Literature DB >> 26870500

Crystal structure of 4,8-di-tert-butyl-6,6-di-chloro-13-ethyl-2,10-dimethyl-13,14-di-hydro-12H-dibenzo[d,i][1,3,7,2]dioxaza-silecine toluene 0.25-solvate.

Ekaterina A Kuchuk1, Kirill V Zaitsev1, Sergey S Karlov1, Mikhail P Egorov2, Andrei V Churakov3.   

Abstract

The coordination polyhedron at the silicon atom in the title compound, C26H37Cl2NO2Si·0.25C7H8, is typical for penta-coordinated silicon derivatives and represents a slightly distorted trigonal bipyramid with an N atom and a Cl atom in the apical positions and the two O atoms and the other Cl atom occupying the equatorial sites. There are two independent mol-ecules in the asymmetric unit. The N-Si-Cl fragment in each is close to linear [178.24 (5) and 178.71 (5)°], in good agreement with 4e-3c theory, as is the elongation of the apical bond lengths [Si-Cl = 2.1663 (7) and 2.1797 (7) Å] in comparison with the equatorial bonds [Si-Cl = 2.0784 (7) and 2.0748 (7) Å]. Orthogonal least-squares fitting of the two independent mol-ecules resulted in r.m.s. deviation of 0.017 Å. The conformations of the two mol-ecules are almost the same, with corresponding torsion angles differing by less than 5.5°. The toluene solvent mol-ecule is disordered about an inversion centre.

Entities:  

Keywords:  crystal structure; heavy carbenes; penta­coordinated silicon

Year:  2015        PMID: 26870500      PMCID: PMC4719981          DOI: 10.1107/S2056989015023889

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Related literature

For general background to the chemistry affording the 2,2-[(alkyl­imino)­dimethanedi­yl]diphenols as ligands, see: Wichmann et al. (2012 ▸). For hypervalent silicon compounds, see: Holmes (1996 ▸); Rendler & Oestreich (2005 ▸); Selina et al. (2006 ▸). The title compound was obtained as part of our study of the ability of different types of tridentate ligands to stabilize ‘heavier carbenes’, see: Huang et al. (2012 ▸, 2013 ▸); Kireenko et al. (2013 ▸).

Experimental

Crystal data

2C26H37Cl2NO2Si·0.5C7H8 M = 1035.18 Triclinic, a = 13.9017 (9) Å b = 13.9542 (9) Å c = 16.9827 (11) Å α = 69.649 (1)° β = 65.978 (1)° γ = 83.585 (1)° V = 2819.6 (3) Å3 Z = 2 Mo Kα radiation μ = 0.30 mm−1 T = 150 K 0.35 × 0.35 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▸) T min = 0.903, T max = 0.943 27366 measured reflections 12314 independent reflections 9442 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043 wR(F 2) = 0.109 S = 1.04 12314 reflections 659 parameters 15 restraints H-atom parameters constrained Δρmax = 0.33 e Å−3 Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2008 ▸); cell refinement: SAINT (Bruker, 2008 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL. Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015023889/zp2021sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015023889/zp2021Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015023889/zp2021Isup3.mol Click here for additional data file. Supporting information file. DOI: 10.1107/S2056989015023889/zp2021Isup4.cml Click here for additional data file. . DOI: 10.1107/S2056989015023889/zp2021fig1.tif The mol­ecular structure of one of the independent mol­ecules of the title compound, with displacement ellipsoids shown at the 50% probability level. The toluene solvent mol­ecule and hydrogen atoms are omitted for clarity. CCDC reference: 1442032 Additional supporting information: crystallographic information; 3D view; checkCIF report
2C26H37Cl2NO2Si·0.5C7H8Z = 2
Mr = 1035.18F(000) = 1106
Triclinic, P1Dx = 1.219 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.9017 (9) ÅCell parameters from 5818 reflections
b = 13.9542 (9) Åθ = 2.2–27.9°
c = 16.9827 (11) ŵ = 0.30 mm1
α = 69.649 (1)°T = 150 K
β = 65.978 (1)°Block, colourless
γ = 83.585 (1)°0.35 × 0.35 × 0.20 mm
V = 2819.6 (3) Å3
Bruker SMART APEXII diffractometer12314 independent reflections
Radiation source: fine-focus sealed tube9442 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω scansθmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −17→17
Tmin = 0.903, Tmax = 0.943k = −17→17
27366 measured reflectionsl = −21→21
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) = 0.109H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.049P)2 + 0.4643P] where P = (Fo2 + 2Fc2)/3
12314 reflections(Δ/σ)max = 0.001
659 parametersΔρmax = 0.33 e Å3
15 restraintsΔρmin = −0.27 e Å3
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.
xyzUiso*/UeqOcc. (<1)
Si10.19585 (4)0.68718 (4)0.22126 (3)0.02161 (12)
Cl110.05925 (4)0.58326 (4)0.29544 (3)0.02928 (12)
Cl120.13951 (4)0.76756 (4)0.12122 (4)0.03714 (13)
O110.16095 (10)0.72681 (9)0.30901 (8)0.0253 (3)
O120.27134 (9)0.58945 (9)0.21036 (8)0.0242 (3)
N10.32674 (11)0.78269 (11)0.15403 (10)0.0206 (3)
C10.37796 (14)0.79998 (14)0.05230 (12)0.0246 (4)
H1A0.33390.84640.02290.029*
H1B0.37830.73370.04300.029*
C20.49005 (15)0.84486 (15)0.00403 (13)0.0279 (4)
H2A0.51220.8637−0.06220.042*
H2B0.53740.79400.02390.042*
H2C0.49280.90580.01930.042*
C110.19693 (14)0.79602 (14)0.33347 (13)0.0231 (4)
C120.26165 (14)0.87820 (13)0.26483 (12)0.0233 (4)
C130.29633 (14)0.94926 (14)0.28856 (13)0.0274 (4)
H130.34071.00550.24190.033*
C140.26703 (15)0.93927 (15)0.37945 (14)0.0293 (4)
C150.20453 (14)0.85404 (14)0.44615 (13)0.0265 (4)
H150.18600.84600.50850.032*
C160.16763 (14)0.77981 (14)0.42635 (12)0.0227 (4)
C170.29669 (15)0.88514 (13)0.16676 (13)0.0260 (4)
H17A0.35790.93380.12840.031*
H17B0.23900.91200.14600.031*
C180.30313 (19)1.01687 (18)0.40609 (16)0.0451 (6)
H18A0.30611.08520.36180.068*
H18B0.37331.00010.40660.068*
H18C0.25341.01570.46720.068*
C190.09926 (14)0.68634 (14)0.50205 (12)0.0232 (4)
C210.37690 (14)0.56835 (13)0.18610 (12)0.0214 (4)
C220.44557 (14)0.63868 (13)0.17896 (11)0.0201 (4)
C230.55179 (14)0.61776 (14)0.15658 (12)0.0227 (4)
H230.59880.66620.15150.027*
C240.58972 (14)0.52621 (14)0.14157 (12)0.0239 (4)
C250.51845 (15)0.45813 (14)0.14912 (12)0.0255 (4)
H250.54420.39570.13880.031*
C260.41128 (14)0.47537 (13)0.17086 (12)0.0224 (4)
C270.40367 (14)0.73555 (13)0.19768 (12)0.0211 (4)
H27A0.46300.78490.17380.025*
H27B0.36820.72090.26460.025*
C280.70451 (15)0.50268 (16)0.11784 (15)0.0330 (5)
H28A0.74790.56190.06920.050*
H28B0.71990.44340.09680.050*
H28C0.72040.48740.17210.050*
C290.33642 (15)0.39742 (15)0.17690 (13)0.0279 (4)
C51−0.00963 (14)0.68871 (15)0.49817 (13)0.0280 (4)
H51A−0.00120.68690.43850.042*
H51B−0.04430.75150.50690.042*
H51C−0.05280.62920.54660.042*
C520.15263 (16)0.58609 (15)0.49100 (14)0.0311 (4)
H52A0.16120.58240.43190.047*
H52B0.10870.52760.54040.047*
H52C0.22190.58450.49370.047*
C530.08142 (17)0.68508 (16)0.59760 (13)0.0334 (5)
H53A0.03940.62370.64360.050*
H53B0.04380.74610.60820.050*
H53C0.14960.68470.60200.050*
C540.28570 (18)0.44778 (18)0.10799 (15)0.0395 (5)
H54A0.34100.47570.04660.059*
H54B0.24150.50320.12480.059*
H54C0.24220.39670.10850.059*
C550.25061 (18)0.35823 (16)0.27391 (14)0.0403 (5)
H55A0.28340.32300.31720.060*
H55B0.20210.31060.27610.060*
H55C0.21160.41610.29040.060*
C560.39518 (18)0.30526 (17)0.15303 (19)0.0474 (6)
H56A0.44930.32850.09060.071*
H56B0.34530.25750.15730.071*
H56C0.42870.27080.19590.071*
Si20.66618 (4)0.86357 (4)0.23586 (4)0.02274 (12)
Cl210.60060 (4)0.96967 (4)0.14308 (3)0.03124 (12)
Cl220.51693 (4)0.80356 (4)0.32911 (3)0.03298 (12)
O210.73042 (10)0.81090 (9)0.15725 (9)0.0271 (3)
O220.71224 (10)0.96067 (9)0.24424 (9)0.0277 (3)
N20.73095 (12)0.76561 (11)0.32095 (10)0.0222 (3)
C30.67413 (15)0.75990 (15)0.41947 (12)0.0272 (4)
H3A0.60580.72260.44490.033*
H3B0.65870.83030.42110.033*
C40.73222 (17)0.70847 (17)0.48170 (14)0.0365 (5)
H4A0.68510.70000.54520.055*
H4B0.79400.75100.46390.055*
H4C0.75490.64130.47600.055*
C310.79903 (14)0.73245 (14)0.14741 (13)0.0246 (4)
C320.79811 (15)0.65335 (14)0.22523 (13)0.0242 (4)
C330.86638 (15)0.57413 (15)0.21636 (14)0.0288 (4)
H330.86570.52030.26950.035*
C340.93526 (16)0.57225 (16)0.13141 (15)0.0323 (5)
C350.93625 (15)0.65319 (16)0.05522 (15)0.0321 (5)
H350.98550.6528−0.00320.039*
C360.86891 (15)0.73541 (15)0.05932 (13)0.0277 (4)
C370.72758 (15)0.65970 (14)0.31734 (13)0.0258 (4)
H37A0.74980.61010.36440.031*
H37B0.65430.64090.33150.031*
C381.0096 (2)0.4855 (2)0.12239 (18)0.0517 (7)
H38A1.04190.47090.16680.078*
H38B1.06470.50480.06040.078*
H38C0.97040.42440.13410.078*
C390.87329 (16)0.82352 (16)−0.02677 (14)0.0358 (5)
C410.78091 (14)0.97685 (14)0.27893 (12)0.0235 (4)
C420.85004 (14)0.90168 (14)0.29709 (12)0.0228 (4)
C430.92354 (14)0.91930 (14)0.32735 (12)0.0241 (4)
H430.97170.86800.33890.029*
C440.92693 (15)1.01084 (15)0.34079 (12)0.0250 (4)
C450.85391 (14)1.08397 (14)0.32416 (12)0.0260 (4)
H450.85501.14630.33470.031*
C460.77966 (14)1.07051 (14)0.29293 (13)0.0250 (4)
C470.84438 (14)0.80205 (14)0.28365 (13)0.0239 (4)
H47A0.88300.75010.31530.029*
H47B0.87840.81090.21770.029*
C481.00732 (17)1.03121 (16)0.37228 (15)0.0351 (5)
H48A1.05170.97190.38000.053*
H48B0.97101.04340.43080.053*
H48C1.05141.09160.32660.053*
C490.70090 (17)1.15270 (16)0.27494 (16)0.0369 (5)
C610.76516 (17)0.83455 (17)−0.03338 (14)0.0369 (5)
H61A0.71350.85430.01780.055*
H61B0.74250.7691−0.03090.055*
H61C0.77070.8872−0.09120.055*
C620.9068 (2)0.92360 (18)−0.02516 (18)0.0550 (7)
H62A0.85440.93990.02760.083*
H62B0.91200.9790−0.08150.083*
H62C0.97550.9158−0.02060.083*
C630.9513 (2)0.8040 (2)−0.11370 (16)0.0634 (8)
H63A1.02220.7984−0.11380.095*
H63B0.95090.8609−0.16740.095*
H63C0.93070.7402−0.11570.095*
C640.7148 (2)1.24614 (18)0.2974 (2)0.0546 (7)
H64A0.78701.27440.26060.082*
H64B0.70131.22570.36250.082*
H64C0.66511.29810.28360.082*
C650.7177 (2)1.18947 (17)0.17336 (18)0.0509 (7)
H65A0.78861.22080.13540.076*
H65B0.66521.24000.16340.076*
H65C0.71011.13100.15670.076*
C660.58778 (18)1.1097 (2)0.3360 (2)0.0555 (7)
H66A0.57941.08300.40010.083*
H66B0.57371.05450.31860.083*
H66C0.53801.16420.32840.083*
C710.4903 (3)0.5234 (3)0.5414 (3)0.0369 (10)0.50
C720.438 (2)0.562 (2)0.4837 (16)0.040 (4)0.50
H720.38950.61420.49230.048*0.50
C730.4569 (4)0.5248 (4)0.4135 (4)0.0494 (13)0.50
H730.41980.55060.37460.059*0.50
C740.5291 (11)0.4508 (12)0.4005 (9)0.051 (3)0.50
H740.54140.42460.35270.061*0.50
C750.5841 (4)0.4137 (4)0.4556 (4)0.0457 (12)0.50
H750.63520.36330.44540.055*0.50
C760.564 (2)0.4509 (19)0.5261 (16)0.038 (3)0.50
H760.60170.42580.56450.045*0.50
C770.4664 (14)0.5609 (13)0.6206 (11)0.054 (3)0.50
H77A0.47180.63580.59840.081*0.50
H77B0.51700.53330.64890.081*0.50
H77C0.39480.53800.66590.081*0.50
U11U22U33U12U13U23
Si10.0199 (3)0.0228 (3)0.0223 (3)0.0003 (2)−0.0087 (2)−0.0071 (2)
Cl110.0228 (2)0.0321 (3)0.0331 (3)−0.00531 (19)−0.0087 (2)−0.0119 (2)
Cl120.0303 (3)0.0441 (3)0.0354 (3)−0.0001 (2)−0.0197 (2)−0.0029 (2)
O110.0252 (7)0.0234 (7)0.0240 (7)−0.0061 (5)−0.0042 (5)−0.0085 (5)
O120.0206 (6)0.0223 (7)0.0300 (7)−0.0006 (5)−0.0086 (6)−0.0104 (6)
N10.0214 (8)0.0189 (8)0.0196 (8)0.0023 (6)−0.0073 (6)−0.0055 (6)
C10.0272 (10)0.0248 (10)0.0183 (9)0.0016 (8)−0.0081 (8)−0.0045 (8)
C20.0277 (10)0.0251 (10)0.0238 (10)0.0012 (8)−0.0065 (8)−0.0044 (8)
C110.0202 (9)0.0210 (9)0.0303 (10)0.0028 (7)−0.0105 (8)−0.0111 (8)
C120.0196 (9)0.0207 (9)0.0265 (10)0.0037 (7)−0.0070 (8)−0.0077 (8)
C130.0224 (9)0.0202 (9)0.0333 (11)−0.0002 (7)−0.0055 (8)−0.0081 (8)
C140.0241 (10)0.0262 (10)0.0370 (11)−0.0004 (8)−0.0081 (9)−0.0144 (9)
C150.0240 (10)0.0288 (10)0.0281 (10)0.0013 (8)−0.0092 (8)−0.0124 (8)
C160.0184 (9)0.0222 (9)0.0260 (10)0.0028 (7)−0.0073 (8)−0.0086 (8)
C170.0273 (10)0.0169 (9)0.0285 (10)0.0021 (7)−0.0083 (8)−0.0049 (8)
C180.0478 (14)0.0434 (13)0.0445 (13)−0.0174 (11)−0.0081 (11)−0.0216 (11)
C190.0222 (9)0.0220 (9)0.0237 (10)0.0005 (7)−0.0089 (8)−0.0058 (8)
C210.0207 (9)0.0227 (9)0.0195 (9)0.0008 (7)−0.0083 (7)−0.0053 (7)
C220.0245 (9)0.0192 (9)0.0172 (9)0.0003 (7)−0.0101 (7)−0.0042 (7)
C230.0255 (9)0.0222 (9)0.0219 (9)−0.0014 (7)−0.0127 (8)−0.0045 (7)
C240.0261 (10)0.0239 (10)0.0247 (10)0.0029 (8)−0.0140 (8)−0.0074 (8)
C250.0303 (10)0.0223 (9)0.0278 (10)0.0053 (8)−0.0156 (8)−0.0093 (8)
C260.0275 (10)0.0210 (9)0.0200 (9)0.0000 (7)−0.0115 (8)−0.0057 (7)
C270.0229 (9)0.0200 (9)0.0211 (9)−0.0001 (7)−0.0106 (8)−0.0050 (7)
C280.0288 (11)0.0304 (11)0.0469 (13)0.0074 (9)−0.0204 (10)−0.0166 (10)
C290.0290 (10)0.0263 (10)0.0336 (11)−0.0012 (8)−0.0123 (9)−0.0155 (9)
C510.0218 (9)0.0303 (10)0.0266 (10)−0.0002 (8)−0.0070 (8)−0.0062 (8)
C520.0290 (11)0.0256 (10)0.0352 (11)0.0019 (8)−0.0118 (9)−0.0075 (9)
C530.0397 (12)0.0321 (11)0.0271 (10)−0.0046 (9)−0.0139 (9)−0.0057 (9)
C540.0392 (12)0.0493 (14)0.0411 (13)−0.0034 (10)−0.0201 (10)−0.0213 (11)
C550.0443 (13)0.0313 (12)0.0376 (12)−0.0132 (10)−0.0078 (10)−0.0082 (10)
C560.0367 (13)0.0394 (13)0.0801 (18)0.0025 (10)−0.0223 (13)−0.0374 (13)
Si20.0236 (3)0.0207 (3)0.0264 (3)0.0031 (2)−0.0142 (2)−0.0062 (2)
Cl210.0355 (3)0.0273 (2)0.0362 (3)0.0078 (2)−0.0241 (2)−0.0069 (2)
Cl220.0254 (2)0.0379 (3)0.0346 (3)−0.0002 (2)−0.0151 (2)−0.0064 (2)
O210.0324 (7)0.0235 (7)0.0259 (7)0.0078 (6)−0.0154 (6)−0.0064 (6)
O220.0307 (7)0.0213 (7)0.0401 (8)0.0049 (6)−0.0249 (6)−0.0087 (6)
N20.0232 (8)0.0192 (8)0.0252 (8)0.0015 (6)−0.0128 (7)−0.0049 (6)
C30.0280 (10)0.0287 (10)0.0242 (10)0.0009 (8)−0.0117 (8)−0.0065 (8)
C40.0407 (12)0.0401 (12)0.0295 (11)−0.0002 (10)−0.0198 (10)−0.0047 (9)
C310.0244 (10)0.0206 (9)0.0340 (11)0.0018 (7)−0.0158 (8)−0.0102 (8)
C320.0258 (10)0.0209 (9)0.0301 (10)−0.0011 (7)−0.0158 (8)−0.0070 (8)
C330.0332 (11)0.0248 (10)0.0408 (12)0.0041 (8)−0.0257 (10)−0.0128 (9)
C340.0294 (11)0.0348 (11)0.0472 (13)0.0099 (9)−0.0246 (10)−0.0219 (10)
C350.0241 (10)0.0414 (12)0.0374 (12)0.0035 (9)−0.0129 (9)−0.0205 (10)
C360.0227 (10)0.0293 (10)0.0326 (11)−0.0012 (8)−0.0121 (8)−0.0102 (9)
C370.0306 (10)0.0183 (9)0.0288 (10)0.0005 (8)−0.0146 (8)−0.0047 (8)
C380.0521 (15)0.0574 (16)0.0641 (17)0.0314 (13)−0.0354 (13)−0.0357 (14)
C390.0305 (11)0.0362 (12)0.0301 (11)−0.0016 (9)−0.0053 (9)−0.0058 (9)
C410.0233 (9)0.0228 (9)0.0257 (10)0.0003 (7)−0.0132 (8)−0.0054 (8)
C420.0235 (9)0.0202 (9)0.0231 (9)0.0011 (7)−0.0098 (8)−0.0048 (7)
C430.0220 (9)0.0257 (10)0.0239 (10)0.0036 (8)−0.0112 (8)−0.0058 (8)
C440.0256 (10)0.0296 (10)0.0204 (9)−0.0003 (8)−0.0099 (8)−0.0078 (8)
C450.0282 (10)0.0241 (10)0.0269 (10)0.0011 (8)−0.0104 (8)−0.0104 (8)
C460.0243 (10)0.0226 (10)0.0268 (10)0.0021 (8)−0.0104 (8)−0.0069 (8)
C470.0217 (9)0.0226 (9)0.0290 (10)0.0035 (7)−0.0140 (8)−0.0063 (8)
C480.0380 (12)0.0365 (12)0.0437 (13)0.0071 (9)−0.0259 (10)−0.0184 (10)
C490.0356 (12)0.0267 (11)0.0608 (15)0.0110 (9)−0.0281 (11)−0.0209 (10)
C610.0422 (13)0.0394 (12)0.0266 (11)0.0054 (10)−0.0155 (10)−0.0068 (9)
C620.0530 (15)0.0389 (14)0.0603 (17)−0.0166 (12)−0.0214 (13)0.0029 (12)
C630.0490 (16)0.075 (2)0.0319 (13)0.0121 (14)0.0024 (12)−0.0035 (13)
C640.0608 (16)0.0366 (13)0.095 (2)0.0250 (12)−0.0511 (16)−0.0375 (14)
C650.0695 (17)0.0269 (12)0.0738 (18)0.0110 (11)−0.0537 (15)−0.0094 (12)
C660.0309 (13)0.0536 (16)0.089 (2)0.0167 (11)−0.0228 (13)−0.0372 (15)
C710.033 (2)0.038 (3)0.025 (2)−0.009 (2)−0.002 (2)−0.002 (2)
C720.032 (6)0.029 (5)0.043 (8)−0.003 (4)−0.008 (4)0.000 (4)
C730.042 (3)0.057 (3)0.037 (3)−0.016 (3)−0.018 (2)0.006 (3)
C740.052 (5)0.060 (6)0.032 (7)−0.024 (4)0.000 (5)−0.016 (4)
C750.036 (3)0.034 (3)0.055 (3)0.001 (2)−0.006 (2)−0.015 (3)
C760.026 (5)0.038 (7)0.038 (6)−0.004 (4)−0.011 (4)0.000 (4)
C770.060 (5)0.054 (5)0.032 (6)−0.007 (4)0.000 (4)−0.017 (4)
Si1—O111.6391 (13)N2—C31.508 (2)
Si1—O121.6412 (13)N2—C471.513 (2)
Si1—N12.0452 (15)C3—C41.524 (3)
Si1—Cl122.0784 (7)C3—H3A0.9900
Si1—Cl112.1663 (7)C3—H3B0.9900
O11—C111.383 (2)C4—H4A0.9800
O12—C211.380 (2)C4—H4B0.9800
N1—C171.508 (2)C4—H4C0.9800
N1—C271.508 (2)C31—C321.393 (3)
N1—C11.516 (2)C31—C361.402 (3)
C1—C21.521 (3)C32—C331.382 (3)
C1—H1A0.9900C32—C371.498 (3)
C1—H1B0.9900C33—C341.376 (3)
C2—H2A0.9800C33—H330.9500
C2—H2B0.9800C34—C351.387 (3)
C2—H2C0.9800C34—C381.509 (3)
C11—C121.389 (2)C35—C361.400 (3)
C11—C161.398 (3)C35—H350.9500
C12—C131.386 (3)C36—C391.532 (3)
C12—C171.503 (3)C37—H37A0.9900
C13—C141.385 (3)C37—H37B0.9900
C13—H130.9500C38—H38A0.9800
C14—C151.395 (3)C38—H38B0.9800
C14—C181.509 (3)C38—H38C0.9800
C15—C161.396 (3)C39—C631.530 (3)
C15—H150.9500C39—C621.533 (3)
C16—C191.541 (2)C39—C611.539 (3)
C17—H17A0.9900C41—C421.382 (2)
C17—H17B0.9900C41—C461.405 (3)
C18—H18A0.9800C42—C431.393 (3)
C18—H18B0.9800C42—C471.500 (2)
C18—H18C0.9800C43—C441.382 (3)
C19—C531.533 (3)C43—H430.9500
C19—C511.538 (2)C44—C451.397 (3)
C19—C521.543 (3)C44—C481.510 (3)
C21—C221.386 (2)C45—C461.393 (3)
C21—C261.405 (2)C45—H450.9500
C22—C231.391 (2)C46—C491.535 (3)
C22—C271.497 (2)C47—H47A0.9900
C23—C241.393 (3)C47—H47B0.9900
C23—H230.9500C48—H48A0.9800
C24—C251.387 (3)C48—H48B0.9800
C24—C281.506 (3)C48—H48C0.9800
C25—C261.396 (3)C49—C641.532 (3)
C25—H250.9500C49—C661.536 (3)
C26—C291.538 (3)C49—C651.542 (3)
C27—H27A0.9900C61—H61A0.9800
C27—H27B0.9900C61—H61B0.9800
C28—H28A0.9800C61—H61C0.9800
C28—H28B0.9800C62—H62A0.9800
C28—H28C0.9800C62—H62B0.9800
C29—C561.531 (3)C62—H62C0.9800
C29—C541.533 (3)C63—H63A0.9800
C29—C551.535 (3)C63—H63B0.9800
C51—H51A0.9800C63—H63C0.9800
C51—H51B0.9800C64—H64A0.9800
C51—H51C0.9800C64—H64B0.9800
C52—H52A0.9800C64—H64C0.9800
C52—H52B0.9800C65—H65A0.9800
C52—H52C0.9800C65—H65B0.9800
C53—H53A0.9800C65—H65C0.9800
C53—H53B0.9800C66—H66A0.9800
C53—H53C0.9800C66—H66B0.9800
C54—H54A0.9800C66—H66C0.9800
C54—H54B0.9800C71—C761.369 (15)
C54—H54C0.9800C71—C721.375 (15)
C55—H55A0.9800C71—C771.510 (11)
C55—H55B0.9800C72—C731.379 (14)
C55—H55C0.9800C72—H720.9500
C56—H56A0.9800C73—C741.368 (13)
C56—H56B0.9800C73—H730.9500
C56—H56C0.9800C74—C751.373 (13)
Si2—O221.6336 (13)C74—H740.9500
Si2—O211.6386 (14)C75—C761.381 (14)
Si2—N22.0440 (15)C75—H750.9500
Si2—Cl222.0748 (7)C76—H760.9500
Si2—Cl212.1797 (7)C77—H77A0.9800
O21—C311.378 (2)C77—H77B0.9800
O22—C411.381 (2)C77—H77C0.9800
N2—C371.507 (2)
O11—Si1—O12123.12 (7)Cl22—Si2—Cl2191.07 (3)
O11—Si1—N190.11 (6)C31—O21—Si2137.44 (12)
O12—Si1—N189.77 (6)C41—O22—Si2137.34 (12)
O11—Si1—Cl12116.61 (5)C37—N2—C3107.61 (14)
O12—Si1—Cl12120.27 (5)C37—N2—C47109.53 (14)
N1—Si1—Cl1290.09 (5)C3—N2—C47110.89 (14)
O11—Si1—Cl1189.23 (5)C37—N2—Si2108.63 (11)
O12—Si1—Cl1189.23 (5)C3—N2—Si2113.74 (11)
N1—Si1—Cl11178.24 (5)C47—N2—Si2106.38 (10)
Cl12—Si1—Cl1191.66 (3)N2—C3—C4115.99 (16)
C11—O11—Si1138.25 (12)N2—C3—H3A108.3
C21—O12—Si1138.15 (11)C4—C3—H3A108.3
C17—N1—C27108.95 (13)N2—C3—H3B108.3
C17—N1—C1108.05 (13)C4—C3—H3B108.3
C27—N1—C1109.98 (13)H3A—C3—H3B107.4
C17—N1—Si1109.19 (11)C3—C4—H4A109.5
C27—N1—Si1107.07 (10)C3—C4—H4B109.5
C1—N1—Si1113.53 (11)H4A—C4—H4B109.5
N1—C1—C2115.44 (15)C3—C4—H4C109.5
N1—C1—H1A108.4H4A—C4—H4C109.5
C2—C1—H1A108.4H4B—C4—H4C109.5
N1—C1—H1B108.4O21—C31—C32119.12 (17)
C2—C1—H1B108.4O21—C31—C36119.00 (16)
H1A—C1—H1B107.5C32—C31—C36121.88 (17)
C1—C2—H2A109.5C33—C32—C31119.73 (18)
C1—C2—H2B109.5C33—C32—C37121.28 (17)
H2A—C2—H2B109.5C31—C32—C37118.87 (16)
C1—C2—H2C109.5C34—C33—C32120.80 (19)
H2A—C2—H2C109.5C34—C33—H33119.6
H2B—C2—H2C109.5C32—C33—H33119.6
O11—C11—C12118.73 (16)C33—C34—C35118.25 (18)
O11—C11—C16118.62 (16)C33—C34—C38120.4 (2)
C12—C11—C16122.64 (17)C35—C34—C38121.3 (2)
C13—C12—C11119.23 (17)C34—C35—C36123.85 (19)
C13—C12—C17121.52 (16)C34—C35—H35118.1
C11—C12—C17119.19 (16)C36—C35—H35118.1
C14—C13—C12120.82 (17)C35—C36—C31115.47 (18)
C14—C13—H13119.6C35—C36—C39122.00 (18)
C12—C13—H13119.6C31—C36—C39122.53 (17)
C13—C14—C15118.05 (17)C32—C37—N2111.59 (14)
C13—C14—C18121.29 (18)C32—C37—H37A109.3
C15—C14—C18120.65 (18)N2—C37—H37A109.3
C14—C15—C16123.64 (18)C32—C37—H37B109.3
C14—C15—H15118.2N2—C37—H37B109.3
C16—C15—H15118.2H37A—C37—H37B108.0
C15—C16—C11115.56 (16)C34—C38—H38A109.5
C15—C16—C19122.07 (16)C34—C38—H38B109.5
C11—C16—C19122.37 (16)H38A—C38—H38B109.5
C12—C17—N1111.94 (14)C34—C38—H38C109.5
C12—C17—H17A109.2H38A—C38—H38C109.5
N1—C17—H17A109.2H38B—C38—H38C109.5
C12—C17—H17B109.2C63—C39—C36111.58 (18)
N1—C17—H17B109.2C63—C39—C62108.6 (2)
H17A—C17—H17B107.9C36—C39—C62110.02 (18)
C14—C18—H18A109.5C63—C39—C61106.17 (19)
C14—C18—H18B109.5C36—C39—C61110.40 (16)
H18A—C18—H18B109.5C62—C39—C61109.98 (19)
C14—C18—H18C109.5O22—C41—C42119.30 (16)
H18A—C18—H18C109.5O22—C41—C46118.72 (16)
H18B—C18—H18C109.5C42—C41—C46121.96 (17)
C53—C19—C51107.39 (15)C41—C42—C43119.83 (17)
C53—C19—C16111.91 (15)C41—C42—C47119.06 (16)
C51—C19—C16109.89 (15)C43—C42—C47121.11 (16)
C53—C19—C52107.37 (16)C44—C43—C42120.57 (17)
C51—C19—C52109.50 (15)C44—C43—H43119.7
C16—C19—C52110.68 (15)C42—C43—H43119.7
O12—C21—C22119.11 (16)C43—C44—C45118.02 (17)
O12—C21—C26118.97 (15)C43—C44—C48120.94 (17)
C22—C21—C26121.91 (16)C45—C44—C48121.03 (17)
C21—C22—C23119.94 (16)C46—C45—C44123.61 (17)
C21—C22—C27119.32 (16)C46—C45—H45118.2
C23—C22—C27120.72 (16)C44—C45—H45118.2
C22—C23—C24120.39 (17)C45—C46—C41115.97 (17)
C22—C23—H23119.8C45—C46—C49122.25 (17)
C24—C23—H23119.8C41—C46—C49121.78 (17)
C25—C24—C23117.82 (17)C42—C47—N2110.54 (14)
C25—C24—C28121.44 (17)C42—C47—H47A109.5
C23—C24—C28120.74 (17)N2—C47—H47A109.5
C24—C25—C26124.22 (17)C42—C47—H47B109.5
C24—C25—H25117.9N2—C47—H47B109.5
C26—C25—H25117.9H47A—C47—H47B108.1
C25—C26—C21115.72 (16)C44—C48—H48A109.5
C25—C26—C29121.76 (16)C44—C48—H48B109.5
C21—C26—C29122.52 (16)H48A—C48—H48B109.5
C22—C27—N1111.68 (14)C44—C48—H48C109.5
C22—C27—H27A109.3H48A—C48—H48C109.5
N1—C27—H27A109.3H48B—C48—H48C109.5
C22—C27—H27B109.3C64—C49—C46111.23 (17)
N1—C27—H27B109.3C64—C49—C66107.4 (2)
H27A—C27—H27B107.9C46—C49—C66109.82 (18)
C24—C28—H28A109.5C64—C49—C65107.58 (19)
C24—C28—H28B109.5C46—C49—C65110.38 (18)
H28A—C28—H28B109.5C66—C49—C65110.33 (19)
C24—C28—H28C109.5C39—C61—H61A109.5
H28A—C28—H28C109.5C39—C61—H61B109.5
H28B—C28—H28C109.5H61A—C61—H61B109.5
C56—C29—C54107.07 (17)C39—C61—H61C109.5
C56—C29—C55108.17 (18)H61A—C61—H61C109.5
C54—C29—C55109.91 (17)H61B—C61—H61C109.5
C56—C29—C26111.70 (16)C39—C62—H62A109.5
C54—C29—C26109.51 (16)C39—C62—H62B109.5
C55—C29—C26110.41 (16)H62A—C62—H62B109.5
C19—C51—H51A109.5C39—C62—H62C109.5
C19—C51—H51B109.5H62A—C62—H62C109.5
H51A—C51—H51B109.5H62B—C62—H62C109.5
C19—C51—H51C109.5C39—C63—H63A109.5
H51A—C51—H51C109.5C39—C63—H63B109.5
H51B—C51—H51C109.5H63A—C63—H63B109.5
C19—C52—H52A109.5C39—C63—H63C109.5
C19—C52—H52B109.5H63A—C63—H63C109.5
H52A—C52—H52B109.5H63B—C63—H63C109.5
C19—C52—H52C109.5C49—C64—H64A109.5
H52A—C52—H52C109.5C49—C64—H64B109.5
H52B—C52—H52C109.5H64A—C64—H64B109.5
C19—C53—H53A109.5C49—C64—H64C109.5
C19—C53—H53B109.5H64A—C64—H64C109.5
H53A—C53—H53B109.5H64B—C64—H64C109.5
C19—C53—H53C109.5C49—C65—H65A109.5
H53A—C53—H53C109.5C49—C65—H65B109.5
H53B—C53—H53C109.5H65A—C65—H65B109.5
C29—C54—H54A109.5C49—C65—H65C109.5
C29—C54—H54B109.5H65A—C65—H65C109.5
H54A—C54—H54B109.5H65B—C65—H65C109.5
C29—C54—H54C109.5C49—C66—H66A109.5
H54A—C54—H54C109.5C49—C66—H66B109.5
H54B—C54—H54C109.5H66A—C66—H66B109.5
C29—C55—H55A109.5C49—C66—H66C109.5
C29—C55—H55B109.5H66A—C66—H66C109.5
H55A—C55—H55B109.5H66B—C66—H66C109.5
C29—C55—H55C109.5C76—C71—C72119.1 (11)
H55A—C55—H55C109.5C76—C71—C77120.5 (9)
H55B—C55—H55C109.5C72—C71—C77120.4 (10)
C29—C56—H56A109.5C71—C72—C73120.6 (14)
C29—C56—H56B109.5C71—C72—H72119.7
H56A—C56—H56B109.5C73—C72—H72119.7
C29—C56—H56C109.5C74—C73—C72119.3 (10)
H56A—C56—H56C109.5C74—C73—H73120.4
H56B—C56—H56C109.5C72—C73—H73120.4
O22—Si2—O21123.90 (7)C73—C74—C75121.0 (8)
O22—Si2—N289.82 (6)C73—C74—H74119.5
O21—Si2—N290.50 (6)C75—C74—H74119.5
O22—Si2—Cl22118.45 (6)C74—C75—C76118.9 (10)
O21—Si2—Cl22117.65 (6)C74—C75—H75120.6
N2—Si2—Cl2290.22 (5)C76—C75—H75120.6
O22—Si2—Cl2189.46 (5)C71—C76—C75121.0 (13)
O21—Si2—Cl2189.01 (5)C71—C76—H76119.5
N2—Si2—Cl21178.71 (5)C75—C76—H76119.5
O12—Si1—O11—C1191.20 (18)O21—Si2—O22—C41−80.39 (19)
N1—Si1—O11—C111.39 (18)N2—Si2—O22—C4110.09 (19)
Cl12—Si1—O11—C11−88.76 (18)Cl22—Si2—O22—C41100.24 (18)
Cl11—Si1—O11—C11179.77 (17)Cl21—Si2—O22—C41−168.83 (18)
O11—Si1—O12—C21−77.28 (18)O22—Si2—N2—C37−167.49 (12)
N1—Si1—O12—C2112.71 (17)O21—Si2—N2—C37−43.59 (12)
Cl12—Si1—O12—C21102.68 (17)Cl22—Si2—N2—C3774.06 (11)
Cl11—Si1—O12—C21−165.85 (17)O22—Si2—N2—C372.70 (12)
O11—Si1—N1—C17−43.24 (12)O21—Si2—N2—C3−163.40 (12)
O12—Si1—N1—C17−166.36 (11)Cl22—Si2—N2—C3−45.75 (11)
Cl12—Si1—N1—C1773.36 (11)O22—Si2—N2—C47−49.67 (11)
O11—Si1—N1—C2774.56 (11)O21—Si2—N2—C4774.23 (11)
O12—Si1—N1—C27−48.56 (11)Cl22—Si2—N2—C47−168.12 (10)
Cl12—Si1—N1—C27−168.83 (10)C37—N2—C3—C473.33 (19)
O11—Si1—N1—C1−163.86 (12)C47—N2—C3—C4−46.4 (2)
O12—Si1—N1—C173.02 (12)Si2—N2—C3—C4−166.29 (14)
Cl12—Si1—N1—C1−47.26 (11)Si2—O21—C31—C3224.3 (3)
C17—N1—C1—C275.05 (19)Si2—O21—C31—C36−154.78 (15)
C27—N1—C1—C2−43.8 (2)O21—C31—C32—C33179.90 (16)
Si1—N1—C1—C2−163.69 (12)C36—C31—C32—C33−1.1 (3)
Si1—O11—C11—C1223.8 (3)O21—C31—C32—C37−4.0 (2)
Si1—O11—C11—C16−155.50 (15)C36—C31—C32—C37174.98 (16)
O11—C11—C12—C13178.62 (16)C31—C32—C33—C34−0.1 (3)
C16—C11—C12—C13−2.1 (3)C37—C32—C33—C34−176.11 (17)
O11—C11—C12—C17−4.4 (2)C32—C33—C34—C351.7 (3)
C16—C11—C12—C17174.91 (16)C32—C33—C34—C38179.93 (19)
C11—C12—C13—C14−0.2 (3)C33—C34—C35—C36−2.1 (3)
C17—C12—C13—C14−177.11 (17)C38—C34—C35—C36179.7 (2)
C12—C13—C14—C152.0 (3)C34—C35—C36—C310.9 (3)
C12—C13—C14—C18−179.20 (19)C34—C35—C36—C39179.66 (19)
C13—C14—C15—C16−1.8 (3)O21—C31—C36—C35179.72 (16)
C18—C14—C15—C16179.43 (19)C32—C31—C36—C350.7 (3)
C14—C15—C16—C11−0.3 (3)O21—C31—C36—C391.0 (3)
C14—C15—C16—C19179.62 (17)C32—C31—C36—C39−178.05 (17)
O11—C11—C16—C15−178.42 (15)C33—C32—C37—N2133.06 (17)
C12—C11—C16—C152.3 (3)C31—C32—C37—N2−42.9 (2)
O11—C11—C16—C191.6 (3)C3—N2—C37—C32−169.87 (14)
C12—C11—C16—C19−177.65 (16)C47—N2—C37—C32−49.23 (19)
C13—C12—C17—N1135.31 (18)Si2—N2—C37—C3266.57 (16)
C11—C12—C17—N1−41.6 (2)C35—C36—C39—C635.0 (3)
C27—N1—C17—C12−51.11 (19)C31—C36—C39—C63−176.3 (2)
C1—N1—C17—C12−170.57 (15)C35—C36—C39—C62−115.6 (2)
Si1—N1—C17—C1265.51 (16)C31—C36—C39—C6263.1 (2)
C15—C16—C19—C53−1.7 (2)C35—C36—C39—C61122.8 (2)
C11—C16—C19—C53178.25 (17)C31—C36—C39—C61−58.5 (2)
C15—C16—C19—C51117.50 (19)Si2—O22—C41—C4217.2 (3)
C11—C16—C19—C51−62.5 (2)Si2—O22—C41—C46−164.12 (15)
C15—C16—C19—C52−121.43 (19)O22—C41—C42—C43176.50 (16)
C11—C16—C19—C5258.5 (2)C46—C41—C42—C43−2.2 (3)
Si1—O12—C21—C2211.8 (3)O22—C41—C42—C47−3.5 (3)
Si1—O12—C21—C26−169.27 (13)C46—C41—C42—C47177.87 (17)
O12—C21—C22—C23178.57 (15)C41—C42—C43—C441.0 (3)
C26—C21—C22—C23−0.3 (3)C47—C42—C43—C44−179.02 (17)
O12—C21—C22—C270.0 (2)C42—C43—C44—C450.7 (3)
C26—C21—C22—C27−178.91 (16)C42—C43—C44—C48−179.12 (18)
C21—C22—C23—C24−0.2 (3)C43—C44—C45—C46−1.5 (3)
C27—C22—C23—C24178.33 (16)C48—C44—C45—C46178.39 (18)
C22—C23—C24—C250.4 (3)C44—C45—C46—C410.4 (3)
C22—C23—C24—C28−179.64 (17)C44—C45—C46—C49−179.71 (18)
C23—C24—C25—C26−0.1 (3)O22—C41—C46—C45−177.23 (16)
C28—C24—C25—C26180.00 (18)C42—C41—C46—C451.4 (3)
C24—C25—C26—C21−0.5 (3)O22—C41—C46—C492.9 (3)
C24—C25—C26—C29179.11 (17)C42—C41—C46—C49−178.46 (18)
O12—C21—C26—C25−178.25 (15)C41—C42—C47—N2−43.1 (2)
C22—C21—C26—C250.6 (3)C43—C42—C47—N2136.89 (17)
O12—C21—C26—C292.2 (3)C37—N2—C47—C42−173.05 (14)
C22—C21—C26—C29−178.92 (16)C3—N2—C47—C42−54.44 (18)
C21—C22—C27—N1−43.6 (2)Si2—N2—C47—C4269.72 (15)
C23—C22—C27—N1137.84 (16)C45—C46—C49—C64−1.1 (3)
C17—N1—C27—C22−173.96 (14)C41—C46—C49—C64178.8 (2)
C1—N1—C27—C22−55.71 (18)C45—C46—C49—C66−119.9 (2)
Si1—N1—C27—C2268.07 (15)C41—C46—C49—C6660.0 (3)
C25—C26—C29—C56−2.1 (3)C45—C46—C49—C65118.3 (2)
C21—C26—C29—C56177.42 (18)C41—C46—C49—C65−61.8 (2)
C25—C26—C29—C54−120.56 (19)C76—C71—C72—C733 (5)
C21—C26—C29—C5459.0 (2)C77—C71—C72—C73−177.4 (18)
C25—C26—C29—C55118.3 (2)C71—C72—C73—C74−1 (3)
C21—C26—C29—C55−62.2 (2)C72—C73—C74—C75−1 (2)
O22—Si2—O21—C3191.19 (18)C73—C74—C75—C761 (2)
N2—Si2—O21—C311.08 (18)C72—C71—C76—C75−2 (5)
Cl22—Si2—O21—C31−89.43 (18)C77—C71—C76—C75178.0 (18)
Cl21—Si2—O21—C31179.88 (17)C74—C75—C76—C710 (3)
  3 in total

1.  Comparison of Phosphorus and Silicon: Hypervalency, Stereochemistry, and Reactivity.

Authors:  Robert R. Holmes
Journal:  Chem Rev       Date:  1996-05-09       Impact factor: 60.622

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

3.  Palladium complexes with stabilized germylene and stannylene ligands.

Authors:  Marina M Kireenko; Kirill V Zaitsev; Yuri F Oprunenko; Andrei V Churakov; Viktor A Tafeenko; Sergey S Karlov; Galina S Zaitseva
Journal:  Dalton Trans       Date:  2013-02-11       Impact factor: 4.390

  3 in total

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