Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013432/wn2021sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013432/wn2021Isup2.hkl |
CCDC reference: 608527
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.004 Å
- R factor = 0.045
- wR factor = 0.132
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.67 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.36 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993); cell refinement: CAD-4 EXPRESS; data reduction: CAD-4 EXPRESS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C15H19NO3S | F(000) = 624 |
Mr = 293.39 | Dx = 1.355 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3026 reflections |
a = 6.0285 (12) Å | θ = 10.0–18.1° |
b = 16.4319 (11) Å | µ = 0.23 mm−1 |
c = 14.7046 (14) Å | T = 100 K |
β = 99.258 (3)° | Block, colourless |
V = 1437.7 (3) Å3 | 0.25 × 0.20 × 0.15 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 2928 independent reflections |
Radiation source: fine-focus sealed tube | 1739 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 9 pixels mm-1 | θmax = 26.3°, θmin = 2.5° |
ω/2θ scans | h = 0→7 |
Absorption correction: multi-scan (MolEN; Fair, 1990) | k = 0→20 |
Tmin = 0.946, Tmax = 0.966 | l = −18→17 |
3026 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.132 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0643P)2 + 0.2195P] where P = (Fo2 + 2Fc2)/3 |
2776 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
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 | 0.2573 (4) | 0.43806 (17) | 0.77735 (17) | 0.0419 (6) | |
C2 | 0.4335 (6) | 0.41035 (19) | 0.8411 (2) | 0.0665 (9) | |
H2 | 0.4471 | 0.3552 | 0.8549 | 0.080* | |
C3 | 0.5904 (6) | 0.4651 (2) | 0.8845 (2) | 0.0805 (11) | |
H3 | 0.7093 | 0.4459 | 0.9273 | 0.097* | |
C4 | 0.5754 (6) | 0.5472 (2) | 0.8660 (2) | 0.0623 (9) | |
C5 | 0.7505 (7) | 0.6064 (3) | 0.9117 (3) | 0.1051 (15) | |
H5A | 0.8621 | 0.5774 | 0.9534 | 0.158* | |
H5B | 0.6801 | 0.6463 | 0.9453 | 0.158* | |
H5C | 0.8206 | 0.6330 | 0.8656 | 0.158* | |
C6 | 0.3964 (6) | 0.57351 (19) | 0.8028 (2) | 0.0615 (9) | |
H6 | 0.3820 | 0.6288 | 0.7895 | 0.074* | |
C7 | 0.2380 (5) | 0.52039 (18) | 0.7585 (2) | 0.0551 (8) | |
H7 | 0.1186 | 0.5398 | 0.7160 | 0.066* | |
C8 | 0.3855 (4) | 0.29602 (17) | 0.63535 (19) | 0.0455 (7) | |
H8A | 0.3556 | 0.2393 | 0.6472 | 0.055* | |
H8B | 0.4940 | 0.3170 | 0.6858 | 0.055* | |
C9 | 0.4687 (4) | 0.30583 (16) | 0.54487 (17) | 0.0393 (6) | |
H9 | 0.6329 | 0.3018 | 0.5537 | 0.047* | |
C10 | 0.3624 (5) | 0.24895 (18) | 0.46695 (19) | 0.0515 (7) | |
H10A | 0.4775 | 0.2229 | 0.4380 | 0.062* | |
H10B | 0.2729 | 0.2072 | 0.4904 | 0.062* | |
C11 | 0.2144 (4) | 0.30408 (19) | 0.39830 (18) | 0.0498 (7) | |
H11 | 0.1990 | 0.2823 | 0.3356 | 0.060* | |
C12 | 0.3456 (5) | 0.3839 (2) | 0.4069 (2) | 0.0546 (8) | |
H12A | 0.4830 | 0.3799 | 0.3807 | 0.066* | |
H12B | 0.2558 | 0.4289 | 0.3786 | 0.066* | |
C13 | 0.3926 (4) | 0.39107 (16) | 0.51121 (18) | 0.0419 (7) | |
H13 | 0.5043 | 0.4331 | 0.5326 | 0.050* | |
C15 | −0.0166 (4) | 0.31978 (19) | 0.42630 (19) | 0.0475 (7) | |
H15A | −0.1288 | 0.3233 | 0.3712 | 0.057* | |
H15 | −0.0554 | 0.2741 | 0.4625 | 0.057* | |
C14 | 0.1687 (4) | 0.40415 (16) | 0.54707 (17) | 0.0405 (6) | |
H14 | 0.1655 | 0.4594 | 0.5720 | 0.049* | |
N | 0.1745 (3) | 0.34489 (13) | 0.62286 (14) | 0.0392 (5) | |
O1 | 0.0693 (4) | 0.29603 (13) | 0.76723 (14) | 0.0717 (7) | |
O2 | −0.1370 (3) | 0.41168 (15) | 0.68347 (16) | 0.0711 (7) | |
O3 | −0.0217 (3) | 0.39261 (12) | 0.47838 (12) | 0.0465 (5) | |
S1 | 0.06803 (12) | 0.36894 (5) | 0.71418 (5) | 0.0497 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0429 (15) | 0.0455 (16) | 0.0373 (14) | −0.0031 (12) | 0.0061 (12) | −0.0055 (12) |
C2 | 0.092 (3) | 0.0460 (18) | 0.0537 (19) | −0.0028 (17) | −0.0130 (18) | 0.0023 (15) |
C3 | 0.084 (3) | 0.071 (3) | 0.071 (2) | 0.001 (2) | −0.033 (2) | −0.011 (2) |
C4 | 0.064 (2) | 0.061 (2) | 0.061 (2) | −0.0143 (17) | 0.0058 (17) | −0.0163 (17) |
C5 | 0.094 (3) | 0.103 (3) | 0.111 (3) | −0.039 (3) | −0.003 (3) | −0.039 (3) |
C6 | 0.083 (2) | 0.0408 (17) | 0.061 (2) | −0.0058 (16) | 0.0114 (18) | −0.0115 (15) |
C7 | 0.0582 (19) | 0.0506 (18) | 0.0531 (18) | 0.0086 (15) | −0.0015 (14) | −0.0073 (15) |
C8 | 0.0457 (16) | 0.0428 (16) | 0.0471 (16) | 0.0026 (13) | 0.0044 (13) | 0.0060 (13) |
C9 | 0.0279 (13) | 0.0449 (15) | 0.0454 (15) | 0.0019 (11) | 0.0071 (11) | 0.0044 (12) |
C10 | 0.0476 (17) | 0.0565 (18) | 0.0513 (17) | 0.0084 (15) | 0.0109 (14) | −0.0089 (14) |
C11 | 0.0435 (16) | 0.071 (2) | 0.0351 (15) | 0.0060 (15) | 0.0055 (13) | −0.0083 (14) |
C12 | 0.0382 (15) | 0.077 (2) | 0.0505 (17) | −0.0005 (15) | 0.0121 (13) | 0.0174 (16) |
C13 | 0.0311 (14) | 0.0454 (16) | 0.0490 (16) | −0.0069 (12) | 0.0061 (12) | 0.0070 (13) |
C15 | 0.0374 (15) | 0.0599 (19) | 0.0431 (15) | −0.0007 (13) | 0.0001 (12) | −0.0067 (14) |
C14 | 0.0408 (15) | 0.0360 (14) | 0.0437 (16) | 0.0008 (12) | 0.0037 (12) | −0.0007 (12) |
N | 0.0378 (12) | 0.0427 (13) | 0.0373 (12) | −0.0014 (10) | 0.0064 (9) | −0.0034 (10) |
O1 | 0.1001 (18) | 0.0647 (14) | 0.0572 (13) | −0.0372 (13) | 0.0331 (13) | −0.0042 (11) |
O2 | 0.0329 (11) | 0.1042 (18) | 0.0779 (15) | −0.0028 (11) | 0.0136 (10) | −0.0302 (13) |
O3 | 0.0335 (10) | 0.0548 (12) | 0.0489 (11) | 0.0104 (8) | −0.0002 (8) | −0.0009 (9) |
S1 | 0.0444 (4) | 0.0598 (5) | 0.0480 (4) | −0.0168 (4) | 0.0168 (3) | −0.0120 (4) |
C1—C2 | 1.376 (4) | C9—H9 | 0.9800 |
C1—C7 | 1.382 (4) | C10—C11 | 1.532 (4) |
C1—S1 | 1.765 (3) | C10—H10A | 0.9700 |
C2—C3 | 1.385 (4) | C10—H10B | 0.9700 |
C2—H2 | 0.9300 | C11—C12 | 1.527 (4) |
C3—C4 | 1.376 (5) | C11—C15 | 1.536 (4) |
C3—H3 | 0.9300 | C11—H11 | 0.9800 |
C4—C6 | 1.375 (4) | C12—C13 | 1.519 (4) |
C4—C5 | 1.511 (5) | C12—H12A | 0.9700 |
C5—H5A | 0.9600 | C12—H12B | 0.9700 |
C5—H5B | 0.9600 | C13—C14 | 1.541 (4) |
C5—H5C | 0.9600 | C13—H13 | 0.9800 |
C6—C7 | 1.378 (4) | C15—O3 | 1.424 (3) |
C6—H6 | 0.9300 | C15—H15A | 0.9700 |
C7—H7 | 0.9300 | C15—H15 | 0.9700 |
C8—N | 1.491 (3) | C14—O3 | 1.415 (3) |
C8—C9 | 1.504 (4) | C14—N | 1.476 (3) |
C8—H8A | 0.9700 | C14—H14 | 0.9800 |
C8—H8B | 0.9700 | N—S1 | 1.627 (2) |
C9—C13 | 1.531 (4) | O1—S1 | 1.429 (2) |
C9—C10 | 1.536 (4) | O2—S1 | 1.430 (2) |
C2—C1—C7 | 119.4 (3) | H10A—C10—H10B | 108.8 |
C2—C1—S1 | 120.6 (2) | C12—C11—C15 | 108.3 (2) |
C7—C1—S1 | 119.8 (2) | C12—C11—C10 | 102.4 (2) |
C1—C2—C3 | 119.6 (3) | C15—C11—C10 | 112.3 (2) |
C1—C2—H2 | 120.2 | C12—C11—H11 | 111.2 |
C3—C2—H2 | 120.2 | C15—C11—H11 | 111.2 |
C4—C3—C2 | 121.8 (3) | C10—C11—H11 | 111.2 |
C4—C3—H3 | 119.1 | C13—C12—C11 | 99.2 (2) |
C2—C3—H3 | 119.1 | C13—C12—H12A | 111.9 |
C6—C4—C3 | 117.5 (3) | C11—C12—H12A | 111.9 |
C6—C4—C5 | 121.0 (3) | C13—C12—H12B | 111.9 |
C3—C4—C5 | 121.6 (3) | C11—C12—H12B | 111.9 |
C4—C5—H5A | 109.5 | H12A—C12—H12B | 109.6 |
C4—C5—H5B | 109.5 | C12—C13—C9 | 104.7 (2) |
H5A—C5—H5B | 109.5 | C12—C13—C14 | 109.0 (2) |
C4—C5—H5C | 109.5 | C9—C13—C14 | 104.5 (2) |
H5A—C5—H5C | 109.5 | C12—C13—H13 | 112.7 |
H5B—C5—H5C | 109.5 | C9—C13—H13 | 112.7 |
C4—C6—C7 | 122.0 (3) | C14—C13—H13 | 112.7 |
C4—C6—H6 | 119.0 | O3—C15—C11 | 112.6 (2) |
C7—C6—H6 | 119.0 | O3—C15—H15A | 109.1 |
C6—C7—C1 | 119.7 (3) | C11—C15—H15A | 109.1 |
C6—C7—H7 | 120.1 | O3—C15—H15 | 109.1 |
C1—C7—H7 | 120.1 | C11—C15—H15 | 109.1 |
N—C8—C9 | 103.4 (2) | H15A—C15—H15 | 107.8 |
N—C8—H8A | 111.1 | O3—C14—N | 111.6 (2) |
C9—C8—H8A | 111.1 | O3—C14—C13 | 113.1 (2) |
N—C8—H8B | 111.1 | N—C14—C13 | 104.5 (2) |
C9—C8—H8B | 111.1 | O3—C14—H14 | 109.2 |
H8A—C8—H8B | 109.0 | N—C14—H14 | 109.2 |
C8—C9—C13 | 105.0 (2) | C13—C14—H14 | 109.2 |
C8—C9—C10 | 115.9 (2) | C14—N—C8 | 111.36 (19) |
C13—C9—C10 | 104.4 (2) | C14—N—S1 | 119.89 (17) |
C8—C9—H9 | 110.4 | C8—N—S1 | 118.12 (17) |
C13—C9—H9 | 110.4 | C14—O3—C15 | 114.28 (19) |
C10—C9—H9 | 110.4 | O2—S1—O1 | 120.83 (14) |
C11—C10—C9 | 105.1 (2) | O2—S1—N | 107.12 (12) |
C11—C10—H10A | 110.7 | O1—S1—N | 106.17 (12) |
C9—C10—H10A | 110.7 | O2—S1—C1 | 107.65 (13) |
C11—C10—H10B | 110.7 | O1—S1—C1 | 107.81 (14) |
C9—C10—H10B | 110.7 | N—S1—C1 | 106.45 (12) |
C7—C1—C2—C3 | −0.8 (5) | C12—C13—C14—O3 | 10.0 (3) |
S1—C1—C2—C3 | 174.8 (3) | C9—C13—C14—O3 | −101.4 (2) |
C1—C2—C3—C4 | 0.2 (6) | C12—C13—C14—N | 131.6 (2) |
C2—C3—C4—C6 | 0.5 (5) | C9—C13—C14—N | 20.2 (2) |
C2—C3—C4—C5 | −178.4 (4) | O3—C14—N—C8 | 122.1 (2) |
C3—C4—C6—C7 | −0.6 (5) | C13—C14—N—C8 | −0.4 (3) |
C5—C4—C6—C7 | 178.3 (3) | O3—C14—N—S1 | −94.0 (2) |
C4—C6—C7—C1 | 0.0 (5) | C13—C14—N—S1 | 143.48 (18) |
C2—C1—C7—C6 | 0.8 (4) | C9—C8—N—C14 | −19.7 (3) |
S1—C1—C7—C6 | −174.9 (2) | C9—C8—N—S1 | −164.36 (17) |
N—C8—C9—C13 | 31.8 (2) | N—C14—O3—C15 | −69.3 (3) |
N—C8—C9—C10 | −82.7 (3) | C13—C14—O3—C15 | 48.2 (3) |
C8—C9—C10—C11 | 109.6 (3) | C11—C15—O3—C14 | −43.5 (3) |
C13—C9—C10—C11 | −5.4 (3) | C14—N—S1—O2 | 41.3 (2) |
C9—C10—C11—C12 | 33.3 (3) | C8—N—S1—O2 | −177.18 (19) |
C9—C10—C11—C15 | −82.7 (3) | C14—N—S1—O1 | 171.62 (18) |
C15—C11—C12—C13 | 71.1 (3) | C8—N—S1—O1 | −46.8 (2) |
C10—C11—C12—C13 | −47.8 (2) | C14—N—S1—C1 | −73.7 (2) |
C11—C12—C13—C9 | 45.0 (2) | C8—N—S1—C1 | 67.9 (2) |
C11—C12—C13—C14 | −66.3 (3) | C2—C1—S1—O2 | 157.2 (3) |
C8—C9—C13—C12 | −147.2 (2) | C7—C1—S1—O2 | −27.1 (3) |
C10—C9—C13—C12 | −24.8 (3) | C2—C1—S1—O1 | 25.4 (3) |
C8—C9—C13—C14 | −32.6 (3) | C7—C1—S1—O1 | −159.0 (2) |
C10—C9—C13—C14 | 89.7 (2) | C2—C1—S1—N | −88.2 (3) |
C12—C11—C15—O3 | −18.5 (3) | C7—C1—S1—N | 87.4 (2) |
C10—C11—C15—O3 | 93.9 (3) |
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