |
C12—Ge1—C18—C19 | −3.8 (2) | C29—Ge2—C41—C42 | −111.4 (2) |
C3—Ge1—C18—C19 | −124.9 (2) | C26—Ge2—C41—C42 | 126.4 (2) |
C6—Ge1—C18—C23 | −65.2 (2) | C35—Ge2—C41—C46 | −168.7 (2) |
C12—Ge1—C18—C23 | 175.9 (2) | C29—Ge2—C41—C46 | 70.0 (2) |
C3—Ge1—C18—C23 | 54.8 (2) | C26—Ge2—C41—C46 | −52.2 (2) |
C23—C18—C19—C20 | −0.6 (4) | C46—C41—C42—C43 | 1.1 (4) |
Ge1—C18—C19—C20 | 179.1 (2) | Ge2—C41—C42—C43 | −177.5 (2) |
C18—C19—C20—C21 | −0.3 (4) | C41—C42—C43—C44 | −0.1 (5) |
C19—C20—C21—C22 | 0.2 (4) | C42—C43—C44—C45 | −0.3 (5) |
C20—C21—C22—C23 | 0.8 (5) | C43—C44—C45—C46 | −0.3 (5) |
C21—C22—C23—C18 | −1.7 (4) | C44—C45—C46—C41 | 1.4 (5) |
C19—C18—C23—C22 | 1.6 (4) | C42—C41—C46—C45 | −1.7 (4) |
Ge1—C18—C23—C22 | −178.1 (2) | Ge2—C41—C46—C45 | 176.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 | 1.82 | 2.645 (3) | 169 |
O4—H4···O1 | 0.84 | 1.81 | 2.638 (3) | 170 |
[Ge(C7H7)3(C5H9O2)] | F(000) = 936 |
Mr = 447.09 | Dx = 1.301 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 9035 reflections |
a = 20.041 (3) Å | θ = 3.0–27.4° |
b = 9.370 (2) Å | µ = 1.36 mm−1 |
c = 12.816 (5) Å | T = 173 K |
β = 108.436 (9)° | Block, colorless |
V = 2283.1 (11) Å3 | 0.20 × 0.16 × 0.10 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 5123 independent reflections |
Radiation source: fine-focus sealed tube | 3474 reflections with I > 2.0σ(I) |
Graphite monochromator | Rint = 0.044 |
ω and ϕ scans | θmax = 27.4°, θmin = 3.0° |
Absorption correction: multi-scan SORTAV: (Blessing, 1997) | h = −25→25 |
Tmin = 0.773, Tmax = 0.876 | k = −11→11 |
9035 measured reflections | l = −16→16 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.037P)2] where P = (Fo2 + 2Fc2)/3 |
5123 reflections | (Δ/σ)max = 0.001 |
268 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
[Ge(C7H7)3(C5H9O2)] | V = 2283.1 (11) Å3 |
Mr = 447.09 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 20.041 (3) Å | µ = 1.36 mm−1 |
b = 9.370 (2) Å | T = 173 K |
c = 12.816 (5) Å | 0.20 × 0.16 × 0.10 mm |
β = 108.436 (9)° |
Nonius KappaCCD diffractometer | 5123 independent reflections |
Absorption correction: multi-scan SORTAV: (Blessing, 1997) | 3474 reflections with I > 2.0σ(I) |
Tmin = 0.773, Tmax = 0.876 | Rint = 0.044 |
9035 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.095 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.46 e Å−3 |
5123 reflections | Δρmin = −0.47 e Å−3 |
268 parameters |
x | y | z | Uiso*/Ueq | ||
Ge1 | 0.256174 (14) | −0.04353 (3) | 0.43781 (2) | 0.02532 (10) | |
O1 | 0.46558 (10) | −0.1580 (2) | 0.53763 (18) | 0.0462 (5) | |
H1 | 0.4981 | −0.0973 | 0.5544 | 0.069* | |
O2 | 0.43144 (10) | −0.0265 (2) | 0.38483 (17) | 0.0403 (5) | |
C1 | 0.42372 (14) | −0.1310 (3) | 0.4415 (2) | 0.0316 (6) | |
C2 | 0.36389 (14) | −0.2324 (3) | 0.3952 (2) | 0.0335 (6) | |
H2A | 0.3836 | −0.3301 | 0.4016 | 0.040* | |
H2B | 0.3431 | −0.2115 | 0.3158 | 0.040* | |
C3 | 0.30357 (13) | −0.2328 (2) | 0.4464 (2) | 0.0273 (6) | |
C4 | 0.25006 (14) | −0.3417 (3) | 0.3779 (3) | 0.0393 (7) | |
H4A | 0.2300 | −0.3063 | 0.3024 | 0.059* | |
H4B | 0.2124 | −0.3550 | 0.4105 | 0.059* | |
H4C | 0.2737 | −0.4330 | 0.3771 | 0.059* | |
C5 | 0.33039 (14) | −0.2811 (3) | 0.5670 (2) | 0.0344 (7) | |
H5A | 0.3515 | −0.3761 | 0.5714 | 0.052* | |
H5B | 0.2910 | −0.2847 | 0.5967 | 0.052* | |
H5C | 0.3657 | −0.2133 | 0.6097 | 0.052* | |
C6 | 0.32253 (13) | 0.1073 (3) | 0.5099 (2) | 0.0253 (6) | |
C7 | 0.35878 (14) | 0.1060 (3) | 0.6225 (2) | 0.0314 (6) | |
H7 | 0.3492 | 0.0324 | 0.6666 | 0.038* | |
C8 | 0.40845 (14) | 0.2089 (3) | 0.6719 (2) | 0.0345 (7) | |
H8 | 0.4320 | 0.2047 | 0.7489 | 0.041* | |
C9 | 0.42403 (13) | 0.3178 (3) | 0.6103 (2) | 0.0301 (6) | |
C10 | 0.38756 (14) | 0.3214 (3) | 0.4990 (2) | 0.0330 (7) | |
H10 | 0.3973 | 0.3953 | 0.4553 | 0.040* | |
C11 | 0.33700 (13) | 0.2197 (3) | 0.4494 (2) | 0.0291 (6) | |
H11 | 0.3120 | 0.2270 | 0.3731 | 0.035* | |
C12 | 0.47945 (15) | 0.4284 (3) | 0.6630 (3) | 0.0421 (8) | |
H12A | 0.4616 | 0.4929 | 0.7083 | 0.063* | |
H12B | 0.4906 | 0.4833 | 0.6056 | 0.063* | |
H12C | 0.5220 | 0.3807 | 0.7094 | 0.063* | |
C13 | 0.21189 (14) | 0.0081 (2) | 0.2838 (2) | 0.0273 (6) | |
C14 | 0.25233 (14) | 0.0358 (2) | 0.2144 (2) | 0.0286 (6) | |
H14 | 0.3021 | 0.0288 | 0.2425 | 0.034* | |
C15 | 0.22060 (16) | 0.0730 (3) | 0.1056 (2) | 0.0337 (7) | |
H15 | 0.2491 | 0.0918 | 0.0604 | 0.040* | |
C16 | 0.14814 (17) | 0.0836 (3) | 0.0608 (2) | 0.0398 (7) | |
C17 | 0.10787 (16) | 0.0556 (3) | 0.1286 (3) | 0.0443 (8) | |
H17 | 0.0581 | 0.0610 | 0.0995 | 0.053* | |
C18 | 0.13918 (15) | 0.0197 (3) | 0.2382 (2) | 0.0375 (7) | |
H18 | 0.1104 | 0.0026 | 0.2832 | 0.045* | |
C19 | 0.11449 (19) | 0.1242 (4) | −0.0583 (3) | 0.0599 (10) | |
H19A | 0.0643 | 0.1007 | −0.0812 | 0.090* | |
H19B | 0.1371 | 0.0715 | −0.1040 | 0.090* | |
H19C | 0.1202 | 0.2270 | −0.0671 | 0.090* | |
C20 | 0.18446 (13) | −0.0569 (2) | 0.5111 (2) | 0.0278 (6) | |
C21 | 0.18119 (15) | 0.0430 (3) | 0.5883 (2) | 0.0341 (6) | |
H21 | 0.2152 | 0.1172 | 0.6065 | 0.041* | |
C22 | 0.13013 (15) | 0.0394 (3) | 0.6407 (3) | 0.0398 (7) | |
H22 | 0.1301 | 0.1109 | 0.6932 | 0.048* | |
C23 | 0.07977 (15) | −0.0657 (3) | 0.6177 (2) | 0.0379 (7) | |
C24 | 0.08188 (17) | −0.1667 (3) | 0.5404 (3) | 0.0564 (10) | |
H24 | 0.0480 | −0.2413 | 0.5232 | 0.068* | |
C25 | 0.13267 (16) | −0.1617 (3) | 0.4870 (3) | 0.0497 (9) | |
H25 | 0.1319 | −0.2316 | 0.4329 | 0.060* | |
C26 | 0.02396 (17) | −0.0722 (4) | 0.6738 (3) | 0.0563 (9) | |
H26A | 0.0362 | −0.1465 | 0.7306 | 0.084* | |
H26B | −0.0216 | −0.0946 | 0.6194 | 0.084* | |
H26C | 0.0211 | 0.0203 | 0.7079 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ge1 | 0.02497 (17) | 0.02528 (15) | 0.02687 (17) | −0.00194 (12) | 0.00986 (12) | −0.00123 (12) |
O1 | 0.0330 (12) | 0.0532 (13) | 0.0479 (14) | −0.0101 (9) | 0.0063 (11) | 0.0128 (11) |
O2 | 0.0346 (12) | 0.0436 (11) | 0.0435 (13) | −0.0022 (9) | 0.0134 (10) | 0.0122 (10) |
C1 | 0.0279 (15) | 0.0371 (15) | 0.0333 (17) | 0.0056 (12) | 0.0147 (14) | 0.0018 (13) |
C2 | 0.0350 (16) | 0.0307 (14) | 0.0352 (17) | 0.0016 (12) | 0.0115 (14) | −0.0025 (12) |
C3 | 0.0261 (14) | 0.0273 (13) | 0.0308 (16) | −0.0026 (11) | 0.0124 (12) | −0.0017 (11) |
C4 | 0.0372 (17) | 0.0310 (15) | 0.048 (2) | −0.0032 (12) | 0.0108 (15) | −0.0056 (13) |
C5 | 0.0350 (16) | 0.0327 (14) | 0.0374 (18) | −0.0013 (12) | 0.0141 (14) | 0.0044 (12) |
C6 | 0.0233 (14) | 0.0258 (13) | 0.0284 (16) | 0.0019 (10) | 0.0105 (12) | −0.0025 (11) |
C7 | 0.0354 (16) | 0.0281 (13) | 0.0315 (17) | 0.0020 (12) | 0.0117 (13) | 0.0028 (12) |
C8 | 0.0320 (16) | 0.0345 (15) | 0.0306 (17) | 0.0032 (12) | 0.0007 (13) | −0.0035 (12) |
C9 | 0.0246 (14) | 0.0276 (14) | 0.0389 (18) | 0.0019 (11) | 0.0115 (13) | −0.0072 (12) |
C10 | 0.0372 (17) | 0.0276 (14) | 0.0378 (18) | −0.0048 (12) | 0.0171 (14) | −0.0017 (12) |
C11 | 0.0314 (15) | 0.0314 (14) | 0.0251 (15) | −0.0015 (11) | 0.0099 (13) | −0.0018 (11) |
C12 | 0.0345 (17) | 0.0406 (16) | 0.051 (2) | −0.0071 (13) | 0.0124 (15) | −0.0137 (14) |
C13 | 0.0314 (15) | 0.0201 (12) | 0.0298 (16) | −0.0009 (10) | 0.0089 (13) | −0.0014 (10) |
C14 | 0.0292 (15) | 0.0279 (13) | 0.0281 (16) | 0.0028 (11) | 0.0080 (12) | −0.0002 (12) |
C15 | 0.0456 (18) | 0.0275 (14) | 0.0309 (17) | 0.0047 (12) | 0.0162 (15) | −0.0010 (11) |
C16 | 0.051 (2) | 0.0341 (15) | 0.0289 (17) | 0.0104 (13) | 0.0047 (15) | −0.0035 (12) |
C17 | 0.0291 (17) | 0.0557 (19) | 0.0395 (19) | 0.0100 (14) | −0.0014 (15) | −0.0031 (15) |
C18 | 0.0305 (16) | 0.0439 (16) | 0.0402 (19) | −0.0015 (13) | 0.0145 (14) | −0.0031 (14) |
C19 | 0.070 (2) | 0.066 (2) | 0.034 (2) | 0.0209 (19) | 0.0023 (18) | 0.0023 (17) |
C20 | 0.0253 (14) | 0.0291 (13) | 0.0290 (15) | 0.0009 (11) | 0.0088 (12) | 0.0023 (11) |
C21 | 0.0335 (16) | 0.0353 (15) | 0.0380 (17) | −0.0062 (12) | 0.0177 (14) | −0.0032 (13) |
C22 | 0.0427 (18) | 0.0412 (16) | 0.0407 (19) | 0.0004 (14) | 0.0207 (15) | −0.0074 (14) |
C23 | 0.0324 (16) | 0.0487 (17) | 0.0369 (18) | −0.0012 (13) | 0.0172 (14) | 0.0038 (14) |
C24 | 0.048 (2) | 0.058 (2) | 0.076 (3) | −0.0225 (16) | 0.037 (2) | −0.0198 (18) |
C25 | 0.0447 (19) | 0.0510 (19) | 0.064 (2) | −0.0178 (15) | 0.0328 (18) | −0.0253 (17) |
C26 | 0.046 (2) | 0.081 (2) | 0.054 (2) | −0.0111 (17) | 0.0325 (18) | −0.0062 (18) |
Ge1—C13 | 1.952 (3) | C12—H12B | 0.9800 |
Ge1—C20 | 1.954 (3) | C12—H12C | 0.9800 |
Ge1—C6 | 1.960 (2) | C13—C18 | 1.392 (4) |
Ge1—C3 | 1.999 (2) | C13—C14 | 1.404 (4) |
O1—C1 | 1.278 (3) | C14—C15 | 1.382 (4) |
O1—H1 | 0.8400 | C14—H14 | 0.9500 |
O2—C1 | 1.257 (3) | C15—C16 | 1.386 (4) |
C1—C2 | 1.497 (4) | C15—H15 | 0.9500 |
C2—C3 | 1.547 (4) | C16—C17 | 1.385 (4) |
C2—H2A | 0.9900 | C16—C19 | 1.510 (4) |
C2—H2B | 0.9900 | C17—C18 | 1.387 (4) |
C3—C5 | 1.534 (4) | C17—H17 | 0.9500 |
C3—C4 | 1.538 (3) | C18—H18 | 0.9500 |
C4—H4A | 0.9800 | C19—H19A | 0.9800 |
C4—H4B | 0.9800 | C19—H19B | 0.9800 |
C4—H4C | 0.9800 | C19—H19C | 0.9800 |
C5—H5A | 0.9800 | C20—C21 | 1.379 (4) |
C5—H5B | 0.9800 | C20—C25 | 1.391 (4) |
C5—H5C | 0.9800 | C21—C22 | 1.390 (4) |
C6—C11 | 1.392 (3) | C21—H21 | 0.9500 |
C6—C7 | 1.394 (4) | C22—C23 | 1.374 (4) |
C7—C8 | 1.387 (4) | C22—H22 | 0.9500 |
C7—H7 | 0.9500 | C23—C24 | 1.381 (4) |
C8—C9 | 1.385 (4) | C23—C26 | 1.510 (4) |
C8—H8 | 0.9500 | C24—C25 | 1.395 (4) |
C9—C10 | 1.382 (4) | C24—H24 | 0.9500 |
C9—C12 | 1.513 (4) | C25—H25 | 0.9500 |
C10—C11 | 1.390 (3) | C26—H26A | 0.9800 |
C10—H10 | 0.9500 | C26—H26B | 0.9800 |
C11—H11 | 0.9500 | C26—H26C | 0.9800 |
C12—H12A | 0.9800 | ||
C13—Ge1—C20 | 109.50 (11) | C9—C12—H12B | 109.5 |
C13—Ge1—C6 | 108.77 (10) | H12A—C12—H12B | 109.5 |
C20—Ge1—C6 | 108.18 (10) | C9—C12—H12C | 109.5 |
C13—Ge1—C3 | 109.39 (10) | H12A—C12—H12C | 109.5 |
C20—Ge1—C3 | 109.00 (10) | H12B—C12—H12C | 109.5 |
C6—Ge1—C3 | 111.97 (10) | C18—C13—C14 | 117.2 (3) |
C1—O1—H1 | 109.5 | C18—C13—Ge1 | 121.6 (2) |
O2—C1—O1 | 123.2 (3) | C14—C13—Ge1 | 121.2 (2) |
O2—C1—C2 | 119.7 (3) | C15—C14—C13 | 120.8 (3) |
O1—C1—C2 | 117.1 (2) | C15—C14—H14 | 119.6 |
C1—C2—C3 | 118.0 (2) | C13—C14—H14 | 119.6 |
C1—C2—H2A | 107.8 | C14—C15—C16 | 121.6 (3) |
C3—C2—H2A | 107.8 | C14—C15—H15 | 119.2 |
C1—C2—H2B | 107.8 | C16—C15—H15 | 119.2 |
C3—C2—H2B | 107.8 | C17—C16—C15 | 118.0 (3) |
H2A—C2—H2B | 107.1 | C17—C16—C19 | 121.3 (3) |
C5—C3—C4 | 109.8 (2) | C15—C16—C19 | 120.7 (3) |
C5—C3—C2 | 110.9 (2) | C16—C17—C18 | 121.0 (3) |
C4—C3—C2 | 104.9 (2) | C16—C17—H17 | 119.5 |
C5—C3—Ge1 | 109.03 (16) | C18—C17—H17 | 119.5 |
C4—C3—Ge1 | 108.88 (17) | C17—C18—C13 | 121.5 (3) |
C2—C3—Ge1 | 113.30 (16) | C17—C18—H18 | 119.3 |
C3—C4—H4A | 109.5 | C13—C18—H18 | 119.3 |
C3—C4—H4B | 109.5 | C16—C19—H19A | 109.5 |
H4A—C4—H4B | 109.5 | C16—C19—H19B | 109.5 |
C3—C4—H4C | 109.5 | H19A—C19—H19B | 109.5 |
H4A—C4—H4C | 109.5 | C16—C19—H19C | 109.5 |
H4B—C4—H4C | 109.5 | H19A—C19—H19C | 109.5 |
C3—C5—H5A | 109.5 | H19B—C19—H19C | 109.5 |
C3—C5—H5B | 109.5 | C21—C20—C25 | 115.9 (2) |
H5A—C5—H5B | 109.5 | C21—C20—Ge1 | 120.71 (19) |
C3—C5—H5C | 109.5 | C25—C20—Ge1 | 123.3 (2) |
H5A—C5—H5C | 109.5 | C20—C21—C22 | 122.7 (3) |
H5B—C5—H5C | 109.5 | C20—C21—H21 | 118.7 |
C11—C6—C7 | 116.8 (2) | C22—C21—H21 | 118.7 |
C11—C6—Ge1 | 120.82 (19) | C23—C22—C21 | 121.1 (3) |
C7—C6—Ge1 | 122.37 (19) | C23—C22—H22 | 119.4 |
C8—C7—C6 | 122.1 (2) | C21—C22—H22 | 119.4 |
C8—C7—H7 | 119.0 | C22—C23—C24 | 117.3 (3) |
C6—C7—H7 | 119.0 | C22—C23—C26 | 122.1 (3) |
C9—C8—C7 | 120.7 (3) | C24—C23—C26 | 120.6 (3) |
C9—C8—H8 | 119.7 | C23—C24—C25 | 121.4 (3) |
C7—C8—H8 | 119.7 | C23—C24—H24 | 119.3 |
C10—C9—C8 | 117.7 (2) | C25—C24—H24 | 119.3 |
C10—C9—C12 | 121.2 (2) | C20—C25—C24 | 121.6 (3) |
C8—C9—C12 | 121.1 (3) | C20—C25—H25 | 119.2 |
C9—C10—C11 | 121.8 (2) | C24—C25—H25 | 119.2 |
C9—C10—H10 | 119.1 | C23—C26—H26A | 109.5 |
C11—C10—H10 | 119.1 | C23—C26—H26B | 109.5 |
C10—C11—C6 | 120.9 (3) | H26A—C26—H26B | 109.5 |
C10—C11—H11 | 119.5 | C23—C26—H26C | 109.5 |
C6—C11—H11 | 119.5 | H26A—C26—H26C | 109.5 |
C9—C12—H12A | 109.5 | H26B—C26—H26C | 109.5 |
O2—C1—C2—C3 | −110.6 (3) | C6—Ge1—C13—C18 | −122.8 (2) |
O1—C1—C2—C3 | 70.6 (3) | C3—Ge1—C13—C18 | 114.6 (2) |
C1—C2—C3—C5 | −64.1 (3) | C20—Ge1—C13—C14 | 174.96 (18) |
C1—C2—C3—C4 | 177.5 (2) | C6—Ge1—C13—C14 | 56.9 (2) |
C1—C2—C3—Ge1 | 58.8 (3) | C3—Ge1—C13—C14 | −65.7 (2) |
C13—Ge1—C3—C5 | −173.15 (16) | C18—C13—C14—C15 | 0.1 (4) |
C20—Ge1—C3—C5 | −53.45 (19) | Ge1—C13—C14—C15 | −179.66 (17) |
C6—Ge1—C3—C5 | 66.20 (19) | C13—C14—C15—C16 | −0.4 (4) |
C13—Ge1—C3—C4 | −53.4 (2) | C14—C15—C16—C17 | 0.0 (4) |
C20—Ge1—C3—C4 | 66.3 (2) | C14—C15—C16—C19 | −179.9 (3) |
C6—Ge1—C3—C4 | −174.04 (17) | C15—C16—C17—C18 | 0.7 (4) |
C13—Ge1—C3—C2 | 62.9 (2) | C19—C16—C17—C18 | −179.3 (3) |
C20—Ge1—C3—C2 | −177.40 (18) | C16—C17—C18—C13 | −1.1 (4) |
C6—Ge1—C3—C2 | −57.8 (2) | C14—C13—C18—C17 | 0.6 (4) |
C13—Ge1—C6—C11 | −6.4 (2) | Ge1—C13—C18—C17 | −179.6 (2) |
C20—Ge1—C6—C11 | −125.3 (2) | C13—Ge1—C20—C21 | −110.0 (2) |
C3—Ge1—C6—C11 | 114.6 (2) | C6—Ge1—C20—C21 | 8.4 (2) |
C13—Ge1—C6—C7 | 175.4 (2) | C3—Ge1—C20—C21 | 130.3 (2) |
C20—Ge1—C6—C7 | 56.5 (2) | C13—Ge1—C20—C25 | 67.5 (3) |
C3—Ge1—C6—C7 | −63.6 (2) | C6—Ge1—C20—C25 | −174.1 (2) |
C11—C6—C7—C8 | −1.8 (4) | C3—Ge1—C20—C25 | −52.1 (3) |
Ge1—C6—C7—C8 | 176.45 (19) | C25—C20—C21—C22 | 0.8 (4) |
C6—C7—C8—C9 | −0.1 (4) | Ge1—C20—C21—C22 | 178.5 (2) |
C7—C8—C9—C10 | 1.2 (4) | C20—C21—C22—C23 | 0.1 (5) |
C7—C8—C9—C12 | −178.4 (2) | C21—C22—C23—C24 | −0.3 (4) |
C8—C9—C10—C11 | −0.2 (4) | C21—C22—C23—C26 | 179.7 (3) |
C12—C9—C10—C11 | 179.4 (2) | C22—C23—C24—C25 | −0.6 (5) |
C9—C10—C11—C6 | −1.8 (4) | C26—C23—C24—C25 | 179.4 (3) |
C7—C6—C11—C10 | 2.8 (4) | C21—C20—C25—C24 | −1.6 (5) |
Ge1—C6—C11—C10 | −175.54 (19) | Ge1—C20—C25—C24 | −179.3 (3) |
C20—Ge1—C13—C18 | −4.8 (2) | C23—C24—C25—C20 | 1.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.80 | 2.634 (3) | 170 |
Symmetry code: (i) −x+1, −y, −z+1. |
Experimental details
(I) | (II) | (III) | |
Crystal data | |||
Chemical formula | [Ge(C5H9O2)Cl3] | [Ge(C6H5)3(C5H9O2)] | [Ge(C7H7)3(C5H9O2)] |
Mr | 280.06 | 405.01 | 447.09 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 173 | 173 | 173 |
a, b, c (Å) | 15.526 (4), 11.521 (4), 11.828 (6) | 7.785 (1), 15.678 (2), 32.703 (5) | 20.041 (3), 9.370 (2), 12.816 (5) |
α, β, γ (°) | 90, 98.423 (15), 90 | 90, 96.668 (5), 90 | 90, 108.436 (9), 90 |
V (Å3) | 2092.9 (14) | 3964.5 (9) | 2283.1 (11) |
Z | 8 | 8 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 3.65 | 1.56 | 1.36 |
Crystal size (mm) | 0.22 × 0.18 × 0.15 | 0.16 × 0.14 × 0.12 | 0.20 × 0.16 × 0.10 |
Data collection | |||
Diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) | Multi-scan (SORTAV; Blessing, 1997) | Multi-scan SORTAV: (Blessing, 1997) |
Tmin, Tmax | 0.501, 0.611 | 0.789, 0.835 | 0.773, 0.876 |
No. of measured, independent and observed [I > 2.0σ(I)] reflections | 8438, 4760, 3200 | 16723, 9032, 6226 | 9035, 5123, 3474 |
Rint | 0.037 | 0.043 | 0.044 |
(sin θ/λ)max (Å−1) | 0.652 | 0.650 | 0.647 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.079, 1.00 | 0.040, 0.093, 1.01 | 0.040, 0.095, 1.03 |
No. of reflections | 4760 | 9032 | 5123 |
No. of parameters | 201 | 475 | 268 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.50 | 0.59, −0.39 | 0.46, −0.47 |
Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.
Ge1—C3 | 1.978 (3) | Ge2—C8 | 1.971 (3) |
Ge1—Cl3 | 2.1356 (12) | Ge2—Cl6 | 2.1330 (12) |
Ge1—Cl1 | 2.1431 (10) | Ge2—Cl5 | 2.1422 (11) |
Ge1—Cl2 | 2.1446 (10) | Ge2—Cl4 | 2.1525 (10) |
O1—C1 | 1.227 (4) | O3—C6 | 1.222 (3) |
O2—C1 | 1.308 (3) | O4—C6 | 1.305 (3) |
C3—Ge1—Cl3 | 117.63 (10) | C8—Ge2—Cl6 | 118.47 (10) |
C3—Ge1—Cl1 | 110.73 (9) | C8—Ge2—Cl5 | 113.62 (9) |
Cl3—Ge1—Cl1 | 101.64 (4) | Cl6—Ge2—Cl5 | 110.02 (4) |
C3—Ge1—Cl2 | 114.30 (10) | C8—Ge2—Cl4 | 108.92 (9) |
Cl3—Ge1—Cl2 | 107.77 (4) | Cl6—Ge2—Cl4 | 100.61 (5) |
Cl1—Ge1—Cl2 | 103.09 (4) | Cl5—Ge2—Cl4 | 103.27 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 | 1.83 | 2.665 (3) | 179 |
O4—H4···O1 | 0.84 | 1.81 | 2.649 (3) | 176 |
Ge1—C6 | 1.953 (3) | Ge2—C41 | 1.955 (3) |
Ge1—C18 | 1.954 (3) | Ge2—C35 | 1.956 (3) |
Ge1—C12 | 1.955 (3) | Ge2—C29 | 1.960 (3) |
Ge1—C3 | 1.998 (3) | Ge2—C26 | 2.005 (3) |
O1—C1 | 1.231 (3) | O3—C24 | 1.246 (3) |
O2—C1 | 1.297 (3) | O4—C24 | 1.295 (3) |
C6—Ge1—C18 | 109.98 (11) | C41—Ge2—C35 | 110.01 (12) |
C6—Ge1—C12 | 108.89 (11) | C41—Ge2—C29 | 109.00 (11) |
C18—Ge1—C12 | 108.22 (11) | C35—Ge2—C29 | 110.49 (11) |
C6—Ge1—C3 | 108.92 (11) | C41—Ge2—C26 | 109.49 (10) |
C18—Ge1—C3 | 110.07 (11) | C35—Ge2—C26 | 106.35 (11) |
C12—Ge1—C3 | 110.75 (11) | C29—Ge2—C26 | 111.48 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.84 | 1.82 | 2.645 (3) | 169 |
O4—H4···O1 | 0.84 | 1.81 | 2.638 (3) | 170 |
Ge1—C13 | 1.952 (3) | Ge1—C3 | 1.999 (2) |
Ge1—C20 | 1.954 (3) | O1—C1 | 1.278 (3) |
Ge1—C6 | 1.960 (2) | O2—C1 | 1.257 (3) |
C13—Ge1—C20 | 109.50 (11) | C13—Ge1—C3 | 109.39 (10) |
C13—Ge1—C6 | 108.77 (10) | C20—Ge1—C3 | 109.00 (10) |
C20—Ge1—C6 | 108.18 (10) | C6—Ge1—C3 | 111.97 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.80 | 2.634 (3) | 170 |
Symmetry code: (i) −x+1, −y, −z+1. |
Organotin carboxylates have been studied extensively because of their richness in structural motifs, biological activities, commercial values and potential as antitumour agents (Davis & Smith, 1982). It is well known that the biological activities and selectivities of trialkyltin derivatives depend mainly on the alkyl groups attached to Sn atom. Organogermanium is another class of compounds that has a wide range of biological activity (Lukevics, 1992). The first organogermanium pharmaceutical, propagermanium, was launched in Japan in 1994; its biological activity spectrum modulates protection against viruses, immunostimulation and hepatoprolation (William et al., 1997; Kakimoto et al., 1985; Lukevics et al., 1992, 1998). In this paper, we report the crystal structures of the 3,3-dimethyl(3-germyl)propionic acid derivatives 3,3-dimethyl(3-trichlorogermyl)propionic acid, (I), 3,3-dimethyl(3-triphenylgermyl)propionic acid, (II), and 3,3-dimethyl(3-p-methylphenylgermyl)propionic acid, (III).
The structure of (I) is composed of two independent molecules in the asymmetric unit, forming dimers via strong O—H···O hydrogen bonds, resulting in eight-membered rings that can be best described in terms of graph-set notation R22(8) (Bernstein et al., 1994) (Fig. 1). Details of the hydrogen-bonding geometry are given in Table 2. The geometry around the Ge atoms is slightly distorted tetrahedral. The Ge—Cl distances in both molecules are essentially identical within 3σ limits and lie within a narrow range. The Ge—C distances are also identical. These distances agree with the corresponding distances reported for trichlorogermyl complexes in the Cambridge Structural Database, with refcodes BOSBIU01, CUBMUH, CUBYUT, DADKEY, JIRLOL and SIWZON (CSD; Version 5.25, 2003 release; Allen, 2002).
The structure of (II) is also composed of two independent molecules in the asymmetric unit, forming dimers (Fig. 2) as in (I), resulting in eight-membered R22(8) rings. Details of the hydrogen-bonding geometry are given in Table 4. The geometry around the Ge atoms is slightly distorted tetrahedral. The Ge—Caromatic distances in both molecules are essentially identical within 3σ limits. The Ge—Caliphatic distances are also identical and are significantly longer than Ge—Caromatic distances, as expected. These distances agree with the corresponding distances reported for a handful of triarylgermyl complexes contained in the Cambridge Structural Database, with refcodes ATPGER, IHELIQ, IHELOW, SUCZOF, TPENGE, XUQZOY and ZAHKIC (CSD; Version 5.25, 2003 release; Allen, 2002).
Unlike the structures of (I) and (II), the structure of (III) is composed of one molecule in the asymmetric unit (Fig. 3); these molecules form dimers about inversion centers, resulting in eight-membered R22(8) rings, as observed in (I) and (II). Details of the hydrogen-bonding geometry are in Table 6. The geometry around the Ge atoms is slightly distorted tetrahedral. The Ge—Caromatic and Ge—Caliphatic distances show the same pattern as observed in the structure of (II). The fact that the Ge—Caliphatic distances in (I) are significantly shorter than those in (II) and (III) may be attributed to the Cl atoms bonded to the Ge atom in (I).
In all of the structures, the carboxyl groups adopt the more prevalent synplanar conformation. However, the rings formed by the intermolecular interactions between carboxyl groups in (I) and (III) are more or less planar [the maximum deviation of any atom from the plane defined by four O and two C atoms being 0.054 (2) and 0.010 (2) Å, respectively], in contrast to the ring in (II), which is substantially twisted [the maximum deviation is 0.224 (2) Å]. Moreover, the propyl and carboxyl groups in the two molecules of (I) are oriented at 12.4 (3) and 30.2 (2)°, compared with 78.6 (3) and 80.6 (2)° in (II), and 70.0 (2)° in (III). The differences in the orientation of these groups appear to influence the O···O interactions, which are somewhat longer in (I) than in (II) and (III), and have also been observed in the germyl complexes mentioned above.