Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013455/hg6051sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013455/hg6051IIsup2.hkl |
CCDC reference: 248801
Data collection: IPDS (Stoe & Cie, 1997); cell refinement: IPDS; data reduction: IPDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97.
C13H22O8S | Dx = 1.408 Mg m−3 |
Mr = 338.37 | Melting point: 355(1) K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.866 (3) Å | Cell parameters from 5000 reflections |
b = 9.2962 (16) Å | θ = 2.5–25.0° |
c = 19.361 (3) Å | µ = 0.24 mm−1 |
V = 1595.8 (7) Å3 | T = 150 K |
Z = 4 | Block, white |
F(000) = 720 | 0.48 × 0.40 × 0.20 mm |
Stoe IPDS diffractometer | 2236 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.086 |
Planar graphite monochromator | θmax = 25.3°, θmin = 2.5° |
Detector resolution: 6.667 pixels mm-1 | h = −10→10 |
φ scans | k = −11→8 |
6444 measured reflections | l = −19→23 |
2686 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0459P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.090 | (Δ/σ)max = 0.005 |
S = 0.93 | Δρmax = 0.23 e Å−3 |
2686 reflections | Δρmin = −0.43 e Å−3 |
209 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.010 (2) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.03 (10) |
Experimental. Recrystallized from methylcyclohexane. During data collection the crystal was in cold N2 gas of the Cryostream Cooler (Oxford Cryosystems) mounted on a φ-axis diffractometer supplied with an area detector. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3896 (3) | 0.1403 (3) | 0.23268 (14) | 0.0162 (6) | |
H1 | 0.3243 | 0.2279 | 0.2303 | 0.019* | |
C2 | 0.5182 (3) | 0.1668 (3) | 0.28368 (14) | 0.0172 (6) | |
H2 | 0.5628 | 0.2651 | 0.2789 | 0.026 (9)* | |
C3 | 0.4396 (3) | 0.1454 (4) | 0.35284 (15) | 0.0177 (6) | |
H3 | 0.5082 | 0.1069 | 0.3894 | 0.010 (7)* | |
C4 | 0.2208 (3) | 0.2415 (3) | 0.39829 (15) | 0.0193 (6) | |
C5 | 0.3071 (3) | 0.0434 (3) | 0.33604 (14) | 0.0186 (6) | |
H5 | 0.3178 | −0.0505 | 0.3607 | 0.011 (7)* | |
C6 | 0.4290 (3) | 0.0925 (4) | 0.16034 (14) | 0.0196 (7) | |
H6 | 0.4934 | 0.0042 | 0.1616 | 0.015 (7)* | |
C7 | 0.2869 (3) | 0.0664 (4) | 0.11592 (14) | 0.0261 (7) | |
H7A | 0.2741 | −0.0374 | 0.1060 | 0.031* | |
H7B | 0.1955 | 0.1021 | 0.1398 | 0.031* | |
C8 | 0.4667 (3) | 0.1935 (4) | 0.05373 (15) | 0.0205 (7) | |
C9 | 0.5659 (3) | 0.0832 (4) | 0.01820 (17) | 0.0294 (7) | |
H9A | 0.6706 | 0.1172 | 0.0180 | 0.035* | |
H9B | 0.5314 | 0.0696 | −0.0294 | 0.035* | |
H9C | 0.5600 | −0.0084 | 0.0431 | 0.035* | |
C10 | 0.4739 (3) | 0.3396 (4) | 0.02064 (17) | 0.0263 (7) | |
H10A | 0.4070 | 0.4058 | 0.0454 | 0.032* | |
H10B | 0.4418 | 0.3325 | −0.0277 | 0.032* | |
H10C | 0.5777 | 0.3758 | 0.0226 | 0.032* | |
C11 | 0.8813 (3) | 0.1886 (4) | 0.24291 (18) | 0.0283 (7) | |
H11A | 0.8693 | 0.1480 | 0.1965 | 0.034* | |
H11B | 0.9889 | 0.1979 | 0.2536 | 0.034* | |
H11C | 0.8336 | 0.2837 | 0.2447 | 0.034* | |
C12 | 0.1165 (3) | 0.3639 (4) | 0.38226 (18) | 0.0286 (7) | |
H12A | 0.1178 | 0.3828 | 0.3325 | 0.034* | |
H12B | 0.1498 | 0.4500 | 0.4071 | 0.034* | |
H12C | 0.0139 | 0.3388 | 0.3967 | 0.034* | |
C13 | 0.2290 (3) | 0.2040 (4) | 0.47382 (17) | 0.0288 (7) | |
H13A | 0.1300 | 0.1708 | 0.4897 | 0.035* | |
H13B | 0.2589 | 0.2892 | 0.5003 | 0.035* | |
H13C | 0.3036 | 0.1275 | 0.4807 | 0.035* | |
O1 | 0.36905 (19) | 0.2773 (2) | 0.37190 (11) | 0.0197 (5) | |
O2 | 0.17704 (19) | 0.1184 (2) | 0.35810 (11) | 0.0231 (5) | |
O3 | 0.3061 (2) | 0.0241 (2) | 0.26381 (10) | 0.0208 (5) | |
O4 | 0.31308 (19) | 0.1447 (3) | 0.05423 (10) | 0.0258 (5) | |
O5 | 0.50549 (19) | 0.2067 (2) | 0.12545 (10) | 0.0210 (5) | |
O6 | 0.62951 (18) | 0.0529 (2) | 0.27332 (10) | 0.0193 (5) | |
O7 | 0.8601 (2) | −0.0646 (3) | 0.29966 (12) | 0.0293 (5) | |
O8 | 0.7867 (2) | 0.1481 (3) | 0.36831 (11) | 0.0278 (5) | |
S | 0.79571 (7) | 0.07493 (8) | 0.30346 (4) | 0.01918 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0147 (12) | 0.0147 (14) | 0.0192 (15) | −0.0019 (10) | −0.0014 (10) | −0.0020 (13) |
C2 | 0.0145 (11) | 0.0161 (16) | 0.0212 (15) | 0.0015 (10) | −0.0009 (10) | −0.0035 (13) |
C3 | 0.0184 (12) | 0.0185 (16) | 0.0162 (15) | −0.0011 (12) | −0.0036 (10) | 0.0000 (14) |
C4 | 0.0136 (12) | 0.0227 (16) | 0.0217 (15) | −0.0045 (12) | 0.0056 (11) | −0.0005 (13) |
C5 | 0.0213 (12) | 0.0178 (16) | 0.0168 (14) | 0.0013 (13) | 0.0028 (11) | −0.0007 (12) |
C6 | 0.0178 (12) | 0.0237 (17) | 0.0175 (15) | −0.0035 (11) | −0.0015 (10) | −0.0037 (14) |
C7 | 0.0230 (13) | 0.0385 (18) | 0.0168 (14) | −0.0135 (15) | −0.0032 (11) | −0.0021 (15) |
C8 | 0.0127 (12) | 0.0281 (18) | 0.0208 (16) | −0.0036 (11) | −0.0005 (10) | −0.0012 (14) |
C9 | 0.0282 (14) | 0.0322 (19) | 0.0276 (18) | 0.0021 (14) | 0.0060 (12) | −0.0011 (18) |
C10 | 0.0244 (13) | 0.0270 (18) | 0.0276 (17) | 0.0015 (13) | 0.0015 (12) | 0.0030 (15) |
C11 | 0.0235 (14) | 0.0283 (19) | 0.0331 (19) | −0.0012 (13) | 0.0045 (12) | −0.0009 (16) |
C12 | 0.0253 (13) | 0.0296 (18) | 0.0310 (18) | 0.0048 (14) | −0.0002 (13) | −0.0062 (16) |
C13 | 0.0296 (15) | 0.0322 (19) | 0.0246 (17) | −0.0052 (13) | 0.0071 (12) | −0.0017 (16) |
O1 | 0.0174 (8) | 0.0205 (11) | 0.0211 (11) | −0.0043 (8) | 0.0067 (8) | −0.0031 (10) |
O2 | 0.0172 (9) | 0.0260 (12) | 0.0260 (11) | −0.0046 (8) | 0.0036 (8) | −0.0092 (10) |
O3 | 0.0204 (9) | 0.0234 (11) | 0.0186 (11) | −0.0068 (9) | 0.0012 (8) | −0.0035 (9) |
O4 | 0.0143 (8) | 0.0364 (13) | 0.0266 (12) | −0.0054 (9) | −0.0054 (8) | 0.0053 (10) |
O5 | 0.0180 (9) | 0.0283 (12) | 0.0166 (10) | −0.0064 (8) | −0.0014 (7) | 0.0023 (10) |
O6 | 0.0125 (8) | 0.0221 (11) | 0.0234 (10) | −0.0001 (8) | −0.0026 (7) | −0.0059 (10) |
O7 | 0.0212 (8) | 0.0285 (12) | 0.0380 (13) | 0.0034 (9) | −0.0032 (9) | 0.0009 (13) |
O8 | 0.0192 (8) | 0.0398 (13) | 0.0243 (11) | 0.0009 (10) | −0.0032 (8) | −0.0086 (11) |
S | 0.0141 (3) | 0.0223 (4) | 0.0211 (4) | 0.0011 (3) | −0.0019 (3) | −0.0020 (3) |
C1—O3 | 1.442 (3) | C8—O5 | 1.436 (4) |
C1—C6 | 1.510 (4) | C8—O4 | 1.436 (3) |
C1—C2 | 1.528 (4) | C8—C10 | 1.503 (5) |
C1—H1 | 1.0000 | C8—C9 | 1.516 (4) |
C2—O6 | 1.462 (3) | C9—H9A | 0.9800 |
C2—C3 | 1.522 (4) | C9—H9B | 0.9800 |
C2—H2 | 1.0000 | C9—H9C | 0.9800 |
C3—O1 | 1.425 (4) | C10—H10A | 0.9800 |
C3—C5 | 1.544 (4) | C10—H10B | 0.9800 |
C3—H3 | 1.0000 | C10—H10C | 0.9800 |
C4—O2 | 1.437 (4) | C11—S | 1.752 (3) |
C4—O1 | 1.449 (3) | C11—H11A | 0.9800 |
C4—C12 | 1.498 (4) | C11—H11B | 0.9800 |
C4—C13 | 1.505 (4) | C11—H11C | 0.9800 |
C5—O3 | 1.410 (3) | C12—H12A | 0.9800 |
C5—O2 | 1.414 (3) | C12—H12B | 0.9800 |
C5—H5 | 1.0000 | C12—H12C | 0.9800 |
C6—O5 | 1.429 (4) | C13—H13A | 0.9800 |
C6—C7 | 1.545 (3) | C13—H13B | 0.9800 |
C6—H6 | 1.0000 | C13—H13C | 0.9800 |
C7—O4 | 1.418 (4) | O6—S | 1.5982 (17) |
C7—H7A | 0.9900 | O7—S | 1.419 (2) |
C7—H7B | 0.9900 | O8—S | 1.430 (2) |
O3—C1—C6 | 106.6 (2) | O5—C8—C9 | 110.9 (2) |
O3—C1—C2 | 103.5 (2) | O4—C8—C9 | 109.9 (3) |
C6—C1—C2 | 118.3 (2) | C10—C8—C9 | 113.1 (3) |
O3—C1—H1 | 109.3 | C8—C9—H9A | 109.5 |
C6—C1—H1 | 109.3 | C8—C9—H9B | 109.5 |
C2—C1—H1 | 109.3 | H9A—C9—H9B | 109.5 |
O6—C2—C3 | 109.6 (2) | C8—C9—H9C | 109.5 |
O6—C2—C1 | 107.4 (2) | H9A—C9—H9C | 109.5 |
C3—C2—C1 | 101.9 (2) | H9B—C9—H9C | 109.5 |
O6—C2—H2 | 112.5 | C8—C10—H10A | 109.5 |
C3—C2—H2 | 112.5 | C8—C10—H10B | 109.5 |
C1—C2—H2 | 112.5 | H10A—C10—H10B | 109.5 |
O1—C3—C2 | 108.4 (2) | C8—C10—H10C | 109.5 |
O1—C3—C5 | 104.4 (2) | H10A—C10—H10C | 109.5 |
C2—C3—C5 | 104.1 (2) | H10B—C10—H10C | 109.5 |
O1—C3—H3 | 113.1 | S—C11—H11A | 109.5 |
C2—C3—H3 | 113.1 | S—C11—H11B | 109.5 |
C5—C3—H3 | 113.1 | H11A—C11—H11B | 109.5 |
O2—C4—O1 | 103.7 (2) | S—C11—H11C | 109.5 |
O2—C4—C12 | 109.0 (2) | H11A—C11—H11C | 109.5 |
O1—C4—C12 | 108.2 (2) | H11B—C11—H11C | 109.5 |
O2—C4—C13 | 110.8 (3) | C4—C12—H12A | 109.5 |
O1—C4—C13 | 110.6 (2) | C4—C12—H12B | 109.5 |
C12—C4—C13 | 114.0 (3) | H12A—C12—H12B | 109.5 |
O3—C5—O2 | 110.9 (2) | C4—C12—H12C | 109.5 |
O3—C5—C3 | 107.0 (2) | H12A—C12—H12C | 109.5 |
O2—C5—C3 | 104.7 (2) | H12B—C12—H12C | 109.5 |
O3—C5—H5 | 111.3 | C4—C13—H13A | 109.5 |
O2—C5—H5 | 111.3 | C4—C13—H13B | 109.5 |
C3—C5—H5 | 111.3 | H13A—C13—H13B | 109.5 |
O5—C6—C1 | 109.2 (2) | C4—C13—H13C | 109.5 |
O5—C6—C7 | 103.9 (2) | H13A—C13—H13C | 109.5 |
C1—C6—C7 | 112.0 (2) | H13B—C13—H13C | 109.5 |
O5—C6—H6 | 110.5 | C3—O1—C4 | 107.0 (2) |
C1—C6—H6 | 110.5 | C5—O2—C4 | 109.64 (19) |
C7—C6—H6 | 110.5 | C5—O3—C1 | 108.4 (2) |
O4—C7—C6 | 104.8 (2) | C7—O4—C8 | 108.9 (2) |
O4—C7—H7A | 110.8 | C6—O5—C8 | 106.3 (2) |
C6—C7—H7A | 110.8 | C2—O6—S | 118.66 (17) |
O4—C7—H7B | 110.8 | O7—S—O8 | 120.19 (14) |
C6—C7—H7B | 110.8 | O7—S—O6 | 103.55 (12) |
H7A—C7—H7B | 108.9 | O8—S—O6 | 109.27 (11) |
O5—C8—O4 | 104.3 (2) | O7—S—C11 | 110.05 (15) |
O5—C8—C10 | 109.0 (3) | O8—S—C11 | 108.94 (16) |
O4—C8—C10 | 109.2 (2) | O6—S—C11 | 103.46 (13) |
O3—C1—C2—O6 | 77.0 (2) | O3—C5—O2—C4 | −126.2 (2) |
C6—C1—C2—O6 | −40.6 (3) | C3—C5—O2—C4 | −11.2 (3) |
O3—C1—C2—C3 | −38.1 (3) | O1—C4—O2—C5 | 27.3 (3) |
C6—C1—C2—C3 | −155.7 (3) | C12—C4—O2—C5 | 142.4 (2) |
O6—C2—C3—O1 | 161.88 (19) | C13—C4—O2—C5 | −91.3 (3) |
C1—C2—C3—O1 | −84.6 (3) | O2—C5—O3—C1 | 94.1 (2) |
O6—C2—C3—C5 | −87.4 (2) | C3—C5—O3—C1 | −19.6 (3) |
C1—C2—C3—C5 | 26.1 (3) | C6—C1—O3—C5 | 162.1 (2) |
O1—C3—C5—O3 | 108.3 (2) | C2—C1—O3—C5 | 36.6 (3) |
C2—C3—C5—O3 | −5.3 (3) | C6—C7—O4—C8 | 9.6 (3) |
O1—C3—C5—O2 | −9.5 (3) | O5—C8—O4—C7 | −27.7 (3) |
C2—C3—C5—O2 | −123.1 (2) | C10—C8—O4—C7 | −144.1 (3) |
O3—C1—C6—O5 | 177.01 (19) | C9—C8—O4—C7 | 91.3 (3) |
C2—C1—C6—O5 | −67.0 (3) | C1—C6—O5—C8 | −148.7 (2) |
O3—C1—C6—C7 | 62.5 (3) | C7—C6—O5—C8 | −29.0 (3) |
C2—C1—C6—C7 | 178.4 (3) | O4—C8—O5—C6 | 35.5 (3) |
O5—C6—C7—O4 | 11.9 (3) | C10—C8—O5—C6 | 152.0 (2) |
C1—C6—C7—O4 | 129.7 (3) | C9—C8—O5—C6 | −82.8 (3) |
C2—C3—O1—C4 | 136.9 (2) | C3—C2—O6—S | −87.0 (2) |
C5—C3—O1—C4 | 26.4 (3) | C1—C2—O6—S | 163.10 (17) |
O2—C4—O1—C3 | −33.4 (3) | C2—O6—S—O7 | 166.3 (2) |
C12—C4—O1—C3 | −149.1 (2) | C2—O6—S—O8 | 37.0 (2) |
C13—C4—O1—C3 | 85.4 (3) | C2—O6—S—C11 | −78.9 (2) |