3-Germyl-3,3-di­methyl­propionic acid derivatives

The crystal structures of 3,3-di­methyl-3-(tri­chloro­germyl)­propionic acid, [Ge(C₅H₉O₂)Cl₃], 3,3-di­methyl-3-(tri­phenyl­germyl)­propionic acid, [Ge(C₆H₅)₃(C₅H₉O₂)], and 3,3-di­methyl-3-(tri-p-toly­lgermyl)­propionic acid, [Ge(C₇H₇)₃(C₅H₉O₂)], have slightly distorted tetrahedral geometries about the Ge atoms. All the structures form dimers via strong O—H...O hydrogen bonds, resulting in eight-membered rings that can be best described in terms of graph-set notation (8).

S1. Comment

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 R₂^{2_{(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 R₂^{2_{(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—C}aromatic _{distances in both molecules are essentially identical within 3σ limits. The Ge—C}aliphatic _{distances are also identical and are significantly longer than Ge—C}aromatic _{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 R₂^{2_{(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—C}aromatic _{and Ge—C}aliphatic _{distances show the same pattern as observed in the structure of (II). The fact that the Ge—C}aliphatic _{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.

S2. Experimental

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).

S3. Refinement

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 U_iso(H) values of 1.5 (hydroxyl and methyl) and 1.2 (aromatic and CH₂) times U_eq of the parent atoms. The final difference map was free of any chemically significant features.

Computing details

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).

Figures

	Fig. 1. An ORTEPII (Johnson, 1976) drawing showing two hydrogen-bonded molecules in the asymmetric unit of (I), with displacement ellipsoids plotted at the 50% probability level.
	Fig. 2. An ORTEPII (Johnson, 1976) drawing showing two hydorgen-bonded molecules in the asymmetric unit of (II), with displacement ellipsoids plotted at the 50% probability level.
	Fig. 3. An ORTEPII (Johnson, 1976) drawing of (III), with displacement ellipsoids plotted at the 50% probability level.

(I) 3,3-dimethyl-3-(trichlorogermyl)propionic acid

Crystal data

[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) Å^3	Block, colorless
Z = 8	0.22 × 0.18 × 0.15 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.079	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.028P)^2 + 0.5P] where P = (Fo^2 + 2Fc^2)/3
4760 reflections	(Δ/σ)max = 0.001
201 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.50 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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

(II) 3,3-dimethyl-3-(triphenylgermyl)propionic acid

Crystal data

[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) Å^3	Block, colorless
Z = 8	0.16 × 0.14 × 0.12 mm

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0344P)^2 + 1.542P] where P = (Fo^2 + 2Fc^2)/3
9032 reflections	(Δ/σ)max = 0.003
475 parameters	Δρmax = 0.59 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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

(III) 3,3-dimethyl-3-(tri-p-tolylgermyl)propionic acid

Crystal data

[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) Å^3	0.20 × 0.16 × 0.10 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.095	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.037P)^2] where P = (Fo^2 + 2Fc^2)/3
5123 reflections	(Δ/σ)max = 0.001
268 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.47 e Å^−3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.84	1.80	2.634 (3)	170

Symmetry code: (i) −x+1, −y, −z+1.