Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620007702/bm5126sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620007702/bm5126Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620007702/bm5126sup3.pdf |
CCDC references: 2008258; 2012245; 2012246; 2012247; 2012248; 2012249; 2012250; 2012251; 2012252; 2012253; 2012254; 2012255; 2012256; 2012257; 2012258; 2012259; 2012260; 2012261; 2012262; 2012263; 2012264
Data collection: Local Elettra software for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300. Cell refinement: XDS (Kabsch, 2010) for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300. Data reduction: XDS (Kabsch, 2010)) for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300. Program(s) used to solve structure: Superflip (Palatinus and Chapuis, 2007 for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300. Program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2018) for A110, A120, A130, A140, A150, A160, A170, A180, A190, A200, A210, A220, A230, A240, A250, A260, A270, A280, A290, A300.
C22H24O2S2 | β = 106.988 (3)° |
Mr = 384.56 | V = 935.24 (5) Å3 |
Monoclinic, p121/c1 | Z = 2.0 |
Hall symbol: -p 2ybc | Dx = 1.365 Mg m−3 |
a = 13.4387 (4) Å | µ = 0.25 mm−1 |
b = 5.09342 (10) Å | Stick, colourless |
c = 14.2867 (4) Å | 0.5 × 0.2 × 0.1 mm |
2897 independent reflections | k = → |
2897 reflections with F > 0 & F/u(F) > 3.0 & |F_calc| > 10−3 | l = → |
h = → |
Least-squares matrix: full | 72 constraints |
R[F2 > 2σ(F2)] = 0.030 | Hydrogen site location: HAR |
wR(F2) = 0.029 | Only H-atom coordinates refined |
S = 2.58 | Weighting scheme based on measured s.u.'s w = 1/σ(F) |
2897 reflections | (Δ/σ)max = 0.001 |
154 parameters | Δρmax = 0.42 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Refinement. . If constraints were applied they are defined by zero eigenvalues of the least-squares hessian, see the value of _refine_ls_SVD_threshold |
x | y | z | Uiso*/Ueq | ||
S1 | 0.647325 (17) | 0.32314 (4) | 0.537855 (15) | 0.02239 (12) | |
C2 | 0.64910 (7) | 0.55467 (16) | 0.62878 (6) | 0.0202 (4) | |
C3 | 0.55405 (6) | 0.69162 (16) | 0.61177 (6) | 0.0193 (4) | |
C4 | 0.48065 (6) | 0.59765 (16) | 0.52316 (6) | 0.0198 (4) | |
C5 | 0.54449 (7) | 0.88766 (17) | 0.67753 (6) | 0.0232 (4) | |
H5 | 0.4723 (8) | 0.9956 (19) | 0.6653 (7) | 0.027903 (1)* | |
C6 | 0.62900 (7) | 0.94065 (17) | 0.75831 (6) | 0.0233 (4) | |
H6 | 0.6228 (8) | 1.103 (2) | 0.8096 (7) | 0.028603 (1)* | |
C7 | 0.72378 (7) | 0.80264 (17) | 0.77628 (6) | 0.0215 (4) | |
C8 | 0.73354 (7) | 0.60776 (18) | 0.71101 (6) | 0.0226 (4) | |
H8 | 0.8023 (7) | 0.5077 (19) | 0.7252 (7) | 0.027314 (1)* | |
C9 | 0.81196 (7) | 0.86099 (18) | 0.86716 (6) | 0.0235 (4) | |
H9A | 0.8045 (8) | 1.0589 (19) | 0.8937 (7) | 0.028860 (1)* | |
H9B | 0.8864 (8) | 0.8645 (18) | 0.8516 (7) | 0.028860 (1)* | |
C10 | 0.81803 (8) | 0.66231 (18) | 0.94848 (6) | 0.0250 (5) | |
H10A | 0.8320 (8) | 0.470 (2) | 0.9206 (8) | 0.030570 (1)* | |
H10B | 0.7439 (8) | 0.6643 (19) | 0.9611 (7) | 0.030570 (1)* | |
C11 | 0.90223 (7) | 0.72552 (17) | 1.04372 (6) | 0.0228 (4) | |
H11A | 0.9774 (8) | 0.7461 (19) | 1.0320 (7) | 0.027961 (1)* | |
H11B | 0.8864 (8) | 0.9071 (19) | 1.0714 (7) | 0.027961 (1)* | |
C12 | 0.91161 (7) | 0.51262 (18) | 1.11944 (6) | 0.0244 (4) | |
H12A | 0.8398 (7) | 0.4893 (19) | 1.1358 (7) | 0.030085 (1)* | |
H12B | 0.9294 (7) | 0.3234 (19) | 1.0913 (7) | 0.030085 (1)* | |
O13 | 0.99092 (5) | 0.57593 (13) | 1.20706 (4) | 0.0276 (3) | |
H13 | 1.0025 (10) | 0.419 (3) | 1.2490 (9) | 0.041965 (1)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02104 (10) | 0.02602 (13) | 0.01892 (12) | 0.00299 (8) | 0.00397 (8) | −0.00490 (9) |
C2 | 0.0214 (4) | 0.0227 (4) | 0.0160 (4) | 0.0002 (3) | 0.0049 (3) | −0.0020 (3) |
C3 | 0.0208 (4) | 0.0211 (4) | 0.0164 (4) | −0.0006 (3) | 0.0061 (3) | −0.0024 (3) |
C4 | 0.0203 (4) | 0.0221 (4) | 0.0170 (4) | 0.0009 (3) | 0.0058 (3) | −0.0030 (3) |
C5 | 0.0242 (4) | 0.0255 (4) | 0.0191 (4) | 0.0008 (3) | 0.0051 (3) | −0.0053 (3) |
C6 | 0.0260 (4) | 0.0248 (4) | 0.0182 (4) | −0.0014 (3) | 0.0048 (3) | −0.0045 (3) |
C7 | 0.0242 (4) | 0.0239 (4) | 0.0148 (4) | −0.0037 (3) | 0.0031 (3) | −0.0015 (3) |
C8 | 0.0209 (4) | 0.0262 (4) | 0.0191 (4) | 0.0003 (3) | 0.0032 (3) | −0.0029 (3) |
C9 | 0.0263 (4) | 0.0243 (4) | 0.0172 (4) | −0.0054 (3) | 0.0020 (3) | −0.0006 (3) |
C10 | 0.0318 (5) | 0.0212 (4) | 0.0178 (4) | −0.0050 (4) | 0.0005 (3) | −0.0006 (3) |
C11 | 0.0288 (4) | 0.0195 (4) | 0.0169 (4) | −0.0032 (3) | 0.0016 (3) | −0.0018 (3) |
C12 | 0.0309 (5) | 0.0210 (4) | 0.0183 (4) | −0.0014 (3) | 0.0024 (4) | −0.0005 (3) |
O13 | 0.0329 (4) | 0.0267 (4) | 0.0187 (3) | −0.0008 (3) | 0.0006 (3) | −0.0015 (3) |
S1—C2 | 1.7495 (8) | C11—C12 | 1.5107 (12) |
O13—C12 | 1.4238 (10) | C5—H5 | 1.084 (10) |
O13—H13 | 0.985 (13) | C6—H6 | 1.124 (10) |
C2—C3 | 1.4128 (11) | C8—H8 | 1.022 (9) |
C2—C8 | 1.4007 (11) | C9—H9A | 1.092 (10) |
C3—C4 | 1.4405 (11) | C9—H9B | 1.086 (10) |
C3—C5 | 1.4024 (11) | C10—H10A | 1.095 (10) |
C5—C6 | 1.3887 (11) | C10—H10B | 1.064 (10) |
C6—C7 | 1.4112 (12) | C11—H11A | 1.077 (10) |
C7—C8 | 1.3940 (12) | C11—H11B | 1.052 (9) |
C7—C9 | 1.5097 (12) | C12—H12A | 1.063 (10) |
C9—C10 | 1.5249 (12) | C12—H12B | 1.097 (10) |
C10—C11 | 1.5283 (12) | ||
S1—C2—C3 | 112.93 (6) | C6—C5—H5 | 120.8 (5) |
S1—C2—C8 | 125.79 (7) | C7—C6—H6 | 118.9 (5) |
O13—C12—C11 | 110.57 (7) | C7—C8—H8 | 118.6 (5) |
O13—C12—H12A | 109.1 (5) | C7—C9—H9A | 110.6 (5) |
O13—C12—H12B | 109.5 (5) | C7—C9—H9B | 111.4 (5) |
C12—O13—H13 | 107.2 (7) | C9—C10—H10A | 107.1 (5) |
C2—C3—C4 | 109.85 (7) | C9—C10—H10B | 106.2 (5) |
C2—C3—C5 | 119.44 (7) | C10—C9—H9A | 109.8 (5) |
C2—C8—C7 | 119.14 (8) | C10—C9—H9B | 108.6 (5) |
C3—C2—C8 | 121.28 (7) | C10—C11—H11A | 111.5 (5) |
C3—C5—C6 | 118.84 (8) | C10—C11—H11B | 110.0 (5) |
C4—C3—C5 | 130.70 (8) | C11—C10—H10A | 110.6 (5) |
C5—C6—C7 | 122.00 (8) | C11—C10—H10B | 109.5 (5) |
C6—C7—C8 | 119.29 (8) | C11—C12—H12A | 110.2 (5) |
C6—C7—C9 | 119.89 (8) | C11—C12—H12B | 110.4 (5) |
C7—C9—C10 | 112.23 (7) | C12—C11—H11A | 107.2 (5) |
C8—C7—C9 | 120.79 (8) | C12—C11—H11B | 110.2 (5) |
C9—C10—C11 | 113.54 (7) | H9A—C9—H9B | 103.8 (7) |
C10—C11—C12 | 111.81 (7) | H10A—C10—H10B | 109.8 (7) |
C2—C8—H8 | 122.3 (5) | H11A—C11—H11B | 106.0 (7) |
C3—C5—H5 | 120.4 (5) | H12A—C12—H12B | 107.0 (7) |
C5—C6—H6 | 119.1 (5) |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.377 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.438 (3) Å | Cell parameters from 7090 reflections |
b = 5.061 (1) Å | θ = 2.5–25.0° |
c = 14.262 (1) Å | µ = 0.29 mm−1 |
β = 106.973 (15)° | T = 110 K |
V = 927.7 (3) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.025 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8303 measured reflections | h = −19→19 |
2748 independent reflections | k = −6→6 |
2488 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0546P)2 + 0.561P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2748 reflections | Δρmax = 0.95 e Å−3 |
121 parameters | Δρmin = −0.43 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.003 (2) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64732 (2) | 0.32338 (7) | 0.53732 (2) | 0.02323 (12) | |
C2 | 0.64913 (10) | 0.5558 (3) | 0.62860 (9) | 0.0208 (2) | |
C3 | 0.55401 (10) | 0.6922 (3) | 0.61188 (9) | 0.0205 (2) | |
C4 | 0.48088 (10) | 0.5974 (3) | 0.52338 (9) | 0.0205 (2) | |
C5 | 0.54471 (10) | 0.8887 (3) | 0.67775 (9) | 0.0237 (3) | |
H5 | 0.481553 | 0.984169 | 0.667387 | 0.028* | |
C6 | 0.62896 (10) | 0.9416 (3) | 0.75822 (9) | 0.0244 (3) | |
H6 | 0.622742 | 1.075183 | 0.802984 | 0.029* | |
C7 | 0.72359 (10) | 0.8039 (3) | 0.77586 (9) | 0.0221 (3) | |
C8 | 0.73353 (10) | 0.6092 (3) | 0.71059 (9) | 0.0230 (3) | |
H8 | 0.796754 | 0.513668 | 0.721522 | 0.028* | |
C9 | 0.81195 (11) | 0.8624 (3) | 0.86665 (9) | 0.0237 (3) | |
H9A | 0.802476 | 1.041443 | 0.890683 | 0.028* | |
H9B | 0.878310 | 0.861098 | 0.849668 | 0.028* | |
C10 | 0.81829 (12) | 0.6625 (3) | 0.94811 (10) | 0.0253 (3) | |
H10A | 0.832570 | 0.485571 | 0.925332 | 0.030* | |
H10B | 0.749998 | 0.654404 | 0.961293 | 0.030* | |
C11 | 0.90210 (11) | 0.7273 (3) | 1.04344 (9) | 0.0229 (3) | |
H11A | 0.969711 | 0.750140 | 1.029769 | 0.027* | |
H11B | 0.884640 | 0.896144 | 1.069977 | 0.027* | |
C12 | 0.91190 (11) | 0.5125 (3) | 1.11888 (9) | 0.0249 (3) | |
H12A | 0.844640 | 0.489809 | 1.133243 | 0.030* | |
H12B | 0.929605 | 0.343230 | 1.092803 | 0.030* | |
O13 | 0.99097 (8) | 0.5794 (2) | 1.20678 (7) | 0.0272 (2) | |
H13 | 1.0010 (12) | 0.456 (4) | 1.2441 (12) | 0.041* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02192 (17) | 0.02674 (19) | 0.02021 (17) | 0.00306 (11) | 0.00485 (12) | −0.00497 (11) |
C2 | 0.0238 (6) | 0.0218 (6) | 0.0179 (5) | −0.0002 (4) | 0.0076 (4) | −0.0009 (4) |
C3 | 0.0230 (5) | 0.0217 (6) | 0.0179 (5) | −0.0015 (4) | 0.0075 (4) | −0.0011 (4) |
C4 | 0.0210 (5) | 0.0229 (6) | 0.0183 (5) | 0.0003 (4) | 0.0067 (4) | −0.0012 (4) |
C5 | 0.0257 (6) | 0.0255 (6) | 0.0205 (5) | 0.0006 (5) | 0.0074 (5) | −0.0039 (5) |
C6 | 0.0293 (6) | 0.0247 (6) | 0.0195 (5) | −0.0028 (5) | 0.0076 (5) | −0.0039 (5) |
C7 | 0.0254 (6) | 0.0238 (6) | 0.0166 (5) | −0.0049 (5) | 0.0053 (4) | 0.0003 (4) |
C8 | 0.0231 (6) | 0.0258 (6) | 0.0197 (5) | −0.0005 (5) | 0.0055 (4) | −0.0012 (5) |
C9 | 0.0270 (6) | 0.0236 (6) | 0.0182 (5) | −0.0054 (5) | 0.0030 (4) | −0.0007 (4) |
C10 | 0.0323 (7) | 0.0206 (6) | 0.0192 (5) | −0.0051 (5) | 0.0017 (5) | −0.0003 (4) |
C11 | 0.0292 (6) | 0.0192 (6) | 0.0180 (5) | −0.0032 (5) | 0.0034 (4) | −0.0009 (4) |
C12 | 0.0318 (6) | 0.0212 (6) | 0.0187 (5) | −0.0024 (5) | 0.0025 (5) | −0.0007 (5) |
O13 | 0.0334 (5) | 0.0247 (5) | 0.0187 (4) | −0.0013 (4) | 0.0001 (4) | 0.0003 (4) |
S1—C4i | 1.7342 (13) | C9—C10 | 1.5241 (19) |
S1—C2 | 1.7496 (13) | C9—H9A | 0.9900 |
C2—C8 | 1.3972 (17) | C9—H9B | 0.9900 |
C2—C3 | 1.4104 (18) | C10—C11 | 1.5267 (18) |
C3—C5 | 1.3983 (18) | C10—H10A | 0.9900 |
C3—C4 | 1.4369 (17) | C10—H10B | 0.9900 |
C4—C4i | 1.372 (2) | C11—C12 | 1.5083 (19) |
C5—C6 | 1.3828 (18) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.4069 (19) | C12—O13 | 1.4274 (16) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.3887 (19) | C12—H12B | 0.9900 |
C7—C9 | 1.5088 (18) | O13—H13 | 0.81 (2) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.69 (6) | C10—C9—H9A | 109.2 |
C8—C2—C3 | 121.41 (12) | C7—C9—H9B | 109.2 |
C8—C2—S1 | 125.75 (10) | C10—C9—H9B | 109.2 |
C3—C2—S1 | 112.84 (9) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.26 (12) | C9—C10—C11 | 113.49 (11) |
C5—C3—C4 | 130.94 (12) | C9—C10—H10A | 108.9 |
C2—C3—C4 | 109.80 (11) | C11—C10—H10A | 108.9 |
C4i—C4—C3 | 114.20 (14) | C9—C10—H10B | 108.9 |
C4i—C4—S1i | 112.46 (13) | C11—C10—H10B | 108.9 |
C3—C4—S1i | 133.34 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.90 (12) | C12—C11—C10 | 111.61 (11) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 122.05 (12) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 108.0 |
C8—C7—C6 | 119.37 (12) | O13—C12—C11 | 110.06 (11) |
C8—C7—C9 | 120.59 (12) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 120.01 (12) | C11—C12—H12A | 109.6 |
C7—C8—C2 | 119.00 (12) | O13—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.2 |
C7—C9—C10 | 112.26 (11) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.2 | ||
C4i—S1—C2—C8 | 179.45 (12) | C3—C5—C6—C7 | −0.1 (2) |
C4i—S1—C2—C3 | −0.70 (10) | C5—C6—C7—C8 | 0.3 (2) |
C8—C2—C3—C5 | 1.29 (19) | C5—C6—C7—C9 | −177.82 (12) |
S1—C2—C3—C5 | −178.57 (10) | C6—C7—C8—C2 | 0.3 (2) |
C8—C2—C3—C4 | −179.51 (12) | C9—C7—C8—C2 | 178.37 (12) |
S1—C2—C3—C4 | 0.64 (14) | C3—C2—C8—C7 | −1.1 (2) |
C5—C3—C4—C4i | 178.88 (15) | S1—C2—C8—C7 | 178.76 (10) |
C2—C3—C4—C4i | −0.20 (19) | C8—C7—C9—C10 | −79.29 (16) |
C5—C3—C4—S1i | −1.5 (2) | C6—C7—C9—C10 | 98.78 (15) |
C2—C3—C4—S1i | 179.39 (11) | C7—C9—C10—C11 | −175.92 (12) |
C2—C3—C5—C6 | −0.7 (2) | C9—C10—C11—C12 | −175.02 (12) |
C4—C3—C5—C6 | −179.71 (13) | C10—C11—C12—O13 | 179.86 (11) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.81 | 2.02 | 2.7942 (9) | 160 |
C6—H6···S1iii | 0.95 | 3.30 | 4.0922 (13) | 142 |
C9—H9A···S1iii | 0.99 | 3.43 | 4.0609 (15) | 124 |
C10—H10B···S1iii | 0.99 | 3.31 | 3.9212 (16) | 122 |
C10—H10B···S1iv | 0.99 | 3.13 | 3.8276 (15) | 129 |
C11—H11B···S1iii | 0.99 | 3.40 | 4.0897 (16) | 129 |
C12—H12A···S1iv | 0.99 | 3.05 | 3.8037 (16) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.374 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.450 (3) Å | Cell parameters from 6962 reflections |
b = 5.063 (1) Å | θ = 2.3–24.3° |
c = 14.270 (1) Å | µ = 0.29 mm−1 |
β = 107.026 (15)° | T = 120 K |
V = 929.2 (3) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.023 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8199 measured reflections | h = −19→19 |
2739 independent reflections | k = −6→6 |
2497 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0565P)2 + 0.4952P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2739 reflections | Δρmax = 0.93 e Å−3 |
121 parameters | Δρmin = −0.45 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.003 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64721 (2) | 0.32336 (7) | 0.53739 (2) | 0.02441 (12) | |
C2 | 0.64899 (10) | 0.5559 (3) | 0.62858 (9) | 0.0218 (2) | |
C3 | 0.55402 (10) | 0.6920 (3) | 0.61191 (9) | 0.0216 (2) | |
C4 | 0.48089 (9) | 0.5974 (3) | 0.52340 (9) | 0.0216 (2) | |
C5 | 0.54474 (10) | 0.8884 (3) | 0.67769 (9) | 0.0250 (3) | |
H5 | 0.481631 | 0.983903 | 0.667235 | 0.030* | |
C6 | 0.62895 (10) | 0.9413 (3) | 0.75828 (9) | 0.0255 (3) | |
H6 | 0.622717 | 1.074594 | 0.803094 | 0.031* | |
C7 | 0.72360 (10) | 0.8037 (3) | 0.77586 (9) | 0.0233 (3) | |
C8 | 0.73341 (10) | 0.6090 (3) | 0.71070 (9) | 0.0241 (3) | |
H8 | 0.796540 | 0.513274 | 0.721708 | 0.029* | |
C9 | 0.81190 (11) | 0.8620 (3) | 0.86678 (9) | 0.0249 (3) | |
H9A | 0.802437 | 1.040962 | 0.890785 | 0.030* | |
H9B | 0.878236 | 0.860707 | 0.849881 | 0.030* | |
C10 | 0.81827 (12) | 0.6623 (3) | 0.94816 (10) | 0.0265 (3) | |
H10A | 0.832527 | 0.485499 | 0.925423 | 0.032* | |
H10B | 0.750029 | 0.654314 | 0.961301 | 0.032* | |
C11 | 0.90204 (11) | 0.7272 (3) | 1.04349 (9) | 0.0241 (3) | |
H11A | 0.969603 | 0.749838 | 1.029867 | 0.029* | |
H11B | 0.884625 | 0.896039 | 1.069954 | 0.029* | |
C12 | 0.91182 (11) | 0.5128 (3) | 1.11892 (9) | 0.0262 (3) | |
H12A | 0.844620 | 0.490403 | 1.133263 | 0.031* | |
H12B | 0.929413 | 0.343493 | 1.092882 | 0.031* | |
O13 | 0.99087 (8) | 0.5794 (2) | 1.20676 (7) | 0.0286 (2) | |
H13 | 1.0000 (12) | 0.457 (4) | 1.2444 (12) | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02290 (17) | 0.0281 (2) | 0.02137 (17) | 0.00317 (11) | 0.00508 (12) | −0.00530 (11) |
C2 | 0.0246 (6) | 0.0229 (6) | 0.0187 (5) | −0.0005 (4) | 0.0078 (4) | −0.0010 (4) |
C3 | 0.0244 (5) | 0.0225 (6) | 0.0188 (5) | −0.0015 (4) | 0.0078 (4) | −0.0009 (4) |
C4 | 0.0217 (5) | 0.0240 (6) | 0.0195 (5) | 0.0005 (4) | 0.0068 (4) | −0.0008 (4) |
C5 | 0.0273 (6) | 0.0266 (6) | 0.0214 (6) | 0.0006 (5) | 0.0077 (5) | −0.0041 (5) |
C6 | 0.0305 (6) | 0.0260 (6) | 0.0204 (5) | −0.0028 (5) | 0.0079 (5) | −0.0037 (5) |
C7 | 0.0267 (6) | 0.0251 (6) | 0.0175 (5) | −0.0051 (5) | 0.0055 (4) | 0.0002 (4) |
C8 | 0.0241 (6) | 0.0270 (6) | 0.0207 (5) | −0.0006 (5) | 0.0056 (4) | −0.0014 (5) |
C9 | 0.0285 (6) | 0.0250 (6) | 0.0188 (5) | −0.0058 (5) | 0.0033 (4) | −0.0007 (4) |
C10 | 0.0338 (7) | 0.0213 (6) | 0.0204 (5) | −0.0056 (5) | 0.0016 (5) | −0.0001 (4) |
C11 | 0.0304 (6) | 0.0204 (6) | 0.0189 (5) | −0.0034 (5) | 0.0032 (5) | −0.0010 (4) |
C12 | 0.0330 (6) | 0.0225 (6) | 0.0195 (5) | −0.0025 (5) | 0.0021 (5) | −0.0004 (5) |
O13 | 0.0351 (5) | 0.0259 (5) | 0.0196 (4) | −0.0011 (4) | −0.0001 (4) | 0.0006 (4) |
S1—C4i | 1.7340 (13) | C9—C10 | 1.5231 (19) |
S1—C2 | 1.7497 (13) | C9—H9A | 0.9900 |
C2—C8 | 1.3985 (17) | C9—H9B | 0.9900 |
C2—C3 | 1.4090 (18) | C10—C11 | 1.5265 (18) |
C3—C5 | 1.3977 (18) | C10—H10A | 0.9900 |
C3—C4 | 1.4368 (17) | C10—H10B | 0.9900 |
C4—C4i | 1.373 (2) | C11—C12 | 1.5072 (19) |
C5—C6 | 1.3837 (18) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.408 (2) | C12—O13 | 1.4265 (15) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.3876 (19) | C12—H12B | 0.9900 |
C7—C9 | 1.5095 (18) | O13—H13 | 0.80 (2) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.67 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.39 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.70 (10) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.91 (9) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.30 (12) | C9—C10—C11 | 113.50 (11) |
C5—C3—C4 | 130.89 (12) | C9—C10—H10A | 108.9 |
C2—C3—C4 | 109.80 (11) | C11—C10—H10A | 108.9 |
C4i—C4—C3 | 114.18 (14) | C9—C10—H10B | 108.9 |
C4i—C4—S1i | 112.43 (13) | C11—C10—H10B | 108.9 |
C3—C4—S1i | 133.39 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.93 (13) | C12—C11—C10 | 111.64 (11) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 121.97 (12) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 108.0 |
C8—C7—C6 | 119.39 (12) | O13—C12—C11 | 110.12 (11) |
C8—C7—C9 | 120.63 (13) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 119.95 (12) | C11—C12—H12A | 109.6 |
C7—C8—C2 | 119.01 (12) | O13—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.2 |
C7—C9—C10 | 112.34 (11) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.39 (12) | C3—C5—C6—C7 | 0.1 (2) |
C4i—S1—C2—C3 | −0.62 (10) | C5—C6—C7—C8 | 0.1 (2) |
C8—C2—C3—C5 | 1.43 (19) | C5—C6—C7—C9 | −177.79 (12) |
S1—C2—C3—C5 | −178.56 (10) | C6—C7—C8—C2 | 0.5 (2) |
C8—C2—C3—C4 | −179.46 (12) | C9—C7—C8—C2 | 178.35 (12) |
S1—C2—C3—C4 | 0.55 (14) | C3—C2—C8—C7 | −1.3 (2) |
C5—C3—C4—C4i | 178.82 (15) | S1—C2—C8—C7 | 178.73 (10) |
C2—C3—C4—C4i | −0.15 (19) | C8—C7—C9—C10 | −79.19 (16) |
C5—C3—C4—S1i | −1.6 (2) | C6—C7—C9—C10 | 98.66 (15) |
C2—C3—C4—S1i | 179.45 (11) | C7—C9—C10—C11 | −175.94 (12) |
C2—C3—C5—C6 | −0.8 (2) | C9—C10—C11—C12 | −175.06 (12) |
C4—C3—C5—C6 | −179.71 (13) | C10—C11—C12—O13 | 179.82 (12) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.80 | 2.03 | 2.7954 (9) | 160 |
C6—H6···S1iii | 0.95 | 3.30 | 4.0951 (13) | 142 |
C9—H9A···S1iii | 0.99 | 3.43 | 4.0657 (15) | 124 |
C10—H10B···S1iii | 0.99 | 3.31 | 3.9257 (17) | 122 |
C10—H10B···S1iv | 0.99 | 3.13 | 3.8312 (15) | 129 |
C11—H11B···S1iii | 0.99 | 3.40 | 4.0937 (16) | 129 |
C12—H12A···S1iv | 0.99 | 3.05 | 3.8068 (16) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.373 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.462 (2) Å | Cell parameters from 6972 reflections |
b = 5.064 (1) Å | θ = 2.5–24.8° |
c = 14.278 (1) Å | µ = 0.29 mm−1 |
β = 107.080 (14)° | T = 130 K |
V = 930.4 (2) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.023 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8277 measured reflections | h = −19→19 |
2748 independent reflections | k = −6→7 |
2496 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.110 | w = 1/[σ2(Fo2) + (0.0566P)2 + 0.4659P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2748 reflections | Δρmax = 0.91 e Å−3 |
121 parameters | Δρmin = −0.40 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.003 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64710 (2) | 0.32342 (7) | 0.53747 (2) | 0.02573 (12) | |
C2 | 0.64890 (10) | 0.5559 (3) | 0.62866 (9) | 0.0228 (2) | |
C3 | 0.55395 (10) | 0.6919 (3) | 0.61190 (9) | 0.0225 (2) | |
C4 | 0.48091 (9) | 0.5975 (3) | 0.52342 (9) | 0.0227 (2) | |
C5 | 0.54472 (10) | 0.8881 (3) | 0.67773 (9) | 0.0262 (3) | |
H5 | 0.481635 | 0.983473 | 0.667335 | 0.031* | |
C6 | 0.62893 (10) | 0.9410 (3) | 0.75825 (9) | 0.0267 (3) | |
H6 | 0.622760 | 1.074441 | 0.802976 | 0.032* | |
C7 | 0.72350 (10) | 0.8033 (3) | 0.77597 (9) | 0.0245 (3) | |
C8 | 0.73327 (10) | 0.6088 (3) | 0.71080 (9) | 0.0253 (3) | |
H8 | 0.796337 | 0.512999 | 0.721826 | 0.030* | |
C9 | 0.81171 (11) | 0.8618 (3) | 0.86675 (9) | 0.0263 (3) | |
H9A | 0.802211 | 1.040754 | 0.890704 | 0.032* | |
H9B | 0.877968 | 0.860599 | 0.849875 | 0.032* | |
C10 | 0.81821 (12) | 0.6623 (3) | 0.94819 (10) | 0.0280 (3) | |
H10A | 0.750034 | 0.654191 | 0.961321 | 0.034* | |
H10B | 0.832454 | 0.485443 | 0.925490 | 0.034* | |
C11 | 0.90197 (11) | 0.7272 (3) | 1.04349 (9) | 0.0254 (3) | |
H11A | 0.969474 | 0.749858 | 1.029905 | 0.030* | |
H11B | 0.884575 | 0.895995 | 1.069950 | 0.030* | |
C12 | 0.91174 (11) | 0.5127 (3) | 1.11885 (9) | 0.0275 (3) | |
H12A | 0.844589 | 0.490238 | 1.133143 | 0.033* | |
H12B | 0.929337 | 0.343453 | 1.092833 | 0.033* | |
O13 | 0.99080 (8) | 0.5795 (2) | 1.20673 (7) | 0.0302 (2) | |
H13 | 1.0001 (12) | 0.457 (4) | 1.2443 (12) | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02391 (17) | 0.0298 (2) | 0.02238 (17) | 0.00335 (11) | 0.00504 (12) | −0.00564 (11) |
C2 | 0.0257 (5) | 0.0242 (6) | 0.0191 (5) | −0.0005 (4) | 0.0075 (4) | −0.0009 (4) |
C3 | 0.0251 (5) | 0.0238 (6) | 0.0195 (5) | −0.0015 (4) | 0.0080 (4) | −0.0010 (4) |
C4 | 0.0229 (5) | 0.0255 (6) | 0.0200 (5) | 0.0004 (4) | 0.0068 (4) | −0.0010 (4) |
C5 | 0.0280 (6) | 0.0282 (6) | 0.0225 (5) | 0.0006 (5) | 0.0075 (5) | −0.0043 (5) |
C6 | 0.0317 (6) | 0.0268 (6) | 0.0216 (5) | −0.0031 (5) | 0.0078 (5) | −0.0041 (5) |
C7 | 0.0277 (6) | 0.0263 (6) | 0.0185 (5) | −0.0055 (5) | 0.0052 (4) | 0.0001 (4) |
C8 | 0.0254 (6) | 0.0281 (6) | 0.0215 (5) | −0.0010 (5) | 0.0057 (4) | −0.0016 (5) |
C9 | 0.0297 (6) | 0.0260 (6) | 0.0204 (5) | −0.0065 (5) | 0.0032 (4) | −0.0010 (4) |
C10 | 0.0359 (7) | 0.0224 (6) | 0.0211 (5) | −0.0060 (5) | 0.0013 (5) | −0.0003 (4) |
C11 | 0.0318 (6) | 0.0219 (6) | 0.0197 (5) | −0.0038 (5) | 0.0032 (5) | −0.0012 (4) |
C12 | 0.0345 (6) | 0.0234 (6) | 0.0207 (5) | −0.0025 (5) | 0.0022 (5) | −0.0008 (5) |
O13 | 0.0370 (5) | 0.0272 (5) | 0.0206 (4) | −0.0012 (4) | −0.0005 (4) | 0.0003 (4) |
S1—C4i | 1.7337 (13) | C9—C10 | 1.5235 (18) |
S1—C2 | 1.7503 (13) | C9—H9A | 0.9900 |
C2—C8 | 1.3981 (17) | C9—H9B | 0.9900 |
C2—C3 | 1.4090 (18) | C10—C11 | 1.5264 (18) |
C3—C5 | 1.3982 (17) | C10—H10A | 0.9900 |
C3—C4 | 1.4358 (17) | C10—H10B | 0.9900 |
C4—C4i | 1.375 (2) | C11—C12 | 1.5075 (18) |
C5—C6 | 1.3831 (18) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.4079 (19) | C12—O13 | 1.4273 (15) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.3874 (18) | C12—H12B | 0.9900 |
C7—C9 | 1.5079 (18) | O13—H13 | 0.80 (2) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.70 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.45 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.68 (10) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.87 (9) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.23 (12) | C11—C10—C9 | 113.53 (11) |
C5—C3—C4 | 130.91 (12) | C11—C10—H10A | 108.9 |
C2—C3—C4 | 109.85 (11) | C9—C10—H10A | 108.9 |
C4i—C4—C3 | 114.19 (14) | C11—C10—H10B | 108.9 |
C4i—C4—S1i | 112.38 (12) | C9—C10—H10B | 108.9 |
C3—C4—S1i | 133.43 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.91 (12) | C12—C11—C10 | 111.58 (11) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 122.05 (12) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 108.0 |
C8—C7—C6 | 119.33 (12) | O13—C12—C11 | 110.05 (11) |
C8—C7—C9 | 120.68 (12) | O13—C12—H12A | 109.7 |
C6—C7—C9 | 119.96 (12) | C11—C12—H12A | 109.7 |
C7—C8—C2 | 119.01 (12) | O13—C12—H12B | 109.7 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.7 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.2 |
C7—C9—C10 | 112.33 (11) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.34 (12) | C3—C5—C6—C7 | −0.1 (2) |
C4i—S1—C2—C3 | −0.60 (10) | C5—C6—C7—C8 | 0.2 (2) |
C8—C2—C3—C5 | 1.46 (19) | C5—C6—C7—C9 | −177.81 (12) |
S1—C2—C3—C5 | −178.59 (10) | C6—C7—C8—C2 | 0.45 (19) |
C8—C2—C3—C4 | −179.45 (12) | C9—C7—C8—C2 | 178.48 (12) |
S1—C2—C3—C4 | 0.50 (14) | C3—C2—C8—C7 | −1.3 (2) |
C5—C3—C4—C4i | 178.87 (15) | S1—C2—C8—C7 | 178.76 (10) |
C2—C3—C4—C4i | −0.09 (19) | C8—C7—C9—C10 | −79.25 (16) |
C5—C3—C4—S1i | −1.6 (2) | C6—C7—C9—C10 | 98.77 (15) |
C2—C3—C4—S1i | 179.45 (11) | C7—C9—C10—C11 | −175.96 (12) |
C2—C3—C5—C6 | −0.8 (2) | C9—C10—C11—C12 | −175.06 (12) |
C4—C3—C5—C6 | −179.62 (13) | C10—C11—C12—O13 | 179.84 (12) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.80 | 2.03 | 2.7963 (9) | 160 |
C6—H6···S1iii | 0.95 | 3.31 | 4.0993 (13) | 142 |
C9—H9A···S1iii | 0.99 | 3.43 | 4.0700 (15) | 124 |
C10—H10A···S1iii | 0.99 | 3.31 | 3.9292 (16) | 122 |
C10—H10A···S1iv | 0.99 | 3.14 | 3.8346 (15) | 129 |
C11—H11B···S1iii | 0.99 | 3.40 | 4.0968 (15) | 129 |
C12—H12A···S1iv | 0.99 | 3.05 | 3.8088 (15) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.371 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.473 (2) Å | Cell parameters from 6963 reflections |
b = 5.066 (1) Å | θ = 2.4–26.0° |
c = 14.286 (1) Å | µ = 0.29 mm−1 |
β = 107.137 (14)° | T = 140 K |
V = 931.8 (2) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.024 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8296 measured reflections | h = −19→19 |
2749 independent reflections | k = −6→7 |
2484 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.109 | w = 1/[σ2(Fo2) + (0.0541P)2 + 0.465P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2749 reflections | Δρmax = 0.91 e Å−3 |
121 parameters | Δρmin = −0.37 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.004 (2) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64700 (2) | 0.32344 (7) | 0.53754 (2) | 0.02705 (12) | |
C2 | 0.64886 (10) | 0.5556 (3) | 0.62875 (9) | 0.0239 (2) | |
C3 | 0.55395 (10) | 0.6918 (3) | 0.61189 (9) | 0.0235 (2) | |
C4 | 0.48091 (9) | 0.5972 (3) | 0.52336 (9) | 0.0235 (2) | |
C5 | 0.54474 (11) | 0.8876 (3) | 0.67773 (9) | 0.0274 (3) | |
H5 | 0.481678 | 0.982818 | 0.667359 | 0.033* | |
C6 | 0.62892 (11) | 0.9404 (3) | 0.75822 (9) | 0.0281 (3) | |
H6 | 0.622778 | 1.073735 | 0.802955 | 0.034* | |
C7 | 0.72340 (10) | 0.8029 (3) | 0.77594 (9) | 0.0257 (3) | |
C8 | 0.73318 (10) | 0.6089 (3) | 0.71079 (9) | 0.0264 (3) | |
H8 | 0.796292 | 0.513485 | 0.721769 | 0.032* | |
C9 | 0.81155 (11) | 0.8615 (3) | 0.86684 (9) | 0.0276 (3) | |
H9A | 0.802019 | 1.040429 | 0.890726 | 0.033* | |
H9B | 0.877798 | 0.860396 | 0.850058 | 0.033* | |
C10 | 0.81808 (12) | 0.6622 (3) | 0.94826 (10) | 0.0295 (3) | |
H10A | 0.749971 | 0.654316 | 0.961379 | 0.035* | |
H10B | 0.832242 | 0.485408 | 0.925585 | 0.035* | |
C11 | 0.90186 (11) | 0.7270 (3) | 1.04354 (9) | 0.0267 (3) | |
H11A | 0.969306 | 0.749398 | 1.029962 | 0.032* | |
H11B | 0.884566 | 0.895816 | 1.069948 | 0.032* | |
C12 | 0.91168 (11) | 0.5130 (3) | 1.11892 (9) | 0.0289 (3) | |
H12A | 0.844583 | 0.490746 | 1.133199 | 0.035* | |
H12B | 0.929181 | 0.343694 | 1.092955 | 0.035* | |
O13 | 0.99072 (8) | 0.5796 (2) | 1.20674 (7) | 0.0319 (2) | |
H13 | 1.0002 (13) | 0.457 (4) | 1.2441 (13) | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02489 (17) | 0.0314 (2) | 0.02349 (17) | 0.00360 (11) | 0.00509 (12) | −0.00586 (11) |
C2 | 0.0270 (6) | 0.0253 (6) | 0.0202 (5) | −0.0005 (5) | 0.0080 (4) | −0.0010 (4) |
C3 | 0.0262 (6) | 0.0252 (6) | 0.0199 (5) | −0.0014 (4) | 0.0079 (4) | −0.0008 (4) |
C4 | 0.0237 (5) | 0.0264 (6) | 0.0208 (5) | 0.0004 (4) | 0.0071 (4) | −0.0013 (4) |
C5 | 0.0291 (6) | 0.0295 (6) | 0.0238 (6) | 0.0004 (5) | 0.0080 (5) | −0.0046 (5) |
C6 | 0.0337 (6) | 0.0285 (6) | 0.0221 (5) | −0.0031 (5) | 0.0083 (5) | −0.0045 (5) |
C7 | 0.0289 (6) | 0.0278 (6) | 0.0192 (5) | −0.0061 (5) | 0.0054 (4) | 0.0002 (4) |
C8 | 0.0261 (6) | 0.0297 (6) | 0.0225 (5) | −0.0012 (5) | 0.0057 (4) | −0.0014 (5) |
C9 | 0.0312 (6) | 0.0276 (6) | 0.0210 (5) | −0.0067 (5) | 0.0030 (5) | −0.0010 (5) |
C10 | 0.0375 (7) | 0.0237 (6) | 0.0223 (6) | −0.0061 (5) | 0.0010 (5) | −0.0004 (4) |
C11 | 0.0329 (6) | 0.0231 (6) | 0.0209 (5) | −0.0039 (5) | 0.0031 (5) | −0.0016 (4) |
C12 | 0.0365 (7) | 0.0249 (6) | 0.0211 (5) | −0.0029 (5) | 0.0019 (5) | −0.0008 (5) |
O13 | 0.0388 (5) | 0.0289 (5) | 0.0218 (4) | −0.0014 (4) | −0.0009 (4) | 0.0001 (4) |
S1—C4i | 1.7333 (13) | C9—C10 | 1.5233 (19) |
S1—C2 | 1.7501 (13) | C9—H9A | 0.9900 |
C2—C8 | 1.3972 (17) | C9—H9B | 0.9900 |
C2—C3 | 1.4099 (18) | C10—C11 | 1.5260 (18) |
C3—C5 | 1.3973 (18) | C10—H10A | 0.9900 |
C3—C4 | 1.4366 (17) | C10—H10B | 0.9900 |
C4—C4i | 1.372 (2) | C11—C12 | 1.5062 (19) |
C5—C6 | 1.3826 (18) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.407 (2) | C12—O13 | 1.4265 (16) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.3865 (19) | C12—H12B | 0.9900 |
C7—C9 | 1.5086 (18) | O13—H13 | 0.80 (2) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.68 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.41 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.74 (10) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.85 (9) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.22 (12) | C11—C10—C9 | 113.56 (11) |
C5—C3—C4 | 130.97 (12) | C11—C10—H10A | 108.9 |
C2—C3—C4 | 109.80 (11) | C9—C10—H10A | 108.9 |
C4i—C4—C3 | 114.20 (14) | C11—C10—H10B | 108.9 |
C4i—C4—S1i | 112.46 (13) | C9—C10—H10B | 108.9 |
C3—C4—S1i | 133.34 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.92 (13) | C12—C11—C10 | 111.65 (11) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 122.05 (12) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 108.0 |
C8—C7—C6 | 119.35 (12) | O13—C12—C11 | 110.12 (11) |
C8—C7—C9 | 120.73 (13) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 119.90 (12) | C11—C12—H12A | 109.6 |
C7—C8—C2 | 119.04 (12) | O13—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.2 |
C7—C9—C10 | 112.36 (11) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.52 (13) | C3—C5—C6—C7 | −0.1 (2) |
C4i—S1—C2—C3 | −0.65 (10) | C5—C6—C7—C8 | 0.3 (2) |
C8—C2—C3—C5 | 1.2 (2) | C5—C6—C7—C9 | −177.79 (13) |
S1—C2—C3—C5 | −178.64 (10) | C6—C7—C8—C2 | 0.3 (2) |
C8—C2—C3—C4 | −179.54 (12) | C9—C7—C8—C2 | 178.35 (12) |
S1—C2—C3—C4 | 0.62 (14) | C3—C2—C8—C7 | −1.0 (2) |
C5—C3—C4—C4i | 178.91 (15) | S1—C2—C8—C7 | 178.78 (10) |
C2—C3—C4—C4i | −0.24 (19) | C8—C7—C9—C10 | −79.32 (17) |
C5—C3—C4—S1i | −1.4 (2) | C6—C7—C9—C10 | 98.72 (16) |
C2—C3—C4—S1i | 179.44 (11) | C7—C9—C10—C11 | −176.06 (12) |
C2—C3—C5—C6 | −0.6 (2) | C9—C10—C11—C12 | −175.08 (12) |
C4—C3—C5—C6 | −179.68 (13) | C10—C11—C12—O13 | 179.84 (12) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.80 | 2.03 | 2.7972 (10) | 160 |
C6—H6···S1iii | 0.95 | 3.31 | 4.1037 (13) | 142 |
C9—H9A···S1iii | 0.99 | 3.44 | 4.0738 (16) | 124 |
C10—H10A···S1iii | 0.99 | 3.32 | 3.9321 (17) | 122 |
C10—H10A···S1iv | 0.99 | 3.14 | 3.8373 (15) | 129 |
C11—H11B···S1iii | 0.99 | 3.41 | 4.1003 (16) | 129 |
C12—H12A···S1iv | 0.99 | 3.06 | 3.8117 (15) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.369 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.484 (2) Å | Cell parameters from 6940 reflections |
b = 5.068 (1) Å | θ = 2.4–24.9° |
c = 14.294 (1) Å | µ = 0.29 mm−1 |
β = 107.194 (12)° | T = 150 K |
V = 933.2 (2) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.023 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8300 measured reflections | h = −19→19 |
2741 independent reflections | k = −6→7 |
2472 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.111 | w = 1/[σ2(Fo2) + (0.0552P)2 + 0.473P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2741 reflections | Δρmax = 0.87 e Å−3 |
121 parameters | Δρmin = −0.38 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.004 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64689 (2) | 0.32342 (7) | 0.53763 (2) | 0.02843 (12) | |
C2 | 0.64878 (10) | 0.5555 (3) | 0.62876 (9) | 0.0249 (2) | |
C3 | 0.55399 (10) | 0.6915 (3) | 0.61196 (9) | 0.0246 (2) | |
C4 | 0.48093 (10) | 0.5971 (3) | 0.52333 (9) | 0.0246 (2) | |
C5 | 0.54480 (11) | 0.8872 (3) | 0.67774 (10) | 0.0287 (3) | |
H5 | 0.481761 | 0.982410 | 0.667308 | 0.034* | |
C6 | 0.62893 (11) | 0.9401 (3) | 0.75826 (9) | 0.0293 (3) | |
H6 | 0.622804 | 1.073344 | 0.802980 | 0.035* | |
C7 | 0.72333 (11) | 0.8026 (3) | 0.77600 (9) | 0.0269 (3) | |
C8 | 0.73313 (10) | 0.6085 (3) | 0.71084 (10) | 0.0277 (3) | |
H8 | 0.796186 | 0.513039 | 0.721856 | 0.033* | |
C9 | 0.81154 (11) | 0.8612 (3) | 0.86693 (10) | 0.0292 (3) | |
H9A | 0.802090 | 1.040047 | 0.890790 | 0.035* | |
H9B | 0.877727 | 0.859826 | 0.850182 | 0.035* | |
C10 | 0.81806 (12) | 0.6623 (3) | 0.94825 (10) | 0.0308 (3) | |
H10A | 0.749996 | 0.654588 | 0.961332 | 0.037* | |
H10B | 0.832125 | 0.485486 | 0.925599 | 0.037* | |
C11 | 0.90190 (11) | 0.7269 (3) | 1.04359 (9) | 0.0280 (3) | |
H11A | 0.969310 | 0.748952 | 1.030062 | 0.034* | |
H11B | 0.884725 | 0.895815 | 1.069944 | 0.034* | |
C12 | 0.91162 (12) | 0.5132 (3) | 1.11898 (10) | 0.0304 (3) | |
H12A | 0.844545 | 0.491266 | 1.133178 | 0.037* | |
H12B | 0.929044 | 0.343871 | 1.093085 | 0.037* | |
O13 | 0.99058 (9) | 0.5797 (2) | 1.20677 (7) | 0.0336 (2) | |
H13 | 1.0001 (13) | 0.455 (4) | 1.2448 (13) | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02608 (18) | 0.0330 (2) | 0.02467 (18) | 0.00379 (12) | 0.00520 (12) | −0.00617 (12) |
C2 | 0.0280 (6) | 0.0263 (6) | 0.0211 (5) | −0.0006 (5) | 0.0082 (4) | −0.0011 (4) |
C3 | 0.0266 (6) | 0.0267 (6) | 0.0211 (5) | −0.0016 (4) | 0.0081 (4) | −0.0009 (4) |
C4 | 0.0246 (5) | 0.0276 (6) | 0.0217 (5) | 0.0002 (5) | 0.0072 (4) | −0.0013 (5) |
C5 | 0.0307 (6) | 0.0310 (7) | 0.0246 (6) | 0.0007 (5) | 0.0083 (5) | −0.0049 (5) |
C6 | 0.0347 (7) | 0.0297 (7) | 0.0232 (6) | −0.0029 (5) | 0.0083 (5) | −0.0045 (5) |
C7 | 0.0304 (6) | 0.0290 (7) | 0.0200 (5) | −0.0061 (5) | 0.0055 (5) | 0.0000 (4) |
C8 | 0.0272 (6) | 0.0308 (7) | 0.0241 (6) | −0.0013 (5) | 0.0060 (5) | −0.0017 (5) |
C9 | 0.0331 (6) | 0.0289 (7) | 0.0222 (5) | −0.0073 (5) | 0.0030 (5) | −0.0009 (5) |
C10 | 0.0387 (7) | 0.0250 (6) | 0.0233 (6) | −0.0067 (5) | 0.0008 (5) | −0.0005 (5) |
C11 | 0.0343 (6) | 0.0241 (6) | 0.0223 (5) | −0.0041 (5) | 0.0030 (5) | −0.0017 (5) |
C12 | 0.0385 (7) | 0.0257 (6) | 0.0225 (6) | −0.0028 (5) | 0.0019 (5) | −0.0008 (5) |
O13 | 0.0407 (6) | 0.0306 (5) | 0.0227 (4) | −0.0015 (4) | −0.0011 (4) | 0.0001 (4) |
S1—C4i | 1.7332 (13) | C9—C10 | 1.5214 (19) |
S1—C2 | 1.7495 (13) | C9—H9A | 0.9900 |
C2—C8 | 1.3976 (18) | C9—H9B | 0.9900 |
C2—C3 | 1.4090 (18) | C10—C11 | 1.5269 (18) |
C3—C5 | 1.3971 (18) | C10—H10A | 0.9900 |
C3—C4 | 1.4375 (17) | C10—H10B | 0.9900 |
C4—C4i | 1.372 (3) | C11—C12 | 1.5059 (19) |
C5—C6 | 1.3826 (18) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.407 (2) | C12—O13 | 1.4254 (16) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.3879 (19) | C12—H12B | 0.9900 |
C7—C9 | 1.5093 (18) | O13—H13 | 0.82 (2) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.66 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.41 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.68 (10) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.91 (9) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.28 (12) | C11—C10—C9 | 113.59 (11) |
C5—C3—C4 | 130.95 (12) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.76 (11) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.18 (14) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.48 (13) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.34 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.93 (13) | C12—C11—C10 | 111.68 (11) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 122.01 (13) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.39 (12) | O13—C12—C11 | 110.15 (12) |
C8—C7—C9 | 120.67 (13) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 119.91 (12) | C11—C12—H12A | 109.6 |
C7—C8—C2 | 118.97 (13) | O13—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.37 (11) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.50 (13) | C3—C5—C6—C7 | −0.1 (2) |
C4i—S1—C2—C3 | −0.58 (10) | C5—C6—C7—C8 | 0.3 (2) |
C8—C2—C3—C5 | 1.3 (2) | C5—C6—C7—C9 | −177.80 (13) |
S1—C2—C3—C5 | −178.64 (10) | C6—C7—C8—C2 | 0.3 (2) |
C8—C2—C3—C4 | −179.54 (12) | C9—C7—C8—C2 | 178.39 (12) |
S1—C2—C3—C4 | 0.54 (14) | C3—C2—C8—C7 | −1.1 (2) |
C5—C3—C4—C4i | 178.87 (15) | S1—C2—C8—C7 | 178.80 (10) |
C2—C3—C4—C4i | −0.2 (2) | C8—C7—C9—C10 | −79.38 (17) |
C5—C3—C4—S1i | −1.5 (2) | C6—C7—C9—C10 | 98.67 (16) |
C2—C3—C4—S1i | 179.49 (11) | C7—C9—C10—C11 | −176.06 (13) |
C2—C3—C5—C6 | −0.7 (2) | C9—C10—C11—C12 | −175.13 (13) |
C4—C3—C5—C6 | −179.63 (14) | C10—C11—C12—O13 | 179.88 (12) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.82 | 2.02 | 2.7977 (10) | 160 |
C6—H6···S1iii | 0.95 | 3.31 | 4.1072 (14) | 142 |
C9—H9A···S1iii | 0.99 | 3.44 | 4.0793 (16) | 124 |
C10—H10A···S1iii | 0.99 | 3.32 | 3.9365 (17) | 122 |
C10—H10A···S1iv | 0.99 | 3.14 | 3.8421 (16) | 129 |
C11—H11B···S1iii | 0.99 | 3.41 | 4.1051 (16) | 129 |
C12—H12A···S1iv | 0.99 | 3.06 | 3.8146 (16) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.366 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.496 (3) Å | Cell parameters from 7083 reflections |
b = 5.070 (1) Å | θ = 2.4–25.5° |
c = 14.303 (1) Å | µ = 0.29 mm−1 |
β = 107.255 (14)° | T = 160 K |
V = 934.6 (3) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.021 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8282 measured reflections | h = −19→19 |
2741 independent reflections | k = −6→7 |
2463 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0604P)2 + 0.3814P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
2741 reflections | Δρmax = 0.83 e Å−3 |
121 parameters | Δρmin = −0.43 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.006 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64677 (2) | 0.32349 (7) | 0.53772 (2) | 0.02997 (13) | |
C2 | 0.64870 (10) | 0.5553 (3) | 0.62887 (9) | 0.0263 (3) | |
C3 | 0.55388 (10) | 0.6914 (3) | 0.61197 (9) | 0.0259 (3) | |
C4 | 0.48095 (10) | 0.5971 (3) | 0.52328 (9) | 0.0260 (3) | |
C5 | 0.54481 (11) | 0.8869 (3) | 0.67770 (10) | 0.0305 (3) | |
H5 | 0.481858 | 0.982238 | 0.667242 | 0.037* | |
C6 | 0.62899 (11) | 0.9394 (3) | 0.75829 (10) | 0.0309 (3) | |
H6 | 0.622901 | 1.072455 | 0.803035 | 0.037* | |
C7 | 0.72326 (11) | 0.8021 (3) | 0.77607 (9) | 0.0286 (3) | |
C8 | 0.73296 (11) | 0.6081 (3) | 0.71098 (10) | 0.0293 (3) | |
H8 | 0.795958 | 0.512629 | 0.722060 | 0.035* | |
C9 | 0.81147 (11) | 0.8606 (3) | 0.86704 (10) | 0.0308 (3) | |
H9A | 0.802077 | 1.039503 | 0.890843 | 0.037* | |
H9B | 0.877615 | 0.859090 | 0.850363 | 0.037* | |
C10 | 0.81792 (12) | 0.6620 (3) | 0.94833 (10) | 0.0326 (3) | |
H10A | 0.749901 | 0.654449 | 0.961342 | 0.039* | |
H10B | 0.831959 | 0.485176 | 0.925755 | 0.039* | |
C11 | 0.90174 (11) | 0.7268 (3) | 1.04363 (9) | 0.0297 (3) | |
H11A | 0.969086 | 0.748944 | 1.030131 | 0.036* | |
H11B | 0.884553 | 0.895686 | 1.069925 | 0.036* | |
C12 | 0.91156 (12) | 0.5135 (3) | 1.11897 (10) | 0.0322 (3) | |
H12A | 0.844544 | 0.491627 | 1.133139 | 0.039* | |
H12B | 0.928919 | 0.344250 | 1.093084 | 0.039* | |
O13 | 0.99050 (9) | 0.5796 (2) | 1.20678 (7) | 0.0355 (3) | |
H13 | 0.9989 (13) | 0.459 (4) | 1.2443 (13) | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02736 (18) | 0.0348 (2) | 0.02615 (18) | 0.00399 (12) | 0.00544 (12) | −0.00640 (12) |
C2 | 0.0288 (6) | 0.0282 (6) | 0.0224 (5) | −0.0007 (5) | 0.0083 (4) | −0.0013 (4) |
C3 | 0.0288 (6) | 0.0275 (6) | 0.0222 (5) | −0.0015 (4) | 0.0088 (4) | −0.0013 (4) |
C4 | 0.0264 (5) | 0.0290 (6) | 0.0227 (5) | 0.0003 (5) | 0.0077 (4) | −0.0010 (5) |
C5 | 0.0322 (6) | 0.0326 (7) | 0.0266 (6) | 0.0009 (5) | 0.0087 (5) | −0.0055 (5) |
C6 | 0.0366 (7) | 0.0313 (7) | 0.0245 (6) | −0.0033 (5) | 0.0085 (5) | −0.0050 (5) |
C7 | 0.0324 (6) | 0.0307 (7) | 0.0213 (5) | −0.0064 (5) | 0.0058 (5) | 0.0003 (5) |
C8 | 0.0285 (6) | 0.0329 (7) | 0.0252 (6) | −0.0013 (5) | 0.0060 (5) | −0.0013 (5) |
C9 | 0.0343 (7) | 0.0308 (7) | 0.0238 (6) | −0.0078 (5) | 0.0031 (5) | −0.0010 (5) |
C10 | 0.0407 (7) | 0.0267 (7) | 0.0245 (6) | −0.0072 (5) | 0.0008 (5) | −0.0010 (5) |
C11 | 0.0364 (6) | 0.0255 (6) | 0.0233 (6) | −0.0041 (5) | 0.0030 (5) | −0.0018 (5) |
C12 | 0.0402 (7) | 0.0272 (6) | 0.0244 (6) | −0.0030 (5) | 0.0021 (5) | −0.0009 (5) |
O13 | 0.0425 (6) | 0.0322 (6) | 0.0247 (5) | −0.0017 (4) | −0.0012 (4) | −0.0001 (4) |
S1—C4i | 1.7327 (14) | C9—C10 | 1.521 (2) |
S1—C2 | 1.7495 (13) | C9—H9A | 0.9900 |
C2—C8 | 1.3971 (18) | C9—H9B | 0.9900 |
C2—C3 | 1.4102 (18) | C10—C11 | 1.5267 (19) |
C3—C5 | 1.3964 (18) | C10—H10A | 0.9900 |
C3—C4 | 1.4372 (17) | C10—H10B | 0.9900 |
C4—C4i | 1.371 (3) | C11—C12 | 1.5044 (19) |
C5—C6 | 1.3833 (18) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.406 (2) | C12—O13 | 1.4251 (16) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.3869 (19) | C12—H12B | 0.9900 |
C7—C9 | 1.5097 (18) | O13—H13 | 0.80 (2) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.68 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.41 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.72 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.87 (10) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.23 (12) | C11—C10—C9 | 113.53 (12) |
C5—C3—C4 | 131.02 (12) | C11—C10—H10A | 108.9 |
C2—C3—C4 | 109.74 (11) | C9—C10—H10A | 108.9 |
C4i—C4—C3 | 114.21 (14) | C11—C10—H10B | 108.9 |
C4i—C4—S1i | 112.50 (13) | C9—C10—H10B | 108.9 |
C3—C4—S1i | 133.30 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.90 (13) | C12—C11—C10 | 111.67 (12) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 122.07 (13) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.36 (12) | O13—C12—C11 | 110.26 (12) |
C8—C7—C9 | 120.70 (13) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 119.91 (13) | C11—C12—H12A | 109.6 |
C7—C8—C2 | 119.01 (13) | O13—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.35 (11) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.49 (13) | C3—C5—C6—C7 | 0.0 (2) |
C4i—S1—C2—C3 | −0.60 (11) | C5—C6—C7—C8 | 0.2 (2) |
C8—C2—C3—C5 | 1.3 (2) | C5—C6—C7—C9 | −177.86 (13) |
S1—C2—C3—C5 | −178.58 (11) | C6—C7—C8—C2 | 0.4 (2) |
C8—C2—C3—C4 | −179.57 (12) | C9—C7—C8—C2 | 178.44 (12) |
S1—C2—C3—C4 | 0.51 (14) | C3—C2—C8—C7 | −1.2 (2) |
C5—C3—C4—C4i | 178.84 (15) | S1—C2—C8—C7 | 178.74 (11) |
C2—C3—C4—C4i | −0.1 (2) | C8—C7—C9—C10 | −79.43 (17) |
C5—C3—C4—S1i | −1.6 (2) | C6—C7—C9—C10 | 98.61 (16) |
C2—C3—C4—S1i | 179.45 (11) | C7—C9—C10—C11 | −176.05 (13) |
C2—C3—C5—C6 | −0.7 (2) | C9—C10—C11—C12 | −175.07 (13) |
C4—C3—C5—C6 | −179.59 (14) | C10—C11—C12—O13 | 179.84 (12) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.80 | 2.04 | 2.7986 (10) | 159 |
C6—H6···S1iii | 0.95 | 3.32 | 4.1118 (14) | 142 |
C9—H9A···S1iii | 0.99 | 3.45 | 4.0847 (17) | 124 |
C10—H10A···S1iii | 0.99 | 3.32 | 3.9404 (18) | 122 |
C10—H10A···S1iv | 0.99 | 3.15 | 3.8446 (16) | 129 |
C11—H11B···S1iii | 0.99 | 3.41 | 4.1078 (17) | 129 |
C12—H12A···S1iv | 0.99 | 3.06 | 3.8180 (17) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.364 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.508 (3) Å | Cell parameters from 6920 reflections |
b = 5.073 (1) Å | θ = 2.4–24.3° |
c = 14.312 (1) Å | µ = 0.29 mm−1 |
β = 107.316 (13)° | T = 170 K |
V = 936.3 (3) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.023 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8289 measured reflections | h = −19→19 |
2751 independent reflections | k = −6→7 |
2471 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.0605P)2 + 0.3871P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
2751 reflections | Δρmax = 0.80 e Å−3 |
121 parameters | Δρmin = −0.41 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.005 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64665 (3) | 0.32349 (8) | 0.53781 (2) | 0.03141 (13) | |
C2 | 0.64861 (10) | 0.5552 (3) | 0.62891 (9) | 0.0274 (3) | |
C3 | 0.55389 (10) | 0.6911 (3) | 0.61197 (9) | 0.0270 (3) | |
C4 | 0.48100 (10) | 0.5970 (3) | 0.52330 (9) | 0.0273 (3) | |
C5 | 0.54484 (11) | 0.8864 (3) | 0.67777 (10) | 0.0319 (3) | |
H5 | 0.481888 | 0.981428 | 0.667326 | 0.038* | |
C6 | 0.62888 (11) | 0.9391 (3) | 0.75830 (10) | 0.0325 (3) | |
H6 | 0.622802 | 1.072171 | 0.802957 | 0.039* | |
C7 | 0.72317 (11) | 0.8017 (3) | 0.77618 (9) | 0.0299 (3) | |
C8 | 0.73277 (11) | 0.6080 (3) | 0.71100 (10) | 0.0308 (3) | |
H8 | 0.795731 | 0.512520 | 0.722082 | 0.037* | |
C9 | 0.81135 (12) | 0.8603 (3) | 0.86708 (10) | 0.0324 (3) | |
H9A | 0.801991 | 1.039086 | 0.890831 | 0.039* | |
H9B | 0.877422 | 0.858637 | 0.850426 | 0.039* | |
C10 | 0.81785 (13) | 0.6618 (3) | 0.94840 (10) | 0.0342 (3) | |
H10A | 0.749905 | 0.654434 | 0.961403 | 0.041* | |
H10B | 0.831824 | 0.485071 | 0.925866 | 0.041* | |
C11 | 0.90164 (12) | 0.7266 (3) | 1.04360 (9) | 0.0311 (3) | |
H11A | 0.968926 | 0.748464 | 1.030113 | 0.037* | |
H11B | 0.884548 | 0.895476 | 1.069830 | 0.037* | |
C12 | 0.91148 (12) | 0.5136 (3) | 1.11901 (10) | 0.0336 (3) | |
H12A | 0.844514 | 0.491900 | 1.133126 | 0.040* | |
H12B | 0.928781 | 0.344342 | 1.093189 | 0.040* | |
O13 | 0.99036 (9) | 0.5796 (2) | 1.20677 (7) | 0.0373 (3) | |
H13 | 0.9998 (13) | 0.456 (4) | 1.2447 (13) | 0.056* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02865 (18) | 0.0365 (2) | 0.02729 (18) | 0.00422 (12) | 0.00559 (13) | −0.00672 (12) |
C2 | 0.0298 (6) | 0.0292 (6) | 0.0233 (5) | −0.0008 (5) | 0.0083 (4) | −0.0012 (5) |
C3 | 0.0295 (6) | 0.0290 (6) | 0.0231 (5) | −0.0017 (5) | 0.0089 (4) | −0.0013 (4) |
C4 | 0.0278 (5) | 0.0306 (6) | 0.0239 (5) | 0.0003 (5) | 0.0081 (4) | −0.0012 (5) |
C5 | 0.0339 (6) | 0.0342 (7) | 0.0275 (6) | 0.0007 (5) | 0.0090 (5) | −0.0054 (5) |
C6 | 0.0388 (7) | 0.0330 (7) | 0.0255 (6) | −0.0036 (5) | 0.0092 (5) | −0.0054 (5) |
C7 | 0.0338 (6) | 0.0324 (7) | 0.0218 (5) | −0.0068 (5) | 0.0057 (5) | 0.0002 (5) |
C8 | 0.0301 (6) | 0.0339 (7) | 0.0268 (6) | −0.0017 (5) | 0.0061 (5) | −0.0018 (5) |
C9 | 0.0362 (7) | 0.0325 (7) | 0.0245 (6) | −0.0083 (5) | 0.0029 (5) | −0.0010 (5) |
C10 | 0.0430 (8) | 0.0280 (7) | 0.0255 (6) | −0.0077 (5) | 0.0007 (5) | −0.0009 (5) |
C11 | 0.0381 (7) | 0.0268 (6) | 0.0243 (6) | −0.0046 (5) | 0.0029 (5) | −0.0021 (5) |
C12 | 0.0422 (7) | 0.0280 (7) | 0.0254 (6) | −0.0031 (5) | 0.0020 (5) | −0.0009 (5) |
O13 | 0.0445 (6) | 0.0337 (6) | 0.0258 (5) | −0.0016 (4) | −0.0017 (4) | 0.0001 (4) |
S1—C4i | 1.7330 (14) | C9—C10 | 1.521 (2) |
S1—C2 | 1.7499 (13) | C9—H9A | 0.9900 |
C2—C8 | 1.3962 (18) | C9—H9B | 0.9900 |
C2—C3 | 1.4095 (19) | C10—C11 | 1.5255 (19) |
C3—C5 | 1.3968 (18) | C10—H10A | 0.9900 |
C3—C4 | 1.4368 (17) | C10—H10B | 0.9900 |
C4—C4i | 1.371 (3) | C11—C12 | 1.505 (2) |
C5—C6 | 1.3819 (19) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.407 (2) | C12—O13 | 1.4242 (16) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.388 (2) | C12—H12B | 0.9900 |
C7—C9 | 1.5090 (18) | O13—H13 | 0.82 (2) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.67 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.41 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.71 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.88 (10) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.21 (12) | C11—C10—C9 | 113.54 (12) |
C5—C3—C4 | 131.05 (13) | C11—C10—H10A | 108.9 |
C2—C3—C4 | 109.73 (11) | C9—C10—H10A | 108.9 |
C4i—C4—C3 | 114.26 (15) | C11—C10—H10B | 108.9 |
C4i—C4—S1i | 112.45 (13) | C9—C10—H10B | 108.9 |
C3—C4—S1i | 133.29 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.98 (13) | C12—C11—C10 | 111.70 (12) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 122.03 (13) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.30 (12) | O13—C12—C11 | 110.31 (12) |
C8—C7—C9 | 120.75 (13) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 119.93 (13) | C11—C12—H12A | 109.6 |
C7—C8—C2 | 119.07 (13) | O13—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.36 (12) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.49 (13) | C3—C5—C6—C7 | −0.2 (2) |
C4i—S1—C2—C3 | −0.55 (11) | C5—C6—C7—C8 | 0.3 (2) |
C8—C2—C3—C5 | 1.3 (2) | C5—C6—C7—C9 | −177.86 (13) |
S1—C2—C3—C5 | −178.67 (11) | C6—C7—C8—C2 | 0.3 (2) |
C8—C2—C3—C4 | −179.55 (12) | C9—C7—C8—C2 | 178.50 (13) |
S1—C2—C3—C4 | 0.49 (15) | C3—C2—C8—C7 | −1.2 (2) |
C5—C3—C4—C4i | 178.88 (16) | S1—C2—C8—C7 | 178.81 (11) |
C2—C3—C4—C4i | −0.1 (2) | C8—C7—C9—C10 | −79.53 (18) |
C5—C3—C4—S1i | −1.5 (2) | C6—C7—C9—C10 | 98.62 (17) |
C2—C3—C4—S1i | 179.52 (11) | C7—C9—C10—C11 | −176.07 (13) |
C2—C3—C5—C6 | −0.6 (2) | C9—C10—C11—C12 | −175.10 (13) |
C4—C3—C5—C6 | −179.57 (14) | C10—C11—C12—O13 | 179.87 (13) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.82 | 2.02 | 2.8002 (10) | 160 |
C6—H6···S1iii | 0.95 | 3.32 | 4.1158 (14) | 142 |
C9—H9A···S1iii | 0.99 | 3.46 | 4.0902 (17) | 124 |
C10—H10A···S1iii | 0.99 | 3.33 | 3.9450 (18) | 122 |
C10—H10A···S1iv | 0.99 | 3.15 | 3.8482 (16) | 129 |
C11—H11B···S1iii | 0.99 | 3.42 | 4.1123 (17) | 129 |
C12—H12A···S1iv | 0.99 | 3.06 | 3.8207 (17) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.361 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.521 (3) Å | Cell parameters from 6914 reflections |
b = 5.076 (1) Å | θ = 2.4–24.7° |
c = 14.322 (1) Å | µ = 0.29 mm−1 |
β = 107.384 (14)° | T = 180 K |
V = 938.1 (3) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.022 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8298 measured reflections | h = −19→19 |
2758 independent reflections | k = −6→7 |
2465 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0603P)2 + 0.4239P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
2758 reflections | Δρmax = 0.81 e Å−3 |
121 parameters | Δρmin = −0.45 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.006 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64652 (3) | 0.32353 (8) | 0.53791 (2) | 0.03306 (13) | |
C2 | 0.64847 (11) | 0.5551 (3) | 0.62900 (9) | 0.0288 (3) | |
C3 | 0.55387 (11) | 0.6910 (3) | 0.61195 (10) | 0.0283 (3) | |
C4 | 0.48101 (10) | 0.5969 (3) | 0.52329 (9) | 0.0285 (3) | |
C5 | 0.54489 (12) | 0.8858 (3) | 0.67780 (10) | 0.0333 (3) | |
H5 | 0.481935 | 0.980543 | 0.667410 | 0.040* | |
C6 | 0.62893 (12) | 0.9386 (3) | 0.75832 (10) | 0.0339 (3) | |
H6 | 0.622884 | 1.071749 | 0.802915 | 0.041* | |
C7 | 0.72307 (11) | 0.8014 (3) | 0.77625 (10) | 0.0312 (3) | |
C8 | 0.73270 (11) | 0.6078 (3) | 0.71110 (10) | 0.0321 (3) | |
H8 | 0.795643 | 0.512570 | 0.722182 | 0.038* | |
C9 | 0.81118 (12) | 0.8599 (3) | 0.86713 (10) | 0.0342 (3) | |
H9A | 0.801884 | 1.038682 | 0.890817 | 0.041* | |
H9B | 0.877207 | 0.858089 | 0.850549 | 0.041* | |
C10 | 0.81772 (13) | 0.6620 (3) | 0.94844 (11) | 0.0358 (3) | |
H10A | 0.749825 | 0.654868 | 0.961382 | 0.043* | |
H10B | 0.831566 | 0.485256 | 0.925930 | 0.043* | |
C11 | 0.90150 (12) | 0.7263 (3) | 1.04369 (10) | 0.0326 (3) | |
H11A | 0.968745 | 0.747966 | 1.030275 | 0.039* | |
H11B | 0.884513 | 0.895114 | 1.069920 | 0.039* | |
C12 | 0.91131 (12) | 0.5136 (3) | 1.11905 (10) | 0.0351 (3) | |
H12A | 0.844415 | 0.491987 | 1.133145 | 0.042* | |
H12B | 0.928558 | 0.344296 | 1.093285 | 0.042* | |
O13 | 0.99025 (9) | 0.5798 (2) | 1.20678 (8) | 0.0393 (3) | |
H13 | 0.9996 (14) | 0.458 (4) | 1.2441 (14) | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.02995 (19) | 0.0385 (2) | 0.02873 (19) | 0.00444 (13) | 0.00576 (13) | −0.00705 (13) |
C2 | 0.0315 (6) | 0.0309 (7) | 0.0245 (5) | −0.0008 (5) | 0.0090 (5) | −0.0013 (5) |
C3 | 0.0308 (6) | 0.0302 (7) | 0.0244 (6) | −0.0017 (5) | 0.0091 (5) | −0.0014 (5) |
C4 | 0.0291 (6) | 0.0317 (7) | 0.0246 (5) | −0.0001 (5) | 0.0081 (5) | −0.0013 (5) |
C5 | 0.0347 (7) | 0.0358 (7) | 0.0291 (6) | 0.0006 (5) | 0.0089 (5) | −0.0058 (5) |
C6 | 0.0399 (7) | 0.0345 (7) | 0.0270 (6) | −0.0036 (6) | 0.0092 (5) | −0.0057 (5) |
C7 | 0.0353 (7) | 0.0330 (7) | 0.0235 (6) | −0.0071 (5) | 0.0060 (5) | 0.0003 (5) |
C8 | 0.0312 (6) | 0.0357 (7) | 0.0277 (6) | −0.0013 (5) | 0.0064 (5) | −0.0013 (5) |
C9 | 0.0380 (7) | 0.0342 (7) | 0.0259 (6) | −0.0086 (6) | 0.0027 (5) | −0.0009 (5) |
C10 | 0.0448 (8) | 0.0292 (7) | 0.0267 (6) | −0.0078 (6) | 0.0006 (5) | −0.0007 (5) |
C11 | 0.0397 (7) | 0.0275 (7) | 0.0259 (6) | −0.0053 (5) | 0.0027 (5) | −0.0021 (5) |
C12 | 0.0437 (8) | 0.0293 (7) | 0.0267 (6) | −0.0032 (6) | 0.0018 (5) | −0.0010 (5) |
O13 | 0.0466 (6) | 0.0358 (6) | 0.0269 (5) | −0.0019 (5) | −0.0020 (4) | 0.0003 (4) |
S1—C4i | 1.7325 (14) | C9—C10 | 1.520 (2) |
S1—C2 | 1.7505 (14) | C9—H9A | 0.9900 |
C2—C8 | 1.3968 (19) | C9—H9B | 0.9900 |
C2—C3 | 1.4088 (19) | C10—C11 | 1.5255 (19) |
C3—C5 | 1.3965 (19) | C10—H10A | 0.9900 |
C3—C4 | 1.4364 (18) | C10—H10B | 0.9900 |
C4—C4i | 1.372 (3) | C11—C12 | 1.504 (2) |
C5—C6 | 1.3819 (19) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.406 (2) | C12—O13 | 1.4246 (17) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.388 (2) | C12—H12B | 0.9900 |
C7—C9 | 1.5084 (19) | O13—H13 | 0.80 (3) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.67 (7) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.46 (13) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.66 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.88 (10) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.15 (12) | C11—C10—C9 | 113.67 (12) |
C5—C3—C4 | 131.09 (13) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.75 (12) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.25 (15) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.44 (14) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.30 (11) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 119.03 (14) | C12—C11—C10 | 111.78 (12) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 122.02 (13) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.33 (13) | O13—C12—C11 | 110.23 (12) |
C8—C7—C9 | 120.72 (14) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 119.93 (13) | C11—C12—H12A | 109.6 |
C7—C8—C2 | 119.00 (14) | O13—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.41 (12) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.57 (14) | C3—C5—C6—C7 | −0.3 (2) |
C4i—S1—C2—C3 | −0.58 (11) | C5—C6—C7—C8 | 0.4 (2) |
C8—C2—C3—C5 | 1.1 (2) | C5—C6—C7—C9 | −177.80 (14) |
S1—C2—C3—C5 | −178.74 (11) | C6—C7—C8—C2 | 0.3 (2) |
C8—C2—C3—C4 | −179.59 (13) | C9—C7—C8—C2 | 178.45 (13) |
S1—C2—C3—C4 | 0.55 (15) | C3—C2—C8—C7 | −1.0 (2) |
C5—C3—C4—C4i | 178.97 (16) | S1—C2—C8—C7 | 178.81 (11) |
C2—C3—C4—C4i | −0.2 (2) | C8—C7—C9—C10 | −79.61 (19) |
C5—C3—C4—S1i | −1.3 (3) | C6—C7—C9—C10 | 98.56 (17) |
C2—C3—C4—S1i | 179.51 (12) | C7—C9—C10—C11 | −176.11 (14) |
C2—C3—C5—C6 | −0.4 (2) | C9—C10—C11—C12 | −175.07 (14) |
C4—C3—C5—C6 | −179.55 (14) | C10—C11—C12—O13 | 179.88 (13) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.80 | 2.04 | 2.8015 (10) | 160 |
C6—H6···S1iii | 0.95 | 3.33 | 4.1206 (14) | 142 |
C9—H9A···S1iii | 0.99 | 3.46 | 4.0958 (18) | 124 |
C10—H10A···S1iii | 0.99 | 3.33 | 3.9486 (19) | 122 |
C10—H10A···S1iv | 0.99 | 3.16 | 3.8532 (17) | 129 |
C11—H11B···S1iii | 0.99 | 3.42 | 4.1164 (18) | 129 |
C12—H12A···S1iv | 0.99 | 3.07 | 3.8224 (18) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.359 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.535 (3) Å | Cell parameters from 7082 reflections |
b = 5.078 (1) Å | θ = 2.3–24.6° |
c = 14.332 (1) Å | µ = 0.29 mm−1 |
β = 107.455 (15)° | T = 190 K |
V = 939.7 (3) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.022 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8316 measured reflections | h = −19→19 |
2767 independent reflections | k = −6→7 |
2452 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0645P)2 + 0.3676P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
2767 reflections | Δρmax = 0.80 e Å−3 |
121 parameters | Δρmin = −0.50 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.007 (3) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64639 (3) | 0.32366 (8) | 0.53801 (3) | 0.03487 (14) | |
C2 | 0.64839 (11) | 0.5549 (3) | 0.62917 (10) | 0.0303 (3) | |
C3 | 0.55377 (11) | 0.6905 (3) | 0.61193 (10) | 0.0298 (3) | |
C4 | 0.48105 (11) | 0.5970 (3) | 0.52324 (10) | 0.0300 (3) | |
C5 | 0.54489 (12) | 0.8852 (3) | 0.67774 (11) | 0.0352 (3) | |
H5 | 0.481966 | 0.979859 | 0.667304 | 0.042* | |
C6 | 0.62890 (12) | 0.9383 (3) | 0.75827 (10) | 0.0360 (3) | |
H6 | 0.622866 | 1.071633 | 0.802744 | 0.043* | |
C7 | 0.72297 (12) | 0.8011 (3) | 0.77638 (10) | 0.0329 (3) | |
C8 | 0.73256 (11) | 0.6077 (3) | 0.71111 (11) | 0.0340 (3) | |
H8 | 0.795504 | 0.512824 | 0.722110 | 0.041* | |
C9 | 0.81105 (13) | 0.8594 (3) | 0.86716 (11) | 0.0360 (3) | |
H9A | 0.801878 | 1.038257 | 0.890750 | 0.043* | |
H9B | 0.876980 | 0.857233 | 0.850580 | 0.043* | |
C10 | 0.81767 (14) | 0.6618 (3) | 0.94866 (11) | 0.0377 (3) | |
H10A | 0.749865 | 0.654952 | 0.961623 | 0.045* | |
H10B | 0.831417 | 0.484939 | 0.926274 | 0.045* | |
C11 | 0.90139 (12) | 0.7262 (3) | 1.04369 (10) | 0.0344 (3) | |
H11A | 0.968558 | 0.747532 | 1.030265 | 0.041* | |
H11B | 0.884521 | 0.895187 | 1.069812 | 0.041* | |
C12 | 0.91118 (13) | 0.5138 (3) | 1.11914 (11) | 0.0371 (3) | |
H12A | 0.844348 | 0.492610 | 1.133219 | 0.045* | |
H12B | 0.928284 | 0.344412 | 1.093455 | 0.045* | |
O13 | 0.99007 (10) | 0.5798 (2) | 1.20674 (8) | 0.0415 (3) | |
H13 | 0.9994 (14) | 0.457 (4) | 1.2444 (14) | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0315 (2) | 0.0406 (2) | 0.0304 (2) | 0.00461 (13) | 0.00597 (14) | −0.00738 (13) |
C2 | 0.0327 (6) | 0.0327 (7) | 0.0257 (6) | −0.0008 (5) | 0.0091 (5) | −0.0013 (5) |
C3 | 0.0323 (6) | 0.0321 (7) | 0.0256 (6) | −0.0021 (5) | 0.0095 (5) | −0.0013 (5) |
C4 | 0.0306 (6) | 0.0334 (7) | 0.0260 (6) | 0.0004 (5) | 0.0084 (5) | −0.0016 (5) |
C5 | 0.0375 (7) | 0.0377 (7) | 0.0302 (6) | 0.0005 (6) | 0.0097 (5) | −0.0060 (6) |
C6 | 0.0422 (8) | 0.0367 (8) | 0.0283 (6) | −0.0038 (6) | 0.0095 (6) | −0.0058 (5) |
C7 | 0.0370 (7) | 0.0347 (7) | 0.0249 (6) | −0.0069 (5) | 0.0064 (5) | 0.0003 (5) |
C8 | 0.0328 (6) | 0.0379 (7) | 0.0294 (6) | −0.0015 (5) | 0.0066 (5) | −0.0016 (5) |
C9 | 0.0402 (7) | 0.0358 (7) | 0.0273 (6) | −0.0089 (6) | 0.0032 (5) | −0.0013 (5) |
C10 | 0.0469 (8) | 0.0310 (7) | 0.0279 (6) | −0.0080 (6) | 0.0002 (6) | −0.0006 (5) |
C11 | 0.0419 (7) | 0.0293 (7) | 0.0270 (6) | −0.0052 (6) | 0.0026 (5) | −0.0023 (5) |
C12 | 0.0461 (8) | 0.0305 (7) | 0.0285 (6) | −0.0035 (6) | 0.0017 (5) | −0.0010 (5) |
O13 | 0.0492 (6) | 0.0374 (6) | 0.0286 (5) | −0.0017 (5) | −0.0021 (4) | 0.0004 (4) |
S1—C4i | 1.7321 (15) | C9—C10 | 1.522 (2) |
S1—C2 | 1.7509 (14) | C9—H9A | 0.9900 |
C2—C8 | 1.3951 (19) | C9—H9B | 0.9900 |
C2—C3 | 1.409 (2) | C10—C11 | 1.523 (2) |
C3—C5 | 1.3961 (19) | C10—H10A | 0.9900 |
C3—C4 | 1.4350 (18) | C10—H10B | 0.9900 |
C4—C4i | 1.372 (3) | C11—C12 | 1.505 (2) |
C5—C6 | 1.382 (2) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.406 (2) | C12—O13 | 1.4228 (17) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.389 (2) | C12—H12B | 0.9900 |
C7—C9 | 1.507 (2) | O13—H13 | 0.81 (3) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.71 (7) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.56 (13) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.67 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.77 (10) | H9A—C9—H9B | 107.8 |
C5—C3—C2 | 119.04 (13) | C11—C10—C9 | 113.67 (12) |
C5—C3—C4 | 131.11 (13) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.84 (12) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.25 (16) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.42 (14) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.33 (11) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 119.11 (14) | C12—C11—C10 | 111.73 (12) |
C6—C5—H5 | 120.4 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.4 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 122.02 (14) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.24 (13) | O13—C12—C11 | 110.27 (13) |
C8—C7—C9 | 120.72 (14) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 120.02 (14) | C11—C12—H12A | 109.6 |
C7—C8—C2 | 119.03 (14) | O13—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.49 (12) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.68 (14) | C3—C5—C6—C7 | −0.4 (2) |
C4i—S1—C2—C3 | −0.61 (11) | C5—C6—C7—C8 | 0.6 (2) |
C8—C2—C3—C5 | 1.1 (2) | C5—C6—C7—C9 | −177.76 (14) |
S1—C2—C3—C5 | −178.65 (11) | C6—C7—C8—C2 | 0.0 (2) |
C8—C2—C3—C4 | −179.81 (13) | C9—C7—C8—C2 | 178.39 (13) |
S1—C2—C3—C4 | 0.48 (16) | C3—C2—C8—C7 | −0.9 (2) |
C5—C3—C4—C4i | 178.96 (17) | S1—C2—C8—C7 | 178.82 (11) |
C2—C3—C4—C4i | 0.0 (2) | C8—C7—C9—C10 | −79.83 (19) |
C5—C3—C4—S1i | −1.6 (3) | C6—C7—C9—C10 | 98.52 (18) |
C2—C3—C4—S1i | 179.42 (12) | C7—C9—C10—C11 | −176.09 (14) |
C2—C3—C5—C6 | −0.4 (2) | C9—C10—C11—C12 | −175.08 (14) |
C4—C3—C5—C6 | −179.33 (15) | C10—C11—C12—O13 | 179.87 (14) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.81 | 2.03 | 2.8029 (10) | 160 |
C6—H6···S1iii | 0.95 | 3.33 | 4.1257 (15) | 142 |
C9—H9A···S1iii | 0.99 | 3.47 | 4.1021 (18) | 124 |
C10—H10A···S1iii | 0.99 | 3.33 | 3.9523 (19) | 123 |
C10—H10A···S1iv | 0.99 | 3.16 | 3.8563 (18) | 129 |
C11—H11B···S1iii | 0.99 | 3.43 | 4.1201 (19) | 129 |
C12—H12A···S1iv | 0.99 | 3.07 | 3.8253 (18) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.357 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.550 (2) Å | Cell parameters from 7071 reflections |
b = 5.078 (1) Å | θ = 2.4–24.3° |
c = 14.344 (2) Å | µ = 0.29 mm−1 |
β = 107.529 (17)° | T = 200 K |
V = 941.1 (2) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.023 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8206 measured reflections | h = −19→19 |
2773 independent reflections | k = −6→7 |
2418 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.137 | w = 1/[σ2(Fo2) + (0.0697P)2 + 0.4379P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max = 0.001 |
2773 reflections | Δρmax = 0.82 e Å−3 |
121 parameters | Δρmin = −0.64 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.012 (4) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64631 (3) | 0.32361 (9) | 0.53812 (3) | 0.03699 (15) | |
C2 | 0.64831 (12) | 0.5547 (3) | 0.62921 (11) | 0.0323 (3) | |
C3 | 0.55386 (12) | 0.6903 (3) | 0.61199 (11) | 0.0318 (3) | |
C4 | 0.48109 (12) | 0.5967 (3) | 0.52328 (11) | 0.0317 (3) | |
C5 | 0.54478 (13) | 0.8847 (4) | 0.67768 (12) | 0.0371 (3) | |
H5 | 0.481879 | 0.979281 | 0.667196 | 0.044* | |
C6 | 0.62884 (14) | 0.9374 (4) | 0.75828 (11) | 0.0380 (4) | |
H6 | 0.622785 | 1.070326 | 0.802850 | 0.046* | |
C7 | 0.72288 (13) | 0.8008 (3) | 0.77638 (11) | 0.0349 (3) | |
C8 | 0.73246 (13) | 0.6072 (4) | 0.71127 (11) | 0.0359 (3) | |
H8 | 0.795306 | 0.511947 | 0.722405 | 0.043* | |
C9 | 0.81104 (14) | 0.8590 (4) | 0.86728 (12) | 0.0384 (4) | |
H9A | 0.801990 | 1.037969 | 0.890819 | 0.046* | |
H9B | 0.876928 | 0.856458 | 0.850809 | 0.046* | |
C10 | 0.81746 (15) | 0.6621 (3) | 0.94849 (12) | 0.0398 (4) | |
H10A | 0.749676 | 0.655627 | 0.961305 | 0.048* | |
H10B | 0.831073 | 0.485135 | 0.926135 | 0.048* | |
C11 | 0.90124 (14) | 0.7262 (3) | 1.04373 (11) | 0.0366 (3) | |
H11A | 0.968359 | 0.747626 | 1.030411 | 0.044* | |
H11B | 0.884396 | 0.895081 | 1.069884 | 0.044* | |
C12 | 0.91109 (15) | 0.5137 (3) | 1.11908 (12) | 0.0395 (4) | |
H12A | 0.844317 | 0.492335 | 1.133071 | 0.047* | |
H12B | 0.928251 | 0.344436 | 1.093430 | 0.047* | |
O13 | 0.98997 (11) | 0.5800 (3) | 1.20676 (9) | 0.0441 (3) | |
H13 | 0.9985 (15) | 0.458 (5) | 1.2451 (16) | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0339 (2) | 0.0427 (3) | 0.0319 (2) | 0.00472 (15) | 0.00612 (15) | −0.00774 (15) |
C2 | 0.0351 (7) | 0.0351 (8) | 0.0268 (6) | −0.0008 (6) | 0.0096 (5) | −0.0013 (5) |
C3 | 0.0350 (7) | 0.0342 (8) | 0.0265 (6) | −0.0019 (6) | 0.0096 (5) | −0.0014 (5) |
C4 | 0.0332 (7) | 0.0342 (8) | 0.0272 (6) | 0.0000 (6) | 0.0084 (5) | −0.0018 (5) |
C5 | 0.0398 (8) | 0.0387 (8) | 0.0320 (7) | 0.0008 (6) | 0.0097 (6) | −0.0061 (6) |
C6 | 0.0446 (9) | 0.0391 (9) | 0.0293 (7) | −0.0044 (7) | 0.0096 (6) | −0.0066 (6) |
C7 | 0.0401 (8) | 0.0367 (8) | 0.0254 (6) | −0.0076 (6) | 0.0063 (6) | 0.0003 (5) |
C8 | 0.0357 (7) | 0.0398 (8) | 0.0300 (7) | −0.0021 (6) | 0.0066 (6) | −0.0019 (6) |
C9 | 0.0437 (8) | 0.0381 (8) | 0.0285 (7) | −0.0096 (7) | 0.0036 (6) | −0.0010 (6) |
C10 | 0.0495 (9) | 0.0330 (8) | 0.0297 (7) | −0.0086 (7) | 0.0008 (6) | −0.0007 (6) |
C11 | 0.0448 (8) | 0.0308 (7) | 0.0283 (7) | −0.0054 (6) | 0.0022 (6) | −0.0021 (6) |
C12 | 0.0497 (9) | 0.0324 (8) | 0.0294 (7) | −0.0036 (7) | 0.0014 (6) | −0.0007 (6) |
O13 | 0.0526 (7) | 0.0397 (7) | 0.0301 (6) | −0.0023 (6) | −0.0023 (5) | 0.0004 (5) |
S1—C4i | 1.7330 (16) | C9—C10 | 1.517 (2) |
S1—C2 | 1.7503 (16) | C9—H9A | 0.9900 |
C2—C8 | 1.396 (2) | C9—H9B | 0.9900 |
C2—C3 | 1.408 (2) | C10—C11 | 1.525 (2) |
C3—C5 | 1.395 (2) | C10—H10A | 0.9900 |
C3—C4 | 1.436 (2) | C10—H10B | 0.9900 |
C4—C4i | 1.371 (3) | C11—C12 | 1.504 (2) |
C5—C6 | 1.383 (2) | C11—H11A | 0.9900 |
C5—H5 | 0.9500 | C11—H11B | 0.9900 |
C6—C7 | 1.405 (3) | C12—O13 | 1.4239 (19) |
C6—H6 | 0.9500 | C12—H12A | 0.9900 |
C7—C8 | 1.389 (2) | C12—H12B | 0.9900 |
C7—C9 | 1.509 (2) | O13—H13 | 0.81 (3) |
C8—H8 | 0.9500 | ||
C4i—S1—C2 | 90.68 (7) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.54 (15) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.63 (13) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.83 (11) | H9A—C9—H9B | 107.8 |
C5—C3—C2 | 119.20 (14) | C11—C10—C9 | 113.71 (14) |
C5—C3—C4 | 130.99 (15) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.81 (14) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.28 (18) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.39 (15) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.33 (12) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.92 (16) | C12—C11—C10 | 111.81 (14) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 122.12 (15) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 118.9 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 118.9 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.26 (15) | O13—C12—C11 | 110.22 (14) |
C8—C7—C9 | 120.65 (16) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 120.07 (15) | C11—C12—H12A | 109.6 |
C7—C8—C2 | 118.95 (16) | O13—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.44 (14) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.66 (16) | C3—C5—C6—C7 | −0.3 (3) |
C4i—S1—C2—C3 | −0.57 (13) | C5—C6—C7—C8 | 0.3 (3) |
C8—C2—C3—C5 | 1.1 (2) | C5—C6—C7—C9 | −177.81 (16) |
S1—C2—C3—C5 | −178.72 (13) | C6—C7—C8—C2 | 0.3 (2) |
C8—C2—C3—C4 | −179.69 (15) | C9—C7—C8—C2 | 178.46 (15) |
S1—C2—C3—C4 | 0.53 (17) | C3—C2—C8—C7 | −1.0 (2) |
C5—C3—C4—C4i | 178.94 (18) | S1—C2—C8—C7 | 178.72 (13) |
C2—C3—C4—C4i | −0.2 (2) | C8—C7—C9—C10 | −79.8 (2) |
C5—C3—C4—S1i | −1.4 (3) | C6—C7—C9—C10 | 98.3 (2) |
C2—C3—C4—S1i | 179.51 (13) | C7—C9—C10—C11 | −176.08 (16) |
C2—C3—C5—C6 | −0.4 (2) | C9—C10—C11—C12 | −174.94 (16) |
C4—C3—C5—C6 | −179.45 (16) | C10—C11—C12—O13 | 179.91 (16) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.81 | 2.03 | 2.8029 (10) | 159 |
C6—H6···S1iii | 0.95 | 3.34 | 4.1314 (17) | 143 |
C9—H9A···S1iii | 0.99 | 3.48 | 4.109 (2) | 124 |
C10—H10A···S1iii | 0.99 | 3.33 | 3.956 (2) | 123 |
C10—H10A···S1iv | 0.99 | 3.17 | 3.8614 (19) | 129 |
C11—H11B···S1iii | 0.99 | 3.43 | 4.123 (2) | 129 |
C12—H12A···S1iv | 0.99 | 3.07 | 3.8270 (19) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.355 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.569 (2) Å | Cell parameters from 7094 reflections |
b = 5.078 (1) Å | θ = 2.4–24.1° |
c = 14.355 (2) Å | µ = 0.29 mm−1 |
β = 107.612 (18)° | T = 210 K |
V = 942.7 (2) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.026 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8423 measured reflections | h = −19→19 |
2785 independent reflections | k = −6→7 |
2507 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0657P)2 + 0.3341P] where P = (Fo2 + 2Fc2)/3 |
2785 reflections | (Δ/σ)max = 0.001 |
120 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.54 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64615 (3) | 0.32373 (8) | 0.53817 (2) | 0.03642 (13) | |
C2 | 0.64810 (10) | 0.5545 (3) | 0.62911 (9) | 0.0313 (3) | |
C3 | 0.55382 (10) | 0.6902 (3) | 0.61197 (9) | 0.0304 (3) | |
C4 | 0.48107 (10) | 0.5967 (3) | 0.52317 (9) | 0.0309 (3) | |
C5 | 0.54488 (11) | 0.8844 (3) | 0.67770 (10) | 0.0366 (3) | |
H5 | 0.482697 | 0.977918 | 0.667313 | 0.044* | |
C6 | 0.62892 (12) | 0.9373 (3) | 0.75841 (10) | 0.0376 (3) | |
H6 | 0.623008 | 1.068842 | 0.802484 | 0.045* | |
C7 | 0.72273 (11) | 0.8005 (3) | 0.77643 (9) | 0.0344 (3) | |
C8 | 0.73236 (11) | 0.6072 (3) | 0.71137 (10) | 0.0352 (3) | |
H8 | 0.794532 | 0.513265 | 0.722420 | 0.042* | |
C9 | 0.81092 (12) | 0.8590 (3) | 0.86743 (10) | 0.0379 (3) | |
H9A | 0.801955 | 1.036134 | 0.890701 | 0.046* | |
H9B | 0.876071 | 0.856506 | 0.851211 | 0.046* | |
C10 | 0.81734 (13) | 0.6621 (3) | 0.94856 (10) | 0.0394 (3) | |
H10A | 0.750354 | 0.655765 | 0.961239 | 0.047* | |
H10B | 0.830748 | 0.486836 | 0.926457 | 0.047* | |
C11 | 0.90121 (12) | 0.7263 (3) | 1.04376 (9) | 0.0362 (3) | |
H11A | 0.967540 | 0.747249 | 1.030556 | 0.043* | |
H11B | 0.884661 | 0.893763 | 1.069536 | 0.043* | |
C12 | 0.91109 (12) | 0.5142 (3) | 1.11922 (10) | 0.0392 (3) | |
H12A | 0.845080 | 0.493447 | 1.133053 | 0.047* | |
H12B | 0.927885 | 0.346444 | 1.093882 | 0.047* | |
O13 | 0.98987 (9) | 0.5799 (2) | 1.20676 (7) | 0.0442 (3) | |
H13 | 0.9982 (13) | 0.461 (4) | 1.2439 (14) | 0.066* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.03197 (18) | 0.0430 (2) | 0.03142 (18) | 0.00506 (12) | 0.00521 (13) | −0.00803 (12) |
C2 | 0.0327 (6) | 0.0350 (6) | 0.0256 (5) | −0.0006 (5) | 0.0079 (4) | −0.0017 (5) |
C3 | 0.0322 (6) | 0.0333 (6) | 0.0255 (5) | −0.0017 (5) | 0.0084 (4) | −0.0015 (4) |
C4 | 0.0302 (5) | 0.0354 (6) | 0.0264 (5) | 0.0004 (5) | 0.0072 (4) | −0.0018 (5) |
C5 | 0.0376 (7) | 0.0395 (7) | 0.0313 (6) | 0.0010 (5) | 0.0086 (5) | −0.0067 (5) |
C6 | 0.0442 (7) | 0.0384 (7) | 0.0287 (6) | −0.0040 (6) | 0.0089 (5) | −0.0067 (5) |
C7 | 0.0387 (7) | 0.0372 (7) | 0.0245 (5) | −0.0081 (5) | 0.0054 (5) | 0.0000 (5) |
C8 | 0.0334 (6) | 0.0400 (7) | 0.0295 (6) | −0.0015 (5) | 0.0053 (5) | −0.0015 (5) |
C9 | 0.0422 (7) | 0.0380 (7) | 0.0279 (6) | −0.0100 (6) | 0.0020 (5) | −0.0008 (5) |
C10 | 0.0486 (8) | 0.0322 (7) | 0.0291 (6) | −0.0091 (6) | −0.0006 (5) | −0.0009 (5) |
C11 | 0.0436 (7) | 0.0308 (6) | 0.0278 (6) | −0.0054 (5) | 0.0014 (5) | −0.0021 (5) |
C12 | 0.0483 (8) | 0.0324 (7) | 0.0291 (6) | −0.0041 (6) | 0.0001 (5) | −0.0010 (5) |
O13 | 0.0516 (6) | 0.0404 (6) | 0.0297 (5) | −0.0019 (5) | −0.0040 (4) | 0.0003 (4) |
S1—C4i | 1.7316 (14) | C9—C10 | 1.517 (2) |
S1—C2 | 1.7486 (13) | C9—H9A | 0.9800 |
C2—C8 | 1.3987 (18) | C9—H9B | 0.9800 |
C2—C3 | 1.4074 (18) | C10—C11 | 1.5258 (19) |
C3—C5 | 1.3954 (18) | C10—H10A | 0.9800 |
C3—C4 | 1.4364 (17) | C10—H10B | 0.9800 |
C4—C4i | 1.370 (3) | C11—C12 | 1.505 (2) |
C5—C6 | 1.3840 (19) | C11—H11A | 0.9800 |
C5—H5 | 0.9400 | C11—H11B | 0.9800 |
C6—C7 | 1.404 (2) | C12—O13 | 1.4213 (16) |
C6—H6 | 0.9400 | C12—H12A | 0.9800 |
C7—C8 | 1.388 (2) | C12—H12B | 0.9800 |
C7—C9 | 1.5103 (19) | O13—H13 | 0.79 (3) |
C8—H8 | 0.9400 | ||
C4i—S1—C2 | 90.62 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.43 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.62 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.95 (9) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.22 (12) | C11—C10—C9 | 113.61 (12) |
C5—C3—C4 | 131.05 (13) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.73 (11) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.19 (15) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.51 (13) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.30 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 119.02 (13) | C12—C11—C10 | 111.81 (12) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.3 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.3 |
C5—C6—C7 | 121.99 (13) | C12—C11—H11B | 109.3 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.3 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.39 (12) | O13—C12—C11 | 110.35 (12) |
C8—C7—C9 | 120.64 (14) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 119.95 (13) | C11—C12—H12A | 109.6 |
C2—C8—C7 | 118.95 (13) | O13—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.39 (12) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.66 (13) | C3—C5—C6—C7 | −0.3 (2) |
C4i—S1—C2—C3 | −0.58 (11) | C5—C6—C7—C8 | 0.4 (2) |
C8—C2—C3—C5 | 1.1 (2) | C5—C6—C7—C9 | −177.84 (13) |
S1—C2—C3—C5 | −178.72 (11) | C3—C2—C8—C7 | −1.0 (2) |
C8—C2—C3—C4 | −179.74 (12) | S1—C2—C8—C7 | 178.77 (11) |
S1—C2—C3—C4 | 0.49 (15) | C6—C7—C8—C2 | 0.2 (2) |
C5—C3—C4—C4i | 178.99 (16) | C9—C7—C8—C2 | 178.49 (13) |
C2—C3—C4—C4i | −0.1 (2) | C8—C7—C9—C10 | −79.95 (18) |
C5—C3—C4—S1i | −1.4 (2) | C6—C7—C9—C10 | 98.31 (17) |
C2—C3—C4—S1i | 179.47 (11) | C7—C9—C10—C11 | −176.15 (14) |
C2—C3—C5—C6 | −0.4 (2) | C9—C10—C11—C12 | −175.02 (14) |
C4—C3—C5—C6 | −179.40 (14) | C10—C11—C12—O13 | 179.89 (13) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.79 | 2.05 | 2.8030 (9) | 159 |
C6—H6···S1iii | 0.94 | 3.35 | 4.1336 (15) | 143 |
C9—H9A···S1iii | 0.98 | 3.49 | 4.1132 (18) | 124 |
C10—H10A···S1iii | 0.98 | 3.34 | 3.9594 (18) | 123 |
C10—H10A···S1iv | 0.98 | 3.18 | 3.8657 (16) | 129 |
C11—H11B···S1iii | 0.98 | 3.44 | 4.1275 (17) | 129 |
C12—H12A···S1iv | 0.98 | 3.08 | 3.8330 (17) | 134 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.352 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.587 (2) Å | Cell parameters from 6932 reflections |
b = 5.077 (1) Å | θ = 2.2–25.5° |
c = 14.368 (2) Å | µ = 0.28 mm−1 |
β = 107.690 (16)° | T = 220 K |
V = 944.3 (2) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.024 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8507 measured reflections | h = −19→19 |
2798 independent reflections | k = −6→7 |
2563 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.117 | w = 1/[σ2(Fo2) + (0.067P)2 + 0.2715P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2798 reflections | Δρmax = 0.70 e Å−3 |
121 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.034 (4) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64601 (2) | 0.32374 (7) | 0.53824 (2) | 0.03750 (13) | |
C2 | 0.64812 (9) | 0.5542 (3) | 0.62923 (8) | 0.0320 (2) | |
C3 | 0.55384 (9) | 0.6901 (2) | 0.61200 (9) | 0.0314 (2) | |
C4 | 0.48110 (9) | 0.5966 (2) | 0.52319 (8) | 0.0315 (2) | |
C5 | 0.54487 (10) | 0.8842 (3) | 0.67770 (9) | 0.0377 (3) | |
H5 | 0.482728 | 0.977647 | 0.667287 | 0.045* | |
C6 | 0.62874 (11) | 0.9370 (3) | 0.75832 (9) | 0.0386 (3) | |
H6 | 0.622805 | 1.068372 | 0.802394 | 0.046* | |
C7 | 0.72264 (10) | 0.8003 (3) | 0.77644 (9) | 0.0353 (3) | |
C8 | 0.73220 (10) | 0.6073 (3) | 0.71140 (9) | 0.0362 (3) | |
H8 | 0.794373 | 0.513635 | 0.722444 | 0.043* | |
C9 | 0.81079 (11) | 0.8587 (3) | 0.86744 (9) | 0.0393 (3) | |
H9A | 0.801869 | 1.035996 | 0.890656 | 0.047* | |
H9B | 0.875863 | 0.856155 | 0.851293 | 0.047* | |
C10 | 0.81719 (12) | 0.6618 (3) | 0.94856 (10) | 0.0407 (3) | |
H10A | 0.750259 | 0.655548 | 0.961140 | 0.049* | |
H10B | 0.830581 | 0.486499 | 0.926527 | 0.049* | |
C11 | 0.90099 (11) | 0.7262 (3) | 1.04378 (9) | 0.0370 (3) | |
H11A | 0.967238 | 0.747350 | 1.030654 | 0.044* | |
H11B | 0.884400 | 0.893579 | 1.069529 | 0.044* | |
C12 | 0.91101 (11) | 0.5143 (3) | 1.11913 (9) | 0.0403 (3) | |
H12A | 0.845051 | 0.493148 | 1.132798 | 0.048* | |
H12B | 0.927936 | 0.346664 | 1.093839 | 0.048* | |
O13 | 0.98962 (9) | 0.5801 (2) | 1.20679 (7) | 0.0458 (3) | |
H13 | 0.9986 (13) | 0.459 (4) | 1.2442 (13) | 0.069* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.03189 (18) | 0.0447 (2) | 0.03289 (18) | 0.00539 (11) | 0.00540 (12) | −0.00829 (11) |
C2 | 0.0331 (5) | 0.0357 (6) | 0.0268 (5) | −0.0007 (4) | 0.0083 (4) | −0.0017 (4) |
C3 | 0.0327 (5) | 0.0344 (6) | 0.0272 (5) | −0.0019 (4) | 0.0092 (4) | −0.0020 (4) |
C4 | 0.0300 (5) | 0.0365 (6) | 0.0272 (5) | 0.0001 (4) | 0.0073 (4) | −0.0019 (4) |
C5 | 0.0382 (6) | 0.0411 (7) | 0.0329 (6) | 0.0011 (5) | 0.0094 (5) | −0.0067 (5) |
C6 | 0.0442 (7) | 0.0402 (7) | 0.0301 (5) | −0.0038 (5) | 0.0091 (5) | −0.0070 (5) |
C7 | 0.0383 (6) | 0.0386 (6) | 0.0259 (5) | −0.0083 (5) | 0.0053 (4) | 0.0002 (4) |
C8 | 0.0330 (6) | 0.0422 (7) | 0.0306 (5) | −0.0016 (5) | 0.0053 (4) | −0.0015 (5) |
C9 | 0.0428 (7) | 0.0400 (7) | 0.0292 (5) | −0.0104 (5) | 0.0023 (5) | −0.0012 (5) |
C10 | 0.0495 (7) | 0.0336 (6) | 0.0304 (6) | −0.0093 (5) | −0.0005 (5) | −0.0009 (4) |
C11 | 0.0438 (6) | 0.0316 (6) | 0.0294 (5) | −0.0055 (5) | 0.0020 (5) | −0.0025 (4) |
C12 | 0.0487 (7) | 0.0339 (6) | 0.0302 (5) | −0.0043 (5) | −0.0002 (5) | −0.0012 (5) |
O13 | 0.0535 (6) | 0.0414 (5) | 0.0310 (4) | −0.0024 (4) | −0.0046 (4) | 0.0003 (4) |
S1—C4i | 1.7318 (12) | C9—C10 | 1.5180 (19) |
S1—C2 | 1.7481 (12) | C9—H9A | 0.9800 |
C2—C8 | 1.3971 (16) | C9—H9B | 0.9800 |
C2—C3 | 1.4093 (17) | C10—C11 | 1.5260 (18) |
C3—C5 | 1.3953 (17) | C10—H10A | 0.9800 |
C3—C4 | 1.4367 (16) | C10—H10B | 0.9800 |
C4—C4i | 1.370 (2) | C11—C12 | 1.5026 (18) |
C5—C6 | 1.3820 (17) | C11—H11A | 0.9800 |
C5—H5 | 0.9400 | C11—H11B | 0.9800 |
C6—C7 | 1.405 (2) | C12—O13 | 1.4217 (15) |
C6—H6 | 0.9400 | C12—H12A | 0.9800 |
C7—C8 | 1.3869 (18) | C12—H12B | 0.9800 |
C7—C9 | 1.5101 (17) | O13—H13 | 0.80 (2) |
C8—H8 | 0.9400 | ||
C4i—S1—C2 | 90.69 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.33 (11) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.78 (10) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.89 (9) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.25 (11) | C11—C10—C9 | 113.59 (11) |
C5—C3—C4 | 131.03 (11) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.72 (11) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.22 (13) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.48 (12) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.30 (9) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.99 (12) | C12—C11—C10 | 111.84 (11) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.2 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.2 |
C5—C6—C7 | 122.03 (12) | C12—C11—H11B | 109.2 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.2 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.31 (11) | O13—C12—C11 | 110.44 (11) |
C8—C7—C9 | 120.68 (13) | O13—C12—H12A | 109.6 |
C6—C7—C9 | 119.99 (12) | C11—C12—H12A | 109.6 |
C2—C8—C7 | 119.07 (12) | O13—C12—H12B | 109.6 |
C2—C8—H8 | 120.5 | C11—C12—H12B | 109.6 |
C7—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.37 (11) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.80 (12) | C3—C5—C6—C7 | −0.3 (2) |
C4i—S1—C2—C3 | −0.61 (10) | C5—C6—C7—C8 | 0.4 (2) |
C8—C2—C3—C5 | 0.89 (19) | C5—C6—C7—C9 | −177.87 (12) |
S1—C2—C3—C5 | −178.72 (10) | C3—C2—C8—C7 | −0.8 (2) |
C8—C2—C3—C4 | −179.81 (11) | S1—C2—C8—C7 | 178.76 (10) |
S1—C2—C3—C4 | 0.58 (13) | C6—C7—C8—C2 | 0.1 (2) |
C5—C3—C4—C4i | 178.96 (15) | C9—C7—C8—C2 | 178.43 (12) |
C2—C3—C4—C4i | −0.22 (19) | C8—C7—C9—C10 | −80.06 (17) |
C5—C3—C4—S1i | −1.3 (2) | C6—C7—C9—C10 | 98.21 (16) |
C2—C3—C4—S1i | 179.48 (10) | C7—C9—C10—C11 | −176.12 (13) |
C2—C3—C5—C6 | −0.3 (2) | C9—C10—C11—C12 | −174.93 (13) |
C4—C3—C5—C6 | −179.44 (13) | C10—C11—C12—O13 | 179.97 (12) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.80 | 2.04 | 2.8022 (8) | 160 |
C6—H6···S1iii | 0.94 | 3.35 | 4.1392 (14) | 143 |
C9—H9A···S1iii | 0.98 | 3.50 | 4.1198 (17) | 124 |
C10—H10A···S1iii | 0.98 | 3.34 | 3.9639 (17) | 123 |
C10—H10A···S1iv | 0.98 | 3.18 | 3.8687 (15) | 129 |
C11—H11B···S1iii | 0.98 | 3.44 | 4.1306 (16) | 129 |
C12—H12A···S1iv | 0.98 | 3.08 | 3.8364 (15) | 135 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.350 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.606 (2) Å | Cell parameters from 6988 reflections |
b = 5.077 (1) Å | θ = 2.2–24.4° |
c = 14.379 (2) Å | µ = 0.28 mm−1 |
β = 107.770 (18)° | T = 230 K |
V = 945.9 (2) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.024 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8516 measured reflections | h = −19→19 |
2802 independent reflections | k = −6→7 |
2550 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0726P)2 + 0.2488P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2802 reflections | Δρmax = 0.67 e Å−3 |
121 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.038 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64588 (2) | 0.32379 (7) | 0.53831 (2) | 0.03939 (14) | |
C2 | 0.64803 (9) | 0.5542 (3) | 0.62927 (8) | 0.0336 (2) | |
C3 | 0.55384 (10) | 0.6899 (2) | 0.61204 (9) | 0.0328 (2) | |
C4 | 0.48108 (9) | 0.5966 (3) | 0.52318 (8) | 0.0330 (2) | |
C5 | 0.54490 (11) | 0.8838 (3) | 0.67762 (10) | 0.0395 (3) | |
H5 | 0.482848 | 0.977374 | 0.667102 | 0.047* | |
C6 | 0.62881 (11) | 0.9364 (3) | 0.75848 (9) | 0.0405 (3) | |
H6 | 0.622839 | 1.067370 | 0.802644 | 0.049* | |
C7 | 0.72250 (11) | 0.8001 (3) | 0.77653 (9) | 0.0371 (3) | |
C8 | 0.73210 (10) | 0.6071 (3) | 0.71146 (9) | 0.0382 (3) | |
H8 | 0.794212 | 0.513466 | 0.722520 | 0.046* | |
C9 | 0.81070 (12) | 0.8586 (3) | 0.86742 (10) | 0.0412 (3) | |
H9A | 0.801942 | 1.035979 | 0.890561 | 0.049* | |
H9B | 0.875649 | 0.855524 | 0.851275 | 0.049* | |
C10 | 0.81706 (12) | 0.6615 (3) | 0.94872 (10) | 0.0424 (3) | |
H10A | 0.750247 | 0.655763 | 0.961305 | 0.051* | |
H10B | 0.830288 | 0.486078 | 0.926764 | 0.051* | |
C11 | 0.90089 (11) | 0.7260 (3) | 1.04379 (9) | 0.0390 (3) | |
H11A | 0.967019 | 0.746800 | 1.030625 | 0.047* | |
H11B | 0.884450 | 0.893533 | 1.069466 | 0.047* | |
C12 | 0.91095 (12) | 0.5147 (3) | 1.11910 (10) | 0.0423 (3) | |
H12A | 0.845072 | 0.493758 | 1.132744 | 0.051* | |
H12B | 0.927731 | 0.346870 | 1.093862 | 0.051* | |
O13 | 0.98953 (9) | 0.5802 (2) | 1.20674 (7) | 0.0481 (3) | |
H13 | 0.9976 (13) | 0.457 (4) | 1.2457 (13) | 0.072* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.03333 (19) | 0.0470 (2) | 0.03469 (19) | 0.00566 (11) | 0.00573 (13) | −0.00871 (12) |
C2 | 0.0347 (5) | 0.0372 (6) | 0.0281 (5) | −0.0006 (4) | 0.0086 (4) | −0.0015 (4) |
C3 | 0.0342 (5) | 0.0362 (6) | 0.0278 (5) | −0.0021 (4) | 0.0092 (4) | −0.0018 (4) |
C4 | 0.0311 (5) | 0.0383 (6) | 0.0286 (5) | 0.0004 (4) | 0.0077 (4) | −0.0022 (4) |
C5 | 0.0401 (6) | 0.0429 (7) | 0.0343 (6) | 0.0011 (5) | 0.0098 (5) | −0.0067 (5) |
C6 | 0.0457 (7) | 0.0424 (7) | 0.0317 (6) | −0.0040 (5) | 0.0093 (5) | −0.0074 (5) |
C7 | 0.0404 (6) | 0.0403 (6) | 0.0275 (5) | −0.0091 (5) | 0.0058 (4) | −0.0003 (4) |
C8 | 0.0343 (6) | 0.0445 (7) | 0.0329 (6) | −0.0021 (5) | 0.0058 (4) | −0.0022 (5) |
C9 | 0.0448 (7) | 0.0418 (7) | 0.0306 (5) | −0.0113 (5) | 0.0021 (5) | −0.0010 (5) |
C10 | 0.0513 (8) | 0.0355 (6) | 0.0313 (6) | −0.0099 (5) | −0.0008 (5) | −0.0012 (5) |
C11 | 0.0459 (7) | 0.0333 (6) | 0.0313 (6) | −0.0059 (5) | 0.0022 (5) | −0.0026 (5) |
C12 | 0.0509 (7) | 0.0356 (6) | 0.0319 (6) | −0.0046 (5) | −0.0002 (5) | −0.0014 (5) |
O13 | 0.0557 (6) | 0.0435 (6) | 0.0326 (5) | −0.0024 (5) | −0.0050 (4) | 0.0002 (4) |
S1—C4i | 1.7311 (13) | C9—C10 | 1.5208 (19) |
S1—C2 | 1.7484 (13) | C9—H9A | 0.9800 |
C2—C8 | 1.3971 (17) | C9—H9B | 0.9800 |
C2—C3 | 1.4089 (17) | C10—C11 | 1.5248 (18) |
C3—C5 | 1.3937 (17) | C10—H10A | 0.9800 |
C3—C4 | 1.4371 (16) | C10—H10B | 0.9800 |
C4—C4i | 1.371 (2) | C11—C12 | 1.5006 (19) |
C5—C6 | 1.3843 (18) | C11—H11A | 0.9800 |
C5—H5 | 0.9400 | C11—H11B | 0.9800 |
C6—C7 | 1.403 (2) | C12—O13 | 1.4210 (16) |
C6—H6 | 0.9400 | C12—H12A | 0.9800 |
C7—C8 | 1.3881 (19) | C12—H12B | 0.9800 |
C7—C9 | 1.5096 (18) | O13—H13 | 0.82 (2) |
C8—H8 | 0.9400 | ||
C4i—S1—C2 | 90.69 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.38 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.72 (10) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.90 (9) | H9A—C9—H9B | 107.9 |
C5—C3—C2 | 119.27 (11) | C11—C10—C9 | 113.55 (11) |
C5—C3—C4 | 130.98 (12) | C11—C10—H10A | 108.9 |
C2—C3—C4 | 109.74 (11) | C9—C10—H10A | 108.9 |
C4i—C4—C3 | 114.15 (14) | C11—C10—H10B | 108.9 |
C4i—C4—S1i | 112.51 (12) | C9—C10—H10B | 108.9 |
C3—C4—S1i | 133.34 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.99 (13) | C12—C11—C10 | 111.84 (11) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.2 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.2 |
C5—C6—C7 | 122.00 (12) | C12—C11—H11B | 109.2 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.2 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.36 (12) | O13—C12—C11 | 110.54 (11) |
C8—C7—C9 | 120.59 (13) | O13—C12—H12A | 109.5 |
C6—C7—C9 | 120.02 (12) | C11—C12—H12A | 109.5 |
C2—C8—C7 | 118.99 (13) | O13—C12—H12B | 109.5 |
C2—C8—H8 | 120.5 | C11—C12—H12B | 109.5 |
C7—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.33 (11) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.78 (13) | C3—C5—C6—C7 | −0.1 (2) |
C4i—S1—C2—C3 | −0.55 (10) | C5—C6—C7—C8 | 0.3 (2) |
C8—C2—C3—C5 | 0.97 (19) | C5—C6—C7—C9 | −178.06 (13) |
S1—C2—C3—C5 | −178.71 (10) | C3—C2—C8—C7 | −0.8 (2) |
C8—C2—C3—C4 | −179.80 (12) | S1—C2—C8—C7 | 178.80 (10) |
S1—C2—C3—C4 | 0.52 (14) | C6—C7—C8—C2 | 0.2 (2) |
C5—C3—C4—C4i | 178.92 (15) | C9—C7—C8—C2 | 178.53 (12) |
C2—C3—C4—C4i | −0.19 (19) | C8—C7—C9—C10 | −80.28 (17) |
C5—C3—C4—S1i | −1.4 (2) | C6—C7—C9—C10 | 98.02 (16) |
C2—C3—C4—S1i | 179.52 (11) | C7—C9—C10—C11 | −176.12 (13) |
C2—C3—C5—C6 | −0.5 (2) | C9—C10—C11—C12 | −174.90 (13) |
C4—C3—C5—C6 | −179.51 (13) | C10—C11—C12—O13 | 180.00 (13) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.82 | 2.02 | 2.8030 (9) | 158 |
C6—H6···S1iii | 0.94 | 3.35 | 4.1419 (14) | 143 |
C9—H9A···S1iii | 0.98 | 3.50 | 4.1268 (17) | 124 |
C10—H10A···S1iii | 0.98 | 3.34 | 3.9677 (18) | 123 |
C10—H10A···S1iv | 0.98 | 3.18 | 3.8713 (16) | 129 |
C11—H11B···S1iii | 0.98 | 3.45 | 4.1356 (16) | 129 |
C12—H12A···S1iv | 0.98 | 3.09 | 3.8409 (16) | 135 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.348 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.625 (2) Å | Cell parameters from 6920 reflections |
b = 5.076 (1) Å | θ = 2.5–24.5° |
c = 14.392 (2) Å | µ = 0.28 mm−1 |
β = 107.852 (19)° | T = 240 K |
V = 947.4 (2) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.026 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8471 measured reflections | h = −19→19 |
2793 independent reflections | k = −6→7 |
2534 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0699P)2 + 0.272P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.001 |
2793 reflections | Δρmax = 0.65 e Å−3 |
121 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.036 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64574 (2) | 0.32381 (7) | 0.53835 (2) | 0.04124 (14) | |
C2 | 0.64790 (10) | 0.5542 (3) | 0.62927 (9) | 0.0351 (3) | |
C3 | 0.55388 (10) | 0.6896 (3) | 0.61211 (9) | 0.0343 (3) | |
C4 | 0.48115 (9) | 0.5965 (3) | 0.52315 (9) | 0.0345 (3) | |
C5 | 0.54499 (11) | 0.8832 (3) | 0.67771 (10) | 0.0412 (3) | |
H5 | 0.482972 | 0.976699 | 0.667220 | 0.049* | |
C6 | 0.62887 (11) | 0.9358 (3) | 0.75855 (9) | 0.0424 (3) | |
H6 | 0.622970 | 1.066688 | 0.802731 | 0.051* | |
C7 | 0.72235 (11) | 0.7997 (3) | 0.77650 (9) | 0.0391 (3) | |
C8 | 0.73185 (10) | 0.6072 (3) | 0.71158 (10) | 0.0398 (3) | |
H8 | 0.793896 | 0.513433 | 0.722733 | 0.048* | |
C9 | 0.81049 (12) | 0.8580 (3) | 0.86756 (10) | 0.0431 (3) | |
H9A | 0.801692 | 1.035384 | 0.890703 | 0.052* | |
H9B | 0.875372 | 0.855275 | 0.851498 | 0.052* | |
C10 | 0.81710 (13) | 0.6614 (3) | 0.94869 (10) | 0.0448 (3) | |
H10A | 0.750353 | 0.655163 | 0.961169 | 0.054* | |
H10B | 0.830475 | 0.486048 | 0.926791 | 0.054* | |
C11 | 0.90075 (12) | 0.7261 (3) | 1.04380 (9) | 0.0410 (3) | |
H11A | 0.966805 | 0.747367 | 1.030771 | 0.049* | |
H11B | 0.884166 | 0.893495 | 1.069443 | 0.049* | |
C12 | 0.91094 (12) | 0.5146 (3) | 1.11903 (10) | 0.0445 (3) | |
H12A | 0.845120 | 0.493116 | 1.132504 | 0.053* | |
H12B | 0.927933 | 0.346975 | 1.093859 | 0.053* | |
O13 | 0.98933 (9) | 0.5806 (2) | 1.20674 (7) | 0.0506 (3) | |
H13 | 0.9983 (14) | 0.457 (4) | 1.2449 (14) | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.03491 (19) | 0.0493 (2) | 0.03614 (19) | 0.00581 (12) | 0.00589 (13) | −0.00905 (12) |
C2 | 0.0362 (6) | 0.0392 (6) | 0.0293 (5) | −0.0012 (5) | 0.0090 (4) | −0.0018 (4) |
C3 | 0.0361 (6) | 0.0375 (6) | 0.0293 (5) | −0.0023 (4) | 0.0099 (4) | −0.0017 (4) |
C4 | 0.0327 (5) | 0.0401 (6) | 0.0296 (5) | 0.0002 (4) | 0.0081 (4) | −0.0021 (4) |
C5 | 0.0418 (6) | 0.0443 (7) | 0.0360 (6) | 0.0014 (5) | 0.0099 (5) | −0.0069 (5) |
C6 | 0.0485 (7) | 0.0437 (7) | 0.0332 (6) | −0.0039 (5) | 0.0099 (5) | −0.0075 (5) |
C7 | 0.0427 (6) | 0.0425 (7) | 0.0288 (5) | −0.0095 (5) | 0.0059 (5) | 0.0002 (5) |
C8 | 0.0359 (6) | 0.0463 (7) | 0.0337 (6) | −0.0019 (5) | 0.0056 (5) | −0.0017 (5) |
C9 | 0.0468 (7) | 0.0439 (7) | 0.0320 (6) | −0.0116 (6) | 0.0022 (5) | −0.0013 (5) |
C10 | 0.0547 (8) | 0.0373 (7) | 0.0329 (6) | −0.0100 (6) | −0.0004 (5) | −0.0012 (5) |
C11 | 0.0478 (7) | 0.0358 (6) | 0.0325 (6) | −0.0060 (5) | 0.0020 (5) | −0.0028 (5) |
C12 | 0.0530 (8) | 0.0377 (7) | 0.0335 (6) | −0.0049 (6) | −0.0004 (5) | −0.0014 (5) |
O13 | 0.0581 (6) | 0.0463 (6) | 0.0344 (5) | −0.0024 (5) | −0.0052 (4) | 0.0000 (4) |
S1—C4i | 1.7313 (13) | C9—C10 | 1.517 (2) |
S1—C2 | 1.7485 (13) | C9—H9A | 0.9800 |
C2—C8 | 1.3975 (17) | C9—H9B | 0.9800 |
C2—C3 | 1.4071 (18) | C10—C11 | 1.5244 (18) |
C3—C5 | 1.3938 (18) | C10—H10A | 0.9800 |
C3—C4 | 1.4375 (16) | C10—H10B | 0.9800 |
C4—C4i | 1.370 (2) | C11—C12 | 1.500 (2) |
C5—C6 | 1.3841 (18) | C11—H11A | 0.9800 |
C5—H5 | 0.9400 | C11—H11B | 0.9800 |
C6—C7 | 1.402 (2) | C12—O13 | 1.4212 (16) |
C6—H6 | 0.9400 | C12—H12A | 0.9800 |
C7—C8 | 1.385 (2) | C12—H12B | 0.9800 |
C7—C9 | 1.5107 (18) | O13—H13 | 0.82 (3) |
C8—H8 | 0.9400 | ||
C4i—S1—C2 | 90.66 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.29 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.77 (10) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.93 (9) | H9A—C9—H9B | 107.8 |
C5—C3—C2 | 119.27 (12) | C11—C10—C9 | 113.64 (11) |
C5—C3—C4 | 130.97 (12) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.75 (11) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.15 (14) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.51 (12) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.34 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.98 (13) | C12—C11—C10 | 111.85 (11) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.2 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.2 |
C5—C6—C7 | 121.98 (13) | C12—C11—H11B | 109.2 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.2 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.40 (12) | O13—C12—C11 | 110.51 (12) |
C8—C7—C9 | 120.63 (13) | O13—C12—H12A | 109.5 |
C6—C7—C9 | 119.95 (13) | C11—C12—H12A | 109.5 |
C2—C8—C7 | 119.07 (13) | O13—C12—H12B | 109.5 |
C2—C8—H8 | 120.5 | C11—C12—H12B | 109.5 |
C7—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.50 (11) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.69 (13) | C3—C5—C6—C7 | −0.2 (2) |
C4i—S1—C2—C3 | −0.47 (10) | C5—C6—C7—C8 | 0.2 (2) |
C8—C2—C3—C5 | 1.1 (2) | C5—C6—C7—C9 | −177.94 (13) |
S1—C2—C3—C5 | −178.76 (10) | C3—C2—C8—C7 | −1.0 (2) |
C8—C2—C3—C4 | −179.79 (12) | S1—C2—C8—C7 | 178.82 (10) |
S1—C2—C3—C4 | 0.36 (14) | C6—C7—C8—C2 | 0.3 (2) |
C5—C3—C4—C4i | 178.97 (15) | C9—C7—C8—C2 | 178.51 (12) |
C2—C3—C4—C4i | 0.0 (2) | C8—C7—C9—C10 | −80.18 (18) |
C5—C3—C4—S1i | −1.5 (2) | C6—C7—C9—C10 | 97.98 (17) |
C2—C3—C4—S1i | 179.55 (11) | C7—C9—C10—C11 | −176.05 (14) |
C2—C3—C5—C6 | −0.5 (2) | C9—C10—C11—C12 | −174.89 (14) |
C4—C3—C5—C6 | −179.40 (14) | C10—C11—C12—O13 | −179.95 (13) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.82 | 2.02 | 2.8026 (9) | 159 |
C6—H6···S1iii | 0.94 | 3.36 | 4.1462 (14) | 143 |
C9—H9A···S1iii | 0.98 | 3.51 | 4.1319 (18) | 124 |
C10—H10A···S1iii | 0.98 | 3.35 | 3.9738 (18) | 123 |
C10—H10A···S1iv | 0.98 | 3.19 | 3.8769 (16) | 129 |
C11—H11B···S1iii | 0.98 | 3.45 | 4.1390 (17) | 129 |
C12—H12A···S1iv | 0.98 | 3.09 | 3.8449 (16) | 135 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.345 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.644 (3) Å | Cell parameters from 7096 reflections |
b = 5.076 (1) Å | θ = 2.3–25.4° |
c = 14.405 (3) Å | µ = 0.28 mm−1 |
β = 107.94 (2)° | T = 250 K |
V = 949.2 (3) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.024 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.6° |
8491 measured reflections | h = −19→19 |
2806 independent reflections | k = −6→7 |
2530 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.119 | w = 1/[σ2(Fo2) + (0.0676P)2 + 0.277P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.001 |
2806 reflections | Δρmax = 0.63 e Å−3 |
121 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.035 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64559 (2) | 0.32387 (7) | 0.53841 (2) | 0.04310 (13) | |
C2 | 0.64784 (10) | 0.5539 (3) | 0.62938 (9) | 0.0366 (3) | |
C3 | 0.55390 (10) | 0.6894 (2) | 0.61213 (9) | 0.0357 (3) | |
C4 | 0.48125 (9) | 0.5965 (3) | 0.52311 (9) | 0.0359 (3) | |
C5 | 0.54503 (11) | 0.8828 (3) | 0.67774 (10) | 0.0431 (3) | |
H5 | 0.483029 | 0.975985 | 0.667263 | 0.052* | |
C6 | 0.62877 (11) | 0.9354 (3) | 0.75848 (10) | 0.0445 (3) | |
H6 | 0.622903 | 1.066465 | 0.802569 | 0.053* | |
C7 | 0.72223 (11) | 0.7992 (3) | 0.77659 (9) | 0.0407 (3) | |
C8 | 0.73177 (10) | 0.6068 (3) | 0.71171 (10) | 0.0417 (3) | |
H8 | 0.793780 | 0.513202 | 0.722894 | 0.050* | |
C9 | 0.81036 (12) | 0.8577 (3) | 0.86769 (10) | 0.0452 (3) | |
H9A | 0.801534 | 1.035079 | 0.890795 | 0.054* | |
H9B | 0.875157 | 0.855083 | 0.851700 | 0.054* | |
C10 | 0.81702 (13) | 0.6614 (3) | 0.94865 (10) | 0.0462 (3) | |
H10A | 0.750358 | 0.655168 | 0.961058 | 0.055* | |
H10B | 0.830334 | 0.486049 | 0.926736 | 0.055* | |
C11 | 0.90064 (12) | 0.7258 (3) | 1.04380 (9) | 0.0427 (3) | |
H11A | 0.966632 | 0.746757 | 1.030849 | 0.051* | |
H11B | 0.884179 | 0.893311 | 1.069373 | 0.051* | |
C12 | 0.91084 (12) | 0.5148 (3) | 1.11903 (10) | 0.0468 (3) | |
H12A | 0.845110 | 0.493654 | 1.132482 | 0.056* | |
H12B | 0.927710 | 0.347017 | 1.093954 | 0.056* | |
O13 | 0.98922 (9) | 0.5808 (2) | 1.20666 (8) | 0.0528 (3) | |
H13 | 0.9979 (13) | 0.457 (4) | 1.2453 (13) | 0.079* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.03661 (19) | 0.0514 (2) | 0.03782 (19) | 0.00608 (12) | 0.00634 (13) | −0.00933 (13) |
C2 | 0.0376 (6) | 0.0409 (6) | 0.0304 (5) | −0.0010 (5) | 0.0092 (4) | −0.0019 (4) |
C3 | 0.0378 (6) | 0.0388 (6) | 0.0305 (5) | −0.0024 (4) | 0.0105 (4) | −0.0020 (4) |
C4 | 0.0341 (5) | 0.0415 (6) | 0.0310 (5) | 0.0004 (5) | 0.0086 (4) | −0.0019 (5) |
C5 | 0.0438 (7) | 0.0472 (7) | 0.0367 (6) | 0.0014 (5) | 0.0100 (5) | −0.0076 (5) |
C6 | 0.0511 (7) | 0.0461 (7) | 0.0344 (6) | −0.0049 (6) | 0.0105 (5) | −0.0079 (5) |
C7 | 0.0443 (7) | 0.0443 (7) | 0.0300 (5) | −0.0097 (5) | 0.0063 (5) | 0.0000 (5) |
C8 | 0.0378 (6) | 0.0480 (7) | 0.0357 (6) | −0.0020 (5) | 0.0063 (5) | −0.0019 (5) |
C9 | 0.0491 (7) | 0.0460 (7) | 0.0336 (6) | −0.0119 (6) | 0.0027 (5) | −0.0014 (5) |
C10 | 0.0559 (8) | 0.0387 (7) | 0.0344 (6) | −0.0099 (6) | −0.0005 (5) | −0.0015 (5) |
C11 | 0.0498 (7) | 0.0373 (6) | 0.0341 (6) | −0.0062 (5) | 0.0025 (5) | −0.0030 (5) |
C12 | 0.0555 (8) | 0.0397 (7) | 0.0354 (6) | −0.0053 (6) | −0.0006 (5) | −0.0016 (5) |
O13 | 0.0611 (7) | 0.0475 (6) | 0.0361 (5) | −0.0024 (5) | −0.0053 (4) | −0.0002 (4) |
S1—C4i | 1.7318 (13) | C9—C10 | 1.515 (2) |
S1—C2 | 1.7483 (13) | C9—H9A | 0.9800 |
C2—C8 | 1.3977 (17) | C9—H9B | 0.9800 |
C2—C3 | 1.4076 (18) | C10—C11 | 1.5244 (19) |
C3—C5 | 1.3935 (18) | C10—H10A | 0.9800 |
C3—C4 | 1.4375 (17) | C10—H10B | 0.9800 |
C4—C4i | 1.369 (2) | C11—C12 | 1.499 (2) |
C5—C6 | 1.3825 (19) | C11—H11A | 0.9800 |
C5—H5 | 0.9400 | C11—H11B | 0.9800 |
C6—C7 | 1.403 (2) | C12—O13 | 1.4206 (16) |
C6—H6 | 0.9400 | C12—H12A | 0.9800 |
C7—C8 | 1.385 (2) | C12—H12B | 0.9800 |
C7—C9 | 1.5114 (18) | O13—H13 | 0.82 (3) |
C8—H8 | 0.9400 | ||
C4i—S1—C2 | 90.67 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.29 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.80 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.90 (9) | H9A—C9—H9B | 107.8 |
C5—C3—C2 | 119.28 (12) | C11—C10—C9 | 113.71 (12) |
C5—C3—C4 | 130.99 (12) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.72 (11) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.21 (14) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.49 (12) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.30 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 119.00 (13) | C12—C11—C10 | 111.97 (12) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.2 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.2 |
C5—C6—C7 | 121.99 (13) | C12—C11—H11B | 109.2 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.2 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.40 (12) | O13—C12—C11 | 110.54 (12) |
C8—C7—C9 | 120.62 (13) | O13—C12—H12A | 109.5 |
C6—C7—C9 | 119.95 (13) | C11—C12—H12A | 109.5 |
C2—C8—C7 | 119.03 (13) | O13—C12—H12B | 109.5 |
C2—C8—H8 | 120.5 | C11—C12—H12B | 109.5 |
C7—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.48 (12) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.71 (13) | C3—C5—C6—C7 | −0.3 (2) |
C4i—S1—C2—C3 | −0.57 (10) | C5—C6—C7—C8 | 0.4 (2) |
C8—C2—C3—C5 | 1.0 (2) | C5—C6—C7—C9 | −177.93 (13) |
S1—C2—C3—C5 | −178.76 (10) | C3—C2—C8—C7 | −0.9 (2) |
C8—C2—C3—C4 | −179.86 (12) | S1—C2—C8—C7 | 178.78 (11) |
S1—C2—C3—C4 | 0.40 (14) | C6—C7—C8—C2 | 0.3 (2) |
C5—C3—C4—C4i | 179.08 (15) | C9—C7—C8—C2 | 178.53 (12) |
C2—C3—C4—C4i | 0.0 (2) | C8—C7—C9—C10 | −80.22 (18) |
C5—C3—C4—S1i | −1.5 (2) | C6—C7—C9—C10 | 98.04 (17) |
C2—C3—C4—S1i | 179.44 (11) | C7—C9—C10—C11 | −176.10 (14) |
C2—C3—C5—C6 | −0.3 (2) | C9—C10—C11—C12 | −174.99 (14) |
C4—C3—C5—C6 | −179.31 (14) | C10—C11—C12—O13 | −179.97 (13) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.82 | 2.02 | 2.8037 (9) | 159 |
C6—H6···S1iii | 0.94 | 3.36 | 4.1516 (16) | 143 |
C9—H9A···S1iii | 0.98 | 3.51 | 4.1374 (19) | 124 |
C10—H10A···S1iii | 0.98 | 3.36 | 3.9788 (18) | 123 |
C10—H10A···S1iv | 0.98 | 3.19 | 3.8825 (16) | 129 |
C11—H11B···S1iii | 0.98 | 3.46 | 4.1443 (18) | 129 |
C12—H12A···S1iv | 0.98 | 3.09 | 3.8488 (17) | 135 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.343 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.664 (4) Å | Cell parameters from 6937 reflections |
b = 5.075 (1) Å | θ = 2.4–25.7° |
c = 14.419 (4) Å | µ = 0.28 mm−1 |
β = 108.02 (3)° | T = 260 K |
V = 950.8 (4) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.026 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.5° |
8501 measured reflections | h = −19→19 |
2820 independent reflections | k = −6→7 |
2523 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.126 | w = 1/[σ2(Fo2) + (0.0729P)2 + 0.2289P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.007 |
2820 reflections | Δρmax = 0.61 e Å−3 |
121 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.039 (6) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64544 (2) | 0.32385 (8) | 0.53848 (2) | 0.04517 (14) | |
C2 | 0.64781 (10) | 0.5539 (3) | 0.62946 (9) | 0.0384 (3) | |
C3 | 0.55387 (10) | 0.6892 (3) | 0.61214 (9) | 0.0374 (3) | |
C4 | 0.48133 (10) | 0.5963 (3) | 0.52310 (9) | 0.0377 (3) | |
C5 | 0.54504 (11) | 0.8824 (3) | 0.67779 (10) | 0.0452 (3) | |
H5 | 0.483776 | 0.974635 | 0.667425 | 0.054* | |
C6 | 0.62873 (12) | 0.9348 (3) | 0.75854 (10) | 0.0464 (3) | |
H6 | 0.622886 | 1.064072 | 0.802231 | 0.056* | |
C7 | 0.72226 (11) | 0.7991 (3) | 0.77666 (9) | 0.0427 (3) | |
C8 | 0.73161 (11) | 0.6065 (3) | 0.71170 (10) | 0.0437 (3) | |
H8 | 0.792851 | 0.513668 | 0.722778 | 0.052* | |
C9 | 0.81021 (12) | 0.8574 (3) | 0.86774 (10) | 0.0476 (3) | |
H9A | 0.801509 | 1.033087 | 0.890517 | 0.057* | |
H9B | 0.874279 | 0.854711 | 0.852011 | 0.057* | |
C10 | 0.81694 (13) | 0.6614 (3) | 0.94873 (10) | 0.0486 (3) | |
H10A | 0.751029 | 0.655324 | 0.960919 | 0.058* | |
H10B | 0.830091 | 0.487744 | 0.927140 | 0.058* | |
C11 | 0.90046 (12) | 0.7258 (3) | 1.04389 (10) | 0.0450 (3) | |
H11A | 0.965695 | 0.746709 | 1.031157 | 0.054* | |
H11B | 0.884152 | 0.891680 | 1.069140 | 0.054* | |
C12 | 0.91075 (13) | 0.5150 (3) | 1.11909 (10) | 0.0490 (3) | |
H12A | 0.845777 | 0.493960 | 1.132332 | 0.059* | |
H12B | 0.927451 | 0.348877 | 1.094332 | 0.059* | |
O13 | 0.98905 (10) | 0.5811 (2) | 1.20671 (8) | 0.0556 (3) | |
H13 | 0.9972 (14) | 0.459 (5) | 1.2452 (14) | 0.083* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0386 (2) | 0.0539 (2) | 0.0393 (2) | 0.00628 (13) | 0.00669 (13) | −0.00964 (13) |
C2 | 0.0397 (6) | 0.0425 (6) | 0.0320 (5) | −0.0010 (5) | 0.0097 (4) | −0.0016 (5) |
C3 | 0.0393 (6) | 0.0410 (6) | 0.0316 (5) | −0.0029 (5) | 0.0107 (4) | −0.0018 (4) |
C4 | 0.0363 (5) | 0.0433 (6) | 0.0324 (5) | 0.0000 (5) | 0.0091 (4) | −0.0021 (5) |
C5 | 0.0461 (7) | 0.0490 (7) | 0.0390 (6) | 0.0015 (6) | 0.0108 (5) | −0.0076 (5) |
C6 | 0.0528 (8) | 0.0481 (7) | 0.0363 (6) | −0.0052 (6) | 0.0111 (5) | −0.0086 (5) |
C7 | 0.0468 (7) | 0.0462 (7) | 0.0314 (6) | −0.0100 (5) | 0.0067 (5) | 0.0001 (5) |
C8 | 0.0401 (6) | 0.0502 (7) | 0.0374 (6) | −0.0017 (5) | 0.0070 (5) | −0.0015 (5) |
C9 | 0.0519 (8) | 0.0485 (7) | 0.0352 (6) | −0.0133 (6) | 0.0029 (5) | −0.0015 (5) |
C10 | 0.0587 (8) | 0.0405 (7) | 0.0364 (6) | −0.0102 (6) | −0.0003 (6) | −0.0016 (5) |
C11 | 0.0524 (7) | 0.0392 (6) | 0.0354 (6) | −0.0068 (5) | 0.0017 (5) | −0.0035 (5) |
C12 | 0.0583 (8) | 0.0411 (7) | 0.0369 (6) | −0.0051 (6) | −0.0007 (5) | −0.0009 (5) |
O13 | 0.0645 (7) | 0.0498 (6) | 0.0377 (5) | −0.0028 (5) | −0.0057 (5) | 0.0002 (4) |
S1—C4i | 1.7324 (14) | C9—C10 | 1.515 (2) |
S1—C2 | 1.7489 (13) | C9—H9A | 0.9700 |
C2—C8 | 1.3959 (18) | C9—H9B | 0.9700 |
C2—C3 | 1.4082 (18) | C10—C11 | 1.5241 (19) |
C3—C5 | 1.3939 (18) | C10—H10A | 0.9700 |
C3—C4 | 1.4371 (17) | C10—H10B | 0.9700 |
C4—C4i | 1.368 (3) | C11—C12 | 1.499 (2) |
C5—C6 | 1.3820 (19) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C6—C7 | 1.403 (2) | C12—O13 | 1.4201 (17) |
C6—H6 | 0.9300 | C12—H12A | 0.9700 |
C7—C8 | 1.387 (2) | C12—H12B | 0.9700 |
C7—C9 | 1.5100 (19) | O13—H13 | 0.82 (3) |
C8—H8 | 0.9300 | ||
C4i—S1—C2 | 90.68 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.37 (12) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.79 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.84 (9) | H9A—C9—H9B | 107.8 |
C5—C3—C2 | 119.22 (12) | C11—C10—C9 | 113.78 (12) |
C5—C3—C4 | 131.05 (12) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.72 (11) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.29 (14) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.46 (13) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.25 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 118.99 (14) | C12—C11—C10 | 112.02 (12) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.2 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.2 |
C5—C6—C7 | 122.06 (13) | C12—C11—H11B | 109.2 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.2 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.28 (13) | O13—C12—C11 | 110.57 (12) |
C8—C7—C9 | 120.72 (14) | O13—C12—H12A | 109.5 |
C6—C7—C9 | 119.97 (13) | C11—C12—H12A | 109.5 |
C2—C8—C7 | 119.06 (13) | O13—C12—H12B | 109.5 |
C2—C8—H8 | 120.5 | C11—C12—H12B | 109.5 |
C7—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.57 (12) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.69 (13) | C3—C5—C6—C7 | −0.2 (2) |
C4i—S1—C2—C3 | −0.50 (11) | C5—C6—C7—C8 | 0.1 (2) |
C8—C2—C3—C5 | 1.0 (2) | C5—C6—C7—C9 | −177.94 (13) |
S1—C2—C3—C5 | −178.82 (11) | C3—C2—C8—C7 | −1.0 (2) |
C8—C2—C3—C4 | −179.85 (12) | S1—C2—C8—C7 | 178.76 (11) |
S1—C2—C3—C4 | 0.33 (14) | C6—C7—C8—C2 | 0.5 (2) |
C5—C3—C4—C4i | 179.10 (16) | C9—C7—C8—C2 | 178.52 (13) |
C2—C3—C4—C4i | 0.1 (2) | C8—C7—C9—C10 | −80.25 (19) |
C5—C3—C4—S1i | −1.5 (2) | C6—C7—C9—C10 | 97.81 (18) |
C2—C3—C4—S1i | 179.49 (11) | C7—C9—C10—C11 | −176.09 (14) |
C2—C3—C5—C6 | −0.4 (2) | C9—C10—C11—C12 | −174.93 (15) |
C4—C3—C5—C6 | −179.32 (14) | C10—C11—C12—O13 | −179.98 (14) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.82 | 2.03 | 2.8028 (9) | 158 |
C6—H6···S1iii | 0.93 | 3.37 | 4.1564 (17) | 143 |
C9—H9A···S1iii | 0.97 | 3.53 | 4.144 (2) | 124 |
C10—H10A···S1iii | 0.97 | 3.36 | 3.9832 (19) | 124 |
C10—H10A···S1iv | 0.97 | 3.20 | 3.8870 (17) | 129 |
C11—H11B···S1iii | 0.97 | 3.47 | 4.1477 (19) | 129 |
C12—H12A···S1iv | 0.97 | 3.10 | 3.8528 (19) | 135 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.341 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.684 (4) Å | Cell parameters from 7068 reflections |
b = 5.074 (1) Å | θ = 2.3–24.8° |
c = 14.433 (4) Å | µ = 0.28 mm−1 |
β = 108.11 (3)° | T = 270 K |
V = 952.5 (4) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.028 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.5° |
8556 measured reflections | h = −19→19 |
2820 independent reflections | k = −6→7 |
2505 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0721P)2 + 0.223P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.027 |
2820 reflections | Δρmax = 0.58 e Å−3 |
121 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.037 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64527 (3) | 0.32388 (8) | 0.53853 (2) | 0.04703 (14) | |
C2 | 0.64764 (10) | 0.5535 (3) | 0.62945 (9) | 0.0400 (3) | |
C3 | 0.55373 (10) | 0.6890 (3) | 0.61207 (9) | 0.0391 (3) | |
C4 | 0.48127 (10) | 0.5962 (3) | 0.52312 (9) | 0.0391 (3) | |
C5 | 0.54510 (12) | 0.8820 (3) | 0.67776 (10) | 0.0472 (3) | |
H5 | 0.483932 | 0.974372 | 0.667356 | 0.057* | |
C6 | 0.62871 (12) | 0.9341 (3) | 0.75862 (10) | 0.0485 (3) | |
H6 | 0.622860 | 1.063060 | 0.802394 | 0.058* | |
C7 | 0.72218 (11) | 0.7984 (3) | 0.77668 (9) | 0.0446 (3) | |
C8 | 0.73146 (11) | 0.6066 (3) | 0.71186 (10) | 0.0454 (3) | |
H8 | 0.792702 | 0.514089 | 0.722947 | 0.054* | |
C9 | 0.81006 (13) | 0.8567 (3) | 0.86778 (10) | 0.0499 (3) | |
H9A | 0.801434 | 1.032486 | 0.890469 | 0.060* | |
H9B | 0.874053 | 0.853790 | 0.852130 | 0.060* | |
C10 | 0.81686 (14) | 0.6613 (3) | 0.94871 (11) | 0.0507 (4) | |
H10A | 0.751042 | 0.655458 | 0.960845 | 0.061* | |
H10B | 0.829900 | 0.487484 | 0.927189 | 0.061* | |
C11 | 0.90039 (12) | 0.7255 (3) | 1.04391 (10) | 0.0468 (3) | |
H11A | 0.965557 | 0.746026 | 1.031251 | 0.056* | |
H11B | 0.884223 | 0.891586 | 1.069074 | 0.056* | |
C12 | 0.91063 (13) | 0.5154 (3) | 1.11903 (10) | 0.0511 (3) | |
H12A | 0.845732 | 0.494723 | 1.132215 | 0.061* | |
H12B | 0.927211 | 0.349064 | 1.094381 | 0.061* | |
O13 | 0.98896 (10) | 0.5816 (2) | 1.20666 (8) | 0.0582 (3) | |
H13 | 0.9969 (14) | 0.462 (5) | 1.2444 (14) | 0.087* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0402 (2) | 0.0562 (2) | 0.0407 (2) | 0.00652 (13) | 0.00694 (14) | −0.00996 (13) |
C2 | 0.0410 (6) | 0.0448 (7) | 0.0333 (5) | −0.0012 (5) | 0.0102 (4) | −0.0018 (5) |
C3 | 0.0417 (6) | 0.0427 (6) | 0.0328 (5) | −0.0029 (5) | 0.0116 (5) | −0.0019 (4) |
C4 | 0.0378 (5) | 0.0448 (6) | 0.0336 (5) | 0.0004 (5) | 0.0094 (4) | −0.0021 (5) |
C5 | 0.0482 (7) | 0.0515 (7) | 0.0404 (6) | 0.0014 (6) | 0.0115 (6) | −0.0078 (6) |
C6 | 0.0554 (8) | 0.0508 (8) | 0.0370 (6) | −0.0052 (6) | 0.0111 (6) | −0.0092 (5) |
C7 | 0.0491 (7) | 0.0483 (7) | 0.0324 (6) | −0.0109 (5) | 0.0068 (5) | 0.0001 (5) |
C8 | 0.0415 (6) | 0.0522 (8) | 0.0385 (6) | −0.0021 (5) | 0.0068 (5) | −0.0020 (5) |
C9 | 0.0542 (8) | 0.0509 (8) | 0.0368 (6) | −0.0135 (6) | 0.0030 (6) | −0.0017 (5) |
C10 | 0.0614 (9) | 0.0427 (7) | 0.0374 (6) | −0.0111 (6) | −0.0003 (6) | −0.0019 (5) |
C11 | 0.0546 (7) | 0.0408 (7) | 0.0367 (6) | −0.0065 (6) | 0.0023 (5) | −0.0034 (5) |
C12 | 0.0607 (8) | 0.0436 (7) | 0.0380 (6) | −0.0054 (6) | −0.0008 (6) | −0.0019 (5) |
O13 | 0.0673 (7) | 0.0522 (6) | 0.0396 (5) | −0.0036 (5) | −0.0061 (5) | 0.0000 (4) |
S1—C4i | 1.7311 (14) | C9—C10 | 1.513 (2) |
S1—C2 | 1.7477 (14) | C9—H9A | 0.9700 |
C2—C8 | 1.3980 (18) | C9—H9B | 0.9700 |
C2—C3 | 1.4094 (19) | C10—C11 | 1.524 (2) |
C3—C5 | 1.3931 (18) | C10—H10A | 0.9700 |
C3—C4 | 1.4359 (17) | C10—H10B | 0.9700 |
C4—C4i | 1.369 (3) | C11—C12 | 1.496 (2) |
C5—C6 | 1.382 (2) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C6—C7 | 1.404 (2) | C12—O13 | 1.4207 (17) |
C6—H6 | 0.9300 | C12—H12A | 0.9700 |
C7—C8 | 1.383 (2) | C12—H12B | 0.9700 |
C7—C9 | 1.5097 (19) | O13—H13 | 0.80 (3) |
C8—H8 | 0.9300 | ||
C4i—S1—C2 | 90.68 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.26 (13) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.88 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.86 (10) | H9A—C9—H9B | 107.8 |
C5—C3—C2 | 119.15 (12) | C11—C10—C9 | 113.89 (12) |
C5—C3—C4 | 131.14 (13) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.70 (11) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.25 (15) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.51 (13) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.24 (10) | H10A—C10—H10B | 107.7 |
C6—C5—C3 | 119.08 (14) | C12—C11—C10 | 112.10 (12) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.2 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.2 |
C5—C6—C7 | 122.00 (13) | C12—C11—H11B | 109.2 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.2 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.31 (13) | O13—C12—C11 | 110.59 (12) |
C8—C7—C9 | 120.74 (14) | O13—C12—H12A | 109.5 |
C6—C7—C9 | 119.91 (14) | C11—C12—H12A | 109.5 |
C2—C8—C7 | 119.18 (13) | O13—C12—H12B | 109.5 |
C2—C8—H8 | 120.4 | C11—C12—H12B | 109.5 |
C7—C8—H8 | 120.4 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.67 (12) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.82 (13) | C3—C5—C6—C7 | 0.0 (2) |
C4i—S1—C2—C3 | −0.48 (11) | C5—C6—C7—C8 | 0.1 (2) |
C8—C2—C3—C5 | 0.9 (2) | C5—C6—C7—C9 | −178.01 (14) |
S1—C2—C3—C5 | −178.80 (11) | C3—C2—C8—C7 | −0.9 (2) |
C8—C2—C3—C4 | −179.86 (13) | S1—C2—C8—C7 | 178.77 (11) |
S1—C2—C3—C4 | 0.42 (14) | C6—C7—C8—C2 | 0.4 (2) |
C5—C3—C4—C4i | 178.99 (16) | C9—C7—C8—C2 | 178.46 (13) |
C2—C3—C4—C4i | −0.1 (2) | C8—C7—C9—C10 | −80.40 (19) |
C5—C3—C4—S1i | −1.3 (2) | C6—C7—C9—C10 | 97.64 (18) |
C2—C3—C4—S1i | 179.57 (11) | C7—C9—C10—C11 | −176.12 (15) |
C2—C3—C5—C6 | −0.4 (2) | C9—C10—C11—C12 | −174.96 (15) |
C4—C3—C5—C6 | −179.46 (14) | C10—C11—C12—O13 | −179.97 (14) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.80 | 2.05 | 2.8032 (10) | 158 |
C6—H6···S1iii | 0.93 | 3.37 | 4.1606 (18) | 144 |
C9—H9A···S1iii | 0.97 | 3.54 | 4.152 (2) | 124 |
C10—H10A···S1iii | 0.97 | 3.37 | 3.989 (2) | 124 |
C10—H10A···S1iv | 0.97 | 3.21 | 3.8920 (18) | 129 |
C11—H11B···S1iii | 0.97 | 3.47 | 4.1536 (19) | 129 |
C12—H12A···S1iv | 0.97 | 3.11 | 3.8570 (19) | 135 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.338 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.705 (3) Å | Cell parameters from 6934 reflections |
b = 5.074 (1) Å | θ = 2.3–25.8° |
c = 14.447 (3) Å | µ = 0.28 mm−1 |
β = 108.20 (2)° | T = 280 K |
V = 954.4 (3) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.024 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.5° |
8550 measured reflections | h = −19→19 |
2833 independent reflections | k = −6→7 |
2496 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.130 | w = 1/[σ2(Fo2) + (0.075P)2 + 0.230P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.023 |
2833 reflections | Δρmax = 0.56 e Å−3 |
121 parameters | Δρmin = −0.27 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.041 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64509 (3) | 0.32388 (8) | 0.53858 (3) | 0.04930 (15) | |
C2 | 0.64762 (10) | 0.5535 (3) | 0.62956 (9) | 0.0418 (3) | |
C3 | 0.55374 (10) | 0.6887 (3) | 0.61223 (9) | 0.0410 (3) | |
C4 | 0.48133 (10) | 0.5962 (3) | 0.52311 (9) | 0.0409 (3) | |
C5 | 0.54511 (12) | 0.8814 (3) | 0.67781 (11) | 0.0494 (3) | |
H5 | 0.483993 | 0.973760 | 0.667355 | 0.059* | |
C6 | 0.62866 (12) | 0.9336 (3) | 0.75869 (10) | 0.0508 (3) | |
H6 | 0.622841 | 1.062307 | 0.802482 | 0.061* | |
C7 | 0.72204 (12) | 0.7980 (3) | 0.77669 (10) | 0.0466 (3) | |
C8 | 0.73134 (11) | 0.6061 (3) | 0.71192 (10) | 0.0475 (3) | |
H8 | 0.792497 | 0.513513 | 0.723063 | 0.057* | |
C9 | 0.81003 (13) | 0.8562 (3) | 0.86786 (11) | 0.0522 (4) | |
H9A | 0.801544 | 1.032180 | 0.890453 | 0.063* | |
H9B | 0.873910 | 0.852914 | 0.852252 | 0.063* | |
C10 | 0.81682 (14) | 0.6614 (3) | 0.94879 (11) | 0.0530 (4) | |
H10A | 0.751071 | 0.655811 | 0.960820 | 0.064* | |
H10B | 0.829754 | 0.487413 | 0.927359 | 0.064* | |
C11 | 0.90021 (13) | 0.7253 (3) | 1.04398 (10) | 0.0492 (3) | |
H11A | 0.965304 | 0.745653 | 1.031400 | 0.059* | |
H11B | 0.884118 | 0.891468 | 1.069049 | 0.059* | |
C12 | 0.91053 (13) | 0.5158 (3) | 1.11912 (11) | 0.0540 (4) | |
H12A | 0.845726 | 0.495255 | 1.132243 | 0.065* | |
H12B | 0.927039 | 0.349301 | 1.094568 | 0.065* | |
O13 | 0.98872 (10) | 0.5817 (3) | 1.20666 (8) | 0.0612 (3) | |
H13 | 0.9968 (14) | 0.461 (5) | 1.2446 (14) | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0422 (2) | 0.0588 (3) | 0.0427 (2) | 0.00682 (13) | 0.00721 (14) | −0.01032 (14) |
C2 | 0.0427 (6) | 0.0465 (7) | 0.0350 (5) | −0.0011 (5) | 0.0105 (5) | −0.0016 (5) |
C3 | 0.0432 (6) | 0.0449 (7) | 0.0345 (6) | −0.0026 (5) | 0.0118 (5) | −0.0017 (5) |
C4 | 0.0396 (6) | 0.0472 (7) | 0.0348 (5) | 0.0002 (5) | 0.0099 (4) | −0.0017 (5) |
C5 | 0.0505 (7) | 0.0539 (8) | 0.0422 (7) | 0.0014 (6) | 0.0120 (6) | −0.0083 (6) |
C6 | 0.0581 (8) | 0.0533 (8) | 0.0386 (6) | −0.0055 (6) | 0.0116 (6) | −0.0095 (6) |
C7 | 0.0514 (7) | 0.0501 (7) | 0.0338 (6) | −0.0112 (6) | 0.0069 (5) | 0.0000 (5) |
C8 | 0.0434 (7) | 0.0545 (8) | 0.0406 (6) | −0.0021 (6) | 0.0072 (5) | −0.0019 (6) |
C9 | 0.0563 (8) | 0.0535 (8) | 0.0383 (6) | −0.0140 (6) | 0.0024 (6) | −0.0017 (6) |
C10 | 0.0633 (9) | 0.0448 (7) | 0.0395 (7) | −0.0110 (6) | −0.0004 (6) | −0.0022 (5) |
C11 | 0.0571 (8) | 0.0432 (7) | 0.0383 (6) | −0.0076 (6) | 0.0020 (6) | −0.0041 (5) |
C12 | 0.0640 (9) | 0.0452 (7) | 0.0407 (7) | −0.0053 (6) | −0.0012 (6) | −0.0020 (6) |
O13 | 0.0707 (8) | 0.0547 (6) | 0.0413 (5) | −0.0037 (5) | −0.0067 (5) | 0.0000 (5) |
S1—C4i | 1.7309 (14) | C9—C10 | 1.512 (2) |
S1—C2 | 1.7485 (14) | C9—H9A | 0.9700 |
C2—C8 | 1.3966 (19) | C9—H9B | 0.9700 |
C2—C3 | 1.4099 (19) | C10—C11 | 1.523 (2) |
C3—C5 | 1.3919 (19) | C10—H10A | 0.9700 |
C3—C4 | 1.4370 (18) | C10—H10B | 0.9700 |
C4—C4i | 1.369 (3) | C11—C12 | 1.494 (2) |
C5—C6 | 1.382 (2) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C6—C7 | 1.404 (2) | C12—O13 | 1.4187 (17) |
C6—H6 | 0.9300 | C12—H12A | 0.9700 |
C7—C8 | 1.383 (2) | C12—H12B | 0.9700 |
C7—C9 | 1.5112 (19) | O13—H13 | 0.81 (3) |
C8—H8 | 0.9300 | ||
C4i—S1—C2 | 90.72 (7) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.29 (13) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.87 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.83 (10) | H9A—C9—H9B | 107.8 |
C5—C3—C2 | 119.20 (12) | C11—C10—C9 | 114.00 (12) |
C5—C3—C4 | 131.12 (13) | C11—C10—H10A | 108.8 |
C2—C3—C4 | 109.66 (12) | C9—C10—H10A | 108.8 |
C4i—C4—C3 | 114.29 (15) | C11—C10—H10B | 108.8 |
C4i—C4—S1i | 112.49 (13) | C9—C10—H10B | 108.8 |
C3—C4—S1i | 133.22 (11) | H10A—C10—H10B | 107.6 |
C6—C5—C3 | 119.06 (14) | C12—C11—C10 | 112.25 (12) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.2 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.2 |
C5—C6—C7 | 121.96 (14) | C12—C11—H11B | 109.2 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.2 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.39 (13) | O13—C12—C11 | 110.71 (13) |
C8—C7—C9 | 120.67 (15) | O13—C12—H12A | 109.5 |
C6—C7—C9 | 119.91 (14) | C11—C12—H12A | 109.5 |
C2—C8—C7 | 119.08 (14) | O13—C12—H12B | 109.5 |
C2—C8—H8 | 120.5 | C11—C12—H12B | 109.5 |
C7—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.69 (12) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.76 (14) | C3—C5—C6—C7 | 0.0 (2) |
C4i—S1—C2—C3 | −0.39 (11) | C5—C6—C7—C8 | 0.0 (2) |
C8—C2—C3—C5 | 1.1 (2) | C5—C6—C7—C9 | −178.05 (14) |
S1—C2—C3—C5 | −178.80 (11) | C3—C2—C8—C7 | −1.1 (2) |
C8—C2—C3—C4 | −179.90 (13) | S1—C2—C8—C7 | 178.78 (11) |
S1—C2—C3—C4 | 0.25 (15) | C6—C7—C8—C2 | 0.5 (2) |
C5—C3—C4—C4i | 178.97 (16) | C9—C7—C8—C2 | 178.55 (13) |
C2—C3—C4—C4i | 0.1 (2) | C8—C7—C9—C10 | −80.6 (2) |
C5—C3—C4—S1i | −1.5 (3) | C6—C7—C9—C10 | 97.46 (18) |
C2—C3—C4—S1i | 179.60 (11) | C7—C9—C10—C11 | −176.07 (15) |
C2—C3—C5—C6 | −0.5 (2) | C9—C10—C11—C12 | −174.92 (16) |
C4—C3—C5—C6 | −179.33 (14) | C10—C11—C12—O13 | −179.98 (15) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.81 | 2.04 | 2.8033 (10) | 158 |
C6—H6···S1iii | 0.93 | 3.38 | 4.1651 (16) | 144 |
C9—H9A···S1iii | 0.97 | 3.55 | 4.161 (2) | 124 |
C10—H10A···S1iii | 0.97 | 3.37 | 3.994 (2) | 124 |
C10—H10A···S1iv | 0.97 | 3.21 | 3.8978 (18) | 129 |
C11—H11B···S1iii | 0.97 | 3.48 | 4.1586 (19) | 129 |
C12—H12A···S1iv | 0.97 | 3.11 | 3.8619 (19) | 135 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.336 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.725 (2) Å | Cell parameters from 7019 reflections |
b = 5.073 (1) Å | θ = 2.2–24.9° |
c = 14.461 (2) Å | µ = 0.28 mm−1 |
β = 108.301 (19)° | T = 290 K |
V = 955.9 (2) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.026 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.5° |
8549 measured reflections | h = −19→19 |
2837 independent reflections | k = −6→7 |
2459 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.042 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.131 | w = 1/[σ2(Fo2) + (0.0738P)2 + 0.2136P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.020 |
2837 reflections | Δρmax = 0.57 e Å−3 |
121 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.038 (5) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64493 (3) | 0.32387 (8) | 0.53867 (3) | 0.05145 (15) | |
C2 | 0.64750 (10) | 0.5533 (3) | 0.62957 (9) | 0.0435 (3) | |
C3 | 0.55371 (10) | 0.6887 (3) | 0.61224 (9) | 0.0425 (3) | |
C4 | 0.48135 (10) | 0.5960 (3) | 0.52307 (9) | 0.0426 (3) | |
C5 | 0.54518 (12) | 0.8809 (3) | 0.67780 (11) | 0.0513 (3) | |
H5 | 0.484116 | 0.973137 | 0.667379 | 0.062* | |
C6 | 0.62864 (12) | 0.9328 (3) | 0.75863 (10) | 0.0530 (3) | |
H6 | 0.622847 | 1.061523 | 0.802391 | 0.064* | |
C7 | 0.72190 (12) | 0.7974 (3) | 0.77677 (10) | 0.0486 (3) | |
C8 | 0.73118 (11) | 0.6058 (3) | 0.71199 (10) | 0.0494 (3) | |
H8 | 0.792290 | 0.513319 | 0.723158 | 0.059* | |
C9 | 0.80976 (13) | 0.8560 (3) | 0.86797 (11) | 0.0544 (4) | |
H9A | 0.801187 | 1.031930 | 0.890519 | 0.065* | |
H9B | 0.873588 | 0.852910 | 0.852498 | 0.065* | |
C10 | 0.81663 (14) | 0.6613 (3) | 0.94876 (11) | 0.0553 (4) | |
H10A | 0.750973 | 0.655757 | 0.960749 | 0.066* | |
H10B | 0.829480 | 0.487280 | 0.927323 | 0.066* | |
C11 | 0.90008 (13) | 0.7250 (3) | 1.04400 (10) | 0.0513 (3) | |
H11A | 0.965088 | 0.745096 | 1.031468 | 0.062* | |
H11B | 0.884126 | 0.891420 | 1.068996 | 0.062* | |
C12 | 0.91040 (14) | 0.5163 (3) | 1.11904 (11) | 0.0565 (4) | |
H12A | 0.845674 | 0.496019 | 1.132114 | 0.068* | |
H12B | 0.926783 | 0.349583 | 1.094572 | 0.068* | |
O13 | 0.98862 (10) | 0.5822 (3) | 1.20658 (8) | 0.0641 (3) | |
H13 | 0.9951 (14) | 0.466 (5) | 1.2447 (14) | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0439 (2) | 0.0612 (3) | 0.0448 (2) | 0.00709 (14) | 0.00761 (14) | −0.01063 (14) |
C2 | 0.0450 (6) | 0.0480 (7) | 0.0361 (5) | −0.0018 (5) | 0.0108 (5) | −0.0015 (5) |
C3 | 0.0448 (6) | 0.0461 (7) | 0.0361 (6) | −0.0029 (5) | 0.0123 (5) | −0.0019 (5) |
C4 | 0.0417 (6) | 0.0487 (7) | 0.0364 (5) | 0.0001 (5) | 0.0107 (5) | −0.0019 (5) |
C5 | 0.0522 (7) | 0.0554 (8) | 0.0441 (7) | 0.0016 (6) | 0.0119 (6) | −0.0086 (6) |
C6 | 0.0603 (8) | 0.0557 (8) | 0.0405 (6) | −0.0056 (6) | 0.0120 (6) | −0.0098 (6) |
C7 | 0.0535 (7) | 0.0528 (8) | 0.0350 (6) | −0.0117 (6) | 0.0072 (5) | −0.0001 (5) |
C8 | 0.0460 (7) | 0.0560 (8) | 0.0420 (6) | −0.0023 (6) | 0.0075 (5) | −0.0016 (6) |
C9 | 0.0587 (8) | 0.0559 (8) | 0.0402 (6) | −0.0146 (6) | 0.0035 (6) | −0.0016 (6) |
C10 | 0.0657 (9) | 0.0468 (7) | 0.0413 (7) | −0.0114 (6) | −0.0005 (6) | −0.0022 (6) |
C11 | 0.0591 (8) | 0.0455 (7) | 0.0399 (6) | −0.0075 (6) | 0.0021 (6) | −0.0039 (5) |
C12 | 0.0673 (9) | 0.0472 (7) | 0.0423 (7) | −0.0058 (6) | −0.0010 (6) | −0.0016 (6) |
O13 | 0.0740 (8) | 0.0569 (7) | 0.0437 (6) | −0.0035 (6) | −0.0067 (5) | 0.0000 (5) |
S1—C4i | 1.7305 (14) | C9—C10 | 1.510 (2) |
S1—C2 | 1.7476 (14) | C9—H9A | 0.9700 |
C2—C8 | 1.3969 (18) | C9—H9B | 0.9700 |
C2—C3 | 1.4105 (19) | C10—C11 | 1.524 (2) |
C3—C5 | 1.3901 (19) | C10—H10A | 0.9700 |
C3—C4 | 1.4373 (18) | C10—H10B | 0.9700 |
C4—C4i | 1.368 (3) | C11—C12 | 1.491 (2) |
C5—C6 | 1.381 (2) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C6—C7 | 1.403 (2) | C12—O13 | 1.4190 (17) |
C6—H6 | 0.9300 | C12—H12A | 0.9700 |
C7—C8 | 1.383 (2) | C12—H12B | 0.9700 |
C7—C9 | 1.5110 (19) | O13—H13 | 0.79 (3) |
C8—H8 | 0.9300 | ||
C4i—S1—C2 | 90.69 (6) | C10—C9—H9A | 109.1 |
C8—C2—C3 | 121.24 (13) | C7—C9—H9B | 109.1 |
C8—C2—S1 | 125.87 (11) | C10—C9—H9B | 109.1 |
C3—C2—S1 | 112.90 (10) | H9A—C9—H9B | 107.8 |
C5—C3—C2 | 119.21 (12) | C11—C10—C9 | 114.02 (13) |
C5—C3—C4 | 131.22 (13) | C11—C10—H10A | 108.7 |
C2—C3—C4 | 109.57 (12) | C9—C10—H10A | 108.7 |
C4i—C4—C3 | 114.31 (15) | C11—C10—H10B | 108.7 |
C4i—C4—S1i | 112.53 (13) | C9—C10—H10B | 108.7 |
C3—C4—S1i | 133.15 (11) | H10A—C10—H10B | 107.6 |
C6—C5—C3 | 119.07 (14) | C12—C11—C10 | 112.32 (13) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.1 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.1 |
C5—C6—C7 | 122.05 (14) | C12—C11—H11B | 109.1 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.1 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.33 (13) | O13—C12—C11 | 110.75 (13) |
C8—C7—C9 | 120.75 (15) | O13—C12—H12A | 109.5 |
C6—C7—C9 | 119.88 (14) | C11—C12—H12A | 109.5 |
C2—C8—C7 | 119.09 (14) | O13—C12—H12B | 109.5 |
C2—C8—H8 | 120.5 | C11—C12—H12B | 109.5 |
C7—C8—H8 | 120.5 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.68 (12) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.1 | ||
C4i—S1—C2—C8 | 179.76 (14) | C3—C5—C6—C7 | −0.1 (2) |
C4i—S1—C2—C3 | −0.38 (11) | C5—C6—C7—C8 | 0.1 (2) |
C8—C2—C3—C5 | 1.0 (2) | C5—C6—C7—C9 | −178.08 (14) |
S1—C2—C3—C5 | −178.86 (11) | C3—C2—C8—C7 | −1.0 (2) |
C8—C2—C3—C4 | −179.87 (13) | S1—C2—C8—C7 | 178.84 (11) |
S1—C2—C3—C4 | 0.27 (15) | C6—C7—C8—C2 | 0.5 (2) |
C5—C3—C4—C4i | 179.02 (16) | C9—C7—C8—C2 | 178.60 (14) |
C2—C3—C4—C4i | 0.0 (2) | C8—C7—C9—C10 | −80.6 (2) |
C5—C3—C4—S1i | −1.4 (3) | C6—C7—C9—C10 | 97.50 (19) |
C2—C3—C4—S1i | 179.62 (11) | C7—C9—C10—C11 | −176.20 (15) |
C2—C3—C5—C6 | −0.5 (2) | C9—C10—C11—C12 | −175.02 (16) |
C4—C3—C5—C6 | −179.36 (15) | C10—C11—C12—O13 | −179.97 (15) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.79 | 2.06 | 2.8039 (10) | 157 |
C6—H6···S1iii | 0.93 | 3.38 | 4.1720 (15) | 144 |
C9—H9A···S1iii | 0.97 | 3.55 | 4.166 (2) | 124 |
C10—H10A···S1iii | 0.97 | 3.37 | 3.999 (2) | 124 |
C10—H10A···S1iv | 0.97 | 3.22 | 3.9020 (18) | 129 |
C11—H11B···S1iii | 0.97 | 3.49 | 4.1637 (18) | 129 |
C12—H12A···S1iv | 0.97 | 3.12 | 3.8657 (18) | 135 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |
C22H24O2S2 | F(000) = 408 |
Mr = 384.53 | Dx = 1.333 Mg m−3 |
Monoclinic, P21/c | Synchrotron radiation, λ = 0.700 Å |
a = 13.748 (6) Å | Cell parameters from 7097 reflections |
b = 5.072 (1) Å | θ = 2.2–26.0° |
c = 14.477 (2) Å | µ = 0.28 mm−1 |
β = 108.402 (19)° | T = 300 K |
V = 957.9 (5) Å3 | Prism, colourless |
Z = 2 | 0.12 × 0.06 × 0.02 mm |
Huber 4-circles Kappa Goniometer, Pilatus 2M detector diffractometer | Rint = 0.029 |
Rotating crystal scans | θmax = 29.9°, θmin = 1.5° |
8661 measured reflections | h = −19→19 |
2848 independent reflections | k = −6→7 |
2430 reflections with I > 2σ(I) | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0542P)2 + 0.4979P] where P = (Fo2 + 2Fc2)/3 |
S = 0.87 | (Δ/σ)max = 0.002 |
2848 reflections | Δρmax = 0.55 e Å−3 |
121 parameters | Δρmin = −0.29 e Å−3 |
0 restraints | Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: iterative | Extinction coefficient: 0.041 (4) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.64475 (3) | 0.32392 (9) | 0.53874 (3) | 0.05383 (15) | |
C2 | 0.64721 (11) | 0.5528 (3) | 0.62963 (10) | 0.0456 (3) | |
C3 | 0.55382 (11) | 0.6883 (3) | 0.61223 (10) | 0.0442 (3) | |
C4 | 0.48133 (11) | 0.5959 (3) | 0.52300 (10) | 0.0444 (3) | |
C5 | 0.54530 (13) | 0.8803 (3) | 0.67786 (11) | 0.0536 (4) | |
H5 | 0.484299 | 0.972510 | 0.667429 | 0.064* | |
C6 | 0.62870 (13) | 0.9321 (4) | 0.75869 (11) | 0.0554 (4) | |
H6 | 0.622949 | 1.060750 | 0.802436 | 0.066* | |
C7 | 0.72192 (12) | 0.7966 (3) | 0.77694 (10) | 0.0507 (3) | |
C8 | 0.73081 (12) | 0.6058 (4) | 0.71227 (11) | 0.0517 (3) | |
H8 | 0.791831 | 0.513193 | 0.723485 | 0.062* | |
C9 | 0.80957 (14) | 0.8555 (4) | 0.86810 (11) | 0.0570 (4) | |
H9A | 0.800908 | 1.031508 | 0.890522 | 0.068* | |
H9B | 0.873323 | 0.852622 | 0.852740 | 0.068* | |
C10 | 0.81662 (15) | 0.6613 (3) | 0.94886 (11) | 0.0577 (4) | |
H10A | 0.751038 | 0.655556 | 0.960716 | 0.069* | |
H10B | 0.829526 | 0.487236 | 0.927515 | 0.069* | |
C11 | 0.89981 (14) | 0.7250 (3) | 1.04406 (11) | 0.0538 (4) | |
H11A | 0.964736 | 0.745490 | 1.031656 | 0.065* | |
H11B | 0.883759 | 0.891276 | 1.069011 | 0.065* | |
C12 | 0.91033 (14) | 0.5164 (3) | 1.11899 (11) | 0.0586 (4) | |
H12A | 0.845703 | 0.495663 | 1.131943 | 0.070* | |
H12B | 0.926876 | 0.349836 | 1.094608 | 0.070* | |
O13 | 0.98838 (11) | 0.5828 (3) | 1.20654 (8) | 0.0669 (4) | |
H13 | 0.9966 (15) | 0.467 (5) | 1.2428 (15) | 0.100* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0455 (2) | 0.0642 (3) | 0.0470 (2) | 0.00729 (16) | 0.00796 (15) | −0.01114 (17) |
C2 | 0.0470 (7) | 0.0505 (8) | 0.0378 (6) | −0.0018 (6) | 0.0114 (5) | −0.0012 (6) |
C3 | 0.0463 (7) | 0.0486 (8) | 0.0375 (6) | −0.0032 (6) | 0.0128 (5) | −0.0023 (5) |
C4 | 0.0428 (6) | 0.0509 (8) | 0.0383 (6) | −0.0005 (6) | 0.0111 (5) | −0.0023 (6) |
C5 | 0.0538 (8) | 0.0586 (9) | 0.0467 (8) | 0.0014 (7) | 0.0133 (6) | −0.0084 (7) |
C6 | 0.0634 (9) | 0.0580 (9) | 0.0423 (7) | −0.0063 (7) | 0.0132 (6) | −0.0103 (7) |
C7 | 0.0551 (8) | 0.0550 (9) | 0.0372 (6) | −0.0121 (7) | 0.0079 (6) | 0.0006 (6) |
C8 | 0.0470 (7) | 0.0588 (9) | 0.0447 (7) | −0.0026 (6) | 0.0081 (6) | −0.0016 (7) |
C9 | 0.0609 (9) | 0.0588 (9) | 0.0424 (7) | −0.0148 (7) | 0.0034 (6) | −0.0025 (7) |
C10 | 0.0681 (10) | 0.0492 (8) | 0.0434 (7) | −0.0113 (7) | 0.0001 (7) | −0.0026 (6) |
C11 | 0.0614 (9) | 0.0476 (8) | 0.0425 (7) | −0.0079 (7) | 0.0024 (6) | −0.0045 (6) |
C12 | 0.0680 (10) | 0.0507 (9) | 0.0440 (7) | −0.0057 (7) | −0.0010 (7) | −0.0021 (7) |
O13 | 0.0771 (8) | 0.0596 (7) | 0.0452 (6) | −0.0036 (6) | −0.0074 (6) | −0.0006 (5) |
S1—C4i | 1.7294 (16) | C9—C10 | 1.508 (2) |
S1—C2 | 1.7471 (15) | C9—H9A | 0.9700 |
C2—C8 | 1.399 (2) | C9—H9B | 0.9700 |
C2—C3 | 1.407 (2) | C10—C11 | 1.522 (2) |
C3—C5 | 1.391 (2) | C10—H10A | 0.9700 |
C3—C4 | 1.4384 (19) | C10—H10B | 0.9700 |
C4—C4i | 1.367 (3) | C11—C12 | 1.489 (2) |
C5—C6 | 1.381 (2) | C11—H11A | 0.9700 |
C5—H5 | 0.9300 | C11—H11B | 0.9700 |
C6—C7 | 1.404 (3) | C12—O13 | 1.4186 (18) |
C6—H6 | 0.9300 | C12—H12A | 0.9700 |
C7—C8 | 1.378 (2) | C12—H12B | 0.9700 |
C7—C9 | 1.510 (2) | O13—H13 | 0.77 (3) |
C8—H8 | 0.9300 | ||
C4i—S1—C2 | 90.62 (7) | C10—C9—H9A | 109.0 |
C8—C2—C3 | 121.07 (14) | C7—C9—H9B | 109.0 |
C8—C2—S1 | 125.96 (12) | C10—C9—H9B | 109.0 |
C3—C2—S1 | 112.96 (10) | H9A—C9—H9B | 107.8 |
C5—C3—C2 | 119.24 (13) | C11—C10—C9 | 114.16 (14) |
C5—C3—C4 | 131.13 (14) | C11—C10—H10A | 108.7 |
C2—C3—C4 | 109.62 (13) | C9—C10—H10A | 108.7 |
C4i—C4—C3 | 114.16 (16) | C11—C10—H10B | 108.7 |
C4i—C4—S1i | 112.63 (14) | C9—C10—H10B | 108.7 |
C3—C4—S1i | 133.21 (12) | H10A—C10—H10B | 107.6 |
C6—C5—C3 | 119.06 (15) | C12—C11—C10 | 112.41 (14) |
C6—C5—H5 | 120.5 | C12—C11—H11A | 109.1 |
C3—C5—H5 | 120.5 | C10—C11—H11A | 109.1 |
C5—C6—C7 | 122.07 (15) | C12—C11—H11B | 109.1 |
C5—C6—H6 | 119.0 | C10—C11—H11B | 109.1 |
C7—C6—H6 | 119.0 | H11A—C11—H11B | 107.9 |
C8—C7—C6 | 119.16 (14) | O13—C12—C11 | 110.76 (14) |
C8—C7—C9 | 121.02 (16) | O13—C12—H12A | 109.5 |
C6—C7—C9 | 119.80 (15) | C11—C12—H12A | 109.5 |
C2—C8—C7 | 119.39 (15) | O13—C12—H12B | 109.5 |
C2—C8—H8 | 120.3 | C11—C12—H12B | 109.5 |
C7—C8—H8 | 120.3 | H12A—C12—H12B | 108.1 |
C7—C9—C10 | 112.74 (14) | C12—O13—H13 | 109.5 |
C7—C9—H9A | 109.0 | ||
C4i—S1—C2—C8 | 179.82 (15) | C3—C5—C6—C7 | −0.1 (3) |
C4i—S1—C2—C3 | −0.52 (12) | C5—C6—C7—C8 | 0.0 (3) |
C8—C2—C3—C5 | 0.8 (2) | C5—C6—C7—C9 | −178.14 (16) |
S1—C2—C3—C5 | −178.84 (12) | C3—C2—C8—C7 | −0.9 (2) |
C8—C2—C3—C4 | −179.87 (14) | S1—C2—C8—C7 | 178.70 (12) |
S1—C2—C3—C4 | 0.45 (16) | C6—C7—C8—C2 | 0.5 (2) |
C5—C3—C4—C4i | 179.07 (18) | C9—C7—C8—C2 | 178.65 (15) |
C2—C3—C4—C4i | −0.1 (2) | C8—C7—C9—C10 | −80.6 (2) |
C5—C3—C4—S1i | −1.3 (3) | C6—C7—C9—C10 | 97.5 (2) |
C2—C3—C4—S1i | 179.53 (12) | C7—C9—C10—C11 | −176.21 (16) |
C2—C3—C5—C6 | −0.3 (2) | C9—C10—C11—C12 | −174.94 (17) |
C4—C3—C5—C6 | −179.41 (16) | C10—C11—C12—O13 | −179.94 (16) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O13—H13···O13ii | 0.77 | 2.07 | 2.8041 (11) | 159 |
C6—H6···S1iii | 0.93 | 3.39 | 4.1776 (17) | 144 |
C9—H9A···S1iii | 0.97 | 3.56 | 4.173 (2) | 124 |
C10—H10A···S1iii | 0.97 | 3.38 | 4.004 (2) | 124 |
C10—H10A···S1iv | 0.97 | 3.22 | 3.908 (2) | 129 |
C11—H11B···S1iii | 0.97 | 3.49 | 4.167 (2) | 129 |
C12—H12A···S1iv | 0.97 | 3.12 | 3.871 (2) | 136 |
Symmetry codes: (ii) −x+2, y−1/2, −z+5/2; (iii) x, −y+3/2, z+1/2; (iv) x, −y+1/2, z+1/2. |