Di­methyl­phenyl­sulfonium tri­fluoro­methane­sulfonate and methyl­di­phenyl­sulfonium tri­fluoro­methane­sulfonate

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.

Computing details

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

Crystal data

C8H11S^+·CF3SO3^−	Dx = 1.557 Mg m^−3
Mr = 288.30	Melting point: 381(1) K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.659 (2) Å	Cell parameters from 2000 reflections
b = 10.045 (2) Å	θ = 2.5–25.0°
c = 9.4366 (16) Å	µ = 0.46 mm^−1
β = 108.205 (18)°	T = 180 K
V = 1229.9 (4) Å^3	Block, colorless
Z = 4	0.84 × 0.60 × 0.40 mm
F(000) = 592

Data collection

Stoe IPDS diffractometer	2221 independent reflections
Radiation source: fine-focus sealed X-ray tube	1975 reflections with I > 2σ(I)
Planar graphite monochromator	Rint = 0.072
Detector resolution: 6.667 pixels mm^-1	θmax = 25.5°, θmin = 2.6°
φ–rotation, φ–incr. = 1.6°, 138 exposures scans	h = −16→16
Absorption correction: part of the refinement model (ΔF) (ABSCOR; stoe & Cie, 1997) see publ_section_exptl_prep	k = −12→12
Tmin = 0.697, Tmax = 0.836	l = −11→11
7424 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H-atom parameters not refined
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0703P)^2 + 0.7631P] where P = (Fo^2 + 2Fc^2)/3
2221 reflections	(Δ/σ)max = 0.007
156 parameters	Δρmax = 0.89 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.92645 (19)	0.6737 (2)	0.3857 (3)	0.0316 (5)
H1A	0.9081	0.7666	0.3965	0.038*
H1B	1.0015	0.6660	0.4105	0.038*
H1C	0.9026	0.6175	0.4532	0.038*
C2	0.89535 (19)	0.4467 (2)	0.2122 (3)	0.0333 (6)
H2A	0.8624	0.4038	0.1157	0.040*
H2B	0.8692	0.4070	0.2881	0.040*
H2C	0.9701	0.4339	0.2406	0.040*
C3	0.73214 (17)	0.6237 (2)	0.1755 (3)	0.0249 (5)
C4	0.69032 (19)	0.5554 (3)	0.2692 (3)	0.0339 (6)
H4	0.7331	0.5064	0.3514	0.041*
C5	0.5841 (2)	0.5597 (3)	0.2409 (3)	0.0413 (6)
H5	0.5539	0.5121	0.3036	0.050*
C6	0.5227 (2)	0.6318 (3)	0.1235 (3)	0.0459 (7)
H6	0.4504	0.6347	0.1060	0.055*
C7	0.5656 (2)	0.7000 (3)	0.0309 (4)	0.0503 (8)
H7	0.5226	0.7496	−0.0506	0.060*
C8	0.6715 (2)	0.6966 (3)	0.0564 (3)	0.0390 (6)
H8	0.7015	0.7436	−0.0071	0.047*
C9	1.2917 (2)	0.6302 (3)	0.3395 (3)	0.0372 (6)
S1	0.86672 (4)	0.62105 (5)	0.19766 (6)	0.02348 (19)
S2	1.17383 (4)	0.54367 (6)	0.24099 (7)	0.0291 (2)
O1	1.09978 (14)	0.64693 (18)	0.1844 (2)	0.0445 (5)
O2	1.15595 (16)	0.4583 (2)	0.3507 (3)	0.0513 (6)
O3	1.2031 (2)	0.4723 (2)	0.1290 (3)	0.0587 (6)
F1	1.31857 (14)	0.71878 (19)	0.2566 (2)	0.0609 (5)
F2	1.28002 (17)	0.6974 (2)	0.4558 (2)	0.0675 (6)
F3	1.37012 (13)	0.54818 (18)	0.3958 (2)	0.0579 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0329 (13)	0.0348 (12)	0.0249 (12)	−0.0043 (10)	0.0056 (11)	−0.0002 (9)
C2	0.0283 (12)	0.0234 (11)	0.0456 (16)	0.0042 (9)	0.0076 (12)	0.0010 (10)
C3	0.0228 (11)	0.0252 (11)	0.0260 (12)	0.0026 (8)	0.0066 (10)	−0.0014 (8)
C4	0.0271 (12)	0.0454 (14)	0.0285 (13)	0.0022 (10)	0.0075 (11)	0.0057 (10)
C5	0.0311 (14)	0.0580 (17)	0.0383 (15)	−0.0021 (12)	0.0158 (12)	−0.0004 (12)
C6	0.0240 (13)	0.0629 (19)	0.0495 (18)	0.0078 (12)	0.0097 (13)	−0.0065 (13)
C7	0.0317 (14)	0.0634 (19)	0.0496 (18)	0.0153 (13)	0.0039 (14)	0.0177 (14)
C8	0.0343 (13)	0.0407 (14)	0.0409 (15)	0.0095 (11)	0.0101 (12)	0.0129 (11)
C9	0.0312 (13)	0.0398 (14)	0.0390 (15)	−0.0064 (10)	0.0089 (12)	0.0065 (11)
S1	0.0238 (3)	0.0231 (3)	0.0235 (3)	0.00190 (19)	0.0072 (3)	0.00317 (19)
S2	0.0254 (3)	0.0282 (3)	0.0311 (4)	−0.0033 (2)	0.0052 (3)	0.0012 (2)
O1	0.0313 (10)	0.0383 (10)	0.0567 (13)	0.0041 (8)	0.0032 (10)	0.0047 (9)
O2	0.0387 (11)	0.0595 (13)	0.0543 (13)	−0.0132 (9)	0.0126 (10)	0.0224 (10)
O3	0.0710 (16)	0.0591 (14)	0.0456 (13)	0.0030 (11)	0.0178 (12)	−0.0221 (10)
F1	0.0501 (10)	0.0628 (11)	0.0685 (13)	−0.0231 (8)	0.0167 (10)	0.0218 (9)
F2	0.0778 (14)	0.0722 (13)	0.0455 (11)	−0.0150 (11)	0.0090 (10)	−0.0285 (9)
F3	0.0270 (8)	0.0632 (12)	0.0731 (14)	0.0012 (7)	0.0008 (9)	0.0169 (9)

Geometric parameters (Å, º)

C1—S1	1.786 (2)	C7—C8	1.392 (4)
C2—S1	1.790 (2)	C9—F1	1.310 (3)
C3—C4	1.376 (3)	C9—F3	1.324 (3)
C3—C8	1.380 (3)	C9—F2	1.339 (3)
C3—S1	1.784 (2)	C9—S2	1.810 (3)
C4—C5	1.392 (4)	S2—O2	1.423 (2)
C5—C6	1.368 (4)	S2—O1	1.4306 (19)
C6—C7	1.377 (4)	S2—O3	1.433 (2)
C4—C3—C8	121.6 (2)	F3—C9—S2	112.65 (18)
C4—C3—S1	122.46 (19)	F2—C9—S2	110.35 (19)
C8—C3—S1	115.91 (18)	C3—S1—C1	104.25 (11)
C3—C4—C5	118.6 (2)	C3—S1—C2	102.48 (11)
C6—C5—C4	120.7 (3)	C1—S1—C2	101.11 (12)
C5—C6—C7	120.2 (3)	O2—S2—O1	116.51 (13)
C6—C7—C8	120.3 (3)	O2—S2—O3	112.70 (15)
C3—C8—C7	118.7 (2)	O1—S2—O3	114.52 (14)
F1—C9—F3	108.7 (2)	O2—S2—C9	104.08 (13)
F1—C9—F2	105.9 (2)	O1—S2—C9	104.78 (12)
F3—C9—F2	105.8 (2)	O3—S2—C9	102.15 (14)
F1—C9—S2	112.9 (2)
C8—C3—C4—C5	0.7 (4)	C8—C3—S1—C2	−128.6 (2)
S1—C3—C4—C5	−178.0 (2)	F1—C9—S2—O2	−177.3 (2)
C3—C4—C5—C6	−0.9 (4)	F3—C9—S2—O2	59.1 (2)
C4—C5—C6—C7	0.7 (5)	F2—C9—S2—O2	−59.0 (2)
C5—C6—C7—C8	−0.3 (5)	F1—C9—S2—O1	−54.5 (2)
C4—C3—C8—C7	−0.3 (4)	F3—C9—S2—O1	−178.07 (19)
S1—C3—C8—C7	178.5 (2)	F2—C9—S2—O1	63.9 (2)
C6—C7—C8—C3	0.1 (5)	F1—C9—S2—O3	65.2 (2)
C4—C3—S1—C1	−54.9 (2)	F3—C9—S2—O3	−58.3 (2)
C8—C3—S1—C1	126.3 (2)	F2—C9—S2—O3	−176.4 (2)
C4—C3—S1—C2	50.1 (2)

(II) Methyldiphenylsulfonium trifluoromethansulfonate

Crystal data

C13H13S^+·CF3SO3^−	Dx = 1.460 Mg m^−3
Mr = 350.36	Melting point: 370(1) K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.5122 (13) Å	Cell parameters from 116 reflections
b = 9.0284 (6) Å	θ = 14.1–15.0°
c = 15.3932 (14) Å	µ = 0.37 mm^−1
β = 113.552 (8)°	T = 180 K
V = 1594.0 (2) Å^3	Block, colorless
Z = 4	0.98 × 0.76 × 0.50 mm
F(000) = 720

Data collection

Stoe Stadi-4 diffractometer	3137 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tube	Rint = 0.024
Planar graphite monochromator	θmax = 27.0°, θmin = 1.8°
2θ/ω scan, ratio = 1.0, width (ω) = 1.35–1.5°	h = −16→16
Absorption correction: ψ scan (north et al., 1968) see publ_section_exptl_prep	k = 0→11
Tmin = 0.712, Tmax = 0.836	l = −19→19
5742 measured reflections	3 standard reflections every 120 min
3480 independent reflections	intensity decay: 2.4%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	All H-atom parameters refined
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.0376P)^2 + 0.6612P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.007
3480 reflections	Δρmax = 0.44 e Å^−3
252 parameters	Δρmin = −0.37 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0108 (12)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.68155 (12)	0.49379 (16)	0.73609 (10)	0.0278 (3)
C2	0.64715 (15)	0.5795 (2)	0.79453 (13)	0.0456 (4)
H2	0.702 (2)	0.614 (3)	0.8565 (17)	0.058 (6)*
C3	0.53013 (17)	0.6165 (3)	0.76442 (17)	0.0615 (6)
H3	0.503 (3)	0.673 (4)	0.802 (2)	0.098 (10)*
C4	0.45133 (17)	0.5695 (3)	0.67772 (16)	0.0591 (6)
H4	0.372 (3)	0.599 (4)	0.655 (2)	0.096 (10)*
C5	0.48592 (17)	0.4834 (3)	0.61997 (15)	0.0539 (5)
H5	0.433 (2)	0.447 (3)	0.5640 (19)	0.072 (8)*
C6	0.60282 (15)	0.4451 (2)	0.64852 (12)	0.0401 (4)
H6	0.6300 (18)	0.386 (3)	0.6092 (15)	0.052 (6)*
C7	0.84419 (12)	0.28788 (15)	0.84885 (9)	0.0240 (3)
C8	0.83605 (14)	0.30799 (17)	0.93553 (11)	0.0326 (3)
H8	0.8235 (16)	0.402 (2)	0.9556 (14)	0.041 (5)*
C9	0.84478 (15)	0.1847 (2)	0.99144 (12)	0.0387 (4)
H9	0.8398 (18)	0.197 (2)	1.0515 (16)	0.050 (6)*
C10	0.85987 (14)	0.04515 (19)	0.96078 (13)	0.0399 (4)
H10	0.8662 (18)	−0.033 (3)	0.9991 (16)	0.052 (6)*
C11	0.86846 (16)	0.02784 (18)	0.87498 (14)	0.0411 (4)
H11	0.8772 (17)	−0.067 (2)	0.8544 (15)	0.047 (6)*
C12	0.86120 (13)	0.14903 (17)	0.81806 (11)	0.0323 (3)
H12	0.8644 (17)	0.136 (2)	0.7560 (15)	0.045 (5)*
C13	0.91564 (13)	0.58193 (16)	0.84189 (11)	0.0284 (3)
H13A	0.9941 (18)	0.545 (2)	0.8673 (14)	0.046 (5)*
H13B	0.8927 (16)	0.603 (2)	0.8929 (13)	0.036 (5)*
H13C	0.9062 (18)	0.663 (2)	0.8013 (15)	0.046 (5)*
C14	0.67973 (16)	0.5954 (2)	1.08493 (14)	0.0461 (4)
O1	0.83674 (11)	0.65414 (14)	1.02169 (8)	0.0409 (3)
O2	0.78743 (12)	0.84488 (12)	1.11079 (9)	0.0416 (3)
O3	0.89716 (10)	0.62889 (14)	1.19154 (8)	0.0396 (3)
S1	0.82880 (3)	0.43621 (4)	0.76829 (2)	0.02407 (11)
S2	0.81527 (3)	0.69194 (4)	1.10427 (3)	0.02840 (11)
F1	0.69149 (12)	0.45006 (14)	1.07622 (11)	0.0716 (4)
F2	0.59314 (11)	0.6417 (2)	1.00716 (10)	0.0776 (4)
F3	0.64850 (12)	0.61477 (18)	1.15668 (11)	0.0712 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0273 (7)	0.0286 (7)	0.0269 (7)	0.0009 (5)	0.0101 (5)	0.0055 (6)
C2	0.0338 (8)	0.0625 (12)	0.0375 (9)	0.0103 (8)	0.0112 (7)	−0.0079 (8)
C3	0.0395 (10)	0.0867 (17)	0.0574 (12)	0.0205 (10)	0.0182 (9)	−0.0049 (12)
C4	0.0293 (9)	0.0810 (15)	0.0608 (12)	0.0086 (9)	0.0113 (8)	0.0113 (11)
C5	0.0381 (9)	0.0658 (13)	0.0421 (10)	−0.0066 (9)	−0.0004 (8)	0.0062 (9)
C6	0.0398 (8)	0.0432 (9)	0.0316 (8)	−0.0037 (7)	0.0082 (7)	0.0008 (7)
C7	0.0270 (6)	0.0214 (6)	0.0237 (6)	−0.0001 (5)	0.0103 (5)	0.0018 (5)
C8	0.0441 (8)	0.0285 (7)	0.0280 (7)	−0.0021 (6)	0.0172 (6)	−0.0005 (6)
C9	0.0433 (9)	0.0437 (9)	0.0299 (8)	−0.0036 (7)	0.0156 (7)	0.0074 (7)
C10	0.0365 (8)	0.0329 (8)	0.0449 (9)	−0.0001 (6)	0.0106 (7)	0.0164 (7)
C11	0.0480 (9)	0.0231 (7)	0.0513 (10)	0.0054 (7)	0.0190 (8)	0.0035 (7)
C12	0.0365 (8)	0.0268 (7)	0.0348 (8)	0.0037 (6)	0.0154 (6)	−0.0021 (6)
C13	0.0313 (7)	0.0235 (7)	0.0312 (7)	−0.0023 (5)	0.0134 (6)	−0.0010 (6)
C14	0.0437 (9)	0.0497 (10)	0.0501 (10)	−0.0052 (8)	0.0241 (8)	0.0016 (8)
O1	0.0562 (7)	0.0417 (6)	0.0360 (6)	−0.0027 (5)	0.0301 (5)	−0.0112 (5)
O2	0.0656 (8)	0.0262 (5)	0.0446 (7)	0.0076 (5)	0.0342 (6)	0.0001 (5)
O3	0.0435 (6)	0.0400 (6)	0.0373 (6)	0.0054 (5)	0.0183 (5)	0.0054 (5)
S1	0.03032 (18)	0.02215 (17)	0.02248 (17)	0.00127 (12)	0.01343 (13)	0.00022 (12)
S2	0.0386 (2)	0.02456 (18)	0.02900 (19)	0.00139 (13)	0.02077 (15)	−0.00184 (13)
F1	0.0772 (9)	0.0451 (7)	0.0971 (11)	−0.0236 (6)	0.0398 (8)	−0.0103 (7)
F2	0.0426 (6)	0.1044 (12)	0.0718 (9)	−0.0079 (7)	0.0080 (6)	0.0165 (8)
F3	0.0673 (8)	0.0906 (10)	0.0806 (9)	−0.0072 (7)	0.0559 (7)	0.0052 (8)

Geometric parameters (Å, º)

C1—C2	1.380 (2)	C9—H9	0.96 (2)
C1—C6	1.386 (2)	C10—C11	1.376 (3)
C1—S1	1.7835 (14)	C10—H10	0.91 (2)
C2—C3	1.388 (3)	C11—C12	1.382 (2)
C2—H2	0.98 (2)	C11—H11	0.94 (2)
C3—C4	1.372 (3)	C12—H12	0.98 (2)
C3—H3	0.93 (3)	C13—S1	1.7920 (15)
C4—C5	1.374 (3)	C13—H13A	0.96 (2)
C4—H4	0.94 (3)	C13—H13B	0.96 (2)
C5—C6	1.392 (3)	C13—H13C	0.94 (2)
C5—H5	0.91 (3)	C14—F2	1.321 (2)
C6—H6	0.97 (2)	C14—F3	1.322 (2)
C7—C12	1.386 (2)	C14—F1	1.333 (2)
C7—C8	1.390 (2)	C14—S2	1.8224 (19)
C7—S1	1.7826 (14)	O1—S2	1.4413 (11)
C8—C9	1.385 (2)	O2—S2	1.4373 (11)
C8—H8	0.94 (2)	O3—S2	1.4418 (12)
C9—C10	1.384 (3)
C2—C1—C6	121.79 (15)	C9—C10—H10	118.6 (14)
C2—C1—S1	122.63 (12)	C10—C11—C12	120.53 (16)
C6—C1—S1	115.58 (12)	C10—C11—H11	119.5 (13)
C1—C2—C3	118.64 (17)	C12—C11—H11	119.9 (13)
C1—C2—H2	122.3 (14)	C11—C12—C7	118.64 (15)
C3—C2—H2	119.1 (14)	C11—C12—H12	120.5 (12)
C4—C3—C2	120.2 (2)	C7—C12—H12	120.8 (12)
C4—C3—H3	118.5 (19)	S1—C13—H13A	105.3 (12)
C2—C3—H3	121.3 (19)	S1—C13—H13B	111.1 (11)
C3—C4—C5	120.96 (18)	H13A—C13—H13B	109.1 (16)
C3—C4—H4	120.9 (19)	S1—C13—H13C	105.5 (13)
C5—C4—H4	118.1 (19)	H13A—C13—H13C	112.3 (18)
C4—C5—C6	119.93 (18)	H13B—C13—H13C	113.2 (17)
C4—C5—H5	121.2 (17)	F2—C14—F3	107.81 (16)
C6—C5—H5	118.8 (17)	F2—C14—F1	107.70 (18)
C1—C6—C5	118.49 (18)	F3—C14—F1	107.19 (17)
C1—C6—H6	119.6 (12)	F2—C14—S2	111.67 (14)
C5—C6—H6	121.9 (12)	F3—C14—S2	111.51 (14)
C12—C7—C8	121.77 (13)	F1—C14—S2	110.76 (14)
C12—C7—S1	115.47 (11)	C7—S1—C1	102.98 (6)
C8—C7—S1	122.73 (11)	C7—S1—C13	104.01 (7)
C9—C8—C7	118.27 (15)	C1—S1—C13	105.06 (7)
C9—C8—H8	120.4 (12)	O2—S2—O1	115.14 (7)
C7—C8—H8	121.3 (12)	O2—S2—O3	114.59 (8)
C10—C9—C8	120.49 (15)	O1—S2—O3	114.51 (7)
C10—C9—H9	120.5 (13)	O2—S2—C14	103.60 (9)
C8—C9—H9	119.0 (14)	O1—S2—C14	103.40 (8)
C11—C10—C9	120.27 (15)	O3—S2—C14	103.40 (8)
C11—C10—H10	121.0 (14)
C6—C1—C2—C3	0.5 (3)	C8—C7—S1—C1	−64.21 (14)
S1—C1—C2—C3	−178.65 (17)	C12—C7—S1—C13	−136.82 (12)
C1—C2—C3—C4	−0.7 (4)	C8—C7—S1—C13	45.19 (14)
C2—C3—C4—C5	1.1 (4)	C2—C1—S1—C7	77.47 (16)
C3—C4—C5—C6	−1.2 (4)	C6—C1—S1—C7	−101.72 (13)
C2—C1—C6—C5	−0.6 (3)	C2—C1—S1—C13	−31.15 (16)
S1—C1—C6—C5	178.61 (14)	C6—C1—S1—C13	149.67 (12)
C4—C5—C6—C1	0.9 (3)	F2—C14—S2—O2	59.26 (16)
C12—C7—C8—C9	−0.3 (2)	F3—C14—S2—O2	−61.43 (16)
S1—C7—C8—C9	177.53 (12)	F1—C14—S2—O2	179.29 (14)
C7—C8—C9—C10	−0.7 (2)	F2—C14—S2—O1	−61.21 (16)
C8—C9—C10—C11	1.2 (3)	F3—C14—S2—O1	178.11 (14)
C9—C10—C11—C12	−0.5 (3)	F1—C14—S2—O1	58.82 (16)
C10—C11—C12—C7	−0.5 (3)	F2—C14—S2—O3	179.11 (14)
C8—C7—C12—C11	0.9 (2)	F3—C14—S2—O3	58.43 (16)
S1—C7—C12—C11	−177.06 (13)	F1—C14—S2—O3	−60.86 (16)
C12—C7—S1—C1	113.77 (12)