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The bonding geometry of sulfur in the cations of the title compounds, C8H11S+·CF3SO3- and C13H13S+·CF3SO3-, respectively, is similar and is independent of the ratio of the Me/Ph substituents. As expected, in both cations, the S-Ph bonds are somewhat shorter than the S-Me bonds. In both crystal structures, the interaction between cations and anions is similar.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100006077/qa0284sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006077/qa0284Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100006077/qa0284IIsup3.hkl
Contains datablock II

CCDC references: 146094; 146095

Computing details top

Data collection: IPDS2.87 (Stoe & Cie, 1997) for (I); STADI4-1.06 (Stoe & Cie, 1997) for (II). Cell refinement: IPDS2.87 for (I); STADI4-1.06 for (II). Data reduction: IPDS2.87 for (I); X-RED1.07 (Stoe & Cie, 1997) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XSTEP-2.18 (Stoe, 1997); software used to prepare material for publication: SHELXL97.

(I) Dimethylphenylsulfonium trifluormethansulfonate top
Crystal data top
C8H11S+·CF3SO3Dx = 1.557 Mg m3
Mr = 288.30Melting point: 381(1) K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 13.659 (2) ÅCell parameters from 2000 reflections
b = 10.045 (2) Åθ = 2.5–25.0°
c = 9.4366 (16) ŵ = 0.46 mm1
β = 108.205 (18)°T = 180 K
V = 1229.9 (4) Å3Block, colorless
Z = 40.84 × 0.60 × 0.40 mm
F(000) = 592
Data collection top
Stoe IPDS
diffractometer
2221 independent reflections
Radiation source: fine-focus sealed X-ray tube1975 reflections with I > 2σ(I)
Planar graphite monochromatorRint = 0.072
Detector resolution: 6.667 pixels mm-1θmax = 25.5°, θmin = 2.6°
φ–rotation, φ–incr. = 1.6°, 138 exposures scansh = 1616
Absorption correction: part of the refinement model (ΔF) (ABSCOR; stoe & Cie, 1997)
see publ_section_exptl_prep
k = 1212
Tmin = 0.697, Tmax = 0.836l = 1111
7424 measured reflections
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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters not refined
S = 1.06 w = 1/[σ2(Fo2) + (0.0703P)2 + 0.7631P]
where P = (Fo2 + 2Fc2)/3
2221 reflections(Δ/σ)max = 0.007
156 parametersΔρmax = 0.89 e Å3
0 restraintsΔρmin = 0.44 e Å3
Special details top

Experimental. Recrystallized from 2-propanol. During data collection the crystal was in cold N2 gas of the Cryostream Cooler (Oxford Cryosystems, 1992) mounted on a φ-axis diffractometer supplied with an area detector.

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
C10.92645 (19)0.6737 (2)0.3857 (3)0.0316 (5)
H1A0.90810.76660.39650.038*
H1B1.00150.66600.41050.038*
H1C0.90260.61750.45320.038*
C20.89535 (19)0.4467 (2)0.2122 (3)0.0333 (6)
H2A0.86240.40380.11570.040*
H2B0.86920.40700.28810.040*
H2C0.97010.43390.24060.040*
C30.73214 (17)0.6237 (2)0.1755 (3)0.0249 (5)
C40.69032 (19)0.5554 (3)0.2692 (3)0.0339 (6)
H40.73310.50640.35140.041*
C50.5841 (2)0.5597 (3)0.2409 (3)0.0413 (6)
H50.55390.51210.30360.050*
C60.5227 (2)0.6318 (3)0.1235 (3)0.0459 (7)
H60.45040.63470.10600.055*
C70.5656 (2)0.7000 (3)0.0309 (4)0.0503 (8)
H70.52260.74960.05060.060*
C80.6715 (2)0.6966 (3)0.0564 (3)0.0390 (6)
H80.70150.74360.00710.047*
C91.2917 (2)0.6302 (3)0.3395 (3)0.0372 (6)
S10.86672 (4)0.62105 (5)0.19766 (6)0.02348 (19)
S21.17383 (4)0.54367 (6)0.24099 (7)0.0291 (2)
O11.09978 (14)0.64693 (18)0.1844 (2)0.0445 (5)
O21.15595 (16)0.4583 (2)0.3507 (3)0.0513 (6)
O31.2031 (2)0.4723 (2)0.1290 (3)0.0587 (6)
F11.31857 (14)0.71878 (19)0.2566 (2)0.0609 (5)
F21.28002 (17)0.6974 (2)0.4558 (2)0.0675 (6)
F31.37012 (13)0.54818 (18)0.3958 (2)0.0579 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0329 (13)0.0348 (12)0.0249 (12)0.0043 (10)0.0056 (11)0.0002 (9)
C20.0283 (12)0.0234 (11)0.0456 (16)0.0042 (9)0.0076 (12)0.0010 (10)
C30.0228 (11)0.0252 (11)0.0260 (12)0.0026 (8)0.0066 (10)0.0014 (8)
C40.0271 (12)0.0454 (14)0.0285 (13)0.0022 (10)0.0075 (11)0.0057 (10)
C50.0311 (14)0.0580 (17)0.0383 (15)0.0021 (12)0.0158 (12)0.0004 (12)
C60.0240 (13)0.0629 (19)0.0495 (18)0.0078 (12)0.0097 (13)0.0065 (13)
C70.0317 (14)0.0634 (19)0.0496 (18)0.0153 (13)0.0039 (14)0.0177 (14)
C80.0343 (13)0.0407 (14)0.0409 (15)0.0095 (11)0.0101 (12)0.0129 (11)
C90.0312 (13)0.0398 (14)0.0390 (15)0.0064 (10)0.0089 (12)0.0065 (11)
S10.0238 (3)0.0231 (3)0.0235 (3)0.00190 (19)0.0072 (3)0.00317 (19)
S20.0254 (3)0.0282 (3)0.0311 (4)0.0033 (2)0.0052 (3)0.0012 (2)
O10.0313 (10)0.0383 (10)0.0567 (13)0.0041 (8)0.0032 (10)0.0047 (9)
O20.0387 (11)0.0595 (13)0.0543 (13)0.0132 (9)0.0126 (10)0.0224 (10)
O30.0710 (16)0.0591 (14)0.0456 (13)0.0030 (11)0.0178 (12)0.0221 (10)
F10.0501 (10)0.0628 (11)0.0685 (13)0.0231 (8)0.0167 (10)0.0218 (9)
F20.0778 (14)0.0722 (13)0.0455 (11)0.0150 (11)0.0090 (10)0.0285 (9)
F30.0270 (8)0.0632 (12)0.0731 (14)0.0012 (7)0.0008 (9)0.0169 (9)
Geometric parameters (Å, º) top
C1—S11.786 (2)C7—C81.392 (4)
C2—S11.790 (2)C9—F11.310 (3)
C3—C41.376 (3)C9—F31.324 (3)
C3—C81.380 (3)C9—F21.339 (3)
C3—S11.784 (2)C9—S21.810 (3)
C4—C51.392 (4)S2—O21.423 (2)
C5—C61.368 (4)S2—O11.4306 (19)
C6—C71.377 (4)S2—O31.433 (2)
C4—C3—C8121.6 (2)F3—C9—S2112.65 (18)
C4—C3—S1122.46 (19)F2—C9—S2110.35 (19)
C8—C3—S1115.91 (18)C3—S1—C1104.25 (11)
C3—C4—C5118.6 (2)C3—S1—C2102.48 (11)
C6—C5—C4120.7 (3)C1—S1—C2101.11 (12)
C5—C6—C7120.2 (3)O2—S2—O1116.51 (13)
C6—C7—C8120.3 (3)O2—S2—O3112.70 (15)
C3—C8—C7118.7 (2)O1—S2—O3114.52 (14)
F1—C9—F3108.7 (2)O2—S2—C9104.08 (13)
F1—C9—F2105.9 (2)O1—S2—C9104.78 (12)
F3—C9—F2105.8 (2)O3—S2—C9102.15 (14)
F1—C9—S2112.9 (2)
C8—C3—C4—C50.7 (4)C8—C3—S1—C2128.6 (2)
S1—C3—C4—C5178.0 (2)F1—C9—S2—O2177.3 (2)
C3—C4—C5—C60.9 (4)F3—C9—S2—O259.1 (2)
C4—C5—C6—C70.7 (5)F2—C9—S2—O259.0 (2)
C5—C6—C7—C80.3 (5)F1—C9—S2—O154.5 (2)
C4—C3—C8—C70.3 (4)F3—C9—S2—O1178.07 (19)
S1—C3—C8—C7178.5 (2)F2—C9—S2—O163.9 (2)
C6—C7—C8—C30.1 (5)F1—C9—S2—O365.2 (2)
C4—C3—S1—C154.9 (2)F3—C9—S2—O358.3 (2)
C8—C3—S1—C1126.3 (2)F2—C9—S2—O3176.4 (2)
C4—C3—S1—C250.1 (2)
(II) Methyldiphenylsulfonium trifluoromethansulfonate top
Crystal data top
C13H13S+·CF3SO3Dx = 1.460 Mg m3
Mr = 350.36Melting point: 370(1) K
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.5122 (13) ÅCell parameters from 116 reflections
b = 9.0284 (6) Åθ = 14.1–15.0°
c = 15.3932 (14) ŵ = 0.37 mm1
β = 113.552 (8)°T = 180 K
V = 1594.0 (2) Å3Block, colorless
Z = 40.98 × 0.76 × 0.50 mm
F(000) = 720
Data collection top
Stoe Stadi-4
diffractometer
3137 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.024
Planar graphite monochromatorθmax = 27.0°, θmin = 1.8°
2θ/ω scan, ratio = 1.0, width (ω) = 1.35–1.5°h = 1616
Absorption correction: ψ scan (north et al., 1968)
see publ_section_exptl_prep
k = 011
Tmin = 0.712, Tmax = 0.836l = 1919
5742 measured reflections3 standard reflections every 120 min
3480 independent reflections intensity decay: 2.4%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031All H-atom parameters refined
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0376P)2 + 0.6612P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.007
3480 reflectionsΔρmax = 0.44 e Å3
252 parametersΔρmin = 0.37 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0108 (12)
Special details top

Experimental. Recrystallized from 2-propanol. During data collection the crystal was in cold N2 gas of a cryostream cooler (Oxford Cryosystems, 1992).

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
C10.68155 (12)0.49379 (16)0.73609 (10)0.0278 (3)
C20.64715 (15)0.5795 (2)0.79453 (13)0.0456 (4)
H20.702 (2)0.614 (3)0.8565 (17)0.058 (6)*
C30.53013 (17)0.6165 (3)0.76442 (17)0.0615 (6)
H30.503 (3)0.673 (4)0.802 (2)0.098 (10)*
C40.45133 (17)0.5695 (3)0.67772 (16)0.0591 (6)
H40.372 (3)0.599 (4)0.655 (2)0.096 (10)*
C50.48592 (17)0.4834 (3)0.61997 (15)0.0539 (5)
H50.433 (2)0.447 (3)0.5640 (19)0.072 (8)*
C60.60282 (15)0.4451 (2)0.64852 (12)0.0401 (4)
H60.6300 (18)0.386 (3)0.6092 (15)0.052 (6)*
C70.84419 (12)0.28788 (15)0.84885 (9)0.0240 (3)
C80.83605 (14)0.30799 (17)0.93553 (11)0.0326 (3)
H80.8235 (16)0.402 (2)0.9556 (14)0.041 (5)*
C90.84478 (15)0.1847 (2)0.99144 (12)0.0387 (4)
H90.8398 (18)0.197 (2)1.0515 (16)0.050 (6)*
C100.85987 (14)0.04515 (19)0.96078 (13)0.0399 (4)
H100.8662 (18)0.033 (3)0.9991 (16)0.052 (6)*
C110.86846 (16)0.02784 (18)0.87498 (14)0.0411 (4)
H110.8772 (17)0.067 (2)0.8544 (15)0.047 (6)*
C120.86120 (13)0.14903 (17)0.81806 (11)0.0323 (3)
H120.8644 (17)0.136 (2)0.7560 (15)0.045 (5)*
C130.91564 (13)0.58193 (16)0.84189 (11)0.0284 (3)
H13A0.9941 (18)0.545 (2)0.8673 (14)0.046 (5)*
H13B0.8927 (16)0.603 (2)0.8929 (13)0.036 (5)*
H13C0.9062 (18)0.663 (2)0.8013 (15)0.046 (5)*
C140.67973 (16)0.5954 (2)1.08493 (14)0.0461 (4)
O10.83674 (11)0.65414 (14)1.02169 (8)0.0409 (3)
O20.78743 (12)0.84488 (12)1.11079 (9)0.0416 (3)
O30.89716 (10)0.62889 (14)1.19154 (8)0.0396 (3)
S10.82880 (3)0.43621 (4)0.76829 (2)0.02407 (11)
S20.81527 (3)0.69194 (4)1.10427 (3)0.02840 (11)
F10.69149 (12)0.45006 (14)1.07622 (11)0.0716 (4)
F20.59314 (11)0.6417 (2)1.00716 (10)0.0776 (4)
F30.64850 (12)0.61477 (18)1.15668 (11)0.0712 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0273 (7)0.0286 (7)0.0269 (7)0.0009 (5)0.0101 (5)0.0055 (6)
C20.0338 (8)0.0625 (12)0.0375 (9)0.0103 (8)0.0112 (7)0.0079 (8)
C30.0395 (10)0.0867 (17)0.0574 (12)0.0205 (10)0.0182 (9)0.0049 (12)
C40.0293 (9)0.0810 (15)0.0608 (12)0.0086 (9)0.0113 (8)0.0113 (11)
C50.0381 (9)0.0658 (13)0.0421 (10)0.0066 (9)0.0004 (8)0.0062 (9)
C60.0398 (8)0.0432 (9)0.0316 (8)0.0037 (7)0.0082 (7)0.0008 (7)
C70.0270 (6)0.0214 (6)0.0237 (6)0.0001 (5)0.0103 (5)0.0018 (5)
C80.0441 (8)0.0285 (7)0.0280 (7)0.0021 (6)0.0172 (6)0.0005 (6)
C90.0433 (9)0.0437 (9)0.0299 (8)0.0036 (7)0.0156 (7)0.0074 (7)
C100.0365 (8)0.0329 (8)0.0449 (9)0.0001 (6)0.0106 (7)0.0164 (7)
C110.0480 (9)0.0231 (7)0.0513 (10)0.0054 (7)0.0190 (8)0.0035 (7)
C120.0365 (8)0.0268 (7)0.0348 (8)0.0037 (6)0.0154 (6)0.0021 (6)
C130.0313 (7)0.0235 (7)0.0312 (7)0.0023 (5)0.0134 (6)0.0010 (6)
C140.0437 (9)0.0497 (10)0.0501 (10)0.0052 (8)0.0241 (8)0.0016 (8)
O10.0562 (7)0.0417 (6)0.0360 (6)0.0027 (5)0.0301 (5)0.0112 (5)
O20.0656 (8)0.0262 (5)0.0446 (7)0.0076 (5)0.0342 (6)0.0001 (5)
O30.0435 (6)0.0400 (6)0.0373 (6)0.0054 (5)0.0183 (5)0.0054 (5)
S10.03032 (18)0.02215 (17)0.02248 (17)0.00127 (12)0.01343 (13)0.00022 (12)
S20.0386 (2)0.02456 (18)0.02900 (19)0.00139 (13)0.02077 (15)0.00184 (13)
F10.0772 (9)0.0451 (7)0.0971 (11)0.0236 (6)0.0398 (8)0.0103 (7)
F20.0426 (6)0.1044 (12)0.0718 (9)0.0079 (7)0.0080 (6)0.0165 (8)
F30.0673 (8)0.0906 (10)0.0806 (9)0.0072 (7)0.0559 (7)0.0052 (8)
Geometric parameters (Å, º) top
C1—C21.380 (2)C9—H90.96 (2)
C1—C61.386 (2)C10—C111.376 (3)
C1—S11.7835 (14)C10—H100.91 (2)
C2—C31.388 (3)C11—C121.382 (2)
C2—H20.98 (2)C11—H110.94 (2)
C3—C41.372 (3)C12—H120.98 (2)
C3—H30.93 (3)C13—S11.7920 (15)
C4—C51.374 (3)C13—H13A0.96 (2)
C4—H40.94 (3)C13—H13B0.96 (2)
C5—C61.392 (3)C13—H13C0.94 (2)
C5—H50.91 (3)C14—F21.321 (2)
C6—H60.97 (2)C14—F31.322 (2)
C7—C121.386 (2)C14—F11.333 (2)
C7—C81.390 (2)C14—S21.8224 (19)
C7—S11.7826 (14)O1—S21.4413 (11)
C8—C91.385 (2)O2—S21.4373 (11)
C8—H80.94 (2)O3—S21.4418 (12)
C9—C101.384 (3)
C2—C1—C6121.79 (15)C9—C10—H10118.6 (14)
C2—C1—S1122.63 (12)C10—C11—C12120.53 (16)
C6—C1—S1115.58 (12)C10—C11—H11119.5 (13)
C1—C2—C3118.64 (17)C12—C11—H11119.9 (13)
C1—C2—H2122.3 (14)C11—C12—C7118.64 (15)
C3—C2—H2119.1 (14)C11—C12—H12120.5 (12)
C4—C3—C2120.2 (2)C7—C12—H12120.8 (12)
C4—C3—H3118.5 (19)S1—C13—H13A105.3 (12)
C2—C3—H3121.3 (19)S1—C13—H13B111.1 (11)
C3—C4—C5120.96 (18)H13A—C13—H13B109.1 (16)
C3—C4—H4120.9 (19)S1—C13—H13C105.5 (13)
C5—C4—H4118.1 (19)H13A—C13—H13C112.3 (18)
C4—C5—C6119.93 (18)H13B—C13—H13C113.2 (17)
C4—C5—H5121.2 (17)F2—C14—F3107.81 (16)
C6—C5—H5118.8 (17)F2—C14—F1107.70 (18)
C1—C6—C5118.49 (18)F3—C14—F1107.19 (17)
C1—C6—H6119.6 (12)F2—C14—S2111.67 (14)
C5—C6—H6121.9 (12)F3—C14—S2111.51 (14)
C12—C7—C8121.77 (13)F1—C14—S2110.76 (14)
C12—C7—S1115.47 (11)C7—S1—C1102.98 (6)
C8—C7—S1122.73 (11)C7—S1—C13104.01 (7)
C9—C8—C7118.27 (15)C1—S1—C13105.06 (7)
C9—C8—H8120.4 (12)O2—S2—O1115.14 (7)
C7—C8—H8121.3 (12)O2—S2—O3114.59 (8)
C10—C9—C8120.49 (15)O1—S2—O3114.51 (7)
C10—C9—H9120.5 (13)O2—S2—C14103.60 (9)
C8—C9—H9119.0 (14)O1—S2—C14103.40 (8)
C11—C10—C9120.27 (15)O3—S2—C14103.40 (8)
C11—C10—H10121.0 (14)
C6—C1—C2—C30.5 (3)C8—C7—S1—C164.21 (14)
S1—C1—C2—C3178.65 (17)C12—C7—S1—C13136.82 (12)
C1—C2—C3—C40.7 (4)C8—C7—S1—C1345.19 (14)
C2—C3—C4—C51.1 (4)C2—C1—S1—C777.47 (16)
C3—C4—C5—C61.2 (4)C6—C1—S1—C7101.72 (13)
C2—C1—C6—C50.6 (3)C2—C1—S1—C1331.15 (16)
S1—C1—C6—C5178.61 (14)C6—C1—S1—C13149.67 (12)
C4—C5—C6—C10.9 (3)F2—C14—S2—O259.26 (16)
C12—C7—C8—C90.3 (2)F3—C14—S2—O261.43 (16)
S1—C7—C8—C9177.53 (12)F1—C14—S2—O2179.29 (14)
C7—C8—C9—C100.7 (2)F2—C14—S2—O161.21 (16)
C8—C9—C10—C111.2 (3)F3—C14—S2—O1178.11 (14)
C9—C10—C11—C120.5 (3)F1—C14—S2—O158.82 (16)
C10—C11—C12—C70.5 (3)F2—C14—S2—O3179.11 (14)
C8—C7—C12—C110.9 (2)F3—C14—S2—O358.43 (16)
S1—C7—C12—C11177.06 (13)F1—C14—S2—O360.86 (16)
C12—C7—S1—C1113.77 (12)
 

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