research communications
of trimethyl({tris[(phenylsulfanyl)methyl]silyl}methoxy)silane and Hirshfeld surface analysis of 3-bromo-2,2-bis(bromomethyl)propan-1-ol
aTechnische Universität Dortmund, Fakultät Chemie und Chemische Biologie, Otto-Hahn-Strasse 6, 44227 Dortmund, Germany
*Correspondence e-mail: carsten.strohmann@tu-dortmund.de
Trimethyl({tris[(phenylsulfanyl)methyl]silyl}methoxy)silane (3), C26H32OS3Si, is a new ligand for transition-metal coordination chemistry derived from 3-bromo-2,2-bis(bromomethyl)propan-1-ol (1), C5H9Br3O, through silylation and following exchange of bromine groups with NaSPh. Silylated thioether ligand 3 crystallizes in the centrosymmetric C2/c. Bromomethylalcohol 1 crystallizes in the P in the triclinic with four molecules in the Analysis of the Hirshfeld surface shows structure-defining interactions for bromomethylalcohol 1, resulting in intermolecular hydrogen bonds between the hydroxyl groups along the a-axis direction.
Keywords: crystal structure; thioether ligand; Hirshfeld surface analysis.
1. Chemical context
Thioether ligands offer an attractive alternative to known phosphine or amine ligands. As a result of the soft property of thioethers, they coordinate to transition metals (Awaleh et al., 2008; Knaust & Keller, 2003; Knorr et al., 2012, 2014; Schlachter et al., 2022). Furthermore, because of its two lone pairs, sulfur can act as a bridging ligand between two metal centres and thus favour coordination polymers (Awaleh et al., 2010; Peindy et al., 2009; Schlachter et al., 2018, 2020, 2021; Viau et al., 2022).
In addition, thioether ligands are increasingly gaining interest for redox catalysis, as their stabilizing effect towards the metal centres differ from those of the common phosphine or amine ligands, and thus new catalytic accesses can be created (Petuker et al., 2017).
Furthermore, the solubility of ligands in polar and non-polar solvents plays a major role. Polar hydroxyl groups, such as bromomethylalcohol 1, will reduce solubility in non-polar solvents and can cause problems like the reduced formation of catalytic species in the process. To prevent this, the hydroxyl group was silylated via conditions known from the literature, thus increasing the of ligand 3.
In the following, the structure of bromomethylalcohol 1 and silylated thioether ligand 3, as well as the surface interactions of 1 are discussed in terms of Hirshfeld surface analysis.
2. Structural commentary
Bromomethylalcohol 1 crystallizes at 243.15 K from diethyl ether in the centrosymmetric P with four molecules present in the (Z′ = 4, Z = 2). The molecular structure of bromomethylalcohol 1 is shown in Fig. 1 and selected bond lengths and angles are given in Table 1.
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The bond lengths to be expected for a C(alkyl)–Br bond are in the range 1.880–1.940 Å (Allen et al., 1987). The C(alkyl)—Br bonds listed in Table 1 are located in the upper range of these bond lengths. The O1—C2 bond length of 1.432 (3) Å corresponds to an expected length for a C(alkyl)—OH bond of between 1.393–1.456 Å. Furthermore, the bond angles C1—C3—Br1, C1—C4—Br2 and C1—C5—Br3 are similar and in general comparable in size with similar structural motifs (Bukowska-Strzyżewska & Skoweranda, 1980).
The molecular structure of silylated thioether ligand 3 is shown in Fig. 2 and selected bond lengths and angles are given in Table 2.
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The S—C(alkyl) bonds are of comparable lengths to each other and correspond to the expected bond lengths for alkyl–sulfur bonds (1.778–1.856 Å; Allen et al., 1987). The S—C(Ph) bonds, on the other hand, are significantly shorter than the S—C(alkyl) bonds, but are within the range of expected bond lengths (1.700–1.802 Å). Comparing the bond angles at sulfur to similar structural motifs, the angles are quite similar (Tinant et al., 1987; Crundwell et al., 1999). The length of the C—O bond of the ether from silylated thioether ligand 3 lies in a comparable range to the -C–O bond from bromomethylalcohol 1. The occupancies at the disordered TMSO group are 50.9 (3)% for O1/Si1/C24–C26 and 49.1 (3)% for O1′/Si1′/C24′–C26′. The disorder at the TMSO group also shows a shorter O1—C23 [1.384 (15) Å] bond length than O1′—C23 [1.479 (14) Å]. The expected bond length for a C—O—Si bond is between 1.365 and 1.467 Å (Allen et al., 1987). Furthermore, the bond lengths O1—Si1 [1.632 (12) Å] and O1′—Si1′ [1.672 (13) Å] are similar, as are the bond angles between C23—O1—Si1 [123.6°(7)] and C23—O1′—Si1′ [123.7°(7)].
3. Supramolecular features
The crystal packing of bromomethylalcohol 1 is shown in Fig. 3 and is defined by intermolecular hydrogen bonds along the a-axis direction, which are given in Table 3. Here, the contacts between O1—H1⋯O2 [2.712 (3) Å] and O3—H3⋯O4 [2.729 (3) Å] are slightly shorter than those between O2—H2⋯O3 [2.766 (3) Å] and O4—H4⋯O1i [2.773 (3) Å]. Moreover, the angles are approximately linear at 175 (4)° (O3—H3⋯O4) and 168 (4)° (O1—H1⋯O2). These hydrogen bonds can be assigned the graph-set symbol D11(2). This means that a hydrogen bond between two adjacent hydroxyl groups, O1—H1⋯O2, is established. The contact between O4—H4⋯O1 is created via the (i) x − 1, y, z.
To gain further insight into the supramolecular packing interactions, a Hirshfeld surface analysis was performed (Spackman & Jayatilaka, 2009). The Hirshfeld surfaces and fingerprint plots were generated and analysed using the program CrystalExplorer21 (Spackman et al., 2021). The Hirshfeld surface was mapped over dnorm in the range −0.66 to 1.14 a.u. (Fig. 4). The contributions of the different intermolecular interactions for 1 are shown in the two-dimensional fingerprint plots (Fig. 5; McKinnon et al., 2007). The different strength of the interactions is reflected here by the colouring of the surface. The red dots represent close contacts, whereas blue areas represent no contact. The fingerprint plots show that the O⋯H/H⋯O interactions account for only 8.9% of the total surface area, although they are probably the strongest contributors to the intermolecular interactions. The largest contribution to the surface interactions comes from the Br⋯H/H⋯Br contacts at 50.4%. This is followed by the contributions of the H⋯H/H⋯H contacts (27.7%). There is no contribution to the surface interactions by C⋯H/H⋯C contacts, which is mainly due to the fact that the carbon atoms of the CH2 groups in question are shielded from the outside by the terminal Br and OH groups so that they cannot make any contribution. The smallest contribution to the surface interactions is made by the Br⋯O/O⋯Br contacts (0.4%), which is due to the spatial arrangement of the bromine substituents in relation to the hydroxyl group.
The crystal packing of silylated thioether ligand 3 is shown in Fig. 6 and is characterized by propagation along the b-axis direction. For silylated thioether ligand 3, apart from the packing effects, there are no overriding intermolecular interactions between the molecules that influences the arrangement of the molecules.
4. Database survey
A search of the Cambridge crystallographic database (Groom et al., 2016; WebCSD January 2023) for 1,3-dibromo-2-(bromomethyl)propanes revealed the following molecules structurally related to bromomethylalcohol 1: 4-[3-bromo-2,2-bis(bromomethyl)propoxy]benzene-1,2-dicarbonitrile (VUJBOU; Canımkurbey et al., 2020), 3-[3-bromo-2,2-bis(bromomethyl)propoxy]benzene-1,2-dicarbonitrile (VUJBUA; Canımkurbey et al., 2020) and dimethyl 5-[3-bromo-2,2-bis(bromomethyl)propoxy]benzene-1,3-dicarboxylate (BANYOI; Najafi Khosroshahi et al., 2021). For the C—Br bond lengths, similar values are found as in bromomethylalcohol 1. Furthermore, the C—CH2—Br angles observed in 1 correspond to the angles in the selected structures.
A search for 1,3-bis(phenylthio)-2-[(phenylthio)methyl]propan-2-ol yielded no hits in the WebCSD. By replacing the quaternary carbon with a silicon atom, the comparable structural motif of catena-[[μ2-tetrakis(methylthiomethyl)silane]dibromomercury(II)] (WAMYUF; Peindy et al., 2005) was obtained. Here, the C(alkyl)—S bonds are shorter than in silylated thioether ligand 3. The same applies to the related structure of dibromo[tetrakis(phenylthiomethyl)silane-S,S′]mercury(II) (WAMZAM; Peindy et al., 2005).
Another related structure motif could be found where the thioether groups act as bridging ligands between Cu2I2 rhomboids (Schlachter et al., 2022).
5. Synthesis and crystallization
Bromomethylalcohol 1 is commercially available and was crystallized at 243.15 K from diethyl ether as clear and colourless plates.
Methyllithium (1.6 M in n-hexane, 16.93 mmol) was dropped into diethyl ether (50 mL) at 273.15 K to 1 (15.39 mmol). The solution was stirred for 1 h at room temperature and then chlorotrimethylsilane (16.93 mmol) was added at 273.15 K. It was stirred again for 1 h at room temperature, then the reaction solution was quenched with water. The aqueous phase was extracted three times with dichloromethane and the combined organic layers were dried over magnesium sulfate. The volatiles were removed to give compound 2 crude.
1H NMR (600 MHz, C6D6) δ = 3.33 (s, 2H; OCH2C), 3.18 (s, 6H; CCH2Br), 0.03 (s, 9H; Si(CH3)3) ppm.
{1H}13C NMR (151 MHz, C6D6) δ = 61.6 (1C; OCH2C), 44.3 [1C; (C(CH2)4], 34.6 (3C; CCH2Br), −0.7 [3C; Si(CH3)3] ppm.
Thiophenol (5.83 mmol) was then added to sodium hydride (5.83 mmol) in DMF (5 mL) at 273.15 K and stirred for 10 minutes. The NaSPh solution was added to 2 in DMF (10 mL) at 273.15 K and stirred for 10 minutes. The reaction solution was irradiated with microwaves (150 W, 323.15 K, 1 h) and then quenched with water. The aqueous phase was extracted three times with dichloromethane, the combined organic layers were dried over magnesium sulfate and the volatiles were removed. The residue was separated by fractional distillation under reduced pressure. Crystallization from diethyl ether at 243.15 K provided silylated thioether ligand 3 as clear and colourless blocks.
1H NMR (600 MHz, CDCl3) δ = 7.38–7.34 (m, 6H; CHortho), 7.30–7.23 (m, 6H; CHmeta), 7.19–7.15 (m, 3H; CHpara), 3.60 (s, 2H; OCH2C), 3.22 (s, 6H; SCH2C), 0.04 [s, 9H; Si(CH3)3] ppm.
{1H}13C NMR (151 MHz, CDCl3) δ = 137.2 (3C; Cipso), 129.8 (3C; Cortho), 128.9 (3C; Cmeta), 126.2 (3C; Cpara), 64.1 (1C; OCH2C), 46.0 (1C; (C(CH2)4), 38.7 (3C; SCH2C), −0.6 [3C; Si(CH3)3] ppm.
6. Refinement
Crystal data, data collection and structure . H atoms were positioned geometrically (C—H = 0.95–1.00 Å) and were refined using a riding model, with Uiso(H) = 1.2Ueq(C) for CH2 and CH hydrogen atoms and Uiso(H) = 1.5Ueq(C) for CH3 hydrogen atoms. Hydrogen atoms H1, H2, H3 and H4 for compound 1 were refined independently. The TMSO group in 3 is disordered with occupancies converging to 50.9 (3)% for O1/Si1/C24–C26 and 49.1 (3)% for O1′/Si1′/C24′–C26′.
details are summarized in Table 4
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Supporting information
https://doi.org/10.1107/S205698902300227X/vm2278sup1.cif
contains datablocks 1, 3, global. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S205698902300227X/vm22781sup2.hkl
Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S205698902300227X/vm22783sup3.hkl
Supporting information file. DOI: https://doi.org/10.1107/S205698902300227X/vm22781sup4.cml
Supporting information file. DOI: https://doi.org/10.1107/S205698902300227X/vm22783sup5.cml
Cell
SAINT V8.40B (Bruker, 2016) for (1); SAINT V8.38A (Bruker, 2018) for (3). Data reduction: SAINT V8.40B (Bruker, 2016) for (1); SAINT V8.38A (Bruker, 2018) for (3). For both structures, program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: Olex2 1.3 (Dolomanov et al., 2009). Software used to prepare material for publication: CrystalExplorer21 (Spackman et al., 2021), Mercury (Macrae et al., 2020), publCIF (Westrip, 2010) for (1); Olex2 1.3 (Dolomanov et al., 2009) for (3).4C5H9Br3O | Z = 2 |
Mr = 1299.35 | F(000) = 1216 |
Triclinic, P1 | Dx = 2.465 Mg m−3 |
a = 8.7763 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.4409 (3) Å | Cell parameters from 7029 reflections |
c = 21.2951 (6) Å | θ = 2.3–15.9° |
α = 96.762 (1)° | µ = 13.75 mm−1 |
β = 92.198 (1)° | T = 100 K |
γ = 90.552 (1)° | Block, clear colourless |
V = 1750.69 (8) Å3 | 0.19 × 0.14 × 0.1 mm |
Bruker D8 VENTURE diffractometer | 10208 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 8756 reflections with I > 2σ(I) |
HELIOS mirror optics monochromator | Rint = 0.049 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 30.0°, θmin = 1.9° |
ω and φ scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −13→13 |
Tmin = 0.337, Tmax = 0.565 | l = −29→29 |
61804 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.069 | w = 1/[σ2(Fo2) + (0.0285P)2 + 2.5017P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max = 0.002 |
10208 reflections | Δρmax = 1.30 e Å−3 |
341 parameters | Δρmin = −1.02 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Br6 | 0.30125 (3) | 0.63039 (3) | 0.93269 (2) | 0.02037 (6) | |
Br4 | 0.86961 (3) | 0.53671 (3) | 0.92653 (2) | 0.02067 (6) | |
Br12 | −0.19710 (3) | 0.09408 (3) | 0.93843 (2) | 0.02543 (7) | |
Br8 | 0.16003 (3) | 0.66948 (3) | 0.52163 (2) | 0.02341 (6) | |
Br11 | 0.01625 (3) | −0.18319 (3) | 0.81305 (2) | 0.02304 (6) | |
Br5 | 0.51228 (3) | 0.84879 (3) | 0.81175 (2) | 0.02386 (7) | |
Br10 | 0.36938 (3) | 0.18854 (3) | 0.93546 (2) | 0.02617 (7) | |
Br2 | 0.65686 (3) | −0.15652 (3) | 0.52219 (2) | 0.02328 (6) | |
Br9 | 0.57548 (3) | 0.49690 (3) | 0.59268 (2) | 0.02586 (7) | |
Br3 | 1.07850 (3) | 0.04690 (3) | 0.59305 (2) | 0.02689 (7) | |
Br7 | −0.05124 (3) | 0.56946 (3) | 0.67027 (2) | 0.02622 (7) | |
Br1 | 0.45074 (3) | 0.02393 (3) | 0.67092 (2) | 0.02651 (7) | |
O2 | 0.6078 (3) | 0.3698 (2) | 0.78090 (11) | 0.0242 (5) | |
O4 | 0.1096 (3) | 0.2803 (2) | 0.78670 (12) | 0.0251 (5) | |
O3 | 0.3270 (3) | 0.4014 (2) | 0.72095 (10) | 0.0210 (4) | |
O1 | 0.8317 (3) | 0.2138 (2) | 0.72320 (10) | 0.0204 (4) | |
C10 | 0.4056 (3) | 0.5476 (3) | 0.85794 (13) | 0.0179 (5) | |
H10A | 0.3892 | 0.4429 | 0.8528 | 0.022* | |
H10B | 0.3591 | 0.5846 | 0.8202 | 0.022* | |
C11 | 0.2610 (3) | 0.5306 (3) | 0.63072 (13) | 0.0145 (5) | |
C1 | 0.7645 (3) | 0.0382 (3) | 0.63190 (13) | 0.0147 (5) | |
C6 | 0.5773 (3) | 0.5793 (3) | 0.86066 (13) | 0.0156 (5) | |
C4 | 0.7044 (3) | 0.0353 (3) | 0.56350 (14) | 0.0188 (5) | |
H4A | 0.7816 | 0.0798 | 0.5391 | 0.023* | |
H4B | 0.6111 | 0.0934 | 0.5628 | 0.023* | |
C14 | 0.2011 (3) | 0.4988 (3) | 0.56232 (14) | 0.0183 (5) | |
H14A | 0.1059 | 0.4413 | 0.5613 | 0.022* | |
H14B | 0.2768 | 0.4408 | 0.5378 | 0.022* | |
C20 | −0.0922 (3) | 0.1385 (3) | 0.86366 (14) | 0.0198 (5) | |
H20A | −0.1390 | 0.0808 | 0.8259 | 0.024* | |
H20B | −0.1081 | 0.2403 | 0.8585 | 0.024* | |
C16 | 0.0793 (3) | 0.1105 (3) | 0.86637 (13) | 0.0175 (5) | |
C9 | 0.6137 (3) | 0.7389 (3) | 0.87314 (14) | 0.0186 (5) | |
H9A | 0.7253 | 0.7537 | 0.8720 | 0.022* | |
H9B | 0.5820 | 0.7752 | 0.9161 | 0.022* | |
C8 | 0.6491 (3) | 0.5059 (3) | 0.91482 (14) | 0.0184 (5) | |
H8A | 0.6276 | 0.4021 | 0.9064 | 0.022* | |
H8B | 0.6001 | 0.5418 | 0.9546 | 0.022* | |
C7 | 0.6409 (3) | 0.5181 (3) | 0.79682 (14) | 0.0196 (5) | |
H7A | 0.5972 | 0.5710 | 0.7631 | 0.024* | |
H7B | 0.7529 | 0.5332 | 0.7986 | 0.024* | |
C13 | 0.1613 (3) | 0.6329 (3) | 0.67193 (14) | 0.0186 (5) | |
H13A | 0.1659 | 0.7283 | 0.6571 | 0.022* | |
H13B | 0.2028 | 0.6424 | 0.7161 | 0.022* | |
C3 | 0.6604 (3) | −0.0418 (3) | 0.67253 (14) | 0.0189 (5) | |
H3A | 0.7016 | −0.0296 | 0.7168 | 0.023* | |
H3B | 0.6612 | −0.1449 | 0.6571 | 0.023* | |
C17 | 0.1445 (3) | 0.1412 (3) | 0.80276 (14) | 0.0203 (5) | |
H17A | 0.2566 | 0.1309 | 0.8051 | 0.024* | |
H17B | 0.1031 | 0.0693 | 0.7687 | 0.024* | |
C18 | 0.1501 (3) | 0.2131 (3) | 0.92103 (15) | 0.0217 (6) | |
H18A | 0.0978 | 0.1992 | 0.9603 | 0.026* | |
H18B | 0.1319 | 0.3122 | 0.9121 | 0.026* | |
C15 | 0.4154 (3) | 0.6086 (3) | 0.63522 (14) | 0.0184 (5) | |
H15A | 0.4467 | 0.6330 | 0.6804 | 0.022* | |
H15B | 0.4042 | 0.6990 | 0.6163 | 0.022* | |
C12 | 0.2713 (3) | 0.3858 (3) | 0.65646 (13) | 0.0173 (5) | |
H12A | 0.1691 | 0.3397 | 0.6534 | 0.021* | |
H12B | 0.3403 | 0.3233 | 0.6303 | 0.021* | |
C2 | 0.7795 (3) | 0.1961 (3) | 0.65817 (13) | 0.0174 (5) | |
H2A | 0.8522 | 0.2441 | 0.6329 | 0.021* | |
H2B | 0.6792 | 0.2421 | 0.6542 | 0.021* | |
C19 | 0.1148 (3) | −0.0427 (3) | 0.87699 (14) | 0.0199 (5) | |
H19A | 0.0808 | −0.0598 | 0.9193 | 0.024* | |
H19B | 0.2265 | −0.0558 | 0.8766 | 0.024* | |
C5 | 0.9158 (3) | −0.0390 (3) | 0.63634 (15) | 0.0202 (5) | |
H5A | 0.9009 | −0.1395 | 0.6178 | 0.024* | |
H5B | 0.9472 | −0.0387 | 0.6815 | 0.024* | |
H2 | 0.535 (5) | 0.361 (5) | 0.761 (2) | 0.034 (12)* | |
H4 | 0.036 (5) | 0.280 (5) | 0.768 (2) | 0.046 (14)* | |
H3 | 0.264 (5) | 0.369 (5) | 0.737 (2) | 0.031 (11)* | |
H1 | 0.766 (5) | 0.245 (4) | 0.7388 (19) | 0.027 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br6 | 0.01720 (12) | 0.02772 (14) | 0.01664 (13) | 0.00405 (10) | 0.00425 (10) | 0.00301 (10) |
Br4 | 0.01508 (12) | 0.02315 (13) | 0.02331 (14) | 0.00189 (10) | −0.00250 (10) | 0.00171 (11) |
Br12 | 0.02147 (14) | 0.03204 (15) | 0.02229 (15) | −0.00074 (11) | 0.00614 (11) | −0.00048 (12) |
Br8 | 0.02755 (15) | 0.02032 (13) | 0.02272 (15) | 0.00141 (11) | −0.00450 (11) | 0.00575 (11) |
Br11 | 0.02468 (14) | 0.01963 (13) | 0.02347 (15) | −0.00413 (10) | 0.00482 (11) | −0.00391 (11) |
Br5 | 0.02543 (14) | 0.02445 (14) | 0.02381 (15) | 0.00620 (11) | 0.00529 (11) | 0.00985 (11) |
Br10 | 0.01955 (14) | 0.02889 (15) | 0.02851 (16) | −0.00311 (11) | −0.00459 (11) | −0.00105 (12) |
Br2 | 0.02747 (15) | 0.01877 (13) | 0.02193 (15) | −0.00285 (10) | −0.00348 (11) | −0.00290 (10) |
Br9 | 0.01620 (13) | 0.02863 (15) | 0.03546 (18) | 0.00502 (10) | 0.00516 (12) | 0.01344 (13) |
Br3 | 0.01618 (13) | 0.02337 (14) | 0.03854 (18) | −0.00393 (10) | 0.00650 (12) | −0.00860 (12) |
Br7 | 0.01773 (13) | 0.02374 (14) | 0.03600 (18) | −0.00242 (10) | 0.00665 (12) | −0.00308 (12) |
Br1 | 0.01738 (13) | 0.02924 (15) | 0.03493 (18) | 0.00410 (11) | 0.00650 (12) | 0.01025 (13) |
O2 | 0.0205 (11) | 0.0261 (11) | 0.0239 (12) | 0.0031 (8) | −0.0009 (9) | −0.0056 (9) |
O4 | 0.0208 (11) | 0.0281 (11) | 0.0277 (12) | −0.0036 (9) | 0.0004 (9) | 0.0091 (9) |
O3 | 0.0220 (10) | 0.0240 (10) | 0.0173 (10) | −0.0044 (8) | −0.0020 (8) | 0.0042 (8) |
O1 | 0.0198 (10) | 0.0219 (10) | 0.0181 (10) | 0.0044 (8) | −0.0016 (8) | −0.0027 (8) |
C10 | 0.0176 (12) | 0.0222 (13) | 0.0136 (13) | 0.0003 (10) | 0.0011 (10) | 0.0003 (10) |
C11 | 0.0145 (11) | 0.0134 (11) | 0.0151 (12) | −0.0010 (9) | −0.0008 (9) | 0.0008 (9) |
C1 | 0.0159 (12) | 0.0124 (11) | 0.0160 (13) | 0.0000 (9) | 0.0002 (10) | 0.0026 (9) |
C6 | 0.0142 (11) | 0.0185 (12) | 0.0140 (12) | −0.0006 (9) | 0.0017 (9) | 0.0013 (9) |
C4 | 0.0217 (13) | 0.0135 (11) | 0.0208 (14) | −0.0008 (10) | −0.0018 (11) | 0.0011 (10) |
C14 | 0.0203 (13) | 0.0154 (12) | 0.0182 (13) | −0.0004 (9) | −0.0040 (10) | 0.0002 (10) |
C20 | 0.0199 (13) | 0.0228 (13) | 0.0164 (13) | 0.0013 (10) | 0.0017 (10) | 0.0006 (10) |
C16 | 0.0172 (12) | 0.0174 (12) | 0.0173 (13) | −0.0002 (9) | 0.0018 (10) | −0.0012 (10) |
C9 | 0.0187 (12) | 0.0199 (12) | 0.0184 (13) | 0.0012 (10) | 0.0015 (10) | 0.0063 (10) |
C8 | 0.0135 (12) | 0.0228 (13) | 0.0191 (13) | 0.0005 (10) | −0.0006 (10) | 0.0029 (10) |
C7 | 0.0178 (13) | 0.0242 (13) | 0.0167 (13) | −0.0002 (10) | 0.0019 (10) | 0.0018 (10) |
C13 | 0.0168 (12) | 0.0168 (12) | 0.0210 (14) | −0.0016 (9) | −0.0004 (10) | −0.0026 (10) |
C3 | 0.0170 (12) | 0.0190 (12) | 0.0214 (14) | 0.0009 (10) | −0.0009 (10) | 0.0053 (10) |
C17 | 0.0205 (13) | 0.0222 (13) | 0.0181 (14) | −0.0016 (10) | 0.0011 (10) | 0.0014 (10) |
C18 | 0.0179 (13) | 0.0246 (14) | 0.0207 (14) | −0.0008 (10) | −0.0011 (11) | −0.0040 (11) |
C15 | 0.0161 (12) | 0.0152 (11) | 0.0238 (14) | −0.0021 (9) | −0.0003 (10) | 0.0026 (10) |
C12 | 0.0198 (13) | 0.0145 (11) | 0.0171 (13) | −0.0008 (9) | 0.0003 (10) | −0.0001 (10) |
C2 | 0.0203 (13) | 0.0144 (11) | 0.0170 (13) | 0.0019 (9) | 0.0007 (10) | −0.0005 (10) |
C19 | 0.0215 (13) | 0.0184 (12) | 0.0186 (14) | 0.0002 (10) | −0.0017 (11) | −0.0025 (10) |
C5 | 0.0164 (12) | 0.0175 (12) | 0.0259 (15) | 0.0025 (10) | −0.0009 (11) | 0.0004 (11) |
Br1—C3 | 1.948 (3) | C4—H4A | 0.9900 |
Br2—C4 | 1.952 (3) | C4—H4B | 0.9900 |
Br3—C5 | 1.950 (3) | C14—H14A | 0.9900 |
Br4—C8 | 1.956 (3) | C14—H14B | 0.9900 |
Br5—C9 | 1.956 (3) | C20—H20A | 0.9900 |
Br6—C10 | 1.954 (3) | C20—H20B | 0.9900 |
Br7—C13 | 1.951 (3) | C20—C16 | 1.531 (4) |
Br8—C14 | 1.947 (3) | C16—C17 | 1.548 (4) |
Br9—C15 | 1.951 (3) | C16—C18 | 1.532 (4) |
Br10—C18 | 1.957 (3) | C16—C19 | 1.523 (4) |
Br11—C19 | 1.955 (3) | C9—H9A | 0.9900 |
Br12—C20 | 1.955 (3) | C9—H9B | 0.9900 |
O2—C7 | 1.426 (4) | C8—H8A | 0.9900 |
O2—H2 | 0.75 (4) | C8—H8B | 0.9900 |
O4—C17 | 1.428 (4) | C7—H7A | 0.9900 |
O4—H4 | 0.75 (5) | C7—H7B | 0.9900 |
O3—C12 | 1.431 (3) | C13—H13A | 0.9900 |
O3—H3 | 0.74 (4) | C13—H13B | 0.9900 |
O1—C2 | 1.432 (3) | C3—H3A | 0.9900 |
O1—H1 | 0.72 (4) | C3—H3B | 0.9900 |
C10—H10A | 0.9900 | C17—H17A | 0.9900 |
C10—H10B | 0.9900 | C17—H17B | 0.9900 |
C10—C6 | 1.531 (4) | C18—H18A | 0.9900 |
C11—C14 | 1.524 (4) | C18—H18B | 0.9900 |
C11—C13 | 1.531 (4) | C15—H15A | 0.9900 |
C11—C15 | 1.530 (4) | C15—H15B | 0.9900 |
C11—C12 | 1.534 (4) | C12—H12A | 0.9900 |
C1—C4 | 1.527 (4) | C12—H12B | 0.9900 |
C1—C3 | 1.535 (4) | C2—H2A | 0.9900 |
C1—C2 | 1.532 (4) | C2—H2B | 0.9900 |
C1—C5 | 1.526 (4) | C19—H19A | 0.9900 |
C6—C9 | 1.528 (4) | C19—H19B | 0.9900 |
C6—C8 | 1.532 (4) | C5—H5A | 0.9900 |
C6—C7 | 1.540 (4) | C5—H5B | 0.9900 |
C7—O2—H2 | 109 (3) | H8A—C8—H8B | 107.7 |
C17—O4—H4 | 111 (4) | O2—C7—C6 | 113.0 (2) |
C12—O3—H3 | 102 (3) | O2—C7—H7A | 109.0 |
C2—O1—H1 | 102 (3) | O2—C7—H7B | 109.0 |
Br6—C10—H10A | 108.8 | C6—C7—H7A | 109.0 |
Br6—C10—H10B | 108.8 | C6—C7—H7B | 109.0 |
H10A—C10—H10B | 107.7 | H7A—C7—H7B | 107.8 |
C6—C10—Br6 | 113.95 (19) | Br7—C13—H13A | 109.0 |
C6—C10—H10A | 108.8 | Br7—C13—H13B | 109.0 |
C6—C10—H10B | 108.8 | C11—C13—Br7 | 112.91 (18) |
C14—C11—C13 | 113.7 (2) | C11—C13—H13A | 109.0 |
C14—C11—C15 | 111.6 (2) | C11—C13—H13B | 109.0 |
C14—C11—C12 | 105.9 (2) | H13A—C13—H13B | 107.8 |
C13—C11—C12 | 110.9 (2) | Br1—C3—H3A | 109.0 |
C15—C11—C13 | 103.0 (2) | Br1—C3—H3B | 109.0 |
C15—C11—C12 | 111.9 (2) | C1—C3—Br1 | 112.99 (18) |
C4—C1—C3 | 113.2 (2) | C1—C4—Br2 | 113.48 (18) |
C4—C1—C2 | 105.9 (2) | C1—C3—H3A | 109.0 |
C2—C1—C3 | 110.8 (2) | C1—C3—H3B | 109.0 |
C5—C1—C4 | 111.9 (2) | H3A—C3—H3B | 107.8 |
C5—C1—C3 | 103.2 (2) | O4—C17—C16 | 113.3 (2) |
C5—C1—C2 | 112.0 (2) | O4—C17—H17A | 108.9 |
C10—C6—C8 | 107.7 (2) | O4—C17—H17B | 108.9 |
C10—C6—C7 | 107.9 (2) | C16—C17—H17A | 108.9 |
C9—C6—C10 | 112.4 (2) | C16—C17—H17B | 108.9 |
C9—C6—C8 | 108.6 (2) | H17A—C17—H17B | 107.7 |
C9—C6—C7 | 109.6 (2) | Br10—C18—H18A | 108.8 |
C8—C6—C7 | 110.7 (2) | Br10—C18—H18B | 108.8 |
Br2—C4—H4A | 108.9 | C16—C18—Br10 | 113.95 (19) |
Br2—C4—H4B | 108.9 | C16—C18—H18A | 108.8 |
C1—C4—H4A | 108.9 | C16—C18—H18B | 108.8 |
C1—C4—H4B | 108.9 | H18A—C18—H18B | 107.7 |
H4A—C4—H4B | 107.7 | Br9—C15—H15A | 108.9 |
Br8—C14—H14A | 108.9 | Br9—C15—H15B | 108.9 |
Br8—C14—H14B | 108.9 | C11—C15—Br9 | 113.19 (18) |
C11—C14—Br8 | 113.49 (18) | C11—C15—H15A | 108.9 |
C11—C14—H14A | 108.9 | C11—C15—H15B | 108.9 |
C11—C14—H14B | 108.9 | H15A—C15—H15B | 107.8 |
H14A—C14—H14B | 107.7 | O3—C12—C11 | 111.4 (2) |
Br12—C20—H20A | 108.8 | O3—C12—H12A | 109.4 |
Br12—C20—H20B | 108.8 | O3—C12—H12B | 109.4 |
H20A—C20—H20B | 107.7 | C11—C12—H12A | 109.4 |
C16—C20—Br12 | 114.0 (2) | C11—C12—H12B | 109.4 |
C16—C20—H20A | 108.8 | H12A—C12—H12B | 108.0 |
C16—C20—H20B | 108.8 | O1—C2—H2A | 109.3 |
C20—C16—C17 | 108.1 (2) | O1—C2—H2B | 109.3 |
C20—C16—C18 | 107.3 (2) | C1—C2—H2A | 109.3 |
C18—C16—C17 | 110.4 (2) | C1—C2—H2B | 109.3 |
C19—C16—C20 | 112.4 (2) | H2A—C2—H2B | 108.0 |
C19—C16—C17 | 109.0 (2) | Br11—C19—H19A | 109.0 |
C19—C16—C18 | 109.7 (2) | Br11—C19—H19B | 109.0 |
Br5—C9—H9A | 109.0 | C16—C19—Br11 | 112.9 (2) |
Br5—C9—H9B | 109.0 | C16—C19—H19A | 109.0 |
C6—C9—Br5 | 113.0 (2) | C16—C19—H19B | 109.0 |
C6—C9—H9A | 109.0 | H19A—C19—H19B | 107.8 |
C6—C9—H9B | 109.0 | Br3—C5—H5A | 108.9 |
H9A—C9—H9B | 107.8 | Br3—C5—H5B | 108.9 |
Br4—C8—H8A | 108.8 | C1—C5—Br3 | 113.21 (19) |
Br4—C8—H8B | 108.8 | O1—C2—C1 | 111.6 (2) |
C6—C8—Br4 | 113.72 (19) | C1—C5—H5A | 108.9 |
C6—C8—H8A | 108.8 | C1—C5—H5B | 108.9 |
C6—C8—H8B | 108.8 | H5A—C5—H5B | 107.7 |
Br6—C10—C6—C9 | −54.5 (3) | C13—C11—C14—Br8 | 52.6 (3) |
Br6—C10—C6—C8 | 65.0 (3) | C13—C11—C15—Br9 | 175.11 (19) |
Br6—C10—C6—C7 | −175.47 (18) | C13—C11—C12—O3 | −56.3 (3) |
Br12—C20—C16—C17 | 176.50 (18) | C3—C1—C4—Br2 | −52.8 (3) |
Br12—C20—C16—C18 | −64.5 (3) | C3—C1—C2—O1 | 55.4 (3) |
Br12—C20—C16—C19 | 56.1 (3) | C3—C1—C5—Br3 | −176.37 (18) |
C10—C6—C9—Br5 | −55.4 (3) | C17—C16—C18—Br10 | −65.2 (3) |
C10—C6—C8—Br4 | −179.21 (18) | C17—C16—C19—Br11 | −63.5 (3) |
C10—C6—C7—O2 | −55.7 (3) | C18—C16—C17—O4 | −62.8 (3) |
C4—C1—C3—Br1 | −54.4 (3) | C18—C16—C19—Br11 | 175.64 (19) |
C4—C1—C2—O1 | 178.5 (2) | C15—C11—C14—Br8 | −63.4 (3) |
C4—C1—C5—Br3 | 61.6 (3) | C15—C11—C13—Br7 | 175.29 (18) |
C14—C11—C13—Br7 | 54.3 (3) | C15—C11—C12—O3 | 58.1 (3) |
C14—C11—C15—Br9 | −62.5 (3) | C12—C11—C14—Br8 | 174.59 (18) |
C14—C11—C12—O3 | 179.9 (2) | C12—C11—C13—Br7 | −64.9 (3) |
C20—C16—C17—O4 | 54.2 (3) | C12—C11—C15—Br9 | 56.0 (3) |
C20—C16—C18—Br10 | 177.22 (19) | C2—C1—C4—Br2 | −174.38 (18) |
C20—C16—C19—Br11 | 56.4 (3) | C2—C1—C3—Br1 | 64.4 (3) |
C9—C6—C8—Br4 | −57.3 (3) | C2—C1—C5—Br3 | −57.1 (3) |
C9—C6—C7—O2 | −178.4 (2) | C19—C16—C17—O4 | 176.7 (2) |
C8—C6—C9—Br5 | −174.45 (17) | C19—C16—C18—Br10 | 54.8 (3) |
C8—C6—C7—O2 | 61.9 (3) | C5—C1—C4—Br2 | 63.4 (3) |
C7—C6—C9—Br5 | 64.5 (3) | C5—C1—C3—Br1 | −175.56 (18) |
C7—C6—C8—Br4 | 63.0 (3) | C5—C1—C2—O1 | −59.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O3 | 0.75 (4) | 2.04 (4) | 2.766 (3) | 162 (5) |
O4—H4···O1i | 0.75 (5) | 2.05 (5) | 2.773 (3) | 161 (5) |
O3—H3···O4 | 0.74 (4) | 1.99 (4) | 2.729 (3) | 175 (4) |
O1—H1···O2 | 0.72 (4) | 2.00 (4) | 2.712 (3) | 168 (4) |
Symmetry code: (i) x−1, y, z. |
C26H32OS3Si | F(000) = 2064 |
Mr = 484.78 | Dx = 1.245 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 27.0415 (12) Å | Cell parameters from 9874 reflections |
b = 6.9329 (3) Å | θ = 2.2–31.0° |
c = 27.7963 (14) Å | µ = 0.35 mm−1 |
β = 96.939 (2)° | T = 100 K |
V = 5173.0 (4) Å3 | Block, clear colourless |
Z = 8 | 0.62 × 0.56 × 0.46 mm |
Bruker D8 VENTURE diffractometer | 8253 independent reflections |
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs | 6927 reflections with I > 2σ(I) |
HELIOS mirror optics monochromator | Rint = 0.035 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 31.1°, θmin = 2.2° |
φ and ω scans | h = −39→39 |
Absorption correction: multi-scan (SADABS; Krause et al., 2015) | k = −10→10 |
Tmin = 0.671, Tmax = 0.746 | l = −40→40 |
40629 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.077 | w = 1/[σ2(Fo2) + (0.0273P)2 + 3.6217P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.003 |
8253 reflections | Δρmax = 0.36 e Å−3 |
340 parameters | Δρmin = −0.24 e Å−3 |
0 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.29397 (2) | 0.49136 (4) | 0.53826 (2) | 0.01817 (6) | |
S2 | 0.20238 (2) | 0.78150 (4) | 0.58269 (2) | 0.02262 (6) | |
S3 | 0.31216 (2) | 1.14605 (4) | 0.66285 (2) | 0.02538 (7) | |
C8 | 0.30483 (4) | 0.80744 (14) | 0.60358 (4) | 0.01565 (18) | |
C7 | 0.30656 (4) | 0.74642 (14) | 0.55036 (4) | 0.01713 (18) | |
H7A | 0.3399 | 0.7775 | 0.5412 | 0.021* | |
H7B | 0.2819 | 0.8238 | 0.5294 | 0.021* | |
C9 | 0.25831 (4) | 0.72995 (14) | 0.62389 (4) | 0.01716 (18) | |
H9A | 0.2556 | 0.7904 | 0.6557 | 0.021* | |
H9B | 0.2615 | 0.5889 | 0.6288 | 0.021* | |
C16 | 0.30594 (4) | 1.02993 (15) | 0.60364 (4) | 0.0201 (2) | |
H16A | 0.2749 | 1.0768 | 0.5848 | 0.024* | |
H16B | 0.3340 | 1.0724 | 0.5864 | 0.024* | |
C1 | 0.34951 (4) | 0.39457 (15) | 0.52076 (4) | 0.0198 (2) | |
C23 | 0.34988 (4) | 0.72598 (16) | 0.63568 (4) | 0.01953 (19) | |
C15 | 0.16005 (4) | 0.70047 (17) | 0.66701 (4) | 0.0246 (2) | |
H15 | 0.1914 | 0.6503 | 0.6805 | 0.029* | |
C2 | 0.34409 (5) | 0.23215 (16) | 0.49074 (4) | 0.0250 (2) | |
H2 | 0.3117 | 0.1857 | 0.4793 | 0.030* | |
C6 | 0.39722 (4) | 0.46279 (18) | 0.53680 (4) | 0.0277 (2) | |
H6 | 0.4014 | 0.5728 | 0.5573 | 0.033* | |
C17 | 0.25090 (5) | 1.14867 (15) | 0.67960 (4) | 0.0255 (2) | |
C10 | 0.15440 (4) | 0.77326 (17) | 0.62029 (4) | 0.0230 (2) | |
C22 | 0.24394 (5) | 1.07987 (17) | 0.72557 (4) | 0.0300 (3) | |
H22 | 0.2712 | 1.0258 | 0.7459 | 0.036* | |
C18 | 0.21056 (5) | 1.22418 (17) | 0.64960 (5) | 0.0307 (3) | |
H18 | 0.2150 | 1.2712 | 0.6183 | 0.037* | |
C14 | 0.12017 (5) | 0.7002 (2) | 0.69433 (5) | 0.0330 (3) | |
H14 | 0.1245 | 0.6515 | 0.7265 | 0.040* | |
C3 | 0.38577 (5) | 0.13854 (18) | 0.47757 (5) | 0.0332 (3) | |
H3 | 0.3818 | 0.0272 | 0.4576 | 0.040* | |
C21 | 0.19743 (6) | 1.09037 (19) | 0.74155 (5) | 0.0375 (3) | |
H21 | 0.1930 | 1.0455 | 0.7730 | 0.045* | |
C5 | 0.43855 (5) | 0.3689 (2) | 0.52267 (5) | 0.0371 (3) | |
H5 | 0.4710 | 0.4167 | 0.5332 | 0.044* | |
C11 | 0.10797 (4) | 0.8453 (2) | 0.60058 (5) | 0.0355 (3) | |
H11 | 0.1036 | 0.8962 | 0.5686 | 0.043* | |
C4 | 0.43306 (5) | 0.2064 (2) | 0.49342 (5) | 0.0377 (3) | |
H4 | 0.4615 | 0.1422 | 0.4843 | 0.045* | |
C20 | 0.15751 (6) | 1.16595 (19) | 0.71180 (6) | 0.0414 (3) | |
H20 | 0.1257 | 1.1738 | 0.7229 | 0.050* | |
C19 | 0.16397 (5) | 1.23047 (19) | 0.66560 (6) | 0.0384 (3) | |
H19 | 0.1363 | 1.2792 | 0.6449 | 0.046* | |
C13 | 0.07437 (5) | 0.7706 (3) | 0.67479 (6) | 0.0442 (4) | |
H13 | 0.0471 | 0.7701 | 0.6934 | 0.053* | |
C12 | 0.06846 (5) | 0.8419 (3) | 0.62797 (6) | 0.0482 (4) | |
H12 | 0.0368 | 0.8892 | 0.6144 | 0.058* | |
Si1' | 0.44785 (2) | 0.8553 (2) | 0.64956 (3) | 0.0190 (2) | 0.491 (3) |
Si1 | 0.44762 (2) | 0.7677 (2) | 0.65917 (3) | 0.0212 (2) | 0.509 (3) |
C26' | 0.49264 (14) | 0.8897 (5) | 0.60512 (14) | 0.0309 (7) | 0.491 (3) |
H26A | 0.4950 | 0.7705 | 0.5866 | 0.046* | 0.491 (3) |
H26B | 0.5254 | 0.9218 | 0.6222 | 0.046* | 0.491 (3) |
H26C | 0.4812 | 0.9949 | 0.5830 | 0.046* | 0.491 (3) |
C25 | 0.45259 (9) | 0.5178 (4) | 0.68366 (9) | 0.0302 (6) | 0.509 (3) |
H25A | 0.4263 | 0.4959 | 0.7044 | 0.045* | 0.509 (3) |
H25B | 0.4852 | 0.5003 | 0.7027 | 0.045* | 0.509 (3) |
H25C | 0.4489 | 0.4254 | 0.6568 | 0.045* | 0.509 (3) |
C26 | 0.49628 (13) | 0.8198 (6) | 0.61941 (14) | 0.0355 (7) | 0.509 (3) |
H26D | 0.4953 | 0.7212 | 0.5941 | 0.053* | 0.509 (3) |
H26E | 0.5291 | 0.8190 | 0.6387 | 0.053* | 0.509 (3) |
H26F | 0.4902 | 0.9469 | 0.6044 | 0.053* | 0.509 (3) |
C24 | 0.44964 (10) | 0.9441 (4) | 0.70963 (9) | 0.0321 (6) | 0.509 (3) |
H24A | 0.4819 | 0.9348 | 0.7298 | 0.048* | 0.509 (3) |
H24B | 0.4228 | 0.9157 | 0.7293 | 0.048* | 0.509 (3) |
H24C | 0.4453 | 1.0748 | 0.6964 | 0.048* | 0.509 (3) |
C24' | 0.44206 (10) | 1.0777 (4) | 0.68546 (11) | 0.0341 (7) | 0.491 (3) |
H24D | 0.4307 | 1.1841 | 0.6637 | 0.051* | 0.491 (3) |
H24E | 0.4745 | 1.1101 | 0.7032 | 0.051* | 0.491 (3) |
H24F | 0.4179 | 1.0565 | 0.7085 | 0.051* | 0.491 (3) |
C25' | 0.46508 (10) | 0.6452 (4) | 0.68981 (11) | 0.0346 (7) | 0.491 (3) |
H25D | 0.4425 | 0.6380 | 0.7148 | 0.052* | 0.491 (3) |
H25E | 0.4994 | 0.6607 | 0.7053 | 0.052* | 0.491 (3) |
H25F | 0.4625 | 0.5264 | 0.6706 | 0.052* | 0.491 (3) |
O1' | 0.3933 (5) | 0.813 (2) | 0.6162 (5) | 0.0183 (11) | 0.491 (3) |
O1 | 0.3954 (5) | 0.788 (2) | 0.6234 (5) | 0.0193 (11) | 0.509 (3) |
H23A | 0.3479 (5) | 0.7632 (18) | 0.6703 (5) | 0.021 (3)* | |
H23B | 0.3497 (5) | 0.5849 (19) | 0.6332 (5) | 0.019 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.01888 (11) | 0.01749 (11) | 0.01825 (12) | −0.00061 (9) | 0.00277 (9) | −0.00230 (9) |
S2 | 0.01735 (11) | 0.03543 (15) | 0.01493 (12) | 0.00120 (10) | 0.00136 (9) | −0.00211 (10) |
S3 | 0.03324 (15) | 0.02129 (12) | 0.02207 (13) | −0.00472 (11) | 0.00528 (11) | −0.00615 (10) |
C8 | 0.0167 (4) | 0.0162 (4) | 0.0140 (4) | −0.0005 (3) | 0.0020 (3) | 0.0005 (3) |
C7 | 0.0191 (4) | 0.0170 (4) | 0.0153 (4) | −0.0002 (4) | 0.0022 (3) | −0.0002 (3) |
C9 | 0.0182 (4) | 0.0189 (4) | 0.0145 (4) | −0.0010 (4) | 0.0025 (3) | −0.0002 (3) |
C16 | 0.0264 (5) | 0.0174 (4) | 0.0174 (5) | −0.0018 (4) | 0.0058 (4) | −0.0006 (4) |
C1 | 0.0234 (5) | 0.0207 (5) | 0.0156 (5) | 0.0035 (4) | 0.0030 (4) | −0.0004 (4) |
C23 | 0.0178 (4) | 0.0226 (5) | 0.0177 (5) | 0.0000 (4) | 0.0004 (4) | −0.0010 (4) |
C15 | 0.0225 (5) | 0.0276 (5) | 0.0244 (5) | −0.0024 (4) | 0.0061 (4) | −0.0026 (4) |
C2 | 0.0308 (6) | 0.0227 (5) | 0.0225 (5) | −0.0004 (4) | 0.0063 (4) | −0.0040 (4) |
C6 | 0.0228 (5) | 0.0340 (6) | 0.0255 (6) | 0.0040 (5) | 0.0001 (4) | −0.0091 (5) |
C17 | 0.0377 (6) | 0.0157 (4) | 0.0246 (5) | −0.0008 (4) | 0.0103 (5) | −0.0049 (4) |
C10 | 0.0180 (5) | 0.0295 (5) | 0.0219 (5) | −0.0023 (4) | 0.0039 (4) | −0.0065 (4) |
C22 | 0.0471 (7) | 0.0225 (5) | 0.0218 (6) | −0.0035 (5) | 0.0095 (5) | −0.0062 (4) |
C18 | 0.0409 (7) | 0.0192 (5) | 0.0336 (7) | 0.0043 (5) | 0.0113 (5) | 0.0003 (4) |
C14 | 0.0299 (6) | 0.0432 (7) | 0.0281 (6) | −0.0080 (5) | 0.0129 (5) | −0.0038 (5) |
C3 | 0.0426 (7) | 0.0280 (6) | 0.0306 (6) | 0.0054 (5) | 0.0102 (5) | −0.0072 (5) |
C21 | 0.0580 (9) | 0.0275 (6) | 0.0313 (7) | −0.0067 (6) | 0.0229 (6) | −0.0097 (5) |
C5 | 0.0230 (6) | 0.0510 (8) | 0.0368 (7) | 0.0078 (6) | 0.0021 (5) | −0.0108 (6) |
C11 | 0.0206 (5) | 0.0593 (9) | 0.0259 (6) | 0.0044 (6) | 0.0005 (4) | −0.0050 (6) |
C4 | 0.0347 (7) | 0.0446 (7) | 0.0347 (7) | 0.0163 (6) | 0.0080 (5) | −0.0067 (6) |
C20 | 0.0495 (8) | 0.0259 (6) | 0.0546 (9) | −0.0009 (6) | 0.0302 (7) | −0.0126 (6) |
C19 | 0.0403 (7) | 0.0246 (6) | 0.0522 (9) | 0.0087 (5) | 0.0130 (6) | −0.0040 (6) |
C13 | 0.0212 (6) | 0.0742 (11) | 0.0396 (8) | −0.0059 (6) | 0.0136 (5) | −0.0133 (7) |
C12 | 0.0183 (6) | 0.0866 (12) | 0.0394 (8) | 0.0053 (7) | 0.0028 (5) | −0.0113 (8) |
Si1' | 0.0157 (3) | 0.0224 (5) | 0.0190 (3) | −0.0008 (3) | 0.0016 (2) | −0.0026 (3) |
Si1 | 0.0166 (3) | 0.0259 (6) | 0.0208 (3) | −0.0004 (3) | 0.0014 (2) | −0.0031 (3) |
C26' | 0.0251 (13) | 0.0358 (18) | 0.0338 (18) | −0.0041 (13) | 0.0118 (12) | −0.0020 (13) |
C25 | 0.0293 (12) | 0.0294 (13) | 0.0315 (13) | 0.0064 (10) | 0.0017 (10) | 0.0022 (10) |
C26 | 0.0256 (13) | 0.042 (2) | 0.041 (2) | −0.0075 (14) | 0.0115 (13) | −0.0063 (14) |
C24 | 0.0323 (12) | 0.0354 (13) | 0.0272 (12) | −0.0013 (10) | −0.0024 (9) | −0.0072 (10) |
C24' | 0.0216 (11) | 0.0366 (14) | 0.0437 (16) | −0.0031 (10) | 0.0021 (10) | −0.0184 (12) |
C25' | 0.0277 (12) | 0.0378 (16) | 0.0373 (15) | 0.0041 (11) | −0.0003 (10) | 0.0125 (12) |
O1' | 0.0127 (13) | 0.025 (3) | 0.016 (3) | −0.0020 (18) | −0.0013 (17) | 0.0021 (18) |
O1 | 0.0191 (16) | 0.022 (3) | 0.016 (3) | −0.0006 (15) | 0.0003 (18) | 0.0033 (17) |
S1—C7 | 1.8244 (10) | C21—H21 | 0.9500 |
S1—C1 | 1.7661 (11) | C21—C20 | 1.381 (2) |
S2—C9 | 1.8188 (10) | C5—H5 | 0.9500 |
S2—C10 | 1.7625 (12) | C5—C4 | 1.3864 (19) |
S3—C16 | 1.8214 (11) | C11—H11 | 0.9500 |
S3—C17 | 1.7742 (13) | C11—C12 | 1.3850 (19) |
C8—C7 | 1.5446 (14) | C4—H4 | 0.9500 |
C8—C9 | 1.5367 (14) | C20—H20 | 0.9500 |
C8—C16 | 1.5428 (14) | C20—C19 | 1.391 (2) |
C8—C23 | 1.5286 (14) | C19—H19 | 0.9500 |
C7—H7A | 0.9900 | C13—H13 | 0.9500 |
C7—H7B | 0.9900 | C13—C12 | 1.383 (2) |
C9—H9A | 0.9900 | C12—H12 | 0.9500 |
C9—H9B | 0.9900 | Si1'—C26' | 1.847 (4) |
C16—H16A | 0.9900 | Si1'—C24' | 1.853 (3) |
C16—H16B | 0.9900 | Si1'—C25' | 1.861 (3) |
C1—C2 | 1.3986 (15) | O1—Si1 | 1.632 (12) |
C1—C6 | 1.3957 (15) | O1'—Si1' | 1.672 (13) |
O1—C23 | 1.384 (15) | Si1—C25 | 1.861 (3) |
O1'—C23 | 1.479 (14) | Si1—C26 | 1.853 (4) |
C23—H23A | 1.004 (14) | Si1—C24 | 1.856 (3) |
C23—H23B | 0.981 (13) | C26'—H26A | 0.9800 |
C15—H15 | 0.9500 | C26'—H26B | 0.9800 |
C15—C10 | 1.3845 (16) | C26'—H26C | 0.9800 |
C15—C14 | 1.3918 (16) | C25—H25A | 0.9800 |
C2—H2 | 0.9500 | C25—H25B | 0.9800 |
C2—C3 | 1.3875 (17) | C25—H25C | 0.9800 |
C6—H6 | 0.9500 | C26—H26D | 0.9800 |
C6—C5 | 1.3905 (17) | C26—H26E | 0.9800 |
C17—C22 | 1.3977 (17) | C26—H26F | 0.9800 |
C17—C18 | 1.3925 (18) | C24—H24A | 0.9800 |
C10—C11 | 1.3998 (16) | C24—H24B | 0.9800 |
C22—H22 | 0.9500 | C24—H24C | 0.9800 |
C22—C21 | 1.3856 (19) | C24'—H24D | 0.9800 |
C18—H18 | 0.9500 | C24'—H24E | 0.9800 |
C18—C19 | 1.3865 (19) | C24'—H24F | 0.9800 |
C14—H14 | 0.9500 | C25'—H25D | 0.9800 |
C14—C13 | 1.380 (2) | C25'—H25E | 0.9800 |
C3—H3 | 0.9500 | C25'—H25F | 0.9800 |
C3—C4 | 1.384 (2) | ||
C1—S1—C7 | 105.85 (5) | C4—C5—C6 | 120.88 (12) |
C10—S2—C9 | 103.65 (5) | C4—C5—H5 | 119.6 |
C17—S3—C16 | 104.74 (5) | C10—C11—H11 | 120.2 |
C9—C8—C7 | 112.14 (8) | C12—C11—C10 | 119.60 (13) |
C9—C8—C16 | 111.46 (8) | C12—C11—H11 | 120.2 |
C16—C8—C7 | 105.78 (8) | C3—C4—C5 | 119.50 (12) |
C23—C8—C7 | 110.11 (8) | C3—C4—H4 | 120.3 |
C23—C8—C9 | 106.65 (8) | C5—C4—H4 | 120.3 |
C23—C8—C16 | 110.77 (8) | C21—C20—H20 | 120.1 |
S1—C7—H7A | 108.6 | C21—C20—C19 | 119.90 (13) |
S1—C7—H7B | 108.6 | C19—C20—H20 | 120.1 |
C8—C7—S1 | 114.55 (7) | C18—C19—C20 | 120.43 (14) |
C8—C7—H7A | 108.6 | C18—C19—H19 | 119.8 |
C8—C7—H7B | 108.6 | C20—C19—H19 | 119.8 |
H7A—C7—H7B | 107.6 | C14—C13—H13 | 120.2 |
S2—C9—H9A | 109.5 | C14—C13—C12 | 119.53 (12) |
S2—C9—H9B | 109.5 | C12—C13—H13 | 120.2 |
C8—C9—S2 | 110.82 (7) | C11—C12—H12 | 119.5 |
C8—C9—H9A | 109.5 | C13—C12—C11 | 120.94 (13) |
C8—C9—H9B | 109.5 | C13—C12—H12 | 119.5 |
H9A—C9—H9B | 108.1 | C26'—Si1'—C24' | 110.96 (16) |
S3—C16—H16A | 108.2 | C26'—Si1'—C25' | 111.49 (15) |
S3—C16—H16B | 108.2 | C24'—Si1'—C25' | 111.01 (15) |
C8—C16—S3 | 116.27 (7) | O1'—Si1'—C26' | 104.9 (5) |
C8—C16—H16A | 108.2 | O1'—Si1'—C24' | 108.7 (6) |
C8—C16—H16B | 108.2 | O1'—Si1'—C25' | 109.6 (4) |
H16A—C16—H16B | 107.4 | C26—Si1—C25 | 112.00 (15) |
C2—C1—S1 | 116.04 (8) | C26—Si1—C24 | 111.33 (15) |
C6—C1—S1 | 124.56 (8) | C24—Si1—C25 | 110.04 (13) |
C6—C1—C2 | 119.31 (10) | O1—Si1—C25 | 108.8 (5) |
C8—C23—H23A | 109.5 (7) | O1—Si1—C26 | 104.2 (5) |
C8—C23—H23B | 109.2 (7) | O1—Si1—C24 | 110.4 (6) |
O1'—C23—C8 | 104.4 (4) | Si1'—C26'—H26A | 109.5 |
O1'—C23—H23A | 112.6 (10) | Si1'—C26'—H26B | 109.5 |
O1'—C23—H23B | 112.1 (10) | Si1'—C26'—H26C | 109.5 |
O1—C23—C8 | 114.3 (4) | H26A—C26'—H26B | 109.5 |
O1—C23—H23A | 108.0 (10) | H26A—C26'—H26C | 109.5 |
O1—C23—H23B | 106.8 (10) | H26B—C26'—H26C | 109.5 |
H23A—C23—H23B | 108.9 (11) | Si1—C25—H25A | 109.5 |
C10—C15—H15 | 119.8 | Si1—C25—H25B | 109.5 |
C10—C15—C14 | 120.49 (11) | Si1—C25—H25C | 109.5 |
C14—C15—H15 | 119.8 | H25A—C25—H25B | 109.5 |
C1—C2—H2 | 119.9 | H25A—C25—H25C | 109.5 |
C3—C2—C1 | 120.28 (11) | H25B—C25—H25C | 109.5 |
C3—C2—H2 | 119.9 | Si1—C26—H26D | 109.5 |
C1—C6—H6 | 120.2 | Si1—C26—H26E | 109.5 |
C5—C6—C1 | 119.65 (11) | Si1—C26—H26F | 109.5 |
C5—C6—H6 | 120.2 | H26D—C26—H26E | 109.5 |
C22—C17—S3 | 118.00 (10) | H26D—C26—H26F | 109.5 |
C18—C17—S3 | 122.37 (10) | H26E—C26—H26F | 109.5 |
C18—C17—C22 | 119.57 (12) | Si1—C24—H24A | 109.5 |
C15—C10—S2 | 124.22 (9) | Si1—C24—H24B | 109.5 |
C15—C10—C11 | 119.28 (11) | Si1—C24—H24C | 109.5 |
C11—C10—S2 | 116.50 (10) | H24A—C24—H24B | 109.5 |
C17—C22—H22 | 119.9 | H24A—C24—H24C | 109.5 |
C21—C22—C17 | 120.19 (13) | H24B—C24—H24C | 109.5 |
C21—C22—H22 | 119.9 | Si1'—C24'—H24D | 109.5 |
C17—C18—H18 | 120.1 | Si1'—C24'—H24E | 109.5 |
C19—C18—C17 | 119.75 (13) | Si1'—C24'—H24F | 109.5 |
C19—C18—H18 | 120.1 | H24D—C24'—H24E | 109.5 |
C15—C14—H14 | 119.9 | H24D—C24'—H24F | 109.5 |
C13—C14—C15 | 120.15 (13) | H24E—C24'—H24F | 109.5 |
C13—C14—H14 | 119.9 | Si1'—C25'—H25D | 109.5 |
C2—C3—H3 | 119.8 | Si1'—C25'—H25E | 109.5 |
C4—C3—C2 | 120.38 (12) | Si1'—C25'—H25F | 109.5 |
C4—C3—H3 | 119.8 | H25D—C25'—H25E | 109.5 |
C22—C21—H21 | 119.9 | H25D—C25'—H25F | 109.5 |
C20—C21—C22 | 120.13 (13) | H25E—C25'—H25F | 109.5 |
C20—C21—H21 | 119.9 | C23—O1'—Si1' | 123.7 (7) |
C6—C5—H5 | 119.6 | C23—O1—Si1 | 123.6 (7) |
S1—C1—C2—C3 | −175.92 (10) | C23—C8—C7—S1 | 71.19 (9) |
S1—C1—C6—C5 | 176.56 (10) | C23—C8—C9—S2 | −169.94 (7) |
S2—C10—C11—C12 | 179.49 (12) | C23—C8—C16—S3 | −53.29 (11) |
S3—C17—C22—C21 | 175.84 (9) | C15—C10—C11—C12 | −0.3 (2) |
S3—C17—C18—C19 | −176.99 (9) | C15—C14—C13—C12 | −0.2 (2) |
C8—C23—O1'—Si1' | 151.5 (9) | C2—C1—C6—C5 | 0.14 (18) |
C8—C23—O1—Si1 | 163.9 (8) | C2—C3—C4—C5 | 0.1 (2) |
C7—S1—C1—C2 | −153.61 (8) | C6—C1—C2—C3 | 0.80 (18) |
C7—S1—C1—C6 | 29.86 (11) | C6—C5—C4—C3 | 0.9 (2) |
C7—C8—C9—S2 | −49.35 (10) | C17—S3—C16—C8 | −81.99 (9) |
C7—C8—C16—S3 | −172.59 (7) | C17—C22—C21—C20 | 1.09 (18) |
C7—C8—C23—O1' | 60.9 (7) | C17—C18—C19—C20 | 1.48 (19) |
C7—C8—C23—O1 | 60.3 (8) | C10—S2—C9—C8 | −157.51 (7) |
C9—S2—C10—C15 | −12.64 (11) | C10—C15—C14—C13 | 0.8 (2) |
C9—S2—C10—C11 | 167.62 (10) | C10—C11—C12—C13 | 0.9 (2) |
C9—C8—C7—S1 | −47.38 (10) | C22—C17—C18—C19 | 0.02 (17) |
C9—C8—C16—S3 | 65.28 (10) | C22—C21—C20—C19 | 0.4 (2) |
C9—C8—C23—O1' | −177.2 (7) | C18—C17—C22—C21 | −1.30 (17) |
C9—C8—C23—O1 | −177.8 (8) | C14—C15—C10—S2 | 179.72 (10) |
C16—S3—C17—C22 | 129.90 (9) | C14—C15—C10—C11 | −0.55 (18) |
C16—S3—C17—C18 | −53.05 (11) | C14—C13—C12—C11 | −0.6 (3) |
C16—C8—C7—S1 | −169.08 (7) | C21—C20—C19—C18 | −1.7 (2) |
C16—C8—C9—S2 | 69.04 (9) | C26'—Si1'—O1'—C23 | 163.0 (10) |
C16—C8—C23—O1' | −55.8 (7) | C25—Si1—O1—C23 | 47.9 (13) |
C16—C8—C23—O1 | −56.3 (8) | C26—Si1—O1—C23 | 167.5 (11) |
C1—S1—C7—C8 | −115.70 (7) | C24—Si1—O1—C23 | −72.9 (12) |
C1—C2—C3—C4 | −0.9 (2) | C24'—Si1'—O1'—C23 | −78.3 (11) |
C1—C6—C5—C4 | −1.0 (2) | C25'—Si1'—O1'—C23 | 43.2 (13) |
Br1–C3 | 1.948 (3) | C1–C3–Br1 | 112.99 (18) |
Br2–C4 | 1.952 (3) | C1–C4–Br2 | 113.48 (18) |
Br3–C5 | 1.950 (3) | C1–C5–Br3 | 113.21 (19) |
O1–C2 | 1.432 (3) | O1–C2–C1 | 111.6 (2) |
S1–C7 | 1.8242 (11) | C1–S1–C7 | 105.84 (5) |
S1–C1 | 1.7661 (11) | C10–S2–C16 | 103.67 (5) |
S2–C9 | 1.8183 (11) | C17–S3–C16 | 104.74 (5) |
S2–C10 | 1.7621 (12) | C23–O1–Si1 | 123.3 (8) |
S3–C16 | 1.8211 (11) | C23–O1'–Si1' | 123.8 (8) |
S3–C17 | 1.7739 (13) | ||
O1–C23 | 1.385 (17) | ||
O1'–C23 | 1.480 (15) | ||
O1–Si1 | 1.636 (14) | ||
O1'–Si1' | 1.669 (15) |
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