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Logo of actae2this articlesearchopen accesssubmitActa Crystallographica Section E: Crystallographic CommunicationsActa Crystallographica Section E: Crystallographic Communications
 
Acta Crystallogr E Crystallogr Commun. 2017 March 1; 73(Pt 3): 448–452.
Published online 2017 February 28. doi:  10.1107/S2056989017002602
PMCID: PMC5347074

Crystal structures of three sterically congested disilanes

Abstract

In the three sterically congested silanes, C24H38Si2 (1) (1,1,2,2-tetra­isopropyl-1,2-di­phenyl­disilane), C24H34Br4Si2 (2) [1,1,2,2-tetra­kis­(2-bromo­propan-2-yl)-1,2-di­phenyl­disilane] and C32H38Si2 (3) (1,2-di-tert-butyl-1,1,2,2-tetra­phenyl­disilane), the Si—Si bond length is shortest in (1) and longest in (2), with (3) having an inter­mediate value, which parallels the increasing steric congestion. A comparison of the two isopropyl derivatives, (1 and 2), shows a significant increase in the Si—C(ipso) distance with the introduction of bromine. Also, in the brominated compound 2, attractive inter­molecular Br(...)Br inter­actions exist with Br(...)Br separations ca 0.52 Å shorter than the sum of the van der Waals radii. In compound 2, one of the bromo­isopropyl groups is rotationally disordered in an 0.8812 (9):0.1188 (9) ratio. Compound 3 exhibits ‘whole mol­ecule’ disorder in a 0.9645 (7):0.0355 (7) ratio with the Si—Si bonds in the two components making an angle of ca 66°.

Keywords: crystal structure, disilane, halogen–halogen inter­action

Chemical context  

The study of tetra­isopropyl- and tetra­kis­(2-bromo­propan-2-yl)-substituted disilanes is of inter­est due to their importance in the synthesis of bis­(silanes), which are precursors for generating transient disilynes (Pichaandi et al., 2011  ; Kabe et al., 2000  ; Ando et al., 1997  ). The synthesis of 1,1,2,2-tetra­isopropyl-1,2-di-tert-butyl­disilane and 1,1,2,2-tetra­kis­(2-bromo­propan-2-yl)-1,2-di-tert-butyl­disilane were recently reported by our group (Pichaandi et al., 2011  ) and the crystal structure of the former determined. However, the structure of the latter could not be solved due to its highly disordered nature, so the exact nature of the influence of the bromine atom in the isopropyl group on the disilane structure could not be determined. We report here a comparison of the structures of 1,1,2,2-tetra­isopropyl-1,2-di­phenyl­disilane (1) and 1,1,2,2-tetra­kis­(2-bromo­propan-2-yl)-1,2-di­phenyl­disilane (2), as well as that of the related 1,2-di-tert-butyl-1,1,2,2-tetra­phenyl­disilane (3).

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Structural commentary  

The asymmetric unit for 1 consists of two independent mol­ecules (Fig. 1  ), one having an anti­clinal conformation and the other a gauche conformation about the Si—Si bond. Thus, the torsion angle defined by the Si—Si bond and the ipso carbon atoms of the phenyl groups are −140.15 (5)° (C2—Si1—Si2—C19) for the former and 59.58 (6)° (C31—Si3—Si4—C43) for the latter. In contrast, the two independent mol­ecules in the low-temperature form of 1,1,2,2-tetra-tert-butyl-1,2-di­phenyl­disilane both adopt the gauche arrangement with corresponding torsion angles of −71.47 (9) and −68.61 (9)° (Scholz et al., 2014  ). Disilane 2 (Fig. 2  ) has a gauche conformation with the corresponding torsion angle being 75.55 (5)° (C7—Si1—Si2—C19). The gauche conformation in 2 appears to be preferred over other conformations when the rotational barrier around the Si—Si bond is high. This trend is observed in the crowded 1,1,2,2-tetra­isopropyl-1,2-di-tert-butyl­disilane (Pichaandi et al., 2011  ) and 1,1,2,2-tetra-tert-butyl-1,2-di­phenyl­disilane (Lerner et al., 2001  ), which both exhibit a gauche conformation. However, the sterically less hindered 1,1,2,2-tetra-tert-butyl-1,2-di­chloro­disilane (Peters et al., 1998  ) and tetra-tert-butyl-1,2-di­hydroxy­disilane (West & Pham, 1991  ) have an anti­clinal conformation, similar to 1. The higher rotational barrier in 2 comes from the presence of the bulky bromo­isopropyl group.

Figure 1
Perspective view of the two independent mol­ecules of 1, with labeling scheme and 50% probability displacement ellipsoids.
Figure 2
Perspective view of 2, with labeling scheme and 50% probability displacement ellipsoids. Only the major orientation of the disordered bromo­isopropyl group is shown.

Compound 3 has crystallographically imposed centrosymmetry and so adopts a staggered conformation (Fig. 3  ). Inter­estingly, in this crystal there is an example of ‘whole mol­ecule’ disorder with 4% of the contents of the asymmetric unit adopting an orientation in which the Si—Si bond is inclined by approximately 66° to that of the major component. Since this work was undertaken, the structure of 3 has been reported by two different groups (Monakhov et al., 2010  ; Wei et al., 2014  ), but only mentioned cursorily and with no discussion of structural details. The Si—Si bond lengths in 13 are, respectively, 2.3898 (4), 2.4746 (10) and 2.4002 (6) Å, significantly longer than the typical values for less-congested disilanes, e.g. 2.340 (9) Å in hexa­methyl­disilane (Beagley et al., 1971  ). The longest compares favorably with those found in the sterically congested disilanes 1,1,2,2-tetra­isopropyl-1,2-di-tert-butyl­disilane [2.4787 (6) Å; Pichaandi et al., 2011  ] and 1,1,2,2-tetra-tert-butyl-1,2-di­phenyl­disilane [2.4973 (8) Å; Lerner et al., 2001  ; Scholz et al., 2014  ], but is shorter than that in the extremely congested hexa-tert-butyl­disilane [2.6863 (5) Å; Scholz et al., 2014  ]. The effects of the steric congestion are also seen in the Si—C bond lengths, e.g. Si1—C2 = 1.9005 (12) Å in 1, Si1—C1 = 1.965 (3) Å in 2 and Si1—C13 = 1.9226 (12) Å in 3, all of which are significantly longer than a typical Si—C single bond (1.87 Å; Sheldrick, 1989  ). Additionally, the significant increase in the quoted Si—C bond length between 2 and 1 indicates the increase in steric congestion on brominating the isopropyl group.

Figure 3
Perspective view of 3, with labeling scheme and 50% probability displacement ellipsoids. Only the major orientation of the disorder is shown [symmetry code: (i) 2 − x, −y, −z].

Supra­molecular features  

In 1, the packing consists of layers two mol­ecules thick which are parallel to (001) with only normal van der Waals contacts between mol­ecules (Fig. 4  ). In 2, the mol­ecules form chains running parallel to the b-axis direction through weak C—H(...)Br hydrogen bonds (see Table 1  ). These chains pair up through Br4(...)Br4 (−x + 1, −y + 1, −z + 1) inter­actions, where the Br(...)Br separation of 3.1755 (7) Å is 0.52 Å shorter than the sum of the van der Waals radii (3.70 Å) (see Fig. 5  ). We consider these to be attractive inter­actions as has been argued previously (Desiraju & Parthasarthy, 1989  ). Only normal van der Waals contacts occur between the double chains. The primary inter­molecular inter­action in 3 is a C—H(...)π inter­action (see Table 2  ), which forms chains running parallel to the c-axis direction (Fig. 6  ).

Figure 4
Packing of 1, viewed along the b-axis direction.
Figure 5
Packing of 2, viewed along the a-axis direction, with the C—H(...)Br hydrogen bonds (Table 1  ) shown as black dotted lines and Br(...)Br inter­actions as brown dotted lines.
Figure 6
Packing of 3, viewed along the b-axis direction, with the C—H(...)π(ring) inter­actions (Table 2  ) shown as dotted lines.
Table 1
Hydrogen-bond geometry (Å, °) for 2
Table 2
Hydrogen-bond geometry (Å, °) for 3

Database survey  

There are 390 structures of disilanes containing only Si—C bonds to the substituents in the Cambridge Crystallographic Database (CSD, V5.38, last update November, 2016; Groom et al., 2016  ), but in only 43 of these is the Si—Si distance greater than 2.40 Å. In this set, the distances range from 2.401 (2) Å in 4 (Kyushin et al., 1996  ) (Fig. 7  ). to 2.6863 (5) Å in one structure of hexa-tert-butyl­disilane (Scholz et al., 2014  ). In addition to the four reported structures of hexa-tert-butyl­disilane (Scholz et al., 2012  , 2014  ; Wiberg et al., 1986  ; Wiberg & Niedermayer, 2000  ), but excluding the five examples where it is co-crystallized with [NaOR]4 (Lerner et al., 2002  ), [SnR]6 (Wiberg et al., 1999  ), [SiR]4 (Wiberg et al., 1993  ; Meyer-Wegner et al., 2009  ) and [GeR]4 (Wiberg et al., 1996  ) [R = Si(t-Bu)3 in all cases], only four other mol­ecules have Si—Si distances greater than 2.5 Å. These are 5 [2.5149 (13) Å; Kabe et al., 2000  ), Ph6Si2 as a solid solution with Ph6Pb2 [2.519 (4) Å; Kleiner & Dräger, 1984  ], 6 [2.5428 (18) Å; Gottschling et al., 2005  ] and 7 [2.6468 (9) Å; Goetze et al., 1997  ] (Fig. 7  ).

Figure 7
Compounds from the database survey.

Synthesis and crystallization  

Disilanes 1 and 2 were prepared according to the literature procedures (Lambert & Urdaneta-Perez, 1978  ; Pichaandi et al., 2011  ). Colorless crystals of 1 and 2 were obtained from hexane and di­chloro­methane solutions, respectively. To prepare 3, a 50 ml Schlenk flask was loaded with tert-butyl­diphenyl­chloro­silane (10 g, 37 mmol), finely cut Li wire (0.26 g, 0.038 g-atom) and 20 ml of THF under nitro­gen and the mixture was stirred overnight at 298 K. The reaction mixture was then diluted with 350 ml of CH2Cl2 and dilute HCl (10 ml) and 20 ml of water were added. The organic layer was then separated from the aqueous layer, dried with MgSO4 and the solvent removed in vacuo to give 3 as a white powder. Crystals suitable for X-ray diffraction were obtained from CH2Cl2 solution (yield 8.1 g, 94%). 1H NMR (δ, CD2Cl2) 0.76–1.02 (s, 18H) 7.27–7.52 (m, 12H) 7.65–7.85 (m, 8H); 13C{1H} NMR (δ, CD2Cl2) 20.0, 28.8, 127.8, 128.9, 136.6, 137.5; 29Si{1H} NMR (δ, CD2Cl2) −13.5.

Refinement  

Crystal data, data collection and structure refinement details are summarized in Table 3  . In compound 2, the bromo­isopropyl group containing Br4 is rotationally disordered about the Si2—C16 axis in an 0.8812 (9):0.1188 (9) ratio. The two components of the disorder were refined with restraints that their geometries be comparable to one another and to those of the other three bromo­isopropyl groups. Compound 3 exhibits ‘whole mol­ecule’ disorder in a 0.9645 (7):0.0355 (7) ratio with the Si—Si bonds in the two components making an angle of ca 66°. The alternate location of the unique Si atom was obtained from a difference Fourier map and its inclusion in the structure-factor calculation allowed enough atoms of its phenyl groups to be located so that these could be completed and refined as rigid hexa­gons. Following this, the remaining atoms of the minor component could be located and they were refined with restraints that the geometry be comparable with that of the major component. In all three structures, the H atoms were included as riding contributions in idealized positions: C—H = 0.95–0.98 Å with U iso(H) = 1.5U eq(C-meth­yl) and 1.2U eq(C) for other H atoms.

Table 3
Experimental details

Supplementary Material

Crystal structure: contains datablock(s) 1, 2, 3, global. DOI: 10.1107/S2056989017002602/su5352sup1.cif

Structure factors: contains datablock(s) 1. DOI: 10.1107/S2056989017002602/su53521sup2.hkl

Structure factors: contains datablock(s) 2. DOI: 10.1107/S2056989017002602/su53522sup3.hkl

Structure factors: contains datablock(s) 3. DOI: 10.1107/S2056989017002602/su53523sup4.hkl

CCDC references: 1532770, 1532769, 1532768

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The financial support of NSF Grant CHE-0445637 (to MJF) and Tulane University for the Tulane X-ray Crystallography Laboratory is gratefully acknowledged.

supplementary crystallographic information

Crystal data

C32H38Si2F(000) = 516
Mr = 478.80Dx = 1.182 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 8.5622 (5) ÅCell parameters from 9973 reflections
b = 10.2107 (6) Åθ = 2.4–29.3°
c = 15.4586 (10) ŵ = 0.15 mm1
β = 95.452 (1)°T = 100 K
V = 1345.37 (14) Å3Block, colorless
Z = 20.17 × 0.15 × 0.13 mm

Data collection

Bruker SMART APEX CCD diffractometer3566 independent reflections
Radiation source: fine-focus sealed tube3065 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.031
[var phi] and ω scansθmax = 29.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2016)h = −11→11
Tmin = 0.98, Tmax = 0.98k = −13→14
23513 measured reflectionsl = −21→21

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0409P)2 + 0.5552P] where P = (Fo2 + 2Fc2)/3
3566 reflections(Δ/σ)max = 0.001
179 parametersΔρmax = 0.38 e Å3
43 restraintsΔρmin = −0.29 e Å3

Special details

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at [var phi] = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in [var phi], collected at ω = –30.00 and 210.00°. The scan time was 20 sec/frame.
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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 - 0.98 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. The centrosymmetric molecule is disordered over two orientations about the center in a 96:4 ratio. The two components of the disorder were refined subject to restraints that their geometries be comparable. In addition, the phenyl ring of the minor component overlapping with one from the major component was refined as a rigid hexagon.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Si10.97798 (4)0.05498 (3)0.06638 (2)0.01404 (9)0.9645 (7)
C11.17324 (13)0.10306 (10)0.12738 (7)0.0163 (2)0.9645 (7)
C21.24616 (14)0.03226 (11)0.19771 (7)0.0191 (2)0.9645 (7)
H21.1978−0.04550.21590.023*0.9645 (7)
C31.38770 (17)0.07272 (13)0.24168 (8)0.0223 (2)0.9645 (7)
H31.43420.02270.28920.027*0.9645 (7)
C41.46102 (14)0.18583 (13)0.21639 (8)0.0219 (3)0.9645 (7)
H41.55670.21430.24680.026*0.9645 (7)
C51.39259 (15)0.25668 (13)0.14615 (8)0.0227 (3)0.9645 (7)
H51.44260.33340.12760.027*0.9645 (7)
C61.25096 (14)0.21603 (11)0.10265 (7)0.0195 (2)0.9645 (7)
H61.20570.26620.05490.023*0.9645 (7)
C70.86874 (13)0.21393 (10)0.04130 (7)0.0164 (2)0.9645 (7)
C80.89979 (14)0.32572 (11)0.09251 (7)0.0204 (2)0.9645 (7)
H80.97850.32200.14010.024*0.9645 (7)
C90.81825 (15)0.44211 (11)0.07537 (8)0.0239 (3)0.9645 (7)
H90.84280.51700.11050.029*0.9645 (7)
C100.70130 (16)0.44902 (12)0.00709 (8)0.0242 (3)0.9645 (7)
H100.64630.5287−0.00510.029*0.9645 (7)
C110.66515 (16)0.33862 (12)−0.04334 (8)0.0255 (3)0.9645 (7)
H110.58350.3421−0.08940.031*0.9645 (7)
C120.74836 (14)0.22282 (12)−0.02654 (8)0.0215 (2)0.9645 (7)
H120.72300.1482−0.06180.026*0.9645 (7)
C130.85261 (14)−0.04591 (11)0.13883 (7)0.0173 (2)0.9645 (7)
C140.85115 (15)0.02324 (12)0.22736 (8)0.0210 (2)0.9645 (7)
H14A0.7804−0.02340.26300.032*0.9645 (7)
H14B0.81470.11360.21830.032*0.9645 (7)
H14C0.95740.02350.25720.032*0.9645 (7)
C150.91134 (15)−0.18758 (12)0.15272 (8)0.0218 (3)0.9645 (7)
H15A1.0199−0.18660.17940.033*0.9645 (7)
H15B0.9068−0.23270.09660.033*0.9645 (7)
H15C0.8448−0.23360.19100.033*0.9645 (7)
C160.68191 (15)−0.05123 (12)0.09687 (8)0.0219 (2)0.9645 (7)
H16A0.6184−0.10410.13320.033*0.9645 (7)
H16B0.6797−0.09080.03900.033*0.9645 (7)
H16C0.63910.03770.09170.033*0.9645 (7)
Si1A0.8638 (8)0.0135 (6)0.0097 (4)0.01404 (9)0.0355 (7)
C1A0.7401 (14)−0.0682 (9)−0.0846 (6)0.0163 (2)0.0355 (7)
C2A0.712 (2)−0.0099 (12)−0.1659 (6)0.0191 (2)0.0355 (7)
H2A0.75280.0749−0.17570.023*0.0355 (7)
C3A0.625 (3)−0.0757 (16)−0.2329 (8)0.0223 (2)0.0355 (7)
H3A0.6063−0.0359−0.28840.027*0.0355 (7)
C4A0.566 (3)−0.1998 (17)−0.2186 (12)0.0219 (3)0.0355 (7)
H4A0.5065−0.2448−0.26430.026*0.0355 (7)
C5A0.594 (2)−0.2580 (13)−0.1373 (12)0.0227 (3)0.0355 (7)
H5A0.5532−0.3428−0.12750.027*0.0355 (7)
C6A0.681 (2)−0.1922 (9)−0.0703 (9)0.0195 (2)0.0355 (7)
H6A0.6997−0.2320−0.01480.023*0.0355 (7)
C7A0.8171 (13)0.1959 (7)0.0073 (6)0.0164 (2)0.0355 (7)
C8A0.9272 (17)0.2764 (8)0.0526 (9)0.0204 (2)0.0355 (7)
H8A1.02520.24140.07580.024*0.0355 (7)
C9A0.894 (2)0.4082 (8)0.0640 (11)0.0239 (3)0.0355 (7)
H9A0.96940.46330.09500.029*0.0355 (7)
C10A0.751 (2)0.4595 (8)0.0300 (12)0.0242 (3)0.0355 (7)
H10A0.72820.54950.03780.029*0.0355 (7)
C11A0.641 (2)0.3789 (10)−0.0153 (13)0.0255 (3)0.0355 (7)
H11A0.54270.4139−0.03850.031*0.0355 (7)
C12A0.6738 (15)0.2471 (9)−0.0267 (9)0.0215 (2)0.0355 (7)
H12A0.59850.1920−0.05770.026*0.0355 (7)
C13A0.8088 (19)−0.0519 (11)0.1193 (6)0.0173 (2)0.0355 (7)
C14A0.871 (3)0.043 (2)0.1921 (7)0.0210 (2)0.0355 (7)
H14D0.98550.04850.19400.032*0.0355 (7)
H14E0.82530.12990.18070.032*0.0355 (7)
H14F0.84170.01050.24810.032*0.0355 (7)
C15A0.874 (4)−0.1902 (16)0.1401 (13)0.0218 (3)0.0355 (7)
H15D0.8350−0.25080.09400.033*0.0355 (7)
H15E0.9892−0.18780.14400.033*0.0355 (7)
H15F0.8404−0.21980.19570.033*0.0355 (7)
C16A0.6288 (19)−0.058 (3)0.1189 (13)0.0219 (2)0.0355 (7)
H16D0.5859−0.11740.07300.033*0.0355 (7)
H16E0.6013−0.08920.17530.033*0.0355 (7)
H16F0.58490.03010.10800.033*0.0355 (7)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Si10.01699 (16)0.01075 (15)0.01390 (15)0.00070 (11)−0.00100 (11)−0.00031 (10)
C10.0185 (5)0.0142 (5)0.0159 (5)0.0017 (4)−0.0001 (4)−0.0030 (4)
C20.0224 (6)0.0151 (5)0.0194 (5)0.0022 (4)−0.0006 (4)−0.0014 (4)
C30.0226 (6)0.0213 (5)0.0217 (6)0.0056 (5)−0.0054 (4)−0.0002 (4)
C40.0167 (6)0.0249 (6)0.0234 (6)0.0016 (5)−0.0022 (4)−0.0065 (4)
C50.0244 (6)0.0212 (6)0.0221 (6)−0.0045 (5)0.0007 (5)−0.0025 (4)
C60.0230 (6)0.0175 (5)0.0175 (5)−0.0011 (4)−0.0007 (4)−0.0010 (4)
C70.0197 (5)0.0135 (5)0.0159 (5)0.0014 (4)0.0005 (4)0.0004 (4)
C80.0249 (6)0.0146 (5)0.0207 (5)0.0026 (4)−0.0024 (4)−0.0017 (4)
C90.0287 (7)0.0134 (5)0.0286 (6)0.0027 (5)−0.0016 (5)−0.0014 (4)
C100.0282 (7)0.0168 (5)0.0271 (6)0.0073 (5)−0.0008 (5)0.0043 (4)
C110.0291 (7)0.0257 (6)0.0204 (6)0.0080 (5)−0.0053 (5)0.0011 (5)
C120.0243 (6)0.0201 (6)0.0193 (5)0.0046 (5)−0.0028 (5)−0.0030 (4)
C130.0195 (6)0.0155 (5)0.0168 (5)−0.0004 (4)0.0009 (4)−0.0001 (4)
C140.0241 (6)0.0222 (6)0.0171 (5)0.0005 (5)0.0033 (4)−0.0007 (4)
C150.0270 (7)0.0151 (5)0.0234 (6)−0.0016 (5)0.0028 (5)0.0024 (4)
C160.0201 (6)0.0235 (6)0.0223 (6)−0.0027 (5)0.0025 (4)−0.0019 (5)
Si1A0.01699 (16)0.01075 (15)0.01390 (15)0.00070 (11)−0.00100 (11)−0.00031 (10)
C1A0.0185 (5)0.0142 (5)0.0159 (5)0.0017 (4)−0.0001 (4)−0.0030 (4)
C2A0.0224 (6)0.0151 (5)0.0194 (5)0.0022 (4)−0.0006 (4)−0.0014 (4)
C3A0.0226 (6)0.0213 (5)0.0217 (6)0.0056 (5)−0.0054 (4)−0.0002 (4)
C4A0.0167 (6)0.0249 (6)0.0234 (6)0.0016 (5)−0.0022 (4)−0.0065 (4)
C5A0.0244 (6)0.0212 (6)0.0221 (6)−0.0045 (5)0.0007 (5)−0.0025 (4)
C6A0.0230 (6)0.0175 (5)0.0175 (5)−0.0011 (4)−0.0007 (4)−0.0010 (4)
C7A0.0197 (5)0.0135 (5)0.0159 (5)0.0014 (4)0.0005 (4)0.0004 (4)
C8A0.0249 (6)0.0146 (5)0.0207 (5)0.0026 (4)−0.0024 (4)−0.0017 (4)
C9A0.0287 (7)0.0134 (5)0.0286 (6)0.0027 (5)−0.0016 (5)−0.0014 (4)
C10A0.0282 (7)0.0168 (5)0.0271 (6)0.0073 (5)−0.0008 (5)0.0043 (4)
C11A0.0291 (7)0.0257 (6)0.0204 (6)0.0080 (5)−0.0053 (5)0.0011 (5)
C12A0.0243 (6)0.0201 (6)0.0193 (5)0.0046 (5)−0.0028 (5)−0.0030 (4)
C13A0.0195 (6)0.0155 (5)0.0168 (5)−0.0004 (4)0.0009 (4)−0.0001 (4)
C14A0.0241 (6)0.0222 (6)0.0171 (5)0.0005 (5)0.0033 (4)−0.0007 (4)
C15A0.0270 (7)0.0151 (5)0.0234 (6)−0.0016 (5)0.0028 (5)0.0024 (4)
C16A0.0201 (6)0.0235 (6)0.0223 (6)−0.0027 (5)0.0025 (4)−0.0019 (5)

Geometric parameters (Å, º)

Si1—C71.8949 (11)Si1A—C7A1.904 (3)
Si1—C11.9041 (11)Si1A—C1A1.911 (3)
Si1—C131.9226 (12)Si1A—C13A1.921 (4)
Si1—Si1i2.4002 (6)Si1A—Si1Ai2.396 (14)
C1—C21.4020 (14)C1A—C2A1.3900
C1—C61.4028 (15)C1A—C6A1.3900
C2—C31.3946 (16)C2A—C3A1.3900
C2—H20.9500C2A—H2A0.9500
C3—C41.3884 (16)C3A—C4A1.3900
C3—H30.9500C3A—H3A0.9500
C4—C51.3873 (16)C4A—C5A1.3900
C4—H40.9500C4A—H4A0.9500
C5—C61.3929 (15)C5A—C6A1.3900
C5—H50.9500C5A—H5A0.9500
C6—H60.9500C6A—H6A0.9500
C7—C81.4000 (14)C7A—C8A1.3900
C7—C121.4018 (14)C7A—C12A1.3900
C8—C91.3910 (15)C8A—C9A1.3900
C8—H80.9500C8A—H8A0.9500
C9—C101.3860 (16)C9A—C10A1.3900
C9—H90.9500C9A—H9A0.9500
C10—C111.3887 (16)C10A—C11A1.3900
C10—H100.9500C10A—H10A0.9500
C11—C121.3922 (15)C11A—C12A1.3900
C11—H110.9500C11A—H11A0.9500
C12—H120.9500C12A—H12A0.9500
C13—C151.5398 (16)C13A—C14A1.540 (4)
C13—C141.5411 (16)C13A—C16A1.542 (4)
C13—C161.5427 (17)C13A—C15A1.542 (4)
C14—H14A0.9800C14A—H14D0.9800
C14—H14B0.9800C14A—H14E0.9800
C14—H14C0.9800C14A—H14F0.9800
C15—H15A0.9800C15A—H15D0.9800
C15—H15B0.9800C15A—H15E0.9800
C15—H15C0.9800C15A—H15F0.9800
C16—H16A0.9800C16A—H16D0.9800
C16—H16B0.9800C16A—H16E0.9800
C16—H16C0.9800C16A—H16F0.9800
C7—Si1—C1105.87 (5)C7A—Si1A—C1A108.15 (19)
C7—Si1—C13106.62 (5)C7A—Si1A—C13A106.8 (4)
C1—Si1—C13111.24 (5)C1A—Si1A—C13A110.9 (4)
C7—Si1—Si1i109.90 (4)C7A—Si1A—Si1Ai108.4 (5)
C1—Si1—Si1i110.01 (4)C1A—Si1A—Si1Ai109.3 (5)
C13—Si1—Si1i112.91 (4)C13A—Si1A—Si1Ai113.2 (6)
C2—C1—C6116.58 (10)C2A—C1A—C6A120.0
C2—C1—Si1123.81 (8)C2A—C1A—Si1A122.5 (3)
C6—C1—Si1119.61 (8)C6A—C1A—Si1A117.4 (3)
C3—C2—C1121.85 (11)C3A—C2A—C1A120.0
C3—C2—H2119.1C3A—C2A—H2A120.0
C1—C2—H2119.1C1A—C2A—H2A120.0
C4—C3—C2120.29 (11)C2A—C3A—C4A120.0
C4—C3—H3119.9C2A—C3A—H3A120.0
C2—C3—H3119.9C4A—C3A—H3A120.0
C5—C4—C3119.05 (11)C3A—C4A—C5A120.0
C5—C4—H4120.5C3A—C4A—H4A120.0
C3—C4—H4120.5C5A—C4A—H4A120.0
C4—C5—C6120.40 (11)C6A—C5A—C4A120.0
C4—C5—H5119.8C6A—C5A—H5A120.0
C6—C5—H5119.8C4A—C5A—H5A120.0
C5—C6—C1121.82 (11)C5A—C6A—C1A120.0
C5—C6—H6119.1C5A—C6A—H6A120.0
C1—C6—H6119.1C1A—C6A—H6A120.0
C8—C7—C12117.19 (10)C8A—C7A—C12A120.0
C8—C7—Si1121.28 (8)C8A—C7A—Si1A115.94 (17)
C12—C7—Si1121.47 (8)C12A—C7A—Si1A123.5 (2)
C9—C8—C7121.60 (10)C9A—C8A—C7A120.0
C9—C8—H8119.2C9A—C8A—H8A120.0
C7—C8—H8119.2C7A—C8A—H8A120.0
C10—C9—C8120.12 (11)C8A—C9A—C10A120.0
C10—C9—H9119.9C8A—C9A—H9A120.0
C8—C9—H9119.9C10A—C9A—H9A120.0
C9—C10—C11119.51 (11)C11A—C10A—C9A120.0
C9—C10—H10120.2C11A—C10A—H10A120.0
C11—C10—H10120.2C9A—C10A—H10A120.0
C10—C11—C12120.12 (11)C12A—C11A—C10A120.0
C10—C11—H11119.9C12A—C11A—H11A120.0
C12—C11—H11119.9C10A—C11A—H11A120.0
C11—C12—C7121.43 (11)C11A—C12A—C7A120.0
C11—C12—H12119.3C11A—C12A—H12A120.0
C7—C12—H12119.3C7A—C12A—H12A120.0
C15—C13—C14109.68 (9)C14A—C13A—C16A107.7 (5)
C15—C13—C16108.02 (9)C14A—C13A—C15A109.2 (5)
C14—C13—C16107.60 (9)C16A—C13A—C15A108.0 (5)
C15—C13—Si1113.05 (8)C14A—C13A—Si1A109.2 (5)
C14—C13—Si1108.90 (8)C16A—C13A—Si1A109.7 (5)
C16—C13—Si1109.45 (8)C15A—C13A—Si1A112.8 (5)
C13—C14—H14A109.5C13A—C14A—H14D109.5
C13—C14—H14B109.5C13A—C14A—H14E109.5
H14A—C14—H14B109.5H14D—C14A—H14E109.5
C13—C14—H14C109.5C13A—C14A—H14F109.5
H14A—C14—H14C109.5H14D—C14A—H14F109.5
H14B—C14—H14C109.5H14E—C14A—H14F109.5
C13—C15—H15A109.5C13A—C15A—H15D109.5
C13—C15—H15B109.5C13A—C15A—H15E109.5
H15A—C15—H15B109.5H15D—C15A—H15E109.5
C13—C15—H15C109.5C13A—C15A—H15F109.5
H15A—C15—H15C109.5H15D—C15A—H15F109.5
H15B—C15—H15C109.5H15E—C15A—H15F109.5
C13—C16—H16A109.5C13A—C16A—H16D109.5
C13—C16—H16B109.5C13A—C16A—H16E109.5
H16A—C16—H16B109.5H16D—C16A—H16E109.5
C13—C16—H16C109.5C13A—C16A—H16F109.5
H16A—C16—H16C109.5H16D—C16A—H16F109.5
H16B—C16—H16C109.5H16E—C16A—H16F109.5
C6—C1—C2—C30.80 (18)C10—C11—C12—C70.5 (2)
Si1—C1—C2—C3−178.60 (10)C8—C7—C12—C111.18 (18)
C1—C2—C3—C4−0.1 (2)Si1—C7—C12—C11178.14 (10)
C2—C3—C4—C5−0.9 (2)C6A—C1A—C2A—C3A0.0
C3—C4—C5—C61.11 (19)Si1A—C1A—C2A—C3A178.1 (4)
C4—C5—C6—C1−0.36 (19)C1A—C2A—C3A—C4A0.0
C2—C1—C6—C5−0.59 (18)C2A—C3A—C4A—C5A0.0
Si1—C1—C6—C5178.83 (10)C3A—C4A—C5A—C6A0.0
C1—Si1—C7—C8−25.36 (11)C4A—C5A—C6A—C1A0.0
C13—Si1—C7—C893.19 (10)C2A—C1A—C6A—C5A0.0
Si1i—Si1—C7—C8−144.13 (9)Si1A—C1A—C6A—C5A−178.2 (4)
C1—Si1—C7—C12157.80 (10)C12A—C7A—C8A—C9A0.0
C13—Si1—C7—C12−83.65 (11)Si1A—C7A—C8A—C9A−171.7 (4)
Si1i—Si1—C7—C1239.03 (11)C7A—C8A—C9A—C10A0.0
C12—C7—C8—C9−1.94 (18)C8A—C9A—C10A—C11A0.0
Si1—C7—C8—C9−178.91 (10)C9A—C10A—C11A—C12A0.0
C7—C8—C9—C101.0 (2)C10A—C11A—C12A—C7A0.0
C8—C9—C10—C110.7 (2)C8A—C7A—C12A—C11A0.0
C9—C10—C11—C12−1.5 (2)Si1A—C7A—C12A—C11A171.0 (4)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º)

Cg1 is the centroid of C1–C6 the ring.

D—H···AD—HH···AD···AD—H···A
C15—H15C···Cg1ii0.982.933.8955 (14)171

Symmetry code: (ii) −x+2, y−1/2, −z+1/2.

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Articles from Acta Crystallographica Section E: Crystallographic Communications are provided here courtesy of International Union of Crystallography