Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803019007/om6170sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803019007/om6170Isup2.hkl |
CCDC reference: 225709
Data collection: COLLECT (Nonius, 1999); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELX97 (Sheldrick, 1997) and local procedures.
C12H13NOS | F(000) = 464 |
Mr = 219.29 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 11.321 (1) Å | Cell parameters from 6483 reflections |
b = 5.8790 (6) Å | θ = 1.0–27.5° |
c = 16.100 (2) Å | µ = 0.27 mm−1 |
β = 94.058 (10)° | T = 173 K |
V = 1068.9 (2) Å3 | Rod, yellow |
Z = 4 | 0.40 × 0.33 × 0.20 mm |
Nonius KappaCCD diffractometer | 2452 independent reflections |
Radiation source: fine-focus sealed tube | 1802 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
Detector resolution: 18 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
ω scans at fixed χ = 55° | h = −14→14 |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | k = −7→7 |
Tmin = 0.899, Tmax = 0.947 | l = −20→20 |
7996 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)] = 0.045 | H-atom parameters constrained |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0604P)2 + 0.2115P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.002 |
2452 reflections | Δρmax = 0.24 e Å−3 |
143 parameters | Δρmin = −0.25 e Å−3 |
8 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.020 (3) |
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 | Occ. (<1) | |
S1 | −0.1702 (3) | −0.3427 (5) | 0.29234 (16) | 0.0389 (4) | 0.50 |
C5' | −0.1557 (11) | −0.317 (2) | 0.2840 (7) | 0.0389 (4) | 0.50 |
H5' | −0.2144 | −0.4059 | 0.3082 | 0.047* | 0.50 |
C2 | −0.11178 (15) | −0.3704 (3) | 0.20480 (11) | 0.0374 (4) | |
H2 | −0.1329 | −0.4921 | 0.1678 | 0.045* | |
C3 | −0.02826 (14) | −0.2065 (3) | 0.18579 (10) | 0.0296 (4) | |
C4 | −0.01283 (15) | −0.0427 (3) | 0.24936 (10) | 0.0333 (4) | |
H4 | 0.0395 | 0.0838 | 0.2502 | 0.040* | |
C5 | −0.0883 (8) | −0.0997 (15) | 0.3110 (4) | 0.0366 (3) | 0.50 |
H5 | −0.0940 | −0.0106 | 0.3598 | 0.044* | 0.50 |
S1' | −0.09402 (17) | −0.0817 (3) | 0.33130 (8) | 0.0366 (3) | 0.50 |
C6 | 0.03386 (14) | −0.2198 (3) | 0.11007 (10) | 0.0294 (4) | |
H6 | 0.0006 | −0.3209 | 0.0687 | 0.035* | |
C7 | 0.13123 (14) | −0.1097 (3) | 0.09042 (10) | 0.0272 (4) | |
N8 | 0.19491 (12) | 0.0516 (2) | 0.14457 (8) | 0.0304 (4) | |
C9 | 0.21488 (18) | 0.2604 (3) | 0.09625 (12) | 0.0415 (5) | |
H9A | 0.2560 | 0.3744 | 0.1332 | 0.050* | |
H9B | 0.1375 | 0.3252 | 0.0759 | 0.050* | |
C10 | 0.28946 (18) | 0.2139 (3) | 0.02131 (12) | 0.0440 (5) | |
H10A | 0.2472 | 0.2696 | −0.0307 | 0.053* | |
H10B | 0.3664 | 0.2940 | 0.0289 | 0.053* | |
C11 | 0.30970 (15) | −0.0440 (3) | 0.01581 (10) | 0.0351 (4) | |
H11 | 0.3527 | −0.0837 | −0.0344 | 0.042* | |
C12 | 0.37970 (16) | −0.1217 (3) | 0.09611 (10) | 0.0370 (4) | |
H12A | 0.4594 | −0.0515 | 0.1000 | 0.044* | |
H12B | 0.3893 | −0.2891 | 0.0958 | 0.044* | |
C13 | 0.31109 (15) | −0.0486 (3) | 0.17110 (10) | 0.0354 (4) | |
H13A | 0.2991 | −0.1826 | 0.2068 | 0.043* | |
H13B | 0.3586 | 0.0642 | 0.2047 | 0.043* | |
C14 | 0.19134 (15) | −0.1599 (3) | 0.01362 (10) | 0.0323 (4) | |
O15 | 0.15168 (12) | −0.2842 (2) | −0.04277 (7) | 0.0451 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0353 (9) | 0.0493 (8) | 0.0325 (7) | −0.0044 (5) | 0.0049 (5) | −0.0035 (6) |
C5' | 0.0353 (9) | 0.0493 (8) | 0.0325 (7) | −0.0044 (5) | 0.0049 (5) | −0.0035 (6) |
C2 | 0.0299 (9) | 0.0437 (11) | 0.0379 (10) | −0.0042 (8) | −0.0021 (8) | 0.0008 (8) |
C3 | 0.0242 (8) | 0.0339 (9) | 0.0303 (9) | 0.0038 (7) | −0.0013 (6) | 0.0009 (7) |
C4 | 0.0305 (9) | 0.0352 (10) | 0.0342 (9) | 0.0036 (8) | 0.0018 (7) | −0.0056 (7) |
C5 | 0.0321 (5) | 0.0473 (6) | 0.0305 (8) | 0.0003 (4) | 0.0040 (6) | −0.0064 (6) |
S1' | 0.0321 (5) | 0.0473 (6) | 0.0305 (8) | 0.0003 (4) | 0.0040 (6) | −0.0064 (6) |
C6 | 0.0276 (9) | 0.0309 (9) | 0.0290 (9) | 0.0010 (7) | −0.0033 (7) | −0.0044 (7) |
C7 | 0.0287 (9) | 0.0263 (9) | 0.0265 (8) | 0.0013 (7) | 0.0002 (6) | −0.0018 (6) |
N8 | 0.0339 (8) | 0.0264 (7) | 0.0308 (7) | −0.0042 (6) | 0.0018 (6) | −0.0034 (6) |
C9 | 0.0540 (11) | 0.0256 (9) | 0.0453 (11) | −0.0028 (9) | 0.0060 (9) | −0.0007 (8) |
C10 | 0.0592 (13) | 0.0355 (10) | 0.0376 (11) | −0.0087 (9) | 0.0056 (9) | 0.0080 (8) |
C11 | 0.0392 (10) | 0.0386 (10) | 0.0283 (9) | −0.0043 (8) | 0.0085 (7) | −0.0003 (7) |
C12 | 0.0319 (9) | 0.0394 (10) | 0.0399 (10) | −0.0009 (8) | 0.0035 (7) | −0.0008 (8) |
C13 | 0.0354 (10) | 0.0400 (10) | 0.0303 (9) | −0.0059 (8) | −0.0017 (7) | 0.0018 (8) |
C14 | 0.0384 (10) | 0.0310 (9) | 0.0272 (9) | 0.0007 (8) | 0.0011 (7) | 0.0002 (7) |
O15 | 0.0531 (8) | 0.0502 (8) | 0.0320 (7) | −0.0098 (7) | 0.0035 (6) | −0.0123 (6) |
S1—C2 | 1.607 (3) | N8—C13 | 1.476 (2) |
S1—C5 | 1.718 (8) | N8—C9 | 1.480 (2) |
C5'—C2 | 1.436 (10) | C9—C10 | 1.545 (3) |
C5'—S1' | 1.705 (11) | C9—H9A | 0.9900 |
C5'—H5' | 0.9500 | C9—H9B | 0.9900 |
C2—C3 | 1.399 (2) | C10—C11 | 1.537 (3) |
C2—H2 | 0.9500 | C10—H10A | 0.9900 |
C3—C4 | 1.407 (2) | C10—H10B | 0.9900 |
C3—C6 | 1.452 (2) | C11—C14 | 1.501 (2) |
C4—C5 | 1.395 (7) | C11—C12 | 1.537 (2) |
C4—S1' | 1.676 (2) | C11—H11 | 1.0000 |
C4—H4 | 0.9500 | C12—C13 | 1.542 (2) |
C5—H5 | 0.9500 | C12—H12A | 0.9900 |
C6—C7 | 1.335 (2) | C12—H12B | 0.9900 |
C6—H6 | 0.9500 | C13—H13A | 0.9900 |
C7—N8 | 1.4456 (19) | C13—H13B | 0.9900 |
C7—C14 | 1.483 (2) | C14—O15 | 1.2255 (19) |
C2—S1—C5 | 89.3 (2) | N8—C9—H9A | 109.2 |
C2—C5'—S1' | 114.7 (7) | C10—C9—H9A | 109.2 |
C2—C5'—H5' | 122.7 | N8—C9—H9B | 109.2 |
S1'—C5'—H5' | 122.7 | C10—C9—H9B | 109.2 |
C3—C2—C5' | 109.0 (4) | H9A—C9—H9B | 107.9 |
C3—C2—S1 | 116.65 (17) | C11—C10—C9 | 108.16 (14) |
C5'—C2—S1 | 7.7 (5) | C11—C10—H10A | 110.1 |
C3—C2—H2 | 121.7 | C9—C10—H10A | 110.1 |
C5'—C2—H2 | 129.3 | C11—C10—H10B | 110.1 |
S1—C2—H2 | 121.7 | C9—C10—H10B | 110.1 |
C2—C3—C4 | 111.30 (15) | H10A—C10—H10B | 108.4 |
C2—C3—C6 | 121.44 (15) | C14—C11—C10 | 108.21 (15) |
C4—C3—C6 | 127.22 (15) | C14—C11—C12 | 106.92 (14) |
C5—C4—C3 | 107.6 (3) | C10—C11—C12 | 108.34 (15) |
C5—C4—S1' | 8.1 (4) | C14—C11—H11 | 111.1 |
C3—C4—S1' | 115.59 (15) | C10—C11—H11 | 111.1 |
C5—C4—H4 | 126.2 | C12—C11—H11 | 111.1 |
C3—C4—H4 | 126.2 | C11—C12—C13 | 108.51 (14) |
S1'—C4—H4 | 118.2 | C11—C12—H12A | 110.0 |
C4—C5—S1 | 115.2 (4) | C13—C12—H12A | 110.0 |
C4—C5—H5 | 122.4 | C11—C12—H12B | 110.0 |
S1—C5—H5 | 122.4 | C13—C12—H12B | 110.0 |
C4—S1'—C5' | 89.4 (4) | H12A—C12—H12B | 108.4 |
C7—C6—C3 | 129.04 (15) | N8—C13—C12 | 111.86 (13) |
C7—C6—H6 | 115.5 | N8—C13—H13A | 109.2 |
C3—C6—H6 | 115.5 | C12—C13—H13A | 109.2 |
C6—C7—N8 | 124.03 (15) | N8—C13—H13B | 109.2 |
C6—C7—C14 | 122.43 (14) | C12—C13—H13B | 109.2 |
N8—C7—C14 | 113.26 (13) | H13A—C13—H13B | 107.9 |
C7—N8—C13 | 107.99 (12) | O15—C14—C7 | 124.81 (16) |
C7—N8—C9 | 108.39 (13) | O15—C14—C11 | 124.58 (16) |
C13—N8—C9 | 108.48 (14) | C7—C14—C11 | 110.58 (13) |
N8—C9—C10 | 112.07 (14) | ||
S1'—C5'—C2—C3 | −1.1 (10) | C6—C7—N8—C13 | 112.28 (17) |
S1'—C5'—C2—S1 | 173 (6) | C14—C7—N8—C13 | −61.85 (17) |
C5—S1—C2—C3 | 1.2 (4) | C6—C7—N8—C9 | −130.39 (17) |
C5—S1—C2—C5' | −5 (5) | C14—C7—N8—C9 | 55.48 (17) |
C5'—C2—C3—C4 | 0.2 (6) | C7—N8—C9—C10 | −60.80 (19) |
S1—C2—C3—C4 | −0.7 (2) | C13—N8—C9—C10 | 56.22 (19) |
C5'—C2—C3—C6 | 178.3 (6) | N8—C9—C10—C11 | 5.4 (2) |
S1—C2—C3—C6 | 177.40 (19) | C9—C10—C11—C14 | 53.67 (19) |
C2—C3—C4—C5 | −0.4 (4) | C9—C10—C11—C12 | −61.91 (19) |
C6—C3—C4—C5 | −178.3 (4) | C14—C11—C12—C13 | −60.59 (18) |
C2—C3—C4—S1' | 0.7 (2) | C10—C11—C12—C13 | 55.84 (18) |
C6—C3—C4—S1' | −177.21 (15) | C7—N8—C13—C12 | 54.49 (18) |
C3—C4—C5—S1 | 1.2 (7) | C9—N8—C13—C12 | −62.79 (17) |
S1'—C4—C5—S1 | −172 (4) | C11—C12—C13—N8 | 5.7 (2) |
C2—S1—C5—C4 | −1.4 (6) | C6—C7—C14—O15 | 8.8 (3) |
C5—C4—S1'—C5' | 6 (3) | N8—C7—C14—O15 | −176.96 (15) |
C3—C4—S1'—C5' | −1.1 (5) | C6—C7—C14—C11 | −169.17 (15) |
C2—C5'—S1'—C4 | 1.3 (9) | N8—C7—C14—C11 | 5.06 (18) |
C2—C3—C6—C7 | −164.64 (16) | C10—C11—C14—O15 | 121.19 (18) |
C4—C3—C6—C7 | 13.1 (3) | C12—C11—C14—O15 | −122.30 (18) |
C3—C6—C7—N8 | −0.2 (3) | C10—C11—C14—C7 | −60.82 (17) |
C3—C6—C7—C14 | 173.45 (15) | C12—C11—C14—C7 | 55.69 (18) |