Anthracene derivative compounds are currently investigated because of their unique physical properties (e.g. bright luminescence and emission tunability), which make them ideal candidates for advanced optoelectronic devices. Intermolecular interactions are the basis of the tunability of the optical and electronic properties of these compounds, whose prediction and exploitation benefit from knowledge of the crystal structure and the packing architecture. Polymorphism can occur due to the weak intermolecular interactions, requiring detailed structural analysis to clarify the origin of observed material property modifications. Here, two silylethyne-substituted anthracene compounds are characterized by single-crystal synchrotron X-ray diffraction, identifying a new polymorph in the process. Additionally, laser confocal microscopy and fluorescence lifetime imaging microscopy confirm the results obtained by the X-ray diffraction characterization, i.e. shifting the substituents towards the external benzene rings of the anthracene unit favours π–π interactions, impacting on both the morphology and the microscopic optical properties of the crystals. The compounds with more isolated anthracene units feature shorter lifetime and emission spectra, more similar to those of isolated molecules. The crystallographic study, supported by the optical investigation, sheds light on the influence of non-covalent interactions on the crystal packing and luminescence properties of anthracene derivatives, providing a further step towards their efficient use as building blocks in active components of light sources and photonic networks.
Supporting information
CCDC references: 1962253; 1962254
For both structures, program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2014).
Crystal data top
C24H22F4Si2 | F(000) = 920 |
Mr = 442.59 | Dx = 1.208 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.72932 Å |
a = 6.9050 (14) Å | Cell parameters from 421 reflections |
b = 14.948 (3) Å | θ = 1.7–26.8° |
c = 23.660 (5) Å | µ = 0.19 mm−1 |
β = 94.82 (3)° | T = 296 K |
V = 2433.5 (8) Å3 | Needle, yellow |
Z = 4 | 0.09 × 0.01 × 0.01 mm |
Data collection top
Multi-axis PRIGo goniometer diffractometer | θmax = 26.8°, θmin = 1.7° |
ω scans, shutterless continuous rotation method | h = −8→8 |
62204 measured reflections | k = −18→18 |
4807 independent reflections | l = −29→29 |
3237 reflections with I > 2σ(I) | 4807 standard reflections every 0.00167 min |
Rint = 0.059 | intensity decay: 0.5% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0702P)2 + 0.5392P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
4807 reflections | Δρmax = 0.22 e Å−3 |
277 parameters | Δρmin = −0.32 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Si1 | 0.77925 (12) | 0.84835 (5) | 0.22633 (4) | 0.0897 (3) | |
Si2 | 0.64819 (16) | 1.45054 (5) | −0.09270 (4) | 0.1057 (3) | |
F1 | 0.7797 (2) | 0.80384 (8) | −0.00591 (6) | 0.0807 (4) | |
F2 | 0.7872 (2) | 0.77163 (10) | −0.11865 (7) | 0.1013 (5) | |
F3 | 0.7719 (3) | 0.90604 (13) | −0.19354 (6) | 0.1106 (6) | |
F4 | 0.7492 (2) | 1.07801 (10) | −0.15848 (6) | 0.0898 (4) | |
C1 | 0.7337 (3) | 1.08694 (14) | 0.11365 (9) | 0.0595 (5) | |
C2 | 0.7382 (3) | 1.06734 (12) | 0.05430 (8) | 0.0527 (4) | |
C3 | 0.7522 (3) | 0.97987 (12) | 0.03488 (8) | 0.0536 (5) | |
H3 | 0.7581 | 0.9331 | 0.0609 | 0.064* | |
C4 | 0.7576 (3) | 0.96084 (12) | −0.02229 (9) | 0.0539 (5) | |
C5 | 0.7715 (3) | 0.87214 (14) | −0.04318 (10) | 0.0636 (5) | |
C6 | 0.7754 (3) | 0.85560 (16) | −0.09880 (12) | 0.0739 (6) | |
C7 | 0.7679 (4) | 0.92591 (19) | −0.13812 (10) | 0.0771 (6) | |
C8 | 0.7559 (3) | 1.01123 (17) | −0.12058 (9) | 0.0685 (6) | |
C9 | 0.7493 (3) | 1.03292 (14) | −0.06245 (9) | 0.0569 (5) | |
C10 | 0.7343 (3) | 1.12031 (13) | −0.04307 (9) | 0.0595 (5) | |
H10 | 0.7281 | 1.1671 | −0.0691 | 0.071* | |
C11 | 0.7283 (3) | 1.13933 (12) | 0.01422 (9) | 0.0558 (5) | |
C12 | 0.7119 (3) | 1.22989 (13) | 0.03469 (10) | 0.0669 (6) | |
C13 | 0.7098 (4) | 1.24464 (15) | 0.09152 (12) | 0.0770 (6) | |
H13 | 0.7008 | 1.3031 | 0.1045 | 0.092* | |
C14 | 0.7207 (3) | 1.17456 (15) | 0.13110 (11) | 0.0717 (6) | |
H14 | 0.7193 | 1.1874 | 0.1695 | 0.086* | |
C15 | 0.7448 (3) | 1.01472 (15) | 0.15357 (9) | 0.0633 (5) | |
C16 | 0.7560 (3) | 0.95084 (16) | 0.18430 (10) | 0.0714 (6) | |
C17 | 0.9936 (5) | 0.8601 (3) | 0.27760 (17) | 0.1577 (19) | |
H17A | 1.0110 | 0.8063 | 0.2996 | 0.237* | |
H17B | 0.9748 | 0.9097 | 0.3024 | 0.237* | |
H17C | 1.1068 | 0.8705 | 0.2576 | 0.237* | |
C18 | 0.5596 (4) | 0.8325 (3) | 0.26395 (16) | 0.1257 (13) | |
H18A | 0.5786 | 0.7832 | 0.2898 | 0.189* | |
H18B | 0.4511 | 0.8203 | 0.2370 | 0.189* | |
H18C | 0.5345 | 0.8859 | 0.2847 | 0.189* | |
C19 | 0.8126 (9) | 0.7584 (3) | 0.1759 (2) | 0.200 (3) | |
H19A | 0.8515 | 0.7049 | 0.1962 | 0.300* | |
H19B | 0.9112 | 0.7752 | 0.1517 | 0.300* | |
H19C | 0.6926 | 0.7479 | 0.1534 | 0.300* | |
C20 | 0.6958 (4) | 1.30201 (14) | −0.00519 (12) | 0.0808 (7) | |
C21 | 0.6799 (5) | 1.36126 (16) | −0.03916 (14) | 0.0945 (8) | |
C22 | 0.3877 (6) | 1.4793 (3) | −0.10196 (18) | 0.1435 (15) | |
H22A | 0.3630 | 1.5156 | −0.1353 | 0.215* | |
H22B | 0.3524 | 1.5118 | −0.0694 | 0.215* | |
H22C | 0.3121 | 1.4254 | −0.1061 | 0.215* | |
C23 | 0.7880 (8) | 1.5485 (2) | −0.06689 (19) | 0.1564 (17) | |
H23A | 0.7752 | 1.5950 | −0.0950 | 0.235* | |
H23B | 0.9224 | 1.5325 | −0.0598 | 0.235* | |
H23C | 0.7396 | 1.5695 | −0.0324 | 0.235* | |
C24 | 0.7293 (8) | 1.4056 (3) | −0.15961 (18) | 0.1625 (18) | |
H24A | 0.6947 | 1.4468 | −0.1900 | 0.244* | |
H24B | 0.6676 | 1.3490 | −0.1679 | 0.244* | |
H24C | 0.8678 | 1.3978 | −0.1557 | 0.244* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0933 (5) | 0.0888 (5) | 0.0896 (5) | 0.0186 (4) | 0.0234 (4) | 0.0364 (4) |
Si2 | 0.1574 (9) | 0.0561 (4) | 0.1054 (6) | 0.0177 (4) | 0.0213 (6) | 0.0216 (4) |
F1 | 0.0933 (9) | 0.0467 (7) | 0.1017 (10) | 0.0006 (6) | 0.0063 (8) | 0.0056 (6) |
F2 | 0.1177 (12) | 0.0757 (9) | 0.1104 (12) | −0.0027 (8) | 0.0082 (9) | −0.0338 (8) |
F3 | 0.1314 (13) | 0.1274 (14) | 0.0730 (10) | −0.0060 (11) | 0.0087 (9) | −0.0245 (10) |
F4 | 0.1034 (10) | 0.1000 (10) | 0.0660 (8) | 0.0003 (8) | 0.0061 (7) | 0.0221 (7) |
C1 | 0.0573 (11) | 0.0557 (11) | 0.0655 (12) | −0.0003 (9) | 0.0051 (9) | 0.0047 (9) |
C2 | 0.0470 (10) | 0.0470 (10) | 0.0638 (12) | 0.0002 (8) | 0.0041 (8) | 0.0076 (8) |
C3 | 0.0504 (10) | 0.0461 (10) | 0.0640 (12) | 0.0001 (8) | 0.0034 (8) | 0.0112 (9) |
C4 | 0.0465 (10) | 0.0480 (10) | 0.0666 (12) | −0.0018 (8) | 0.0018 (8) | 0.0044 (9) |
C5 | 0.0575 (12) | 0.0554 (11) | 0.0773 (14) | −0.0030 (9) | 0.0017 (10) | 0.0001 (10) |
C6 | 0.0698 (14) | 0.0645 (13) | 0.0872 (17) | −0.0032 (11) | 0.0050 (12) | −0.0161 (12) |
C7 | 0.0744 (15) | 0.0929 (18) | 0.0638 (14) | −0.0051 (13) | 0.0037 (11) | −0.0137 (13) |
C8 | 0.0638 (13) | 0.0790 (15) | 0.0619 (13) | −0.0023 (11) | 0.0013 (10) | 0.0101 (11) |
C9 | 0.0483 (10) | 0.0593 (11) | 0.0626 (12) | −0.0019 (8) | 0.0016 (8) | 0.0070 (9) |
C10 | 0.0565 (11) | 0.0529 (11) | 0.0689 (13) | −0.0007 (9) | 0.0031 (9) | 0.0169 (10) |
C11 | 0.0525 (10) | 0.0447 (10) | 0.0698 (13) | −0.0010 (8) | 0.0027 (9) | 0.0084 (9) |
C12 | 0.0684 (13) | 0.0462 (11) | 0.0861 (16) | 0.0013 (9) | 0.0059 (11) | 0.0076 (10) |
C13 | 0.0890 (16) | 0.0477 (11) | 0.0941 (18) | 0.0026 (11) | 0.0069 (13) | −0.0059 (11) |
C14 | 0.0800 (15) | 0.0632 (13) | 0.0717 (14) | 0.0022 (11) | 0.0047 (11) | −0.0060 (11) |
C15 | 0.0642 (12) | 0.0654 (12) | 0.0605 (12) | 0.0023 (10) | 0.0065 (9) | 0.0042 (10) |
C16 | 0.0763 (15) | 0.0776 (15) | 0.0608 (13) | 0.0045 (11) | 0.0087 (11) | 0.0089 (11) |
C17 | 0.089 (2) | 0.246 (5) | 0.138 (3) | 0.024 (3) | 0.009 (2) | 0.109 (3) |
C18 | 0.089 (2) | 0.162 (3) | 0.129 (3) | 0.006 (2) | 0.0206 (18) | 0.077 (2) |
C19 | 0.297 (7) | 0.089 (3) | 0.227 (6) | 0.027 (3) | 0.096 (5) | 0.005 (3) |
C20 | 0.0915 (17) | 0.0479 (12) | 0.1032 (19) | 0.0036 (11) | 0.0092 (14) | 0.0097 (12) |
C21 | 0.117 (2) | 0.0529 (13) | 0.114 (2) | 0.0075 (13) | 0.0113 (17) | 0.0174 (14) |
C22 | 0.175 (4) | 0.105 (3) | 0.150 (3) | 0.050 (3) | 0.003 (3) | 0.017 (2) |
C23 | 0.236 (5) | 0.078 (2) | 0.155 (4) | −0.031 (3) | 0.013 (3) | 0.034 (2) |
C24 | 0.246 (5) | 0.113 (3) | 0.136 (3) | 0.037 (3) | 0.063 (3) | 0.010 (3) |
Geometric parameters (Å, º) top
Si1—C19 | 1.825 (5) | C10—H10 | 0.9300 |
Si1—C16 | 1.826 (2) | C11—C12 | 1.445 (3) |
Si1—C18 | 1.837 (3) | C12—C13 | 1.364 (3) |
Si1—C17 | 1.842 (4) | C12—C20 | 1.431 (3) |
Si2—C23 | 1.831 (4) | C13—C14 | 1.403 (3) |
Si2—C21 | 1.841 (3) | C13—H13 | 0.9300 |
Si2—C22 | 1.844 (4) | C14—H14 | 0.9300 |
Si2—C24 | 1.849 (4) | C15—C16 | 1.199 (3) |
F1—C5 | 1.347 (2) | C17—H17A | 0.9600 |
F2—C6 | 1.345 (3) | C17—H17B | 0.9600 |
F3—C7 | 1.347 (3) | C17—H17C | 0.9600 |
F4—C8 | 1.340 (3) | C18—H18A | 0.9600 |
C1—C14 | 1.378 (3) | C18—H18B | 0.9600 |
C1—C15 | 1.432 (3) | C18—H18C | 0.9600 |
C1—C2 | 1.437 (3) | C19—H19A | 0.9600 |
C2—C3 | 1.392 (3) | C19—H19B | 0.9600 |
C2—C11 | 1.432 (3) | C19—H19C | 0.9600 |
C3—C4 | 1.386 (3) | C20—C21 | 1.195 (3) |
C3—H3 | 0.9300 | C22—H22A | 0.9600 |
C4—C5 | 1.421 (3) | C22—H22B | 0.9600 |
C4—C9 | 1.435 (3) | C22—H22C | 0.9600 |
C5—C6 | 1.341 (3) | C23—H23A | 0.9600 |
C6—C7 | 1.402 (4) | C23—H23B | 0.9600 |
C7—C8 | 1.346 (3) | C23—H23C | 0.9600 |
C8—C9 | 1.418 (3) | C24—H24A | 0.9600 |
C9—C10 | 1.391 (3) | C24—H24B | 0.9600 |
C10—C11 | 1.389 (3) | C24—H24C | 0.9600 |
| | | |
C19—Si1—C16 | 105.79 (18) | C20—C12—C11 | 119.3 (2) |
C19—Si1—C18 | 112.1 (2) | C12—C13—C14 | 122.2 (2) |
C16—Si1—C18 | 109.48 (13) | C12—C13—H13 | 118.9 |
C19—Si1—C17 | 111.3 (3) | C14—C13—H13 | 118.9 |
C16—Si1—C17 | 107.91 (16) | C1—C14—C13 | 120.7 (2) |
C18—Si1—C17 | 110.11 (17) | C1—C14—H14 | 119.6 |
C23—Si2—C21 | 108.76 (17) | C13—C14—H14 | 119.6 |
C23—Si2—C22 | 109.6 (2) | C16—C15—C1 | 176.0 (2) |
C21—Si2—C22 | 108.01 (17) | C15—C16—Si1 | 175.4 (2) |
C23—Si2—C24 | 112.8 (2) | Si1—C17—H17A | 109.5 |
C21—Si2—C24 | 107.39 (16) | Si1—C17—H17B | 109.5 |
C22—Si2—C24 | 110.2 (2) | H17A—C17—H17B | 109.5 |
C14—C1—C15 | 121.3 (2) | Si1—C17—H17C | 109.5 |
C14—C1—C2 | 119.58 (19) | H17A—C17—H17C | 109.5 |
C15—C1—C2 | 119.09 (18) | H17B—C17—H17C | 109.5 |
C3—C2—C11 | 119.21 (18) | Si1—C18—H18A | 109.5 |
C3—C2—C1 | 121.45 (17) | Si1—C18—H18B | 109.5 |
C11—C2—C1 | 119.34 (17) | H18A—C18—H18B | 109.5 |
C4—C3—C2 | 121.55 (17) | Si1—C18—H18C | 109.5 |
C4—C3—H3 | 119.2 | H18A—C18—H18C | 109.5 |
C2—C3—H3 | 119.2 | H18B—C18—H18C | 109.5 |
C3—C4—C5 | 122.62 (18) | Si1—C19—H19A | 109.5 |
C3—C4—C9 | 119.30 (18) | Si1—C19—H19B | 109.5 |
C5—C4—C9 | 118.07 (19) | H19A—C19—H19B | 109.5 |
C6—C5—F1 | 119.9 (2) | Si1—C19—H19C | 109.5 |
C6—C5—C4 | 121.4 (2) | H19A—C19—H19C | 109.5 |
F1—C5—C4 | 118.7 (2) | H19B—C19—H19C | 109.5 |
C5—C6—F2 | 121.4 (2) | C21—C20—C12 | 178.7 (3) |
C5—C6—C7 | 120.7 (2) | C20—C21—Si2 | 178.0 (3) |
F2—C6—C7 | 117.9 (2) | Si2—C22—H22A | 109.5 |
C8—C7—F3 | 121.1 (2) | Si2—C22—H22B | 109.5 |
C8—C7—C6 | 120.4 (2) | H22A—C22—H22B | 109.5 |
F3—C7—C6 | 118.6 (2) | Si2—C22—H22C | 109.5 |
F4—C8—C7 | 120.0 (2) | H22A—C22—H22C | 109.5 |
F4—C8—C9 | 118.5 (2) | H22B—C22—H22C | 109.5 |
C7—C8—C9 | 121.6 (2) | Si2—C23—H23A | 109.5 |
C10—C9—C8 | 122.95 (19) | Si2—C23—H23B | 109.5 |
C10—C9—C4 | 119.14 (19) | H23A—C23—H23B | 109.5 |
C8—C9—C4 | 117.91 (19) | Si2—C23—H23C | 109.5 |
C11—C10—C9 | 121.53 (18) | H23A—C23—H23C | 109.5 |
C11—C10—H10 | 119.2 | H23B—C23—H23C | 109.5 |
C9—C10—H10 | 119.2 | Si2—C24—H24A | 109.5 |
C10—C11—C2 | 119.26 (18) | Si2—C24—H24B | 109.5 |
C10—C11—C12 | 121.89 (18) | H24A—C24—H24B | 109.5 |
C2—C11—C12 | 118.86 (19) | Si2—C24—H24C | 109.5 |
C13—C12—C20 | 121.4 (2) | H24A—C24—H24C | 109.5 |
C13—C12—C11 | 119.3 (2) | H24B—C24—H24C | 109.5 |
| | | |
C14—C1—C2—C3 | 179.66 (19) | C7—C8—C9—C10 | −179.1 (2) |
C15—C1—C2—C3 | 0.3 (3) | F4—C8—C9—C4 | −179.70 (17) |
C14—C1—C2—C11 | −0.3 (3) | C7—C8—C9—C4 | 0.5 (3) |
C15—C1—C2—C11 | −179.63 (18) | C3—C4—C9—C10 | −0.6 (3) |
C11—C2—C3—C4 | 0.3 (3) | C5—C4—C9—C10 | 179.53 (18) |
C1—C2—C3—C4 | −179.67 (17) | C3—C4—C9—C8 | 179.75 (18) |
C2—C3—C4—C5 | −179.87 (18) | C5—C4—C9—C8 | −0.1 (3) |
C2—C3—C4—C9 | 0.3 (3) | C8—C9—C10—C11 | −179.96 (19) |
C3—C4—C5—C6 | 179.7 (2) | C4—C9—C10—C11 | 0.4 (3) |
C9—C4—C5—C6 | −0.5 (3) | C9—C10—C11—C2 | 0.1 (3) |
C3—C4—C5—F1 | 0.0 (3) | C9—C10—C11—C12 | −179.77 (19) |
C9—C4—C5—F1 | 179.88 (17) | C3—C2—C11—C10 | −0.4 (3) |
F1—C5—C6—F2 | 0.1 (3) | C1—C2—C11—C10 | 179.48 (17) |
C4—C5—C6—F2 | −179.55 (19) | C3—C2—C11—C12 | 179.43 (18) |
F1—C5—C6—C7 | −179.7 (2) | C1—C2—C11—C12 | −0.6 (3) |
C4—C5—C6—C7 | 0.7 (4) | C10—C11—C12—C13 | −179.0 (2) |
C5—C6—C7—C8 | −0.2 (4) | C2—C11—C12—C13 | 1.1 (3) |
F2—C6—C7—C8 | 180.0 (2) | C10—C11—C12—C20 | 1.8 (3) |
C5—C6—C7—F3 | −179.9 (2) | C2—C11—C12—C20 | −178.1 (2) |
F2—C6—C7—F3 | 0.3 (3) | C20—C12—C13—C14 | 178.4 (2) |
F3—C7—C8—F4 | −0.5 (3) | C11—C12—C13—C14 | −0.8 (4) |
C6—C7—C8—F4 | 179.9 (2) | C15—C1—C14—C13 | −180.0 (2) |
F3—C7—C8—C9 | 179.3 (2) | C2—C1—C14—C13 | 0.7 (3) |
C6—C7—C8—C9 | −0.4 (4) | C12—C13—C14—C1 | −0.2 (4) |
F4—C8—C9—C10 | 0.7 (3) | | |
Crystal data top
C36H50Si2 | Z = 1 |
Mr = 538.94 | F(000) = 294 |
Triclinic, P1 | Dx = 1.084 Mg m−3 |
a = 8.6020 (17) Å | Synchrotron radiation, λ = 0.72932 Å |
b = 10.085 (2) Å | Cell parameters from 1335 reflections |
c = 11.209 (2) Å | θ = 2.2–31.5° |
α = 115.07 (3)° | µ = 0.14 mm−1 |
β = 102.61 (3)° | T = 296 K |
γ = 98.82 (3)° | Block, yellow |
V = 825.6 (4) Å3 | 0.09 × 0.08 × 0.08 mm |
Data collection top
Multi-axis PRIGo goniometer diffractometer | θmax = 31.5°, θmin = 2.2° |
ω scans, shutterless continuous rotation method | h = −12→12 |
27676 measured reflections | k = −14→14 |
4620 independent reflections | l = −15→16 |
4447 reflections with I > 2σ(I) | 4620 standard reflections every 0.00167 min |
Rint = 0.026 | intensity decay: 0.5% |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0706P)2 + 0.1231P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
4620 reflections | Δρmax = 0.32 e Å−3 |
178 parameters | Δρmin = −0.32 e Å−3 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Si1 | 0.18459 (3) | 0.18680 (3) | 0.32597 (2) | 0.03045 (9) | |
C1 | 0.12184 (13) | 0.29554 (12) | 0.23562 (11) | 0.0383 (2) | |
C2 | 0.04121 (12) | 0.43215 (10) | 0.08574 (9) | 0.03209 (18) | |
C3 | −0.12671 (11) | 0.40482 (10) | 0.01398 (9) | 0.03191 (18) | |
C4 | 0.16818 (11) | 0.52677 (10) | 0.07290 (9) | 0.03271 (18) | |
C5 | 0.14913 (14) | 0.27582 (12) | 0.49964 (10) | 0.0399 (2) | |
H5 | 0.1746 | 0.2134 | 0.5445 | 0.048* | |
C6 | 0.08369 (13) | 0.35981 (11) | 0.16930 (10) | 0.0363 (2) | |
C7 | 0.05679 (13) | −0.01820 (12) | 0.21266 (11) | 0.0395 (2) | |
H7 | 0.1102 | −0.0643 | 0.1424 | 0.047* | |
C8 | 0.41254 (13) | 0.20975 (14) | 0.35141 (12) | 0.0443 (2) | |
H8 | 0.4682 | 0.3188 | 0.4105 | 0.053* | |
C9 | −0.25754 (13) | 0.30944 (12) | 0.02455 (11) | 0.0403 (2) | |
H9 | −0.2325 | 0.2646 | 0.0810 | 0.048* | |
C10 | 0.33841 (13) | 0.55747 (14) | 0.14507 (12) | 0.0439 (2) | |
H10 | 0.3673 | 0.5137 | 0.2019 | 0.053* | |
C11 | −0.41805 (15) | 0.28305 (15) | −0.04652 (13) | 0.0495 (3) | |
H11 | −0.5017 | 0.2200 | −0.0386 | 0.059* | |
C12 | 0.45931 (14) | 0.64956 (16) | 0.13241 (14) | 0.0523 (3) | |
H12 | 0.5698 | 0.6683 | 0.1805 | 0.063* | |
C13 | −0.03051 (18) | 0.27784 (18) | 0.48561 (15) | 0.0568 (3) | |
H13A | −0.1008 | 0.1751 | 0.4377 | 0.085* | |
H13B | −0.0624 | 0.3302 | 0.4341 | 0.085* | |
H13C | −0.0416 | 0.3295 | 0.5763 | 0.085* | |
C14 | 0.45544 (17) | 0.16374 (19) | 0.21661 (16) | 0.0597 (3) | |
H14A | 0.4160 | 0.2215 | 0.1731 | 0.090* | |
H14B | 0.4037 | 0.0570 | 0.1552 | 0.090* | |
H14C | 0.5735 | 0.1838 | 0.2369 | 0.090* | |
C15 | 0.2658 (2) | 0.43708 (16) | 0.59437 (14) | 0.0606 (3) | |
H15A | 0.3788 | 0.4329 | 0.6096 | 0.091* | |
H15B | 0.2446 | 0.4793 | 0.6817 | 0.091* | |
H15C | 0.2471 | 0.5000 | 0.5511 | 0.091* | |
C16 | 0.0579 (2) | −0.10950 (15) | 0.29180 (16) | 0.0649 (4) | |
H16A | 0.1703 | −0.1015 | 0.3362 | 0.097* | |
H16B | −0.0002 | −0.2145 | 0.2282 | 0.097* | |
H16C | 0.0042 | −0.0699 | 0.3608 | 0.097* | |
C17 | −0.12106 (17) | −0.03768 (17) | 0.13345 (16) | 0.0635 (4) | |
H17A | −0.1197 | 0.0169 | 0.0812 | 0.095* | |
H17B | −0.1803 | 0.0017 | 0.1981 | 0.095* | |
H17C | −0.1749 | −0.1439 | 0.0713 | 0.095* | |
C18 | 0.4854 (2) | 0.1290 (3) | 0.4289 (2) | 0.0851 (6) | |
H18A | 0.4509 | 0.1540 | 0.5098 | 0.128* | |
H18B | 0.6042 | 0.1615 | 0.4564 | 0.128* | |
H18C | 0.4469 | 0.0208 | 0.3692 | 0.128* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.03174 (14) | 0.03600 (15) | 0.03312 (14) | 0.01022 (9) | 0.00693 (9) | 0.02610 (12) |
C1 | 0.0423 (5) | 0.0439 (5) | 0.0393 (5) | 0.0140 (4) | 0.0096 (4) | 0.0301 (4) |
C2 | 0.0414 (4) | 0.0338 (4) | 0.0297 (4) | 0.0147 (3) | 0.0091 (3) | 0.0222 (4) |
C3 | 0.0394 (4) | 0.0332 (4) | 0.0308 (4) | 0.0132 (3) | 0.0102 (3) | 0.0214 (4) |
C4 | 0.0387 (4) | 0.0350 (4) | 0.0313 (4) | 0.0139 (3) | 0.0083 (3) | 0.0218 (4) |
C5 | 0.0495 (5) | 0.0438 (5) | 0.0356 (4) | 0.0168 (4) | 0.0121 (4) | 0.0264 (4) |
C6 | 0.0434 (5) | 0.0396 (5) | 0.0352 (4) | 0.0150 (4) | 0.0102 (4) | 0.0259 (4) |
C7 | 0.0447 (5) | 0.0380 (5) | 0.0393 (5) | 0.0088 (4) | 0.0134 (4) | 0.0223 (4) |
C8 | 0.0345 (4) | 0.0566 (6) | 0.0524 (6) | 0.0121 (4) | 0.0107 (4) | 0.0367 (5) |
C9 | 0.0454 (5) | 0.0444 (5) | 0.0431 (5) | 0.0128 (4) | 0.0149 (4) | 0.0309 (4) |
C10 | 0.0405 (5) | 0.0544 (6) | 0.0457 (5) | 0.0149 (4) | 0.0061 (4) | 0.0348 (5) |
C11 | 0.0424 (5) | 0.0578 (7) | 0.0580 (7) | 0.0097 (5) | 0.0157 (5) | 0.0375 (6) |
C12 | 0.0376 (5) | 0.0670 (8) | 0.0588 (7) | 0.0119 (5) | 0.0071 (5) | 0.0403 (6) |
C13 | 0.0586 (7) | 0.0679 (8) | 0.0598 (7) | 0.0280 (6) | 0.0298 (6) | 0.0356 (7) |
C14 | 0.0495 (6) | 0.0780 (9) | 0.0670 (8) | 0.0211 (6) | 0.0280 (6) | 0.0422 (7) |
C15 | 0.0700 (8) | 0.0508 (7) | 0.0455 (6) | 0.0132 (6) | 0.0061 (6) | 0.0161 (6) |
C16 | 0.0935 (11) | 0.0435 (6) | 0.0630 (8) | 0.0069 (6) | 0.0211 (7) | 0.0358 (6) |
C17 | 0.0451 (6) | 0.0599 (8) | 0.0617 (8) | 0.0019 (5) | 0.0011 (5) | 0.0198 (6) |
C18 | 0.0542 (8) | 0.1471 (18) | 0.1147 (14) | 0.0528 (10) | 0.0306 (9) | 0.1055 (15) |
Geometric parameters (Å, º) top
Si1—C1 | 1.8449 (11) | C10—H10 | 0.9300 |
Si1—C8 | 1.8816 (11) | C11—C12i | 1.4120 (16) |
Si1—C5 | 1.8843 (12) | C11—H11 | 0.9300 |
Si1—C7 | 1.8877 (15) | C12—C11i | 1.4120 (16) |
C1—C6 | 1.2031 (13) | C12—H12 | 0.9300 |
C2—C4 | 1.4106 (14) | C13—H13A | 0.9600 |
C2—C3 | 1.4114 (13) | C13—H13B | 0.9600 |
C2—C6 | 1.4334 (12) | C13—H13C | 0.9600 |
C3—C9 | 1.4242 (14) | C14—H14A | 0.9600 |
C3—C4i | 1.4300 (12) | C14—H14B | 0.9600 |
C4—C10 | 1.4233 (14) | C14—H14C | 0.9600 |
C4—C3i | 1.4299 (11) | C15—H15A | 0.9600 |
C5—C13 | 1.5229 (17) | C15—H15B | 0.9600 |
C5—C15 | 1.533 (2) | C15—H15C | 0.9600 |
C5—H5 | 0.9800 | C16—H16A | 0.9600 |
C7—C16 | 1.5251 (16) | C16—H16B | 0.9600 |
C7—C17 | 1.5278 (18) | C16—H16C | 0.9600 |
C7—H7 | 0.9800 | C17—H17A | 0.9600 |
C8—C18 | 1.5258 (17) | C17—H17B | 0.9600 |
C8—C14 | 1.5285 (18) | C17—H17C | 0.9600 |
C8—H8 | 0.9800 | C18—H18A | 0.9600 |
C9—C11 | 1.3561 (16) | C18—H18B | 0.9600 |
C9—H9 | 0.9300 | C18—H18C | 0.9600 |
C10—C12 | 1.3580 (17) | | |
| | | |
C1—Si1—C8 | 106.22 (5) | C9—C11—H11 | 119.7 |
C1—Si1—C5 | 107.65 (5) | C12i—C11—H11 | 119.7 |
C8—Si1—C5 | 109.92 (6) | C10—C12—C11i | 120.32 (11) |
C1—Si1—C7 | 107.78 (5) | C10—C12—H12 | 119.8 |
C8—Si1—C7 | 112.32 (6) | C11i—C12—H12 | 119.8 |
C5—Si1—C7 | 112.61 (6) | C5—C13—H13A | 109.5 |
C6—C1—Si1 | 175.59 (10) | C5—C13—H13B | 109.5 |
C4—C2—C3 | 120.57 (8) | H13A—C13—H13B | 109.5 |
C4—C2—C6 | 119.59 (8) | C5—C13—H13C | 109.5 |
C3—C2—C6 | 119.82 (9) | H13A—C13—H13C | 109.5 |
C2—C3—C9 | 121.84 (8) | H13B—C13—H13C | 109.5 |
C2—C3—C4i | 119.63 (8) | C8—C14—H14A | 109.5 |
C9—C3—C4i | 118.53 (9) | C8—C14—H14B | 109.5 |
C2—C4—C10 | 121.77 (8) | H14A—C14—H14B | 109.5 |
C2—C4—C3i | 119.80 (8) | C8—C14—H14C | 109.5 |
C10—C4—C3i | 118.43 (9) | H14A—C14—H14C | 109.5 |
C13—C5—C15 | 110.31 (11) | H14B—C14—H14C | 109.5 |
C13—C5—Si1 | 112.25 (9) | C5—C15—H15A | 109.5 |
C15—C5—Si1 | 111.48 (9) | C5—C15—H15B | 109.5 |
C13—C5—H5 | 107.5 | H15A—C15—H15B | 109.5 |
C15—C5—H5 | 107.5 | C5—C15—H15C | 109.5 |
Si1—C5—H5 | 107.5 | H15A—C15—H15C | 109.5 |
C1—C6—C2 | 177.43 (11) | H15B—C15—H15C | 109.5 |
C16—C7—C17 | 110.38 (11) | C7—C16—H16A | 109.5 |
C16—C7—Si1 | 112.71 (8) | C7—C16—H16B | 109.5 |
C17—C7—Si1 | 114.07 (9) | H16A—C16—H16B | 109.5 |
C16—C7—H7 | 106.4 | C7—C16—H16C | 109.5 |
C17—C7—H7 | 106.4 | H16A—C16—H16C | 109.5 |
Si1—C7—H7 | 106.4 | H16B—C16—H16C | 109.5 |
C18—C8—C14 | 110.76 (12) | C7—C17—H17A | 109.5 |
C18—C8—Si1 | 112.81 (9) | C7—C17—H17B | 109.5 |
C14—C8—Si1 | 113.35 (9) | H17A—C17—H17B | 109.5 |
C18—C8—H8 | 106.5 | C7—C17—H17C | 109.5 |
C14—C8—H8 | 106.5 | H17A—C17—H17C | 109.5 |
Si1—C8—H8 | 106.5 | H17B—C17—H17C | 109.5 |
C11—C9—C3 | 120.98 (9) | C8—C18—H18A | 109.5 |
C11—C9—H9 | 119.5 | C8—C18—H18B | 109.5 |
C3—C9—H9 | 119.5 | H18A—C18—H18B | 109.5 |
C12—C10—C4 | 121.14 (10) | C8—C18—H18C | 109.5 |
C12—C10—H10 | 119.4 | H18A—C18—H18C | 109.5 |
C4—C10—H10 | 119.4 | H18B—C18—H18C | 109.5 |
C9—C11—C12i | 120.59 (11) | | |
| | | |
C4—C2—C3—C9 | 179.79 (9) | C5—Si1—C7—C16 | −44.13 (11) |
C6—C2—C3—C9 | 1.58 (14) | C1—Si1—C7—C17 | −35.82 (10) |
C4—C2—C3—C4i | 0.26 (15) | C8—Si1—C7—C17 | −152.49 (9) |
C6—C2—C3—C4i | −177.94 (8) | C5—Si1—C7—C17 | 82.76 (10) |
C3—C2—C4—C10 | 179.40 (9) | C1—Si1—C8—C18 | 178.52 (12) |
C6—C2—C4—C10 | −2.39 (15) | C5—Si1—C8—C18 | 62.33 (13) |
C3—C2—C4—C3i | −0.26 (15) | C7—Si1—C8—C18 | −63.88 (13) |
C6—C2—C4—C3i | 177.95 (8) | C1—Si1—C8—C14 | −54.59 (11) |
C1—Si1—C5—C13 | 57.78 (10) | C5—Si1—C8—C14 | −170.77 (9) |
C8—Si1—C5—C13 | 173.07 (8) | C7—Si1—C8—C14 | 63.01 (11) |
C7—Si1—C5—C13 | −60.88 (10) | C2—C3—C9—C11 | −179.20 (10) |
C1—Si1—C5—C15 | −66.56 (9) | C4i—C3—C9—C11 | 0.34 (16) |
C8—Si1—C5—C15 | 48.73 (10) | C2—C4—C10—C12 | −179.58 (11) |
C7—Si1—C5—C15 | 174.78 (8) | C3i—C4—C10—C12 | 0.08 (17) |
C1—Si1—C7—C16 | −162.71 (10) | C3—C9—C11—C12i | −0.33 (19) |
C8—Si1—C7—C16 | 80.62 (11) | C4—C10—C12—C11i | −0.1 (2) |
Symmetry code: (i) −x, −y+1, −z. |