research communications
μ-4-hydroxybenzenethiolato-κ2S:S)bis(μ-phenylmethanethiolato-κ2S:S)bis[(η6-1-isopropyl-4-methylbenzene)ruthenium(II)] tetrafluoridoborate
of (aInstitut de Chimie, Université de Neuchâtel, Avenue de Bellevaux 51, CH-2000 Neuchâtel, Switzerland
*Correspondence e-mail: bruno.therrien@unine.ch
The 2(C6H5OS)(C7H7S)2(C10H14)2]BF4, shows the two RuII atoms to be bridged by two benzylthiophenolate units and one 4-hydroxythiophenolate unit, with the remaining three coordination sites of each RuII atom being occupied by p-cymene ligands, completing the typical piano-stool coordination geometry. The BF4− counter-anion is surrounded by four cationic dinuclear complexes, showing an O—H⋯F hydrogen bond and several weak C—H⋯F interactions. This is the first example of an X-ray analysis of a mixed dinuclear trithiolate arene ruthenium(II) complex.
of the dinuclear arene ruthenium title complex, [RuKeywords: crystal structure; ruthenium complex; piano-stool coordination geometry; thiolate ligands.
CCDC reference: 1423473
1. Chemical context
In the search for novel metal-based anticancer agents, several series of dinuclear trithiolate arene ruthenium complexes have been synthesized by our group (Gras et al., 2010; Giannini et al., 2012, 2013a). The biological studies in vitro showed the chloride salts of these complexes to have IC50 values regularly in the nanomolar range, making them some of the most active ruthenium complexes found to date. The recent discovery of dithiolate complexes (Ibao et al., 2012) allowed us to synthesize the so-called mixed trithiolate complexes of the type [(p-MeC6H4iPr)2Ru2(SCH2R1)2(S-p-C6H4-R2]+ (R1 = C6H5, CH2C6H5, p-C6H4tBu; R2 = H, OH, F, Br, iPr, tBu). All of the complexes were found to be highly cytotoxic against ovarian cancer cell lines A2780 and A2780cisR as chloride salts, none of them could however be crystallized and analyzed by X-ray crystallography (Giannini et al., 2013b). Herein we report the isolation and the of the title compound, [(p-MeC6H4iPr)2Ru2(SCH2C6H5)2(S-p-C6H4OH)]BF4, (I), the first reported structure of a mixed trithiolate complex.
2. Structural commentary
The structures of the molecular components of compound (I) are presented in Fig. 1. Both RuII atoms adopt the typical piano-stool geometry with the p-cymene ligand being bound facially, formally occupying three coordination sites; the other three positions are occupied by two benzylthiophenolate units and one 4-hydroxythiophenolate unit. In agreement with the electron count, there is no metal–metal bond, the Ru⋯Ru distance being 3.3632 (4) Å. The interatomic distances between Ru1 and S1, S2 and S3 are 2.3878 (9), 2.4023 (9) and 2.3813 (8) Å, respectively, and between Ru2 and S1, S2 and S3 2.3992 (9), 2.3991 (8) and 2.3882 (8) Å, respectively, showing that the central diruthenium trithiolate unit is not symmetric. The presence of the two bent benzylthiolate ligands forces the dinuclear arene ruthenium unit to adopt a distorted geometry – the angle between the two p-cymene planes (C1–C6 and C11–C16) is 6.2 (2)°. The distances between the RuII atoms and the centroids of the associated rings are 1.708 and 1.709 Å.
3. Supramolecular features
In the crystal packing of (I), the BF4− anion interacts with the –OH group of the 4-hydroxythiophenolate unit. In addition, weak C—H⋯F interactions are observed (Table 1), thus creating around the BF4 anion a densely packed arrangement (Fig. 2). No significant C—H⋯π or π–π stacking interactions are observed in the crystal structure.
4. Synthesis and crystallization
Complex (I) was obtained from the reaction of 0.127 mmol (100 mg) of the neutral dithiolate precursor [(p-MeC6H4iPr)2Ru2(SCH2C6H5)2Cl2] (Ibao et al., 2012) with three equivalents of 4-hydroxythiophenol in refluxing ethanol. The product was isolated by on silica gel, using the solvent mixture CH2Cl2/EtOH 7:1 (v/v) as The orange band was collected; the product was stirred overnight with ten equivalents of NaBF4 and isolated by filtration and evaporation of the solvent. X-ray quality crystals were obtained by slow diffusion of diethyl ether vapors into the solution of (I) in dichloromethane.
Yield: 111 mg (94%). ESI–MS (MeOH/CH2Cl2): m/z = 842.3 [M]+. 1H NMR (400 MHz, CDCl3): δ = 7.41 (m, 10H, SCH2C6H5; 2H, S-p-C6H4OH), 7.00 (d, 3J = 8 Hz, 2H, S-p-C6H4OH) 5.06 [d, 3J = 6.0 Hz, 2H, p-CH3C6H4CH(CH3)2], 4.94 [d, 3J = 6.0 Hz, 2H, p-CH3C6H4CH(CH3)2], 4.71 [m, 4H, p-CH3C6H4CH(CH3)2], 3.62 (s, 2H, SCH2C6H5), 3.45 (s, 2H, SCH2C6H5), 2.04 [sept, 3J = 6.8 Hz, 2H, p-CH3C6H4CH(CH3)2], 1.73 (s, 6H, p-CH3C6H4CH(CH3)2), 1.05 [d, 3J = 6.8 Hz, 6H, p-CH3C6H4CH(CH3)2], 0.99 [d, 3J = 6.8 Hz, 6H, p-CH3C6H4CH(CH3)2] p.p.m. 13C{1H} NMR (100 MHz,CDCl3): δ = 159.9, 139.9, 139.7, 133.3, 129.5, 129.2, 128.8, 128.7, 128.2, 128.1, 124.0, 117.1, 107.5, 99.7, 84.1, 83.7, 83.2, 82.0, 39.9, 39.5, 31.0, 23.1, 22.7, 18.0 p.p.m.
5. Refinement
Crystal data, data collection and structure . All H atoms were included in calculated positions and treated as riding atoms, with C—H = 0.93 Å for Carom and 0.96 Å for CH3, and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.
details are summarized in Table 2Supporting information
CCDC reference: 1423473
10.1107/S2056989015016953/wm5210sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989015016953/wm5210Isup2.hkl
\ In the search for novel metal-based anticancer agents, several series of dinuclear trithiolate arene ruthenium complexes have been synthesized by our group (Gras et al., 2010; Giannini et al., 2012, 2013a). The biological studies in vitro showed the chloride salts of these complexes to have IC50 values regularly in the nanomolar range, making them some of the most active ruthenium complexes found to date. The recent discovery of dithiolate complexes (Ibao et al., 2012) allowed us to synthesize the so-called mixed trithiolate complexes of the type [(p-MeC6H4iPr)2Ru2(SCH2R1)2(S-p-\ C6H4-R2]+ (R1 = C6H5, CH2C6H5, p-C6H4tBu; R2 = H, OH, F, Br, iPr, tBu). All of the complexes were found to be highly cytotoxic against ovarian cancer cell lines A2780 and A2780cisR as chloride salts, none of them could however be crystallized and analyzed by X-ray crystallography (Giannini et al., 2013b). Herein we report the isolation and the
of the title compound, [(p-MeC6H4iPr)2Ru2(SCH2C6H5)2(S-p-\ C6H4OH)]BF4, (I), the first reported structure of a mixed trithiolate complex.The structure of the molecular components of compound (I) is presented in Fig. 1. Both RuII atoms adopt the typical piano-stool geometry with the p-cymene ligand being bound facially, formally occupying three coordination sites; the other three positions are occupied by two benzylthiophenolate units and one 4-hydroxythiophenolate unit. In agreement with the electron count, there is no metal–metal bond, the Ru···Ru distance being 3.3632 (4) Å. The interatomic distances between Ru1 and S1, S2 and S3 are 2.3878 (9), 2.4023 (9) and 2.3813 (8) Å, respectively, and between Ru2 and S1, S2 and S3 2.3992 (9), 2.3991 (8) and 2.3882 (8) Å, respectively, showing that the central diruthenium trithiolate unit is not symmetric. The presence of the two bent benzylthiolate ligands forces the dinuclear arene ruthenium unit to adopt a distorted geometry – the angle between the two p-cymene planes (C1–C6 and C11–C16) is 6.2 (2)°. The distances between the RuII atoms and the centroid of the associated ring are 1.708 and 1.709 Å.
In the crystal packing of (I), the BF4- anion interacts with the –OH group of the 4-hydroxythiophenolate unit. In addition, weak C—H···F interactions are observed (Table 1), thus creating around the BF4 anion a densely packed arrangement (Fig. 2). No significant C—H···π or π–π stacking interactions are observed in the crystal structure.
Complex (I) was obtained from the reaction of 0.127 mmol (100 mg) of the neutral dithiolate precursor [(p-MeC6H4iPr)2Ru2(SCH2C6H5)2Cl2] (Ibao et al., 2012) with three equivalents of 4-hydroxythiophenol in refluxing ethanol. The product was isolated by
on silica gel, using the solvent mixture CH2Cl2/EtOH 7:1 (v/v) as The orange band was collected; the product was stirred overnight with ten equivalents of NaBF4 and isolated by filtration and evaporation of the solvent. X-ray quality crystals were obtained by slow diffusion of diethyl ether vapors into the solution of (I) in dichloromethane.Yield: 111 mg (94%). ESI–MS (MeOH/CH2Cl2): m/z = 842.3 [M]+. 1H NMR (400 MHz, CDCl3): δ = 7.41 (m, 10H, SCH2C6H5; 2H, S-p-C6H4OH), 7.00 (d, 3J = 8 Hz, 2H, S-p-C6H4OH) 5.06 [d, 3J = 6.0 Hz, 2H, p-CH3C6H4CH(CH3)2], 4.94 [d, 3J = 6.0 Hz, 2H, p-CH3C6H4CH(CH3)2], 4.71 [m, 4H, p-CH3C6H4CH(CH3)2], 3.62 (s, 2H, SCH2C6H5), 3.45 (s, 2H, SCH2C6H5), 2.04 [sept, 3J = 6.8 Hz, 2H, p-CH3C6H4CH(CH3)2], 1.73 (s, 6H, p-CH3C6H4CH(CH3)2), 1.05 [d, 3J = 6.8 Hz, 6H, p-CH3C6H4CH(CH3)2], 0.99 [d, 3J = 6.8 Hz, 6H, p-CH3C6H4CH(CH3)2] p.p.m. 13C{1H} NMR (100 MHz,CDCl3): δ = 159.9, 139.9, 139.7, 133.3, 129.5, 129.2, 128.8, 128.7, 128.2, 128.1, 124.0, 117.1, 107.5, 99.7, 84.1, 83.7, 83.2, 82.0, 39.9, 39.5, 31.0, 23.1, 22.7, 18.0 ppm.
Data collection: EXPOSE in IPDS Software (Stoe & Cie, 2000); cell
CELL in IPDS Software (Stoe & Cie, 2000); data reduction: INTEGRATE in IPDS Software (Stoe & Cie, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-32 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).Fig. 1. The structure of the molecular components of (I). Displacement ellipsoids are drawn at the 50% probability level. | |
Fig. 2. Surroundings of the BF4- anion in the crystal packing of (I). |
[Ru2(C6H5OS)(C7H7S)2(C10H14)2]BF4 | F(000) = 1888 |
Mr = 928.91 | Dx = 1.586 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 8000 reflections |
a = 15.4807 (10) Å | θ = 2.1–28.7° |
b = 14.3435 (11) Å | µ = 0.99 mm−1 |
c = 17.7605 (10) Å | T = 173 K |
β = 99.435 (5)° | Block, red |
V = 3890.3 (4) Å3 | 0.22 × 0.20 × 0.18 mm |
Z = 4 |
Stoe IPDS diffractometer | 8902 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
Graphite monochromator | θmax = 29.4°, θmin = 2.0° |
Detector resolution: 0.81 pixels mm-1 | h = −21→21 |
phi oscillation scans | k = −19→19 |
34511 measured reflections | l = −24→24 |
10178 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.074 | w = 1/[σ2(Fo2) + (0.0431P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max = 0.001 |
10178 reflections | Δρmax = 0.52 e Å−3 |
466 parameters | Δρmin = −0.69 e Å−3 |
2 restraints | Absolute structure: Flack x determined using 3741 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013). |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.01 (2) |
[Ru2(C6H5OS)(C7H7S)2(C10H14)2]BF4 | V = 3890.3 (4) Å3 |
Mr = 928.91 | Z = 4 |
Monoclinic, Cc | Mo Kα radiation |
a = 15.4807 (10) Å | µ = 0.99 mm−1 |
b = 14.3435 (11) Å | T = 173 K |
c = 17.7605 (10) Å | 0.22 × 0.20 × 0.18 mm |
β = 99.435 (5)° |
Stoe IPDS diffractometer | 8902 reflections with I > 2σ(I) |
34511 measured reflections | Rint = 0.060 |
10178 independent reflections |
R[F2 > 2σ(F2)] = 0.032 | H-atom parameters constrained |
wR(F2) = 0.074 | Δρmax = 0.52 e Å−3 |
S = 0.95 | Δρmin = −0.69 e Å−3 |
10178 reflections | Absolute structure: Flack x determined using 3741 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013). |
466 parameters | Absolute structure parameter: −0.01 (2) |
2 restraints |
Experimental. A crystal was mounted at 173 K on a Stoe Image Plate Diffraction System (Stoe & Cie, 2000) using Mo Kα graphite monochromated radiation. Image plate distance 100 mm, φ oscillation scans 0 - 180°, step Δφ = 1.2°, 5 minutes per frame. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.3292 (2) | 0.1913 (3) | −0.0509 (2) | 0.0418 (9) | |
C2 | 0.3924 (2) | 0.1437 (2) | 0.0030 (2) | 0.0331 (8) | |
H2 | 0.4249 | 0.0957 | −0.0136 | 0.040* | |
C3 | 0.4066 (2) | 0.1680 (3) | 0.0807 (3) | 0.0374 (8) | |
H3 | 0.4490 | 0.1366 | 0.1146 | 0.045* | |
C4 | 0.3569 (3) | 0.2402 (3) | 0.1080 (3) | 0.0465 (10) | |
C5 | 0.2935 (3) | 0.2860 (3) | 0.0556 (3) | 0.0528 (13) | |
H5 | 0.2601 | 0.3330 | 0.0725 | 0.063* | |
C6 | 0.2797 (3) | 0.2620 (3) | −0.0221 (3) | 0.0539 (13) | |
H6 | 0.2369 | 0.2934 | −0.0555 | 0.065* | |
C7 | 0.3156 (3) | 0.1726 (5) | −0.1358 (3) | 0.0646 (15) | |
H7 | 0.2531 | 0.1806 | −0.1556 | 0.077* | |
C8 | 0.3413 (5) | 0.0761 (5) | −0.1566 (3) | 0.085 (2) | |
H8A | 0.4037 | 0.0691 | −0.1436 | 0.128* | |
H8B | 0.3238 | 0.0665 | −0.2104 | 0.128* | |
H8C | 0.3130 | 0.0310 | −0.1290 | 0.128* | |
C9 | 0.3654 (6) | 0.2436 (6) | −0.1742 (5) | 0.110 (3) | |
H9A | 0.4271 | 0.2323 | −0.1605 | 0.165* | |
H9B | 0.3520 | 0.3050 | −0.1581 | 0.165* | |
H9C | 0.3489 | 0.2386 | −0.2286 | 0.165* | |
C10 | 0.3719 (3) | 0.2648 (4) | 0.1917 (3) | 0.0667 (16) | |
H10A | 0.4222 | 0.3047 | 0.2030 | 0.100* | |
H10B | 0.3817 | 0.2088 | 0.2215 | 0.100* | |
H10C | 0.3213 | 0.2965 | 0.2038 | 0.100* | |
C11 | −0.0326 (3) | −0.0067 (3) | 0.0892 (3) | 0.0397 (10) | |
C12 | 0.0199 (3) | −0.0321 (3) | 0.1574 (3) | 0.0441 (10) | |
H12 | 0.0179 | 0.0032 | 0.2010 | 0.053* | |
C13 | 0.0767 (3) | −0.1107 (3) | 0.1620 (3) | 0.0466 (10) | |
H13 | 0.1105 | −0.1268 | 0.2084 | 0.056* | |
C14 | 0.0818 (3) | −0.1643 (3) | 0.0962 (3) | 0.0484 (11) | |
C15 | 0.0298 (3) | −0.1365 (3) | 0.0277 (3) | 0.0472 (10) | |
H15 | 0.0328 | −0.1701 | −0.0166 | 0.057* | |
C16 | −0.0262 (2) | −0.0602 (3) | 0.0242 (3) | 0.0419 (9) | |
H16 | −0.0601 | −0.0443 | −0.0222 | 0.050* | |
C17 | −0.0956 (3) | 0.0766 (3) | 0.0801 (3) | 0.0545 (12) | |
H17 | −0.0907 | 0.1071 | 0.0316 | 0.065* | |
C18 | −0.0757 (4) | 0.1487 (4) | 0.1421 (5) | 0.082 (2) | |
H18A | −0.0799 | 0.1208 | 0.1905 | 0.123* | |
H18B | −0.1170 | 0.1989 | 0.1324 | 0.123* | |
H18C | −0.0175 | 0.1724 | 0.1430 | 0.123* | |
C19 | −0.1899 (3) | 0.0414 (4) | 0.0745 (6) | 0.095 (3) | |
H19A | −0.2025 | −0.0017 | 0.0328 | 0.143* | |
H19B | −0.2296 | 0.0932 | 0.0660 | 0.143* | |
H19C | −0.1967 | 0.0107 | 0.1212 | 0.143* | |
C20 | 0.1397 (3) | −0.2491 (3) | 0.0989 (5) | 0.091 (3) | |
H20A | 0.1881 | −0.2428 | 0.1399 | 0.137* | |
H20B | 0.1613 | −0.2550 | 0.0515 | 0.137* | |
H20C | 0.1065 | −0.3037 | 0.1071 | 0.137* | |
C21 | 0.1759 (2) | 0.1523 (2) | 0.2144 (2) | 0.0318 (7) | |
C22 | 0.1763 (2) | 0.1270 (3) | 0.2903 (2) | 0.0381 (8) | |
H22 | 0.1959 | 0.0680 | 0.3069 | 0.046* | |
C23 | 0.1479 (3) | 0.1880 (3) | 0.3412 (2) | 0.0456 (9) | |
H23 | 0.1476 | 0.1698 | 0.3914 | 0.055* | |
C24 | 0.1202 (2) | 0.2753 (3) | 0.3176 (2) | 0.0431 (9) | |
C25 | 0.1177 (3) | 0.3026 (3) | 0.2427 (2) | 0.0407 (8) | |
H25 | 0.0976 | 0.3617 | 0.2269 | 0.049* | |
C26 | 0.1457 (2) | 0.2409 (3) | 0.1908 (2) | 0.0365 (8) | |
H26 | 0.1440 | 0.2589 | 0.1403 | 0.044* | |
C27 | 0.3138 (2) | −0.1002 (3) | 0.0697 (3) | 0.0413 (9) | |
H27A | 0.3159 | −0.0859 | 0.1234 | 0.050* | |
H27B | 0.2955 | −0.1646 | 0.0617 | 0.050* | |
C28 | 0.4040 (2) | −0.0887 (3) | 0.0494 (3) | 0.0382 (9) | |
C29 | 0.4732 (3) | −0.0540 (3) | 0.1000 (3) | 0.0463 (10) | |
H29 | 0.4660 | −0.0401 | 0.1497 | 0.056* | |
C30 | 0.5543 (3) | −0.0392 (3) | 0.0774 (3) | 0.0540 (12) | |
H30 | 0.6005 | −0.0153 | 0.1121 | 0.065* | |
C31 | 0.5663 (3) | −0.0597 (3) | 0.0048 (3) | 0.0536 (11) | |
H31 | 0.6203 | −0.0487 | −0.0101 | 0.064* | |
C32 | 0.4971 (3) | −0.0975 (3) | −0.0476 (3) | 0.0601 (13) | |
H32 | 0.5052 | −0.1129 | −0.0968 | 0.072* | |
C33 | 0.4171 (3) | −0.1112 (3) | −0.0250 (3) | 0.0500 (11) | |
H33 | 0.3710 | −0.1358 | −0.0595 | 0.060* | |
C34 | 0.0879 (2) | 0.1145 (3) | −0.0955 (2) | 0.0406 (8) | |
H34A | 0.1073 | 0.1690 | −0.1205 | 0.049* | |
H34B | 0.1209 | 0.0612 | −0.1088 | 0.049* | |
C35 | −0.0078 (2) | 0.0988 (3) | −0.1235 (2) | 0.0376 (8) | |
C36 | −0.0411 (3) | 0.0170 (3) | −0.1584 (3) | 0.0511 (10) | |
H36 | −0.0032 | −0.0302 | −0.1678 | 0.061* | |
C37 | −0.1319 (4) | 0.0053 (4) | −0.1796 (3) | 0.0602 (13) | |
H37 | −0.1538 | −0.0494 | −0.2036 | 0.072* | |
C38 | −0.1877 (3) | 0.0729 (4) | −0.1652 (3) | 0.0652 (14) | |
H38 | −0.2478 | 0.0638 | −0.1782 | 0.078* | |
C39 | −0.1565 (3) | 0.1543 (5) | −0.1317 (3) | 0.0691 (15) | |
H39 | −0.1950 | 0.2013 | −0.1229 | 0.083* | |
C40 | −0.0678 (3) | 0.1665 (3) | −0.1112 (3) | 0.0494 (10) | |
H40 | −0.0472 | 0.2222 | −0.0882 | 0.059* | |
O1 | 0.0975 (2) | 0.3350 (3) | 0.3719 (2) | 0.0593 (8) | |
H1 | 0.0820 | 0.3852 | 0.3519 | 0.089* | |
S1 | 0.22003 (5) | 0.07062 (6) | 0.15529 (5) | 0.02976 (16) | |
S2 | 0.23352 (5) | −0.02440 (6) | 0.01262 (5) | 0.02999 (17) | |
S3 | 0.11024 (5) | 0.13178 (6) | 0.00909 (5) | 0.02880 (17) | |
Ru1 | 0.265363 (15) | 0.136095 (17) | 0.044464 (15) | 0.02751 (6) | |
Ru2 | 0.107114 (15) | −0.013494 (17) | 0.074285 (15) | 0.02631 (6) | |
B1 | 0.1140 (3) | 0.5937 (4) | 0.2810 (3) | 0.0508 (12) | |
F1 | 0.0880 (5) | 0.5128 (3) | 0.3096 (4) | 0.161 (3) | |
F2 | 0.1726 (2) | 0.5769 (3) | 0.23242 (19) | 0.0842 (11) | |
F3 | 0.0429 (4) | 0.6320 (7) | 0.2444 (4) | 0.196 (4) | |
F4 | 0.1457 (4) | 0.6454 (6) | 0.3380 (4) | 0.212 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0331 (17) | 0.046 (2) | 0.049 (2) | −0.0089 (16) | 0.0128 (17) | 0.0188 (18) |
C2 | 0.0272 (16) | 0.0314 (17) | 0.043 (2) | −0.0065 (13) | 0.0120 (15) | 0.0043 (15) |
C3 | 0.0244 (15) | 0.0380 (19) | 0.050 (2) | −0.0071 (14) | 0.0069 (15) | 0.0017 (18) |
C4 | 0.0360 (18) | 0.035 (2) | 0.070 (3) | −0.0164 (16) | 0.0148 (19) | −0.009 (2) |
C5 | 0.044 (2) | 0.0277 (19) | 0.093 (4) | −0.0083 (16) | 0.030 (3) | 0.002 (2) |
C6 | 0.037 (2) | 0.037 (2) | 0.091 (4) | −0.0002 (16) | 0.020 (2) | 0.033 (2) |
C7 | 0.044 (2) | 0.104 (4) | 0.048 (3) | −0.009 (3) | 0.015 (2) | 0.029 (3) |
C8 | 0.111 (5) | 0.102 (5) | 0.041 (3) | −0.062 (4) | 0.011 (3) | −0.002 (3) |
C9 | 0.147 (7) | 0.088 (4) | 0.119 (6) | 0.024 (4) | 0.089 (5) | 0.058 (4) |
C10 | 0.048 (2) | 0.073 (3) | 0.082 (4) | −0.022 (2) | 0.021 (2) | −0.042 (3) |
C11 | 0.0280 (17) | 0.0348 (19) | 0.060 (3) | −0.0046 (14) | 0.0184 (18) | 0.0097 (18) |
C12 | 0.046 (2) | 0.050 (2) | 0.044 (2) | −0.0096 (18) | 0.0295 (19) | 0.0008 (19) |
C13 | 0.0347 (18) | 0.058 (2) | 0.049 (2) | −0.0050 (17) | 0.0108 (17) | 0.030 (2) |
C14 | 0.0350 (19) | 0.0304 (18) | 0.086 (4) | −0.0031 (15) | 0.029 (2) | 0.017 (2) |
C15 | 0.041 (2) | 0.040 (2) | 0.066 (3) | −0.0169 (17) | 0.028 (2) | −0.014 (2) |
C16 | 0.0275 (17) | 0.054 (2) | 0.045 (2) | −0.0154 (17) | 0.0077 (16) | 0.0044 (19) |
C17 | 0.038 (2) | 0.041 (2) | 0.088 (4) | 0.0049 (17) | 0.020 (2) | 0.014 (2) |
C18 | 0.058 (3) | 0.047 (3) | 0.147 (6) | 0.004 (2) | 0.034 (4) | −0.018 (3) |
C19 | 0.036 (2) | 0.049 (3) | 0.205 (8) | 0.001 (2) | 0.032 (4) | −0.002 (4) |
C20 | 0.051 (3) | 0.037 (2) | 0.197 (8) | 0.004 (2) | 0.053 (4) | 0.031 (4) |
C21 | 0.0247 (14) | 0.0372 (18) | 0.0332 (18) | −0.0013 (13) | 0.0034 (13) | 0.0016 (14) |
C22 | 0.0385 (18) | 0.041 (2) | 0.0360 (19) | 0.0022 (15) | 0.0097 (15) | 0.0095 (15) |
C23 | 0.047 (2) | 0.060 (3) | 0.033 (2) | 0.0005 (19) | 0.0154 (17) | 0.0044 (18) |
C24 | 0.0354 (19) | 0.056 (2) | 0.041 (2) | 0.0008 (17) | 0.0153 (16) | −0.0088 (18) |
C25 | 0.0425 (19) | 0.0381 (19) | 0.042 (2) | 0.0079 (16) | 0.0078 (17) | −0.0012 (16) |
C26 | 0.0432 (19) | 0.0360 (18) | 0.0303 (18) | 0.0049 (15) | 0.0062 (15) | 0.0029 (14) |
C27 | 0.0338 (18) | 0.0351 (19) | 0.058 (3) | 0.0087 (15) | 0.0176 (18) | 0.0067 (18) |
C28 | 0.0307 (17) | 0.0327 (19) | 0.054 (2) | 0.0045 (14) | 0.0142 (17) | 0.0050 (17) |
C29 | 0.041 (2) | 0.045 (2) | 0.054 (3) | 0.0077 (17) | 0.0079 (18) | 0.0115 (19) |
C30 | 0.0323 (19) | 0.056 (3) | 0.070 (3) | −0.0020 (18) | −0.002 (2) | 0.014 (2) |
C31 | 0.034 (2) | 0.051 (3) | 0.080 (3) | 0.0052 (18) | 0.022 (2) | 0.006 (2) |
C32 | 0.054 (3) | 0.053 (3) | 0.082 (4) | −0.005 (2) | 0.038 (3) | −0.015 (3) |
C33 | 0.040 (2) | 0.047 (2) | 0.067 (3) | −0.0054 (17) | 0.020 (2) | −0.014 (2) |
C34 | 0.0354 (18) | 0.058 (2) | 0.0292 (19) | 0.0035 (16) | 0.0076 (15) | 0.0106 (17) |
C35 | 0.0370 (18) | 0.043 (2) | 0.033 (2) | −0.0005 (15) | 0.0069 (15) | 0.0046 (16) |
C36 | 0.064 (3) | 0.050 (2) | 0.040 (2) | 0.003 (2) | 0.008 (2) | −0.0050 (19) |
C37 | 0.067 (3) | 0.054 (3) | 0.055 (3) | −0.022 (2) | −0.004 (2) | −0.005 (2) |
C38 | 0.047 (2) | 0.079 (4) | 0.064 (3) | −0.006 (3) | −0.008 (2) | 0.008 (3) |
C39 | 0.039 (2) | 0.092 (4) | 0.071 (4) | 0.010 (2) | −0.006 (2) | −0.015 (3) |
C40 | 0.039 (2) | 0.048 (2) | 0.057 (3) | 0.0047 (17) | −0.0073 (19) | −0.005 (2) |
O1 | 0.071 (2) | 0.064 (2) | 0.0481 (18) | 0.0128 (17) | 0.0241 (16) | −0.0114 (16) |
S1 | 0.0282 (4) | 0.0300 (4) | 0.0310 (4) | 0.0016 (3) | 0.0046 (3) | 0.0047 (3) |
S2 | 0.0257 (4) | 0.0291 (4) | 0.0370 (5) | −0.0027 (3) | 0.0104 (3) | 0.0007 (3) |
S3 | 0.0242 (4) | 0.0319 (4) | 0.0307 (4) | −0.0001 (3) | 0.0057 (3) | 0.0069 (3) |
Ru1 | 0.02280 (11) | 0.02572 (12) | 0.03464 (14) | −0.00190 (10) | 0.00659 (10) | 0.00523 (11) |
Ru2 | 0.02355 (11) | 0.02625 (12) | 0.03065 (13) | −0.00107 (11) | 0.00895 (9) | 0.00414 (12) |
B1 | 0.045 (2) | 0.054 (3) | 0.053 (3) | 0.005 (2) | 0.008 (2) | −0.008 (2) |
F1 | 0.235 (7) | 0.072 (3) | 0.220 (7) | 0.026 (3) | 0.171 (6) | 0.007 (3) |
F2 | 0.080 (2) | 0.118 (3) | 0.060 (2) | 0.033 (2) | 0.0282 (17) | 0.0103 (19) |
F3 | 0.111 (4) | 0.341 (11) | 0.141 (5) | 0.118 (5) | 0.035 (4) | 0.067 (6) |
F4 | 0.189 (6) | 0.306 (9) | 0.170 (6) | −0.184 (7) | 0.113 (5) | −0.171 (6) |
C1—C6 | 1.416 (7) | C20—H20A | 0.9600 |
C1—C2 | 1.425 (6) | C20—H20B | 0.9600 |
C1—C7 | 1.513 (7) | C20—H20C | 0.9600 |
C1—Ru1 | 2.240 (4) | C21—C26 | 1.395 (5) |
C2—C3 | 1.406 (6) | C21—C22 | 1.396 (5) |
C2—Ru1 | 2.213 (3) | C21—S1 | 1.782 (4) |
C2—H2 | 0.9300 | C22—C23 | 1.382 (6) |
C3—C4 | 1.421 (6) | C22—H22 | 0.9300 |
C3—Ru1 | 2.224 (4) | C23—C24 | 1.367 (6) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.400 (7) | C24—O1 | 1.376 (5) |
C4—C10 | 1.508 (7) | C24—C25 | 1.382 (6) |
C4—Ru1 | 2.233 (4) | C25—C26 | 1.396 (5) |
C5—C6 | 1.404 (8) | C25—H25 | 0.9300 |
C5—Ru1 | 2.196 (4) | C26—H26 | 0.9300 |
C5—H5 | 0.9300 | C27—C28 | 1.508 (5) |
C6—Ru1 | 2.189 (4) | C27—S2 | 1.828 (4) |
C6—H6 | 0.9300 | C27—H27A | 0.9700 |
C7—C8 | 1.504 (9) | C27—H27B | 0.9700 |
C7—C9 | 1.507 (8) | C28—C29 | 1.375 (6) |
C7—H7 | 0.9800 | C28—C33 | 1.406 (6) |
C8—H8A | 0.9600 | C29—C30 | 1.395 (6) |
C8—H8B | 0.9600 | C29—H29 | 0.9300 |
C8—H8C | 0.9600 | C30—C31 | 1.364 (8) |
C9—H9A | 0.9600 | C30—H30 | 0.9300 |
C9—H9B | 0.9600 | C31—C32 | 1.408 (8) |
C9—H9C | 0.9600 | C31—H31 | 0.9300 |
C10—H10A | 0.9600 | C32—C33 | 1.377 (6) |
C10—H10B | 0.9600 | C32—H32 | 0.9300 |
C10—H10C | 0.9600 | C33—H33 | 0.9300 |
C11—C12 | 1.392 (7) | C34—C35 | 1.501 (5) |
C11—C16 | 1.403 (6) | C34—S3 | 1.849 (4) |
C11—C17 | 1.534 (6) | C34—H34A | 0.9700 |
C11—Ru2 | 2.223 (4) | C34—H34B | 0.9700 |
C12—C13 | 1.424 (6) | C35—C40 | 1.385 (6) |
C12—Ru2 | 2.174 (4) | C35—C36 | 1.386 (6) |
C12—H12 | 0.9300 | C36—C37 | 1.405 (7) |
C13—C14 | 1.411 (7) | C36—H36 | 0.9300 |
C13—Ru2 | 2.199 (4) | C37—C38 | 1.350 (8) |
C13—H13 | 0.9300 | C37—H37 | 0.9300 |
C14—C15 | 1.402 (7) | C38—C39 | 1.363 (8) |
C14—C20 | 1.507 (6) | C38—H38 | 0.9300 |
C14—Ru2 | 2.244 (4) | C39—C40 | 1.372 (6) |
C15—C16 | 1.391 (6) | C39—H39 | 0.9300 |
C15—Ru2 | 2.215 (4) | C40—H40 | 0.9300 |
C15—H15 | 0.9300 | O1—H1 | 0.8200 |
C16—Ru2 | 2.213 (4) | S1—Ru1 | 2.3878 (9) |
C16—H16 | 0.9300 | S1—Ru2 | 2.3992 (9) |
C17—C18 | 1.505 (8) | S2—Ru2 | 2.3991 (8) |
C17—C19 | 1.532 (6) | S2—Ru1 | 2.4023 (9) |
C17—H17 | 0.9800 | S3—Ru1 | 2.3813 (8) |
C18—H18A | 0.9600 | S3—Ru2 | 2.3882 (8) |
C18—H18B | 0.9600 | B1—F4 | 1.286 (7) |
C18—H18C | 0.9600 | B1—F3 | 1.304 (7) |
C19—H19A | 0.9600 | B1—F1 | 1.355 (7) |
C19—H19B | 0.9600 | B1—F2 | 1.372 (6) |
C19—H19C | 0.9600 | ||
C6—C1—C2 | 117.0 (4) | C25—C26—H26 | 119.8 |
C6—C1—C7 | 119.4 (4) | C28—C27—S2 | 112.0 (3) |
C2—C1—C7 | 123.6 (4) | C28—C27—H27A | 109.2 |
C6—C1—Ru1 | 69.4 (2) | S2—C27—H27A | 109.2 |
C2—C1—Ru1 | 70.3 (2) | C28—C27—H27B | 109.2 |
C7—C1—Ru1 | 133.2 (3) | S2—C27—H27B | 109.2 |
C3—C2—C1 | 121.4 (4) | H27A—C27—H27B | 107.9 |
C3—C2—Ru1 | 71.9 (2) | C29—C28—C33 | 118.7 (4) |
C1—C2—Ru1 | 72.4 (2) | C29—C28—C27 | 122.4 (4) |
C3—C2—H2 | 119.3 | C33—C28—C27 | 118.8 (4) |
C1—C2—H2 | 119.3 | C28—C29—C30 | 120.6 (4) |
Ru1—C2—H2 | 128.7 | C28—C29—H29 | 119.7 |
C2—C3—C4 | 120.6 (4) | C30—C29—H29 | 119.7 |
C2—C3—Ru1 | 71.1 (2) | C31—C30—C29 | 120.5 (4) |
C4—C3—Ru1 | 71.7 (2) | C31—C30—H30 | 119.7 |
C2—C3—H3 | 119.7 | C29—C30—H30 | 119.7 |
C4—C3—H3 | 119.7 | C30—C31—C32 | 120.0 (4) |
Ru1—C3—H3 | 130.0 | C30—C31—H31 | 120.0 |
C5—C4—C3 | 118.4 (4) | C32—C31—H31 | 120.0 |
C5—C4—C10 | 121.5 (4) | C33—C32—C31 | 119.1 (5) |
C3—C4—C10 | 120.1 (4) | C33—C32—H32 | 120.5 |
C5—C4—Ru1 | 70.2 (2) | C31—C32—H32 | 120.5 |
C3—C4—Ru1 | 71.1 (2) | C32—C33—C28 | 121.0 (4) |
C10—C4—Ru1 | 129.5 (3) | C32—C33—H33 | 119.5 |
C4—C5—C6 | 121.0 (4) | C28—C33—H33 | 119.5 |
C4—C5—Ru1 | 73.0 (2) | C35—C34—S3 | 111.4 (3) |
C6—C5—Ru1 | 71.1 (2) | C35—C34—H34A | 109.3 |
C4—C5—H5 | 119.5 | S3—C34—H34A | 109.3 |
C6—C5—H5 | 119.5 | C35—C34—H34B | 109.3 |
Ru1—C5—H5 | 128.8 | S3—C34—H34B | 109.3 |
C5—C6—C1 | 121.7 (4) | H34A—C34—H34B | 108.0 |
C5—C6—Ru1 | 71.6 (2) | C40—C35—C36 | 117.0 (4) |
C1—C6—Ru1 | 73.3 (2) | C40—C35—C34 | 119.6 (4) |
C5—C6—H6 | 119.1 | C36—C35—C34 | 123.4 (4) |
C1—C6—H6 | 119.1 | C35—C36—C37 | 120.3 (4) |
Ru1—C6—H6 | 128.2 | C35—C36—H36 | 119.9 |
C8—C7—C9 | 109.5 (5) | C37—C36—H36 | 119.9 |
C8—C7—C1 | 114.1 (4) | C38—C37—C36 | 120.4 (4) |
C9—C7—C1 | 109.5 (6) | C38—C37—H37 | 119.8 |
C8—C7—H7 | 107.8 | C36—C37—H37 | 119.8 |
C9—C7—H7 | 107.8 | C37—C38—C39 | 120.4 (5) |
C1—C7—H7 | 107.8 | C37—C38—H38 | 119.8 |
C7—C8—H8A | 109.5 | C39—C38—H38 | 119.8 |
C7—C8—H8B | 109.5 | C38—C39—C40 | 119.5 (5) |
H8A—C8—H8B | 109.5 | C38—C39—H39 | 120.3 |
C7—C8—H8C | 109.5 | C40—C39—H39 | 120.3 |
H8A—C8—H8C | 109.5 | C39—C40—C35 | 122.5 (5) |
H8B—C8—H8C | 109.5 | C39—C40—H40 | 118.8 |
C7—C9—H9A | 109.5 | C35—C40—H40 | 118.8 |
C7—C9—H9B | 109.5 | C24—O1—H1 | 109.5 |
H9A—C9—H9B | 109.5 | C21—S1—Ru1 | 114.81 (12) |
C7—C9—H9C | 109.5 | C21—S1—Ru2 | 111.85 (11) |
H9A—C9—H9C | 109.5 | Ru1—S1—Ru2 | 89.27 (3) |
H9B—C9—H9C | 109.5 | C27—S2—Ru2 | 108.48 (13) |
C4—C10—H10A | 109.5 | C27—S2—Ru1 | 110.18 (15) |
C4—C10—H10B | 109.5 | Ru2—S2—Ru1 | 88.93 (3) |
H10A—C10—H10B | 109.5 | C34—S3—Ru1 | 106.43 (12) |
C4—C10—H10C | 109.5 | C34—S3—Ru2 | 110.79 (14) |
H10A—C10—H10C | 109.5 | Ru1—S3—Ru2 | 89.68 (3) |
H10B—C10—H10C | 109.5 | C6—Ru1—C5 | 37.3 (2) |
C12—C11—C16 | 117.6 (4) | C6—Ru1—C2 | 66.74 (14) |
C12—C11—C17 | 124.4 (4) | C5—Ru1—C2 | 78.89 (15) |
C16—C11—C17 | 118.0 (4) | C6—Ru1—C3 | 78.73 (16) |
C12—C11—Ru2 | 69.6 (2) | C5—Ru1—C3 | 66.47 (16) |
C16—C11—Ru2 | 71.2 (2) | C2—Ru1—C3 | 36.95 (15) |
C17—C11—Ru2 | 129.5 (3) | C6—Ru1—C4 | 66.98 (19) |
C11—C12—C13 | 121.6 (4) | C5—Ru1—C4 | 36.83 (18) |
C11—C12—Ru2 | 73.5 (2) | C2—Ru1—C4 | 67.04 (15) |
C13—C12—Ru2 | 71.9 (2) | C3—Ru1—C4 | 37.19 (15) |
C11—C12—H12 | 119.2 | C6—Ru1—C1 | 37.27 (17) |
C13—C12—H12 | 119.2 | C5—Ru1—C1 | 67.45 (18) |
Ru2—C12—H12 | 127.5 | C2—Ru1—C1 | 37.31 (14) |
C14—C13—C12 | 120.1 (4) | C3—Ru1—C1 | 67.13 (15) |
C14—C13—Ru2 | 73.2 (2) | C4—Ru1—C1 | 79.82 (16) |
C12—C13—Ru2 | 70.0 (2) | C6—Ru1—S3 | 93.80 (11) |
C14—C13—H13 | 119.9 | C5—Ru1—S3 | 103.06 (12) |
C12—C13—H13 | 119.9 | C2—Ru1—S3 | 145.72 (11) |
Ru2—C13—H13 | 129.1 | C3—Ru1—S3 | 169.43 (11) |
C15—C14—C13 | 117.4 (4) | C4—Ru1—S3 | 132.82 (11) |
C15—C14—C20 | 120.7 (5) | C1—Ru1—S3 | 111.14 (11) |
C13—C14—C20 | 121.8 (5) | C6—Ru1—S1 | 147.03 (15) |
C15—C14—Ru2 | 70.5 (2) | C5—Ru1—S1 | 113.05 (15) |
C13—C14—Ru2 | 69.7 (2) | C2—Ru1—S1 | 133.72 (11) |
C20—C14—Ru2 | 131.6 (3) | C3—Ru1—S1 | 104.49 (11) |
C16—C15—C14 | 121.9 (4) | C4—Ru1—S1 | 95.42 (12) |
C16—C15—Ru2 | 71.6 (2) | C1—Ru1—S1 | 170.98 (11) |
C14—C15—Ru2 | 72.8 (2) | S3—Ru1—S1 | 77.72 (3) |
C16—C15—H15 | 119.1 | C6—Ru1—S2 | 134.30 (16) |
C14—C15—H15 | 119.1 | C5—Ru1—S2 | 171.64 (15) |
Ru2—C15—H15 | 129.0 | C2—Ru1—S2 | 97.38 (10) |
C15—C16—C11 | 121.4 (4) | C3—Ru1—S2 | 114.82 (11) |
C15—C16—Ru2 | 71.8 (2) | C4—Ru1—S2 | 148.05 (12) |
C11—C16—Ru2 | 72.0 (2) | C1—Ru1—S2 | 105.05 (12) |
C15—C16—H16 | 119.3 | S3—Ru1—S2 | 75.75 (3) |
C11—C16—H16 | 119.3 | S1—Ru1—S2 | 74.95 (3) |
Ru2—C16—H16 | 129.5 | C12—Ru2—C13 | 38.01 (17) |
C18—C17—C19 | 110.6 (5) | C12—Ru2—C16 | 66.05 (17) |
C18—C17—C11 | 114.1 (5) | C13—Ru2—C16 | 78.40 (16) |
C19—C17—C11 | 109.4 (4) | C12—Ru2—C15 | 78.34 (16) |
C18—C17—H17 | 107.5 | C13—Ru2—C15 | 66.03 (18) |
C19—C17—H17 | 107.5 | C16—Ru2—C15 | 36.62 (17) |
C11—C17—H17 | 107.5 | C12—Ru2—C11 | 36.90 (18) |
C17—C18—H18A | 109.5 | C13—Ru2—C11 | 67.55 (15) |
C17—C18—H18B | 109.5 | C16—Ru2—C11 | 36.87 (16) |
H18A—C18—H18B | 109.5 | C15—Ru2—C11 | 66.59 (15) |
C17—C18—H18C | 109.5 | C12—Ru2—C14 | 67.56 (16) |
H18A—C18—H18C | 109.5 | C13—Ru2—C14 | 37.03 (19) |
H18B—C18—H18C | 109.5 | C16—Ru2—C14 | 66.43 (17) |
C17—C19—H19A | 109.5 | C15—Ru2—C14 | 36.65 (19) |
C17—C19—H19B | 109.5 | C11—Ru2—C14 | 79.68 (14) |
H19A—C19—H19B | 109.5 | C12—Ru2—S3 | 120.02 (12) |
C17—C19—H19C | 109.5 | C13—Ru2—S3 | 157.02 (13) |
H19A—C19—H19C | 109.5 | C16—Ru2—S3 | 99.26 (12) |
H19B—C19—H19C | 109.5 | C15—Ru2—S3 | 124.53 (14) |
C14—C20—H20A | 109.5 | C11—Ru2—S3 | 96.70 (10) |
C14—C20—H20B | 109.5 | C14—Ru2—S3 | 160.63 (15) |
H20A—C20—H20B | 109.5 | C12—Ru2—S2 | 161.04 (13) |
C14—C20—H20C | 109.5 | C13—Ru2—S2 | 124.58 (12) |
H20A—C20—H20C | 109.5 | C16—Ru2—S2 | 124.98 (12) |
H20B—C20—H20C | 109.5 | C15—Ru2—S2 | 102.07 (11) |
C26—C21—C22 | 118.4 (3) | C11—Ru2—S2 | 159.91 (13) |
C26—C21—S1 | 124.4 (3) | C14—Ru2—S2 | 101.26 (10) |
C22—C21—S1 | 117.2 (3) | S3—Ru2—S2 | 75.68 (3) |
C23—C22—C21 | 121.1 (4) | C12—Ru2—S1 | 97.29 (12) |
C23—C22—H22 | 119.5 | C13—Ru2—S1 | 96.53 (12) |
C21—C22—H22 | 119.5 | C16—Ru2—S1 | 158.92 (12) |
C24—C23—C22 | 119.9 (4) | C15—Ru2—S1 | 157.00 (14) |
C24—C23—H23 | 120.1 | C11—Ru2—S1 | 122.26 (13) |
C22—C23—H23 | 120.1 | C14—Ru2—S1 | 120.75 (14) |
C23—C24—O1 | 117.3 (4) | S3—Ru2—S1 | 77.37 (3) |
C23—C24—C25 | 120.8 (4) | S2—Ru2—S1 | 74.81 (3) |
O1—C24—C25 | 121.9 (4) | F4—B1—F3 | 109.4 (7) |
C24—C25—C26 | 119.6 (4) | F4—B1—F1 | 107.3 (6) |
C24—C25—H25 | 120.2 | F3—B1—F1 | 105.7 (6) |
C26—C25—H25 | 120.2 | F4—B1—F2 | 113.0 (5) |
C21—C26—C25 | 120.3 (4) | F3—B1—F2 | 110.6 (5) |
C21—C26—H26 | 119.8 | F1—B1—F2 | 110.6 (5) |
C6—C1—C2—C3 | −1.9 (5) | C2—C1—Ru1—S2 | −82.3 (2) |
C7—C1—C2—C3 | 175.7 (4) | C7—C1—Ru1—S2 | 35.7 (5) |
Ru1—C1—C2—C3 | −54.9 (3) | C34—S3—Ru1—C6 | 63.2 (2) |
C6—C1—C2—Ru1 | 53.1 (3) | Ru2—S3—Ru1—C6 | 174.80 (16) |
C7—C1—C2—Ru1 | −129.4 (4) | C34—S3—Ru1—C5 | 99.8 (2) |
C1—C2—C3—C4 | 1.1 (5) | Ru2—S3—Ru1—C5 | −148.57 (15) |
Ru1—C2—C3—C4 | −54.1 (3) | C34—S3—Ru1—C2 | 10.4 (2) |
C1—C2—C3—Ru1 | 55.1 (3) | Ru2—S3—Ru1—C2 | 122.06 (17) |
C2—C3—C4—C5 | 0.2 (5) | C34—S3—Ru1—C3 | 107.7 (6) |
Ru1—C3—C4—C5 | −53.6 (3) | Ru2—S3—Ru1—C3 | −140.7 (6) |
C2—C3—C4—C10 | 179.2 (4) | C34—S3—Ru1—C4 | 125.0 (2) |
Ru1—C3—C4—C10 | 125.4 (4) | Ru2—S3—Ru1—C4 | −123.41 (17) |
C2—C3—C4—Ru1 | 53.8 (3) | C34—S3—Ru1—C1 | 29.23 (19) |
C3—C4—C5—C6 | −0.5 (6) | Ru2—S3—Ru1—C1 | 140.85 (12) |
C10—C4—C5—C6 | −179.5 (4) | C34—S3—Ru1—S1 | −149.03 (15) |
Ru1—C4—C5—C6 | −54.6 (3) | Ru2—S3—Ru1—S1 | −37.41 (3) |
C3—C4—C5—Ru1 | 54.1 (3) | C34—S3—Ru1—S2 | −71.67 (15) |
C10—C4—C5—Ru1 | −124.9 (4) | Ru2—S3—Ru1—S2 | 39.95 (3) |
C4—C5—C6—C1 | −0.4 (6) | C21—S1—Ru1—C6 | 1.2 (3) |
Ru1—C5—C6—C1 | −55.9 (3) | Ru2—S1—Ru1—C6 | 115.0 (2) |
C4—C5—C6—Ru1 | 55.5 (3) | C21—S1—Ru1—C5 | 22.52 (19) |
C2—C1—C6—C5 | 1.6 (5) | Ru2—S1—Ru1—C5 | 136.35 (13) |
C7—C1—C6—C5 | −176.1 (4) | C21—S1—Ru1—C2 | 119.24 (18) |
Ru1—C1—C6—C5 | 55.1 (3) | Ru2—S1—Ru1—C2 | −126.92 (14) |
C2—C1—C6—Ru1 | −53.5 (3) | C21—S1—Ru1—C3 | 92.76 (17) |
C7—C1—C6—Ru1 | 128.8 (4) | Ru2—S1—Ru1—C3 | −153.41 (11) |
C6—C1—C7—C8 | −156.4 (4) | C21—S1—Ru1—C4 | 56.07 (17) |
C2—C1—C7—C8 | 26.1 (6) | Ru2—S1—Ru1—C4 | 169.91 (11) |
Ru1—C1—C7—C8 | −67.8 (6) | C21—S1—Ru1—S3 | −76.62 (13) |
C6—C1—C7—C9 | 80.4 (6) | Ru2—S1—Ru1—S3 | 37.22 (3) |
C2—C1—C7—C9 | −97.1 (6) | C21—S1—Ru1—S2 | −154.94 (13) |
Ru1—C1—C7—C9 | 169.0 (4) | Ru2—S1—Ru1—S2 | −41.11 (3) |
C16—C11—C12—C13 | −1.5 (5) | C27—S2—Ru1—C6 | 129.7 (2) |
C17—C11—C12—C13 | 179.6 (3) | Ru2—S2—Ru1—C6 | −120.97 (15) |
Ru2—C11—C12—C13 | −55.8 (3) | C27—S2—Ru1—C2 | 65.17 (18) |
C16—C11—C12—Ru2 | 54.4 (3) | Ru2—S2—Ru1—C2 | 174.49 (11) |
C17—C11—C12—Ru2 | −124.6 (4) | C27—S2—Ru1—C3 | 31.07 (18) |
C11—C12—C13—C14 | 1.0 (6) | Ru2—S2—Ru1—C3 | 140.39 (12) |
Ru2—C12—C13—C14 | −55.6 (3) | C27—S2—Ru1—C4 | 7.6 (3) |
C11—C12—C13—Ru2 | 56.5 (3) | Ru2—S2—Ru1—C4 | 116.9 (2) |
C12—C13—C14—C15 | 0.4 (5) | C27—S2—Ru1—C1 | 102.46 (17) |
Ru2—C13—C14—C15 | −53.7 (3) | Ru2—S2—Ru1—C1 | −148.22 (11) |
C12—C13—C14—C20 | −178.8 (4) | C27—S2—Ru1—S3 | −149.06 (14) |
Ru2—C13—C14—C20 | 127.1 (3) | Ru2—S2—Ru1—S3 | −39.74 (3) |
C12—C13—C14—Ru2 | 54.1 (3) | C27—S2—Ru1—S1 | −68.20 (14) |
C13—C14—C15—C16 | −1.1 (5) | Ru2—S2—Ru1—S1 | 41.11 (3) |
C20—C14—C15—C16 | 178.0 (3) | C11—C12—Ru2—C13 | −132.2 (4) |
Ru2—C14—C15—C16 | −54.5 (3) | C11—C12—Ru2—C16 | −30.0 (2) |
C13—C14—C15—Ru2 | 53.3 (3) | C13—C12—Ru2—C16 | 102.2 (3) |
C20—C14—C15—Ru2 | −127.5 (3) | C11—C12—Ru2—C15 | −66.4 (3) |
C14—C15—C16—C11 | 0.6 (6) | C13—C12—Ru2—C15 | 65.8 (3) |
Ru2—C15—C16—C11 | −54.4 (3) | C13—C12—Ru2—C11 | 132.2 (4) |
C14—C15—C16—Ru2 | 55.0 (3) | C11—C12—Ru2—C14 | −103.1 (3) |
C12—C11—C16—C15 | 0.7 (5) | C13—C12—Ru2—C14 | 29.0 (3) |
C17—C11—C16—C15 | 179.7 (3) | C11—C12—Ru2—S3 | 57.0 (3) |
Ru2—C11—C16—C15 | 54.3 (3) | C13—C12—Ru2—S3 | −170.9 (2) |
C12—C11—C16—Ru2 | −53.6 (3) | C11—C12—Ru2—S2 | −159.6 (3) |
C17—C11—C16—Ru2 | 125.4 (3) | C13—C12—Ru2—S2 | −27.4 (5) |
C12—C11—C17—C18 | 20.0 (6) | C11—C12—Ru2—S1 | 136.5 (2) |
C16—C11—C17—C18 | −159.0 (4) | C13—C12—Ru2—S1 | −91.3 (3) |
Ru2—C11—C17—C18 | −71.1 (6) | C14—C13—Ru2—C12 | 131.8 (4) |
C12—C11—C17—C19 | −104.6 (6) | C14—C13—Ru2—C16 | 66.1 (3) |
C16—C11—C17—C19 | 76.4 (6) | C12—C13—Ru2—C16 | −65.8 (3) |
Ru2—C11—C17—C19 | 164.4 (5) | C14—C13—Ru2—C15 | 29.7 (2) |
C26—C21—C22—C23 | −0.4 (6) | C12—C13—Ru2—C15 | −102.1 (3) |
S1—C21—C22—C23 | 176.4 (3) | C14—C13—Ru2—C11 | 103.0 (3) |
C21—C22—C23—C24 | −1.0 (6) | C12—C13—Ru2—C11 | −28.8 (3) |
C22—C23—C24—O1 | −176.3 (4) | C12—C13—Ru2—C14 | −131.8 (4) |
C22—C23—C24—C25 | 1.9 (6) | C14—C13—Ru2—S3 | 152.4 (3) |
C23—C24—C25—C26 | −1.4 (6) | C12—C13—Ru2—S3 | 20.6 (5) |
O1—C24—C25—C26 | 176.8 (4) | C14—C13—Ru2—S2 | −58.6 (3) |
C22—C21—C26—C25 | 1.0 (5) | C12—C13—Ru2—S2 | 169.5 (2) |
S1—C21—C26—C25 | −175.6 (3) | C14—C13—Ru2—S1 | −134.7 (2) |
C24—C25—C26—C21 | −0.1 (6) | C12—C13—Ru2—S1 | 93.5 (3) |
S2—C27—C28—C29 | 115.2 (4) | C15—C16—Ru2—C12 | −103.1 (3) |
S2—C27—C28—C33 | −62.6 (4) | C11—C16—Ru2—C12 | 30.0 (2) |
C33—C28—C29—C30 | 1.6 (6) | C15—C16—Ru2—C13 | −65.2 (3) |
C27—C28—C29—C30 | −176.2 (4) | C11—C16—Ru2—C13 | 67.9 (3) |
C28—C29—C30—C31 | −0.5 (7) | C11—C16—Ru2—C15 | 133.1 (4) |
C29—C30—C31—C32 | −1.1 (7) | C15—C16—Ru2—C11 | −133.1 (4) |
C30—C31—C32—C33 | 1.5 (7) | C15—C16—Ru2—C14 | −28.3 (3) |
C31—C32—C33—C28 | −0.3 (7) | C11—C16—Ru2—C14 | 104.8 (3) |
C29—C28—C33—C32 | −1.1 (7) | C15—C16—Ru2—S3 | 138.0 (3) |
C27—C28—C33—C32 | 176.7 (4) | C11—C16—Ru2—S3 | −88.8 (2) |
S3—C34—C35—C40 | 59.4 (5) | C15—C16—Ru2—S2 | 59.1 (3) |
S3—C34—C35—C36 | −117.3 (4) | C11—C16—Ru2—S2 | −167.78 (19) |
C40—C35—C36—C37 | −0.1 (7) | C15—C16—Ru2—S1 | −143.1 (3) |
C34—C35—C36—C37 | 176.6 (4) | C11—C16—Ru2—S1 | −10.0 (5) |
C35—C36—C37—C38 | −0.9 (8) | C16—C15—Ru2—C12 | 65.3 (3) |
C36—C37—C38—C39 | 1.7 (9) | C14—C15—Ru2—C12 | −67.9 (3) |
C37—C38—C39—C40 | −1.3 (9) | C16—C15—Ru2—C13 | 103.3 (3) |
C38—C39—C40—C35 | 0.3 (9) | C14—C15—Ru2—C13 | −30.0 (2) |
C36—C35—C40—C39 | 0.4 (7) | C14—C15—Ru2—C16 | −133.3 (4) |
C34—C35—C40—C39 | −176.4 (5) | C16—C15—Ru2—C11 | 28.5 (3) |
C26—C21—S1—Ru1 | 17.9 (3) | C14—C15—Ru2—C11 | −104.8 (3) |
C22—C21—S1—Ru1 | −158.7 (2) | C16—C15—Ru2—C14 | 133.3 (4) |
C26—C21—S1—Ru2 | −81.9 (3) | C16—C15—Ru2—S3 | −53.2 (3) |
C22—C21—S1—Ru2 | 101.5 (3) | C14—C15—Ru2—S3 | 173.49 (19) |
C28—C27—S2—Ru2 | −162.8 (3) | C16—C15—Ru2—S2 | −134.0 (2) |
C28—C27—S2—Ru1 | −67.0 (3) | C14—C15—Ru2—S2 | 92.7 (2) |
C35—C34—S3—Ru1 | 173.0 (3) | C16—C15—Ru2—S1 | 146.4 (2) |
C35—C34—S3—Ru2 | 76.9 (3) | C14—C15—Ru2—S1 | 13.2 (4) |
C1—C6—Ru1—C5 | 132.7 (4) | C16—C11—Ru2—C12 | −130.4 (4) |
C5—C6—Ru1—C2 | −102.6 (3) | C17—C11—Ru2—C12 | 118.4 (6) |
C1—C6—Ru1—C2 | 30.1 (2) | C12—C11—Ru2—C13 | 29.6 (3) |
C5—C6—Ru1—C3 | −65.8 (3) | C16—C11—Ru2—C13 | −100.9 (3) |
C1—C6—Ru1—C3 | 66.9 (3) | C17—C11—Ru2—C13 | 148.0 (5) |
C5—C6—Ru1—C4 | −28.7 (2) | C12—C11—Ru2—C16 | 130.4 (4) |
C1—C6—Ru1—C4 | 104.0 (3) | C17—C11—Ru2—C16 | −111.2 (6) |
C5—C6—Ru1—C1 | −132.7 (4) | C12—C11—Ru2—C15 | 102.1 (3) |
C5—C6—Ru1—S3 | 106.6 (2) | C16—C11—Ru2—C15 | −28.3 (3) |
C1—C6—Ru1—S3 | −120.7 (3) | C17—C11—Ru2—C15 | −139.5 (5) |
C5—C6—Ru1—S1 | 33.5 (4) | C12—C11—Ru2—C14 | 66.2 (3) |
C1—C6—Ru1—S1 | 166.17 (19) | C16—C11—Ru2—C14 | −64.2 (3) |
C5—C6—Ru1—S2 | −179.61 (19) | C17—C11—Ru2—C14 | −175.4 (5) |
C1—C6—Ru1—S2 | −46.9 (3) | C12—C11—Ru2—S3 | −133.0 (2) |
C4—C5—Ru1—C6 | −132.4 (4) | C16—C11—Ru2—S3 | 96.5 (2) |
C4—C5—Ru1—C2 | −66.4 (3) | C17—C11—Ru2—S3 | −14.7 (5) |
C6—C5—Ru1—C2 | 66.0 (2) | C12—C11—Ru2—S2 | 160.8 (3) |
C4—C5—Ru1—C3 | −29.8 (3) | C16—C11—Ru2—S2 | 30.3 (4) |
C6—C5—Ru1—C3 | 102.7 (3) | C17—C11—Ru2—S2 | −80.9 (6) |
C6—C5—Ru1—C4 | 132.4 (4) | C12—C11—Ru2—S1 | −53.8 (3) |
C4—C5—Ru1—C1 | −103.6 (3) | C16—C11—Ru2—S1 | 175.8 (2) |
C6—C5—Ru1—C1 | 28.8 (2) | C17—C11—Ru2—S1 | 64.6 (5) |
C4—C5—Ru1—S3 | 148.7 (2) | C15—C14—Ru2—C12 | 100.9 (3) |
C6—C5—Ru1—S3 | −78.9 (2) | C13—C14—Ru2—C12 | −29.8 (3) |
C4—C5—Ru1—S1 | 66.6 (3) | C20—C14—Ru2—C12 | −144.9 (7) |
C6—C5—Ru1—S1 | −161.0 (2) | C15—C14—Ru2—C13 | 130.6 (3) |
C3—C2—Ru1—C6 | 102.6 (3) | C20—C14—Ru2—C13 | −115.1 (7) |
C1—C2—Ru1—C6 | −30.1 (3) | C15—C14—Ru2—C16 | 28.3 (2) |
C3—C2—Ru1—C5 | 65.4 (3) | C13—C14—Ru2—C16 | −102.4 (3) |
C1—C2—Ru1—C5 | −67.2 (3) | C20—C14—Ru2—C16 | 142.5 (7) |
C1—C2—Ru1—C3 | −132.7 (3) | C13—C14—Ru2—C15 | −130.6 (3) |
C3—C2—Ru1—C4 | 28.8 (2) | C20—C14—Ru2—C15 | 114.3 (7) |
C1—C2—Ru1—C4 | −103.8 (3) | C15—C14—Ru2—C11 | 64.4 (3) |
C3—C2—Ru1—C1 | 132.7 (3) | C13—C14—Ru2—C11 | −66.2 (3) |
C3—C2—Ru1—S3 | 162.38 (19) | C20—C14—Ru2—C11 | 178.7 (7) |
C1—C2—Ru1—S3 | 29.7 (3) | C15—C14—Ru2—S3 | −16.3 (5) |
C3—C2—Ru1—S1 | −45.9 (3) | C13—C14—Ru2—S3 | −147.0 (3) |
C1—C2—Ru1—S1 | −178.6 (2) | C20—C14—Ru2—S3 | 97.9 (7) |
C3—C2—Ru1—S2 | −122.1 (2) | C15—C14—Ru2—S2 | −95.1 (2) |
C1—C2—Ru1—S2 | 105.2 (2) | C13—C14—Ru2—S2 | 134.2 (2) |
C2—C3—Ru1—C6 | −66.1 (3) | C20—C14—Ru2—S2 | 19.1 (6) |
C4—C3—Ru1—C6 | 66.6 (3) | C15—C14—Ru2—S1 | −174.05 (19) |
C2—C3—Ru1—C5 | −103.2 (3) | C13—C14—Ru2—S1 | 55.3 (3) |
C4—C3—Ru1—C5 | 29.5 (3) | C20—C14—Ru2—S1 | −59.8 (7) |
C4—C3—Ru1—C2 | 132.7 (4) | C34—S3—Ru2—C12 | −124.07 (19) |
C2—C3—Ru1—C4 | −132.7 (4) | Ru1—S3—Ru2—C12 | 128.45 (14) |
C2—C3—Ru1—C1 | −28.9 (2) | C34—S3—Ru2—C13 | −138.6 (3) |
C4—C3—Ru1—C1 | 103.8 (3) | Ru1—S3—Ru2—C13 | 114.0 (3) |
C2—C3—Ru1—S3 | −111.6 (6) | C34—S3—Ru2—C16 | −56.46 (17) |
C4—C3—Ru1—S3 | 21.1 (8) | Ru1—S3—Ru2—C16 | −163.94 (12) |
C2—C3—Ru1—S1 | 147.6 (2) | C34—S3—Ru2—C15 | −27.50 (18) |
C4—C3—Ru1—S1 | −79.7 (3) | Ru1—S3—Ru2—C15 | −134.98 (13) |
C2—C3—Ru1—S2 | 67.7 (2) | C34—S3—Ru2—C11 | −93.62 (18) |
C4—C3—Ru1—S2 | −159.6 (2) | Ru1—S3—Ru2—C11 | 158.90 (13) |
C5—C4—Ru1—C6 | 29.1 (3) | C34—S3—Ru2—C14 | −15.7 (3) |
C3—C4—Ru1—C6 | −102.0 (3) | Ru1—S3—Ru2—C14 | −123.2 (3) |
C10—C4—Ru1—C6 | 144.1 (5) | C34—S3—Ru2—S2 | 67.45 (13) |
C3—C4—Ru1—C5 | −131.1 (4) | Ru1—S3—Ru2—S2 | −40.03 (3) |
C10—C4—Ru1—C5 | 115.0 (5) | C34—S3—Ru2—S1 | 144.75 (13) |
C5—C4—Ru1—C2 | 102.5 (3) | Ru1—S3—Ru2—S1 | 37.27 (3) |
C3—C4—Ru1—C2 | −28.6 (2) | C27—S2—Ru2—C12 | 2.7 (4) |
C10—C4—Ru1—C2 | −142.5 (5) | Ru1—S2—Ru2—C12 | −108.2 (4) |
C5—C4—Ru1—C3 | 131.1 (4) | C27—S2—Ru2—C13 | −17.4 (2) |
C10—C4—Ru1—C3 | −113.8 (5) | Ru1—S2—Ru2—C13 | −128.38 (16) |
C5—C4—Ru1—C1 | 65.8 (3) | C27—S2—Ru2—C16 | −118.1 (2) |
C3—C4—Ru1—C1 | −65.4 (3) | Ru1—S2—Ru2—C16 | 130.99 (14) |
C10—C4—Ru1—C1 | −179.2 (5) | C27—S2—Ru2—C15 | −86.5 (2) |
C5—C4—Ru1—S3 | −43.7 (3) | Ru1—S2—Ru2—C15 | 162.55 (14) |
C3—C4—Ru1—S3 | −174.84 (19) | C27—S2—Ru2—C11 | −139.8 (3) |
C10—C4—Ru1—S3 | 71.3 (5) | Ru1—S2—Ru2—C11 | 109.3 (3) |
C5—C4—Ru1—S1 | −122.0 (3) | C27—S2—Ru2—C14 | −49.1 (2) |
C3—C4—Ru1—S1 | 106.9 (2) | Ru1—S2—Ru2—C14 | −160.00 (15) |
C10—C4—Ru1—S1 | −6.9 (4) | C27—S2—Ru2—S3 | 150.56 (16) |
C5—C4—Ru1—S2 | 167.9 (2) | Ru1—S2—Ru2—S3 | 39.61 (3) |
C3—C4—Ru1—S2 | 36.8 (4) | C27—S2—Ru2—S1 | 70.03 (15) |
C10—C4—Ru1—S2 | −77.0 (5) | Ru1—S2—Ru2—S1 | −40.91 (3) |
C2—C1—Ru1—C6 | 130.4 (4) | C21—S1—Ru2—C12 | −39.83 (18) |
C7—C1—Ru1—C6 | −111.6 (6) | Ru1—S1—Ru2—C12 | −156.38 (13) |
C6—C1—Ru1—C5 | −28.9 (3) | C21—S1—Ru2—C13 | −78.12 (18) |
C2—C1—Ru1—C5 | 101.6 (3) | Ru1—S1—Ru2—C13 | 165.33 (12) |
C7—C1—Ru1—C5 | −140.4 (5) | C21—S1—Ru2—C16 | −3.5 (3) |
C6—C1—Ru1—C2 | −130.4 (4) | Ru1—S1—Ru2—C16 | −120.1 (3) |
C7—C1—Ru1—C2 | 118.0 (6) | C21—S1—Ru2—C15 | −117.1 (3) |
C6—C1—Ru1—C3 | −101.8 (3) | Ru1—S1—Ru2—C15 | 126.3 (3) |
C2—C1—Ru1—C3 | 28.7 (2) | C21—S1—Ru2—C11 | −10.60 (19) |
C7—C1—Ru1—C3 | 146.7 (5) | Ru1—S1—Ru2—C11 | −127.14 (13) |
C6—C1—Ru1—C4 | −65.2 (3) | C21—S1—Ru2—C14 | −108.01 (18) |
C2—C1—Ru1—C4 | 65.3 (2) | Ru1—S1—Ru2—C14 | 135.44 (13) |
C7—C1—Ru1—C4 | −176.7 (5) | C21—S1—Ru2—S3 | 79.40 (13) |
C6—C1—Ru1—S3 | 67.0 (3) | Ru1—S1—Ru2—S3 | −37.15 (3) |
C2—C1—Ru1—S3 | −162.58 (19) | C21—S1—Ru2—S2 | 157.76 (13) |
C7—C1—Ru1—S3 | −44.6 (5) | Ru1—S1—Ru2—S2 | 41.21 (3) |
C6—C1—Ru1—S2 | 147.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···F1 | 0.82 | 1.99 | 2.773 (9) | 161 |
C3—H3···F3i | 0.93 | 2.52 | 3.340 (11) | 148 |
C30—H30···F2i | 0.93 | 2.60 | 3.472 (9) | 156 |
C6—H6···F4ii | 0.93 | 2.34 | 3.249 (10) | 166 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, −y+1, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···F1 | 0.82 | 1.99 | 2.773 (9) | 160.5 |
C3—H3···F3i | 0.93 | 2.52 | 3.340 (11) | 147.7 |
C30—H30···F2i | 0.93 | 2.60 | 3.472 (9) | 155.6 |
C6—H6···F4ii | 0.93 | 2.34 | 3.249 (10) | 166.1 |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) x, −y+1, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ru2(C6H5OS)(C7H7S)2(C10H14)2]BF4 |
Mr | 928.91 |
Crystal system, space group | Monoclinic, Cc |
Temperature (K) | 173 |
a, b, c (Å) | 15.4807 (10), 14.3435 (11), 17.7605 (10) |
β (°) | 99.435 (5) |
V (Å3) | 3890.3 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.99 |
Crystal size (mm) | 0.22 × 0.20 × 0.18 |
Data collection | |
Diffractometer | Stoe IPDS diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 34511, 10178, 8902 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.690 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.074, 0.95 |
No. of reflections | 10178 |
No. of parameters | 466 |
No. of restraints | 2 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.52, −0.69 |
Absolute structure | Flack x determined using 3741 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013). |
Absolute structure parameter | −0.01 (2) |
Computer programs: EXPOSE in IPDS Software (Stoe & Cie, 2000), CELL in IPDS Software (Stoe & Cie, 2000), INTEGRATE in IPDS Software (Stoe & Cie, 2000), SHELXS97 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-32 (Farrugia, 2012), SHELXL97 (Sheldrick, 2008).
Acknowledgements
We would like to acknowledge the financial support of the Swiss National Science Foundation (grant No. 200020-143254).
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