research papers
The synthesis, growth from solutions and structure of crystals of a new linear thiophene–phenylene co-oligomer with a central benzothiadiazole fragment with a conjugated core, (TMS-2T-Ph)2-BTD, are presented. Single-crystal samples in the form of needles with a length of up to 7 mm were grown and their crystal structure was determined at 85 K and 293 K using single-crystal X-ray diffraction. The conformational differences between the crystal structures are insignificant. The parameters of melting and liquid crystalline phase transitions of (TMS-2T-Ph)2-BTD were established using differential scanning calorimetry and the thermal stability of the crystals was investigated using thermogravimetric analysis. The optical absorption and photoluminescence spectra of the solutions and crystals of (TMS-2T-Ph)2-BTD were obtained, and the kinetics of their photodegradation under the action of UV radiation were studied.
Keywords: linear π-conjugated co-oligomer; crystal growth; crystal structure; X-ray diffraction; spectroscopy; functional materials.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619012484/aw5029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520619012484/aw5029293Ksup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520619012484/aw502985Ksup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619012484/aw5029sup4.pdf |
CCDC references: 1868193; 1912459
Computing details top
(293K) top
Crystal data top
C40H36N2S5Si2 | Z = 2 |
Mr = 761.2 | F(000) = 796 |
Triclinic, P1 | Dx = 1.323 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0612 (5) Å | Cell parameters from 8747 reflections |
b = 14.6933 (6) Å | θ = 4.4–31.8° |
c = 14.3275 (9) Å | µ = 0.40 mm−1 |
α = 72.2555 (5)° | T = 293 K |
β = 71.6334 (5)° | Plate, yellow-green |
γ = 87.9619 (4)° | 0.28 × 0.19 × 0.03 mm |
V = 1910.25 (2) Å3 |
Data collection top
Oxford Diffraction CCD diffractometer | 16766 independent reflections |
Radiation source: X-ray tube | 3596 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.076 |
Detector resolution: 16.0628 pixels mm-1 | θmax = 38.5°, θmin = 4.2° |
ω scans | h = −15→17 |
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −25→25 |
Tmin = 0.993, Tmax = 0.999 | l = −15→23 |
38156 measured reflections |
Refinement top
Refinement on F | 0 constraints |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
S = 1.26 | (Δ/σ)max = 0.050 |
16766 reflections | Δρmax = 1.56 e Å−3 |
554 parameters | Δρmin = −1.02 e Å−3 |
0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.50322 (10) | 0.35593 (7) | 0.15204 (6) | 0.0557 (4) | |
S2 | 0.27979 (10) | 0.21663 (7) | −0.33196 (6) | 0.0544 (4) | |
S3 | 0.28380 (9) | 0.72049 (7) | 0.55406 (6) | 0.0535 (4) | |
S4 | 0.25218 (10) | 0.17871 (7) | −0.61085 (6) | 0.0564 (4) | |
S5 | 0.13200 (11) | 0.76829 (8) | 0.85561 (7) | 0.0681 (5) | |
Si1 | 0.21849 (13) | 0.01314 (10) | −0.69922 (8) | 0.0797 (6) | |
Si2 | 0.23585 (12) | 0.87122 (9) | 0.98758 (8) | 0.0699 (6) | |
N1 | 0.4338 (3) | 0.36610 (19) | 0.06298 (18) | 0.0492 (13) | |
N2 | 0.4142 (3) | 0.42724 (18) | 0.20986 (18) | 0.0462 (12) | |
C1 | 0.1419 (4) | 0.5584 (3) | 0.1214 (3) | 0.0540 (18) | |
C2 | 0.3254 (4) | 0.3898 (3) | −0.4435 (3) | 0.0504 (17) | |
C3 | 0.1539 (4) | 0.5230 (3) | 0.0376 (3) | 0.0555 (18) | |
C4 | 0.3371 (12) | −0.0827 (7) | −0.7210 (7) | 0.165 (6) | |
C5 | 0.3611 (9) | 0.8021 (7) | 1.0502 (6) | 0.113 (4) | |
C6 | 0.2086 (3) | 0.5693 (2) | 0.2708 (2) | 0.0429 (15) | |
C7 | 0.3094 (5) | 0.0150 (3) | −0.5257 (3) | 0.073 (2) | |
C8 | 0.2864 (4) | 0.3334 (3) | −0.0770 (3) | 0.0533 (17) | |
C9 | 0.2440 (4) | 0.4883 (3) | −0.1680 (3) | 0.0498 (17) | |
C10 | 0.3307 (4) | 0.3362 (3) | −0.5105 (3) | 0.0501 (17) | |
C11 | 0.1730 (3) | 0.6387 (2) | 0.4399 (2) | 0.0433 (15) | |
C12 | 0.0781 (4) | 0.5865 (3) | 0.3295 (3) | 0.0580 (19) | |
C13 | 0.2571 (4) | 0.4590 (3) | −0.2534 (3) | 0.0508 (17) | |
C14 | 0.2431 (9) | 0.1163 (6) | −0.8189 (5) | 0.138 (4) | |
C15 | 0.2238 (3) | 0.5317 (2) | 0.1835 (2) | 0.0436 (14) | |
C16 | 0.3289 (4) | 0.0710 (3) | −0.4666 (3) | 0.063 (2) | |
C17 | 0.3228 (4) | 0.5904 (2) | 0.2969 (3) | 0.0471 (16) | |
C18 | 0.2988 (4) | 0.3038 (3) | −0.1624 (3) | 0.0512 (17) | |
C19 | 0.0605 (4) | 0.6203 (3) | 0.4118 (3) | 0.0584 (19) | |
C20 | 0.2585 (3) | 0.4259 (2) | −0.0783 (2) | 0.0422 (15) | |
C21 | 0.0320 (5) | 0.6586 (3) | 0.6126 (3) | 0.059 (2) | |
C22 | 0.0440 (4) | 0.6928 (3) | 0.6914 (3) | 0.0618 (19) | |
C23 | 0.3045 (4) | 0.6249 (2) | 0.3798 (2) | 0.0455 (16) | |
C24 | 0.1497 (3) | 0.6681 (2) | 0.5329 (2) | 0.0463 (15) | |
C25 | 0.2460 (3) | 0.4590 (2) | 0.0115 (2) | 0.0440 (15) | |
C26 | 0.0551 (9) | 0.8408 (7) | 1.0749 (7) | 0.157 (6) | |
C27 | 0.1757 (3) | 0.7298 (2) | 0.6709 (2) | 0.0439 (15) | |
C28 | 0.0307 (12) | −0.0292 (13) | −0.6441 (9) | 0.270 (11) | |
C29 | 0.2833 (13) | 1.0015 (6) | 0.9432 (7) | 0.156 (6) | |
C30 | 0.2851 (3) | 0.3661 (2) | −0.2521 (2) | 0.0407 (14) | |
C31 | 0.2270 (4) | 0.7747 (2) | 0.7308 (2) | 0.0471 (15) | |
C32 | 0.3492 (4) | 0.8278 (3) | 0.7007 (3) | 0.0530 (17) | |
C33 | 0.3026 (3) | 0.1625 (3) | −0.5032 (2) | 0.0445 (15) | |
C34 | 0.2998 (3) | 0.3359 (2) | −0.3437 (2) | 0.0404 (14) | |
C35 | 0.3615 (5) | 0.8632 (3) | 0.7787 (3) | 0.0599 (19) | |
C36 | 0.3228 (3) | 0.4642 (2) | 0.1592 (2) | 0.0374 (13) | |
C37 | 0.3086 (3) | 0.2412 (3) | −0.4629 (2) | 0.0415 (14) | |
C38 | 0.3338 (3) | 0.4280 (2) | 0.0750 (2) | 0.0399 (13) | |
C39 | 0.2665 (4) | 0.0615 (2) | −0.6071 (2) | 0.0543 (16) | |
C40 | 0.2544 (4) | 0.8380 (2) | 0.8686 (3) | 0.0552 (17) | |
H29_1 | 0.216 (7) | 1.030 (5) | 0.920 (5) | 0.18 (4)* | |
H29_3 | 0.274 (5) | 1.015 (4) | 0.978 (3) | 0.075 (17)* | |
H5_1 | 0.336 (6) | 0.789 (5) | 1.100 (4) | 0.14 (3)* | |
H5_2 | 0.427 (5) | 0.846 (3) | 1.012 (3) | 0.10 (2)* | |
H26_1 | 0.054 (5) | 0.853 (4) | 1.119 (3) | 0.095 (18)* | |
H26_2 | 0.018 (5) | 0.798 (3) | 1.084 (3) | 0.073 (17)* | |
H14_1 | 0.227 (5) | 0.107 (3) | −0.847 (3) | 0.062 (15)* | |
H28_1 | 0.067 (4) | −0.085 (3) | −0.602 (3) | 0.045 (11)* | |
H28_2 | 0.007 (7) | −0.026 (5) | −0.675 (5) | 0.13 (3)* | |
H4_2 | 0.362 (5) | −0.090 (4) | −0.751 (4) | 0.071 (17)* | |
H7 | 0.324 (3) | −0.042 (2) | −0.510 (2) | 0.042 (10)* | |
H16 | 0.358 (3) | 0.049 (2) | −0.414 (2) | 0.041 (9)* | |
H10 | 0.349 (3) | 0.3614 (19) | −0.576 (2) | 0.035 (8)* | |
H2 | 0.349 (3) | 0.4524 (19) | −0.4652 (18) | 0.024 (8)* | |
H13 | 0.246 (3) | 0.501 (2) | −0.310 (2) | 0.048 (9)* | |
H9 | 0.223 (3) | 0.551 (2) | −0.1714 (18) | 0.031 (8)* | |
H8 | 0.300 (3) | 0.288 (2) | −0.017 (2) | 0.054 (9)* | |
H18 | 0.319 (2) | 0.2414 (19) | −0.1593 (18) | 0.027 (8)* | |
H3 | 0.096 (3) | 0.548 (2) | 0.002 (2) | 0.043 (9)* | |
H1 | 0.079 (3) | 0.6022 (19) | 0.1333 (18) | 0.028 (8)* | |
H17 | 0.412 (3) | 0.5838 (19) | 0.2586 (19) | 0.034 (8)* | |
H12 | 0.002 (3) | 0.576 (2) | 0.314 (2) | 0.045 (9)* | |
H23 | 0.387 (3) | 0.6401 (18) | 0.3899 (18) | 0.029 (7)* | |
H19 | −0.026 (3) | 0.6257 (19) | 0.4500 (19) | 0.029 (8)* | |
H21 | −0.049 (3) | 0.633 (2) | 0.617 (2) | 0.058 (11)* | |
H22 | −0.040 (4) | 0.692 (3) | 0.757 (3) | 0.090 (12)* | |
H32 | 0.420 (3) | 0.842 (2) | 0.631 (2) | 0.060 (10)* | |
H35 | 0.437 (4) | 0.903 (3) | 0.768 (3) | 0.082 (13)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0663 (6) | 0.0569 (6) | 0.0522 (5) | 0.0162 (5) | −0.0280 (5) | −0.0205 (5) |
S2 | 0.0798 (7) | 0.0467 (6) | 0.0371 (5) | −0.0006 (5) | −0.0179 (5) | −0.0140 (4) |
S3 | 0.0562 (6) | 0.0603 (7) | 0.0502 (5) | −0.0010 (5) | −0.0177 (5) | −0.0246 (5) |
S4 | 0.0733 (7) | 0.0569 (6) | 0.0456 (5) | 0.0061 (5) | −0.0238 (5) | −0.0203 (5) |
S5 | 0.0730 (7) | 0.0784 (8) | 0.0570 (6) | −0.0038 (6) | −0.0135 (5) | −0.0335 (6) |
Si1 | 0.0928 (9) | 0.0914 (10) | 0.0581 (7) | −0.0227 (7) | −0.0103 (6) | −0.0389 (7) |
Si2 | 0.0862 (9) | 0.0740 (9) | 0.0631 (7) | 0.0127 (7) | −0.0218 (6) | −0.0431 (6) |
N1 | 0.0629 (19) | 0.0455 (18) | 0.0451 (16) | 0.0087 (15) | −0.0219 (15) | −0.0181 (14) |
N2 | 0.0557 (17) | 0.0451 (18) | 0.0407 (15) | 0.0081 (14) | −0.0204 (14) | −0.0126 (13) |
C1 | 0.055 (2) | 0.057 (3) | 0.066 (2) | 0.019 (2) | −0.027 (2) | −0.038 (2) |
C2 | 0.060 (2) | 0.037 (2) | 0.050 (2) | −0.0038 (19) | −0.0215 (18) | −0.0046 (19) |
C3 | 0.060 (2) | 0.067 (3) | 0.058 (2) | 0.011 (2) | −0.036 (2) | −0.029 (2) |
C4 | 0.307 (12) | 0.104 (5) | 0.124 (6) | 0.058 (5) | −0.071 (6) | −0.092 (5) |
C5 | 0.127 (6) | 0.155 (7) | 0.077 (5) | 0.023 (5) | −0.051 (5) | −0.048 (5) |
C6 | 0.043 (2) | 0.043 (2) | 0.0471 (19) | 0.0001 (16) | −0.0172 (17) | −0.0165 (16) |
C7 | 0.108 (4) | 0.045 (3) | 0.070 (3) | 0.017 (3) | −0.030 (3) | −0.023 (2) |
C8 | 0.077 (3) | 0.046 (2) | 0.040 (2) | 0.001 (2) | −0.0255 (19) | −0.0088 (18) |
C9 | 0.067 (2) | 0.039 (2) | 0.062 (2) | 0.0145 (19) | −0.037 (2) | −0.025 (2) |
C10 | 0.065 (2) | 0.058 (3) | 0.0289 (19) | 0.004 (2) | −0.0169 (18) | −0.0128 (19) |
C11 | 0.050 (2) | 0.036 (2) | 0.053 (2) | 0.0066 (16) | −0.0228 (18) | −0.0193 (16) |
C12 | 0.051 (3) | 0.075 (3) | 0.069 (3) | 0.007 (2) | −0.031 (2) | −0.039 (2) |
C13 | 0.062 (2) | 0.052 (3) | 0.046 (2) | 0.0070 (19) | −0.0343 (19) | −0.0103 (19) |
C14 | 0.244 (8) | 0.127 (6) | 0.083 (4) | 0.010 (5) | −0.103 (5) | −0.034 (4) |
C15 | 0.046 (2) | 0.048 (2) | 0.0424 (18) | −0.0018 (17) | −0.0154 (17) | −0.0199 (16) |
C16 | 0.094 (3) | 0.058 (3) | 0.049 (2) | 0.017 (2) | −0.035 (2) | −0.022 (2) |
C17 | 0.042 (2) | 0.049 (2) | 0.048 (2) | −0.0007 (18) | −0.0108 (19) | −0.0158 (17) |
C18 | 0.078 (3) | 0.034 (2) | 0.048 (2) | 0.0071 (19) | −0.0257 (19) | −0.0150 (18) |
C19 | 0.042 (2) | 0.078 (3) | 0.066 (3) | 0.013 (2) | −0.014 (2) | −0.041 (2) |
C20 | 0.050 (2) | 0.040 (2) | 0.0435 (19) | 0.0022 (16) | −0.0224 (16) | −0.0154 (16) |
C21 | 0.061 (3) | 0.067 (3) | 0.059 (2) | 0.007 (2) | −0.019 (2) | −0.032 (2) |
C22 | 0.059 (3) | 0.067 (3) | 0.064 (3) | 0.006 (2) | −0.015 (2) | −0.031 (2) |
C23 | 0.049 (2) | 0.043 (2) | 0.053 (2) | −0.0022 (17) | −0.0259 (19) | −0.0163 (17) |
C24 | 0.051 (2) | 0.047 (2) | 0.050 (2) | 0.0052 (17) | −0.0225 (19) | −0.0205 (17) |
C25 | 0.050 (2) | 0.042 (2) | 0.0451 (19) | −0.0028 (17) | −0.0191 (17) | −0.0166 (16) |
C26 | 0.115 (6) | 0.213 (10) | 0.151 (7) | −0.027 (6) | 0.018 (5) | −0.128 (8) |
C27 | 0.055 (2) | 0.040 (2) | 0.0426 (18) | 0.0122 (17) | −0.0185 (17) | −0.0194 (16) |
C28 | 0.174 (10) | 0.48 (2) | 0.167 (11) | −0.176 (12) | −0.004 (7) | −0.152 (13) |
C29 | 0.290 (13) | 0.078 (5) | 0.126 (7) | 0.018 (6) | −0.064 (7) | −0.069 (5) |
C30 | 0.0426 (19) | 0.041 (2) | 0.0434 (19) | 0.0018 (16) | −0.0181 (16) | −0.0153 (16) |
C31 | 0.062 (2) | 0.043 (2) | 0.0429 (19) | 0.0141 (18) | −0.0229 (18) | −0.0175 (16) |
C32 | 0.061 (3) | 0.061 (3) | 0.041 (2) | 0.008 (2) | −0.019 (2) | −0.0198 (19) |
C33 | 0.046 (2) | 0.054 (2) | 0.0350 (17) | 0.0084 (17) | −0.0087 (15) | −0.0207 (17) |
C34 | 0.0392 (19) | 0.042 (2) | 0.0441 (19) | 0.0048 (15) | −0.0188 (16) | −0.0140 (16) |
C35 | 0.072 (3) | 0.060 (3) | 0.054 (2) | 0.003 (2) | −0.023 (2) | −0.023 (2) |
C36 | 0.0404 (19) | 0.0327 (19) | 0.0357 (17) | −0.0051 (15) | −0.0085 (15) | −0.0087 (14) |
C37 | 0.0402 (19) | 0.053 (2) | 0.0319 (16) | 0.0074 (17) | −0.0096 (15) | −0.0166 (17) |
C38 | 0.050 (2) | 0.0312 (19) | 0.0348 (17) | −0.0053 (16) | −0.0108 (16) | −0.0077 (14) |
C39 | 0.068 (2) | 0.052 (2) | 0.0408 (19) | −0.0007 (19) | −0.0104 (18) | −0.0175 (18) |
C40 | 0.069 (3) | 0.053 (2) | 0.056 (2) | 0.008 (2) | −0.025 (2) | −0.0290 (19) |
Geometric parameters (Å, º) top
S1—N1 | 1.605 (3) | C9—H9 | 0.92 (3) |
S1—N2 | 1.606 (3) | C10—C37 | 1.346 (5) |
S2—C34 | 1.722 (4) | C10—H10 | 0.85 (3) |
S2—C37 | 1.728 (3) | C11—C19 | 1.376 (6) |
S3—C24 | 1.726 (4) | C11—C23 | 1.380 (5) |
S3—C27 | 1.728 (3) | C11—C24 | 1.471 (5) |
S4—C33 | 1.719 (4) | C12—C19 | 1.373 (6) |
S4—C39 | 1.709 (4) | C12—H12 | 0.90 (3) |
S5—C31 | 1.717 (3) | C13—C30 | 1.379 (5) |
S5—C40 | 1.718 (4) | C13—H13 | 0.89 (3) |
Si1—C4 | 1.848 (10) | C14—H14_1 | 0.52 (5) |
Si1—C14 | 1.864 (6) | C15—C36 | 1.421 (5) |
Si1—C28 | 1.851 (12) | C16—C33 | 1.336 (5) |
Si1—C39 | 1.865 (4) | C16—H16 | 0.87 (3) |
Si2—C5 | 1.868 (10) | C17—C23 | 1.387 (6) |
Si2—C26 | 1.832 (8) | C17—H17 | 0.91 (3) |
Si2—C29 | 1.851 (9) | C18—C30 | 1.377 (5) |
Si2—C40 | 1.866 (4) | C18—H18 | 0.92 (3) |
N1—C38 | 1.339 (4) | C19—H19 | 0.89 (2) |
N2—C36 | 1.346 (4) | C20—C25 | 1.477 (5) |
C1—C3 | 1.419 (6) | C21—C22 | 1.406 (7) |
C1—C15 | 1.360 (6) | C21—C24 | 1.337 (5) |
C1—H1 | 0.90 (3) | C21—H21 | 0.89 (4) |
C2—C10 | 1.403 (6) | C22—C27 | 1.358 (6) |
C2—C34 | 1.353 (4) | C22—H22 | 1.05 (3) |
C2—H2 | 0.89 (3) | C23—H23 | 0.93 (3) |
C3—C25 | 1.348 (5) | C25—C38 | 1.429 (5) |
C3—H3 | 0.89 (3) | C26—H26_1 | 0.70 (6) |
C4—H4_2 | 0.46 (6) | C26—H26_2 | 0.70 (5) |
C5—H5_1 | 0.65 (5) | C27—C31 | 1.445 (6) |
C5—H5_2 | 0.86 (4) | C28—H28_1 | 0.99 (4) |
C6—C12 | 1.381 (5) | C28—H28_2 | 0.56 (8) |
C6—C15 | 1.479 (5) | C29—H29_1 | 0.89 (8) |
C6—C17 | 1.386 (6) | C29—H29_3 | 0.57 (6) |
C7—C16 | 1.404 (8) | C30—C34 | 1.473 (5) |
C7—C39 | 1.351 (6) | C31—C32 | 1.354 (5) |
C7—H7 | 0.82 (3) | C32—C35 | 1.407 (7) |
C8—C18 | 1.388 (6) | C32—H32 | 0.99 (3) |
C8—C20 | 1.374 (5) | C33—C37 | 1.453 (6) |
C8—H8 | 0.95 (3) | C35—C40 | 1.349 (5) |
C9—C13 | 1.385 (6) | C35—H35 | 0.92 (4) |
C9—C20 | 1.380 (5) | C36—C38 | 1.433 (5) |
N1—S1—N2 | 101.14 (15) | C30—C18—H18 | 119.5 (17) |
C34—S2—C37 | 92.48 (17) | C11—C19—C12 | 121.4 (3) |
C24—S3—C27 | 92.58 (17) | C11—C19—H19 | 120 (2) |
C33—S4—C39 | 93.92 (19) | C12—C19—H19 | 118 (2) |
C31—S5—C40 | 94.09 (18) | C8—C20—C9 | 117.4 (4) |
C4—Si1—C14 | 112.7 (4) | C8—C20—C25 | 122.1 (3) |
C4—Si1—C28 | 113.3 (7) | C9—C20—C25 | 120.5 (3) |
C4—Si1—C39 | 107.1 (4) | C22—C21—C24 | 115.2 (4) |
C14—Si1—C28 | 108.6 (5) | C22—C21—H21 | 121 (2) |
C14—Si1—C39 | 105.9 (3) | C24—C21—H21 | 124 (2) |
C28—Si1—C39 | 108.8 (5) | C21—C22—C27 | 112.5 (3) |
C5—Si2—C26 | 110.5 (4) | C21—C22—H22 | 124 (2) |
C5—Si2—C29 | 111.0 (5) | C27—C22—H22 | 124 (3) |
C5—Si2—C40 | 107.6 (3) | C11—C23—C17 | 121.7 (4) |
C26—Si2—C29 | 112.2 (5) | C11—C23—H23 | 122.9 (16) |
C26—Si2—C40 | 109.3 (4) | C17—C23—H23 | 115.4 (16) |
C29—Si2—C40 | 106.0 (4) | S3—C24—C11 | 121.6 (2) |
S1—N1—C38 | 106.5 (2) | S3—C24—C21 | 109.5 (3) |
S1—N2—C36 | 106.4 (2) | C11—C24—C21 | 128.8 (4) |
C3—C1—C15 | 123.2 (4) | C3—C25—C20 | 122.5 (3) |
C3—C1—H1 | 119 (2) | C3—C25—C38 | 115.0 (4) |
C15—C1—H1 | 118 (2) | C20—C25—C38 | 122.5 (3) |
C10—C2—C34 | 113.9 (3) | Si2—C26—H26_1 | 105 (4) |
C10—C2—H2 | 123.5 (17) | Si2—C26—H26_2 | 122 (4) |
C34—C2—H2 | 122.1 (18) | H26_1—C26—H26_2 | 117 (5) |
C1—C3—C25 | 124.0 (4) | S3—C27—C22 | 110.1 (3) |
C1—C3—H3 | 114 (2) | S3—C27—C31 | 121.2 (2) |
C25—C3—H3 | 122 (2) | C22—C27—C31 | 128.7 (3) |
Si1—C4—H4_2 | 132 (7) | Si1—C28—H28_1 | 83 (2) |
Si2—C5—H5_1 | 112 (6) | Si1—C28—H28_2 | 112 (6) |
Si2—C5—H5_2 | 90 (3) | H28_1—C28—H28_2 | 131 (8) |
H5_1—C5—H5_2 | 126 (7) | Si2—C29—H29_1 | 106 (5) |
C12—C6—C15 | 120.8 (4) | Si2—C29—H29_3 | 110 (5) |
C12—C6—C17 | 116.8 (4) | H29_1—C29—H29_3 | 99 (7) |
C15—C6—C17 | 122.4 (3) | C13—C30—C18 | 117.3 (4) |
C16—C7—C39 | 115.7 (4) | C13—C30—C34 | 120.8 (3) |
C16—C7—H7 | 121 (3) | C18—C30—C34 | 121.9 (3) |
C39—C7—H7 | 124 (3) | S5—C31—C27 | 122.2 (2) |
C18—C8—C20 | 121.3 (3) | S5—C31—C32 | 109.9 (3) |
C18—C8—H8 | 118 (2) | C27—C31—C32 | 127.9 (3) |
C20—C8—H8 | 120 (2) | C31—C32—C35 | 112.1 (3) |
C13—C9—C20 | 121.3 (4) | C31—C32—H32 | 124 (2) |
C13—C9—H9 | 118.7 (17) | C35—C32—H32 | 124 (2) |
C20—C9—H9 | 119.9 (17) | S4—C33—C16 | 109.9 (3) |
C2—C10—C37 | 113.7 (3) | S4—C33—C37 | 121.1 (2) |
C2—C10—H10 | 123 (2) | C16—C33—C37 | 129.0 (4) |
C37—C10—H10 | 123 (2) | S2—C34—C2 | 109.9 (3) |
C19—C11—C23 | 117.1 (4) | S2—C34—C30 | 120.6 (2) |
C19—C11—C24 | 120.0 (3) | C2—C34—C30 | 129.5 (3) |
C23—C11—C24 | 122.9 (4) | C32—C35—C40 | 116.3 (4) |
C6—C12—C19 | 122.1 (4) | C32—C35—H35 | 122 (2) |
C6—C12—H12 | 119.3 (19) | C40—C35—H35 | 122 (2) |
C19—C12—H12 | 118.6 (19) | N2—C36—C15 | 125.7 (3) |
C9—C13—C30 | 121.2 (3) | N2—C36—C38 | 112.8 (3) |
C9—C13—H13 | 119 (2) | C15—C36—C38 | 121.6 (3) |
C30—C13—H13 | 120 (2) | S2—C37—C10 | 110.1 (3) |
Si1—C14—H14_1 | 112 (5) | S2—C37—C33 | 119.0 (2) |
C1—C15—C6 | 122.2 (3) | C10—C37—C33 | 130.9 (3) |
C1—C15—C36 | 115.1 (3) | N1—C38—C25 | 125.6 (3) |
C6—C15—C36 | 122.8 (3) | N1—C38—C36 | 113.2 (3) |
C7—C16—C33 | 112.7 (4) | C25—C38—C36 | 121.2 (3) |
C7—C16—H16 | 123 (2) | S4—C39—Si1 | 122.8 (2) |
C33—C16—H16 | 124 (2) | S4—C39—C7 | 107.9 (3) |
C6—C17—C23 | 120.9 (3) | Si1—C39—C7 | 129.3 (3) |
C6—C17—H17 | 121 (2) | S5—C40—Si2 | 124.43 (18) |
C23—C17—H17 | 118 (2) | S5—C40—C35 | 107.7 (3) |
C8—C18—C30 | 121.4 (4) | Si2—C40—C35 | 127.9 (4) |
C8—C18—H18 | 119.1 (17) |
(85K) top
Crystal data top
C40H36N2S5Si2 | Z = 2 |
Mr = 761.2 | F(000) = 796 |
Triclinic, P1 | Dx = 1.362 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.805 (1) Å | Cell parameters from 8747 reflections |
b = 14.4191 (7) Å | θ = 4.4–31.8° |
c = 14.4368 (9) Å | µ = 0.41 mm−1 |
α = 72.3867 (5)° | T = 85 K |
β = 72.9136 (5)° | Plate, yellow-green |
γ = 87.8897 (4)° | 0.28 × 0.19 × 0.03 mm |
V = 1856.48 (2) Å3 |
Data collection top
Oxford Diffraction CCD diffractometer | 16298 independent reflections |
Radiation source: X-ray tube | 6629 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.066 |
Detector resolution: 16.0628 pixels mm-1 | θmax = 38.6°, θmin = 4.2° |
ω scans | h = −16→14 |
Absorption correction: analytical CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −24→24 |
Tmin = 0.993, Tmax = 0.999 | l = −23→16 |
37121 measured reflections |
Refinement top
Refinement on F | 0 constraints |
R[F2 > 2σ(F2)] = 0.059 | All H-atom parameters refined |
wR(F2) = 0.064 | Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2) |
S = 1.24 | (Δ/σ)max = 0.047 |
16298 reflections | Δρmax = 0.99 e Å−3 |
586 parameters | Δρmin = −0.92 e Å−3 |
0 restraints |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.50691 (6) | 0.35355 (4) | 0.15741 (4) | 0.0192 (2) | |
S2 | 0.27897 (7) | 0.22008 (4) | −0.33038 (4) | 0.0194 (2) | |
S3 | 0.28643 (6) | 0.72749 (4) | 0.55582 (4) | 0.0185 (2) | |
S4 | 0.25049 (7) | 0.18857 (4) | −0.60991 (4) | 0.0205 (2) | |
S5 | 0.13795 (7) | 0.77177 (5) | 0.85600 (5) | 0.0228 (2) | |
Si1 | 0.20754 (8) | 0.02409 (6) | −0.70063 (5) | 0.0291 (3) | |
Si2 | 0.24777 (8) | 0.87582 (5) | 0.98767 (5) | 0.0254 (3) | |
N1 | 0.43506 (19) | 0.36528 (14) | 0.06856 (13) | 0.0178 (7) | |
N2 | 0.41662 (19) | 0.42649 (13) | 0.21485 (13) | 0.0174 (7) | |
C1 | 0.1365 (3) | 0.56406 (17) | 0.12558 (17) | 0.0179 (9) | |
C2 | 0.3272 (2) | 0.39861 (18) | −0.43769 (18) | 0.0179 (8) | |
C3 | 0.1462 (2) | 0.52921 (17) | 0.04225 (18) | 0.0177 (9) | |
C4 | 0.3046 (5) | −0.0853 (2) | −0.7140 (3) | 0.0476 (16) | |
C5 | 0.3620 (4) | 0.7967 (2) | 1.0571 (2) | 0.0333 (13) | |
C6 | 0.2075 (2) | 0.57251 (16) | 0.27474 (16) | 0.0165 (8) | |
C7 | 0.3152 (3) | 0.01844 (19) | −0.52970 (19) | 0.0246 (10) | |
C8 | 0.2823 (3) | 0.33375 (18) | −0.07249 (18) | 0.0196 (9) | |
C9 | 0.2348 (2) | 0.49361 (18) | −0.16180 (18) | 0.0176 (9) | |
C10 | 0.3346 (2) | 0.34586 (18) | −0.50654 (18) | 0.0176 (8) | |
C11 | 0.1731 (2) | 0.64074 (16) | 0.44328 (16) | 0.0162 (8) | |
C12 | 0.0726 (3) | 0.58918 (17) | 0.33239 (18) | 0.0197 (9) | |
C13 | 0.2490 (2) | 0.46560 (17) | −0.24714 (18) | 0.0170 (8) | |
C14 | 0.2442 (4) | 0.1243 (2) | −0.8228 (2) | 0.0328 (12) | |
C15 | 0.2216 (2) | 0.53524 (16) | 0.18750 (16) | 0.0151 (8) | |
C16 | 0.3386 (3) | 0.07439 (18) | −0.46965 (19) | 0.0223 (9) | |
C17 | 0.3256 (3) | 0.59385 (17) | 0.30127 (17) | 0.0173 (8) | |
C18 | 0.2952 (2) | 0.30455 (18) | −0.15762 (18) | 0.0191 (9) | |
C19 | 0.0556 (3) | 0.62248 (18) | 0.41492 (18) | 0.0202 (9) | |
C20 | 0.2524 (2) | 0.42906 (16) | −0.07288 (16) | 0.0157 (8) | |
C21 | 0.0316 (3) | 0.65478 (17) | 0.61705 (18) | 0.0196 (9) | |
C22 | 0.0458 (3) | 0.69055 (17) | 0.69455 (18) | 0.0199 (9) | |
C23 | 0.3088 (2) | 0.62821 (16) | 0.38310 (17) | 0.0169 (8) | |
C24 | 0.1510 (2) | 0.66968 (16) | 0.53613 (16) | 0.0156 (8) | |
C25 | 0.2411 (2) | 0.46250 (16) | 0.01644 (16) | 0.0165 (8) | |
C26 | 0.0576 (3) | 0.8588 (3) | 1.0662 (3) | 0.0397 (14) | |
C27 | 0.1775 (2) | 0.73317 (16) | 0.67297 (16) | 0.0171 (8) | |
C28 | 0.0101 (4) | −0.0042 (3) | −0.6510 (3) | 0.0506 (17) | |
C29 | 0.3130 (4) | 1.0052 (2) | 0.9491 (3) | 0.0400 (14) | |
C30 | 0.2807 (2) | 0.37058 (16) | −0.24698 (16) | 0.0148 (8) | |
C31 | 0.2317 (2) | 0.78096 (17) | 0.73124 (17) | 0.0181 (8) | |
C32 | 0.3532 (3) | 0.83888 (17) | 0.70120 (18) | 0.0190 (9) | |
C33 | 0.3077 (2) | 0.16928 (17) | −0.50396 (16) | 0.0180 (8) | |
C34 | 0.2974 (2) | 0.34137 (16) | −0.33854 (16) | 0.0150 (8) | |
C35 | 0.3688 (3) | 0.87585 (18) | 0.77790 (18) | 0.0206 (9) | |
C36 | 0.3229 (2) | 0.46545 (16) | 0.16394 (16) | 0.0153 (8) | |
C37 | 0.3116 (2) | 0.24777 (17) | −0.46052 (16) | 0.0158 (8) | |
C38 | 0.3323 (2) | 0.42961 (16) | 0.07975 (16) | 0.0165 (8) | |
C39 | 0.2672 (2) | 0.06923 (18) | −0.60932 (17) | 0.0219 (9) | |
C40 | 0.2622 (3) | 0.84624 (17) | 0.86785 (18) | 0.0207 (9) | |
H29_1 | 0.251 (3) | 1.053 (3) | 0.907 (2) | 0.073 (11)* | |
H29_2 | 0.417 (4) | 1.014 (2) | 0.910 (2) | 0.068 (11)* | |
H29_3 | 0.305 (3) | 1.023 (2) | 1.006 (2) | 0.061 (10)* | |
H5_1 | 0.345 (3) | 0.802 (2) | 1.116 (2) | 0.054 (10)* | |
H5_2 | 0.457 (3) | 0.818 (2) | 1.022 (2) | 0.035 (8)* | |
H5_3 | 0.342 (3) | 0.728 (3) | 1.067 (2) | 0.058 (10)* | |
H26_1 | 0.054 (3) | 0.8762 (19) | 1.128 (2) | 0.034 (8)* | |
H26_2 | 0.017 (3) | 0.796 (3) | 1.087 (2) | 0.061 (11)* | |
H26_3 | −0.002 (4) | 0.900 (3) | 1.027 (3) | 0.083 (13)* | |
H14_1 | 0.195 (3) | 0.1047 (19) | −0.8635 (19) | 0.035 (8)* | |
H14_2 | 0.344 (4) | 0.139 (2) | −0.856 (2) | 0.058 (10)* | |
H14_3 | 0.199 (4) | 0.182 (3) | −0.810 (2) | 0.081 (12)* | |
H28_1 | 0.021 (3) | −0.063 (2) | −0.600 (2) | 0.031 (8)* | |
H28_2 | −0.016 (3) | −0.023 (3) | −0.704 (2) | 0.070 (11)* | |
H28_3 | −0.058 (5) | 0.056 (4) | −0.638 (3) | 0.136 (19)* | |
H4_1 | 0.274 (3) | −0.109 (2) | −0.759 (2) | 0.060 (10)* | |
H4_2 | 0.412 (3) | −0.0802 (19) | −0.7348 (18) | 0.025 (8)* | |
H4_3 | 0.278 (4) | −0.144 (3) | −0.646 (3) | 0.106 (14)* | |
H7 | 0.324 (3) | −0.048 (2) | −0.5115 (18) | 0.029 (7)* | |
H16 | 0.364 (2) | 0.0535 (16) | −0.4170 (16) | 0.008 (6)* | |
H10 | 0.356 (2) | 0.3716 (16) | −0.5722 (16) | 0.008 (6)* | |
H2 | 0.342 (2) | 0.4620 (17) | −0.4542 (16) | 0.014 (6)* | |
H13 | 0.236 (2) | 0.5103 (18) | −0.3031 (17) | 0.019 (7)* | |
H9 | 0.217 (2) | 0.5561 (17) | −0.1666 (15) | 0.010 (6)* | |
H8 | 0.296 (2) | 0.2905 (17) | −0.0149 (16) | 0.016 (6)* | |
H18 | 0.319 (2) | 0.2397 (18) | −0.1538 (16) | 0.020 (6)* | |
H3 | 0.082 (2) | 0.5544 (16) | 0.0046 (15) | 0.009 (6)* | |
H1 | 0.070 (2) | 0.6099 (18) | 0.1364 (16) | 0.017 (6)* | |
H17 | 0.415 (2) | 0.5898 (17) | 0.2636 (17) | 0.022 (7)* | |
H12 | −0.007 (2) | 0.5796 (16) | 0.3137 (15) | 0.012 (6)* | |
H23 | 0.391 (2) | 0.6402 (14) | 0.3972 (14) | 0.002 (5)* | |
H19 | −0.035 (2) | 0.6329 (15) | 0.4509 (15) | 0.007 (6)* | |
H21 | −0.046 (2) | 0.6288 (17) | 0.6214 (16) | 0.015 (6)* | |
H22 | −0.028 (3) | 0.6850 (19) | 0.7589 (19) | 0.036 (8)* | |
H32 | 0.420 (2) | 0.8560 (16) | 0.6371 (16) | 0.011 (6)* | |
H35 | 0.448 (2) | 0.9154 (18) | 0.7681 (16) | 0.021 (6)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0226 (3) | 0.0164 (3) | 0.0206 (3) | 0.0063 (2) | −0.0083 (3) | −0.0075 (2) |
S2 | 0.0283 (3) | 0.0129 (3) | 0.0161 (3) | 0.0021 (2) | −0.0046 (3) | −0.0054 (2) |
S3 | 0.0205 (3) | 0.0169 (3) | 0.0198 (3) | 0.0006 (2) | −0.0059 (2) | −0.0080 (2) |
S4 | 0.0267 (3) | 0.0168 (3) | 0.0189 (3) | 0.0040 (2) | −0.0067 (3) | −0.0071 (2) |
S5 | 0.0268 (3) | 0.0202 (3) | 0.0222 (3) | 0.0008 (3) | −0.0044 (3) | −0.0104 (3) |
Si1 | 0.0393 (5) | 0.0255 (4) | 0.0219 (4) | −0.0068 (3) | −0.0030 (3) | −0.0110 (3) |
Si2 | 0.0312 (4) | 0.0213 (4) | 0.0264 (4) | 0.0027 (3) | −0.0052 (3) | −0.0144 (3) |
N1 | 0.0195 (10) | 0.0131 (9) | 0.0205 (10) | 0.0037 (8) | −0.0058 (8) | −0.0053 (8) |
N2 | 0.0199 (10) | 0.0132 (9) | 0.0191 (10) | 0.0018 (8) | −0.0059 (8) | −0.0051 (8) |
C1 | 0.0180 (12) | 0.0150 (11) | 0.0223 (13) | 0.0048 (9) | −0.0053 (10) | −0.0088 (10) |
C2 | 0.0154 (11) | 0.0135 (11) | 0.0240 (13) | 0.0017 (9) | −0.0047 (10) | −0.0057 (10) |
C3 | 0.0189 (12) | 0.0153 (11) | 0.0230 (13) | 0.0025 (9) | −0.0117 (10) | −0.0066 (10) |
C4 | 0.088 (3) | 0.0244 (17) | 0.0365 (19) | 0.0063 (18) | −0.021 (2) | −0.0159 (15) |
C5 | 0.045 (2) | 0.0356 (19) | 0.0241 (16) | 0.0012 (15) | −0.0119 (15) | −0.0136 (14) |
C6 | 0.0177 (12) | 0.0149 (11) | 0.0171 (11) | 0.0018 (9) | −0.0060 (10) | −0.0047 (9) |
C7 | 0.0333 (15) | 0.0150 (12) | 0.0237 (13) | 0.0056 (11) | −0.0041 (11) | −0.0084 (11) |
C8 | 0.0251 (13) | 0.0145 (12) | 0.0190 (13) | 0.0029 (10) | −0.0096 (11) | −0.0021 (10) |
C9 | 0.0204 (12) | 0.0117 (11) | 0.0263 (13) | 0.0059 (9) | −0.0123 (10) | −0.0090 (10) |
C10 | 0.0181 (12) | 0.0188 (12) | 0.0145 (12) | 0.0042 (9) | −0.0037 (10) | −0.0048 (10) |
C11 | 0.0226 (12) | 0.0106 (10) | 0.0168 (11) | 0.0026 (9) | −0.0077 (10) | −0.0048 (9) |
C12 | 0.0167 (12) | 0.0209 (13) | 0.0273 (14) | 0.0024 (10) | −0.0116 (11) | −0.0107 (10) |
C13 | 0.0180 (12) | 0.0165 (12) | 0.0181 (12) | 0.0030 (9) | −0.0105 (10) | −0.0029 (10) |
C14 | 0.0407 (19) | 0.0324 (18) | 0.0307 (16) | 0.0053 (15) | −0.0148 (15) | −0.0137 (13) |
C15 | 0.0148 (11) | 0.0126 (10) | 0.0183 (11) | −0.0009 (8) | −0.0037 (9) | −0.0063 (9) |
C16 | 0.0298 (14) | 0.0199 (13) | 0.0180 (13) | 0.0079 (11) | −0.0081 (11) | −0.0068 (10) |
C17 | 0.0165 (12) | 0.0135 (11) | 0.0183 (12) | 0.0000 (9) | −0.0023 (10) | −0.0024 (9) |
C18 | 0.0228 (13) | 0.0124 (11) | 0.0226 (13) | 0.0042 (10) | −0.0067 (10) | −0.0063 (10) |
C19 | 0.0173 (12) | 0.0212 (13) | 0.0259 (13) | 0.0071 (10) | −0.0072 (11) | −0.0123 (11) |
C20 | 0.0150 (11) | 0.0139 (11) | 0.0205 (12) | 0.0015 (9) | −0.0080 (9) | −0.0058 (9) |
C21 | 0.0185 (12) | 0.0163 (12) | 0.0279 (14) | 0.0038 (10) | −0.0105 (11) | −0.0091 (10) |
C22 | 0.0209 (12) | 0.0170 (12) | 0.0210 (13) | 0.0043 (10) | −0.0035 (11) | −0.0075 (10) |
C23 | 0.0172 (12) | 0.0128 (11) | 0.0220 (12) | 0.0000 (9) | −0.0092 (10) | −0.0038 (9) |
C24 | 0.0151 (11) | 0.0130 (11) | 0.0205 (12) | 0.0036 (9) | −0.0078 (10) | −0.0057 (9) |
C25 | 0.0203 (12) | 0.0124 (11) | 0.0169 (11) | −0.0004 (9) | −0.0061 (10) | −0.0040 (9) |
C26 | 0.0397 (18) | 0.036 (2) | 0.0421 (19) | −0.0002 (16) | 0.0001 (16) | −0.0211 (16) |
C27 | 0.0220 (12) | 0.0132 (11) | 0.0154 (11) | 0.0070 (9) | −0.0048 (10) | −0.0049 (9) |
C28 | 0.048 (2) | 0.065 (3) | 0.039 (2) | −0.016 (2) | −0.0119 (17) | −0.015 (2) |
C29 | 0.054 (2) | 0.0258 (16) | 0.045 (2) | −0.0041 (15) | −0.0093 (18) | −0.0224 (15) |
C30 | 0.0144 (11) | 0.0126 (11) | 0.0183 (12) | 0.0022 (8) | −0.0043 (9) | −0.0066 (9) |
C31 | 0.0235 (12) | 0.0135 (11) | 0.0190 (12) | 0.0088 (9) | −0.0087 (10) | −0.0063 (9) |
C32 | 0.0231 (13) | 0.0165 (12) | 0.0177 (12) | 0.0050 (10) | −0.0066 (11) | −0.0055 (10) |
C33 | 0.0188 (12) | 0.0174 (12) | 0.0163 (11) | 0.0045 (9) | −0.0019 (9) | −0.0067 (9) |
C34 | 0.0117 (10) | 0.0137 (11) | 0.0204 (12) | 0.0032 (8) | −0.0048 (9) | −0.0065 (9) |
C35 | 0.0229 (13) | 0.0166 (12) | 0.0255 (13) | 0.0031 (10) | −0.0107 (11) | −0.0078 (10) |
C36 | 0.0172 (11) | 0.0132 (11) | 0.0147 (11) | −0.0010 (9) | −0.0043 (9) | −0.0034 (9) |
C37 | 0.0144 (11) | 0.0180 (12) | 0.0157 (11) | 0.0045 (9) | −0.0045 (9) | −0.0064 (9) |
C38 | 0.0189 (11) | 0.0110 (10) | 0.0181 (12) | −0.0006 (9) | −0.0035 (10) | −0.0041 (9) |
C39 | 0.0241 (13) | 0.0183 (12) | 0.0218 (13) | 0.0022 (10) | −0.0015 (10) | −0.0092 (10) |
C40 | 0.0252 (13) | 0.0139 (11) | 0.0275 (13) | 0.0054 (10) | −0.0100 (11) | −0.0110 (10) |
Geometric parameters (Å, º) top
S1—N1 | 1.600 (2) | C10—C37 | 1.364 (3) |
S1—N2 | 1.614 (2) | C10—H10 | 0.87 (2) |
S2—C34 | 1.729 (2) | C11—C19 | 1.389 (4) |
S2—C37 | 1.730 (2) | C11—C23 | 1.398 (3) |
S3—C24 | 1.728 (3) | C11—C24 | 1.476 (4) |
S3—C27 | 1.739 (2) | C12—C19 | 1.379 (4) |
S4—C33 | 1.723 (3) | C12—H12 | 0.93 (3) |
S4—C39 | 1.720 (3) | C13—C30 | 1.393 (3) |
S5—C31 | 1.732 (2) | C13—H13 | 0.91 (2) |
S5—C40 | 1.731 (3) | C14—H14_1 | 0.97 (3) |
Si1—C4 | 1.844 (4) | C14—H14_2 | 0.95 (3) |
Si1—C14 | 1.857 (3) | C14—H14_3 | 0.97 (4) |
Si1—C28 | 1.869 (4) | C15—C36 | 1.432 (3) |
Si1—C39 | 1.872 (3) | C16—C33 | 1.363 (3) |
Si2—C5 | 1.854 (4) | C16—H16 | 0.84 (2) |
Si2—C26 | 1.856 (3) | C17—C23 | 1.379 (4) |
Si2—C29 | 1.858 (3) | C17—H17 | 0.89 (2) |
Si2—C40 | 1.869 (3) | C18—C30 | 1.395 (3) |
N1—C38 | 1.352 (3) | C18—H18 | 0.94 (3) |
N2—C36 | 1.345 (3) | C19—H19 | 0.92 (2) |
C1—C3 | 1.416 (4) | C20—C25 | 1.482 (4) |
C1—C15 | 1.362 (4) | C21—C22 | 1.408 (4) |
C1—H1 | 0.92 (2) | C21—C24 | 1.358 (3) |
C2—C10 | 1.408 (4) | C21—H21 | 0.84 (3) |
C2—C34 | 1.368 (3) | C22—C27 | 1.360 (3) |
C2—H2 | 0.88 (2) | C22—H22 | 0.98 (2) |
C3—C25 | 1.370 (3) | C23—H23 | 0.92 (2) |
C3—H3 | 0.94 (2) | C25—C38 | 1.430 (4) |
C4—H4_1 | 0.94 (4) | C26—H26_1 | 0.98 (3) |
C4—H4_2 | 1.00 (3) | C26—H26_2 | 0.92 (4) |
C5—H5_1 | 0.85 (4) | C26—H26_3 | 1.00 (4) |
C5—H5_2 | 0.94 (3) | C27—C31 | 1.451 (4) |
C5—H5_3 | 0.98 (4) | C28—H28_1 | 0.97 (3) |
C6—C12 | 1.397 (3) | C28—H28_2 | 0.99 (4) |
C6—C15 | 1.482 (4) | C29—H29_2 | 1.00 (3) |
C6—C17 | 1.393 (4) | C29—H29_3 | 0.91 (4) |
C7—C16 | 1.417 (5) | C30—C34 | 1.468 (4) |
C7—C39 | 1.365 (4) | C31—C32 | 1.362 (3) |
C7—H7 | 0.92 (3) | C32—C35 | 1.413 (4) |
C8—C18 | 1.386 (4) | C32—H32 | 0.928 (19) |
C8—C20 | 1.393 (4) | C33—C37 | 1.457 (4) |
C8—H8 | 0.92 (2) | C35—C40 | 1.364 (3) |
C9—C13 | 1.377 (4) | C35—H35 | 0.93 (3) |
C9—C20 | 1.393 (3) | C36—C38 | 1.436 (4) |
C9—H9 | 0.90 (2) | ||
N1—S1—N2 | 101.13 (11) | C6—C17—H17 | 121.3 (19) |
C34—S2—C37 | 92.27 (11) | C23—C17—H17 | 117.7 (19) |
C24—S3—C27 | 92.04 (12) | C8—C18—C30 | 120.7 (2) |
C33—S4—C39 | 93.40 (13) | C8—C18—H18 | 117.7 (15) |
C31—S5—C40 | 93.45 (12) | C30—C18—H18 | 121.5 (15) |
C4—Si1—C14 | 112.72 (15) | C11—C19—C12 | 120.7 (2) |
C4—Si1—C28 | 111.2 (2) | C11—C19—H19 | 120.2 (16) |
C4—Si1—C39 | 108.04 (17) | C12—C19—H19 | 119.1 (16) |
C14—Si1—C28 | 107.55 (17) | C8—C20—C9 | 117.4 (2) |
C14—Si1—C39 | 107.92 (14) | C8—C20—C25 | 122.2 (2) |
C28—Si1—C39 | 109.31 (16) | C9—C20—C25 | 120.3 (2) |
C5—Si2—C26 | 111.23 (14) | C22—C21—C24 | 114.1 (2) |
C5—Si2—C29 | 109.64 (18) | C22—C21—H21 | 121.1 (16) |
C5—Si2—C40 | 109.79 (14) | C24—C21—H21 | 124.7 (16) |
C26—Si2—C29 | 110.67 (17) | C21—C22—C27 | 113.0 (2) |
C26—Si2—C40 | 108.73 (16) | C21—C22—H22 | 125.7 (19) |
C29—Si2—C40 | 106.67 (14) | C27—C22—H22 | 121.3 (19) |
S1—N1—C38 | 106.76 (18) | C11—C23—C17 | 121.3 (2) |
S1—N2—C36 | 106.47 (18) | C11—C23—H23 | 122.1 (13) |
C3—C1—C15 | 123.3 (2) | C17—C23—H23 | 116.6 (13) |
C3—C1—H1 | 117.1 (17) | S3—C24—C11 | 121.54 (15) |
C15—C1—H1 | 119.5 (17) | S3—C24—C21 | 110.3 (2) |
C10—C2—C34 | 113.7 (2) | C11—C24—C21 | 128.1 (2) |
C10—C2—H2 | 125.4 (15) | C3—C25—C20 | 122.5 (2) |
C34—C2—H2 | 120.8 (15) | C3—C25—C38 | 115.4 (2) |
C1—C3—C25 | 123.3 (2) | C20—C25—C38 | 122.1 (2) |
C1—C3—H3 | 115.9 (15) | Si2—C26—H26_1 | 106.5 (14) |
C25—C3—H3 | 120.8 (15) | Si2—C26—H26_2 | 116 (2) |
Si1—C4—H4_1 | 108 (2) | Si2—C26—H26_3 | 109.8 (17) |
Si1—C4—H4_2 | 118.3 (16) | H26_1—C26—H26_2 | 108 (3) |
H4_1—C4—H4_2 | 110 (2) | H26_1—C26—H26_3 | 112 (3) |
Si2—C5—H5_1 | 111 (2) | H26_2—C26—H26_3 | 105 (3) |
Si2—C5—H5_2 | 108.0 (17) | S3—C27—C22 | 110.5 (2) |
Si2—C5—H5_3 | 111 (2) | S3—C27—C31 | 119.97 (16) |
H5_1—C5—H5_2 | 107 (3) | C22—C27—C31 | 129.5 (2) |
H5_1—C5—H5_3 | 106 (3) | Si1—C28—H28_1 | 91.6 (15) |
H5_2—C5—H5_3 | 114 (3) | Si1—C28—H28_2 | 105.9 (17) |
C12—C6—C15 | 120.0 (2) | H28_1—C28—H28_2 | 108 (3) |
C12—C6—C17 | 117.7 (2) | Si2—C29—H29_2 | 111 (2) |
C15—C6—C17 | 122.26 (19) | Si2—C29—H29_3 | 109.5 (19) |
C16—C7—C39 | 114.7 (2) | H29_2—C29—H29_3 | 106 (3) |
C16—C7—H7 | 121.2 (18) | C13—C30—C18 | 118.1 (2) |
C39—C7—H7 | 123.9 (19) | C13—C30—C34 | 120.5 (2) |
C18—C8—C20 | 121.3 (2) | C18—C30—C34 | 121.4 (2) |
C18—C8—H8 | 120.1 (17) | S5—C31—C27 | 121.30 (16) |
C20—C8—H8 | 118.6 (17) | S5—C31—C32 | 109.9 (2) |
C13—C9—C20 | 121.7 (2) | C27—C31—C32 | 128.8 (2) |
C13—C9—H9 | 117.2 (15) | C31—C32—C35 | 113.0 (2) |
C20—C9—H9 | 121.0 (15) | C31—C32—H32 | 125.9 (17) |
C2—C10—C37 | 113.1 (2) | C35—C32—H32 | 121.1 (17) |
C2—C10—H10 | 124.7 (17) | S4—C33—C16 | 110.4 (2) |
C37—C10—H10 | 122.1 (17) | S4—C33—C37 | 120.68 (17) |
C19—C11—C23 | 117.9 (2) | C16—C33—C37 | 128.8 (2) |
C19—C11—C24 | 119.5 (2) | S2—C34—C2 | 110.2 (2) |
C23—C11—C24 | 122.5 (2) | S2—C34—C30 | 120.89 (15) |
C6—C12—C19 | 121.5 (3) | C2—C34—C30 | 128.9 (2) |
C6—C12—H12 | 119.5 (14) | C32—C35—C40 | 114.9 (2) |
C19—C12—H12 | 119.0 (14) | C32—C35—H35 | 122.1 (15) |
C9—C13—C30 | 120.7 (2) | C40—C35—H35 | 122.9 (15) |
C9—C13—H13 | 118.4 (18) | N2—C36—C15 | 125.9 (2) |
C30—C13—H13 | 120.9 (18) | N2—C36—C38 | 113.0 (2) |
Si1—C14—H14_1 | 106.4 (13) | C15—C36—C38 | 121.1 (2) |
Si1—C14—H14_2 | 112.5 (18) | S2—C37—C10 | 110.7 (2) |
Si1—C14—H14_3 | 109.4 (18) | S2—C37—C33 | 119.21 (15) |
H14_1—C14—H14_2 | 113 (3) | C10—C37—C33 | 130.1 (2) |
H14_1—C14—H14_3 | 105 (3) | N1—C38—C25 | 126.1 (2) |
H14_2—C14—H14_3 | 110 (3) | N1—C38—C36 | 112.7 (2) |
C1—C15—C6 | 121.9 (2) | C25—C38—C36 | 121.2 (2) |
C1—C15—C36 | 115.7 (2) | S4—C39—Si1 | 121.16 (14) |
C6—C15—C36 | 122.5 (2) | S4—C39—C7 | 109.1 (2) |
C7—C16—C33 | 112.4 (2) | Si1—C39—C7 | 129.5 (2) |
C7—C16—H16 | 126.2 (17) | S5—C40—Si2 | 123.63 (12) |
C33—C16—H16 | 121.3 (17) | S5—C40—C35 | 108.7 (2) |
C6—C17—C23 | 120.8 (2) | Si2—C40—C35 | 127.6 (2) |