Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805023901/fl6178sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805023901/fl6178Isup2.hkl |
CCDC reference: 282350
Key indicators
- Single-crystal X-ray study
- T = 300 K
- Mean (C-C) = 0.004 Å
- R factor = 0.047
- wR factor = 0.145
- Data-to-parameter ratio = 13.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.78 mm PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Oxford Diffraction, 2002); cell refinement: CrysAlis RED (Oxford Diffraction, 2002); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON2002 (Spek, 1990, 2003) and ORTEP-3 for Windows (Farrugia, 1997, 2005); software used to prepare material for publication: SHELXL97.
C12H12O2S2 | F(000) = 528 |
Mr = 252.34 | Dx = 1.403 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.287 (6) Å | Cell parameters from 703 reflections |
b = 11.606 (6) Å | θ = 2.9–19.1° |
c = 9.864 (6) Å | µ = 0.43 mm−1 |
β = 112.39 (7)° | T = 300 K |
V = 1194.7 (11) Å3 | Prism, yellow |
Z = 4 | 0.78 × 0.76 × 0.42 mm |
Oxford Diffraction Xcalibur with Sapphire CCD detector diffractometer | 2426 independent reflections |
Radiation source: fine-focus sealed tube | 1561 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.042 |
rotation method data acquisition using ω scans | θmax = 26.4°, θmin = 4.1° |
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2002) | h = −9→14 |
Tmin = 0.718, Tmax = 0.881 | k = −14→14 |
6892 measured reflections | l = −12→11 |
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)] = 0.047 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.145 | Only H-atom coordinates refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0844P)2] where P = (Fo2 + 2Fc2)/3 |
2426 reflections | (Δ/σ)max = 0.010 |
182 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.29 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 | ||
C1 | 0.3052 (2) | 0.4960 (2) | 0.2047 (2) | 0.0589 (6) | |
C2 | 0.4466 (3) | 0.3585 (4) | 0.3647 (4) | 0.0836 (10) | |
H11A | 0.458 (3) | 0.309 (3) | 0.298 (4) | 0.100* | |
H11B | 0.510 (3) | 0.421 (3) | 0.397 (4) | 0.100* | |
C3 | 0.4493 (4) | 0.2894 (4) | 0.4885 (4) | 0.0923 (11) | |
H12A | 0.524 (3) | 0.259 (3) | 0.527 (4) | 0.111* | |
H12B | 0.429 (3) | 0.341 (3) | 0.561 (4) | 0.111* | |
H12C | 0.377 (4) | 0.238 (3) | 0.457 (4) | 0.111* | |
C4 | 0.0731 (2) | 0.5027 (2) | 0.2535 (3) | 0.0516 (6) | |
H1 | −0.004 (2) | 0.544 (2) | 0.220 (3) | 0.062* | |
C5 | 0.0457 (3) | 0.3743 (2) | 0.2375 (3) | 0.0566 (6) | |
H2A | −0.040 (2) | 0.359 (2) | 0.204 (3) | 0.068* | |
H2B | 0.081 (2) | 0.338 (2) | 0.174 (3) | 0.068* | |
C6 | 0.0989 (2) | 0.3255 (2) | 0.3895 (3) | 0.0547 (6) | |
C7 | 0.1479 (2) | 0.42054 (18) | 0.4922 (3) | 0.0490 (5) | |
C8 | 0.1366 (2) | 0.52186 (19) | 0.4157 (2) | 0.0475 (6) | |
C9 | 0.1816 (2) | 0.6229 (2) | 0.4911 (3) | 0.0649 (7) | |
H8 | 0.175 (3) | 0.691 (3) | 0.443 (3) | 0.078* | |
C10 | 0.2338 (3) | 0.6197 (3) | 0.6407 (3) | 0.0741 (8) | |
H7 | 0.267 (3) | 0.693 (3) | 0.691 (3) | 0.089* | |
C11 | 0.2436 (3) | 0.5187 (3) | 0.7161 (3) | 0.0739 (8) | |
H6 | 0.276 (3) | 0.519 (2) | 0.824 (3) | 0.089* | |
C12 | 0.2009 (3) | 0.4190 (3) | 0.6425 (3) | 0.0647 (7) | |
H5 | 0.206 (3) | 0.353 (2) | 0.691 (3) | 0.078* | |
O1 | 0.32358 (15) | 0.41718 (15) | 0.30607 (18) | 0.0619 (5) | |
O2 | 0.1003 (2) | 0.22494 (16) | 0.4202 (2) | 0.0847 (6) | |
S1 | 0.40507 (8) | 0.53620 (9) | 0.13130 (9) | 0.0953 (4) | |
S2 | 0.15805 (7) | 0.56180 (6) | 0.14667 (7) | 0.0664 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0612 (15) | 0.0752 (16) | 0.0373 (12) | −0.0107 (13) | 0.0154 (11) | −0.0027 (12) |
C2 | 0.0693 (19) | 0.111 (3) | 0.072 (2) | 0.0316 (18) | 0.0295 (17) | 0.0057 (18) |
C3 | 0.090 (2) | 0.107 (3) | 0.074 (2) | 0.043 (2) | 0.0237 (19) | 0.0164 (19) |
C4 | 0.0467 (12) | 0.0535 (14) | 0.0528 (14) | 0.0067 (11) | 0.0169 (11) | 0.0069 (11) |
C5 | 0.0560 (14) | 0.0588 (16) | 0.0536 (15) | −0.0063 (12) | 0.0193 (12) | −0.0062 (11) |
C6 | 0.0593 (14) | 0.0535 (15) | 0.0556 (14) | −0.0068 (11) | 0.0269 (12) | 0.0001 (11) |
C7 | 0.0470 (12) | 0.0536 (14) | 0.0499 (13) | −0.0015 (10) | 0.0224 (11) | −0.0021 (10) |
C8 | 0.0439 (12) | 0.0488 (13) | 0.0486 (13) | 0.0068 (10) | 0.0164 (10) | −0.0028 (10) |
C9 | 0.0657 (16) | 0.0483 (15) | 0.0764 (19) | 0.0068 (12) | 0.0222 (15) | −0.0092 (13) |
C10 | 0.0663 (17) | 0.078 (2) | 0.072 (2) | 0.0036 (15) | 0.0195 (15) | −0.0289 (16) |
C11 | 0.0623 (17) | 0.105 (2) | 0.0512 (16) | 0.0027 (16) | 0.0177 (14) | −0.0187 (17) |
C12 | 0.0664 (16) | 0.080 (2) | 0.0490 (15) | 0.0013 (14) | 0.0236 (13) | 0.0035 (13) |
O1 | 0.0549 (10) | 0.0800 (12) | 0.0545 (10) | 0.0144 (8) | 0.0251 (8) | 0.0143 (9) |
O2 | 0.1195 (17) | 0.0517 (11) | 0.0822 (14) | −0.0181 (10) | 0.0373 (12) | 0.0041 (9) |
S1 | 0.0829 (6) | 0.1464 (9) | 0.0669 (5) | −0.0268 (5) | 0.0400 (5) | 0.0037 (5) |
S2 | 0.0695 (5) | 0.0711 (5) | 0.0534 (4) | 0.0009 (3) | 0.0174 (3) | 0.0206 (3) |
C1—O1 | 1.312 (3) | C5—H2A | 0.92 (2) |
C1—S1 | 1.624 (3) | C5—H2B | 0.96 (2) |
C1—S2 | 1.716 (3) | C6—O2 | 1.204 (3) |
C2—C3 | 1.451 (5) | C6—C7 | 1.457 (3) |
C2—O1 | 1.455 (3) | C7—C12 | 1.371 (4) |
C2—H11A | 0.92 (3) | C7—C8 | 1.376 (3) |
C2—H11B | 0.99 (3) | C8—C9 | 1.378 (3) |
C3—H12A | 0.85 (3) | C9—C10 | 1.365 (4) |
C3—H12B | 1.03 (4) | C9—H8 | 0.91 (3) |
C3—H12C | 0.96 (3) | C10—C11 | 1.370 (5) |
C4—C8 | 1.500 (3) | C10—H7 | 0.99 (3) |
C4—C5 | 1.518 (4) | C11—C12 | 1.353 (4) |
C4—S2 | 1.808 (3) | C11—H6 | 0.98 (3) |
C4—H1 | 0.94 (2) | C12—H5 | 0.89 (3) |
C5—C6 | 1.498 (4) | ||
O1—C1—S1 | 127.2 (2) | C4—C5—H2B | 112.0 (15) |
O1—C1—S2 | 114.66 (18) | H2A—C5—H2B | 109 (2) |
S1—C1—S2 | 118.13 (16) | O2—C6—C7 | 126.4 (2) |
C3—C2—O1 | 107.7 (3) | O2—C6—C5 | 125.4 (2) |
C3—C2—H11A | 107 (2) | C7—C6—C5 | 108.1 (2) |
O1—C2—H11A | 112 (2) | C12—C7—C8 | 121.0 (2) |
C3—C2—H11B | 111 (2) | C12—C7—C6 | 129.5 (2) |
O1—C2—H11B | 104.6 (19) | C8—C7—C6 | 109.5 (2) |
H11A—C2—H11B | 114 (3) | C7—C8—C9 | 119.6 (2) |
C2—C3—H12A | 107 (2) | C7—C8—C4 | 111.4 (2) |
C2—C3—H12B | 109.1 (18) | C9—C8—C4 | 129.0 (2) |
H12A—C3—H12B | 112 (3) | C10—C9—C8 | 118.6 (3) |
C2—C3—H12C | 109 (2) | C10—C9—H8 | 120.1 (18) |
H12A—C3—H12C | 118 (3) | C8—C9—H8 | 121.3 (18) |
H12B—C3—H12C | 101 (3) | C9—C10—C11 | 121.5 (3) |
C8—C4—C5 | 104.63 (19) | C9—C10—H7 | 116.5 (17) |
C8—C4—S2 | 114.94 (17) | C11—C10—H7 | 121.9 (17) |
C5—C4—S2 | 116.39 (17) | C12—C11—C10 | 120.1 (3) |
C8—C4—H1 | 107.8 (16) | C12—C11—H6 | 119.4 (18) |
C5—C4—H1 | 109.9 (14) | C10—C11—H6 | 120.4 (18) |
S2—C4—H1 | 102.9 (15) | C11—C12—C7 | 119.2 (3) |
C6—C5—C4 | 106.2 (2) | C11—C12—H5 | 120.8 (19) |
C6—C5—H2A | 104.7 (17) | C7—C12—H5 | 120.0 (19) |
C4—C5—H2A | 112.1 (16) | C1—O1—C2 | 118.7 (2) |
C6—C5—H2B | 112.4 (15) | C1—S2—C4 | 107.27 (12) |
C8—C4—C5—C6 | −2.2 (2) | S2—C4—C8—C9 | 51.1 (3) |
S2—C4—C5—C6 | 125.82 (19) | C7—C8—C9—C10 | −1.5 (4) |
C4—C5—C6—O2 | −176.4 (2) | C4—C8—C9—C10 | 178.5 (2) |
C4—C5—C6—C7 | 3.6 (3) | C8—C9—C10—C11 | 0.9 (4) |
O2—C6—C7—C12 | −2.6 (4) | C9—C10—C11—C12 | −0.1 (5) |
C5—C6—C7—C12 | 177.3 (3) | C10—C11—C12—C7 | 0.0 (4) |
O2—C6—C7—C8 | 176.3 (2) | C8—C7—C12—C11 | −0.6 (4) |
C5—C6—C7—C8 | −3.8 (3) | C6—C7—C12—C11 | 178.2 (2) |
C12—C7—C8—C9 | 1.4 (4) | S1—C1—O1—C2 | 1.4 (4) |
C6—C7—C8—C9 | −177.6 (2) | S2—C1—O1—C2 | −178.6 (2) |
C12—C7—C8—C4 | −178.6 (2) | C3—C2—O1—C1 | 171.6 (3) |
C6—C7—C8—C4 | 2.4 (3) | O1—C1—S2—C4 | 2.2 (2) |
C5—C4—C8—C7 | 0.0 (3) | S1—C1—S2—C4 | −177.74 (14) |
S2—C4—C8—C7 | −128.94 (19) | C8—C4—S2—C1 | 60.7 (2) |
C5—C4—C8—C9 | 180.0 (2) | C5—C4—S2—C1 | −62.1 (2) |