metal-organic compounds
(18-Crown-6-κ6O){(trimethylsilyl)[6-(trimethylsilylamino)pyridin-2-yl-κN1]azanido-κN}potassium(I)
aDepartment of Chemistry and Physics, Armstrong State University, Savannah, GA 31419, USA, and bDepartment of Chemistry, The University of Tennessee, Knoxville, TN, USA
*Correspondence e-mail: gary.guillet@armstrong.edu
The title complex, [K(C11H22N3Si2)(C12H24O6)], contains a single K+ cation coordinated by a monoanionic (6-trimethylsilylaminopyridin-2-yl)(trimethylsilyl)azanide (HL) ligand and an 18-crown-6 ligand. One SiMe3 group in HL is disordered over two positions, with an occupancy ratio of 0.727 (7):0.273 (7). The K+ cation is eight-coordinated, distributed between the pyridyl and azanide N atoms of HL, forming a four-membered ring, and a κ6 18-crown-6 ligand. The complex is best described as a and, unlike other similar literature examples, this complex does not dimerize. No intermolecular hydrogen bonding is observed in the likely indicating that weak electrostatic interactions are the dominant feature directing the crystal packing.
Keywords: crystal structure; potassium complex; trimethylsilylaminopyridine; crown ether; contact ion pair.
CCDC reference: 1500232
Structure description
The title compound (Fig. 1) is a monometallic complex comprised of a K+ cation that is eight-coordinate bonded to a monoanionic 6-(trimethylsilylamino)pyridin-2-yl-(trimethylsilyl)azanido ligand via the pyridyl nitrogen (N2) and the azanido nitrogen (N1), as well as to an 18-crown-6 ligand via six O atoms (O1–O6). The complex was synthesized by combining 2,6-bis(trimethylsilylamino)pyridine with excess potassium hydride and 18-crown-6 in tetrahydrofuran (THF) and is best described as a contact ion pair.
There are two prior comparable complexes formed from the similar 2-trimethylsilylaminopyridine ligand and a crown ether derivative, one utilizing 12-crown-4 (Liddle & Clegg, 2001) and the other 15-crown-5 (Liddle & Clegg, 2002). In contrast to the title complex, these structures both form dimers in the The dimer formed with 12-crown-4 bridges the two K+ cations by the pyridyl and azanido N atoms of the 2-trimethylsilylazanidopyridine, while the dimer formed with 15-crown-5 bridges instead via a single O atom in the 15-crown-5 ligand. This difference in the 15-crown-5 complex is attributed by the authors to the increased steric interaction between the bulkier 15-crown-5 and the trimethylsilyl moiety, labelling it a `slipped' dimer. The K—Npyridyl bond length in the title complex, K1—N2 = 2.858 (2) Å, fits in the range set by these two complexes (2.793–2.858 Å) as does the K—Nazanido bond length, K1—N1 = 2.822 (2) Å with the range being 2.800–2.912 Å for the prior complexes. The bonds between the potassium and the crown ether O atoms cover a similar range [2.770 (2)–3.049 (2) Å] to those observed for the 12-crown-4 complex [2.778–3.227 Å] and the 15-crown-5 complex [2.776–2.875 Å]. This is unsurprising since the K+ cation in all three cases is eight-coordinate.
One stark difference is the distance the K+ cation sits above the mean plane of the crown ether O atoms. In the title complex the distance is 1.100 (1) Å, while in the 12-crown-4 complex it is 2.535 Å and in the 15-crown-5 complex it is 1.558 Å. It is commonly accepted that K+ has close to an ideal fit within the 18-crown-6 molecule compared to other crown ether derivatives like 12-crown-4 or 15-crown-5. This is supported by a related complex reported with the less sterically demanding 2-phenylamidopyridine ligand and dibenzo-18-crown-6. This complex exhibits the same coordination environment about the K+ cation as observed in the title complex with similar K—N bond lengths for the NPyridyl and NAzanido of 2.852 and 2.794 Å, respectively, and the K+ cation in this case sits 0.783 Å above the mean plane of O atoms of the dibenzo-18-crown-6 (Clegg & Liddle, 2004). The shorter K+–crown distance compared to the related distance in the title complex could be attributed to the closer approach of the dibenzo-18-crown-6 to the less sterically bulky 2-phenylaminopyridine ligand compared to the 6-(trimethylsilylamino)pyridin-2-yl-(trimethylsilyl)azanido ligand used in this work.
Synthesis and crystallization
The 2,6-bis(trimethylsilylamino)pyridine used herein was synthesized according to a previous report (Danièle et al., 2001). The synthesis of the title complex was carried out in an air-free environment in an N2-filled glovebox. 2,6-Bis(trimethylsilylamino)pyridine (125 mg, 0.493 mmol) was dissolved in 5 ml of THF. Approximately two equivalents of potassium hydride (40 mg, 0.998 mmol) and two equivalents of 18-crown-6 (261 mg, 0.987 mmol) were added to the reaction with an additional 5 ml of THF. The slurry was heated to 45°C to form a golden-yellow solution over the course of one h. The solution was cooled to room temperature and the solvent was removed under reduced pressure to yield a powdery white residue. The residue was dissolved in benzene and filtered through celite. Crystals appropriate for X-ray crystallography were grown by a layering diffusion of the benzene solution with hexanes and the complex was isolated as pale-yellow crystals.
Refinement
Crystal data, data collection, and structure . One SiMe3 group is disordered over two positions, Si2/C9/C10/C11 and Si2′/C9′/C10′/C11′, with site occupancies converging to 0.727 (7) and 0.273 (7), respectively.
details are summarized in Table 1Structural data
CCDC reference: 1500232
10.1107/S2414314616013389/bh4011sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616013389/bh4011Isup2.hkl
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).[K(C11H22N3Si2)(C12H24O6)] | F(000) = 2400 |
Mr = 555.91 | Dx = 1.161 Mg m−3 |
Monoclinic, I2/a | Mo Kα radiation, λ = 0.71073 Å |
a = 20.3301 (10) Å | Cell parameters from 8021 reflections |
b = 17.4558 (6) Å | θ = 1.6–27.5° |
c = 20.5691 (11) Å | µ = 0.28 mm−1 |
β = 119.399 (7)° | T = 173 K |
V = 6359.5 (6) Å3 | Block, pale yellow |
Z = 8 | 0.56 × 0.36 × 0.29 mm |
Rigaku XtaLAB mini diffractometer | 5770 independent reflections |
Radiation source: Sealed Tube | 4565 reflections with I > 2σ(I) |
Graphite Monochromator monochromator | Rint = 0.046 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 25.3°, θmin = 2.3° |
ω scans | h = −24→24 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −20→20 |
Tmin = 0.797, Tmax = 1.000 | l = −24→24 |
27816 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.057 | Hydrogen site location: mixed |
wR(F2) = 0.140 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0533P)2 + 12.3202P] where P = (Fo2 + 2Fc2)/3 |
5770 reflections | (Δ/σ)max < 0.001 |
350 parameters | Δρmax = 0.64 e Å−3 |
6 restraints | Δρmin = −0.28 e Å−3 |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
K1 | 0.37601 (3) | 0.33574 (4) | 0.41659 (3) | 0.03787 (17) | |
Si1 | 0.53829 (5) | 0.24442 (5) | 0.36944 (4) | 0.0440 (2) | |
Si2 | 0.22824 (17) | 0.56321 (18) | 0.16953 (19) | 0.0538 (7) | 0.727 (7) |
O5 | 0.24060 (11) | 0.25955 (12) | 0.33205 (11) | 0.0432 (5) | |
O6 | 0.33257 (12) | 0.20087 (12) | 0.47690 (11) | 0.0493 (5) | |
O2 | 0.48287 (12) | 0.40416 (13) | 0.55274 (12) | 0.0542 (6) | |
O4 | 0.22649 (11) | 0.42225 (13) | 0.34204 (13) | 0.0548 (6) | |
N1 | 0.47290 (12) | 0.31219 (14) | 0.35653 (12) | 0.0382 (5) | |
N2 | 0.38208 (12) | 0.40545 (13) | 0.29390 (12) | 0.0348 (5) | |
O1 | 0.48377 (13) | 0.24315 (13) | 0.53913 (13) | 0.0561 (6) | |
O3 | 0.34216 (13) | 0.47888 (14) | 0.47999 (14) | 0.0636 (7) | |
C1 | 0.44893 (14) | 0.37042 (15) | 0.30789 (14) | 0.0340 (6) | |
N3 | 0.28526 (15) | 0.49256 (17) | 0.2328 (2) | 0.0572 (8) | |
C5 | 0.35350 (15) | 0.46304 (16) | 0.24448 (15) | 0.0392 (7) | |
C2 | 0.48654 (17) | 0.39912 (17) | 0.27002 (17) | 0.0446 (7) | |
H2 | 0.5319 | 0.3773 | 0.2788 | 0.054* | |
C19 | 0.18511 (17) | 0.30613 (19) | 0.27335 (17) | 0.0486 (8) | |
H19A | 0.1408 | 0.2753 | 0.2427 | 0.058* | |
H19B | 0.2053 | 0.3241 | 0.2420 | 0.058* | |
C18 | 0.16240 (17) | 0.3741 (2) | 0.30315 (19) | 0.0532 (8) | |
H18A | 0.1220 | 0.4020 | 0.2623 | 0.064* | |
H18B | 0.1445 | 0.3569 | 0.3366 | 0.064* | |
C4 | 0.3887 (2) | 0.49176 (18) | 0.20632 (18) | 0.0512 (8) | |
H4 | 0.3676 | 0.5317 | 0.1723 | 0.061* | |
C3 | 0.4565 (2) | 0.45838 (19) | 0.22108 (19) | 0.0540 (8) | |
H3A | 0.4819 | 0.4768 | 0.1971 | 0.065* | |
C20 | 0.21142 (17) | 0.2138 (2) | 0.36939 (17) | 0.0505 (8) | |
H20A | 0.1670 | 0.1862 | 0.3333 | 0.061* | |
H20B | 0.1972 | 0.2461 | 0.3989 | 0.061* | |
C6 | 0.53333 (19) | 0.2108 (2) | 0.28003 (18) | 0.0547 (8) | |
H6A | 0.4822 | 0.2145 | 0.2400 | 0.082* | |
H6B | 0.5498 | 0.1585 | 0.2855 | 0.082* | |
H6C | 0.5654 | 0.2423 | 0.2691 | 0.082* | |
C21 | 0.2714 (2) | 0.15905 (19) | 0.41856 (18) | 0.0561 (9) | |
H21A | 0.2511 | 0.1228 | 0.4399 | 0.067* | |
H21B | 0.2892 | 0.1307 | 0.3897 | 0.067* | |
C23 | 0.45575 (19) | 0.2034 (2) | 0.58003 (18) | 0.0581 (9) | |
H23A | 0.4378 | 0.2393 | 0.6038 | 0.070* | |
H23B | 0.4953 | 0.1723 | 0.6184 | 0.070* | |
C22 | 0.39254 (19) | 0.1539 (2) | 0.5265 (2) | 0.0587 (9) | |
H22A | 0.4094 | 0.1220 | 0.4989 | 0.070* | |
H22B | 0.3759 | 0.1207 | 0.5534 | 0.070* | |
C13 | 0.5376 (2) | 0.3591 (2) | 0.6117 (2) | 0.0724 (11) | |
H13A | 0.5204 | 0.3472 | 0.6469 | 0.087* | |
H13B | 0.5847 | 0.3873 | 0.6378 | 0.087* | |
C7 | 0.63966 (19) | 0.2734 (3) | 0.4331 (2) | 0.0780 (12) | |
H7A | 0.6517 | 0.3169 | 0.4124 | 0.117* | |
H7B | 0.6724 | 0.2316 | 0.4380 | 0.117* | |
H7C | 0.6464 | 0.2864 | 0.4813 | 0.117* | |
C8 | 0.5198 (2) | 0.1573 (2) | 0.4111 (2) | 0.0656 (10) | |
H8A | 0.5267 | 0.1696 | 0.4596 | 0.098* | |
H8B | 0.5544 | 0.1174 | 0.4158 | 0.098* | |
H8C | 0.4689 | 0.1402 | 0.3795 | 0.098* | |
C12 | 0.5499 (2) | 0.2879 (3) | 0.5811 (2) | 0.0786 (12) | |
H12A | 0.5712 | 0.3007 | 0.5493 | 0.094* | |
H12B | 0.5868 | 0.2570 | 0.6220 | 0.094* | |
C14 | 0.4656 (2) | 0.4693 (3) | 0.5824 (3) | 0.0738 (13) | |
C15 | 0.4119 (2) | 0.5184 (2) | 0.5220 (3) | 0.0717 (12) | |
H15A | 0.4037 | 0.5650 | 0.5426 | 0.086* | |
H15B | 0.4323 | 0.5323 | 0.4897 | 0.086* | |
C16 | 0.2860 (2) | 0.5253 (2) | 0.4243 (3) | 0.0801 (13) | |
H16A | 0.3025 | 0.5425 | 0.3898 | 0.096* | |
H16B | 0.2773 | 0.5701 | 0.4470 | 0.096* | |
C17 | 0.2145 (2) | 0.4802 (2) | 0.3833 (3) | 0.0798 (13) | |
H17A | 0.2013 | 0.4573 | 0.4184 | 0.096* | |
H17B | 0.1735 | 0.5134 | 0.3500 | 0.096* | |
C10 | 0.2656 (5) | 0.6614 (5) | 0.2001 (7) | 0.0866 (16) | 0.727 (7) |
H10A | 0.2619 | 0.6747 | 0.2435 | 0.130* | 0.727 (7) |
H10B | 0.2366 | 0.6971 | 0.1607 | 0.130* | 0.727 (7) |
H10C | 0.3175 | 0.6633 | 0.2119 | 0.130* | 0.727 (7) |
C9 | 0.2135 (4) | 0.5557 (4) | 0.0737 (3) | 0.0866 (16) | 0.727 (7) |
H9A | 0.2615 | 0.5541 | 0.0754 | 0.130* | 0.727 (7) |
H9B | 0.1854 | 0.5993 | 0.0451 | 0.130* | 0.727 (7) |
H9C | 0.1859 | 0.5097 | 0.0508 | 0.130* | 0.727 (7) |
C11 | 0.1346 (3) | 0.5513 (4) | 0.1639 (4) | 0.0866 (16) | 0.727 (7) |
H11A | 0.1177 | 0.4994 | 0.1506 | 0.130* | 0.727 (7) |
H11B | 0.0987 | 0.5854 | 0.1267 | 0.130* | 0.727 (7) |
H11C | 0.1389 | 0.5631 | 0.2114 | 0.130* | 0.727 (7) |
H14A | 0.515 (2) | 0.493 (2) | 0.615 (2) | 0.089 (13)* | |
H14B | 0.448 (3) | 0.453 (3) | 0.613 (3) | 0.108 (17)* | |
H3 | 0.274 (2) | 0.474 (2) | 0.260 (2) | 0.054 (12)* | |
C9' | 0.1665 (11) | 0.5500 (10) | 0.0965 (10) | 0.113 (6) | 0.273 (7) |
H9'A | 0.1937 | 0.5148 | 0.0826 | 0.169* | 0.273 (7) |
H9'B | 0.1562 | 0.5960 | 0.0676 | 0.169* | 0.273 (7) |
H9'C | 0.1198 | 0.5270 | 0.0873 | 0.169* | 0.273 (7) |
Si2' | 0.2232 (6) | 0.5729 (6) | 0.1957 (6) | 0.068 (2) | 0.273 (7) |
C10' | 0.2770 (15) | 0.6586 (13) | 0.216 (2) | 0.113 (6) | 0.273 (7) |
H10D | 0.2998 | 0.6695 | 0.2683 | 0.169* | 0.273 (7) |
H10E | 0.2445 | 0.7002 | 0.1880 | 0.169* | 0.273 (7) |
H10F | 0.3157 | 0.6524 | 0.2025 | 0.169* | 0.273 (7) |
C11' | 0.1599 (10) | 0.5936 (10) | 0.2300 (13) | 0.113 (6) | 0.273 (7) |
H11D | 0.1404 | 0.5466 | 0.2379 | 0.169* | 0.273 (7) |
H11E | 0.1190 | 0.6245 | 0.1942 | 0.169* | 0.273 (7) |
H11F | 0.1863 | 0.6210 | 0.2763 | 0.169* | 0.273 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
K1 | 0.0336 (3) | 0.0448 (4) | 0.0361 (3) | −0.0076 (3) | 0.0177 (3) | −0.0087 (3) |
Si1 | 0.0349 (4) | 0.0534 (5) | 0.0350 (4) | 0.0100 (4) | 0.0104 (4) | −0.0071 (4) |
Si2 | 0.0354 (9) | 0.0394 (9) | 0.0706 (18) | 0.0066 (6) | 0.0136 (11) | 0.0092 (11) |
O5 | 0.0381 (11) | 0.0529 (12) | 0.0373 (11) | −0.0103 (9) | 0.0175 (9) | −0.0108 (9) |
O6 | 0.0479 (12) | 0.0523 (13) | 0.0407 (11) | −0.0096 (10) | 0.0164 (10) | −0.0067 (10) |
O2 | 0.0497 (13) | 0.0575 (14) | 0.0470 (13) | −0.0146 (11) | 0.0172 (11) | −0.0130 (11) |
O4 | 0.0396 (12) | 0.0573 (14) | 0.0726 (15) | −0.0078 (10) | 0.0316 (11) | −0.0234 (12) |
N1 | 0.0334 (12) | 0.0470 (14) | 0.0307 (12) | 0.0035 (10) | 0.0129 (10) | −0.0056 (10) |
N2 | 0.0290 (11) | 0.0391 (13) | 0.0304 (12) | −0.0017 (10) | 0.0102 (10) | −0.0054 (10) |
O1 | 0.0516 (13) | 0.0570 (14) | 0.0569 (14) | −0.0085 (11) | 0.0244 (12) | −0.0044 (11) |
O3 | 0.0507 (14) | 0.0711 (16) | 0.0800 (17) | −0.0282 (12) | 0.0406 (14) | −0.0419 (14) |
C1 | 0.0297 (13) | 0.0370 (15) | 0.0288 (13) | −0.0040 (12) | 0.0093 (11) | −0.0141 (12) |
N3 | 0.0378 (15) | 0.0503 (18) | 0.076 (2) | 0.0042 (12) | 0.0225 (15) | 0.0138 (16) |
C5 | 0.0361 (15) | 0.0354 (15) | 0.0344 (15) | −0.0024 (12) | 0.0083 (13) | −0.0071 (12) |
C2 | 0.0456 (17) | 0.0433 (17) | 0.0542 (18) | −0.0031 (14) | 0.0316 (15) | −0.0109 (14) |
C19 | 0.0391 (16) | 0.059 (2) | 0.0389 (17) | −0.0070 (14) | 0.0123 (14) | −0.0097 (14) |
C18 | 0.0329 (16) | 0.063 (2) | 0.061 (2) | −0.0083 (15) | 0.0212 (15) | −0.0112 (17) |
C4 | 0.069 (2) | 0.0396 (17) | 0.0448 (18) | −0.0027 (16) | 0.0275 (17) | 0.0006 (14) |
C3 | 0.074 (2) | 0.0450 (19) | 0.060 (2) | −0.0067 (17) | 0.0469 (19) | −0.0076 (16) |
C20 | 0.0428 (17) | 0.066 (2) | 0.0389 (17) | −0.0227 (16) | 0.0171 (14) | −0.0134 (15) |
C6 | 0.055 (2) | 0.059 (2) | 0.0526 (19) | 0.0118 (16) | 0.0284 (17) | −0.0096 (16) |
C21 | 0.065 (2) | 0.054 (2) | 0.0481 (19) | −0.0271 (17) | 0.0267 (17) | −0.0129 (16) |
C23 | 0.0481 (19) | 0.079 (2) | 0.0417 (18) | 0.0054 (17) | 0.0177 (16) | 0.0048 (17) |
C22 | 0.057 (2) | 0.057 (2) | 0.063 (2) | −0.0006 (17) | 0.0295 (18) | 0.0078 (17) |
C13 | 0.063 (2) | 0.080 (3) | 0.054 (2) | −0.025 (2) | 0.0122 (19) | −0.008 (2) |
C7 | 0.0398 (19) | 0.100 (3) | 0.072 (3) | 0.014 (2) | 0.0098 (18) | −0.026 (2) |
C8 | 0.079 (3) | 0.063 (2) | 0.050 (2) | 0.0204 (19) | 0.0273 (19) | 0.0039 (17) |
C12 | 0.046 (2) | 0.084 (3) | 0.082 (3) | −0.007 (2) | 0.013 (2) | −0.004 (2) |
C14 | 0.059 (2) | 0.098 (3) | 0.075 (3) | −0.043 (2) | 0.041 (2) | −0.057 (3) |
C15 | 0.048 (2) | 0.065 (2) | 0.106 (3) | −0.0242 (19) | 0.040 (2) | −0.047 (2) |
C16 | 0.056 (2) | 0.064 (3) | 0.116 (4) | −0.006 (2) | 0.040 (2) | −0.045 (2) |
C17 | 0.048 (2) | 0.079 (3) | 0.110 (3) | −0.0038 (19) | 0.037 (2) | −0.048 (3) |
C10 | 0.064 (2) | 0.067 (2) | 0.106 (3) | 0.0136 (18) | 0.024 (2) | 0.015 (2) |
C9 | 0.064 (2) | 0.067 (2) | 0.106 (3) | 0.0136 (18) | 0.024 (2) | 0.015 (2) |
C11 | 0.064 (2) | 0.067 (2) | 0.106 (3) | 0.0136 (18) | 0.024 (2) | 0.015 (2) |
C9' | 0.082 (8) | 0.059 (6) | 0.154 (14) | 0.033 (5) | 0.024 (8) | −0.001 (7) |
Si2' | 0.048 (3) | 0.067 (4) | 0.076 (5) | 0.011 (2) | 0.021 (3) | 0.017 (4) |
C10' | 0.082 (8) | 0.059 (6) | 0.154 (14) | 0.033 (5) | 0.024 (8) | −0.001 (7) |
C11' | 0.082 (8) | 0.059 (6) | 0.154 (14) | 0.033 (5) | 0.024 (8) | −0.001 (7) |
K1—O1 | 2.889 (2) | C6—H6C | 0.9600 |
K1—O2 | 2.831 (2) | C21—H21A | 0.9700 |
K1—O3 | 3.049 (2) | C21—H21B | 0.9700 |
K1—O4 | 3.049 (2) | C23—H23A | 0.9700 |
K1—O5 | 2.770 (2) | C23—H23B | 0.9700 |
K1—O6 | 2.990 (2) | C23—C22 | 1.491 (5) |
K1—N1 | 2.822 (2) | C22—H22A | 0.9700 |
K1—N2 | 2.858 (2) | C22—H22B | 0.9700 |
Si1—N1 | 1.700 (2) | C13—H13A | 0.9700 |
Si1—C6 | 1.885 (3) | C13—H13B | 0.9700 |
Si1—C7 | 1.889 (4) | C13—C12 | 1.469 (6) |
Si1—C8 | 1.873 (4) | C7—H7A | 0.9600 |
Si2—N3 | 1.754 (4) | C7—H7B | 0.9600 |
Si2—C10 | 1.856 (9) | C7—H7C | 0.9600 |
Si2—C9 | 1.847 (7) | C8—H8A | 0.9600 |
Si2—C11 | 1.862 (7) | C8—H8B | 0.9600 |
O5—C19 | 1.433 (4) | C8—H8C | 0.9600 |
O5—C20 | 1.423 (4) | C12—H12A | 0.9700 |
O6—C21 | 1.433 (4) | C12—H12B | 0.9700 |
O6—C22 | 1.407 (4) | C14—C15 | 1.462 (6) |
O2—C13 | 1.416 (4) | C14—H14A | 0.98 (5) |
O2—C14 | 1.414 (5) | C14—H14B | 0.91 (5) |
O4—C18 | 1.422 (4) | C15—H15A | 0.9700 |
O4—C17 | 1.417 (4) | C15—H15B | 0.9700 |
N1—C1 | 1.339 (4) | C16—H16A | 0.9700 |
N2—C1 | 1.385 (3) | C16—H16B | 0.9700 |
N2—C5 | 1.342 (4) | C16—C17 | 1.497 (5) |
O1—C23 | 1.409 (4) | C17—H17A | 0.9700 |
O1—C12 | 1.423 (4) | C17—H17B | 0.9700 |
O3—C15 | 1.425 (4) | C10—H10A | 0.9600 |
O3—C16 | 1.410 (5) | C10—H10B | 0.9600 |
C1—C2 | 1.424 (4) | C10—H10C | 0.9600 |
N3—C5 | 1.386 (4) | C9—H9A | 0.9600 |
N3—H3 | 0.76 (3) | C9—H9B | 0.9600 |
N3—Si2' | 1.788 (11) | C9—H9C | 0.9600 |
C5—C4 | 1.389 (4) | C11—H11A | 0.9600 |
C2—H2 | 0.9300 | C11—H11B | 0.9600 |
C2—C3 | 1.361 (5) | C11—H11C | 0.9600 |
C19—H19A | 0.9700 | C9'—H9'A | 0.9600 |
C19—H19B | 0.9700 | C9'—H9'B | 0.9600 |
C19—C18 | 1.507 (4) | C9'—H9'C | 0.9600 |
C18—H18A | 0.9700 | C9'—Si2' | 1.828 (17) |
C18—H18B | 0.9700 | Si2'—C10' | 1.78 (2) |
C4—H4 | 0.9300 | Si2'—C11' | 1.782 (17) |
C4—C3 | 1.387 (5) | C10'—H10D | 0.9600 |
C3—H3A | 0.9300 | C10'—H10E | 0.9600 |
C20—H20A | 0.9700 | C10'—H10F | 0.9600 |
C20—H20B | 0.9700 | C11'—H11D | 0.9600 |
C20—C21 | 1.488 (5) | C11'—H11E | 0.9600 |
C6—H6A | 0.9600 | C11'—H11F | 0.9600 |
C6—H6B | 0.9600 | ||
O5—K1—O6 | 58.49 (6) | H6B—C6—H6C | 109.5 |
O5—K1—O2 | 150.12 (6) | O6—C21—C20 | 109.1 (3) |
O5—K1—O4 | 58.92 (6) | O6—C21—H21A | 109.9 |
O5—K1—N1 | 110.33 (6) | O6—C21—H21B | 109.9 |
O5—K1—N2 | 96.35 (6) | C20—C21—H21A | 109.9 |
O5—K1—O1 | 111.93 (6) | C20—C21—H21B | 109.9 |
O5—K1—O3 | 107.36 (6) | H21A—C21—H21B | 108.3 |
O6—K1—O4 | 100.02 (6) | O1—C23—H23A | 110.2 |
O6—K1—O3 | 107.05 (6) | O1—C23—H23B | 110.2 |
O2—K1—O6 | 99.28 (6) | O1—C23—C22 | 107.4 (3) |
O2—K1—O4 | 112.34 (7) | H23A—C23—H23B | 108.5 |
O2—K1—N2 | 110.43 (7) | C22—C23—H23A | 110.2 |
O2—K1—O1 | 59.19 (7) | C22—C23—H23B | 110.2 |
O2—K1—O3 | 57.04 (7) | O6—C22—C23 | 108.8 (3) |
O4—K1—O3 | 55.30 (6) | O6—C22—H22A | 109.9 |
N1—K1—O6 | 118.60 (7) | O6—C22—H22B | 109.9 |
N1—K1—O2 | 97.64 (7) | C23—C22—H22A | 109.9 |
N1—K1—O4 | 126.14 (7) | C23—C22—H22B | 109.9 |
N1—K1—N2 | 48.21 (6) | H22A—C22—H22B | 108.3 |
N1—K1—O1 | 84.67 (7) | O2—C13—H13A | 109.8 |
N1—K1—O3 | 131.24 (7) | O2—C13—H13B | 109.8 |
N2—K1—O6 | 148.34 (6) | O2—C13—C12 | 109.3 (3) |
N2—K1—O4 | 79.02 (6) | H13A—C13—H13B | 108.3 |
N2—K1—O1 | 131.73 (7) | C12—C13—H13A | 109.8 |
N2—K1—O3 | 98.36 (7) | C12—C13—H13B | 109.8 |
O1—K1—O6 | 56.58 (6) | Si1—C7—H7A | 109.5 |
O1—K1—O4 | 149.08 (7) | Si1—C7—H7B | 109.5 |
O1—K1—O3 | 108.60 (7) | Si1—C7—H7C | 109.5 |
N1—Si1—C6 | 113.64 (13) | H7A—C7—H7B | 109.5 |
N1—Si1—C7 | 115.16 (15) | H7A—C7—H7C | 109.5 |
N1—Si1—C8 | 108.62 (15) | H7B—C7—H7C | 109.5 |
C6—Si1—C7 | 106.12 (17) | Si1—C8—H8A | 109.5 |
C8—Si1—C6 | 105.50 (16) | Si1—C8—H8B | 109.5 |
C8—Si1—C7 | 107.20 (19) | Si1—C8—H8C | 109.5 |
N3—Si2—C10 | 112.8 (3) | H8A—C8—H8B | 109.5 |
N3—Si2—C9 | 116.3 (3) | H8A—C8—H8C | 109.5 |
N3—Si2—C11 | 104.5 (3) | H8B—C8—H8C | 109.5 |
C10—Si2—C11 | 111.1 (5) | O1—C12—C13 | 114.5 (3) |
C9—Si2—C10 | 104.6 (5) | O1—C12—H12A | 108.6 |
C9—Si2—C11 | 107.5 (3) | O1—C12—H12B | 108.6 |
C19—O5—K1 | 112.66 (16) | C13—C12—H12A | 108.6 |
C20—O5—K1 | 118.66 (16) | C13—C12—H12B | 108.6 |
C20—O5—C19 | 114.1 (2) | H12A—C12—H12B | 107.6 |
C21—O6—K1 | 111.44 (17) | O2—C14—C15 | 110.1 (3) |
C22—O6—K1 | 115.64 (18) | O2—C14—H14A | 105 (2) |
C22—O6—C21 | 113.4 (3) | O2—C14—H14B | 108 (3) |
C13—O2—K1 | 120.8 (2) | C15—C14—H14A | 115 (2) |
C14—O2—K1 | 122.3 (2) | C15—C14—H14B | 113 (3) |
C14—O2—C13 | 109.6 (3) | H14A—C14—H14B | 105 (4) |
C18—O4—K1 | 113.71 (18) | O3—C15—C14 | 109.8 (3) |
C17—O4—K1 | 118.3 (2) | O3—C15—H15A | 109.7 |
C17—O4—C18 | 112.3 (2) | O3—C15—H15B | 109.7 |
Si1—N1—K1 | 133.89 (12) | C14—C15—H15A | 109.7 |
C1—N1—K1 | 98.06 (16) | C14—C15—H15B | 109.7 |
C1—N1—Si1 | 127.94 (19) | H15A—C15—H15B | 108.2 |
C1—N2—K1 | 95.27 (16) | O3—C16—H16A | 109.8 |
C5—N2—K1 | 142.86 (18) | O3—C16—H16B | 109.8 |
C5—N2—C1 | 120.2 (2) | O3—C16—C17 | 109.3 (4) |
C23—O1—K1 | 116.16 (18) | H16A—C16—H16B | 108.3 |
C23—O1—C12 | 116.6 (3) | C17—C16—H16A | 109.8 |
C12—O1—K1 | 108.0 (2) | C17—C16—H16B | 109.8 |
C15—O3—K1 | 106.81 (19) | O4—C17—C16 | 108.0 (3) |
C16—O3—K1 | 112.76 (19) | O4—C17—H17A | 110.1 |
C16—O3—C15 | 112.5 (3) | O4—C17—H17B | 110.1 |
N1—C1—K1 | 58.17 (14) | C16—C17—H17A | 110.1 |
N1—C1—N2 | 116.8 (2) | C16—C17—H17B | 110.1 |
N1—C1—C2 | 125.4 (3) | H17A—C17—H17B | 108.4 |
N2—C1—K1 | 59.93 (14) | Si2—C10—H10A | 109.5 |
N2—C1—C2 | 117.8 (3) | Si2—C10—H10B | 109.5 |
C2—C1—K1 | 168.24 (18) | Si2—C10—H10C | 109.5 |
Si2—N3—H3 | 121 (3) | H10A—C10—H10B | 109.5 |
C5—N3—Si2 | 129.1 (3) | H10A—C10—H10C | 109.5 |
C5—N3—H3 | 110 (3) | H10B—C10—H10C | 109.5 |
C5—N3—Si2' | 143.3 (4) | Si2—C9—H9A | 109.5 |
Si2'—N3—H3 | 104 (3) | Si2—C9—H9B | 109.5 |
N2—C5—N3 | 115.7 (3) | Si2—C9—H9C | 109.5 |
N2—C5—C4 | 123.1 (3) | H9A—C9—H9B | 109.5 |
N3—C5—C4 | 121.1 (3) | H9A—C9—H9C | 109.5 |
C1—C2—H2 | 119.8 | H9B—C9—H9C | 109.5 |
C3—C2—C1 | 120.4 (3) | Si2—C11—H11A | 109.5 |
C3—C2—H2 | 119.8 | Si2—C11—H11B | 109.5 |
O5—C19—H19A | 109.2 | Si2—C11—H11C | 109.5 |
O5—C19—H19B | 109.2 | H11A—C11—H11B | 109.5 |
O5—C19—C18 | 112.0 (2) | H11A—C11—H11C | 109.5 |
H19A—C19—H19B | 107.9 | H11B—C11—H11C | 109.5 |
C18—C19—H19A | 109.2 | H9'A—C9'—H9'B | 109.5 |
C18—C19—H19B | 109.2 | H9'A—C9'—H9'C | 109.5 |
O4—C18—C19 | 108.4 (2) | H9'B—C9'—H9'C | 109.5 |
O4—C18—H18A | 110.0 | Si2'—C9'—H9'A | 109.5 |
O4—C18—H18B | 110.0 | Si2'—C9'—H9'B | 109.5 |
C19—C18—H18A | 110.0 | Si2'—C9'—H9'C | 109.5 |
C19—C18—H18B | 110.0 | N3—Si2'—C9' | 103.4 (7) |
H18A—C18—H18B | 108.4 | C10'—Si2'—N3 | 109.7 (10) |
C5—C4—H4 | 121.4 | C10'—Si2'—C9' | 115.2 (16) |
C3—C4—C5 | 117.2 (3) | C10'—Si2'—C11' | 102.5 (16) |
C3—C4—H4 | 121.4 | C11'—Si2'—N3 | 119.0 (8) |
C2—C3—C4 | 121.2 (3) | C11'—Si2'—C9' | 107.7 (11) |
C2—C3—H3A | 119.4 | Si2'—C10'—H10D | 109.5 |
C4—C3—H3A | 119.4 | Si2'—C10'—H10E | 109.5 |
O5—C20—H20A | 110.1 | Si2'—C10'—H10F | 109.5 |
O5—C20—H20B | 110.1 | H10D—C10'—H10E | 109.5 |
O5—C20—C21 | 107.9 (3) | H10D—C10'—H10F | 109.5 |
H20A—C20—H20B | 108.4 | H10E—C10'—H10F | 109.5 |
C21—C20—H20A | 110.1 | Si2'—C11'—H11D | 109.5 |
C21—C20—H20B | 110.1 | Si2'—C11'—H11E | 109.5 |
Si1—C6—H6A | 109.5 | Si2'—C11'—H11F | 109.5 |
Si1—C6—H6B | 109.5 | H11D—C11'—H11E | 109.5 |
Si1—C6—H6C | 109.5 | H11D—C11'—H11F | 109.5 |
H6A—C6—H6B | 109.5 | H11E—C11'—H11F | 109.5 |
H6A—C6—H6C | 109.5 | ||
K1—O5—C19—C18 | −64.4 (3) | C1—N2—C5—C4 | −1.4 (4) |
K1—O5—C20—C21 | −53.6 (3) | C1—C2—C3—C4 | −0.6 (5) |
K1—O6—C21—C20 | −47.2 (3) | N3—C5—C4—C3 | −179.5 (3) |
K1—O6—C22—C23 | 44.1 (3) | C5—N2—C1—K1 | 168.7 (3) |
K1—O2—C13—C12 | 23.9 (4) | C5—N2—C1—N1 | −178.4 (2) |
K1—O2—C14—C15 | −32.7 (4) | C5—N2—C1—C2 | 1.9 (3) |
K1—O4—C18—C19 | −31.6 (3) | C5—N3—Si2'—C9' | 85.7 (12) |
K1—O4—C17—C16 | 42.1 (5) | C5—N3—Si2'—C10' | −37.6 (19) |
K1—N1—C1—N2 | −13.2 (2) | C5—N3—Si2'—C11' | −155.1 (9) |
K1—N1—C1—C2 | 166.5 (2) | C5—C4—C3—C2 | 1.1 (5) |
K1—N2—C1—N1 | 12.9 (2) | C19—O5—C20—C21 | 169.9 (2) |
K1—N2—C1—C2 | −166.8 (2) | C18—O4—C17—C16 | 177.7 (4) |
K1—N2—C5—N3 | −20.9 (4) | C20—O5—C19—C18 | 74.7 (3) |
K1—N2—C5—C4 | 159.7 (2) | C6—Si1—N1—K1 | 136.60 (17) |
K1—O1—C23—C22 | 57.4 (3) | C6—Si1—N1—C1 | −38.6 (3) |
K1—O1—C12—C13 | 59.2 (4) | C21—O6—C22—C23 | 174.5 (3) |
K1—O3—C15—C14 | −60.4 (3) | C23—O1—C12—C13 | −73.7 (4) |
K1—O3—C16—C17 | 59.7 (4) | C22—O6—C21—C20 | −179.8 (3) |
K1—C1—C2—C3 | −76.7 (10) | C13—O2—C14—C15 | 177.2 (3) |
Si1—N1—C1—K1 | 176.5 (3) | C7—Si1—N1—K1 | −100.7 (2) |
Si1—N1—C1—N2 | 163.35 (19) | C7—Si1—N1—C1 | 84.1 (3) |
Si1—N1—C1—C2 | −16.9 (4) | C8—Si1—N1—K1 | 19.5 (2) |
Si2—N3—C5—N2 | −175.9 (3) | C8—Si1—N1—C1 | −155.7 (2) |
Si2—N3—C5—C4 | 3.5 (5) | C12—O1—C23—C22 | −173.6 (3) |
O5—C19—C18—O4 | 64.3 (3) | C14—O2—C13—C12 | 174.6 (3) |
O5—C20—C21—O6 | 66.8 (3) | C15—O3—C16—C17 | −179.4 (3) |
O2—C13—C12—O1 | −57.3 (5) | C16—O3—C15—C14 | 175.4 (3) |
O2—C14—C15—O3 | 64.3 (4) | C17—O4—C18—C19 | −169.3 (3) |
N1—C1—C2—C3 | 179.4 (3) | C10—Si2—N3—C5 | −76.5 (6) |
N2—C1—C2—C3 | −0.9 (4) | C9—Si2—N3—C5 | 44.4 (5) |
N2—C5—C4—C3 | −0.1 (4) | C11—Si2—N3—C5 | 162.7 (4) |
O1—C23—C22—O6 | −66.8 (3) | Si2'—N3—C5—N2 | 163.3 (7) |
O3—C16—C17—O4 | −68.1 (5) | Si2'—N3—C5—C4 | −17.3 (8) |
C1—N2—C5—N3 | 178.0 (2) |
Acknowledgements
The authors would like to thank Armstrong State University for funding.
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