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Acta Cryst. (2002). E58, o77-o78
https://doi.org/10.1107/S160053680102027X
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Tetra­hydro­thio­phene tris­(penta­fluoro­phenyl)­borane

F. Schaper and H.-H. Brintzinger
In the title compound, (C4H8S)B(C6F5)3, a comparatively long boron-sulfur distance of 2.0843 (16) Å is found, most probably due to the sterically demanding penta­fluoro­phenyl­substituents. Bond distances and angles of the boron-aryl fragment are comparable to those found for uncoordinated MeB(C6F5)3- anions.
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Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680102027X/ob6091sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680102027X/ob6091Isup2.hkl
Contains datablock I

CCDC reference: 180554

checkCIF report

Key indicators

  • Single-crystal X-ray study
  • T = 230 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.031
  • wR factor = 0.083
  • Data-to-parameter ratio = 11.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:



REFLT_03
         From the CIF: _diffrn_reflns_theta_max           27.00
         From the CIF: _reflns_number_total               4359
         TEST2: Reflns within _diffrn_reflns_theta_max
         Count of symmetry unique reflns         4609
         Completeness (_total/calc)             94.58%
          Alert C: < 95% complete


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check
Comment top

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.

Experimental top

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).

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] Fig. 1. View of the title compound showing the labelling of non-H atoms. Displacement ellipsoids are shown at the 50% probability level.
(I) top
Crystal data top
C22H8BF15SZ = 2
Mr = 600.15F(000) = 592
Triclinic, P1Dx = 1.889 Mg m−3
a = 9.5892 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.8264 (10) ÅCell parameters from 42 reflections
c = 11.3959 (9) Åθ = 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) Å30.6 × 0.5 × 0.3 mm
Data collection top
Siemens P4
diffractometer		Rint = 0.034
Radiation source: fine-focus sealed tubeθmax = 27.0°, θmin = 2.0°
Graphite monochromatorh = −10→12
ω scansk = −12→12
7694 measured reflectionsl = −14→14
4359 independent reflections3 standard reflections every 97 reflections
3938 reflections with I > 2σ(I) intensity decay: 1.8%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: difference Fourier map
wR(F2) = 0.083All 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 parametersΔρmax = 0.28 e Å−3
0 restraintsΔρmin = −0.24 e Å−3
Crystal data top
C22H8BF15Sγ = 100.727 (7)°
Mr = 600.15V = 1055.29 (16) Å3
Triclinic, P1Z = 2
a = 9.5892 (8) ÅMo Kα radiation
b = 10.8264 (10) ŵ = 0.30 mm−1
c = 11.3959 (9) ÅT = 230 K
α = 111.904 (6)°0.6 × 0.5 × 0.3 mm
β = 96.814 (7)°
Data collection top
Siemens P4
diffractometer		Rint = 0.034
7694 measured reflections3 standard reflections every 97 reflections
4359 independent reflections intensity decay: 1.8%
3938 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.083All H-atom parameters refined
S = 1.05Δρmax = 0.28 e Å−3
4359 reflectionsΔρmin = −0.24 e Å−3
384 parameters
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
xyzUiso*/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)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.03329 (19)0.02845 (19)0.02452 (17)0.01169 (15)0.00670 (13)0.01057 (14)
B10.0281 (8)0.0221 (7)0.0233 (7)0.0067 (6)0.0043 (6)0.0085 (6)
C10.0317 (7)0.0227 (7)0.0236 (6)0.0053 (6)0.0077 (5)0.0076 (5)
C20.0318 (8)0.0291 (8)0.0298 (7)0.0055 (6)0.0086 (6)0.0107 (6)
C30.0370 (9)0.0316 (8)0.0299 (7)−0.0070 (7)0.0059 (6)0.0065 (6)
C40.0588 (11)0.0205 (7)0.0342 (8)−0.0015 (7)0.0182 (8)0.0052 (6)
C50.0513 (10)0.0254 (8)0.0359 (8)0.0144 (7)0.0218 (7)0.0147 (6)
C60.0350 (8)0.0266 (7)0.0287 (7)0.0074 (6)0.0081 (6)0.0116 (6)
C70.0265 (7)0.0275 (7)0.0235 (6)0.0074 (6)0.0037 (5)0.0093 (5)
C80.0349 (8)0.0272 (8)0.0266 (7)0.0074 (6)0.0070 (6)0.0110 (6)
C90.0387 (8)0.0300 (8)0.0266 (7)0.0121 (7)0.0069 (6)0.0071 (6)
C100.0343 (8)0.0446 (9)0.0238 (7)0.0116 (7)0.0101 (6)0.0117 (6)
C110.0325 (8)0.0379 (9)0.0305 (7)0.0053 (7)0.0069 (6)0.0178 (6)
C120.0325 (8)0.0267 (7)0.0271 (7)0.0074 (6)0.0045 (6)0.0099 (6)
C130.0290 (7)0.0210 (7)0.0269 (7)0.0072 (6)0.0044 (5)0.0093 (5)
C140.0297 (7)0.0256 (7)0.0254 (7)0.0068 (6)0.0027 (6)0.0085 (5)
C150.0322 (8)0.0332 (8)0.0353 (8)0.0105 (6)0.0106 (6)0.0140 (6)
C160.0259 (7)0.0330 (8)0.0444 (9)0.0035 (6)0.0020 (6)0.0171 (7)
C170.0341 (8)0.0298 (8)0.0308 (7)0.0028 (6)−0.0039 (6)0.0095 (6)
C180.0336 (8)0.0255 (7)0.0257 (7)0.0073 (6)0.0050 (6)0.0095 (6)
C190.0368 (9)0.0368 (9)0.0229 (7)0.0104 (7)0.0028 (6)0.0094 (6)
C200.0494 (10)0.0496 (11)0.0293 (8)0.0151 (8)0.0106 (7)0.0193 (7)
C210.0501 (10)0.0344 (9)0.0384 (9)0.0108 (8)0.0147 (7)0.0183 (7)
C220.0520 (10)0.0252 (8)0.0325 (8)0.0087 (7)0.0099 (7)0.0125 (6)
F10.0284 (5)0.0405 (5)0.0462 (5)0.0061 (4)0.0033 (4)0.0141 (4)
F20.0426 (6)0.0466 (6)0.0453 (6)−0.0134 (5)−0.0008 (5)0.0062 (5)
F30.0843 (9)0.0217 (5)0.0568 (7)−0.0041 (5)0.0205 (6)−0.0016 (5)
F40.0738 (8)0.0317 (5)0.0524 (6)0.0267 (5)0.0298 (5)0.0215 (5)
F50.0401 (5)0.0336 (5)0.0472 (5)0.0133 (4)−0.0001 (4)0.0165 (4)
F60.0599 (6)0.0242 (5)0.0331 (5)0.0087 (4)0.0168 (4)0.0105 (4)
F70.0681 (7)0.0343 (5)0.0374 (5)0.0206 (5)0.0205 (5)0.0065 (4)
F80.0561 (7)0.0592 (7)0.0332 (5)0.0175 (5)0.0242 (5)0.0158 (5)
F90.0591 (7)0.0482 (6)0.0445 (6)0.0063 (5)0.0210 (5)0.0271 (5)
F100.0634 (7)0.0271 (5)0.0409 (5)0.0121 (5)0.0195 (5)0.0162 (4)
F110.0339 (5)0.0398 (5)0.0240 (4)0.0079 (4)0.0056 (4)0.0048 (4)
F120.0368 (5)0.0615 (7)0.0441 (6)0.0102 (5)0.0182 (4)0.0152 (5)
F130.0264 (5)0.0612 (7)0.0600 (7)−0.0001 (5)0.0018 (5)0.0203 (6)
F140.0436 (6)0.0558 (7)0.0342 (5)−0.0045 (5)−0.0089 (4)0.0065 (5)
F150.0413 (5)0.0443 (6)0.0226 (4)0.0047 (4)0.0049 (4)0.0058 (4)
Geometric parameters (Å, º) top
S1—C191.8261 (15)C11—F91.3402 (19)
S1—C221.8286 (18)C11—C121.379 (2)
S1—B12.0843 (16)C12—F101.3444 (18)
B1—C131.624 (2)C13—C141.385 (2)
B1—C71.628 (2)C13—C181.386 (2)
B1—C11.628 (2)C14—F111.3552 (16)
C1—C21.384 (2)C14—C151.372 (2)
C1—C61.384 (2)C15—F121.3356 (18)
C2—F11.3513 (19)C15—C161.377 (2)
C2—C31.374 (2)C16—F131.3314 (19)
C3—F21.337 (2)C16—C171.367 (2)
C3—C41.368 (3)C17—F141.3341 (17)
C4—F31.3338 (18)C17—C181.382 (2)
C4—C51.371 (3)C18—F151.3435 (17)
C5—F41.341 (2)C19—C201.520 (3)
C5—C61.377 (2)C19—H19A0.957 (19)
C6—F51.3438 (18)C19—H19B0.95 (2)
C7—C121.384 (2)C20—C211.512 (3)
C7—C81.389 (2)C20—H20B1.02 (2)
C8—F61.3532 (18)C20—H20A0.97 (2)
C8—C91.371 (2)C21—C221.515 (2)
C9—F71.3379 (18)C21—H21A1.02 (2)
C9—C101.369 (2)C21—H21B0.96 (2)
C10—F81.3360 (18)C22—H22A0.944 (19)
C10—C111.370 (2)C22—H22B0.99 (2)
C19—S1—C2294.25 (8)C11—C12—C7123.99 (14)
C19—S1—B1111.20 (7)C14—C13—C18112.81 (13)
C22—S1—B1109.36 (8)C14—C13—B1121.35 (12)
C13—B1—C7115.42 (12)C18—C13—B1125.84 (13)
C13—B1—C1113.86 (12)F11—C14—C15115.46 (13)
C7—B1—C1112.10 (12)F11—C14—C13119.28 (13)
C13—B1—S1106.45 (10)C15—C14—C13125.26 (14)
C7—B1—S1101.67 (9)F12—C15—C14120.90 (14)
C1—B1—S1105.93 (9)F12—C15—C16120.05 (15)
C2—C1—C6113.46 (13)C14—C15—C16119.05 (15)
C2—C1—B1123.53 (13)F13—C16—C17121.18 (15)
C6—C1—B1122.91 (13)F13—C16—C15119.97 (16)
F1—C2—C3115.95 (14)C17—C16—C15118.85 (15)
F1—C2—C1119.45 (13)F14—C17—C16119.96 (15)
C3—C2—C1124.60 (15)F14—C17—C18120.18 (15)
F2—C3—C4120.25 (15)C16—C17—C18119.86 (14)
F2—C3—C2120.57 (16)F15—C18—C17114.62 (13)
C4—C3—C2119.18 (15)F15—C18—C13121.23 (14)
F3—C4—C3120.67 (17)C17—C18—C13124.14 (14)
F3—C4—C5120.35 (17)C20—C19—S1104.94 (11)
C3—C4—C5118.98 (14)C20—C19—H19A113.0 (11)
F4—C5—C4119.83 (15)S1—C19—H19A108.1 (11)
F4—C5—C6120.27 (16)C20—C19—H19B112.4 (11)
C4—C5—C6119.89 (16)S1—C19—H19B107.7 (11)
F5—C6—C5115.70 (14)H19A—C19—H19B110.4 (16)
F5—C6—C1120.55 (13)C21—C20—C19107.86 (14)
C5—C6—C1123.74 (15)C21—C20—H20B108.3 (12)
C12—C7—C8113.03 (13)C19—C20—H20B108.9 (13)
C12—C7—B1124.58 (13)C21—C20—H20A112.8 (14)
C8—C7—B1122.36 (13)C19—C20—H20A109.2 (13)
F6—C8—C9116.14 (13)H20B—C20—H20A109.7 (17)
F6—C8—C7118.89 (13)C20—C21—C22106.77 (15)
C9—C8—C7124.94 (15)C20—C21—H21A109.5 (11)
F7—C9—C10120.00 (14)C22—C21—H21A110.2 (11)
F7—C9—C8120.83 (15)C20—C21—H21B110.9 (13)
C10—C9—C8119.17 (15)C22—C21—H21B109.8 (13)
F8—C10—C9120.74 (15)H21A—C21—H21B109.7 (18)
F8—C10—C11120.26 (15)C21—C22—S1107.10 (12)
C9—C10—C11119.00 (14)C21—C22—H22A113.5 (12)
F9—C11—C10119.72 (14)S1—C22—H22A109.3 (12)
F9—C11—C12120.42 (15)C21—C22—H22B114.5 (12)
C10—C11—C12119.86 (15)S1—C22—H22B102.3 (12)
F10—C12—C11114.91 (14)H22A—C22—H22B109.4 (16)
F10—C12—C7121.08 (13)
C19—S1—B1—C13−89.32 (11)F7—C9—C10—C11179.16 (14)
C22—S1—B1—C1313.42 (11)C8—C9—C10—C11−0.6 (2)
C19—S1—B1—C7149.48 (10)F8—C10—C11—F91.5 (2)
C22—S1—B1—C7−107.78 (10)C9—C10—C11—F9−178.39 (14)
C19—S1—B1—C132.20 (12)F8—C10—C11—C12−179.17 (14)
C22—S1—B1—C1134.94 (10)C9—C10—C11—C121.0 (2)
C13—B1—C1—C2155.39 (14)F9—C11—C12—F100.4 (2)
C7—B1—C1—C2−71.29 (18)C10—C11—C12—F10−178.95 (14)
S1—B1—C1—C238.76 (17)F9—C11—C12—C7178.82 (14)
C13—B1—C1—C6−28.42 (19)C10—C11—C12—C7−0.5 (2)
C7—B1—C1—C6104.91 (16)C8—C7—C12—F10178.05 (13)
S1—B1—C1—C6−145.04 (13)B1—C7—C12—F100.0 (2)
C6—C1—C2—F1−175.64 (13)C8—C7—C12—C11−0.3 (2)
B1—C1—C2—F10.9 (2)B1—C7—C12—C11−178.31 (14)
C6—C1—C2—C34.5 (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—C1468.09 (15)
C1—C2—C3—F2176.59 (14)C7—B1—C13—C18−0.4 (2)
F1—C2—C3—C4176.46 (14)C1—B1—C13—C18131.32 (15)
C1—C2—C3—C4−3.6 (3)S1—B1—C13—C18−112.36 (14)
F2—C3—C4—F30.0 (3)C18—C13—C14—F11−177.09 (13)
C2—C3—C4—F3−179.76 (15)B1—C13—C14—F112.5 (2)
F2—C3—C4—C5−179.90 (15)C18—C13—C14—C152.0 (2)
C2—C3—C4—C50.3 (2)B1—C13—C14—C15−178.36 (14)
F3—C4—C5—F41.6 (2)F11—C14—C15—F12−1.4 (2)
C3—C4—C5—F4−178.48 (15)C13—C14—C15—F12179.44 (14)
F3—C4—C5—C6−178.25 (15)F11—C14—C15—C16178.33 (14)
C3—C4—C5—C61.7 (2)C13—C14—C15—C16−0.8 (3)
F4—C5—C6—F51.0 (2)F12—C15—C16—F13−0.7 (2)
C4—C5—C6—F5−179.17 (14)C14—C15—C16—F13179.56 (15)
F4—C5—C6—C1179.54 (14)F12—C15—C16—C17178.91 (15)
C4—C5—C6—C1−0.6 (2)C14—C15—C16—C17−0.8 (2)
C2—C1—C6—F5176.19 (13)F13—C16—C17—F141.3 (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—C181.1 (2)
C13—B1—C7—C12110.83 (16)F14—C17—C18—F150.7 (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—C13179.67 (14)
C13—B1—C7—C8−67.01 (18)C16—C17—C18—C130.3 (3)
C1—B1—C7—C8160.43 (13)C14—C13—C18—F15177.10 (13)
S1—B1—C7—C847.71 (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—F60.5 (2)B1—C13—C18—C17178.65 (15)
C12—C7—C8—C90.7 (2)C22—S1—C19—C2017.15 (13)
B1—C7—C8—C9178.76 (14)B1—S1—C19—C20129.82 (12)
F6—C8—C9—F7−1.7 (2)S1—C19—C20—C21−39.16 (17)
C7—C8—C9—F7179.98 (14)C19—C20—C21—C2247.13 (19)
F6—C8—C9—C10178.08 (14)C20—C21—C22—S1−32.46 (17)
C7—C8—C9—C10−0.3 (3)C19—S1—C22—C218.66 (14)
F7—C9—C10—F8−0.7 (2)B1—S1—C22—C21−105.57 (13)
C8—C9—C10—F8179.55 (14)

Experimental details

Crystal data
Chemical formulaC22H8BF15S
Mr600.15
Crystal system, space groupTriclinic, 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)
Z2
Radiation typeMo Kα
µ (mm−1)0.30
Crystal size (mm)0.6 × 0.5 × 0.3
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correction–
No. of measured, independent and
observed [I > 2σ(I)] reflections		7694, 4359, 3938
Rint0.034
(sin θ/λ)max (Å−1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.083, 1.05
No. of reflections4359
No. of parameters384
H-atom treatmentAll 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.

Selected geometric parameters (Å, º) top
S1—C191.8261 (15)B1—C131.624 (2)
S1—C221.8286 (18)B1—C71.628 (2)
S1—B12.0843 (16)B1—C11.628 (2)
C13—B1—C7115.42 (12)C13—B1—S1106.45 (10)
C13—B1—C1113.86 (12)C7—B1—S1101.67 (9)
C7—B1—C1112.10 (12)C1—B1—S1105.93 (9)
 

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