organic compounds
1,3,7,9-Tetrakis[2,6-bis(1-methylethyl)phenyl]-2,2,8,8-tetraphenyl-5,10-dithia-1,3,7,9-tetraaza-2,8-disila-4,6-digermadispiro[3.1.3.1]decane acetonitrile monosolvate
aInstitute of Organic Chemistry and College of Chemical and Materials Science, Shanxi Normal University, Gongyuan Street 1, Linfen, Shanxi Province 041004, People's Republic of China
*Correspondence e-mail: wjzheng_sxnu@qq.com;_wjzheng@sxnu.edu.cn
In the compound, [η2(N,N)-Ph2Si(NDipp)2Ge(μ-S)]2·CH3CN (Dipp = 2,6-iPr2C6H3), C72H88Ge2N4S2Si2·CH2CN, the dimeric germanethione complex lies about an inversion centre with the two GeIV atoms bridged by two sulfide ligands forming the central Ge2S2 ring. Each GeIV atom is also coordinated by two N atoms from the bulky bis(amido)silane ligands in a slightly distorted tetrahedral coordination geometry. An acetonitrile solvent molecule, disordered about an inversion centre, is also present.
Keywords: germanium(IV); sulfide; bis(amido)silane; germanethione dimer; crystal structure.
CCDC reference: 1454736
Structure description
Reaction of the arylamido germylene [Ph2Si(DippN)2Ge:] with elemental sulfur gave the new germanethione dimer 1,3,7,9-tetrakis[2,6-bis(1-methylethyl)phenyl]-2,2,8,8-tetrakis(1-phenyl)-5,10-dithia-1,3,7,9-tetraaza-2,8-disila-4,6-digermadispiro[3.1.3.1]decane, [η2(N,N)-Ph2Si(DippN)2Ge(μ-S)]2 (Dipp = 2,6 − iPr2C6H3) which crystallizes as an acetonitrile solvate. A related compound [η2(N,N)-Me2Si(DippN)2Ge(μ-O)]2, was prepared previously by a similar process involving the direct reaction of [η2(N,N)-Me2Si(DippN)2Ge:], with dioxygen (Yang et al., 2012).
The GeIV complex lies about an inversion centre with the two Ge atoms bridged by two sulfido ligands forming the central Ge2S2 ring. Each Ge atom is also coordinated by two nitrogen atoms from the bulky bis(amido)silane ligands in a slightly distorted tetrahedral coordination geometry. The molecular structure is dimeric in the solid state and contains planar NSiNGe and Ge2S2 arrays that are inclined to one another by 89.42 (8)°, with average endocyclic Ge—S and Ge—N bond lengths of 2.2320 (9) and 1.845 (3) Å, respectively (Fig. 1). The Ge—S bond lengths of 2.2590 (10) and 2.2050 (9) Å are reasonably similar to those found in [η2(N,N)-iPr2Si(DippN)2Ge(μ-S)]2 [Ge—S = 2.1992 (3) and 2.2577 (3) Å; Al-Rafia et al., 2010] and also those found in other closely related bis-sulfide derivatives (Sen et al., 2011; Bazinet et al., 2001; Wegner et al., 2000). An acetonitrile solvent molecule, disordered about an inversion centre such that each disorder component has equal occupancy, is found in the crystal lattice.
Synthesis and crystallization
A solution of [Ph2Si(DippN)2Ge:] (0.600 g, 1.0 mmol) (Yang et al., 2012) in 10 ml dry ether was slowly added drop-wise to a stirred solution of sulfur (0.037 g, 1.2 mmol) in dry ether (30 ml) at room temperature. After the mixture was stirred for 36 h at room temperature, the clear yellow solution was filtered through Celite. The volatile components of the filtrate were removed under reduced pressure to afford the title complex as colorless crystals at −30°C (0.45 g, 71%). M.p. 320 K (decomposition). 1H NMR (298 K, CDCl3): δ = 7.29–6.96 (m, 24 H, Ar-H), 3.64 (m, 8 H, Me2CH), 0.98 (d, 24 H, CH3), 0.55 (d, 24 H, CH3) p.p.m.; 13C{1H} NMR (298 K, CDCl3): δ = 26.0 (s, (CH3)2C), 28.3 (s, (CH3)2C), 123.7, 125.1, 127.3, 130.0, 134.7, 135.5, 136.6, 147.6 (8 s, C for Ph ring) p.p.m. Elemental analysis (%): Calculated for C72H88Ge2N4S2Si4 (the solvent molecule was removed under high vacuum): C 67.76, H 6.90, N 4.39; found: C 67.74, H 6.88, N 4.38.
Refinement
Crystal data, data collection and structure . A difference Fourier synthesis following location of all the non-hydrogen atoms of the germanethione complex revealed additional peaks consistent with the presence of an acetonitrile solvent molecule. This solvent molecule was disordered about an inversion centre and was refined with equal occupancy for the atoms of each disorder component.
details are summarized in Table 1Structural data
CCDC reference: 1454736
https://doi.org/10.1107/S2414314616002996/sj4006sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616002996/sj4006Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616002996/sj4006Isup3.cml
Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).C72H88Ge2N4S2Si2·C2H3N | Z = 1 |
Mr = 1316.00 | F(000) = 694 |
Triclinic, P1 | Dx = 1.182 Mg m−3 |
Hall symbol: -P 1 | Melting point: 320 K |
a = 11.0447 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.4587 (6) Å | Cell parameters from 3142 reflections |
c = 13.9291 (6) Å | θ = 2.2–27.0° |
α = 64.297 (4)° | µ = 0.94 mm−1 |
β = 82.371 (4)° | T = 153 K |
γ = 85.629 (4)° | Block, colorless |
V = 1848.74 (14) Å3 | 0.15 × 0.13 × 0.11 mm |
Agilent SuperNova Dual Source diffractometer with an Eos detector | 5534 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.037 |
Graphite monochromator | θmax = 25.7°, θmin = 2.7° |
ω scans | h = −13→13 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −16→16 |
Tmin = 0.871, Tmax = 0.903 | l = −14→16 |
13757 measured reflections | 5839 standard reflections every 1 reflections |
7010 independent reflections | intensity decay: none |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.066P)2 + 1.4505P] where P = (Fo2 + 2Fc2)/3 |
7010 reflections | (Δ/σ)max = 0.001 |
405 parameters | Δρmax = 0.75 e Å−3 |
5 restraints | Δρmin = −0.38 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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) | |
C1 | 0.5999 (3) | 0.8105 (3) | 0.8258 (3) | 0.0343 (8) | |
C2 | 0.7166 (4) | 0.8406 (3) | 0.8332 (3) | 0.0432 (9) | |
C3 | 0.7231 (5) | 0.9309 (4) | 0.8568 (4) | 0.0664 (13) | |
H3 | 0.7992 | 0.9523 | 0.8620 | 0.080* | |
C4 | 0.6212 (6) | 0.9890 (4) | 0.8726 (4) | 0.0758 (15) | |
H4 | 0.6284 | 1.0488 | 0.8880 | 0.091* | |
C5 | 0.5104 (5) | 0.9585 (4) | 0.8656 (4) | 0.0649 (13) | |
H5 | 0.4415 | 0.9978 | 0.8770 | 0.078* | |
C6 | 0.4960 (4) | 0.8698 (3) | 0.8419 (3) | 0.0455 (9) | |
C7 | 0.3688 (4) | 0.8415 (3) | 0.8343 (3) | 0.0526 (10) | |
H7 | 0.3753 | 0.7737 | 0.8239 | 0.063* | |
C8 | 0.3135 (5) | 0.9325 (4) | 0.7373 (4) | 0.0771 (15) | |
H8A | 0.3124 | 1.0014 | 0.7425 | 0.116* | |
H8B | 0.2316 | 0.9138 | 0.7364 | 0.116* | |
H8C | 0.3621 | 0.9390 | 0.6724 | 0.116* | |
C9 | 0.2836 (5) | 0.8191 (5) | 0.9380 (5) | 0.0907 (19) | |
H9A | 0.2061 | 0.7952 | 0.9328 | 0.136* | |
H9B | 0.2721 | 0.8855 | 0.9481 | 0.136* | |
H9C | 0.3195 | 0.7627 | 0.9979 | 0.136* | |
C10 | 0.8328 (4) | 0.7778 (4) | 0.8211 (3) | 0.0529 (10) | |
H10 | 0.8167 | 0.7357 | 0.7819 | 0.063* | |
C11 | 0.8684 (5) | 0.6954 (4) | 0.9310 (4) | 0.0730 (14) | |
H11A | 0.8005 | 0.6490 | 0.9711 | 0.109* | |
H11B | 0.8902 | 0.7347 | 0.9693 | 0.109* | |
H11C | 0.9368 | 0.6507 | 0.9216 | 0.109* | |
C12 | 0.9418 (5) | 0.8525 (5) | 0.7581 (5) | 0.0852 (17) | |
H12A | 1.0091 | 0.8086 | 0.7455 | 0.128* | |
H12B | 0.9655 | 0.8884 | 0.7988 | 0.128* | |
H12C | 0.9187 | 0.9069 | 0.6907 | 0.128* | |
C13 | 0.6486 (4) | 0.4640 (3) | 0.7428 (3) | 0.0407 (8) | |
C14 | 0.5671 (4) | 0.3995 (4) | 0.7257 (4) | 0.0573 (11) | |
C15 | 0.6130 (6) | 0.3145 (5) | 0.7004 (6) | 0.0928 (19) | |
H15 | 0.5597 | 0.2724 | 0.6876 | 0.111* | |
C16 | 0.7335 (8) | 0.2918 (6) | 0.6940 (7) | 0.117 (3) | |
H16 | 0.7626 | 0.2342 | 0.6768 | 0.140* | |
C17 | 0.8142 (6) | 0.3521 (5) | 0.7124 (5) | 0.0923 (19) | |
H17 | 0.8972 | 0.3347 | 0.7076 | 0.111* | |
C18 | 0.7741 (4) | 0.4396 (3) | 0.7384 (4) | 0.0558 (11) | |
C19 | 0.4309 (5) | 0.4185 (5) | 0.7355 (5) | 0.0757 (15) | |
H19 | 0.4156 | 0.4803 | 0.7553 | 0.091* | |
C20 | 0.3639 (9) | 0.3199 (7) | 0.8245 (8) | 0.170 (5) | |
H20A | 0.3710 | 0.2591 | 0.8054 | 0.254* | |
H20B | 0.2792 | 0.3393 | 0.8342 | 0.254* | |
H20C | 0.3993 | 0.2992 | 0.8901 | 0.254* | |
C21 | 0.3781 (7) | 0.4528 (9) | 0.6297 (7) | 0.151 (4) | |
H21A | 0.4010 | 0.3988 | 0.6024 | 0.227* | |
H21B | 0.4095 | 0.5231 | 0.5789 | 0.227* | |
H21C | 0.2907 | 0.4580 | 0.6411 | 0.227* | |
C22 | 0.8674 (4) | 0.4998 (4) | 0.7626 (4) | 0.0694 (14) | |
H22 | 0.8293 | 0.5689 | 0.7602 | 0.083* | |
C23 | 0.9825 (6) | 0.5286 (7) | 0.6815 (6) | 0.135 (3) | |
H23A | 1.0348 | 0.4643 | 0.6977 | 0.203* | |
H23B | 1.0252 | 0.5858 | 0.6857 | 0.203* | |
H23C | 0.9596 | 0.5535 | 0.6105 | 0.203* | |
C24 | 0.9062 (5) | 0.4330 (5) | 0.8741 (5) | 0.0804 (15) | |
H24A | 0.9575 | 0.4766 | 0.8906 | 0.121* | |
H24B | 0.9505 | 0.3679 | 0.8765 | 0.121* | |
H24C | 0.8350 | 0.4121 | 0.9257 | 0.121* | |
C25 | 0.7362 (3) | 0.7545 (3) | 0.5812 (3) | 0.0386 (8) | |
C26 | 0.7889 (4) | 0.8533 (4) | 0.5569 (3) | 0.0545 (11) | |
H26 | 0.7620 | 0.8915 | 0.5978 | 0.065* | |
C27 | 0.8806 (5) | 0.8973 (5) | 0.4733 (4) | 0.0737 (15) | |
H27 | 0.9140 | 0.9646 | 0.4584 | 0.088* | |
C28 | 0.9219 (5) | 0.8424 (5) | 0.4131 (4) | 0.0829 (17) | |
H28 | 0.9851 | 0.8708 | 0.3581 | 0.100* | |
C29 | 0.8699 (6) | 0.7446 (5) | 0.4338 (4) | 0.0883 (19) | |
H29 | 0.8971 | 0.7076 | 0.3918 | 0.106* | |
C30 | 0.7771 (5) | 0.7006 (4) | 0.5170 (3) | 0.0645 (13) | |
H30 | 0.7420 | 0.6347 | 0.5299 | 0.077* | |
C31 | 0.4652 (3) | 0.7543 (3) | 0.6081 (3) | 0.0380 (8) | |
C32 | 0.3480 (4) | 0.7169 (4) | 0.6525 (3) | 0.0536 (10) | |
H32 | 0.3362 | 0.6614 | 0.7219 | 0.064* | |
C33 | 0.2480 (4) | 0.7609 (4) | 0.5951 (4) | 0.0670 (13) | |
H33 | 0.1702 | 0.7349 | 0.6262 | 0.080* | |
C34 | 0.2645 (5) | 0.8431 (4) | 0.4920 (4) | 0.0695 (14) | |
H34 | 0.1976 | 0.8722 | 0.4536 | 0.083* | |
C35 | 0.3779 (5) | 0.8816 (4) | 0.4464 (4) | 0.0703 (14) | |
H35 | 0.3886 | 0.9373 | 0.3770 | 0.084* | |
C36 | 0.4777 (4) | 0.8376 (3) | 0.5037 (3) | 0.0528 (10) | |
H36 | 0.5550 | 0.8643 | 0.4716 | 0.063* | |
C38 | −0.0273 (16) | −0.0191 (14) | 0.9955 (15) | 0.128 (6) | 0.50 |
H38A | −0.1136 | −0.0196 | 0.9925 | 0.193* | 0.50 |
H38B | 0.0120 | −0.0783 | 0.9814 | 0.193* | 0.50 |
H38C | −0.0128 | −0.0286 | 1.0654 | 0.193* | 0.50 |
Ge1 | 0.55890 (3) | 0.57094 (3) | 0.88889 (3) | 0.03020 (13) | |
N1 | 0.5904 (3) | 0.7178 (2) | 0.8016 (2) | 0.0311 (6) | |
N2 | 0.6031 (3) | 0.5576 (2) | 0.7626 (2) | 0.0343 (6) | |
N3 | 0.1041 (12) | 0.1467 (8) | 0.8636 (8) | 0.114 (4) | 0.50 |
S1 | 0.36302 (8) | 0.52913 (8) | 0.95938 (7) | 0.0412 (2) | |
Si1 | 0.60204 (9) | 0.69914 (7) | 0.68380 (7) | 0.0309 (2) | |
C37 | 0.0482 (11) | 0.0770 (9) | 0.9190 (9) | 0.158 (9) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.045 (2) | 0.0297 (17) | 0.0255 (16) | −0.0063 (15) | −0.0003 (14) | −0.0094 (13) |
C2 | 0.051 (2) | 0.044 (2) | 0.0345 (19) | −0.0137 (17) | −0.0031 (17) | −0.0147 (16) |
C3 | 0.081 (4) | 0.063 (3) | 0.067 (3) | −0.026 (3) | −0.012 (3) | −0.033 (2) |
C4 | 0.106 (5) | 0.057 (3) | 0.081 (4) | −0.011 (3) | −0.008 (3) | −0.046 (3) |
C5 | 0.087 (4) | 0.048 (3) | 0.067 (3) | 0.003 (2) | 0.000 (3) | −0.034 (2) |
C6 | 0.058 (3) | 0.037 (2) | 0.0371 (19) | −0.0023 (17) | 0.0035 (17) | −0.0134 (16) |
C7 | 0.046 (3) | 0.041 (2) | 0.062 (3) | 0.0037 (18) | 0.0064 (19) | −0.0183 (19) |
C8 | 0.066 (4) | 0.063 (3) | 0.091 (4) | 0.009 (3) | −0.019 (3) | −0.021 (3) |
C9 | 0.079 (4) | 0.081 (4) | 0.092 (4) | −0.005 (3) | 0.036 (3) | −0.030 (3) |
C10 | 0.045 (2) | 0.066 (3) | 0.052 (2) | −0.016 (2) | −0.0043 (19) | −0.027 (2) |
C11 | 0.066 (3) | 0.071 (3) | 0.080 (3) | 0.000 (3) | −0.024 (3) | −0.026 (3) |
C12 | 0.058 (3) | 0.113 (5) | 0.085 (4) | −0.036 (3) | 0.006 (3) | −0.041 (3) |
C13 | 0.050 (2) | 0.0343 (19) | 0.0366 (19) | −0.0032 (16) | 0.0024 (16) | −0.0155 (15) |
C14 | 0.066 (3) | 0.052 (2) | 0.063 (3) | −0.009 (2) | 0.000 (2) | −0.035 (2) |
C15 | 0.104 (5) | 0.081 (4) | 0.130 (5) | 0.001 (3) | −0.014 (4) | −0.078 (4) |
C16 | 0.124 (7) | 0.102 (5) | 0.170 (8) | 0.028 (5) | −0.019 (5) | −0.105 (6) |
C17 | 0.073 (4) | 0.089 (4) | 0.126 (5) | 0.025 (3) | −0.004 (4) | −0.063 (4) |
C18 | 0.050 (3) | 0.048 (2) | 0.065 (3) | 0.0047 (19) | 0.001 (2) | −0.023 (2) |
C19 | 0.065 (3) | 0.091 (4) | 0.098 (4) | −0.026 (3) | 0.003 (3) | −0.065 (3) |
C20 | 0.151 (8) | 0.147 (7) | 0.220 (11) | −0.093 (6) | 0.100 (8) | −0.107 (8) |
C21 | 0.083 (5) | 0.271 (11) | 0.178 (8) | 0.031 (6) | −0.054 (5) | −0.162 (9) |
C22 | 0.041 (3) | 0.057 (3) | 0.097 (4) | 0.002 (2) | −0.007 (2) | −0.021 (3) |
C23 | 0.058 (4) | 0.160 (7) | 0.119 (6) | −0.027 (4) | 0.002 (4) | 0.005 (5) |
C24 | 0.060 (3) | 0.090 (4) | 0.093 (4) | 0.004 (3) | −0.009 (3) | −0.041 (3) |
C25 | 0.037 (2) | 0.042 (2) | 0.0282 (17) | −0.0048 (15) | 0.0030 (14) | −0.0084 (15) |
C26 | 0.056 (3) | 0.062 (3) | 0.040 (2) | −0.023 (2) | 0.0070 (19) | −0.0171 (19) |
C27 | 0.064 (3) | 0.091 (4) | 0.052 (3) | −0.044 (3) | 0.007 (2) | −0.015 (3) |
C28 | 0.053 (3) | 0.112 (5) | 0.050 (3) | −0.017 (3) | 0.020 (2) | −0.008 (3) |
C29 | 0.097 (5) | 0.101 (4) | 0.051 (3) | 0.011 (4) | 0.028 (3) | −0.030 (3) |
C30 | 0.080 (4) | 0.060 (3) | 0.047 (2) | −0.011 (2) | 0.020 (2) | −0.023 (2) |
C31 | 0.040 (2) | 0.0387 (19) | 0.0339 (18) | −0.0034 (15) | −0.0050 (15) | −0.0139 (15) |
C32 | 0.042 (2) | 0.059 (3) | 0.050 (2) | −0.0059 (19) | −0.0017 (19) | −0.015 (2) |
C33 | 0.037 (3) | 0.079 (3) | 0.085 (4) | −0.005 (2) | −0.009 (2) | −0.034 (3) |
C34 | 0.059 (3) | 0.086 (4) | 0.070 (3) | 0.012 (3) | −0.032 (3) | −0.034 (3) |
C35 | 0.070 (4) | 0.078 (3) | 0.046 (3) | 0.008 (3) | −0.019 (2) | −0.009 (2) |
C36 | 0.048 (3) | 0.061 (3) | 0.038 (2) | −0.004 (2) | −0.0073 (18) | −0.0090 (19) |
C38 | 0.085 (13) | 0.118 (15) | 0.194 (19) | −0.046 (10) | −0.002 (13) | −0.074 (13) |
Ge1 | 0.0324 (2) | 0.0288 (2) | 0.02414 (18) | −0.00556 (14) | 0.00189 (13) | −0.00704 (14) |
N1 | 0.0337 (16) | 0.0311 (14) | 0.0255 (13) | −0.0047 (11) | 0.0001 (11) | −0.0096 (11) |
N2 | 0.0418 (18) | 0.0314 (15) | 0.0276 (14) | −0.0092 (12) | 0.0045 (12) | −0.0116 (12) |
N3 | 0.185 (14) | 0.074 (7) | 0.072 (7) | −0.027 (8) | 0.007 (7) | −0.023 (5) |
S1 | 0.0318 (5) | 0.0476 (5) | 0.0295 (4) | −0.0063 (4) | −0.0011 (4) | −0.0027 (4) |
Si1 | 0.0323 (5) | 0.0330 (5) | 0.0241 (4) | −0.0062 (4) | 0.0015 (4) | −0.0094 (4) |
C37 | 0.20 (2) | 0.103 (16) | 0.16 (2) | −0.043 (15) | 0.008 (18) | −0.046 (14) |
C1—C6 | 1.397 (5) | C21—H21C | 0.9600 |
C1—C2 | 1.410 (5) | C22—C24 | 1.520 (7) |
C1—N1 | 1.441 (4) | C22—C23 | 1.535 (8) |
C2—C3 | 1.399 (6) | C22—H22 | 0.9800 |
C2—C10 | 1.513 (6) | C23—H23A | 0.9600 |
C3—C4 | 1.368 (7) | C23—H23B | 0.9600 |
C3—H3 | 0.9300 | C23—H23C | 0.9600 |
C4—C5 | 1.349 (7) | C24—H24A | 0.9600 |
C4—H4 | 0.9300 | C24—H24B | 0.9600 |
C5—C6 | 1.395 (6) | C24—H24C | 0.9600 |
C5—H5 | 0.9300 | C25—C26 | 1.377 (5) |
C6—C7 | 1.511 (6) | C25—C30 | 1.391 (5) |
C7—C9 | 1.539 (6) | C25—Si1 | 1.864 (4) |
C7—C8 | 1.539 (6) | C26—C27 | 1.383 (6) |
C7—H7 | 0.9800 | C26—H26 | 0.9300 |
C8—H8A | 0.9600 | C27—C28 | 1.358 (8) |
C8—H8B | 0.9600 | C27—H27 | 0.9300 |
C8—H8C | 0.9600 | C28—C29 | 1.374 (8) |
C9—H9A | 0.9600 | C28—H28 | 0.9300 |
C9—H9B | 0.9600 | C29—C30 | 1.388 (7) |
C9—H9C | 0.9600 | C29—H29 | 0.9300 |
C10—C11 | 1.533 (6) | C30—H30 | 0.9300 |
C10—C12 | 1.538 (6) | C31—C32 | 1.388 (6) |
C10—H10 | 0.9800 | C31—C36 | 1.395 (5) |
C11—H11A | 0.9600 | C31—Si1 | 1.877 (4) |
C11—H11B | 0.9600 | C32—C33 | 1.391 (6) |
C11—H11C | 0.9600 | C32—H32 | 0.9300 |
C12—H12A | 0.9600 | C33—C34 | 1.379 (7) |
C12—H12B | 0.9600 | C33—H33 | 0.9300 |
C12—H12C | 0.9600 | C34—C35 | 1.357 (7) |
C13—C18 | 1.400 (6) | C34—H34 | 0.9300 |
C13—C14 | 1.405 (6) | C35—C36 | 1.388 (6) |
C13—N2 | 1.444 (4) | C35—H35 | 0.9300 |
C14—C15 | 1.380 (6) | C36—H36 | 0.9300 |
C14—C19 | 1.505 (7) | C38—C38i | 0.88 (3) |
C15—C16 | 1.343 (9) | C38—C37i | 1.11 (3) |
C15—H15 | 0.9300 | C38—C37 | 1.495 (9) |
C16—C17 | 1.367 (9) | C38—H38A | 0.9600 |
C16—H16 | 0.9300 | C38—H38B | 0.9599 |
C17—C18 | 1.400 (7) | C38—H38C | 0.9600 |
C17—H17 | 0.9300 | Ge1—N2 | 1.843 (3) |
C18—C22 | 1.514 (7) | Ge1—N1 | 1.847 (3) |
C19—C21 | 1.524 (9) | Ge1—S1ii | 2.2050 (9) |
C19—C20 | 1.525 (9) | Ge1—S1 | 2.2590 (10) |
C19—H19 | 0.9800 | Ge1—Si1 | 2.6179 (9) |
C20—H20A | 0.9600 | N1—Si1 | 1.752 (3) |
C20—H20B | 0.9600 | N2—Si1 | 1.738 (3) |
C20—H20C | 0.9600 | N3—C37 | 1.091 (9) |
C21—H21A | 0.9600 | S1—Ge1ii | 2.2050 (9) |
C21—H21B | 0.9600 | C37—C38i | 1.11 (3) |
C6—C1—C2 | 120.3 (3) | C23—C22—H22 | 107.9 |
C6—C1—N1 | 121.0 (3) | C22—C23—H23A | 109.5 |
C2—C1—N1 | 118.7 (3) | C22—C23—H23B | 109.5 |
C3—C2—C1 | 117.5 (4) | H23A—C23—H23B | 109.5 |
C3—C2—C10 | 119.2 (4) | C22—C23—H23C | 109.5 |
C1—C2—C10 | 123.3 (3) | H23A—C23—H23C | 109.5 |
C4—C3—C2 | 122.3 (5) | H23B—C23—H23C | 109.5 |
C4—C3—H3 | 118.9 | C22—C24—H24A | 109.5 |
C2—C3—H3 | 118.9 | C22—C24—H24B | 109.5 |
C5—C4—C3 | 119.3 (4) | H24A—C24—H24B | 109.5 |
C5—C4—H4 | 120.3 | C22—C24—H24C | 109.5 |
C3—C4—H4 | 120.3 | H24A—C24—H24C | 109.5 |
C4—C5—C6 | 122.1 (5) | H24B—C24—H24C | 109.5 |
C4—C5—H5 | 119.0 | C26—C25—C30 | 117.4 (4) |
C6—C5—H5 | 119.0 | C26—C25—Si1 | 123.3 (3) |
C5—C6—C1 | 118.6 (4) | C30—C25—Si1 | 118.8 (3) |
C5—C6—C7 | 118.9 (4) | C25—C26—C27 | 121.9 (4) |
C1—C6—C7 | 122.5 (3) | C25—C26—H26 | 119.0 |
C6—C7—C9 | 111.8 (4) | C27—C26—H26 | 119.0 |
C6—C7—C8 | 111.4 (4) | C28—C27—C26 | 120.0 (5) |
C9—C7—C8 | 110.4 (4) | C28—C27—H27 | 120.0 |
C6—C7—H7 | 107.7 | C26—C27—H27 | 120.0 |
C9—C7—H7 | 107.7 | C27—C28—C29 | 119.7 (4) |
C8—C7—H7 | 107.7 | C27—C28—H28 | 120.2 |
C7—C8—H8A | 109.5 | C29—C28—H28 | 120.2 |
C7—C8—H8B | 109.5 | C28—C29—C30 | 120.5 (5) |
H8A—C8—H8B | 109.5 | C28—C29—H29 | 119.7 |
C7—C8—H8C | 109.5 | C30—C29—H29 | 119.7 |
H8A—C8—H8C | 109.5 | C29—C30—C25 | 120.4 (5) |
H8B—C8—H8C | 109.5 | C29—C30—H30 | 119.8 |
C7—C9—H9A | 109.5 | C25—C30—H30 | 119.8 |
C7—C9—H9B | 109.5 | C32—C31—C36 | 117.0 (4) |
H9A—C9—H9B | 109.5 | C32—C31—Si1 | 122.5 (3) |
C7—C9—H9C | 109.5 | C36—C31—Si1 | 120.4 (3) |
H9A—C9—H9C | 109.5 | C31—C32—C33 | 121.2 (4) |
H9B—C9—H9C | 109.5 | C31—C32—H32 | 119.4 |
C2—C10—C11 | 110.7 (4) | C33—C32—H32 | 119.4 |
C2—C10—C12 | 113.7 (4) | C34—C33—C32 | 119.9 (4) |
C11—C10—C12 | 109.0 (4) | C34—C33—H33 | 120.0 |
C2—C10—H10 | 107.7 | C32—C33—H33 | 120.0 |
C11—C10—H10 | 107.7 | C35—C34—C33 | 120.3 (4) |
C12—C10—H10 | 107.7 | C35—C34—H34 | 119.9 |
C10—C11—H11A | 109.5 | C33—C34—H34 | 119.9 |
C10—C11—H11B | 109.5 | C34—C35—C36 | 119.8 (4) |
H11A—C11—H11B | 109.5 | C34—C35—H35 | 120.1 |
C10—C11—H11C | 109.5 | C36—C35—H35 | 120.1 |
H11A—C11—H11C | 109.5 | C35—C36—C31 | 121.8 (4) |
H11B—C11—H11C | 109.5 | C35—C36—H36 | 119.1 |
C10—C12—H12A | 109.5 | C31—C36—H36 | 119.1 |
C10—C12—H12B | 109.5 | C38i—C38—C37i | 97 (3) |
H12A—C12—H12B | 109.5 | C38i—C38—C37 | 47 (2) |
C10—C12—H12C | 109.5 | C37i—C38—C37 | 144.4 (16) |
H12A—C12—H12C | 109.5 | C38i—C38—H38A | 140.5 |
H12B—C12—H12C | 109.5 | C37i—C38—H38A | 85.0 |
C18—C13—C14 | 120.5 (4) | C37—C38—H38A | 121.2 |
C18—C13—N2 | 119.6 (3) | C38i—C38—H38B | 110.0 |
C14—C13—N2 | 119.9 (4) | C37i—C38—H38B | 89.8 |
C15—C14—C13 | 119.1 (5) | C37—C38—H38B | 101.7 |
C15—C14—C19 | 118.5 (5) | H38A—C38—H38B | 109.5 |
C13—C14—C19 | 122.4 (4) | C38i—C38—H38C | 58.0 |
C16—C15—C14 | 120.9 (6) | C37i—C38—H38C | 39.9 |
C16—C15—H15 | 119.6 | C37—C38—H38C | 104.9 |
C14—C15—H15 | 119.6 | H38A—C38—H38C | 109.5 |
C15—C16—C17 | 121.0 (5) | H38B—C38—H38C | 109.5 |
C15—C16—H16 | 119.5 | N2—Ge1—N1 | 82.41 (12) |
C17—C16—H16 | 119.5 | N2—Ge1—S1ii | 124.77 (9) |
C16—C17—C18 | 121.2 (6) | N1—Ge1—S1ii | 125.33 (9) |
C16—C17—H17 | 119.4 | N2—Ge1—S1 | 114.90 (10) |
C18—C17—H17 | 119.4 | N1—Ge1—S1 | 116.58 (9) |
C13—C18—C17 | 117.3 (5) | S1ii—Ge1—S1 | 94.97 (3) |
C13—C18—C22 | 124.1 (4) | N2—Ge1—Si1 | 41.47 (9) |
C17—C18—C22 | 118.6 (5) | N1—Ge1—Si1 | 41.92 (8) |
C14—C19—C21 | 112.4 (5) | S1ii—Ge1—Si1 | 146.78 (4) |
C14—C19—C20 | 112.5 (6) | S1—Ge1—Si1 | 118.22 (3) |
C21—C19—C20 | 110.9 (6) | C1—N1—Si1 | 135.0 (2) |
C14—C19—H19 | 106.8 | C1—N1—Ge1 | 131.7 (2) |
C21—C19—H19 | 106.8 | Si1—N1—Ge1 | 93.30 (12) |
C20—C19—H19 | 106.8 | C13—N2—Si1 | 133.6 (2) |
C19—C20—H20A | 109.5 | C13—N2—Ge1 | 131.2 (2) |
C19—C20—H20B | 109.5 | Si1—N2—Ge1 | 93.92 (13) |
H20A—C20—H20B | 109.5 | Ge1ii—S1—Ge1 | 85.03 (3) |
C19—C20—H20C | 109.5 | N2—Si1—N1 | 88.31 (13) |
H20A—C20—H20C | 109.5 | N2—Si1—C25 | 116.31 (15) |
H20B—C20—H20C | 109.5 | N1—Si1—C25 | 119.45 (15) |
C19—C21—H21A | 109.5 | N2—Si1—C31 | 114.79 (15) |
C19—C21—H21B | 109.5 | N1—Si1—C31 | 113.02 (15) |
H21A—C21—H21B | 109.5 | C25—Si1—C31 | 104.96 (16) |
C19—C21—H21C | 109.5 | N2—Si1—Ge1 | 44.61 (9) |
H21A—C21—H21C | 109.5 | N1—Si1—Ge1 | 44.78 (9) |
H21B—C21—H21C | 109.5 | C25—Si1—Ge1 | 138.43 (12) |
C18—C22—C24 | 111.4 (4) | C31—Si1—Ge1 | 116.59 (12) |
C18—C22—C23 | 113.1 (5) | N3—C37—C38i | 144.0 (16) |
C24—C22—C23 | 108.3 (5) | N3—C37—C38 | 179.4 (4) |
C18—C22—H22 | 107.9 | C38i—C37—C38 | 35.6 (16) |
C24—C22—H22 | 107.9 | ||
C6—C1—C2—C3 | 0.0 (5) | Si1—Ge1—N1—C1 | 179.5 (4) |
N1—C1—C2—C3 | 180.0 (3) | N2—Ge1—N1—Si1 | 10.54 (13) |
C6—C1—C2—C10 | 177.6 (3) | S1ii—Ge1—N1—Si1 | 138.19 (8) |
N1—C1—C2—C10 | −2.3 (5) | S1—Ge1—N1—Si1 | −103.55 (10) |
C1—C2—C3—C4 | 0.1 (7) | C18—C13—N2—Si1 | 76.5 (5) |
C10—C2—C3—C4 | −177.7 (4) | C14—C13—N2—Si1 | −102.1 (4) |
C2—C3—C4—C5 | 0.2 (8) | C18—C13—N2—Ge1 | −86.7 (4) |
C3—C4—C5—C6 | −0.5 (8) | C14—C13—N2—Ge1 | 94.7 (4) |
C4—C5—C6—C1 | 0.6 (7) | N1—Ge1—N2—C13 | 157.2 (3) |
C4—C5—C6—C7 | −179.4 (4) | S1ii—Ge1—N2—C13 | 29.1 (4) |
C2—C1—C6—C5 | −0.3 (5) | S1—Ge1—N2—C13 | −87.0 (3) |
N1—C1—C6—C5 | 179.7 (3) | Si1—Ge1—N2—C13 | 167.9 (4) |
C2—C1—C6—C7 | 179.7 (3) | N1—Ge1—N2—Si1 | −10.64 (13) |
N1—C1—C6—C7 | −0.4 (5) | S1ii—Ge1—N2—Si1 | −138.79 (8) |
C5—C6—C7—C9 | −56.7 (5) | S1—Ge1—N2—Si1 | 105.20 (11) |
C1—C6—C7—C9 | 123.4 (4) | N2—Ge1—S1—Ge1ii | 132.18 (10) |
C5—C6—C7—C8 | 67.3 (5) | N1—Ge1—S1—Ge1ii | −133.84 (9) |
C1—C6—C7—C8 | −112.7 (4) | S1ii—Ge1—S1—Ge1ii | 0.0 |
C3—C2—C10—C11 | 81.3 (5) | Si1—Ge1—S1—Ge1ii | 178.67 (3) |
C1—C2—C10—C11 | −96.3 (4) | C13—N2—Si1—N1 | −156.2 (3) |
C3—C2—C10—C12 | −41.8 (5) | Ge1—N2—Si1—N1 | 11.13 (13) |
C1—C2—C10—C12 | 140.6 (4) | C13—N2—Si1—C25 | −34.0 (4) |
C18—C13—C14—C15 | −2.5 (7) | Ge1—N2—Si1—C25 | 133.41 (15) |
N2—C13—C14—C15 | 176.1 (4) | C13—N2—Si1—C31 | 89.1 (4) |
C18—C13—C14—C19 | 176.5 (5) | Ge1—N2—Si1—C31 | −103.53 (16) |
N2—C13—C14—C19 | −4.8 (6) | C13—N2—Si1—Ge1 | −167.4 (4) |
C13—C14—C15—C16 | 1.2 (10) | C1—N1—Si1—N2 | 169.4 (3) |
C19—C14—C15—C16 | −177.9 (7) | Ge1—N1—Si1—N2 | −11.09 (13) |
C14—C15—C16—C17 | 0.1 (12) | C1—N1—Si1—C25 | 49.9 (4) |
C15—C16—C17—C18 | −0.1 (12) | Ge1—N1—Si1—C25 | −130.60 (15) |
C14—C13—C18—C17 | 2.4 (7) | C1—N1—Si1—C31 | −74.3 (4) |
N2—C13—C18—C17 | −176.2 (4) | Ge1—N1—Si1—C31 | 105.21 (15) |
C14—C13—C18—C22 | −175.9 (4) | C1—N1—Si1—Ge1 | −179.5 (4) |
N2—C13—C18—C22 | 5.4 (6) | C26—C25—Si1—N2 | −141.4 (3) |
C16—C17—C18—C13 | −1.2 (9) | C30—C25—Si1—N2 | 46.3 (4) |
C16—C17—C18—C22 | 177.3 (6) | C26—C25—Si1—N1 | −37.4 (4) |
C15—C14—C19—C21 | −64.4 (8) | C30—C25—Si1—N1 | 150.2 (3) |
C13—C14—C19—C21 | 116.5 (6) | C26—C25—Si1—C31 | 90.6 (4) |
C15—C14—C19—C20 | 61.7 (7) | C30—C25—Si1—C31 | −81.8 (4) |
C13—C14—C19—C20 | −117.4 (6) | C26—C25—Si1—Ge1 | −91.1 (4) |
C13—C18—C22—C24 | 101.9 (5) | C30—C25—Si1—Ge1 | 96.5 (3) |
C17—C18—C22—C24 | −76.4 (6) | C32—C31—Si1—N2 | 40.0 (4) |
C13—C18—C22—C23 | −135.8 (5) | C36—C31—Si1—N2 | −141.3 (3) |
C17—C18—C22—C23 | 45.9 (7) | C32—C31—Si1—N1 | −59.3 (4) |
C30—C25—C26—C27 | −1.2 (7) | C36—C31—Si1—N1 | 119.4 (3) |
Si1—C25—C26—C27 | −173.6 (4) | C32—C31—Si1—C25 | 168.9 (3) |
C25—C26—C27—C28 | −0.6 (8) | C36—C31—Si1—C25 | −12.4 (4) |
C26—C27—C28—C29 | 1.8 (9) | C32—C31—Si1—Ge1 | −9.8 (4) |
C27—C28—C29—C30 | −1.2 (9) | C36—C31—Si1—Ge1 | 168.9 (3) |
C28—C29—C30—C25 | −0.6 (9) | N1—Ge1—Si1—N2 | 164.10 (19) |
C26—C25—C30—C29 | 1.7 (7) | S1ii—Ge1—Si1—N2 | 81.03 (15) |
Si1—C25—C30—C29 | 174.5 (4) | S1—Ge1—Si1—N2 | −96.56 (15) |
C36—C31—C32—C33 | −0.1 (6) | N2—Ge1—Si1—N1 | −164.10 (19) |
Si1—C31—C32—C33 | 178.7 (3) | S1ii—Ge1—Si1—N1 | −83.07 (14) |
C31—C32—C33—C34 | 0.1 (7) | S1—Ge1—Si1—N1 | 99.34 (13) |
C32—C33—C34—C35 | −0.3 (8) | N2—Ge1—Si1—C25 | −78.9 (2) |
C33—C34—C35—C36 | 0.3 (8) | N1—Ge1—Si1—C25 | 85.2 (2) |
C34—C35—C36—C31 | −0.3 (8) | S1ii—Ge1—Si1—C25 | 2.1 (2) |
C32—C31—C36—C35 | 0.1 (6) | S1—Ge1—Si1—C25 | −175.49 (18) |
Si1—C31—C36—C35 | −178.7 (4) | N2—Ge1—Si1—C31 | 99.21 (19) |
C6—C1—N1—Si1 | 95.0 (4) | N1—Ge1—Si1—C31 | −96.68 (18) |
C2—C1—N1—Si1 | −85.0 (4) | S1ii—Ge1—Si1—C31 | −179.76 (13) |
C6—C1—N1—Ge1 | −84.3 (4) | S1—Ge1—Si1—C31 | 2.66 (14) |
C2—C1—N1—Ge1 | 95.7 (4) | C38i—C38—C37—N3 | 45 (39) |
N2—Ge1—N1—C1 | −170.0 (3) | C37i—C38—C37—N3 | 45 (39) |
S1ii—Ge1—N1—C1 | −42.3 (3) | C37i—C38—C37—C38i | 0.000 (8) |
S1—Ge1—N1—C1 | 76.0 (3) |
Symmetry codes: (i) −x, −y, −z+2; (ii) −x+1, −y+1, −z+2. |
Acknowledgements
This work was supported by the National Natural Science Foundation of China (NSFC; grant No. 21272143).
References
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Al-Rafia, S. M. I., Lummis, P. A., Ferguson, M. J., McDonald, R. & Rivard, E. (2010). Inorg. Chem. 49, 9709–9717. CAS PubMed Google Scholar
Bazinet, P., Yap, G. P. A. & Richeson, D. S. (2001). J. Am. Chem. Soc. 123, 11162–11167. CrossRef PubMed CAS Google Scholar
Sen, S. S., Ghadwal, R. S., Kratzert, D., Stern, D., Roesky, H. W. & Stalke, D. (2011). Organometallics, 30, 1030–1033. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wegner, G. L., Jockisch, A., Schier, A. & Schmidbaur, H. (2000). Z. Naturforsch. Teil B, 55, 347–351. CAS Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Yang, D., Guo, J., Wu, H., Ding, Y. & Zheng, W. (2012). Dalton Trans. 41, 2187–2194. CrossRef CAS PubMed Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.