Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620014869/rm5041sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620014869/rm50411sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520620014869/rm50412sup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620014869/rm5041sup4.pdf |
CCDC references: 2000467; 2000468
For both structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C18H10Cl2O2S2 | F(000) = 400 |
Mr = 393.28 | Dx = 1.740 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 4.6455 (3) Å | Cell parameters from 1880 reflections |
b = 15.9427 (8) Å | θ = 2.4–28.3° |
c = 10.1908 (6) Å | µ = 0.72 mm−1 |
β = 95.846 (4)° | T = 130 K |
V = 750.82 (8) Å3 | Black needle, black |
Z = 2 | 0.35 × 0.11 × 0.08 mm |
BRUKER AXS (Kappa APEX II Duo) diffractometer | 1410 reflections with I > 2σ(I) |
Radiation source: conventional tube | Rint = 0.056 |
Graphite monochromator | θmax = 28.3°, θmin = 2.4° |
Absorption correction: multi-scan Blessing, 1995 | h = −6→6 |
Tmin = 0.788, Tmax = 0.948 | k = −21→21 |
12979 measured reflections | l = −13→13 |
1882 independent reflections |
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) = 0.201 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.107P)2 + 2.7825P] where P = (Fo2 + 2Fc2)/3 |
1882 reflections | (Δ/σ)max = 0.002 |
115 parameters | Δρmax = 0.85 e Å−3 |
0 restraints | Δρmin = −1.31 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.2746 (2) | 0.54976 (6) | 0.35512 (10) | 0.0121 (3) | |
Cl1 | 0.8916 (3) | 0.39280 (9) | −0.00068 (13) | 0.0337 (4) | |
O1 | −0.0020 (6) | 0.34048 (17) | 0.4845 (3) | 0.0160 (6) | |
C2 | 0.4055 (8) | 0.4608 (2) | 0.2771 (4) | 0.0123 (8) | |
C3 | 0.5920 (8) | 0.4662 (3) | 0.1779 (4) | 0.0139 (8) | |
H3 | 0.6591 | 0.5186 | 0.1488 | 0.016 (12)* | |
C4 | 0.3911 (9) | 0.3087 (2) | 0.2646 (4) | 0.0140 (8) | |
C5 | 0.5771 (9) | 0.3137 (3) | 0.1649 (4) | 0.0158 (8) | |
H5 | 0.6380 | 0.2639 | 0.1246 | 0.019 (13)* | |
C6 | 0.3085 (8) | 0.3837 (2) | 0.3201 (4) | 0.0120 (7) | |
C7 | 0.0834 (8) | 0.4858 (2) | 0.4533 (4) | 0.0111 (7) | |
C9 | 0.6729 (8) | 0.3913 (3) | 0.1248 (4) | 0.0164 (8) | |
C10 | 0.2851 (9) | 0.2253 (3) | 0.3056 (5) | 0.0189 (9) | |
H10A | 0.3599 | 0.1813 | 0.2512 | 0.043 (18)* | |
H10B | 0.0731 | 0.2246 | 0.2941 | 0.06 (2)* | |
H10C | 0.3528 | 0.2153 | 0.3986 | 0.05 (2)* | |
C11 | 0.1172 (8) | 0.3945 (2) | 0.4246 (4) | 0.0115 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0126 (5) | 0.0118 (4) | 0.0126 (5) | 0.0004 (3) | 0.0042 (3) | −0.0006 (4) |
Cl1 | 0.0283 (7) | 0.0453 (8) | 0.0287 (7) | 0.0051 (5) | 0.0093 (5) | −0.0022 (5) |
O1 | 0.0210 (15) | 0.0108 (13) | 0.0168 (15) | 0.0000 (11) | 0.0047 (11) | −0.0001 (11) |
C2 | 0.0082 (17) | 0.0157 (18) | 0.0131 (19) | 0.0000 (13) | 0.0006 (14) | −0.0027 (14) |
C3 | 0.0103 (18) | 0.0192 (19) | 0.0125 (19) | 0.0010 (14) | 0.0030 (14) | 0.0003 (15) |
C4 | 0.0137 (18) | 0.0159 (18) | 0.0117 (19) | 0.0054 (14) | −0.0015 (15) | −0.0013 (15) |
C5 | 0.0158 (19) | 0.019 (2) | 0.0122 (19) | 0.0081 (15) | 0.0004 (15) | −0.0050 (15) |
C6 | 0.0105 (17) | 0.0145 (18) | 0.0110 (18) | 0.0022 (14) | 0.0004 (14) | −0.0012 (14) |
C7 | 0.0102 (16) | 0.0116 (17) | 0.0114 (18) | 0.0009 (13) | 0.0002 (14) | 0.0016 (14) |
C9 | 0.0107 (18) | 0.028 (2) | 0.0103 (19) | 0.0032 (15) | 0.0013 (14) | −0.0041 (16) |
C10 | 0.022 (2) | 0.0146 (19) | 0.020 (2) | 0.0052 (15) | 0.0025 (17) | −0.0009 (16) |
C11 | 0.0093 (16) | 0.0131 (17) | 0.0118 (18) | 0.0030 (13) | −0.0008 (14) | −0.0019 (14) |
S1—C7 | 1.735 (4) | C4—C10 | 1.492 (6) |
S1—C2 | 1.764 (4) | C5—C9 | 1.390 (6) |
Cl1—C9 | 1.713 (4) | C5—H5 | 0.9500 |
O1—C11 | 1.221 (5) | C6—C11 | 1.465 (5) |
C2—C6 | 1.395 (5) | C7—C7i | 1.365 (7) |
C2—C3 | 1.399 (5) | C7—C11 | 1.495 (5) |
C3—C9 | 1.379 (6) | C10—H10A | 0.9800 |
C3—H3 | 0.9500 | C10—H10B | 0.9800 |
C4—C6 | 1.394 (5) | C10—H10C | 0.9800 |
C4—C5 | 1.402 (6) | ||
C7—S1—C2 | 90.41 (18) | C7i—C7—C11 | 122.6 (4) |
C6—C2—C3 | 121.6 (4) | C7i—C7—S1 | 124.5 (4) |
C6—C2—S1 | 115.5 (3) | C11—C7—S1 | 112.9 (3) |
C3—C2—S1 | 122.9 (3) | C3—C9—C5 | 123.2 (4) |
C9—C3—C2 | 116.3 (4) | C3—C9—Cl1 | 119.1 (3) |
C9—C3—H3 | 121.8 | C5—C9—Cl1 | 117.6 (3) |
C2—C3—H3 | 121.8 | C4—C10—H10A | 109.5 |
C6—C4—C5 | 117.4 (4) | C4—C10—H10B | 109.5 |
C6—C4—C10 | 122.6 (4) | H10A—C10—H10B | 109.5 |
C5—C4—C10 | 120.0 (4) | C4—C10—H10C | 109.5 |
C9—C5—C4 | 120.2 (4) | H10A—C10—H10C | 109.5 |
C9—C5—H5 | 119.9 | H10B—C10—H10C | 109.5 |
C4—C5—H5 | 119.9 | O1—C11—C6 | 128.3 (4) |
C4—C6—C2 | 121.2 (4) | O1—C11—C7 | 121.8 (3) |
C4—C6—C11 | 127.5 (4) | C6—C11—C7 | 109.9 (3) |
C2—C6—C11 | 111.3 (3) |
Symmetry code: (i) −x, −y+1, −z+1. |
C18H10Cl2O2S2 | Z = 1 |
Mr = 393.28 | F(000) = 200 |
Triclinic, P1 | Dx = 1.714 Mg m−3 |
a = 3.8612 (2) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 8.8249 (3) Å | Cell parameters from 1288 reflections |
c = 11.2319 (5) Å | θ = 4.0–66.5° |
α = 94.972 (3)° | µ = 6.47 mm−1 |
β = 92.244 (3)° | T = 130 K |
γ = 90.968 (3)° | Red needle, red |
V = 380.91 (3) Å3 | 0.17 × 0.04 × 0.03 mm |
BRUKER AXS (Kappa APEX II Duo) diffractometer | 1141 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 66.6°, θmin = 4.0° |
Absorption correction: multi-scan Blessing 1995 | h = −4→4 |
Tmin = 0.409, Tmax = 0.820 | k = −8→10 |
5028 measured reflections | l = −12→13 |
1290 independent reflections |
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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.083 | H-atom parameters constrained |
S = 0.72 | w = 1/[σ2(Fo2) + (0.0653P)2 + 0.9825P] where P = (Fo2 + 2Fc2)/3 |
1290 reflections | (Δ/σ)max = 0.001 |
115 parameters | Δρmax = 0.33 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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 | 0.75448 (14) | 1.07494 (6) | 0.83555 (5) | 0.01482 (19) | |
Cl4 | 0.11393 (15) | 0.75465 (6) | 0.44718 (5) | 0.02008 (19) | |
O2 | 0.9293 (4) | 0.71215 (18) | 0.99625 (15) | 0.0192 (4) | |
C1 | 0.4183 (6) | 0.9049 (3) | 0.6432 (2) | 0.0154 (5) | |
H1 | 0.3780 | 0.9958 | 0.6058 | 0.018 (7)* | |
C3 | 0.9117 (6) | 0.9700 (3) | 0.9499 (2) | 0.0136 (5) | |
C4 | 0.5212 (6) | 0.6313 (3) | 0.7568 (2) | 0.0146 (5) | |
C5 | 0.8327 (6) | 0.8034 (3) | 0.9265 (2) | 0.0146 (5) | |
C6 | 0.3118 (6) | 0.7640 (3) | 0.5898 (2) | 0.0160 (5) | |
C7 | 0.5879 (6) | 0.9063 (3) | 0.7551 (2) | 0.0150 (5) | |
C8 | 0.6397 (6) | 0.7732 (3) | 0.8113 (2) | 0.0146 (5) | |
C9 | 0.3587 (6) | 0.6290 (3) | 0.6439 (2) | 0.0162 (5) | |
H9 | 0.2791 | 0.5351 | 0.6035 | 0.022 (7)* | |
C10 | 0.5632 (7) | 0.4874 (3) | 0.8172 (2) | 0.0196 (5) | |
H10A | 0.4709 | 0.4011 | 0.7639 | 0.042 (9)* | |
H10B | 0.4365 | 0.4946 | 0.8913 | 0.024 (7)* | |
H10C | 0.8096 | 0.4724 | 0.8359 | 0.036 (9)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0165 (3) | 0.0119 (3) | 0.0156 (3) | −0.0004 (2) | −0.0026 (2) | 0.0005 (2) |
Cl4 | 0.0218 (3) | 0.0208 (3) | 0.0168 (3) | −0.0023 (2) | −0.0056 (2) | 0.0004 (2) |
O2 | 0.0220 (9) | 0.0157 (8) | 0.0196 (9) | 0.0006 (7) | −0.0040 (7) | 0.0021 (7) |
C1 | 0.0148 (11) | 0.0149 (12) | 0.0172 (12) | 0.0018 (9) | 0.0011 (10) | 0.0043 (9) |
C3 | 0.0117 (11) | 0.0128 (11) | 0.0164 (11) | 0.0013 (9) | 0.0017 (9) | 0.0013 (9) |
C4 | 0.0120 (11) | 0.0154 (11) | 0.0165 (12) | 0.0015 (9) | 0.0035 (9) | 0.0003 (9) |
C5 | 0.0125 (11) | 0.0158 (11) | 0.0156 (12) | 0.0012 (9) | 0.0027 (9) | 0.0003 (9) |
C6 | 0.0110 (11) | 0.0218 (12) | 0.0147 (12) | −0.0021 (9) | −0.0003 (9) | −0.0011 (9) |
C7 | 0.0110 (11) | 0.0164 (11) | 0.0174 (12) | −0.0003 (9) | 0.0020 (9) | −0.0007 (9) |
C8 | 0.0123 (11) | 0.0154 (11) | 0.0160 (12) | 0.0005 (9) | 0.0021 (9) | 0.0003 (9) |
C9 | 0.0153 (11) | 0.0135 (11) | 0.0192 (12) | −0.0013 (9) | 0.0010 (9) | −0.0022 (9) |
C10 | 0.0241 (13) | 0.0129 (11) | 0.0215 (13) | −0.0019 (10) | −0.0032 (10) | 0.0022 (9) |
S1—C3 | 1.744 (2) | C4—C8 | 1.407 (3) |
S1—C7 | 1.771 (2) | C4—C10 | 1.499 (3) |
Cl4—C6 | 1.742 (2) | C5—C8 | 1.469 (3) |
O2—C5 | 1.224 (3) | C6—C9 | 1.395 (3) |
C1—C6 | 1.382 (3) | C7—C8 | 1.394 (3) |
C1—C7 | 1.393 (3) | C9—H9 | 0.9500 |
C1—H1 | 0.9500 | C10—H10A | 0.9800 |
C3—C3i | 1.355 (5) | C10—H10B | 0.9800 |
C3—C5 | 1.495 (3) | C10—H10C | 0.9800 |
C4—C9 | 1.391 (3) | ||
C3—S1—C7 | 90.39 (11) | C1—C7—C8 | 121.8 (2) |
C6—C1—C7 | 116.3 (2) | C1—C7—S1 | 122.94 (18) |
C6—C1—H1 | 121.8 | C8—C7—S1 | 115.24 (18) |
C7—C1—H1 | 121.8 | C7—C8—C4 | 121.0 (2) |
C3i—C3—C5 | 122.5 (3) | C7—C8—C5 | 111.7 (2) |
C3i—C3—S1 | 124.7 (2) | C4—C8—C5 | 127.3 (2) |
C5—C3—S1 | 112.84 (17) | C4—C9—C6 | 120.3 (2) |
C9—C4—C8 | 117.3 (2) | C4—C9—H9 | 119.8 |
C9—C4—C10 | 120.7 (2) | C6—C9—H9 | 119.8 |
C8—C4—C10 | 122.0 (2) | C4—C10—H10A | 109.5 |
O2—C5—C8 | 128.4 (2) | C4—C10—H10B | 109.5 |
O2—C5—C3 | 121.8 (2) | H10A—C10—H10B | 109.5 |
C8—C5—C3 | 109.9 (2) | C4—C10—H10C | 109.5 |
C1—C6—C9 | 123.2 (2) | H10A—C10—H10C | 109.5 |
C1—C6—Cl4 | 118.29 (19) | H10B—C10—H10C | 109.5 |
C9—C6—Cl4 | 118.56 (18) |
Symmetry code: (i) −x+2, −y+2, −z+2. |
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