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
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.004 Å
- R factor = 0.039
- wR factor = 0.090
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.50 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.25 From the CIF: _reflns_number_total 2686 Count of symmetry unique reflns 1679 Completeness (_total/calc) 159.98% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1007 Fraction of Friedel pairs measured 0.600 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
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) |
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