Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804015661/wn6259sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804015661/wn6259Isup2.hkl |
CCDC reference: 248767
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.050
- wR factor = 0.127
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.88 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.35 Ratio PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C4 PLAT415_ALERT_2_C Short Inter D-H..H-X H1 .. H23 .. 2.12 Ang. PLAT430_ALERT_2_C Short Inter D...A Contact O3 .. O3 .. 2.86 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C23H23NO4S | Z = 2 |
Mr = 409.49 | F(000) = 432 |
Triclinic, P1 | Dx = 1.329 Mg m−3 |
Hall symbol: -P 1 | Melting point: 399 K |
a = 9.884 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.924 (3) Å | Cell parameters from 991 reflections |
c = 11.738 (3) Å | θ = 3.0–26.4° |
α = 94.267 (5)° | µ = 0.19 mm−1 |
β = 91.985 (4)° | T = 293 K |
γ = 116.676 (4)° | Prism, colorless |
V = 1023.0 (5) Å3 | 0.26 × 0.16 × 0.12 mm |
Bruker SMART 1000 CCD area-detector diffractometer | 3607 independent reflections |
Radiation source: fine-focus sealed tube | 2537 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
ψ and ω scans | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.965, Tmax = 0.978 | k = −11→8 |
5353 measured reflections | l = −13→13 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0503P)2 + 0.4833P] where P = (Fo2 + 2Fc2)/3 |
3607 reflections | (Δ/σ)max = 0.002 |
264 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.36 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. |
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 > 2sigma(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 | ||
S1 | 0.71528 (8) | 0.29972 (9) | 0.23854 (6) | 0.0497 (2) | |
O1 | 0.7606 (2) | 0.4533 (2) | 0.27705 (17) | 0.0699 (6) | |
O2 | 0.8216 (2) | 0.2391 (3) | 0.24615 (18) | 0.0707 (7) | |
O3 | 0.3755 (2) | 0.0346 (2) | −0.01740 (16) | 0.0494 (5) | |
O4 | 0.7045 (2) | 0.4956 (3) | −0.39457 (16) | 0.0672 (6) | |
N1 | 0.6584 (2) | 0.2737 (2) | 0.10482 (17) | 0.0423 (5) | |
H1 | 0.6812 | 0.2164 | 0.0591 | 0.051* | |
C1 | 0.5590 (3) | 0.1879 (3) | 0.3134 (2) | 0.0431 (6) | |
C2 | 0.4877 (4) | 0.2528 (4) | 0.3800 (2) | 0.0587 (8) | |
H2 | 0.5242 | 0.3575 | 0.3889 | 0.070* | |
C3 | 0.3613 (4) | 0.1606 (4) | 0.4335 (2) | 0.0672 (9) | |
H3 | 0.3122 | 0.2044 | 0.4774 | 0.081* | |
C4 | 0.3064 (3) | 0.0060 (4) | 0.4234 (3) | 0.0629 (9) | |
C5 | 0.3799 (4) | −0.0560 (4) | 0.3581 (3) | 0.0673 (9) | |
H5 | 0.3447 | −0.1605 | 0.3510 | 0.081* | |
C6 | 0.5048 (3) | 0.0329 (3) | 0.3026 (3) | 0.0575 (8) | |
H6 | 0.5527 | −0.0116 | 0.2579 | 0.069* | |
C7 | 0.1688 (4) | −0.0940 (5) | 0.4832 (3) | 0.1026 (15) | |
H7A | 0.1208 | −0.0351 | 0.5134 | 0.154* | |
H7B | 0.1998 | −0.1350 | 0.5447 | 0.154* | |
H7C | 0.0985 | −0.1752 | 0.4295 | 0.154* | |
C8 | 0.5690 (3) | 0.3446 (3) | 0.0585 (2) | 0.0384 (6) | |
H8 | 0.6085 | 0.4446 | 0.1019 | 0.046* | |
C9 | 0.6047 (3) | 0.3756 (3) | −0.0646 (2) | 0.0355 (6) | |
C10 | 0.7542 (3) | 0.4607 (3) | −0.0889 (2) | 0.0399 (6) | |
H10 | 0.8306 | 0.4905 | −0.0303 | 0.048* | |
C11 | 0.7938 (3) | 0.5026 (3) | −0.1972 (2) | 0.0418 (6) | |
H11 | 0.8951 | 0.5591 | −0.2111 | 0.050* | |
C12 | 0.6808 (3) | 0.4597 (3) | −0.2847 (2) | 0.0446 (7) | |
C13 | 0.5307 (3) | 0.3752 (3) | −0.2618 (2) | 0.0510 (7) | |
H13 | 0.4539 | 0.3471 | −0.3199 | 0.061* | |
C14 | 0.4942 (3) | 0.3326 (3) | −0.1537 (2) | 0.0440 (7) | |
H14 | 0.3931 | 0.2736 | −0.1404 | 0.053* | |
C15 | 0.8561 (4) | 0.5762 (5) | −0.4235 (3) | 0.0847 (12) | |
H15A | 0.9034 | 0.6736 | −0.3796 | 0.127* | |
H15B | 0.8568 | 0.5896 | −0.5037 | 0.127* | |
H15C | 0.9111 | 0.5202 | −0.4070 | 0.127* | |
C16 | 0.3999 (3) | 0.2628 (3) | 0.0808 (2) | 0.0388 (6) | |
H16A | 0.3906 | 0.2813 | 0.1617 | 0.047* | |
H16B | 0.3469 | 0.3080 | 0.0391 | 0.047* | |
C17 | 0.3209 (3) | 0.0941 (3) | 0.0480 (2) | 0.0371 (6) | |
C18 | 0.1777 (3) | 0.0027 (3) | 0.1024 (2) | 0.0393 (6) | |
C19 | 0.0906 (3) | 0.0655 (3) | 0.1495 (2) | 0.0508 (7) | |
H19 | 0.1187 | 0.1679 | 0.1461 | 0.061* | |
C20 | −0.0388 (3) | −0.0240 (4) | 0.2018 (3) | 0.0640 (9) | |
H20 | −0.0993 | 0.0177 | 0.2312 | 0.077* | |
C21 | −0.0780 (3) | −0.1734 (4) | 0.2104 (3) | 0.0613 (9) | |
H21 | −0.1631 | −0.2321 | 0.2480 | 0.074* | |
C22 | 0.0078 (3) | −0.2372 (4) | 0.1638 (3) | 0.0623 (9) | |
H22 | −0.0191 | −0.3389 | 0.1694 | 0.075* | |
C23 | 0.1334 (3) | −0.1501 (3) | 0.1089 (3) | 0.0555 (8) | |
H23 | 0.1898 | −0.1943 | 0.0754 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0399 (4) | 0.0526 (5) | 0.0439 (4) | 0.0083 (3) | 0.0025 (3) | 0.0143 (3) |
O1 | 0.0763 (15) | 0.0485 (13) | 0.0558 (13) | 0.0019 (11) | 0.0024 (11) | 0.0106 (10) |
O2 | 0.0417 (11) | 0.0996 (18) | 0.0738 (15) | 0.0312 (12) | 0.0045 (10) | 0.0319 (13) |
O3 | 0.0516 (11) | 0.0417 (11) | 0.0602 (12) | 0.0242 (9) | 0.0214 (9) | 0.0072 (9) |
O4 | 0.0568 (13) | 0.0836 (16) | 0.0410 (11) | 0.0123 (11) | 0.0078 (9) | 0.0157 (10) |
N1 | 0.0445 (12) | 0.0479 (13) | 0.0397 (12) | 0.0241 (11) | 0.0104 (10) | 0.0119 (10) |
C1 | 0.0411 (15) | 0.0472 (17) | 0.0367 (14) | 0.0153 (13) | 0.0032 (11) | 0.0100 (12) |
C2 | 0.071 (2) | 0.0543 (19) | 0.0457 (17) | 0.0240 (17) | 0.0083 (15) | 0.0026 (14) |
C3 | 0.068 (2) | 0.098 (3) | 0.0422 (17) | 0.041 (2) | 0.0145 (15) | 0.0099 (17) |
C4 | 0.0482 (17) | 0.085 (3) | 0.0495 (18) | 0.0214 (18) | 0.0061 (14) | 0.0320 (17) |
C5 | 0.058 (2) | 0.055 (2) | 0.084 (2) | 0.0181 (17) | 0.0106 (18) | 0.0293 (18) |
C6 | 0.0566 (18) | 0.0512 (19) | 0.067 (2) | 0.0247 (16) | 0.0136 (15) | 0.0156 (15) |
C7 | 0.061 (2) | 0.149 (4) | 0.084 (3) | 0.027 (2) | 0.023 (2) | 0.061 (3) |
C8 | 0.0382 (14) | 0.0351 (14) | 0.0442 (15) | 0.0176 (12) | 0.0093 (11) | 0.0084 (11) |
C9 | 0.0376 (13) | 0.0317 (14) | 0.0414 (14) | 0.0187 (11) | 0.0055 (11) | 0.0064 (11) |
C10 | 0.0345 (14) | 0.0430 (15) | 0.0427 (15) | 0.0173 (12) | 0.0034 (11) | 0.0090 (12) |
C11 | 0.0342 (13) | 0.0413 (15) | 0.0479 (16) | 0.0141 (12) | 0.0096 (12) | 0.0094 (12) |
C12 | 0.0478 (16) | 0.0438 (16) | 0.0407 (15) | 0.0184 (13) | 0.0096 (12) | 0.0072 (12) |
C13 | 0.0418 (15) | 0.0604 (19) | 0.0412 (16) | 0.0146 (14) | −0.0029 (12) | 0.0080 (13) |
C14 | 0.0323 (13) | 0.0417 (16) | 0.0508 (16) | 0.0095 (12) | 0.0049 (12) | 0.0108 (12) |
C15 | 0.063 (2) | 0.114 (3) | 0.051 (2) | 0.013 (2) | 0.0228 (17) | 0.0234 (19) |
C16 | 0.0397 (14) | 0.0384 (15) | 0.0429 (14) | 0.0203 (12) | 0.0119 (11) | 0.0097 (11) |
C17 | 0.0374 (13) | 0.0406 (15) | 0.0389 (14) | 0.0214 (12) | 0.0071 (11) | 0.0115 (11) |
C18 | 0.0324 (13) | 0.0442 (16) | 0.0414 (15) | 0.0166 (12) | 0.0044 (11) | 0.0098 (12) |
C19 | 0.0441 (16) | 0.0525 (18) | 0.0612 (18) | 0.0244 (14) | 0.0154 (13) | 0.0163 (14) |
C20 | 0.0477 (17) | 0.082 (3) | 0.072 (2) | 0.0363 (18) | 0.0209 (15) | 0.0154 (18) |
C21 | 0.0336 (15) | 0.074 (2) | 0.065 (2) | 0.0120 (16) | 0.0113 (14) | 0.0227 (17) |
C22 | 0.0500 (17) | 0.0484 (19) | 0.078 (2) | 0.0107 (15) | 0.0135 (16) | 0.0183 (16) |
C23 | 0.0473 (16) | 0.0451 (18) | 0.073 (2) | 0.0180 (14) | 0.0192 (15) | 0.0147 (15) |
S1—O1 | 1.413 (2) | C9—C10 | 1.387 (3) |
S1—O2 | 1.430 (2) | C10—C11 | 1.382 (3) |
S1—N1 | 1.611 (2) | C10—H10 | 0.9300 |
S1—C1 | 1.758 (3) | C11—C12 | 1.383 (4) |
O3—C17 | 1.215 (3) | C11—H11 | 0.9300 |
O4—C12 | 1.363 (3) | C12—C13 | 1.386 (4) |
O4—C15 | 1.415 (4) | C13—C14 | 1.376 (4) |
N1—C8 | 1.467 (3) | C13—H13 | 0.9300 |
N1—H1 | 0.8600 | C14—H14 | 0.9300 |
C1—C2 | 1.376 (4) | C15—H15A | 0.9600 |
C1—C6 | 1.377 (4) | C15—H15B | 0.9600 |
C2—C3 | 1.380 (4) | C15—H15C | 0.9600 |
C2—H2 | 0.9300 | C16—C17 | 1.506 (3) |
C3—C4 | 1.372 (5) | C16—H16A | 0.9700 |
C3—H3 | 0.9300 | C16—H16B | 0.9700 |
C4—C5 | 1.365 (5) | C17—C18 | 1.493 (3) |
C4—C7 | 1.511 (4) | C18—C19 | 1.378 (4) |
C5—C6 | 1.375 (4) | C18—C23 | 1.386 (4) |
C5—H5 | 0.9300 | C19—C20 | 1.385 (4) |
C6—H6 | 0.9300 | C19—H19 | 0.9300 |
C7—H7A | 0.9600 | C20—C21 | 1.367 (4) |
C7—H7B | 0.9600 | C20—H20 | 0.9300 |
C7—H7C | 0.9600 | C21—C22 | 1.371 (4) |
C8—C9 | 1.520 (3) | C21—H21 | 0.9300 |
C8—C16 | 1.537 (3) | C22—C23 | 1.370 (4) |
C8—H8 | 0.9800 | C22—H22 | 0.9300 |
C9—C14 | 1.380 (3) | C23—H23 | 0.9300 |
O1—S1—O2 | 120.06 (15) | C10—C11—C12 | 119.2 (2) |
O1—S1—N1 | 107.86 (12) | C10—C11—H11 | 120.4 |
O2—S1—N1 | 105.50 (13) | C12—C11—H11 | 120.4 |
O1—S1—C1 | 107.74 (14) | O4—C12—C11 | 124.9 (2) |
O2—S1—C1 | 107.40 (13) | O4—C12—C13 | 115.9 (2) |
N1—S1—C1 | 107.75 (12) | C11—C12—C13 | 119.2 (2) |
C12—O4—C15 | 118.0 (2) | C14—C13—C12 | 120.6 (2) |
C8—N1—S1 | 122.13 (18) | C14—C13—H13 | 119.7 |
C8—N1—H1 | 118.9 | C12—C13—H13 | 119.7 |
S1—N1—H1 | 118.9 | C13—C14—C9 | 121.3 (2) |
C2—C1—C6 | 119.7 (3) | C13—C14—H14 | 119.3 |
C2—C1—S1 | 120.9 (2) | C9—C14—H14 | 119.3 |
C6—C1—S1 | 119.4 (2) | O4—C15—H15A | 109.5 |
C1—C2—C3 | 119.2 (3) | O4—C15—H15B | 109.5 |
C1—C2—H2 | 120.4 | H15A—C15—H15B | 109.5 |
C3—C2—H2 | 120.4 | O4—C15—H15C | 109.5 |
C4—C3—C2 | 121.7 (3) | H15A—C15—H15C | 109.5 |
C4—C3—H3 | 119.1 | H15B—C15—H15C | 109.5 |
C2—C3—H3 | 119.1 | C17—C16—C8 | 116.0 (2) |
C5—C4—C3 | 118.2 (3) | C17—C16—H16A | 108.3 |
C5—C4—C7 | 120.5 (4) | C8—C16—H16A | 108.3 |
C3—C4—C7 | 121.3 (4) | C17—C16—H16B | 108.3 |
C4—C5—C6 | 121.4 (3) | C8—C16—H16B | 108.3 |
C4—C5—H5 | 119.3 | H16A—C16—H16B | 107.4 |
C6—C5—H5 | 119.3 | O3—C17—C18 | 121.4 (2) |
C5—C6—C1 | 119.9 (3) | O3—C17—C16 | 120.7 (2) |
C5—C6—H6 | 120.1 | C18—C17—C16 | 117.8 (2) |
C1—C6—H6 | 120.1 | C19—C18—C23 | 118.8 (2) |
C4—C7—H7A | 109.5 | C19—C18—C17 | 122.5 (2) |
C4—C7—H7B | 109.5 | C23—C18—C17 | 118.7 (2) |
H7A—C7—H7B | 109.5 | C18—C19—C20 | 119.9 (3) |
C4—C7—H7C | 109.5 | C18—C19—H19 | 120.0 |
H7A—C7—H7C | 109.5 | C20—C19—H19 | 120.0 |
H7B—C7—H7C | 109.5 | C21—C20—C19 | 120.3 (3) |
N1—C8—C9 | 109.68 (19) | C21—C20—H20 | 119.8 |
N1—C8—C16 | 113.49 (19) | C19—C20—H20 | 119.8 |
C9—C8—C16 | 116.4 (2) | C20—C21—C22 | 120.2 (3) |
N1—C8—H8 | 105.4 | C20—C21—H21 | 119.9 |
C9—C8—H8 | 105.4 | C22—C21—H21 | 119.9 |
C16—C8—H8 | 105.4 | C23—C22—C21 | 119.7 (3) |
C14—C9—C10 | 117.3 (2) | C23—C22—H22 | 120.2 |
C14—C9—C8 | 123.2 (2) | C21—C22—H22 | 120.2 |
C10—C9—C8 | 119.3 (2) | C22—C23—C18 | 121.0 (3) |
C11—C10—C9 | 122.4 (2) | C22—C23—H23 | 119.5 |
C11—C10—H10 | 118.8 | C18—C23—H23 | 119.5 |
C9—C10—H10 | 118.8 | ||
O1—S1—N1—C8 | −39.4 (2) | C9—C10—C11—C12 | 0.5 (4) |
O2—S1—N1—C8 | −168.84 (19) | C15—O4—C12—C11 | 3.4 (4) |
C1—S1—N1—C8 | 76.7 (2) | C15—O4—C12—C13 | −177.4 (3) |
O1—S1—C1—C2 | 10.0 (3) | C10—C11—C12—O4 | 179.0 (2) |
O2—S1—C1—C2 | 140.7 (2) | C10—C11—C12—C13 | −0.2 (4) |
N1—S1—C1—C2 | −106.1 (2) | O4—C12—C13—C14 | 179.9 (3) |
O1—S1—C1—C6 | −171.7 (2) | C11—C12—C13—C14 | −0.9 (4) |
O2—S1—C1—C6 | −41.1 (3) | C12—C13—C14—C9 | 1.7 (4) |
N1—S1—C1—C6 | 72.1 (2) | C10—C9—C14—C13 | −1.4 (4) |
C6—C1—C2—C3 | −1.0 (4) | C8—C9—C14—C13 | 173.8 (2) |
S1—C1—C2—C3 | 177.2 (2) | N1—C8—C16—C17 | −50.6 (3) |
C1—C2—C3—C4 | 1.1 (5) | C9—C8—C16—C17 | 78.1 (3) |
C2—C3—C4—C5 | −0.2 (5) | C8—C16—C17—O3 | −18.0 (3) |
C2—C3—C4—C7 | 179.4 (3) | C8—C16—C17—C18 | 159.4 (2) |
C3—C4—C5—C6 | −0.6 (5) | O3—C17—C18—C19 | −161.1 (2) |
C7—C4—C5—C6 | 179.7 (3) | C16—C17—C18—C19 | 21.5 (3) |
C4—C5—C6—C1 | 0.6 (5) | O3—C17—C18—C23 | 20.9 (4) |
C2—C1—C6—C5 | 0.2 (4) | C16—C17—C18—C23 | −156.5 (2) |
S1—C1—C6—C5 | −178.1 (2) | C23—C18—C19—C20 | −0.1 (4) |
S1—N1—C8—C9 | 148.75 (18) | C17—C18—C19—C20 | −178.1 (3) |
S1—N1—C8—C16 | −79.2 (3) | C18—C19—C20—C21 | 2.2 (5) |
N1—C8—C9—C14 | 129.8 (2) | C19—C20—C21—C22 | −2.2 (5) |
C16—C8—C9—C14 | −0.8 (3) | C20—C21—C22—C23 | 0.2 (5) |
N1—C8—C9—C10 | −55.1 (3) | C21—C22—C23—C18 | 1.8 (5) |
C16—C8—C9—C10 | 174.4 (2) | C19—C18—C23—C22 | −1.8 (4) |
C14—C9—C10—C11 | 0.3 (4) | C17—C18—C23—C22 | 176.2 (3) |
C8—C9—C10—C11 | −175.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3i | 0.86 | 2.30 | 3.019 (3) | 141 |
Symmetry code: (i) −x+1, −y, −z. |
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