Table 1.
Crystal data and parameters for structure refinement of 3a to 3i.
| Compound | 3a | 3b | 3c | 3d | 3e | 3f | 3g | 3h | 3i |
|---|---|---|---|---|---|---|---|---|---|
| CCDC deposition number | 939875 | 939876 | 939877 | 942741 | 942742 | 948856 | 944072 | 946445 | 948855 |
| Molecular formula | C13H8ClFOS | C13H8ClFOS | C13H8ClFOS | C13H7Cl2FOS | C14H7BrClFOS | C13H7BrClFOS | C13H8Cl2OS | C13H7Cl3OS | C13H7Cl3OS |
| Molecular weight | 266.70 | 266.70 | 266.70 | 301.15 | 345.61 | 345.61 | 283.15 | 317.60 | 317.60 |
| Crystal system | Orthorhombic | Monoclinic | Orthorhombic | Orthorhombic | Orthorhombic | Monoclinic | Monoclinic | Monoclinic | Monoclinic |
| Space group | Pca21 | P21/c | Pbca | Pbca | Pbca | P21/c | P21/c | P21/c | P21/c |
| a (Å) | 27.963 (9) | 14.282 (6) | 7.9809 (8) | 7.4870 (9) | 7.476 (2) | 3.8704 (7) | 14.5437 (10) | 14.9864(10) | 30.3418 (16) |
| b (Å) | 3.9233 (15) | 7.698 (4) | 11.0207 (11) | 11.6186 (14) | 11.724 (3) | 31.953 (6) | 7.5227 (6) | 3.8085 (3) | 3.7985 (2) |
| c (Å) | 11.146 (4) | 11.376 (5) | 27.518 (3) | 29.239 (4) | 30.009 (8) | 10.273 (2) | 11.7604 (9) | 24.6297 (13) | 23.4311 (12) |
| α (°) | 90 | 90 | 90 | 90 | 90 | 90 | 90 | 90 | 90 |
| β (°) | 90 | 104.430 | 90 | 90 | 90 | 95.243 (3) | 104.721 (1) | 115.264 (3) | 109.297 (1) |
| γ (°) | 90 | 90 | 90 | 90 | 90 | 90 | 90 | 90 | 90 |
| V (Å3) | 1222.8 (7) | 1211.3 (9) | 2420.3 (4) | 2543.4 (5) | 2630.4 (13) | 1265.2 (4) | 1244.44 (16) | 1271.30 (15) | 2548.8 (2) |
| Z | 4 | 4 | 8 | 8 | 8 | 4 | 4 | 4 | 8 |
| Dcalc (g cm−3) | 1.449 | 1.462 | 1.464 | 1.573 | 1.745 | 1.814 | 1.511 | 1.659 | 1.655 |
| Crystal dimensions (mm) | 0.93 × 0.18 × 0.05 | 0.25 × 0.25 × 0.05 | 0.79 × 0.37 × 0.04 | 0.75 × 0.52 × 0.10 | 0.58 × 0.28 × 0.09 | 0.89 × 0.12 × 0.09 | 0.50 × 0.23 × 0.08 | 0.51 × 0.10 × 0.05 | 0.60 × 0.10 × 0.10 |
| Colour | Colourless | Colourless | Colourless | Colourless | Colourless | Colourless | Colourless | Colourless | Colourless |
| μ(mm−1) | 0.47 | 0.48 | 0.48 | 0.67 | 3.48 | 3.62 | 0.67 | 0.87 | 0.86 |
| Radiation λ (Å) | 0.71073 | 0.71073 | 0.71073 | 0.71073 | 0.71073 | 0.71073 | 0.71073 | 0.71073 | 0.71073 |
| Tmin/Tmax | 0.668/0.975 | 0.889/0.975 | 0.704/0.980 | 0.633/0.935 | 0.237/0.752 | 0.141/0.744 | 0.733/0.946 | 0.665/0.955 | 0.624/0.922 |
| Reflections measured | 8618 | 9071 | 24679 | 16026 | 16116 | 2855 | 11650 | 11375 | 20108 |
| Ranges/indices (h, k, l) | −37, 39; −5, 5; −15, 15 | −16, 16; −9, 9; −13, 13 | −11, 11; −15, 15; −38, 37 | −10, 10; −14, 16; −41, 37 | −10, 9; −12, 16; −42, 31 | −5, 5; −41, 41; −1, 13 | −18, 18; −9, 9; −15, 15 | −19, 19; −4, 4; −31, 31 | −39, 39; −4, 4; −30, 30 |
| θ limit (°) | 2.3–22.4 | 3.0–19.5 | 3.2–25.3 | 2.8–26.4 | 2.7–25.3 | 2.8–29.8 | 2.9–29.0 | 2.8–30.1 | 2.9–29.9 |
| Unique reflections | 3368 | 2126 | 3540 | 3738 | 3816 | 2855 | 2829 | 2894 | 5762 |
| Observed reflections (I > 2σ(I)) | 1899 | 1133 | 2016 | 2486 | 1935 | 2624 | 2312 | 2607 | 4784 |
| Parameters | 154 | 154 | 154 | 163 | 163 | 164 | 154 | 163 | 325 |
| Goodness of fit on F2 | 0.99 | 1.00 | 1.03 | 1.03 | 1.01 | 1.09 | 1.04 | 1.05 | 1.03 |
| R1, wR2 [I ≥ 2σ(I)] | 0.049, 0.136 | 0.059, 0.191 | 0.047, 0.135 | 0.041, 0.135 | 0.044, 0.136 | 0.051, 0.127 | 0.030, 0.101 | 0.046, 0.120 | 0.033, 0.091 |