Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804012413/ob6369sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804012413/ob6369Isup2.hkl |
CCDC reference: 245271
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.048
- wR factor = 0.097
- Data-to-parameter ratio = 10.8
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.123 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.51 Ratio PLAT350_ALERT_3_C Short C-H Bond (0.96A) C13 - H13 ... 0.84 Ang. PLAT390_ALERT_3_C Deviating Methyl C8 X-C-H Bond Angle ...... 102.00 Deg. PLAT391_ALERT_3_C Deviating Methyl C8 H-C-H Bond Angle ...... 100.00 Deg. PLAT480_ALERT_4_C Long H...A H-Bond Reported H17B .. CG3 .. 2.86 Ang.
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 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 6 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H20N2O3S | F(000) = 1600 |
Mr = 380.45 | Dx = 1.343 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 10649 reflections |
a = 12.472 (7) Å | θ = 1.6–26.8° |
b = 17.6737 (13) Å | µ = 0.20 mm−1 |
c = 17.0718 (12) Å | T = 293 K |
V = 3763 (2) Å3 | Prism, yellow |
Z = 8 | 0.32 × 0.27 × 0.22 mm |
Stoe IPDS-2 diffractometer | 3313 independent reflections |
Radiation source: sealed X-ray tube | 1903 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.124 |
Detector resolution: 6.67 pixels mm-1 | θmax = 25.0°, θmin = 2.3° |
w rotation scans | h = −14→14 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −20→20 |
Tmin = 0.951, Tmax = 0.975 | l = −20→20 |
33217 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.097 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0365P)2] where P = (Fo2 + 2Fc2)/3 |
3313 reflections | (Δ/σ)max < 0.001 |
306 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Experimental. The melting point was determined on an Electrothermal 9200 apparatus and is uncorrected. Microanalysis was performed with a Carlo Erba Elemental Analyser Model 1108. Experiments were followed by TLC using DC Alufolien Kieselgel 60 F254 Merck and Camag TLC lamp (254/366 nm). After completion of the reactions, solvents were evaporated with rotary evaporator (Buchi RE model 111). Solvents were dried by refluxing with the appropriate drying agents and distilled before use. All other reagents were purchased from Merck, Fluka, Aldrich and Acros Chemical Co., and used without further purification. The IR spectrum was recorded on a Perkin-Elmer 298 and Shimadzu 435 V-04 spectrometers using potassium bromide pellets. The 1H NMR spectrum was obtained on a Varian EM 360 L spectrometer with TMS as an internal standard. |
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 | ||
S1 | 0.18925 (6) | 0.30656 (4) | 0.80959 (5) | 0.0602 (3) | |
O1 | −0.13376 (14) | 0.59757 (11) | 0.80104 (13) | 0.0590 (6) | |
O2 | 0.15103 (16) | 0.74288 (12) | 1.03905 (13) | 0.0695 (7) | |
O3 | −0.59330 (15) | 0.48606 (14) | 0.89267 (14) | 0.0763 (7) | |
N1 | 0.10882 (16) | 0.43842 (12) | 0.85201 (13) | 0.0417 (6) | |
N2 | −0.01333 (17) | 0.35208 (14) | 0.79756 (16) | 0.0590 (6) | |
C1 | −0.1585 (2) | 0.53480 (16) | 0.82323 (17) | 0.0434 (7) | |
C2 | 0.06207 (19) | 0.55809 (14) | 0.90382 (16) | 0.0387 (6) | |
C3 | 0.1659 (2) | 0.58520 (16) | 0.89898 (17) | 0.0421 (7) | |
C4 | 0.1990 (2) | 0.64757 (16) | 0.94178 (18) | 0.0469 (7) | |
C5 | 0.1274 (2) | 0.68234 (16) | 0.99195 (17) | 0.0477 (7) | |
C6 | 0.0239 (2) | 0.65584 (17) | 0.99754 (19) | 0.0483 (7) | |
C7 | −0.0087 (2) | 0.59431 (16) | 0.95408 (17) | 0.0440 (7) | |
C8 | 0.2588 (3) | 0.7698 (3) | 1.0401 (3) | 0.0743 (12) | |
C9 | −0.07405 (19) | 0.47473 (15) | 0.83099 (16) | 0.0409 (7) | |
C10 | 0.03135 (19) | 0.48889 (15) | 0.85988 (15) | 0.0389 (7) | |
C11 | −0.2718 (2) | 0.51634 (15) | 0.84230 (16) | 0.0423 (7) | |
C12 | −0.3027 (2) | 0.45479 (17) | 0.88635 (19) | 0.0523 (8) | |
C13 | −0.4101 (2) | 0.4428 (2) | 0.9045 (2) | 0.0563 (8) | |
C14 | −0.4864 (2) | 0.49243 (19) | 0.87823 (19) | 0.0554 (8) | |
C15 | −0.4563 (2) | 0.5544 (2) | 0.8345 (2) | 0.0571 (9) | |
C16 | −0.3511 (2) | 0.56644 (18) | 0.81701 (19) | 0.0519 (8) | |
C17 | −0.6322 (3) | 0.4264 (3) | 0.9401 (3) | 0.0733 (11) | |
C18 | −0.0915 (2) | 0.40491 (17) | 0.80155 (18) | 0.0517 (8) | |
C19 | 0.09087 (19) | 0.36967 (15) | 0.81903 (17) | 0.0446 (7) | |
C20 | −0.0435 (2) | 0.26995 (18) | 0.7759 (2) | 0.0590 (6) | |
C21 | −0.0200 (3) | 0.2580 (2) | 0.6939 (2) | 0.0869 (12) | |
H21A | −0.0383 | 0.2071 | 0.6797 | 0.130* | |
H21B | 0.0551 | 0.2662 | 0.6847 | 0.130* | |
H21C | −0.0610 | 0.2928 | 0.6628 | 0.130* | |
H3 | 0.2148 (18) | 0.5625 (13) | 0.8617 (14) | 0.037 (7)* | |
H4 | 0.272 (2) | 0.6628 (15) | 0.9351 (16) | 0.058 (8)* | |
H6 | −0.0266 (19) | 0.6821 (15) | 1.0338 (15) | 0.044 (7)* | |
H7 | −0.077 (2) | 0.5756 (14) | 0.9601 (14) | 0.042 (7)* | |
H8A | 0.255 (3) | 0.806 (2) | 1.074 (2) | 0.089 (13)* | |
H8B | 0.285 (3) | 0.788 (2) | 0.985 (2) | 0.096 (14)* | |
H8C | 0.313 (3) | 0.731 (2) | 1.051 (2) | 0.108 (15)* | |
H12 | −0.252 (2) | 0.4217 (15) | 0.9078 (15) | 0.049 (8)* | |
H13 | −0.426 (2) | 0.4062 (16) | 0.9333 (16) | 0.040 (8)* | |
H15 | −0.513 (3) | 0.5904 (19) | 0.8184 (19) | 0.082 (10)* | |
H16 | −0.330 (2) | 0.6090 (15) | 0.7857 (15) | 0.050 (8)* | |
H17A | −0.708 (3) | 0.430 (2) | 0.943 (2) | 0.101 (13)* | |
H17B | −0.595 (3) | 0.429 (2) | 0.989 (2) | 0.101 (14)* | |
H17C | −0.617 (3) | 0.378 (2) | 0.921 (2) | 0.100 (14)* | |
H18 | −0.159 (2) | 0.3905 (15) | 0.7804 (15) | 0.054 (8)* | |
H20A | 0.003 (2) | 0.2309 (17) | 0.8059 (18) | 0.074 (9)* | |
H20B | −0.121 (2) | 0.2565 (15) | 0.7834 (16) | 0.066 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0413 (4) | 0.0502 (5) | 0.0893 (6) | 0.0117 (4) | −0.0038 (4) | −0.0147 (5) |
O1 | 0.0505 (11) | 0.0414 (12) | 0.0851 (16) | 0.0029 (10) | 0.0027 (11) | 0.0063 (11) |
O2 | 0.0713 (14) | 0.0649 (15) | 0.0722 (16) | −0.0151 (12) | 0.0039 (11) | −0.0268 (12) |
O3 | 0.0342 (12) | 0.0960 (19) | 0.0985 (19) | 0.0003 (12) | 0.0019 (11) | 0.0036 (15) |
N1 | 0.0351 (12) | 0.0377 (13) | 0.0523 (15) | 0.0006 (10) | 0.0005 (10) | −0.0026 (11) |
N2 | 0.0431 (11) | 0.0511 (12) | 0.0827 (17) | 0.0050 (10) | −0.0063 (10) | −0.0165 (11) |
C1 | 0.0402 (15) | 0.0399 (17) | 0.0500 (18) | 0.0027 (13) | −0.0037 (13) | −0.0064 (14) |
C2 | 0.0375 (15) | 0.0336 (15) | 0.0451 (17) | 0.0002 (12) | −0.0017 (13) | 0.0010 (13) |
C3 | 0.0371 (15) | 0.0390 (16) | 0.0501 (18) | −0.0008 (13) | 0.0015 (13) | −0.0028 (15) |
C4 | 0.0388 (16) | 0.0469 (17) | 0.055 (2) | −0.0059 (14) | 0.0011 (15) | 0.0021 (15) |
C5 | 0.0551 (17) | 0.0405 (17) | 0.0474 (18) | −0.0031 (14) | −0.0047 (14) | −0.0016 (14) |
C6 | 0.0501 (17) | 0.0481 (18) | 0.0466 (19) | −0.0001 (15) | 0.0056 (14) | −0.0046 (15) |
C7 | 0.0377 (15) | 0.0423 (17) | 0.052 (2) | −0.0057 (14) | 0.0047 (14) | −0.0006 (15) |
C8 | 0.068 (2) | 0.065 (3) | 0.090 (4) | −0.017 (2) | −0.012 (2) | −0.023 (3) |
C9 | 0.0332 (14) | 0.0361 (15) | 0.0534 (18) | 0.0030 (12) | −0.0012 (12) | −0.0026 (14) |
C10 | 0.0370 (15) | 0.0375 (16) | 0.0421 (17) | −0.0021 (13) | 0.0039 (12) | 0.0025 (13) |
C11 | 0.0378 (14) | 0.0408 (16) | 0.0483 (18) | 0.0052 (13) | −0.0035 (12) | −0.0069 (15) |
C12 | 0.0432 (17) | 0.0434 (18) | 0.070 (2) | 0.0086 (15) | −0.0040 (16) | −0.0003 (16) |
C13 | 0.051 (2) | 0.048 (2) | 0.069 (2) | −0.0038 (16) | 0.0083 (17) | 0.0024 (18) |
C14 | 0.0384 (17) | 0.064 (2) | 0.064 (2) | 0.0039 (15) | −0.0051 (14) | −0.0140 (19) |
C15 | 0.0390 (17) | 0.065 (2) | 0.068 (2) | 0.0130 (17) | −0.0070 (15) | −0.0006 (18) |
C16 | 0.0502 (18) | 0.054 (2) | 0.052 (2) | 0.0068 (16) | −0.0038 (15) | 0.0015 (17) |
C17 | 0.055 (2) | 0.077 (3) | 0.088 (3) | −0.014 (2) | 0.007 (2) | −0.015 (3) |
C18 | 0.0369 (15) | 0.0489 (18) | 0.069 (2) | 0.0022 (14) | −0.0080 (15) | −0.0124 (16) |
C19 | 0.0367 (14) | 0.0412 (17) | 0.0558 (19) | 0.0011 (12) | −0.0015 (13) | −0.0034 (14) |
C20 | 0.0431 (11) | 0.0511 (12) | 0.0827 (17) | 0.0050 (10) | −0.0063 (10) | −0.0165 (11) |
C21 | 0.078 (2) | 0.103 (3) | 0.079 (3) | 0.010 (2) | −0.010 (2) | 0.001 (2) |
S1—C19 | 1.666 (3) | C8—H8B | 1.05 (4) |
O1—C1 | 1.212 (3) | C8—H8C | 0.98 (4) |
O2—C5 | 1.370 (3) | C9—C18 | 1.350 (4) |
O2—C8 | 1.426 (4) | C9—C10 | 1.426 (3) |
O3—C14 | 1.360 (3) | C11—C12 | 1.378 (4) |
O3—C17 | 1.415 (5) | C11—C16 | 1.396 (4) |
N1—C10 | 1.322 (3) | C12—C13 | 1.391 (4) |
N1—C19 | 1.358 (3) | C12—H12 | 0.93 (3) |
N2—C18 | 1.352 (3) | C13—C14 | 1.370 (4) |
N2—C19 | 1.386 (3) | C13—H13 | 0.84 (3) |
N2—C20 | 1.544 (4) | C14—C15 | 1.379 (4) |
C1—C11 | 1.486 (4) | C15—C16 | 1.362 (4) |
C1—C9 | 1.501 (4) | C15—H15 | 0.99 (3) |
C2—C3 | 1.384 (3) | C16—H16 | 0.96 (3) |
C2—C7 | 1.387 (4) | C17—H17A | 0.95 (4) |
C2—C10 | 1.485 (4) | C17—H17B | 0.96 (4) |
C3—C4 | 1.385 (4) | C17—H17C | 0.94 (4) |
C3—H3 | 0.97 (2) | C18—H18 | 0.95 (3) |
C4—C5 | 1.381 (4) | C20—C21 | 1.446 (5) |
C4—H4 | 0.95 (3) | C20—H20A | 1.03 (3) |
C5—C6 | 1.376 (4) | C20—H20B | 1.00 (3) |
C6—C7 | 1.378 (4) | C21—H21A | 0.9600 |
C6—H6 | 1.00 (3) | C21—H21B | 0.9600 |
C7—H7 | 0.92 (2) | C21—H21C | 0.9600 |
C8—H8A | 0.86 (4) | ||
C5—O2—C8 | 118.1 (3) | C16—C11—C1 | 117.8 (3) |
C14—O3—C17 | 120.1 (3) | C11—C12—C13 | 120.8 (3) |
C10—N1—C19 | 121.7 (2) | C11—C12—H12 | 121.4 (16) |
C18—N2—C19 | 120.5 (2) | C13—C12—H12 | 117.7 (16) |
C18—N2—C20 | 119.1 (2) | C14—C13—C12 | 119.9 (3) |
C19—N2—C20 | 120.2 (2) | C14—C13—H13 | 121.1 (18) |
O1—C1—C11 | 120.8 (2) | C12—C13—H13 | 118.9 (18) |
O1—C1—C9 | 119.7 (2) | O3—C14—C13 | 124.6 (3) |
C11—C1—C9 | 119.5 (2) | O3—C14—C15 | 115.5 (3) |
C3—C2—C7 | 118.2 (3) | C13—C14—C15 | 119.8 (3) |
C3—C2—C10 | 119.8 (2) | C16—C15—C14 | 120.3 (3) |
C7—C2—C10 | 121.9 (2) | C16—C15—H15 | 121.8 (19) |
C2—C3—C4 | 121.5 (3) | C14—C15—H15 | 117.8 (19) |
C2—C3—H3 | 119.0 (14) | C15—C16—C11 | 121.1 (3) |
C4—C3—H3 | 119.3 (14) | C15—C16—H16 | 120.8 (16) |
C5—C4—C3 | 119.3 (3) | C11—C16—H16 | 118.0 (16) |
C5—C4—H4 | 124.3 (17) | O3—C17—H17A | 108 (2) |
C3—C4—H4 | 116.5 (17) | O3—C17—H17B | 107 (2) |
O2—C5—C6 | 115.2 (3) | H17A—C17—H17B | 116 (3) |
O2—C5—C4 | 124.9 (3) | O3—C17—H17C | 114 (2) |
C6—C5—C4 | 119.8 (3) | H17A—C17—H17C | 107 (3) |
C5—C6—C7 | 120.5 (3) | H17B—C17—H17C | 105 (3) |
C5—C6—H6 | 118.5 (14) | C9—C18—N2 | 122.3 (3) |
C7—C6—H6 | 121.0 (14) | C9—C18—H18 | 122.0 (16) |
C6—C7—C2 | 120.6 (3) | N2—C18—H18 | 115.7 (16) |
C6—C7—H7 | 119.8 (16) | N1—C19—N2 | 117.7 (2) |
C2—C7—H7 | 119.5 (16) | N1—C19—S1 | 121.18 (19) |
O2—C8—H8A | 102 (2) | N2—C19—S1 | 121.0 (2) |
O2—C8—H8B | 113 (2) | C21—C20—N2 | 108.6 (3) |
H8A—C8—H8B | 112 (3) | C21—C20—H20A | 105.6 (17) |
O2—C8—H8C | 115 (2) | N2—C20—H20A | 111.9 (17) |
H8A—C8—H8C | 116 (3) | C21—C20—H20B | 106.5 (16) |
H8B—C8—H8C | 100 (3) | N2—C20—H20B | 115.3 (16) |
C18—C9—C10 | 116.0 (2) | H20A—C20—H20B | 108 (2) |
C18—C9—C1 | 120.0 (2) | C20—C21—H21A | 109.5 |
C10—C9—C1 | 123.6 (2) | C20—C21—H21B | 109.5 |
N1—C10—C9 | 121.3 (2) | H21A—C21—H21B | 109.5 |
N1—C10—C2 | 114.7 (2) | C20—C21—H21C | 109.5 |
C9—C10—C2 | 123.8 (2) | H21A—C21—H21C | 109.5 |
C12—C11—C16 | 118.1 (3) | H21B—C21—H21C | 109.5 |
C12—C11—C1 | 124.0 (2) | ||
C7—C2—C3—C4 | −1.1 (4) | C9—C1—C11—C12 | 18.2 (4) |
C10—C2—C3—C4 | −177.1 (3) | O1—C1—C11—C16 | 14.6 (4) |
C2—C3—C4—C5 | 1.7 (4) | C9—C1—C11—C16 | −164.9 (3) |
C8—O2—C5—C6 | 175.8 (3) | C16—C11—C12—C13 | 0.4 (4) |
C8—O2—C5—C4 | −3.7 (5) | C1—C11—C12—C13 | 177.3 (3) |
C3—C4—C5—O2 | 178.0 (3) | C11—C12—C13—C14 | 0.3 (5) |
C3—C4—C5—C6 | −1.4 (4) | C17—O3—C14—C13 | 2.3 (5) |
O2—C5—C6—C7 | −178.8 (3) | C17—O3—C14—C15 | −177.1 (3) |
C4—C5—C6—C7 | 0.7 (5) | C12—C13—C14—O3 | −179.9 (3) |
C5—C6—C7—C2 | −0.1 (5) | C12—C13—C14—C15 | −0.6 (5) |
C3—C2—C7—C6 | 0.3 (4) | O3—C14—C15—C16 | 179.6 (3) |
C10—C2—C7—C6 | 176.2 (3) | C13—C14—C15—C16 | 0.2 (5) |
O1—C1—C9—C18 | −133.0 (3) | C14—C15—C16—C11 | 0.5 (5) |
C11—C1—C9—C18 | 46.5 (4) | C12—C11—C16—C15 | −0.8 (4) |
O1—C1—C9—C10 | 39.1 (4) | C1—C11—C16—C15 | −177.9 (3) |
C11—C1—C9—C10 | −141.4 (3) | C10—C9—C18—N2 | −1.8 (4) |
C19—N1—C10—C9 | −2.7 (4) | C1—C9—C18—N2 | 170.9 (3) |
C19—N1—C10—C2 | 174.5 (2) | C19—N2—C18—C9 | −4.4 (5) |
C18—C9—C10—N1 | 5.4 (4) | C20—N2—C18—C9 | 170.1 (3) |
C1—C9—C10—N1 | −167.0 (3) | C10—N1—C19—N2 | −3.5 (4) |
C18—C9—C10—C2 | −171.5 (3) | C10—N1—C19—S1 | −179.9 (2) |
C1—C9—C10—C2 | 16.1 (4) | C18—N2—C19—N1 | 7.1 (4) |
C3—C2—C10—N1 | 32.5 (4) | C20—N2—C19—N1 | −167.3 (3) |
C7—C2—C10—N1 | −143.3 (3) | C18—N2—C19—S1 | −176.5 (2) |
C3—C2—C10—C9 | −150.3 (3) | C20—N2—C19—S1 | 9.1 (4) |
C7—C2—C10—C9 | 33.8 (4) | C18—N2—C20—C21 | 99.8 (3) |
O1—C1—C11—C12 | −162.3 (3) | C19—N2—C20—C21 | −85.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C18—H18···S1i | 0.95 (3) | 2.86 (3) | 3.755 (3) | 159 (2) |
C15—H15···O1i | 0.99 (3) | 2.54 (3) | 3.291 (4) | 133 (2) |
C21—H21B···S1 | 0.96 | 2.80 | 3.383 (4) | 120 |
C17—H17B···Cg3ii | 0.94 (4) | 2.86 (3) | 3.618 (6) | 139 (3) |
C21—H21A···Cg2iii | 0.96 | 2.76 | 3.567 (4) | 142 |
Symmetry codes: (i) x−1/2, y, −z+3/2; (ii) −x, −y, −z; (iii) −x+1, y+1/2, −z+1/2. |