Di-μ-oxido-bis-[bis-(diiso-propyl-aceta-midinato)-κN;κ(2) N,N'-germanium(IV)].

The title compound, [Ge2(C8H17N2)4O2], crystallizes with imposed twofold symmetry, which allows the monodentate amidinate ligands to be arranged in a cisoid fashion. The independent Ge-O distances within the central Ge2O2 ring, which is essentially planar (r.m.s. deviation = 0.039 Å), are 1.7797 (8) and 1.8568 (8) Å. The germanium centres adopt a distorted trigonal-bipyramidal geometry, being coordinated by the two O atoms and by one bidentate and one monodentate amidinate ligand (three N atoms). One N-isopropyl group is disordered over two positions; these are mutually exclusive because of 'collisions' between symmetry-equivalent methyl groups and thus each has 0.5 occupancy.

Related literature

For comprehensive reviews on metal amidinates and guanidinates, see: Edelmann (2008 ▶, 2013 ▶). For information on germanium precursors for CVD or ALD production of GST thin layers, see: Chen et al. (2007 ▶, 2009 ▶, 2010 ▶); Lee et al. (2007 ▶). For previous literature on related germanium amidinates, see: Brück et al. (2012 ▶); Cabeza et al. (2013 ▶); Foley et al. (1997 ▶, 2000 ▶); Jones et al. (2008 ▶); Jutzi et al. (1999 ▶); Karsch et al. (1998 ▶); Kühl (2004 ▶); Matioszek et al. (2012 ▶); Yeong et al. (2012 ▶); Zhang & So (2011 ▶).

Experimental

Crystal data

[Ge2(C8H17N2)4O2]

M = 742.12

Monoclinic,

a = 20.1934 (2) Å

b = 12.7424 (1) Å

c = 15.9008 (1) Å

β = 100.038 (1)°

V = 4028.84 (6) Å3

Z = 4

Cu Kα radiation

μ = 2.11 mm−1

T = 100 K

0.08 × 0.08 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.837, T max = 1.000

35712 measured reflections

4173 independent reflections

4014 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.020

wR(F 2) = 0.057

S = 1.08

4173 reflections

245 parameters

28 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Siemens, 1994 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813032133/zl2570sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032133/zl2570Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ge2(C8H17N2)4O2]	F(000) = 1584
Mr = 742.12	Dx = 1.224 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
a = 20.1934 (2) Å	Cell parameters from 28247 reflections
b = 12.7424 (1) Å	θ = 4.1–75.7°
c = 15.9008 (1) Å	µ = 2.11 mm−1
β = 100.038 (1)°	T = 100 K
V = 4028.84 (6) Å3	Plate, colourless
Z = 4	0.08 × 0.08 × 0.04 mm

Oxford Diffraction Xcalibur (Atlas, Nova) diffractometer	4173 independent reflections
Radiation source: Nova (Cu) X-ray Source	4014 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.021
Detector resolution: 10.3543 pixels mm-1	θmax = 75.9°, θmin = 4.1°
ω scan	h = −24→25
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −16→15
Tmin = 0.837, Tmax = 1.000	l = −19→19
35712 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.020	H-atom parameters constrained
wR(F2) = 0.057	w = 1/[σ2(Fo2) + (0.0296P)2 + 2.8972P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.002
4173 reflections	Δρmax = 0.27 e Å−3
245 parameters	Δρmin = −0.29 e Å−3
28 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.000087 (13)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Ge1	0.439398 (6)	0.244195 (9)	0.200846 (8)	0.01509 (6)
O1	0.52408 (4)	0.25038 (5)	0.18371 (5)	0.01763 (17)
N1	0.37824 (5)	0.35942 (7)	0.19850 (6)	0.01908 (19)
N2	0.39972 (5)	0.30266 (8)	0.07745 (6)	0.01980 (19)
N3	0.39391 (5)	0.11656 (7)	0.19497 (6)	0.01919 (19)
C1	0.36719 (5)	0.37371 (9)	0.11299 (7)	0.0202 (2)
C2	0.32297 (7)	0.45872 (10)	0.06893 (8)	0.0308 (3)
H2A	0.3174	0.4490	0.0070	0.046*	0.680 (18)
H2B	0.3437	0.5272	0.0843	0.046*	0.680 (18)
H2C	0.2789	0.4556	0.0867	0.046*	0.680 (18)
H2D	0.3093	0.5055	0.1117	0.046*	0.320 (18)
H2E	0.2830	0.4273	0.0343	0.046*	0.320 (18)
H2F	0.3477	0.4989	0.0320	0.046*	0.320 (18)
C3	0.36233 (6)	0.43549 (9)	0.26152 (7)	0.0231 (2)
H3	0.3236	0.4791	0.2331	0.028*
C4	0.42119 (7)	0.50889 (11)	0.29111 (9)	0.0340 (3)
H4A	0.4595	0.4684	0.3208	0.051*
H4B	0.4081	0.5615	0.3301	0.051*
H4C	0.4339	0.5441	0.2415	0.051*
C5	0.34071 (7)	0.37987 (11)	0.33699 (8)	0.0321 (3)
H5A	0.3003	0.3380	0.3169	0.048*
H5B	0.3309	0.4320	0.3784	0.048*
H5C	0.3770	0.3337	0.3643	0.048*
C6	0.39731 (7)	0.28663 (11)	−0.01370 (8)	0.0301 (3)
H6	0.3740	0.3482	−0.0448	0.036*
C7	0.46850 (10)	0.28230 (19)	−0.03182 (10)	0.0619 (6)
H7A	0.4911	0.3492	−0.0157	0.093*
H7B	0.4673	0.2695	−0.0928	0.093*
H7C	0.4931	0.2254	0.0014	0.093*
C8	0.35668 (12)	0.18830 (13)	−0.04264 (10)	0.0604 (6)
H8A	0.3792	0.1269	−0.0135	0.091*
H8B	0.3532	0.1799	−0.1045	0.091*
H8C	0.3115	0.1949	−0.0285	0.091*
C9	0.40646 (6)	0.02753 (9)	0.15071 (7)	0.0216 (2)
C10	0.47448 (6)	0.02267 (9)	0.12292 (8)	0.0266 (3)
H10A	0.5042	−0.0244	0.1610	0.040*
H10B	0.4942	0.0931	0.1255	0.040*
H10C	0.4690	−0.0039	0.0643	0.040*
C11	0.33400 (6)	0.12089 (9)	0.23715 (8)	0.0236 (2)
H11	0.3388	0.1868	0.2718	0.028*
C12	0.33045 (7)	0.03191 (13)	0.30052 (9)	0.0370 (3)
H12A	0.3182	−0.0335	0.2692	0.055*
H12B	0.2965	0.0485	0.3356	0.055*
H12C	0.3744	0.0236	0.3374	0.055*
C13	0.26852 (6)	0.13273 (11)	0.17384 (9)	0.0320 (3)
H13A	0.2720	0.1928	0.1364	0.048*
H13B	0.2314	0.1442	0.2050	0.048*
H13C	0.2601	0.0688	0.1394	0.048*
N4	0.3607 (6)	−0.0436 (7)	0.1284 (5)	0.0219 (13)	0.50
C14	0.3734 (4)	−0.1437 (6)	0.0885 (4)	0.0274 (15)	0.50
H14	0.4104	−0.1343	0.0548	0.033*	0.50
C15	0.3947 (3)	−0.2241 (3)	0.1584 (3)	0.0514 (9)	0.50
H15A	0.4348	−0.1987	0.1969	0.077*	0.50
H15B	0.4051	−0.2907	0.1327	0.077*	0.50
H15C	0.3581	−0.2347	0.1906	0.077*	0.50
C16	0.30970 (18)	−0.1764 (3)	0.0291 (2)	0.0430 (8)	0.50
H16A	0.2969	−0.1219	−0.0142	0.064*	0.50
H16B	0.2734	−0.1860	0.0620	0.064*	0.50
H16C	0.3176	−0.2426	0.0009	0.064*	0.50
N4'	0.3645 (7)	−0.0479 (7)	0.1505 (5)	0.0255 (15)	0.50
C14'	0.3827 (5)	−0.1470 (7)	0.1139 (5)	0.0335 (16)	0.50
H14'	0.4326	−0.1515	0.1188	0.040*	0.50
C15'	0.3495 (3)	−0.1540 (3)	0.0203 (3)	0.0619 (11)	0.50
H15D	0.3689	−0.1008	−0.0126	0.093*	0.50
H15E	0.3011	−0.1419	0.0153	0.093*	0.50
H15F	0.3573	−0.2239	−0.0018	0.093*	0.50
C16'	0.3578 (3)	−0.2357 (3)	0.1644 (3)	0.0570 (12)	0.50
H16D	0.3818	−0.2337	0.2236	0.086*	0.50
H16E	0.3660	−0.3032	0.1386	0.086*	0.50
H16F	0.3094	−0.2273	0.1638	0.086*	0.50

	U11	U22	U33	U12	U13	U23
Ge1	0.01334 (8)	0.01533 (8)	0.01667 (8)	0.00042 (4)	0.00282 (5)	−0.00043 (4)
O1	0.0150 (4)	0.0206 (4)	0.0175 (4)	−0.0007 (3)	0.0031 (3)	0.0003 (3)
N1	0.0190 (4)	0.0190 (4)	0.0191 (4)	0.0041 (4)	0.0028 (3)	−0.0008 (4)
N2	0.0208 (5)	0.0214 (5)	0.0169 (4)	0.0033 (4)	0.0023 (3)	0.0011 (3)
N3	0.0160 (4)	0.0183 (4)	0.0241 (5)	−0.0020 (3)	0.0058 (3)	−0.0019 (4)
C1	0.0183 (5)	0.0196 (5)	0.0220 (5)	0.0004 (4)	0.0020 (4)	0.0006 (4)
C2	0.0372 (7)	0.0278 (6)	0.0257 (6)	0.0132 (5)	0.0012 (5)	0.0028 (5)
C3	0.0237 (6)	0.0218 (5)	0.0242 (6)	0.0063 (4)	0.0058 (4)	−0.0031 (4)
C4	0.0377 (7)	0.0273 (6)	0.0374 (7)	−0.0013 (5)	0.0074 (6)	−0.0128 (5)
C5	0.0388 (7)	0.0322 (7)	0.0292 (6)	0.0091 (6)	0.0164 (5)	−0.0014 (5)
C6	0.0408 (7)	0.0322 (7)	0.0171 (6)	0.0140 (6)	0.0041 (5)	0.0013 (5)
C7	0.0561 (11)	0.1062 (15)	0.0287 (8)	0.0446 (11)	0.0226 (7)	0.0206 (9)
C8	0.1093 (16)	0.0335 (8)	0.0285 (7)	0.0050 (9)	−0.0156 (9)	−0.0068 (6)
C9	0.0202 (5)	0.0178 (5)	0.0275 (6)	0.0012 (4)	0.0060 (4)	0.0006 (4)
C10	0.0236 (6)	0.0221 (6)	0.0362 (7)	−0.0009 (5)	0.0115 (5)	−0.0049 (5)
C11	0.0190 (5)	0.0241 (6)	0.0295 (6)	−0.0041 (4)	0.0092 (4)	−0.0043 (5)
C12	0.0257 (6)	0.0545 (9)	0.0320 (7)	−0.0064 (6)	0.0087 (5)	0.0118 (6)
C13	0.0184 (6)	0.0322 (7)	0.0458 (8)	0.0016 (5)	0.0067 (5)	0.0079 (6)
N4	0.0254 (19)	0.0206 (16)	0.023 (3)	−0.0030 (12)	0.012 (3)	−0.005 (2)
C14	0.032 (3)	0.0166 (16)	0.037 (4)	−0.0058 (15)	0.015 (3)	−0.012 (2)
C15	0.066 (3)	0.0216 (16)	0.069 (3)	0.0049 (18)	0.021 (2)	−0.0015 (16)
C16	0.0405 (18)	0.0405 (18)	0.0509 (18)	−0.0121 (14)	0.0162 (15)	−0.0264 (14)
N4'	0.034 (2)	0.0169 (16)	0.029 (4)	−0.0040 (12)	0.014 (3)	−0.006 (2)
C14'	0.035 (3)	0.028 (2)	0.040 (4)	−0.0088 (17)	0.013 (3)	−0.016 (2)
C15'	0.072 (3)	0.045 (2)	0.064 (3)	−0.003 (2)	0.002 (2)	−0.0315 (19)
C16'	0.074 (3)	0.0186 (15)	0.088 (3)	−0.0006 (18)	0.041 (3)	−0.0027 (15)

Ge1—O1	1.7797 (8)	C8—H8C	0.9800
Ge1—O1i	1.8568 (8)	C9—N4'	1.281 (12)
Ge1—N3	1.8621 (9)	C9—N4	1.299 (12)
Ge1—N1	1.9148 (9)	C9—C10	1.5157 (15)
Ge1—N2	2.1211 (9)	C10—H10A	0.9800
O1—Ge1i	1.8568 (8)	C10—H10B	0.9800
N1—C1	1.3512 (14)	C10—H10C	0.9800
N1—C3	1.4694 (14)	C11—C13	1.5234 (17)
N2—C1	1.3038 (15)	C11—C12	1.5268 (18)
N2—C6	1.4560 (14)	C11—H11	1.0000
N3—C9	1.3816 (14)	C12—H12A	0.9800
N3—C11	1.4831 (14)	C12—H12B	0.9800
C1—C2	1.4978 (16)	C12—H12C	0.9800
C2—H2A	0.9800	C13—H13A	0.9800
C2—H2B	0.9800	C13—H13B	0.9800
C2—H2C	0.9800	C13—H13C	0.9800
C2—H2D	0.9800	N4—C14	1.467 (9)
C2—H2E	0.9800	C14—C16	1.516 (7)
C2—H2F	0.9800	C14—C15	1.517 (7)
C3—C4	1.5211 (17)	C14—H14	1.0000
C3—C5	1.5218 (17)	C15—H15A	0.9800
C3—H3	1.0000	C15—H15B	0.9800
C4—H4A	0.9800	C15—H15C	0.9800
C4—H4B	0.9800	C16—H16A	0.9800
C4—H4C	0.9800	C16—H16B	0.9800
C5—H5A	0.9800	C16—H16C	0.9800
C5—H5B	0.9800	N4'—C14'	1.463 (9)
C5—H5C	0.9800	C14'—C16'	1.522 (9)
C6—C7	1.516 (2)	C14'—C15'	1.524 (7)
C6—C8	1.524 (2)	C14'—H14'	1.0000
C6—H6	1.0000	C15'—H15D	0.9800
C7—H7A	0.9800	C15'—H15E	0.9800
C7—H7B	0.9800	C15'—H15F	0.9800
C7—H7C	0.9800	C16'—H16D	0.9800
C8—H8A	0.9800	C16'—H16E	0.9800
C8—H8B	0.9800	C16'—H16F	0.9800
O1—Ge1—O1i	85.57 (4)	H7A—C7—H7C	109.5
O1—Ge1—N3	120.65 (4)	H7B—C7—H7C	109.5
O1i—Ge1—N3	101.19 (4)	C6—C8—H8A	109.5
O1—Ge1—N1	126.64 (4)	C6—C8—H8B	109.5
O1i—Ge1—N1	97.49 (4)	H8A—C8—H8B	109.5
N3—Ge1—N1	110.97 (4)	C6—C8—H8C	109.5
O1—Ge1—N2	93.50 (4)	H8A—C8—H8C	109.5
O1i—Ge1—N2	157.00 (3)	H8B—C8—H8C	109.5
N3—Ge1—N2	99.02 (4)	N4'—C9—N3	116.0 (5)
N1—Ge1—N2	64.80 (4)	N4—C9—N3	121.8 (5)
Ge1—O1—Ge1i	94.21 (4)	N4'—C9—C10	126.9 (5)
C1—N1—C3	125.44 (9)	N4—C9—C10	122.0 (5)
C1—N1—Ge1	96.65 (7)	N3—C9—C10	115.98 (10)
C3—N1—Ge1	135.19 (7)	C9—C10—H10A	109.5
C1—N2—C6	126.65 (10)	C9—C10—H10B	109.5
C1—N2—Ge1	88.89 (7)	H10A—C10—H10B	109.5
C6—N2—Ge1	144.41 (8)	C9—C10—H10C	109.5
C9—N3—C11	119.83 (9)	H10A—C10—H10C	109.5
C9—N3—Ge1	127.60 (8)	H10B—C10—H10C	109.5
C11—N3—Ge1	112.27 (7)	N3—C11—C13	112.79 (10)
N2—C1—N1	109.59 (10)	N3—C11—C12	114.00 (10)
N2—C1—C2	127.14 (11)	C13—C11—C12	112.00 (10)
N1—C1—C2	123.27 (10)	N3—C11—H11	105.7
N2—C1—Ge1	59.23 (6)	C13—C11—H11	105.7
N1—C1—Ge1	50.41 (5)	C12—C11—H11	105.7
C2—C1—Ge1	173.51 (9)	C11—C12—H12A	109.5
C1—C2—H2A	109.5	C11—C12—H12B	109.5
C1—C2—H2B	109.5	H12A—C12—H12B	109.5
H2A—C2—H2B	109.5	C11—C12—H12C	109.5
C1—C2—H2C	109.5	H12A—C12—H12C	109.5
H2A—C2—H2C	109.5	H12B—C12—H12C	109.5
H2B—C2—H2C	109.5	C11—C13—H13A	109.5
C1—C2—H2D	109.5	C11—C13—H13B	109.5
H2A—C2—H2D	141.1	H13A—C13—H13B	109.5
H2B—C2—H2D	56.3	C11—C13—H13C	109.5
H2C—C2—H2D	56.3	H13A—C13—H13C	109.5
C1—C2—H2E	109.5	H13B—C13—H13C	109.5
H2A—C2—H2E	56.3	C9—N4—C14	123.7 (9)
H2B—C2—H2E	141.1	N4—C14—C16	108.3 (7)
H2C—C2—H2E	56.3	N4—C14—C15	108.6 (6)
H2D—C2—H2E	109.5	C16—C14—C15	111.9 (6)
C1—C2—H2F	109.5	N4—C14—H14	109.3
H2A—C2—H2F	56.3	C16—C14—H14	109.3
H2B—C2—H2F	56.3	C15—C14—H14	109.3
H2C—C2—H2F	141.1	C14—C15—H15A	109.5
H2D—C2—H2F	109.5	C14—C15—H15B	109.5
H2E—C2—H2F	109.5	H15A—C15—H15B	109.5
N1—C3—C4	111.39 (10)	C14—C15—H15C	109.5
N1—C3—C5	110.94 (10)	H15A—C15—H15C	109.5
C4—C3—C5	111.01 (11)	H15B—C15—H15C	109.5
N1—C3—H3	107.8	C14—C16—H16A	109.5
C4—C3—H3	107.8	C14—C16—H16B	109.5
C5—C3—H3	107.8	H16A—C16—H16B	109.5
C3—C4—H4A	109.5	C14—C16—H16C	109.5
C3—C4—H4B	109.5	H16A—C16—H16C	109.5
H4A—C4—H4B	109.5	H16B—C16—H16C	109.5
C3—C4—H4C	109.5	C9—N4'—C14'	115.9 (10)
H4A—C4—H4C	109.5	N4'—C14'—C16'	107.6 (7)
H4B—C4—H4C	109.5	N4'—C14'—C15'	109.9 (6)
C3—C5—H5A	109.5	C16'—C14'—C15'	110.0 (6)
C3—C5—H5B	109.5	N4'—C14'—H14'	109.8
H5A—C5—H5B	109.5	C16'—C14'—H14'	109.8
C3—C5—H5C	109.5	C15'—C14'—H14'	109.8
H5A—C5—H5C	109.5	C14'—C15'—H15D	109.5
H5B—C5—H5C	109.5	C14'—C15'—H15E	109.5
N2—C6—C7	109.03 (11)	H15D—C15'—H15E	109.5
N2—C6—C8	109.80 (12)	C14'—C15'—H15F	109.5
C7—C6—C8	113.02 (15)	H15D—C15'—H15F	109.5
N2—C6—H6	108.3	H15E—C15'—H15F	109.5
C7—C6—H6	108.3	C14'—C16'—H16D	109.5
C8—C6—H6	108.3	C14'—C16'—H16E	109.5
C6—C7—H7A	109.5	H16D—C16'—H16E	109.5
C6—C7—H7B	109.5	C14'—C16'—H16F	109.5
H7A—C7—H7B	109.5	H16D—C16'—H16F	109.5
C6—C7—H7C	109.5	H16E—C16'—H16F	109.5
O1i—Ge1—O1—Ge1i	4.88 (4)	C3—N1—C1—Ge1	163.67 (13)
N3—Ge1—O1—Ge1i	−95.52 (4)	O1—Ge1—C1—N2	58.62 (7)
N1—Ge1—O1—Ge1i	100.93 (4)	O1i—Ge1—C1—N2	161.01 (6)
N2—Ge1—O1—Ge1i	161.84 (3)	N3—Ge1—C1—N2	−76.93 (7)
O1—Ge1—N1—C1	72.88 (8)	N1—Ge1—C1—N2	−177.09 (11)
O1i—Ge1—N1—C1	162.93 (7)	O1—Ge1—C1—N1	−124.28 (7)
N3—Ge1—N1—C1	−92.00 (7)	O1i—Ge1—C1—N1	−21.89 (9)
N2—Ge1—N1—C1	−1.70 (6)	N3—Ge1—C1—N1	100.16 (7)
O1—Ge1—N1—C3	−88.15 (11)	N2—Ge1—C1—N1	177.09 (11)
O1i—Ge1—N1—C3	1.89 (11)	C1—N1—C3—C4	−89.99 (14)
N3—Ge1—N1—C3	106.97 (11)	Ge1—N1—C3—C4	66.67 (14)
N2—Ge1—N1—C3	−162.73 (12)	C1—N1—C3—C5	145.80 (11)
O1—Ge1—N2—C1	−127.45 (7)	Ge1—N1—C3—C5	−57.54 (14)
O1i—Ge1—N2—C1	−40.55 (12)	C1—N2—C6—C7	129.19 (15)
N3—Ge1—N2—C1	110.76 (7)	Ge1—N2—C6—C7	−54.4 (2)
N1—Ge1—N2—C1	1.75 (7)	C1—N2—C6—C8	−106.49 (15)
O1—Ge1—N2—C6	55.45 (15)	Ge1—N2—C6—C8	69.89 (19)
O1i—Ge1—N2—C6	142.36 (14)	C11—N3—C9—N4'	−1.0 (5)
N3—Ge1—N2—C6	−66.34 (15)	Ge1—N3—C9—N4'	−174.2 (5)
N1—Ge1—N2—C6	−175.35 (16)	C11—N3—C9—N4	15.5 (5)
O1—Ge1—N3—C9	−24.75 (11)	Ge1—N3—C9—N4	−157.6 (4)
O1i—Ge1—N3—C9	−116.23 (10)	C11—N3—C9—C10	−169.85 (10)
N1—Ge1—N3—C9	141.17 (9)	Ge1—N3—C9—C10	17.01 (15)
N2—Ge1—N3—C9	74.80 (10)	C9—N3—C11—C13	−73.08 (14)
O1—Ge1—N3—C11	161.68 (7)	Ge1—N3—C11—C13	101.05 (10)
O1i—Ge1—N3—C11	70.20 (8)	C9—N3—C11—C12	56.10 (15)
N1—Ge1—N3—C11	−32.40 (9)	Ge1—N3—C11—C12	−129.76 (9)
N2—Ge1—N3—C11	−98.78 (8)	N4'—C9—N4—C14	−102 (4)
C6—N2—C1—N1	175.52 (11)	N3—C9—N4—C14	−174.1 (5)
Ge1—N2—C1—N1	−2.38 (9)	C10—C9—N4—C14	11.6 (9)
C6—N2—C1—C2	−3.6 (2)	C9—N4—C14—C16	−148.6 (7)
Ge1—N2—C1—C2	178.47 (12)	C9—N4—C14—C15	89.7 (9)
C6—N2—C1—Ge1	177.89 (13)	N4—C9—N4'—C14'	72 (3)
C3—N1—C1—N2	166.32 (10)	N3—C9—N4'—C14'	−171.9 (5)
Ge1—N1—C1—N2	2.65 (10)	C10—C9—N4'—C14'	−4.5 (9)
C3—N1—C1—C2	−14.48 (18)	C9—N4'—C14'—C16'	145.1 (7)
Ge1—N1—C1—C2	−178.16 (10)	C9—N4'—C14'—C15'	−95.1 (9)