Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017963/ww6110sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017963/ww6110Isup2.hkl |
CCDC reference: 222888
Key indicators
- Single-crystal synchrotron study
- T = 150 K
- Mean (C-C) = 0.005 Å
- R factor = 0.081
- wR factor = 0.187
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.98 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.15 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.38 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.55 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Si21 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C5 - C6 = 1.46 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C105 - C106 = 1.44 Ang. PLAT371_ALERT_2_C Long C(sp2)-C(sp1) Bond C205 - C206 = 1.45 Ang. PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N101 - H101 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N201 - H201 ... ? PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 SI1 -C4 -C5 -C6 0.00 26.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 2 C4 -C5 -C6 -C11 152.00 21.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3 C4 -C5 -C6 -C7 -27.00 21.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 32 SI11-C104-C105-C106 65.00 16.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 33 C104-C105-C106-C111 140.00 6.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 34 C104-C105-C106-C107 -39.00 6.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 63 SI21-C204-C205-C206 89.00 22.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 64 C204-C205-C206-C211 141.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 65 C204-C205-C206-C207 -37.00 8.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 94 C5 -C4 -SI1 -C1 -2.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 95 C5 -C4 -SI1 -C3 117.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 96 C5 -C4 -SI1 -C2 -123.00 7.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 97 C105-C104-SI11-C102 7.00 13.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 98 C105-C104-SI11-C101 128.00 13.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 99 C105-C104-SI11-C103 -110.00 13.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 100 C205-C204-SI21-C203 105.00 21.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 101 C205-C204-SI21-C202 -16.00 21.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 102 C205-C204-SI21-C201 -135.00 21.00 1.555 1.555 1.555 1.555 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C17 H17 N Si
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 32 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 9 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 19 ALERT type 4 Improvement, methodology, query or suggestion
3-Trimethylsilylethynylcarbazole was synthesized by the following procedure. To a stirred solution of 3-bromocarbazole (2.0 g, 6.13 mmol) in iPr2NH/THF (70 ml, 1:1 v/v) under nitrogen was added a catalyst mixture of CuI (15 mg), Pd(OAc)2 (15 mg) and PPh3 (50 mg). The solution was stirred for 20 min. at 323 K and then trimethylsilylethyne (1.5 g, 15.3 mmol) was added and the mixture stirred for another 20 min. The reaction temperature was then raised to 348 K and left with stirring for 20 h. The completion of the reaction was determined by silica TLC and IR spectroscopy. The solution was allowed to cool down to room temperature. The crude product was filtered to eliminate the ammonium salt and the solvent was removed under vacuum. The residue was subjected to silica column chromatography using hexane/CH2Cl2 (1:1) as eluant to afford the target compound as a colorless solid in 77% yield.
Aromatic and methyl H atoms were constrained as riding atoms, fixed to the parent atoms with distances of 0.95 Å and 0.98 Å respectively. The isotropic distplacement parameters were fixed to 120% of that of the parent atom for aromatic and 150% for methyl H atoms.
In this paper, we report the structural characterization of the title compound, (I), which is a TMS-protected mono-alkyne and a precursor of the mononuclear platinum(II) di-yne species, trans-[Pt(PnBu3)2(—C≡ CR)2] (R = carbazol-3-yl). Such platinum-containing species form the building blocks for rigid-rod orgnaometallic poly-ynes of general formula trans-[Pt(PnBu3)2—C≡C—R—C≡C—]∞ (R = aromatic or heteroaromatic linker unit). Platinum poly-ynes are of immense current interest due to π-electron conjugation along the backbone, novel donor-acceptor interactions between the metal centres and the conjugated ligands and the unique photophysical properties arising from the large spin-orbit coupling (Wittmann et al., 1994; Beljonne et al., 1996; Younus et al., 1998; Chawdhury et al., 1998, 1999; Wilson et al., 2000, 2001; Khan, Al-Mandhary, Al-Suti, Feeder et al., 2002; Khan, Al-Mandhary, Al-Suti, Hisahm et al., 2002; Khan, Al-Mandhary, Al-Suti, Ahrens et al., 2003; Khan, Al-Mandhary, Al-Suti, Corcoran et al., 2003; Khan, Al-Suti et al., 2003). Precursors to these species, such as the title compound, are studied as models of the molecular and electronic properties and structurep-property relationships in the metal poly-ynes.
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX publication routines (Farrugia, 1999).
Fig. 1. The molecular structure of 3-trimethylsilylethynylcarbazole, showing the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. |
[Si(CH3)3(C14H8N)] | F(000) = 1680 |
Mr = 263.41 | Dx = 1.196 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.688 Å |
Hall symbol: -P 2ybc | Cell parameters from 13603 reflections |
a = 33.402 (3) Å | θ = 2.3–29.1° |
b = 5.8135 (4) Å | µ = 0.15 mm−1 |
c = 22.8511 (17) Å | T = 150 K |
β = 98.394 (2)° | Plate, white |
V = 4389.7 (6) Å3 | 0.2 × 0.2 × 0.04 mm |
Z = 12 |
Bruker AXS SMART 1K CCD diffractometer | 5999 reflections with I > 2σ(I) |
ω rotation with narrow frames scans | Rint = 0.047 |
Absorption correction: multi-scan (SADABS; Siemens, 1996) | θmax = 24.5°, θmin = 3.4° |
Tmin = 0.971, Tmax = 0.994 | h = −39→40 |
21435 measured reflections | k = −7→6 |
7939 independent reflections | l = −20→27 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.081 | w = 1/[σ2(Fo2) + (0.0602P)2 + 9.4726P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.187 | (Δ/σ)max = 0.001 |
S = 1.14 | Δρmax = 0.37 e Å−3 |
7939 reflections | Δρmin = −0.42 e Å−3 |
514 parameters |
[Si(CH3)3(C14H8N)] | V = 4389.7 (6) Å3 |
Mr = 263.41 | Z = 12 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.688 Å |
a = 33.402 (3) Å | µ = 0.15 mm−1 |
b = 5.8135 (4) Å | T = 150 K |
c = 22.8511 (17) Å | 0.2 × 0.2 × 0.04 mm |
β = 98.394 (2)° |
Bruker AXS SMART 1K CCD diffractometer | 7939 independent reflections |
Absorption correction: multi-scan (SADABS; Siemens, 1996) | 5999 reflections with I > 2σ(I) |
Tmin = 0.971, Tmax = 0.994 | Rint = 0.047 |
21435 measured reflections |
R[F2 > 2σ(F2)] = 0.081 | 0 restraints |
wR(F2) = 0.187 | H-atom parameters constrained |
S = 1.14 | Δρmax = 0.37 e Å−3 |
7939 reflections | Δρmin = −0.42 e Å−3 |
514 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 | ||
C1 | 0.94927 (13) | −0.0968 (8) | 0.6145 (2) | 0.0374 (11) | |
H1A | 0.924 | −0.0131 | 0.6019 | 0.056* | |
H1B | 0.9469 | −0.1848 | 0.6504 | 0.056* | |
H1C | 0.9545 | −0.2022 | 0.5831 | 0.056* | |
C2 | 0.99822 (15) | 0.2811 (8) | 0.5628 (2) | 0.0418 (12) | |
H2A | 0.9737 | 0.3709 | 0.5502 | 0.063* | |
H2B | 1.003 | 0.1761 | 0.531 | 0.063* | |
H2C | 1.0213 | 0.3853 | 0.5719 | 0.063* | |
C3 | 0.98149 (13) | 0.3125 (8) | 0.6897 (2) | 0.0340 (10) | |
H3A | 0.9567 | 0.3998 | 0.6763 | 0.051* | |
H3B | 1.0043 | 0.419 | 0.699 | 0.051* | |
H3C | 0.978 | 0.2243 | 0.7252 | 0.051* | |
C4 | 1.03774 (11) | −0.0556 (7) | 0.65314 (18) | 0.0272 (9) | |
C5 | 1.06694 (11) | −0.1755 (7) | 0.66811 (18) | 0.0239 (8) | |
C6 | 1.10161 (11) | −0.3241 (7) | 0.68605 (17) | 0.0227 (8) | |
C7 | 1.09550 (12) | −0.5361 (7) | 0.71416 (17) | 0.0240 (8) | |
H7 | 1.0691 | −0.5754 | 0.7216 | 0.029* | |
C8 | 1.12717 (12) | −0.6873 (7) | 0.73096 (18) | 0.0258 (9) | |
H8 | 1.1229 | −0.8288 | 0.7499 | 0.031* | |
C9 | 1.16529 (11) | −0.6252 (6) | 0.71922 (17) | 0.0212 (8) | |
C10 | 1.17245 (11) | −0.4130 (6) | 0.69193 (16) | 0.0187 (8) | |
C11 | 1.13991 (11) | −0.2628 (6) | 0.67515 (17) | 0.0200 (8) | |
H11 | 1.1441 | −0.1205 | 0.6565 | 0.024* | |
C12 | 1.23184 (12) | −0.6156 (6) | 0.71115 (17) | 0.0245 (8) | |
C13 | 1.27288 (12) | −0.6655 (7) | 0.71316 (17) | 0.0262 (9) | |
H13 | 1.2841 | −0.8048 | 0.7301 | 0.031* | |
C14 | 1.29661 (12) | −0.5056 (8) | 0.68979 (19) | 0.0320 (10) | |
H14 | 1.3245 | −0.537 | 0.69 | 0.038* | |
C15 | 1.28047 (12) | −0.2972 (7) | 0.66559 (19) | 0.0298 (9) | |
H15 | 1.2977 | −0.1894 | 0.6504 | 0.036* | |
C16 | 1.23991 (11) | −0.2479 (7) | 0.66376 (17) | 0.0238 (8) | |
H16 | 1.229 | −0.1082 | 0.6467 | 0.029* | |
C17 | 1.21512 (11) | −0.4058 (6) | 0.68726 (16) | 0.0208 (8) | |
C101 | 0.58960 (14) | 0.7704 (8) | 0.2666 (2) | 0.0417 (12) | |
H10A | 0.5669 | 0.8638 | 0.2758 | 0.062* | |
H10B | 0.6101 | 0.8708 | 0.2535 | 0.062* | |
H10C | 0.6015 | 0.6862 | 0.3021 | 0.062* | |
C102 | 0.53326 (13) | 0.3609 (8) | 0.2296 (2) | 0.0386 (11) | |
H10D | 0.5098 | 0.4479 | 0.2387 | 0.058* | |
H10E | 0.5453 | 0.2758 | 0.2648 | 0.058* | |
H10F | 0.5246 | 0.2526 | 0.1974 | 0.058* | |
C103 | 0.54720 (15) | 0.7168 (10) | 0.1393 (3) | 0.0539 (14) | |
H10G | 0.5243 | 0.8079 | 0.1487 | 0.081* | |
H10H | 0.5376 | 0.6048 | 0.1084 | 0.081* | |
H10I | 0.5671 | 0.819 | 0.1252 | 0.081* | |
C104 | 0.61408 (12) | 0.3909 (7) | 0.19062 (19) | 0.0289 (9) | |
C105 | 0.64175 (12) | 0.2721 (7) | 0.18010 (19) | 0.0273 (9) | |
C106 | 0.67299 (11) | 0.1251 (6) | 0.16391 (17) | 0.0222 (8) | |
C107 | 0.66163 (11) | −0.0945 (7) | 0.13963 (18) | 0.0248 (9) | |
H107 | 0.6341 | −0.1411 | 0.1366 | 0.03* | |
C108 | 0.68905 (11) | −0.2407 (7) | 0.12054 (18) | 0.0245 (9) | |
H108 | 0.6809 | −0.3861 | 0.104 | 0.029* | |
C109 | 0.72895 (11) | −0.1712 (6) | 0.12597 (16) | 0.0195 (8) | |
C110 | 0.74177 (11) | 0.0455 (6) | 0.15089 (16) | 0.0186 (8) | |
C111 | 0.71361 (11) | 0.1916 (6) | 0.17104 (16) | 0.0196 (8) | |
H111 | 0.7219 | 0.334 | 0.1893 | 0.024* | |
C112 | 0.79577 (11) | −0.1404 (6) | 0.11935 (16) | 0.0191 (8) | |
C113 | 0.83489 (11) | −0.1776 (7) | 0.10763 (17) | 0.0233 (8) | |
H113 | 0.8421 | −0.3151 | 0.0893 | 0.028* | |
C114 | 0.86314 (11) | −0.0036 (7) | 0.12399 (17) | 0.0248 (9) | |
H114 | 0.8901 | −0.0222 | 0.116 | 0.03* | |
C115 | 0.85278 (11) | 0.1970 (7) | 0.15186 (18) | 0.0246 (9) | |
H115 | 0.8729 | 0.3102 | 0.1633 | 0.03* | |
C116 | 0.81385 (11) | 0.2334 (6) | 0.16300 (17) | 0.0215 (8) | |
H116 | 0.807 | 0.3715 | 0.1814 | 0.026* | |
C117 | 0.78442 (10) | 0.0637 (6) | 0.14678 (16) | 0.0180 (8) | |
C201 | 0.58367 (16) | 0.2827 (10) | 0.5181 (2) | 0.0547 (14) | |
H20A | 0.5587 | 0.192 | 0.5131 | 0.082* | |
H20B | 0.5829 | 0.3963 | 0.5496 | 0.082* | |
H20C | 0.6069 | 0.1804 | 0.5287 | 0.082* | |
C202 | 0.54518 (15) | 0.6333 (9) | 0.4287 (3) | 0.0684 (19) | |
H20D | 0.5198 | 0.5459 | 0.4243 | 0.103* | |
H20E | 0.5476 | 0.7125 | 0.3915 | 0.103* | |
H20F | 0.5452 | 0.7468 | 0.4604 | 0.103* | |
C203 | 0.59114 (18) | 0.2198 (9) | 0.3883 (2) | 0.0533 (14) | |
H20G | 0.5665 | 0.1257 | 0.3833 | 0.08* | |
H20H | 0.6148 | 0.1209 | 0.3991 | 0.08* | |
H20I | 0.5934 | 0.2994 | 0.3511 | 0.08* | |
C204 | 0.63507 (13) | 0.6057 (8) | 0.4551 (2) | 0.0368 (11) | |
C205 | 0.66520 (12) | 0.7223 (7) | 0.45955 (19) | 0.0293 (9) | |
C206 | 0.70077 (12) | 0.8676 (7) | 0.46843 (18) | 0.0260 (9) | |
C207 | 0.69732 (12) | 1.0870 (7) | 0.49484 (17) | 0.0257 (9) | |
H207 | 0.6717 | 1.1359 | 0.5037 | 0.031* | |
C208 | 0.73045 (12) | 1.2305 (7) | 0.50781 (18) | 0.0250 (9) | |
H208 | 0.7281 | 1.3763 | 0.5258 | 0.03* | |
C209 | 0.76714 (11) | 1.1539 (6) | 0.49368 (16) | 0.0216 (8) | |
C210 | 0.77150 (11) | 0.9360 (6) | 0.46671 (17) | 0.0226 (8) | |
C211 | 0.73748 (12) | 0.7961 (7) | 0.45339 (17) | 0.0240 (8) | |
H211 | 0.7395 | 0.6526 | 0.4341 | 0.029* | |
C212 | 0.83313 (12) | 1.1194 (6) | 0.48325 (17) | 0.0233 (8) | |
C213 | 0.87428 (12) | 1.1524 (7) | 0.48430 (18) | 0.0292 (9) | |
H213 | 0.8872 | 1.2883 | 0.5007 | 0.035* | |
C214 | 0.89606 (12) | 0.9817 (7) | 0.46078 (18) | 0.0298 (9) | |
H214 | 0.9243 | 1.0015 | 0.4608 | 0.036* | |
C215 | 0.87720 (13) | 0.7799 (7) | 0.43692 (18) | 0.0294 (9) | |
H215 | 0.8929 | 0.6649 | 0.4213 | 0.035* | |
C216 | 0.83621 (12) | 0.7464 (7) | 0.43579 (17) | 0.0253 (9) | |
H216 | 0.8235 | 0.6102 | 0.4192 | 0.03* | |
C217 | 0.81374 (11) | 0.9154 (6) | 0.45937 (16) | 0.0221 (8) | |
Si1 | 0.99182 (3) | 0.11166 (19) | 0.63010 (5) | 0.0244 (3) | |
Si11 | 0.57117 (3) | 0.56253 (19) | 0.20686 (6) | 0.0286 (3) | |
Si21 | 0.58857 (4) | 0.4339 (2) | 0.44733 (6) | 0.0364 (3) | |
N1 | 1.20135 (10) | −0.7431 (5) | 0.73063 (15) | 0.0254 (7) | |
H1 | 1.2045 | −0.8789 | 0.7477 | 0.03* | |
N101 | 0.76177 (9) | −0.2807 (5) | 0.10800 (14) | 0.0225 (7) | |
H101 | 0.7613 | −0.4182 | 0.0918 | 0.027* | |
N201 | 0.80458 (10) | 1.2608 (5) | 0.50257 (15) | 0.0250 (7) | |
H201 | 0.8094 | 1.3982 | 0.5182 | 0.03* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.034 (2) | 0.028 (2) | 0.049 (3) | −0.0016 (19) | −0.001 (2) | 0.001 (2) |
C2 | 0.053 (3) | 0.035 (3) | 0.040 (3) | 0.007 (2) | 0.013 (2) | 0.014 (2) |
C3 | 0.031 (2) | 0.027 (2) | 0.044 (3) | 0.0061 (18) | 0.0067 (19) | −0.002 (2) |
C4 | 0.025 (2) | 0.027 (2) | 0.032 (2) | 0.0007 (17) | 0.0085 (17) | −0.0009 (18) |
C5 | 0.025 (2) | 0.020 (2) | 0.027 (2) | −0.0015 (16) | 0.0061 (16) | −0.0011 (17) |
C6 | 0.026 (2) | 0.0167 (19) | 0.026 (2) | 0.0021 (15) | 0.0026 (16) | −0.0049 (16) |
C7 | 0.027 (2) | 0.020 (2) | 0.025 (2) | −0.0040 (16) | 0.0037 (16) | −0.0009 (17) |
C8 | 0.039 (2) | 0.0130 (19) | 0.026 (2) | −0.0009 (16) | 0.0064 (17) | 0.0023 (17) |
C9 | 0.028 (2) | 0.0133 (19) | 0.022 (2) | −0.0003 (15) | 0.0010 (15) | −0.0017 (16) |
C10 | 0.0260 (19) | 0.0124 (18) | 0.0167 (18) | −0.0008 (15) | −0.0001 (14) | −0.0008 (15) |
C11 | 0.029 (2) | 0.0094 (18) | 0.022 (2) | 0.0009 (15) | 0.0022 (15) | 0.0010 (15) |
C12 | 0.036 (2) | 0.0141 (19) | 0.022 (2) | 0.0001 (16) | −0.0010 (16) | 0.0000 (16) |
C13 | 0.030 (2) | 0.020 (2) | 0.025 (2) | 0.0070 (16) | −0.0064 (16) | −0.0008 (17) |
C14 | 0.028 (2) | 0.033 (2) | 0.033 (2) | 0.0041 (18) | −0.0022 (17) | −0.004 (2) |
C15 | 0.033 (2) | 0.028 (2) | 0.029 (2) | −0.0033 (18) | 0.0073 (18) | −0.0013 (19) |
C16 | 0.028 (2) | 0.018 (2) | 0.024 (2) | −0.0002 (16) | −0.0012 (16) | 0.0001 (16) |
C17 | 0.0273 (19) | 0.0138 (18) | 0.0203 (19) | 0.0019 (15) | 0.0000 (15) | 0.0003 (15) |
C101 | 0.045 (3) | 0.025 (2) | 0.057 (3) | 0.004 (2) | 0.016 (2) | −0.008 (2) |
C102 | 0.032 (2) | 0.025 (2) | 0.059 (3) | 0.0000 (19) | 0.011 (2) | −0.001 (2) |
C103 | 0.036 (3) | 0.059 (4) | 0.065 (4) | 0.010 (2) | 0.003 (2) | 0.019 (3) |
C104 | 0.028 (2) | 0.021 (2) | 0.038 (2) | 0.0022 (17) | 0.0058 (17) | 0.0019 (19) |
C105 | 0.030 (2) | 0.022 (2) | 0.031 (2) | −0.0023 (17) | 0.0060 (17) | 0.0021 (18) |
C106 | 0.0256 (19) | 0.0131 (18) | 0.029 (2) | 0.0041 (15) | 0.0083 (16) | 0.0035 (16) |
C107 | 0.025 (2) | 0.019 (2) | 0.030 (2) | −0.0029 (16) | 0.0051 (16) | 0.0034 (17) |
C108 | 0.029 (2) | 0.0158 (19) | 0.028 (2) | −0.0017 (16) | −0.0001 (16) | 0.0006 (16) |
C109 | 0.0235 (19) | 0.0141 (18) | 0.0205 (19) | 0.0028 (14) | 0.0016 (15) | 0.0027 (15) |
C110 | 0.0275 (19) | 0.0114 (18) | 0.0169 (18) | 0.0019 (14) | 0.0034 (15) | 0.0033 (15) |
C111 | 0.0264 (19) | 0.0115 (18) | 0.0211 (19) | 0.0023 (14) | 0.0042 (15) | 0.0009 (15) |
C112 | 0.0244 (19) | 0.0162 (19) | 0.0161 (18) | 0.0006 (15) | 0.0006 (14) | 0.0034 (15) |
C113 | 0.030 (2) | 0.020 (2) | 0.020 (2) | 0.0081 (16) | 0.0021 (16) | 0.0029 (16) |
C114 | 0.0209 (19) | 0.026 (2) | 0.027 (2) | 0.0050 (16) | 0.0018 (16) | 0.0059 (17) |
C115 | 0.025 (2) | 0.019 (2) | 0.029 (2) | −0.0012 (16) | −0.0009 (16) | 0.0039 (17) |
C116 | 0.028 (2) | 0.0103 (18) | 0.025 (2) | 0.0003 (15) | −0.0013 (16) | −0.0009 (16) |
C117 | 0.0230 (18) | 0.0121 (18) | 0.0186 (18) | 0.0017 (14) | 0.0015 (14) | 0.0014 (15) |
C201 | 0.050 (3) | 0.064 (4) | 0.050 (3) | −0.018 (3) | 0.007 (2) | −0.001 (3) |
C202 | 0.034 (3) | 0.036 (3) | 0.129 (6) | −0.006 (2) | −0.009 (3) | 0.001 (3) |
C203 | 0.077 (4) | 0.032 (3) | 0.046 (3) | −0.012 (3) | −0.008 (3) | −0.004 (2) |
C204 | 0.035 (2) | 0.026 (2) | 0.048 (3) | −0.0018 (19) | 0.002 (2) | 0.001 (2) |
C205 | 0.029 (2) | 0.024 (2) | 0.034 (2) | 0.0012 (17) | −0.0010 (17) | −0.0020 (19) |
C206 | 0.029 (2) | 0.018 (2) | 0.029 (2) | −0.0042 (16) | −0.0015 (16) | 0.0019 (17) |
C207 | 0.032 (2) | 0.019 (2) | 0.026 (2) | 0.0050 (16) | 0.0034 (16) | 0.0049 (17) |
C208 | 0.034 (2) | 0.0133 (19) | 0.027 (2) | 0.0011 (16) | 0.0033 (17) | −0.0001 (16) |
C209 | 0.032 (2) | 0.0139 (19) | 0.0184 (19) | −0.0018 (15) | 0.0017 (15) | 0.0044 (15) |
C210 | 0.031 (2) | 0.0143 (19) | 0.022 (2) | 0.0000 (15) | 0.0008 (16) | 0.0034 (16) |
C211 | 0.031 (2) | 0.0159 (19) | 0.024 (2) | −0.0032 (16) | 0.0009 (16) | 0.0011 (16) |
C212 | 0.034 (2) | 0.0147 (19) | 0.022 (2) | −0.0016 (16) | 0.0050 (16) | 0.0026 (16) |
C213 | 0.033 (2) | 0.027 (2) | 0.026 (2) | −0.0053 (18) | 0.0009 (17) | −0.0016 (18) |
C214 | 0.031 (2) | 0.033 (2) | 0.026 (2) | −0.0004 (18) | 0.0048 (17) | 0.0043 (19) |
C215 | 0.037 (2) | 0.027 (2) | 0.025 (2) | 0.0062 (18) | 0.0051 (17) | 0.0002 (18) |
C216 | 0.042 (2) | 0.015 (2) | 0.017 (2) | 0.0011 (17) | 0.0025 (17) | 0.0003 (16) |
C217 | 0.033 (2) | 0.0145 (19) | 0.0191 (19) | −0.0046 (16) | 0.0044 (15) | 0.0019 (16) |
Si1 | 0.0243 (5) | 0.0179 (6) | 0.0309 (6) | 0.0011 (4) | 0.0033 (4) | 0.0016 (5) |
Si11 | 0.0237 (6) | 0.0197 (6) | 0.0434 (7) | 0.0044 (4) | 0.0082 (5) | 0.0030 (5) |
Si21 | 0.0343 (7) | 0.0235 (6) | 0.0483 (8) | −0.0081 (5) | −0.0044 (5) | −0.0024 (6) |
N1 | 0.0315 (18) | 0.0135 (16) | 0.0304 (19) | 0.0026 (13) | 0.0016 (14) | 0.0053 (14) |
N101 | 0.0281 (17) | 0.0116 (16) | 0.0280 (18) | 0.0016 (13) | 0.0052 (14) | −0.0023 (14) |
N201 | 0.0326 (18) | 0.0132 (16) | 0.0293 (19) | −0.0041 (13) | 0.0051 (14) | −0.0060 (14) |
C1—Si1 | 1.862 (4) | C108—H108 | 0.95 |
C1—H1A | 0.98 | C109—N101 | 1.381 (5) |
C1—H1B | 0.98 | C109—C110 | 1.423 (5) |
C1—H1C | 0.98 | C110—C111 | 1.394 (5) |
C2—Si1 | 1.864 (5) | C110—C117 | 1.445 (5) |
C2—H2A | 0.98 | C111—H111 | 0.95 |
C2—H2B | 0.98 | C112—C113 | 1.389 (5) |
C2—H2C | 0.98 | C112—N101 | 1.391 (5) |
C3—Si1 | 1.864 (4) | C112—C117 | 1.419 (5) |
C3—H3A | 0.98 | C113—C114 | 1.396 (6) |
C3—H3B | 0.98 | C113—H113 | 0.95 |
C3—H3C | 0.98 | C114—C115 | 1.396 (6) |
C4—C5 | 1.207 (5) | C114—H114 | 0.95 |
C4—Si1 | 1.827 (4) | C115—C116 | 1.377 (5) |
C5—C6 | 1.455 (5) | C115—H115 | 0.95 |
C6—C11 | 1.385 (5) | C116—C117 | 1.404 (5) |
C6—C7 | 1.418 (5) | C116—H116 | 0.95 |
C7—C8 | 1.386 (5) | C201—Si21 | 1.869 (6) |
C7—H7 | 0.95 | C201—H20A | 0.98 |
C8—C9 | 1.387 (5) | C201—H20B | 0.98 |
C8—H8 | 0.95 | C201—H20C | 0.98 |
C9—N1 | 1.377 (5) | C202—Si21 | 1.856 (5) |
C9—C10 | 1.418 (5) | C202—H20D | 0.98 |
C10—C11 | 1.403 (5) | C202—H20E | 0.98 |
C10—C17 | 1.445 (5) | C202—H20F | 0.98 |
C11—H11 | 0.95 | C203—Si21 | 1.847 (5) |
C12—N1 | 1.385 (5) | C203—H20G | 0.98 |
C12—C13 | 1.395 (5) | C203—H20H | 0.98 |
C12—C17 | 1.417 (5) | C203—H20I | 0.98 |
C13—C14 | 1.379 (6) | C204—C205 | 1.205 (6) |
C13—H13 | 0.95 | C204—Si21 | 1.833 (4) |
C14—C15 | 1.406 (6) | C205—C206 | 1.448 (5) |
C14—H14 | 0.95 | C206—C211 | 1.385 (6) |
C15—C16 | 1.379 (6) | C206—C207 | 1.423 (6) |
C15—H15 | 0.95 | C207—C208 | 1.383 (5) |
C16—C17 | 1.395 (5) | C207—H207 | 0.95 |
C16—H16 | 0.95 | C208—C209 | 1.386 (5) |
C101—Si11 | 1.860 (5) | C208—H208 | 0.95 |
C101—H10A | 0.98 | C209—N201 | 1.385 (5) |
C101—H10B | 0.98 | C209—C210 | 1.426 (5) |
C101—H10C | 0.98 | C210—C211 | 1.394 (5) |
C102—Si11 | 1.855 (4) | C210—C217 | 1.450 (5) |
C102—H10D | 0.98 | C211—H211 | 0.95 |
C102—H10E | 0.98 | C212—N201 | 1.379 (5) |
C102—H10F | 0.98 | C212—C213 | 1.385 (5) |
C103—Si11 | 1.862 (5) | C212—C217 | 1.422 (5) |
C103—H10G | 0.98 | C213—C214 | 1.385 (6) |
C103—H10H | 0.98 | C213—H213 | 0.95 |
C103—H10I | 0.98 | C214—C215 | 1.403 (6) |
C104—C105 | 1.206 (6) | C214—H214 | 0.95 |
C104—Si11 | 1.828 (4) | C215—C216 | 1.380 (6) |
C105—C106 | 1.438 (5) | C215—H215 | 0.95 |
C106—C111 | 1.397 (5) | C216—C217 | 1.392 (5) |
C106—C107 | 1.421 (5) | C216—H216 | 0.95 |
C107—C108 | 1.367 (5) | N1—H1 | 0.88 |
C107—H107 | 0.95 | N101—H101 | 0.88 |
C108—C109 | 1.381 (5) | N201—H201 | 0.88 |
Si1—C1—H1A | 109.5 | C112—C113—H113 | 121.5 |
Si1—C1—H1B | 109.5 | C114—C113—H113 | 121.5 |
H1A—C1—H1B | 109.5 | C115—C114—C113 | 121.6 (4) |
Si1—C1—H1C | 109.5 | C115—C114—H114 | 119.2 |
H1A—C1—H1C | 109.5 | C113—C114—H114 | 119.2 |
H1B—C1—H1C | 109.5 | C116—C115—C114 | 121.1 (4) |
Si1—C2—H2A | 109.5 | C116—C115—H115 | 119.5 |
Si1—C2—H2B | 109.5 | C114—C115—H115 | 119.5 |
H2A—C2—H2B | 109.5 | C115—C116—C117 | 119.1 (3) |
Si1—C2—H2C | 109.5 | C115—C116—H116 | 120.4 |
H2A—C2—H2C | 109.5 | C117—C116—H116 | 120.4 |
H2B—C2—H2C | 109.5 | C116—C117—C112 | 118.8 (3) |
Si1—C3—H3A | 109.5 | C116—C117—C110 | 133.9 (3) |
Si1—C3—H3B | 109.5 | C112—C117—C110 | 107.3 (3) |
H3A—C3—H3B | 109.5 | Si21—C201—H20A | 109.5 |
Si1—C3—H3C | 109.5 | Si21—C201—H20B | 109.5 |
H3A—C3—H3C | 109.5 | H20A—C201—H20B | 109.5 |
H3B—C3—H3C | 109.5 | Si21—C201—H20C | 109.5 |
C5—C4—Si1 | 176.8 (4) | H20A—C201—H20C | 109.5 |
C4—C5—C6 | 178.9 (4) | H20B—C201—H20C | 109.5 |
C11—C6—C7 | 120.2 (3) | Si21—C202—H20D | 109.5 |
C11—C6—C5 | 121.0 (4) | Si21—C202—H20E | 109.5 |
C7—C6—C5 | 118.8 (3) | H20D—C202—H20E | 109.5 |
C8—C7—C6 | 121.5 (4) | Si21—C202—H20F | 109.5 |
C8—C7—H7 | 119.3 | H20D—C202—H20F | 109.5 |
C6—C7—H7 | 119.3 | H20E—C202—H20F | 109.5 |
C7—C8—C9 | 117.8 (4) | Si21—C203—H20G | 109.5 |
C7—C8—H8 | 121.1 | Si21—C203—H20H | 109.5 |
C9—C8—H8 | 121.1 | H20G—C203—H20H | 109.5 |
N1—C9—C8 | 129.5 (4) | Si21—C203—H20I | 109.5 |
N1—C9—C10 | 108.5 (3) | H20G—C203—H20I | 109.5 |
C8—C9—C10 | 122.0 (3) | H20H—C203—H20I | 109.5 |
C11—C10—C9 | 119.2 (3) | C205—C204—Si21 | 178.7 (4) |
C11—C10—C17 | 134.0 (3) | C204—C205—C206 | 176.4 (5) |
C9—C10—C17 | 106.8 (3) | C211—C206—C207 | 120.3 (4) |
C6—C11—C10 | 119.3 (3) | C211—C206—C205 | 121.9 (4) |
C6—C11—H11 | 120.3 | C207—C206—C205 | 117.8 (4) |
C10—C11—H11 | 120.3 | C208—C207—C206 | 121.3 (4) |
N1—C12—C13 | 130.1 (4) | C208—C207—H207 | 119.3 |
N1—C12—C17 | 108.5 (3) | C206—C207—H207 | 119.3 |
C13—C12—C17 | 121.4 (4) | C207—C208—C209 | 117.6 (4) |
C14—C13—C12 | 117.7 (4) | C207—C208—H208 | 121.2 |
C14—C13—H13 | 121.2 | C209—C208—H208 | 121.2 |
C12—C13—H13 | 121.2 | N201—C209—C208 | 129.2 (4) |
C13—C14—C15 | 121.6 (4) | N201—C209—C210 | 108.4 (3) |
C13—C14—H14 | 119.2 | C208—C209—C210 | 122.4 (3) |
C15—C14—H14 | 119.2 | C211—C210—C209 | 118.8 (4) |
C16—C15—C14 | 120.6 (4) | C211—C210—C217 | 134.6 (4) |
C16—C15—H15 | 119.7 | C209—C210—C217 | 106.6 (3) |
C14—C15—H15 | 119.7 | C206—C211—C210 | 119.6 (4) |
C15—C16—C17 | 119.1 (4) | C206—C211—H211 | 120.2 |
C15—C16—H16 | 120.4 | C210—C211—H211 | 120.2 |
C17—C16—H16 | 120.4 | N201—C212—C213 | 130.0 (4) |
C16—C17—C12 | 119.5 (3) | N201—C212—C217 | 108.8 (3) |
C16—C17—C10 | 134.0 (3) | C213—C212—C217 | 121.2 (4) |
C12—C17—C10 | 106.5 (3) | C212—C213—C214 | 118.0 (4) |
Si11—C101—H10A | 109.5 | C212—C213—H213 | 121 |
Si11—C101—H10B | 109.5 | C214—C213—H213 | 121 |
H10A—C101—H10B | 109.5 | C213—C214—C215 | 121.2 (4) |
Si11—C101—H10C | 109.5 | C213—C214—H214 | 119.4 |
H10A—C101—H10C | 109.5 | C215—C214—H214 | 119.4 |
H10B—C101—H10C | 109.5 | C216—C215—C214 | 120.9 (4) |
Si11—C102—H10D | 109.5 | C216—C215—H215 | 119.6 |
Si11—C102—H10E | 109.5 | C214—C215—H215 | 119.6 |
H10D—C102—H10E | 109.5 | C215—C216—C217 | 118.9 (4) |
Si11—C102—H10F | 109.5 | C215—C216—H216 | 120.6 |
H10D—C102—H10F | 109.5 | C217—C216—H216 | 120.6 |
H10E—C102—H10F | 109.5 | C216—C217—C212 | 119.8 (4) |
Si11—C103—H10G | 109.5 | C216—C217—C210 | 133.8 (4) |
Si11—C103—H10H | 109.5 | C212—C217—C210 | 106.4 (3) |
H10G—C103—H10H | 109.5 | C4—Si1—C1 | 107.1 (2) |
Si11—C103—H10I | 109.5 | C4—Si1—C3 | 111.1 (2) |
H10G—C103—H10I | 109.5 | C1—Si1—C3 | 109.2 (2) |
H10H—C103—H10I | 109.5 | C4—Si1—C2 | 109.0 (2) |
C105—C104—Si11 | 178.1 (4) | C1—Si1—C2 | 111.3 (2) |
C104—C105—C106 | 176.0 (5) | C3—Si1—C2 | 109.1 (2) |
C111—C106—C107 | 119.6 (3) | C104—Si11—C102 | 107.44 (19) |
C111—C106—C105 | 122.3 (3) | C104—Si11—C101 | 108.6 (2) |
C107—C106—C105 | 118.2 (3) | C102—Si11—C101 | 111.8 (2) |
C108—C107—C106 | 122.0 (4) | C104—Si11—C103 | 110.5 (2) |
C108—C107—H107 | 119 | C102—Si11—C103 | 108.0 (2) |
C106—C107—H107 | 119 | C101—Si11—C103 | 110.6 (3) |
C107—C108—C109 | 118.2 (4) | C204—Si21—C203 | 108.0 (2) |
C107—C108—H108 | 120.9 | C204—Si21—C202 | 107.7 (2) |
C109—C108—H108 | 120.9 | C203—Si21—C202 | 111.8 (3) |
N101—C109—C108 | 129.5 (4) | C204—Si21—C201 | 110.7 (2) |
N101—C109—C110 | 108.8 (3) | C203—Si21—C201 | 109.6 (3) |
C108—C109—C110 | 121.7 (3) | C202—Si21—C201 | 109.2 (3) |
C111—C110—C109 | 119.6 (3) | C9—N1—C12 | 109.7 (3) |
C111—C110—C117 | 134.1 (3) | C9—N1—H1 | 125.2 |
C109—C110—C117 | 106.3 (3) | C12—N1—H1 | 125.2 |
C110—C111—C106 | 118.9 (3) | C109—N101—C112 | 109.6 (3) |
C110—C111—H111 | 120.5 | C109—N101—H101 | 125.2 |
C106—C111—H111 | 120.5 | C112—N101—H101 | 125.2 |
C113—C112—N101 | 129.7 (3) | C212—N201—C209 | 109.7 (3) |
C113—C112—C117 | 122.3 (3) | C212—N201—H201 | 125.2 |
N101—C112—C117 | 108.0 (3) | C209—N201—H201 | 125.2 |
C112—C113—C114 | 117.0 (4) | ||
Si1—C4—C5—C6 | 0 (26) | N101—C112—C117—C110 | −1.1 (4) |
C4—C5—C6—C11 | 152 (21) | C111—C110—C117—C116 | 2.0 (7) |
C4—C5—C6—C7 | −27 (21) | C109—C110—C117—C116 | 179.5 (4) |
C11—C6—C7—C8 | −0.5 (6) | C111—C110—C117—C112 | −177.2 (4) |
C5—C6—C7—C8 | 178.4 (4) | C109—C110—C117—C112 | 0.4 (4) |
C6—C7—C8—C9 | −0.2 (6) | Si21—C204—C205—C206 | 89 (22) |
C7—C8—C9—N1 | −179.3 (4) | C204—C205—C206—C211 | 141 (7) |
C7—C8—C9—C10 | 1.1 (6) | C204—C205—C206—C207 | −37 (8) |
N1—C9—C10—C11 | 179.1 (3) | C211—C206—C207—C208 | −2.1 (6) |
C8—C9—C10—C11 | −1.3 (5) | C205—C206—C207—C208 | 176.3 (4) |
N1—C9—C10—C17 | −0.2 (4) | C206—C207—C208—C209 | 0.6 (6) |
C8—C9—C10—C17 | 179.4 (3) | C207—C208—C209—N201 | −179.0 (4) |
C7—C6—C11—C10 | 0.3 (6) | C207—C208—C209—C210 | 0.0 (6) |
C5—C6—C11—C10 | −178.6 (3) | N201—C209—C210—C211 | −179.9 (3) |
C9—C10—C11—C6 | 0.5 (5) | C208—C209—C210—C211 | 0.8 (6) |
C17—C10—C11—C6 | 179.6 (4) | N201—C209—C210—C217 | −0.2 (4) |
N1—C12—C13—C14 | 179.6 (4) | C208—C209—C210—C217 | −179.4 (3) |
C17—C12—C13—C14 | −1.5 (6) | C207—C206—C211—C210 | 2.9 (6) |
C12—C13—C14—C15 | 1.1 (6) | C205—C206—C211—C210 | −175.4 (4) |
C13—C14—C15—C16 | −1.0 (6) | C209—C210—C211—C206 | −2.3 (6) |
C14—C15—C16—C17 | 1.2 (6) | C217—C210—C211—C206 | 178.0 (4) |
C15—C16—C17—C12 | −1.6 (6) | N201—C212—C213—C214 | −178.9 (4) |
C15—C16—C17—C10 | −178.7 (4) | C217—C212—C213—C214 | 0.7 (6) |
N1—C12—C17—C16 | −179.1 (3) | C212—C213—C214—C215 | −0.5 (6) |
C13—C12—C17—C16 | 1.8 (6) | C213—C214—C215—C216 | 0.5 (6) |
N1—C12—C17—C10 | −1.2 (4) | C214—C215—C216—C217 | −0.7 (6) |
C13—C12—C17—C10 | 179.6 (3) | C215—C216—C217—C212 | 0.9 (6) |
C11—C10—C17—C16 | −0.8 (7) | C215—C216—C217—C210 | −178.5 (4) |
C9—C10—C17—C16 | 178.3 (4) | N201—C212—C217—C216 | 178.8 (3) |
C11—C10—C17—C12 | −178.3 (4) | C213—C212—C217—C216 | −0.9 (6) |
C9—C10—C17—C12 | 0.9 (4) | N201—C212—C217—C210 | −1.7 (4) |
Si11—C104—C105—C106 | 65 (16) | C213—C212—C217—C210 | 178.6 (4) |
C104—C105—C106—C111 | 140 (6) | C211—C210—C217—C216 | 0.3 (8) |
C104—C105—C106—C107 | −39 (6) | C209—C210—C217—C216 | −179.5 (4) |
C111—C106—C107—C108 | −2.8 (6) | C211—C210—C217—C212 | −179.2 (4) |
C105—C106—C107—C108 | 176.9 (4) | C209—C210—C217—C212 | 1.1 (4) |
C106—C107—C108—C109 | 0.8 (6) | C5—C4—Si1—C1 | −2 (7) |
C107—C108—C109—N101 | −176.9 (4) | C5—C4—Si1—C3 | 117 (7) |
C107—C108—C109—C110 | 0.3 (6) | C5—C4—Si1—C2 | −123 (7) |
N101—C109—C110—C111 | 178.4 (3) | C105—C104—Si11—C102 | 7 (13) |
C108—C109—C110—C111 | 0.7 (5) | C105—C104—Si11—C101 | 128 (13) |
N101—C109—C110—C117 | 0.4 (4) | C105—C104—Si11—C103 | −110 (13) |
C108—C109—C110—C117 | −177.3 (3) | C205—C204—Si21—C203 | 105 (21) |
C109—C110—C111—C106 | −2.7 (5) | C205—C204—Si21—C202 | −16 (21) |
C117—C110—C111—C106 | 174.6 (4) | C205—C204—Si21—C201 | −135 (21) |
C107—C106—C111—C110 | 3.7 (5) | C8—C9—N1—C12 | 179.9 (4) |
C105—C106—C111—C110 | −176.0 (4) | C10—C9—N1—C12 | −0.6 (4) |
N101—C112—C113—C114 | 179.8 (4) | C13—C12—N1—C9 | −179.8 (4) |
C117—C112—C113—C114 | −0.1 (5) | C17—C12—N1—C9 | 1.1 (4) |
C112—C113—C114—C115 | 1.1 (5) | C108—C109—N101—C112 | 176.4 (4) |
C113—C114—C115—C116 | −1.6 (6) | C110—C109—N101—C112 | −1.1 (4) |
C114—C115—C116—C117 | 1.0 (6) | C113—C112—N101—C109 | −178.6 (4) |
C115—C116—C117—C112 | 0.0 (5) | C117—C112—N101—C109 | 1.3 (4) |
C115—C116—C117—C110 | −179.1 (4) | C213—C212—N201—C209 | −178.7 (4) |
C113—C112—C117—C116 | −0.4 (5) | C217—C212—N201—C209 | 1.6 (4) |
N101—C112—C117—C116 | 179.6 (3) | C208—C209—N201—C212 | 178.3 (4) |
C113—C112—C117—C110 | 178.9 (3) | C210—C209—N201—C212 | −0.9 (4) |
Experimental details
Crystal data | |
Chemical formula | [Si(CH3)3(C14H8N)] |
Mr | 263.41 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 150 |
a, b, c (Å) | 33.402 (3), 5.8135 (4), 22.8511 (17) |
β (°) | 98.394 (2) |
V (Å3) | 4389.7 (6) |
Z | 12 |
Radiation type | Synchrotron, λ = 0.688 Å |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.2 × 0.2 × 0.04 |
Data collection | |
Diffractometer | Bruker AXS SMART 1K CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Siemens, 1996) |
Tmin, Tmax | 0.971, 0.994 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21435, 7939, 5999 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.081, 0.187, 1.14 |
No. of reflections | 7939 |
No. of parameters | 514 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.42 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2000), SAINT, SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX publication routines (Farrugia, 1999).
C1—Si1 | 1.862 (4) | C109—N101 | 1.381 (5) |
C2—Si1 | 1.864 (5) | C109—C110 | 1.423 (5) |
C3—Si1 | 1.864 (4) | C110—C117 | 1.445 (5) |
C4—C5 | 1.207 (5) | C112—N101 | 1.391 (5) |
C4—Si1 | 1.827 (4) | C112—C117 | 1.419 (5) |
C5—C6 | 1.455 (5) | C201—Si21 | 1.869 (6) |
C9—N1 | 1.377 (5) | C202—Si21 | 1.856 (5) |
C9—C10 | 1.418 (5) | C203—Si21 | 1.847 (5) |
C10—C17 | 1.445 (5) | C204—C205 | 1.205 (6) |
C12—N1 | 1.385 (5) | C204—Si21 | 1.833 (4) |
C12—C17 | 1.417 (5) | C205—C206 | 1.448 (5) |
C101—Si11 | 1.860 (5) | C209—N201 | 1.385 (5) |
C102—Si11 | 1.855 (4) | C209—C210 | 1.426 (5) |
C103—Si11 | 1.862 (5) | C210—C217 | 1.450 (5) |
C104—C105 | 1.206 (6) | C212—N201 | 1.379 (5) |
C104—Si11 | 1.828 (4) | C212—C217 | 1.422 (5) |
C105—C106 | 1.438 (5) | ||
C5—C4—Si1 | 176.8 (4) | C1—Si1—C3 | 109.2 (2) |
C4—C5—C6 | 178.9 (4) | C4—Si1—C2 | 109.0 (2) |
N1—C9—C10 | 108.5 (3) | C1—Si1—C2 | 111.3 (2) |
C9—C10—C17 | 106.8 (3) | C3—Si1—C2 | 109.1 (2) |
N1—C12—C17 | 108.5 (3) | C104—Si11—C102 | 107.44 (19) |
C12—C17—C10 | 106.5 (3) | C104—Si11—C101 | 108.6 (2) |
C105—C104—Si11 | 178.1 (4) | C102—Si11—C101 | 111.8 (2) |
C104—C105—C106 | 176.0 (5) | C104—Si11—C103 | 110.5 (2) |
N101—C109—C110 | 108.8 (3) | C102—Si11—C103 | 108.0 (2) |
C109—C110—C117 | 106.3 (3) | C101—Si11—C103 | 110.6 (3) |
N101—C112—C117 | 108.0 (3) | C204—Si21—C203 | 108.0 (2) |
C112—C117—C110 | 107.3 (3) | C204—Si21—C202 | 107.7 (2) |
C205—C204—Si21 | 178.7 (4) | C203—Si21—C202 | 111.8 (3) |
C204—C205—C206 | 176.4 (5) | C204—Si21—C201 | 110.7 (2) |
N201—C209—C210 | 108.4 (3) | C203—Si21—C201 | 109.6 (3) |
C209—C210—C217 | 106.6 (3) | C202—Si21—C201 | 109.2 (3) |
N201—C212—C217 | 108.8 (3) | C9—N1—C12 | 109.7 (3) |
C212—C217—C210 | 106.4 (3) | C109—N101—C112 | 109.6 (3) |
C4—Si1—C1 | 107.1 (2) | C212—N201—C209 | 109.7 (3) |
C4—Si1—C3 | 111.1 (2) | ||
C5—C6—C7—C8 | 178.4 (4) | C5—C4—Si1—C2 | −123 (7) |
N1—C9—C10—C17 | −0.2 (4) | C105—C104—Si11—C102 | 7 (13) |
N1—C12—C17—C10 | −1.2 (4) | C105—C104—Si11—C101 | 128 (13) |
C9—C10—C17—C12 | 0.9 (4) | C105—C104—Si11—C103 | −110 (13) |
C105—C106—C107—C108 | 176.9 (4) | C205—C204—Si21—C203 | 105 (21) |
N101—C109—C110—C117 | 0.4 (4) | C205—C204—Si21—C202 | −16 (21) |
N101—C112—C117—C110 | −1.1 (4) | C205—C204—Si21—C201 | −135 (21) |
C109—C110—C117—C112 | 0.4 (4) | C10—C9—N1—C12 | −0.6 (4) |
C205—C206—C207—C208 | 176.3 (4) | C17—C12—N1—C9 | 1.1 (4) |
N201—C209—C210—C217 | −0.2 (4) | C110—C109—N101—C112 | −1.1 (4) |
N201—C212—C217—C210 | −1.7 (4) | C117—C112—N101—C109 | 1.3 (4) |
C209—C210—C217—C212 | 1.1 (4) | C217—C212—N201—C209 | 1.6 (4) |
C5—C4—Si1—C1 | −2 (7) | C210—C209—N201—C212 | −0.9 (4) |
C5—C4—Si1—C3 | 117 (7) |
In this paper, we report the structural characterization of the title compound, (I), which is a TMS-protected mono-alkyne and a precursor of the mononuclear platinum(II) di-yne species, trans-[Pt(PnBu3)2(—C≡ CR)2] (R = carbazol-3-yl). Such platinum-containing species form the building blocks for rigid-rod orgnaometallic poly-ynes of general formula trans-[Pt(PnBu3)2—C≡C—R—C≡C—]∞ (R = aromatic or heteroaromatic linker unit). Platinum poly-ynes are of immense current interest due to π-electron conjugation along the backbone, novel donor-acceptor interactions between the metal centres and the conjugated ligands and the unique photophysical properties arising from the large spin-orbit coupling (Wittmann et al., 1994; Beljonne et al., 1996; Younus et al., 1998; Chawdhury et al., 1998, 1999; Wilson et al., 2000, 2001; Khan, Al-Mandhary, Al-Suti, Feeder et al., 2002; Khan, Al-Mandhary, Al-Suti, Hisahm et al., 2002; Khan, Al-Mandhary, Al-Suti, Ahrens et al., 2003; Khan, Al-Mandhary, Al-Suti, Corcoran et al., 2003; Khan, Al-Suti et al., 2003). Precursors to these species, such as the title compound, are studied as models of the molecular and electronic properties and structurep-property relationships in the metal poly-ynes.