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The title compound, C
14H
14O
2S
2, contains discrete molecules and is a polymorph of a structure reported previously by Caputo, Palumbo, Nardelli & Pelizzi [
Gazz. Chim. Ital. (1984),
114, 421-430]. The present structure contains no intermolecular C-H
O hydrogen bonds, whereas in the previous polymorph, the molecules are linked into continuous chains by such interactions.
Supporting information
CCDC references: 146058; 146059
For both compounds, data collection: Kappa-CCD Server Software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).
(Ia)
S-(4-tolyl) 4-toluenethiosulfonate at 150 K
top
Crystal data top
C14H14O2S2 | F(000) = 584 |
Mr = 278.37 | Dx = 1.418 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.1835 (11) Å | Cell parameters from 2266 reflections |
b = 6.5050 (4) Å | θ = 1.5–25.0° |
c = 15.2171 (9) Å | µ = 0.40 mm−1 |
β = 92.217 (4)° | T = 150 K |
V = 1304.02 (16) Å3 | Lath, colourless |
Z = 4 | 0.30 × 0.20 × 0.15 mm |
Data collection top
Nonius Kappa-CCD diffractometer | 2266 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1849 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
φ scans and ω scans with κ offsets | θmax = 25.0°, θmin = 1.5° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | h = −15→15 |
Tmin = 0.890, Tmax = 0.943 | k = −7→7 |
7404 measured reflections | l = −17→18 |
Refinement top
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.056P)2 + 0.9064P] where P = (Fo2 + 2Fc2)/3 |
2266 reflections | (Δ/σ)max = 0.003 |
173 parameters | Δρmax = 0.33 e Å−3 |
3 restraints | Δρmin = −0.44 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.22172 (4) | 0.25543 (9) | 0.63560 (4) | 0.0220 (2) | |
S2 | 0.37885 (5) | 0.25166 (9) | 0.66447 (4) | 0.0248 (2) | |
O11 | 0.21343 (14) | 0.3765 (3) | 0.55591 (10) | 0.0268 (4) | 0.9375 |
O12 | 0.18324 (13) | 0.0511 (3) | 0.63586 (11) | 0.0255 (4) | 0.9375 |
C11 | 0.16805 (17) | 0.3932 (4) | 0.72206 (14) | 0.0216 (5) | |
C12 | 0.13586 (17) | 0.5946 (4) | 0.70731 (15) | 0.0238 (5) | |
C13 | 0.09846 (18) | 0.7063 (4) | 0.77633 (16) | 0.0259 (5) | |
C14 | 0.09586 (17) | 0.6222 (4) | 0.86083 (15) | 0.0267 (6) | |
C15 | 0.12682 (18) | 0.4195 (4) | 0.87332 (15) | 0.0261 (6) | |
C16 | 0.16187 (18) | 0.3030 (4) | 0.80478 (15) | 0.0243 (5) | |
C17 | 0.0638 (2) | 0.7514 (4) | 0.93730 (18) | 0.0373 (7) | |
C21 | 0.38350 (17) | 0.0886 (4) | 0.75802 (14) | 0.0217 (5) | |
C22 | 0.36020 (18) | −0.1190 (4) | 0.74939 (15) | 0.0239 (5) | |
C23 | 0.35424 (18) | −0.2400 (4) | 0.82388 (16) | 0.0249 (6) | |
C24 | 0.37296 (17) | −0.1587 (4) | 0.90763 (15) | 0.0252 (5) | |
C25 | 0.39986 (18) | 0.0471 (4) | 0.91482 (15) | 0.0253 (5) | |
C26 | 0.40537 (18) | 0.1708 (4) | 0.84125 (15) | 0.0241 (5) | |
C27 | 0.3631 (2) | −0.2916 (5) | 0.98831 (17) | 0.0372 (7) | |
O21 | 0.393 (2) | 0.4675 (9) | 0.6771 (14) | 0.030* | 0.0625 |
O22 | 0.409 (2) | 0.144 (3) | 0.5880 (10) | 0.030* | 0.0625 |
H12 | 0.1395 | 0.6546 | 0.6506 | 0.029* | |
H13 | 0.0742 | 0.8421 | 0.7662 | 0.031* | |
H15 | 0.1238 | 0.3598 | 0.9301 | 0.031* | |
H16 | 0.1814 | 0.1638 | 0.8139 | 0.029* | |
H17A | 0.0567 | 0.6637 | 0.9890 | 0.056* | 0.70 (3) |
H17B | −0.0013 | 0.8176 | 0.9223 | 0.056* | 0.70 (3) |
H17C | 0.1153 | 0.8570 | 0.9503 | 0.056* | 0.70 (3) |
H17D | 0.0571 | 0.8952 | 0.9187 | 0.056* | 0.30 (3) |
H17E | 0.1151 | 0.7413 | 0.9854 | 0.056* | 0.30 (3) |
H17F | −0.0015 | 0.7019 | 0.9574 | 0.056* | 0.30 (3) |
H22 | 0.3484 | −0.1775 | 0.6927 | 0.029* | |
H23 | 0.3371 | −0.3812 | 0.8177 | 0.030* | |
H25 | 0.4148 | 0.1041 | 0.9713 | 0.030* | |
H26 | 0.4240 | 0.3113 | 0.8474 | 0.029* | |
H27A | 0.3514 | −0.2041 | 1.0394 | 0.056* | 0.61 (3) |
H27B | 0.4258 | −0.3705 | 0.9988 | 0.056* | 0.61 (3) |
H27C | 0.3059 | −0.3862 | 0.9791 | 0.056* | 0.61 (3) |
H27D | 0.3706 | −0.4364 | 0.9721 | 0.056* | 0.39 (3) |
H27E | 0.2963 | −0.2701 | 1.0127 | 0.056* | 0.39 (3) |
H27F | 0.4161 | −0.2543 | 1.0324 | 0.056* | 0.39 (3) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0229 (4) | 0.0247 (4) | 0.0183 (3) | 0.0004 (2) | −0.0009 (2) | 0.0009 (2) |
S2 | 0.0219 (4) | 0.0300 (4) | 0.0227 (3) | −0.0006 (2) | 0.0028 (2) | 0.0036 (2) |
O11 | 0.0321 (10) | 0.0312 (11) | 0.0170 (8) | 0.0013 (8) | −0.0006 (7) | 0.0045 (7) |
O12 | 0.0249 (10) | 0.0229 (10) | 0.0287 (9) | −0.0032 (7) | −0.0013 (7) | −0.0018 (7) |
C11 | 0.0176 (12) | 0.0251 (13) | 0.0220 (11) | −0.0016 (9) | 0.0002 (9) | 0.0000 (10) |
C12 | 0.0196 (12) | 0.0263 (13) | 0.0253 (12) | −0.0034 (10) | −0.0026 (9) | 0.0042 (10) |
C13 | 0.0188 (12) | 0.0260 (13) | 0.0327 (13) | −0.0006 (10) | −0.0012 (10) | −0.0015 (11) |
C14 | 0.0158 (12) | 0.0348 (15) | 0.0295 (13) | −0.0040 (10) | 0.0004 (9) | −0.0051 (11) |
C15 | 0.0195 (12) | 0.0380 (15) | 0.0210 (11) | −0.0030 (11) | 0.0016 (9) | 0.0036 (10) |
C16 | 0.0187 (12) | 0.0274 (13) | 0.0268 (12) | −0.0020 (10) | −0.0007 (9) | 0.0043 (10) |
C17 | 0.0298 (16) | 0.0476 (19) | 0.0348 (15) | 0.0013 (12) | 0.0040 (12) | −0.0118 (12) |
C21 | 0.0148 (11) | 0.0269 (13) | 0.0236 (12) | 0.0016 (9) | 0.0030 (9) | 0.0004 (10) |
C22 | 0.0225 (12) | 0.0265 (13) | 0.0227 (12) | 0.0025 (10) | −0.0012 (9) | −0.0036 (10) |
C23 | 0.0203 (13) | 0.0228 (13) | 0.0314 (13) | 0.0003 (9) | −0.0011 (10) | 0.0007 (10) |
C24 | 0.0172 (12) | 0.0335 (15) | 0.0249 (12) | 0.0027 (10) | 0.0005 (9) | 0.0044 (11) |
C25 | 0.0222 (13) | 0.0319 (14) | 0.0217 (12) | 0.0044 (10) | −0.0009 (9) | −0.0033 (10) |
C26 | 0.0209 (12) | 0.0241 (13) | 0.0269 (12) | 0.0024 (10) | −0.0016 (10) | −0.0026 (10) |
C27 | 0.0376 (16) | 0.0441 (17) | 0.0298 (14) | −0.0006 (13) | 0.0005 (12) | 0.0107 (12) |
Geometric parameters (Å, º) top
S1—O11 | 1.4464 (17) | C17—H17D | 0.9800 |
S1—O12 | 1.4226 (18) | C17—H17E | 0.9800 |
S1—C11 | 1.763 (2) | C17—H17F | 0.9800 |
S1—S2 | 2.1011 (9) | C21—C22 | 1.390 (3) |
S2—O21 | 1.428 (3) | C21—C26 | 1.395 (3) |
S2—O22 | 1.429 (3) | C22—C23 | 1.385 (3) |
S2—C21 | 1.774 (2) | C22—H22 | 0.9500 |
C11—C12 | 1.393 (3) | C23—C24 | 1.393 (3) |
C11—C16 | 1.394 (3) | C23—H23 | 0.9500 |
C12—C13 | 1.383 (3) | C24—C25 | 1.388 (4) |
C12—H12 | 0.9500 | C24—C27 | 1.511 (3) |
C13—C14 | 1.399 (3) | C25—C26 | 1.383 (3) |
C13—H13 | 0.9500 | C25—H25 | 0.9500 |
C14—C15 | 1.391 (4) | C26—H26 | 0.9500 |
C14—C17 | 1.509 (3) | C27—H27A | 0.9800 |
C15—C16 | 1.383 (3) | C27—H27B | 0.9800 |
C15—H15 | 0.9500 | C27—H27C | 0.9800 |
C16—H16 | 0.9500 | C27—H27D | 0.9800 |
C17—H17A | 0.9800 | C27—H27E | 0.9800 |
C17—H17B | 0.9800 | C27—H27F | 0.9800 |
C17—H17C | 0.9800 | | |
| | | |
O11—S1—O12 | 119.70 (11) | C14—C17—H17F | 109.5 |
C11—S1—O11 | 109.23 (11) | H17A—C17—H17F | 56.3 |
C11—S1—O12 | 108.63 (11) | H17B—C17—H17F | 56.3 |
S1—S2—C21 | 100.25 (8) | H17C—C17—H17F | 141.1 |
O11—S1—S2 | 102.92 (8) | H17D—C17—H17F | 109.5 |
O12—S1—S2 | 109.72 (8) | H17E—C17—H17F | 109.5 |
C11—S1—S2 | 105.71 (8) | C22—C21—C26 | 119.7 (2) |
O21—S2—O22 | 123.6 (8) | C22—C21—S2 | 120.28 (17) |
O21—S2—C21 | 118.6 (9) | C26—C21—S2 | 119.92 (19) |
O22—S2—C21 | 111.0 (9) | C23—C22—C21 | 119.6 (2) |
O21—S2—S1 | 97.8 (11) | C23—C22—H22 | 120.2 |
O22—S2—S1 | 98.1 (11) | C21—C22—H22 | 120.2 |
C12—C11—C16 | 120.9 (2) | C22—C23—C24 | 121.3 (2) |
C12—C11—S1 | 119.12 (17) | C22—C23—H23 | 119.4 |
C16—C11—S1 | 119.93 (19) | C24—C23—H23 | 119.4 |
C13—C12—C11 | 119.1 (2) | C25—C24—C23 | 118.3 (2) |
C13—C12—H12 | 120.4 | C25—C24—C27 | 121.2 (2) |
C11—C12—H12 | 120.4 | C23—C24—C27 | 120.6 (2) |
C12—C13—C14 | 121.0 (2) | C26—C25—C24 | 121.2 (2) |
C12—C13—H13 | 119.5 | C26—C25—H25 | 119.4 |
C14—C13—H13 | 119.5 | C24—C25—H25 | 119.4 |
C15—C14—C13 | 118.6 (2) | C25—C26—C21 | 119.8 (2) |
C15—C14—C17 | 120.8 (2) | C25—C26—H26 | 120.1 |
C13—C14—C17 | 120.6 (2) | C21—C26—H26 | 120.1 |
C16—C15—C14 | 121.4 (2) | C24—C27—H27A | 109.5 |
C16—C15—H15 | 119.3 | C24—C27—H27B | 109.5 |
C14—C15—H15 | 119.3 | H27A—C27—H27B | 109.5 |
C15—C16—C11 | 118.9 (2) | C24—C27—H27C | 109.5 |
C15—C16—H16 | 120.6 | H27A—C27—H27C | 109.5 |
C11—C16—H16 | 120.6 | H27B—C27—H27C | 109.5 |
C14—C17—H17A | 109.5 | C24—C27—H27D | 109.5 |
C14—C17—H17B | 109.5 | H27A—C27—H27D | 141.1 |
H17A—C17—H17B | 109.5 | H27B—C27—H27D | 56.3 |
C14—C17—H17C | 109.5 | H27C—C27—H27D | 56.3 |
H17A—C17—H17C | 109.5 | C24—C27—H27E | 109.5 |
H17B—C17—H17C | 109.5 | H27A—C27—H27E | 56.3 |
C14—C17—H17D | 109.5 | H27B—C27—H27E | 141.1 |
H17A—C17—H17D | 141.1 | H27C—C27—H27E | 56.3 |
H17B—C17—H17D | 56.3 | H27D—C27—H27E | 109.5 |
H17C—C17—H17D | 56.3 | C24—C27—H27F | 109.5 |
C14—C17—H17E | 109.5 | H27A—C27—H27F | 56.3 |
H17A—C17—H17E | 56.3 | H27B—C27—H27F | 56.3 |
H17B—C17—H17E | 141.1 | H27C—C27—H27F | 141.1 |
H17C—C17—H17E | 56.3 | H27D—C27—H27F | 109.5 |
H17D—C17—H17E | 109.5 | H27E—C27—H27F | 109.5 |
| | | |
S1—S2—C21—C22 | 68.56 (19) | C12—C13—C14—C17 | 174.4 (2) |
S1—S2—C21—C26 | −108.05 (18) | C13—C14—C15—C16 | 1.5 (3) |
S2—S1—C11—C12 | 104.09 (18) | C17—C14—C15—C16 | −176.2 (2) |
S2—S1—C11—C16 | −73.5 (2) | C14—C15—C16—C11 | 1.4 (4) |
O11—S1—S2—C21 | −176.52 (11) | C12—C11—C16—C15 | −2.5 (3) |
O12—S1—S2—C21 | −48.04 (11) | S1—C11—C16—C15 | 175.01 (18) |
C11—S1—S2—C21 | 68.92 (12) | O21—S2—C21—C22 | 173.4 (12) |
O12—S1—S2—O21 | −169.1 (9) | O22—S2—C21—C22 | −34.3 (12) |
O11—S1—S2—O21 | 62.4 (9) | O21—S2—C21—C26 | −3.2 (12) |
C11—S1—S2—O21 | −52.2 (9) | O22—S2—C21—C26 | 149.1 (11) |
O12—S1—S2—O22 | 65.1 (9) | C26—C21—C22—C23 | 3.0 (3) |
O11—S1—S2—O22 | −63.3 (9) | S2—C21—C22—C23 | −173.58 (18) |
C11—S1—S2—O22 | −177.9 (9) | C21—C22—C23—C24 | −1.2 (4) |
O12—S1—C11—C12 | −138.22 (19) | C22—C23—C24—C25 | −1.2 (3) |
O11—S1—C11—C12 | −6.0 (2) | C22—C23—C24—C27 | 178.2 (2) |
O12—S1—C11—C16 | 44.2 (2) | C23—C24—C25—C26 | 1.8 (3) |
O11—S1—C11—C16 | 176.40 (19) | C27—C24—C25—C26 | −177.7 (2) |
C16—C11—C12—C13 | 0.8 (3) | C24—C25—C26—C21 | 0.1 (3) |
S1—C11—C12—C13 | −176.78 (18) | C22—C21—C26—C25 | −2.5 (3) |
C11—C12—C13—C14 | 2.2 (3) | S2—C21—C26—C25 | 174.12 (18) |
C12—C13—C14—C15 | −3.3 (3) | | |
(Ib)
S-(4-tolyl) 4-toluenethiosulfonate at 293 K
top
Crystal data top
C14H14O2S2 | F(000) = 584 |
Mr = 278.37 | Dx = 1.376 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 13.3579 (7) Å | Cell parameters from 2633 reflections |
b = 6.6176 (4) Å | θ = 1.5–26.1° |
c = 15.2123 (11) Å | µ = 0.39 mm−1 |
β = 92.1322 (19)° | T = 293 K |
V = 1343.79 (14) Å3 | Plate, colourless |
Z = 4 | 0.10 × 0.10 × 0.05 mm |
Data collection top
Nonius Kappa-CCD diffractometer | 2633 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1451 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.062 |
φ scans and ω scans with κ offsets | θmax = 26.1°, θmin = 1.5° |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | h = −15→15 |
Tmin = 0.962, Tmax = 0.981 | k = −7→8 |
9656 measured reflections | l = −16→18 |
Refinement top
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0752P)2] where P = (Fo2 + 2Fc2)/3 |
2633 reflections | (Δ/σ)max = 0.002 |
173 parameters | Δρmax = 0.32 e Å−3 |
3 restraints | Δρmin = −0.32 e Å−3 |
Special details top
Experimental. Kappa CCD diffractometer using the following programs. Collect: Data collection
software, is a graphical user interface written by Enraf–Nonius which
encompasses the following programs. DENZO (Otwinowski & Minor, 1997) an
indexing and data collection software package and a scaling package,
SCALEPACK, both of which programs are produced by the company
HKL. Absorption corrections are performed by the SORTAV package
(Blessing, 1995 & 1997). High redundancy data were used in the scaling program
hence the 'multi-scan' code word was used. No transmission coefficients are
available from the program (only scale factors for each frame). The scale
factors in the experimental table are calculated from the 'size' command in
the SHELXL97 input file. Low temperature data are collected using an
Oxford Cryosystems cryostream. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1 | 0.22084 (6) | 0.25607 (12) | 0.63556 (5) | 0.0516 (3) | |
S2 | 0.37588 (6) | 0.25138 (13) | 0.66376 (5) | 0.0577 (3) | |
O11 | 0.21256 (16) | 0.3729 (4) | 0.55599 (14) | 0.0642 (7) | 0.96 |
O12 | 0.18280 (16) | 0.0557 (3) | 0.63676 (15) | 0.0621 (6) | 0.96 |
C11 | 0.1684 (2) | 0.3933 (5) | 0.72145 (19) | 0.0471 (8) | |
C12 | 0.1380 (2) | 0.5921 (5) | 0.7075 (2) | 0.0538 (8) | |
C13 | 0.1018 (2) | 0.7025 (5) | 0.7758 (2) | 0.0577 (9) | |
C14 | 0.0974 (2) | 0.6212 (6) | 0.8594 (2) | 0.0577 (9) | |
C15 | 0.1263 (2) | 0.4218 (5) | 0.8720 (2) | 0.0590 (9) | |
C16 | 0.1607 (2) | 0.3065 (5) | 0.8041 (2) | 0.0547 (8) | |
C17 | 0.0643 (3) | 0.7483 (6) | 0.9351 (3) | 0.0821 (12) | |
C21 | 0.3814 (2) | 0.0896 (5) | 0.75637 (19) | 0.0474 (7) | |
C22 | 0.3615 (2) | −0.1153 (5) | 0.7476 (2) | 0.0531 (8) | |
C23 | 0.3577 (2) | −0.2366 (5) | 0.8208 (2) | 0.0568 (9) | |
C24 | 0.3742 (2) | −0.1589 (6) | 0.9046 (2) | 0.0537 (8) | |
C25 | 0.3980 (2) | 0.0438 (5) | 0.9118 (2) | 0.0556 (8) | |
C26 | 0.4016 (2) | 0.1672 (5) | 0.8396 (2) | 0.0548 (8) | |
C27 | 0.3666 (3) | −0.2917 (6) | 0.9845 (2) | 0.0804 (12) | |
O21 | 0.393 (3) | 0.4639 (12) | 0.672 (2) | 0.030* | 0.04 |
O22 | 0.397 (3) | 0.145 (4) | 0.5846 (13) | 0.030* | 0.04 |
H12 | 0.1423 | 0.6502 | 0.6521 | 0.065* | |
H13 | 0.0798 | 0.8341 | 0.7658 | 0.069* | |
H15 | 0.1223 | 0.3645 | 0.9276 | 0.071* | |
H16 | 0.1786 | 0.1722 | 0.8134 | 0.066* | |
H17A | 0.0568 | 0.6641 | 0.9859 | 0.123* | 0.59 (4) |
H17B | 0.0013 | 0.8113 | 0.9196 | 0.123* | 0.59 (4) |
H17C | 0.1136 | 0.8504 | 0.9483 | 0.123* | 0.59 (4) |
H17D | 0.0577 | 0.8865 | 0.9166 | 0.123* | 0.41 (4) |
H17E | 0.1131 | 0.7392 | 0.9829 | 0.123* | 0.41 (4) |
H17F | 0.0009 | 0.7001 | 0.9542 | 0.123* | 0.41 (4) |
H22 | 0.3507 | −0.1709 | 0.6919 | 0.064* | |
H23 | 0.3437 | −0.3735 | 0.8139 | 0.068* | |
H25 | 0.4120 | 0.0982 | 0.9673 | 0.067* | |
H26 | 0.4177 | 0.3031 | 0.8466 | 0.066* | |
H27A | 0.3609 | −0.2089 | 1.0359 | 0.121* | 0.57 (5) |
H27B | 0.4255 | −0.3744 | 0.9909 | 0.121* | 0.57 (5) |
H27C | 0.3085 | −0.3766 | 0.9778 | 0.121* | 0.57 (5) |
H27D | 0.3690 | −0.4310 | 0.9671 | 0.121* | 0.43 (5) |
H27E | 0.3045 | −0.2655 | 1.0122 | 0.121* | 0.43 (5) |
H27F | 0.4214 | −0.2633 | 1.0253 | 0.121* | 0.43 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0557 (5) | 0.0568 (5) | 0.0421 (5) | −0.0021 (4) | −0.0022 (3) | 0.0031 (4) |
S2 | 0.0523 (5) | 0.0700 (6) | 0.0510 (6) | −0.0035 (4) | 0.0064 (4) | 0.0088 (4) |
O11 | 0.0758 (15) | 0.0736 (17) | 0.0427 (14) | 0.0051 (12) | −0.0027 (11) | 0.0117 (12) |
O12 | 0.0631 (14) | 0.0552 (15) | 0.0674 (16) | −0.0079 (11) | −0.0064 (11) | −0.0033 (12) |
C11 | 0.0440 (16) | 0.054 (2) | 0.0432 (19) | −0.0040 (14) | 0.0000 (13) | 0.0054 (15) |
C12 | 0.0556 (19) | 0.060 (2) | 0.045 (2) | −0.0062 (15) | −0.0027 (14) | 0.0099 (17) |
C13 | 0.0523 (19) | 0.052 (2) | 0.068 (3) | −0.0014 (15) | −0.0013 (16) | −0.0007 (18) |
C14 | 0.0463 (17) | 0.073 (3) | 0.054 (2) | −0.0072 (16) | 0.0015 (14) | −0.0047 (18) |
C15 | 0.0508 (18) | 0.078 (3) | 0.049 (2) | −0.0037 (17) | 0.0041 (14) | 0.0098 (19) |
C16 | 0.0487 (17) | 0.062 (2) | 0.053 (2) | −0.0027 (15) | 0.0039 (15) | 0.0114 (17) |
C17 | 0.067 (2) | 0.107 (3) | 0.073 (3) | 0.006 (2) | 0.0070 (19) | −0.018 (2) |
C21 | 0.0418 (16) | 0.056 (2) | 0.0447 (19) | 0.0015 (14) | 0.0016 (13) | −0.0021 (15) |
C22 | 0.0556 (18) | 0.059 (2) | 0.044 (2) | 0.0041 (15) | −0.0034 (14) | −0.0080 (17) |
C23 | 0.062 (2) | 0.047 (2) | 0.060 (2) | 0.0012 (15) | −0.0110 (16) | −0.0028 (18) |
C24 | 0.0456 (17) | 0.065 (2) | 0.050 (2) | 0.0037 (15) | 0.0008 (14) | 0.0099 (17) |
C25 | 0.0566 (18) | 0.065 (2) | 0.045 (2) | 0.0067 (16) | −0.0026 (14) | −0.0067 (18) |
C26 | 0.0578 (19) | 0.0504 (19) | 0.056 (2) | 0.0010 (15) | −0.0025 (16) | −0.0027 (18) |
C27 | 0.088 (3) | 0.095 (3) | 0.058 (3) | −0.001 (2) | −0.0039 (19) | 0.020 (2) |
Geometric parameters (Å, º) top
S1—O12 | 1.420 (2) | C17—H17D | 0.9600 |
S1—O11 | 1.437 (2) | C17—H17E | 0.9600 |
S1—C11 | 1.758 (3) | C17—H17F | 0.9600 |
S1—S2 | 2.0995 (11) | C21—C26 | 1.384 (4) |
S2—O21 | 1.431 (3) | C21—C22 | 1.387 (4) |
S2—O22 | 1.431 (3) | C22—C23 | 1.376 (4) |
S2—C21 | 1.769 (3) | C22—H22 | 0.9300 |
C11—C16 | 1.389 (4) | C23—C24 | 1.384 (4) |
C11—C12 | 1.391 (4) | C23—H23 | 0.9300 |
C12—C13 | 1.374 (4) | C24—C25 | 1.382 (4) |
C12—H12 | 0.9300 | C24—C27 | 1.508 (4) |
C13—C14 | 1.384 (4) | C25—C26 | 1.371 (4) |
C13—H13 | 0.9300 | C25—H25 | 0.9300 |
C14—C15 | 1.386 (5) | C26—H26 | 0.9300 |
C14—C17 | 1.506 (5) | C27—H27A | 0.9600 |
C15—C16 | 1.377 (4) | C27—H27B | 0.9600 |
C15—H15 | 0.9300 | C27—H27C | 0.9600 |
C16—H16 | 0.9300 | C27—H27D | 0.9600 |
C17—H17A | 0.9600 | C27—H27E | 0.9600 |
C17—H17B | 0.9600 | C27—H27F | 0.9600 |
C17—H17C | 0.9600 | | |
| | | |
O12—S1—O11 | 119.79 (14) | C14—C17—H17F | 109.5 |
O12—S1—C11 | 108.65 (14) | H17A—C17—H17F | 56.3 |
O11—S1—C11 | 109.14 (15) | H17B—C17—H17F | 56.3 |
O12—S1—S2 | 109.53 (10) | H17C—C17—H17F | 141.1 |
O11—S1—S2 | 102.97 (10) | H17D—C17—H17F | 109.5 |
C11—S1—S2 | 105.85 (10) | H17E—C17—H17F | 109.5 |
O21—S2—O22 | 121.5 (8) | C26—C21—C22 | 118.8 (3) |
O21—S2—C21 | 121.5 (14) | C26—C21—S2 | 120.3 (3) |
O22—S2—C21 | 111.6 (13) | C22—C21—S2 | 120.8 (2) |
O21—S2—S1 | 99.3 (16) | C23—C22—C21 | 120.3 (3) |
O22—S2—S1 | 93.2 (15) | C23—C22—H22 | 119.8 |
C21—S2—S1 | 100.55 (10) | C21—C22—H22 | 119.8 |
C16—C11—C12 | 119.9 (3) | C22—C23—C24 | 121.3 (3) |
C16—C11—S1 | 120.3 (2) | C22—C23—H23 | 119.4 |
C12—C11—S1 | 119.8 (2) | C24—C23—H23 | 119.4 |
C13—C12—C11 | 119.8 (3) | C25—C24—C23 | 117.6 (3) |
C13—C12—H12 | 120.1 | C25—C24—C27 | 121.6 (3) |
C11—C12—H12 | 120.1 | C23—C24—C27 | 120.8 (3) |
C12—C13—C14 | 121.1 (3) | C26—C25—C24 | 121.9 (3) |
C12—C13—H13 | 119.5 | C26—C25—H25 | 119.0 |
C14—C13—H13 | 119.5 | C24—C25—H25 | 119.0 |
C13—C14—C15 | 118.4 (3) | C25—C26—C21 | 120.1 (3) |
C13—C14—C17 | 120.6 (3) | C25—C26—H26 | 120.0 |
C15—C14—C17 | 120.9 (3) | C21—C26—H26 | 120.0 |
C16—C15—C14 | 121.5 (3) | C24—C27—H27A | 109.5 |
C16—C15—H15 | 119.2 | C24—C27—H27B | 109.5 |
C14—C15—H15 | 119.2 | H27A—C27—H27B | 109.5 |
C15—C16—C11 | 119.2 (3) | C24—C27—H27C | 109.5 |
C15—C16—H16 | 120.4 | H27A—C27—H27C | 109.5 |
C11—C16—H16 | 120.4 | H27B—C27—H27C | 109.5 |
C14—C17—H17A | 109.5 | C24—C27—H27D | 109.5 |
C14—C17—H17B | 109.5 | H27A—C27—H27D | 141.1 |
H17A—C17—H17B | 109.5 | H27B—C27—H27D | 56.3 |
C14—C17—H17C | 109.5 | H27C—C27—H27D | 56.3 |
H17A—C17—H17C | 109.5 | C24—C27—H27E | 109.5 |
H17B—C17—H17C | 109.5 | H27A—C27—H27E | 56.3 |
C14—C17—H17D | 109.5 | H27B—C27—H27E | 141.1 |
H17A—C17—H17D | 141.1 | H27C—C27—H27E | 56.3 |
H17B—C17—H17D | 56.3 | H27D—C27—H27E | 109.5 |
H17C—C17—H17D | 56.3 | C24—C27—H27F | 109.5 |
C14—C17—H17E | 109.5 | H27A—C27—H27F | 56.3 |
H17A—C17—H17E | 56.3 | H27B—C27—H27F | 56.3 |
H17B—C17—H17E | 141.1 | H27C—C27—H27F | 141.1 |
H17C—C17—H17E | 56.3 | H27D—C27—H27F | 109.5 |
H17D—C17—H17E | 109.5 | H27E—C27—H27F | 109.5 |
| | | |
O12—S1—S2—O21 | −171.7 (13) | C17—C14—C15—C16 | −177.2 (3) |
O11—S1—S2—O21 | 59.8 (13) | C14—C15—C16—C11 | 1.2 (4) |
C11—S1—S2—O21 | −54.7 (13) | C12—C11—C16—C15 | −2.3 (4) |
O12—S1—S2—O22 | 65.7 (13) | S1—C11—C16—C15 | 175.2 (2) |
O11—S1—S2—O22 | −62.8 (13) | O21—S2—C21—C26 | 0.9 (18) |
C11—S1—S2—O22 | −177.3 (13) | O22—S2—C21—C26 | 155.3 (16) |
O12—S1—S2—C21 | −46.97 (15) | S1—S2—C21—C26 | −106.9 (2) |
O11—S1—S2—C21 | −175.48 (15) | O21—S2—C21—C22 | 178.2 (18) |
C11—S1—S2—C21 | 69.99 (15) | O22—S2—C21—C22 | −27.4 (16) |
O12—S1—C11—C16 | 43.1 (3) | S1—S2—C21—C22 | 70.4 (2) |
O11—S1—C11—C16 | 175.4 (2) | C26—C21—C22—C23 | 2.9 (4) |
S2—S1—C11—C16 | −74.4 (2) | S2—C21—C22—C23 | −174.5 (2) |
O12—S1—C11—C12 | −139.4 (2) | C21—C22—C23—C24 | −0.6 (4) |
O11—S1—C11—C12 | −7.1 (3) | C22—C23—C24—C25 | −2.1 (4) |
S2—S1—C11—C12 | 103.1 (2) | C22—C23—C24—C27 | 178.0 (3) |
C16—C11—C12—C13 | 0.8 (4) | C23—C24—C25—C26 | 2.4 (4) |
S1—C11—C12—C13 | −176.7 (2) | C27—C24—C25—C26 | −177.7 (3) |
C11—C12—C13—C14 | 1.8 (4) | C24—C25—C26—C21 | −0.2 (4) |
C12—C13—C14—C15 | −2.9 (4) | C22—C21—C26—C25 | −2.5 (4) |
C12—C13—C14—C17 | 175.7 (3) | S2—C21—C26—C25 | 174.9 (2) |
C13—C14—C15—C16 | 1.3 (4) | | |
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