The co-crystal structure of
N-methylpiperidine betaine with
N-methylpiperidine betaine hexafluorosilicate represents an unusual case of a salt co-crystal with a high
Z′ value (3), unexpected conformational variability, and with nearly 50% of its contents disordered. The betaine units from the salt and co-crystal formers are paired into several homoconjugated dimers
via very short, linear O
−H
+O
− bridges. These hydrogen bonds are the dominating interactions in the co-crystal structure, in variance with the simple hexafluorosilicate salt, which has a structure governed by COOH
F hydrogen bonds. The SiF
anion in the co-crystal structure has only C—H
F interactions with the betaine units. The zwitterion:cation:anion stoichiometry is 3:3:1.5. Some of the betaine units display disorder, but each case is different. One of the SiF
anions is ordered while possessing exact crystallographic symmetry. The other one is disordered in a general position. In addition, there are three water molecules in the crystal structure. One is fully ordered, one has an H atom disordered in two positions and the third one occupies two alternative positions with unequal populations.
Supporting information
CCDC reference: 668712
Data collection: KUMA CCD; cell refinement: KUMA CCD; data reduction: KUMA CrysAlis; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL & pyMOL v0.99; software used to prepare material for publication: SHELX97.
'
N-carboxymethyl-
N-methylpiperidinium hemihexafluorosilicate
hydrate'
top
Crystal data top
(C8H15NO2)·(C8H16NO2)·0.5(SiF6)·(H2O) | Z = 6 |
Mr = 404.49 | F(000) = 1302.0 |
Triclinic, P1 | Dx = 1.362 Mg m−3 |
Hall symbol: -P 1 | Melting point: 483-485 K K |
a = 11.554 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.621 (3) Å | Cell parameters from 27619 reflections |
c = 22.763 (5) Å | θ = 3–30° |
α = 83.87 (3)° | µ = 0.15 mm−1 |
β = 84.81 (3)° | T = 100 K |
γ = 63.86 (3)° | Prism, colourless |
V = 2959.2 (10) Å3 | 0.3 × 0.3 × 0.2 mm |
Data collection top
KM4 CCD diffractometer | 8890 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 27.5°, θmin = 3.4° |
oscillation method scans | h = −15→15 |
27619 measured reflections | k = −16→16 |
13415 independent reflections | l = −17→29 |
Refinement top
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.138 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0636P)2] where P = (Fo2 + 2Fc2)/3 |
13415 reflections | (Δ/σ)max = 0.012 |
847 parameters | Δρmax = 0.66 e Å−3 |
150 restraints | Δρmin = −0.40 e Å−3 |
Special details top
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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Si1 | 0.0000 | 1.0000 | 0.0000 | 0.01683 (19) | |
Si2 | 0.95340 (6) | 0.04205 (6) | 0.33314 (3) | 0.02471 (16) | |
F11 | −0.13709 (13) | 1.03621 (12) | 0.04285 (6) | 0.0301 (3) | |
F12 | 0.05038 (13) | 0.85807 (11) | 0.02649 (6) | 0.0291 (3) | |
F13 | 0.07230 (12) | 1.02583 (11) | 0.05477 (5) | 0.0218 (3) | |
F21 | 0.86375 (13) | 0.02605 (13) | 0.28356 (6) | 0.0328 (3) | |
F22A | 1.0655 (4) | −0.0991 (3) | 0.31796 (17) | 0.0460 (10) | 0.50 |
F23A | 0.8962 (7) | −0.0231 (6) | 0.3886 (3) | 0.0445 (19) | 0.50 |
F24A | 0.8495 (5) | 0.1739 (3) | 0.3508 (2) | 0.0634 (14) | 0.50 |
F25A | 1.0246 (4) | 0.0947 (5) | 0.27868 (16) | 0.0548 (12) | 0.50 |
F22B | 1.0915 (3) | −0.0427 (4) | 0.30274 (17) | 0.0471 (11) | 0.50 |
F23B | 0.9384 (7) | −0.0611 (6) | 0.3785 (3) | 0.0473 (19) | 0.50 |
F24B | 0.8045 (4) | 0.1423 (4) | 0.36137 (19) | 0.0402 (10) | 0.50 |
F25B | 0.9508 (4) | 0.1613 (3) | 0.28741 (15) | 0.0381 (9) | 0.50 |
F26 | 1.04153 (18) | 0.05879 (17) | 0.38323 (6) | 0.0561 (5) | |
O11 | 0.60369 (16) | 0.00620 (15) | 0.49549 (8) | 0.0332 (4) | |
O12 | 0.50628 (17) | 0.18500 (16) | 0.53087 (8) | 0.0365 (4) | |
O21 | 0.91682 (17) | 0.67705 (15) | 0.16659 (7) | 0.0288 (4) | |
O22 | 0.93941 (16) | 0.56825 (14) | 0.09135 (7) | 0.0297 (4) | |
O31 | 0.36537 (15) | 0.01683 (13) | 0.15082 (7) | 0.0237 (4) | |
O32 | 0.46434 (14) | −0.18022 (13) | 0.16158 (7) | 0.0245 (4) | |
O41 | 0.57968 (15) | 0.01404 (14) | 0.14933 (7) | 0.0250 (4) | |
O42 | 0.47466 (14) | 0.20198 (14) | 0.17283 (7) | 0.0264 (4) | |
O51 | 1.04101 (17) | 0.49209 (16) | 0.22747 (8) | 0.0358 (4) | |
O52 | 0.85483 (16) | 0.48943 (14) | 0.26150 (7) | 0.0309 (4) | |
N11 | 0.7528 (2) | 0.20168 (18) | 0.51907 (8) | 0.0324 (5) | |
N21 | 0.75780 (16) | 0.78359 (15) | 0.02602 (8) | 0.0167 (4) | |
N31 | 0.21166 (16) | −0.18582 (15) | 0.17209 (8) | 0.0164 (4) | |
N41 | 0.71834 (16) | 0.22219 (15) | 0.15702 (8) | 0.0171 (4) | |
N51 | 1.18262 (18) | 0.27638 (17) | 0.29860 (9) | 0.0268 (5) | |
N61 | 0.75984 (19) | 0.78445 (17) | 0.35799 (8) | 0.0260 (5) | |
C12 | 0.6735 (3) | 0.3081 (2) | 0.47851 (13) | 0.0488 (8) | |
H12A | 0.6989 | 0.2892 | 0.4377 | 0.059* | |
H12B | 0.5831 | 0.3251 | 0.4849 | 0.059* | |
C13 | 0.6901 (3) | 0.4173 (3) | 0.48853 (14) | 0.0541 (9) | |
H13A | 0.7772 | 0.4052 | 0.4759 | 0.065* | 0.55 |
H13B | 0.6307 | 0.4845 | 0.4647 | 0.065* | 0.55 |
H13C | 0.6376 | 0.4825 | 0.4616 | 0.065* | 0.45 |
H13D | 0.6603 | 0.4392 | 0.5286 | 0.065* | 0.45 |
C14A | 0.6658 (6) | 0.4437 (4) | 0.55177 (18) | 0.0533 (15) | 0.55 |
H14A | 0.5744 | 0.4717 | 0.5621 | 0.064* | 0.55 |
H14B | 0.6895 | 0.5066 | 0.5574 | 0.064* | 0.55 |
C15A | 0.7408 (5) | 0.3371 (4) | 0.5925 (2) | 0.0441 (13) | 0.55 |
H15A | 0.7170 | 0.3574 | 0.6332 | 0.053* | 0.55 |
H15B | 0.8322 | 0.3158 | 0.5858 | 0.053* | 0.55 |
C14B | 0.8250 (4) | 0.3970 (5) | 0.4790 (3) | 0.0455 (16) | 0.45 |
H14C | 0.8359 | 0.4631 | 0.4914 | 0.055* | 0.45 |
H14D | 0.8515 | 0.3887 | 0.4375 | 0.055* | 0.45 |
C15B | 0.9048 (5) | 0.2852 (4) | 0.5152 (3) | 0.0381 (15) | 0.45 |
H15C | 0.8834 | 0.3008 | 0.5566 | 0.046* | 0.45 |
H15D | 0.9946 | 0.2698 | 0.5078 | 0.046* | 0.45 |
C16 | 0.7162 (3) | 0.2287 (3) | 0.58328 (11) | 0.0448 (7) | |
H16A | 0.7682 | 0.1611 | 0.6092 | 0.054* | 0.55 |
H16B | 0.6260 | 0.2467 | 0.5921 | 0.054* | 0.55 |
H17E | 0.6263 | 0.2483 | 0.5912 | 0.067* | 0.45 |
H17F | 0.7322 | 0.2943 | 0.5909 | 0.067* | 0.45 |
H17G | 0.7669 | 0.1605 | 0.6084 | 0.067* | 0.45 |
C18 | 0.7367 (2) | 0.0951 (2) | 0.50628 (11) | 0.0284 (6) | |
H18A | 0.7907 | 0.0290 | 0.5324 | 0.034* | |
H18B | 0.7702 | 0.0764 | 0.4662 | 0.034* | |
C19 | 0.6018 (2) | 0.1015 (2) | 0.51223 (10) | 0.0258 (5) | |
C17 | 0.8945 (3) | 0.1713 (3) | 0.50675 (12) | 0.0409 (7) | |
H17A | 0.9454 | 0.1038 | 0.5322 | 0.061* | 0.55 |
H17B | 0.9099 | 0.2375 | 0.5140 | 0.061* | 0.55 |
H17C | 0.9182 | 0.1534 | 0.4662 | 0.061* | 0.55 |
H16C | 0.9218 | 0.1480 | 0.4667 | 0.049* | 0.45 |
H16D | 0.9473 | 0.1074 | 0.5342 | 0.049* | 0.45 |
C22 | 0.8573 (2) | 0.7185 (2) | −0.02182 (10) | 0.0210 (5) | |
H22A | 0.9064 | 0.7627 | −0.0354 | 0.025* | |
H22B | 0.9168 | 0.6416 | −0.0050 | 0.025* | |
C23 | 0.7967 (2) | 0.7013 (2) | −0.07427 (10) | 0.0223 (5) | |
H23A | 0.8643 | 0.6529 | −0.1015 | 0.027* | |
H23B | 0.7477 | 0.7777 | −0.0950 | 0.027* | |
C24 | 0.7077 (2) | 0.6424 (2) | −0.05514 (10) | 0.0256 (5) | |
H24A | 0.7576 | 0.5630 | −0.0377 | 0.031* | |
H24B | 0.6672 | 0.6364 | −0.0894 | 0.031* | |
C25 | 0.6041 (2) | 0.7147 (2) | −0.01016 (10) | 0.0244 (5) | |
H25A | 0.5503 | 0.7921 | −0.0286 | 0.029* | |
H25B | 0.5497 | 0.6753 | 0.0028 | 0.029* | |
C26 | 0.6651 (2) | 0.7290 (2) | 0.04264 (10) | 0.0207 (5) | |
H26A | 0.7110 | 0.6520 | 0.0633 | 0.025* | |
H26B | 0.5975 | 0.7783 | 0.0696 | 0.025* | |
C28 | 0.8238 (2) | 0.78261 (19) | 0.08053 (10) | 0.0204 (5) | |
H28A | 0.7587 | 0.8327 | 0.1081 | 0.024* | |
H28B | 0.8826 | 0.8181 | 0.0692 | 0.024* | |
C29 | 0.8993 (2) | 0.6621 (2) | 0.11290 (11) | 0.0226 (5) | |
C27 | 0.6854 (2) | 0.91150 (18) | 0.00459 (10) | 0.0212 (5) | |
H27A | 0.6222 | 0.9529 | 0.0346 | 0.032* | |
H27B | 0.6430 | 0.9170 | −0.0308 | 0.032* | |
H27C | 0.7447 | 0.9462 | −0.0037 | 0.032* | |
C32 | 0.2703 (2) | −0.24935 (19) | 0.11603 (9) | 0.0194 (5) | |
H32A | 0.2257 | −0.1988 | 0.0822 | 0.023* | |
H32B | 0.3602 | −0.2639 | 0.1109 | 0.023* | |
C33 | 0.2614 (2) | −0.3662 (2) | 0.11787 (10) | 0.0272 (6) | |
H33A | 0.1714 | −0.3512 | 0.1187 | 0.033* | |
H33B | 0.3039 | −0.4058 | 0.0824 | 0.033* | |
C34 | 0.3238 (3) | −0.4460 (2) | 0.17194 (11) | 0.0335 (6) | |
H34A | 0.4157 | −0.4679 | 0.1691 | 0.040* | |
H34B | 0.3123 | −0.5179 | 0.1733 | 0.040* | |
C35 | 0.2644 (3) | −0.3836 (2) | 0.22855 (11) | 0.0320 (6) | |
H35A | 0.1747 | −0.3699 | 0.2337 | 0.038* | |
H35B | 0.3095 | −0.4341 | 0.2622 | 0.038* | |
C36 | 0.2722 (2) | −0.26606 (19) | 0.22644 (10) | 0.0231 (5) | |
H36A | 0.2283 | −0.2262 | 0.2617 | 0.028* | |
H36B | 0.3620 | −0.2808 | 0.2264 | 0.028* | |
C38 | 0.2296 (2) | −0.07434 (18) | 0.16946 (10) | 0.0173 (5) | |
H38A | 0.1932 | −0.0371 | 0.2062 | 0.021* | |
H38B | 0.1789 | −0.0209 | 0.1378 | 0.021* | |
C39 | 0.3667 (2) | −0.08523 (19) | 0.15991 (9) | 0.0181 (5) | |
C37 | 0.0676 (2) | −0.1469 (2) | 0.17629 (10) | 0.0224 (5) | |
H37A | 0.0314 | −0.1074 | 0.2119 | 0.034* | |
H37B | 0.0505 | −0.2149 | 0.1769 | 0.034* | |
H37C | 0.0292 | −0.0936 | 0.1427 | 0.034* | |
C42 | 0.8625 (2) | 0.19090 (19) | 0.15268 (10) | 0.0190 (5) | |
H42A | 0.8992 | 0.1544 | 0.1905 | 0.023* | |
H42B | 0.9051 | 0.1336 | 0.1234 | 0.023* | |
C43 | 0.8885 (2) | 0.2979 (2) | 0.13592 (10) | 0.0239 (5) | |
H43A | 0.9809 | 0.2733 | 0.1323 | 0.029* | |
H43B | 0.8528 | 0.3524 | 0.1669 | 0.029* | |
C44 | 0.8287 (2) | 0.3605 (2) | 0.07759 (10) | 0.0247 (5) | |
H44A | 0.8431 | 0.4307 | 0.0684 | 0.030* | |
H44B | 0.8692 | 0.3084 | 0.0459 | 0.030* | |
C45 | 0.6844 (2) | 0.3952 (2) | 0.08214 (10) | 0.0230 (5) | |
H45A | 0.6430 | 0.4530 | 0.1113 | 0.028* | |
H45B | 0.6476 | 0.4314 | 0.0443 | 0.028* | |
C46 | 0.6588 (2) | 0.28786 (19) | 0.09965 (9) | 0.0201 (5) | |
H46A | 0.5663 | 0.3131 | 0.1037 | 0.024* | |
H46B | 0.6930 | 0.2341 | 0.0683 | 0.024* | |
C48 | 0.7088 (2) | 0.10651 (18) | 0.16445 (10) | 0.0177 (5) | |
H48A | 0.7435 | 0.0666 | 0.2021 | 0.021* | |
H48B | 0.7632 | 0.0574 | 0.1337 | 0.021* | |
C49 | 0.5741 (2) | 0.11426 (19) | 0.16236 (9) | 0.0190 (5) | |
C47 | 0.6562 (2) | 0.2930 (2) | 0.20984 (10) | 0.0230 (5) | |
H47A | 0.5655 | 0.3133 | 0.2125 | 0.035* | |
H47B | 0.6683 | 0.3639 | 0.2056 | 0.035* | |
H47C | 0.6950 | 0.2467 | 0.2451 | 0.035* | |
C52 | 1.2661 (3) | 0.3413 (3) | 0.29748 (14) | 0.0438 (8) | |
H52A | 1.3536 | 0.2889 | 0.2848 | 0.053* | |
H52B | 1.2346 | 0.4085 | 0.2684 | 0.053* | |
C53 | 1.2688 (4) | 0.3835 (3) | 0.35458 (16) | 0.0744 (13) | |
H53A | 1.1831 | 0.4421 | 0.3656 | 0.089* | |
H53B | 1.3265 | 0.4213 | 0.3509 | 0.089* | |
C54 | 1.3142 (5) | 0.2816 (4) | 0.40344 (19) | 0.1056 (19) | |
H54A | 1.3103 | 0.3121 | 0.4413 | 0.127* | |
H54B | 1.4026 | 0.2254 | 0.3946 | 0.127* | |
C55 | 1.2231 (4) | 0.2203 (3) | 0.40575 (16) | 0.0715 (12) | |
H55A | 1.2510 | 0.1539 | 0.4353 | 0.086* | |
H55B | 1.1360 | 0.2758 | 0.4171 | 0.086* | |
C56 | 1.2238 (3) | 0.1785 (2) | 0.34794 (15) | 0.0486 (8) | |
H56A | 1.1662 | 0.1406 | 0.3507 | 0.058* | |
H56B | 1.3101 | 0.1194 | 0.3381 | 0.058* | |
C58 | 1.0404 (2) | 0.35296 (19) | 0.30845 (10) | 0.0215 (5) | |
H58A | 1.0275 | 0.3884 | 0.3457 | 0.026* | |
H58B | 0.9968 | 0.3019 | 0.3129 | 0.026* | |
C59 | 0.9739 (2) | 0.4515 (2) | 0.26140 (11) | 0.0256 (5) | |
C57 | 1.2046 (3) | 0.2208 (3) | 0.24173 (14) | 0.0538 (9) | |
H57A | 1.1524 | 0.1790 | 0.2421 | 0.081* | |
H57B | 1.2940 | 0.1665 | 0.2367 | 0.081* | |
H57C | 1.1816 | 0.2811 | 0.2096 | 0.081* | |
C62 | 0.6704 (2) | 0.91596 (19) | 0.35671 (10) | 0.0248 (5) | |
H62A | 0.6126 | 0.9314 | 0.3917 | 0.030* | |
H62B | 0.7214 | 0.9595 | 0.3579 | 0.030* | |
C63 | 0.5920 (2) | 0.9599 (2) | 0.30283 (10) | 0.0280 (5) | |
H63A | 0.6493 | 0.9495 | 0.2678 | 0.034* | |
H63B | 0.5359 | 1.0438 | 0.3044 | 0.034* | |
C64 | 0.5109 (3) | 0.8937 (2) | 0.29868 (12) | 0.0352 (6) | |
H64A | 0.4628 | 0.9216 | 0.2630 | 0.042* | |
H64B | 0.4499 | 0.9072 | 0.3324 | 0.042* | |
C65 | 0.6014 (3) | 0.7619 (2) | 0.29754 (12) | 0.0339 (6) | |
H65A | 0.5507 | 0.7181 | 0.2963 | 0.041* | |
H65B | 0.6572 | 0.7488 | 0.2619 | 0.041* | |
C66 | 0.6831 (2) | 0.7159 (2) | 0.35083 (11) | 0.0304 (6) | |
H66A | 0.7421 | 0.6333 | 0.3472 | 0.036* | |
H66B | 0.6276 | 0.7205 | 0.3860 | 0.036* | |
C67 | 0.8657 (2) | 0.7614 (2) | 0.31078 (12) | 0.0357 (6) | |
H67A | 0.9215 | 0.6781 | 0.3118 | 0.054* | |
H67B | 0.9146 | 0.8034 | 0.3176 | 0.054* | |
H67C | 0.8288 | 0.7880 | 0.2728 | 0.054* | |
C68A | 0.7989 (9) | 0.7459 (9) | 0.4243 (4) | 0.0218 (17) | 0.50 |
H68A | 0.8475 | 0.7868 | 0.4344 | 0.026* | 0.50 |
H68B | 0.7208 | 0.7712 | 0.4497 | 0.026* | 0.50 |
C69A | 0.8773 (5) | 0.6158 (5) | 0.4370 (2) | 0.0247 (11) | 0.50 |
O61A | 0.8822 (3) | 0.5935 (3) | 0.49527 (15) | 0.0304 (8) | 0.50 |
O62A | 0.9268 (8) | 0.5406 (7) | 0.4036 (3) | 0.0356 (16) | 0.50 |
C68B | 0.8321 (9) | 0.7592 (9) | 0.4123 (4) | 0.0223 (17) | 0.50 |
H68C | 0.7702 | 0.7805 | 0.4458 | 0.027* | 0.50 |
H68D | 0.8750 | 0.8107 | 0.4098 | 0.027* | 0.50 |
C69B | 0.9348 (5) | 0.6301 (5) | 0.4254 (2) | 0.0257 (11) | 0.50 |
O61B | 0.9799 (3) | 0.6153 (3) | 0.47682 (15) | 0.0291 (8) | 0.50 |
H61 | 1.037 (6) | 0.531 (5) | 0.490 (2) | 0.047 (17)* | 0.50 |
O62B | 0.9614 (8) | 0.5560 (7) | 0.3891 (3) | 0.0316 (14) | 0.50 |
O1 | 0.6562 (2) | 0.5819 (2) | 0.17938 (11) | 0.0526 (6) | |
H1A | 0.609 (4) | 0.650 (4) | 0.1788 (18) | 0.093 (15)* | |
H1B | 0.720 (4) | 0.564 (4) | 0.2047 (19) | 0.102 (15)* | |
O2 | 0.7188 (2) | 0.3953 (2) | 0.33504 (11) | 0.0589 (6) | |
H2A | 0.765 (3) | 0.418 (3) | 0.3122 (13) | 0.071* | |
H2B | 0.6386 (14) | 0.429 (6) | 0.332 (3) | 0.071* | 0.50 |
H2C | 0.759 (6) | 0.3226 (11) | 0.337 (3) | 0.071* | 0.50 |
O3A | 0.4995 (4) | 0.5095 (5) | 0.3076 (3) | 0.0780 (15) | 0.59 |
O3B | 0.4833 (5) | 0.5201 (6) | 0.3510 (3) | 0.0626 (17) | 0.41 |
H21 | 0.968 (3) | 0.600 (3) | 0.1870 (16) | 0.084 (12)* | |
H11 | 0.5000 | 0.0000 | 0.5000 | 0.15 (3)* | |
H41 | 0.478 (4) | 0.013 (3) | 0.1483 (15) | 0.083 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Si1 | 0.0199 (4) | 0.0176 (4) | 0.0146 (4) | −0.0094 (4) | −0.0012 (3) | −0.0025 (3) |
Si2 | 0.0279 (4) | 0.0354 (4) | 0.0167 (3) | −0.0185 (3) | −0.0010 (3) | −0.0046 (3) |
F11 | 0.0280 (7) | 0.0422 (9) | 0.0283 (8) | −0.0211 (7) | 0.0069 (6) | −0.0165 (6) |
F12 | 0.0394 (8) | 0.0206 (7) | 0.0309 (8) | −0.0153 (6) | −0.0132 (6) | 0.0028 (6) |
F13 | 0.0262 (7) | 0.0249 (7) | 0.0187 (7) | −0.0137 (6) | −0.0052 (5) | −0.0037 (5) |
F21 | 0.0364 (8) | 0.0434 (9) | 0.0270 (8) | −0.0245 (7) | −0.0147 (6) | 0.0063 (7) |
F22A | 0.035 (2) | 0.048 (3) | 0.040 (2) | 0.0003 (17) | −0.0088 (17) | −0.0176 (19) |
F23A | 0.053 (4) | 0.084 (5) | 0.020 (2) | −0.052 (4) | −0.003 (2) | −0.001 (3) |
F24A | 0.079 (4) | 0.027 (2) | 0.064 (3) | 0.001 (2) | −0.026 (3) | −0.011 (2) |
F25A | 0.072 (3) | 0.103 (4) | 0.0223 (19) | −0.070 (3) | −0.008 (2) | 0.009 (2) |
F22B | 0.0251 (18) | 0.071 (3) | 0.034 (2) | −0.0047 (19) | −0.0035 (15) | −0.026 (2) |
F23B | 0.071 (5) | 0.047 (3) | 0.042 (4) | −0.042 (3) | −0.037 (3) | 0.025 (3) |
F24B | 0.040 (2) | 0.051 (3) | 0.0282 (19) | −0.0179 (18) | 0.0042 (15) | −0.0124 (18) |
F25B | 0.059 (3) | 0.054 (2) | 0.0231 (18) | −0.044 (2) | −0.0079 (18) | 0.0027 (17) |
F26 | 0.0868 (13) | 0.1056 (15) | 0.0200 (8) | −0.0825 (13) | −0.0098 (8) | 0.0037 (9) |
O11 | 0.0318 (10) | 0.0298 (10) | 0.0362 (10) | −0.0109 (8) | −0.0003 (8) | −0.0082 (8) |
O12 | 0.0330 (10) | 0.0373 (11) | 0.0321 (10) | −0.0079 (9) | 0.0021 (8) | −0.0092 (8) |
O21 | 0.0410 (10) | 0.0261 (10) | 0.0233 (9) | −0.0173 (8) | −0.0155 (8) | 0.0064 (7) |
O22 | 0.0339 (10) | 0.0193 (9) | 0.0318 (10) | −0.0068 (7) | −0.0114 (8) | 0.0012 (7) |
O31 | 0.0204 (8) | 0.0186 (8) | 0.0344 (10) | −0.0107 (7) | −0.0063 (7) | 0.0026 (7) |
O32 | 0.0177 (8) | 0.0197 (8) | 0.0331 (9) | −0.0049 (7) | −0.0029 (7) | −0.0026 (7) |
O41 | 0.0227 (9) | 0.0247 (9) | 0.0317 (9) | −0.0133 (7) | −0.0003 (7) | −0.0058 (7) |
O42 | 0.0173 (8) | 0.0244 (9) | 0.0377 (10) | −0.0091 (7) | 0.0015 (7) | −0.0047 (7) |
O51 | 0.0379 (10) | 0.0379 (11) | 0.0337 (10) | −0.0203 (9) | −0.0141 (8) | 0.0175 (8) |
O52 | 0.0275 (10) | 0.0265 (9) | 0.0354 (10) | −0.0080 (8) | −0.0087 (8) | 0.0005 (8) |
N11 | 0.0477 (14) | 0.0284 (12) | 0.0212 (11) | −0.0161 (10) | −0.0084 (10) | 0.0024 (9) |
N21 | 0.0157 (9) | 0.0157 (9) | 0.0178 (10) | −0.0058 (7) | −0.0015 (7) | −0.0013 (7) |
N31 | 0.0192 (9) | 0.0144 (9) | 0.0164 (9) | −0.0080 (8) | 0.0011 (7) | −0.0024 (7) |
N41 | 0.0145 (9) | 0.0188 (9) | 0.0184 (10) | −0.0075 (8) | 0.0002 (7) | −0.0032 (8) |
N51 | 0.0218 (10) | 0.0210 (10) | 0.0366 (12) | −0.0101 (9) | −0.0033 (9) | 0.0072 (9) |
N61 | 0.0301 (11) | 0.0212 (10) | 0.0212 (11) | −0.0047 (9) | −0.0068 (9) | −0.0028 (8) |
C12 | 0.068 (2) | 0.0382 (17) | 0.0414 (18) | −0.0238 (16) | −0.0256 (16) | 0.0129 (14) |
C13 | 0.077 (2) | 0.0381 (18) | 0.055 (2) | −0.0309 (17) | −0.0211 (18) | 0.0055 (15) |
C14A | 0.068 (4) | 0.049 (4) | 0.054 (4) | −0.032 (3) | 0.000 (3) | −0.025 (3) |
C15A | 0.053 (3) | 0.046 (3) | 0.037 (3) | −0.022 (3) | 0.001 (3) | −0.021 (3) |
C14B | 0.046 (4) | 0.052 (4) | 0.049 (4) | −0.031 (3) | 0.000 (3) | −0.003 (3) |
C15B | 0.032 (3) | 0.048 (4) | 0.042 (4) | −0.027 (3) | −0.005 (3) | 0.009 (3) |
C16 | 0.0582 (19) | 0.0499 (18) | 0.0248 (15) | −0.0197 (15) | −0.0025 (13) | −0.0139 (13) |
C18 | 0.0332 (14) | 0.0264 (13) | 0.0236 (13) | −0.0107 (11) | 0.0003 (11) | −0.0051 (10) |
C19 | 0.0298 (13) | 0.0286 (13) | 0.0136 (12) | −0.0081 (11) | −0.0022 (10) | 0.0008 (10) |
C17 | 0.0486 (17) | 0.0531 (18) | 0.0297 (15) | −0.0304 (15) | −0.0074 (13) | 0.0036 (13) |
C22 | 0.0166 (11) | 0.0217 (12) | 0.0223 (12) | −0.0065 (9) | 0.0014 (9) | −0.0026 (10) |
C23 | 0.0246 (12) | 0.0200 (12) | 0.0181 (12) | −0.0057 (10) | −0.0001 (9) | −0.0035 (9) |
C24 | 0.0307 (13) | 0.0204 (12) | 0.0277 (13) | −0.0112 (10) | −0.0079 (11) | −0.0040 (10) |
C25 | 0.0215 (12) | 0.0289 (13) | 0.0278 (13) | −0.0153 (10) | −0.0070 (10) | 0.0016 (10) |
C26 | 0.0180 (11) | 0.0232 (12) | 0.0228 (12) | −0.0115 (10) | 0.0001 (9) | 0.0011 (9) |
C28 | 0.0247 (12) | 0.0194 (11) | 0.0182 (12) | −0.0102 (10) | −0.0049 (9) | −0.0006 (9) |
C29 | 0.0211 (12) | 0.0228 (12) | 0.0273 (13) | −0.0121 (10) | −0.0054 (10) | −0.0006 (10) |
C27 | 0.0219 (12) | 0.0161 (11) | 0.0235 (12) | −0.0057 (9) | −0.0042 (10) | −0.0015 (9) |
C32 | 0.0224 (11) | 0.0216 (11) | 0.0155 (11) | −0.0102 (10) | 0.0009 (9) | −0.0049 (9) |
C33 | 0.0335 (14) | 0.0225 (12) | 0.0286 (14) | −0.0142 (11) | 0.0054 (11) | −0.0111 (10) |
C34 | 0.0488 (16) | 0.0209 (13) | 0.0326 (15) | −0.0176 (12) | 0.0033 (13) | −0.0031 (11) |
C35 | 0.0485 (16) | 0.0223 (13) | 0.0269 (14) | −0.0182 (12) | 0.0021 (12) | 0.0007 (11) |
C36 | 0.0315 (13) | 0.0209 (12) | 0.0167 (12) | −0.0115 (10) | −0.0008 (10) | 0.0003 (9) |
C38 | 0.0203 (11) | 0.0122 (10) | 0.0206 (12) | −0.0078 (9) | −0.0025 (9) | −0.0020 (9) |
C39 | 0.0214 (11) | 0.0196 (11) | 0.0165 (11) | −0.0114 (10) | −0.0038 (9) | −0.0007 (9) |
C37 | 0.0196 (11) | 0.0248 (12) | 0.0261 (13) | −0.0125 (10) | 0.0023 (10) | −0.0050 (10) |
C42 | 0.0159 (11) | 0.0215 (12) | 0.0197 (12) | −0.0079 (9) | −0.0022 (9) | −0.0026 (9) |
C43 | 0.0205 (12) | 0.0268 (13) | 0.0298 (13) | −0.0142 (10) | 0.0012 (10) | −0.0087 (10) |
C44 | 0.0264 (12) | 0.0227 (12) | 0.0287 (13) | −0.0147 (10) | 0.0032 (10) | −0.0025 (10) |
C45 | 0.0255 (12) | 0.0212 (12) | 0.0217 (12) | −0.0100 (10) | −0.0010 (10) | −0.0001 (10) |
C46 | 0.0188 (11) | 0.0224 (12) | 0.0181 (12) | −0.0079 (9) | −0.0031 (9) | 0.0006 (9) |
C48 | 0.0170 (11) | 0.0161 (11) | 0.0206 (12) | −0.0078 (9) | −0.0012 (9) | −0.0011 (9) |
C49 | 0.0215 (12) | 0.0223 (12) | 0.0149 (11) | −0.0118 (10) | 0.0010 (9) | 0.0000 (9) |
C47 | 0.0245 (12) | 0.0257 (12) | 0.0197 (12) | −0.0107 (10) | 0.0025 (10) | −0.0088 (10) |
C52 | 0.0333 (15) | 0.0449 (17) | 0.060 (2) | −0.0271 (14) | −0.0171 (14) | 0.0239 (15) |
C53 | 0.114 (3) | 0.087 (3) | 0.066 (2) | −0.084 (3) | −0.060 (2) | 0.043 (2) |
C54 | 0.167 (5) | 0.126 (4) | 0.086 (3) | −0.123 (4) | −0.096 (3) | 0.081 (3) |
C55 | 0.108 (3) | 0.075 (3) | 0.060 (2) | −0.068 (2) | −0.048 (2) | 0.045 (2) |
C56 | 0.0297 (15) | 0.0328 (16) | 0.079 (2) | −0.0144 (13) | −0.0150 (15) | 0.0280 (16) |
C58 | 0.0235 (12) | 0.0196 (12) | 0.0202 (12) | −0.0085 (10) | −0.0018 (9) | 0.0000 (9) |
C59 | 0.0303 (14) | 0.0196 (12) | 0.0261 (13) | −0.0090 (11) | −0.0080 (11) | −0.0015 (10) |
C57 | 0.059 (2) | 0.0385 (17) | 0.064 (2) | −0.0240 (15) | 0.0361 (17) | −0.0251 (15) |
C62 | 0.0265 (12) | 0.0177 (12) | 0.0263 (13) | −0.0056 (10) | −0.0040 (10) | −0.0010 (10) |
C63 | 0.0320 (13) | 0.0253 (13) | 0.0228 (13) | −0.0087 (11) | −0.0061 (11) | 0.0018 (10) |
C64 | 0.0332 (14) | 0.0326 (15) | 0.0384 (16) | −0.0107 (12) | −0.0153 (12) | −0.0021 (12) |
C65 | 0.0359 (15) | 0.0309 (14) | 0.0375 (15) | −0.0148 (12) | −0.0056 (12) | −0.0084 (12) |
C66 | 0.0407 (15) | 0.0191 (12) | 0.0283 (14) | −0.0110 (11) | 0.0023 (12) | −0.0018 (10) |
C67 | 0.0282 (14) | 0.0367 (15) | 0.0395 (16) | −0.0101 (12) | 0.0017 (12) | −0.0126 (12) |
C68A | 0.038 (5) | 0.015 (3) | 0.007 (4) | −0.007 (3) | −0.005 (3) | 0.002 (3) |
C69A | 0.023 (3) | 0.020 (3) | 0.029 (3) | −0.006 (2) | −0.007 (2) | −0.003 (2) |
O61A | 0.036 (2) | 0.0227 (18) | 0.0271 (19) | −0.0071 (16) | −0.0052 (16) | 0.0008 (14) |
O62A | 0.050 (4) | 0.021 (3) | 0.020 (3) | −0.001 (2) | −0.005 (3) | −0.001 (2) |
C68B | 0.034 (4) | 0.018 (3) | 0.007 (4) | −0.005 (3) | 0.002 (3) | 0.003 (3) |
C69B | 0.025 (3) | 0.025 (3) | 0.031 (3) | −0.015 (2) | −0.004 (2) | 0.001 (2) |
O61B | 0.037 (2) | 0.0173 (17) | 0.0284 (19) | −0.0052 (15) | −0.0147 (16) | 0.0001 (15) |
O62B | 0.046 (4) | 0.016 (2) | 0.023 (4) | −0.003 (2) | −0.001 (2) | −0.004 (2) |
O1 | 0.0583 (15) | 0.0249 (12) | 0.0657 (16) | −0.0024 (10) | −0.0357 (12) | −0.0103 (11) |
O2 | 0.0569 (15) | 0.0551 (15) | 0.0597 (15) | −0.0216 (13) | 0.0165 (13) | −0.0124 (13) |
O3A | 0.029 (2) | 0.088 (3) | 0.110 (4) | −0.016 (2) | 0.001 (3) | −0.026 (3) |
O3B | 0.024 (3) | 0.078 (4) | 0.078 (5) | −0.011 (3) | −0.003 (3) | −0.021 (4) |
Geometric parameters (Å, º) top
Si1—F12 | 1.6808 (14) | C28—C29 | 1.525 (3) |
Si1—F12i | 1.6808 (14) | C28—H28A | 0.9700 |
Si1—F11i | 1.6872 (14) | C28—H28B | 0.9700 |
Si1—F11 | 1.6873 (14) | C27—H27A | 0.9600 |
Si1—F13 | 1.6951 (13) | C27—H27B | 0.9600 |
Si1—F13i | 1.6952 (13) | C27—H27C | 0.9600 |
Si2—F22B | 1.620 (3) | C32—C33 | 1.519 (3) |
Si2—F24A | 1.633 (4) | C32—H32A | 0.9700 |
Si2—F23B | 1.634 (6) | C32—H32B | 0.9700 |
Si2—F25A | 1.667 (3) | C33—C34 | 1.518 (4) |
Si2—F23A | 1.677 (6) | C33—H33A | 0.9700 |
Si2—F21 | 1.6828 (15) | C33—H33B | 0.9700 |
Si2—F26 | 1.6830 (16) | C34—C35 | 1.527 (3) |
Si2—F25B | 1.726 (3) | C34—H34A | 0.9700 |
Si2—F22A | 1.728 (4) | C34—H34B | 0.9700 |
Si2—F24B | 1.740 (4) | C35—C36 | 1.521 (3) |
O11—C19 | 1.291 (3) | C35—H35A | 0.9700 |
O11—H11 | 1.2291 (17) | C35—H35B | 0.9700 |
O12—C19 | 1.223 (3) | C36—H36A | 0.9700 |
O21—C29 | 1.303 (3) | C36—H36B | 0.9700 |
O21—H21 | 0.98 (4) | C38—C39 | 1.526 (3) |
O22—C29 | 1.207 (3) | C38—H38A | 0.9700 |
O31—C39 | 1.276 (2) | C38—H38B | 0.9700 |
O31—H41 | 1.28 (4) | C37—H37A | 0.9600 |
O32—C39 | 1.232 (3) | C37—H37B | 0.9600 |
O41—C49 | 1.302 (3) | C37—H37C | 0.9600 |
O41—H41 | 1.18 (4) | C42—C43 | 1.512 (3) |
O42—C49 | 1.220 (3) | C42—H42A | 0.9700 |
O51—C59 | 1.272 (3) | C42—H42B | 0.9700 |
O52—C59 | 1.241 (3) | C43—C44 | 1.525 (3) |
N11—C18 | 1.499 (3) | C43—H43A | 0.9700 |
N11—C17 | 1.514 (3) | C43—H43B | 0.9700 |
N11—C16 | 1.516 (3) | C44—C45 | 1.522 (3) |
N11—C12 | 1.517 (3) | C44—H44A | 0.9700 |
N21—C27 | 1.503 (3) | C44—H44B | 0.9700 |
N21—C28 | 1.510 (3) | C45—C46 | 1.516 (3) |
N21—C26 | 1.512 (3) | C45—H45A | 0.9700 |
N21—C22 | 1.521 (3) | C45—H45B | 0.9700 |
N31—C38 | 1.504 (3) | C46—H46A | 0.9700 |
N31—C37 | 1.511 (3) | C46—H46B | 0.9700 |
N31—C36 | 1.520 (3) | C48—C49 | 1.521 (3) |
N31—C32 | 1.521 (3) | C48—H48A | 0.9700 |
N41—C48 | 1.503 (3) | C48—H48B | 0.9700 |
N41—C47 | 1.506 (3) | C47—H47A | 0.9600 |
N41—C46 | 1.515 (3) | C47—H47B | 0.9600 |
N41—C42 | 1.530 (3) | C47—H47C | 0.9600 |
N51—C57 | 1.487 (3) | C52—C53 | 1.464 (5) |
N51—C58 | 1.505 (3) | C52—H52A | 0.9700 |
N51—C52 | 1.513 (3) | C52—H52B | 0.9700 |
N51—C56 | 1.515 (3) | C53—C54 | 1.540 (4) |
N61—C68B | 1.481 (11) | C53—H53A | 0.9700 |
N61—C67 | 1.500 (3) | C53—H53B | 0.9700 |
N61—C66 | 1.514 (3) | C54—C55 | 1.551 (5) |
N61—C62 | 1.519 (3) | C54—H54A | 0.9700 |
N61—C68A | 1.578 (10) | C54—H54B | 0.9700 |
C12—C13 | 1.515 (3) | C55—C56 | 1.468 (5) |
C12—H12A | 0.9700 | C55—H55A | 0.9700 |
C12—H12B | 0.9700 | C55—H55B | 0.9700 |
C13—C14B | 1.463 (4) | C56—H56A | 0.9700 |
C13—C14A | 1.486 (4) | C56—H56B | 0.9700 |
C13—H13A | 0.9700 | C58—C59 | 1.519 (3) |
C13—H13B | 0.9700 | C58—H58A | 0.9700 |
C13—H13C | 0.9701 | C58—H58B | 0.9700 |
C13—H13D | 0.9700 | C57—H57A | 0.9600 |
C14A—C15A | 1.508 (4) | C57—H57B | 0.9600 |
C14A—H13D | 0.5485 | C57—H57C | 0.9600 |
C14A—H14A | 0.9700 | C62—C63 | 1.498 (3) |
C14A—H14B | 0.9700 | C62—H62A | 0.9700 |
C15A—C16 | 1.553 (4) | C62—H62B | 0.9700 |
C15A—H15A | 0.9700 | C63—C64 | 1.519 (3) |
C15A—H15B | 0.9700 | C63—H63A | 0.9700 |
C14B—C15B | 1.504 (5) | C63—H63B | 0.9700 |
C14B—H14C | 0.9700 | C64—C65 | 1.527 (4) |
C14B—H14D | 0.9700 | C64—H64A | 0.9700 |
C15B—C17 | 1.527 (4) | C64—H64B | 0.9700 |
C15B—H15C | 0.9700 | C65—C66 | 1.508 (4) |
C15B—H15D | 0.9700 | C65—H65A | 0.9700 |
C16—H16A | 0.9700 | C65—H65B | 0.9700 |
C16—H16B | 0.9700 | C66—H66A | 0.9700 |
C16—H17E | 0.9600 | C66—H66B | 0.9700 |
C16—H17F | 0.9600 | C67—H67A | 0.9600 |
C16—H17G | 0.9600 | C67—H67B | 0.9600 |
C18—C19 | 1.518 (3) | C67—H67C | 0.9600 |
C18—H18A | 0.9700 | C68A—C69A | 1.495 (11) |
C18—H18B | 0.9700 | C68A—H68A | 0.9700 |
C17—H17A | 0.9600 | C68A—H68B | 0.9700 |
C17—H17B | 0.9600 | C69A—O62A | 1.186 (9) |
C17—H17C | 0.9600 | C69A—O61A | 1.326 (6) |
C17—H16C | 0.9700 | C68B—C69B | 1.551 (12) |
C17—H16D | 0.9700 | C68B—H68C | 0.9700 |
C22—C23 | 1.517 (3) | C68B—H68D | 0.9700 |
C22—H22A | 0.9700 | C69B—O62B | 1.232 (9) |
C22—H22B | 0.9700 | C69B—O61B | 1.287 (6) |
C23—C24 | 1.525 (3) | O61B—H61 | 1.01 (6) |
C23—H23A | 0.9700 | O1—H1A | 0.79 (4) |
C23—H23B | 0.9700 | O1—H1B | 0.91 (5) |
C24—C25 | 1.526 (3) | O1—H1A | 0.79 (4) |
C24—H24A | 0.9700 | O1—H1B | 0.91 (5) |
C24—H24B | 0.9700 | O2—H2C | 0.824 (11) |
C25—C26 | 1.512 (3) | O2—H2B | 0.837 (11) |
C25—H25A | 0.9700 | O2—H2A | 0.831 (10) |
C25—H25B | 0.9700 | O2—H2B | 0.837 (11) |
C26—H26A | 0.9700 | O2—H2C | 0.824 (11) |
C26—H26B | 0.9700 | | |
| | | |
F12—Si1—F12i | 179.9990 (10) | H26A—C26—H26B | 107.8 |
F12—Si1—F11i | 90.46 (8) | N21—C28—C29 | 116.53 (18) |
F12i—Si1—F11i | 89.54 (8) | N21—C28—H28A | 108.2 |
F12—Si1—F11 | 89.54 (8) | C29—C28—H28A | 108.2 |
F12i—Si1—F11 | 90.46 (8) | N21—C28—H28B | 108.2 |
F11i—Si1—F11 | 180.0 | C29—C28—H28B | 108.2 |
F12—Si1—F13 | 90.56 (7) | H28A—C28—H28B | 107.3 |
F12i—Si1—F13 | 89.44 (7) | O22—C29—O21 | 125.7 (2) |
F11i—Si1—F13 | 89.45 (6) | O22—C29—C28 | 125.1 (2) |
F11—Si1—F13 | 90.55 (6) | O21—C29—C28 | 109.19 (19) |
F12—Si1—F13i | 89.44 (7) | N21—C27—H27A | 109.5 |
F12i—Si1—F13i | 90.56 (7) | N21—C27—H27B | 109.5 |
F11i—Si1—F13i | 90.55 (6) | H27A—C27—H27B | 109.5 |
F11—Si1—F13i | 89.45 (6) | N21—C27—H27C | 109.5 |
F13—Si1—F13i | 180.0 | H27A—C27—H27C | 109.5 |
F22B—Si2—F24A | 149.3 (3) | H27B—C27—H27C | 109.5 |
F22B—Si2—F23B | 96.4 (3) | C33—C32—N31 | 112.05 (17) |
F24A—Si2—F23B | 111.3 (3) | C33—C32—H32A | 109.2 |
F22B—Si2—F25A | 58.7 (2) | N31—C32—H32A | 109.2 |
F24A—Si2—F25A | 93.3 (3) | C33—C32—H32B | 109.2 |
F23B—Si2—F25A | 155.1 (3) | N31—C32—H32B | 109.2 |
F22B—Si2—F23A | 115.6 (3) | H32A—C32—H32B | 107.9 |
F24A—Si2—F23A | 91.9 (3) | C34—C33—C32 | 111.2 (2) |
F25A—Si2—F23A | 174.2 (3) | C34—C33—H33A | 109.4 |
F22B—Si2—F21 | 95.56 (14) | C32—C33—H33A | 109.4 |
F24A—Si2—F21 | 96.74 (19) | C34—C33—H33B | 109.4 |
F23B—Si2—F21 | 91.2 (3) | C32—C33—H33B | 109.4 |
F25A—Si2—F21 | 89.70 (14) | H33A—C33—H33B | 108.0 |
F23A—Si2—F21 | 92.4 (3) | C33—C34—C35 | 110.9 (2) |
F22B—Si2—F26 | 85.08 (15) | C33—C34—H34A | 109.5 |
F24A—Si2—F26 | 82.75 (19) | C35—C34—H34A | 109.5 |
F23B—Si2—F26 | 88.6 (3) | C33—C34—H34B | 109.5 |
F25A—Si2—F26 | 90.75 (14) | C35—C34—H34B | 109.5 |
F23A—Si2—F26 | 87.2 (3) | H34A—C34—H34B | 108.1 |
F21—Si2—F26 | 179.34 (9) | C36—C35—C34 | 111.20 (19) |
F22B—Si2—F25B | 90.1 (2) | C36—C35—H35A | 109.4 |
F24A—Si2—F25B | 62.7 (2) | C34—C35—H35A | 109.4 |
F23B—Si2—F25B | 173.4 (3) | C36—C35—H35B | 109.4 |
F23A—Si2—F25B | 154.2 (3) | C34—C35—H35B | 109.4 |
F21—Si2—F25B | 86.85 (13) | H35A—C35—H35B | 108.0 |
F26—Si2—F25B | 93.29 (14) | N31—C36—C35 | 112.21 (19) |
F24A—Si2—F22A | 177.2 (2) | N31—C36—H36A | 109.2 |
F23B—Si2—F22A | 66.9 (3) | C35—C36—H36A | 109.2 |
F25A—Si2—F22A | 88.3 (2) | N31—C36—H36B | 109.2 |
F23A—Si2—F22A | 86.4 (3) | C35—C36—H36B | 109.2 |
F21—Si2—F22A | 85.52 (14) | H36A—C36—H36B | 107.9 |
F26—Si2—F22A | 94.97 (15) | N31—C38—C39 | 117.86 (17) |
F25B—Si2—F22A | 119.2 (2) | N31—C38—H38A | 107.8 |
F22B—Si2—F24B | 175.3 (2) | C39—C38—H38A | 107.8 |
F23B—Si2—F24B | 88.3 (3) | N31—C38—H38B | 107.8 |
F25A—Si2—F24B | 116.6 (2) | C39—C38—H38B | 107.8 |
F23A—Si2—F24B | 69.1 (3) | H38A—C38—H38B | 107.2 |
F21—Si2—F24B | 83.61 (16) | O32—C39—O31 | 125.4 (2) |
F26—Si2—F24B | 95.76 (16) | O32—C39—C38 | 123.93 (19) |
F25B—Si2—F24B | 85.2 (2) | O31—C39—C38 | 110.68 (18) |
F22A—Si2—F24B | 152.7 (2) | N31—C37—H37A | 109.5 |
C29—O21—H21 | 109 (2) | N31—C37—H37B | 109.5 |
C39—O31—H41 | 113.1 (15) | H37A—C37—H37B | 109.5 |
C49—O41—H41 | 114.3 (16) | N31—C37—H37C | 109.5 |
C18—N11—C17 | 106.23 (19) | H37A—C37—H37C | 109.5 |
C18—N11—C16 | 111.04 (19) | H37B—C37—H37C | 109.5 |
C17—N11—C16 | 109.3 (2) | C43—C42—N41 | 112.50 (18) |
C18—N11—C12 | 110.72 (19) | C43—C42—H42A | 109.1 |
C17—N11—C12 | 109.0 (2) | N41—C42—H42A | 109.1 |
C16—N11—C12 | 110.4 (2) | C43—C42—H42B | 109.1 |
C27—N21—C28 | 106.09 (16) | N41—C42—H42B | 109.1 |
C27—N21—C26 | 110.32 (16) | H42A—C42—H42B | 107.8 |
C28—N21—C26 | 109.18 (16) | C42—C43—C44 | 110.90 (19) |
C27—N21—C22 | 109.15 (16) | C42—C43—H43A | 109.5 |
C28—N21—C22 | 110.40 (16) | C44—C43—H43A | 109.5 |
C26—N21—C22 | 111.57 (16) | C42—C43—H43B | 109.5 |
C38—N31—C37 | 105.94 (16) | C44—C43—H43B | 109.5 |
C38—N31—C36 | 110.52 (17) | H43A—C43—H43B | 108.0 |
C37—N31—C36 | 109.71 (16) | C45—C44—C43 | 109.84 (18) |
C38—N31—C32 | 109.91 (15) | C45—C44—H44A | 109.7 |
C37—N31—C32 | 109.99 (17) | C43—C44—H44A | 109.7 |
C36—N31—C32 | 110.66 (16) | C45—C44—H44B | 109.7 |
C48—N41—C47 | 110.62 (16) | C43—C44—H44B | 109.7 |
C48—N41—C46 | 108.75 (16) | H44A—C44—H44B | 108.2 |
C47—N41—C46 | 112.61 (17) | C46—C45—C44 | 110.81 (19) |
C48—N41—C42 | 106.21 (16) | C46—C45—H45A | 109.5 |
C47—N41—C42 | 109.27 (17) | C44—C45—H45A | 109.5 |
C46—N41—C42 | 109.17 (16) | C46—C45—H45B | 109.5 |
C57—N51—C58 | 108.8 (2) | C44—C45—H45B | 109.5 |
C57—N51—C52 | 108.9 (2) | H45A—C45—H45B | 108.1 |
C58—N51—C52 | 114.42 (19) | N41—C46—C45 | 113.15 (18) |
C57—N51—C56 | 108.0 (2) | N41—C46—H46A | 108.9 |
C58—N51—C56 | 107.82 (18) | C45—C46—H46A | 108.9 |
C52—N51—C56 | 108.8 (2) | N41—C46—H46B | 108.9 |
C68B—N61—C67 | 101.4 (3) | C45—C46—H46B | 108.9 |
C68B—N61—C66 | 118.8 (3) | H46A—C46—H46B | 107.8 |
C67—N61—C66 | 111.67 (18) | N41—C48—C49 | 116.04 (18) |
C68B—N61—C62 | 104.7 (4) | N41—C48—H48A | 108.3 |
C67—N61—C62 | 110.03 (19) | C49—C48—H48A | 108.3 |
C66—N61—C62 | 109.74 (18) | N41—C48—H48B | 108.3 |
C67—N61—C68A | 118.1 (3) | C49—C48—H48B | 108.3 |
C66—N61—C68A | 101.2 (3) | H48A—C48—H48B | 107.4 |
C62—N61—C68A | 105.5 (4) | O42—C49—O41 | 124.9 (2) |
C13—C12—N11 | 112.6 (2) | O42—C49—C48 | 124.3 (2) |
C13—C12—H12A | 109.1 | O41—C49—C48 | 110.84 (19) |
N11—C12—H12A | 109.1 | N41—C47—H47A | 109.5 |
C13—C12—H12B | 109.1 | N41—C47—H47B | 109.5 |
N11—C12—H12B | 109.1 | H47A—C47—H47B | 109.5 |
H12A—C12—H12B | 107.8 | N41—C47—H47C | 109.5 |
C14B—C13—C14A | 100.9 (4) | H47A—C47—H47C | 109.5 |
C14B—C13—C12 | 111.5 (4) | H47B—C47—H47C | 109.5 |
C14A—C13—C12 | 111.7 (3) | C53—C52—N51 | 113.9 (2) |
C14A—C13—H13A | 109.3 | C53—C52—H52A | 108.8 |
C12—C13—H13A | 109.3 | N51—C52—H52A | 108.8 |
C14B—C13—H13B | 114.0 | C53—C52—H52B | 108.8 |
C14A—C13—H13B | 109.3 | N51—C52—H52B | 108.8 |
C12—C13—H13B | 109.3 | H52A—C52—H52B | 107.7 |
H13A—C13—H13B | 107.9 | C52—C53—C54 | 111.7 (3) |
C14B—C13—H13C | 109.2 | C52—C53—H53A | 109.3 |
C14A—C13—H13C | 114.0 | C54—C53—H53A | 109.3 |
C12—C13—H13C | 109.3 | C52—C53—H53B | 109.3 |
H13A—C13—H13C | 102.8 | C54—C53—H53B | 109.3 |
C14B—C13—H13D | 109.4 | H53A—C53—H53B | 107.9 |
C12—C13—H13D | 109.4 | C53—C54—C55 | 107.4 (3) |
H13A—C13—H13D | 117.7 | C53—C54—H54A | 110.2 |
H13B—C13—H13D | 102.9 | C55—C54—H54A | 110.2 |
H13C—C13—H13D | 108.0 | C53—C54—H54B | 110.2 |
C13—C14A—C15A | 112.3 (4) | C55—C54—H54B | 110.2 |
C15A—C14A—H13D | 121.1 | H54A—C54—H54B | 108.5 |
C13—C14A—H14A | 109.1 | C56—C55—C54 | 110.7 (3) |
C15A—C14A—H14A | 109.1 | C56—C55—H55A | 109.5 |
H13D—C14A—H14A | 93.5 | C54—C55—H55A | 109.5 |
C13—C14A—H14B | 109.1 | C56—C55—H55B | 109.5 |
C15A—C14A—H14B | 109.1 | C54—C55—H55B | 109.5 |
H13D—C14A—H14B | 114.3 | H55A—C55—H55B | 108.1 |
H14A—C14A—H14B | 107.9 | C55—C56—N51 | 113.4 (2) |
C14A—C15A—C16 | 112.6 (4) | C55—C56—H56A | 108.9 |
C14A—C15A—H15A | 109.1 | N51—C56—H56A | 108.9 |
C16—C15A—H15A | 109.1 | C55—C56—H56B | 108.9 |
C14A—C15A—H15B | 109.1 | N51—C56—H56B | 108.9 |
C16—C15A—H15B | 109.1 | H56A—C56—H56B | 107.7 |
H15A—C15A—H15B | 107.8 | N51—C58—C59 | 117.63 (18) |
C13—C14B—C15B | 107.3 (4) | N51—C58—H58A | 107.9 |
C13—C14B—H14C | 110.2 | C59—C58—H58A | 107.9 |
C15B—C14B—H14C | 110.2 | N51—C58—H58B | 107.9 |
C13—C14B—H14D | 110.2 | C59—C58—H58B | 107.9 |
C15B—C14B—H14D | 110.2 | H58A—C58—H58B | 107.2 |
H14C—C14B—H14D | 108.5 | O52—C59—O51 | 125.4 (2) |
C14B—C15B—C17 | 119.4 (4) | O52—C59—C58 | 115.5 (2) |
C14B—C15B—H15C | 107.5 | O51—C59—C58 | 119.0 (2) |
C17—C15B—H15C | 107.5 | N51—C57—H57A | 109.5 |
C14B—C15B—H15D | 107.5 | N51—C57—H57B | 109.5 |
C17—C15B—H15D | 107.5 | H57A—C57—H57B | 109.5 |
H15C—C15B—H15D | 107.0 | N51—C57—H57C | 109.5 |
N11—C16—C15A | 107.0 (3) | H57A—C57—H57C | 109.5 |
N11—C16—H16A | 110.3 | H57B—C57—H57C | 109.5 |
C15A—C16—H16A | 110.3 | C63—C62—N61 | 112.61 (19) |
N11—C16—H16B | 110.3 | C63—C62—H62A | 109.1 |
C15A—C16—H16B | 110.3 | N61—C62—H62A | 109.1 |
H16A—C16—H16B | 108.6 | C63—C62—H62B | 109.1 |
N11—C16—H17E | 109.5 | N61—C62—H62B | 109.1 |
C15A—C16—H17E | 109.5 | H62A—C62—H62B | 107.8 |
H16A—C16—H17E | 110.2 | C62—C63—C64 | 111.1 (2) |
N11—C16—H17F | 109.5 | C62—C63—H63A | 109.4 |
H16A—C16—H17F | 107.9 | C64—C63—H63A | 109.4 |
H16B—C16—H17F | 110.2 | C62—C63—H63B | 109.4 |
H17E—C16—H17F | 109.5 | C64—C63—H63B | 109.4 |
N11—C16—H17G | 109.5 | H63A—C63—H63B | 108.0 |
C15A—C16—H17G | 111.9 | C63—C64—C65 | 108.2 (2) |
H16B—C16—H17G | 107.9 | C63—C64—H64A | 110.1 |
H17E—C16—H17G | 109.5 | C65—C64—H64A | 110.1 |
H17F—C16—H17G | 109.5 | C63—C64—H64B | 110.1 |
N11—C18—C19 | 118.2 (2) | C65—C64—H64B | 110.1 |
N11—C18—H18A | 107.8 | H64A—C64—H64B | 108.4 |
C19—C18—H18A | 107.8 | C66—C65—C64 | 111.9 (2) |
N11—C18—H18B | 107.8 | C66—C65—H65A | 109.2 |
C19—C18—H18B | 107.8 | C64—C65—H65A | 109.2 |
H18A—C18—H18B | 107.1 | C66—C65—H65B | 109.2 |
O12—C19—O11 | 125.5 (2) | C64—C65—H65B | 109.2 |
O12—C19—C18 | 124.3 (2) | H65A—C65—H65B | 107.9 |
O11—C19—C18 | 110.2 (2) | C65—C66—N61 | 112.64 (19) |
N11—C17—C15B | 104.5 (3) | C65—C66—H66A | 109.1 |
N11—C17—H17A | 109.5 | N61—C66—H66A | 109.1 |
C15B—C17—H17A | 115.4 | C65—C66—H66B | 109.1 |
N11—C17—H17B | 109.5 | N61—C66—H66B | 109.1 |
H17A—C17—H17B | 109.5 | H66A—C66—H66B | 107.8 |
N11—C17—H17C | 109.5 | N61—C67—H67A | 109.5 |
C15B—C17—H17C | 108.3 | N61—C67—H67B | 109.5 |
H17A—C17—H17C | 109.5 | H67A—C67—H67B | 109.5 |
H17B—C17—H17C | 109.5 | N61—C67—H67C | 109.5 |
N11—C17—H16C | 110.8 | H67A—C67—H67C | 109.5 |
C15B—C17—H16C | 110.8 | H67B—C67—H67C | 109.5 |
H17A—C17—H16C | 105.8 | C69A—C68A—N61 | 114.6 (7) |
H17B—C17—H16C | 111.7 | C69A—C68A—H68A | 108.6 |
N11—C17—H16D | 110.8 | N61—C68A—H68A | 108.6 |
C15B—C17—H16D | 110.8 | C69A—C68A—H68B | 108.6 |
H17B—C17—H16D | 105.0 | N61—C68A—H68B | 108.6 |
H17C—C17—H16D | 112.5 | H68A—C68A—H68B | 107.6 |
H16C—C17—H16D | 108.9 | O62A—C69A—O61A | 122.8 (6) |
C23—C22—N21 | 112.73 (17) | O62A—C69A—C68A | 129.1 (7) |
C23—C22—H22A | 109.0 | O61A—C69A—C68A | 108.0 (5) |
N21—C22—H22A | 109.0 | N61—C68B—C69B | 117.0 (7) |
C23—C22—H22B | 109.0 | N61—C68B—H68C | 108.0 |
N21—C22—H22B | 109.0 | C69B—C68B—H68C | 108.0 |
H22A—C22—H22B | 107.8 | N61—C68B—H68D | 108.0 |
C22—C23—C24 | 111.73 (18) | C69B—C68B—H68D | 108.0 |
C22—C23—H23A | 109.3 | H68C—C68B—H68D | 107.3 |
C24—C23—H23A | 109.3 | O62B—C69B—O61B | 128.1 (6) |
C22—C23—H23B | 109.3 | O62B—C69B—C68B | 120.3 (7) |
C24—C23—H23B | 109.3 | O61B—C69B—C68B | 111.5 (6) |
H23A—C23—H23B | 107.9 | C69B—O61B—H61 | 115 (3) |
C23—C24—C25 | 109.96 (18) | H1A—O1—H1B | 110 (4) |
C23—C24—H24A | 109.7 | H1B—O1—H1A | 110 (4) |
C25—C24—H24A | 109.7 | H1A—O1—H1B | 110 (4) |
C23—C24—H24B | 109.7 | H1A—O1—H1B | 110 (4) |
C25—C24—H24B | 109.7 | H2C—O2—H2A | 104 (6) |
H24A—C24—H24B | 108.2 | H2C—O2—H2B | 122 (7) |
C26—C25—C24 | 110.62 (19) | H2A—O2—H2B | 119 (6) |
C26—C25—H25A | 109.5 | H2C—O2—H2A | 104 (6) |
C24—C25—H25A | 109.5 | H2B—O2—H2A | 119 (6) |
C26—C25—H25B | 109.5 | H2C—O2—H2B | 122 (7) |
C24—C25—H25B | 109.5 | H2A—O2—H2B | 119 (6) |
H25A—C25—H25B | 108.1 | H2A—O2—H2B | 119 (6) |
C25—C26—N21 | 113.10 (17) | H2A—O2—H2C | 104 (6) |
C25—C26—H26A | 109.0 | H2B—O2—H2C | 122 (7) |
N21—C26—H26A | 109.0 | H2A—O2—H2C | 104 (6) |
C25—C26—H26B | 109.0 | H2B—O2—H2C | 122 (7) |
N21—C26—H26B | 109.0 | | |
| | | |
C18—N11—C12—C13 | −178.2 (2) | C48—N41—C42—C43 | 171.44 (17) |
C17—N11—C12—C13 | −61.7 (3) | C47—N41—C42—C43 | −69.2 (2) |
C16—N11—C12—C13 | 58.4 (3) | C46—N41—C42—C43 | 54.3 (2) |
N11—C12—C13—C14B | 59.2 (4) | N41—C42—C43—C44 | −57.0 (2) |
N11—C12—C13—C14A | −52.9 (4) | C42—C43—C44—C45 | 56.9 (2) |
C14B—C13—C14A—C15A | −68.0 (5) | C43—C44—C45—C46 | −56.3 (2) |
C12—C13—C14A—C15A | 50.5 (5) | C48—N41—C46—C45 | −169.64 (17) |
C13—C14A—C15A—C16 | −54.7 (6) | C47—N41—C46—C45 | 67.4 (2) |
C14A—C13—C14B—C15B | 67.5 (5) | C42—N41—C46—C45 | −54.2 (2) |
C12—C13—C14B—C15B | −51.2 (5) | C44—C45—C46—N41 | 56.5 (2) |
C13—C14B—C15B—C17 | 55.1 (7) | C47—N41—C48—C49 | 68.7 (2) |
C18—N11—C16—C15A | 178.0 (3) | C46—N41—C48—C49 | −55.5 (2) |
C17—N11—C16—C15A | 61.1 (3) | C42—N41—C48—C49 | −172.87 (18) |
C12—N11—C16—C15A | −58.8 (3) | N41—C48—C49—O42 | −22.9 (3) |
C14A—C15A—C16—N11 | 57.9 (5) | N41—C48—C49—O41 | 158.65 (18) |
C17—N11—C18—C19 | −177.4 (2) | C57—N51—C52—C53 | −170.6 (3) |
C16—N11—C18—C19 | 63.9 (3) | C58—N51—C52—C53 | 67.4 (3) |
C12—N11—C18—C19 | −59.2 (3) | C56—N51—C52—C53 | −53.2 (3) |
N11—C18—C19—O12 | −5.5 (4) | N51—C52—C53—C54 | 56.8 (4) |
N11—C18—C19—O11 | 175.3 (2) | C52—C53—C54—C55 | −56.5 (5) |
C18—N11—C17—C15B | 175.4 (3) | C53—C54—C55—C56 | 57.3 (5) |
C16—N11—C17—C15B | −64.7 (3) | C54—C55—C56—N51 | −58.7 (4) |
C12—N11—C17—C15B | 56.1 (3) | C57—N51—C56—C55 | 172.3 (3) |
C14B—C15B—C17—N11 | −57.4 (5) | C58—N51—C56—C55 | −70.2 (3) |
C27—N21—C22—C23 | −71.9 (2) | C52—N51—C56—C55 | 54.3 (3) |
C28—N21—C22—C23 | 171.84 (17) | C57—N51—C58—C59 | −57.9 (3) |
C26—N21—C22—C23 | 50.3 (2) | C52—N51—C58—C59 | 64.1 (3) |
N21—C22—C23—C24 | −53.4 (2) | C56—N51—C58—C59 | −174.7 (2) |
C22—C23—C24—C25 | 56.4 (2) | N51—C58—C59—O52 | 159.8 (2) |
C23—C24—C25—C26 | −57.3 (2) | N51—C58—C59—O51 | −23.4 (3) |
C24—C25—C26—N21 | 55.9 (2) | C68B—N61—C62—C63 | 177.6 (3) |
C27—N21—C26—C25 | 69.6 (2) | C67—N61—C62—C63 | 69.4 (2) |
C28—N21—C26—C25 | −174.20 (18) | C66—N61—C62—C63 | −53.9 (2) |
C22—N21—C26—C25 | −51.9 (2) | C68A—N61—C62—C63 | −162.2 (3) |
C27—N21—C28—C29 | 177.07 (18) | N61—C62—C63—C64 | 58.4 (3) |
C26—N21—C28—C29 | 58.2 (2) | C62—C63—C64—C65 | −58.0 (3) |
C22—N21—C28—C29 | −64.8 (2) | C63—C64—C65—C66 | 56.9 (3) |
N21—C28—C29—O22 | 21.0 (3) | C64—C65—C66—N61 | −55.6 (3) |
N21—C28—C29—O21 | −161.02 (18) | C68B—N61—C66—C65 | 172.6 (5) |
C38—N31—C32—C33 | 176.84 (19) | C67—N61—C66—C65 | −70.0 (3) |
C37—N31—C32—C33 | −66.9 (2) | C62—N61—C66—C65 | 52.3 (2) |
C36—N31—C32—C33 | 54.5 (2) | C68A—N61—C66—C65 | 163.4 (4) |
N31—C32—C33—C34 | −55.9 (3) | C68B—N61—C68A—C69A | −95 (2) |
C32—C33—C34—C35 | 55.8 (3) | C67—N61—C68A—C69A | −62.3 (6) |
C33—C34—C35—C36 | −55.3 (3) | C66—N61—C68A—C69A | 59.9 (6) |
C38—N31—C36—C35 | −176.05 (18) | C62—N61—C68A—C69A | 174.3 (5) |
C37—N31—C36—C35 | 67.5 (2) | N61—C68A—C69A—O62A | 10.1 (10) |
C32—N31—C36—C35 | −54.1 (2) | N61—C68A—C69A—O61A | −168.4 (5) |
C34—C35—C36—N31 | 54.9 (3) | C67—N61—C68B—C69B | −64.5 (5) |
C37—N31—C38—C39 | −175.09 (18) | C66—N61—C68B—C69B | 58.2 (6) |
C36—N31—C38—C39 | 66.1 (2) | C62—N61—C68B—C69B | −178.9 (4) |
C32—N31—C38—C39 | −56.3 (2) | C68A—N61—C68B—C69B | 86 (2) |
N31—C38—C39—O32 | −9.4 (3) | N61—C68B—C69B—O62B | 6.2 (8) |
N31—C38—C39—O31 | 171.37 (18) | N61—C68B—C69B—O61B | −172.1 (4) |
Symmetry code: (i) −x, −y+2, −z. |