Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802013016/ob6150sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802013016/ob61502sup2.hkl |
CCDC reference: 193776
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.004 Å
- R factor = 0.033
- wR factor = 0.091
- Data-to-parameter ratio = 14.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C13H14Cl2O2S | F(000) = 632 |
Mr = 305.20 | Dx = 1.472 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.162 (4) Å | Cell parameters from 24 reflections |
b = 16.710 (11) Å | θ = 10–11° |
c = 13.403 (7) Å | µ = 0.61 mm−1 |
β = 93.58 (4)° | T = 173 K |
V = 1377.3 (14) Å3 | Squared prism, colorless |
Z = 4 | 0.50 × 0.30 × 0.30 mm |
Siemens P3 diffractometer | Rint = 0.044 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 2.0° |
Graphite monochromator | h = 0→7 |
θ/2θ scans | k = 0→19 |
2602 measured reflections | l = −15→15 |
2372 independent reflections | 2 standard reflections every 98 reflections |
1699 reflections with I > 2σ(I) | intensity decay: 3.2% |
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)] = 0.033 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.091 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0625P)2] where P = (Fo2 + 2Fc2)/3 |
2372 reflections | (Δ/σ)max < 0.001 |
163 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Experimental. Data for compound (2) 1H-NMR(CDCl3): δ (p.p.m)=1.49–1.82 m (2H, H4A,H4B), 2.08–3.43 m (4H, H3A,H3B and H5A,H5B), 3.30–3.40 m (2H, H2, H6), 5.51 m (1H, H7, J=5.7 Hz), 7.52–7.78 m (3H) and 7.90–8.02 m (2H, Harom.). 13C-NMR (CDCl3): δ (p.p.m) = 12.0 (C4), 25.4 (C3 and C5), 48.8 (C2 and C6), 54.2 (C7), 87.4 (C1), 128.6, 130.2, 134.8, 136.7 (C8—C13). Data for compound (3) 13C-NMR (CDCl3): δ (p.p.m) = 12.9 (C4), 22.8 (C3 and C5), 54.3 (C2 and C6), 56.0 (C7), 84.1 (C1), 128.6, 129.1, 133.8, 136.7 (C8—C13). 1H and 13C NMR spectra were recorded on a Bruker AC-300 spectrometer, 300 MHz. Column chromatography was conducted with Al2O3 (II activity grade), eluent: light petroleum ether / (CH3)2O (2:1). |
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 | ||
S1 | 0.21181 (8) | 0.62945 (3) | 0.22954 (3) | 0.03760 (15) | |
Cl1 | 0.14223 (9) | 0.48753 (3) | 0.11317 (4) | 0.05414 (18) | |
Cl2 | 0.71061 (12) | 0.44518 (5) | 0.41168 (6) | 0.0864 (3) | |
O1 | −0.0184 (2) | 0.62872 (9) | 0.23553 (12) | 0.0527 (4) | |
O2 | 0.3414 (3) | 0.66498 (9) | 0.30968 (11) | 0.0571 (4) | |
C1 | 0.2991 (3) | 0.52588 (11) | 0.21868 (14) | 0.0358 (4) | |
C2 | 0.2919 (3) | 0.48122 (12) | 0.32036 (15) | 0.0446 (5) | |
H2 | 0.1879 | 0.5033 | 0.3677 | 0.054* | |
C3 | 0.2772 (4) | 0.39123 (13) | 0.3021 (2) | 0.0585 (6) | |
H3A | 0.1285 | 0.3778 | 0.2750 | 0.070* | |
H3B | 0.3027 | 0.3629 | 0.3667 | 0.070* | |
C4 | 0.4424 (4) | 0.36123 (14) | 0.2290 (2) | 0.0651 (7) | |
H4A | 0.5373 | 0.3210 | 0.2639 | 0.078* | |
H4B | 0.3615 | 0.3337 | 0.1727 | 0.078* | |
C5 | 0.5873 (4) | 0.42551 (13) | 0.1857 (2) | 0.0580 (6) | |
H5A | 0.7415 | 0.4115 | 0.2021 | 0.070* | |
H5B | 0.5632 | 0.4256 | 0.1120 | 0.070* | |
C6 | 0.5451 (3) | 0.50958 (12) | 0.22478 (15) | 0.0429 (5) | |
H6 | 0.6377 | 0.5530 | 0.1987 | 0.052* | |
C7 | 0.5281 (4) | 0.50812 (14) | 0.33851 (17) | 0.0529 (6) | |
H7 | 0.5337 | 0.5639 | 0.3656 | 0.064* | |
C8 | 0.2730 (3) | 0.67785 (11) | 0.11791 (14) | 0.0393 (4) | |
C9 | 0.1114 (4) | 0.68692 (13) | 0.04310 (17) | 0.0525 (5) | |
H9 | −0.0271 | 0.6631 | 0.0492 | 0.063* | |
C10 | 0.1521 (5) | 0.73076 (16) | −0.04068 (19) | 0.0713 (8) | |
H10 | 0.0414 | 0.7375 | −0.0925 | 0.086* | |
C11 | 0.3512 (6) | 0.76439 (16) | −0.0490 (2) | 0.0775 (9) | |
H11 | 0.3776 | 0.7954 | −0.1065 | 0.093* | |
C12 | 0.5147 (5) | 0.75418 (14) | 0.0243 (2) | 0.0735 (9) | |
H12 | 0.6537 | 0.7770 | 0.0164 | 0.088* | |
C13 | 0.4780 (4) | 0.71071 (13) | 0.11006 (18) | 0.0532 (5) | |
H13 | 0.5895 | 0.7037 | 0.1615 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0389 (3) | 0.0353 (3) | 0.0386 (3) | 0.00035 (19) | 0.0020 (2) | −0.00411 (19) |
Cl1 | 0.0588 (4) | 0.0481 (3) | 0.0537 (3) | −0.0065 (2) | −0.0110 (2) | −0.0122 (2) |
Cl2 | 0.0721 (5) | 0.1030 (6) | 0.0811 (5) | 0.0265 (4) | −0.0185 (4) | 0.0218 (4) |
O1 | 0.0393 (8) | 0.0572 (9) | 0.0630 (9) | 0.0037 (6) | 0.0147 (7) | −0.0013 (7) |
O2 | 0.0744 (10) | 0.0453 (8) | 0.0496 (9) | −0.0015 (7) | −0.0126 (7) | −0.0118 (7) |
C1 | 0.0352 (10) | 0.0335 (10) | 0.0387 (10) | −0.0034 (8) | 0.0011 (8) | −0.0019 (8) |
C2 | 0.0436 (11) | 0.0485 (12) | 0.0426 (11) | 0.0033 (9) | 0.0098 (9) | 0.0087 (9) |
C3 | 0.0578 (14) | 0.0449 (12) | 0.0740 (15) | −0.0002 (10) | 0.0151 (12) | 0.0162 (11) |
C4 | 0.0651 (16) | 0.0413 (13) | 0.0907 (19) | 0.0066 (10) | 0.0183 (14) | 0.0030 (12) |
C5 | 0.0521 (13) | 0.0496 (13) | 0.0740 (16) | 0.0079 (10) | 0.0168 (12) | 0.0003 (11) |
C6 | 0.0358 (11) | 0.0420 (11) | 0.0516 (12) | −0.0022 (8) | 0.0076 (9) | 0.0044 (9) |
C7 | 0.0468 (13) | 0.0562 (13) | 0.0543 (13) | 0.0065 (10) | −0.0091 (10) | 0.0070 (10) |
C8 | 0.0409 (11) | 0.0315 (10) | 0.0458 (11) | 0.0049 (8) | 0.0068 (8) | 0.0001 (8) |
C9 | 0.0528 (12) | 0.0499 (13) | 0.0544 (12) | 0.0130 (10) | 0.0011 (10) | 0.0051 (10) |
C10 | 0.094 (2) | 0.0665 (16) | 0.0539 (14) | 0.0278 (15) | 0.0095 (13) | 0.0163 (12) |
C11 | 0.116 (3) | 0.0534 (15) | 0.0676 (17) | 0.0306 (16) | 0.0440 (18) | 0.0206 (13) |
C12 | 0.0779 (19) | 0.0437 (13) | 0.105 (2) | 0.0025 (12) | 0.0519 (18) | 0.0054 (14) |
C13 | 0.0461 (12) | 0.0409 (11) | 0.0740 (15) | 0.0019 (9) | 0.0135 (10) | 0.0012 (10) |
S1—O1 | 1.4260 (17) | C5—C6 | 1.527 (3) |
S1—O2 | 1.4269 (16) | C5—H5A | 0.9900 |
S1—C8 | 1.762 (2) | C5—H5B | 0.9900 |
S1—C1 | 1.821 (2) | C6—C7 | 1.535 (3) |
Cl1—C1 | 1.781 (2) | C6—H6 | 1.0000 |
Cl2—C7 | 1.787 (2) | C7—H7 | 1.0000 |
C1—C6 | 1.538 (3) | C8—C9 | 1.377 (3) |
C1—C2 | 1.557 (3) | C8—C13 | 1.387 (3) |
C2—C3 | 1.525 (3) | C9—C10 | 1.377 (3) |
C2—C7 | 1.528 (3) | C9—H9 | 0.9500 |
C2—H2 | 1.0000 | C10—C11 | 1.360 (4) |
C3—C4 | 1.541 (4) | C10—H10 | 0.9500 |
C3—H3A | 0.9900 | C11—C12 | 1.374 (5) |
C3—H3B | 0.9900 | C11—H11 | 0.9500 |
C4—C5 | 1.534 (3) | C12—C13 | 1.390 (3) |
C4—H4A | 0.9900 | C12—H12 | 0.9500 |
C4—H4B | 0.9900 | C13—H13 | 0.9500 |
O1—S1—O2 | 118.22 (10) | C6—C5—H5B | 108.9 |
O1—S1—C8 | 108.55 (10) | C4—C5—H5B | 108.9 |
O2—S1—C8 | 107.99 (10) | H5A—C5—H5B | 107.7 |
O1—S1—C1 | 107.23 (9) | C5—C6—C7 | 110.47 (18) |
O2—S1—C1 | 107.55 (10) | C5—C6—C1 | 109.46 (17) |
C8—S1—C1 | 106.76 (9) | C7—C6—C1 | 85.82 (15) |
C6—C1—C2 | 87.15 (15) | C5—C6—H6 | 115.8 |
C6—C1—Cl1 | 117.56 (14) | C7—C6—H6 | 115.8 |
C2—C1—Cl1 | 118.61 (14) | C1—C6—H6 | 115.8 |
C6—C1—S1 | 117.34 (13) | C2—C7—C6 | 88.29 (17) |
C2—C1—S1 | 111.16 (13) | C2—C7—Cl2 | 118.34 (16) |
Cl1—C1—S1 | 104.90 (10) | C6—C7—Cl2 | 118.33 (17) |
C3—C2—C7 | 111.22 (18) | C2—C7—H7 | 110.1 |
C3—C2—C1 | 109.69 (18) | C6—C7—H7 | 110.1 |
C7—C2—C1 | 85.39 (15) | Cl2—C7—H7 | 110.1 |
C3—C2—H2 | 115.6 | C9—C8—C13 | 121.5 (2) |
C7—C2—H2 | 115.6 | C9—C8—S1 | 119.05 (16) |
C1—C2—H2 | 115.6 | C13—C8—S1 | 119.35 (17) |
C2—C3—C4 | 112.82 (19) | C8—C9—C10 | 119.5 (2) |
C2—C3—H3A | 109.0 | C8—C9—H9 | 120.3 |
C4—C3—H3A | 109.0 | C10—C9—H9 | 120.3 |
C2—C3—H3B | 109.0 | C11—C10—C9 | 119.9 (3) |
C4—C3—H3B | 109.0 | C11—C10—H10 | 120.1 |
H3A—C3—H3B | 107.8 | C9—C10—H10 | 120.1 |
C5—C4—C3 | 115.85 (19) | C10—C11—C12 | 120.9 (2) |
C5—C4—H4A | 108.3 | C10—C11—H11 | 119.5 |
C3—C4—H4A | 108.3 | C12—C11—H11 | 119.5 |
C5—C4—H4B | 108.3 | C11—C12—C13 | 120.5 (3) |
C3—C4—H4B | 108.3 | C11—C12—H12 | 119.8 |
H4A—C4—H4B | 107.4 | C13—C12—H12 | 119.8 |
C6—C5—C4 | 113.52 (19) | C8—C13—C12 | 117.7 (2) |
C6—C5—H5A | 108.9 | C8—C13—H13 | 121.1 |
C4—C5—H5A | 108.9 | C12—C13—H13 | 121.1 |
O1—S1—C1—C6 | −172.22 (14) | Cl1—C1—C6—C7 | −147.90 (15) |
O2—S1—C1—C6 | −44.10 (17) | S1—C1—C6—C7 | 85.49 (16) |
C8—S1—C1—C6 | 71.59 (17) | C3—C2—C7—C6 | 82.25 (19) |
O1—S1—C1—C2 | −74.16 (16) | C1—C2—C7—C6 | −27.10 (15) |
O2—S1—C1—C2 | 53.95 (16) | C3—C2—C7—Cl2 | −39.3 (2) |
C8—S1—C1—C2 | 169.65 (13) | C1—C2—C7—Cl2 | −148.65 (17) |
O1—S1—C1—Cl1 | 55.20 (12) | C5—C6—C7—C2 | −81.78 (19) |
O2—S1—C1—Cl1 | −176.68 (10) | C1—C6—C7—C2 | 27.45 (15) |
C8—S1—C1—Cl1 | −60.99 (12) | C5—C6—C7—Cl2 | 39.8 (2) |
C6—C1—C2—C3 | −83.84 (18) | C1—C6—C7—Cl2 | 149.01 (16) |
Cl1—C1—C2—C3 | 36.2 (2) | O1—S1—C8—C9 | −17.73 (19) |
S1—C1—C2—C3 | 157.88 (15) | O2—S1—C8—C9 | −147.04 (16) |
C6—C1—C2—C7 | 27.06 (15) | C1—S1—C8—C9 | 97.57 (17) |
Cl1—C1—C2—C7 | 147.10 (15) | O1—S1—C8—C13 | 157.86 (16) |
S1—C1—C2—C7 | −91.22 (15) | O2—S1—C8—C13 | 28.56 (19) |
C7—C2—C3—C4 | −45.3 (3) | C1—S1—C8—C13 | −86.84 (17) |
C1—C2—C3—C4 | 47.4 (3) | C13—C8—C9—C10 | −1.2 (3) |
C2—C3—C4—C5 | −1.3 (3) | S1—C8—C9—C10 | 174.29 (17) |
C3—C4—C5—C6 | 1.1 (3) | C8—C9—C10—C11 | 0.3 (4) |
C4—C5—C6—C7 | 45.3 (3) | C9—C10—C11—C12 | 1.1 (4) |
C4—C5—C6—C1 | −47.5 (3) | C10—C11—C12—C13 | −1.6 (4) |
C2—C1—C6—C5 | 83.33 (18) | C9—C8—C13—C12 | 0.8 (3) |
Cl1—C1—C6—C5 | −37.7 (2) | S1—C8—C13—C12 | −174.72 (17) |
S1—C1—C6—C5 | −164.27 (15) | C11—C12—C13—C8 | 0.6 (3) |
C2—C1—C6—C7 | −26.92 (15) |