Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806020538/hk2046sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806020538/hk2046Isup2.hkl |
CCDC reference: 613716
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.056
- wR factor = 0.158
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 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 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: STADI4 (Stoe & Cie, 1996); cell refinement: STADI4; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
C14H14O2S2 | F(000) = 584 |
Mr = 278.37 | Dx = 1.387 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 25 reflections |
a = 18.106 (6) Å | θ = 9.5–10.7° |
b = 8.936 (3) Å | µ = 0.39 mm−1 |
c = 9.300 (3) Å | T = 298 K |
β = 117.60 (3)° | Prism, colorless |
V = 1333.5 (8) Å3 | 0.53 × 0.31 × 0.19 mm |
Z = 4 |
Stoe Stadi-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 27.4°, θmin = 2.5° |
Graphite monochromator | h = −23→20 |
ω/2θ scans | k = 0→11 |
1526 measured reflections | l = 0→12 |
1526 independent reflections | 3 standard reflections every 60 min |
1138 reflections with I > 2σ(I) | intensity decay: 2.8% |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.158 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0696P)2 + 2.3312P] where P = (Fo2 + 2Fc2)/3 |
1526 reflections | (Δ/σ)max < 0.001 |
82 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.39 e Å−3 |
Experimental. 1H NMR (400 MHz, CDCl3, p.p.m.): δ 2.43 (s, 6H), 2.62 (s, 6H), 7.30 (s, 2H); 13C NMR (100 MHz, CDCl3, p.p.m.): δ 12.65, 22.05, 106.99, 108.97, 122.28, 150.80, 159.67. |
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 | ||
S | 0.41220 (5) | 0.15576 (9) | 0.28877 (10) | 0.0482 (3) | |
O | 0.37281 (17) | 0.5831 (3) | 0.3258 (3) | 0.0668 (8) | |
C1 | 0.41243 (18) | 0.3519 (3) | 0.2936 (3) | 0.0417 (6) | |
C2 | 0.3586 (2) | 0.4317 (4) | 0.3275 (4) | 0.0562 (9) | |
C3 | 0.4370 (2) | 0.6003 (4) | 0.2874 (4) | 0.0553 (9) | |
C4 | 0.46634 (19) | 0.4591 (3) | 0.2692 (3) | 0.0430 (7) | |
C5 | 0.3658 (2) | 0.1239 (4) | 0.0728 (4) | 0.0572 (9) | |
H5A | 0.3618 | 0.0182 | 0.0518 | 0.069* | |
H5B | 0.3999 | 0.1690 | 0.0305 | 0.069* | |
H5C | 0.3112 | 0.1675 | 0.0211 | 0.069* | |
C6 | 0.2903 (2) | 0.3892 (6) | 0.3645 (5) | 0.0768 (13) | |
H6A | 0.2854 | 0.2822 | 0.3629 | 0.092* | |
H6B | 0.2389 | 0.4317 | 0.2846 | 0.092* | |
H6C | 0.3022 | 0.4262 | 0.4700 | 0.092* | |
C7 | 0.4683 (3) | 0.7367 (4) | 0.2707 (5) | 0.0730 (13) | |
H7 | 0.4469 | 0.8259 | 0.2870 | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0574 (5) | 0.0431 (4) | 0.0508 (5) | −0.0023 (4) | 0.0307 (4) | 0.0047 (3) |
O | 0.0755 (17) | 0.0634 (16) | 0.0521 (14) | 0.0303 (14) | 0.0217 (13) | −0.0078 (12) |
C1 | 0.0390 (14) | 0.0437 (15) | 0.0337 (13) | 0.0063 (13) | 0.0093 (11) | −0.0028 (12) |
C2 | 0.0560 (19) | 0.064 (2) | 0.0418 (17) | 0.0155 (17) | 0.0172 (15) | −0.0057 (15) |
C3 | 0.071 (2) | 0.0382 (16) | 0.0412 (16) | 0.0074 (16) | 0.0126 (16) | −0.0087 (13) |
C4 | 0.0546 (17) | 0.0322 (14) | 0.0335 (14) | 0.0052 (13) | 0.0131 (13) | −0.0002 (11) |
C5 | 0.068 (2) | 0.0516 (19) | 0.0544 (19) | −0.0099 (16) | 0.0301 (18) | −0.0062 (15) |
C6 | 0.053 (2) | 0.121 (4) | 0.058 (2) | 0.022 (2) | 0.0269 (18) | −0.008 (2) |
C7 | 0.105 (4) | 0.0343 (16) | 0.054 (2) | 0.0117 (17) | 0.015 (2) | −0.0045 (15) |
S—C1 | 1.753 (3) | C4—C4i | 1.420 (6) |
S—C5 | 1.805 (4) | C5—H5A | 0.9600 |
O—C3 | 1.374 (5) | C5—H5B | 0.9600 |
O—C2 | 1.379 (5) | C5—H5C | 0.9600 |
C1—C2 | 1.356 (4) | C6—H6A | 0.9600 |
C1—C4 | 1.459 (4) | C6—H6B | 0.9600 |
C2—C6 | 1.479 (5) | C6—H6C | 0.9600 |
C3—C7 | 1.382 (5) | C7—C7i | 1.368 (9) |
C3—C4 | 1.409 (4) | C7—H7 | 0.9300 |
C1—S—C5 | 100.4 (2) | S—C5—H5B | 109.5 |
C3—O—C2 | 107.3 (2) | H5A—C5—H5B | 109.5 |
C2—C1—C4 | 107.2 (3) | S—C5—H5C | 109.5 |
C2—C1—S | 122.5 (3) | H5A—C5—H5C | 109.5 |
C4—C1—S | 130.3 (2) | H5B—C5—H5C | 109.5 |
C1—C2—O | 110.8 (3) | C2—C6—H6A | 109.5 |
C1—C2—C6 | 133.4 (4) | C2—C6—H6B | 109.5 |
O—C2—C6 | 115.8 (3) | H6A—C6—H6B | 109.5 |
O—C3—C7 | 124.6 (3) | C2—C6—H6C | 109.5 |
O—C3—C4 | 110.0 (3) | H6A—C6—H6C | 109.5 |
C7—C3—C4 | 125.4 (4) | H6B—C6—H6C | 109.5 |
C3—C4—C4i | 116.4 (2) | C7i—C7—C3 | 118.2 (2) |
C3—C4—C1 | 104.6 (3) | C7i—C7—H7 | 120.9 |
C4i—C4—C1 | 138.9 (2) | C3—C7—H7 | 120.9 |
S—C5—H5A | 109.5 | ||
C1—C2—O—C3 | 0.8 (2) | C3—C4—C1—C2 | −1.6 (3) |
C2—O—C3—C4 | −1.9 (3) | C4—C1—C2—O | 0.5 (2) |
O—C3—C4—C1 | 2.1 (2) |
Symmetry code: (i) −x+1, y, −z+1/2. |