Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229615002624/ly3008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229615002624/ly3008Isup2.hkl |
CCDC reference: 1048237
Crystal data, data collection and structure refinement details are summarized in Table 1.
Data collection: SMART (Bruker, 1999); cell refinement: SMART (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).
C35H31NSi | F(000) = 1048 |
Mr = 493.70 | Dx = 1.175 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.8008 (15) Å | Cell parameters from 1766 reflections |
b = 9.5323 (11) Å | θ = 2.3–18.2° |
c = 22.906 (3) Å | µ = 0.11 mm−1 |
β = 92.817 (3)° | T = 293 K |
V = 2791.6 (6) Å3 | Rod, colourless |
Z = 4 | 0.32 × 0.25 × 0.07 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 2492 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.105 |
ω scans | θmax = 28.3°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→16 |
Tmin = 0.966, Tmax = 0.993 | k = −12→12 |
28211 measured reflections | l = −30→30 |
6938 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.059 | w = 1/[σ2(Fo2) + (0.0782P)2 + 0.6079P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.222 | (Δ/σ)max < 0.001 |
S = 0.97 | Δρmax = 0.23 e Å−3 |
6938 reflections | Δρmin = −0.22 e Å−3 |
339 parameters | Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0068 (12) |
C35H31NSi | V = 2791.6 (6) Å3 |
Mr = 493.70 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.8008 (15) Å | µ = 0.11 mm−1 |
b = 9.5323 (11) Å | T = 293 K |
c = 22.906 (3) Å | 0.32 × 0.25 × 0.07 mm |
β = 92.817 (3)° |
Bruker SMART 1000 CCD area-detector diffractometer | 6938 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2492 reflections with I > 2σ(I) |
Tmin = 0.966, Tmax = 0.993 | Rint = 0.105 |
28211 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.222 | H-atom parameters constrained |
S = 0.97 | Δρmax = 0.23 e Å−3 |
6938 reflections | Δρmin = −0.22 e Å−3 |
339 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Si1 | 0.34148 (7) | 0.47400 (10) | 0.41859 (4) | 0.0604 (3) | |
N1 | 0.6074 (2) | 1.0009 (3) | 0.39635 (12) | 0.0611 (8) | |
C1 | 0.4368 (3) | 0.3401 (4) | 0.44596 (16) | 0.0747 (11) | |
H1A | 0.4027 | 0.2506 | 0.4478 | 0.112* | |
H1B | 0.4638 | 0.3661 | 0.4843 | 0.112* | |
H1C | 0.4932 | 0.3343 | 0.4200 | 0.112* | |
C2 | 0.2407 (3) | 0.5020 (4) | 0.47315 (17) | 0.0858 (13) | |
H2A | 0.1916 | 0.5716 | 0.4588 | 0.129* | |
H2B | 0.2739 | 0.5336 | 0.5093 | 0.129* | |
H2C | 0.2047 | 0.4155 | 0.4795 | 0.129* | |
C3 | 0.4149 (3) | 0.6407 (4) | 0.40697 (15) | 0.0587 (9) | |
C4 | 0.5131 (3) | 0.6356 (4) | 0.38460 (16) | 0.0732 (11) | |
H4 | 0.5379 | 0.5496 | 0.3720 | 0.088* | |
C5 | 0.5764 (3) | 0.7524 (4) | 0.38003 (17) | 0.0728 (11) | |
H5 | 0.6418 | 0.7447 | 0.3644 | 0.087* | |
C6 | 0.5410 (3) | 0.8804 (4) | 0.39895 (15) | 0.0594 (9) | |
C7 | 0.4430 (3) | 0.8901 (4) | 0.42039 (19) | 0.0800 (12) | |
H7 | 0.4179 | 0.9765 | 0.4323 | 0.096* | |
C8 | 0.3818 (3) | 0.7717 (4) | 0.42420 (19) | 0.0805 (12) | |
H8 | 0.3157 | 0.7804 | 0.4389 | 0.097* | |
C9 | 0.5952 (3) | 1.1127 (4) | 0.35806 (15) | 0.0625 (9) | |
C10 | 0.5158 (3) | 1.1371 (5) | 0.31624 (18) | 0.0851 (12) | |
H10 | 0.4603 | 1.0750 | 0.3102 | 0.102* | |
C11 | 0.5234 (5) | 1.2594 (7) | 0.2836 (2) | 0.1092 (18) | |
H11 | 0.4711 | 1.2804 | 0.2553 | 0.131* | |
C12 | 0.6070 (5) | 1.3507 (6) | 0.2923 (2) | 0.1141 (19) | |
H12 | 0.6095 | 1.4314 | 0.2696 | 0.137* | |
C13 | 0.6853 (4) | 1.3252 (4) | 0.3331 (2) | 0.0898 (13) | |
H13 | 0.7413 | 1.3868 | 0.3381 | 0.108* | |
C14 | 0.6799 (3) | 1.2045 (4) | 0.36745 (16) | 0.0632 (10) | |
C15 | 0.7459 (3) | 1.1469 (3) | 0.41367 (15) | 0.0559 (9) | |
C16 | 0.8379 (3) | 1.1892 (4) | 0.44359 (19) | 0.0724 (11) | |
H16 | 0.8699 | 1.2731 | 0.4340 | 0.087* | |
C17 | 0.8807 (3) | 1.1063 (5) | 0.48725 (19) | 0.0800 (12) | |
H17 | 0.9426 | 1.1339 | 0.5069 | 0.096* | |
C18 | 0.8337 (3) | 0.9826 (5) | 0.50259 (17) | 0.0778 (11) | |
H18 | 0.8643 | 0.9290 | 0.5328 | 0.093* | |
C19 | 0.7424 (3) | 0.9361 (4) | 0.47427 (15) | 0.0668 (10) | |
H19 | 0.7114 | 0.8519 | 0.4843 | 0.080* | |
C20 | 0.6991 (3) | 1.0209 (3) | 0.43023 (14) | 0.0540 (8) | |
C21 | 0.2784 (2) | 0.4084 (4) | 0.34864 (15) | 0.0566 (9) | |
C22 | 0.2227 (2) | 0.2814 (3) | 0.34932 (14) | 0.0552 (8) | |
H22 | 0.2163 | 0.2345 | 0.3846 | 0.066* | |
C23 | 0.1771 (2) | 0.2248 (3) | 0.29847 (14) | 0.0491 (8) | |
C24 | 0.1878 (2) | 0.2939 (3) | 0.24516 (14) | 0.0501 (8) | |
C25 | 0.2414 (2) | 0.4198 (4) | 0.24328 (15) | 0.0603 (9) | |
H25 | 0.2474 | 0.4667 | 0.2080 | 0.072* | |
C26 | 0.2858 (3) | 0.4751 (4) | 0.29459 (15) | 0.0611 (9) | |
H26 | 0.3219 | 0.5596 | 0.2931 | 0.073* | |
C27 | 0.1105 (3) | 0.0927 (3) | 0.29055 (14) | 0.0560 (9) | |
C28 | 0.0863 (2) | 0.0962 (3) | 0.22507 (14) | 0.0558 (8) | |
C29 | 0.0267 (3) | 0.0036 (4) | 0.19132 (18) | 0.0735 (11) | |
H29 | −0.0050 | −0.0728 | 0.2085 | 0.088* | |
C30 | 0.0144 (3) | 0.0255 (5) | 0.13179 (19) | 0.0815 (12) | |
H30 | −0.0247 | −0.0378 | 0.1088 | 0.098* | |
C31 | 0.0595 (3) | 0.1402 (5) | 0.10587 (17) | 0.0806 (12) | |
H31 | 0.0505 | 0.1535 | 0.0657 | 0.097* | |
C32 | 0.1177 (3) | 0.2349 (4) | 0.13936 (15) | 0.0650 (10) | |
H32 | 0.1474 | 0.3128 | 0.1222 | 0.078* | |
C33 | 0.1312 (2) | 0.2120 (3) | 0.19883 (14) | 0.0535 (8) | |
C34 | 0.1717 (3) | −0.0392 (4) | 0.30982 (18) | 0.0850 (12) | |
H34A | 0.1298 | −0.1208 | 0.3012 | 0.127* | |
H34B | 0.1883 | −0.0348 | 0.3511 | 0.127* | |
H34C | 0.2351 | −0.0444 | 0.2893 | 0.127* | |
C35 | 0.0106 (3) | 0.1017 (4) | 0.32432 (16) | 0.0745 (11) | |
H35A | −0.0286 | 0.1832 | 0.3119 | 0.112* | |
H35B | 0.0286 | 0.1083 | 0.3654 | 0.112* | |
H35C | −0.0309 | 0.0192 | 0.3168 | 0.112* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si1 | 0.0563 (6) | 0.0655 (6) | 0.0594 (6) | −0.0069 (5) | 0.0009 (5) | −0.0113 (5) |
N1 | 0.0573 (17) | 0.0599 (19) | 0.0649 (19) | −0.0060 (14) | −0.0085 (14) | 0.0004 (15) |
C1 | 0.081 (3) | 0.074 (2) | 0.068 (2) | −0.001 (2) | −0.008 (2) | −0.0045 (19) |
C2 | 0.078 (3) | 0.100 (3) | 0.080 (3) | −0.010 (2) | 0.014 (2) | −0.022 (2) |
C3 | 0.051 (2) | 0.061 (2) | 0.063 (2) | −0.0013 (17) | −0.0055 (17) | −0.0141 (17) |
C4 | 0.076 (3) | 0.064 (2) | 0.080 (3) | −0.009 (2) | 0.016 (2) | −0.025 (2) |
C5 | 0.067 (2) | 0.070 (3) | 0.083 (3) | −0.008 (2) | 0.017 (2) | −0.022 (2) |
C6 | 0.054 (2) | 0.056 (2) | 0.067 (2) | −0.0041 (17) | −0.0052 (17) | −0.0086 (17) |
C7 | 0.057 (2) | 0.056 (2) | 0.128 (4) | 0.003 (2) | 0.013 (2) | −0.021 (2) |
C8 | 0.051 (2) | 0.072 (3) | 0.119 (3) | −0.002 (2) | 0.009 (2) | −0.012 (2) |
C9 | 0.073 (3) | 0.063 (2) | 0.051 (2) | 0.013 (2) | 0.0020 (18) | −0.0050 (18) |
C10 | 0.096 (3) | 0.090 (3) | 0.067 (3) | 0.027 (3) | −0.011 (2) | −0.013 (2) |
C11 | 0.130 (5) | 0.131 (5) | 0.066 (3) | 0.062 (4) | −0.001 (3) | 0.006 (3) |
C12 | 0.139 (5) | 0.109 (4) | 0.097 (4) | 0.055 (4) | 0.038 (4) | 0.036 (3) |
C13 | 0.106 (3) | 0.073 (3) | 0.094 (3) | 0.022 (3) | 0.039 (3) | 0.017 (2) |
C14 | 0.072 (2) | 0.057 (2) | 0.063 (2) | 0.008 (2) | 0.023 (2) | −0.0018 (18) |
C15 | 0.057 (2) | 0.051 (2) | 0.061 (2) | −0.0039 (17) | 0.0174 (18) | −0.0079 (17) |
C16 | 0.055 (2) | 0.061 (2) | 0.102 (3) | −0.0102 (19) | 0.019 (2) | −0.020 (2) |
C17 | 0.055 (2) | 0.093 (3) | 0.092 (3) | −0.005 (2) | 0.001 (2) | −0.022 (3) |
C18 | 0.062 (2) | 0.104 (3) | 0.067 (3) | 0.008 (2) | −0.001 (2) | −0.001 (2) |
C19 | 0.059 (2) | 0.075 (2) | 0.066 (2) | −0.0079 (19) | 0.0040 (19) | 0.001 (2) |
C20 | 0.0531 (19) | 0.059 (2) | 0.050 (2) | −0.0032 (17) | 0.0031 (16) | −0.0056 (17) |
C21 | 0.052 (2) | 0.058 (2) | 0.061 (2) | −0.0064 (17) | 0.0056 (16) | −0.0026 (17) |
C22 | 0.056 (2) | 0.060 (2) | 0.048 (2) | −0.0071 (17) | −0.0006 (16) | −0.0005 (16) |
C23 | 0.0469 (18) | 0.0494 (19) | 0.051 (2) | −0.0030 (15) | 0.0048 (15) | −0.0007 (15) |
C24 | 0.0430 (18) | 0.055 (2) | 0.052 (2) | −0.0040 (15) | 0.0067 (15) | 0.0009 (16) |
C25 | 0.056 (2) | 0.066 (2) | 0.059 (2) | −0.0101 (18) | 0.0053 (17) | 0.0078 (18) |
C26 | 0.055 (2) | 0.060 (2) | 0.068 (2) | −0.0168 (17) | 0.0047 (18) | −0.0036 (19) |
C27 | 0.064 (2) | 0.0471 (19) | 0.057 (2) | −0.0087 (17) | 0.0050 (17) | −0.0050 (16) |
C28 | 0.0522 (19) | 0.055 (2) | 0.060 (2) | −0.0007 (17) | −0.0002 (16) | −0.0099 (17) |
C29 | 0.074 (3) | 0.071 (3) | 0.075 (3) | −0.012 (2) | 0.002 (2) | −0.015 (2) |
C30 | 0.072 (3) | 0.097 (3) | 0.074 (3) | −0.008 (2) | −0.009 (2) | −0.025 (2) |
C31 | 0.076 (3) | 0.109 (3) | 0.055 (2) | 0.004 (3) | −0.010 (2) | −0.012 (2) |
C32 | 0.061 (2) | 0.079 (2) | 0.055 (2) | 0.0027 (19) | 0.0033 (18) | −0.0019 (19) |
C33 | 0.0452 (19) | 0.064 (2) | 0.051 (2) | 0.0013 (16) | 0.0018 (15) | −0.0046 (17) |
C34 | 0.103 (3) | 0.061 (2) | 0.091 (3) | 0.006 (2) | −0.004 (2) | −0.002 (2) |
C35 | 0.075 (2) | 0.076 (3) | 0.074 (3) | −0.026 (2) | 0.017 (2) | −0.0055 (19) |
Si1—C1 | 1.853 (4) | C16—H16 | 0.9300 |
Si1—C2 | 1.859 (4) | C17—C18 | 1.377 (5) |
Si1—C21 | 1.866 (3) | C17—H17 | 0.9300 |
Si1—C3 | 1.872 (4) | C18—C19 | 1.382 (5) |
N1—C9 | 1.384 (4) | C18—H18 | 0.9300 |
N1—C20 | 1.388 (4) | C19—C20 | 1.386 (5) |
N1—C6 | 1.431 (4) | C19—H19 | 0.9300 |
C1—H1A | 0.9600 | C21—C26 | 1.399 (5) |
C1—H1B | 0.9600 | C21—C22 | 1.406 (4) |
C1—H1C | 0.9600 | C22—C23 | 1.386 (4) |
C2—H2A | 0.9600 | C22—H22 | 0.9300 |
C2—H2B | 0.9600 | C23—C24 | 1.400 (4) |
C2—H2C | 0.9600 | C23—C27 | 1.526 (4) |
C3—C4 | 1.382 (5) | C24—C25 | 1.384 (4) |
C3—C8 | 1.383 (5) | C24—C33 | 1.478 (4) |
C4—C5 | 1.384 (5) | C25—C26 | 1.385 (4) |
C4—H4 | 0.9300 | C25—H25 | 0.9300 |
C5—C6 | 1.378 (5) | C26—H26 | 0.9300 |
C5—H5 | 0.9300 | C27—C28 | 1.517 (4) |
C6—C7 | 1.373 (5) | C27—C35 | 1.529 (5) |
C7—C8 | 1.379 (5) | C27—C34 | 1.534 (5) |
C7—H7 | 0.9300 | C28—C29 | 1.379 (4) |
C8—H8 | 0.9300 | C28—C33 | 1.394 (4) |
C9—C10 | 1.381 (5) | C29—C30 | 1.381 (5) |
C9—C14 | 1.403 (5) | C29—H29 | 0.9300 |
C10—C11 | 1.391 (7) | C30—C31 | 1.385 (5) |
C10—H10 | 0.9300 | C30—H30 | 0.9300 |
C11—C12 | 1.386 (7) | C31—C32 | 1.379 (5) |
C11—H11 | 0.9300 | C31—H31 | 0.9300 |
C12—C13 | 1.360 (7) | C32—C33 | 1.382 (4) |
C12—H12 | 0.9300 | C32—H32 | 0.9300 |
C13—C14 | 1.397 (5) | C34—H34A | 0.9600 |
C13—H13 | 0.9300 | C34—H34B | 0.9600 |
C14—C15 | 1.431 (5) | C34—H34C | 0.9600 |
C15—C16 | 1.393 (5) | C35—H35A | 0.9600 |
C15—C20 | 1.403 (4) | C35—H35B | 0.9600 |
C16—C17 | 1.368 (5) | C35—H35C | 0.9600 |
C1—Si1—C2 | 109.78 (19) | C18—C17—H17 | 119.4 |
C1—Si1—C21 | 108.03 (16) | C17—C18—C19 | 121.7 (4) |
C2—Si1—C21 | 109.91 (16) | C17—C18—H18 | 119.2 |
C1—Si1—C3 | 107.83 (16) | C19—C18—H18 | 119.2 |
C2—Si1—C3 | 110.07 (17) | C18—C19—C20 | 117.0 (4) |
C21—Si1—C3 | 111.17 (15) | C18—C19—H19 | 121.5 |
C9—N1—C20 | 108.3 (3) | C20—C19—H19 | 121.5 |
C9—N1—C6 | 126.5 (3) | C19—C20—N1 | 128.6 (3) |
C20—N1—C6 | 125.0 (3) | C19—C20—C15 | 122.3 (3) |
Si1—C1—H1A | 109.5 | N1—C20—C15 | 109.1 (3) |
Si1—C1—H1B | 109.5 | C26—C21—C22 | 117.2 (3) |
H1A—C1—H1B | 109.5 | C26—C21—Si1 | 124.2 (3) |
Si1—C1—H1C | 109.5 | C22—C21—Si1 | 118.5 (3) |
H1A—C1—H1C | 109.5 | C23—C22—C21 | 121.3 (3) |
H1B—C1—H1C | 109.5 | C23—C22—H22 | 119.4 |
Si1—C2—H2A | 109.5 | C21—C22—H22 | 119.4 |
Si1—C2—H2B | 109.5 | C22—C23—C24 | 119.6 (3) |
H2A—C2—H2B | 109.5 | C22—C23—C27 | 129.1 (3) |
Si1—C2—H2C | 109.5 | C24—C23—C27 | 111.2 (3) |
H2A—C2—H2C | 109.5 | C25—C24—C23 | 120.3 (3) |
H2B—C2—H2C | 109.5 | C25—C24—C33 | 131.4 (3) |
C4—C3—C8 | 115.8 (3) | C23—C24—C33 | 108.2 (3) |
C4—C3—Si1 | 119.7 (3) | C24—C25—C26 | 119.2 (3) |
C8—C3—Si1 | 124.3 (3) | C24—C25—H25 | 120.4 |
C3—C4—C5 | 123.1 (3) | C26—C25—H25 | 120.4 |
C3—C4—H4 | 118.4 | C25—C26—C21 | 122.4 (3) |
C5—C4—H4 | 118.4 | C25—C26—H26 | 118.8 |
C6—C5—C4 | 119.1 (3) | C21—C26—H26 | 118.8 |
C6—C5—H5 | 120.5 | C28—C27—C23 | 100.7 (3) |
C4—C5—H5 | 120.5 | C28—C27—C35 | 111.3 (3) |
C7—C6—C5 | 119.5 (3) | C23—C27—C35 | 111.7 (3) |
C7—C6—N1 | 121.0 (3) | C28—C27—C34 | 112.3 (3) |
C5—C6—N1 | 119.5 (3) | C23—C27—C34 | 111.6 (3) |
C6—C7—C8 | 120.0 (3) | C35—C27—C34 | 109.1 (3) |
C6—C7—H7 | 120.0 | C29—C28—C33 | 119.6 (3) |
C8—C7—H7 | 120.0 | C29—C28—C27 | 128.4 (3) |
C7—C8—C3 | 122.5 (3) | C33—C28—C27 | 112.0 (3) |
C7—C8—H8 | 118.7 | C28—C29—C30 | 119.4 (4) |
C3—C8—H8 | 118.7 | C28—C29—H29 | 120.3 |
C10—C9—N1 | 128.7 (4) | C30—C29—H29 | 120.3 |
C10—C9—C14 | 122.5 (4) | C29—C30—C31 | 120.8 (4) |
N1—C9—C14 | 108.7 (3) | C29—C30—H30 | 119.6 |
C9—C10—C11 | 116.5 (5) | C31—C30—H30 | 119.6 |
C9—C10—H10 | 121.8 | C32—C31—C30 | 120.3 (4) |
C11—C10—H10 | 121.8 | C32—C31—H31 | 119.9 |
C12—C11—C10 | 121.5 (5) | C30—C31—H31 | 119.9 |
C12—C11—H11 | 119.2 | C31—C32—C33 | 118.9 (4) |
C10—C11—H11 | 119.2 | C31—C32—H32 | 120.6 |
C13—C12—C11 | 121.6 (5) | C33—C32—H32 | 120.6 |
C13—C12—H12 | 119.2 | C32—C33—C28 | 121.1 (3) |
C11—C12—H12 | 119.2 | C32—C33—C24 | 131.1 (3) |
C12—C13—C14 | 118.7 (5) | C28—C33—C24 | 107.8 (3) |
C12—C13—H13 | 120.7 | C27—C34—H34A | 109.5 |
C14—C13—H13 | 120.7 | C27—C34—H34B | 109.5 |
C13—C14—C9 | 119.1 (4) | H34A—C34—H34B | 109.5 |
C13—C14—C15 | 133.5 (4) | C27—C34—H34C | 109.5 |
C9—C14—C15 | 107.3 (3) | H34A—C34—H34C | 109.5 |
C16—C15—C20 | 118.5 (3) | H34B—C34—H34C | 109.5 |
C16—C15—C14 | 135.0 (3) | C27—C35—H35A | 109.5 |
C20—C15—C14 | 106.5 (3) | C27—C35—H35B | 109.5 |
C17—C16—C15 | 119.4 (4) | H35A—C35—H35B | 109.5 |
C17—C16—H16 | 120.3 | C27—C35—H35C | 109.5 |
C15—C16—H16 | 120.3 | H35A—C35—H35C | 109.5 |
C16—C17—C18 | 121.1 (4) | H35B—C35—H35C | 109.5 |
C16—C17—H17 | 119.4 | ||
C1—Si1—C3—C4 | 38.6 (3) | C16—C15—C20—C19 | −1.4 (5) |
C2—Si1—C3—C4 | 158.4 (3) | C14—C15—C20—C19 | 179.9 (3) |
C21—Si1—C3—C4 | −79.6 (3) | C16—C15—C20—N1 | 178.2 (3) |
C1—Si1—C3—C8 | −135.3 (3) | C14—C15—C20—N1 | −0.6 (4) |
C2—Si1—C3—C8 | −15.5 (4) | C1—Si1—C21—C26 | −117.7 (3) |
C21—Si1—C3—C8 | 106.5 (3) | C2—Si1—C21—C26 | 122.5 (3) |
C8—C3—C4—C5 | 0.9 (6) | C3—Si1—C21—C26 | 0.4 (3) |
Si1—C3—C4—C5 | −173.6 (3) | C1—Si1—C21—C22 | 59.9 (3) |
C3—C4—C5—C6 | 0.5 (6) | C2—Si1—C21—C22 | −59.8 (3) |
C4—C5—C6—C7 | −1.8 (6) | C3—Si1—C21—C22 | 178.0 (2) |
C4—C5—C6—N1 | 177.8 (3) | C26—C21—C22—C23 | 0.0 (5) |
C9—N1—C6—C7 | −72.4 (5) | Si1—C21—C22—C23 | −177.8 (2) |
C20—N1—C6—C7 | 111.5 (4) | C21—C22—C23—C24 | 0.9 (5) |
C9—N1—C6—C5 | 108.1 (4) | C21—C22—C23—C27 | −177.3 (3) |
C20—N1—C6—C5 | −68.0 (5) | C22—C23—C24—C25 | −1.5 (5) |
C5—C6—C7—C8 | 1.6 (6) | C27—C23—C24—C25 | 177.0 (3) |
N1—C6—C7—C8 | −177.9 (3) | C22—C23—C24—C33 | −179.4 (3) |
C6—C7—C8—C3 | −0.2 (7) | C27—C23—C24—C33 | −1.0 (3) |
C4—C3—C8—C7 | −1.0 (6) | C23—C24—C25—C26 | 1.1 (5) |
Si1—C3—C8—C7 | 173.1 (3) | C33—C24—C25—C26 | 178.5 (3) |
C20—N1—C9—C10 | 179.8 (3) | C24—C25—C26—C21 | −0.2 (5) |
C6—N1—C9—C10 | 3.2 (6) | C22—C21—C26—C25 | −0.4 (5) |
C20—N1—C9—C14 | 0.2 (4) | Si1—C21—C26—C25 | 177.3 (3) |
C6—N1—C9—C14 | −176.5 (3) | C22—C23—C27—C28 | 179.0 (3) |
N1—C9—C10—C11 | 179.9 (4) | C24—C23—C27—C28 | 0.7 (3) |
C14—C9—C10—C11 | −0.5 (5) | C22—C23—C27—C35 | 60.8 (4) |
C9—C10—C11—C12 | 0.8 (7) | C24—C23—C27—C35 | −117.5 (3) |
C10—C11—C12—C13 | −0.2 (8) | C22—C23—C27—C34 | −61.7 (4) |
C11—C12—C13—C14 | −0.8 (7) | C24—C23—C27—C34 | 120.0 (3) |
C12—C13—C14—C9 | 1.1 (6) | C23—C27—C28—C29 | −179.0 (3) |
C12—C13—C14—C15 | −179.2 (4) | C35—C27—C28—C29 | −60.5 (4) |
C10—C9—C14—C13 | −0.4 (5) | C34—C27—C28—C29 | 62.2 (5) |
N1—C9—C14—C13 | 179.3 (3) | C23—C27—C28—C33 | −0.2 (3) |
C10—C9—C14—C15 | 179.8 (3) | C35—C27—C28—C33 | 118.4 (3) |
N1—C9—C14—C15 | −0.5 (4) | C34—C27—C28—C33 | −119.0 (3) |
C13—C14—C15—C16 | 2.5 (7) | C33—C28—C29—C30 | 1.5 (5) |
C9—C14—C15—C16 | −177.8 (4) | C27—C28—C29—C30 | −179.8 (3) |
C13—C14—C15—C20 | −179.1 (4) | C28—C29—C30—C31 | −1.2 (6) |
C9—C14—C15—C20 | 0.7 (4) | C29—C30—C31—C32 | 0.0 (6) |
C20—C15—C16—C17 | 1.1 (5) | C30—C31—C32—C33 | 0.9 (5) |
C14—C15—C16—C17 | 179.4 (4) | C31—C32—C33—C28 | −0.6 (5) |
C15—C16—C17—C18 | −0.8 (6) | C31—C32—C33—C24 | −179.5 (3) |
C16—C17—C18—C19 | 0.8 (6) | C29—C28—C33—C32 | −0.6 (5) |
C17—C18—C19—C20 | −1.0 (6) | C27—C28—C33—C32 | −179.5 (3) |
C18—C19—C20—N1 | −178.1 (3) | C29—C28—C33—C24 | 178.6 (3) |
C18—C19—C20—C15 | 1.3 (5) | C27—C28—C33—C24 | −0.4 (4) |
C9—N1—C20—C19 | 179.8 (3) | C25—C24—C33—C32 | 2.3 (6) |
C6—N1—C20—C19 | −3.5 (5) | C23—C24—C33—C32 | 179.9 (3) |
C9—N1—C20—C15 | 0.3 (4) | C25—C24—C33—C28 | −176.8 (3) |
C6—N1—C20—C15 | 177.0 (3) | C23—C24—C33—C28 | 0.8 (3) |
Experimental details
Crystal data | |
Chemical formula | C35H31NSi |
Mr | 493.70 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 12.8008 (15), 9.5323 (11), 22.906 (3) |
β (°) | 92.817 (3) |
V (Å3) | 2791.6 (6) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.11 |
Crystal size (mm) | 0.32 × 0.25 × 0.07 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.966, 0.993 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 28211, 6938, 2492 |
Rint | 0.105 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.222, 0.97 |
No. of reflections | 6938 |
No. of parameters | 339 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.22 |
Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012).