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The crystal structure of the title compound, C
14H
39N
2Si
2+·C
32H
12F
24B
−, reveals a centrosymmetric cation consisting of two 2-(trimethylsilylethyl)dimethylamine molecules held together by a symmetrical N
H
N hydrogen bond. The N—H distance is 1.347 (2) Å, the N
N distance is 2.695 (3) Å and the N
H
N angle is 180°. The tetrakis[3,5-bis(trifluoromethyl)phenyl]borate counter-ion lies on a crystallographic twofold axis of symmetry. The trifluoromethyl groups are disordered and were refined with partial occupancies.
Supporting information
CCDC reference: 232166
Key indicators
- Single-crystal X-ray study
- T = 130 K
- Mean (C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.126
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent F Ueq(max)/Ueq(min) ... 7.56 Ratio
| Author Response: trifluoromethyl groups often have high thermal motion
|
PLAT242_ALERT_2_A Check Low U(eq) as Compared to Neighbors .... C15
| Author Response: C15 is the pivot atom for a disordered trifluoromethyl group
|
PLAT353_ALERT_3_A Long N-H Bond (0.87A) N - H = 1.35 Ang.
| Author Response: Strong intermolecular hydrogen bond
|
PLAT771_ALERT_2_A Suspect N-H Bond in CIF N - H = 1.35 Ang.
| Author Response: Strong intermolecular hydrogen bond
|
Alert level B
PLAT213_ALERT_2_B Atom F8' has ADP max/min Ratio ............. 4.60 prolat
PLAT301_ALERT_3_B Main Residue Disorder ......................... 27.00 Perc.
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
Tmin and Tmax reported: 0.776 0.970
Tmin' and Tmax expected: 0.946 0.973
RR' = 0.823
Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82
PLAT213_ALERT_2_C Atom F1 has ADP max/min Ratio ............. 3.10 prolat
PLAT213_ALERT_2_C Atom F8 has ADP max/min Ratio ............. 3.20 prolat
PLAT213_ALERT_2_C Atom F9 has ADP max/min Ratio ............. 3.50 prolat
PLAT213_ALERT_2_C Atom F7' has ADP max/min Ratio ............. 3.90 prolat
PLAT213_ALERT_2_C Atom F9' has ADP max/min Ratio ............. 3.10 prolat
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C7
| Author Response: C15 is the pivot atom for a disordered trifluoromethyl group
|
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C8
| Author Response: C15 is the pivot atom for a disordered trifluoromethyl group
|
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C16
| Author Response: C15 is the pivot atom for a disordered trifluoromethyl group
|
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Si1
| Author Response: C15 is the pivot atom for a disordered trifluoromethyl group
|
PLAT420_ALERT_2_C D-H Without Acceptor N - H ... ?
PLAT432_ALERT_2_C Short Inter X...Y Contact C5 .. F6' = 2.88 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact C22 .. F4' = 2.96 Ang.
PLAT751_ALERT_4_C Bond Calc 1.34739, Rep 1.3474(19) ...... Senseless su
N -H 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 105.24, Rep 105.24(16) ...... Senseless su
C20 -N -H 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 106.82, Rep 106.82(17) ...... Senseless su
C19 -N -H 1.555 1.555 1.555
PLAT752_ALERT_4_C Angle Calc 109.92, Rep 109.93(15) ...... Senseless su
C18 -N -H 1.555 1.555 1.555
4 ALERT level A = In general: serious problem
2 ALERT level B = Potentially serious problem
19 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
16 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
4 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Crystal data top
C14H39N2Si2+·C32H12F24B− | Dx = 1.401 Mg m−3 |
Mr = 1154.88 | Melting point = 366–367 K |
Orthorhombic, Pbcn | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2n 2ab | Cell parameters from 6546 reflections |
a = 17.1047 (11) Å | θ = 2.4–24.8° |
b = 16.8652 (11) Å | µ = 0.18 mm−1 |
c = 18.9828 (12) Å | T = 130 K |
V = 5476.0 (6) Å3 | Block, colourless |
Z = 4 | 0.30 × 0.30 × 0.15 mm |
F(000) = 2360 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4835 independent reflections |
Radiation source: sealed tube | 3972 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→20 |
Tmin = 0.776, Tmax = 0.970 | k = −20→19 |
29606 measured reflections | l = −12→22 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.126 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0645P)2 + 2.2182P] where P = (Fo2 + 2Fc2)/3 |
4835 reflections | (Δ/σ)max = 0.010 |
407 parameters | Δρmax = 0.30 e Å−3 |
12 restraints | Δρmin = −0.20 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) |
B | 0.0000 | 0.52968 (16) | 0.2500 | 0.0279 (6) | |
F1 | 0.00197 (19) | 0.22634 (10) | 0.36552 (18) | 0.1362 (15) | 0.932 (5) |
F2 | −0.10819 (15) | 0.27829 (13) | 0.38253 (15) | 0.1020 (11) | 0.932 (5) |
F3 | −0.03583 (15) | 0.25463 (11) | 0.46816 (10) | 0.0964 (9) | 0.932 (5) |
F4 | 0.20841 (9) | 0.48916 (15) | 0.47793 (11) | 0.0886 (9) | 0.935 (4) |
F5 | 0.12646 (11) | 0.58033 (9) | 0.49429 (9) | 0.0660 (6) | 0.935 (4) |
F6 | 0.11869 (11) | 0.47602 (12) | 0.55491 (7) | 0.0768 (7) | 0.935 (4) |
F7 | 0.2992 (2) | 0.4900 (2) | 0.2179 (4) | 0.090 (2) | 0.633 (13) |
F8 | 0.3392 (4) | 0.5958 (5) | 0.2495 (7) | 0.161 (6) | 0.633 (13) |
F9 | 0.3311 (4) | 0.5727 (6) | 0.1412 (4) | 0.158 (5) | 0.633 (13) |
F7' | 0.2987 (5) | 0.5002 (7) | 0.1604 (7) | 0.176 (11) | 0.367 (13) |
F8' | 0.3122 (5) | 0.5388 (13) | 0.2639 (8) | 0.204 (13) | 0.367 (13) |
F9' | 0.3488 (3) | 0.6084 (5) | 0.1873 (8) | 0.089 (4) | 0.367 (13) |
F10 | 0.17850 (10) | 0.82104 (9) | 0.12066 (11) | 0.0734 (6) | 0.958 (4) |
F11 | 0.07421 (15) | 0.82749 (9) | 0.18080 (11) | 0.0965 (9) | 0.958 (4) |
F12 | 0.07247 (12) | 0.77881 (10) | 0.07797 (11) | 0.0832 (8) | 0.958 (4) |
F5' | 0.1809 (12) | 0.5573 (13) | 0.4709 (11) | 0.052 (7)* | 0.065 (4) |
F4' | 0.1855 (16) | 0.4453 (14) | 0.5170 (14) | 0.074 (8)* | 0.065 (4) |
F6' | 0.1093 (17) | 0.5378 (14) | 0.5362 (17) | 0.083 (10)* | 0.065 (4) |
F1' | −0.0654 (10) | 0.2544 (9) | 0.3501 (8) | 0.028 (5)* | 0.068 (5) |
F3' | 0.0171 (11) | 0.2325 (13) | 0.4243 (12) | 0.060 (8)* | 0.068 (5) |
F2' | −0.0810 (18) | 0.2755 (18) | 0.4454 (10) | 0.084 (10)* | 0.068 (5) |
F11' | 0.0475 (14) | 0.7995 (14) | 0.1239 (15) | 0.027 (8)* | 0.042 (4) |
F10' | 0.140 (2) | 0.838 (2) | 0.1755 (15) | 0.071 (13)* | 0.042 (4) |
F12' | 0.1447 (15) | 0.794 (3) | 0.081 (3) | 0.093 (16)* | 0.042 (4) |
H | 0.5000 | 0.5000 | 0.5000 | 0.089 (13)* | |
C1 | 0.02190 (10) | 0.47629 (10) | 0.31934 (9) | 0.0286 (4) | |
C2 | 0.06887 (11) | 0.50643 (11) | 0.37323 (10) | 0.0312 (4) | |
H2 | 0.0922 | 0.5557 | 0.3670 | 0.037* | |
C3 | 0.08213 (11) | 0.46572 (11) | 0.43579 (10) | 0.0336 (4) | |
C4 | 0.04914 (12) | 0.39169 (12) | 0.44667 (11) | 0.0386 (5) | |
H4 | 0.0583 | 0.3638 | 0.4881 | 0.046* | |
C5 | 0.00233 (12) | 0.36056 (11) | 0.39442 (11) | 0.0372 (5) | |
C6 | −0.01163 (11) | 0.40212 (10) | 0.33250 (10) | 0.0324 (4) | |
H6 | −0.0443 | 0.3799 | 0.2987 | 0.039* | |
C7 | −0.03372 (17) | 0.28042 (14) | 0.40229 (14) | 0.0571 (6) | |
C8 | 0.13377 (13) | 0.50163 (14) | 0.49044 (11) | 0.0437 (5) | |
C9 | 0.07469 (10) | 0.58334 (10) | 0.22370 (9) | 0.0271 (4) | |
C10 | 0.15106 (11) | 0.55463 (11) | 0.22606 (10) | 0.0326 (4) | |
H10 | 0.1600 | 0.5051 | 0.2460 | 0.039* | |
C11 | 0.21409 (11) | 0.59697 (12) | 0.19991 (11) | 0.0370 (5) | |
C12 | 0.20388 (12) | 0.67162 (11) | 0.17113 (10) | 0.0358 (4) | |
H12 | 0.2463 | 0.7009 | 0.1549 | 0.043* | |
C13 | 0.12884 (11) | 0.70139 (11) | 0.16720 (10) | 0.0322 (4) | |
C14 | 0.06571 (11) | 0.65744 (10) | 0.19187 (9) | 0.0298 (4) | |
H14 | 0.0156 | 0.6782 | 0.1870 | 0.036* | |
C15 | 0.29456 (15) | 0.56303 (17) | 0.20276 (18) | 0.0668 (8) | |
C16 | 0.11440 (13) | 0.78135 (13) | 0.13736 (12) | 0.0460 (5) | |
C20 | 0.48948 (16) | 0.51691 (16) | 0.38296 (14) | 0.0635 (7) | |
H20A | 0.5247 | 0.4740 | 0.3733 | 0.095* | |
H20B | 0.5187 | 0.5651 | 0.3885 | 0.095* | |
H20C | 0.4534 | 0.5225 | 0.3445 | 0.095* | |
C21 | 0.36098 (16) | 0.23280 (15) | 0.36181 (15) | 0.0624 (7) | |
H21A | 0.4009 | 0.2285 | 0.3972 | 0.094* | |
H21B | 0.3846 | 0.2447 | 0.3172 | 0.094* | |
H21C | 0.3331 | 0.1835 | 0.3585 | 0.094* | |
C22 | 0.24977 (16) | 0.28984 (17) | 0.47405 (14) | 0.0635 (7) | |
H22A | 0.2140 | 0.3310 | 0.4876 | 0.095* | |
H22B | 0.2910 | 0.2862 | 0.5082 | 0.095* | |
H22C | 0.2225 | 0.2402 | 0.4717 | 0.095* | |
C23 | 0.21431 (15) | 0.32243 (15) | 0.31828 (14) | 0.0592 (7) | |
H23A | 0.1790 | 0.3642 | 0.3312 | 0.089* | |
H23B | 0.1862 | 0.2733 | 0.3150 | 0.089* | |
H23C | 0.2377 | 0.3345 | 0.2736 | 0.089* | |
C17 | 0.34641 (13) | 0.41028 (12) | 0.38717 (12) | 0.0447 (5) | |
H17A | 0.3739 | 0.4157 | 0.3427 | 0.054* | |
H17B | 0.3084 | 0.4529 | 0.3898 | 0.054* | |
C18 | 0.40476 (13) | 0.42136 (12) | 0.44623 (12) | 0.0446 (5) | |
H18A | 0.3777 | 0.4138 | 0.4906 | 0.054* | |
H18B | 0.4440 | 0.3801 | 0.4425 | 0.054* | |
C19 | 0.39093 (16) | 0.56565 (14) | 0.46442 (17) | 0.0670 (8) | |
H19A | 0.3635 | 0.5542 | 0.5074 | 0.100* | |
H19B | 0.3541 | 0.5710 | 0.4266 | 0.100* | |
H19C | 0.4196 | 0.6142 | 0.4696 | 0.100* | |
N | 0.44578 (11) | 0.50013 (10) | 0.44851 (10) | 0.0469 (5) | |
Si1 | 0.29200 (3) | 0.31336 (3) | 0.38616 (3) | 0.03866 (18) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
B | 0.0290 (15) | 0.0228 (13) | 0.0318 (15) | 0.000 | 0.0027 (12) | 0.000 |
F1 | 0.200 (3) | 0.0315 (9) | 0.178 (3) | −0.0169 (13) | 0.099 (2) | −0.0148 (13) |
F2 | 0.0894 (17) | 0.0797 (14) | 0.137 (2) | −0.0483 (13) | −0.0356 (16) | 0.0454 (14) |
F3 | 0.136 (2) | 0.0802 (13) | 0.0729 (13) | −0.0485 (13) | −0.0174 (13) | 0.0479 (11) |
F4 | 0.0324 (9) | 0.139 (2) | 0.0947 (15) | 0.0104 (10) | −0.0063 (8) | −0.0619 (14) |
F5 | 0.0868 (14) | 0.0540 (10) | 0.0572 (10) | 0.0022 (8) | −0.0218 (9) | −0.0141 (8) |
F6 | 0.0982 (14) | 0.1013 (15) | 0.0308 (8) | −0.0204 (11) | −0.0164 (8) | 0.0131 (8) |
F7 | 0.049 (2) | 0.064 (3) | 0.158 (5) | 0.0267 (16) | 0.008 (3) | 0.031 (3) |
F8 | 0.067 (4) | 0.149 (6) | 0.267 (14) | 0.026 (3) | −0.091 (7) | −0.051 (7) |
F9 | 0.086 (5) | 0.262 (11) | 0.125 (5) | 0.097 (6) | 0.071 (4) | 0.100 (7) |
F7' | 0.089 (6) | 0.158 (12) | 0.28 (2) | 0.076 (7) | −0.021 (10) | −0.128 (15) |
F8' | 0.042 (5) | 0.39 (3) | 0.180 (14) | 0.039 (10) | −0.002 (6) | 0.204 (19) |
F9' | 0.023 (3) | 0.092 (5) | 0.151 (9) | −0.001 (2) | 0.017 (5) | 0.058 (6) |
F10 | 0.0646 (11) | 0.0463 (9) | 0.1092 (15) | −0.0161 (7) | 0.0059 (10) | 0.0332 (9) |
F11 | 0.144 (2) | 0.0393 (8) | 0.1065 (16) | 0.0343 (10) | 0.0621 (14) | 0.0220 (9) |
F12 | 0.1033 (15) | 0.0633 (10) | 0.0831 (15) | −0.0088 (10) | −0.0404 (12) | 0.0383 (10) |
C1 | 0.0293 (10) | 0.0258 (9) | 0.0306 (9) | 0.0034 (7) | 0.0040 (8) | 0.0000 (7) |
C2 | 0.0317 (10) | 0.0291 (9) | 0.0327 (10) | 0.0007 (8) | 0.0050 (8) | 0.0008 (8) |
C3 | 0.0301 (10) | 0.0390 (10) | 0.0315 (10) | 0.0066 (8) | 0.0044 (8) | −0.0007 (8) |
C4 | 0.0390 (11) | 0.0413 (11) | 0.0354 (11) | 0.0083 (9) | 0.0046 (9) | 0.0104 (9) |
C5 | 0.0404 (11) | 0.0311 (10) | 0.0401 (11) | 0.0016 (8) | 0.0080 (9) | 0.0077 (9) |
C6 | 0.0332 (10) | 0.0292 (9) | 0.0346 (10) | −0.0006 (8) | 0.0036 (8) | 0.0007 (8) |
C7 | 0.0730 (18) | 0.0411 (13) | 0.0572 (15) | −0.0077 (12) | 0.0043 (14) | 0.0159 (12) |
C8 | 0.0402 (12) | 0.0555 (13) | 0.0353 (11) | 0.0088 (10) | 0.0023 (9) | −0.0034 (10) |
C9 | 0.0321 (10) | 0.0254 (9) | 0.0236 (9) | 0.0009 (7) | 0.0012 (7) | −0.0020 (7) |
C10 | 0.0360 (11) | 0.0283 (9) | 0.0336 (10) | 0.0040 (8) | 0.0022 (8) | 0.0039 (8) |
C11 | 0.0308 (10) | 0.0405 (11) | 0.0396 (11) | 0.0027 (8) | 0.0039 (8) | 0.0053 (9) |
C12 | 0.0336 (11) | 0.0382 (10) | 0.0356 (10) | −0.0056 (8) | 0.0066 (8) | 0.0035 (8) |
C13 | 0.0377 (11) | 0.0304 (10) | 0.0285 (9) | −0.0011 (8) | 0.0012 (8) | 0.0008 (8) |
C14 | 0.0312 (10) | 0.0287 (9) | 0.0296 (9) | 0.0015 (8) | −0.0005 (8) | 0.0012 (8) |
C15 | 0.0387 (14) | 0.0666 (17) | 0.095 (2) | 0.0092 (13) | 0.0150 (15) | 0.0319 (18) |
C16 | 0.0492 (13) | 0.0370 (11) | 0.0519 (13) | −0.0031 (10) | 0.0052 (11) | 0.0115 (10) |
C20 | 0.0579 (16) | 0.0576 (15) | 0.0751 (18) | −0.0116 (12) | 0.0116 (13) | 0.0035 (13) |
C21 | 0.0668 (16) | 0.0557 (14) | 0.0646 (16) | 0.0232 (13) | −0.0082 (13) | −0.0202 (13) |
C22 | 0.0576 (16) | 0.0701 (17) | 0.0629 (16) | 0.0043 (13) | 0.0132 (13) | 0.0129 (13) |
C23 | 0.0492 (14) | 0.0641 (15) | 0.0642 (16) | 0.0055 (12) | −0.0088 (12) | −0.0053 (13) |
C17 | 0.0501 (13) | 0.0394 (11) | 0.0446 (12) | −0.0013 (9) | 0.0048 (10) | −0.0010 (9) |
C18 | 0.0469 (13) | 0.0366 (11) | 0.0502 (13) | −0.0041 (9) | 0.0015 (10) | −0.0035 (10) |
C19 | 0.0566 (16) | 0.0436 (13) | 0.101 (2) | 0.0030 (11) | 0.0027 (15) | −0.0206 (14) |
N | 0.0428 (10) | 0.0360 (9) | 0.0618 (12) | −0.0028 (8) | 0.0055 (9) | −0.0072 (9) |
Si1 | 0.0362 (3) | 0.0352 (3) | 0.0446 (3) | 0.0032 (2) | 0.0024 (2) | −0.0052 (2) |
Geometric parameters (Å, º) top
B—C1i | 1.638 (2) | C9—C10 | 1.394 (3) |
B—C1 | 1.638 (2) | C9—C14 | 1.397 (2) |
B—C9 | 1.643 (2) | C10—C11 | 1.385 (3) |
B—C9i | 1.643 (2) | C10—H10 | 0.9300 |
F1—C7 | 1.301 (3) | C11—C12 | 1.383 (3) |
F2—C7 | 1.328 (3) | C11—C15 | 1.492 (3) |
F3—C7 | 1.324 (3) | C12—C13 | 1.380 (3) |
F4—C8 | 1.315 (3) | C12—H12 | 0.9300 |
F5—C8 | 1.335 (3) | C13—C14 | 1.391 (3) |
F6—C8 | 1.323 (3) | C13—C16 | 1.483 (3) |
F7—C15 | 1.266 (5) | C14—H14 | 0.9300 |
F8—C15 | 1.294 (6) | C20—N | 1.479 (3) |
F9—C15 | 1.334 (5) | C20—H20A | 0.9600 |
F7'—C15 | 1.333 (8) | C20—H20B | 0.9600 |
F8'—C15 | 1.267 (9) | C20—H20C | 0.9600 |
F9'—C15 | 1.238 (6) | C21—Si1 | 1.858 (2) |
F10—C16 | 1.323 (3) | C21—H21A | 0.9600 |
F11—C16 | 1.326 (3) | C21—H21B | 0.9600 |
F12—C16 | 1.337 (3) | C21—H21C | 0.9600 |
F5'—C8 | 1.29 (2) | C22—Si1 | 1.861 (3) |
F4'—C8 | 1.39 (3) | C22—H22A | 0.9600 |
F6'—C8 | 1.14 (3) | C22—H22B | 0.9600 |
F1'—C7 | 1.211 (15) | C22—H22C | 0.9600 |
F3'—C7 | 1.26 (2) | C23—Si1 | 1.857 (3) |
F2'—C7 | 1.15 (3) | C23—H23A | 0.9600 |
F11'—C16 | 1.21 (2) | C23—H23B | 0.9600 |
F10'—C16 | 1.27 (4) | C23—H23C | 0.9600 |
F12'—C16 | 1.21 (5) | C17—C18 | 1.512 (3) |
C1—C2 | 1.397 (3) | C17—Si1 | 1.881 (2) |
C1—C6 | 1.399 (3) | C17—H17A | 0.9700 |
C2—C3 | 1.390 (3) | C17—H17B | 0.9700 |
C2—H2 | 0.9300 | C18—N | 1.503 (3) |
C3—C4 | 1.385 (3) | C18—H18A | 0.9700 |
C3—C8 | 1.491 (3) | C18—H18B | 0.9700 |
C4—C5 | 1.379 (3) | C19—N | 1.481 (3) |
C4—H4 | 0.9300 | C19—H19A | 0.9600 |
C5—C6 | 1.389 (3) | C19—H19B | 0.9600 |
C5—C7 | 1.493 (3) | C19—H19C | 0.9600 |
C6—H6 | 0.9300 | N—H | 1.3474 (19) |
| | | |
C1i—B—C1 | 113.3 (2) | F8'—C15—C11 | 112.1 (6) |
C1i—B—C9 | 103.68 (8) | F7—C15—C11 | 116.1 (3) |
C1—B—C9 | 111.66 (9) | F8—C15—C11 | 113.9 (4) |
C1i—B—C9i | 111.66 (9) | F7'—C15—C11 | 109.4 (4) |
C1—B—C9i | 103.68 (8) | F9—C15—C11 | 110.7 (3) |
C9—B—C9i | 113.2 (2) | F12'—C16—F11 | 132 (2) |
C2—C1—C6 | 115.51 (16) | F11'—C16—F11 | 59.6 (13) |
C2—C1—B | 121.34 (15) | F10'—C16—F11 | 52.1 (16) |
C6—C1—B | 122.77 (16) | F12'—C16—F10 | 48.8 (19) |
C3—C2—C1 | 122.67 (17) | F11'—C16—F10 | 127.2 (12) |
C3—C2—H2 | 118.7 | F10'—C16—F10 | 58.3 (14) |
C1—C2—H2 | 118.7 | F11—C16—F10 | 106.4 (2) |
C4—C3—C2 | 120.39 (18) | F11—C16—F12 | 105.4 (2) |
C4—C3—C8 | 120.24 (18) | F10—C16—F12 | 104.99 (19) |
C2—C3—C8 | 119.36 (18) | F12'—C16—C13 | 115 (2) |
C5—C4—C3 | 118.19 (18) | F11'—C16—C13 | 117.8 (11) |
C5—C4—H4 | 120.9 | F10'—C16—C13 | 113.8 (17) |
C3—C4—H4 | 120.9 | F11—C16—C13 | 112.49 (18) |
C4—C5—C6 | 121.09 (18) | F10—C16—C13 | 114.42 (19) |
C4—C5—C7 | 120.84 (19) | F12—C16—C13 | 112.46 (18) |
C6—C5—C7 | 118.06 (19) | N—C20—H20A | 109.5 |
C5—C6—C1 | 122.13 (18) | N—C20—H20B | 109.5 |
C5—C6—H6 | 118.9 | H20A—C20—H20B | 109.5 |
C1—C6—H6 | 118.9 | N—C20—H20C | 109.5 |
F2'—C7—F1' | 103.9 (11) | H20A—C20—H20C | 109.5 |
F2'—C7—F3' | 101.6 (12) | H20B—C20—H20C | 109.5 |
F1'—C7—F3' | 110.4 (10) | Si1—C21—H21A | 109.5 |
F1—C7—F3 | 106.8 (2) | Si1—C21—H21B | 109.5 |
F1—C7—F2 | 106.2 (3) | H21A—C21—H21B | 109.5 |
F3—C7—F2 | 103.4 (2) | Si1—C21—H21C | 109.5 |
F2'—C7—C5 | 115.2 (15) | H21A—C21—H21C | 109.5 |
F1'—C7—C5 | 115.5 (8) | H21B—C21—H21C | 109.5 |
F3'—C7—C5 | 109.2 (10) | Si1—C22—H22A | 109.5 |
F1—C7—C5 | 112.8 (2) | Si1—C22—H22B | 109.5 |
F3—C7—C5 | 113.8 (2) | H22A—C22—H22B | 109.5 |
F2—C7—C5 | 113.1 (2) | Si1—C22—H22C | 109.5 |
F6'—C8—F5' | 93.3 (14) | H22A—C22—H22C | 109.5 |
F4—C8—F6 | 107.7 (2) | H22B—C22—H22C | 109.5 |
F4—C8—F5 | 105.1 (2) | Si1—C23—H23A | 109.5 |
F6—C8—F5 | 104.81 (18) | Si1—C23—H23B | 109.5 |
F6'—C8—F4' | 108.8 (16) | H23A—C23—H23B | 109.5 |
F5'—C8—F4' | 101.7 (11) | Si1—C23—H23C | 109.5 |
F6'—C8—C3 | 122.0 (15) | H23A—C23—H23C | 109.5 |
F5'—C8—C3 | 117.7 (9) | H23B—C23—H23C | 109.5 |
F4—C8—C3 | 112.61 (18) | C18—C17—Si1 | 116.20 (15) |
F6—C8—C3 | 113.28 (19) | C18—C17—H17A | 108.2 |
F5—C8—C3 | 112.73 (18) | Si1—C17—H17A | 108.2 |
F4'—C8—C3 | 110.6 (11) | C18—C17—H17B | 108.2 |
C10—C9—C14 | 115.33 (16) | Si1—C17—H17B | 108.2 |
C10—C9—B | 121.83 (15) | H17A—C17—H17B | 107.4 |
C14—C9—B | 122.60 (16) | N—C18—C17 | 116.02 (18) |
C11—C10—C9 | 122.61 (17) | N—C18—H18A | 108.3 |
C11—C10—H10 | 118.7 | C17—C18—H18A | 108.3 |
C9—C10—H10 | 118.7 | N—C18—H18B | 108.3 |
C12—C11—C10 | 120.82 (18) | C17—C18—H18B | 108.3 |
C12—C11—C15 | 118.68 (19) | H18A—C18—H18B | 107.4 |
C10—C11—C15 | 120.50 (18) | N—C19—H19A | 109.5 |
C13—C12—C11 | 118.02 (17) | N—C19—H19B | 109.5 |
C13—C12—H12 | 121.0 | H19A—C19—H19B | 109.5 |
C11—C12—H12 | 121.0 | N—C19—H19C | 109.5 |
C12—C13—C14 | 120.66 (17) | H19A—C19—H19C | 109.5 |
C12—C13—C16 | 120.41 (17) | H19B—C19—H19C | 109.5 |
C14—C13—C16 | 118.93 (18) | C20—N—C19 | 110.4 (2) |
C13—C14—C9 | 122.49 (17) | C20—N—C18 | 112.39 (18) |
C13—C14—H14 | 118.8 | C19—N—C18 | 111.69 (17) |
C9—C14—H14 | 118.8 | C20—N—H | 105.24 (16) |
F9'—C15—F8' | 103.8 (5) | C19—N—H | 106.82 (17) |
F7—C15—F8 | 102.9 (4) | C18—N—H | 109.93 (15) |
F9'—C15—F7' | 108.0 (6) | C23—Si1—C21 | 110.01 (12) |
F8'—C15—F7' | 106.5 (8) | C23—Si1—C22 | 111.22 (13) |
F9'—C15—F9 | 50.7 (4) | C21—Si1—C22 | 108.28 (13) |
F8'—C15—F9 | 136.9 (5) | C23—Si1—C17 | 106.83 (11) |
F7—C15—F9 | 106.7 (4) | C21—Si1—C17 | 108.89 (12) |
F8—C15—F9 | 105.8 (5) | C22—Si1—C17 | 111.60 (12) |
F9'—C15—C11 | 116.5 (4) | | |
| | | |
C1i—B—C1—C2 | 155.61 (18) | C1i—B—C9—C14 | 89.4 (2) |
C9—B—C1—C2 | 39.0 (2) | C1—B—C9—C14 | −148.25 (16) |
C9i—B—C1—C2 | −83.16 (17) | C9i—B—C9—C14 | −31.73 (13) |
C1i—B—C1—C6 | −31.82 (13) | C14—C9—C10—C11 | 1.1 (3) |
C9—B—C1—C6 | −148.44 (17) | B—C9—C10—C11 | 175.69 (16) |
C9i—B—C1—C6 | 89.4 (2) | C9—C10—C11—C12 | 1.4 (3) |
C6—C1—C2—C3 | 0.4 (3) | C9—C10—C11—C15 | −179.1 (2) |
B—C1—C2—C3 | 173.43 (15) | C10—C11—C12—C13 | −2.1 (3) |
C1—C2—C3—C4 | 0.8 (3) | C15—C11—C12—C13 | 178.4 (2) |
C1—C2—C3—C8 | 179.33 (17) | C11—C12—C13—C14 | 0.3 (3) |
C2—C3—C4—C5 | −0.9 (3) | C11—C12—C13—C16 | 179.52 (19) |
C8—C3—C4—C5 | −179.45 (18) | C12—C13—C14—C9 | 2.3 (3) |
C3—C4—C5—C6 | −0.1 (3) | C16—C13—C14—C9 | −176.92 (18) |
C3—C4—C5—C7 | 178.8 (2) | C10—C9—C14—C13 | −2.9 (3) |
C4—C5—C6—C1 | 1.3 (3) | B—C9—C14—C13 | −177.45 (15) |
C7—C5—C6—C1 | −177.67 (19) | C12—C11—C15—F9' | 9.1 (9) |
C2—C1—C6—C5 | −1.4 (3) | C10—C11—C15—F9' | −170.5 (9) |
B—C1—C6—C5 | −174.33 (16) | C12—C11—C15—F8' | 128.4 (12) |
C4—C5—C7—F2' | 67.7 (13) | C10—C11—C15—F8' | −51.1 (12) |
C6—C5—C7—F2' | −113.4 (13) | C12—C11—C15—F7 | −168.1 (4) |
C4—C5—C7—F1' | −171.0 (10) | C10—C11—C15—F7 | 12.4 (5) |
C6—C5—C7—F1' | 8.0 (10) | C12—C11—C15—F8 | 72.8 (8) |
C4—C5—C7—F3' | −45.8 (10) | C10—C11—C15—F8 | −106.8 (7) |
C6—C5—C7—F3' | 133.1 (10) | C12—C11—C15—F7' | −113.7 (8) |
C4—C5—C7—F1 | −103.3 (3) | C10—C11—C15—F7' | 66.8 (8) |
C6—C5—C7—F1 | 75.6 (3) | C12—C11—C15—F9 | −46.3 (6) |
C4—C5—C7—F3 | 18.5 (3) | C10—C11—C15—F9 | 134.2 (6) |
C6—C5—C7—F3 | −162.5 (2) | C12—C13—C16—F12' | 50 (2) |
C4—C5—C7—F2 | 136.1 (3) | C14—C13—C16—F12' | −131 (2) |
C6—C5—C7—F2 | −44.9 (3) | C12—C13—C16—F11' | 167.7 (15) |
C4—C3—C8—F6' | −86.3 (16) | C14—C13—C16—F11' | −13.1 (15) |
C2—C3—C8—F6' | 95.1 (16) | C12—C13—C16—F10' | −68.9 (17) |
C4—C3—C8—F5' | 159.7 (11) | C14—C13—C16—F10' | 110.3 (17) |
C2—C3—C8—F5' | −18.8 (11) | C12—C13—C16—F11 | −126.0 (2) |
C4—C3—C8—F4 | 96.1 (3) | C14—C13—C16—F11 | 53.2 (3) |
C2—C3—C8—F4 | −82.5 (3) | C12—C13—C16—F10 | −4.5 (3) |
C4—C3—C8—F6 | −26.4 (3) | C14—C13—C16—F10 | 174.75 (19) |
C2—C3—C8—F6 | 155.00 (19) | C12—C13—C16—F12 | 115.2 (2) |
C4—C3—C8—F5 | −145.3 (2) | C14—C13—C16—F12 | −65.6 (3) |
C2—C3—C8—F5 | 36.2 (3) | Si1—C17—C18—N | −177.67 (15) |
C4—C3—C8—F4' | 43.5 (12) | C17—C18—N—C20 | −58.6 (3) |
C2—C3—C8—F4' | −135.0 (11) | C17—C18—N—C19 | 66.2 (3) |
C1i—B—C9—C10 | −84.75 (18) | C18—C17—Si1—C23 | 171.01 (17) |
C1—B—C9—C10 | 37.6 (2) | C18—C17—Si1—C21 | −70.2 (2) |
C9i—B—C9—C10 | 154.11 (18) | C18—C17—Si1—C22 | 49.2 (2) |
Symmetry code: (i) −x, y, −z+1/2. |
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