Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S205252061700364X/xm5002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252061700364X/xm5002Compound_1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252061700364X/xm5002Compound_3sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S205252061700364X/xm5002Compound_4sup4.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S205252061700364X/xm5002sup5.pdf |
CCDC references: 698897; 1517582; 1536520
For all compounds, data collection: CrystalClear. Cell refinement: CrystalClear for Compound_1; HKL-2000 for Compound_3, Compound_4. Data reduction: CrystalClear for Compound_1; HKL-2000 for Compound_3, Compound_4. Program(s) used to solve structure: SIR97 for Compound_1, Compound_3; SHELXT-2014/7 (Sheldrick, 2014) for Compound_4. Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for Compound_1, Compound_3; SHELXL2014/7 (Sheldrick, 2014) for Compound_4. Molecular graphics: Yadokari-XG 2011 (Wakita Nemoto et al., 2011) for Compound_4. Software used to prepare material for publication: Yadokari-XG 2011 (Wakita,Nemoto et al., 2011) for Compound_4.
C20H12Cl2S2 | F(000) = 1584 |
Mr = 387.32 | Dx = 1.592 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2c -2ac | Cell parameters from 8080 reflections |
a = 7.824 (2) Å | θ = 2.7–25.5° |
b = 28.782 (8) Å | µ = 0.66 mm−1 |
c = 14.350 (4) Å | T = 103 K |
V = 3231.7 (15) Å3 | Prism, colorless |
Z = 8 | 0.30 × 0.20 × 0.15 mm |
Rigaku Mercury diffractometer | 5988 independent reflections |
Radiation source: fine-focus sealed tube | 5947 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.018 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.5°, θmin = 2.7° |
ω scans | h = −8→9 |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | k = −34→34 |
Tmin = 0.827, Tmax = 0.908 | l = −17→17 |
25939 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.020 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.052 | w = 1/[σ2(Fo2) + (0.0302P)2 + 0.819P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
5988 reflections | Δρmax = 0.21 e Å−3 |
529 parameters | Δρmin = −0.17 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.46 (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 | ||
Cl1 | −0.26851 (5) | 0.514176 (13) | 0.04202 (3) | 0.01793 (9) | |
S1 | −0.23815 (5) | 0.412288 (14) | 0.03544 (3) | 0.01555 (9) | |
S2 | −0.23878 (5) | 0.341462 (14) | 0.04615 (4) | 0.01587 (9) | |
Cl2 | −0.29030 (5) | 0.240607 (13) | 0.04690 (3) | 0.01845 (9) | |
Cl3 | 0.75212 (6) | 0.254507 (14) | −0.20638 (4) | 0.01946 (9) | |
S3 | 0.69906 (5) | 0.155181 (15) | −0.15530 (3) | 0.01622 (9) | |
S4 | 0.69812 (5) | 0.085001 (14) | −0.13178 (3) | 0.01524 (9) | |
Cl4 | 0.75395 (6) | −0.015913 (14) | −0.12061 (3) | 0.01817 (9) | |
C1 | −0.1732 (2) | 0.51333 (6) | −0.06811 (11) | 0.0149 (3) | |
C2 | −0.1403 (2) | 0.55612 (6) | −0.10623 (13) | 0.0196 (4) | |
H1 | −0.170 (3) | 0.5819 (7) | −0.0707 (15) | 0.025 (5)* | |
C3 | −0.0670 (2) | 0.55991 (6) | −0.19501 (13) | 0.0204 (4) | |
H2 | −0.048 (3) | 0.5896 (8) | −0.2175 (15) | 0.028 (6)* | |
C4 | −0.0290 (2) | 0.52053 (6) | −0.24365 (12) | 0.0179 (4) | |
H3 | 0.028 (3) | 0.5218 (7) | −0.3028 (15) | 0.021 (5)* | |
C5 | −0.0627 (2) | 0.47598 (6) | −0.20644 (12) | 0.0159 (3) | |
C6 | −0.0246 (2) | 0.43632 (7) | −0.26148 (13) | 0.0183 (4) | |
H4 | 0.019 (3) | 0.4407 (7) | −0.3233 (15) | 0.019 (5)* | |
C7 | −0.0560 (2) | 0.39281 (6) | −0.22839 (12) | 0.0202 (4) | |
H5 | −0.035 (3) | 0.3654 (7) | −0.2670 (15) | 0.020 (5)* | |
C8 | −0.1220 (2) | 0.38694 (6) | −0.13784 (13) | 0.0180 (4) | |
H6 | −0.138 (3) | 0.3557 (8) | −0.1180 (15) | 0.026 (5)* | |
C9 | −0.1611 (2) | 0.42390 (6) | −0.08167 (12) | 0.0146 (3) | |
C10 | −0.1353 (2) | 0.47067 (6) | −0.11452 (12) | 0.0129 (3) | |
C11 | −0.0189 (2) | 0.32527 (6) | 0.06836 (11) | 0.0145 (3) | |
C12 | 0.1023 (2) | 0.35978 (6) | 0.07207 (12) | 0.0171 (4) | |
H7 | 0.069 (2) | 0.3900 (7) | 0.0584 (15) | 0.022 (5)* | |
C13 | 0.2748 (2) | 0.35012 (7) | 0.09032 (13) | 0.0190 (4) | |
H8 | 0.361 (3) | 0.3769 (7) | 0.0905 (14) | 0.022 (6)* | |
C14 | 0.3259 (2) | 0.30564 (7) | 0.10622 (12) | 0.0169 (4) | |
H9 | 0.439 (3) | 0.2995 (7) | 0.1233 (14) | 0.020 (5)* | |
C15 | 0.2065 (2) | 0.26853 (6) | 0.10221 (11) | 0.0137 (3) | |
C16 | 0.2663 (2) | 0.22231 (6) | 0.11704 (12) | 0.0158 (4) | |
H10 | 0.381 (2) | 0.2186 (6) | 0.1330 (13) | 0.008 (4)* | |
C17 | 0.1581 (2) | 0.18538 (6) | 0.11161 (12) | 0.0174 (4) | |
H11 | 0.197 (2) | 0.1531 (7) | 0.1234 (15) | 0.021 (5)* | |
C18 | −0.0143 (2) | 0.19269 (6) | 0.09071 (12) | 0.0169 (4) | |
H12 | −0.095 (3) | 0.1674 (7) | 0.0887 (14) | 0.020 (5)* | |
C19 | −0.0741 (2) | 0.23682 (6) | 0.07589 (11) | 0.0139 (3) | |
C20 | 0.0307 (2) | 0.27745 (6) | 0.08159 (11) | 0.0131 (3) | |
C21 | 0.5376 (2) | 0.26083 (6) | −0.17565 (11) | 0.0151 (4) | |
C22 | 0.4802 (2) | 0.30578 (6) | −0.17261 (12) | 0.0194 (4) | |
H13 | 0.563 (3) | 0.3292 (8) | −0.1813 (16) | 0.033 (6)* | |
C23 | 0.3075 (2) | 0.31479 (6) | −0.15568 (13) | 0.0205 (4) | |
H14 | 0.270 (3) | 0.3452 (8) | −0.1540 (16) | 0.027 (6)* | |
C24 | 0.1974 (2) | 0.27915 (6) | −0.14316 (12) | 0.0175 (4) | |
H15 | 0.085 (3) | 0.2843 (7) | −0.1293 (16) | 0.026 (5)* | |
C25 | 0.2533 (2) | 0.23209 (6) | −0.14604 (12) | 0.0141 (3) | |
C26 | 0.1322 (2) | 0.19597 (6) | −0.13775 (12) | 0.0166 (3) | |
H16 | 0.018 (3) | 0.2032 (7) | −0.1250 (16) | 0.030 (6)* | |
C27 | 0.1795 (2) | 0.15069 (6) | −0.14334 (12) | 0.0170 (4) | |
H17 | 0.093 (3) | 0.1249 (7) | −0.1356 (15) | 0.028 (6)* | |
C28 | 0.3544 (2) | 0.13936 (6) | −0.15201 (12) | 0.0153 (3) | |
H18 | 0.387 (2) | 0.1077 (6) | −0.1539 (11) | 0.003 (4)* | |
C29 | 0.4775 (2) | 0.17284 (6) | −0.15840 (11) | 0.0142 (3) | |
C30 | 0.4305 (2) | 0.22162 (6) | −0.15979 (12) | 0.0139 (3) | |
C31 | 0.6385 (2) | 0.07745 (6) | −0.01071 (11) | 0.0136 (3) | |
C32 | 0.6017 (2) | 0.11634 (5) | 0.04174 (14) | 0.0163 (3) | |
H19 | 0.612 (2) | 0.1469 (7) | 0.0178 (13) | 0.015 (5)* | |
C33 | 0.5453 (2) | 0.11324 (6) | 0.13445 (13) | 0.0177 (4) | |
H20 | 0.521 (2) | 0.1403 (6) | 0.1672 (12) | 0.006 (4)* | |
C34 | 0.5181 (2) | 0.07093 (6) | 0.17352 (13) | 0.0184 (4) | |
H21 | 0.476 (3) | 0.0685 (7) | 0.2313 (16) | 0.018 (5)* | |
C35 | 0.5520 (2) | 0.02957 (6) | 0.12314 (12) | 0.0147 (3) | |
C36 | 0.5216 (2) | −0.01376 (6) | 0.16656 (13) | 0.0188 (4) | |
H22 | 0.482 (3) | −0.0131 (7) | 0.2260 (16) | 0.024 (5)* | |
C37 | 0.5562 (2) | −0.05468 (7) | 0.12238 (13) | 0.0215 (4) | |
H23 | 0.535 (3) | −0.0831 (7) | 0.1529 (15) | 0.022 (5)* | |
C38 | 0.6291 (2) | −0.05371 (6) | 0.03325 (14) | 0.0198 (4) | |
H24 | 0.658 (3) | −0.0794 (7) | 0.0000 (14) | 0.021 (5)* | |
C39 | 0.6579 (2) | −0.01197 (6) | −0.01096 (11) | 0.0150 (3) | |
C40 | 0.6193 (2) | 0.03191 (5) | 0.02990 (12) | 0.0138 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0245 (2) | 0.0141 (2) | 0.01520 (19) | 0.00411 (15) | 0.00190 (18) | −0.00145 (17) |
S1 | 0.0185 (2) | 0.0115 (2) | 0.0166 (2) | 0.00245 (15) | 0.00381 (18) | 0.00105 (18) |
S2 | 0.01367 (19) | 0.01162 (19) | 0.0223 (2) | 0.00035 (14) | 0.00202 (18) | 0.00276 (19) |
Cl2 | 0.0155 (2) | 0.01368 (19) | 0.0262 (2) | −0.00173 (14) | −0.0034 (2) | −0.00103 (18) |
Cl3 | 0.01465 (19) | 0.0174 (2) | 0.0263 (2) | −0.00234 (17) | 0.00039 (15) | 0.0055 (2) |
S3 | 0.0130 (2) | 0.0125 (2) | 0.0232 (2) | −0.00004 (15) | 0.00197 (18) | 0.00329 (16) |
S4 | 0.0172 (2) | 0.0115 (2) | 0.0170 (2) | 0.00239 (15) | 0.00266 (17) | 0.00087 (16) |
Cl4 | 0.0254 (2) | 0.0139 (2) | 0.01516 (19) | 0.00564 (16) | 0.00102 (17) | −0.00097 (16) |
C1 | 0.0138 (9) | 0.0164 (9) | 0.0144 (8) | 0.0013 (7) | −0.0026 (6) | −0.0006 (7) |
C2 | 0.0244 (10) | 0.0146 (9) | 0.0198 (9) | 0.0038 (7) | −0.0030 (8) | −0.0028 (7) |
C3 | 0.0241 (10) | 0.0140 (9) | 0.0232 (9) | −0.0029 (7) | −0.0036 (8) | 0.0025 (7) |
C4 | 0.0180 (10) | 0.0207 (9) | 0.0150 (9) | −0.0030 (7) | −0.0026 (7) | 0.0034 (7) |
C5 | 0.0134 (9) | 0.0185 (8) | 0.0157 (8) | 0.0003 (7) | −0.0022 (7) | −0.0002 (7) |
C6 | 0.0188 (9) | 0.0225 (9) | 0.0136 (8) | 0.0007 (7) | −0.0005 (7) | −0.0017 (7) |
C7 | 0.0242 (10) | 0.0181 (9) | 0.0183 (9) | 0.0026 (8) | −0.0013 (7) | −0.0048 (7) |
C8 | 0.0194 (9) | 0.0130 (8) | 0.0217 (9) | 0.0016 (7) | −0.0016 (7) | −0.0011 (7) |
C9 | 0.0125 (9) | 0.0160 (8) | 0.0153 (8) | 0.0006 (7) | −0.0012 (7) | −0.0002 (6) |
C10 | 0.0099 (8) | 0.0143 (8) | 0.0144 (8) | 0.0004 (6) | −0.0044 (7) | −0.0003 (6) |
C11 | 0.0146 (8) | 0.0156 (8) | 0.0133 (8) | 0.0002 (7) | 0.0005 (6) | −0.0002 (6) |
C12 | 0.0207 (9) | 0.0125 (9) | 0.0180 (8) | −0.0008 (7) | −0.0006 (7) | 0.0014 (6) |
C13 | 0.0191 (10) | 0.0169 (9) | 0.0210 (9) | −0.0066 (7) | −0.0027 (7) | 0.0003 (7) |
C14 | 0.0146 (9) | 0.0192 (10) | 0.0168 (8) | −0.0011 (7) | 0.0002 (7) | −0.0001 (7) |
C15 | 0.0161 (9) | 0.0123 (9) | 0.0126 (8) | 0.0004 (6) | 0.0009 (7) | 0.0004 (6) |
C16 | 0.0139 (9) | 0.0175 (9) | 0.0159 (9) | 0.0025 (7) | −0.0001 (7) | 0.0012 (7) |
C17 | 0.0195 (9) | 0.0126 (9) | 0.0203 (9) | 0.0031 (7) | 0.0016 (7) | 0.0022 (6) |
C18 | 0.0199 (9) | 0.0133 (8) | 0.0176 (8) | −0.0042 (8) | 0.0020 (7) | −0.0009 (7) |
C19 | 0.0127 (8) | 0.0151 (8) | 0.0138 (7) | 0.0001 (7) | 0.0007 (6) | −0.0009 (6) |
C20 | 0.0164 (9) | 0.0128 (8) | 0.0100 (7) | −0.0020 (7) | 0.0015 (6) | −0.0001 (6) |
C21 | 0.0131 (8) | 0.0164 (9) | 0.0159 (8) | −0.0007 (7) | −0.0031 (7) | 0.0011 (6) |
C22 | 0.0211 (9) | 0.0138 (9) | 0.0231 (9) | −0.0050 (7) | −0.0053 (7) | 0.0005 (7) |
C23 | 0.0237 (9) | 0.0139 (9) | 0.0238 (9) | 0.0043 (7) | −0.0052 (8) | −0.0032 (7) |
C24 | 0.0175 (9) | 0.0180 (9) | 0.0169 (9) | 0.0051 (7) | −0.0021 (7) | −0.0020 (7) |
C25 | 0.0191 (9) | 0.0131 (9) | 0.0100 (8) | 0.0005 (6) | −0.0024 (6) | 0.0001 (6) |
C26 | 0.0128 (8) | 0.0223 (9) | 0.0146 (8) | 0.0003 (7) | −0.0001 (7) | 0.0025 (7) |
C27 | 0.0143 (8) | 0.0195 (9) | 0.0173 (9) | −0.0047 (7) | −0.0022 (7) | 0.0025 (7) |
C28 | 0.0168 (8) | 0.0126 (8) | 0.0163 (8) | −0.0001 (7) | −0.0021 (7) | 0.0017 (7) |
C29 | 0.0140 (8) | 0.0163 (8) | 0.0122 (7) | 0.0011 (6) | 0.0004 (6) | 0.0011 (6) |
C30 | 0.0183 (9) | 0.0128 (8) | 0.0105 (7) | −0.0007 (6) | −0.0028 (7) | −0.0010 (6) |
C31 | 0.0105 (8) | 0.0162 (8) | 0.0142 (8) | 0.0008 (7) | −0.0030 (7) | −0.0007 (6) |
C32 | 0.0174 (8) | 0.0110 (8) | 0.0204 (8) | −0.0002 (6) | −0.0039 (8) | 0.0010 (7) |
C33 | 0.0211 (9) | 0.0128 (8) | 0.0194 (8) | 0.0021 (7) | −0.0042 (7) | −0.0065 (7) |
C34 | 0.0177 (9) | 0.0232 (10) | 0.0142 (9) | 0.0032 (7) | −0.0001 (7) | −0.0038 (7) |
C35 | 0.0115 (8) | 0.0166 (9) | 0.0159 (8) | 0.0005 (6) | −0.0029 (7) | −0.0013 (7) |
C36 | 0.0189 (10) | 0.0229 (9) | 0.0145 (8) | 0.0008 (7) | −0.0007 (7) | 0.0022 (7) |
C37 | 0.0265 (10) | 0.0156 (10) | 0.0223 (9) | 0.0012 (8) | −0.0004 (8) | 0.0050 (7) |
C38 | 0.0253 (9) | 0.0114 (8) | 0.0227 (9) | 0.0028 (7) | −0.0021 (8) | −0.0002 (8) |
C39 | 0.0153 (9) | 0.0171 (9) | 0.0127 (8) | 0.0030 (7) | −0.0021 (7) | −0.0001 (6) |
C40 | 0.0096 (7) | 0.0150 (8) | 0.0168 (8) | 0.0023 (6) | −0.0036 (7) | −0.0001 (7) |
Cl1—C1 | 1.7477 (18) | C17—C18 | 1.397 (3) |
S1—C9 | 1.8164 (18) | C17—H11 | 0.99 (2) |
S1—S2 | 2.0443 (8) | C18—C19 | 1.370 (3) |
S2—C11 | 1.8105 (18) | C18—H12 | 0.96 (2) |
Cl2—C19 | 1.7455 (18) | C19—C20 | 1.431 (2) |
Cl3—C21 | 1.7448 (18) | C21—C22 | 1.370 (3) |
S3—C29 | 1.8072 (18) | C21—C30 | 1.424 (2) |
S3—S4 | 2.0480 (8) | C22—C23 | 1.398 (3) |
S4—C31 | 1.8121 (18) | C22—H13 | 0.94 (2) |
Cl4—C39 | 1.7474 (18) | C23—C24 | 1.351 (3) |
C1—C2 | 1.372 (3) | C23—H14 | 0.92 (2) |
C1—C10 | 1.428 (2) | C24—C25 | 1.424 (2) |
C2—C3 | 1.401 (3) | C24—H15 | 0.91 (2) |
C2—H1 | 0.93 (2) | C25—C26 | 1.412 (2) |
C3—C4 | 1.364 (3) | C25—C30 | 1.433 (2) |
C3—H2 | 0.92 (2) | C26—C27 | 1.357 (3) |
C4—C5 | 1.414 (3) | C26—H16 | 0.94 (2) |
C4—H3 | 0.96 (2) | C27—C28 | 1.412 (3) |
C5—C6 | 1.420 (2) | C27—H17 | 1.01 (2) |
C5—C10 | 1.444 (2) | C28—C29 | 1.366 (2) |
C6—C7 | 1.362 (3) | C28—H18 | 0.947 (17) |
C6—H4 | 0.96 (2) | C29—C30 | 1.451 (2) |
C7—C8 | 1.408 (3) | C31—C32 | 1.379 (2) |
C7—H5 | 0.98 (2) | C31—C40 | 1.442 (2) |
C8—C9 | 1.369 (2) | C32—C33 | 1.404 (3) |
C8—H6 | 0.95 (2) | C32—H19 | 0.947 (19) |
C9—C10 | 1.440 (2) | C33—C34 | 1.358 (3) |
C11—C12 | 1.374 (2) | C33—H20 | 0.930 (18) |
C11—C20 | 1.443 (2) | C34—C35 | 1.418 (2) |
C12—C13 | 1.403 (3) | C34—H21 | 0.89 (2) |
C12—H7 | 0.93 (2) | C35—C36 | 1.414 (3) |
C13—C14 | 1.361 (3) | C35—C40 | 1.440 (2) |
C13—H8 | 1.02 (2) | C36—C37 | 1.365 (3) |
C14—C15 | 1.420 (3) | C36—H22 | 0.91 (2) |
C14—H9 | 0.93 (2) | C37—C38 | 1.401 (3) |
C15—C16 | 1.426 (3) | C37—H23 | 0.94 (2) |
C15—C20 | 1.430 (2) | C38—C39 | 1.377 (2) |
C16—C17 | 1.362 (3) | C38—H24 | 0.91 (2) |
C16—H10 | 0.931 (19) | C39—C40 | 1.425 (2) |
C9—S1—S2 | 104.70 (6) | C15—C20—C11 | 117.22 (15) |
C11—S2—S1 | 105.52 (6) | C19—C20—C11 | 128.18 (16) |
C29—S3—S4 | 106.14 (6) | C22—C21—C30 | 123.41 (16) |
C31—S4—S3 | 106.09 (6) | C22—C21—Cl3 | 114.94 (14) |
C2—C1—C10 | 123.16 (16) | C30—C21—Cl3 | 121.58 (13) |
C2—C1—Cl1 | 115.35 (13) | C21—C22—C23 | 119.84 (17) |
C10—C1—Cl1 | 121.48 (13) | C21—C22—H13 | 116.7 (14) |
C1—C2—C3 | 120.61 (17) | C23—C22—H13 | 123.5 (14) |
C1—C2—H1 | 116.7 (13) | C24—C23—C22 | 119.91 (17) |
C3—C2—H1 | 122.7 (13) | C24—C23—H14 | 120.7 (14) |
C4—C3—C2 | 119.33 (17) | C22—C23—H14 | 119.4 (13) |
C4—C3—H2 | 123.6 (14) | C23—C24—C25 | 121.52 (17) |
C2—C3—H2 | 117.0 (14) | C23—C24—H15 | 121.3 (13) |
C3—C4—C5 | 121.30 (17) | C25—C24—H15 | 117.1 (13) |
C3—C4—H3 | 121.6 (12) | C26—C25—C24 | 119.50 (16) |
C5—C4—H3 | 117.0 (12) | C26—C25—C30 | 120.41 (16) |
C4—C5—C6 | 118.68 (16) | C24—C25—C30 | 120.07 (16) |
C4—C5—C10 | 120.96 (16) | C27—C26—C25 | 121.29 (16) |
C6—C5—C10 | 120.36 (16) | C27—C26—H16 | 119.1 (13) |
C7—C6—C5 | 120.50 (17) | C25—C26—H16 | 119.5 (13) |
C7—C6—H4 | 120.5 (12) | C26—C27—C28 | 119.41 (16) |
C5—C6—H4 | 118.9 (12) | C26—C27—H17 | 121.2 (12) |
C6—C7—C8 | 119.89 (16) | C28—C27—H17 | 119.1 (12) |
C6—C7—H5 | 121.0 (12) | C29—C28—C27 | 121.78 (16) |
C8—C7—H5 | 119.1 (12) | C29—C28—H18 | 119.1 (10) |
C9—C8—C7 | 122.12 (16) | C27—C28—H18 | 119.1 (10) |
C9—C8—H6 | 122.0 (13) | C28—C29—C30 | 120.33 (15) |
C7—C8—H6 | 115.9 (13) | C28—C29—S3 | 118.46 (13) |
C8—C9—C10 | 120.14 (16) | C30—C29—S3 | 121.01 (13) |
C8—C9—S1 | 118.41 (13) | C21—C30—C25 | 115.13 (15) |
C10—C9—S1 | 121.41 (13) | C21—C30—C29 | 128.32 (16) |
C1—C10—C9 | 128.46 (16) | C25—C30—C29 | 116.52 (15) |
C1—C10—C5 | 114.61 (15) | C32—C31—C40 | 119.68 (16) |
C9—C10—C5 | 116.93 (15) | C32—C31—S4 | 118.67 (13) |
C12—C11—C20 | 119.91 (16) | C40—C31—S4 | 121.55 (13) |
C12—C11—S2 | 118.46 (13) | C31—C32—C33 | 122.08 (16) |
C20—C11—S2 | 121.63 (13) | C31—C32—H19 | 122.4 (12) |
C11—C12—C13 | 121.87 (17) | C33—C32—H19 | 115.5 (12) |
C11—C12—H7 | 118.4 (12) | C34—C33—C32 | 119.82 (16) |
C13—C12—H7 | 119.7 (12) | C34—C33—H20 | 120.8 (11) |
C14—C13—C12 | 120.04 (17) | C32—C33—H20 | 119.3 (11) |
C14—C13—H8 | 120.9 (12) | C33—C34—C35 | 120.89 (17) |
C12—C13—H8 | 119.1 (12) | C33—C34—H21 | 120.7 (13) |
C13—C14—C15 | 120.48 (17) | C35—C34—H21 | 118.4 (13) |
C13—C14—H9 | 120.0 (12) | C36—C35—C34 | 118.97 (17) |
C15—C14—H9 | 119.5 (12) | C36—C35—C40 | 120.82 (15) |
C14—C15—C16 | 118.63 (16) | C34—C35—C40 | 120.20 (16) |
C14—C15—C20 | 120.42 (16) | C37—C36—C35 | 121.54 (17) |
C16—C15—C20 | 120.94 (16) | C37—C36—H22 | 121.5 (13) |
C17—C16—C15 | 121.03 (17) | C35—C36—H22 | 116.9 (13) |
C17—C16—H10 | 121.5 (11) | C36—C37—C38 | 119.18 (17) |
C15—C16—H10 | 117.4 (11) | C36—C37—H23 | 119.8 (13) |
C16—C17—C18 | 119.67 (17) | C38—C37—H23 | 120.9 (13) |
C16—C17—H11 | 121.9 (11) | C39—C38—C37 | 120.32 (16) |
C18—C17—H11 | 118.4 (11) | C39—C38—H24 | 115.3 (13) |
C19—C18—C17 | 120.17 (17) | C37—C38—H24 | 124.3 (13) |
C19—C18—H12 | 118.3 (13) | C38—C39—C40 | 123.29 (16) |
C17—C18—H12 | 121.5 (13) | C38—C39—Cl4 | 115.38 (13) |
C18—C19—C20 | 123.58 (16) | C40—C39—Cl4 | 121.29 (13) |
C18—C19—Cl2 | 115.21 (13) | C39—C40—C35 | 114.74 (14) |
C20—C19—Cl2 | 121.20 (13) | C39—C40—C31 | 128.11 (16) |
C15—C20—C19 | 114.60 (16) | C35—C40—C31 | 117.15 (14) |
C9—S1—S2—C11 | 79.29 (8) | S2—C11—C20—C19 | 2.9 (2) |
C29—S3—S4—C31 | −73.20 (8) | C30—C21—C22—C23 | −1.8 (3) |
C10—C1—C2—C3 | 0.4 (3) | Cl3—C21—C22—C23 | 175.19 (14) |
Cl1—C1—C2—C3 | −178.79 (14) | C21—C22—C23—C24 | −0.6 (3) |
C1—C2—C3—C4 | 0.2 (3) | C22—C23—C24—C25 | 0.5 (3) |
C2—C3—C4—C5 | 0.3 (3) | C23—C24—C25—C26 | −176.49 (17) |
C3—C4—C5—C6 | 178.26 (16) | C23—C24—C25—C30 | 1.8 (3) |
C3—C4—C5—C10 | −1.4 (3) | C24—C25—C26—C27 | 177.73 (16) |
C4—C5—C6—C7 | −179.65 (17) | C30—C25—C26—C27 | −0.6 (3) |
C10—C5—C6—C7 | 0.0 (3) | C25—C26—C27—C28 | 3.8 (3) |
C5—C6—C7—C8 | −1.9 (3) | C26—C27—C28—C29 | −2.4 (3) |
C6—C7—C8—C9 | 1.9 (3) | C27—C28—C29—C30 | −2.2 (3) |
C7—C8—C9—C10 | 0.1 (3) | C27—C28—C29—S3 | 172.73 (13) |
C7—C8—C9—S1 | −177.81 (14) | S4—S3—C29—C28 | −4.31 (15) |
S2—S1—C9—C8 | 0.64 (15) | S4—S3—C29—C30 | 170.61 (12) |
S2—S1—C9—C10 | −177.23 (12) | C22—C21—C30—C25 | 3.9 (2) |
C2—C1—C10—C9 | 178.96 (17) | Cl3—C21—C30—C25 | −172.89 (12) |
Cl1—C1—C10—C9 | −1.9 (3) | C22—C21—C30—C29 | −177.96 (17) |
C2—C1—C10—C5 | −1.4 (2) | Cl3—C21—C30—C29 | 5.3 (3) |
Cl1—C1—C10—C5 | 177.76 (12) | C26—C25—C30—C21 | 174.49 (15) |
C8—C9—C10—C1 | 177.73 (16) | C24—C25—C30—C21 | −3.8 (2) |
S1—C9—C10—C1 | −4.4 (3) | C26—C25—C30—C29 | −3.9 (2) |
C8—C9—C10—C5 | −1.9 (2) | C24—C25—C30—C29 | 177.80 (15) |
S1—C9—C10—C5 | 175.90 (12) | C28—C29—C30—C21 | −172.88 (16) |
C4—C5—C10—C1 | 1.8 (2) | S3—C29—C30—C21 | 12.3 (2) |
C6—C5—C10—C1 | −177.81 (16) | C28—C29—C30—C25 | 5.3 (2) |
C4—C5—C10—C9 | −178.45 (16) | S3—C29—C30—C25 | −169.57 (12) |
C6—C5—C10—C9 | 1.9 (2) | S3—S4—C31—C32 | 1.59 (14) |
S1—S2—C11—C12 | −1.29 (15) | S3—S4—C31—C40 | 177.95 (12) |
S1—S2—C11—C20 | 179.01 (12) | C40—C31—C32—C33 | −0.1 (3) |
C20—C11—C12—C13 | −1.3 (3) | S4—C31—C32—C33 | 176.36 (13) |
S2—C11—C12—C13 | 179.04 (14) | C31—C32—C33—C34 | −3.0 (3) |
C11—C12—C13—C14 | −0.9 (3) | C32—C33—C34—C35 | 2.4 (3) |
C12—C13—C14—C15 | 1.6 (3) | C33—C34—C35—C36 | −179.92 (16) |
C13—C14—C15—C16 | 178.46 (16) | C33—C34—C35—C40 | 1.2 (3) |
C13—C14—C15—C20 | −0.1 (3) | C34—C35—C36—C37 | −178.22 (17) |
C14—C15—C16—C17 | −178.31 (16) | C40—C35—C36—C37 | 0.6 (3) |
C20—C15—C16—C17 | 0.3 (3) | C35—C36—C37—C38 | 2.3 (3) |
C15—C16—C17—C18 | 0.3 (3) | C36—C37—C38—C39 | −3.1 (3) |
C16—C17—C18—C19 | −0.1 (3) | C37—C38—C39—C40 | 0.9 (3) |
C17—C18—C19—C20 | −0.8 (3) | C37—C38—C39—Cl4 | 178.60 (14) |
C17—C18—C19—Cl2 | 178.09 (13) | C38—C39—C40—C35 | 1.9 (2) |
C14—C15—C20—C19 | 177.50 (15) | Cl4—C39—C40—C35 | −175.68 (12) |
C16—C15—C20—C19 | −1.1 (2) | C38—C39—C40—C31 | −177.73 (16) |
C14—C15—C20—C11 | −1.9 (2) | Cl4—C39—C40—C31 | 4.7 (3) |
C16—C15—C20—C11 | 179.50 (15) | C36—C35—C40—C39 | −2.6 (2) |
C18—C19—C20—C15 | 1.3 (2) | C34—C35—C40—C39 | 176.22 (16) |
Cl2—C19—C20—C15 | −177.49 (12) | C36—C35—C40—C31 | 177.03 (16) |
C18—C19—C20—C11 | −179.29 (16) | C34—C35—C40—C31 | −4.1 (2) |
Cl2—C19—C20—C11 | 1.9 (2) | C32—C31—C40—C39 | −176.87 (16) |
C12—C11—C20—C15 | 2.6 (2) | S4—C31—C40—C39 | 6.8 (2) |
S2—C11—C20—C15 | −177.71 (12) | C32—C31—C40—C35 | 3.6 (2) |
C12—C11—C20—C19 | −176.74 (16) | S4—C31—C40—C35 | −172.77 (12) |
C20H12Cl2Se2 | F(000) = 1872 |
Mr = 481.12 | Dx = 1.920 Mg m−3 |
Orthorhombic, Pca21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2c -2ac | Cell parameters from 6129 reflections |
a = 7.8933 (1) Å | θ = 2.1–25.5° |
b = 29.1713 (4) Å | µ = 4.76 mm−1 |
c = 14.4594 (2) Å | T = 103 K |
V = 3329.39 (8) Å3 | Prism, yellow |
Z = 8 | 0.35 × 0.30 × 0.05 mm |
Rigaku Mercury diffractometer | 6129 independent reflections |
Radiation source: fine-focus sealed tube | 5798 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.5°, θmin = 2.1° |
ω scans | h = −9→9 |
Absorption correction: multi-scan Jacobson, R. (1998) Private communication | k = −35→24 |
Tmin = 0.287, Tmax = 0.797 | l = −17→17 |
22104 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.060 | w = 1/[σ2(Fo2) + (0.0339P)2 + 0.0876P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
6129 reflections | Δρmax = 0.41 e Å−3 |
433 parameters | Δρmin = −0.59 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.122 (6) |
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 | ||
Se1 | 0.74230 (4) | 0.337194 (10) | 0.16680 (3) | 0.01725 (8) | |
Se2 | 0.75315 (4) | 0.416685 (10) | 0.16063 (3) | 0.01776 (8) | |
C1 | 0.9777 (4) | 0.31953 (11) | 0.1918 (2) | 0.0176 (7) | |
C2 | 1.0970 (4) | 0.35394 (10) | 0.1928 (2) | 0.0174 (7) | |
H1 | 1.0629 | 0.3845 | 0.1801 | 0.021* | |
C3 | 1.2685 (4) | 0.34480 (12) | 0.2125 (3) | 0.0218 (7) | |
H2 | 1.3491 | 0.3690 | 0.2113 | 0.026* | |
C4 | 1.3187 (4) | 0.30151 (12) | 0.2330 (2) | 0.0179 (7) | |
H3 | 1.4335 | 0.2959 | 0.2492 | 0.021* | |
C5 | 1.2014 (4) | 0.26422 (12) | 0.2308 (2) | 0.0170 (7) | |
C6 | 1.2593 (4) | 0.21996 (11) | 0.2493 (2) | 0.0183 (7) | |
H4 | 1.3751 | 0.2154 | 0.2645 | 0.022* | |
C7 | 1.1521 (4) | 0.18292 (12) | 0.2459 (2) | 0.0202 (7) | |
H5 | 1.1934 | 0.1529 | 0.2578 | 0.024* | |
C8 | 0.9815 (4) | 0.19007 (11) | 0.2248 (2) | 0.0195 (7) | |
H6 | 0.9062 | 0.1647 | 0.2228 | 0.023* | |
C9 | 0.9214 (4) | 0.23307 (10) | 0.2071 (2) | 0.0156 (6) | |
C10 | 1.0265 (4) | 0.27293 (10) | 0.2087 (2) | 0.0156 (6) | |
Cl1 | 0.70751 (9) | 0.23651 (3) | 0.17768 (6) | 0.01977 (17) | |
C11 | 0.8443 (4) | 0.42799 (10) | 0.0360 (2) | 0.0189 (7) | |
C12 | 0.8871 (4) | 0.39000 (10) | −0.0164 (2) | 0.0190 (6) | |
H7 | 0.8686 | 0.3601 | 0.0077 | 0.023* | |
C13 | 0.9574 (4) | 0.39526 (11) | −0.1046 (2) | 0.0236 (7) | |
H8 | 0.9837 | 0.3687 | −0.1398 | 0.028* | |
C14 | 0.9892 (4) | 0.43721 (11) | −0.1413 (2) | 0.0205 (7) | |
H9 | 1.0386 | 0.4399 | −0.2009 | 0.025* | |
C15 | 0.9476 (4) | 0.47719 (11) | −0.0895 (2) | 0.0199 (7) | |
C16 | 0.9808 (4) | 0.52096 (11) | −0.1289 (2) | 0.0231 (7) | |
H10 | 1.0308 | 0.5228 | −0.1886 | 0.028* | |
C17 | 0.9419 (4) | 0.56024 (11) | −0.0826 (2) | 0.0248 (7) | |
H11 | 0.9647 | 0.5892 | −0.1098 | 0.030* | |
C18 | 0.8681 (4) | 0.55764 (11) | 0.0053 (2) | 0.0244 (7) | |
H12 | 0.8412 | 0.5850 | 0.0379 | 0.029* | |
C19 | 0.8348 (4) | 0.51607 (10) | 0.0444 (2) | 0.0190 (7) | |
C20 | 0.8732 (4) | 0.47362 (10) | 0.0007 (2) | 0.0175 (6) | |
Cl2 | 0.73688 (10) | 0.51832 (3) | 0.15364 (6) | 0.02253 (18) | |
Se3 | 0.72583 (4) | 0.157601 (11) | −0.03026 (2) | 0.01737 (9) | |
Se4 | 0.71530 (4) | 0.078749 (10) | −0.00639 (2) | 0.01684 (8) | |
C21 | 0.4888 (3) | 0.17690 (10) | −0.0289 (2) | 0.0163 (6) | |
C22 | 0.3686 (4) | 0.14380 (10) | −0.0171 (2) | 0.0197 (7) | |
H13 | 0.4018 | 0.1125 | −0.0165 | 0.024* | |
C23 | 0.1963 (4) | 0.15506 (10) | −0.0057 (2) | 0.0213 (7) | |
H14 | 0.1141 | 0.1315 | 0.0001 | 0.026* | |
C24 | 0.1477 (4) | 0.19985 (10) | −0.0032 (2) | 0.0192 (6) | |
H15 | 0.0323 | 0.2072 | 0.0079 | 0.023* | |
C25 | 0.2664 (4) | 0.23554 (11) | −0.0167 (2) | 0.0172 (7) | |
C26 | 0.2099 (4) | 0.28113 (11) | −0.0177 (2) | 0.0205 (7) | |
H16 | 0.0939 | 0.2874 | −0.0057 | 0.025* | |
C27 | 0.3168 (4) | 0.31655 (11) | −0.0353 (2) | 0.0225 (7) | |
H17 | 0.2756 | 0.3471 | −0.0363 | 0.027* | |
C28 | 0.4893 (4) | 0.30746 (11) | −0.0521 (2) | 0.0217 (7) | |
H18 | 0.5650 | 0.3320 | −0.0643 | 0.026* | |
C29 | 0.5481 (4) | 0.26339 (11) | −0.0508 (2) | 0.0167 (7) | |
C30 | 0.4428 (4) | 0.22471 (10) | −0.0317 (2) | 0.0152 (6) | |
Cl3 | 0.76188 (9) | 0.25699 (3) | −0.07752 (7) | 0.02151 (17) | |
C31 | 0.6413 (4) | 0.07263 (10) | 0.1219 (2) | 0.0162 (6) | |
C32 | 0.6050 (4) | 0.11194 (10) | 0.1698 (2) | 0.0191 (6) | |
H19 | 0.6241 | 0.1407 | 0.1410 | 0.023* | |
C33 | 0.5402 (4) | 0.11088 (11) | 0.2604 (2) | 0.0208 (7) | |
H20 | 0.5193 | 0.1387 | 0.2926 | 0.025* | |
C34 | 0.5076 (4) | 0.07036 (11) | 0.3017 (2) | 0.0187 (7) | |
H21 | 0.4587 | 0.0699 | 0.3617 | 0.022* | |
C35 | 0.5458 (4) | 0.02833 (11) | 0.2562 (2) | 0.0174 (7) | |
C36 | 0.5114 (4) | −0.01362 (12) | 0.3030 (2) | 0.0218 (7) | |
H22 | 0.4641 | −0.0129 | 0.3634 | 0.026* | |
C37 | 0.5455 (4) | −0.05473 (11) | 0.2622 (2) | 0.0236 (7) | |
H23 | 0.5201 | −0.0825 | 0.2935 | 0.028* | |
C38 | 0.6184 (4) | −0.05573 (10) | 0.1739 (2) | 0.0228 (7) | |
H24 | 0.6455 | −0.0843 | 0.1459 | 0.027* | |
C39 | 0.6508 (4) | −0.01562 (10) | 0.1277 (2) | 0.0184 (7) | |
C40 | 0.6167 (4) | 0.02867 (10) | 0.1646 (2) | 0.0166 (6) | |
Cl4 | 0.74763 (10) | −0.02179 (3) | 0.01936 (6) | 0.02071 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.01572 (14) | 0.01433 (16) | 0.02168 (17) | −0.00062 (11) | −0.00001 (13) | 0.00227 (16) |
Se2 | 0.02007 (15) | 0.01465 (16) | 0.01855 (17) | 0.00169 (11) | 0.00142 (12) | 0.00062 (16) |
C1 | 0.0195 (16) | 0.0192 (17) | 0.0140 (16) | 0.0002 (12) | 0.0020 (12) | −0.0004 (12) |
C2 | 0.0193 (16) | 0.0153 (16) | 0.0177 (16) | −0.0019 (12) | −0.0018 (13) | 0.0015 (12) |
C3 | 0.0210 (18) | 0.0201 (19) | 0.0244 (18) | −0.0042 (13) | −0.0005 (14) | −0.0009 (15) |
C4 | 0.0168 (16) | 0.0182 (18) | 0.0187 (16) | −0.0002 (14) | −0.0011 (12) | 0.0017 (12) |
C5 | 0.0164 (17) | 0.0169 (17) | 0.0177 (17) | −0.0002 (13) | 0.0037 (13) | −0.0011 (12) |
C6 | 0.0216 (17) | 0.0176 (17) | 0.0157 (16) | −0.0008 (14) | 0.0008 (12) | 0.0036 (14) |
C7 | 0.0244 (19) | 0.0168 (18) | 0.0193 (17) | 0.0067 (14) | 0.0013 (13) | −0.0006 (12) |
C8 | 0.0246 (18) | 0.0150 (18) | 0.0188 (17) | −0.0050 (13) | 0.0012 (14) | −0.0020 (13) |
C9 | 0.0151 (15) | 0.0158 (16) | 0.0159 (15) | −0.0028 (12) | 0.0006 (12) | −0.0014 (13) |
C10 | 0.0190 (16) | 0.0168 (17) | 0.0110 (14) | 0.0011 (12) | −0.0002 (13) | 0.0004 (12) |
Cl1 | 0.0171 (3) | 0.0162 (4) | 0.0260 (4) | −0.0020 (3) | −0.0022 (3) | −0.0007 (3) |
C11 | 0.0173 (16) | 0.0213 (17) | 0.0180 (16) | −0.0024 (13) | −0.0014 (13) | 0.0026 (13) |
C12 | 0.0196 (15) | 0.0183 (16) | 0.0191 (16) | 0.0036 (12) | −0.0051 (14) | −0.0040 (14) |
C13 | 0.0296 (17) | 0.0183 (17) | 0.0230 (18) | 0.0035 (13) | −0.0026 (14) | −0.0062 (14) |
C14 | 0.0212 (16) | 0.0257 (18) | 0.0146 (16) | −0.0009 (13) | −0.0004 (13) | 0.0010 (14) |
C15 | 0.0190 (15) | 0.0199 (17) | 0.0208 (16) | −0.0009 (12) | −0.0036 (15) | 0.0012 (15) |
C16 | 0.0230 (17) | 0.027 (2) | 0.0192 (16) | −0.0041 (13) | −0.0034 (14) | 0.0053 (15) |
C17 | 0.0323 (18) | 0.0161 (16) | 0.0259 (17) | −0.0052 (14) | −0.0036 (16) | 0.0043 (15) |
C18 | 0.0289 (18) | 0.0169 (16) | 0.0274 (18) | 0.0019 (13) | −0.0083 (16) | −0.0008 (14) |
C19 | 0.0177 (16) | 0.0195 (17) | 0.0198 (16) | 0.0018 (13) | −0.0020 (13) | −0.0007 (13) |
C20 | 0.0141 (14) | 0.0209 (16) | 0.0176 (15) | −0.0010 (11) | −0.0040 (14) | 0.0002 (14) |
Cl2 | 0.0295 (4) | 0.0177 (4) | 0.0204 (4) | 0.0037 (3) | 0.0007 (3) | −0.0023 (4) |
Se3 | 0.01571 (15) | 0.01336 (17) | 0.0231 (2) | −0.00035 (11) | 0.00131 (16) | 0.00212 (13) |
Se4 | 0.01997 (14) | 0.01314 (16) | 0.01742 (17) | 0.00077 (11) | 0.00120 (16) | 0.00031 (13) |
C21 | 0.0166 (14) | 0.0193 (17) | 0.0131 (15) | −0.0002 (12) | 0.0020 (12) | 0.0013 (13) |
C22 | 0.0236 (16) | 0.0147 (16) | 0.0208 (17) | 0.0005 (12) | −0.0033 (14) | 0.0021 (13) |
C23 | 0.0203 (16) | 0.0238 (17) | 0.0199 (17) | −0.0049 (12) | −0.0011 (14) | 0.0055 (16) |
C24 | 0.0170 (14) | 0.0217 (16) | 0.0190 (15) | 0.0007 (12) | −0.0019 (14) | 0.0014 (14) |
C25 | 0.0177 (15) | 0.0192 (17) | 0.0146 (17) | 0.0014 (11) | −0.0025 (13) | −0.0015 (14) |
C26 | 0.0211 (15) | 0.0218 (17) | 0.0187 (18) | 0.0031 (13) | −0.0021 (14) | −0.0031 (14) |
C27 | 0.0266 (17) | 0.0138 (16) | 0.0270 (18) | 0.0042 (13) | −0.0060 (16) | −0.0049 (14) |
C28 | 0.0241 (16) | 0.0181 (18) | 0.0228 (17) | −0.0047 (13) | −0.0054 (13) | 0.0008 (13) |
C29 | 0.0159 (15) | 0.0191 (17) | 0.0150 (15) | −0.0011 (12) | −0.0017 (12) | −0.0005 (12) |
C30 | 0.0179 (15) | 0.0160 (16) | 0.0118 (15) | −0.0010 (11) | −0.0014 (13) | −0.0004 (12) |
Cl3 | 0.0183 (3) | 0.0173 (4) | 0.0289 (4) | −0.0024 (3) | 0.0010 (3) | 0.0045 (4) |
C31 | 0.0136 (14) | 0.0182 (16) | 0.0168 (15) | −0.0013 (12) | −0.0060 (13) | −0.0011 (12) |
C32 | 0.0201 (15) | 0.0148 (15) | 0.0225 (16) | 0.0013 (12) | −0.0067 (15) | 0.0014 (14) |
C33 | 0.0248 (18) | 0.0185 (17) | 0.0192 (17) | 0.0039 (14) | −0.0013 (15) | −0.0061 (14) |
C34 | 0.0202 (16) | 0.0210 (18) | 0.0149 (16) | 0.0049 (13) | −0.0026 (13) | −0.0023 (13) |
C35 | 0.0166 (16) | 0.0176 (17) | 0.0179 (16) | −0.0001 (13) | −0.0022 (13) | 0.0001 (13) |
C36 | 0.0230 (17) | 0.0235 (17) | 0.0191 (18) | −0.0001 (13) | −0.0029 (13) | 0.0036 (14) |
C37 | 0.0304 (19) | 0.0173 (18) | 0.0232 (17) | 0.0003 (14) | 0.0020 (16) | 0.0063 (15) |
C38 | 0.0284 (17) | 0.0154 (16) | 0.0245 (17) | 0.0011 (13) | −0.0050 (15) | −0.0006 (14) |
C39 | 0.0210 (16) | 0.0193 (17) | 0.0149 (15) | 0.0048 (12) | −0.0026 (13) | −0.0015 (13) |
C40 | 0.0155 (14) | 0.0181 (16) | 0.0162 (15) | 0.0015 (11) | −0.0074 (14) | −0.0012 (13) |
Cl4 | 0.0288 (4) | 0.0155 (4) | 0.0179 (5) | 0.0047 (3) | 0.0007 (3) | −0.0014 (3) |
Se1—C1 | 1.962 (3) | Se3—C21 | 1.954 (3) |
Se1—Se2 | 2.3222 (4) | Se3—Se4 | 2.3275 (4) |
Se2—C11 | 1.968 (3) | Se4—C31 | 1.953 (3) |
C1—C2 | 1.376 (4) | C21—C22 | 1.365 (4) |
C1—C10 | 1.434 (4) | C21—C30 | 1.442 (4) |
C2—C3 | 1.409 (4) | C22—C23 | 1.408 (4) |
C2—H1 | 0.9500 | C22—H13 | 0.9500 |
C3—C4 | 1.357 (5) | C23—C24 | 1.362 (4) |
C3—H2 | 0.9500 | C23—H14 | 0.9500 |
C4—C5 | 1.429 (5) | C24—C25 | 1.414 (4) |
C4—H3 | 0.9500 | C24—H15 | 0.9500 |
C5—C6 | 1.396 (5) | C25—C26 | 1.402 (4) |
C5—C10 | 1.440 (4) | C25—C30 | 1.444 (4) |
C6—C7 | 1.373 (5) | C26—C27 | 1.358 (4) |
C6—H4 | 0.9500 | C26—H16 | 0.9500 |
C7—C8 | 1.397 (5) | C27—C28 | 1.408 (4) |
C7—H5 | 0.9500 | C27—H17 | 0.9500 |
C8—C9 | 1.365 (4) | C28—C29 | 1.367 (4) |
C8—H6 | 0.9500 | C28—H18 | 0.9500 |
C9—C10 | 1.429 (4) | C29—C30 | 1.428 (4) |
C9—Cl1 | 1.744 (3) | C29—Cl3 | 1.741 (3) |
C11—C12 | 1.384 (4) | C31—C32 | 1.370 (4) |
C11—C20 | 1.444 (4) | C31—C40 | 1.437 (4) |
C12—C13 | 1.399 (4) | C32—C33 | 1.408 (5) |
C12—H7 | 0.9500 | C32—H19 | 0.9500 |
C13—C14 | 1.357 (4) | C33—C34 | 1.348 (4) |
C13—H8 | 0.9500 | C33—H20 | 0.9500 |
C14—C15 | 1.424 (4) | C34—C35 | 1.423 (4) |
C14—H9 | 0.9500 | C34—H21 | 0.9500 |
C15—C16 | 1.423 (4) | C35—C36 | 1.424 (5) |
C15—C20 | 1.434 (5) | C35—C40 | 1.438 (5) |
C16—C17 | 1.363 (5) | C36—C37 | 1.363 (5) |
C16—H10 | 0.9500 | C36—H22 | 0.9500 |
C17—C18 | 1.400 (5) | C37—C38 | 1.402 (5) |
C17—H11 | 0.9500 | C37—H23 | 0.9500 |
C18—C19 | 1.363 (4) | C38—C39 | 1.372 (4) |
C18—H12 | 0.9500 | C38—H24 | 0.9500 |
C19—C20 | 1.423 (4) | C39—C40 | 1.424 (4) |
C19—Cl2 | 1.760 (3) | C39—Cl4 | 1.752 (3) |
C1—Se1—Se2 | 103.56 (9) | C21—Se3—Se4 | 104.42 (9) |
C11—Se2—Se1 | 102.47 (9) | C31—Se4—Se3 | 104.00 (9) |
C2—C1—C10 | 120.4 (3) | C22—C21—C30 | 120.8 (3) |
C2—C1—Se1 | 117.3 (2) | C22—C21—Se3 | 117.6 (2) |
C10—C1—Se1 | 122.3 (2) | C30—C21—Se3 | 121.3 (2) |
C1—C2—C3 | 121.4 (3) | C21—C22—C23 | 121.4 (3) |
C1—C2—H1 | 119.3 | C21—C22—H13 | 119.3 |
C3—C2—H1 | 119.3 | C23—C22—H13 | 119.3 |
C4—C3—C2 | 120.1 (3) | C24—C23—C22 | 119.9 (3) |
C4—C3—H2 | 120.0 | C24—C23—H14 | 120.0 |
C2—C3—H2 | 120.0 | C22—C23—H14 | 120.0 |
C3—C4—C5 | 121.0 (3) | C23—C24—C25 | 121.1 (3) |
C3—C4—H3 | 119.5 | C23—C24—H15 | 119.5 |
C5—C4—H3 | 119.5 | C25—C24—H15 | 119.5 |
C6—C5—C4 | 119.2 (3) | C26—C25—C24 | 119.3 (3) |
C6—C5—C10 | 121.3 (3) | C26—C25—C30 | 120.8 (3) |
C4—C5—C10 | 119.5 (3) | C24—C25—C30 | 119.9 (3) |
C7—C6—C5 | 121.3 (3) | C27—C26—C25 | 121.8 (3) |
C7—C6—H4 | 119.3 | C27—C26—H16 | 119.1 |
C5—C6—H4 | 119.3 | C25—C26—H16 | 119.1 |
C6—C7—C8 | 119.0 (3) | C26—C27—C28 | 119.3 (3) |
C6—C7—H5 | 120.5 | C26—C27—H17 | 120.4 |
C8—C7—H5 | 120.5 | C28—C27—H17 | 120.4 |
C9—C8—C7 | 120.9 (3) | C29—C28—C27 | 120.2 (3) |
C9—C8—H6 | 119.6 | C29—C28—H18 | 119.9 |
C7—C8—H6 | 119.6 | C27—C28—H18 | 119.9 |
C8—C9—C10 | 122.9 (3) | C28—C29—C30 | 123.2 (3) |
C8—C9—Cl1 | 115.8 (2) | C28—C29—Cl3 | 115.3 (2) |
C10—C9—Cl1 | 121.3 (2) | C30—C29—Cl3 | 121.5 (2) |
C9—C10—C1 | 127.8 (3) | C29—C30—C21 | 128.5 (3) |
C9—C10—C5 | 114.6 (3) | C29—C30—C25 | 114.7 (3) |
C1—C10—C5 | 117.6 (3) | C21—C30—C25 | 116.8 (3) |
C12—C11—C20 | 120.4 (3) | C32—C31—C40 | 120.1 (3) |
C12—C11—Se2 | 117.1 (2) | C32—C31—Se4 | 117.8 (2) |
C20—C11—Se2 | 122.4 (2) | C40—C31—Se4 | 122.1 (2) |
C11—C12—C13 | 120.5 (3) | C31—C32—C33 | 121.9 (3) |
C11—C12—H7 | 119.7 | C31—C32—H19 | 119.0 |
C13—C12—H7 | 119.7 | C33—C32—H19 | 119.0 |
C14—C13—C12 | 121.9 (3) | C34—C33—C32 | 120.0 (3) |
C14—C13—H8 | 119.1 | C34—C33—H20 | 120.0 |
C12—C13—H8 | 119.1 | C32—C33—H20 | 120.0 |
C13—C14—C15 | 119.4 (3) | C33—C34—C35 | 120.7 (3) |
C13—C14—H9 | 120.3 | C33—C34—H21 | 119.6 |
C15—C14—H9 | 120.3 | C35—C34—H21 | 119.6 |
C16—C15—C14 | 118.8 (3) | C34—C35—C36 | 118.8 (3) |
C16—C15—C20 | 120.3 (3) | C34—C35—C40 | 120.1 (3) |
C14—C15—C20 | 120.8 (3) | C36—C35—C40 | 121.1 (3) |
C17—C16—C15 | 121.1 (3) | C37—C36—C35 | 120.9 (3) |
C17—C16—H10 | 119.5 | C37—C36—H22 | 119.6 |
C15—C16—H10 | 119.5 | C35—C36—H22 | 119.6 |
C16—C17—C18 | 119.6 (3) | C36—C37—C38 | 119.6 (3) |
C16—C17—H11 | 120.2 | C36—C37—H23 | 120.2 |
C18—C17—H11 | 120.2 | C38—C37—H23 | 120.2 |
C19—C18—C17 | 120.3 (3) | C39—C38—C37 | 120.2 (3) |
C19—C18—H12 | 119.9 | C39—C38—H24 | 119.9 |
C17—C18—H12 | 119.9 | C37—C38—H24 | 119.9 |
C18—C19—C20 | 123.3 (3) | C38—C39—C40 | 123.8 (3) |
C18—C19—Cl2 | 115.0 (2) | C38—C39—Cl4 | 115.4 (2) |
C20—C19—Cl2 | 121.6 (2) | C40—C39—Cl4 | 120.8 (2) |
C19—C20—C15 | 115.3 (3) | C39—C40—C31 | 128.5 (3) |
C19—C20—C11 | 127.7 (3) | C39—C40—C35 | 114.4 (3) |
C15—C20—C11 | 117.0 (3) | C31—C40—C35 | 117.1 (3) |
C1—Se1—Se2—C11 | 78.78 (13) | C21—Se3—Se4—C31 | −69.44 (13) |
Se2—Se1—C1—C2 | −5.1 (2) | Se4—Se3—C21—C22 | −1.2 (3) |
Se2—Se1—C1—C10 | 174.7 (2) | Se4—Se3—C21—C30 | 173.3 (2) |
C10—C1—C2—C3 | −1.4 (5) | C30—C21—C22—C23 | −1.1 (5) |
Se1—C1—C2—C3 | 178.4 (3) | Se3—C21—C22—C23 | 173.4 (2) |
C1—C2—C3—C4 | −1.6 (5) | C21—C22—C23—C24 | −2.3 (5) |
C2—C3—C4—C5 | 3.1 (5) | C22—C23—C24—C25 | 3.4 (5) |
C3—C4—C5—C6 | 177.8 (3) | C23—C24—C25—C26 | 177.1 (3) |
C3—C4—C5—C10 | −1.7 (5) | C23—C24—C25—C30 | −1.3 (5) |
C4—C5—C6—C7 | −178.5 (3) | C24—C25—C26—C27 | −176.4 (3) |
C10—C5—C6—C7 | 0.9 (5) | C30—C25—C26—C27 | 1.9 (5) |
C5—C6—C7—C8 | −0.9 (5) | C25—C26—C27—C28 | −0.7 (5) |
C6—C7—C8—C9 | 0.5 (5) | C26—C27—C28—C29 | 0.2 (5) |
C7—C8—C9—C10 | 0.1 (5) | C27—C28—C29—C30 | −0.9 (5) |
C7—C8—C9—Cl1 | 177.7 (2) | C27—C28—C29—Cl3 | 177.4 (3) |
C8—C9—C10—C1 | −179.7 (3) | C28—C29—C30—C21 | 179.6 (3) |
Cl1—C9—C10—C1 | 2.8 (5) | Cl3—C29—C30—C21 | 1.4 (4) |
C8—C9—C10—C5 | −0.1 (5) | C28—C29—C30—C25 | 2.0 (4) |
Cl1—C9—C10—C5 | −177.7 (2) | Cl3—C29—C30—C25 | −176.2 (2) |
C2—C1—C10—C9 | −177.7 (3) | C22—C21—C30—C29 | −174.4 (3) |
Se1—C1—C10—C9 | 2.6 (4) | Se3—C21—C30—C29 | 11.3 (4) |
C2—C1—C10—C5 | 2.8 (4) | C22—C21—C30—C25 | 3.2 (4) |
Se1—C1—C10—C5 | −177.0 (2) | Se3—C21—C30—C25 | −171.2 (2) |
C6—C5—C10—C9 | −0.3 (5) | C26—C25—C30—C29 | −2.5 (4) |
C4—C5—C10—C9 | 179.1 (3) | C24—C25—C30—C29 | 175.9 (3) |
C6—C5—C10—C1 | 179.3 (3) | C26—C25—C30—C21 | 179.6 (3) |
C4—C5—C10—C1 | −1.3 (4) | C24—C25—C30—C21 | −2.0 (4) |
Se1—Se2—C11—C12 | −2.7 (3) | Se3—Se4—C31—C32 | 2.5 (3) |
Se1—Se2—C11—C20 | 179.9 (2) | Se3—Se4—C31—C40 | 179.4 (2) |
C20—C11—C12—C13 | −0.6 (5) | C40—C31—C32—C33 | −1.2 (5) |
Se2—C11—C12—C13 | −178.1 (2) | Se4—C31—C32—C33 | 175.7 (2) |
C11—C12—C13—C14 | 1.2 (5) | C31—C32—C33—C34 | −1.9 (5) |
C12—C13—C14—C15 | −1.0 (5) | C32—C33—C34—C35 | 3.1 (5) |
C13—C14—C15—C16 | −179.7 (3) | C33—C34—C35—C36 | 179.1 (3) |
C13—C14—C15—C20 | 0.1 (5) | C33—C34—C35—C40 | −1.3 (5) |
C14—C15—C16—C17 | 179.4 (3) | C34—C35—C36—C37 | 179.9 (3) |
C20—C15—C16—C17 | −0.4 (5) | C40—C35—C36—C37 | 0.3 (5) |
C15—C16—C17—C18 | 0.0 (5) | C35—C36—C37—C38 | 1.2 (5) |
C16—C17—C18—C19 | −0.2 (5) | C36—C37—C38—C39 | −1.8 (5) |
C17—C18—C19—C20 | 0.8 (5) | C37—C38—C39—C40 | 0.9 (5) |
C17—C18—C19—Cl2 | −178.4 (2) | C37—C38—C39—Cl4 | 178.2 (3) |
C18—C19—C20—C15 | −1.1 (5) | C38—C39—C40—C31 | −178.3 (3) |
Cl2—C19—C20—C15 | 178.0 (2) | Cl4—C39—C40—C31 | 4.5 (5) |
C18—C19—C20—C11 | 179.6 (3) | C38—C39—C40—C35 | 0.6 (5) |
Cl2—C19—C20—C11 | −1.3 (5) | Cl4—C39—C40—C35 | −176.6 (2) |
C16—C15—C20—C19 | 0.9 (4) | C32—C31—C40—C39 | −178.2 (3) |
C14—C15—C20—C19 | −178.9 (3) | Se4—C31—C40—C39 | 4.9 (4) |
C16—C15—C20—C11 | −179.7 (3) | C32—C31—C40—C35 | 2.9 (4) |
C14—C15—C20—C11 | 0.5 (4) | Se4—C31—C40—C35 | −173.9 (2) |
C12—C11—C20—C19 | 179.0 (3) | C34—C35—C40—C39 | 179.2 (3) |
Se2—C11—C20—C19 | −3.6 (5) | C36—C35—C40—C39 | −1.2 (4) |
C12—C11—C20—C15 | −0.3 (4) | C34—C35—C40—C31 | −1.7 (4) |
Se2—C11—C20—C15 | 177.1 (2) | C36—C35—C40—C31 | 177.9 (3) |
C20H12Br2Se2 | Z = 2 |
Mr = 570.04 | F(000) = 540 |
Triclinic, P1 | Dx = 2.179 Mg m−3 |
a = 7.8394 (1) Å | Mo Kα radiation, λ = 0.71075 Å |
b = 8.0986 (2) Å | Cell parameters from 19136 reflections |
c = 15.0650 (4) Å | θ = 2.9–27.1° |
α = 90.941 (1)° | µ = 8.85 mm−1 |
β = 101.888 (1)° | T = 103 K |
γ = 111.093 (1)° | Platelet, colorless |
V = 868.92 (3) Å3 | 0.04 × 0.03 × 0.01 mm |
Rigaku VariMax Saturn diffractometer | 3813 independent reflections |
Radiation source: rotating-anode X-ray tube | 3566 reflections with I > 2σ(I) |
Detector resolution: 28.5714 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 27.1°, θmin = 2.9° |
Absorption correction: multi-scan MULABS - Empirical Correction for Absorption Anisotropy. Blessing, R. H., Acta Cryst., A51, 33-38 (1995). | h = −10→10 |
Tmin = 0.734, Tmax = 0.915 | k = −10→10 |
19136 measured reflections | l = −19→19 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0128P)2 + 4.9343P] where P = (Fo2 + 2Fc2)/3 |
S = 1.20 | (Δ/σ)max < 0.001 |
3813 reflections | Δρmax = 1.68 e Å−3 |
217 parameters | Δρmin = −1.28 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. |
x | y | z | Uiso*/Ueq | ||
Se1 | 0.26581 (6) | 0.37824 (6) | 0.22084 (3) | 0.02072 (11) | |
C1 | 0.4946 (6) | 0.4073 (6) | 0.1793 (3) | 0.0186 (9) | |
C2 | 0.5691 (6) | 0.2788 (6) | 0.1976 (3) | 0.0211 (9) | |
H1 | 0.5129 | 0.1860 | 0.2324 | 0.025* | |
C3 | 0.7285 (6) | 0.2813 (6) | 0.1657 (3) | 0.0226 (9) | |
H2 | 0.7792 | 0.1924 | 0.1809 | 0.027* | |
C4 | 0.8081 (6) | 0.4076 (6) | 0.1144 (3) | 0.0211 (9) | |
H3 | 0.9106 | 0.4044 | 0.0910 | 0.025* | |
C6 | 0.8282 (7) | 0.6830 (7) | 0.0423 (3) | 0.0254 (10) | |
H4 | 0.9310 | 0.6771 | 0.0200 | 0.030* | |
C5 | 0.7383 (6) | 0.5480 (6) | 0.0948 (3) | 0.0202 (9) | |
C7 | 0.7700 (7) | 0.8208 (7) | 0.0232 (3) | 0.0278 (11) | |
H5 | 0.8294 | 0.9081 | −0.0133 | 0.033* | |
C8 | 0.6223 (7) | 0.8323 (6) | 0.0580 (3) | 0.0248 (10) | |
H6 | 0.5837 | 0.9300 | 0.0465 | 0.030* | |
C9 | 0.5324 (6) | 0.7036 (6) | 0.1086 (3) | 0.0198 (9) | |
C10 | 0.5800 (6) | 0.5522 (6) | 0.1289 (3) | 0.0176 (9) | |
Br1 | 0.34007 (7) | 0.75008 (6) | 0.15271 (3) | 0.02680 (12) | |
Se2 | 0.16608 (6) | 0.08531 (6) | 0.25856 (3) | 0.02035 (11) | |
C11 | 0.2914 (6) | 0.1141 (6) | 0.3882 (3) | 0.0176 (8) | |
C12 | 0.4468 (6) | 0.2661 (6) | 0.4198 (3) | 0.0187 (9) | |
H7 | 0.4981 | 0.3442 | 0.3775 | 0.022* | |
C13 | 0.5315 (6) | 0.3083 (6) | 0.5130 (3) | 0.0210 (9) | |
H8 | 0.6410 | 0.4124 | 0.5330 | 0.025* | |
C14 | 0.4577 (6) | 0.2013 (6) | 0.5749 (3) | 0.0207 (9) | |
H9 | 0.5115 | 0.2346 | 0.6381 | 0.025* | |
C15 | 0.3004 (6) | 0.0396 (6) | 0.5457 (3) | 0.0199 (9) | |
C16 | 0.2284 (7) | −0.0706 (6) | 0.6114 (3) | 0.0225 (9) | |
H10 | 0.2832 | −0.0333 | 0.6743 | 0.027* | |
C17 | 0.0816 (7) | −0.2296 (6) | 0.5866 (3) | 0.0252 (10) | |
H11 | 0.0332 | −0.3012 | 0.6317 | 0.030* | |
C18 | 0.0037 (7) | −0.2859 (6) | 0.4943 (3) | 0.0239 (10) | |
H12 | −0.0972 | −0.3972 | 0.4764 | 0.029* | |
C19 | 0.0718 (6) | −0.1816 (6) | 0.4294 (3) | 0.0208 (9) | |
C20 | 0.2182 (6) | −0.0107 (6) | 0.4500 (3) | 0.0174 (8) | |
Br2 | −0.03156 (8) | −0.29027 (7) | 0.30718 (4) | 0.03614 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Se1 | 0.0214 (2) | 0.0259 (2) | 0.0209 (2) | 0.01372 (19) | 0.00830 (17) | 0.00804 (17) |
C1 | 0.018 (2) | 0.023 (2) | 0.017 (2) | 0.0100 (18) | 0.0025 (17) | 0.0023 (17) |
C2 | 0.025 (2) | 0.022 (2) | 0.017 (2) | 0.0138 (19) | −0.0009 (18) | 0.0029 (17) |
C3 | 0.021 (2) | 0.026 (2) | 0.023 (2) | 0.0131 (19) | 0.0006 (18) | 0.0011 (18) |
C4 | 0.013 (2) | 0.038 (3) | 0.013 (2) | 0.0108 (19) | 0.0026 (16) | −0.0023 (18) |
C6 | 0.020 (2) | 0.035 (3) | 0.020 (2) | 0.008 (2) | 0.0071 (18) | 0.007 (2) |
C5 | 0.017 (2) | 0.028 (2) | 0.014 (2) | 0.0082 (18) | 0.0020 (17) | 0.0007 (17) |
C7 | 0.025 (2) | 0.028 (2) | 0.023 (2) | 0.001 (2) | 0.0043 (19) | 0.0081 (19) |
C8 | 0.029 (3) | 0.020 (2) | 0.021 (2) | 0.0064 (19) | 0.0012 (19) | 0.0045 (18) |
C9 | 0.019 (2) | 0.025 (2) | 0.017 (2) | 0.0099 (18) | 0.0018 (17) | −0.0002 (17) |
C10 | 0.019 (2) | 0.020 (2) | 0.0115 (19) | 0.0075 (17) | −0.0009 (16) | 0.0016 (16) |
Br1 | 0.0313 (3) | 0.0274 (2) | 0.0295 (3) | 0.0188 (2) | 0.0090 (2) | 0.00727 (19) |
Se2 | 0.0202 (2) | 0.0233 (2) | 0.0169 (2) | 0.00678 (18) | 0.00514 (17) | 0.00346 (17) |
C11 | 0.018 (2) | 0.018 (2) | 0.019 (2) | 0.0087 (17) | 0.0048 (17) | 0.0015 (16) |
C12 | 0.021 (2) | 0.019 (2) | 0.020 (2) | 0.0100 (18) | 0.0077 (17) | 0.0055 (17) |
C13 | 0.021 (2) | 0.016 (2) | 0.027 (2) | 0.0090 (18) | 0.0056 (19) | 0.0030 (18) |
C14 | 0.022 (2) | 0.024 (2) | 0.019 (2) | 0.0131 (18) | 0.0017 (18) | 0.0030 (17) |
C15 | 0.025 (2) | 0.019 (2) | 0.023 (2) | 0.0156 (18) | 0.0083 (18) | 0.0059 (17) |
C16 | 0.029 (2) | 0.025 (2) | 0.022 (2) | 0.018 (2) | 0.0094 (19) | 0.0076 (18) |
C17 | 0.028 (2) | 0.026 (2) | 0.032 (3) | 0.016 (2) | 0.016 (2) | 0.015 (2) |
C18 | 0.020 (2) | 0.020 (2) | 0.034 (3) | 0.0088 (18) | 0.009 (2) | 0.0063 (19) |
C19 | 0.020 (2) | 0.020 (2) | 0.026 (2) | 0.0105 (18) | 0.0072 (18) | 0.0034 (18) |
C20 | 0.020 (2) | 0.017 (2) | 0.019 (2) | 0.0112 (17) | 0.0064 (17) | 0.0053 (16) |
Br2 | 0.0418 (3) | 0.0234 (2) | 0.0269 (3) | −0.0043 (2) | 0.0032 (2) | −0.00139 (19) |
Se1—C1 | 1.956 (4) | Se2—C11 | 1.966 (4) |
Se1—Se2 | 2.3354 (6) | C11—C12 | 1.374 (6) |
C1—C2 | 1.371 (6) | C11—C20 | 1.431 (6) |
C1—C10 | 1.441 (6) | C12—C13 | 1.403 (6) |
C2—C3 | 1.422 (6) | C12—H7 | 0.9500 |
C2—H1 | 0.9500 | C13—C14 | 1.357 (6) |
C3—C4 | 1.341 (7) | C13—H8 | 0.9500 |
C3—H2 | 0.9500 | C14—C15 | 1.423 (6) |
C4—C5 | 1.439 (6) | C14—H9 | 0.9500 |
C4—H3 | 0.9500 | C15—C16 | 1.412 (6) |
C6—C7 | 1.363 (7) | C15—C20 | 1.439 (6) |
C6—C5 | 1.422 (6) | C16—C17 | 1.365 (7) |
C6—H4 | 0.9500 | C16—H10 | 0.9500 |
C5—C10 | 1.448 (6) | C17—C18 | 1.393 (7) |
C7—C8 | 1.396 (7) | C17—H11 | 0.9500 |
C7—H5 | 0.9500 | C18—C19 | 1.368 (6) |
C8—C9 | 1.372 (6) | C18—H12 | 0.9500 |
C8—H6 | 0.9500 | C19—C20 | 1.424 (6) |
C9—C10 | 1.425 (6) | C19—Br2 | 1.908 (5) |
C9—Br1 | 1.916 (4) | ||
C1—Se1—Se2 | 103.37 (13) | C11—Se2—Se1 | 102.15 (13) |
C2—C1—C10 | 120.4 (4) | C12—C11—C20 | 120.3 (4) |
C2—C1—Se1 | 116.9 (3) | C12—C11—Se2 | 117.5 (3) |
C10—C1—Se1 | 122.6 (3) | C20—C11—Se2 | 122.1 (3) |
C1—C2—C3 | 121.4 (4) | C11—C12—C13 | 121.4 (4) |
C1—C2—H1 | 119.3 | C11—C12—H7 | 119.3 |
C3—C2—H1 | 119.3 | C13—C12—H7 | 119.3 |
C4—C3—C2 | 120.8 (4) | C14—C13—C12 | 120.3 (4) |
C4—C3—H2 | 119.6 | C14—C13—H8 | 119.8 |
C2—C3—H2 | 119.6 | C12—C13—H8 | 119.8 |
C3—C4—C5 | 120.0 (4) | C13—C14—C15 | 120.5 (4) |
C3—C4—H3 | 120.0 | C13—C14—H9 | 119.7 |
C5—C4—H3 | 120.0 | C15—C14—H9 | 119.7 |
C7—C6—C5 | 121.3 (4) | C16—C15—C14 | 119.3 (4) |
C7—C6—H4 | 119.3 | C16—C15—C20 | 120.8 (4) |
C5—C6—H4 | 119.3 | C14—C15—C20 | 119.8 (4) |
C6—C5—C4 | 119.0 (4) | C17—C16—C15 | 121.4 (5) |
C6—C5—C10 | 120.7 (4) | C17—C16—H10 | 119.3 |
C4—C5—C10 | 120.4 (4) | C15—C16—H10 | 119.3 |
C6—C7—C8 | 119.4 (4) | C16—C17—C18 | 119.3 (4) |
C6—C7—H5 | 120.3 | C16—C17—H11 | 120.4 |
C8—C7—H5 | 120.3 | C18—C17—H11 | 120.4 |
C9—C8—C7 | 120.5 (4) | C19—C18—C17 | 120.4 (4) |
C9—C8—H6 | 119.8 | C19—C18—H12 | 119.8 |
C7—C8—H6 | 119.8 | C17—C18—H12 | 119.8 |
C8—C9—C10 | 123.7 (4) | C18—C19—C20 | 123.7 (4) |
C8—C9—Br1 | 113.4 (3) | C18—C19—Br2 | 114.7 (3) |
C10—C9—Br1 | 122.9 (3) | C20—C19—Br2 | 121.5 (3) |
C9—C10—C1 | 128.9 (4) | C19—C20—C11 | 128.4 (4) |
C9—C10—C5 | 114.3 (4) | C19—C20—C15 | 114.3 (4) |
C1—C10—C5 | 116.8 (4) | C11—C20—C15 | 117.2 (4) |
C10—C1—C2—C3 | −1.7 (7) | C20—C11—C12—C13 | −3.6 (6) |
Se1—C1—C2—C3 | 176.1 (3) | Se2—C11—C12—C13 | 172.1 (3) |
C1—C2—C3—C4 | −1.8 (7) | C11—C12—C13—C14 | −1.8 (7) |
C2—C3—C4—C5 | 3.1 (7) | C12—C13—C14—C15 | 3.7 (7) |
C7—C6—C5—C4 | −178.8 (4) | C13—C14—C15—C16 | 179.0 (4) |
C7—C6—C5—C10 | 0.7 (7) | C13—C14—C15—C20 | −0.3 (6) |
C3—C4—C5—C6 | 178.3 (4) | C14—C15—C16—C17 | −177.8 (4) |
C3—C4—C5—C10 | −1.1 (7) | C20—C15—C16—C17 | 1.4 (7) |
C5—C6—C7—C8 | 1.7 (7) | C15—C16—C17—C18 | 1.3 (7) |
C6—C7—C8—C9 | −1.9 (7) | C16—C17—C18—C19 | −0.9 (7) |
C7—C8—C9—C10 | −0.3 (7) | C17—C18—C19—C20 | −2.1 (7) |
C7—C8—C9—Br1 | 178.0 (4) | C17—C18—C19—Br2 | 173.2 (3) |
C8—C9—C10—C1 | −178.6 (4) | C18—C19—C20—C11 | −175.4 (4) |
Br1—C9—C10—C1 | 3.2 (7) | Br2—C19—C20—C11 | 9.5 (6) |
C8—C9—C10—C5 | 2.5 (6) | C18—C19—C20—C15 | 4.5 (6) |
Br1—C9—C10—C5 | −175.6 (3) | Br2—C19—C20—C15 | −170.6 (3) |
C2—C1—C10—C9 | −175.2 (4) | C12—C11—C20—C19 | −173.3 (4) |
Se1—C1—C10—C9 | 7.0 (7) | Se2—C11—C20—C19 | 11.2 (6) |
C2—C1—C10—C5 | 3.6 (6) | C12—C11—C20—C15 | 6.8 (6) |
Se1—C1—C10—C5 | −174.2 (3) | Se2—C11—C20—C15 | −168.8 (3) |
C6—C5—C10—C9 | −2.7 (6) | C16—C15—C20—C19 | −4.1 (6) |
C4—C5—C10—C9 | 176.8 (4) | C14—C15—C20—C19 | 175.2 (4) |
C6—C5—C10—C1 | 178.4 (4) | C16—C15—C20—C11 | 175.8 (4) |
C4—C5—C10—C1 | −2.2 (6) | C14—C15—C20—C11 | −4.9 (6) |
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