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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001455/lh6346sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001455/lh6346Isup2.hkl
Contains datablock I

CCDC reference: 249963

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](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.

β-Methyl-γ-bis(N,O-8-quinolinoxy)germa-γ-lactone top
Crystal data top
[Ge(C9H7NO)2(C4H6O2)]Dx = 1.507 Mg m3
Mr = 446.97Melting point: 538-540 K (decomp.) K
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 8481 reflections
a = 9.695 (2) Åθ = 3.0–27.5°
b = 17.266 (4) ŵ = 1.59 mm1
c = 23.543 (4) ÅT = 173 K
V = 3941.0 (14) Å3Prism, yellow
Z = 80.14 × 0.12 × 0.10 mm
F(000) = 1824
Data collection top
Nonius KappaCCD area-detector
diffractometer
4504 independent reflections
Radiation source: fine-focus sealed tube3256 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
ω and φ scansθmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)
h = 1212
Tmin = 0.809, Tmax = 0.858k = 2222
8481 measured reflectionsl = 3030
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-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 parametersΔρmax = 0.96 e Å3
0 restraintsΔρmin = 0.84 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ge10.58191 (3)0.074891 (17)0.617519 (12)0.02929 (11)
O10.4988 (2)0.16969 (11)0.64242 (8)0.0321 (4)
O20.3078 (2)0.23837 (13)0.63178 (9)0.0418 (5)
O30.6515 (2)0.11923 (11)0.54949 (8)0.0308 (4)
O40.5583 (2)0.02909 (13)0.69016 (9)0.0409 (5)
N10.7599 (2)0.12613 (13)0.65037 (9)0.0273 (5)
N20.7057 (3)0.02130 (14)0.60480 (11)0.0347 (6)
C10.3701 (3)0.17768 (18)0.62647 (12)0.0315 (6)
C20.3056 (4)0.1050 (2)0.6026 (2)0.0609 (11)
H2A0.24610.08180.63220.073*
H2B0.24540.11980.57040.073*
C30.4053 (3)0.04405 (18)0.58229 (14)0.0390 (7)
H30.41610.05170.54040.047*
C40.3610 (5)0.0375 (2)0.5907 (2)0.0711 (12)
H4A0.27150.04570.57240.085*
H4B0.35280.04830.63150.085*
H4C0.42950.07240.57390.085*
C50.8120 (3)0.12527 (18)0.70226 (12)0.0360 (7)
H50.76700.09590.73090.043*
C60.9310 (3)0.1662 (2)0.71616 (13)0.0418 (8)
H60.96700.16380.75370.050*
C70.9955 (3)0.2096 (2)0.67585 (13)0.0401 (7)
H71.07630.23790.68540.048*
C80.9431 (3)0.21278 (17)0.61977 (12)0.0321 (6)
C90.9994 (3)0.25552 (19)0.57457 (13)0.0385 (7)
H91.07850.28700.58050.046*
C100.9398 (3)0.2516 (2)0.52203 (13)0.0400 (7)
H100.97890.28060.49180.048*
C110.8221 (3)0.20570 (17)0.51128 (12)0.0338 (7)
H110.78390.20370.47420.041*
C120.7632 (3)0.16404 (15)0.55447 (11)0.0280 (6)
C130.8240 (3)0.16815 (16)0.60915 (11)0.0262 (6)
C140.7795 (3)0.04096 (19)0.55989 (14)0.0420 (8)
H140.77420.01040.52640.050*
C150.8657 (4)0.1063 (2)0.56091 (16)0.0512 (9)
H150.91690.12040.52810.061*
C160.8758 (4)0.1494 (2)0.60915 (17)0.0529 (10)
H160.93600.19270.61010.063*
C170.7980 (3)0.13044 (18)0.65750 (15)0.0444 (8)
C180.7985 (4)0.1704 (2)0.70970 (19)0.0589 (10)
H180.85510.21480.71460.071*
C190.7175 (4)0.1450 (2)0.75287 (18)0.0591 (11)
H190.71740.17330.78750.071*
C200.6329 (4)0.0778 (2)0.74871 (16)0.0530 (9)
H200.57820.06170.78000.064*
C210.6313 (3)0.03654 (18)0.69845 (14)0.0410 (8)
C220.7125 (3)0.06371 (16)0.65323 (14)0.0362 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ge10.02843 (16)0.02435 (16)0.03510 (18)0.00087 (12)0.00095 (13)0.00114 (12)
O10.0294 (10)0.0305 (10)0.0364 (10)0.0024 (8)0.0030 (9)0.0034 (9)
O20.0340 (11)0.0408 (13)0.0507 (13)0.0104 (10)0.0040 (10)0.0100 (10)
O30.0322 (10)0.0303 (10)0.0299 (10)0.0013 (9)0.0066 (9)0.0005 (8)
O40.0436 (13)0.0380 (12)0.0411 (12)0.0002 (10)0.0094 (10)0.0089 (9)
N10.0276 (11)0.0278 (12)0.0265 (11)0.0034 (10)0.0022 (10)0.0002 (9)
N20.0344 (13)0.0247 (12)0.0450 (15)0.0016 (10)0.0038 (11)0.0004 (11)
C10.0289 (14)0.0345 (16)0.0310 (15)0.0022 (12)0.0020 (12)0.0007 (12)
C20.0345 (18)0.048 (2)0.100 (3)0.0051 (16)0.0173 (19)0.025 (2)
C30.0334 (16)0.0342 (16)0.0496 (18)0.0050 (13)0.0035 (14)0.0073 (14)
C40.065 (3)0.045 (2)0.104 (3)0.014 (2)0.025 (3)0.002 (2)
C50.0369 (16)0.0427 (17)0.0286 (15)0.0046 (14)0.0022 (13)0.0029 (12)
C60.0381 (17)0.058 (2)0.0289 (15)0.0037 (16)0.0082 (14)0.0047 (14)
C70.0258 (15)0.053 (2)0.0410 (17)0.0016 (14)0.0058 (13)0.0092 (15)
C80.0253 (14)0.0355 (16)0.0354 (15)0.0028 (12)0.0008 (12)0.0039 (13)
C90.0279 (15)0.0428 (18)0.0449 (17)0.0040 (13)0.0044 (13)0.0013 (14)
C100.0343 (16)0.0456 (19)0.0401 (17)0.0020 (14)0.0089 (14)0.0088 (14)
C110.0364 (16)0.0386 (17)0.0265 (14)0.0084 (13)0.0003 (12)0.0050 (12)
C120.0278 (14)0.0274 (14)0.0286 (13)0.0041 (12)0.0029 (11)0.0018 (11)
C130.0236 (13)0.0258 (13)0.0291 (14)0.0041 (11)0.0007 (11)0.0004 (11)
C140.0411 (18)0.0390 (17)0.0460 (18)0.0060 (14)0.0031 (15)0.0087 (14)
C150.052 (2)0.046 (2)0.056 (2)0.0172 (17)0.0079 (18)0.0124 (17)
C160.0471 (19)0.0318 (18)0.080 (3)0.0098 (15)0.0150 (19)0.0134 (17)
C170.0428 (18)0.0273 (16)0.063 (2)0.0027 (13)0.0202 (16)0.0048 (15)
C180.063 (2)0.0345 (19)0.079 (3)0.0022 (18)0.026 (2)0.0130 (19)
C190.069 (3)0.0408 (19)0.067 (2)0.0110 (19)0.018 (2)0.0270 (19)
C200.059 (2)0.046 (2)0.054 (2)0.0121 (18)0.0011 (18)0.0168 (17)
C210.0422 (18)0.0312 (17)0.0497 (19)0.0083 (14)0.0040 (15)0.0130 (14)
C220.0352 (16)0.0260 (15)0.0475 (18)0.0034 (12)0.0072 (14)0.0035 (13)
Geometric parameters (Å, º) top
Ge1—O41.898 (2)C7—C81.416 (4)
Ge1—O31.899 (2)C7—H70.9500
Ge1—O11.916 (2)C8—C91.405 (4)
Ge1—C31.976 (3)C8—C131.410 (4)
Ge1—N22.071 (2)C9—C101.367 (4)
Ge1—N12.087 (2)C9—H90.9500
O1—C11.310 (3)C10—C111.412 (4)
O2—C11.216 (4)C10—H100.9500
O3—C121.336 (3)C11—C121.371 (4)
O4—C211.350 (4)C11—H110.9500
N1—C51.322 (4)C12—C131.418 (4)
N1—C131.362 (3)C14—C151.404 (5)
N2—C141.321 (4)C14—H140.9500
N2—C221.357 (4)C15—C161.361 (5)
C1—C21.510 (5)C15—H150.9500
C2—C31.507 (5)C16—C171.404 (5)
C2—H2A0.9900C16—H160.9500
C2—H2B0.9900C17—C181.409 (5)
C3—C41.486 (5)C17—C221.423 (4)
C3—H31.0000C18—C191.358 (6)
C4—H4A0.9800C18—H180.9500
C4—H4B0.9800C19—C201.424 (5)
C4—H4C0.9800C19—H190.9500
C5—C61.391 (4)C20—C211.382 (4)
C5—H50.9500C20—H200.9500
C6—C71.362 (5)C21—C221.405 (5)
C6—H60.9500
O4—Ge1—O3166.11 (9)C5—C6—H6120.1
O4—Ge1—O191.70 (9)C6—C7—C8120.4 (3)
O3—Ge1—O193.61 (8)C6—C7—H7119.8
O4—Ge1—C399.29 (12)C8—C7—H7119.8
O3—Ge1—C393.58 (12)C9—C8—C13118.1 (3)
O1—Ge1—C389.67 (11)C9—C8—C7126.0 (3)
O4—Ge1—N282.30 (10)C13—C8—C7116.0 (3)
O3—Ge1—N289.75 (9)C10—C9—C8119.7 (3)
O1—Ge1—N2166.66 (9)C10—C9—H9120.2
C3—Ge1—N2103.02 (12)C8—C9—H9120.2
O4—Ge1—N186.69 (9)C9—C10—C11122.1 (3)
O3—Ge1—N181.27 (8)C9—C10—H10118.9
O1—Ge1—N182.66 (8)C11—C10—H10118.9
C3—Ge1—N1170.43 (11)C12—C11—C10119.9 (3)
N2—Ge1—N185.10 (9)C12—C11—H11120.1
C1—O1—Ge1113.8 (2)C10—C11—H11120.1
C12—O3—Ge1116.6 (2)O3—C12—C11125.2 (2)
C21—O4—Ge1114.6 (2)O3—C12—C13116.5 (2)
C5—N1—C13119.3 (3)C11—C12—C13118.3 (3)
C5—N1—Ge1130.8 (2)N1—C13—C8122.6 (2)
C13—N1—Ge1109.8 (2)N1—C13—C12115.5 (2)
C14—N2—C22120.5 (3)C8—C13—C12121.9 (2)
C14—N2—Ge1129.5 (2)N2—C14—C15121.0 (3)
C22—N2—Ge1109.9 (2)N2—C14—H14119.5
O2—C1—O1122.3 (3)C15—C14—H14119.5
O2—C1—C2123.3 (3)C16—C15—C14119.7 (3)
O1—C1—C2114.4 (3)C16—C15—H15120.1
C3—C2—C1115.6 (3)C14—C15—H15120.1
C3—C2—H2A108.4C15—C16—C17120.7 (3)
C1—C2—H2A108.4C15—C16—H16119.6
C3—C2—H2B108.4C17—C16—H16119.6
C1—C2—H2B108.4C16—C17—C18126.2 (3)
H2A—C2—H2B107.4C16—C17—C22116.4 (3)
C4—C3—C2115.8 (3)C18—C17—C22117.4 (3)
C4—C3—Ge1116.7 (3)C19—C18—C17119.5 (3)
C2—C3—Ge1103.5 (2)C19—C18—H18120.3
C4—C3—H3106.7C17—C18—H18120.3
C2—C3—H3106.7C18—C19—C20123.1 (3)
Ge1—C3—H3106.7C18—C19—H19118.5
C3—C4—H4A109.5C20—C19—H19118.5
C3—C4—H4B109.5C21—C20—C19119.0 (4)
H4A—C4—H4B109.5C21—C20—H20120.5
C3—C4—H4C109.5C19—C20—H20120.5
H4A—C4—H4C109.5O4—C21—C20124.3 (3)
H4B—C4—H4C109.5O4—C21—C22117.7 (3)
N1—C5—C6121.9 (3)C20—C21—C22118.1 (3)
N1—C5—H5119.0N2—C22—C21115.4 (3)
C6—C5—H5119.0N2—C22—C17121.7 (3)
C7—C6—C5119.8 (3)C21—C22—C17122.9 (3)
C7—C6—H6120.1
O4—Ge1—O1—C1101.0 (2)C5—C6—C7—C80.6 (5)
O3—Ge1—O1—C191.81 (19)C6—C7—C8—C9179.6 (3)
C3—Ge1—O1—C11.8 (2)C6—C7—C8—C130.9 (4)
N2—Ge1—O1—C1163.9 (4)C13—C8—C9—C101.3 (4)
N1—Ge1—O1—C1172.5 (2)C7—C8—C9—C10178.2 (3)
O4—Ge1—O3—C1235.8 (5)C8—C9—C10—C110.1 (5)
O1—Ge1—O3—C1276.48 (18)C9—C10—C11—C120.7 (5)
C3—Ge1—O3—C12166.37 (19)Ge1—O3—C12—C11174.7 (2)
N2—Ge1—O3—C1290.60 (19)Ge1—O3—C12—C135.2 (3)
N1—Ge1—O3—C125.52 (18)C10—C11—C12—O3179.5 (3)
O3—Ge1—O4—C2153.3 (5)C10—C11—C12—C130.4 (4)
O1—Ge1—O4—C21165.8 (2)C5—N1—C13—C81.6 (4)
C3—Ge1—O4—C21104.3 (2)Ge1—N1—C13—C8176.4 (2)
N2—Ge1—O4—C212.3 (2)C5—N1—C13—C12178.3 (3)
N1—Ge1—O4—C2183.2 (2)Ge1—N1—C13—C123.7 (3)
O4—Ge1—N1—C54.3 (3)C9—C8—C13—N1178.5 (3)
O3—Ge1—N1—C5177.4 (3)C7—C8—C13—N12.0 (4)
O1—Ge1—N1—C587.8 (3)C9—C8—C13—C121.6 (4)
N2—Ge1—N1—C586.9 (3)C7—C8—C13—C12177.9 (3)
O4—Ge1—N1—C13177.96 (18)O3—C12—C13—N10.6 (3)
O3—Ge1—N1—C134.92 (17)C11—C12—C13—N1179.3 (2)
O1—Ge1—N1—C1389.90 (18)O3—C12—C13—C8179.3 (2)
N2—Ge1—N1—C1395.42 (18)C11—C12—C13—C80.8 (4)
O4—Ge1—N2—C14178.2 (3)C22—N2—C14—C150.6 (5)
O3—Ge1—N2—C149.6 (3)Ge1—N2—C14—C15175.2 (2)
O1—Ge1—N2—C14114.3 (4)N2—C14—C15—C161.3 (5)
C3—Ge1—N2—C1484.0 (3)C14—C15—C16—C171.7 (6)
N1—Ge1—N2—C1490.9 (3)C15—C16—C17—C18179.7 (4)
O4—Ge1—N2—C223.09 (19)C15—C16—C17—C221.4 (5)
O3—Ge1—N2—C22165.5 (2)C16—C17—C18—C19179.9 (4)
O1—Ge1—N2—C2260.8 (5)C22—C17—C18—C191.0 (5)
C3—Ge1—N2—C22100.9 (2)C17—C18—C19—C201.5 (6)
N1—Ge1—N2—C2284.2 (2)C18—C19—C20—C210.6 (6)
Ge1—O1—C1—O2169.7 (2)Ge1—O4—C21—C20177.8 (3)
Ge1—O1—C1—C211.8 (3)Ge1—O4—C21—C221.1 (4)
O2—C1—C2—C3161.7 (3)C19—C20—C21—O4178.0 (3)
O1—C1—C2—C319.8 (5)C19—C20—C21—C220.9 (5)
C1—C2—C3—C4145.5 (4)C14—N2—C22—C21179.0 (3)
C1—C2—C3—Ge116.5 (4)Ge1—N2—C22—C213.4 (3)
O4—Ge1—C3—C445.0 (3)C14—N2—C22—C170.3 (4)
O3—Ge1—C3—C4129.7 (3)Ge1—N2—C22—C17175.9 (2)
O1—Ge1—C3—C4136.7 (3)O4—C21—C22—N21.7 (4)
N2—Ge1—C3—C439.1 (3)C20—C21—C22—N2179.3 (3)
O4—Ge1—C3—C283.4 (3)O4—C21—C22—C17177.5 (3)
O3—Ge1—C3—C2101.9 (3)C20—C21—C22—C171.4 (5)
O1—Ge1—C3—C28.3 (3)C16—C17—C22—N20.7 (4)
N2—Ge1—C3—C2167.6 (2)C18—C17—C22—N2179.7 (3)
C13—N1—C5—C60.0 (4)C16—C17—C22—C21178.5 (3)
Ge1—N1—C5—C6177.5 (2)C18—C17—C22—C210.5 (5)
N1—C5—C6—C71.0 (5)
 

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