Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802008528/cm6005sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802008528/cm6005Isup2.hkl |
CCDC reference: 189401
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.063
- wR factor = 0.194
- Data-to-parameter ratio = 12.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5882 General Notes
CELLZ_01 From the CIF: _cell_formula_units_Z 8 From the CIF: _chemical_formula_sum C10 H8 O2 S2 TEST: Compare cell contents of formula and atom_site data atom Z*formula cif sites diff C 80.00 80.03 -0.03 H 64.00 64.02 -0.02 O 16.00 16.00 0.00 S 16.00 16.01 -0.01 Difference between formula and atom_site contents detected. ALERT: check formula stoichiometry or atom site occupancies.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SHELXTL-Plus (Sheldrick, 1990); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.
C10H8O2S2 | Dx = 1.489 Mg m−3 |
Mr = 224.28 | Melting point: 108-109° K |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.2503 (17) Å | Cell parameters from 12182 reflections |
b = 16.421 (3) Å | θ = 1.9–24.7° |
c = 15.041 (3) Å | µ = 0.50 mm−1 |
β = 100.86 (3)° | T = 293 K |
V = 2001.2 (7) Å3 | Needle, colorless |
Z = 8 | 0.3 × 0.1 × 0.05 mm |
F(000) = 928 |
Siemens SMART P3/512CCD diffractometer | 2086 reflections with I > 2s(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 24.7°, θmin = 1.9° |
ω scans | h = −9→9 |
11939 measured reflections | k = −19→19 |
3412 independent reflections | l = −17→17 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.194 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.1P)2] where = P = (Fo2 + 2Fc2)/3 |
3412 reflections | (Δ/σ)max = 0.007 |
269 parameters | Δρmax = 0.34 e Å−3 |
22 restraints | Δρmin = −0.35 e Å−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) | |
S1A | 0.0763 (2) | 0.26808 (12) | 0.1338 (2) | 0.0753 (7) | 0.890 (5) |
C2A | 0.2432 (5) | 0.2116 (3) | 0.1261 (3) | 0.0576 (12) | 0.890 (5) |
H2AA | 0.2486 | 0.1554 | 0.1340 | 0.069* | 0.890 (5) |
C3A | 0.3703 (5) | 0.2579 (2) | 0.1067 (2) | 0.0415 (10) | 0.890 (5) |
C4A | 0.3281 (6) | 0.3406 (3) | 0.0977 (3) | 0.0603 (13) | 0.890 (5) |
H4AA | 0.3997 | 0.3810 | 0.0853 | 0.072* | 0.890 (5) |
C5A | 0.1709 (14) | 0.3555 (6) | 0.1093 (8) | 0.069 (3) | 0.890 (5) |
H5AA | 0.1216 | 0.4066 | 0.1045 | 0.083* | 0.890 (5) |
S1B | 0.142 (3) | 0.3573 (15) | 0.124 (2) | 0.0753 (7) | 0.111 (5) |
C2B | 0.3281 (6) | 0.3406 (3) | 0.0977 (3) | 0.0603 (13) | 0.111 (5) |
H2BA | 0.3943 | 0.3808 | 0.0796 | 0.072* | 0.111 (5) |
C3B | 0.3703 (5) | 0.2579 (2) | 0.1067 (2) | 0.0415 (10) | 0.111 (5) |
C4B | 0.2432 (5) | 0.2116 (3) | 0.1261 (3) | 0.0576 (12) | 0.111 (5) |
H4BA | 0.2484 | 0.1552 | 0.1312 | 0.069* | 0.111 (5) |
C5B | 0.109 (6) | 0.256 (2) | 0.137 (7) | 0.069 (3) | 0.111 (5) |
H5BA | 0.0121 | 0.2335 | 0.1499 | 0.083* | 0.111 (5) |
S4A | 0.8768 (4) | 0.53846 (15) | 0.11860 (11) | 0.0674 (7) | 0.856 (4) |
C17A | 0.9452 (5) | 0.5456 (3) | 0.2321 (3) | 0.0548 (12) | 0.856 (4) |
H17A | 1.0146 | 0.5866 | 0.2596 | 0.066* | 0.856 (4) |
C18A | 0.8865 (4) | 0.4840 (2) | 0.2783 (3) | 0.0392 (10) | 0.856 (4) |
C19A | 0.7848 (5) | 0.4306 (2) | 0.2189 (3) | 0.0468 (11) | 0.856 (4) |
H19A | 0.7360 | 0.3848 | 0.2389 | 0.056* | 0.856 (4) |
C20A | 0.7636 (13) | 0.4515 (6) | 0.1295 (5) | 0.049 (2) | 0.856 (4) |
H20A | 0.6987 | 0.4234 | 0.0820 | 0.059* | 0.856 (4) |
S4B | 0.772 (3) | 0.4614 (15) | 0.1093 (10) | 0.0674 (7) | 0.145 (4) |
C17B | 0.7848 (5) | 0.4306 (2) | 0.2189 (3) | 0.0468 (11) | 0.145 (4) |
H17B | 0.7321 | 0.3851 | 0.2368 | 0.056* | 0.145 (4) |
C18B | 0.8865 (4) | 0.4840 (2) | 0.2783 (3) | 0.0392 (10) | 0.145 (4) |
C19B | 0.9452 (5) | 0.5456 (3) | 0.2321 (3) | 0.0548 (12) | 0.145 (4) |
H19B | 1.0142 | 0.5858 | 0.2618 | 0.066* | 0.145 (4) |
C20B | 0.898 (8) | 0.545 (3) | 0.1406 (14) | 0.049 (2) | 0.145 (4) |
H20B | 0.9277 | 0.5835 | 0.1012 | 0.059* | 0.145 (4) |
C1 | 0.5301 (5) | 0.2269 (2) | 0.0935 (2) | 0.0400 (10) | |
O1 | 0.6288 (4) | 0.26981 (17) | 0.0638 (2) | 0.0553 (8) | |
C6 | 0.5779 (5) | 0.1398 (2) | 0.1190 (3) | 0.0414 (10) | |
H6A | 0.4872 | 0.1036 | 0.0925 | 0.050* | |
O2 | 0.7224 (4) | 0.11864 (17) | 0.0842 (2) | 0.0586 (8) | |
H2A | 0.6966 | 0.0885 | 0.0403 | 0.088* | |
S2 | 0.61484 (16) | 0.07675 (8) | 0.37966 (8) | 0.0619 (4) | |
C7 | 0.5485 (5) | 0.0702 (2) | 0.2660 (3) | 0.0464 (11) | |
H7A | 0.4769 | 0.0301 | 0.2382 | 0.056* | |
C8 | 0.6116 (5) | 0.1299 (2) | 0.2201 (3) | 0.0374 (9) | |
C9 | 0.7170 (5) | 0.1831 (2) | 0.2809 (3) | 0.0460 (10) | |
H9A | 0.7704 | 0.2279 | 0.2620 | 0.055* | |
C10 | 0.7306 (5) | 0.1611 (3) | 0.3686 (3) | 0.0492 (11) | |
H10A | 0.7948 | 0.1885 | 0.4169 | 0.059* | |
C11 | 0.9785 (5) | 0.3886 (2) | 0.4042 (3) | 0.0420 (10) | |
O3 | 0.8874 (4) | 0.34420 (18) | 0.4366 (2) | 0.0591 (8) | |
S3 | 1.42651 (16) | 0.35210 (11) | 0.35236 (10) | 0.0824 (5) | |
C12 | 1.2630 (5) | 0.4071 (3) | 0.3690 (3) | 0.0622 (13) | |
H12A | 1.2590 | 0.4637 | 0.3670 | 0.075* | |
C13 | 1.1374 (5) | 0.3596 (3) | 0.3855 (2) | 0.0409 (10) | |
C14 | 1.1791 (5) | 0.2756 (3) | 0.3858 (3) | 0.0543 (12) | |
H14A | 1.1092 | 0.2342 | 0.3977 | 0.065* | |
C15 | 1.3346 (5) | 0.2617 (3) | 0.3666 (3) | 0.0497 (11) | |
H15A | 1.3815 | 0.2107 | 0.3622 | 0.060* | |
C16 | 0.9245 (5) | 0.4760 (2) | 0.3789 (3) | 0.0434 (10) | |
H16A | 1.0146 | 0.5133 | 0.4034 | 0.052* | |
O4 | 0.7839 (4) | 0.49583 (18) | 0.41610 (19) | 0.0616 (9) | |
H4A | 0.7776 | 0.4646 | 0.4579 | 0.092* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1A | 0.0465 (10) | 0.1006 (16) | 0.0805 (12) | 0.0124 (9) | 0.0166 (10) | −0.0003 (12) |
C2A | 0.054 (3) | 0.055 (3) | 0.063 (3) | 0.000 (2) | 0.010 (2) | −0.001 (2) |
C3A | 0.041 (2) | 0.047 (3) | 0.036 (2) | 0.002 (2) | 0.0060 (18) | −0.0006 (18) |
C4A | 0.057 (3) | 0.048 (3) | 0.076 (3) | 0.011 (2) | 0.015 (2) | 0.003 (2) |
C5A | 0.077 (7) | 0.063 (4) | 0.070 (6) | 0.026 (4) | 0.020 (4) | 0.005 (3) |
S1B | 0.0465 (10) | 0.1006 (16) | 0.0805 (12) | 0.0124 (9) | 0.0166 (10) | −0.0003 (12) |
C2B | 0.057 (3) | 0.048 (3) | 0.076 (3) | 0.011 (2) | 0.015 (2) | 0.003 (2) |
C3B | 0.041 (2) | 0.047 (3) | 0.036 (2) | 0.002 (2) | 0.0060 (18) | −0.0006 (18) |
C4B | 0.054 (3) | 0.055 (3) | 0.063 (3) | 0.000 (2) | 0.010 (2) | −0.001 (2) |
C5B | 0.077 (7) | 0.063 (4) | 0.070 (6) | 0.026 (4) | 0.020 (4) | 0.005 (3) |
S4A | 0.0791 (16) | 0.0668 (13) | 0.0583 (11) | 0.0088 (9) | 0.0179 (11) | 0.0202 (10) |
C17A | 0.061 (3) | 0.045 (3) | 0.058 (3) | −0.004 (2) | 0.010 (2) | 0.003 (2) |
C18A | 0.035 (2) | 0.034 (2) | 0.048 (2) | 0.0060 (18) | 0.0081 (18) | 0.0024 (19) |
C19A | 0.046 (3) | 0.044 (3) | 0.050 (3) | −0.001 (2) | 0.009 (2) | −0.004 (2) |
C20A | 0.042 (3) | 0.049 (5) | 0.058 (5) | −0.004 (3) | 0.011 (4) | −0.009 (4) |
S4B | 0.0791 (16) | 0.0668 (13) | 0.0583 (11) | 0.0088 (9) | 0.0179 (11) | 0.0202 (10) |
C17B | 0.046 (3) | 0.044 (3) | 0.050 (3) | −0.001 (2) | 0.009 (2) | −0.004 (2) |
C18B | 0.035 (2) | 0.034 (2) | 0.048 (2) | 0.0060 (18) | 0.0081 (18) | 0.0024 (19) |
C19B | 0.061 (3) | 0.045 (3) | 0.058 (3) | −0.004 (2) | 0.010 (2) | 0.003 (2) |
C20B | 0.042 (3) | 0.049 (5) | 0.058 (5) | −0.004 (3) | 0.011 (4) | −0.009 (4) |
C1 | 0.045 (2) | 0.040 (2) | 0.035 (2) | 0.002 (2) | 0.0074 (19) | 0.0023 (18) |
O1 | 0.0530 (19) | 0.0459 (18) | 0.071 (2) | −0.0030 (15) | 0.0212 (16) | 0.0101 (15) |
C6 | 0.043 (2) | 0.037 (2) | 0.046 (2) | 0.0037 (19) | 0.0121 (19) | −0.0033 (18) |
O2 | 0.065 (2) | 0.055 (2) | 0.0620 (19) | 0.0152 (16) | 0.0281 (16) | −0.0029 (15) |
S2 | 0.0756 (9) | 0.0600 (8) | 0.0513 (8) | 0.0026 (7) | 0.0152 (6) | 0.0115 (6) |
C7 | 0.051 (3) | 0.032 (2) | 0.057 (3) | −0.0049 (19) | 0.013 (2) | 0.0006 (19) |
C8 | 0.037 (2) | 0.030 (2) | 0.047 (2) | 0.0071 (18) | 0.0137 (18) | 0.0011 (18) |
C9 | 0.045 (2) | 0.040 (3) | 0.055 (3) | −0.004 (2) | 0.014 (2) | −0.001 (2) |
C10 | 0.040 (2) | 0.050 (3) | 0.056 (3) | 0.004 (2) | 0.005 (2) | −0.007 (2) |
C11 | 0.043 (2) | 0.047 (3) | 0.037 (2) | 0.006 (2) | 0.0099 (19) | −0.0022 (19) |
O3 | 0.0587 (19) | 0.054 (2) | 0.072 (2) | 0.0069 (16) | 0.0310 (16) | 0.0145 (16) |
S3 | 0.0525 (8) | 0.1061 (12) | 0.0931 (11) | 0.0141 (8) | 0.0254 (7) | 0.0047 (9) |
C12 | 0.053 (3) | 0.060 (3) | 0.076 (3) | 0.002 (2) | 0.019 (2) | 0.007 (2) |
C13 | 0.038 (2) | 0.048 (3) | 0.036 (2) | 0.000 (2) | 0.0059 (18) | 0.0021 (18) |
C14 | 0.057 (3) | 0.043 (3) | 0.063 (3) | 0.008 (2) | 0.011 (2) | 0.001 (2) |
C15 | 0.047 (3) | 0.048 (3) | 0.053 (3) | 0.019 (2) | 0.008 (2) | −0.001 (2) |
C16 | 0.049 (3) | 0.038 (2) | 0.044 (2) | 0.0046 (19) | 0.0103 (19) | −0.0038 (18) |
O4 | 0.070 (2) | 0.062 (2) | 0.0587 (19) | 0.0252 (17) | 0.0269 (16) | 0.0074 (15) |
S1A—C5A | 1.707 (9) | C6—C8 | 1.501 (5) |
S1A—C2A | 1.683 (5) | C6—H6A | 0.9800 |
C2A—C3A | 1.370 (5) | O2—H2A | 0.8200 |
C2A—H2AA | 0.9300 | S2—C7 | 1.697 (4) |
C3A—C4A | 1.403 (5) | S2—C10 | 1.708 (4) |
C3A—C1 | 1.461 (5) | C7—C8 | 1.358 (5) |
C4A—C5A | 1.362 (10) | C7—H7A | 0.9300 |
C4A—H4AA | 0.9300 | C8—C9 | 1.434 (5) |
C5A—H5AA | 0.9300 | C9—C10 | 1.352 (6) |
S1B—C5B | 1.709 (19) | C9—H9A | 0.9300 |
C5B—H5BA | 0.9300 | C10—H10A | 0.9300 |
S4A—C17A | 1.698 (5) | C11—O3 | 1.214 (5) |
S4A—C20A | 1.731 (8) | C11—C13 | 1.471 (5) |
C17A—C18A | 1.366 (5) | C11—C16 | 1.529 (5) |
C17A—H17A | 0.9300 | S3—C12 | 1.681 (5) |
C18A—C19A | 1.410 (5) | S3—C15 | 1.699 (4) |
C18A—C16 | 1.492 (5) | C12—C13 | 1.357 (6) |
C19A—C20A | 1.366 (9) | C12—H12A | 0.9300 |
C19A—H19A | 0.9300 | C13—C14 | 1.422 (6) |
C20A—H20A | 0.9300 | C14—C15 | 1.386 (5) |
S4B—C20B | 1.732 (19) | C14—H14A | 0.9300 |
C20B—H20B | 0.9300 | C15—H15A | 0.9300 |
C1—O1 | 1.223 (4) | C16—O4 | 1.418 (5) |
C1—C6 | 1.515 (5) | C16—H16A | 0.9800 |
C6—O2 | 1.433 (4) | O4—H4A | 0.8200 |
C5A—S1A—C2A | 92.0 (4) | C6—O2—H2A | 109.5 |
C3A—C2A—S1A | 112.2 (3) | C7—S2—C10 | 91.9 (2) |
C3A—C2A—H2AA | 123.9 | C8—C7—S2 | 112.6 (3) |
S1A—C2A—H2AA | 123.9 | C8—C7—H7A | 123.7 |
C2A—C3A—C4A | 111.8 (4) | S2—C7—H7A | 123.7 |
C2A—C3A—C1 | 125.6 (4) | C7—C8—C9 | 111.1 (4) |
C4A—C3A—C1 | 122.5 (4) | C7—C8—C6 | 125.2 (4) |
C5A—C4A—C3A | 112.7 (6) | C9—C8—C6 | 123.7 (3) |
C5A—C4A—H4AA | 123.6 | C10—C9—C8 | 112.9 (4) |
C3A—C4A—H4AA | 123.6 | C10—C9—H9A | 123.6 |
C4A—C5A—S1A | 111.2 (6) | C8—C9—H9A | 123.6 |
C4A—C5A—H5AA | 124.4 | C9—C10—S2 | 111.5 (3) |
S1A—C5A—H5AA | 124.4 | C9—C10—H10A | 124.3 |
S1B—C5B—H5BA | 124.7 | S2—C10—H10A | 124.3 |
C17A—S4A—C20A | 92.5 (3) | O3—C11—C13 | 121.6 (4) |
C18A—C17A—S4A | 112.2 (3) | O3—C11—C16 | 119.4 (4) |
C18A—C17A—H17A | 123.9 | C13—C11—C16 | 119.0 (4) |
S4A—C17A—H17A | 123.9 | C12—S3—C15 | 93.5 (2) |
C17A—C18A—C19A | 111.3 (4) | C13—C12—S3 | 112.3 (4) |
C17A—C18A—C16 | 123.6 (3) | C13—C12—H12A | 123.9 |
C19A—C18A—C16 | 125.0 (4) | S3—C12—H12A | 123.9 |
C20A—C19A—C18A | 114.7 (5) | C12—C13—C14 | 111.5 (4) |
C20A—C19A—H19A | 122.7 | C12—C13—C11 | 125.9 (4) |
C18A—C19A—H19A | 122.7 | C14—C13—C11 | 122.5 (4) |
C19A—C20A—S4A | 109.2 (6) | C15—C14—C13 | 113.1 (4) |
C19A—C20A—H20A | 125.4 | C15—C14—H14A | 123.5 |
S4A—C20A—H20A | 125.4 | C13—C14—H14A | 123.5 |
S4B—C20B—H20B | 125.6 | C14—C15—S3 | 109.6 (3) |
O1—C1—C3A | 122.0 (4) | C14—C15—H15A | 125.2 |
O1—C1—C6 | 118.5 (4) | S3—C15—H15A | 125.2 |
C3A—C1—C6 | 119.5 (3) | O4—C16—C18A | 110.4 (3) |
O2—C6—C8 | 109.6 (3) | O4—C16—C11 | 109.8 (3) |
O2—C6—C1 | 109.3 (3) | C18A—C16—C11 | 109.3 (3) |
C8—C6—C1 | 110.4 (3) | O4—C16—H16A | 109.1 |
O2—C6—H6A | 109.1 | C18A—C16—H16A | 109.1 |
C8—C6—H6A | 109.1 | C11—C16—H16A | 109.1 |
C1—C6—H6A | 109.1 | C16—O4—H4A | 109.5 |
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