organic compounds
N-[1-Phenyl-2,5-bis(trimethylsilyl)pent-2-en-4-yn-1-yl]aniline
aA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov St. 28, 119991, Moscow, Russia, and bLeibniz-Institut für Katalyse e.V. an der Universität Rostock, Albert-Einstein-Strasse 29a, 18059 Rostock, Germany
*Correspondence e-mail: uwe.rosenthal@catalysis.de
The molecular structure of the title compound, C23H31NSi2, reveals an acyclic conjugated enyne unit as the main feature. The central pent-2-en-4-yl fragment is essentially planar, with a maximum deviation of 0.0492 (7) Å from the mean plane defined by the C—C=C—C≡C unit. The dihedral angle between the phenyl rings is 84.44 (5)°.
Keywords: crystal structure; acyclic enyne chain; aniline; trimethylsilyl.
CCDC reference: 1508008
Structure description
Compounds that contain conjugated enyne fragments are valuable building blocks in organic synthesis, since these are important units in medicinal and material science (Ochiai et al., 1999; Saito et al., 2001). The title compound (Fig. 1) was synthesized by hydrolysis of the corresponding zirconocene aza-metallacycle in toluene. The observed bond lengths and angles of the central acyclic amino-pent-2-en-4-yl fragment [C1—C2 1.2048 (17), C2—C3 1.4325 (16), C3—C4 1.3448 (15) Å; C1—C2—C3 175.03 (13), C2—C3—C4 126.26 (12)°] are comparable with those of similar derivatives with acyclic pent-2-en-4-yn-amides (Feng et al., 2014; Li et al., 2014; Meng & Wan, 2013; Cheng et al., 2012; Borbulevych et al., 1999, 2001), a polymer containing [(Ph)2N—CH2—C=C—C≡C–] building blocks (Enkelmann & Schleier, 1980) and an ammonium salt (Kuminek et al., 2013; Tedesco et al., 2002). As expected, the central pent-2-en-4-yl fragment of the title compound is nearly planar; mean deviation of the best plane defined by C1, C2, C3, C4 and C5 is 0.037 Å. The observed dihedral angle between the phenyl rings is 84.44 (5)°.
Synthesis and crystallization
All manipulations were carried out under an argon atmosphere using standard Schlenk techniques. Toluene and n-hexane were dried over two columns with activated aluminium oxide with an Inert PureSolv MD5 solvent purification system (Innovative Technology). To a dark-red toluene solution (10 ml) of bis(cyclopentadienyl){N-[1-phenyl-2,5-bis(trimethylsilyl)pent-2-en-4-yn-1-yl]anilido}zirconium (0.242 g, 0.405 mmol), which was prepared according to the method of Burlakov et al. (2014), was added 8.5 ml of water saturated toluene and the resulting mixture was kept at room temperature without stirring. After one day, the light-yellow solution had evaporated to dryness. The residue was extracted with 10 ml of n-hexane. The colourless solution was filtered, concentrated to 1–1.5 ml and allowed to stand at room temperature. After one day, colourless crystals were separated from the mother liquor, washed with cold n-hexane, and dried in vacuum to give 0.088 g (58%) of the title compound. Single crystals were obtained from a dissolved in n-hexane at room temperature.
M.p.: 99–100°C under Ar. Elemental analysis: calculated for C23H31NSi2: C 73.14, H 8.27, N 3.71%; found: C 72.83, H 8.02, N 3.50%. IR (ATR, cm−1): 2125, 2182 (C≡C), 3401(N—H). MS (70 eV, m/z): 377 [M]+, 304 [M - SiMe3]+, 197 [Me3SiC2—CH=CH—SiMe3 + H]+, 182 [PhN=CHPh + H]+, 73 [SiMe3]+.
1H NMR (300 MHz, C6D6, 297 K): δ (p.p.m.) 0.19 (s, 9H, SiMe3); 0.29 (s, 9H, SiMe3); 3.50 (d, 1H, NH); 5.07 (d, 1H, CHPh); 6.38 (m, 2H, o-Ph); 6.52 (s, 1H, CH=C); 6.69 (m, 1H, p-Ph) 7.03–7.11 (m, 7H, Ph). 13C NMR (75 MHz, C6D6, 297 K): δ (p.p.m.) −0.9, −0.3 (SiMe3); 63.1 (CHPh); 101.5, 105.7 (C≡C); 113.6 (o,m-Ph); 118.1, 121.3 (p-Ph); 127.9 (CH=C); 128.8, 128.8, 129.5 (o,m-Ph); 141.2, 147.1 (i-Ph); 156.8 (CH=C).
Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1508008
https://doi.org/10.1107/S2414314616015595/is4011sup1.cif
contains datablocks I, ax0535. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616015595/is4011Isup2.hkl
Data collection: APEX2 (Bruker, 2011); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).C23H31NSi2 | Z = 2 |
Mr = 377.67 | F(000) = 408 |
Triclinic, P1 | Dx = 1.096 Mg m−3 |
a = 11.0662 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.1661 (5) Å | Cell parameters from 9956 reflections |
c = 11.2508 (5) Å | θ = 2.4–28.8° |
α = 65.2268 (6)° | µ = 0.16 mm−1 |
β = 67.0573 (6)° | T = 150 K |
γ = 71.9789 (6)° | Prism, pale yellow |
V = 1144.57 (9) Å3 | 0.46 × 0.31 × 0.31 mm |
Bruker APEXII CCD diffractometer | 5526 independent reflections |
Radiation source: fine-focus sealed tube | 4641 reflections with I > 2σ(I) |
Detector resolution: 8.3333 pixels mm-1 | Rint = 0.026 |
φ and ω scans | θmax = 28.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | h = −14→14 |
Tmin = 0.93, Tmax = 0.95 | k = −14→14 |
22773 measured reflections | l = −14→14 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0362P)2 + 0.4111P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5526 reflections | Δρmax = 0.35 e Å−3 |
245 parameters | Δρmin = −0.20 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.74405 (12) | 0.65953 (14) | 0.53612 (12) | 0.0277 (3) | |
C2 | 0.70399 (11) | 0.63622 (13) | 0.46400 (11) | 0.0242 (2) | |
C3 | 0.65238 (11) | 0.59872 (12) | 0.38833 (11) | 0.0223 (2) | |
H3 | 0.6319 | 0.5110 | 0.4276 | 0.027* | |
C4 | 0.63021 (10) | 0.67573 (11) | 0.26706 (11) | 0.0181 (2) | |
C5 | 0.56351 (11) | 0.62132 (11) | 0.20861 (11) | 0.0189 (2) | |
H5 | 0.6128 | 0.6409 | 0.1086 | 0.023* | |
C6 | 0.97016 (16) | 0.55728 (17) | 0.65491 (18) | 0.0444 (4) | |
H6A | 0.9518 | 0.4662 | 0.6896 | 0.067* | |
H6B | 1.0089 | 0.5657 | 0.7154 | 0.067* | |
H6C | 1.0331 | 0.5754 | 0.5620 | 0.067* | |
C7 | 0.84118 (16) | 0.85404 (15) | 0.58691 (16) | 0.0405 (3) | |
H7A | 0.8996 | 0.8762 | 0.4919 | 0.061* | |
H7B | 0.8832 | 0.8624 | 0.6446 | 0.061* | |
H7C | 0.7557 | 0.9156 | 0.5906 | 0.061* | |
C8 | 0.68621 (17) | 0.64354 (17) | 0.82272 (14) | 0.0427 (4) | |
H8A | 0.6046 | 0.7101 | 0.8176 | 0.064* | |
H8B | 0.7211 | 0.6478 | 0.8884 | 0.064* | |
H8C | 0.6662 | 0.5539 | 0.8530 | 0.064* | |
C9 | 0.84620 (12) | 0.84738 (14) | 0.15867 (14) | 0.0300 (3) | |
H9A | 0.9082 | 0.7767 | 0.1239 | 0.045* | |
H9B | 0.8487 | 0.8302 | 0.2506 | 0.045* | |
H9C | 0.8723 | 0.9343 | 0.0969 | 0.045* | |
C10 | 0.55181 (13) | 0.96905 (14) | 0.25251 (15) | 0.0320 (3) | |
H10A | 0.5759 | 1.0584 | 0.2024 | 0.048* | |
H10B | 0.5532 | 0.9393 | 0.3473 | 0.048* | |
H10C | 0.4622 | 0.9725 | 0.2526 | 0.048* | |
C11 | 0.66940 (14) | 0.89749 (13) | −0.01128 (12) | 0.0296 (3) | |
H11A | 0.6802 | 0.9913 | −0.0616 | 0.044* | |
H11B | 0.5837 | 0.8862 | −0.0083 | 0.044* | |
H11C | 0.7419 | 0.8403 | −0.0578 | 0.044* | |
C12 | 0.41890 (11) | 0.69124 (12) | 0.22133 (12) | 0.0213 (2) | |
C13 | 0.34076 (12) | 0.73615 (13) | 0.33064 (13) | 0.0258 (3) | |
H13 | 0.3789 | 0.7283 | 0.3966 | 0.031* | |
C14 | 0.20694 (13) | 0.79257 (15) | 0.34416 (16) | 0.0351 (3) | |
H14 | 0.1541 | 0.8232 | 0.4191 | 0.042* | |
C15 | 0.15117 (13) | 0.80401 (15) | 0.24842 (17) | 0.0396 (3) | |
H15 | 0.0598 | 0.8422 | 0.2579 | 0.048* | |
C16 | 0.22787 (14) | 0.76003 (15) | 0.13902 (16) | 0.0378 (3) | |
H16 | 0.1893 | 0.7679 | 0.0735 | 0.045* | |
C17 | 0.36149 (13) | 0.70431 (13) | 0.12505 (13) | 0.0282 (3) | |
H17 | 0.4142 | 0.6749 | 0.0493 | 0.034* | |
C18 | 0.67654 (12) | 0.38337 (12) | 0.24183 (12) | 0.0229 (2) | |
C19 | 0.66529 (14) | 0.24778 (13) | 0.29765 (14) | 0.0309 (3) | |
H19 | 0.5813 | 0.2219 | 0.3539 | 0.037* | |
C20 | 0.77569 (16) | 0.15132 (15) | 0.27136 (16) | 0.0395 (3) | |
H20 | 0.7666 | 0.0597 | 0.3102 | 0.047* | |
C21 | 0.89939 (15) | 0.18612 (16) | 0.18919 (17) | 0.0412 (3) | |
H21 | 0.9747 | 0.1193 | 0.1712 | 0.049* | |
C22 | 0.91101 (14) | 0.31931 (15) | 0.13411 (15) | 0.0371 (3) | |
H22 | 0.9953 | 0.3442 | 0.0775 | 0.044* | |
C23 | 0.80156 (12) | 0.41802 (14) | 0.15989 (13) | 0.0291 (3) | |
H23 | 0.8118 | 0.5093 | 0.1217 | 0.035* | |
N1 | 0.56481 (10) | 0.47771 (10) | 0.27120 (11) | 0.0242 (2) | |
Si1 | 0.81276 (3) | 0.67930 (4) | 0.65053 (3) | 0.02577 (9) | |
Si2 | 0.67391 (3) | 0.84901 (3) | 0.16732 (3) | 0.01984 (8) | |
H1 | 0.4925 (16) | 0.4510 (16) | 0.3107 (16) | 0.034 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0228 (6) | 0.0382 (7) | 0.0211 (5) | −0.0022 (5) | −0.0065 (5) | −0.0116 (5) |
C2 | 0.0208 (5) | 0.0291 (6) | 0.0185 (5) | −0.0018 (5) | −0.0051 (4) | −0.0069 (5) |
C3 | 0.0211 (5) | 0.0248 (6) | 0.0201 (5) | −0.0042 (4) | −0.0060 (4) | −0.0069 (5) |
C4 | 0.0146 (5) | 0.0212 (6) | 0.0189 (5) | −0.0018 (4) | −0.0039 (4) | −0.0090 (4) |
C5 | 0.0196 (5) | 0.0202 (6) | 0.0170 (5) | −0.0056 (4) | −0.0047 (4) | −0.0057 (4) |
C6 | 0.0427 (8) | 0.0459 (9) | 0.0596 (10) | 0.0066 (7) | −0.0325 (8) | −0.0262 (8) |
C7 | 0.0422 (8) | 0.0365 (8) | 0.0416 (8) | −0.0083 (6) | −0.0097 (6) | −0.0139 (7) |
C8 | 0.0617 (10) | 0.0441 (9) | 0.0233 (6) | −0.0158 (7) | −0.0046 (6) | −0.0153 (6) |
C9 | 0.0237 (6) | 0.0345 (7) | 0.0348 (7) | −0.0100 (5) | −0.0094 (5) | −0.0107 (6) |
C10 | 0.0314 (7) | 0.0277 (7) | 0.0405 (7) | −0.0007 (5) | −0.0122 (6) | −0.0171 (6) |
C11 | 0.0390 (7) | 0.0259 (7) | 0.0247 (6) | −0.0123 (5) | −0.0130 (5) | −0.0018 (5) |
C12 | 0.0205 (5) | 0.0193 (6) | 0.0237 (5) | −0.0070 (4) | −0.0084 (4) | −0.0028 (4) |
C13 | 0.0210 (5) | 0.0264 (6) | 0.0287 (6) | −0.0057 (5) | −0.0067 (5) | −0.0076 (5) |
C14 | 0.0210 (6) | 0.0335 (7) | 0.0467 (8) | −0.0048 (5) | −0.0048 (5) | −0.0149 (6) |
C15 | 0.0213 (6) | 0.0341 (8) | 0.0613 (9) | −0.0043 (5) | −0.0174 (6) | −0.0102 (7) |
C16 | 0.0351 (7) | 0.0344 (8) | 0.0504 (8) | −0.0110 (6) | −0.0276 (7) | −0.0034 (6) |
C17 | 0.0302 (6) | 0.0273 (7) | 0.0305 (6) | −0.0099 (5) | −0.0140 (5) | −0.0051 (5) |
C18 | 0.0259 (6) | 0.0232 (6) | 0.0236 (5) | −0.0024 (5) | −0.0105 (5) | −0.0102 (5) |
C19 | 0.0345 (7) | 0.0254 (7) | 0.0351 (7) | −0.0064 (5) | −0.0125 (5) | −0.0095 (5) |
C20 | 0.0491 (9) | 0.0228 (7) | 0.0509 (9) | 0.0003 (6) | −0.0226 (7) | −0.0143 (6) |
C21 | 0.0382 (8) | 0.0357 (8) | 0.0544 (9) | 0.0100 (6) | −0.0194 (7) | −0.0262 (7) |
C22 | 0.0263 (6) | 0.0423 (8) | 0.0445 (8) | −0.0010 (6) | −0.0068 (6) | −0.0237 (7) |
C23 | 0.0269 (6) | 0.0271 (7) | 0.0333 (6) | −0.0045 (5) | −0.0068 (5) | −0.0126 (5) |
N1 | 0.0206 (5) | 0.0204 (5) | 0.0295 (5) | −0.0066 (4) | −0.0033 (4) | −0.0082 (4) |
Si1 | 0.02876 (18) | 0.0307 (2) | 0.02222 (16) | −0.00232 (14) | −0.01080 (13) | −0.01223 (14) |
Si2 | 0.01964 (15) | 0.01973 (17) | 0.02223 (15) | −0.00389 (12) | −0.00781 (12) | −0.00738 (12) |
C1—C2 | 1.2048 (17) | C10—H10C | 0.9800 |
C1—Si1 | 1.8408 (13) | C11—Si2 | 1.8664 (13) |
C2—C3 | 1.4325 (16) | C11—H11A | 0.9800 |
C3—C4 | 1.3448 (15) | C11—H11B | 0.9800 |
C3—H3 | 0.9500 | C11—H11C | 0.9800 |
C4—C5 | 1.5288 (15) | C12—C13 | 1.3897 (17) |
C4—Si2 | 1.8903 (12) | C12—C17 | 1.3945 (16) |
C5—N1 | 1.4543 (15) | C13—C14 | 1.3930 (17) |
C5—C12 | 1.5274 (15) | C13—H13 | 0.9500 |
C5—H5 | 1.0000 | C14—C15 | 1.383 (2) |
C6—Si1 | 1.8534 (15) | C14—H14 | 0.9500 |
C6—H6A | 0.9800 | C15—C16 | 1.382 (2) |
C6—H6B | 0.9800 | C15—H15 | 0.9500 |
C6—H6C | 0.9800 | C16—C17 | 1.3892 (19) |
C7—Si1 | 1.8579 (16) | C16—H16 | 0.9500 |
C7—H7A | 0.9800 | C17—H17 | 0.9500 |
C7—H7B | 0.9800 | C18—N1 | 1.3838 (15) |
C7—H7C | 0.9800 | C18—C23 | 1.3970 (17) |
C8—Si1 | 1.8591 (15) | C18—C19 | 1.4004 (18) |
C8—H8A | 0.9800 | C19—C20 | 1.382 (2) |
C8—H8B | 0.9800 | C19—H19 | 0.9500 |
C8—H8C | 0.9800 | C20—C21 | 1.386 (2) |
C9—Si2 | 1.8656 (12) | C20—H20 | 0.9500 |
C9—H9A | 0.9800 | C21—C22 | 1.377 (2) |
C9—H9B | 0.9800 | C21—H21 | 0.9500 |
C9—H9C | 0.9800 | C22—C23 | 1.3907 (19) |
C10—Si2 | 1.8675 (13) | C22—H22 | 0.9500 |
C10—H10A | 0.9800 | C23—H23 | 0.9500 |
C10—H10B | 0.9800 | N1—H1 | 0.829 (16) |
C2—C1—Si1 | 174.85 (12) | C13—C12—C5 | 121.57 (10) |
C1—C2—C3 | 175.03 (13) | C17—C12—C5 | 119.36 (11) |
C4—C3—C2 | 126.26 (12) | C12—C13—C14 | 120.44 (12) |
C4—C3—H3 | 116.9 | C12—C13—H13 | 119.8 |
C2—C3—H3 | 116.9 | C14—C13—H13 | 119.8 |
C3—C4—C5 | 118.20 (10) | C15—C14—C13 | 119.92 (13) |
C3—C4—Si2 | 123.35 (9) | C15—C14—H14 | 120.0 |
C5—C4—Si2 | 118.43 (8) | C13—C14—H14 | 120.0 |
N1—C5—C12 | 107.86 (9) | C16—C15—C14 | 120.23 (12) |
N1—C5—C4 | 114.45 (9) | C16—C15—H15 | 119.9 |
C12—C5—C4 | 111.42 (9) | C14—C15—H15 | 119.9 |
N1—C5—H5 | 107.6 | C15—C16—C17 | 119.92 (13) |
C12—C5—H5 | 107.6 | C15—C16—H16 | 120.0 |
C4—C5—H5 | 107.6 | C17—C16—H16 | 120.0 |
Si1—C6—H6A | 109.5 | C16—C17—C12 | 120.51 (13) |
Si1—C6—H6B | 109.5 | C16—C17—H17 | 119.7 |
H6A—C6—H6B | 109.5 | C12—C17—H17 | 119.7 |
Si1—C6—H6C | 109.5 | N1—C18—C23 | 122.40 (11) |
H6A—C6—H6C | 109.5 | N1—C18—C19 | 119.22 (11) |
H6B—C6—H6C | 109.5 | C23—C18—C19 | 118.38 (12) |
Si1—C7—H7A | 109.5 | C20—C19—C18 | 120.40 (13) |
Si1—C7—H7B | 109.5 | C20—C19—H19 | 119.8 |
H7A—C7—H7B | 109.5 | C18—C19—H19 | 119.8 |
Si1—C7—H7C | 109.5 | C19—C20—C21 | 121.08 (14) |
H7A—C7—H7C | 109.5 | C19—C20—H20 | 119.5 |
H7B—C7—H7C | 109.5 | C21—C20—H20 | 119.5 |
Si1—C8—H8A | 109.5 | C22—C21—C20 | 118.75 (13) |
Si1—C8—H8B | 109.5 | C22—C21—H21 | 120.6 |
H8A—C8—H8B | 109.5 | C20—C21—H21 | 120.6 |
Si1—C8—H8C | 109.5 | C21—C22—C23 | 121.20 (13) |
H8A—C8—H8C | 109.5 | C21—C22—H22 | 119.4 |
H8B—C8—H8C | 109.5 | C23—C22—H22 | 119.4 |
Si2—C9—H9A | 109.5 | C22—C23—C18 | 120.19 (13) |
Si2—C9—H9B | 109.5 | C22—C23—H23 | 119.9 |
H9A—C9—H9B | 109.5 | C18—C23—H23 | 119.9 |
Si2—C9—H9C | 109.5 | C18—N1—C5 | 123.30 (10) |
H9A—C9—H9C | 109.5 | C18—N1—H1 | 116.6 (11) |
H9B—C9—H9C | 109.5 | C5—N1—H1 | 118.3 (11) |
Si2—C10—H10A | 109.5 | C1—Si1—C6 | 107.81 (6) |
Si2—C10—H10B | 109.5 | C1—Si1—C7 | 109.84 (7) |
H10A—C10—H10B | 109.5 | C6—Si1—C7 | 111.43 (8) |
Si2—C10—H10C | 109.5 | C1—Si1—C8 | 106.75 (7) |
H10A—C10—H10C | 109.5 | C6—Si1—C8 | 111.28 (8) |
H10B—C10—H10C | 109.5 | C7—Si1—C8 | 109.60 (7) |
Si2—C11—H11A | 109.5 | C9—Si2—C11 | 108.21 (6) |
Si2—C11—H11B | 109.5 | C9—Si2—C10 | 110.05 (6) |
H11A—C11—H11B | 109.5 | C11—Si2—C10 | 111.04 (6) |
Si2—C11—H11C | 109.5 | C9—Si2—C4 | 110.10 (6) |
H11A—C11—H11C | 109.5 | C11—Si2—C4 | 107.97 (5) |
H11B—C11—H11C | 109.5 | C10—Si2—C4 | 109.44 (6) |
C13—C12—C17 | 118.98 (11) | ||
C2—C3—C4—C5 | −174.92 (10) | N1—C18—C19—C20 | −179.19 (12) |
C2—C3—C4—Si2 | 3.72 (17) | C23—C18—C19—C20 | −0.21 (19) |
C3—C4—C5—N1 | −16.43 (14) | C18—C19—C20—C21 | −0.3 (2) |
Si2—C4—C5—N1 | 164.86 (7) | C19—C20—C21—C22 | 0.3 (2) |
C3—C4—C5—C12 | 106.27 (11) | C20—C21—C22—C23 | 0.2 (2) |
Si2—C4—C5—C12 | −72.45 (10) | C21—C22—C23—C18 | −0.6 (2) |
N1—C5—C12—C13 | 93.63 (13) | N1—C18—C23—C22 | 179.59 (12) |
C4—C5—C12—C13 | −32.78 (15) | C19—C18—C23—C22 | 0.65 (19) |
N1—C5—C12—C17 | −82.99 (13) | C23—C18—N1—C5 | 6.77 (18) |
C4—C5—C12—C17 | 150.60 (11) | C19—C18—N1—C5 | −174.29 (11) |
C17—C12—C13—C14 | 0.39 (18) | C12—C5—N1—C18 | 158.89 (10) |
C5—C12—C13—C14 | −176.24 (11) | C4—C5—N1—C18 | −76.51 (13) |
C12—C13—C14—C15 | 0.1 (2) | C3—C4—Si2—C9 | 46.86 (11) |
C13—C14—C15—C16 | −0.2 (2) | C5—C4—Si2—C9 | −134.49 (8) |
C14—C15—C16—C17 | −0.1 (2) | C3—C4—Si2—C11 | 164.81 (10) |
C15—C16—C17—C12 | 0.5 (2) | C5—C4—Si2—C11 | −16.55 (10) |
C13—C12—C17—C16 | −0.70 (19) | C3—C4—Si2—C10 | −74.21 (11) |
C5—C12—C17—C16 | 176.01 (11) | C5—C4—Si2—C10 | 104.43 (9) |
Acknowledgements
We thank our technical and analytical staff, in particular Kathleen Schubert, for assistance. Financial support by the Deutsche Forschungsgemeinschaft (RO 1269/9–1) and the Russian Foundation for Basic Research (Project code 15–03-03485) is gratefully acknowledged.
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