The nature of E2X2 σ(4c–6e) of the X-*-E-*-E-*-X type is elucidated for 1-(8-XC10H6)E–E(C10H6X-8′)-1′ [(1) E, X = S, Cl; (2) S, Br; (3) Se, Cl; (4) Se, Br] after structural determination of (1), (3) and (4), together with model A [MeX---E(H)—E(H)---XMe (E = S and Se; X = Cl and Br)]. The quantum theory of atoms-in-molecules dual functional analysis (QTAIM-DFA) is applied. The total electron energy densities Hb(rc) are plotted versus Hb(rc) – Vb(rc)/2 for the interactions at the bond critical points (BCPs; *), where Vb(rc) show the potential energy densities at the BCPs. Data for the perturbed structures around the fully optimized structures are employed for the plots, in addition to those of the fully optimized structures. The plots were analysed using the polar coordinate (R, θ) representation of the data of the fully optimized structures. Data containing the perturbed structures were analysed by (θp, κp), where θp corresponds to the tangent line of the plot and κp is the curvature. Whereas (R, θ) shows the static nature, (θp, κp) represents the dynamic nature of interactions. E-*-E are all classified as shared shell (S) interactions for (1)–(4) and as weak covalent (Cov-w) in nature (S/Cov-w). The nature of pure CS (closed shell)/typical-HB (hydrogen bond) with no covalency is predicted for E-*-X in (1) and (3), regular CS/typical-HB nature with covalency is predicted for (4), and an intermediate nature is predicted for (2). The NBO energies evaluated for E-*-X in (1)–(4) are substantially larger than those in model A due the shortened length at the naphthalene 1,8-positions. The nature of E2X2 of σ(4c–6e) is well elucidated via QTAIM-DFA.
Supporting information
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.
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Crystal data top
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 |
Data collection top
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 top
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 |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |