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The central Ge atoms in the structures of 3-(2-fluoro­phenyl)-3-(tri­phenyl­germyl)­propionic acid, [Ge(C6H5)3(C9H8FO2)], 3-(2-tolyl)-3-(tri-4-tolyl­germyl)­propionic acid, [Ge(C7H7)3(C10H11O2)], and 3-(4-tolyl)-3-(tri­benzyl­germyl)­propionic acid, [Ge(C7H7)3(C10H11O2)], are four-coordinate with slightly distorted tetrahedral geometry. The Ge-Csp3 distances [1.970 (3)-1.997 (3) Å] are significantly longer than the Ge-Caromatic distances [1.940 (3)-1.959 (2) Å]. In all three structures, the mol­ecules form dimeric pairs about inversion centres through strong hydrogen-bonding interactions between carboxyl­ic acid groups.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010201795X/fr1392sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010201795X/fr1392Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010201795X/fr1392IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010201795X/fr1392IIIsup4.hkl
Contains datablock III

CCDC references: 199415; 199416; 199417

Comment top

There has been considerable interest in recent years in the chemistry of germanium compounds, due to their diverse applications in the fields of medicine, electronics and optics, and as radiation detectors. A number of reports have been published regarding the structural chemistry of these compounds and their applications (Mackay, 1995; Westaway & Joly, 1995). In order to develop new kinds of organogermanium compounds with potential therapeutic properties, we have synthesized three derivatives of triorganogermyl propionic acid, 3-(2-fluorophenyl)-3-(triphenylgermyl)propionic acid, (I), 3-(2-tolyl)-3-(tri-4-tolylgermyl)propionic acid, (II) and 3-(tribenzylgermyl)-3-(4-tolyl)propionic acid, (III), and characterized them using X-ray diffraction methods, and the results are presented in this paper. The crystal structure of 2-methyl-3-phenyl-3-[(tri-p-tolyl)germylpropionic acid has recently been reported by our group (Imtiaz-ud-Din et al., 2002). \sch

Figs. 1–3 show the structures of (I)-(III), respectively. The central Ge atom in each compound is four-coordinate and the geometry about the Ge atoms is slightly distorted from tetrahedral, with C—Ge—C angles in the three compounds in the ranges 106.08 (6)–112.29 (7)° in (I), 105.31 (11)–115.63 (11)° in (II) and 106.94 (13)–113.30 (12)° in (III). The Ge-Csp3 distances (Ge—C3) in (I) and (II) are significantly longer [1.997 (2) and 1.984 (2) Å, respectively] than the Ge—Caromatic distances, which are identical to within 3σ limits in each of the two structures, with mean values of 1.954 (2) and 1.945 (2) Å, respectively. On the other hand, the Ge—C3 distance of 1.981 (3) Å in (III) is barely longer than the Ge—Cbenzyl distances, which are also identical with a mean value of 1.971 (1) Å. These Ge—Caromatic distances are in agreement with those reported in the related structures (C9H11)3GeCN·0.5C4H8O, (C9H11)3GeNCS and (C9H11)3GeN3 (Hihara et al., 2000), Ph3GeOH (Ferguson et al., 1992), (C7H7)4Ge (Belsky et al., 1984), and (C6H5)4Ge (Karipides & Haller, 1972).

The propionate moiety in (I) (O1/O2/C1/C2/C3) is essentially planar, with atom Ge1 lying 0.380 (2)° out of the plane formed by these atoms, and is inclined at an angle of 88.11 (5)° with the mean plane of the phenyl ring C4—C9 atoms. The mean planes of the phenyl rings C11—C16 (ring 1), C18—C23 (ring 2) and C25—C30 (ring 3) bonded to atom Ge1 are inclined with respect to each other at angles of 69.09 (6), 59.92 (7) and 68.21 (5)° for the pairs of rings 1/2, 1/3 and 2/3, respectively.

The propionate moiety in (II) is not planar, in contrast to (I). In this case, only atoms O1, O2, C1 and C2 are planar to within 0.012 (3) Å, while atoms C3 and Ge1 lie 0.679 (5) and 0.086 (7) Å, respectively, out of the plane of these atoms. The mean planes of the phenyl rings [rings 1–3, as defined for (I)] bonded to atom Ge1 are inclined with respect to each other at angles of 80.90 (10), 64.21 (12) and 67.42 (12)° for the pairs of rings 1/2, 1/3 and 2/3, respectively.

The propionate moiety in (III) is also non-planar, as observed in (II), wherein only atoms O1, O2, C1 and C2 are planar to within 0.012 (3) Å, while atoms C3 and Ge1 are 0.814 (5) and 0.277 (8) Å, respectively, out of the plane of these atoms. The mean planes of the benzyl rings [rings 1–3, as defined for (I)] bonded to atom Ge1 are inclined with respect to each other at angles of 71.7 (4), 74.3 (3) and 84.7 (1)° for the pairs of rings 1/2, 1/3 and 2/3, respectively. One of the phenyl rings in (III) is disordered over sites C19—C24 and C19'-C24' with site occupancy factors of 0.65 (4) and 0.35 (4), respectively, and with the mean planes of these rings lying at 7.0 (5)° with respect to each other.

In all three structures, the molecules form dimeric pairs about inversion centres through strong hydrogen-bonding interactions between carboxylate groups. These hydrogen-bonding interactions can be described in terms of graph-set presentations of R22(8) (Bernstein et al., 1994). In addition, there are short intermolecular C—H···O interactions (involving atoms C8 and O1) and intramolecular C3—H3···F1 contacts present in (I). The structure of (II) exhibits short intermolecular H8···H8i interactions involving adjacent molecules [2.08 Å; symmetry code: (ii) -x, 1 - y, 2 - z], resulting in a phenyl ring of the phenylpropionate ligand with C—C distances spanning a wide range; the shortest distance is C7—C8. Intramolecular C3—H3···O1 contacts are also observed in (II) and (III). Details of the hydrogen-bonding geometry for (I)-(III) are given in Tables 2, 4 and 6, respectively.

Experimental top

Compounds (I)-(III) were prepared following the standard methods described by Choudhary et al. (2002). Crystals suitable for X-ray analysis were grown 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 several days yielded fine crystals which were subsequently washed with acetone.

Refinement top

For the three structures, the H atoms were located from difference Fourier syntheses and were included in the refinements at idealized positions, with Uiso(H) = 1.5Ueq(OH) and 1.2Ueq(C). Default C—H and O—H distances were allowed for the various types of H atoms, as set by the program SHELXL97 (Sheldrick, 1997). One of the phenyl rings in (III) is disordered over sites C19—C24 and C19'-C24' with unequal site occupancy factors of 0.65 (4) and 0.35 (4), respectively. The final difference maps were free of any chemically significant features in the three structures.

Computing details top

For all compounds, data collection: COLLECT (Nonius, 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.

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), with displacement ellipsoids plotted at the 50% probability level. H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A view of the molecule of (II), with displacement ellipsoids plotted at the 50% probability level. H atoms are shown as small spheres of arbitrary radii.
[Figure 3] Fig. 3. A view of the molecule of (III), with displacement ellipsoids plotted at the 50% probability level. H atoms are shown as small spheres of arbitrary radii. The phenyl ring C19'-C24', representing the minor fraction, is not illustrated.
(I) 3-(2-fluorophenyl)-3-(triphenylgermyl)propionic acid top
Crystal data top
[Ge(C6H5)3(C9H8FO2)]F(000) = 968
Mr = 471.04Dx = 1.420 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9816 reflections
a = 9.7278 (10) Åθ = 1.0–27.5°
b = 17.907 (3) ŵ = 1.42 mm1
c = 13.541 (2) ÅT = 170 K
β = 110.907 (8)°Block, colourless
V = 2203.5 (6) Å30.20 × 0.15 × 0.14 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
5026 independent reflections
Radiation source: fine-focus sealed tube4338 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.017
ω and ϕ scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1212
Tmin = 0.711, Tmax = 0.820k = 2323
9816 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.070H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0332P)2 + 0.8526P]
where P = (Fo2 + 2Fc2)/3
5026 reflections(Δ/σ)max = 0.002
281 parametersΔρmax = 0.30 e Å3
0 restraintsΔρmin = 0.44 e Å3
Crystal data top
[Ge(C6H5)3(C9H8FO2)]V = 2203.5 (6) Å3
Mr = 471.04Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.7278 (10) ŵ = 1.42 mm1
b = 17.907 (3) ÅT = 170 K
c = 13.541 (2) Å0.20 × 0.15 × 0.14 mm
β = 110.907 (8)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
5026 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
4338 reflections with I > 2σ(I)
Tmin = 0.711, Tmax = 0.820Rint = 0.017
9816 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.070H-atom parameters constrained
S = 1.03Δρmax = 0.30 e Å3
5026 reflectionsΔρmin = 0.44 e Å3
281 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ge10.839925 (17)0.183673 (9)0.828679 (12)0.02017 (6)
F10.61906 (12)0.00707 (6)0.69416 (9)0.0392 (3)
O10.88991 (12)0.02038 (6)0.56415 (9)0.0279 (3)
O21.07267 (14)0.09183 (7)0.55351 (10)0.0341 (3)
H21.08240.05650.51580.051*
C10.96590 (17)0.07620 (9)0.58850 (12)0.0231 (3)
C20.95146 (18)0.13483 (9)0.66445 (13)0.0260 (3)
H2A0.93010.18360.62770.031*
H2B1.04650.13930.72410.031*
C30.83045 (16)0.11711 (9)0.70813 (12)0.0225 (3)
H30.84810.06500.73650.027*
C40.67724 (17)0.11887 (9)0.62599 (12)0.0220 (3)
C50.6257 (2)0.17702 (10)0.55313 (14)0.0304 (4)
H50.69110.21600.55130.036*
C60.4808 (2)0.17886 (11)0.48336 (15)0.0392 (5)
H60.44790.21940.43540.047*
C70.3844 (2)0.12260 (12)0.48314 (14)0.0401 (5)
H70.28600.12380.43430.048*
C80.43100 (19)0.06432 (11)0.55400 (14)0.0348 (4)
H80.36560.02530.55530.042*
C90.57508 (18)0.06432 (9)0.62294 (13)0.0269 (3)
C110.66775 (17)0.15948 (9)0.86442 (12)0.0224 (3)
C120.52581 (18)0.16953 (10)0.78972 (13)0.0267 (4)
H120.51360.19340.72450.032*
C130.40272 (19)0.14504 (11)0.80971 (15)0.0348 (4)
H130.30740.15070.75750.042*
C140.4194 (2)0.11243 (12)0.90557 (15)0.0401 (5)
H140.33540.09590.91960.048*
C150.5585 (2)0.10372 (12)0.98131 (15)0.0386 (4)
H150.56940.08181.04760.046*
C160.68217 (19)0.12679 (10)0.96110 (13)0.0294 (4)
H160.77720.12031.01340.035*
C181.02127 (17)0.16128 (9)0.94756 (12)0.0231 (3)
C191.06854 (18)0.08792 (9)0.97522 (13)0.0270 (3)
H191.01470.04780.93300.032*
C201.19301 (19)0.07254 (11)1.06353 (14)0.0335 (4)
H201.22280.02231.08130.040*
C211.2733 (2)0.13015 (12)1.12541 (15)0.0395 (4)
H211.35770.11981.18610.047*
C221.2295 (2)0.20313 (12)1.09784 (16)0.0433 (5)
H221.28540.24301.13940.052*
C231.1049 (2)0.21889 (10)1.01034 (14)0.0335 (4)
H231.07610.26930.99300.040*
C250.83946 (18)0.28931 (9)0.79274 (12)0.0246 (3)
C260.7291 (2)0.33745 (10)0.79790 (14)0.0318 (4)
H260.65220.31830.81850.038*
C270.7298 (2)0.41287 (11)0.77340 (15)0.0402 (5)
H270.65380.44480.77710.048*
C280.8411 (2)0.44124 (11)0.74363 (15)0.0414 (5)
H280.84100.49260.72610.050*
C290.9525 (2)0.39507 (11)0.73934 (15)0.0379 (4)
H291.02950.41480.71940.045*
C300.9521 (2)0.31984 (9)0.76410 (14)0.0302 (4)
H301.02970.28860.76150.036*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ge10.01820 (9)0.02157 (10)0.02182 (10)0.00053 (6)0.00844 (7)0.00249 (6)
F10.0352 (6)0.0321 (6)0.0454 (6)0.0083 (5)0.0083 (5)0.0083 (5)
O10.0255 (6)0.0278 (6)0.0346 (6)0.0037 (5)0.0159 (5)0.0092 (5)
O20.0371 (7)0.0284 (7)0.0488 (8)0.0086 (5)0.0300 (6)0.0135 (6)
C10.0191 (7)0.0248 (8)0.0259 (8)0.0013 (6)0.0088 (6)0.0018 (6)
C20.0218 (8)0.0263 (8)0.0328 (8)0.0037 (6)0.0134 (7)0.0084 (7)
C30.0197 (7)0.0231 (8)0.0262 (8)0.0006 (6)0.0100 (6)0.0029 (6)
C40.0213 (7)0.0257 (8)0.0218 (7)0.0004 (6)0.0111 (6)0.0044 (6)
C50.0334 (9)0.0326 (10)0.0286 (9)0.0013 (7)0.0153 (8)0.0029 (7)
C60.0349 (10)0.0476 (12)0.0315 (10)0.0115 (9)0.0075 (8)0.0102 (8)
C70.0245 (9)0.0603 (13)0.0302 (9)0.0054 (9)0.0033 (7)0.0043 (9)
C80.0245 (9)0.0421 (11)0.0369 (10)0.0078 (8)0.0099 (8)0.0102 (8)
C90.0275 (8)0.0274 (9)0.0262 (8)0.0013 (7)0.0101 (7)0.0015 (6)
C110.0224 (8)0.0226 (8)0.0243 (8)0.0002 (6)0.0107 (6)0.0034 (6)
C120.0227 (8)0.0343 (9)0.0254 (8)0.0027 (7)0.0116 (7)0.0006 (7)
C130.0218 (8)0.0478 (11)0.0358 (9)0.0013 (8)0.0116 (7)0.0017 (8)
C140.0329 (10)0.0528 (12)0.0420 (10)0.0102 (9)0.0225 (9)0.0013 (9)
C150.0400 (10)0.0498 (12)0.0305 (9)0.0056 (9)0.0183 (8)0.0059 (8)
C160.0275 (9)0.0357 (10)0.0248 (8)0.0009 (7)0.0090 (7)0.0003 (7)
C180.0197 (7)0.0274 (8)0.0241 (8)0.0017 (6)0.0102 (6)0.0029 (6)
C190.0254 (8)0.0265 (9)0.0301 (8)0.0019 (7)0.0111 (7)0.0002 (7)
C200.0271 (9)0.0370 (10)0.0364 (9)0.0044 (7)0.0113 (8)0.0089 (8)
C210.0243 (9)0.0554 (13)0.0334 (9)0.0007 (8)0.0036 (7)0.0044 (9)
C220.0327 (10)0.0462 (12)0.0400 (11)0.0092 (9)0.0006 (8)0.0111 (9)
C230.0325 (9)0.0274 (9)0.0357 (9)0.0033 (7)0.0062 (8)0.0066 (7)
C250.0278 (8)0.0232 (8)0.0216 (7)0.0011 (7)0.0073 (6)0.0028 (6)
C260.0300 (9)0.0302 (9)0.0346 (9)0.0015 (7)0.0107 (7)0.0030 (7)
C270.0415 (11)0.0285 (10)0.0416 (11)0.0083 (8)0.0040 (9)0.0048 (8)
C280.0531 (12)0.0244 (9)0.0356 (10)0.0060 (9)0.0022 (9)0.0007 (8)
C290.0469 (11)0.0321 (10)0.0348 (10)0.0121 (9)0.0146 (9)0.0014 (8)
C300.0336 (9)0.0274 (9)0.0313 (9)0.0043 (7)0.0137 (8)0.0039 (7)
Geometric parameters (Å, º) top
Ge1—C111.951 (2)C13—H130.9500
Ge1—C251.953 (2)C14—C151.384 (3)
Ge1—C181.959 (2)C14—H140.9500
Ge1—C31.997 (2)C15—C161.388 (2)
F1—C91.367 (2)C15—H150.9500
O1—C11.217 (2)C16—H160.9500
O2—C11.316 (2)C18—C191.398 (2)
O2—H20.8400C18—C231.398 (2)
C1—C21.511 (2)C19—C201.392 (2)
C2—C31.527 (2)C19—H190.9500
C2—H2A0.9900C20—C211.382 (3)
C2—H2B0.9900C20—H200.9500
C3—C41.509 (2)C21—C221.384 (3)
C3—H31.0000C21—H210.9500
C4—C91.383 (2)C22—C231.388 (3)
C4—C51.399 (2)C22—H220.9500
C5—C61.390 (3)C23—H230.9500
C5—H50.9500C25—C301.397 (2)
C6—C71.375 (3)C25—C261.398 (2)
C6—H60.9500C26—C271.391 (3)
C7—C81.380 (3)C26—H260.9500
C7—H70.9500C27—C281.380 (3)
C8—C91.379 (2)C27—H270.9500
C8—H80.9500C28—C291.381 (3)
C11—C161.395 (2)C28—H280.9500
C11—C121.402 (2)C29—C301.389 (3)
C12—C131.389 (2)C29—H290.9500
C12—H120.9500C30—H300.9500
C13—C141.379 (3)
C11—Ge1—C25110.55 (7)C14—C13—H13120.1
C11—Ge1—C18110.60 (6)C12—C13—H13120.1
C25—Ge1—C18108.93 (7)C13—C14—C15120.06 (17)
C11—Ge1—C3106.08 (6)C13—C14—H14120.0
C25—Ge1—C3112.29 (7)C15—C14—H14120.0
C18—Ge1—C3108.35 (6)C14—C15—C16120.46 (17)
C1—O2—H2109.5C14—C15—H15119.8
O1—C1—O2123.93 (14)C16—C15—H15119.8
O1—C1—C2124.07 (14)C15—C16—C11120.39 (16)
O2—C1—C2111.98 (13)C15—C16—H16119.8
C1—C2—C3113.01 (13)C11—C16—H16119.8
C1—C2—H2A109.0C19—C18—C23117.79 (15)
C3—C2—H2A109.0C19—C18—Ge1121.75 (12)
C1—C2—H2B109.0C23—C18—Ge1120.42 (13)
C3—C2—H2B109.0C20—C19—C18121.21 (16)
H2A—C2—H2B107.8C20—C19—H19119.4
C4—C3—C2113.91 (13)C18—C19—H19119.4
C4—C3—Ge1109.60 (10)C21—C20—C19120.22 (17)
C2—C3—Ge1112.05 (10)C21—C20—H20119.9
C4—C3—H3107.0C19—C20—H20119.9
C2—C3—H3107.0C20—C21—C22119.22 (17)
Ge1—C3—H3107.0C20—C21—H21120.4
C9—C4—C5115.59 (15)C22—C21—H21120.4
C9—C4—C3121.16 (14)C21—C22—C23120.89 (18)
C5—C4—C3123.13 (15)C21—C22—H22119.6
C6—C5—C4121.23 (17)C23—C22—H22119.6
C6—C5—H5119.4C22—C23—C18120.66 (18)
C4—C5—H5119.4C22—C23—H23119.7
C7—C6—C5120.62 (17)C18—C23—H23119.7
C7—C6—H6119.7C30—C25—C26117.71 (16)
C5—C6—H6119.7C30—C25—Ge1121.05 (13)
C6—C7—C8119.87 (17)C26—C25—Ge1121.22 (13)
C6—C7—H7120.1C27—C26—C25121.15 (18)
C8—C7—H7120.1C27—C26—H26119.4
C9—C8—C7118.21 (17)C25—C26—H26119.4
C9—C8—H8120.9C28—C27—C26119.89 (18)
C7—C8—H8120.9C28—C27—H27120.1
F1—C9—C8117.64 (15)C26—C27—H27120.1
F1—C9—C4117.88 (14)C27—C28—C29120.09 (18)
C8—C9—C4124.47 (16)C27—C28—H28120.0
C16—C11—C12118.32 (15)C29—C28—H28120.0
C16—C11—Ge1121.22 (12)C28—C29—C30120.03 (18)
C12—C11—Ge1120.29 (12)C28—C29—H29120.0
C13—C12—C11120.96 (16)C30—C29—H29120.0
C13—C12—H12119.5C29—C30—C25121.12 (17)
C11—C12—H12119.5C29—C30—H30119.4
C14—C13—C12119.77 (17)C25—C30—H30119.4
O1—C1—C2—C30.1 (2)C12—C13—C14—C150.4 (3)
O2—C1—C2—C3178.73 (14)C13—C14—C15—C160.8 (3)
C1—C2—C3—C466.29 (18)C14—C15—C16—C110.4 (3)
C1—C2—C3—Ge1168.58 (11)C12—C11—C16—C151.2 (3)
C11—Ge1—C3—C447.19 (12)Ge1—C11—C16—C15174.07 (14)
C25—Ge1—C3—C473.68 (12)C11—Ge1—C18—C1973.15 (14)
C18—Ge1—C3—C4165.96 (10)C25—Ge1—C18—C19165.16 (13)
C11—Ge1—C3—C2174.66 (11)C3—Ge1—C18—C1942.73 (14)
C25—Ge1—C3—C253.79 (13)C11—Ge1—C18—C23104.30 (14)
C18—Ge1—C3—C266.56 (13)C25—Ge1—C18—C2317.39 (15)
C2—C3—C4—C9136.78 (15)C3—Ge1—C18—C23139.82 (13)
Ge1—C3—C4—C996.80 (15)C23—C18—C19—C201.3 (2)
C2—C3—C4—C547.4 (2)Ge1—C18—C19—C20176.26 (13)
Ge1—C3—C4—C578.99 (16)C18—C19—C20—C210.5 (3)
C9—C4—C5—C60.3 (2)C19—C20—C21—C220.7 (3)
C3—C4—C5—C6175.71 (16)C20—C21—C22—C231.2 (3)
C4—C5—C6—C71.0 (3)C21—C22—C23—C180.4 (3)
C5—C6—C7—C81.2 (3)C19—C18—C23—C220.8 (3)
C6—C7—C8—C90.5 (3)Ge1—C18—C23—C22176.77 (15)
C7—C8—C9—F1178.72 (16)C11—Ge1—C25—C30179.87 (13)
C7—C8—C9—C40.2 (3)C18—Ge1—C25—C3058.41 (15)
C5—C4—C9—F1178.60 (14)C3—Ge1—C25—C3061.61 (15)
C3—C4—C9—F12.5 (2)C11—Ge1—C25—C262.13 (15)
C5—C4—C9—C80.3 (2)C18—Ge1—C25—C26119.59 (14)
C3—C4—C9—C8176.41 (15)C3—Ge1—C25—C26120.39 (13)
C25—Ge1—C11—C16124.11 (14)C30—C25—C26—C271.2 (3)
C18—Ge1—C11—C163.38 (16)Ge1—C25—C26—C27179.28 (14)
C3—Ge1—C11—C16113.91 (14)C25—C26—C27—C280.2 (3)
C25—Ge1—C11—C1260.74 (15)C26—C27—C28—C290.7 (3)
C18—Ge1—C11—C12178.53 (13)C27—C28—C29—C300.6 (3)
C3—Ge1—C11—C1261.24 (14)C28—C29—C30—C250.5 (3)
C16—C11—C12—C132.4 (2)C26—C25—C30—C291.4 (3)
Ge1—C11—C12—C13172.91 (14)Ge1—C25—C30—C29179.48 (13)
C11—C12—C13—C142.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.841.832.6689 (16)178
C8—H8···O1ii0.952.573.323 (2)137
C3—H3···F11.002.342.805 (2)108
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+1.
(II) 3-(2-tolyl)-3-(tri-4-tolylgermyl)propionic acid top
Crystal data top
[Ge(C7H7)3(C10H11O2)]F(000) = 1064
Mr = 509.16Dx = 1.213 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 10731 reflections
a = 10.984 (3) Åθ = 1.0–27.5°
b = 13.710 (4) ŵ = 1.12 mm1
c = 20.245 (5) ÅT = 293 K
β = 113.857 (14)°Prismatic, colourless
V = 2788.3 (13) Å30.20 × 0.17 × 0.13 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
6346 independent reflections
Radiation source: fine-focus sealed tube4185 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.025
ω and ϕ scansθmax = 27.5°, θmin = 4.0°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1414
Tmin = 0.749, Tmax = 0.864k = 1617
10731 measured reflectionsl = 2626
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.047P)2 + 0.8585P]
where P = (Fo2 + 2Fc2)/3
6346 reflections(Δ/σ)max = 0.002
308 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.42 e Å3
Crystal data top
[Ge(C7H7)3(C10H11O2)]V = 2788.3 (13) Å3
Mr = 509.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.984 (3) ŵ = 1.12 mm1
b = 13.710 (4) ÅT = 293 K
c = 20.245 (5) Å0.20 × 0.17 × 0.13 mm
β = 113.857 (14)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
6346 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
4185 reflections with I > 2σ(I)
Tmin = 0.749, Tmax = 0.864Rint = 0.025
10731 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.01Δρmax = 0.38 e Å3
6346 reflectionsΔρmin = 0.42 e Å3
308 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ge10.39820 (2)0.22013 (2)0.916746 (13)0.05927 (12)
O10.0505 (2)0.0675 (2)0.94832 (13)0.1132 (9)
O20.1742 (2)0.0017 (2)1.05274 (12)0.1025 (8)
H20.10070.01201.05160.154*
C10.1601 (3)0.0526 (2)0.99729 (15)0.0661 (7)
C20.2845 (3)0.0900 (2)0.99328 (15)0.0665 (7)
H2A0.31140.04470.96560.080*
H2B0.35270.09431.04130.080*
C30.2659 (2)0.19052 (19)0.95768 (13)0.0600 (6)
H30.18250.18390.91670.072*
C40.2549 (3)0.2736 (2)1.00368 (15)0.0654 (7)
C50.3500 (4)0.2842 (3)1.07418 (18)0.0881 (9)
H50.41870.23591.09330.106*
C60.3461 (5)0.3626 (4)1.1169 (2)0.1227 (15)
H60.41010.36871.16590.147*
C70.2499 (7)0.4317 (4)1.0886 (4)0.142 (2)
H70.24860.48781.11670.171*
C80.1567 (6)0.4220 (3)1.0208 (4)0.1273 (16)
H80.08920.47121.00200.153*
C90.1541 (3)0.3436 (3)0.9758 (2)0.0901 (9)
C100.0462 (4)0.3376 (3)0.9011 (2)0.1234 (14)
H10A0.01330.39190.89300.148*
H10B0.00270.27780.89500.148*
H10C0.08670.33990.86710.148*
C110.3877 (3)0.1113 (2)0.85285 (13)0.0634 (7)
C120.5015 (3)0.0706 (2)0.85117 (15)0.0763 (8)
H120.58670.09940.87900.092*
C130.4952 (3)0.0114 (3)0.80993 (17)0.0897 (10)
H130.57560.03780.80920.108*
C140.3762 (4)0.0558 (2)0.76907 (16)0.0836 (9)
C150.2625 (4)0.0155 (3)0.76972 (16)0.0883 (10)
H150.17790.04390.74040.106*
C160.2673 (3)0.0671 (3)0.81019 (16)0.0817 (9)
H160.18510.09150.80990.098*
C170.3732 (5)0.1474 (3)0.7262 (2)0.1250 (15)
H17A0.28300.16920.70110.150*
H17B0.42420.19720.75910.150*
H17C0.41120.13420.69200.150*
C180.5818 (3)0.2322 (2)0.98661 (14)0.0626 (6)
C190.6641 (3)0.2995 (3)0.97437 (18)0.0973 (11)
H190.62760.34270.93370.117*
C200.7980 (3)0.3043 (3)1.0189 (2)0.1192 (15)
H200.85600.34951.00960.143*
C210.8543 (3)0.2468 (3)1.0781 (2)0.0964 (11)
C220.7734 (3)0.1802 (3)1.09125 (18)0.0885 (9)
H220.81160.13711.13190.106*
C230.6396 (3)0.1729 (2)1.04638 (15)0.0719 (7)
H230.58570.12661.05800.086*
C241.0011 (4)0.2551 (4)1.1269 (3)0.162 (2)
H24A1.04060.30571.10930.194*
H24B1.04420.19411.12700.194*
H24C1.01160.27061.17520.194*
C250.3440 (3)0.3417 (2)0.86385 (14)0.0650 (7)
C260.2784 (3)0.3438 (2)0.78938 (15)0.0813 (8)
H260.26650.28420.76260.098*
C270.2318 (4)0.4314 (3)0.75303 (19)0.1026 (12)
H270.18840.43150.70130.123*
C280.2486 (4)0.5176 (3)0.7886 (2)0.1040 (12)
C290.3158 (4)0.5167 (3)0.8623 (2)0.0992 (11)
H290.33030.57700.88860.119*
C300.3620 (3)0.4304 (2)0.89941 (17)0.0838 (9)
H300.40920.43220.95100.101*
C310.1958 (6)0.6114 (3)0.7468 (3)0.164 (2)
H31A0.15260.59600.69640.197*
H31B0.26760.65610.75450.197*
H31C0.13280.64090.76260.197*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ge10.04470 (16)0.0744 (2)0.05520 (17)0.00848 (13)0.01654 (11)0.00079 (13)
O10.0560 (13)0.159 (2)0.1050 (17)0.0269 (14)0.0122 (12)0.0545 (16)
O20.0617 (13)0.145 (2)0.0912 (15)0.0257 (14)0.0213 (11)0.0361 (15)
C10.0532 (15)0.0749 (17)0.0665 (16)0.0116 (13)0.0203 (13)0.0038 (14)
C20.0529 (14)0.0701 (16)0.0781 (17)0.0061 (13)0.0282 (13)0.0050 (14)
C30.0443 (13)0.0717 (16)0.0614 (14)0.0071 (11)0.0186 (11)0.0002 (12)
C40.0594 (15)0.0697 (17)0.0747 (17)0.0065 (13)0.0351 (14)0.0004 (14)
C50.084 (2)0.103 (3)0.079 (2)0.0117 (19)0.0344 (17)0.0114 (19)
C60.139 (4)0.139 (4)0.104 (3)0.042 (3)0.063 (3)0.053 (3)
C70.167 (5)0.111 (4)0.192 (6)0.026 (4)0.117 (5)0.059 (4)
C80.129 (4)0.087 (3)0.198 (5)0.014 (3)0.100 (4)0.010 (3)
C90.077 (2)0.086 (2)0.121 (3)0.0065 (18)0.054 (2)0.004 (2)
C100.076 (2)0.135 (3)0.149 (4)0.037 (2)0.036 (2)0.034 (3)
C110.0533 (14)0.0801 (18)0.0537 (13)0.0054 (13)0.0187 (11)0.0011 (13)
C120.0605 (17)0.096 (2)0.0684 (17)0.0013 (15)0.0222 (14)0.0028 (16)
C130.079 (2)0.108 (3)0.079 (2)0.0178 (19)0.0300 (17)0.0034 (19)
C140.105 (3)0.081 (2)0.0625 (17)0.0037 (19)0.0325 (17)0.0002 (15)
C150.088 (2)0.104 (3)0.0666 (18)0.024 (2)0.0245 (16)0.0170 (18)
C160.0625 (18)0.104 (2)0.0751 (18)0.0105 (16)0.0242 (15)0.0160 (18)
C170.166 (4)0.101 (3)0.100 (3)0.005 (3)0.045 (3)0.019 (2)
C180.0488 (13)0.0755 (17)0.0596 (14)0.0095 (13)0.0180 (11)0.0017 (13)
C190.0564 (17)0.129 (3)0.088 (2)0.0212 (18)0.0099 (15)0.040 (2)
C200.058 (2)0.138 (3)0.129 (3)0.033 (2)0.004 (2)0.050 (3)
C210.0510 (17)0.106 (2)0.103 (2)0.0149 (17)0.0004 (16)0.023 (2)
C220.0636 (18)0.094 (2)0.087 (2)0.0016 (17)0.0094 (15)0.0262 (18)
C230.0555 (16)0.0711 (17)0.0829 (18)0.0065 (13)0.0216 (14)0.0151 (15)
C240.066 (2)0.179 (4)0.170 (4)0.029 (3)0.025 (3)0.057 (4)
C250.0494 (14)0.0791 (18)0.0608 (14)0.0130 (13)0.0162 (11)0.0054 (14)
C260.0742 (19)0.090 (2)0.0668 (17)0.0145 (17)0.0153 (14)0.0076 (17)
C270.104 (3)0.109 (3)0.0708 (19)0.017 (2)0.0100 (18)0.024 (2)
C280.107 (3)0.087 (2)0.101 (3)0.015 (2)0.025 (2)0.024 (2)
C290.111 (3)0.077 (2)0.099 (3)0.013 (2)0.031 (2)0.006 (2)
C300.087 (2)0.083 (2)0.0723 (18)0.0155 (17)0.0220 (16)0.0032 (17)
C310.200 (5)0.105 (3)0.150 (4)0.002 (3)0.033 (4)0.050 (3)
Geometric parameters (Å, º) top
Ge1—C251.940 (3)C15—C161.386 (4)
Ge1—C181.946 (3)C15—H150.9601
Ge1—C111.948 (3)C16—H160.9600
Ge1—C31.984 (2)C17—H17A0.9600
O1—C11.228 (3)C17—H17B0.9599
O2—C11.276 (3)C17—H17C0.9601
O2—H20.8200C18—C231.381 (4)
C1—C21.493 (4)C18—C191.381 (4)
C2—C31.530 (4)C19—C201.382 (4)
C2—H2A0.9600C19—H190.9599
C2—H2B0.9600C20—C211.357 (5)
C3—C41.507 (4)C20—H200.9600
C3—H30.9600C21—C221.373 (5)
C4—C51.394 (4)C21—C241.517 (5)
C4—C91.400 (4)C22—C231.383 (4)
C5—C61.391 (5)C22—H220.9599
C5—H50.9600C23—H230.9601
C6—C71.361 (7)C24—H24A0.9599
C6—H60.9601C24—H24B0.9601
C7—C81.345 (7)C24—H24C0.9601
C7—H70.9600C25—C261.384 (4)
C8—C91.402 (6)C25—C301.387 (4)
C8—H80.9601C26—C271.393 (5)
C9—C101.499 (5)C26—H260.9600
C10—H10A0.9600C27—C281.358 (5)
C10—H10B0.9601C27—H270.9600
C10—H10C0.9600C28—C291.371 (5)
C11—C121.381 (4)C28—C311.520 (5)
C11—C161.393 (4)C29—C301.383 (5)
C12—C131.386 (4)C29—H290.9600
C12—H120.9600C30—H300.9601
C13—C141.374 (5)C31—H31A0.9600
C13—H130.9600C31—H31B0.9601
C14—C151.370 (5)C31—H31C0.9600
C14—C171.520 (5)
C25—Ge1—C18108.93 (11)C14—C15—H15119.3
C25—Ge1—C11111.67 (11)C16—C15—H15119.5
C18—Ge1—C11108.26 (11)C15—C16—C11121.4 (3)
C25—Ge1—C3107.07 (11)C15—C16—H16118.1
C18—Ge1—C3115.63 (11)C11—C16—H16120.5
C11—Ge1—C3105.31 (11)C14—C17—H17A109.8
C1—O2—H2109.5C14—C17—H17B108.7
O1—C1—O2122.1 (3)H17A—C17—H17B109.5
O1—C1—C2121.2 (3)C14—C17—H17C109.9
O2—C1—C2116.6 (2)H17A—C17—H17C109.5
C1—C2—C3112.7 (2)H17B—C17—H17C109.5
C1—C2—H2A108.3C23—C18—C19116.6 (3)
C3—C2—H2A108.7C23—C18—Ge1124.1 (2)
C1—C2—H2B108.8C19—C18—Ge1119.1 (2)
C3—C2—H2B108.8C18—C19—C20121.1 (3)
H2A—C2—H2B109.5C18—C19—H19119.3
C4—C3—C2114.7 (2)C20—C19—H19119.6
C4—C3—Ge1111.04 (17)C21—C20—C19122.2 (3)
C2—C3—Ge1113.61 (17)C21—C20—H20116.5
C4—C3—H3108.6C19—C20—H20121.3
C2—C3—H3102.7C20—C21—C22117.3 (3)
Ge1—C3—H3105.2C20—C21—C24121.1 (3)
C5—C4—C9119.0 (3)C22—C21—C24121.6 (3)
C5—C4—C3119.8 (3)C21—C22—C23121.3 (3)
C9—C4—C3121.1 (3)C21—C22—H22118.8
C6—C5—C4121.2 (4)C23—C22—H22119.9
C6—C5—H5119.9C18—C23—C22121.5 (3)
C4—C5—H5118.8C18—C23—H23119.5
C7—C6—C5119.3 (4)C22—C23—H23118.9
C7—C6—H6119.6C21—C24—H24A109.5
C5—C6—H6121.1C21—C24—H24B109.2
C8—C7—C6120.1 (5)H24A—C24—H24B109.5
C8—C7—H7119.8C21—C24—H24C109.8
C6—C7—H7120.1H24A—C24—H24C109.5
C7—C8—C9123.1 (5)H24B—C24—H24C109.5
C7—C8—H8118.8C26—C25—C30116.7 (3)
C9—C8—H8118.1C26—C25—Ge1121.9 (2)
C4—C9—C8117.2 (4)C30—C25—Ge1121.3 (2)
C4—C9—C10122.9 (3)C25—C26—C27120.8 (3)
C8—C9—C10119.9 (4)C25—C26—H26119.2
C9—C10—H10A109.6C27—C26—H26120.0
C9—C10—H10B110.4C28—C27—C26121.9 (3)
H10A—C10—H10B109.5C28—C27—H27118.6
C9—C10—H10C108.3C26—C27—H27119.5
H10A—C10—H10C109.5C27—C28—C29117.9 (3)
H10B—C10—H10C109.5C27—C28—C31120.1 (4)
C12—C11—C16116.8 (3)C29—C28—C31122.0 (4)
C12—C11—Ge1121.0 (2)C28—C29—C30121.1 (3)
C16—C11—Ge1122.1 (2)C28—C29—H29119.3
C11—C12—C13121.1 (3)C30—C29—H29119.6
C11—C12—H12119.8C29—C30—C25121.7 (3)
C13—C12—H12119.1C29—C30—H30119.1
C14—C13—C12121.7 (3)C25—C30—H30119.2
C14—C13—H13118.8C28—C31—H31A108.6
C12—C13—H13119.5C28—C31—H31B110.2
C15—C14—C13117.7 (3)H31A—C31—H31B109.5
C15—C14—C17122.0 (4)C28—C31—H31C109.5
C13—C14—C17120.3 (4)H31A—C31—H31C109.5
C14—C15—C16121.2 (3)H31B—C31—H31C109.5
O1—C1—C2—C336.9 (4)C17—C14—C15—C16178.8 (3)
O2—C1—C2—C3145.4 (3)C14—C15—C16—C111.3 (5)
C1—C2—C3—C473.4 (3)C12—C11—C16—C151.9 (4)
C1—C2—C3—Ge1157.31 (19)Ge1—C11—C16—C15174.4 (2)
C25—Ge1—C3—C456.2 (2)C25—Ge1—C18—C23160.3 (2)
C18—Ge1—C3—C465.4 (2)C11—Ge1—C18—C2378.1 (3)
C11—Ge1—C3—C4175.13 (18)C3—Ge1—C18—C2339.7 (3)
C25—Ge1—C3—C2172.76 (18)C25—Ge1—C18—C1924.2 (3)
C18—Ge1—C3—C265.7 (2)C11—Ge1—C18—C1997.4 (3)
C11—Ge1—C3—C253.8 (2)C3—Ge1—C18—C19144.8 (3)
C2—C3—C4—C550.8 (3)C23—C18—C19—C201.9 (6)
Ge1—C3—C4—C579.7 (3)Ge1—C18—C19—C20173.9 (3)
C2—C3—C4—C9132.4 (3)C18—C19—C20—C212.9 (7)
Ge1—C3—C4—C997.1 (3)C19—C20—C21—C222.2 (7)
C9—C4—C5—C60.1 (5)C19—C20—C21—C24178.7 (5)
C3—C4—C5—C6177.0 (3)C20—C21—C22—C230.7 (7)
C4—C5—C6—C71.9 (6)C24—C21—C22—C23179.9 (4)
C5—C6—C7—C82.5 (8)C19—C18—C23—C220.5 (5)
C6—C7—C8—C91.3 (8)Ge1—C18—C23—C22175.1 (3)
C5—C4—C9—C81.1 (5)C21—C22—C23—C180.1 (6)
C3—C4—C9—C8175.8 (3)C18—Ge1—C25—C26133.1 (2)
C5—C4—C9—C10178.9 (3)C11—Ge1—C25—C2613.6 (3)
C3—C4—C9—C104.2 (5)C3—Ge1—C25—C26101.2 (2)
C7—C8—C9—C40.5 (6)C18—Ge1—C25—C3051.0 (3)
C7—C8—C9—C10179.5 (5)C11—Ge1—C25—C30170.5 (2)
C25—Ge1—C11—C12106.1 (2)C3—Ge1—C25—C3074.7 (3)
C18—Ge1—C11—C1213.8 (3)C30—C25—C26—C270.9 (5)
C3—Ge1—C11—C12138.0 (2)Ge1—C25—C26—C27175.2 (3)
C25—Ge1—C11—C1677.7 (3)C25—C26—C27—C280.1 (6)
C18—Ge1—C11—C16162.3 (2)C26—C27—C28—C291.2 (6)
C3—Ge1—C11—C1638.1 (3)C26—C27—C28—C31179.8 (4)
C16—C11—C12—C131.3 (4)C27—C28—C29—C301.7 (6)
Ge1—C11—C12—C13175.1 (2)C31—C28—C29—C30179.4 (4)
C11—C12—C13—C140.0 (5)C28—C29—C30—C250.9 (6)
C12—C13—C14—C150.6 (5)C26—C25—C30—C290.4 (5)
C12—C13—C14—C17178.2 (3)Ge1—C25—C30—C29175.7 (3)
C13—C14—C15—C160.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.832.637 (3)169
C3—H3···O10.962.412.849 (4)107
Symmetry code: (i) x, y, z+2.
(III) 3-(tribenzylgermyl)-3-(4-tolyl)propionic acid top
Crystal data top
[Ge(C7H7)3(C10H11O2)]F(000) = 1064
Mr = 509.16Dx = 1.308 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 16881 reflections
a = 10.476 (2) Åθ = 1.0–25.0°
b = 16.337 (3) ŵ = 1.21 mm1
c = 15.119 (5) ÅT = 123 K
β = 92.018 (8)°Prism, colourless
V = 2586.0 (11) Å30.12 × 0.10 × 0.10 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
4533 independent reflections
Radiation source: fine-focus sealed tube3586 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω and ϕ scansθmax = 25.0°, θmin = 3.5°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1212
Tmin = 0.769, Tmax = 0.886k = 1919
16881 measured reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.042P)2 + 1.7P]
where P = (Fo2 + 2Fc2)/3
4533 reflections(Δ/σ)max = 0.001
339 parametersΔρmax = 0.64 e Å3
2 restraintsΔρmin = 0.33 e Å3
Crystal data top
[Ge(C7H7)3(C10H11O2)]V = 2586.0 (11) Å3
Mr = 509.16Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.476 (2) ŵ = 1.21 mm1
b = 16.337 (3) ÅT = 123 K
c = 15.119 (5) Å0.12 × 0.10 × 0.10 mm
β = 92.018 (8)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
4533 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
3586 reflections with I > 2σ(I)
Tmin = 0.769, Tmax = 0.886Rint = 0.054
16881 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0372 restraints
wR(F2) = 0.094H-atom parameters constrained
S = 1.04Δρmax = 0.64 e Å3
4533 reflectionsΔρmin = 0.33 e Å3
339 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Ge10.22676 (3)0.183568 (18)0.818794 (17)0.03043 (11)
O10.0586 (2)0.01191 (15)0.59993 (13)0.0490 (6)
O20.0365 (2)0.10915 (14)0.49876 (14)0.0497 (6)
H20.00220.07090.46940.075*
C10.0691 (3)0.08333 (19)0.57577 (19)0.0359 (7)
C20.1186 (3)0.14847 (19)0.64045 (19)0.0400 (7)
H2A0.16020.19250.60680.048*
H2B0.04520.17300.67040.048*
C30.2132 (2)0.11599 (18)0.71010 (17)0.0328 (6)
H30.17670.06260.72940.039*
C40.3410 (2)0.09469 (17)0.67203 (16)0.0296 (6)
C50.3876 (3)0.01564 (18)0.67800 (18)0.0373 (7)
H50.33960.02490.70730.045*
C60.5033 (3)0.00578 (19)0.64199 (19)0.0423 (7)
H60.53220.06080.64650.051*
C70.5768 (3)0.0512 (2)0.59986 (18)0.0390 (7)
C80.5321 (3)0.1310 (2)0.59508 (19)0.0404 (7)
H80.58180.17170.56740.048*
C90.4154 (3)0.15268 (18)0.63023 (18)0.0342 (6)
H90.38640.20770.62560.041*
C100.7025 (3)0.0271 (3)0.5605 (2)0.0602 (10)
H10A0.74090.07510.53310.072*
H10B0.68730.01540.51560.072*
H10C0.76060.00600.60740.072*
C110.2007 (3)0.30143 (18)0.7963 (2)0.0400 (7)
H11A0.11170.30980.77400.048*
H11B0.21090.33100.85330.048*
C120.2891 (3)0.33909 (17)0.73165 (19)0.0381 (7)
C130.2479 (3)0.35592 (19)0.6448 (2)0.0479 (8)
H130.16180.34560.62620.058*
C140.3341 (5)0.3881 (2)0.5852 (2)0.0655 (11)
H140.30610.39960.52610.079*
C150.4583 (5)0.4032 (2)0.6112 (3)0.0735 (13)
H150.51650.42420.57010.088*
C160.4981 (4)0.3877 (2)0.6968 (3)0.0663 (11)
H160.58400.39900.71510.080*
C170.4154 (3)0.3561 (2)0.7569 (2)0.0495 (8)
H170.44480.34590.81600.059*
C180.3925 (3)0.1615 (2)0.87966 (17)0.0433 (8)
H18A0.43430.11450.85120.052*
H18B0.44870.20980.87460.052*
C190.3742 (15)0.1426 (7)0.9756 (3)0.030 (3)0.65 (4)
C200.3750 (10)0.2006 (6)1.0429 (6)0.040 (2)0.65 (4)
H200.38300.25711.02920.048*0.65 (4)
C210.3641 (9)0.1760 (11)1.1303 (4)0.060 (4)0.65 (4)
H210.36470.21571.17630.072*0.65 (4)
C220.3524 (9)0.0934 (12)1.1505 (4)0.071 (4)0.65 (4)
H220.34490.07661.21020.085*0.65 (4)
C230.3516 (11)0.0354 (8)1.0832 (9)0.073 (3)0.65 (4)
H230.34360.02111.09690.087*0.65 (4)
C240.3624 (15)0.0600 (6)0.9958 (8)0.049 (2)0.65 (4)
H240.36190.02040.94980.058*0.65 (4)
C19'0.395 (3)0.1424 (15)0.9769 (4)0.035 (5)0.35 (4)
C20'0.386 (3)0.2143 (14)1.0255 (16)0.075 (7)0.35 (4)
H20'0.39580.26570.99730.090*0.35 (4)
C21'0.363 (2)0.211 (2)1.1153 (16)0.095 (8)0.35 (4)
H21'0.35640.25991.14850.114*0.35 (4)
C22'0.3485 (16)0.135 (3)1.1566 (6)0.072 (9)0.35 (4)
H22'0.33250.13311.21800.086*0.35 (4)
C23'0.358 (2)0.064 (2)1.1080 (14)0.074 (7)0.35 (4)
H23'0.34810.01221.13620.089*0.35 (4)
C24'0.381 (2)0.0671 (13)1.0182 (14)0.049 (5)0.35 (4)
H24'0.38750.01800.98500.059*0.35 (4)
C250.0925 (2)0.1486 (2)0.89873 (18)0.0373 (7)
H25A0.09760.08840.90590.045*
H25B0.11010.17350.95760.045*
C260.0411 (3)0.17073 (17)0.86840 (18)0.0338 (7)
C270.0977 (3)0.2432 (2)0.8926 (2)0.0494 (8)
H270.05260.28060.93020.059*
C280.2245 (3)0.2619 (2)0.8608 (3)0.0606 (10)
H280.26480.31110.87830.073*
C290.2879 (3)0.2082 (3)0.8047 (3)0.0641 (11)
H290.37130.22120.78240.077*
C300.2325 (3)0.1370 (3)0.7811 (3)0.0617 (10)
H300.27730.10020.74260.074*
C310.1115 (3)0.1178 (2)0.8128 (2)0.0487 (8)
H310.07480.06710.79640.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ge10.02815 (16)0.03580 (19)0.02762 (16)0.00188 (13)0.00492 (11)0.00239 (13)
O10.0562 (14)0.0572 (16)0.0332 (11)0.0055 (11)0.0044 (10)0.0032 (10)
O20.0608 (14)0.0464 (14)0.0417 (12)0.0093 (11)0.0033 (11)0.0045 (10)
C10.0284 (14)0.0372 (18)0.0422 (17)0.0010 (13)0.0036 (12)0.0006 (14)
C20.0378 (16)0.0416 (18)0.0406 (16)0.0022 (14)0.0014 (13)0.0053 (14)
C30.0304 (14)0.0333 (16)0.0349 (14)0.0019 (12)0.0034 (12)0.0029 (12)
C40.0292 (14)0.0330 (16)0.0265 (13)0.0005 (12)0.0003 (11)0.0040 (12)
C50.0414 (16)0.0322 (17)0.0388 (15)0.0014 (13)0.0057 (13)0.0009 (13)
C60.0478 (18)0.0355 (18)0.0435 (17)0.0109 (14)0.0009 (14)0.0034 (14)
C70.0315 (15)0.052 (2)0.0336 (15)0.0112 (14)0.0013 (12)0.0028 (14)
C80.0352 (16)0.0461 (19)0.0403 (16)0.0002 (14)0.0085 (13)0.0067 (14)
C90.0343 (15)0.0296 (15)0.0388 (15)0.0011 (12)0.0037 (12)0.0003 (13)
C100.0416 (18)0.084 (3)0.055 (2)0.0197 (19)0.0090 (16)0.008 (2)
C110.0395 (16)0.0388 (18)0.0423 (16)0.0007 (13)0.0119 (13)0.0077 (13)
C120.0478 (18)0.0239 (16)0.0439 (17)0.0013 (13)0.0191 (14)0.0084 (13)
C130.066 (2)0.0293 (17)0.0494 (18)0.0055 (16)0.0104 (16)0.0032 (15)
C140.117 (4)0.032 (2)0.049 (2)0.013 (2)0.030 (2)0.0002 (16)
C150.098 (3)0.036 (2)0.090 (3)0.003 (2)0.064 (3)0.000 (2)
C160.057 (2)0.040 (2)0.105 (3)0.0070 (17)0.035 (2)0.001 (2)
C170.0508 (19)0.0367 (18)0.062 (2)0.0052 (16)0.0129 (16)0.0056 (16)
C180.0310 (15)0.061 (2)0.0377 (16)0.0021 (14)0.0051 (13)0.0026 (15)
C190.012 (5)0.049 (6)0.030 (4)0.004 (4)0.003 (2)0.000 (4)
C200.030 (3)0.061 (5)0.030 (4)0.012 (3)0.002 (3)0.011 (3)
C210.034 (4)0.121 (9)0.026 (4)0.022 (5)0.009 (3)0.004 (5)
C220.038 (5)0.124 (13)0.051 (6)0.007 (6)0.015 (4)0.026 (6)
C230.048 (5)0.077 (6)0.092 (7)0.002 (5)0.006 (5)0.046 (6)
C240.034 (5)0.057 (5)0.054 (4)0.004 (4)0.012 (5)0.015 (3)
C19'0.008 (7)0.046 (11)0.050 (10)0.010 (6)0.009 (5)0.002 (8)
C20'0.074 (13)0.108 (16)0.044 (9)0.013 (11)0.021 (8)0.011 (9)
C21'0.068 (12)0.16 (2)0.054 (11)0.028 (14)0.014 (9)0.025 (12)
C22'0.032 (7)0.14 (3)0.047 (9)0.007 (11)0.023 (6)0.044 (9)
C23'0.042 (9)0.103 (16)0.077 (13)0.016 (10)0.014 (9)0.044 (14)
C24'0.029 (8)0.063 (9)0.053 (8)0.011 (6)0.024 (7)0.012 (8)
C250.0315 (15)0.0494 (19)0.0311 (14)0.0002 (14)0.0037 (12)0.0008 (14)
C260.0298 (14)0.0389 (18)0.0332 (14)0.0041 (13)0.0078 (12)0.0049 (13)
C270.0504 (19)0.049 (2)0.0505 (19)0.0013 (16)0.0210 (16)0.0020 (16)
C280.057 (2)0.059 (2)0.068 (2)0.0213 (19)0.0191 (19)0.010 (2)
C290.0323 (18)0.085 (3)0.076 (3)0.0044 (19)0.0077 (18)0.012 (2)
C300.044 (2)0.069 (3)0.071 (2)0.0188 (19)0.0096 (18)0.010 (2)
C310.0448 (18)0.046 (2)0.0544 (19)0.0119 (15)0.0036 (15)0.0036 (16)
Geometric parameters (Å, º) top
Ge1—C181.970 (3)C18—C191.502 (4)
Ge1—C251.971 (3)C18—C19'1.502 (5)
Ge1—C111.973 (3)C18—H18A0.9900
Ge1—C31.981 (3)C18—H18B0.9900
O1—C11.229 (4)C19—C201.3900
O2—C11.274 (3)C19—C241.3900
O2—H20.8400C20—C211.3900
C1—C21.524 (4)C20—H200.9500
C2—C31.516 (4)C21—C221.3900
C2—H2A0.9900C21—H210.9500
C2—H2B0.9900C22—C231.3900
C3—C41.516 (4)C22—H220.9500
C3—H31.0000C23—C241.3900
C4—C51.383 (4)C23—H230.9500
C4—C91.393 (4)C24—H240.9500
C5—C61.391 (4)C19'—C20'1.3900
C5—H50.9500C19'—C24'1.3900
C6—C71.378 (4)C20'—C21'1.3900
C6—H60.9500C20'—H20'0.9500
C7—C81.388 (4)C21'—C22'1.4000
C7—C101.515 (4)C21'—H21'0.9500
C8—C91.396 (4)C22'—C23'1.3796
C8—H80.9500C22'—H22'0.9500
C9—H90.9500C23'—C24'1.3900
C10—H10A0.9800C23'—H23'0.9500
C10—H10B0.9800C24'—H24'0.9500
C10—H10C0.9800C25—C261.502 (4)
C11—C121.502 (4)C25—H25A0.9900
C11—H11A0.9900C25—H25B0.9900
C11—H11B0.9900C26—C271.380 (4)
C12—C171.392 (4)C26—C311.398 (4)
C12—C131.395 (4)C27—C281.430 (5)
C13—C141.401 (5)C27—H270.9500
C13—H130.9500C28—C291.374 (5)
C14—C151.368 (6)C28—H280.9500
C14—H140.9500C29—C301.353 (6)
C15—C161.370 (6)C29—H290.9500
C15—H150.9500C30—C311.375 (5)
C16—C171.377 (5)C30—H300.9500
C16—H160.9500C31—H310.9500
C17—H170.9500
C18—Ge1—C25107.26 (11)C19—C18—C19'8.5 (15)
C18—Ge1—C11111.93 (14)C19—C18—Ge1110.4 (6)
C25—Ge1—C11106.94 (13)C19'—C18—Ge1118.8 (11)
C18—Ge1—C3108.79 (12)C19—C18—H18A109.6
C25—Ge1—C3108.38 (12)C19'—C18—H18A105.7
C11—Ge1—C3113.30 (12)Ge1—C18—H18A109.6
C1—O2—H2109.5C19—C18—H18B109.6
O1—C1—O2124.2 (3)C19'—C18—H18B104.5
O1—C1—C2120.3 (3)Ge1—C18—H18B109.6
O2—C1—C2115.4 (3)H18A—C18—H18B108.1
C3—C2—C1113.6 (3)C20—C19—C24120.0
C3—C2—H2A108.8C20—C19—C18124.7 (8)
C1—C2—H2A108.8C24—C19—C18115.2 (8)
C3—C2—H2B108.8C21—C20—C19120.0
C1—C2—H2B108.8C21—C20—H20120.0
H2A—C2—H2B107.7C19—C20—H20120.0
C2—C3—C4112.4 (2)C20—C21—C22120.0
C2—C3—Ge1114.04 (19)C20—C21—H21120.0
C4—C3—Ge1113.84 (17)C22—C21—H21120.0
C2—C3—H3105.2C23—C22—C21120.0
C4—C3—H3105.2C23—C22—H22120.0
Ge1—C3—H3105.2C21—C22—H22120.0
C5—C4—C9117.6 (2)C24—C23—C22120.0
C5—C4—C3120.3 (2)C24—C23—H23120.0
C9—C4—C3122.1 (3)C22—C23—H23120.0
C4—C5—C6121.3 (3)C23—C24—C19120.0
C4—C5—H5119.3C23—C24—H24120.0
C6—C5—H5119.3C19—C24—H24120.0
C7—C6—C5121.3 (3)C20'—C19'—C24'120.0
C7—C6—H6119.3C20'—C19'—C18110.0 (17)
C5—C6—H6119.3C24'—C19'—C18128.6 (16)
C6—C7—C8117.7 (3)C21'—C20'—C19'120.0
C6—C7—C10120.9 (3)C21'—C20'—H20'120.0
C8—C7—C10121.3 (3)C19'—C20'—H20'120.0
C7—C8—C9121.1 (3)C20'—C21'—C22'120.0
C7—C8—H8119.4C20'—C21'—H21'120.0
C9—C8—H8119.4C22'—C21'—H21'120.0
C4—C9—C8120.8 (3)C21'—C22'—C23'120.0
C4—C9—H9119.6C21'—C22'—H22'120.0
C8—C9—H9119.6C23'—C22'—H22'120.0
C7—C10—H10A109.5C22'—C23'—C24'120.0
C7—C10—H10B109.5C22'—C23'—H23'120.0
H10A—C10—H10B109.5C24'—C23'—H23'120.0
C7—C10—H10C109.5C23'—C24'—C19'120.0
H10A—C10—H10C109.5C23'—C24'—H24'120.0
H10B—C10—H10C109.5C19'—C24'—H24'120.0
C12—C11—Ge1115.31 (19)C26—C25—Ge1114.86 (19)
C12—C11—H11A108.4C26—C25—H25A108.6
Ge1—C11—H11A108.4Ge1—C25—H25A108.6
C12—C11—H11B108.4C26—C25—H25B108.6
Ge1—C11—H11B108.4Ge1—C25—H25B108.6
H11A—C11—H11B107.5H25A—C25—H25B107.5
C17—C12—C13118.6 (3)C27—C26—C31117.8 (3)
C17—C12—C11120.4 (3)C27—C26—C25122.1 (3)
C13—C12—C11121.0 (3)C31—C26—C25120.1 (3)
C12—C13—C14119.6 (3)C26—C27—C28119.8 (3)
C12—C13—H13120.2C26—C27—H27120.1
C14—C13—H13120.2C28—C27—H27120.1
C15—C14—C13120.8 (4)C29—C28—C27119.6 (3)
C15—C14—H14119.6C29—C28—H28120.2
C13—C14—H14119.6C27—C28—H28120.2
C14—C15—C16119.5 (3)C30—C29—C28120.6 (3)
C14—C15—H15120.2C30—C29—H29119.7
C16—C15—H15120.2C28—C29—H29119.7
C15—C16—C17121.0 (4)C29—C30—C31120.1 (4)
C15—C16—H16119.5C29—C30—H30119.9
C17—C16—H16119.5C31—C30—H30119.9
C16—C17—C12120.6 (4)C30—C31—C26122.0 (3)
C16—C17—H17119.7C30—C31—H31119.0
C12—C17—H17119.7C26—C31—H31119.0
O1—C1—C2—C331.0 (4)C25—Ge1—C18—C19'13.5 (11)
O2—C1—C2—C3151.4 (3)C11—Ge1—C18—C19'103.5 (11)
C1—C2—C3—C471.3 (3)C3—Ge1—C18—C19'130.6 (11)
C1—C2—C3—Ge1157.19 (19)C19'—C18—C19—C2085 (9)
C18—Ge1—C3—C2157.9 (2)Ge1—C18—C19—C2090.1 (10)
C25—Ge1—C3—C285.8 (2)C19'—C18—C19—C2492 (9)
C11—Ge1—C3—C232.7 (2)Ge1—C18—C19—C2493.3 (6)
C18—Ge1—C3—C427.2 (2)C24—C19—C20—C210.0
C25—Ge1—C3—C4143.5 (2)C18—C19—C20—C21176.4 (12)
C11—Ge1—C3—C498.0 (2)C19—C20—C21—C220.0
C2—C3—C4—C5120.1 (3)C20—C21—C22—C230.0
Ge1—C3—C4—C5108.3 (3)C21—C22—C23—C240.0
C2—C3—C4—C959.8 (3)C22—C23—C24—C190.0
Ge1—C3—C4—C971.7 (3)C20—C19—C24—C230.0
C9—C4—C5—C61.3 (4)C18—C19—C24—C23176.8 (11)
C3—C4—C5—C6178.7 (3)C19—C18—C19'—C20'85 (9)
C4—C5—C6—C70.8 (4)Ge1—C18—C19'—C20'79.5 (13)
C5—C6—C7—C80.5 (4)C19—C18—C19'—C24'82 (9)
C5—C6—C7—C10179.7 (3)Ge1—C18—C19'—C24'87.0 (18)
C6—C7—C8—C91.2 (4)C24'—C19'—C20'—C21'0.0
C10—C7—C8—C9179.0 (3)C18—C19'—C20'—C21'167.9 (19)
C5—C4—C9—C80.6 (4)C19'—C20'—C21'—C22'0.0
C3—C4—C9—C8179.4 (2)C20'—C21'—C22'—C23'0.0
C7—C8—C9—C40.7 (4)C21'—C22'—C23'—C24'0.0
C18—Ge1—C11—C1266.5 (3)C22'—C23'—C24'—C19'0.0
C25—Ge1—C11—C12176.3 (2)C20'—C19'—C24'—C23'0.0
C3—Ge1—C11—C1256.9 (3)C18—C19'—C24'—C23'165 (2)
Ge1—C11—C12—C1775.7 (3)C18—Ge1—C25—C26172.4 (2)
Ge1—C11—C12—C13102.7 (3)C11—Ge1—C25—C2652.2 (3)
C17—C12—C13—C141.0 (4)C3—Ge1—C25—C2670.3 (2)
C11—C12—C13—C14177.5 (3)Ge1—C25—C26—C2791.0 (3)
C12—C13—C14—C150.0 (5)Ge1—C25—C26—C3188.0 (3)
C13—C14—C15—C160.9 (5)C31—C26—C27—C280.0 (4)
C14—C15—C16—C170.9 (6)C25—C26—C27—C28179.1 (3)
C15—C16—C17—C120.1 (5)C26—C27—C28—C291.5 (5)
C13—C12—C17—C161.0 (5)C27—C28—C29—C301.6 (5)
C11—C12—C17—C16177.5 (3)C28—C29—C30—C310.3 (6)
C25—Ge1—C18—C1912.7 (5)C29—C30—C31—C261.2 (5)
C11—Ge1—C18—C19104.3 (5)C27—C26—C31—C301.3 (4)
C3—Ge1—C18—C19129.7 (5)C25—C26—C31—C30177.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.841.812.651 (3)175
C3—H3···O11.002.422.845 (4)105
Symmetry code: (i) x, y, z+1.

Experimental details

(I)(II)(III)
Crystal data
Chemical formula[Ge(C6H5)3(C9H8FO2)][Ge(C7H7)3(C10H11O2)][Ge(C7H7)3(C10H11O2)]
Mr471.04509.16509.16
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/cMonoclinic, P21/n
Temperature (K)170293123
a, b, c (Å)9.7278 (10), 17.907 (3), 13.541 (2)10.984 (3), 13.710 (4), 20.245 (5)10.476 (2), 16.337 (3), 15.119 (5)
β (°) 110.907 (8) 113.857 (14) 92.018 (8)
V3)2203.5 (6)2788.3 (13)2586.0 (11)
Z444
Radiation typeMo KαMo KαMo Kα
µ (mm1)1.421.121.21
Crystal size (mm)0.20 × 0.15 × 0.140.20 × 0.17 × 0.130.12 × 0.10 × 0.10
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Multi-scan
(SORTAV; Blessing, 1997)
Multi-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.711, 0.8200.749, 0.8640.769, 0.886
No. of measured, independent and
observed [I > 2σ(I)] reflections
9816, 5026, 4338 10731, 6346, 4185 16881, 4533, 3586
Rint0.0170.0250.054
(sin θ/λ)max1)0.6500.6500.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.070, 1.03 0.043, 0.115, 1.01 0.037, 0.094, 1.04
No. of reflections502663464533
No. of parameters281308339
No. of restraints002
H-atom treatmentH-atom parameters constrainedH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.30, 0.440.38, 0.420.64, 0.33

Computer programs: COLLECT (Nonius, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) for (I) top
Ge1—C111.951 (2)F1—C91.367 (2)
Ge1—C251.953 (2)O1—C11.217 (2)
Ge1—C181.959 (2)O2—C11.316 (2)
Ge1—C31.997 (2)
C11—Ge1—C25110.55 (7)C11—Ge1—C3106.08 (6)
C11—Ge1—C18110.60 (6)C25—Ge1—C3112.29 (7)
C25—Ge1—C18108.93 (7)C18—Ge1—C3108.35 (6)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.841.832.6689 (16)178
C8—H8···O1ii0.952.573.323 (2)137
C3—H3···F11.002.342.805 (2)108
Symmetry codes: (i) x+2, y, z+1; (ii) x+1, y, z+1.
Selected geometric parameters (Å, º) for (II) top
Ge1—C251.940 (3)Ge1—C31.984 (2)
Ge1—C181.946 (3)O1—C11.228 (3)
Ge1—C111.948 (3)O2—C11.276 (3)
C25—Ge1—C18108.93 (11)C25—Ge1—C3107.07 (11)
C25—Ge1—C11111.67 (11)C18—Ge1—C3115.63 (11)
C18—Ge1—C11108.26 (11)C11—Ge1—C3105.31 (11)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.821.832.637 (3)169
C3—H3···O10.962.412.849 (4)107
Symmetry code: (i) x, y, z+2.
Selected geometric parameters (Å, º) for (III) top
Ge1—C181.970 (3)Ge1—C31.981 (3)
Ge1—C251.971 (3)O1—C11.229 (4)
Ge1—C111.973 (3)O2—C11.274 (3)
C18—Ge1—C25107.26 (11)C18—Ge1—C3108.79 (12)
C18—Ge1—C11111.93 (14)C25—Ge1—C3108.38 (12)
C25—Ge1—C11106.94 (13)C11—Ge1—C3113.30 (12)
Hydrogen-bond geometry (Å, º) for (III) top
D—H···AD—HH···AD···AD—H···A
O2—H2···O1i0.841.812.651 (3)175
C3—H3···O11.002.422.845 (4)105
Symmetry code: (i) x, y, z+1.
 

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