The molecular structure of the title compound, C39H62N2O5Si2, obtained as an unexpected side product, was determined in the course of our studies on the synthesis of N-triisopropyl-1H-indol-3-yl derivatives. Interestingly, although the triisopropylsilyl group was intended as a temporary protecting group, the compound comprises a remarkably stable N—Si bond. The vinyl C=C double bond possesses a Z configuration.
Supporting information
CCDC reference: 640279
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- Disorder in main residue
- R factor = 0.055
- wR factor = 0.149
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) ....... 3
PLAT220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.78 Ratio
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C44
Alert level C
GOODF01_ALERT_2_C The least squares goodness of fit parameter lies
outside the range 0.80 <> 2.00
Goodness of fit given = 0.779
RINTA01_ALERT_3_C The value of Rint is greater than 0.10
Rint given 0.111
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 45 Perc.
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.04
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg.
PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.58 Ratio
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C29
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C35
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C38
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C41
PLAT301_ALERT_3_C Main Residue Disorder ......................... 6.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 22.10 Deg.
C32A -SI2 -C32B 1.555 1.555 1.555
0 ALERT level A = In general: serious problem
3 ALERT level B = Potentially serious problem
14 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
9 ALERT type 2 Indicator that the structure model may be wrong or deficient
6 ALERT type 3 Indicator that the structure quality may be low
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
Crystal data top
C39H62N2O5Si2 | Z = 2 |
Mr = 695.09 | F(000) = 756 |
Triclinic, P1 | Dx = 1.112 Mg m−3 |
Hall symbol: -P 1 | Melting point: 128.5 K |
a = 9.0114 (13) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 14.886 (2) Å | Cell parameters from 2764 reflections |
c = 16.023 (2) Å | θ = 2–20° |
α = 87.639 (4)° | µ = 0.13 mm−1 |
β = 84.428 (4)° | T = 298 K |
γ = 76.011 (4)° | Needle, colourless |
V = 2075.4 (5) Å3 | 0.60 × 0.32 × 0.19 mm |
Data collection top
Bruker SMART CCD diffractometer | 7301 independent reflections |
Radiation source: sealed Tube | 3296 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.111 |
ω and φ scans | θmax = 25.0°, θmin = 2.4° |
Absorption correction: multi-scan (MULABS; Blessing, 1995) | h = −10→10 |
Tmin = 0.904, Tmax = 0.94 | k = −17→17 |
19562 measured reflections | l = −19→19 |
Refinement top
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.149 | H-atom parameters constrained |
S = 0.78 | w = 1/[σ2(Fo2) + (0.0761P)2] where P = (Fo2 + 2Fc2)/3 |
7301 reflections | (Δ/σ)max < 0.001 |
444 parameters | Δρmax = 0.30 e Å−3 |
8 restraints | Δρmin = −0.29 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Si1 | 1.00619 (10) | 0.30396 (6) | 0.10177 (5) | 0.0579 (3) | |
Si2 | 0.77463 (11) | 0.30835 (6) | 0.46439 (5) | 0.0609 (3) | |
O14 | 0.6959 (3) | −0.08684 (16) | 0.47820 (14) | 0.0943 (9) | |
O22 | 0.3655 (3) | 0.21876 (19) | 0.74538 (16) | 0.1012 (9) | |
O24 | 0.5544 (3) | 0.2229 (2) | 0.86225 (15) | 0.0964 (9) | |
O26 | 0.8350 (3) | 0.11445 (18) | 0.85523 (16) | 0.0979 (9) | |
O28 | 0.8601 (2) | 0.20087 (12) | 0.43417 (11) | 0.0565 (5) | |
N1 | 0.9197 (3) | 0.22683 (15) | 0.16673 (14) | 0.0507 (6) | |
N12 | 0.7751 (3) | 0.04140 (16) | 0.49630 (13) | 0.0549 (7) | |
H12 | 0.7655 | 0.0859 | 0.5383 | 0.066* | |
C2 | 0.8136 (3) | 0.17639 (19) | 0.14899 (18) | 0.0503 (8) | |
C3 | 0.7639 (4) | 0.1602 (2) | 0.07280 (19) | 0.0625 (9) | |
H3 | 0.7996 | 0.1859 | 0.0233 | 0.075* | |
C4 | 0.6614 (4) | 0.1057 (2) | 0.0720 (2) | 0.0689 (9) | |
H4 | 0.6282 | 0.0938 | 0.0213 | 0.083* | |
C5 | 0.6063 (4) | 0.0679 (2) | 0.1459 (2) | 0.0714 (10) | |
H5 | 0.5365 | 0.0312 | 0.1439 | 0.086* | |
C6 | 0.6530 (4) | 0.0836 (2) | 0.2212 (2) | 0.0610 (8) | |
H6 | 0.6143 | 0.0586 | 0.2703 | 0.073* | |
C7 | 0.7598 (3) | 0.13776 (19) | 0.22431 (18) | 0.0492 (7) | |
C8 | 0.8355 (3) | 0.16493 (18) | 0.29047 (17) | 0.0474 (7) | |
C9 | 0.9281 (3) | 0.21730 (19) | 0.25248 (17) | 0.0502 (7) | |
H9 | 0.9907 | 0.2440 | 0.2813 | 0.060* | |
C10 | 0.8213 (3) | 0.14201 (19) | 0.37967 (18) | 0.0492 (7) | |
C11 | 0.7863 (3) | 0.0652 (2) | 0.41106 (17) | 0.0540 (8) | |
H11 | 0.7680 | 0.0239 | 0.3735 | 0.065* | |
C13 | 0.7294 (4) | −0.0344 (2) | 0.52507 (18) | 0.0551 (8) | |
C15 | 0.7287 (4) | −0.05580 (19) | 0.61771 (16) | 0.0587 (8) | |
H15A | 0.8300 | −0.0924 | 0.6281 | 0.070* | |
H15B | 0.6574 | −0.0948 | 0.6317 | 0.070* | |
C16 | 0.6876 (4) | 0.0238 (2) | 0.67815 (17) | 0.0512 (8) | |
C17 | 0.5457 (4) | 0.0859 (2) | 0.67862 (18) | 0.0585 (8) | |
H17 | 0.4793 | 0.0818 | 0.6388 | 0.070* | |
C18 | 0.5027 (4) | 0.1541 (2) | 0.7382 (2) | 0.0680 (9) | |
C19 | 0.6014 (4) | 0.1606 (2) | 0.7977 (2) | 0.0707 (10) | |
C20 | 0.7449 (4) | 0.1002 (2) | 0.7958 (2) | 0.0672 (9) | |
C21 | 0.7870 (4) | 0.0316 (2) | 0.73639 (18) | 0.0617 (9) | |
H21 | 0.8828 | −0.0096 | 0.7357 | 0.074* | |
C23 | 0.2485 (4) | 0.2087 (3) | 0.6976 (3) | 0.1117 (15) | |
H23A | 0.1610 | 0.2599 | 0.7073 | 0.134* | |
H23B | 0.2197 | 0.1519 | 0.7135 | 0.134* | |
H23C | 0.2846 | 0.2073 | 0.6391 | 0.134* | |
C25 | 0.5757 (6) | 0.3086 (3) | 0.8422 (3) | 0.1349 (19) | |
H25A | 0.5322 | 0.3497 | 0.8877 | 0.162* | |
H25B | 0.5263 | 0.3314 | 0.7925 | 0.162* | |
H25C | 0.6836 | 0.3055 | 0.8324 | 0.162* | |
C27 | 0.9804 (5) | 0.0547 (3) | 0.8580 (3) | 0.1312 (19) | |
H27A | 1.0288 | 0.0704 | 0.9043 | 0.157* | |
H27B | 1.0419 | 0.0606 | 0.8067 | 0.157* | |
H27C | 0.9702 | −0.0080 | 0.8651 | 0.157* | |
C29 | 0.8697 (4) | 0.3897 (2) | 0.4001 (2) | 0.0664 (9) | |
H29 | 0.8588 | 0.3783 | 0.3414 | 0.080* | |
C30 | 0.7962 (5) | 0.4927 (2) | 0.4140 (3) | 0.1058 (14) | |
H30A | 0.6906 | 0.5061 | 0.4022 | 0.127* | |
H30B | 0.8500 | 0.5292 | 0.3774 | 0.127* | |
H30C | 0.8020 | 0.5073 | 0.4713 | 0.127* | |
C31 | 1.0440 (4) | 0.3693 (3) | 0.4085 (3) | 0.1012 (13) | |
H31A | 1.0896 | 0.3051 | 0.3977 | 0.121* | |
H31B | 1.0611 | 0.3831 | 0.4643 | 0.121* | |
H31C | 1.0899 | 0.4070 | 0.3688 | 0.121* | |
C32A | 0.7715 (10) | 0.3013 (5) | 0.5808 (4) | 0.074 (3)* | 0.446 (10) |
H32A | 0.6891 | 0.2744 | 0.6072 | 0.089* | 0.446 (10) |
C33A | 0.9335 (12) | 0.2460 (7) | 0.6022 (7) | 0.119 (4)* | 0.446 (10) |
H33A | 0.9527 | 0.1841 | 0.5820 | 0.179* | 0.446 (10) |
H33B | 0.9381 | 0.2440 | 0.6619 | 0.179* | 0.446 (10) |
H33C | 1.0098 | 0.2758 | 0.5760 | 0.179* | 0.446 (10) |
C34A | 0.7698 (12) | 0.4002 (5) | 0.6191 (6) | 0.083 (3)* | 0.446 (10) |
H34A | 0.6727 | 0.4425 | 0.6121 | 0.125* | 0.446 (10) |
H34B | 0.8507 | 0.4243 | 0.5902 | 0.125* | 0.446 (10) |
H34C | 0.7849 | 0.3925 | 0.6777 | 0.125* | 0.446 (10) |
C32B | 0.8442 (10) | 0.3158 (4) | 0.5745 (4) | 0.085 (3)* | 0.554 (10) |
H32B | 0.9386 | 0.3381 | 0.5702 | 0.102* | 0.554 (10) |
C33B | 0.8638 (9) | 0.2253 (4) | 0.6241 (4) | 0.079 (3)* | 0.554 (10) |
H33D | 0.9318 | 0.1767 | 0.5918 | 0.118* | 0.554 (10) |
H33E | 0.7657 | 0.2108 | 0.6361 | 0.118* | 0.554 (10) |
H33F | 0.9063 | 0.2313 | 0.6757 | 0.118* | 0.554 (10) |
C34B | 0.7026 (11) | 0.3890 (5) | 0.6246 (6) | 0.118 (4)* | 0.554 (10) |
H34D | 0.6793 | 0.4461 | 0.5931 | 0.177* | 0.554 (10) |
H34E | 0.7313 | 0.4003 | 0.6787 | 0.177* | 0.554 (10) |
H34F | 0.6138 | 0.3636 | 0.6316 | 0.177* | 0.554 (10) |
C35 | 0.5657 (4) | 0.3379 (2) | 0.4514 (2) | 0.0761 (10) | |
H35 | 0.5249 | 0.3986 | 0.4770 | 0.091* | |
C36 | 0.5247 (4) | 0.3503 (3) | 0.3616 (3) | 0.1074 (14) | |
H36A | 0.5786 | 0.3922 | 0.3324 | 0.129* | |
H36B | 0.4161 | 0.3752 | 0.3609 | 0.129* | |
H36C | 0.5534 | 0.2915 | 0.3345 | 0.129* | |
C37 | 0.4799 (5) | 0.2729 (3) | 0.4999 (3) | 0.143 (2) | |
H37A | 0.4974 | 0.2718 | 0.5581 | 0.171* | |
H37B | 0.5161 | 0.2116 | 0.4781 | 0.171* | |
H37C | 0.3719 | 0.2943 | 0.4941 | 0.171* | |
C38 | 0.8514 (4) | 0.4114 (2) | 0.0823 (2) | 0.0752 (10) | |
H38 | 0.9028 | 0.4542 | 0.0499 | 0.090* | |
C39 | 0.7818 (5) | 0.4599 (3) | 0.1636 (3) | 0.1332 (19) | |
H39A | 0.8622 | 0.4703 | 0.1943 | 0.160* | |
H39B | 0.7255 | 0.4219 | 0.1967 | 0.160* | |
H39C | 0.7137 | 0.5182 | 0.1511 | 0.160* | |
C40 | 0.7273 (5) | 0.3973 (3) | 0.0303 (3) | 0.1165 (16) | |
H40A | 0.7739 | 0.3674 | −0.0210 | 0.140* | |
H40B | 0.6614 | 0.4563 | 0.0175 | 0.140* | |
H40C | 0.6680 | 0.3594 | 0.0612 | 0.140* | |
C41 | 1.1479 (4) | 0.3359 (2) | 0.1664 (2) | 0.0725 (10) | |
H41 | 1.0903 | 0.3575 | 0.2198 | 0.087* | |
C42 | 1.2109 (6) | 0.4179 (3) | 0.1291 (3) | 0.1269 (17) | |
H42A | 1.2710 | 0.4364 | 0.1685 | 0.152* | |
H42B | 1.1268 | 0.4689 | 0.1176 | 0.152* | |
H42C | 1.2740 | 0.3994 | 0.0780 | 0.152* | |
C43 | 1.2833 (4) | 0.2564 (3) | 0.1893 (2) | 0.0939 (12) | |
H43A | 1.3533 | 0.2392 | 0.1403 | 0.113* | |
H43B | 1.2453 | 0.2041 | 0.2101 | 0.113* | |
H43C | 1.3357 | 0.2766 | 0.2317 | 0.113* | |
C44 | 1.0941 (4) | 0.2465 (3) | 0.0021 (2) | 0.0792 (10) | |
H44 | 1.0079 | 0.2311 | −0.0223 | 0.095* | |
C45 | 1.2076 (5) | 0.1546 (3) | 0.0100 (3) | 0.1083 (14) | |
H45A | 1.1623 | 0.1144 | 0.0472 | 0.130* | |
H45B | 1.2981 | 0.1638 | 0.0320 | 0.130* | |
H45C | 1.2346 | 0.1271 | −0.0442 | 0.130* | |
C46 | 1.1500 (7) | 0.3092 (3) | −0.0620 (3) | 0.179 (3) | |
H46A | 1.2414 | 0.3231 | −0.0454 | 0.215* | |
H46B | 1.0721 | 0.3655 | −0.0666 | 0.215* | |
H46C | 1.1724 | 0.2792 | −0.1152 | 0.215* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0659 (6) | 0.0499 (6) | 0.0532 (6) | −0.0102 (5) | 0.0046 (4) | 0.0079 (4) |
Si2 | 0.0748 (7) | 0.0543 (6) | 0.0533 (5) | −0.0138 (5) | −0.0046 (5) | −0.0103 (4) |
O14 | 0.173 (3) | 0.0790 (17) | 0.0532 (14) | −0.0703 (18) | −0.0167 (15) | −0.0013 (13) |
O22 | 0.0617 (17) | 0.131 (2) | 0.0977 (19) | 0.0178 (16) | −0.0212 (15) | −0.0570 (17) |
O24 | 0.098 (2) | 0.101 (2) | 0.0760 (17) | 0.0142 (17) | −0.0185 (14) | −0.0392 (16) |
O26 | 0.0856 (19) | 0.103 (2) | 0.0928 (19) | 0.0213 (16) | −0.0434 (16) | −0.0431 (15) |
O28 | 0.0693 (14) | 0.0469 (12) | 0.0538 (12) | −0.0134 (11) | −0.0083 (10) | −0.0029 (10) |
N1 | 0.0613 (17) | 0.0444 (14) | 0.0440 (15) | −0.0107 (13) | −0.0007 (12) | 0.0065 (11) |
N12 | 0.087 (2) | 0.0444 (15) | 0.0359 (14) | −0.0236 (14) | 0.0031 (13) | −0.0057 (11) |
C2 | 0.059 (2) | 0.0431 (18) | 0.0450 (18) | −0.0050 (16) | −0.0027 (15) | −0.0002 (14) |
C3 | 0.071 (2) | 0.064 (2) | 0.049 (2) | −0.0117 (19) | −0.0045 (17) | 0.0074 (16) |
C4 | 0.069 (2) | 0.073 (2) | 0.066 (2) | −0.016 (2) | −0.0150 (19) | −0.0046 (19) |
C5 | 0.069 (2) | 0.069 (2) | 0.079 (3) | −0.0215 (19) | −0.009 (2) | −0.002 (2) |
C6 | 0.065 (2) | 0.059 (2) | 0.058 (2) | −0.0156 (18) | −0.0007 (17) | 0.0035 (16) |
C7 | 0.0531 (19) | 0.0386 (17) | 0.0511 (19) | −0.0044 (15) | 0.0023 (15) | 0.0009 (14) |
C8 | 0.0535 (19) | 0.0385 (17) | 0.0460 (18) | −0.0053 (15) | 0.0015 (15) | 0.0013 (14) |
C9 | 0.057 (2) | 0.0423 (17) | 0.0467 (19) | −0.0046 (15) | −0.0030 (15) | −0.0006 (14) |
C10 | 0.054 (2) | 0.0408 (18) | 0.0486 (18) | −0.0050 (15) | 0.0016 (15) | −0.0046 (15) |
C11 | 0.077 (2) | 0.0446 (18) | 0.0409 (18) | −0.0173 (16) | 0.0022 (15) | −0.0030 (14) |
C13 | 0.075 (2) | 0.0456 (19) | 0.0449 (19) | −0.0162 (17) | 0.0018 (16) | −0.0053 (15) |
C15 | 0.083 (2) | 0.0502 (19) | 0.0416 (18) | −0.0175 (17) | 0.0039 (16) | 0.0014 (15) |
C16 | 0.063 (2) | 0.0516 (19) | 0.0378 (17) | −0.0137 (17) | 0.0024 (16) | −0.0028 (14) |
C17 | 0.062 (2) | 0.073 (2) | 0.0423 (18) | −0.0200 (19) | −0.0019 (16) | −0.0106 (17) |
C18 | 0.054 (2) | 0.085 (3) | 0.058 (2) | 0.000 (2) | −0.0071 (18) | −0.0141 (19) |
C19 | 0.068 (2) | 0.081 (2) | 0.055 (2) | 0.003 (2) | −0.0043 (19) | −0.0307 (19) |
C20 | 0.068 (2) | 0.074 (2) | 0.055 (2) | −0.002 (2) | −0.0181 (18) | −0.0187 (18) |
C21 | 0.066 (2) | 0.060 (2) | 0.052 (2) | 0.0010 (17) | −0.0069 (18) | −0.0046 (17) |
C23 | 0.061 (3) | 0.157 (4) | 0.108 (3) | 0.003 (3) | −0.017 (2) | −0.040 (3) |
C25 | 0.150 (5) | 0.097 (4) | 0.153 (5) | −0.004 (3) | −0.030 (4) | −0.055 (3) |
C27 | 0.096 (4) | 0.134 (4) | 0.147 (4) | 0.033 (3) | −0.065 (3) | −0.060 (3) |
C29 | 0.074 (2) | 0.054 (2) | 0.075 (2) | −0.0214 (18) | −0.0048 (18) | −0.0166 (17) |
C30 | 0.131 (4) | 0.059 (2) | 0.129 (4) | −0.034 (2) | 0.020 (3) | −0.024 (2) |
C31 | 0.091 (3) | 0.114 (3) | 0.113 (3) | −0.048 (3) | −0.007 (2) | −0.029 (3) |
C35 | 0.069 (2) | 0.058 (2) | 0.097 (3) | −0.0110 (19) | 0.012 (2) | −0.015 (2) |
C36 | 0.067 (3) | 0.116 (3) | 0.134 (4) | −0.003 (2) | −0.020 (3) | −0.041 (3) |
C37 | 0.086 (3) | 0.095 (3) | 0.234 (6) | −0.022 (3) | 0.038 (3) | 0.025 (4) |
C38 | 0.083 (3) | 0.060 (2) | 0.072 (2) | −0.006 (2) | 0.005 (2) | 0.0175 (19) |
C39 | 0.152 (4) | 0.090 (3) | 0.108 (4) | 0.050 (3) | 0.022 (3) | 0.015 (3) |
C40 | 0.091 (3) | 0.089 (3) | 0.165 (4) | −0.011 (3) | −0.040 (3) | 0.046 (3) |
C41 | 0.080 (3) | 0.065 (2) | 0.074 (2) | −0.028 (2) | 0.002 (2) | 0.0110 (18) |
C42 | 0.155 (4) | 0.124 (4) | 0.125 (4) | −0.083 (3) | −0.018 (3) | 0.030 (3) |
C43 | 0.077 (3) | 0.114 (3) | 0.094 (3) | −0.025 (3) | −0.019 (2) | −0.002 (2) |
C44 | 0.085 (3) | 0.078 (3) | 0.067 (2) | −0.015 (2) | 0.020 (2) | −0.0010 (19) |
C45 | 0.101 (3) | 0.102 (3) | 0.112 (3) | −0.003 (3) | 0.002 (3) | −0.036 (3) |
C46 | 0.277 (7) | 0.113 (4) | 0.118 (4) | −0.037 (4) | 0.110 (4) | −0.007 (3) |
Geometric parameters (Å, º) top
Si1—N1 | 1.785 (2) | C29—H29 | 0.9800 |
Si1—C44 | 1.857 (3) | C30—H30A | 0.9600 |
Si1—C41 | 1.876 (3) | C30—H30B | 0.9600 |
Si1—C38 | 1.888 (3) | C30—H30C | 0.9600 |
Si2—O28 | 1.668 (2) | C31—H31A | 0.9600 |
Si2—C35 | 1.857 (4) | C31—H31B | 0.9600 |
Si2—C32A | 1.862 (6) | C31—H31C | 0.9600 |
Si2—C29 | 1.868 (3) | C32A—C33A | 1.555 (9) |
Si2—C32B | 1.945 (6) | C32A—C34A | 1.614 (8) |
O14—C13 | 1.213 (3) | C32A—H32A | 0.9800 |
O22—C18 | 1.369 (4) | C33A—H33A | 0.9600 |
O22—C23 | 1.402 (4) | C33A—H33B | 0.9600 |
O24—C25 | 1.357 (5) | C33A—H33C | 0.9600 |
O24—C19 | 1.383 (4) | C34A—H34A | 0.9600 |
O26—C20 | 1.364 (3) | C34A—H34B | 0.9600 |
O26—C27 | 1.398 (4) | C34A—H34C | 0.9600 |
O28—C10 | 1.387 (3) | C32B—C33B | 1.516 (7) |
N1—C9 | 1.383 (3) | C32B—C34B | 1.631 (8) |
N1—C2 | 1.406 (3) | C32B—H32B | 0.9800 |
N12—C13 | 1.342 (3) | C33B—H33D | 0.9600 |
N12—C11 | 1.397 (3) | C33B—H33E | 0.9600 |
N12—H12 | 0.9467 | C33B—H33F | 0.9600 |
C2—C3 | 1.390 (4) | C34B—H34D | 0.9600 |
C2—C7 | 1.409 (4) | C34B—H34E | 0.9600 |
C3—C4 | 1.370 (4) | C34B—H34F | 0.9600 |
C3—H3 | 0.9300 | C35—C36 | 1.513 (5) |
C4—C5 | 1.389 (4) | C35—C37 | 1.524 (5) |
C4—H4 | 0.9300 | C35—H35 | 0.9800 |
C5—C6 | 1.364 (4) | C36—H36A | 0.9600 |
C5—H5 | 0.9300 | C36—H36B | 0.9600 |
C6—C7 | 1.402 (4) | C36—H36C | 0.9600 |
C6—H6 | 0.9300 | C37—H37A | 0.9600 |
C7—C8 | 1.436 (4) | C37—H37B | 0.9600 |
C8—C9 | 1.361 (4) | C37—H37C | 0.9600 |
C8—C10 | 1.456 (4) | C38—C40 | 1.516 (5) |
C9—H9 | 0.9300 | C38—C39 | 1.520 (5) |
C10—C11 | 1.326 (3) | C38—H38 | 0.9800 |
C11—H11 | 0.9300 | C39—H39A | 0.9600 |
C13—C15 | 1.505 (4) | C39—H39B | 0.9600 |
C15—C16 | 1.514 (4) | C39—H39C | 0.9600 |
C15—H15A | 0.9700 | C40—H40A | 0.9600 |
C15—H15B | 0.9700 | C40—H40B | 0.9600 |
C16—C21 | 1.381 (4) | C40—H40C | 0.9600 |
C16—C17 | 1.384 (4) | C41—C43 | 1.541 (5) |
C17—C18 | 1.382 (4) | C41—C42 | 1.542 (4) |
C17—H17 | 0.9300 | C41—H41 | 0.9800 |
C18—C19 | 1.387 (4) | C42—H42A | 0.9600 |
C19—C20 | 1.383 (4) | C42—H42B | 0.9600 |
C20—C21 | 1.385 (4) | C42—H42C | 0.9600 |
C21—H21 | 0.9300 | C43—H43A | 0.9600 |
C23—H23A | 0.9600 | C43—H43B | 0.9600 |
C23—H23B | 0.9600 | C43—H43C | 0.9600 |
C23—H23C | 0.9600 | C44—C46 | 1.492 (5) |
C25—H25A | 0.9600 | C44—C45 | 1.506 (5) |
C25—H25B | 0.9600 | C44—H44 | 0.9800 |
C25—H25C | 0.9600 | C45—H45A | 0.9600 |
C27—H27A | 0.9600 | C45—H45B | 0.9600 |
C27—H27B | 0.9600 | C45—H45C | 0.9600 |
C27—H27C | 0.9600 | C46—H46A | 0.9600 |
C29—C30 | 1.532 (4) | C46—H46B | 0.9600 |
C29—C31 | 1.545 (5) | C46—H46C | 0.9600 |
| | | |
N1—Si1—C44 | 109.69 (14) | C29—C31—H31B | 109.5 |
N1—Si1—C41 | 105.32 (13) | H31A—C31—H31B | 109.5 |
C44—Si1—C41 | 113.85 (17) | C29—C31—H31C | 109.5 |
N1—Si1—C38 | 107.63 (14) | H31A—C31—H31C | 109.5 |
C44—Si1—C38 | 111.45 (17) | H31B—C31—H31C | 109.5 |
C41—Si1—C38 | 108.56 (17) | C33A—C32A—C34A | 99.5 (7) |
O28—Si2—C35 | 112.10 (13) | C33A—C32A—Si2 | 107.1 (7) |
O28—Si2—C32A | 103.9 (2) | C34A—C32A—Si2 | 111.2 (6) |
C35—Si2—C32A | 100.7 (3) | C33A—C32A—H32A | 112.7 |
O28—Si2—C29 | 107.90 (13) | C34A—C32A—H32A | 112.7 |
C35—Si2—C29 | 109.96 (15) | Si2—C32A—H32A | 112.7 |
C32A—Si2—C29 | 122.1 (3) | C32A—C33A—H33A | 109.5 |
O28—Si2—C32B | 104.0 (2) | C32A—C33A—H33B | 109.5 |
C35—Si2—C32B | 119.6 (3) | H33A—C33A—H33B | 109.5 |
C32A—Si2—C32B | 22.1 (3) | C32A—C33A—H33C | 109.5 |
C29—Si2—C32B | 102.3 (3) | H33A—C33A—H33C | 109.5 |
C18—O22—C23 | 118.6 (3) | H33B—C33A—H33C | 109.5 |
C25—O24—C19 | 113.8 (3) | C32A—C34A—H34A | 109.5 |
C20—O26—C27 | 118.2 (3) | C32A—C34A—H34B | 109.5 |
C10—O28—Si2 | 132.17 (18) | H34A—C34A—H34B | 109.5 |
C9—N1—C2 | 105.1 (2) | C32A—C34A—H34C | 109.5 |
C9—N1—Si1 | 123.8 (2) | H34A—C34A—H34C | 109.5 |
C2—N1—Si1 | 130.35 (19) | H34B—C34A—H34C | 109.5 |
C13—N12—C11 | 122.4 (2) | C33B—C32B—C34B | 106.1 (6) |
C13—N12—H12 | 112.9 | C33B—C32B—Si2 | 112.9 (5) |
C11—N12—H12 | 121.6 | C34B—C32B—Si2 | 104.3 (5) |
C3—C2—N1 | 130.1 (3) | C33B—C32B—H32B | 111.1 |
C3—C2—C7 | 120.9 (3) | C34B—C32B—H32B | 111.1 |
N1—C2—C7 | 109.0 (2) | Si2—C32B—H32B | 111.1 |
C4—C3—C2 | 118.8 (3) | C32B—C33B—H33D | 109.5 |
C4—C3—H3 | 120.6 | C32B—C33B—H33E | 109.5 |
C2—C3—H3 | 120.6 | H33D—C33B—H33E | 109.5 |
C3—C4—C5 | 120.9 (3) | C32B—C33B—H33F | 109.5 |
C3—C4—H4 | 119.5 | H33D—C33B—H33F | 109.5 |
C5—C4—H4 | 119.5 | H33E—C33B—H33F | 109.5 |
C6—C5—C4 | 121.0 (3) | C32B—C34B—H34D | 109.5 |
C6—C5—H5 | 119.5 | C32B—C34B—H34E | 109.5 |
C4—C5—H5 | 119.5 | H34D—C34B—H34E | 109.5 |
C5—C6—C7 | 119.7 (3) | C32B—C34B—H34F | 109.5 |
C5—C6—H6 | 120.2 | H34D—C34B—H34F | 109.5 |
C7—C6—H6 | 120.2 | H34E—C34B—H34F | 109.5 |
C6—C7—C2 | 118.7 (3) | C36—C35—C37 | 110.7 (4) |
C6—C7—C8 | 134.1 (3) | C36—C35—Si2 | 115.2 (3) |
C2—C7—C8 | 107.2 (2) | C37—C35—Si2 | 113.4 (3) |
C9—C8—C7 | 105.4 (2) | C36—C35—H35 | 105.5 |
C9—C8—C10 | 125.8 (3) | C37—C35—H35 | 105.5 |
C7—C8—C10 | 128.8 (3) | Si2—C35—H35 | 105.5 |
C8—C9—N1 | 113.3 (3) | C35—C36—H36A | 109.5 |
C8—C9—H9 | 123.4 | C35—C36—H36B | 109.5 |
N1—C9—H9 | 123.4 | H36A—C36—H36B | 109.5 |
C11—C10—O28 | 118.2 (3) | C35—C36—H36C | 109.5 |
C11—C10—C8 | 124.3 (3) | H36A—C36—H36C | 109.5 |
O28—C10—C8 | 117.3 (2) | H36B—C36—H36C | 109.5 |
C10—C11—N12 | 124.9 (3) | C35—C37—H37A | 109.5 |
C10—C11—H11 | 117.5 | C35—C37—H37B | 109.5 |
N12—C11—H11 | 117.5 | H37A—C37—H37B | 109.5 |
O14—C13—N12 | 121.7 (3) | C35—C37—H37C | 109.5 |
O14—C13—C15 | 120.3 (3) | H37A—C37—H37C | 109.5 |
N12—C13—C15 | 117.9 (3) | H37B—C37—H37C | 109.5 |
C13—C15—C16 | 118.7 (2) | C40—C38—C39 | 111.0 (4) |
C13—C15—H15A | 107.6 | C40—C38—Si1 | 115.2 (3) |
C16—C15—H15A | 107.6 | C39—C38—Si1 | 111.6 (2) |
C13—C15—H15B | 107.6 | C40—C38—H38 | 106.1 |
C16—C15—H15B | 107.6 | C39—C38—H38 | 106.1 |
H15A—C15—H15B | 107.1 | Si1—C38—H38 | 106.1 |
C21—C16—C17 | 119.6 (3) | C38—C39—H39A | 109.5 |
C21—C16—C15 | 120.4 (3) | C38—C39—H39B | 109.5 |
C17—C16—C15 | 119.9 (3) | H39A—C39—H39B | 109.5 |
C18—C17—C16 | 120.1 (3) | C38—C39—H39C | 109.5 |
C18—C17—H17 | 119.9 | H39A—C39—H39C | 109.5 |
C16—C17—H17 | 119.9 | H39B—C39—H39C | 109.5 |
O22—C18—C17 | 125.4 (3) | C38—C40—H40A | 109.5 |
O22—C18—C19 | 114.4 (3) | C38—C40—H40B | 109.5 |
C17—C18—C19 | 120.2 (3) | H40A—C40—H40B | 109.5 |
O24—C19—C20 | 119.4 (3) | C38—C40—H40C | 109.5 |
O24—C19—C18 | 120.7 (3) | H40A—C40—H40C | 109.5 |
C20—C19—C18 | 119.8 (3) | H40B—C40—H40C | 109.5 |
O26—C20—C19 | 115.2 (3) | C43—C41—C42 | 109.0 (3) |
O26—C20—C21 | 125.1 (3) | C43—C41—Si1 | 116.2 (2) |
C19—C20—C21 | 119.8 (3) | C42—C41—Si1 | 113.4 (2) |
C16—C21—C20 | 120.5 (3) | C43—C41—H41 | 105.8 |
C16—C21—H21 | 119.7 | C42—C41—H41 | 105.8 |
C20—C21—H21 | 119.7 | Si1—C41—H41 | 105.8 |
O22—C23—H23A | 109.5 | C41—C42—H42A | 109.5 |
O22—C23—H23B | 109.5 | C41—C42—H42B | 109.5 |
H23A—C23—H23B | 109.5 | H42A—C42—H42B | 109.5 |
O22—C23—H23C | 109.5 | C41—C42—H42C | 109.5 |
H23A—C23—H23C | 109.5 | H42A—C42—H42C | 109.5 |
H23B—C23—H23C | 109.5 | H42B—C42—H42C | 109.5 |
O24—C25—H25A | 109.5 | C41—C43—H43A | 109.5 |
O24—C25—H25B | 109.5 | C41—C43—H43B | 109.5 |
H25A—C25—H25B | 109.5 | H43A—C43—H43B | 109.5 |
O24—C25—H25C | 109.5 | C41—C43—H43C | 109.5 |
H25A—C25—H25C | 109.5 | H43A—C43—H43C | 109.5 |
H25B—C25—H25C | 109.5 | H43B—C43—H43C | 109.5 |
O26—C27—H27A | 109.5 | C46—C44—C45 | 112.5 (3) |
O26—C27—H27B | 109.5 | C46—C44—Si1 | 114.2 (3) |
H27A—C27—H27B | 109.5 | C45—C44—Si1 | 116.4 (3) |
O26—C27—H27C | 109.5 | C46—C44—H44 | 104.0 |
H27A—C27—H27C | 109.5 | C45—C44—H44 | 104.0 |
H27B—C27—H27C | 109.5 | Si1—C44—H44 | 104.0 |
C30—C29—C31 | 110.1 (3) | C44—C45—H45A | 109.5 |
C30—C29—Si2 | 115.1 (2) | C44—C45—H45B | 109.5 |
C31—C29—Si2 | 112.6 (2) | H45A—C45—H45B | 109.5 |
C30—C29—H29 | 106.1 | C44—C45—H45C | 109.5 |
C31—C29—H29 | 106.1 | H45A—C45—H45C | 109.5 |
Si2—C29—H29 | 106.1 | H45B—C45—H45C | 109.5 |
C29—C30—H30A | 109.5 | C44—C46—H46A | 109.5 |
C29—C30—H30B | 109.5 | C44—C46—H46B | 109.5 |
H30A—C30—H30B | 109.5 | H46A—C46—H46B | 109.5 |
C29—C30—H30C | 109.5 | C44—C46—H46C | 109.5 |
H30A—C30—H30C | 109.5 | H46A—C46—H46C | 109.5 |
H30B—C30—H30C | 109.5 | H46B—C46—H46C | 109.5 |
C29—C31—H31A | 109.5 | | |
| | | |
C35—Si2—O28—C10 | 23.2 (3) | C27—O26—C20—C19 | 178.7 (4) |
C32A—Si2—O28—C10 | 131.1 (4) | C27—O26—C20—C21 | −1.2 (5) |
C29—Si2—O28—C10 | −98.0 (3) | O24—C19—C20—O26 | −6.4 (5) |
C32B—Si2—O28—C10 | 153.9 (3) | C18—C19—C20—O26 | 177.8 (3) |
C44—Si1—N1—C9 | 139.1 (2) | O24—C19—C20—C21 | 173.6 (3) |
C41—Si1—N1—C9 | 16.2 (3) | C18—C19—C20—C21 | −2.3 (5) |
C38—Si1—N1—C9 | −99.4 (2) | C17—C16—C21—C20 | 0.9 (4) |
C44—Si1—N1—C2 | −52.2 (3) | C15—C16—C21—C20 | −175.1 (3) |
C41—Si1—N1—C2 | −175.1 (2) | O26—C20—C21—C16 | −179.2 (3) |
C38—Si1—N1—C2 | 69.2 (3) | C19—C20—C21—C16 | 0.9 (5) |
C9—N1—C2—C3 | −178.2 (3) | O28—Si2—C29—C30 | 174.8 (2) |
Si1—N1—C2—C3 | 11.6 (5) | C35—Si2—C29—C30 | 52.3 (3) |
C9—N1—C2—C7 | 0.2 (3) | C32A—Si2—C29—C30 | −65.2 (4) |
Si1—N1—C2—C7 | −170.04 (19) | C32B—Si2—C29—C30 | −75.8 (3) |
N1—C2—C3—C4 | 178.1 (3) | O28—Si2—C29—C31 | −57.8 (3) |
C7—C2—C3—C4 | −0.1 (4) | C35—Si2—C29—C31 | 179.6 (2) |
C2—C3—C4—C5 | 0.7 (5) | C32A—Si2—C29—C31 | 62.2 (4) |
C3—C4—C5—C6 | −0.2 (5) | C32B—Si2—C29—C31 | 51.5 (3) |
C4—C5—C6—C7 | −0.8 (5) | O28—Si2—C32A—C33A | 45.4 (7) |
C5—C6—C7—C2 | 1.4 (4) | C35—Si2—C32A—C33A | 161.5 (6) |
C5—C6—C7—C8 | −177.6 (3) | C29—Si2—C32A—C33A | −76.5 (7) |
C3—C2—C7—C6 | −0.9 (4) | C32B—Si2—C32A—C33A | −47.8 (8) |
N1—C2—C7—C6 | −179.5 (2) | O28—Si2—C32A—C34A | 153.1 (6) |
C3—C2—C7—C8 | 178.3 (3) | C35—Si2—C32A—C34A | −90.7 (6) |
N1—C2—C7—C8 | −0.2 (3) | C29—Si2—C32A—C34A | 31.2 (7) |
C6—C7—C8—C9 | 179.3 (3) | C32B—Si2—C32A—C34A | 60.0 (9) |
C2—C7—C8—C9 | 0.2 (3) | O28—Si2—C32B—C33B | −35.0 (6) |
C6—C7—C8—C10 | 0.0 (5) | C35—Si2—C32B—C33B | 91.0 (6) |
C2—C7—C8—C10 | −179.1 (3) | C32A—Si2—C32B—C33B | 57.4 (8) |
C7—C8—C9—N1 | 0.0 (3) | C29—Si2—C32B—C33B | −147.3 (6) |
C10—C8—C9—N1 | 179.3 (2) | O28—Si2—C32B—C34B | −149.7 (5) |
C2—N1—C9—C8 | −0.1 (3) | C35—Si2—C32B—C34B | −23.7 (6) |
Si1—N1—C9—C8 | 170.96 (19) | C32A—Si2—C32B—C34B | −57.3 (8) |
Si2—O28—C10—C11 | −114.3 (3) | C29—Si2—C32B—C34B | 98.0 (6) |
Si2—O28—C10—C8 | 71.3 (3) | O28—Si2—C35—C36 | −70.8 (3) |
C9—C8—C10—C11 | −150.6 (3) | C32A—Si2—C35—C36 | 179.4 (3) |
C7—C8—C10—C11 | 28.6 (5) | C29—Si2—C35—C36 | 49.3 (3) |
C9—C8—C10—O28 | 23.6 (4) | C32B—Si2—C35—C36 | 167.1 (3) |
C7—C8—C10—O28 | −157.3 (3) | O28—Si2—C35—C37 | 58.3 (3) |
O28—C10—C11—N12 | 4.7 (4) | C32A—Si2—C35—C37 | −51.6 (4) |
C8—C10—C11—N12 | 178.8 (3) | C29—Si2—C35—C37 | 178.3 (3) |
C13—N12—C11—C10 | 175.5 (3) | C32B—Si2—C35—C37 | −63.9 (4) |
C11—N12—C13—O14 | 0.3 (5) | N1—Si1—C38—C40 | −66.7 (3) |
C11—N12—C13—C15 | 177.1 (3) | C44—Si1—C38—C40 | 53.6 (3) |
O14—C13—C15—C16 | −148.2 (3) | C41—Si1—C38—C40 | 179.8 (3) |
N12—C13—C15—C16 | 34.9 (4) | N1—Si1—C38—C39 | 61.1 (3) |
C13—C15—C16—C21 | −124.5 (3) | C44—Si1—C38—C39 | −178.6 (3) |
C13—C15—C16—C17 | 59.5 (4) | C41—Si1—C38—C39 | −52.4 (3) |
C21—C16—C17—C18 | −1.3 (4) | N1—Si1—C41—C43 | 64.6 (3) |
C15—C16—C17—C18 | 174.7 (3) | C44—Si1—C41—C43 | −55.6 (3) |
C23—O22—C18—C17 | 10.0 (5) | C38—Si1—C41—C43 | 179.7 (2) |
C23—O22—C18—C19 | −169.5 (3) | N1—Si1—C41—C42 | −167.8 (3) |
C16—C17—C18—O22 | −179.4 (3) | C44—Si1—C41—C42 | 72.0 (3) |
C16—C17—C18—C19 | 0.0 (5) | C38—Si1—C41—C42 | −52.8 (3) |
C25—O24—C19—C20 | 97.3 (4) | N1—Si1—C44—C46 | 171.7 (3) |
C25—O24—C19—C18 | −86.8 (4) | C41—Si1—C44—C46 | −70.6 (4) |
O22—C18—C19—O24 | 5.5 (5) | C38—Si1—C44—C46 | 52.6 (4) |
C17—C18—C19—O24 | −174.0 (3) | N1—Si1—C44—C45 | −54.7 (3) |
O22—C18—C19—C20 | −178.7 (3) | C41—Si1—C44—C45 | 63.0 (3) |
C17—C18—C19—C20 | 1.8 (5) | C38—Si1—C44—C45 | −173.8 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C17—H17···O14i | 0.93 | 2.55 | 3.479 (4) | 174 |
Symmetry code: (i) −x+1, −y, −z+1. |