Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680102027X/ob6091sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680102027X/ob6091Isup2.hkl |
CCDC reference: 180554
A toluene solution containing B(C6F5)3 and C4H8S in an approximately 1:1 ratio was slowly evaporated under an argon atmosphere over three weeks to yield colorless crystals of the adduct complex (I).
A relatively low completeness (94.58%) was caused by the presence of a cooling device. The C—H bond lengths are 0.94 (2)–1.02 (2) Å.
Data collection: XSCANS (Siemens, 1992); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1991); software used to prepare material for publication: SHELXL97.
Fig. 1. View of the title compound showing the labelling of non-H atoms. Displacement ellipsoids are shown at the 50% probability level. |
C22H8BF15S | Z = 2 |
Mr = 600.15 | F(000) = 592 |
Triclinic, P1 | Dx = 1.889 Mg m−3 |
a = 9.5892 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.8264 (10) Å | Cell parameters from 42 reflections |
c = 11.3959 (9) Å | θ = 11.3–12.4° |
α = 111.904 (6)° | µ = 0.30 mm−1 |
β = 96.814 (7)° | T = 230 K |
γ = 100.727 (7)° | Prism, colorless |
V = 1055.29 (16) Å3 | 0.6 × 0.5 × 0.3 mm |
Siemens P4 diffractometer | Rint = 0.034 |
Radiation source: fine-focus sealed tube | θmax = 27.0°, θmin = 2.0° |
Graphite monochromator | h = −10→12 |
ω scans | k = −12→12 |
7694 measured reflections | l = −14→14 |
4359 independent reflections | 3 standard reflections every 97 reflections |
3938 reflections with I > 2σ(I) | intensity decay: 1.8% |
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)] = 0.031 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.083 | All H-atom parameters refined |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0271P)2 + 0.4601P] where P = (Fo2 + 2Fc2)/3 |
4359 reflections | (Δ/σ)max = 0.001 |
384 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C22H8BF15S | γ = 100.727 (7)° |
Mr = 600.15 | V = 1055.29 (16) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.5892 (8) Å | Mo Kα radiation |
b = 10.8264 (10) Å | µ = 0.30 mm−1 |
c = 11.3959 (9) Å | T = 230 K |
α = 111.904 (6)° | 0.6 × 0.5 × 0.3 mm |
β = 96.814 (7)° |
Siemens P4 diffractometer | Rint = 0.034 |
7694 measured reflections | 3 standard reflections every 97 reflections |
4359 independent reflections | intensity decay: 1.8% |
3938 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.031 | 0 restraints |
wR(F2) = 0.083 | All H-atom parameters refined |
S = 1.05 | Δρmax = 0.28 e Å−3 |
4359 reflections | Δρmin = −0.24 e Å−3 |
384 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. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | −0.77773 (4) | −0.22428 (4) | −0.21870 (3) | 0.02816 (10) | |
B1 | −0.86616 (18) | −0.12540 (16) | −0.32354 (15) | 0.0247 (3) | |
C1 | −0.81356 (16) | 0.03818 (14) | −0.23091 (13) | 0.0266 (3) | |
C2 | −0.67681 (17) | 0.10162 (16) | −0.15288 (14) | 0.0307 (3) | |
C3 | −0.63060 (19) | 0.23900 (17) | −0.07253 (15) | 0.0370 (4) | |
C4 | −0.7210 (2) | 0.32302 (16) | −0.07256 (16) | 0.0405 (4) | |
C5 | −0.8556 (2) | 0.26750 (16) | −0.15242 (15) | 0.0350 (4) | |
C6 | −0.89915 (17) | 0.12856 (16) | −0.22841 (14) | 0.0299 (3) | |
C7 | −0.78774 (16) | −0.16591 (15) | −0.44701 (13) | 0.0262 (3) | |
C8 | −0.78044 (17) | −0.29978 (15) | −0.51700 (14) | 0.0295 (3) | |
C9 | −0.71829 (18) | −0.34035 (16) | −0.62297 (14) | 0.0326 (3) | |
C10 | −0.65837 (18) | −0.24438 (18) | −0.66599 (14) | 0.0342 (3) | |
C11 | −0.66342 (18) | −0.11060 (17) | −0.60252 (15) | 0.0329 (3) | |
C12 | −0.72629 (17) | −0.07426 (15) | −0.49589 (14) | 0.0292 (3) | |
C13 | −1.04071 (16) | −0.18730 (14) | −0.35671 (13) | 0.0258 (3) | |
C14 | −1.12083 (16) | −0.16068 (15) | −0.26064 (13) | 0.0278 (3) | |
C15 | −1.26767 (17) | −0.21124 (17) | −0.27942 (15) | 0.0329 (3) | |
C16 | −1.34531 (17) | −0.29414 (17) | −0.40268 (17) | 0.0350 (3) | |
C17 | −1.27374 (18) | −0.32197 (16) | −0.50273 (15) | 0.0341 (3) | |
C18 | −1.12553 (17) | −0.26887 (15) | −0.47864 (14) | 0.0286 (3) | |
C19 | −0.76441 (19) | −0.13122 (17) | −0.04552 (14) | 0.0332 (3) | |
C20 | −0.8336 (2) | −0.2393 (2) | −0.00059 (16) | 0.0412 (4) | |
C21 | −0.9643 (2) | −0.33475 (19) | −0.10389 (17) | 0.0394 (4) | |
C22 | −0.9161 (2) | −0.37275 (17) | −0.23197 (16) | 0.0364 (4) | |
F1 | −0.57905 (10) | 0.02638 (10) | −0.15305 (10) | 0.0402 (2) | |
F2 | −0.49884 (12) | 0.29035 (11) | 0.00451 (10) | 0.0530 (3) | |
F3 | −0.67925 (15) | 0.45688 (10) | 0.00391 (12) | 0.0616 (3) | |
F4 | −0.94441 (14) | 0.34878 (10) | −0.15595 (10) | 0.0478 (3) | |
F5 | −1.03193 (11) | 0.08372 (10) | −0.30475 (10) | 0.0405 (2) | |
F6 | −0.84149 (12) | −0.40038 (9) | −0.48195 (9) | 0.0390 (2) | |
F7 | −0.71620 (13) | −0.47193 (10) | −0.68451 (10) | 0.0471 (3) | |
F8 | −0.59605 (13) | −0.28018 (12) | −0.76845 (9) | 0.0486 (3) | |
F9 | −0.60839 (13) | −0.01609 (11) | −0.64533 (10) | 0.0481 (3) | |
F10 | −0.72751 (13) | 0.05909 (10) | −0.44236 (9) | 0.0421 (2) | |
F11 | −1.05289 (10) | −0.07705 (10) | −0.13716 (8) | 0.0353 (2) | |
F12 | −1.33537 (11) | −0.18062 (12) | −0.18023 (10) | 0.0487 (3) | |
F13 | −1.48775 (11) | −0.34495 (12) | −0.42282 (11) | 0.0527 (3) | |
F14 | −1.34720 (12) | −0.39914 (12) | −0.62344 (10) | 0.0521 (3) | |
F15 | −1.06742 (11) | −0.30049 (10) | −0.58448 (8) | 0.0395 (2) | |
H19A | −0.815 (2) | −0.0604 (19) | −0.0338 (17) | 0.033 (5)* | |
H21A | −1.045 (2) | −0.285 (2) | −0.1034 (19) | 0.043 (5)* | |
H19B | −0.664 (2) | −0.0921 (19) | −0.0063 (18) | 0.036 (5)* | |
H22A | −0.992 (2) | −0.3958 (19) | −0.3030 (19) | 0.038 (5)* | |
H20B | −0.761 (2) | −0.295 (2) | 0.008 (2) | 0.050 (6)* | |
H22B | −0.863 (2) | −0.446 (2) | −0.2511 (19) | 0.045 (5)* | |
H21B | −0.999 (2) | −0.417 (2) | −0.090 (2) | 0.055 (6)* | |
H20A | −0.858 (3) | −0.194 (2) | 0.082 (2) | 0.054 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.03329 (19) | 0.02845 (19) | 0.02452 (17) | 0.01169 (15) | 0.00670 (13) | 0.01057 (14) |
B1 | 0.0281 (8) | 0.0221 (7) | 0.0233 (7) | 0.0067 (6) | 0.0043 (6) | 0.0085 (6) |
C1 | 0.0317 (7) | 0.0227 (7) | 0.0236 (6) | 0.0053 (6) | 0.0077 (5) | 0.0076 (5) |
C2 | 0.0318 (8) | 0.0291 (8) | 0.0298 (7) | 0.0055 (6) | 0.0086 (6) | 0.0107 (6) |
C3 | 0.0370 (9) | 0.0316 (8) | 0.0299 (7) | −0.0070 (7) | 0.0059 (6) | 0.0065 (6) |
C4 | 0.0588 (11) | 0.0205 (7) | 0.0342 (8) | −0.0015 (7) | 0.0182 (8) | 0.0052 (6) |
C5 | 0.0513 (10) | 0.0254 (8) | 0.0359 (8) | 0.0144 (7) | 0.0218 (7) | 0.0147 (6) |
C6 | 0.0350 (8) | 0.0266 (7) | 0.0287 (7) | 0.0074 (6) | 0.0081 (6) | 0.0116 (6) |
C7 | 0.0265 (7) | 0.0275 (7) | 0.0235 (6) | 0.0074 (6) | 0.0037 (5) | 0.0093 (5) |
C8 | 0.0349 (8) | 0.0272 (8) | 0.0266 (7) | 0.0074 (6) | 0.0070 (6) | 0.0110 (6) |
C9 | 0.0387 (8) | 0.0300 (8) | 0.0266 (7) | 0.0121 (7) | 0.0069 (6) | 0.0071 (6) |
C10 | 0.0343 (8) | 0.0446 (9) | 0.0238 (7) | 0.0116 (7) | 0.0101 (6) | 0.0117 (6) |
C11 | 0.0325 (8) | 0.0379 (9) | 0.0305 (7) | 0.0053 (7) | 0.0069 (6) | 0.0178 (6) |
C12 | 0.0325 (8) | 0.0267 (7) | 0.0271 (7) | 0.0074 (6) | 0.0045 (6) | 0.0099 (6) |
C13 | 0.0290 (7) | 0.0210 (7) | 0.0269 (7) | 0.0072 (6) | 0.0044 (5) | 0.0093 (5) |
C14 | 0.0297 (7) | 0.0256 (7) | 0.0254 (7) | 0.0068 (6) | 0.0027 (6) | 0.0085 (5) |
C15 | 0.0322 (8) | 0.0332 (8) | 0.0353 (8) | 0.0105 (6) | 0.0106 (6) | 0.0140 (6) |
C16 | 0.0259 (7) | 0.0330 (8) | 0.0444 (9) | 0.0035 (6) | 0.0020 (6) | 0.0171 (7) |
C17 | 0.0341 (8) | 0.0298 (8) | 0.0308 (7) | 0.0028 (6) | −0.0039 (6) | 0.0095 (6) |
C18 | 0.0336 (8) | 0.0255 (7) | 0.0257 (7) | 0.0073 (6) | 0.0050 (6) | 0.0095 (6) |
C19 | 0.0368 (9) | 0.0368 (9) | 0.0229 (7) | 0.0104 (7) | 0.0028 (6) | 0.0094 (6) |
C20 | 0.0494 (10) | 0.0496 (11) | 0.0293 (8) | 0.0151 (8) | 0.0106 (7) | 0.0193 (7) |
C21 | 0.0501 (10) | 0.0344 (9) | 0.0384 (9) | 0.0108 (8) | 0.0147 (7) | 0.0183 (7) |
C22 | 0.0520 (10) | 0.0252 (8) | 0.0325 (8) | 0.0087 (7) | 0.0099 (7) | 0.0125 (6) |
F1 | 0.0284 (5) | 0.0405 (5) | 0.0462 (5) | 0.0061 (4) | 0.0033 (4) | 0.0141 (4) |
F2 | 0.0426 (6) | 0.0466 (6) | 0.0453 (6) | −0.0134 (5) | −0.0008 (5) | 0.0062 (5) |
F3 | 0.0843 (9) | 0.0217 (5) | 0.0568 (7) | −0.0041 (5) | 0.0205 (6) | −0.0016 (5) |
F4 | 0.0738 (8) | 0.0317 (5) | 0.0524 (6) | 0.0267 (5) | 0.0298 (5) | 0.0215 (5) |
F5 | 0.0401 (5) | 0.0336 (5) | 0.0472 (5) | 0.0133 (4) | −0.0001 (4) | 0.0165 (4) |
F6 | 0.0599 (6) | 0.0242 (5) | 0.0331 (5) | 0.0087 (4) | 0.0168 (4) | 0.0105 (4) |
F7 | 0.0681 (7) | 0.0343 (5) | 0.0374 (5) | 0.0206 (5) | 0.0205 (5) | 0.0065 (4) |
F8 | 0.0561 (7) | 0.0592 (7) | 0.0332 (5) | 0.0175 (5) | 0.0242 (5) | 0.0158 (5) |
F9 | 0.0591 (7) | 0.0482 (6) | 0.0445 (6) | 0.0063 (5) | 0.0210 (5) | 0.0271 (5) |
F10 | 0.0634 (7) | 0.0271 (5) | 0.0409 (5) | 0.0121 (5) | 0.0195 (5) | 0.0162 (4) |
F11 | 0.0339 (5) | 0.0398 (5) | 0.0240 (4) | 0.0079 (4) | 0.0056 (4) | 0.0048 (4) |
F12 | 0.0368 (5) | 0.0615 (7) | 0.0441 (6) | 0.0102 (5) | 0.0182 (4) | 0.0152 (5) |
F13 | 0.0264 (5) | 0.0612 (7) | 0.0600 (7) | −0.0001 (5) | 0.0018 (5) | 0.0203 (6) |
F14 | 0.0436 (6) | 0.0558 (7) | 0.0342 (5) | −0.0045 (5) | −0.0089 (4) | 0.0065 (5) |
F15 | 0.0413 (5) | 0.0443 (6) | 0.0226 (4) | 0.0047 (4) | 0.0049 (4) | 0.0058 (4) |
S1—C19 | 1.8261 (15) | C11—F9 | 1.3402 (19) |
S1—C22 | 1.8286 (18) | C11—C12 | 1.379 (2) |
S1—B1 | 2.0843 (16) | C12—F10 | 1.3444 (18) |
B1—C13 | 1.624 (2) | C13—C14 | 1.385 (2) |
B1—C7 | 1.628 (2) | C13—C18 | 1.386 (2) |
B1—C1 | 1.628 (2) | C14—F11 | 1.3552 (16) |
C1—C2 | 1.384 (2) | C14—C15 | 1.372 (2) |
C1—C6 | 1.384 (2) | C15—F12 | 1.3356 (18) |
C2—F1 | 1.3513 (19) | C15—C16 | 1.377 (2) |
C2—C3 | 1.374 (2) | C16—F13 | 1.3314 (19) |
C3—F2 | 1.337 (2) | C16—C17 | 1.367 (2) |
C3—C4 | 1.368 (3) | C17—F14 | 1.3341 (17) |
C4—F3 | 1.3338 (18) | C17—C18 | 1.382 (2) |
C4—C5 | 1.371 (3) | C18—F15 | 1.3435 (17) |
C5—F4 | 1.341 (2) | C19—C20 | 1.520 (3) |
C5—C6 | 1.377 (2) | C19—H19A | 0.957 (19) |
C6—F5 | 1.3438 (18) | C19—H19B | 0.95 (2) |
C7—C12 | 1.384 (2) | C20—C21 | 1.512 (3) |
C7—C8 | 1.389 (2) | C20—H20B | 1.02 (2) |
C8—F6 | 1.3532 (18) | C20—H20A | 0.97 (2) |
C8—C9 | 1.371 (2) | C21—C22 | 1.515 (2) |
C9—F7 | 1.3379 (18) | C21—H21A | 1.02 (2) |
C9—C10 | 1.369 (2) | C21—H21B | 0.96 (2) |
C10—F8 | 1.3360 (18) | C22—H22A | 0.944 (19) |
C10—C11 | 1.370 (2) | C22—H22B | 0.99 (2) |
C19—S1—C22 | 94.25 (8) | C11—C12—C7 | 123.99 (14) |
C19—S1—B1 | 111.20 (7) | C14—C13—C18 | 112.81 (13) |
C22—S1—B1 | 109.36 (8) | C14—C13—B1 | 121.35 (12) |
C13—B1—C7 | 115.42 (12) | C18—C13—B1 | 125.84 (13) |
C13—B1—C1 | 113.86 (12) | F11—C14—C15 | 115.46 (13) |
C7—B1—C1 | 112.10 (12) | F11—C14—C13 | 119.28 (13) |
C13—B1—S1 | 106.45 (10) | C15—C14—C13 | 125.26 (14) |
C7—B1—S1 | 101.67 (9) | F12—C15—C14 | 120.90 (14) |
C1—B1—S1 | 105.93 (9) | F12—C15—C16 | 120.05 (15) |
C2—C1—C6 | 113.46 (13) | C14—C15—C16 | 119.05 (15) |
C2—C1—B1 | 123.53 (13) | F13—C16—C17 | 121.18 (15) |
C6—C1—B1 | 122.91 (13) | F13—C16—C15 | 119.97 (16) |
F1—C2—C3 | 115.95 (14) | C17—C16—C15 | 118.85 (15) |
F1—C2—C1 | 119.45 (13) | F14—C17—C16 | 119.96 (15) |
C3—C2—C1 | 124.60 (15) | F14—C17—C18 | 120.18 (15) |
F2—C3—C4 | 120.25 (15) | C16—C17—C18 | 119.86 (14) |
F2—C3—C2 | 120.57 (16) | F15—C18—C17 | 114.62 (13) |
C4—C3—C2 | 119.18 (15) | F15—C18—C13 | 121.23 (14) |
F3—C4—C3 | 120.67 (17) | C17—C18—C13 | 124.14 (14) |
F3—C4—C5 | 120.35 (17) | C20—C19—S1 | 104.94 (11) |
C3—C4—C5 | 118.98 (14) | C20—C19—H19A | 113.0 (11) |
F4—C5—C4 | 119.83 (15) | S1—C19—H19A | 108.1 (11) |
F4—C5—C6 | 120.27 (16) | C20—C19—H19B | 112.4 (11) |
C4—C5—C6 | 119.89 (16) | S1—C19—H19B | 107.7 (11) |
F5—C6—C5 | 115.70 (14) | H19A—C19—H19B | 110.4 (16) |
F5—C6—C1 | 120.55 (13) | C21—C20—C19 | 107.86 (14) |
C5—C6—C1 | 123.74 (15) | C21—C20—H20B | 108.3 (12) |
C12—C7—C8 | 113.03 (13) | C19—C20—H20B | 108.9 (13) |
C12—C7—B1 | 124.58 (13) | C21—C20—H20A | 112.8 (14) |
C8—C7—B1 | 122.36 (13) | C19—C20—H20A | 109.2 (13) |
F6—C8—C9 | 116.14 (13) | H20B—C20—H20A | 109.7 (17) |
F6—C8—C7 | 118.89 (13) | C20—C21—C22 | 106.77 (15) |
C9—C8—C7 | 124.94 (15) | C20—C21—H21A | 109.5 (11) |
F7—C9—C10 | 120.00 (14) | C22—C21—H21A | 110.2 (11) |
F7—C9—C8 | 120.83 (15) | C20—C21—H21B | 110.9 (13) |
C10—C9—C8 | 119.17 (15) | C22—C21—H21B | 109.8 (13) |
F8—C10—C9 | 120.74 (15) | H21A—C21—H21B | 109.7 (18) |
F8—C10—C11 | 120.26 (15) | C21—C22—S1 | 107.10 (12) |
C9—C10—C11 | 119.00 (14) | C21—C22—H22A | 113.5 (12) |
F9—C11—C10 | 119.72 (14) | S1—C22—H22A | 109.3 (12) |
F9—C11—C12 | 120.42 (15) | C21—C22—H22B | 114.5 (12) |
C10—C11—C12 | 119.86 (15) | S1—C22—H22B | 102.3 (12) |
F10—C12—C11 | 114.91 (14) | H22A—C22—H22B | 109.4 (16) |
F10—C12—C7 | 121.08 (13) | ||
C19—S1—B1—C13 | −89.32 (11) | F7—C9—C10—C11 | 179.16 (14) |
C22—S1—B1—C13 | 13.42 (11) | C8—C9—C10—C11 | −0.6 (2) |
C19—S1—B1—C7 | 149.48 (10) | F8—C10—C11—F9 | 1.5 (2) |
C22—S1—B1—C7 | −107.78 (10) | C9—C10—C11—F9 | −178.39 (14) |
C19—S1—B1—C1 | 32.20 (12) | F8—C10—C11—C12 | −179.17 (14) |
C22—S1—B1—C1 | 134.94 (10) | C9—C10—C11—C12 | 1.0 (2) |
C13—B1—C1—C2 | 155.39 (14) | F9—C11—C12—F10 | 0.4 (2) |
C7—B1—C1—C2 | −71.29 (18) | C10—C11—C12—F10 | −178.95 (14) |
S1—B1—C1—C2 | 38.76 (17) | F9—C11—C12—C7 | 178.82 (14) |
C13—B1—C1—C6 | −28.42 (19) | C10—C11—C12—C7 | −0.5 (2) |
C7—B1—C1—C6 | 104.91 (16) | C8—C7—C12—F10 | 178.05 (13) |
S1—B1—C1—C6 | −145.04 (13) | B1—C7—C12—F10 | 0.0 (2) |
C6—C1—C2—F1 | −175.64 (13) | C8—C7—C12—C11 | −0.3 (2) |
B1—C1—C2—F1 | 0.9 (2) | B1—C7—C12—C11 | −178.31 (14) |
C6—C1—C2—C3 | 4.5 (2) | C7—B1—C13—C14 | −179.96 (13) |
B1—C1—C2—C3 | −179.02 (14) | C1—B1—C13—C14 | −48.23 (18) |
F1—C2—C3—F2 | −3.3 (2) | S1—B1—C13—C14 | 68.09 (15) |
C1—C2—C3—F2 | 176.59 (14) | C7—B1—C13—C18 | −0.4 (2) |
F1—C2—C3—C4 | 176.46 (14) | C1—B1—C13—C18 | 131.32 (15) |
C1—C2—C3—C4 | −3.6 (3) | S1—B1—C13—C18 | −112.36 (14) |
F2—C3—C4—F3 | 0.0 (3) | C18—C13—C14—F11 | −177.09 (13) |
C2—C3—C4—F3 | −179.76 (15) | B1—C13—C14—F11 | 2.5 (2) |
F2—C3—C4—C5 | −179.90 (15) | C18—C13—C14—C15 | 2.0 (2) |
C2—C3—C4—C5 | 0.3 (2) | B1—C13—C14—C15 | −178.36 (14) |
F3—C4—C5—F4 | 1.6 (2) | F11—C14—C15—F12 | −1.4 (2) |
C3—C4—C5—F4 | −178.48 (15) | C13—C14—C15—F12 | 179.44 (14) |
F3—C4—C5—C6 | −178.25 (15) | F11—C14—C15—C16 | 178.33 (14) |
C3—C4—C5—C6 | 1.7 (2) | C13—C14—C15—C16 | −0.8 (3) |
F4—C5—C6—F5 | 1.0 (2) | F12—C15—C16—F13 | −0.7 (2) |
C4—C5—C6—F5 | −179.17 (14) | C14—C15—C16—F13 | 179.56 (15) |
F4—C5—C6—C1 | 179.54 (14) | F12—C15—C16—C17 | 178.91 (15) |
C4—C5—C6—C1 | −0.6 (2) | C14—C15—C16—C17 | −0.8 (2) |
C2—C1—C6—F5 | 176.19 (13) | F13—C16—C17—F14 | 1.3 (3) |
B1—C1—C6—F5 | −0.4 (2) | C15—C16—C17—F14 | −178.29 (15) |
C2—C1—C6—C5 | −2.3 (2) | F13—C16—C17—C18 | −179.34 (15) |
B1—C1—C6—C5 | −178.84 (14) | C15—C16—C17—C18 | 1.1 (2) |
C13—B1—C7—C12 | 110.83 (16) | F14—C17—C18—F15 | 0.7 (2) |
C1—B1—C7—C12 | −21.72 (19) | C16—C17—C18—F15 | −178.61 (14) |
S1—B1—C7—C12 | −134.45 (13) | F14—C17—C18—C13 | 179.67 (14) |
C13—B1—C7—C8 | −67.01 (18) | C16—C17—C18—C13 | 0.3 (3) |
C1—B1—C7—C8 | 160.43 (13) | C14—C13—C18—F15 | 177.10 (13) |
S1—B1—C7—C8 | 47.71 (16) | B1—C13—C18—F15 | −2.5 (2) |
C12—C7—C8—F6 | −177.62 (13) | C14—C13—C18—C17 | −1.8 (2) |
B1—C7—C8—F6 | 0.5 (2) | B1—C13—C18—C17 | 178.65 (15) |
C12—C7—C8—C9 | 0.7 (2) | C22—S1—C19—C20 | 17.15 (13) |
B1—C7—C8—C9 | 178.76 (14) | B1—S1—C19—C20 | 129.82 (12) |
F6—C8—C9—F7 | −1.7 (2) | S1—C19—C20—C21 | −39.16 (17) |
C7—C8—C9—F7 | 179.98 (14) | C19—C20—C21—C22 | 47.13 (19) |
F6—C8—C9—C10 | 178.08 (14) | C20—C21—C22—S1 | −32.46 (17) |
C7—C8—C9—C10 | −0.3 (3) | C19—S1—C22—C21 | 8.66 (14) |
F7—C9—C10—F8 | −0.7 (2) | B1—S1—C22—C21 | −105.57 (13) |
C8—C9—C10—F8 | 179.55 (14) |
Experimental details
Crystal data | |
Chemical formula | C22H8BF15S |
Mr | 600.15 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 230 |
a, b, c (Å) | 9.5892 (8), 10.8264 (10), 11.3959 (9) |
α, β, γ (°) | 111.904 (6), 96.814 (7), 100.727 (7) |
V (Å3) | 1055.29 (16) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.30 |
Crystal size (mm) | 0.6 × 0.5 × 0.3 |
Data collection | |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7694, 4359, 3938 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.031, 0.083, 1.05 |
No. of reflections | 4359 |
No. of parameters | 384 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.28, −0.24 |
Computer programs: XSCANS (Siemens, 1992), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1991), SHELXL97.
S1—C19 | 1.8261 (15) | B1—C13 | 1.624 (2) |
S1—C22 | 1.8286 (18) | B1—C7 | 1.628 (2) |
S1—B1 | 2.0843 (16) | B1—C1 | 1.628 (2) |
C13—B1—C7 | 115.42 (12) | C13—B1—S1 | 106.45 (10) |
C13—B1—C1 | 113.86 (12) | C7—B1—S1 | 101.67 (9) |
C7—B1—C1 | 112.10 (12) | C1—B1—S1 | 105.93 (9) |
As a part of our investigations on the displacement of methylborate anions from zirconocene contact ion pairs, we have investigated the coordination of Lewis bases to tris(pentafluorophenyl)borane for comparison. Single crystals of a Lewis base–Lewis acid adduct of tetrahydrothiophene and tris(pentafluorophenyl)borane were obtained by slow evaporation of a toluene solution containing the Lewis base and the Lewis acid in a ratio of approximately 1:1.
Bond distances and angles of the boron–aryl fragment [dB,C = 1.624 (2)–1.628 (2) Å, αC,B,S = 101.67 (9)–106.45 (10)°] are comparable to those found for uncoordinated methylborate anions MeB(C6F5)3- [dB,C = 1.60–1.73 Å, αC,B,Me = 101–116° (CCSD; Allen et al., 1993): BIQREY, BIQREY, CACVEH, CACVOR, CACWAE, CACXIN, CEWFAL, CEWFOZ, FEQDAG, GEGYUM, GEHFAA, GUCXAD, HIMJOC, HIWQIN, HOHYUY, KICYEA, NUWWIL, NUWWOR, POQVEW, POWTUQ, POWVAY, POZWIK, QAPGET, QAPGIX, QAPGOD, QAWZIX, QEMWUA, REZBIH, RIDYOS, RIDYUY, RIRLEJ, TOPBUV, WEMLAB, WEYHAJ, WILQAJ, WILQEN, WORJOC, WORJUI, WORKAP, YEKLEF, YUVPAG, ZAFQAY]. The boron–sulfur distance of 2.0843 (16) Å is the longest observed so far for the coordination of a thioether to a Lewis acidic boron centre [dB,S = 1.82–2.07 Å, 54 structures in the CCSD (Allen et al., 1993): BEGYIV, BUPBOD, CAFNUS, CHMSDB, CONBEM, DIMBEG10, DIMBOQ10, DONXIN, FEBROT, FIJNIV, FIJNOB, FIJPAP, GALZEY, GAMBUR, GAMGOQ, GAMHIL, GAMHUX, GICDIF, GICDOL, JESWIN, KOMZAN, MOMSHB, NAQPIE, NEDLAJ, NITWUI, NITXAP, NORNEN, NUHCOI, NUHCUO, NUHDAV, PIBXED, PIBXIH, PIJTUX, PUCNAC, PUCNEG, RUHBOR, SOGMAC, TAJBEL, TAJBIP, TOJXUL, TOJYAS, TOJYEW, VEMVIS, VUYHIG, WARGAX, WARGEB, WARGIF, WICHAR, WICHEV, YAKCOC, YEDHUK, ZEJCAS, ZEKQEL, ZONVAZ], most probably due to the sterically demanding pentafluorophenyl substituents.