syn-exo-4,7-Bis(trimethyl­sil­yl)-4,7-dihydro­[2.2]paracyclo­phane

In the title compound, C₂₂H₃₄Si₂, the two independent mol­ecules are closely similar. The reduced rings show a flattened twist conformation. Several features of [2.2]paracyclo­phane strain (e.g. lengthened bridge bonds) are apparent; an exception is furnished by the normal sp² values of the angles at the bridgehead atoms of the reduced rings.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.055
• wR factor = 0.164
• Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.70 mm
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.90 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       Si2'
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: P3 (Nicolet, 1987); cell refinement: P3; data reduction: XDISK (Nicolet, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

syn-exo-4,7-Bis(trimethylsilyl)-4,7-dihydro[2.2]paracyclophane

Crystal data

C22H34Si2	F(000) = 1552
Mr = 354.67	Dx = 1.079 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.485 (4) Å	Cell parameters from 50 reflections
b = 33.972 (8) Å	θ = 10–11°
c = 12.544 (4) Å	µ = 0.16 mm^−1
β = 102.12 (3)°	T = 173 K
V = 4369 (2) Å^3	Tablet, colourless
Z = 8	0.7 × 0.5 × 0.2 mm

Data collection

Nicolet R3 diffractometer	Rint = 0.031
Radiation source: fine-focus sealed tube	θmax = 25.1°, θmin = 3.1°
Graphite monochromator	h = −12→0
ω scans	k = −40→0
7846 measured reflections	l = −14→14
7710 independent reflections	3 standard reflections every 147 reflections
4194 reflections with I > 2σ(I)	intensity decay: 5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.065P)^2 + 3.2193P] where P = (Fo^2 + 2Fc^2)/3
7710 reflections	(Δ/σ)max = 0.001
445 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.28 e Å^−3

Special details

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

Contact distances: 2.8024 (0.0046) C3 - C14 2.7781 (0.0048) C6 - C11 2.7954 (0.0048) C3' - C14' 2.7783 (0.0048) C6' - C11'

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 8.9850 (0.0135) x - 15.8767 (0.0736) y - 0.4089 (0.0183) z = 0.8245 (0.0139)

* -0.0026 (0.0017) C12 * 0.0026 (0.0017) C13 * -0.0026 (0.0017) C15 * 0.0026 (0.0017) C16 - 0.1443 (0.0052) C11 - 0.1520 (0.0050) C14

Rms deviation of fitted atoms = 0.0026

8.6150 (0.0141) x + 18.4481 (0.0539) y - 0.0395 (0.0276) z = 3.3990 (0.0203)

Angle to previous plane (with approximate e.s.d.) = 5.41 (0.29)

* 0.0030 (0.0017) C12' * -0.0030 (0.0017) C13' * 0.0029 (0.0017) C15' * -0.0029 (0.0017) C16' 0.1460 (0.0052) C11' 0.1414 (0.0052) C14'

Rms deviation of fitted atoms = 0.0030

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

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

	x	y	z	Uiso*/Ueq
Si1	0.21787 (10)	0.13255 (3)	0.31606 (9)	0.0390 (3)
Si2	0.04543 (10)	0.20939 (3)	0.58075 (9)	0.0381 (3)
C1	−0.0955 (4)	0.04026 (11)	0.3708 (3)	0.0435 (10)
H1A	−0.0801	0.0335	0.2978	0.052*
H1B	−0.1150	0.0156	0.4063	0.052*
C2	0.0314 (3)	0.05967 (10)	0.4412 (3)	0.0362 (9)
H2A	0.0393	0.0521	0.5185	0.043*
H2B	0.1086	0.0493	0.4166	0.043*
C3	0.0313 (3)	0.10417 (10)	0.4331 (3)	0.0286 (8)
C4	0.0419 (3)	0.12341 (10)	0.3273 (3)	0.0320 (8)
H4	0.0065	0.1039	0.2690	0.038*
C5	−0.0478 (3)	0.15866 (10)	0.3052 (3)	0.0307 (8)
H5	−0.0695	0.1684	0.2327	0.037*
C6	−0.0984 (3)	0.17694 (10)	0.3808 (3)	0.0296 (8)
C7	−0.0510 (3)	0.16749 (10)	0.5001 (3)	0.0318 (8)
H7	−0.1329	0.1662	0.5290	0.038*
C8	0.0012 (3)	0.12584 (10)	0.5131 (3)	0.0298 (8)
H8	0.0136	0.1143	0.5834	0.036*
C9	−0.2157 (3)	0.20361 (11)	0.3482 (3)	0.0396 (9)
H9A	−0.2256	0.2107	0.2703	0.048*
H9B	−0.2001	0.2282	0.3914	0.048*
C10	−0.3466 (4)	0.18414 (12)	0.3656 (4)	0.0465 (11)
H10A	−0.3612	0.1912	0.4387	0.056*
H10B	−0.4209	0.1943	0.3104	0.056*
C11	−0.3393 (3)	0.14001 (12)	0.3559 (3)	0.0387 (9)
C12	−0.3179 (3)	0.11659 (11)	0.4485 (3)	0.0394 (9)
H12	−0.3466	0.1253	0.5115	0.047*
C13	−0.2551 (3)	0.08068 (11)	0.4498 (3)	0.0362 (9)
H13	−0.2421	0.0648	0.5135	0.043*
C14	−0.2106 (3)	0.06757 (11)	0.3585 (3)	0.0353 (9)
C15	−0.2574 (3)	0.08718 (11)	0.2610 (3)	0.0404 (10)
H15	−0.2455	0.0759	0.1944	0.048*
C16	−0.3211 (3)	0.12294 (12)	0.2593 (3)	0.0400 (10)
H16	−0.3526	0.1359	0.1918	0.048*
C17	0.3140 (4)	0.15582 (15)	0.4415 (4)	0.0619 (13)
H17A	0.3080	0.1396	0.5050	0.074*
H17B	0.2793	0.1821	0.4501	0.074*
H17C	0.4055	0.1580	0.4357	0.074*
C18	0.2172 (5)	0.16533 (14)	0.1977 (4)	0.0633 (13)
H18A	0.1630	0.1537	0.1321	0.076*
H18B	0.3066	0.1685	0.1870	0.076*
H18C	0.1818	0.1911	0.2114	0.076*
C19	0.2980 (4)	0.08496 (13)	0.2967 (4)	0.0569 (12)
H19A	0.2438	0.0705	0.2361	0.068*
H19B	0.3085	0.0693	0.3635	0.068*
H19C	0.3838	0.0901	0.2802	0.068*
C20	0.1802 (4)	0.19004 (13)	0.6887 (4)	0.0582 (13)
H20A	0.2347	0.1722	0.6560	0.070*
H20B	0.1435	0.1757	0.7431	0.070*
H20C	0.2334	0.2120	0.7241	0.070*
C21	0.1076 (4)	0.24473 (12)	0.4899 (4)	0.0565 (12)
H21A	0.1472	0.2301	0.4377	0.068*
H21B	0.1733	0.2619	0.5340	0.068*
H21C	0.0352	0.2607	0.4503	0.068*
C22	−0.0684 (4)	0.23575 (13)	0.6525 (4)	0.0561 (12)
H22A	−0.1454	0.2444	0.5992	0.067*
H22B	−0.0241	0.2587	0.6908	0.067*
H22C	−0.0953	0.2180	0.7052	0.067*
Si1'	0.57710 (11)	0.18088 (3)	0.86757 (10)	0.0457 (3)
Si2'	0.83606 (10)	0.06454 (4)	0.86098 (10)	0.0426 (3)
C1'	0.2841 (4)	0.09502 (13)	0.9757 (3)	0.0511 (11)
H1'1	0.2478	0.0837	1.0358	0.061*
H1'2	0.2313	0.1184	0.9473	0.061*
C2'	0.4298 (3)	0.10793 (13)	1.0208 (3)	0.0432 (10)
H2'1	0.4309	0.1357	1.0452	0.052*
H2'2	0.4670	0.0916	1.0853	0.052*
C3'	0.5155 (3)	0.10408 (11)	0.9378 (3)	0.0328 (9)
C4'	0.4929 (3)	0.13113 (11)	0.8410 (3)	0.0347 (9)
H4'	0.3975	0.1372	0.8263	0.042*
C5'	0.5128 (3)	0.10908 (11)	0.7409 (3)	0.0345 (9)
H5'	0.4784	0.1206	0.6718	0.041*
C6'	0.5745 (3)	0.07511 (11)	0.7423 (3)	0.0334 (9)
C7'	0.6527 (3)	0.05888 (11)	0.8484 (3)	0.0341 (9)
H7'	0.6362	0.0299	0.8452	0.041*
C8'	0.5961 (3)	0.07370 (11)	0.9424 (3)	0.0321 (8)
H8'	0.6202	0.0602	1.0100	0.039*
C9'	0.5524 (4)	0.04854 (12)	0.6427 (3)	0.0436 (10)
H9'1	0.6371	0.0372	0.6355	0.052*
H9'2	0.5194	0.0647	0.5770	0.052*
C10'	0.4536 (4)	0.01406 (12)	0.6467 (3)	0.0502 (11)
H10C	0.4030	0.0087	0.5722	0.060*
H10D	0.5023	−0.0101	0.6742	0.060*
C11'	0.3621 (4)	0.02463 (11)	0.7197 (3)	0.0387 (9)
C12'	0.3796 (4)	0.00890 (11)	0.8246 (3)	0.0405 (10)
H12'	0.4217	−0.0159	0.8398	0.049*
C13'	0.3370 (4)	0.02867 (12)	0.9063 (3)	0.0416 (10)
H13'	0.3495	0.0173	0.9769	0.050*
C14'	0.2756 (3)	0.06512 (12)	0.8866 (3)	0.0393 (9)
C15'	0.2352 (3)	0.07623 (12)	0.7786 (3)	0.0411 (10)
H15'	0.1778	0.0980	0.7605	0.049*
C16'	0.2775 (3)	0.05599 (11)	0.6962 (3)	0.0396 (10)
H16'	0.2477	0.0639	0.6225	0.047*
C17'	0.7408 (4)	0.17711 (14)	0.9591 (4)	0.0651 (14)
H17D	0.7826	0.2030	0.9665	0.078*
H17E	0.7946	0.1585	0.9281	0.078*
H17F	0.7315	0.1678	1.0310	0.078*
C18'	0.4789 (5)	0.21374 (13)	0.9385 (5)	0.0751 (15)
H18D	0.3896	0.2156	0.8953	0.090*
H18E	0.5183	0.2400	0.9468	0.090*
H18F	0.4771	0.2029	1.0105	0.090*
C19'	0.5869 (5)	0.20280 (13)	0.7342 (4)	0.0664 (14)
H19D	0.4995	0.2039	0.6875	0.080*
H19E	0.6436	0.1866	0.6991	0.080*
H19F	0.6229	0.2295	0.7455	0.080*
C20'	0.8992 (5)	0.02048 (16)	0.8011 (5)	0.094 (2)
H20D	0.8511	0.0169	0.7258	0.113*
H20E	0.8877	−0.0028	0.8441	0.113*
H20F	0.9921	0.0241	0.8017	0.113*
C21'	0.9175 (4)	0.06862 (17)	1.0069 (4)	0.0698 (15)
H21D	0.8871	0.0924	1.0379	0.084*
H21E	1.0122	0.0701	1.0133	0.084*
H21F	0.8962	0.0455	1.0464	0.084*
C22'	0.8750 (4)	0.10815 (14)	0.7836 (4)	0.0605 (13)
H22D	0.9672	0.1150	0.8084	0.073*
H22E	0.8205	0.1304	0.7959	0.073*
H22F	0.8576	0.1019	0.7056	0.073*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Si1	0.0350 (6)	0.0410 (6)	0.0444 (7)	0.0013 (5)	0.0160 (5)	0.0005 (5)
Si2	0.0403 (6)	0.0317 (6)	0.0408 (6)	−0.0024 (5)	0.0051 (5)	−0.0082 (5)
C1	0.042 (2)	0.032 (2)	0.053 (3)	−0.0035 (18)	0.0026 (19)	−0.0071 (19)
C2	0.035 (2)	0.028 (2)	0.045 (2)	−0.0012 (16)	0.0059 (17)	0.0008 (17)
C3	0.0234 (17)	0.0292 (19)	0.031 (2)	−0.0040 (15)	0.0003 (15)	0.0018 (16)
C4	0.0295 (19)	0.034 (2)	0.031 (2)	−0.0016 (16)	0.0047 (15)	−0.0029 (17)
C5	0.0282 (19)	0.033 (2)	0.030 (2)	0.0001 (16)	0.0023 (15)	0.0062 (17)
C6	0.0289 (18)	0.0242 (19)	0.035 (2)	−0.0041 (15)	0.0047 (16)	0.0040 (16)
C7	0.0291 (19)	0.034 (2)	0.032 (2)	0.0001 (16)	0.0054 (15)	−0.0026 (16)
C8	0.0287 (18)	0.033 (2)	0.0246 (19)	−0.0028 (15)	−0.0005 (15)	0.0033 (16)
C9	0.034 (2)	0.031 (2)	0.051 (3)	0.0040 (17)	0.0032 (18)	0.0055 (19)
C10	0.031 (2)	0.047 (3)	0.061 (3)	0.0086 (18)	0.0074 (19)	0.006 (2)
C11	0.0213 (18)	0.044 (2)	0.049 (3)	−0.0015 (16)	0.0031 (17)	0.002 (2)
C12	0.030 (2)	0.045 (2)	0.045 (2)	−0.0069 (18)	0.0134 (17)	0.001 (2)
C13	0.0311 (19)	0.036 (2)	0.041 (2)	−0.0075 (17)	0.0063 (17)	0.0075 (18)
C14	0.0316 (19)	0.031 (2)	0.041 (2)	−0.0133 (17)	0.0017 (17)	−0.0042 (18)
C15	0.037 (2)	0.044 (2)	0.037 (2)	−0.0107 (19)	0.0025 (18)	−0.0108 (19)
C16	0.033 (2)	0.045 (2)	0.037 (2)	−0.0083 (18)	−0.0058 (17)	0.0067 (19)
C17	0.035 (2)	0.081 (4)	0.072 (3)	−0.010 (2)	0.017 (2)	−0.019 (3)
C18	0.068 (3)	0.062 (3)	0.072 (3)	0.009 (3)	0.041 (3)	0.010 (3)
C19	0.050 (3)	0.053 (3)	0.074 (3)	0.009 (2)	0.027 (2)	0.000 (2)
C20	0.056 (3)	0.051 (3)	0.058 (3)	0.000 (2)	−0.010 (2)	−0.013 (2)
C21	0.065 (3)	0.045 (3)	0.060 (3)	−0.017 (2)	0.014 (2)	−0.010 (2)
C22	0.063 (3)	0.048 (3)	0.059 (3)	0.001 (2)	0.016 (2)	−0.020 (2)
Si1'	0.0444 (7)	0.0340 (6)	0.0547 (8)	−0.0090 (5)	0.0010 (6)	−0.0045 (6)
Si2'	0.0281 (5)	0.0508 (7)	0.0496 (7)	−0.0010 (5)	0.0099 (5)	−0.0046 (6)
C1'	0.038 (2)	0.067 (3)	0.051 (3)	−0.009 (2)	0.017 (2)	−0.011 (2)
C2'	0.037 (2)	0.054 (3)	0.039 (2)	−0.0074 (19)	0.0089 (18)	−0.010 (2)
C3'	0.0264 (18)	0.044 (2)	0.027 (2)	−0.0094 (17)	0.0031 (15)	−0.0045 (17)
C4'	0.0257 (18)	0.036 (2)	0.040 (2)	−0.0018 (16)	0.0007 (16)	−0.0006 (18)
C5'	0.036 (2)	0.037 (2)	0.028 (2)	−0.0108 (18)	−0.0007 (16)	0.0035 (17)
C6'	0.0286 (19)	0.040 (2)	0.032 (2)	−0.0105 (17)	0.0080 (16)	−0.0022 (17)
C7'	0.0284 (19)	0.036 (2)	0.038 (2)	−0.0035 (16)	0.0071 (16)	0.0027 (17)
C8'	0.0259 (18)	0.041 (2)	0.028 (2)	−0.0076 (17)	0.0003 (15)	0.0043 (17)
C9'	0.046 (2)	0.050 (3)	0.038 (2)	−0.010 (2)	0.0149 (19)	−0.007 (2)
C10'	0.057 (3)	0.049 (3)	0.045 (3)	−0.017 (2)	0.010 (2)	−0.016 (2)
C11'	0.039 (2)	0.040 (2)	0.035 (2)	−0.0173 (18)	0.0032 (17)	−0.0073 (19)
C12'	0.038 (2)	0.032 (2)	0.048 (3)	−0.0130 (17)	0.0029 (19)	0.0035 (19)
C13'	0.038 (2)	0.051 (3)	0.035 (2)	−0.018 (2)	0.0052 (18)	0.007 (2)
C14'	0.0259 (19)	0.050 (3)	0.041 (2)	−0.0109 (18)	0.0047 (17)	−0.004 (2)
C15'	0.0247 (19)	0.041 (2)	0.055 (3)	−0.0063 (17)	0.0033 (18)	0.000 (2)
C16'	0.033 (2)	0.046 (2)	0.035 (2)	−0.0138 (18)	−0.0059 (17)	0.0027 (19)
C17'	0.054 (3)	0.058 (3)	0.074 (3)	−0.016 (2)	−0.009 (2)	−0.005 (3)
C18'	0.081 (4)	0.045 (3)	0.095 (4)	−0.005 (3)	0.011 (3)	−0.021 (3)
C19'	0.078 (3)	0.043 (3)	0.074 (3)	−0.022 (2)	0.009 (3)	0.005 (2)
C20'	0.046 (3)	0.083 (4)	0.153 (6)	0.011 (3)	0.019 (3)	−0.045 (4)
C21'	0.035 (2)	0.113 (4)	0.060 (3)	0.003 (3)	0.005 (2)	0.016 (3)
C22'	0.044 (3)	0.085 (4)	0.057 (3)	−0.018 (2)	0.021 (2)	0.001 (3)

Geometric parameters (Å, º)

Si1—C18	1.855 (4)	Si1'—C19'	1.854 (5)
Si1—C17	1.858 (4)	Si1'—C17'	1.858 (4)
Si1—C19	1.861 (4)	Si1'—C18'	1.866 (5)
Si1—C4	1.905 (4)	Si1'—C4'	1.903 (4)
Si2—C20	1.860 (4)	Si2'—C21'	1.855 (5)
Si2—C21	1.865 (4)	Si2'—C20'	1.858 (5)
Si2—C22	1.867 (4)	Si2'—C22'	1.863 (5)
Si2—C7	1.909 (4)	Si2'—C7'	1.905 (4)
C1—C14	1.504 (5)	C1'—C14'	1.499 (5)
C1—C2	1.578 (5)	C1'—C2'	1.576 (5)
C1—H1A	0.9900	C1'—H1'1	0.9900
C1—H1B	0.9900	C1'—H1'2	0.9900
C2—C3	1.515 (5)	C2'—C3'	1.518 (5)
C2—H2A	0.9900	C2'—H2'1	0.9900
C2—H2B	0.9900	C2'—H2'2	0.9900
C3—C8	1.335 (5)	C3'—C8'	1.328 (5)
C3—C4	1.504 (5)	C3'—C4'	1.502 (5)
C4—C5	1.512 (5)	C4'—C5'	1.513 (5)
C4—H4	1.0000	C4'—H4'	1.0000
C5—C6	1.334 (5)	C5'—C6'	1.321 (5)
C5—H5	0.9500	C5'—H5'	0.9500
C6—C7	1.509 (5)	C6'—C7'	1.513 (5)
C6—C9	1.513 (5)	C6'—C9'	1.519 (5)
C7—C8	1.514 (5)	C7'—C8'	1.514 (5)
C7—H7	1.0000	C7'—H7'	1.0000
C8—H8	0.9500	C8'—H8'	0.9500
C9—C10	1.579 (5)	C9'—C10'	1.572 (5)
C9—H9A	0.9900	C9'—H9'1	0.9900
C9—H9B	0.9900	C9'—H9'2	0.9900
C10—C11	1.507 (5)	C10'—C11'	1.503 (5)
C10—H10A	0.9900	C10'—H10C	0.9900
C10—H10B	0.9900	C10'—H10D	0.9900
C11—C12	1.387 (5)	C11'—C16'	1.378 (5)
C11—C16	1.392 (5)	C11'—C12'	1.396 (5)
C12—C13	1.385 (5)	C12'—C13'	1.376 (5)
C12—H12	0.9500	C12'—H12'	0.9500
C13—C14	1.398 (5)	C13'—C14'	1.393 (5)
C13—H13	0.9500	C13'—H13'	0.9500
C14—C15	1.389 (5)	C14'—C15'	1.385 (5)
C15—C16	1.385 (5)	C15'—C16'	1.389 (5)
C15—H15	0.9500	C15'—H15'	0.9500
C16—H16	0.9500	C16'—H16'	0.9500
C17—H17A	0.9800	C17'—H17D	0.9800
C17—H17B	0.9800	C17'—H17E	0.9800
C17—H17C	0.9800	C17'—H17F	0.9800
C18—H18A	0.9800	C18'—H18D	0.9800
C18—H18B	0.9800	C18'—H18E	0.9800
C18—H18C	0.9800	C18'—H18F	0.9800
C19—H19A	0.9800	C19'—H19D	0.9800
C19—H19B	0.9800	C19'—H19E	0.9800
C19—H19C	0.9800	C19'—H19F	0.9800
C20—H20A	0.9800	C20'—H20D	0.9800
C20—H20B	0.9800	C20'—H20E	0.9800
C20—H20C	0.9800	C20'—H20F	0.9800
C21—H21A	0.9800	C21'—H21D	0.9800
C21—H21B	0.9800	C21'—H21E	0.9800
C21—H21C	0.9800	C21'—H21F	0.9800
C22—H22A	0.9800	C22'—H22D	0.9800
C22—H22B	0.9800	C22'—H22E	0.9800
C22—H22C	0.9800	C22'—H22F	0.9800
C18—Si1—C17	109.4 (2)	C19'—Si1'—C17'	111.5 (2)
C18—Si1—C19	110.1 (2)	C19'—Si1'—C18'	109.3 (2)
C17—Si1—C19	107.5 (2)	C17'—Si1'—C18'	106.1 (2)
C18—Si1—C4	108.43 (19)	C19'—Si1'—C4'	108.07 (19)
C17—Si1—C4	111.62 (18)	C17'—Si1'—C4'	112.41 (19)
C19—Si1—C4	109.79 (18)	C18'—Si1'—C4'	109.4 (2)
C20—Si2—C21	111.3 (2)	C21'—Si2'—C20'	109.3 (3)
C20—Si2—C22	106.4 (2)	C21'—Si2'—C22'	110.4 (2)
C21—Si2—C22	109.1 (2)	C20'—Si2'—C22'	107.1 (3)
C20—Si2—C7	111.06 (18)	C21'—Si2'—C7'	109.69 (19)
C21—Si2—C7	111.77 (18)	C20'—Si2'—C7'	108.9 (2)
C22—Si2—C7	106.97 (18)	C22'—Si2'—C7'	111.38 (19)
C14—C1—C2	111.3 (3)	C14'—C1'—C2'	111.0 (3)
C14—C1—H1A	109.4	C14'—C1'—H1'1	109.4
C2—C1—H1A	109.4	C2'—C1'—H1'1	109.4
C14—C1—H1B	109.4	C14'—C1'—H1'2	109.4
C2—C1—H1B	109.4	C2'—C1'—H1'2	109.4
H1A—C1—H1B	108.0	H1'1—C1'—H1'2	108.0
C3—C2—C1	113.0 (3)	C3'—C2'—C1'	113.5 (3)
C3—C2—H2A	109.0	C3'—C2'—H2'1	108.9
C1—C2—H2A	109.0	C1'—C2'—H2'1	108.9
C3—C2—H2B	109.0	C3'—C2'—H2'2	108.9
C1—C2—H2B	109.0	C1'—C2'—H2'2	108.9
H2A—C2—H2B	107.8	H2'1—C2'—H2'2	107.7
C8—C3—C4	119.8 (3)	C8'—C3'—C4'	120.1 (3)
C8—C3—C2	119.8 (3)	C8'—C3'—C2'	120.0 (3)
C4—C3—C2	119.6 (3)	C4'—C3'—C2'	119.1 (3)
C3—C4—C5	110.3 (3)	C3'—C4'—C5'	110.0 (3)
C3—C4—Si1	112.9 (2)	C3'—C4'—Si1'	114.4 (2)
C5—C4—Si1	115.6 (2)	C5'—C4'—Si1'	116.4 (3)
C3—C4—H4	105.7	C3'—C4'—H4'	104.9
C5—C4—H4	105.7	C5'—C4'—H4'	104.9
Si1—C4—H4	105.7	Si1'—C4'—H4'	104.9
C6—C5—C4	124.3 (3)	C6'—C5'—C4'	125.0 (3)
C6—C5—H5	117.8	C6'—C5'—H5'	117.5
C4—C5—H5	117.8	C4'—C5'—H5'	117.5
C5—C6—C7	120.6 (3)	C5'—C6'—C7'	120.2 (3)
C5—C6—C9	120.6 (3)	C5'—C6'—C9'	121.2 (3)
C7—C6—C9	118.4 (3)	C7'—C6'—C9'	117.9 (3)
C6—C7—C8	110.0 (3)	C6'—C7'—C8'	109.6 (3)
C6—C7—Si2	113.2 (2)	C6'—C7'—Si2'	112.8 (2)
C8—C7—Si2	120.0 (2)	C8'—C7'—Si2'	117.1 (2)
C6—C7—H7	103.9	C6'—C7'—H7'	105.4
C8—C7—H7	103.9	C8'—C7'—H7'	105.4
Si2—C7—H7	103.9	Si2'—C7'—H7'	105.4
C3—C8—C7	124.9 (3)	C3'—C8'—C7'	125.1 (3)
C3—C8—H8	117.5	C3'—C8'—H8'	117.5
C7—C8—H8	117.5	C7'—C8'—H8'	117.5
C6—C9—C10	113.1 (3)	C6'—C9'—C10'	113.9 (3)
C6—C9—H9A	109.0	C6'—C9'—H9'1	108.8
C10—C9—H9A	109.0	C10'—C9'—H9'1	108.8
C6—C9—H9B	109.0	C6'—C9'—H9'2	108.8
C10—C9—H9B	109.0	C10'—C9'—H9'2	108.8
H9A—C9—H9B	107.8	H9'1—C9'—H9'2	107.7
C11—C10—C9	110.2 (3)	C11'—C10'—C9'	110.5 (3)
C11—C10—H10A	109.6	C11'—C10'—H10C	109.5
C9—C10—H10A	109.6	C9'—C10'—H10C	109.5
C11—C10—H10B	109.6	C11'—C10'—H10D	109.5
C9—C10—H10B	109.6	C9'—C10'—H10D	109.5
H10A—C10—H10B	108.1	H10C—C10'—H10D	108.1
C12—C11—C16	117.5 (4)	C16'—C11'—C12'	116.7 (4)
C12—C11—C10	120.3 (4)	C16'—C11'—C10'	121.3 (4)
C16—C11—C10	120.2 (4)	C12'—C11'—C10'	120.5 (4)
C13—C12—C11	120.6 (4)	C13'—C12'—C11'	121.0 (4)
C13—C12—H12	119.7	C13'—C12'—H12'	119.5
C11—C12—H12	119.7	C11'—C12'—H12'	119.5
C12—C13—C14	120.7 (4)	C12'—C13'—C14'	120.8 (4)
C12—C13—H13	119.7	C12'—C13'—H13'	119.6
C14—C13—H13	119.7	C14'—C13'—H13'	119.6
C15—C14—C13	116.9 (4)	C15'—C14'—C13'	116.7 (4)
C15—C14—C1	121.0 (4)	C15'—C14'—C1'	120.2 (4)
C13—C14—C1	120.7 (3)	C13'—C14'—C1'	121.2 (4)
C16—C15—C14	120.9 (4)	C14'—C15'—C16'	120.9 (4)
C16—C15—H15	119.5	C14'—C15'—H15'	119.5
C14—C15—H15	119.5	C16'—C15'—H15'	119.5
C15—C16—C11	120.4 (4)	C11'—C16'—C15'	121.0 (4)
C15—C16—H16	119.8	C11'—C16'—H16'	119.5
C11—C16—H16	119.8	C15'—C16'—H16'	119.5
Si1—C17—H17A	109.5	Si1'—C17'—H17D	109.5
Si1—C17—H17B	109.5	Si1'—C17'—H17E	109.5
H17A—C17—H17B	109.5	H17D—C17'—H17E	109.5
Si1—C17—H17C	109.5	Si1'—C17'—H17F	109.5
H17A—C17—H17C	109.5	H17D—C17'—H17F	109.5
H17B—C17—H17C	109.5	H17E—C17'—H17F	109.5
Si1—C18—H18A	109.5	Si1'—C18'—H18D	109.5
Si1—C18—H18B	109.5	Si1'—C18'—H18E	109.5
H18A—C18—H18B	109.5	H18D—C18'—H18E	109.5
Si1—C18—H18C	109.5	Si1'—C18'—H18F	109.5
H18A—C18—H18C	109.5	H18D—C18'—H18F	109.5
H18B—C18—H18C	109.5	H18E—C18'—H18F	109.5
Si1—C19—H19A	109.5	Si1'—C19'—H19D	109.5
Si1—C19—H19B	109.5	Si1'—C19'—H19E	109.5
H19A—C19—H19B	109.5	H19D—C19'—H19E	109.5
Si1—C19—H19C	109.5	Si1'—C19'—H19F	109.5
H19A—C19—H19C	109.5	H19D—C19'—H19F	109.5
H19B—C19—H19C	109.5	H19E—C19'—H19F	109.5
Si2—C20—H20A	109.5	Si2'—C20'—H20D	109.5
Si2—C20—H20B	109.5	Si2'—C20'—H20E	109.5
H20A—C20—H20B	109.5	H20D—C20'—H20E	109.5
Si2—C20—H20C	109.5	Si2'—C20'—H20F	109.5
H20A—C20—H20C	109.5	H20D—C20'—H20F	109.5
H20B—C20—H20C	109.5	H20E—C20'—H20F	109.5
Si2—C21—H21A	109.5	Si2'—C21'—H21D	109.5
Si2—C21—H21B	109.5	Si2'—C21'—H21E	109.5
H21A—C21—H21B	109.5	H21D—C21'—H21E	109.5
Si2—C21—H21C	109.5	Si2'—C21'—H21F	109.5
H21A—C21—H21C	109.5	H21D—C21'—H21F	109.5
H21B—C21—H21C	109.5	H21E—C21'—H21F	109.5
Si2—C22—H22A	109.5	Si2'—C22'—H22D	109.5
Si2—C22—H22B	109.5	Si2'—C22'—H22E	109.5
H22A—C22—H22B	109.5	H22D—C22'—H22E	109.5
Si2—C22—H22C	109.5	Si2'—C22'—H22F	109.5
H22A—C22—H22C	109.5	H22D—C22'—H22F	109.5
H22B—C22—H22C	109.5	H22E—C22'—H22F	109.5
C14—C1—C2—C3	−28.4 (5)	C14'—C1'—C2'—C3'	27.2 (5)
C1—C2—C3—C8	101.0 (4)	C1'—C2'—C3'—C8'	−101.6 (4)
C1—C2—C3—C4	−68.4 (4)	C1'—C2'—C3'—C4'	68.7 (5)
C8—C3—C4—C5	−29.7 (4)	C8'—C3'—C4'—C5'	28.0 (4)
C2—C3—C4—C5	139.8 (3)	C2'—C3'—C4'—C5'	−142.4 (3)
C8—C3—C4—Si1	101.4 (3)	C8'—C3'—C4'—Si1'	−105.3 (3)
C2—C3—C4—Si1	−89.2 (3)	C2'—C3'—C4'—Si1'	84.4 (3)
C18—Si1—C4—C3	−168.2 (3)	C19'—Si1'—C4'—C3'	161.0 (3)
C17—Si1—C4—C3	−47.6 (3)	C17'—Si1'—C4'—C3'	37.5 (3)
C19—Si1—C4—C3	71.5 (3)	C18'—Si1'—C4'—C3'	−80.1 (3)
C18—Si1—C4—C5	−39.9 (3)	C19'—Si1'—C4'—C5'	30.8 (3)
C17—Si1—C4—C5	80.7 (3)	C17'—Si1'—C4'—C5'	−92.6 (3)
C19—Si1—C4—C5	−160.2 (3)	C18'—Si1'—C4'—C5'	149.7 (3)
C3—C4—C5—C6	18.4 (5)	C3'—C4'—C5'—C6'	−17.2 (5)
Si1—C4—C5—C6	−111.2 (3)	Si1'—C4'—C5'—C6'	115.0 (4)
C4—C5—C6—C7	10.3 (5)	C4'—C5'—C6'—C7'	−11.2 (5)
C4—C5—C6—C9	−161.9 (3)	C4'—C5'—C6'—C9'	159.2 (3)
C5—C6—C7—C8	−26.8 (4)	C5'—C6'—C7'—C8'	27.8 (4)
C9—C6—C7—C8	145.5 (3)	C9'—C6'—C7'—C8'	−142.9 (3)
C5—C6—C7—Si2	110.5 (3)	C5'—C6'—C7'—Si2'	−104.6 (3)
C9—C6—C7—Si2	−77.1 (3)	C9'—C6'—C7'—Si2'	84.7 (3)
C20—Si2—C7—C6	−144.4 (3)	C21'—Si2'—C7'—C6'	151.4 (3)
C21—Si2—C7—C6	−19.5 (3)	C20'—Si2'—C7'—C6'	−89.1 (4)
C22—Si2—C7—C6	99.8 (3)	C22'—Si2'—C7'—C6'	28.8 (3)
C20—Si2—C7—C8	−11.7 (4)	C21'—Si2'—C7'—C8'	22.8 (4)
C21—Si2—C7—C8	113.2 (3)	C20'—Si2'—C7'—C8'	142.3 (3)
C22—Si2—C7—C8	−127.5 (3)	C22'—Si2'—C7'—C8'	−99.7 (3)
C4—C3—C8—C7	13.3 (5)	C4'—C3'—C8'—C7'	−11.2 (5)
C2—C3—C8—C7	−156.1 (3)	C2'—C3'—C8'—C7'	159.0 (3)
C6—C7—C8—C3	15.3 (5)	C6'—C7'—C8'—C3'	−17.0 (5)
Si2—C7—C8—C3	−118.7 (3)	Si2'—C7'—C8'—C3'	113.1 (3)
C5—C6—C9—C10	104.0 (4)	C5'—C6'—C9'—C10'	−98.6 (4)
C7—C6—C9—C10	−68.4 (4)	C7'—C6'—C9'—C10'	72.0 (4)
C6—C9—C10—C11	−28.2 (5)	C6'—C9'—C10'—C11'	24.6 (5)
C9—C10—C11—C12	103.5 (4)	C9'—C10'—C11'—C16'	62.7 (5)
C9—C10—C11—C16	−60.3 (5)	C9'—C10'—C11'—C12'	−102.9 (4)
C16—C11—C12—C13	13.2 (5)	C16'—C11'—C12'—C13'	−13.3 (5)
C10—C11—C12—C13	−151.1 (3)	C10'—C11'—C12'—C13'	153.0 (3)
C11—C12—C13—C14	0.8 (5)	C11'—C12'—C13'—C14'	−0.4 (5)
C12—C13—C14—C15	−14.3 (5)	C12'—C13'—C14'—C15'	13.4 (5)
C12—C13—C14—C1	152.1 (3)	C12'—C13'—C14'—C1'	−151.1 (4)
C2—C1—C14—C15	104.9 (4)	C2'—C1'—C14'—C15'	−102.1 (4)
C2—C1—C14—C13	−60.9 (5)	C2'—C1'—C14'—C13'	61.8 (5)
C13—C14—C15—C16	13.8 (5)	C13'—C14'—C15'—C16'	−12.8 (5)
C1—C14—C15—C16	−152.5 (3)	C1'—C14'—C15'—C16'	151.8 (3)
C14—C15—C16—C11	0.1 (5)	C12'—C11'—C16'—C15'	13.8 (5)
C12—C11—C16—C15	−13.7 (5)	C10'—C11'—C16'—C15'	−152.3 (3)
C10—C11—C16—C15	150.6 (3)	C14'—C15'—C16'—C11'	−0.8 (5)