Nature of E2X2 σ(4c–6e) of the X---E—E---X type at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

Tsubomoto, Y.; Hayashi, S.; Nakanishi, W.; Sasamori, T.; Tokitoh, N.

doi:10.1107/S205252061700364X

Nature of E₂X₂ σ(4c–6e) of the X---E—E---X type at naphthalene 1,8-positions and model, elucidated by X-ray crystallographic analysis and QC calculations with the QTAIM approach

Y. Tsubomoto, S. Hayashi, W. Nakanishi, T. Sasamori and N. Tokitoh

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 H_b(r_c) are plotted versus H_b(r_c) – V_b(r_c)/2 for the interactions at the bond critical points (BCPs; *), where V_b(r_c) 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 (θ_p, κ_p), where θ_p corresponds to the tangent line of the plot and κ_p is the curvature. Whereas (R, θ) shows the static nature, (θ_p, κ_p) 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.

Keywords: ab initio calculations; quantum theory of atoms-in-molecules (QTAIM); halogen bonds; extended hypervalent interactions; hydrogen-bond nature.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S205252061700364X/xm5002sup1.cif Contains datablocks Compound_1, Compound_3, Compound_4
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061700364X/xm5002Compound_1sup2.hkl Contains datablock samp11_1
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061700364X/xm5002Compound_3sup3.hkl Contains datablock Compound_3
	Structure factor file (CIF format) https://doi.org/10.1107/S205252061700364X/xm5002Compound_4sup4.hkl Contains datablock Compound_4
	Portable Document Format (PDF) file https://doi.org/10.1107/S205252061700364X/xm5002sup5.pdf Supporting figures and tables

CCDC references: 698897; 1517582; 1536520

Computing details top

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.

(Compound_1) top

Crystal data top

C₂₀H₁₂Cl₂S₂	F(000) = 1584
M_r = 387.32	D_x = 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	R_int = 0.018
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.5°, θ_min = 2.7°
ω scans	h = −8→9
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	k = −34→34
T_min = 0.827, T_max = 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(F_o²) + (0.0302P)² + 0.819P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.002
5988 reflections	Δρ_max = 0.21 e Å⁻³
529 parameters	Δρ_min = −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	U_iso*/U_eq
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)

(Compound_3) top

Crystal data top

C₂₀H₁₂Cl₂Se₂	F(000) = 1872
M_r = 481.12	D_x = 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	R_int = 0.048
Detector resolution: 7.31 pixels mm^-1	θ_max = 25.5°, θ_min = 2.1°
ω scans	h = −9→9
Absorption correction: multi-scan Jacobson, R. (1998) Private communication	k = −35→24
T_min = 0.287, T_max = 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(F_o²) + (0.0339P)² + 0.0876P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
6129 reflections	Δρ_max = 0.41 e Å⁻³
433 parameters	Δρ_min = −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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

(Compound_4) top

Crystal data top

C₂₀H₁₂Br₂Se₂	Z = 2
M_r = 570.04	F(000) = 540
Triclinic, P1	D_x = 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	R_int = 0.035
ω scans	θ_max = 27.1°, θ_min = 2.9°
Absorption correction: multi-scan MULABS - Empirical Correction for Absorption Anisotropy. Blessing, R. H., Acta Cryst., A51, 33-38 (1995).	h = −10→10
T_min = 0.734, T_max = 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(F_o²) + (0.0128P)² + 4.9343P] where P = (F_o² + 2F_c²)/3
S = 1.20	(Δ/σ)_max < 0.001
3813 reflections	Δρ_max = 1.68 e Å⁻³
217 parameters	Δρ_min = −1.28 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

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