research communications
Crystal structures of three sterically congested disilanes
aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
*Correspondence e-mail: joelt@tulane.edu
In the three sterically congested 24H38Si2 (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°.
CKeywords: crystal structure; disilane; halogen–halogen interaction.
1. 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 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).
2. Structural commentary
The 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 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 in 2 comes from the presence of the bulky bromoisopropyl group.
forCompound 3 has crystallographically imposed centrosymmetry and so adopts a (Fig. 3). Interestingly, in this crystal there is an example of `whole molecule' disorder with 4% of the contents of the 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 1–3 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.
3. 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).
4. 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 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).
5. 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.
6. Refinement
Crystal data, data collection and structure . 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 Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.
details are summarized in Table 3Supporting information
https://doi.org/10.1107/S2056989017002602/su5352sup1.cif
contains datablocks 1, 2, 3, global. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989017002602/su53521sup2.hkl
Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989017002602/su53522sup3.hkl
Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S2056989017002602/su53523sup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989017002602/su53521sup5.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989017002602/su53522sup6.cml
Supporting information file. DOI: https://doi.org/10.1107/S2056989017002602/su53523sup7.cml
For all compounds, data collection: APEX3 (Bruker, 2016); cell
SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C24H38Si2 | F(000) = 1680 |
Mr = 382.72 | Dx = 1.101 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 19.8418 (14) Å | Cell parameters from 9612 reflections |
b = 8.2554 (6) Å | θ = 2.4–29.4° |
c = 28.454 (2) Å | µ = 0.16 mm−1 |
β = 97.838 (1)° | T = 100 K |
V = 4617.3 (6) Å3 | Block, colorless |
Z = 8 | 0.22 × 0.19 × 0.14 mm |
Bruker SMART APEX CCD diffractometer | 12375 independent reflections |
Radiation source: fine-focus sealed tube | 10320 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.046 |
φ and ω scans | θmax = 29.7°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −27→27 |
Tmin = 0.96, Tmax = 0.98 | k = −11→11 |
81051 measured reflections | l = −39→38 |
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)] = 0.036 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0424P)2 + 1.8169P] where P = (Fo2 + 2Fc2)/3 |
12375 reflections | (Δ/σ)max = 0.002 |
485 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.29 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = –30.00 and 210.00°. The scan time was 15 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 - 1.00 Å). All were included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached atoms. |
x | y | z | Uiso*/Ueq | ||
Si1 | 0.94710 (2) | 0.33575 (4) | 0.11131 (2) | 0.01283 (7) | |
Si2 | 0.84650 (2) | 0.49225 (4) | 0.11451 (2) | 0.01282 (7) | |
C1 | 0.94625 (7) | 0.22143 (17) | 0.20748 (4) | 0.0246 (3) | |
H1A | 0.9414 | 0.1265 | 0.2274 | 0.037* | |
H1B | 0.9060 | 0.2905 | 0.2068 | 0.037* | |
H1C | 0.9868 | 0.2827 | 0.2205 | 0.037* | |
C2 | 0.95337 (6) | 0.16598 (14) | 0.15680 (4) | 0.0182 (2) | |
H2 | 0.9133 | 0.0944 | 0.1469 | 0.022* | |
C3 | 1.01631 (7) | 0.05704 (16) | 0.15684 (5) | 0.0246 (3) | |
H3A | 1.0576 | 0.1232 | 0.1628 | 0.037* | |
H3B | 1.0146 | 0.0036 | 0.1259 | 0.037* | |
H3C | 1.0168 | −0.0251 | 0.1818 | 0.037* | |
C4 | 0.89382 (6) | 0.09978 (15) | 0.04237 (4) | 0.0211 (2) | |
H4A | 0.8897 | 0.0626 | 0.0094 | 0.032* | |
H4B | 0.8490 | 0.1325 | 0.0498 | 0.032* | |
H4C | 0.9116 | 0.0117 | 0.0636 | 0.032* | |
C5 | 0.94264 (6) | 0.24497 (14) | 0.04919 (4) | 0.0153 (2) | |
H5 | 0.9232 | 0.3305 | 0.0264 | 0.018* | |
C6 | 1.01195 (6) | 0.19787 (15) | 0.03505 (4) | 0.0197 (2) | |
H6A | 1.0315 | 0.1089 | 0.0553 | 0.030* | |
H6B | 1.0426 | 0.2915 | 0.0390 | 0.030* | |
H6C | 1.0060 | 0.1632 | 0.0018 | 0.030* | |
C7 | 1.02387 (6) | 0.47398 (14) | 0.12040 (4) | 0.0155 (2) | |
C8 | 1.07141 (6) | 0.47422 (15) | 0.16149 (4) | 0.0192 (2) | |
H8 | 1.0659 | 0.4006 | 0.1863 | 0.023* | |
C9 | 1.12668 (6) | 0.57976 (16) | 0.16690 (5) | 0.0228 (3) | |
H9 | 1.1581 | 0.5779 | 0.1953 | 0.027* | |
C10 | 1.13605 (6) | 0.68737 (16) | 0.13106 (5) | 0.0235 (3) | |
H10 | 1.1738 | 0.7591 | 0.1347 | 0.028* | |
C11 | 1.08994 (7) | 0.68980 (16) | 0.08981 (5) | 0.0247 (3) | |
H11 | 1.0961 | 0.7631 | 0.0650 | 0.030* | |
C12 | 1.03465 (6) | 0.58479 (15) | 0.08477 (4) | 0.0207 (2) | |
H12 | 1.0033 | 0.5881 | 0.0564 | 0.025* | |
C13 | 0.81154 (7) | 0.81277 (15) | 0.14411 (5) | 0.0250 (3) | |
H13A | 0.7766 | 0.7606 | 0.1601 | 0.037* | |
H13B | 0.7922 | 0.8414 | 0.1116 | 0.037* | |
H13C | 0.8276 | 0.9111 | 0.1614 | 0.037* | |
C14 | 0.87141 (6) | 0.69571 (14) | 0.14283 (4) | 0.0180 (2) | |
H14 | 0.9017 | 0.7480 | 0.1219 | 0.022* | |
C15 | 0.91391 (7) | 0.68311 (16) | 0.19195 (4) | 0.0233 (3) | |
H15A | 0.9278 | 0.7917 | 0.2033 | 0.035* | |
H15B | 0.9544 | 0.6171 | 0.1898 | 0.035* | |
H15C | 0.8867 | 0.6324 | 0.2142 | 0.035* | |
C16 | 0.72602 (6) | 0.57119 (16) | 0.04877 (4) | 0.0218 (2) | |
H16A | 0.7231 | 0.6757 | 0.0647 | 0.033* | |
H16B | 0.7010 | 0.4892 | 0.0643 | 0.033* | |
H16C | 0.7061 | 0.5811 | 0.0154 | 0.033* | |
C17 | 0.80103 (6) | 0.52024 (14) | 0.05162 (4) | 0.0163 (2) | |
H17 | 0.8013 | 0.4123 | 0.0357 | 0.020* | |
C18 | 0.83872 (7) | 0.63765 (17) | 0.02249 (5) | 0.0252 (3) | |
H18A | 0.8181 | 0.6341 | −0.0108 | 0.038* | |
H18B | 0.8867 | 0.6060 | 0.0249 | 0.038* | |
H18C | 0.8355 | 0.7479 | 0.0348 | 0.038* | |
C19 | 0.78538 (6) | 0.37687 (14) | 0.14769 (4) | 0.0164 (2) | |
C20 | 0.76958 (7) | 0.41958 (18) | 0.19242 (5) | 0.0263 (3) | |
H20 | 0.7888 | 0.5151 | 0.2073 | 0.032* | |
C21 | 0.72620 (7) | 0.3252 (2) | 0.21575 (5) | 0.0330 (3) | |
H21 | 0.7168 | 0.3558 | 0.2464 | 0.040* | |
C22 | 0.69685 (7) | 0.18726 (18) | 0.19442 (5) | 0.0274 (3) | |
H22 | 0.6679 | 0.1220 | 0.2106 | 0.033* | |
C23 | 0.70962 (7) | 0.14443 (16) | 0.14959 (5) | 0.0241 (3) | |
H23 | 0.6884 | 0.0516 | 0.1344 | 0.029* | |
C24 | 0.75370 (6) | 0.23788 (15) | 0.12678 (5) | 0.0206 (2) | |
H24 | 0.7626 | 0.2065 | 0.0961 | 0.025* | |
Si3 | 0.44829 (2) | 0.13947 (4) | 0.11813 (2) | 0.01413 (7) | |
Si4 | 0.33848 (2) | 0.01815 (4) | 0.10635 (2) | 0.01342 (7) | |
C25 | 0.43042 (7) | 0.20987 (16) | 0.21584 (4) | 0.0218 (2) | |
H25A | 0.4572 | 0.1139 | 0.2266 | 0.033* | |
H25B | 0.3824 | 0.1796 | 0.2081 | 0.033* | |
H25C | 0.4351 | 0.2916 | 0.2411 | 0.033* | |
C26 | 0.45634 (6) | 0.27984 (14) | 0.17149 (4) | 0.0185 (2) | |
H26 | 0.4259 | 0.3739 | 0.1616 | 0.022* | |
C27 | 0.52755 (7) | 0.35206 (17) | 0.18431 (5) | 0.0270 (3) | |
H27A | 0.5271 | 0.4307 | 0.2101 | 0.041* | |
H27B | 0.5412 | 0.4063 | 0.1565 | 0.041* | |
H27C | 0.5600 | 0.2653 | 0.1946 | 0.041* | |
C28 | 0.42502 (7) | 0.41899 (17) | 0.05920 (5) | 0.0300 (3) | |
H28A | 0.4446 | 0.4922 | 0.0845 | 0.045* | |
H28B | 0.3771 | 0.3985 | 0.0622 | 0.045* | |
H28C | 0.4282 | 0.4688 | 0.0283 | 0.045* | |
C29 | 0.46428 (6) | 0.25840 (15) | 0.06313 (4) | 0.0212 (2) | |
H29 | 0.4451 | 0.1918 | 0.0351 | 0.025* | |
C30 | 0.53954 (7) | 0.28767 (18) | 0.05824 (5) | 0.0301 (3) | |
H30A | 0.5430 | 0.3365 | 0.0273 | 0.045* | |
H30B | 0.5640 | 0.1843 | 0.0609 | 0.045* | |
H30C | 0.5596 | 0.3609 | 0.0834 | 0.045* | |
C31 | 0.51227 (6) | −0.03158 (14) | 0.12520 (4) | 0.0164 (2) | |
C32 | 0.52628 (6) | −0.11673 (15) | 0.08469 (4) | 0.0206 (2) | |
H32 | 0.5030 | −0.0873 | 0.0545 | 0.025* | |
C33 | 0.57320 (7) | −0.24251 (16) | 0.08779 (5) | 0.0238 (3) | |
H33 | 0.5816 | −0.2977 | 0.0599 | 0.029* | |
C34 | 0.60787 (6) | −0.28779 (16) | 0.13150 (5) | 0.0237 (3) | |
H34 | 0.6402 | −0.3733 | 0.1336 | 0.028* | |
C35 | 0.59481 (6) | −0.20691 (15) | 0.17197 (5) | 0.0225 (3) | |
H35 | 0.6182 | −0.2375 | 0.2020 | 0.027* | |
C36 | 0.54761 (6) | −0.08103 (15) | 0.16883 (4) | 0.0190 (2) | |
H36 | 0.5392 | −0.0274 | 0.1970 | 0.023* | |
C37 | 0.27046 (7) | 0.31327 (16) | 0.13141 (5) | 0.0252 (3) | |
H37A | 0.2352 | 0.3932 | 0.1207 | 0.038* | |
H37B | 0.3152 | 0.3653 | 0.1345 | 0.038* | |
H37C | 0.2627 | 0.2695 | 0.1622 | 0.038* | |
C38 | 0.26779 (6) | 0.17514 (14) | 0.09508 (4) | 0.0177 (2) | |
H38 | 0.2743 | 0.2282 | 0.0644 | 0.021* | |
C39 | 0.19554 (6) | 0.10389 (16) | 0.08694 (5) | 0.0237 (3) | |
H39A | 0.1863 | 0.0475 | 0.1157 | 0.035* | |
H39B | 0.1919 | 0.0272 | 0.0604 | 0.035* | |
H39C | 0.1625 | 0.1915 | 0.0795 | 0.035* | |
C40 | 0.28249 (7) | −0.26623 (17) | 0.05571 (5) | 0.0276 (3) | |
H40A | 0.2362 | −0.2221 | 0.0514 | 0.041* | |
H40B | 0.2914 | −0.3210 | 0.0865 | 0.041* | |
H40C | 0.2872 | −0.3439 | 0.0303 | 0.041* | |
C41 | 0.33377 (6) | −0.12780 (16) | 0.05397 (4) | 0.0203 (2) | |
H41 | 0.3796 | −0.1794 | 0.0556 | 0.024* | |
C42 | 0.32034 (7) | −0.0415 (2) | 0.00566 (4) | 0.0298 (3) | |
H42A | 0.3226 | −0.1205 | −0.0198 | 0.045* | |
H42B | 0.3548 | 0.0425 | 0.0040 | 0.045* | |
H42C | 0.2751 | 0.0083 | 0.0020 | 0.045* | |
C43 | 0.33233 (6) | −0.10919 (14) | 0.16082 (4) | 0.0156 (2) | |
C44 | 0.28518 (6) | −0.08099 (16) | 0.19235 (4) | 0.0202 (2) | |
H44 | 0.2534 | 0.0050 | 0.1860 | 0.024* | |
C45 | 0.28362 (7) | −0.17546 (17) | 0.23271 (4) | 0.0246 (3) | |
H45 | 0.2507 | −0.1547 | 0.2532 | 0.030* | |
C46 | 0.33015 (7) | −0.29972 (17) | 0.24291 (5) | 0.0254 (3) | |
H46 | 0.3297 | −0.3633 | 0.2707 | 0.031* | |
C47 | 0.37739 (7) | −0.33090 (15) | 0.21243 (5) | 0.0239 (3) | |
H47 | 0.4093 | −0.4163 | 0.2193 | 0.029* | |
C48 | 0.37817 (6) | −0.23746 (14) | 0.17185 (4) | 0.0194 (2) | |
H48 | 0.4105 | −0.2610 | 0.1511 | 0.023* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si1 | 0.01238 (14) | 0.01453 (14) | 0.01153 (14) | −0.00076 (11) | 0.00148 (11) | 0.00086 (11) |
Si2 | 0.01241 (15) | 0.01469 (14) | 0.01148 (14) | −0.00064 (11) | 0.00200 (11) | −0.00024 (11) |
C1 | 0.0270 (7) | 0.0314 (7) | 0.0158 (6) | 0.0038 (5) | 0.0040 (5) | 0.0076 (5) |
C2 | 0.0184 (6) | 0.0185 (5) | 0.0176 (5) | −0.0008 (4) | 0.0020 (4) | 0.0040 (4) |
C3 | 0.0274 (7) | 0.0220 (6) | 0.0241 (6) | 0.0061 (5) | 0.0025 (5) | 0.0058 (5) |
C4 | 0.0182 (6) | 0.0236 (6) | 0.0218 (6) | −0.0034 (5) | 0.0035 (5) | −0.0057 (5) |
C5 | 0.0143 (5) | 0.0166 (5) | 0.0149 (5) | −0.0001 (4) | 0.0021 (4) | −0.0010 (4) |
C6 | 0.0171 (6) | 0.0228 (6) | 0.0201 (6) | 0.0007 (5) | 0.0058 (4) | −0.0024 (5) |
C7 | 0.0141 (5) | 0.0162 (5) | 0.0164 (5) | −0.0005 (4) | 0.0022 (4) | −0.0012 (4) |
C8 | 0.0183 (6) | 0.0219 (6) | 0.0170 (5) | −0.0008 (5) | 0.0004 (4) | 0.0013 (4) |
C9 | 0.0177 (6) | 0.0268 (6) | 0.0224 (6) | −0.0026 (5) | −0.0024 (5) | −0.0029 (5) |
C10 | 0.0180 (6) | 0.0222 (6) | 0.0299 (7) | −0.0052 (5) | 0.0019 (5) | −0.0020 (5) |
C11 | 0.0241 (6) | 0.0236 (6) | 0.0261 (6) | −0.0073 (5) | 0.0023 (5) | 0.0059 (5) |
C12 | 0.0185 (6) | 0.0235 (6) | 0.0191 (6) | −0.0043 (5) | −0.0014 (4) | 0.0039 (5) |
C13 | 0.0239 (6) | 0.0193 (6) | 0.0314 (7) | 0.0015 (5) | 0.0029 (5) | −0.0068 (5) |
C14 | 0.0174 (6) | 0.0176 (5) | 0.0191 (6) | −0.0018 (4) | 0.0036 (4) | −0.0029 (4) |
C15 | 0.0211 (6) | 0.0277 (6) | 0.0207 (6) | −0.0034 (5) | 0.0012 (5) | −0.0078 (5) |
C16 | 0.0177 (6) | 0.0272 (6) | 0.0195 (6) | 0.0050 (5) | −0.0006 (4) | −0.0007 (5) |
C17 | 0.0160 (5) | 0.0188 (5) | 0.0139 (5) | 0.0014 (4) | 0.0010 (4) | 0.0001 (4) |
C18 | 0.0238 (6) | 0.0313 (7) | 0.0206 (6) | 0.0021 (5) | 0.0034 (5) | 0.0101 (5) |
C19 | 0.0133 (5) | 0.0198 (5) | 0.0161 (5) | 0.0010 (4) | 0.0025 (4) | 0.0029 (4) |
C20 | 0.0251 (7) | 0.0361 (7) | 0.0184 (6) | −0.0095 (6) | 0.0057 (5) | −0.0044 (5) |
C21 | 0.0296 (7) | 0.0532 (9) | 0.0182 (6) | −0.0108 (7) | 0.0105 (5) | −0.0001 (6) |
C22 | 0.0185 (6) | 0.0358 (7) | 0.0289 (7) | −0.0031 (5) | 0.0071 (5) | 0.0111 (6) |
C23 | 0.0194 (6) | 0.0198 (6) | 0.0340 (7) | −0.0022 (5) | 0.0068 (5) | 0.0022 (5) |
C24 | 0.0191 (6) | 0.0206 (6) | 0.0236 (6) | −0.0006 (5) | 0.0085 (5) | −0.0011 (5) |
Si3 | 0.01442 (15) | 0.01542 (14) | 0.01257 (14) | −0.00162 (11) | 0.00185 (11) | 0.00045 (11) |
Si4 | 0.01289 (15) | 0.01534 (14) | 0.01194 (14) | −0.00043 (11) | 0.00134 (11) | −0.00046 (11) |
C25 | 0.0242 (6) | 0.0246 (6) | 0.0165 (5) | −0.0027 (5) | 0.0028 (5) | −0.0042 (5) |
C26 | 0.0208 (6) | 0.0171 (5) | 0.0170 (5) | −0.0013 (4) | 0.0004 (4) | −0.0015 (4) |
C27 | 0.0284 (7) | 0.0268 (6) | 0.0249 (6) | −0.0098 (5) | −0.0001 (5) | −0.0032 (5) |
C28 | 0.0286 (7) | 0.0293 (7) | 0.0316 (7) | −0.0009 (6) | 0.0028 (6) | 0.0148 (6) |
C29 | 0.0234 (6) | 0.0235 (6) | 0.0166 (5) | −0.0049 (5) | 0.0027 (5) | 0.0040 (5) |
C30 | 0.0294 (7) | 0.0304 (7) | 0.0330 (7) | −0.0038 (6) | 0.0135 (6) | 0.0083 (6) |
C31 | 0.0129 (5) | 0.0178 (5) | 0.0189 (5) | −0.0025 (4) | 0.0032 (4) | 0.0005 (4) |
C32 | 0.0183 (6) | 0.0237 (6) | 0.0198 (6) | −0.0003 (5) | 0.0032 (4) | −0.0002 (5) |
C33 | 0.0223 (6) | 0.0244 (6) | 0.0262 (6) | 0.0006 (5) | 0.0089 (5) | −0.0038 (5) |
C34 | 0.0182 (6) | 0.0206 (6) | 0.0333 (7) | 0.0017 (5) | 0.0077 (5) | 0.0039 (5) |
C35 | 0.0201 (6) | 0.0237 (6) | 0.0239 (6) | 0.0007 (5) | 0.0030 (5) | 0.0063 (5) |
C36 | 0.0177 (6) | 0.0207 (6) | 0.0191 (6) | −0.0013 (4) | 0.0042 (4) | 0.0010 (5) |
C37 | 0.0232 (6) | 0.0218 (6) | 0.0310 (7) | 0.0054 (5) | 0.0048 (5) | −0.0021 (5) |
C38 | 0.0146 (5) | 0.0203 (5) | 0.0181 (5) | 0.0019 (4) | 0.0012 (4) | 0.0039 (4) |
C39 | 0.0152 (6) | 0.0281 (6) | 0.0269 (6) | 0.0013 (5) | 0.0002 (5) | 0.0053 (5) |
C40 | 0.0292 (7) | 0.0248 (6) | 0.0271 (7) | −0.0044 (5) | −0.0025 (5) | −0.0079 (5) |
C41 | 0.0174 (6) | 0.0263 (6) | 0.0166 (5) | −0.0001 (5) | 0.0003 (4) | −0.0060 (5) |
C42 | 0.0300 (7) | 0.0453 (8) | 0.0139 (6) | −0.0067 (6) | 0.0018 (5) | −0.0051 (6) |
C43 | 0.0151 (5) | 0.0167 (5) | 0.0143 (5) | −0.0035 (4) | −0.0001 (4) | 0.0002 (4) |
C44 | 0.0176 (6) | 0.0253 (6) | 0.0176 (6) | 0.0000 (5) | 0.0022 (4) | 0.0010 (5) |
C45 | 0.0235 (6) | 0.0342 (7) | 0.0172 (6) | −0.0041 (5) | 0.0061 (5) | 0.0024 (5) |
C46 | 0.0277 (7) | 0.0286 (7) | 0.0190 (6) | −0.0081 (5) | −0.0001 (5) | 0.0067 (5) |
C47 | 0.0255 (7) | 0.0194 (6) | 0.0253 (6) | −0.0008 (5) | −0.0013 (5) | 0.0051 (5) |
C48 | 0.0196 (6) | 0.0179 (5) | 0.0207 (6) | −0.0016 (4) | 0.0027 (4) | 0.0005 (4) |
Si1—C7 | 1.8926 (12) | Si3—C31 | 1.8911 (12) |
Si1—C2 | 1.9005 (12) | Si3—C26 | 1.8993 (12) |
Si1—C5 | 1.9107 (12) | Si3—C29 | 1.9101 (12) |
Si1—Si2 | 2.3898 (4) | Si3—Si4 | 2.3799 (5) |
Si2—C19 | 1.8926 (12) | Si4—C43 | 1.8906 (12) |
Si2—C14 | 1.8990 (12) | Si4—C38 | 1.9045 (12) |
Si2—C17 | 1.9051 (12) | Si4—C41 | 1.9087 (12) |
C1—C2 | 1.5375 (17) | C25—C26 | 1.5387 (17) |
C1—H1A | 0.9800 | C25—H25A | 0.9800 |
C1—H1B | 0.9800 | C25—H25B | 0.9800 |
C1—H1C | 0.9800 | C25—H25C | 0.9800 |
C2—C3 | 1.5388 (17) | C26—C27 | 1.5312 (17) |
C2—H2 | 1.0000 | C26—H26 | 1.0000 |
C3—H3A | 0.9800 | C27—H27A | 0.9800 |
C3—H3B | 0.9800 | C27—H27B | 0.9800 |
C3—H3C | 0.9800 | C27—H27C | 0.9800 |
C4—C5 | 1.5367 (16) | C28—C29 | 1.5340 (19) |
C4—H4A | 0.9800 | C28—H28A | 0.9800 |
C4—H4B | 0.9800 | C28—H28B | 0.9800 |
C4—H4C | 0.9800 | C28—H28C | 0.9800 |
C5—C6 | 1.5347 (16) | C29—C30 | 1.5379 (18) |
C5—H5 | 1.0000 | C29—H29 | 1.0000 |
C6—H6A | 0.9800 | C30—H30A | 0.9800 |
C6—H6B | 0.9800 | C30—H30B | 0.9800 |
C6—H6C | 0.9800 | C30—H30C | 0.9800 |
C7—C8 | 1.3987 (16) | C31—C36 | 1.4008 (16) |
C7—C12 | 1.4033 (16) | C31—C32 | 1.4096 (17) |
C8—C9 | 1.3927 (17) | C32—C33 | 1.3893 (17) |
C8—H8 | 0.9500 | C32—H32 | 0.9500 |
C9—C10 | 1.3839 (18) | C33—C34 | 1.3881 (19) |
C9—H9 | 0.9500 | C33—H33 | 0.9500 |
C10—C11 | 1.3864 (18) | C34—C35 | 1.3860 (19) |
C10—H10 | 0.9500 | C34—H34 | 0.9500 |
C11—C12 | 1.3903 (17) | C35—C36 | 1.3935 (17) |
C11—H11 | 0.9500 | C35—H35 | 0.9500 |
C12—H12 | 0.9500 | C36—H36 | 0.9500 |
C13—C14 | 1.5357 (17) | C37—C38 | 1.5350 (17) |
C13—H13A | 0.9800 | C37—H37A | 0.9800 |
C13—H13B | 0.9800 | C37—H37B | 0.9800 |
C13—H13C | 0.9800 | C37—H37C | 0.9800 |
C14—C15 | 1.5342 (17) | C38—C39 | 1.5375 (17) |
C14—H14 | 1.0000 | C38—H38 | 1.0000 |
C15—H15A | 0.9800 | C39—H39A | 0.9800 |
C15—H15B | 0.9800 | C39—H39B | 0.9800 |
C15—H15C | 0.9800 | C39—H39C | 0.9800 |
C16—C17 | 1.5381 (16) | C40—C41 | 1.5354 (18) |
C16—H16A | 0.9800 | C40—H40A | 0.9800 |
C16—H16B | 0.9800 | C40—H40B | 0.9800 |
C16—H16C | 0.9800 | C40—H40C | 0.9800 |
C17—C18 | 1.5346 (17) | C41—C42 | 1.5388 (18) |
C17—H17 | 1.0000 | C41—H41 | 1.0000 |
C18—H18A | 0.9800 | C42—H42A | 0.9800 |
C18—H18B | 0.9800 | C42—H42B | 0.9800 |
C18—H18C | 0.9800 | C42—H42C | 0.9800 |
C19—C20 | 1.3968 (17) | C43—C44 | 1.4011 (16) |
C19—C24 | 1.4014 (17) | C43—C48 | 1.4033 (16) |
C20—C21 | 1.3944 (18) | C44—C45 | 1.3921 (17) |
C20—H20 | 0.9500 | C44—H44 | 0.9500 |
C21—C22 | 1.381 (2) | C45—C46 | 1.3842 (19) |
C21—H21 | 0.9500 | C45—H45 | 0.9500 |
C22—C23 | 1.3801 (19) | C46—C47 | 1.3851 (19) |
C22—H22 | 0.9500 | C46—H46 | 0.9500 |
C23—C24 | 1.3915 (17) | C47—C48 | 1.3903 (17) |
C23—H23 | 0.9500 | C47—H47 | 0.9500 |
C24—H24 | 0.9500 | C48—H48 | 0.9500 |
C7—Si1—C2 | 112.02 (5) | C31—Si3—C26 | 112.86 (5) |
C7—Si1—C5 | 107.32 (5) | C31—Si3—C29 | 106.67 (5) |
C2—Si1—C5 | 109.35 (5) | C26—Si3—C29 | 109.63 (6) |
C7—Si1—Si2 | 109.25 (4) | C31—Si3—Si4 | 106.81 (4) |
C2—Si1—Si2 | 110.49 (4) | C26—Si3—Si4 | 110.18 (4) |
C5—Si1—Si2 | 108.29 (4) | C29—Si3—Si4 | 110.61 (4) |
C19—Si2—C14 | 112.39 (5) | C43—Si4—C38 | 112.83 (5) |
C19—Si2—C17 | 106.02 (5) | C43—Si4—C41 | 106.70 (5) |
C14—Si2—C17 | 110.72 (5) | C38—Si4—C41 | 109.98 (5) |
C19—Si2—Si1 | 110.02 (4) | C43—Si4—Si3 | 106.18 (4) |
C14—Si2—Si1 | 108.90 (4) | C38—Si4—Si3 | 112.11 (4) |
C17—Si2—Si1 | 108.71 (4) | C41—Si4—Si3 | 108.79 (4) |
C2—C1—H1A | 109.5 | C26—C25—H25A | 109.5 |
C2—C1—H1B | 109.5 | C26—C25—H25B | 109.5 |
H1A—C1—H1B | 109.5 | H25A—C25—H25B | 109.5 |
C2—C1—H1C | 109.5 | C26—C25—H25C | 109.5 |
H1A—C1—H1C | 109.5 | H25A—C25—H25C | 109.5 |
H1B—C1—H1C | 109.5 | H25B—C25—H25C | 109.5 |
C1—C2—C3 | 110.59 (10) | C27—C26—C25 | 110.58 (10) |
C1—C2—Si1 | 114.42 (8) | C27—C26—Si3 | 113.72 (9) |
C3—C2—Si1 | 114.16 (8) | C25—C26—Si3 | 115.18 (8) |
C1—C2—H2 | 105.6 | C27—C26—H26 | 105.5 |
C3—C2—H2 | 105.6 | C25—C26—H26 | 105.5 |
Si1—C2—H2 | 105.6 | Si3—C26—H26 | 105.5 |
C2—C3—H3A | 109.5 | C26—C27—H27A | 109.5 |
C2—C3—H3B | 109.5 | C26—C27—H27B | 109.5 |
H3A—C3—H3B | 109.5 | H27A—C27—H27B | 109.5 |
C2—C3—H3C | 109.5 | C26—C27—H27C | 109.5 |
H3A—C3—H3C | 109.5 | H27A—C27—H27C | 109.5 |
H3B—C3—H3C | 109.5 | H27B—C27—H27C | 109.5 |
C5—C4—H4A | 109.5 | C29—C28—H28A | 109.5 |
C5—C4—H4B | 109.5 | C29—C28—H28B | 109.5 |
H4A—C4—H4B | 109.5 | H28A—C28—H28B | 109.5 |
C5—C4—H4C | 109.5 | C29—C28—H28C | 109.5 |
H4A—C4—H4C | 109.5 | H28A—C28—H28C | 109.5 |
H4B—C4—H4C | 109.5 | H28B—C28—H28C | 109.5 |
C6—C5—C4 | 109.95 (10) | C28—C29—C30 | 110.32 (11) |
C6—C5—Si1 | 114.32 (8) | C28—C29—Si3 | 111.38 (9) |
C4—C5—Si1 | 111.81 (8) | C30—C29—Si3 | 115.26 (9) |
C6—C5—H5 | 106.8 | C28—C29—H29 | 106.4 |
C4—C5—H5 | 106.8 | C30—C29—H29 | 106.4 |
Si1—C5—H5 | 106.8 | Si3—C29—H29 | 106.4 |
C5—C6—H6A | 109.5 | C29—C30—H30A | 109.5 |
C5—C6—H6B | 109.5 | C29—C30—H30B | 109.5 |
H6A—C6—H6B | 109.5 | H30A—C30—H30B | 109.5 |
C5—C6—H6C | 109.5 | C29—C30—H30C | 109.5 |
H6A—C6—H6C | 109.5 | H30A—C30—H30C | 109.5 |
H6B—C6—H6C | 109.5 | H30B—C30—H30C | 109.5 |
C8—C7—C12 | 116.81 (11) | C36—C31—C32 | 116.65 (11) |
C8—C7—Si1 | 123.61 (9) | C36—C31—Si3 | 124.02 (9) |
C12—C7—Si1 | 119.57 (9) | C32—C31—Si3 | 119.33 (9) |
C9—C8—C7 | 121.63 (11) | C33—C32—C31 | 121.74 (12) |
C9—C8—H8 | 119.2 | C33—C32—H32 | 119.1 |
C7—C8—H8 | 119.2 | C31—C32—H32 | 119.1 |
C10—C9—C8 | 120.20 (11) | C34—C33—C32 | 120.27 (12) |
C10—C9—H9 | 119.9 | C34—C33—H33 | 119.9 |
C8—C9—H9 | 119.9 | C32—C33—H33 | 119.9 |
C9—C10—C11 | 119.59 (11) | C35—C34—C33 | 119.26 (12) |
C9—C10—H10 | 120.2 | C35—C34—H34 | 120.4 |
C11—C10—H10 | 120.2 | C33—C34—H34 | 120.4 |
C10—C11—C12 | 119.90 (12) | C34—C35—C36 | 120.41 (12) |
C10—C11—H11 | 120.0 | C34—C35—H35 | 119.8 |
C12—C11—H11 | 120.0 | C36—C35—H35 | 119.8 |
C11—C12—C7 | 121.87 (11) | C35—C36—C31 | 121.67 (11) |
C11—C12—H12 | 119.1 | C35—C36—H36 | 119.2 |
C7—C12—H12 | 119.1 | C31—C36—H36 | 119.2 |
C14—C13—H13A | 109.5 | C38—C37—H37A | 109.5 |
C14—C13—H13B | 109.5 | C38—C37—H37B | 109.5 |
H13A—C13—H13B | 109.5 | H37A—C37—H37B | 109.5 |
C14—C13—H13C | 109.5 | C38—C37—H37C | 109.5 |
H13A—C13—H13C | 109.5 | H37A—C37—H37C | 109.5 |
H13B—C13—H13C | 109.5 | H37B—C37—H37C | 109.5 |
C15—C14—C13 | 110.61 (10) | C37—C38—C39 | 109.36 (10) |
C15—C14—Si2 | 113.92 (8) | C37—C38—Si4 | 115.80 (8) |
C13—C14—Si2 | 114.15 (8) | C39—C38—Si4 | 114.52 (8) |
C15—C14—H14 | 105.8 | C37—C38—H38 | 105.4 |
C13—C14—H14 | 105.8 | C39—C38—H38 | 105.4 |
Si2—C14—H14 | 105.8 | Si4—C38—H38 | 105.4 |
C14—C15—H15A | 109.5 | C38—C39—H39A | 109.5 |
C14—C15—H15B | 109.5 | C38—C39—H39B | 109.5 |
H15A—C15—H15B | 109.5 | H39A—C39—H39B | 109.5 |
C14—C15—H15C | 109.5 | C38—C39—H39C | 109.5 |
H15A—C15—H15C | 109.5 | H39A—C39—H39C | 109.5 |
H15B—C15—H15C | 109.5 | H39B—C39—H39C | 109.5 |
C17—C16—H16A | 109.5 | C41—C40—H40A | 109.5 |
C17—C16—H16B | 109.5 | C41—C40—H40B | 109.5 |
H16A—C16—H16B | 109.5 | H40A—C40—H40B | 109.5 |
C17—C16—H16C | 109.5 | C41—C40—H40C | 109.5 |
H16A—C16—H16C | 109.5 | H40A—C40—H40C | 109.5 |
H16B—C16—H16C | 109.5 | H40B—C40—H40C | 109.5 |
C18—C17—C16 | 109.76 (10) | C40—C41—C42 | 109.78 (10) |
C18—C17—Si2 | 112.38 (8) | C40—C41—Si4 | 114.00 (9) |
C16—C17—Si2 | 114.43 (8) | C42—C41—Si4 | 112.92 (9) |
C18—C17—H17 | 106.6 | C40—C41—H41 | 106.5 |
C16—C17—H17 | 106.6 | C42—C41—H41 | 106.5 |
Si2—C17—H17 | 106.6 | Si4—C41—H41 | 106.5 |
C17—C18—H18A | 109.5 | C41—C42—H42A | 109.5 |
C17—C18—H18B | 109.5 | C41—C42—H42B | 109.5 |
H18A—C18—H18B | 109.5 | H42A—C42—H42B | 109.5 |
C17—C18—H18C | 109.5 | C41—C42—H42C | 109.5 |
H18A—C18—H18C | 109.5 | H42A—C42—H42C | 109.5 |
H18B—C18—H18C | 109.5 | H42B—C42—H42C | 109.5 |
C20—C19—C24 | 116.76 (11) | C44—C43—C48 | 116.82 (11) |
C20—C19—Si2 | 124.48 (9) | C44—C43—Si4 | 123.77 (9) |
C24—C19—Si2 | 118.76 (9) | C48—C43—Si4 | 119.38 (9) |
C21—C20—C19 | 121.49 (13) | C45—C44—C43 | 121.81 (12) |
C21—C20—H20 | 119.3 | C45—C44—H44 | 119.1 |
C19—C20—H20 | 119.3 | C43—C44—H44 | 119.1 |
C22—C21—C20 | 120.16 (13) | C46—C45—C44 | 119.92 (12) |
C22—C21—H21 | 119.9 | C46—C45—H45 | 120.0 |
C20—C21—H21 | 119.9 | C44—C45—H45 | 120.0 |
C23—C22—C21 | 119.85 (12) | C45—C46—C47 | 119.71 (12) |
C23—C22—H22 | 120.1 | C45—C46—H46 | 120.1 |
C21—C22—H22 | 120.1 | C47—C46—H46 | 120.1 |
C22—C23—C24 | 119.69 (12) | C46—C47—C48 | 120.13 (12) |
C22—C23—H23 | 120.2 | C46—C47—H47 | 119.9 |
C24—C23—H23 | 120.2 | C48—C47—H47 | 119.9 |
C23—C24—C19 | 122.00 (12) | C47—C48—C43 | 121.61 (12) |
C23—C24—H24 | 119.0 | C47—C48—H48 | 119.2 |
C19—C24—H24 | 119.0 | C43—C48—H48 | 119.2 |
C2—Si1—C7—C8 | −13.73 (12) | C31—Si3—C26—C27 | 55.71 (10) |
C5—Si1—C7—C8 | −133.76 (10) | C29—Si3—C26—C27 | −63.04 (10) |
Si2—Si1—C7—C8 | 109.03 (10) | Si4—Si3—C26—C27 | 175.01 (8) |
C2—Si1—C7—C12 | 166.95 (9) | C31—Si3—C26—C25 | −73.40 (10) |
C5—Si1—C7—C12 | 46.92 (11) | C29—Si3—C26—C25 | 167.85 (9) |
Si2—Si1—C7—C12 | −70.28 (10) | Si4—Si3—C26—C25 | 45.90 (10) |
C12—C7—C8—C9 | 0.23 (18) | C26—Si3—C31—C36 | 18.23 (12) |
Si1—C7—C8—C9 | −179.10 (10) | C29—Si3—C31—C36 | 138.69 (10) |
C7—C8—C9—C10 | −0.42 (19) | Si4—Si3—C31—C36 | −103.00 (10) |
C8—C9—C10—C11 | 0.2 (2) | C26—Si3—C31—C32 | −161.78 (9) |
C9—C10—C11—C12 | 0.2 (2) | C29—Si3—C31—C32 | −41.32 (11) |
C10—C11—C12—C7 | −0.4 (2) | Si4—Si3—C31—C32 | 76.99 (9) |
C8—C7—C12—C11 | 0.17 (18) | C36—C31—C32—C33 | −0.53 (18) |
Si1—C7—C12—C11 | 179.53 (10) | Si3—C31—C32—C33 | 179.48 (10) |
C19—Si2—C14—C15 | 66.80 (10) | C31—C32—C33—C34 | −0.02 (19) |
C17—Si2—C14—C15 | −174.84 (8) | C32—C33—C34—C35 | 0.44 (19) |
Si1—Si2—C14—C15 | −55.37 (9) | C33—C34—C35—C36 | −0.29 (19) |
C19—Si2—C14—C13 | −61.59 (10) | C34—C35—C36—C31 | −0.29 (19) |
C17—Si2—C14—C13 | 56.77 (10) | C32—C31—C36—C35 | 0.69 (17) |
Si1—Si2—C14—C13 | 176.24 (8) | Si3—C31—C36—C35 | −179.32 (9) |
C14—Si2—C19—C20 | −11.15 (13) | C38—Si4—C43—C44 | −6.11 (12) |
C17—Si2—C19—C20 | −132.24 (11) | C41—Si4—C43—C44 | −127.00 (10) |
Si1—Si2—C19—C20 | 110.39 (11) | Si3—Si4—C43—C44 | 117.08 (10) |
C14—Si2—C19—C24 | 169.45 (9) | C38—Si4—C43—C48 | 175.65 (9) |
C17—Si2—C19—C24 | 48.35 (11) | C41—Si4—C43—C48 | 54.76 (10) |
Si1—Si2—C19—C24 | −69.02 (10) | Si3—Si4—C43—C48 | −61.16 (10) |
C24—C19—C20—C21 | 2.1 (2) | C48—C43—C44—C45 | −0.07 (18) |
Si2—C19—C20—C21 | −177.28 (11) | Si4—C43—C44—C45 | −178.34 (10) |
C19—C20—C21—C22 | −1.0 (2) | C43—C44—C45—C46 | 0.94 (19) |
C20—C21—C22—C23 | −1.1 (2) | C44—C45—C46—C47 | −1.0 (2) |
C21—C22—C23—C24 | 2.0 (2) | C45—C46—C47—C48 | 0.2 (2) |
C22—C23—C24—C19 | −0.8 (2) | C46—C47—C48—C43 | 0.70 (19) |
C20—C19—C24—C23 | −1.23 (18) | C44—C43—C48—C47 | −0.75 (17) |
Si2—C19—C24—C23 | 178.22 (10) | Si4—C43—C48—C47 | 177.61 (9) |
C24H34Br4Si2 | F(000) = 1384 |
Mr = 698.33 | Dx = 1.691 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.8779 (7) Å | Cell parameters from 9033 reflections |
b = 10.4042 (8) Å | θ = 2.4–28.4° |
c = 29.699 (2) Å | µ = 5.97 mm−1 |
β = 90.975 (1)° | T = 100 K |
V = 2742.8 (4) Å3 | Thick plate, colorless |
Z = 4 | 0.14 × 0.12 × 0.07 mm |
Bruker SMART APEX CCD diffractometer | 6875 independent reflections |
Radiation source: fine-focus sealed tube | 5471 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 28.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −11→11 |
Tmin = 0.49, Tmax = 0.69 | k = −13→13 |
47392 measured reflections | l = −39→39 |
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)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.062 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0222P)2 + 2.5797P] where P = (Fo2 + 2Fc2)/3 |
6875 reflections | (Δ/σ)max = 0.001 |
287 parameters | Δρmax = 1.00 e Å−3 |
38 restraints | Δρmin = −1.05 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, 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 bromodimethyl group based on C16 is rotationally disordered over two nearly superimposable sites in an 88:12 ratio. The two components of the disorder were refined subject to restraints that their geometries be comparable. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.02503 (3) | −0.16520 (3) | 0.33755 (2) | 0.02338 (7) | |
Br2 | 0.50578 (3) | 0.15264 (3) | 0.28016 (2) | 0.02263 (7) | |
Br3 | 0.01829 (3) | 0.41338 (3) | 0.33412 (2) | 0.02135 (7) | |
Si1 | 0.23670 (7) | 0.08194 (7) | 0.34048 (2) | 0.01256 (14) | |
Si2 | 0.28642 (7) | 0.27865 (7) | 0.38516 (2) | 0.01214 (13) | |
C1 | 0.0249 (3) | 0.0278 (2) | 0.34221 (8) | 0.0167 (5) | |
C2 | −0.0765 (3) | 0.0699 (3) | 0.30209 (9) | 0.0227 (6) | |
H2A | −0.1798 | 0.0402 | 0.3069 | 0.034* | |
H2B | −0.0384 | 0.0325 | 0.2742 | 0.034* | |
H2C | −0.0758 | 0.1639 | 0.2997 | 0.034* | |
C3 | −0.0557 (3) | 0.0586 (3) | 0.38559 (9) | 0.0207 (6) | |
H3A | −0.0742 | 0.1513 | 0.3873 | 0.031* | |
H3B | 0.0071 | 0.0318 | 0.4114 | 0.031* | |
H3C | −0.1520 | 0.0126 | 0.3861 | 0.031* | |
C4 | 0.2913 (3) | 0.0898 (3) | 0.27793 (8) | 0.0171 (5) | |
C5 | 0.2928 (3) | −0.0419 (3) | 0.25465 (9) | 0.0233 (6) | |
H5A | 0.1897 | −0.0752 | 0.2522 | 0.035* | |
H5B | 0.3551 | −0.1017 | 0.2724 | 0.035* | |
H5C | 0.3345 | −0.0329 | 0.2245 | 0.035* | |
C6 | 0.2083 (3) | 0.1864 (3) | 0.24738 (9) | 0.0243 (6) | |
H6A | 0.2686 | 0.2034 | 0.2207 | 0.037* | |
H6B | 0.1928 | 0.2667 | 0.2639 | 0.037* | |
H6C | 0.1105 | 0.1507 | 0.2380 | 0.037* | |
C7 | 0.3517 (3) | −0.0469 (2) | 0.37044 (8) | 0.0144 (5) | |
C8 | 0.4842 (3) | −0.1028 (2) | 0.35435 (9) | 0.0180 (5) | |
H8 | 0.5176 | −0.0806 | 0.3251 | 0.022* | |
C9 | 0.5678 (3) | −0.1897 (3) | 0.38002 (9) | 0.0215 (6) | |
H9 | 0.6568 | −0.2261 | 0.3681 | 0.026* | |
C10 | 0.5231 (3) | −0.2238 (3) | 0.42260 (9) | 0.0219 (6) | |
H10 | 0.5815 | −0.2822 | 0.4402 | 0.026* | |
C11 | 0.3912 (3) | −0.1715 (3) | 0.43940 (9) | 0.0210 (6) | |
H11 | 0.3587 | −0.1943 | 0.4687 | 0.025* | |
C12 | 0.3071 (3) | −0.0861 (2) | 0.41333 (8) | 0.0174 (5) | |
H12 | 0.2160 | −0.0529 | 0.4250 | 0.021* | |
C13 | 0.2337 (3) | 0.4393 (2) | 0.35601 (9) | 0.0180 (5) | |
C14 | 0.3172 (3) | 0.4782 (3) | 0.31345 (9) | 0.0249 (6) | |
H14A | 0.2579 | 0.5425 | 0.2968 | 0.037* | |
H14B | 0.3317 | 0.4024 | 0.2944 | 0.037* | |
H14C | 0.4155 | 0.5146 | 0.3219 | 0.037* | |
C15 | 0.2331 (3) | 0.5527 (3) | 0.38851 (10) | 0.0259 (6) | |
H15A | 0.3356 | 0.5675 | 0.4002 | 0.039* | |
H15B | 0.1663 | 0.5336 | 0.4136 | 0.039* | |
H15C | 0.1972 | 0.6297 | 0.3727 | 0.039* | |
C16 | 0.4955 (3) | 0.2899 (2) | 0.40556 (7) | 0.0183 (5) | |
Br4 | 0.50066 (3) | 0.39238 (3) | 0.46210 (2) | 0.01971 (9) | 0.8812 (9) |
C17 | 0.5787 (3) | 0.1649 (2) | 0.41677 (13) | 0.0185 (6) | 0.8812 (9) |
H17A | 0.5162 | 0.1116 | 0.4362 | 0.028* | 0.8812 (9) |
H17B | 0.5993 | 0.1183 | 0.3889 | 0.028* | 0.8812 (9) |
H17C | 0.6740 | 0.1849 | 0.4324 | 0.028* | 0.8812 (9) |
C18 | 0.6092 (5) | 0.3659 (3) | 0.37416 (12) | 0.0237 (10) | 0.8812 (9) |
H18A | 0.5644 | 0.4484 | 0.3653 | 0.036* | 0.8812 (9) |
H18B | 0.7039 | 0.3814 | 0.3907 | 0.036* | 0.8812 (9) |
H18C | 0.6293 | 0.3148 | 0.3472 | 0.036* | 0.8812 (9) |
Br4A | 0.6209 (3) | 0.4004 (3) | 0.37171 (11) | 0.01971 (9) | 0.1188 (9) |
C17A | 0.464 (2) | 0.3531 (13) | 0.4519 (3) | 0.0185 (6) | 0.1188 (9) |
H17D | 0.4135 | 0.4358 | 0.4472 | 0.028* | 0.1188 (9) |
H17E | 0.4000 | 0.2964 | 0.4696 | 0.028* | 0.1188 (9) |
H17F | 0.5599 | 0.3671 | 0.4682 | 0.028* | 0.1188 (9) |
C18A | 0.575 (2) | 0.1610 (11) | 0.4144 (8) | 0.0237 (10) | 0.1188 (9) |
H18D | 0.5960 | 0.1190 | 0.3856 | 0.036* | 0.1188 (9) |
H18E | 0.6699 | 0.1761 | 0.4309 | 0.036* | 0.1188 (9) |
H18F | 0.5099 | 0.1055 | 0.4323 | 0.036* | 0.1188 (9) |
C19 | 0.1718 (3) | 0.2614 (2) | 0.43854 (8) | 0.0148 (5) | |
C20 | 0.0389 (3) | 0.3299 (3) | 0.44706 (9) | 0.0208 (6) | |
H20 | −0.0002 | 0.3869 | 0.4248 | 0.025* | |
C21 | −0.0368 (3) | 0.3163 (3) | 0.48729 (9) | 0.0257 (6) | |
H21 | −0.1256 | 0.3648 | 0.4923 | 0.031* | |
C22 | 0.0156 (3) | 0.2331 (3) | 0.52014 (9) | 0.0272 (6) | |
H22 | −0.0364 | 0.2243 | 0.5477 | 0.033* | |
C23 | 0.1445 (3) | 0.1626 (3) | 0.51256 (9) | 0.0249 (6) | |
H23 | 0.1805 | 0.1037 | 0.5347 | 0.030* | |
C24 | 0.2215 (3) | 0.1777 (3) | 0.47253 (8) | 0.0182 (5) | |
H24 | 0.3109 | 0.1295 | 0.4681 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.02017 (13) | 0.01707 (13) | 0.03266 (15) | −0.00137 (10) | −0.00704 (11) | −0.00487 (11) |
Br2 | 0.01913 (13) | 0.02930 (16) | 0.01961 (13) | 0.00066 (11) | 0.00462 (10) | 0.00286 (11) |
Br3 | 0.01822 (13) | 0.02552 (15) | 0.02019 (13) | 0.00314 (10) | −0.00308 (10) | 0.00377 (11) |
Si1 | 0.0119 (3) | 0.0145 (3) | 0.0112 (3) | 0.0016 (3) | −0.0008 (2) | −0.0004 (3) |
Si2 | 0.0125 (3) | 0.0135 (3) | 0.0105 (3) | 0.0000 (3) | 0.0009 (2) | −0.0001 (3) |
C1 | 0.0160 (12) | 0.0139 (12) | 0.0200 (13) | 0.0010 (10) | −0.0032 (10) | −0.0017 (10) |
C2 | 0.0164 (13) | 0.0244 (15) | 0.0271 (14) | 0.0039 (11) | −0.0062 (11) | −0.0013 (12) |
C3 | 0.0141 (13) | 0.0220 (14) | 0.0260 (14) | −0.0027 (10) | 0.0034 (10) | −0.0012 (11) |
C4 | 0.0168 (12) | 0.0235 (14) | 0.0110 (11) | 0.0032 (10) | 0.0003 (9) | −0.0014 (10) |
C5 | 0.0259 (14) | 0.0292 (16) | 0.0148 (13) | 0.0045 (12) | 0.0001 (11) | −0.0079 (11) |
C6 | 0.0285 (15) | 0.0315 (16) | 0.0129 (12) | 0.0057 (12) | −0.0013 (11) | 0.0030 (11) |
C7 | 0.0146 (12) | 0.0121 (12) | 0.0165 (12) | −0.0011 (9) | −0.0027 (9) | −0.0021 (10) |
C8 | 0.0187 (13) | 0.0180 (13) | 0.0172 (12) | 0.0001 (10) | −0.0026 (10) | −0.0004 (10) |
C9 | 0.0160 (13) | 0.0187 (14) | 0.0297 (15) | 0.0028 (10) | −0.0038 (11) | −0.0021 (11) |
C10 | 0.0218 (14) | 0.0159 (13) | 0.0275 (14) | 0.0003 (11) | −0.0109 (11) | 0.0026 (11) |
C11 | 0.0266 (14) | 0.0181 (13) | 0.0183 (13) | −0.0035 (11) | −0.0050 (11) | 0.0059 (11) |
C12 | 0.0173 (12) | 0.0153 (13) | 0.0195 (13) | −0.0030 (10) | −0.0019 (10) | −0.0015 (10) |
C13 | 0.0152 (12) | 0.0178 (13) | 0.0209 (13) | 0.0008 (10) | −0.0035 (10) | 0.0017 (11) |
C14 | 0.0257 (15) | 0.0263 (15) | 0.0226 (14) | −0.0025 (12) | 0.0020 (11) | 0.0095 (12) |
C15 | 0.0333 (16) | 0.0134 (14) | 0.0309 (16) | 0.0010 (11) | −0.0035 (12) | 0.0013 (12) |
C16 | 0.0190 (13) | 0.0205 (14) | 0.0154 (12) | −0.0018 (10) | −0.0007 (10) | −0.0055 (10) |
Br4 | 0.02271 (16) | 0.02007 (17) | 0.01624 (15) | −0.00242 (12) | −0.00282 (11) | −0.00367 (12) |
C17 | 0.0059 (12) | 0.0196 (15) | 0.0300 (16) | 0.0003 (11) | −0.0014 (11) | −0.0114 (13) |
C18 | 0.041 (2) | 0.0069 (19) | 0.0240 (18) | 0.0023 (15) | 0.0040 (14) | 0.0091 (15) |
Br4A | 0.02271 (16) | 0.02007 (17) | 0.01624 (15) | −0.00242 (12) | −0.00282 (11) | −0.00367 (12) |
C17A | 0.0059 (12) | 0.0196 (15) | 0.0300 (16) | 0.0003 (11) | −0.0014 (11) | −0.0114 (13) |
C18A | 0.041 (2) | 0.0069 (19) | 0.0240 (18) | 0.0023 (15) | 0.0040 (14) | 0.0091 (15) |
C19 | 0.0163 (12) | 0.0146 (12) | 0.0135 (12) | −0.0020 (10) | −0.0003 (9) | −0.0034 (10) |
C20 | 0.0204 (13) | 0.0261 (15) | 0.0159 (12) | −0.0007 (11) | 0.0011 (10) | −0.0015 (11) |
C21 | 0.0195 (14) | 0.0328 (17) | 0.0251 (15) | 0.0005 (12) | 0.0077 (11) | −0.0046 (12) |
C22 | 0.0269 (15) | 0.0392 (18) | 0.0156 (13) | −0.0085 (13) | 0.0081 (11) | −0.0025 (12) |
C23 | 0.0263 (15) | 0.0319 (16) | 0.0166 (13) | −0.0075 (12) | 0.0031 (11) | 0.0041 (12) |
C24 | 0.0177 (13) | 0.0186 (13) | 0.0182 (13) | −0.0012 (10) | 0.0020 (10) | 0.0011 (11) |
Br1—C1 | 2.013 (3) | C13—C15 | 1.524 (4) |
Br2—C4 | 2.014 (3) | C13—C14 | 1.531 (4) |
Br3—C13 | 2.027 (2) | C14—H14A | 0.9800 |
Si1—C7 | 1.897 (2) | C14—H14B | 0.9800 |
Si1—C4 | 1.929 (3) | C14—H14C | 0.9800 |
Si1—C1 | 1.965 (3) | C15—H15A | 0.9800 |
Si1—Si2 | 2.4746 (10) | C15—H15B | 0.9800 |
Si2—C19 | 1.907 (3) | C15—H15C | 0.9800 |
Si2—C13 | 1.936 (3) | C16—C17 | 1.529 (3) |
Si2—C16 | 1.946 (2) | C16—C18A | 1.536 (6) |
C1—C3 | 1.518 (4) | C16—C17A | 1.555 (6) |
C1—C2 | 1.544 (3) | C16—C18 | 1.596 (3) |
C2—H2A | 0.9800 | C16—Br4A | 1.901 (3) |
C2—H2B | 0.9800 | C16—Br4 | 1.989 (2) |
C2—H2C | 0.9800 | C17—H17A | 0.9800 |
C3—H3A | 0.9800 | C17—H17B | 0.9800 |
C3—H3B | 0.9800 | C17—H17C | 0.9800 |
C3—H3C | 0.9800 | C18—H18A | 0.9800 |
C4—C6 | 1.534 (3) | C18—H18B | 0.9800 |
C4—C5 | 1.535 (4) | C18—H18C | 0.9800 |
C5—H5A | 0.9800 | C17A—H17D | 0.9800 |
C5—H5B | 0.9800 | C17A—H17E | 0.9800 |
C5—H5C | 0.9800 | C17A—H17F | 0.9800 |
C6—H6A | 0.9800 | C18A—H18D | 0.9800 |
C6—H6B | 0.9800 | C18A—H18E | 0.9800 |
C6—H6C | 0.9800 | C18A—H18F | 0.9800 |
C7—C12 | 1.401 (3) | C19—C24 | 1.399 (3) |
C7—C8 | 1.403 (3) | C19—C20 | 1.405 (4) |
C8—C9 | 1.389 (3) | C20—C21 | 1.388 (4) |
C8—H8 | 0.9500 | C20—H20 | 0.9500 |
C9—C10 | 1.378 (4) | C21—C22 | 1.380 (4) |
C9—H9 | 0.9500 | C21—H21 | 0.9500 |
C10—C11 | 1.391 (4) | C22—C23 | 1.381 (4) |
C10—H10 | 0.9500 | C22—H22 | 0.9500 |
C11—C12 | 1.388 (3) | C23—C24 | 1.390 (4) |
C11—H11 | 0.9500 | C23—H23 | 0.9500 |
C12—H12 | 0.9500 | C24—H24 | 0.9500 |
C7—Si1—C4 | 109.83 (11) | C15—C13—Br3 | 107.03 (18) |
C7—Si1—C1 | 107.04 (11) | C14—C13—Br3 | 103.77 (16) |
C4—Si1—C1 | 107.07 (11) | Si2—C13—Br3 | 104.37 (12) |
C7—Si1—Si2 | 104.08 (8) | C13—C14—H14A | 109.5 |
C4—Si1—Si2 | 115.84 (9) | C13—C14—H14B | 109.5 |
C1—Si1—Si2 | 112.65 (8) | H14A—C14—H14B | 109.5 |
C19—Si2—C13 | 108.93 (11) | C13—C14—H14C | 109.5 |
C19—Si2—C16 | 105.45 (10) | H14A—C14—H14C | 109.5 |
C13—Si2—C16 | 108.03 (10) | H14B—C14—H14C | 109.5 |
C19—Si2—Si1 | 105.98 (8) | C13—C15—H15A | 109.5 |
C13—Si2—Si1 | 115.77 (8) | C13—C15—H15B | 109.5 |
C16—Si2—Si1 | 112.15 (7) | H15A—C15—H15B | 109.5 |
C3—C1—C2 | 108.5 (2) | C13—C15—H15C | 109.5 |
C3—C1—Si1 | 115.27 (17) | H15A—C15—H15C | 109.5 |
C2—C1—Si1 | 116.37 (18) | H15B—C15—H15C | 109.5 |
C3—C1—Br1 | 105.64 (17) | C18A—C16—C17A | 107.8 (6) |
C2—C1—Br1 | 103.36 (16) | C17—C16—C18 | 103.9 (2) |
Si1—C1—Br1 | 106.40 (12) | C18A—C16—Br4A | 110.3 (4) |
C1—C2—H2A | 109.5 | C17A—C16—Br4A | 109.1 (4) |
C1—C2—H2B | 109.5 | C17—C16—Si2 | 118.14 (18) |
H2A—C2—H2B | 109.5 | C18A—C16—Si2 | 115.7 (10) |
C1—C2—H2C | 109.5 | C17A—C16—Si2 | 96.8 (8) |
H2A—C2—H2C | 109.5 | C18—C16—Si2 | 117.2 (2) |
H2B—C2—H2C | 109.5 | Br4A—C16—Si2 | 115.84 (15) |
C1—C3—H3A | 109.5 | C17—C16—Br4 | 105.53 (19) |
C1—C3—H3B | 109.5 | C18—C16—Br4 | 102.80 (18) |
H3A—C3—H3B | 109.5 | Si2—C16—Br4 | 107.65 (11) |
C1—C3—H3C | 109.5 | C16—C17—H17A | 109.5 |
H3A—C3—H3C | 109.5 | C16—C17—H17B | 109.5 |
H3B—C3—H3C | 109.5 | H17A—C17—H17B | 109.5 |
C6—C4—C5 | 109.0 (2) | C16—C17—H17C | 109.5 |
C6—C4—Si1 | 118.12 (18) | H17A—C17—H17C | 109.5 |
C5—C4—Si1 | 113.59 (18) | H17B—C17—H17C | 109.5 |
C6—C4—Br2 | 104.53 (18) | C16—C18—H18A | 109.5 |
C5—C4—Br2 | 106.82 (17) | C16—C18—H18B | 109.5 |
Si1—C4—Br2 | 103.59 (11) | H18A—C18—H18B | 109.5 |
C4—C5—H5A | 109.5 | C16—C18—H18C | 109.5 |
C4—C5—H5B | 109.5 | H18A—C18—H18C | 109.5 |
H5A—C5—H5B | 109.5 | H18B—C18—H18C | 109.5 |
C4—C5—H5C | 109.5 | C16—C17A—H17D | 109.5 |
H5A—C5—H5C | 109.5 | C16—C17A—H17E | 109.5 |
H5B—C5—H5C | 109.5 | H17D—C17A—H17E | 109.5 |
C4—C6—H6A | 109.5 | C16—C17A—H17F | 109.5 |
C4—C6—H6B | 109.5 | H17D—C17A—H17F | 109.5 |
H6A—C6—H6B | 109.5 | H17E—C17A—H17F | 109.5 |
C4—C6—H6C | 109.5 | C16—C18A—H18D | 109.5 |
H6A—C6—H6C | 109.5 | C16—C18A—H18E | 109.5 |
H6B—C6—H6C | 109.5 | H18D—C18A—H18E | 109.5 |
C12—C7—C8 | 116.1 (2) | C16—C18A—H18F | 109.5 |
C12—C7—Si1 | 118.27 (19) | H18D—C18A—H18F | 109.5 |
C8—C7—Si1 | 125.50 (19) | H18E—C18A—H18F | 109.5 |
C9—C8—C7 | 121.7 (2) | C24—C19—C20 | 116.2 (2) |
C9—C8—H8 | 119.1 | C24—C19—Si2 | 119.50 (19) |
C7—C8—H8 | 119.1 | C20—C19—Si2 | 124.32 (19) |
C10—C9—C8 | 120.7 (3) | C21—C20—C19 | 121.6 (3) |
C10—C9—H9 | 119.6 | C21—C20—H20 | 119.2 |
C8—C9—H9 | 119.6 | C19—C20—H20 | 119.2 |
C9—C10—C11 | 119.1 (2) | C22—C21—C20 | 120.7 (3) |
C9—C10—H10 | 120.5 | C22—C21—H21 | 119.6 |
C11—C10—H10 | 120.5 | C20—C21—H21 | 119.6 |
C12—C11—C10 | 119.9 (3) | C21—C22—C23 | 119.2 (3) |
C12—C11—H11 | 120.1 | C21—C22—H22 | 120.4 |
C10—C11—H11 | 120.1 | C23—C22—H22 | 120.4 |
C11—C12—C7 | 122.4 (2) | C22—C23—C24 | 120.0 (3) |
C11—C12—H12 | 118.8 | C22—C23—H23 | 120.0 |
C7—C12—H12 | 118.8 | C24—C23—H23 | 120.0 |
C15—C13—C14 | 109.0 (2) | C23—C24—C19 | 122.3 (2) |
C15—C13—Si2 | 112.85 (17) | C23—C24—H24 | 118.9 |
C14—C13—Si2 | 118.71 (19) | C19—C24—H24 | 118.9 |
C4—Si1—C7—C12 | −166.77 (18) | C10—C11—C12—C7 | −1.6 (4) |
C1—Si1—C7—C12 | −50.9 (2) | C8—C7—C12—C11 | 2.3 (4) |
Si2—Si1—C7—C12 | 68.61 (19) | Si1—C7—C12—C11 | −174.4 (2) |
C4—Si1—C7—C8 | 16.8 (2) | C24—C19—C20—C21 | 1.0 (4) |
C1—Si1—C7—C8 | 132.7 (2) | Si2—C19—C20—C21 | −177.8 (2) |
Si2—Si1—C7—C8 | −107.8 (2) | C19—C20—C21—C22 | −0.9 (4) |
C12—C7—C8—C9 | −1.4 (4) | C20—C21—C22—C23 | −0.2 (4) |
Si1—C7—C8—C9 | 175.0 (2) | C21—C22—C23—C24 | 1.2 (4) |
C7—C8—C9—C10 | −0.2 (4) | C22—C23—C24—C19 | −1.1 (4) |
C8—C9—C10—C11 | 1.1 (4) | C20—C19—C24—C23 | 0.0 (4) |
C9—C10—C11—C12 | −0.2 (4) | Si2—C19—C24—C23 | 178.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15C···Br1i | 0.98 | 2.82 | 3.771 (3) | 166 |
Symmetry code: (i) x, y+1, z. |
C32H38Si2 | F(000) = 516 |
Mr = 478.80 | Dx = 1.182 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.5622 (5) Å | Cell parameters from 9973 reflections |
b = 10.2107 (6) Å | θ = 2.4–29.3° |
c = 15.4586 (10) Å | µ = 0.15 mm−1 |
β = 95.452 (1)° | T = 100 K |
V = 1345.37 (14) Å3 | Block, colorless |
Z = 2 | 0.17 × 0.15 × 0.13 mm |
Bruker SMART APEX CCD diffractometer | 3566 independent reflections |
Radiation source: fine-focus sealed tube | 3065 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 29.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2016) | h = −11→11 |
Tmin = 0.98, Tmax = 0.98 | k = −13→14 |
23513 measured reflections | l = −21→21 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0409P)2 + 0.5552P] where P = (Fo2 + 2Fc2)/3 |
3566 reflections | (Δ/σ)max = 0.001 |
179 parameters | Δρmax = 0.38 e Å−3 |
43 restraints | Δρmin = −0.29 e Å−3 |
Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Si1 | 0.97798 (4) | 0.05498 (3) | 0.06638 (2) | 0.01404 (9) | 0.9645 (7) |
C1 | 1.17324 (13) | 0.10306 (10) | 0.12738 (7) | 0.0163 (2) | 0.9645 (7) |
C2 | 1.24616 (14) | 0.03226 (11) | 0.19771 (7) | 0.0191 (2) | 0.9645 (7) |
H2 | 1.1978 | −0.0455 | 0.2159 | 0.023* | 0.9645 (7) |
C3 | 1.38770 (17) | 0.07272 (13) | 0.24168 (8) | 0.0223 (2) | 0.9645 (7) |
H3 | 1.4342 | 0.0227 | 0.2892 | 0.027* | 0.9645 (7) |
C4 | 1.46102 (14) | 0.18583 (13) | 0.21639 (8) | 0.0219 (3) | 0.9645 (7) |
H4 | 1.5567 | 0.2143 | 0.2468 | 0.026* | 0.9645 (7) |
C5 | 1.39259 (15) | 0.25668 (13) | 0.14615 (8) | 0.0227 (3) | 0.9645 (7) |
H5 | 1.4426 | 0.3334 | 0.1276 | 0.027* | 0.9645 (7) |
C6 | 1.25096 (14) | 0.21603 (11) | 0.10265 (7) | 0.0195 (2) | 0.9645 (7) |
H6 | 1.2057 | 0.2662 | 0.0549 | 0.023* | 0.9645 (7) |
C7 | 0.86874 (13) | 0.21393 (10) | 0.04130 (7) | 0.0164 (2) | 0.9645 (7) |
C8 | 0.89979 (14) | 0.32572 (11) | 0.09251 (7) | 0.0204 (2) | 0.9645 (7) |
H8 | 0.9785 | 0.3220 | 0.1401 | 0.024* | 0.9645 (7) |
C9 | 0.81825 (15) | 0.44211 (11) | 0.07537 (8) | 0.0239 (3) | 0.9645 (7) |
H9 | 0.8428 | 0.5170 | 0.1105 | 0.029* | 0.9645 (7) |
C10 | 0.70130 (16) | 0.44902 (12) | 0.00709 (8) | 0.0242 (3) | 0.9645 (7) |
H10 | 0.6463 | 0.5287 | −0.0051 | 0.029* | 0.9645 (7) |
C11 | 0.66515 (16) | 0.33862 (12) | −0.04334 (8) | 0.0255 (3) | 0.9645 (7) |
H11 | 0.5835 | 0.3421 | −0.0894 | 0.031* | 0.9645 (7) |
C12 | 0.74836 (14) | 0.22282 (12) | −0.02654 (8) | 0.0215 (2) | 0.9645 (7) |
H12 | 0.7230 | 0.1482 | −0.0618 | 0.026* | 0.9645 (7) |
C13 | 0.85261 (14) | −0.04591 (11) | 0.13883 (7) | 0.0173 (2) | 0.9645 (7) |
C14 | 0.85115 (15) | 0.02324 (12) | 0.22736 (8) | 0.0210 (2) | 0.9645 (7) |
H14A | 0.7804 | −0.0234 | 0.2630 | 0.032* | 0.9645 (7) |
H14B | 0.8147 | 0.1136 | 0.2183 | 0.032* | 0.9645 (7) |
H14C | 0.9574 | 0.0235 | 0.2572 | 0.032* | 0.9645 (7) |
C15 | 0.91134 (15) | −0.18758 (12) | 0.15272 (8) | 0.0218 (3) | 0.9645 (7) |
H15A | 1.0199 | −0.1866 | 0.1794 | 0.033* | 0.9645 (7) |
H15B | 0.9068 | −0.2327 | 0.0966 | 0.033* | 0.9645 (7) |
H15C | 0.8448 | −0.2336 | 0.1910 | 0.033* | 0.9645 (7) |
C16 | 0.68191 (15) | −0.05123 (12) | 0.09687 (8) | 0.0219 (2) | 0.9645 (7) |
H16A | 0.6184 | −0.1041 | 0.1332 | 0.033* | 0.9645 (7) |
H16B | 0.6797 | −0.0908 | 0.0390 | 0.033* | 0.9645 (7) |
H16C | 0.6391 | 0.0377 | 0.0917 | 0.033* | 0.9645 (7) |
Si1A | 0.8638 (8) | 0.0135 (6) | 0.0097 (4) | 0.01404 (9) | 0.0355 (7) |
C1A | 0.7401 (14) | −0.0682 (9) | −0.0846 (6) | 0.0163 (2) | 0.0355 (7) |
C2A | 0.712 (2) | −0.0099 (12) | −0.1659 (6) | 0.0191 (2) | 0.0355 (7) |
H2A | 0.7528 | 0.0749 | −0.1757 | 0.023* | 0.0355 (7) |
C3A | 0.625 (3) | −0.0757 (16) | −0.2329 (8) | 0.0223 (2) | 0.0355 (7) |
H3A | 0.6063 | −0.0359 | −0.2884 | 0.027* | 0.0355 (7) |
C4A | 0.566 (3) | −0.1998 (17) | −0.2186 (12) | 0.0219 (3) | 0.0355 (7) |
H4A | 0.5065 | −0.2448 | −0.2643 | 0.026* | 0.0355 (7) |
C5A | 0.594 (2) | −0.2580 (13) | −0.1373 (12) | 0.0227 (3) | 0.0355 (7) |
H5A | 0.5532 | −0.3428 | −0.1275 | 0.027* | 0.0355 (7) |
C6A | 0.681 (2) | −0.1922 (9) | −0.0703 (9) | 0.0195 (2) | 0.0355 (7) |
H6A | 0.6997 | −0.2320 | −0.0148 | 0.023* | 0.0355 (7) |
C7A | 0.8171 (13) | 0.1959 (7) | 0.0073 (6) | 0.0164 (2) | 0.0355 (7) |
C8A | 0.9272 (17) | 0.2764 (8) | 0.0526 (9) | 0.0204 (2) | 0.0355 (7) |
H8A | 1.0252 | 0.2414 | 0.0758 | 0.024* | 0.0355 (7) |
C9A | 0.894 (2) | 0.4082 (8) | 0.0640 (11) | 0.0239 (3) | 0.0355 (7) |
H9A | 0.9694 | 0.4633 | 0.0950 | 0.029* | 0.0355 (7) |
C10A | 0.751 (2) | 0.4595 (8) | 0.0300 (12) | 0.0242 (3) | 0.0355 (7) |
H10A | 0.7282 | 0.5495 | 0.0378 | 0.029* | 0.0355 (7) |
C11A | 0.641 (2) | 0.3789 (10) | −0.0153 (13) | 0.0255 (3) | 0.0355 (7) |
H11A | 0.5427 | 0.4139 | −0.0385 | 0.031* | 0.0355 (7) |
C12A | 0.6738 (15) | 0.2471 (9) | −0.0267 (9) | 0.0215 (2) | 0.0355 (7) |
H12A | 0.5985 | 0.1920 | −0.0577 | 0.026* | 0.0355 (7) |
C13A | 0.8088 (19) | −0.0519 (11) | 0.1193 (6) | 0.0173 (2) | 0.0355 (7) |
C14A | 0.871 (3) | 0.043 (2) | 0.1921 (7) | 0.0210 (2) | 0.0355 (7) |
H14D | 0.9855 | 0.0485 | 0.1940 | 0.032* | 0.0355 (7) |
H14E | 0.8253 | 0.1299 | 0.1807 | 0.032* | 0.0355 (7) |
H14F | 0.8417 | 0.0105 | 0.2481 | 0.032* | 0.0355 (7) |
C15A | 0.874 (4) | −0.1902 (16) | 0.1401 (13) | 0.0218 (3) | 0.0355 (7) |
H15D | 0.8350 | −0.2508 | 0.0940 | 0.033* | 0.0355 (7) |
H15E | 0.9892 | −0.1878 | 0.1440 | 0.033* | 0.0355 (7) |
H15F | 0.8404 | −0.2198 | 0.1957 | 0.033* | 0.0355 (7) |
C16A | 0.6288 (19) | −0.058 (3) | 0.1189 (13) | 0.0219 (2) | 0.0355 (7) |
H16D | 0.5859 | −0.1174 | 0.0730 | 0.033* | 0.0355 (7) |
H16E | 0.6013 | −0.0892 | 0.1753 | 0.033* | 0.0355 (7) |
H16F | 0.5849 | 0.0301 | 0.1080 | 0.033* | 0.0355 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si1 | 0.01699 (16) | 0.01075 (15) | 0.01390 (15) | 0.00070 (11) | −0.00100 (11) | −0.00031 (10) |
C1 | 0.0185 (5) | 0.0142 (5) | 0.0159 (5) | 0.0017 (4) | −0.0001 (4) | −0.0030 (4) |
C2 | 0.0224 (6) | 0.0151 (5) | 0.0194 (5) | 0.0022 (4) | −0.0006 (4) | −0.0014 (4) |
C3 | 0.0226 (6) | 0.0213 (5) | 0.0217 (6) | 0.0056 (5) | −0.0054 (4) | −0.0002 (4) |
C4 | 0.0167 (6) | 0.0249 (6) | 0.0234 (6) | 0.0016 (5) | −0.0022 (4) | −0.0065 (4) |
C5 | 0.0244 (6) | 0.0212 (6) | 0.0221 (6) | −0.0045 (5) | 0.0007 (5) | −0.0025 (4) |
C6 | 0.0230 (6) | 0.0175 (5) | 0.0175 (5) | −0.0011 (4) | −0.0007 (4) | −0.0010 (4) |
C7 | 0.0197 (5) | 0.0135 (5) | 0.0159 (5) | 0.0014 (4) | 0.0005 (4) | 0.0004 (4) |
C8 | 0.0249 (6) | 0.0146 (5) | 0.0207 (5) | 0.0026 (4) | −0.0024 (4) | −0.0017 (4) |
C9 | 0.0287 (7) | 0.0134 (5) | 0.0286 (6) | 0.0027 (5) | −0.0016 (5) | −0.0014 (4) |
C10 | 0.0282 (7) | 0.0168 (5) | 0.0271 (6) | 0.0073 (5) | −0.0008 (5) | 0.0043 (4) |
C11 | 0.0291 (7) | 0.0257 (6) | 0.0204 (6) | 0.0080 (5) | −0.0053 (5) | 0.0011 (5) |
C12 | 0.0243 (6) | 0.0201 (6) | 0.0193 (5) | 0.0046 (5) | −0.0028 (5) | −0.0030 (4) |
C13 | 0.0195 (6) | 0.0155 (5) | 0.0168 (5) | −0.0004 (4) | 0.0009 (4) | −0.0001 (4) |
C14 | 0.0241 (6) | 0.0222 (6) | 0.0171 (5) | 0.0005 (5) | 0.0033 (4) | −0.0007 (4) |
C15 | 0.0270 (7) | 0.0151 (5) | 0.0234 (6) | −0.0016 (5) | 0.0028 (5) | 0.0024 (4) |
C16 | 0.0201 (6) | 0.0235 (6) | 0.0223 (6) | −0.0027 (5) | 0.0025 (4) | −0.0019 (5) |
Si1A | 0.01699 (16) | 0.01075 (15) | 0.01390 (15) | 0.00070 (11) | −0.00100 (11) | −0.00031 (10) |
C1A | 0.0185 (5) | 0.0142 (5) | 0.0159 (5) | 0.0017 (4) | −0.0001 (4) | −0.0030 (4) |
C2A | 0.0224 (6) | 0.0151 (5) | 0.0194 (5) | 0.0022 (4) | −0.0006 (4) | −0.0014 (4) |
C3A | 0.0226 (6) | 0.0213 (5) | 0.0217 (6) | 0.0056 (5) | −0.0054 (4) | −0.0002 (4) |
C4A | 0.0167 (6) | 0.0249 (6) | 0.0234 (6) | 0.0016 (5) | −0.0022 (4) | −0.0065 (4) |
C5A | 0.0244 (6) | 0.0212 (6) | 0.0221 (6) | −0.0045 (5) | 0.0007 (5) | −0.0025 (4) |
C6A | 0.0230 (6) | 0.0175 (5) | 0.0175 (5) | −0.0011 (4) | −0.0007 (4) | −0.0010 (4) |
C7A | 0.0197 (5) | 0.0135 (5) | 0.0159 (5) | 0.0014 (4) | 0.0005 (4) | 0.0004 (4) |
C8A | 0.0249 (6) | 0.0146 (5) | 0.0207 (5) | 0.0026 (4) | −0.0024 (4) | −0.0017 (4) |
C9A | 0.0287 (7) | 0.0134 (5) | 0.0286 (6) | 0.0027 (5) | −0.0016 (5) | −0.0014 (4) |
C10A | 0.0282 (7) | 0.0168 (5) | 0.0271 (6) | 0.0073 (5) | −0.0008 (5) | 0.0043 (4) |
C11A | 0.0291 (7) | 0.0257 (6) | 0.0204 (6) | 0.0080 (5) | −0.0053 (5) | 0.0011 (5) |
C12A | 0.0243 (6) | 0.0201 (6) | 0.0193 (5) | 0.0046 (5) | −0.0028 (5) | −0.0030 (4) |
C13A | 0.0195 (6) | 0.0155 (5) | 0.0168 (5) | −0.0004 (4) | 0.0009 (4) | −0.0001 (4) |
C14A | 0.0241 (6) | 0.0222 (6) | 0.0171 (5) | 0.0005 (5) | 0.0033 (4) | −0.0007 (4) |
C15A | 0.0270 (7) | 0.0151 (5) | 0.0234 (6) | −0.0016 (5) | 0.0028 (5) | 0.0024 (4) |
C16A | 0.0201 (6) | 0.0235 (6) | 0.0223 (6) | −0.0027 (5) | 0.0025 (4) | −0.0019 (5) |
Si1—C7 | 1.8949 (11) | Si1A—C7A | 1.904 (3) |
Si1—C1 | 1.9041 (11) | Si1A—C1A | 1.911 (3) |
Si1—C13 | 1.9226 (12) | Si1A—C13A | 1.921 (4) |
Si1—Si1i | 2.4002 (6) | Si1A—Si1Ai | 2.396 (14) |
C1—C2 | 1.4020 (14) | C1A—C2A | 1.3900 |
C1—C6 | 1.4028 (15) | C1A—C6A | 1.3900 |
C2—C3 | 1.3946 (16) | C2A—C3A | 1.3900 |
C2—H2 | 0.9500 | C2A—H2A | 0.9500 |
C3—C4 | 1.3884 (16) | C3A—C4A | 1.3900 |
C3—H3 | 0.9500 | C3A—H3A | 0.9500 |
C4—C5 | 1.3873 (16) | C4A—C5A | 1.3900 |
C4—H4 | 0.9500 | C4A—H4A | 0.9500 |
C5—C6 | 1.3929 (15) | C5A—C6A | 1.3900 |
C5—H5 | 0.9500 | C5A—H5A | 0.9500 |
C6—H6 | 0.9500 | C6A—H6A | 0.9500 |
C7—C8 | 1.4000 (14) | C7A—C8A | 1.3900 |
C7—C12 | 1.4018 (14) | C7A—C12A | 1.3900 |
C8—C9 | 1.3910 (15) | C8A—C9A | 1.3900 |
C8—H8 | 0.9500 | C8A—H8A | 0.9500 |
C9—C10 | 1.3860 (16) | C9A—C10A | 1.3900 |
C9—H9 | 0.9500 | C9A—H9A | 0.9500 |
C10—C11 | 1.3887 (16) | C10A—C11A | 1.3900 |
C10—H10 | 0.9500 | C10A—H10A | 0.9500 |
C11—C12 | 1.3922 (15) | C11A—C12A | 1.3900 |
C11—H11 | 0.9500 | C11A—H11A | 0.9500 |
C12—H12 | 0.9500 | C12A—H12A | 0.9500 |
C13—C15 | 1.5398 (16) | C13A—C14A | 1.540 (4) |
C13—C14 | 1.5411 (16) | C13A—C16A | 1.542 (4) |
C13—C16 | 1.5427 (17) | C13A—C15A | 1.542 (4) |
C14—H14A | 0.9800 | C14A—H14D | 0.9800 |
C14—H14B | 0.9800 | C14A—H14E | 0.9800 |
C14—H14C | 0.9800 | C14A—H14F | 0.9800 |
C15—H15A | 0.9800 | C15A—H15D | 0.9800 |
C15—H15B | 0.9800 | C15A—H15E | 0.9800 |
C15—H15C | 0.9800 | C15A—H15F | 0.9800 |
C16—H16A | 0.9800 | C16A—H16D | 0.9800 |
C16—H16B | 0.9800 | C16A—H16E | 0.9800 |
C16—H16C | 0.9800 | C16A—H16F | 0.9800 |
C7—Si1—C1 | 105.87 (5) | C7A—Si1A—C1A | 108.15 (19) |
C7—Si1—C13 | 106.62 (5) | C7A—Si1A—C13A | 106.8 (4) |
C1—Si1—C13 | 111.24 (5) | C1A—Si1A—C13A | 110.9 (4) |
C7—Si1—Si1i | 109.90 (4) | C7A—Si1A—Si1Ai | 108.4 (5) |
C1—Si1—Si1i | 110.01 (4) | C1A—Si1A—Si1Ai | 109.3 (5) |
C13—Si1—Si1i | 112.91 (4) | C13A—Si1A—Si1Ai | 113.2 (6) |
C2—C1—C6 | 116.58 (10) | C2A—C1A—C6A | 120.0 |
C2—C1—Si1 | 123.81 (8) | C2A—C1A—Si1A | 122.5 (3) |
C6—C1—Si1 | 119.61 (8) | C6A—C1A—Si1A | 117.4 (3) |
C3—C2—C1 | 121.85 (11) | C3A—C2A—C1A | 120.0 |
C3—C2—H2 | 119.1 | C3A—C2A—H2A | 120.0 |
C1—C2—H2 | 119.1 | C1A—C2A—H2A | 120.0 |
C4—C3—C2 | 120.29 (11) | C2A—C3A—C4A | 120.0 |
C4—C3—H3 | 119.9 | C2A—C3A—H3A | 120.0 |
C2—C3—H3 | 119.9 | C4A—C3A—H3A | 120.0 |
C5—C4—C3 | 119.05 (11) | C3A—C4A—C5A | 120.0 |
C5—C4—H4 | 120.5 | C3A—C4A—H4A | 120.0 |
C3—C4—H4 | 120.5 | C5A—C4A—H4A | 120.0 |
C4—C5—C6 | 120.40 (11) | C6A—C5A—C4A | 120.0 |
C4—C5—H5 | 119.8 | C6A—C5A—H5A | 120.0 |
C6—C5—H5 | 119.8 | C4A—C5A—H5A | 120.0 |
C5—C6—C1 | 121.82 (11) | C5A—C6A—C1A | 120.0 |
C5—C6—H6 | 119.1 | C5A—C6A—H6A | 120.0 |
C1—C6—H6 | 119.1 | C1A—C6A—H6A | 120.0 |
C8—C7—C12 | 117.19 (10) | C8A—C7A—C12A | 120.0 |
C8—C7—Si1 | 121.28 (8) | C8A—C7A—Si1A | 115.94 (17) |
C12—C7—Si1 | 121.47 (8) | C12A—C7A—Si1A | 123.5 (2) |
C9—C8—C7 | 121.60 (10) | C9A—C8A—C7A | 120.0 |
C9—C8—H8 | 119.2 | C9A—C8A—H8A | 120.0 |
C7—C8—H8 | 119.2 | C7A—C8A—H8A | 120.0 |
C10—C9—C8 | 120.12 (11) | C8A—C9A—C10A | 120.0 |
C10—C9—H9 | 119.9 | C8A—C9A—H9A | 120.0 |
C8—C9—H9 | 119.9 | C10A—C9A—H9A | 120.0 |
C9—C10—C11 | 119.51 (11) | C11A—C10A—C9A | 120.0 |
C9—C10—H10 | 120.2 | C11A—C10A—H10A | 120.0 |
C11—C10—H10 | 120.2 | C9A—C10A—H10A | 120.0 |
C10—C11—C12 | 120.12 (11) | C12A—C11A—C10A | 120.0 |
C10—C11—H11 | 119.9 | C12A—C11A—H11A | 120.0 |
C12—C11—H11 | 119.9 | C10A—C11A—H11A | 120.0 |
C11—C12—C7 | 121.43 (11) | C11A—C12A—C7A | 120.0 |
C11—C12—H12 | 119.3 | C11A—C12A—H12A | 120.0 |
C7—C12—H12 | 119.3 | C7A—C12A—H12A | 120.0 |
C15—C13—C14 | 109.68 (9) | C14A—C13A—C16A | 107.7 (5) |
C15—C13—C16 | 108.02 (9) | C14A—C13A—C15A | 109.2 (5) |
C14—C13—C16 | 107.60 (9) | C16A—C13A—C15A | 108.0 (5) |
C15—C13—Si1 | 113.05 (8) | C14A—C13A—Si1A | 109.2 (5) |
C14—C13—Si1 | 108.90 (8) | C16A—C13A—Si1A | 109.7 (5) |
C16—C13—Si1 | 109.45 (8) | C15A—C13A—Si1A | 112.8 (5) |
C13—C14—H14A | 109.5 | C13A—C14A—H14D | 109.5 |
C13—C14—H14B | 109.5 | C13A—C14A—H14E | 109.5 |
H14A—C14—H14B | 109.5 | H14D—C14A—H14E | 109.5 |
C13—C14—H14C | 109.5 | C13A—C14A—H14F | 109.5 |
H14A—C14—H14C | 109.5 | H14D—C14A—H14F | 109.5 |
H14B—C14—H14C | 109.5 | H14E—C14A—H14F | 109.5 |
C13—C15—H15A | 109.5 | C13A—C15A—H15D | 109.5 |
C13—C15—H15B | 109.5 | C13A—C15A—H15E | 109.5 |
H15A—C15—H15B | 109.5 | H15D—C15A—H15E | 109.5 |
C13—C15—H15C | 109.5 | C13A—C15A—H15F | 109.5 |
H15A—C15—H15C | 109.5 | H15D—C15A—H15F | 109.5 |
H15B—C15—H15C | 109.5 | H15E—C15A—H15F | 109.5 |
C13—C16—H16A | 109.5 | C13A—C16A—H16D | 109.5 |
C13—C16—H16B | 109.5 | C13A—C16A—H16E | 109.5 |
H16A—C16—H16B | 109.5 | H16D—C16A—H16E | 109.5 |
C13—C16—H16C | 109.5 | C13A—C16A—H16F | 109.5 |
H16A—C16—H16C | 109.5 | H16D—C16A—H16F | 109.5 |
H16B—C16—H16C | 109.5 | H16E—C16A—H16F | 109.5 |
C6—C1—C2—C3 | 0.80 (18) | C10—C11—C12—C7 | 0.5 (2) |
Si1—C1—C2—C3 | −178.60 (10) | C8—C7—C12—C11 | 1.18 (18) |
C1—C2—C3—C4 | −0.1 (2) | Si1—C7—C12—C11 | 178.14 (10) |
C2—C3—C4—C5 | −0.9 (2) | C6A—C1A—C2A—C3A | 0.0 |
C3—C4—C5—C6 | 1.11 (19) | Si1A—C1A—C2A—C3A | 178.1 (4) |
C4—C5—C6—C1 | −0.36 (19) | C1A—C2A—C3A—C4A | 0.0 |
C2—C1—C6—C5 | −0.59 (18) | C2A—C3A—C4A—C5A | 0.0 |
Si1—C1—C6—C5 | 178.83 (10) | C3A—C4A—C5A—C6A | 0.0 |
C1—Si1—C7—C8 | −25.36 (11) | C4A—C5A—C6A—C1A | 0.0 |
C13—Si1—C7—C8 | 93.19 (10) | C2A—C1A—C6A—C5A | 0.0 |
Si1i—Si1—C7—C8 | −144.13 (9) | Si1A—C1A—C6A—C5A | −178.2 (4) |
C1—Si1—C7—C12 | 157.80 (10) | C12A—C7A—C8A—C9A | 0.0 |
C13—Si1—C7—C12 | −83.65 (11) | Si1A—C7A—C8A—C9A | −171.7 (4) |
Si1i—Si1—C7—C12 | 39.03 (11) | C7A—C8A—C9A—C10A | 0.0 |
C12—C7—C8—C9 | −1.94 (18) | C8A—C9A—C10A—C11A | 0.0 |
Si1—C7—C8—C9 | −178.91 (10) | C9A—C10A—C11A—C12A | 0.0 |
C7—C8—C9—C10 | 1.0 (2) | C10A—C11A—C12A—C7A | 0.0 |
C8—C9—C10—C11 | 0.7 (2) | C8A—C7A—C12A—C11A | 0.0 |
C9—C10—C11—C12 | −1.5 (2) | Si1A—C7A—C12A—C11A | 171.0 (4) |
Symmetry code: (i) −x+2, −y, −z. |
Cg1 is the centroid of C1–C6 the ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15C···Cg1ii | 0.98 | 2.93 | 3.8955 (14) | 171 |
Symmetry code: (ii) −x+2, y−1/2, −z+1/2. |
Acknowledgements
The financial support of NSF Grant CHE-0445637 (to MJF) and Tulane University for the Tulane X-ray Crystallography Laboratory is gratefully acknowledged.
References
Ando, W., Shiba, T., Hidaka, T., Morihashi, K. & Kikuchi, O. (1997). J. Am. Chem. Soc. 119, 3629–3630. CrossRef CAS Google Scholar
Beagley, B. A., Monaghan, J. J. & Hewitt, T. G. (1971). J. Mol. Struct. 8, 401–411. CrossRef CAS Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Desiraju, G. R. & Parthasarathy, R. (1989). J. Am. Chem. Soc. 111, 8725–8726. CrossRef CAS Web of Science Google Scholar
Goetze, B., Herrschaft, B. & Auner, N. (1997). Chem. Eur. J. 3, 948–957. CrossRef CAS Google Scholar
Gottschling, S. E., Milnes, K. K., Jennings, M. C. & Baines, K. M. (2005). Organometallics, 24, 3811–3814. CrossRef CAS Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Kabe, Y., Ohkubo, Z., Ishikawa, H. & Ando, W. (2000). J. Am. Chem. Soc. 122, 3775–3776. CrossRef CAS Google Scholar
Kleiner, N. & Dräger, M. (1984). J. Organomet. Chem. 270, 151–170. CrossRef CAS Google Scholar
Kyushin, S., Ikarugi, M., Takatsuna, K., Goto, M. & Matsumoto, H. (1996). J. Organomet. Chem. 510, 121–133. CrossRef CAS Google Scholar
Lambert, J. B. & Urdaneta-Perez, M. (1978). J. Am. Chem. Soc. 100, 157–162. CrossRef CAS Google Scholar
Lerner, H. W., Scholz, S. & Bolte, M. (2001). Z. Anorg. Allg. Chem. 627, 1638–1642. CrossRef CAS Google Scholar
Lerner, H. W., Scholz, S. & Bolte, M. (2002). Organometallics, 21, 3827–3830. CrossRef CAS Google Scholar
Meyer-Wegner, F., Scholz, S., Sänger, I., Schödel, F., Bolte, M., Wagner, M. & Lerner, H.-W. (2009). Organometallics, 28, 6835–6837. Web of Science CSD CrossRef CAS Google Scholar
Monakhov, K. Yu., Zessin, T. & Linti, G. (2010). Eur. J. Inorg. Chem. pp. 322–332. CrossRef Google Scholar
Peters, K., Peters, E.-M., Kirmaier, L. & Weidenbruch, M. (1998). Z. Kristallogr. New Cryst. Struct. 213, 747–748. CAS Google Scholar
Pichaandi, K. R., Mague, J. T. & Fink, M. J. (2011). J. Organomet. Chem. 696, 1957–1963. CrossRef CAS Google Scholar
Scholz, S., Lerner, H.-W. & Bats, J. W. (2014). Acta Cryst. C70, 697–701. CrossRef IUCr Journals Google Scholar
Scholz, S., Lerner, H.-W. & Bolte, M. (2012). CCDC Private Communication. CSD refcode DIVKIC03. CCDC, Cambridge, UK. Google Scholar
Sheldrick, W. S. (1989). Vol. 1. The Chemistry of Organic Silicon Compounds, edited by S. Patai & Z. Rappaport, p. 245. Chichester: John Wiley & Sons Ltd. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Wei, Y.-L., Yang, K.-F., Li, F., Zheng, Z.-J., Xu, Z. & Xu, L.-W. (2014). RSC Adv. 4, 37859–37867. CrossRef CAS Google Scholar
West, R. & Pham, E. K. (1991). J. Organomet. Chem. 403, 43–48. CrossRef CAS Google Scholar
Wiberg, N., Finger, C. M. M. & Polborn, K. (1993). Angew. Chem. Int. Ed. Engl. 32, 1054–1056. CrossRef Google Scholar
Wiberg, N., Hochmuth, W., Nöth, H., Appel, A. & Schmidt-Amelunxen, M. (1996). Angew. Chem. Int. Ed. Engl. 35, 1333–1334. CrossRef CAS Google Scholar
Wiberg, N., Lerner, H.-W., Nöth, H. & Ponikwar, W. (1999). Angew. Chem. Int. Ed. 38, 1103–1105. CrossRef CAS Google Scholar
Wiberg, N. & Niedermayer, W. (2000). Z. Naturforsch. Teil B, 55, 398–405. Google Scholar
Wiberg, N., Schuster, H., Simon, A. & Peters, K. (1986). Angew. Chem. 98, 100–101. CrossRef CAS 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.