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metal-organic compounds
In the hexacoordinated title germanium compound [alternatively called (butanoato-κ2C3,O)bis(8-quinolato-κ2N,O)germanium(IV)], [Ge(C9H7NO)2(C4H6O2)], the Ge atom adopts a slightly distorted octahedral geometry, where the Ge—N coordinate covalent bonds [mean 2.079 (8) Å] are significantly longer than the Ge—O [mean 1.904 (8) Å] and Ge—C [1.976 (3) Å] covalent bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001455/lh6346sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001455/lh6346Isup2.hkl |
CCDC reference: 249963
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.040
- wR factor = 0.107
- Data-to-parameter ratio = 17.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.72 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
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.
Crystal data top
[Ge(C9H7NO)2(C4H6O2)] | Dx = 1.507 Mg m−3 |
Mr = 446.97 | Melting point: 538-540 K (decomp.) K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 8481 reflections |
a = 9.695 (2) Å | θ = 3.0–27.5° |
b = 17.266 (4) Å | µ = 1.59 mm−1 |
c = 23.543 (4) Å | T = 173 K |
V = 3941.0 (14) Å3 | Prism, yellow |
Z = 8 | 0.14 × 0.12 × 0.10 mm |
F(000) = 1824 |
Data collection top
Nonius KappaCCD area-detector diffractometer | 4504 independent reflections |
Radiation source: fine-focus sealed tube | 3256 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω and φ scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | h = −12→12 |
Tmin = 0.809, Tmax = 0.858 | k = −22→22 |
8481 measured reflections | l = −30→30 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.107 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0471P)2 + 4.162P] where P = (Fo2 + 2Fc2)/3 |
4504 reflections | (Δ/σ)max = 0.001 |
263 parameters | Δρmax = 0.96 e Å−3 |
0 restraints | Δρmin = −0.84 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ge1 | 0.58191 (3) | 0.074891 (17) | 0.617519 (12) | 0.02929 (11) | |
O1 | 0.4988 (2) | 0.16969 (11) | 0.64242 (8) | 0.0321 (4) | |
O2 | 0.3078 (2) | 0.23837 (13) | 0.63178 (9) | 0.0418 (5) | |
O3 | 0.6515 (2) | 0.11923 (11) | 0.54949 (8) | 0.0308 (4) | |
O4 | 0.5583 (2) | 0.02909 (13) | 0.69016 (9) | 0.0409 (5) | |
N1 | 0.7599 (2) | 0.12613 (13) | 0.65037 (9) | 0.0273 (5) | |
N2 | 0.7057 (3) | −0.02130 (14) | 0.60480 (11) | 0.0347 (6) | |
C1 | 0.3701 (3) | 0.17768 (18) | 0.62647 (12) | 0.0315 (6) | |
C2 | 0.3056 (4) | 0.1050 (2) | 0.6026 (2) | 0.0609 (11) | |
H2A | 0.2461 | 0.0818 | 0.6322 | 0.073* | |
H2B | 0.2454 | 0.1198 | 0.5704 | 0.073* | |
C3 | 0.4053 (3) | 0.04405 (18) | 0.58229 (14) | 0.0390 (7) | |
H3 | 0.4161 | 0.0517 | 0.5404 | 0.047* | |
C4 | 0.3610 (5) | −0.0375 (2) | 0.5907 (2) | 0.0711 (12) | |
H4A | 0.2715 | −0.0457 | 0.5724 | 0.085* | |
H4B | 0.3528 | −0.0483 | 0.6315 | 0.085* | |
H4C | 0.4295 | −0.0724 | 0.5739 | 0.085* | |
C5 | 0.8120 (3) | 0.12527 (18) | 0.70226 (12) | 0.0360 (7) | |
H5 | 0.7670 | 0.0959 | 0.7309 | 0.043* | |
C6 | 0.9310 (3) | 0.1662 (2) | 0.71616 (13) | 0.0418 (8) | |
H6 | 0.9670 | 0.1638 | 0.7537 | 0.050* | |
C7 | 0.9955 (3) | 0.2096 (2) | 0.67585 (13) | 0.0401 (7) | |
H7 | 1.0763 | 0.2379 | 0.6854 | 0.048* | |
C8 | 0.9431 (3) | 0.21278 (17) | 0.61977 (12) | 0.0321 (6) | |
C9 | 0.9994 (3) | 0.25552 (19) | 0.57457 (13) | 0.0385 (7) | |
H9 | 1.0785 | 0.2870 | 0.5805 | 0.046* | |
C10 | 0.9398 (3) | 0.2516 (2) | 0.52203 (13) | 0.0400 (7) | |
H10 | 0.9789 | 0.2806 | 0.4918 | 0.048* | |
C11 | 0.8221 (3) | 0.20570 (17) | 0.51128 (12) | 0.0338 (7) | |
H11 | 0.7839 | 0.2037 | 0.4742 | 0.041* | |
C12 | 0.7632 (3) | 0.16404 (15) | 0.55447 (11) | 0.0280 (6) | |
C13 | 0.8240 (3) | 0.16815 (16) | 0.60915 (11) | 0.0262 (6) | |
C14 | 0.7795 (3) | −0.04096 (19) | 0.55989 (14) | 0.0420 (8) | |
H14 | 0.7742 | −0.0104 | 0.5264 | 0.050* | |
C15 | 0.8657 (4) | −0.1063 (2) | 0.56091 (16) | 0.0512 (9) | |
H15 | 0.9169 | −0.1204 | 0.5281 | 0.061* | |
C16 | 0.8758 (4) | −0.1494 (2) | 0.60915 (17) | 0.0529 (10) | |
H16 | 0.9360 | −0.1927 | 0.6101 | 0.063* | |
C17 | 0.7980 (3) | −0.13044 (18) | 0.65750 (15) | 0.0444 (8) | |
C18 | 0.7985 (4) | −0.1704 (2) | 0.70970 (19) | 0.0589 (10) | |
H18 | 0.8551 | −0.2148 | 0.7146 | 0.071* | |
C19 | 0.7175 (4) | −0.1450 (2) | 0.75287 (18) | 0.0591 (11) | |
H19 | 0.7174 | −0.1733 | 0.7875 | 0.071* | |
C20 | 0.6329 (4) | −0.0778 (2) | 0.74871 (16) | 0.0530 (9) | |
H20 | 0.5782 | −0.0617 | 0.7800 | 0.064* | |
C21 | 0.6313 (3) | −0.03654 (18) | 0.69845 (14) | 0.0410 (8) | |
C22 | 0.7125 (3) | −0.06371 (16) | 0.65323 (14) | 0.0362 (7) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ge1 | 0.02843 (16) | 0.02435 (16) | 0.03510 (18) | 0.00087 (12) | −0.00095 (13) | 0.00114 (12) |
O1 | 0.0294 (10) | 0.0305 (10) | 0.0364 (10) | 0.0024 (8) | −0.0030 (9) | −0.0034 (9) |
O2 | 0.0340 (11) | 0.0408 (13) | 0.0507 (13) | 0.0104 (10) | −0.0040 (10) | −0.0100 (10) |
O3 | 0.0322 (10) | 0.0303 (10) | 0.0299 (10) | −0.0013 (9) | −0.0066 (9) | 0.0005 (8) |
O4 | 0.0436 (13) | 0.0380 (12) | 0.0411 (12) | 0.0002 (10) | 0.0094 (10) | 0.0089 (9) |
N1 | 0.0276 (11) | 0.0278 (12) | 0.0265 (11) | 0.0034 (10) | −0.0022 (10) | −0.0002 (9) |
N2 | 0.0344 (13) | 0.0247 (12) | 0.0450 (15) | 0.0016 (10) | −0.0038 (11) | 0.0004 (11) |
C1 | 0.0289 (14) | 0.0345 (16) | 0.0310 (15) | 0.0022 (12) | 0.0020 (12) | 0.0007 (12) |
C2 | 0.0345 (18) | 0.048 (2) | 0.100 (3) | 0.0051 (16) | −0.0173 (19) | −0.025 (2) |
C3 | 0.0334 (16) | 0.0342 (16) | 0.0496 (18) | −0.0050 (13) | −0.0035 (14) | −0.0073 (14) |
C4 | 0.065 (3) | 0.045 (2) | 0.104 (3) | −0.014 (2) | −0.025 (3) | 0.002 (2) |
C5 | 0.0369 (16) | 0.0427 (17) | 0.0286 (15) | 0.0046 (14) | −0.0022 (13) | 0.0029 (12) |
C6 | 0.0381 (17) | 0.058 (2) | 0.0289 (15) | 0.0037 (16) | −0.0082 (14) | −0.0047 (14) |
C7 | 0.0258 (15) | 0.053 (2) | 0.0410 (17) | −0.0016 (14) | −0.0058 (13) | −0.0092 (15) |
C8 | 0.0253 (14) | 0.0355 (16) | 0.0354 (15) | 0.0028 (12) | 0.0008 (12) | −0.0039 (13) |
C9 | 0.0279 (15) | 0.0428 (18) | 0.0449 (17) | −0.0040 (13) | 0.0044 (13) | 0.0013 (14) |
C10 | 0.0343 (16) | 0.0456 (19) | 0.0401 (17) | 0.0020 (14) | 0.0089 (14) | 0.0088 (14) |
C11 | 0.0364 (16) | 0.0386 (17) | 0.0265 (14) | 0.0084 (13) | 0.0003 (12) | 0.0050 (12) |
C12 | 0.0278 (14) | 0.0274 (14) | 0.0286 (13) | 0.0041 (12) | −0.0029 (11) | −0.0018 (11) |
C13 | 0.0236 (13) | 0.0258 (13) | 0.0291 (14) | 0.0041 (11) | 0.0007 (11) | −0.0004 (11) |
C14 | 0.0411 (18) | 0.0390 (17) | 0.0460 (18) | 0.0060 (14) | −0.0031 (15) | −0.0087 (14) |
C15 | 0.052 (2) | 0.046 (2) | 0.056 (2) | 0.0172 (17) | −0.0079 (18) | −0.0124 (17) |
C16 | 0.0471 (19) | 0.0318 (18) | 0.080 (3) | 0.0098 (15) | −0.0150 (19) | −0.0134 (17) |
C17 | 0.0428 (18) | 0.0273 (16) | 0.063 (2) | −0.0027 (13) | −0.0202 (16) | 0.0048 (15) |
C18 | 0.063 (2) | 0.0345 (19) | 0.079 (3) | −0.0022 (18) | −0.026 (2) | 0.0130 (19) |
C19 | 0.069 (3) | 0.0408 (19) | 0.067 (2) | −0.0110 (19) | −0.018 (2) | 0.0270 (19) |
C20 | 0.059 (2) | 0.046 (2) | 0.054 (2) | −0.0121 (18) | −0.0011 (18) | 0.0168 (17) |
C21 | 0.0422 (18) | 0.0312 (17) | 0.0497 (19) | −0.0083 (14) | −0.0040 (15) | 0.0130 (14) |
C22 | 0.0352 (16) | 0.0260 (15) | 0.0475 (18) | −0.0034 (12) | −0.0072 (14) | 0.0035 (13) |
Geometric parameters (Å, º) top
Ge1—O4 | 1.898 (2) | C7—C8 | 1.416 (4) |
Ge1—O3 | 1.899 (2) | C7—H7 | 0.9500 |
Ge1—O1 | 1.916 (2) | C8—C9 | 1.405 (4) |
Ge1—C3 | 1.976 (3) | C8—C13 | 1.410 (4) |
Ge1—N2 | 2.071 (2) | C9—C10 | 1.367 (4) |
Ge1—N1 | 2.087 (2) | C9—H9 | 0.9500 |
O1—C1 | 1.310 (3) | C10—C11 | 1.412 (4) |
O2—C1 | 1.216 (4) | C10—H10 | 0.9500 |
O3—C12 | 1.336 (3) | C11—C12 | 1.371 (4) |
O4—C21 | 1.350 (4) | C11—H11 | 0.9500 |
N1—C5 | 1.322 (4) | C12—C13 | 1.418 (4) |
N1—C13 | 1.362 (3) | C14—C15 | 1.404 (5) |
N2—C14 | 1.321 (4) | C14—H14 | 0.9500 |
N2—C22 | 1.357 (4) | C15—C16 | 1.361 (5) |
C1—C2 | 1.510 (5) | C15—H15 | 0.9500 |
C2—C3 | 1.507 (5) | C16—C17 | 1.404 (5) |
C2—H2A | 0.9900 | C16—H16 | 0.9500 |
C2—H2B | 0.9900 | C17—C18 | 1.409 (5) |
C3—C4 | 1.486 (5) | C17—C22 | 1.423 (4) |
C3—H3 | 1.0000 | C18—C19 | 1.358 (6) |
C4—H4A | 0.9800 | C18—H18 | 0.9500 |
C4—H4B | 0.9800 | C19—C20 | 1.424 (5) |
C4—H4C | 0.9800 | C19—H19 | 0.9500 |
C5—C6 | 1.391 (4) | C20—C21 | 1.382 (4) |
C5—H5 | 0.9500 | C20—H20 | 0.9500 |
C6—C7 | 1.362 (5) | C21—C22 | 1.405 (5) |
C6—H6 | 0.9500 | ||
O4—Ge1—O3 | 166.11 (9) | C5—C6—H6 | 120.1 |
O4—Ge1—O1 | 91.70 (9) | C6—C7—C8 | 120.4 (3) |
O3—Ge1—O1 | 93.61 (8) | C6—C7—H7 | 119.8 |
O4—Ge1—C3 | 99.29 (12) | C8—C7—H7 | 119.8 |
O3—Ge1—C3 | 93.58 (12) | C9—C8—C13 | 118.1 (3) |
O1—Ge1—C3 | 89.67 (11) | C9—C8—C7 | 126.0 (3) |
O4—Ge1—N2 | 82.30 (10) | C13—C8—C7 | 116.0 (3) |
O3—Ge1—N2 | 89.75 (9) | C10—C9—C8 | 119.7 (3) |
O1—Ge1—N2 | 166.66 (9) | C10—C9—H9 | 120.2 |
C3—Ge1—N2 | 103.02 (12) | C8—C9—H9 | 120.2 |
O4—Ge1—N1 | 86.69 (9) | C9—C10—C11 | 122.1 (3) |
O3—Ge1—N1 | 81.27 (8) | C9—C10—H10 | 118.9 |
O1—Ge1—N1 | 82.66 (8) | C11—C10—H10 | 118.9 |
C3—Ge1—N1 | 170.43 (11) | C12—C11—C10 | 119.9 (3) |
N2—Ge1—N1 | 85.10 (9) | C12—C11—H11 | 120.1 |
C1—O1—Ge1 | 113.8 (2) | C10—C11—H11 | 120.1 |
C12—O3—Ge1 | 116.6 (2) | O3—C12—C11 | 125.2 (2) |
C21—O4—Ge1 | 114.6 (2) | O3—C12—C13 | 116.5 (2) |
C5—N1—C13 | 119.3 (3) | C11—C12—C13 | 118.3 (3) |
C5—N1—Ge1 | 130.8 (2) | N1—C13—C8 | 122.6 (2) |
C13—N1—Ge1 | 109.8 (2) | N1—C13—C12 | 115.5 (2) |
C14—N2—C22 | 120.5 (3) | C8—C13—C12 | 121.9 (2) |
C14—N2—Ge1 | 129.5 (2) | N2—C14—C15 | 121.0 (3) |
C22—N2—Ge1 | 109.9 (2) | N2—C14—H14 | 119.5 |
O2—C1—O1 | 122.3 (3) | C15—C14—H14 | 119.5 |
O2—C1—C2 | 123.3 (3) | C16—C15—C14 | 119.7 (3) |
O1—C1—C2 | 114.4 (3) | C16—C15—H15 | 120.1 |
C3—C2—C1 | 115.6 (3) | C14—C15—H15 | 120.1 |
C3—C2—H2A | 108.4 | C15—C16—C17 | 120.7 (3) |
C1—C2—H2A | 108.4 | C15—C16—H16 | 119.6 |
C3—C2—H2B | 108.4 | C17—C16—H16 | 119.6 |
C1—C2—H2B | 108.4 | C16—C17—C18 | 126.2 (3) |
H2A—C2—H2B | 107.4 | C16—C17—C22 | 116.4 (3) |
C4—C3—C2 | 115.8 (3) | C18—C17—C22 | 117.4 (3) |
C4—C3—Ge1 | 116.7 (3) | C19—C18—C17 | 119.5 (3) |
C2—C3—Ge1 | 103.5 (2) | C19—C18—H18 | 120.3 |
C4—C3—H3 | 106.7 | C17—C18—H18 | 120.3 |
C2—C3—H3 | 106.7 | C18—C19—C20 | 123.1 (3) |
Ge1—C3—H3 | 106.7 | C18—C19—H19 | 118.5 |
C3—C4—H4A | 109.5 | C20—C19—H19 | 118.5 |
C3—C4—H4B | 109.5 | C21—C20—C19 | 119.0 (4) |
H4A—C4—H4B | 109.5 | C21—C20—H20 | 120.5 |
C3—C4—H4C | 109.5 | C19—C20—H20 | 120.5 |
H4A—C4—H4C | 109.5 | O4—C21—C20 | 124.3 (3) |
H4B—C4—H4C | 109.5 | O4—C21—C22 | 117.7 (3) |
N1—C5—C6 | 121.9 (3) | C20—C21—C22 | 118.1 (3) |
N1—C5—H5 | 119.0 | N2—C22—C21 | 115.4 (3) |
C6—C5—H5 | 119.0 | N2—C22—C17 | 121.7 (3) |
C7—C6—C5 | 119.8 (3) | C21—C22—C17 | 122.9 (3) |
C7—C6—H6 | 120.1 | ||
O4—Ge1—O1—C1 | −101.0 (2) | C5—C6—C7—C8 | −0.6 (5) |
O3—Ge1—O1—C1 | 91.81 (19) | C6—C7—C8—C9 | 179.6 (3) |
C3—Ge1—O1—C1 | −1.8 (2) | C6—C7—C8—C13 | −0.9 (4) |
N2—Ge1—O1—C1 | −163.9 (4) | C13—C8—C9—C10 | −1.3 (4) |
N1—Ge1—O1—C1 | 172.5 (2) | C7—C8—C9—C10 | 178.2 (3) |
O4—Ge1—O3—C12 | −35.8 (5) | C8—C9—C10—C11 | 0.1 (5) |
O1—Ge1—O3—C12 | 76.48 (18) | C9—C10—C11—C12 | 0.7 (5) |
C3—Ge1—O3—C12 | 166.37 (19) | Ge1—O3—C12—C11 | −174.7 (2) |
N2—Ge1—O3—C12 | −90.60 (19) | Ge1—O3—C12—C13 | 5.2 (3) |
N1—Ge1—O3—C12 | −5.52 (18) | C10—C11—C12—O3 | 179.5 (3) |
O3—Ge1—O4—C21 | −53.3 (5) | C10—C11—C12—C13 | −0.4 (4) |
O1—Ge1—O4—C21 | −165.8 (2) | C5—N1—C13—C8 | −1.6 (4) |
C3—Ge1—O4—C21 | 104.3 (2) | Ge1—N1—C13—C8 | 176.4 (2) |
N2—Ge1—O4—C21 | 2.3 (2) | C5—N1—C13—C12 | 178.3 (3) |
N1—Ge1—O4—C21 | −83.2 (2) | Ge1—N1—C13—C12 | −3.7 (3) |
O4—Ge1—N1—C5 | −4.3 (3) | C9—C8—C13—N1 | −178.5 (3) |
O3—Ge1—N1—C5 | −177.4 (3) | C7—C8—C13—N1 | 2.0 (4) |
O1—Ge1—N1—C5 | 87.8 (3) | C9—C8—C13—C12 | 1.6 (4) |
N2—Ge1—N1—C5 | −86.9 (3) | C7—C8—C13—C12 | −177.9 (3) |
O4—Ge1—N1—C13 | 177.96 (18) | O3—C12—C13—N1 | −0.6 (3) |
O3—Ge1—N1—C13 | 4.92 (17) | C11—C12—C13—N1 | 179.3 (2) |
O1—Ge1—N1—C13 | −89.90 (18) | O3—C12—C13—C8 | 179.3 (2) |
N2—Ge1—N1—C13 | 95.42 (18) | C11—C12—C13—C8 | −0.8 (4) |
O4—Ge1—N2—C14 | −178.2 (3) | C22—N2—C14—C15 | 0.6 (5) |
O3—Ge1—N2—C14 | −9.6 (3) | Ge1—N2—C14—C15 | 175.2 (2) |
O1—Ge1—N2—C14 | −114.3 (4) | N2—C14—C15—C16 | −1.3 (5) |
C3—Ge1—N2—C14 | 84.0 (3) | C14—C15—C16—C17 | 1.7 (6) |
N1—Ge1—N2—C14 | −90.9 (3) | C15—C16—C17—C18 | 179.7 (4) |
O4—Ge1—N2—C22 | −3.09 (19) | C15—C16—C17—C22 | −1.4 (5) |
O3—Ge1—N2—C22 | 165.5 (2) | C16—C17—C18—C19 | 179.9 (4) |
O1—Ge1—N2—C22 | 60.8 (5) | C22—C17—C18—C19 | 1.0 (5) |
C3—Ge1—N2—C22 | −100.9 (2) | C17—C18—C19—C20 | −1.5 (6) |
N1—Ge1—N2—C22 | 84.2 (2) | C18—C19—C20—C21 | 0.6 (6) |
Ge1—O1—C1—O2 | −169.7 (2) | Ge1—O4—C21—C20 | 177.8 (3) |
Ge1—O1—C1—C2 | 11.8 (3) | Ge1—O4—C21—C22 | −1.1 (4) |
O2—C1—C2—C3 | 161.7 (3) | C19—C20—C21—O4 | −178.0 (3) |
O1—C1—C2—C3 | −19.8 (5) | C19—C20—C21—C22 | 0.9 (5) |
C1—C2—C3—C4 | 145.5 (4) | C14—N2—C22—C21 | 179.0 (3) |
C1—C2—C3—Ge1 | 16.5 (4) | Ge1—N2—C22—C21 | 3.4 (3) |
O4—Ge1—C3—C4 | −45.0 (3) | C14—N2—C22—C17 | −0.3 (4) |
O3—Ge1—C3—C4 | 129.7 (3) | Ge1—N2—C22—C17 | −175.9 (2) |
O1—Ge1—C3—C4 | −136.7 (3) | O4—C21—C22—N2 | −1.7 (4) |
N2—Ge1—C3—C4 | 39.1 (3) | C20—C21—C22—N2 | 179.3 (3) |
O4—Ge1—C3—C2 | 83.4 (3) | O4—C21—C22—C17 | 177.5 (3) |
O3—Ge1—C3—C2 | −101.9 (3) | C20—C21—C22—C17 | −1.4 (5) |
O1—Ge1—C3—C2 | −8.3 (3) | C16—C17—C22—N2 | 0.7 (4) |
N2—Ge1—C3—C2 | 167.6 (2) | C18—C17—C22—N2 | 179.7 (3) |
C13—N1—C5—C6 | 0.0 (4) | C16—C17—C22—C21 | −178.5 (3) |
Ge1—N1—C5—C6 | −177.5 (2) | C18—C17—C22—C21 | 0.5 (5) |
N1—C5—C6—C7 | 1.0 (5) |
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