Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805018684/ob6534sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805018684/ob6534Isup2.hkl |
CCDC reference: 277739
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.141
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C7 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C19
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: CRYSTALS (Watkin et al., 1996); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C22H18O3S | F(000) = 760.00 |
Mr = 362.44 | Dx = 1.279 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2yn | Cell parameters from 12090 reflections |
a = 13.6890 (4) Å | θ = 2.5–27.4° |
b = 8.2386 (2) Å | µ = 0.19 mm−1 |
c = 16.7066 (5) Å | T = 296 K |
β = 92.9198 (9)° | Block, colorless |
V = 1881.69 (9) Å3 | 0.60 × 0.40 × 0.20 mm |
Z = 4 |
Rigaku R-AXIS RAPID diffractometer | 3067 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.025 |
ω scans | θmax = 27.4° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −17→17 |
Tmin = 0.827, Tmax = 0.963 | k = −10→10 |
18258 measured reflections | l = −21→21 |
4301 independent reflections |
Refinement on F2 | w = 1/[0.0024Fo2 + σ(Fo2)]/(4Fo2) |
R[F2 > 2σ(F2)] = 0.045 | (Δ/σ)max < 0.001 |
wR(F2) = 0.141 | Δρmax = 0.29 e Å−3 |
S = 1.00 | Δρmin = −0.28 e Å−3 |
4116 reflections | Extinction correction: Larson (1970) |
236 parameters | Extinction coefficient: 124 (37) |
H-atom parameters constrained |
Geometry. ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY |
Refinement. Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.67670 (3) | 0.46093 (5) | 0.84053 (3) | 0.0479 (1) | |
O1 | 0.4345 (1) | 0.4160 (2) | 0.8205 (1) | 0.0884 (6) | |
O2 | 0.76991 (9) | 0.4379 (2) | 0.80708 (8) | 0.0634 (4) | |
O3 | 0.6593 (1) | 0.6096 (1) | 0.88222 (9) | 0.0680 (4) | |
C1 | 0.5857 (1) | 0.4447 (2) | 0.7617 (1) | 0.0449 (4) | |
C2 | 0.6102 (1) | 0.3744 (2) | 0.6938 (1) | 0.0479 (5) | |
C3 | 0.5507 (1) | 0.3365 (2) | 0.6207 (1) | 0.0519 (5) | |
C4 | 0.4514 (2) | 0.3688 (3) | 0.6091 (2) | 0.0756 (7) | |
C5 | 0.4010 (2) | 0.3252 (3) | 0.5391 (2) | 0.0854 (8) | |
C6 | 0.4465 (2) | 0.2479 (3) | 0.4801 (2) | 0.0871 (8) | |
C7 | 0.5434 (2) | 0.2137 (4) | 0.4907 (2) | 0.101 (1) | |
C8 | 0.5958 (2) | 0.2572 (3) | 0.5604 (1) | 0.0724 (7) | |
C9 | 0.4858 (1) | 0.5030 (2) | 0.7832 (1) | 0.0500 (5) | |
C10 | 0.4540 (1) | 0.6672 (2) | 0.7564 (1) | 0.0473 (4) | |
C11 | 0.5197 (1) | 0.7878 (2) | 0.7389 (1) | 0.0513 (5) | |
C12 | 0.4867 (2) | 0.9402 (2) | 0.7164 (1) | 0.0660 (6) | |
C13 | 0.3882 (2) | 0.9697 (3) | 0.7078 (2) | 0.0819 (8) | |
C14 | 0.3222 (2) | 0.8496 (3) | 0.7218 (2) | 0.0893 (8) | |
C15 | 0.3551 (1) | 0.7005 (2) | 0.7470 (2) | 0.0765 (7) | |
C16 | 0.6558 (1) | 0.2977 (2) | 0.9052 (1) | 0.0454 (4) | |
C17 | 0.6717 (1) | 0.1405 (2) | 0.8792 (1) | 0.0532 (5) | |
C18 | 0.6598 (1) | 0.0126 (2) | 0.9307 (1) | 0.0624 (6) | |
C19 | 0.6333 (2) | 0.0374 (3) | 1.0086 (1) | 0.0671 (6) | |
C20 | 0.6155 (2) | 0.1941 (3) | 1.0325 (1) | 0.0805 (8) | |
C21 | 0.6256 (2) | 0.3255 (3) | 0.9815 (1) | 0.0675 (6) | |
C22 | 0.6252 (2) | −0.1042 (4) | 1.0653 (2) | 0.107 (1) | |
H1 | 0.6791 | 0.3428 | 0.6924 | 0.057* | |
H2 | 0.4168 | 0.4239 | 0.6513 | 0.090* | |
H3 | 0.3311 | 0.3502 | 0.5320 | 0.101* | |
H4 | 0.4102 | 0.2171 | 0.4304 | 0.103* | |
H5 | 0.5767 | 0.1569 | 0.4484 | 0.120* | |
H6 | 0.6657 | 0.2316 | 0.5667 | 0.087* | |
H7 | 0.5900 | 0.7650 | 0.7425 | 0.062* | |
H8 | 0.5336 | 1.0270 | 0.7068 | 0.079* | |
H9 | 0.3648 | 1.0777 | 0.6913 | 0.098* | |
H10 | 0.2519 | 0.8704 | 0.7138 | 0.107* | |
H11 | 0.3076 | 0.6158 | 0.7587 | 0.092* | |
H12 | 0.6912 | 0.1206 | 0.8245 | 0.064* | |
H13 | 0.6704 | −0.0983 | 0.9119 | 0.075* | |
H14 | 0.5951 | 0.2135 | 1.0871 | 0.097* | |
H15 | 0.6115 | 0.4359 | 0.9994 | 0.082* | |
H16 | 0.5598 | −0.1466 | 1.0611 | 0.129* | |
H17 | 0.6401 | −0.0684 | 1.1193 | 0.129* | |
H18 | 0.6705 | −0.1874 | 1.0516 | 0.129* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0419 (3) | 0.0405 (3) | 0.0605 (3) | −0.0029 (2) | −0.0048 (2) | −0.0008 (2) |
O1 | 0.0531 (8) | 0.077 (1) | 0.137 (2) | −0.0007 (7) | 0.0250 (9) | 0.048 (1) |
O2 | 0.0365 (6) | 0.0791 (9) | 0.0739 (9) | −0.0048 (6) | −0.0024 (6) | 0.0101 (7) |
O3 | 0.080 (1) | 0.0389 (7) | 0.083 (1) | −0.0023 (6) | −0.0143 (8) | −0.0095 (7) |
C1 | 0.0367 (8) | 0.0359 (8) | 0.062 (1) | −0.0006 (6) | −0.0018 (7) | 0.0057 (7) |
C2 | 0.0421 (8) | 0.0407 (8) | 0.060 (1) | 0.0017 (7) | −0.0037 (7) | 0.0058 (8) |
C3 | 0.053 (1) | 0.0391 (8) | 0.062 (1) | −0.0017 (7) | −0.0098 (8) | 0.0083 (8) |
C4 | 0.059 (1) | 0.074 (1) | 0.091 (2) | 0.014 (1) | −0.021 (1) | −0.017 (1) |
C5 | 0.069 (1) | 0.083 (2) | 0.100 (2) | 0.004 (1) | −0.034 (1) | −0.001 (1) |
C6 | 0.093 (2) | 0.094 (2) | 0.071 (2) | −0.016 (1) | −0.028 (1) | 0.004 (1) |
C7 | 0.105 (2) | 0.135 (2) | 0.061 (1) | −0.005 (2) | −0.005 (1) | −0.018 (2) |
C8 | 0.067 (1) | 0.089 (2) | 0.061 (1) | −0.002 (1) | −0.000 (1) | −0.004 (1) |
C9 | 0.0385 (8) | 0.0449 (9) | 0.067 (1) | −0.0043 (7) | 0.0040 (8) | 0.0065 (8) |
C10 | 0.0374 (8) | 0.0420 (8) | 0.063 (1) | 0.0006 (7) | 0.0067 (7) | −0.0038 (8) |
C11 | 0.0415 (9) | 0.0454 (9) | 0.067 (1) | −0.0027 (7) | 0.0028 (8) | 0.0046 (8) |
C12 | 0.060 (1) | 0.046 (1) | 0.092 (2) | −0.0044 (8) | 0.002 (1) | 0.009 (1) |
C13 | 0.068 (1) | 0.048 (1) | 0.129 (2) | 0.014 (1) | −0.001 (1) | 0.005 (1) |
C14 | 0.048 (1) | 0.057 (1) | 0.163 (3) | 0.014 (1) | 0.003 (1) | −0.002 (1) |
C15 | 0.0398 (9) | 0.048 (1) | 0.142 (2) | 0.0001 (8) | 0.012 (1) | −0.001 (1) |
C16 | 0.0418 (8) | 0.0425 (8) | 0.0517 (9) | 0.0035 (7) | −0.0002 (7) | −0.0034 (7) |
C17 | 0.060 (1) | 0.0442 (9) | 0.055 (1) | 0.0059 (8) | 0.0021 (8) | −0.0056 (8) |
C18 | 0.065 (1) | 0.0443 (9) | 0.077 (1) | 0.0034 (9) | −0.006 (1) | 0.0020 (9) |
C19 | 0.062 (1) | 0.067 (1) | 0.072 (1) | −0.002 (1) | −0.001 (1) | 0.018 (1) |
C20 | 0.099 (2) | 0.088 (2) | 0.056 (1) | 0.006 (1) | 0.019 (1) | 0.004 (1) |
C21 | 0.084 (1) | 0.057 (1) | 0.063 (1) | 0.010 (1) | 0.013 (1) | −0.009 (1) |
C22 | 0.107 (2) | 0.104 (2) | 0.109 (2) | −0.013 (2) | −0.007 (2) | 0.054 (2) |
S1—O2 | 1.431 (1) | C17—C18 | 1.375 (3) |
S1—O3 | 1.435 (1) | C18—C19 | 1.383 (3) |
S1—C1 | 1.770 (2) | C19—C20 | 1.377 (3) |
S1—C16 | 1.758 (2) | C19—C22 | 1.511 (4) |
O1—C9 | 1.201 (3) | C20—C21 | 1.389 (3) |
C1—C2 | 1.332 (3) | C2—H1 | 0.9800 |
C1—C9 | 1.510 (2) | C4—H2 | 0.9800 |
C2—C3 | 1.467 (2) | C5—H3 | 0.9800 |
C3—C4 | 1.389 (3) | C6—H4 | 0.9800 |
C3—C8 | 1.374 (3) | C7—H5 | 0.9800 |
C4—C5 | 1.375 (4) | C8—H6 | 0.9800 |
C5—C6 | 1.352 (4) | C11—H7 | 0.9800 |
C6—C7 | 1.359 (4) | C12—H8 | 0.9800 |
C7—C8 | 1.383 (4) | C13—H9 | 0.9800 |
C9—C10 | 1.483 (2) | C14—H10 | 0.9800 |
C10—C11 | 1.381 (2) | C15—H11 | 0.9800 |
C10—C15 | 1.383 (3) | C17—H12 | 0.9800 |
C11—C12 | 1.380 (3) | C18—H13 | 0.9800 |
C12—C13 | 1.371 (3) | C20—H14 | 0.9800 |
C13—C14 | 1.368 (3) | C21—H15 | 0.9800 |
C14—C15 | 1.367 (3) | C22—H16 | 0.9600 |
C16—C17 | 1.386 (2) | C22—H17 | 0.9600 |
C16—C21 | 1.379 (3) | C22—H18 | 0.9600 |
O3—S1—O2 | 118.45 (9) | C22—C19—C20 | 121.5 (2) |
C1—S1—O2 | 107.87 (8) | C1—C2—H1 | 114.7830 |
C16—S1—O2 | 108.34 (8) | H1—C2—C3 | 114.7090 |
C1—S1—O3 | 107.31 (8) | C3—C4—H2 | 119.5638 |
C16—S1—O3 | 108.57 (9) | C3—C8—H6 | 119.7561 |
S1—C1—C2 | 118.0 (1) | H2—C4—C5 | 119.5273 |
S1—C1—C9 | 114.3 (1) | C4—C5—H3 | 119.5360 |
C16—S1—C1 | 105.58 (8) | H3—C5—C6 | 119.5859 |
S1—C16—C17 | 119.3 (1) | C5—C6—H4 | 120.4741 |
S1—C16—C21 | 120.4 (1) | C6—C7—H5 | 119.4192 |
O1—C9—C1 | 119.6 (2) | H4—C6—C7 | 120.4840 |
O1—C9—C10 | 122.0 (2) | C7—C8—H6 | 119.7643 |
C9—C1—C2 | 127.6 (2) | H5—C7—C8 | 119.4226 |
C1—C2—C3 | 130.5 (2) | C10—C11—H7 | 119.8600 |
C1—C9—C10 | 118.4 (2) | C10—C15—H11 | 119.4179 |
C2—C3—C4 | 125.0 (2) | H7—C11—C12 | 119.8188 |
C2—C3—C8 | 117.4 (2) | C11—C12—H8 | 120.0883 |
C8—C3—C4 | 117.5 (2) | H8—C12—C13 | 120.1358 |
C3—C4—C5 | 120.9 (2) | C12—C13—H9 | 119.7136 |
C3—C8—C7 | 120.5 (2) | C13—C14—H10 | 120.2164 |
C4—C5—C6 | 120.9 (2) | H9—C13—C14 | 119.7399 |
C5—C6—C7 | 119.0 (3) | C14—C15—H11 | 119.3338 |
C6—C7—C8 | 121.2 (3) | H10—C14—C15 | 120.2811 |
C9—C10—C11 | 122.4 (1) | C16—C17—H12 | 120.1804 |
C9—C10—C15 | 119.1 (2) | C16—C21—H15 | 120.6509 |
C15—C10—C11 | 118.5 (2) | H12—C17—C18 | 120.1588 |
C10—C11—C12 | 120.3 (2) | C17—C18—H13 | 119.2909 |
C10—C15—C14 | 121.2 (2) | H13—C18—C19 | 119.3733 |
C11—C12—C13 | 119.8 (2) | C19—C20—H14 | 119.0922 |
C12—C13—C14 | 120.5 (2) | C19—C22—H16 | 109.4586 |
C13—C14—C15 | 119.5 (2) | C19—C22—H17 | 109.4853 |
C21—C16—C17 | 120.2 (2) | C19—C22—H18 | 109.4293 |
C16—C17—C18 | 119.7 (2) | C20—C21—H15 | 120.5637 |
C16—C21—C20 | 118.8 (2) | H14—C20—C21 | 119.0561 |
C17—C18—C19 | 121.3 (2) | H17—C22—H16 | 109.4959 |
C18—C19—C20 | 118.1 (2) | H18—C22—H16 | 109.4737 |
C18—C19—C22 | 120.5 (2) | H18—C22—H17 | 109.4844 |
C19—C20—C21 | 121.9 (2) | ||
O2—S1—C1—C2 | 17.5 (2) | C4—C5—C6—C7 | −0.2 (4) |
O2—S1—C1—C9 | −166.9 (1) | C5—C6—C7—C8 | −0.3 (5) |
O3—S1—C1—C2 | 146.2 (1) | C6—C7—C8—C3 | 0.1 (4) |
O3—S1—C1—C9 | −38.2 (2) | O1—C9—C10—C11 | 157.3 (2) |
C16—S1—C1—C2 | −98.1 (2) | O1—C9—C10—C15 | −24.2 (4) |
C16—S1—C1—C9 | 77.5 (1) | C1—C9—C10—C11 | −23.3 (3) |
O2—S1—C16—C17 | −47.7 (2) | C1—C9—C10—C15 | 155.3 (2) |
O2—S1—C16—C21 | 131.2 (2) | C9—C10—C11—C12 | −178.1 (2) |
O3—S1—C16—C17 | −177.5 (1) | C15—C10—C11—C12 | 3.3 (3) |
O3—S1—C16—C21 | 1.3 (2) | C9—C10—C15—C14 | −179.5 (3) |
C1—S1—C16—C17 | 67.6 (2) | C11—C10—C15—C14 | −0.9 (4) |
C1—S1—C16—C21 | −113.5 (2) | C10—C11—C12—C13 | −3.1 (4) |
S1—C1—C2—C3 | 176.5 (2) | C11—C12—C13—C14 | 0.5 (5) |
C9—C1—C2—C3 | 1.6 (3) | C12—C13—C14—C15 | 1.9 (5) |
S1—C1—C9—O1 | −80.2 (2) | C13—C14—C15—C10 | −1.7 (5) |
S1—C1—C9—C10 | 100.4 (2) | S1—C16—C17—C18 | 177.0 (2) |
C2—C1—C9—O1 | 94.9 (3) | C21—C16—C17—C18 | −1.8 (3) |
C2—C1—C9—C10 | −84.5 (3) | S1—C16—C21—C20 | −176.3 (2) |
C1—C2—C3—C4 | −0.5 (4) | C17—C16—C21—C20 | 2.6 (4) |
C1—C2—C3—C8 | −177.7 (2) | C16—C17—C18—C19 | −0.7 (4) |
C2—C3—C4—C5 | −178.4 (2) | C17—C18—C19—C20 | 2.3 (4) |
C8—C3—C4—C5 | −1.2 (4) | C17—C18—C19—C22 | −177.1 (3) |
C2—C3—C8—C7 | 178.1 (3) | C18—C19—C20—C21 | −1.5 (4) |
C4—C3—C8—C7 | 0.7 (4) | C22—C19—C20—C21 | 177.9 (3) |
C3—C4—C5—C6 | 1.0 (5) | C19—C20—C21—C16 | −0.9 (4) |
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