Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009923/na6169sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009923/na6169Isup2.hkl |
CCDC reference: 189892
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.006 Å
- R factor = 0.050
- wR factor = 0.136
- Data-to-parameter ratio = 12.5
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
GOODF_01 Alert C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.794 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.98 From the CIF: _reflns_number_total 2867 Count of symmetry unique reflns 1793 Completeness (_total/calc) 159.90% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1074 Fraction of Friedel pairs measured 0.599 Are heavy atom types Z>Si present yes 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97.
C17H21N3O3S | Dx = 1.334 Mg m−3 |
Mr = 347.43 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 8676 reflections |
a = 6.1391 (4) Å | θ = 2.9–27.5° |
b = 9.9755 (6) Å | µ = 0.21 mm−1 |
c = 28.248 (2) Å | T = 120 K |
V = 1729.9 (2) Å3 | Block, colourless |
Z = 4 | 0.10 × 0.07 × 0.06 mm |
F(000) = 736 |
Bruker–Nonius KappaCCD area detector diffractometer | 2867 independent reflections |
Radiation source: Bruker–Nonius FR591 rotating anode | 2175 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.073 |
Detector resolution: 9.091 pixels mm-1 | θmax = 25.0°, θmin = 3.0° |
φ and ω scans | h = −6→7 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −11→11 |
Tmin = 0.980, Tmax = 0.988 | l = −33→18 |
6163 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.050 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.136 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.79 | (Δ/σ)max < 0.001 |
2867 reflections | Δρmax = 0.26 e Å−3 |
229 parameters | Δρmin = −0.22 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 706 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.19 (13) |
Geometry. Mean plane data ex SHELXL97 ########################### Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 3.4665 (0.0094) x - 6.2890 (0.0108) y + 15.0459 (0.0543) z = 0.1624 (0.0138) * -0.0026 (0.0016) S1 * 0.0034 (0.0022) C2 * -0.0026 (0.0017) N3 * 0.0009 (0.0006) C5 * 0.0009 (0.0006) C5 Rms deviation of fitted atoms = 0.0023 2.6057 (0.0088) x - 3.3983 (0.0154) y + 23.6980 (0.0252) z = 2.1328 (0.0264) Angle to previous plane (with approximate e.s.d.) = 25.67 (0.23) * 0.0013 (0.0028) C24 * -0.0042 (0.0028) C25 * 0.0045 (0.0028) C26 * -0.0020 (0.0029) C27 * -0.0008 (0.0029) C28 * 0.0011 (0.0028) C29 Rms deviation of fitted atoms = 0.0027 |
x | y | z | Uiso*/Ueq | ||
S1 | −0.03482 (16) | −0.26387 (10) | 0.09594 (3) | 0.0201 (3) | |
C2 | 0.1869 (6) | −0.1605 (4) | 0.08846 (14) | 0.0192 (9) | |
N3 | 0.2119 (5) | −0.0682 (3) | 0.12088 (12) | 0.0184 (8) | |
C4 | 0.0523 (6) | −0.0733 (4) | 0.15504 (13) | 0.0184 (9) | |
C5 | −0.0972 (6) | −0.1752 (4) | 0.14761 (14) | 0.0187 (9) | |
N21 | 0.3266 (6) | −0.1741 (4) | 0.05020 (12) | 0.0207 (8) | |
H21 | 0.295 (6) | −0.235 (4) | 0.0317 (14) | 0.013 (11)* | |
C22 | 0.5050 (6) | −0.0960 (4) | 0.03774 (13) | 0.0169 (9) | |
O22 | 0.6105 (4) | −0.1253 (3) | 0.00222 (9) | 0.0217 (7) | |
N23 | 0.5454 (6) | 0.0100 (3) | 0.06644 (12) | 0.0199 (8) | |
H23 | 0.435 (6) | 0.013 (4) | 0.0919 (14) | 0.020 (10)* | |
C24 | 0.7084 (7) | 0.1097 (4) | 0.06134 (13) | 0.0176 (9) | |
C25 | 0.9038 (7) | 0.0898 (4) | 0.03677 (15) | 0.0242 (10) | |
H25 | 0.9323 | 0.0069 | 0.0214 | 0.030* | |
C26 | 1.0545 (7) | 0.1924 (4) | 0.03529 (14) | 0.0239 (10) | |
H26 | 1.1882 | 0.1788 | 0.0191 | 0.030* | |
C27 | 1.0158 (7) | 0.3142 (5) | 0.05673 (14) | 0.0278 (10) | |
H27 | 1.1208 | 0.3840 | 0.0550 | 0.035* | |
C28 | 0.8207 (7) | 0.3338 (4) | 0.08104 (14) | 0.0254 (10) | |
H28 | 0.7919 | 0.4170 | 0.0961 | 0.032* | |
C29 | 0.6703 (7) | 0.2320 (4) | 0.08305 (14) | 0.0247 (10) | |
H29 | 0.5376 | 0.2457 | 0.0997 | 0.031* | |
C41 | 0.0621 (6) | 0.0311 (4) | 0.19464 (13) | 0.0201 (9) | |
C42 | 0.2408 (6) | 0.1330 (4) | 0.18309 (14) | 0.0230 (10) | |
H421 | 0.3813 | 0.0868 | 0.1807 | 0.029* | |
H422 | 0.2481 | 0.2004 | 0.2083 | 0.029* | |
H423 | 0.2075 | 0.1770 | 0.1529 | 0.029* | |
C43 | 0.1224 (7) | −0.0389 (5) | 0.24145 (14) | 0.0259 (10) | |
H431 | 0.2629 | −0.0844 | 0.2379 | 0.032* | |
H432 | 0.0099 | −0.1048 | 0.2495 | 0.032* | |
H433 | 0.1327 | 0.0280 | 0.2668 | 0.032* | |
C44 | −0.1527 (7) | 0.1061 (4) | 0.19972 (16) | 0.0256 (11) | |
H441 | −0.1400 | 0.1728 | 0.2251 | 0.032* | |
H442 | −0.2690 | 0.0425 | 0.2075 | 0.032* | |
H443 | −0.1874 | 0.1514 | 0.1699 | 0.032* | |
C51 | −0.2832 (6) | −0.2207 (4) | 0.17572 (14) | 0.0176 (9) | |
O51 | −0.3433 (4) | −0.1748 (3) | 0.21338 (10) | 0.0253 (7) | |
O52 | −0.3826 (4) | −0.3260 (3) | 0.15494 (10) | 0.0240 (7) | |
C53 | −0.5728 (7) | −0.3790 (4) | 0.18000 (15) | 0.0238 (10) | |
H531 | −0.6964 | −0.3156 | 0.1775 | 0.030* | |
H532 | −0.5384 | −0.3924 | 0.2139 | 0.030* | |
C54 | −0.6305 (8) | −0.5105 (5) | 0.15721 (18) | 0.0387 (13) | |
H541 | −0.5153 | −0.5760 | 0.1636 | 0.048* | |
H542 | −0.6453 | −0.4979 | 0.1229 | 0.048* | |
H543 | −0.7686 | −0.5432 | 0.1702 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0218 (6) | 0.0207 (6) | 0.0179 (5) | −0.0039 (5) | 0.0001 (4) | −0.0021 (5) |
C2 | 0.019 (2) | 0.018 (2) | 0.020 (2) | 0.0048 (18) | 0.0021 (18) | −0.0006 (19) |
N3 | 0.0176 (19) | 0.016 (2) | 0.022 (2) | −0.0037 (15) | 0.0022 (15) | −0.0015 (15) |
C4 | 0.024 (2) | 0.017 (2) | 0.014 (2) | −0.0001 (18) | 0.0002 (18) | 0.0042 (16) |
C5 | 0.020 (2) | 0.018 (2) | 0.019 (2) | −0.0029 (18) | 0.0003 (17) | 0.0008 (18) |
N21 | 0.023 (2) | 0.020 (2) | 0.0192 (19) | −0.0013 (18) | 0.0018 (16) | −0.0052 (17) |
C22 | 0.021 (2) | 0.016 (2) | 0.014 (2) | 0.0021 (18) | −0.0010 (18) | 0.0029 (16) |
O22 | 0.0234 (16) | 0.0240 (16) | 0.0178 (15) | 0.0020 (12) | 0.0018 (12) | −0.0031 (13) |
N23 | 0.0206 (19) | 0.0215 (19) | 0.0175 (18) | −0.0043 (17) | 0.0043 (16) | −0.0022 (15) |
C24 | 0.021 (2) | 0.020 (2) | 0.012 (2) | −0.0046 (19) | −0.0015 (16) | 0.0017 (17) |
C25 | 0.027 (3) | 0.027 (3) | 0.019 (2) | 0.0027 (19) | −0.0006 (18) | 0.0029 (18) |
C26 | 0.016 (2) | 0.033 (3) | 0.023 (2) | −0.003 (2) | −0.0009 (18) | 0.0064 (19) |
C27 | 0.029 (3) | 0.031 (3) | 0.023 (2) | −0.010 (2) | −0.006 (2) | 0.0067 (19) |
C28 | 0.029 (3) | 0.025 (2) | 0.022 (2) | −0.009 (2) | 0.001 (2) | −0.0039 (19) |
C29 | 0.026 (2) | 0.024 (2) | 0.023 (2) | −0.005 (2) | 0.0056 (18) | −0.0023 (19) |
C41 | 0.024 (2) | 0.020 (2) | 0.016 (2) | −0.005 (2) | 0.0026 (18) | −0.0004 (17) |
C42 | 0.030 (3) | 0.021 (3) | 0.018 (2) | −0.003 (2) | 0.0020 (18) | −0.0069 (19) |
C43 | 0.029 (2) | 0.029 (3) | 0.020 (2) | −0.002 (2) | −0.0015 (19) | −0.004 (2) |
C44 | 0.025 (3) | 0.027 (3) | 0.025 (2) | 0.002 (2) | 0.005 (2) | −0.003 (2) |
C51 | 0.017 (2) | 0.018 (2) | 0.017 (2) | 0.0044 (18) | −0.0019 (17) | 0.0014 (18) |
O51 | 0.0238 (16) | 0.0306 (17) | 0.0213 (16) | −0.0054 (14) | 0.0028 (13) | −0.0047 (14) |
O52 | 0.0240 (15) | 0.0239 (16) | 0.0241 (15) | −0.0086 (13) | 0.0034 (12) | −0.0050 (13) |
C53 | 0.022 (2) | 0.024 (2) | 0.025 (2) | −0.0053 (19) | 0.0047 (18) | 0.001 (2) |
C54 | 0.032 (3) | 0.036 (3) | 0.048 (3) | −0.013 (2) | 0.016 (2) | −0.010 (2) |
S1—C2 | 1.721 (4) | C28—H28 | 0.95 |
S1—C5 | 1.749 (4) | C29—H29 | 0.95 |
C2—N3 | 1.308 (5) | C41—C44 | 1.523 (6) |
C2—N21 | 1.387 (5) | C41—C42 | 1.531 (5) |
N3—C4 | 1.376 (5) | C41—C43 | 1.540 (6) |
C4—C5 | 1.385 (6) | C42—H421 | 0.98 |
C4—C41 | 1.529 (5) | C42—H422 | 0.98 |
C5—C51 | 1.463 (5) | C42—H423 | 0.98 |
N21—C22 | 1.389 (5) | C43—H431 | 0.98 |
N21—H21 | 0.82 (4) | C43—H432 | 0.98 |
C22—O22 | 1.229 (4) | C43—H433 | 0.98 |
C22—N23 | 1.356 (5) | C44—H441 | 0.98 |
N23—C24 | 1.418 (5) | C44—H442 | 0.98 |
N23—H23 | 0.99 (4) | C44—H443 | 0.98 |
C24—C29 | 1.385 (6) | C51—O51 | 1.215 (4) |
C24—C25 | 1.400 (6) | C51—O52 | 1.350 (5) |
C25—C26 | 1.381 (6) | O52—C53 | 1.464 (5) |
C25—H25 | 0.95 | C53—C54 | 1.504 (6) |
C26—C27 | 1.378 (6) | C53—H531 | 0.99 |
C26—H26 | 0.95 | C53—H532 | 0.99 |
C27—C28 | 1.394 (6) | C54—H541 | 0.98 |
C27—H27 | 0.95 | C54—H542 | 0.98 |
C28—C29 | 1.374 (6) | C54—H543 | 0.98 |
C2—S1—C5 | 88.4 (2) | C44—C41—C42 | 108.3 (3) |
N3—C2—N21 | 122.9 (4) | C4—C41—C42 | 108.9 (3) |
N3—C2—S1 | 115.4 (3) | C44—C41—C43 | 110.5 (3) |
N21—C2—S1 | 121.8 (3) | C4—C41—C43 | 109.2 (3) |
C2—N3—C4 | 112.4 (3) | C42—C41—C43 | 108.1 (3) |
N3—C4—C5 | 113.1 (3) | C41—C42—H421 | 109.5 |
N3—C4—C41 | 117.4 (3) | C41—C42—H422 | 109.5 |
C5—C4—C41 | 129.5 (4) | H421—C42—H422 | 109.5 |
C4—C5—C51 | 131.5 (4) | C41—C42—H423 | 109.5 |
C4—C5—S1 | 110.6 (3) | H421—C42—H423 | 109.5 |
C51—C5—S1 | 117.8 (3) | H422—C42—H423 | 109.5 |
C2—N21—C22 | 129.1 (4) | C41—C43—H431 | 109.5 |
C2—N21—H21 | 115 (3) | C41—C43—H432 | 109.5 |
C22—N21—H21 | 116 (3) | H431—C43—H432 | 109.5 |
O22—C22—N23 | 125.2 (4) | C41—C43—H433 | 109.5 |
O22—C22—N21 | 119.3 (3) | H431—C43—H433 | 109.5 |
N23—C22—N21 | 115.5 (3) | H432—C43—H433 | 109.5 |
C22—N23—C24 | 128.0 (3) | C41—C44—H441 | 109.5 |
C22—N23—H23 | 109 (2) | C41—C44—H442 | 109.5 |
C24—N23—H23 | 122 (2) | H441—C44—H442 | 109.5 |
C29—C24—C25 | 119.3 (4) | C41—C44—H443 | 109.5 |
C29—C24—N23 | 117.0 (4) | H441—C44—H443 | 109.5 |
C25—C24—N23 | 123.7 (4) | H442—C44—H443 | 109.5 |
C26—C25—C24 | 118.9 (4) | O51—C51—O52 | 122.4 (4) |
C26—C25—H25 | 120.5 | O51—C51—C5 | 126.5 (4) |
C24—C25—H25 | 120.5 | O52—C51—C5 | 111.0 (3) |
C27—C26—C25 | 121.7 (4) | C51—O52—C53 | 115.5 (3) |
C27—C26—H26 | 119.1 | O52—C53—C54 | 107.2 (3) |
C25—C26—H26 | 119.1 | O52—C53—H531 | 110.3 |
C26—C27—C28 | 119.2 (4) | C54—C53—H531 | 110.3 |
C26—C27—H27 | 120.4 | O52—C53—H532 | 110.3 |
C28—C27—H27 | 120.4 | C54—C53—H532 | 110.3 |
C29—C28—C27 | 119.6 (4) | H531—C53—H532 | 108.5 |
C29—C28—H28 | 120.2 | C53—C54—H541 | 109.5 |
C27—C28—H28 | 120.2 | C53—C54—H542 | 109.5 |
C28—C29—C24 | 121.3 (4) | H541—C54—H542 | 109.5 |
C28—C29—H29 | 119.4 | C53—C54—H543 | 109.5 |
C24—C29—H29 | 119.4 | H541—C54—H543 | 109.5 |
C44—C41—C4 | 111.7 (3) | H542—C54—H543 | 109.5 |
C5—S1—C2—N3 | −0.5 (3) | N23—C24—C25—C26 | −177.9 (4) |
C5—S1—C2—N21 | −179.7 (4) | C24—C25—C26—C27 | −1.0 (6) |
N21—C2—N3—C4 | 179.3 (4) | C25—C26—C27—C28 | 0.8 (6) |
S1—C2—N3—C4 | 0.1 (4) | C26—C27—C28—C29 | −0.3 (6) |
C2—N3—C4—C5 | 0.5 (5) | C27—C28—C29—C24 | 0.0 (6) |
C2—N3—C4—C41 | −179.2 (3) | C25—C24—C29—C28 | −0.2 (6) |
N3—C4—C5—C51 | 176.5 (4) | N23—C24—C29—C28 | 178.5 (4) |
C41—C4—C5—C51 | −3.9 (7) | N3—C4—C41—C44 | 126.8 (4) |
N3—C4—C5—S1 | −0.8 (4) | C5—C4—C41—C44 | −52.8 (5) |
C41—C4—C5—S1 | 178.8 (3) | N3—C4—C41—C42 | 7.2 (5) |
C2—S1—C5—C4 | 0.7 (3) | C5—C4—C41—C42 | −172.4 (4) |
C2—S1—C5—C51 | −177.0 (3) | N3—C4—C41—C43 | −110.7 (4) |
N3—C2—N21—C22 | −2.6 (7) | C5—C4—C41—C43 | 69.7 (5) |
S1—C2—N21—C22 | 176.6 (3) | C4—C5—C51—O51 | −0.6 (7) |
C2—N21—C22—O22 | 179.5 (4) | S1—C5—C51—O51 | 176.6 (3) |
C2—N21—C22—N23 | −1.5 (6) | C4—C5—C51—O52 | −179.1 (4) |
O22—C22—N23—C24 | 2.0 (6) | S1—C5—C51—O52 | −1.9 (4) |
N21—C22—N23—C24 | −176.9 (4) | O51—C51—O52—C53 | 2.0 (5) |
C22—N23—C24—C29 | 156.1 (4) | C5—C51—O52—C53 | −179.5 (3) |
C22—N23—C24—C25 | −25.3 (6) | C51—O52—C53—C54 | −168.5 (3) |
C29—C24—C25—C26 | 0.7 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N21—H21···O22i | 0.82 (4) | 2.03 (4) | 2.821 (5) | 159 (4) |
N23—H23···N3 | 0.99 (4) | 1.79 (4) | 2.677 (5) | 148 (3) |
C25—H25···O22 | 0.95 | 2.44 | 2.966 (5) | 115 |
C43—H432···O51 | 0.98 | 2.50 | 3.262 (5) | 135 |
C44—H442···O51 | 0.98 | 2.22 | 3.061 (5) | 143 |
Symmetry code: (i) x−1/2, −y−1/2, −z. |
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