The title compound, C18H2BF15O·H2O·C2H6O2, obtained by crystallization of a product formed from a reaction mixture containing B(C6F5)3 and Me2SO2 (and H2O) in hexane, was characterized in the solid state as a supramolecular assembly containing water adducts of tris(pentafluorophenyl)borane, (H2O)B(C6F5)3, linked together by a network of hydrogen bonds involving one additional H2O and one additional Me2SO2 molecule per adduct molecule.
Supporting information
CCDC reference: 222893
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.002 Å
- R factor = 0.035
- wR factor = 0.095
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.99
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.05
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........ O1
PLAT431_ALERT_2_C Short Inter HL..A Contact F15 .. O2 = 2.92 Ang.
Alert level G
ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be
replaced by the scaled T values. Since the ratio of scaled T's
is identical to the ratio of reported T values, the scaling
does not imply a change to the absorption corrections used in
the study.
Ratio of Tmax expected/reported 1.051
Tmax scaled 0.972 Tmin scaled 0.837
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
6 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
2 ALERT type 2 Indicator that the structure model may be wrong or deficient
2 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
To a stirred solution of B(B6F5)3 (0.25 g, 0.48 mmol) in hexane was added Me2SO2 (0.12 g, 0.48 mmol). The product, (C6F5)3B(H2O)·Me2SO2·H2O, precipitated out of the reaction mixture as a white solid (0.21; 67%). M.p. 336 K. NMR (δ/p.p.m.; CDCl3/RT): 1H (250 MHz): 2.98 (s, 6H), 5.97 (br, s, 4H); 11B 80.2 MHz: −0.6; IR (KBr disc, \vmax)/cm−1): 3,500 (br), 3020 (w) 2940 (w), 1648 (s), 1519 (s) 1460 (s), 1279 (s), 1144 (s), 1098 (s), 977 (s), 935 (m), 764 (m), 680 (m). Elemental analysis required for C20H10BF15SO4: C 37.4, H 1.6%; found: C 37.7, H 1.0%. A single-crystal suitable for X-ray diffraction was grown by diffusion of hexane into a CHCl3 solution of the adduct.
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2002).
Crystal data top
C18H2BF15O·H2O·C2H6O2S | Z = 2 |
Mr = 642.15 | F(000) = 636 |
Triclinic, P1 | Dx = 1.836 Mg m−3 |
a = 10.357 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.397 (2) Å | Cell parameters from 28129 reflections |
c = 11.671 (2) Å | θ = 1–27.5° |
α = 77.76 (3)° | µ = 0.29 mm−1 |
β = 71.14 (3)° | T = 150 K |
γ = 83.95 (3)° | Block, colourless |
V = 1161.4 (4) Å3 | 0.5 × 0.3 × 0.1 mm |
Data collection top
Bruker–Nonius KappaCCD area-detector diffractometer | 5282 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 4488 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.3° |
ϕ and ω scans | h = −13→13 |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | k = −13→13 |
Tmin = 0.796, Tmax = 0.924 | l = −14→15 |
21780 measured reflections | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0521P)2 + 0.3645P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.035 | (Δ/σ)max = 0.007 |
wR(F2) = 0.096 | Δρmax = 0.31 e Å−3 |
S = 1.03 | Δρmin = −0.35 e Å−3 |
5282 reflections | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
389 parameters | Extinction coefficient: 0.053 (3) |
0 restraints | |
Crystal data top
C18H2BF15O·H2O·C2H6O2S | γ = 83.95 (3)° |
Mr = 642.15 | V = 1161.4 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.357 (2) Å | Mo Kα radiation |
b = 10.397 (2) Å | µ = 0.29 mm−1 |
c = 11.671 (2) Å | T = 150 K |
α = 77.76 (3)° | 0.5 × 0.3 × 0.1 mm |
β = 71.14 (3)° | |
Data collection top
Bruker–Nonius KappaCCD area-detector diffractometer | 5282 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1997) | 4488 reflections with I > 2σ(I) |
Tmin = 0.796, Tmax = 0.924 | Rint = 0.048 |
21780 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.035 | 0 restraints |
wR(F2) = 0.096 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.31 e Å−3 |
5282 reflections | Δρmin = −0.35 e Å−3 |
389 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C19 | 0.2625 (2) | 0.8571 (2) | 0.70859 (17) | 0.0413 (5) | |
H19A | 0.1842 | 0.898 | 0.6827 | 0.062* | |
H19B | 0.2704 | 0.7631 | 0.705 | 0.062* | |
H19C | 0.3461 | 0.8997 | 0.6534 | 0.062* | |
C20 | 0.08256 (18) | 0.80419 (19) | 0.94796 (19) | 0.0386 (4) | |
H20A | 0.0597 | 0.8171 | 1.0332 | 0.058* | |
H20B | 0.09 | 0.7097 | 0.9468 | 0.058* | |
H20C | 0.0107 | 0.8459 | 0.913 | 0.058* | |
O1 | 0.45265 (11) | 0.69772 (10) | 0.08847 (9) | 0.0191 (2) | |
O2 | 0.34720 (11) | 0.80142 (11) | 0.90083 (10) | 0.0285 (3) | |
O3 | 0.22508 (13) | 1.01449 (11) | 0.86389 (11) | 0.0333 (3) | |
C1 | 0.36419 (14) | 0.48334 (14) | 0.23435 (13) | 0.0185 (3) | |
C2 | 0.27463 (14) | 0.46974 (14) | 0.17163 (13) | 0.0204 (3) | |
C3 | 0.23443 (15) | 0.34963 (15) | 0.16471 (14) | 0.0243 (3) | |
C4 | 0.28174 (15) | 0.23669 (15) | 0.22583 (14) | 0.0254 (3) | |
C5 | 0.36667 (16) | 0.24418 (14) | 0.29350 (14) | 0.0245 (3) | |
C6 | 0.40556 (14) | 0.36611 (14) | 0.29685 (13) | 0.0214 (3) | |
C7 | 0.55347 (14) | 0.63743 (13) | 0.25742 (12) | 0.0184 (3) | |
C8 | 0.66924 (15) | 0.56870 (14) | 0.19553 (13) | 0.0200 (3) | |
C9 | 0.79759 (15) | 0.57691 (15) | 0.20311 (14) | 0.0233 (3) | |
C10 | 0.81640 (15) | 0.65633 (16) | 0.27630 (14) | 0.0262 (3) | |
C11 | 0.70654 (16) | 0.72675 (15) | 0.33959 (13) | 0.0241 (3) | |
C12 | 0.57886 (15) | 0.71713 (14) | 0.32865 (13) | 0.0215 (3) | |
C13 | 0.27884 (14) | 0.70868 (13) | 0.31002 (13) | 0.0186 (3) | |
C14 | 0.22710 (15) | 0.66191 (15) | 0.43602 (14) | 0.0234 (3) | |
C15 | 0.11178 (16) | 0.71416 (16) | 0.51282 (13) | 0.0269 (3) | |
C16 | 0.04044 (15) | 0.81871 (15) | 0.46402 (14) | 0.0247 (3) | |
C17 | 0.08604 (14) | 0.86860 (14) | 0.33981 (14) | 0.0218 (3) | |
C18 | 0.20305 (14) | 0.81389 (14) | 0.26681 (13) | 0.0186 (3) | |
B1 | 0.41084 (15) | 0.63123 (15) | 0.22808 (14) | 0.0170 (3) | |
F1 | 0.22276 (9) | 0.57899 (8) | 0.11235 (8) | 0.0249 (2) | |
F2 | 0.15038 (10) | 0.34249 (10) | 0.09959 (9) | 0.0344 (2) | |
F3 | 0.24525 (11) | 0.11841 (9) | 0.22023 (9) | 0.0377 (3) | |
F4 | 0.41141 (10) | 0.13279 (9) | 0.35367 (9) | 0.0341 (2) | |
F5 | 0.48976 (9) | 0.36592 (9) | 0.36452 (8) | 0.0277 (2) | |
F6 | 0.65819 (9) | 0.48882 (9) | 0.12215 (8) | 0.0260 (2) | |
F7 | 0.90480 (9) | 0.50805 (10) | 0.14013 (9) | 0.0331 (2) | |
F8 | 0.94094 (10) | 0.66504 (11) | 0.28561 (10) | 0.0405 (3) | |
F9 | 0.72494 (10) | 0.80583 (10) | 0.40967 (9) | 0.0362 (2) | |
F10 | 0.47789 (9) | 0.79352 (9) | 0.39056 (9) | 0.0300 (2) | |
F11 | 0.29383 (10) | 0.55958 (10) | 0.48881 (8) | 0.0342 (2) | |
F12 | 0.06839 (11) | 0.66398 (11) | 0.63453 (8) | 0.0401 (3) | |
F13 | −0.07282 (9) | 0.87075 (10) | 0.53615 (9) | 0.0353 (2) | |
F14 | 0.01552 (9) | 0.96777 (9) | 0.28960 (9) | 0.0308 (2) | |
F15 | 0.23967 (9) | 0.87007 (8) | 0.14502 (8) | 0.0252 (2) | |
S1 | 0.23883 (4) | 0.87561 (4) | 0.86009 (3) | 0.02401 (12) | |
O4 | 0.59411 (15) | 0.89952 (13) | 0.03606 (14) | 0.0408 (3) | |
H1B | 0.499 (2) | 0.765 (2) | 0.072 (2) | 0.046 (6)* | |
H4B | 0.644 (3) | 0.916 (3) | 0.073 (3) | 0.082 (10)* | |
H1A | 0.393 (2) | 0.712 (2) | 0.048 (2) | 0.050 (6)* | |
H4A | 0.630 (5) | 0.927 (5) | −0.036 (5) | 0.18 (2)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C19 | 0.0421 (10) | 0.0545 (12) | 0.0380 (10) | 0.0217 (9) | −0.0259 (8) | −0.0217 (9) |
C20 | 0.0267 (9) | 0.0378 (10) | 0.0536 (11) | −0.0060 (7) | −0.0169 (8) | −0.0046 (8) |
O1 | 0.0183 (5) | 0.0207 (5) | 0.0189 (5) | −0.0025 (4) | −0.0072 (4) | −0.0022 (4) |
O2 | 0.0260 (6) | 0.0343 (6) | 0.0277 (6) | 0.0043 (5) | −0.0145 (5) | −0.0041 (5) |
O3 | 0.0400 (7) | 0.0234 (6) | 0.0414 (7) | −0.0009 (5) | −0.0193 (5) | −0.0065 (5) |
C1 | 0.0158 (6) | 0.0189 (7) | 0.0200 (7) | −0.0006 (5) | −0.0034 (5) | −0.0053 (5) |
C2 | 0.0179 (7) | 0.0210 (7) | 0.0211 (7) | −0.0002 (5) | −0.0043 (5) | −0.0044 (5) |
C3 | 0.0195 (7) | 0.0307 (8) | 0.0245 (7) | −0.0061 (6) | −0.0042 (6) | −0.0108 (6) |
C4 | 0.0251 (7) | 0.0203 (7) | 0.0275 (8) | −0.0089 (6) | 0.0024 (6) | −0.0099 (6) |
C5 | 0.0257 (7) | 0.0171 (7) | 0.0242 (7) | −0.0006 (6) | −0.0007 (6) | −0.0013 (6) |
C6 | 0.0187 (7) | 0.0226 (7) | 0.0220 (7) | −0.0008 (5) | −0.0047 (5) | −0.0050 (6) |
C7 | 0.0206 (7) | 0.0176 (7) | 0.0172 (7) | −0.0017 (5) | −0.0071 (5) | −0.0017 (5) |
C8 | 0.0218 (7) | 0.0193 (7) | 0.0201 (7) | −0.0033 (5) | −0.0073 (5) | −0.0036 (5) |
C9 | 0.0188 (7) | 0.0251 (7) | 0.0245 (7) | 0.0001 (6) | −0.0056 (6) | −0.0036 (6) |
C10 | 0.0201 (7) | 0.0326 (8) | 0.0282 (8) | −0.0073 (6) | −0.0122 (6) | −0.0005 (6) |
C11 | 0.0306 (8) | 0.0247 (8) | 0.0218 (7) | −0.0075 (6) | −0.0126 (6) | −0.0045 (6) |
C12 | 0.0238 (7) | 0.0192 (7) | 0.0213 (7) | −0.0004 (5) | −0.0069 (6) | −0.0036 (5) |
C13 | 0.0186 (7) | 0.0178 (7) | 0.0207 (7) | −0.0019 (5) | −0.0069 (5) | −0.0047 (5) |
C14 | 0.0246 (7) | 0.0218 (7) | 0.0219 (7) | 0.0005 (6) | −0.0067 (6) | −0.0019 (6) |
C15 | 0.0283 (8) | 0.0303 (8) | 0.0176 (7) | −0.0048 (6) | −0.0004 (6) | −0.0039 (6) |
C16 | 0.0173 (7) | 0.0263 (8) | 0.0287 (8) | −0.0019 (6) | −0.0002 (6) | −0.0118 (6) |
C17 | 0.0180 (7) | 0.0184 (7) | 0.0308 (8) | 0.0008 (5) | −0.0095 (6) | −0.0063 (6) |
C18 | 0.0200 (7) | 0.0181 (7) | 0.0182 (7) | −0.0028 (5) | −0.0058 (5) | −0.0037 (5) |
B1 | 0.0165 (7) | 0.0173 (7) | 0.0171 (7) | 0.0001 (6) | −0.0054 (6) | −0.0031 (6) |
F1 | 0.0237 (4) | 0.0251 (5) | 0.0296 (5) | 0.0012 (3) | −0.0140 (4) | −0.0054 (4) |
F2 | 0.0308 (5) | 0.0409 (6) | 0.0394 (6) | −0.0102 (4) | −0.0147 (4) | −0.0142 (4) |
F3 | 0.0471 (6) | 0.0246 (5) | 0.0391 (6) | −0.0154 (4) | −0.0020 (5) | −0.0121 (4) |
F4 | 0.0419 (6) | 0.0169 (4) | 0.0375 (5) | 0.0019 (4) | −0.0085 (4) | 0.0004 (4) |
F5 | 0.0295 (5) | 0.0242 (5) | 0.0322 (5) | 0.0008 (4) | −0.0168 (4) | −0.0005 (4) |
F6 | 0.0224 (4) | 0.0290 (5) | 0.0306 (5) | 0.0003 (4) | −0.0079 (4) | −0.0156 (4) |
F7 | 0.0187 (4) | 0.0423 (6) | 0.0388 (5) | 0.0052 (4) | −0.0076 (4) | −0.0139 (4) |
F8 | 0.0236 (5) | 0.0585 (7) | 0.0486 (6) | −0.0070 (5) | −0.0183 (4) | −0.0157 (5) |
F9 | 0.0403 (6) | 0.0422 (6) | 0.0362 (5) | −0.0103 (4) | −0.0175 (4) | −0.0161 (4) |
F10 | 0.0301 (5) | 0.0312 (5) | 0.0343 (5) | 0.0044 (4) | −0.0116 (4) | −0.0185 (4) |
F11 | 0.0396 (6) | 0.0332 (5) | 0.0223 (5) | 0.0098 (4) | −0.0082 (4) | 0.0032 (4) |
F12 | 0.0424 (6) | 0.0479 (6) | 0.0183 (5) | 0.0005 (5) | 0.0029 (4) | −0.0016 (4) |
F13 | 0.0235 (5) | 0.0390 (6) | 0.0367 (5) | 0.0021 (4) | 0.0043 (4) | −0.0156 (4) |
F14 | 0.0236 (5) | 0.0274 (5) | 0.0403 (5) | 0.0091 (4) | −0.0117 (4) | −0.0063 (4) |
F15 | 0.0289 (5) | 0.0241 (4) | 0.0198 (4) | 0.0045 (4) | −0.0071 (3) | −0.0014 (3) |
S1 | 0.0244 (2) | 0.0238 (2) | 0.0283 (2) | 0.00225 (14) | −0.01379 (15) | −0.00704 (15) |
O4 | 0.0494 (8) | 0.0372 (7) | 0.0399 (8) | −0.0191 (6) | −0.0209 (6) | 0.0031 (6) |
Geometric parameters (Å, º) top
C19—S1 | 1.7545 (18) | C11—F9 | 1.3417 (17) |
C20—S1 | 1.7550 (19) | C11—C12 | 1.385 (2) |
O1—B1 | 1.5651 (19) | C12—F10 | 1.3515 (17) |
O2—S1 | 1.4449 (12) | C13—C18 | 1.381 (2) |
O3—S1 | 1.4447 (12) | C13—C14 | 1.389 (2) |
C1—C6 | 1.384 (2) | C13—B1 | 1.638 (2) |
C1—C2 | 1.388 (2) | C14—F11 | 1.3533 (18) |
C1—B1 | 1.640 (2) | C14—C15 | 1.379 (2) |
C2—F1 | 1.3550 (17) | C15—F12 | 1.3469 (18) |
C2—C3 | 1.383 (2) | C15—C16 | 1.376 (2) |
C3—F2 | 1.3438 (18) | C16—F13 | 1.3411 (17) |
C3—C4 | 1.370 (2) | C16—C17 | 1.372 (2) |
C4—F3 | 1.3445 (17) | C17—F14 | 1.3423 (18) |
C4—C5 | 1.376 (2) | C17—C18 | 1.382 (2) |
C5—F4 | 1.3422 (18) | C18—F15 | 1.3607 (17) |
C5—C6 | 1.382 (2) | C19—H19A | 0.9800 |
C6—F5 | 1.3522 (17) | C19—H19B | 0.9800 |
C7—C12 | 1.388 (2) | C19—H19C | 0.9800 |
C7—C8 | 1.396 (2) | C20—H20A | 0.9800 |
C7—B1 | 1.631 (2) | C20—H20B | 0.9800 |
C8—F6 | 1.3495 (16) | C20—H20C | 0.9800 |
C8—C9 | 1.373 (2) | O1—H1B | 0.85 (2) |
C9—F7 | 1.3468 (18) | O1—H1A | 0.87 (3) |
C9—C10 | 1.375 (2) | O4—H4B | 0.83 (3) |
C10—F8 | 1.3428 (17) | O4—H4A | 0.80 (5) |
C10—C11 | 1.374 (2) | | |
| | | |
C6—C1—C2 | 114.58 (13) | C15—C14—C13 | 124.26 (14) |
C6—C1—B1 | 126.57 (13) | F12—C15—C16 | 119.81 (14) |
C2—C1—B1 | 118.85 (13) | F12—C15—C14 | 120.84 (15) |
F1—C2—C3 | 116.87 (13) | C16—C15—C14 | 119.35 (14) |
F1—C2—C1 | 119.29 (12) | F13—C16—C17 | 120.23 (14) |
C3—C2—C1 | 123.84 (14) | F13—C16—C15 | 120.72 (14) |
F2—C3—C4 | 120.00 (13) | C17—C16—C15 | 119.05 (13) |
F2—C3—C2 | 121.16 (15) | F14—C17—C16 | 120.03 (13) |
C4—C3—C2 | 118.84 (14) | F14—C17—C18 | 120.47 (13) |
F3—C4—C3 | 120.26 (15) | C16—C17—C18 | 119.48 (14) |
F3—C4—C5 | 119.78 (15) | F15—C18—C13 | 120.72 (12) |
C3—C4—C5 | 119.95 (13) | F15—C18—C17 | 115.01 (13) |
F4—C5—C4 | 119.31 (13) | C13—C18—C17 | 124.27 (13) |
F4—C5—C6 | 121.34 (14) | O1—B1—C7 | 100.50 (11) |
C4—C5—C6 | 119.34 (14) | O1—B1—C13 | 111.53 (11) |
F5—C6—C5 | 116.10 (13) | C7—B1—C13 | 115.45 (11) |
F5—C6—C1 | 120.53 (13) | O1—B1—C1 | 105.60 (11) |
C5—C6—C1 | 123.36 (14) | C7—B1—C1 | 115.70 (12) |
C12—C7—C8 | 113.89 (13) | C13—B1—C1 | 107.52 (11) |
C12—C7—B1 | 126.76 (13) | O3—S1—O2 | 116.69 (7) |
C8—C7—B1 | 118.92 (12) | O3—S1—C19 | 108.63 (9) |
F6—C8—C9 | 116.21 (13) | O2—S1—C19 | 108.23 (8) |
F6—C8—C7 | 119.59 (13) | O3—S1—C20 | 108.27 (9) |
C9—C8—C7 | 124.19 (13) | O2—S1—C20 | 109.15 (8) |
F7—C9—C8 | 120.87 (13) | C19—S1—C20 | 105.27 (10) |
F7—C9—C10 | 119.76 (13) | S1—C19—H19A | 109.5 |
C8—C9—C10 | 119.38 (14) | S1—C19—H19B | 109.5 |
F8—C10—C11 | 120.40 (14) | H19A—C19—H19B | 109.5 |
F8—C10—C9 | 120.30 (15) | S1—C19—H19C | 109.5 |
C11—C10—C9 | 119.30 (14) | H19A—C19—H19C | 109.5 |
F9—C11—C10 | 119.44 (14) | H19B—C19—H19C | 109.5 |
F9—C11—C12 | 120.84 (14) | S1—C20—H20A | 109.5 |
C10—C11—C12 | 119.71 (14) | S1—C20—H20B | 109.5 |
F10—C12—C11 | 115.61 (13) | H20A—C20—H20B | 109.5 |
F10—C12—C7 | 120.85 (13) | S1—C20—H20C | 109.5 |
C11—C12—C7 | 123.52 (14) | H20A—C20—H20C | 109.5 |
C18—C13—C14 | 113.57 (13) | H20B—C20—H20C | 109.5 |
C18—C13—B1 | 127.07 (12) | B1—O1—H1B | 113.0 (15) |
C14—C13—B1 | 119.18 (13) | B1—O1—H1A | 121.0 (15) |
F11—C14—C15 | 116.97 (13) | H1B—O1—H1A | 110 (2) |
F11—C14—C13 | 118.76 (13) | H4B—O4—H4A | 107 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O4 | 0.85 (2) | 1.69 (2) | 2.5391 (18) | 179 (2) |
O1—H1A···F1 | 0.87 (3) | 2.19 (2) | 2.7046 (16) | 117.0 (19) |
O4—H4B···O3i | 0.83 (3) | 1.99 (3) | 2.807 (2) | 169 (3) |
O4—H4B···S1i | 0.83 (3) | 2.94 (3) | 3.6522 (17) | 146 (3) |
O1—H1A···O2ii | 0.87 (3) | 1.95 (2) | 2.7291 (17) | 148 (2) |
O4—H4A···F3iii | 0.80 (5) | 2.24 (5) | 2.950 (2) | 147 (5) |
O4—H4A···F15iv | 0.80 (5) | 2.50 (5) | 3.089 (2) | 131 (5) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+2, −z. |
Experimental details
Crystal data |
Chemical formula | C18H2BF15O·H2O·C2H6O2S |
Mr | 642.15 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 10.357 (2), 10.397 (2), 11.671 (2) |
α, β, γ (°) | 77.76 (3), 71.14 (3), 83.95 (3) |
V (Å3) | 1161.4 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.29 |
Crystal size (mm) | 0.5 × 0.3 × 0.1 |
|
Data collection |
Diffractometer | Bruker–Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1997) |
Tmin, Tmax | 0.796, 0.924 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21780, 5282, 4488 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.096, 1.03 |
No. of reflections | 5282 |
No. of parameters | 389 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.31, −0.35 |
Selected geometric parameters (Å, º) topC19—S1 | 1.7545 (18) | O3—S1 | 1.4447 (12) |
C20—S1 | 1.7550 (19) | C1—B1 | 1.640 (2) |
O1—B1 | 1.5651 (19) | C7—B1 | 1.631 (2) |
O2—S1 | 1.4449 (12) | C13—B1 | 1.638 (2) |
| | | |
O1—B1—C7 | 100.50 (11) | O3—S1—O2 | 116.69 (7) |
O1—B1—C13 | 111.53 (11) | O3—S1—C19 | 108.63 (9) |
C7—B1—C13 | 115.45 (11) | O2—S1—C19 | 108.23 (8) |
O1—B1—C1 | 105.60 (11) | O3—S1—C20 | 108.27 (9) |
C7—B1—C1 | 115.70 (12) | O2—S1—C20 | 109.15 (8) |
C13—B1—C1 | 107.52 (11) | C19—S1—C20 | 105.27 (10) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O4 | 0.85 (2) | 1.69 (2) | 2.5391 (18) | 179 (2) |
O1—H1A···F1 | 0.87 (3) | 2.19 (2) | 2.7046 (16) | 117.0 (19) |
O4—H4B···O3i | 0.83 (3) | 1.99 (3) | 2.807 (2) | 169 (3) |
O4—H4B···S1i | 0.83 (3) | 2.94 (3) | 3.6522 (17) | 146 (3) |
O1—H1A···O2ii | 0.87 (3) | 1.95 (2) | 2.7291 (17) | 148 (2) |
O4—H4A···F3iii | 0.80 (5) | 2.24 (5) | 2.950 (2) | 147 (5) |
O4—H4A···F15iv | 0.80 (5) | 2.50 (5) | 3.089 (2) | 131 (5) |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x, y, z−1; (iii) −x+1, −y+1, −z; (iv) −x+1, −y+2, −z. |
There has been much recent interest in the chemistry of B(C6F5) due to its Lewis acidic properties and it potential as a catalyst for organic transformations (Piers & Chivers, 1997). We have recently explored the chemistry of phosphoryl donors (Beckett et al., 2000, 2001) towards B(C6F5)3 and have now turned our attention to sulfuryl donors. In an attempt to obtain the Me2SO2 adduct of B(C6F5), we inadvertently prepared the title compound (H2O)B(C6F5)3·Me2SO2·H2O, (I), as a consequence of adventitious H2O in our reaction system. Compound (I) was characterized by melting point, elemental analysis, IR and NMR (1H and 11B) spectroscopy, and in the solid state by a single-crystal X-ray diffraction study.
The structure of (I) may be conveniently described as a water adduct of B(C6F5)3 i.e. (H2O)B(C6F5)3 linked to other adduct moieties by a network of hydrogen bonds involving one additional H2O and one Me2SO2 molecule per adduct molecule. Previous crystallographic studies on structures which contain the B(C6F5)3 motif include [(C6F5)3B(OH)B(C6F5)3]− (Danopoulos et al., 1998), [WO{OBC6F5)3}3]2− (Barrada at al., 1999), [Zr(Cp*)2{OB(C6F5)3}] (Siedle et al., 1993), and the adducts B(C6F5)3. L, with L = Et3PO (Beckett et al., 2000), Ph3PO (Beckett et al., 2001), PPh3 (Jacobson et al., 1999), RCN (R = Me, 4-MeC6H4, 4-NO2C6H4) (Jacobson et al., 1999), RNC (R = tBu, CMe2CH2tBu) (Jacobson et al., 1999), H2O (Doerrer & Green, 1999; Danopoulos et al., 1998), PhC(X)O (X = OEt, NiPr2, H, Me) (Parks et al., 1998), PH3 (Bradley et al., 1991), and PtBuH2 (Bradley et al., 1996). The structure of the B(C6F5) moiety in (I) is that of a three-bladed propellor and is geometrically comparable with the structures outlined above.
A view of (I), showing the atomic numbering scheme, is shown in Fig. 1. Bond lengths and internuclear angles (Table 1) for the (H2O)B(C6F5)3 component of (I) are not significantly different to those found within this moiety in the structures of (H2O)B(C6F5)3 (Doerrer & Green, 1999) and (H2O)B(C6F5)3·2H2O (Danopoulos et al., 1998). These earlier structures which contain the (H2O)B(C6F5)3 fragment display hydrogen-bond interactions. Hydrogen-bond interactions and weakly interacting short contacts are apparent in (I) (Table 2) and these are responsible for its supramolecular architecture (Fig. 2). Two dimethyl sulfone and two water molecules associate as a tetramer, which binds two aquatris(pentafluorophenyl)borane moieties through the water ligand and fluoride groups.