metal-organic compounds
Bis(μ4-adamantane-1,3-dicarboxylato-1κO1:2κO1′:3κO3:4κO3′)octacarbonyl-1κ2C,2κ2C,3κ2C,4κ2C-tetrakis[tris(4-methylphenyl)phosphane]-1κP,2κP,3κP,4κP-tetraosmium(I)(2 Os–Os)
aDepartment of Chemistry & Biochemistry, Abilene Christian University, Abilene, Texas 79699-8132, USA, and bRigaku Americas Corp., 9009 New Trails Dr., The Woodlands, TX 77381, USA
*Correspondence e-mail: powellg@acu.edu
The title complex, [{Os2(CO)4(C21H21P)2}2(C12H14O4)2], is a centrosymmetric molecular loop consisting of two Os—Os sawhorse units linked by two adamantane dicarboxylato bridges. It was synthesized by the microwave-mediated reaction between Os3(CO)12 and adamantane-1,3-dicarboxylic acid. In contrast to the related complex [{Os2(CO)6}2(μ4-adamantane-1,3-diacetate)2], the metal–metal axes within each molecule are oriented parallel rather than perpendicular to one another. The exhibits cavities that contain residual electron density peaks, but it was not possible to unambiguously identify the solvent therein. The contribution of the disordered solvent molecules to the scattering was removed using the SQUEEZE (Spek (2015). Acta Cryst. C71, 9–18) routine in PLATON [Spek (2020). Acta Cryst. E76, 1–11]. These solvent molecules are not considered in the given chemical formula and other crystal data.
Keywords: diosmium carbonyl; sawhorse complex; supramolecular loop; adamantane dicarboxylate ligand; crystal structure.
CCDC reference: 2026644
Structure description
Group VIIIB sawhorse units with metal–metal bonds may have potential as building blocks for larger framework compounds including metal–organic frameworks (Köberl et al., 2011; Therrien & Süss-Fink, 2009). There are nine Ru2 carboxylato sawhorse assemblies in the Cambridge Structural Database (Version 5.41, last update November 2019; Groom et al., 2016). Three are molecular loops consisting of two sawhorse units (Bianchi et al., 1981; Shiu et al., 2002; Auzias et al., 2007), five are molecular triangles consisting of three sawhorse units (Auzias et al., 2007; Süss-Fink et al., 1990; Shiu et al., 2003, 2010), and one is a molecular square consisting of four sawhorse units (Shiu et al., 2002). In all of these, the Ru—Ru axes are parallel rather than perpendicular to one another. The CSD also contains six Os2 carboxylato sawhorse assemblies: five are molecular loops of two sawhorse units and one is a molecular triangle consisting of three sawhorse units (Fikes et al., 2014; Gwini et al., 2017). In all but one of these assemblies, the Os—Os axes within a molecule are parallel to one another. Only the molecular loop [Os2(CO)6]2(μ4-adamantane-1,3-diacetate)2 has Os—Os axes that are oriented perpendicular to one another (Fikes et al., 2014). No Ru2 sawhorse assemblies containing adamantane-based dicarboxylato linkers have been reported. Our goal was to investigate the orientation of Os2 units that would result when using adamantane-1,3-dicarboxylic acid rather than adamantane-1,3-diacetic acid as a starting material.
The structure of the cluster molecule in the title compound is illustrated in Fig. 1. The cluster entity resides on an inversion center and consists of a molecular loop in which two Os2(CO)4(phosphine)2 sawhorse units are bridged by two adamantane-1,3-dicarboxylato ligands. The four tri-p-tolylphosphine ligands occupy axial coordination sites with Os—Os—P angles of 170.20 (2) and 170.60 (2)°, which are typical for diosmium sawhorse complexes. Like Ru2 sawhorse carboxylato macrocycles in which the Ru—Ru axes are parallel to one another, the two Os—Os axes in this structure are also parallel. This is in contrast to the related molecular loop [Os2(CO)6]2(μ4-adamantane-1,3-diacetate)2 in which the metal–metal axes within each molecule are oriented perpendicular to one another (Fikes et al., 2014). In the title compound, the Os—Os bond length is 2.7398 (2) Å. In [Os2(CO)6]2(μ4-adamantane-1,3-diacetate)2, where the axial sites are occupied by carbonyl ligands instead of phosphine ligands, the metal–metal bond lengths are somewhat longer at 2.7433 (3) and 2.7561 (3) Å.
The cluster molecules of the title compound stack so that the Os—Os vectors are nearly parallel to the b axis and nearly perpendicular to the a axis. When viewed down the b axis, the central cavities of the molecular loops align to form narrow channels, as shown in Fig. 2. Because sawhorse clusters with dicarboxylato ligands have sometimes crystallized with solvent molecules trapped in the center of the macrocycle, it is common to list the dimensions of the central cavity (Therrien & Süss-Fink, 2009). The cavity in the center of the title compound is a distorted rhombus with unique edge lengths of 4.684 (1) and 4.976 (1) Å as measured from the Os—Os midpoints to the central adamantane carbon atom C58. This cavity is smaller than that in [Os2(CO)6]2(μ4-adamantane-1,3-diacetate)2 in which these distances average 5.2 Å (Fikes et al., 2014). The size difference was expected since there are two fewer carbon atoms per linker ligand in the title compound. As a result of their small sizes, the centers of the molecular loops cannot serve as a trap for solvent molecules in either one of these complexes. As shown in Fig. 3, the central portions of these two molecular loops also display different shapes. Connecting the centroids of the two Os—Os vectors and the centroids of the two adamantane groups leads to a butterfly shape in the case of [Os2(CO)6]2(μ4-adamantane-1,3-diacetate)2 and an approximate square in the case of the title compound. The butterfly wings of the adamantane diacetato complex are joined at an angle of 126°, while all four centroids are coplanar in the square of the title compound. The distances between adamantane centroids for the title cluster and for [Os2(CO)6]2(μ4-adamantane-1,3-diacetate)2 are 7.087 (2) and 7.598 (2) Å, respectively. Despite the differences in dimensions and spacing for the adamantane-based ligands in these two complexes, the distances between Os—Os centroids are remarkably similar at 8.983 (2) and 8.964 (2) Å, respectively.
Synthesis and crystallization
Os3(CO)12 (73.9 mg, 0.0815 mmol) and adamantane-1,3-dicarboxylic acid (29.2 mg, 0.130 mmol) were added to 7 ml of 1,2-dichlorobenzene in a 35 ml microwave vessel. This solution was stirred and heated in the microwave reactor at 478 K for 13 minutes. The resulting solution had a pale-yellow color. The solvent was removed, then the residue was mixed with 25 ml of 1,2-dichloroethane and 5 ml of acetonitrile and added to a 100 ml round-bottom flask equipped with a magnetic stir bar. Tri(p-tolyl)phosphine (64.0 mg, 0.210 mmol) was added and the mixture was refluxed for 60 min. The solution was cooled to 277 K, 4 ml of n-hexane were added, and the products were isolated by fractional crystallization. The first fraction to precipitate was the desired product. Yield: 47.3 mg, 29.2%. IR (νCO, cm−1): 2013 (s), 1967 (w), and 1938 (s). Analysis calculated (%) for C116H112O16Os4P4·C6H14: C 53.61, H 4.65; found: C 53.00, H 4.78. Crystals of the title compound were obtained by slow diffusion of hexanes into a dichloromethane solution.
Refinement
Crystal data, data collection and structure . Interstitial solvent molecules could not be modeled in a satisfactory manner, so a solvent mask was generated revealing voids at (1/2, 0, 1/2) and (1/2, 1/2, 0), each with a volume of 394.4 Å3 and containing about 110 electrons. The contribution of the disordered solvent molecules to the scattering was removed using the SQUEEZE (Spek, 2015) routine in PLATON (Spek, 2020). These solvent molecules are not considered in the given chemical formula and other crystal data.
details are summarized in Table 1Structural data
CCDC reference: 2026644
https://doi.org/10.1107/S2414314620012043/wm4137sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314620012043/wm4137Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314620012043/wm4137Isup3.cdx
Data collection: CrysAlis PRO (Rigaku OD, 2015); cell
CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2018/3 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).[Os4(C12H14O4)2(C21H21P)4(CO)8] | F(000) = 2600 |
Mr = 2646.73 | Dx = 1.560 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54184 Å |
a = 12.71423 (13) Å | Cell parameters from 25347 reflections |
b = 17.04149 (18) Å | θ = 2.6–77.3° |
c = 26.1784 (3) Å | µ = 9.33 mm−1 |
β = 96.7054 (9)° | T = 100 K |
V = 5633.26 (10) Å3 | Block, yellow |
Z = 2 | 0.27 × 0.21 × 0.10 mm |
Rigaku SuperNova, Dual, Cu, Pilatus 200/300K diffractometer | 10059 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 9674 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.033 |
ω scans | θmax = 67.1°, θmin = 5.7° |
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2015) | h = −11→15 |
Tmin = 0.411, Tmax = 1.000 | k = −20→20 |
30975 measured reflections | l = −31→31 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.027 | H-atom parameters constrained |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.0375P)2 + 7.1306P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.003 |
10059 reflections | Δρmax = 1.22 e Å−3 |
637 parameters | Δρmin = −1.34 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
Os2 | 0.25720 (2) | 0.61407 (2) | 0.60158 (2) | 0.01693 (5) | |
Os1 | 0.24924 (2) | 0.45454 (2) | 0.61351 (2) | 0.01735 (5) | |
P2 | 0.29032 (6) | 0.74958 (5) | 0.58494 (3) | 0.02141 (17) | |
P1 | 0.27376 (6) | 0.31514 (5) | 0.62196 (3) | 0.02018 (17) | |
O5 | 0.41485 (18) | 0.46765 (13) | 0.63120 (9) | 0.0219 (5) | |
O7 | 0.70994 (18) | 0.54451 (13) | 0.46337 (9) | 0.0200 (5) | |
O8 | 0.73816 (17) | 0.41608 (13) | 0.47687 (8) | 0.0211 (5) | |
O6 | 0.42202 (16) | 0.59267 (14) | 0.60497 (9) | 0.0217 (5) | |
O4 | 0.02026 (18) | 0.62535 (14) | 0.59194 (10) | 0.0296 (6) | |
O3 | 0.2741 (2) | 0.64628 (16) | 0.71537 (9) | 0.0341 (6) | |
O2 | 0.0191 (2) | 0.44367 (16) | 0.57153 (12) | 0.0384 (7) | |
O1 | 0.1945 (3) | 0.46999 (17) | 0.72174 (11) | 0.0466 (8) | |
C6 | 0.7201 (2) | 0.48462 (19) | 0.49227 (12) | 0.0178 (6) | |
C49 | 0.5819 (2) | 0.51894 (19) | 0.61418 (12) | 0.0184 (6) | |
C51 | 0.7592 (2) | 0.5842 (2) | 0.62477 (13) | 0.0243 (7) | |
H51 | 0.7988 | 0.6327 | 0.6368 | 0.029* | |
C50 | 0.6422 (2) | 0.5942 (2) | 0.63210 (12) | 0.0219 (7) | |
H50A | 0.6121 | 0.6396 | 0.6118 | 0.026* | |
H50B | 0.6351 | 0.6041 | 0.6688 | 0.026* | |
C28 | 0.2264 (3) | 0.8181 (2) | 0.62644 (13) | 0.0253 (7) | |
C54 | 0.6286 (3) | 0.4485 (2) | 0.64515 (13) | 0.0231 (7) | |
H54A | 0.5895 | 0.4003 | 0.6334 | 0.028* | |
H54B | 0.6212 | 0.4562 | 0.6820 | 0.028* | |
C4 | 0.1111 (2) | 0.62182 (18) | 0.59547 (13) | 0.0195 (7) | |
C58 | 0.5922 (2) | 0.50562 (19) | 0.55659 (11) | 0.0176 (6) | |
H58A | 0.5522 | 0.4581 | 0.5443 | 0.021* | |
H58B | 0.5621 | 0.5510 | 0.5363 | 0.021* | |
C8 | 0.2435 (3) | 0.2145 (2) | 0.70621 (13) | 0.0267 (7) | |
H8 | 0.3141 | 0.1970 | 0.7052 | 0.032* | |
C1 | 0.2165 (3) | 0.4633 (2) | 0.68037 (15) | 0.0286 (8) | |
C56 | 0.7100 (2) | 0.49564 (19) | 0.54905 (12) | 0.0184 (6) | |
C53 | 0.7461 (3) | 0.4393 (2) | 0.63792 (13) | 0.0243 (7) | |
H53 | 0.7765 | 0.3936 | 0.6585 | 0.029* | |
C5 | 0.4636 (2) | 0.52736 (19) | 0.61791 (12) | 0.0180 (6) | |
C36 | 0.1640 (3) | 0.7508 (2) | 0.49043 (14) | 0.0287 (8) | |
H36 | 0.1456 | 0.6987 | 0.4988 | 0.034* | |
C2 | 0.1064 (3) | 0.4478 (2) | 0.58887 (15) | 0.0249 (7) | |
C29 | 0.1324 (3) | 0.7978 (2) | 0.64379 (16) | 0.0339 (9) | |
H29 | 0.1044 | 0.7468 | 0.6366 | 0.041* | |
C42 | 0.4299 (3) | 0.7757 (2) | 0.59678 (14) | 0.0257 (7) | |
C55 | 0.7692 (2) | 0.5714 (2) | 0.56791 (12) | 0.0212 (7) | |
H55A | 0.8449 | 0.5670 | 0.5628 | 0.025* | |
H55B | 0.7388 | 0.6168 | 0.5477 | 0.025* | |
C10 | 0.0774 (3) | 0.2041 (2) | 0.74291 (13) | 0.0251 (7) | |
C16 | 0.5683 (3) | 0.2778 (2) | 0.69879 (14) | 0.0333 (8) | |
H16 | 0.6021 | 0.2862 | 0.7327 | 0.040* | |
C52 | 0.8063 (3) | 0.5139 (2) | 0.65596 (13) | 0.0283 (8) | |
H52A | 0.8820 | 0.5081 | 0.6513 | 0.034* | |
H52B | 0.8010 | 0.5226 | 0.6930 | 0.034* | |
C47 | 0.4942 (3) | 0.7828 (2) | 0.55779 (15) | 0.0351 (9) | |
H47 | 0.4646 | 0.7769 | 0.5230 | 0.042* | |
C7 | 0.2028 (3) | 0.2735 (2) | 0.67298 (13) | 0.0224 (7) | |
C25 | 0.1718 (3) | 0.1197 (2) | 0.53986 (15) | 0.0318 (8) | |
H25 | 0.1765 | 0.0645 | 0.5449 | 0.038* | |
C9 | 0.1820 (3) | 0.1808 (2) | 0.74093 (14) | 0.0296 (8) | |
H9 | 0.2118 | 0.1412 | 0.7637 | 0.036* | |
C12 | 0.0982 (3) | 0.2973 (2) | 0.67532 (14) | 0.0266 (7) | |
H12 | 0.0685 | 0.3375 | 0.6530 | 0.032* | |
C3 | 0.2664 (3) | 0.6339 (2) | 0.67137 (15) | 0.0256 (7) | |
C22 | 0.1644 (3) | 0.2799 (2) | 0.52520 (13) | 0.0242 (7) | |
H22 | 0.1625 | 0.3349 | 0.5195 | 0.029* | |
C30 | 0.0769 (3) | 0.8496 (2) | 0.67153 (16) | 0.0356 (9) | |
H30 | 0.0121 | 0.8330 | 0.6828 | 0.043* | |
C35 | 0.2418 (3) | 0.7906 (2) | 0.52221 (13) | 0.0256 (7) | |
C44 | 0.5840 (3) | 0.7957 (3) | 0.65881 (16) | 0.0401 (10) | |
H44 | 0.6140 | 0.7988 | 0.6937 | 0.048* | |
C57 | 0.7557 (2) | 0.4251 (2) | 0.58085 (12) | 0.0213 (7) | |
H57A | 0.7167 | 0.3769 | 0.5692 | 0.026* | |
H57B | 0.8311 | 0.4178 | 0.5758 | 0.026* | |
C14 | 0.4102 (3) | 0.2842 (2) | 0.63794 (13) | 0.0231 (7) | |
C37 | 0.1129 (3) | 0.7861 (2) | 0.44668 (14) | 0.0327 (8) | |
H37 | 0.0594 | 0.7581 | 0.4258 | 0.039* | |
C21 | 0.2208 (3) | 0.2501 (2) | 0.56945 (13) | 0.0234 (7) | |
C11 | 0.0376 (3) | 0.2631 (2) | 0.70974 (14) | 0.0260 (7) | |
H11 | −0.0331 | 0.2805 | 0.7107 | 0.031* | |
C13 | 0.0095 (3) | 0.1657 (2) | 0.77931 (15) | 0.0317 (8) | |
H13A | 0.0155 | 0.1085 | 0.7767 | 0.048* | |
H13B | −0.0645 | 0.1813 | 0.7703 | 0.048* | |
H13C | 0.0335 | 0.1822 | 0.8146 | 0.048* | |
C24 | 0.1110 (3) | 0.1492 (2) | 0.49648 (14) | 0.0277 (7) | |
C15 | 0.4625 (3) | 0.2981 (2) | 0.68698 (13) | 0.0268 (7) | |
H15 | 0.4254 | 0.3217 | 0.7125 | 0.032* | |
C27 | 0.0453 (3) | 0.0956 (2) | 0.46000 (16) | 0.0348 (8) | |
H27A | 0.0649 | 0.0409 | 0.4680 | 0.052* | |
H27B | 0.0579 | 0.1076 | 0.4246 | 0.052* | |
H27C | −0.0299 | 0.1033 | 0.4636 | 0.052* | |
C19 | 0.4682 (3) | 0.2526 (2) | 0.60059 (15) | 0.0329 (8) | |
H19 | 0.4345 | 0.2438 | 0.5667 | 0.039* | |
C17 | 0.6259 (3) | 0.2454 (2) | 0.66182 (15) | 0.0316 (8) | |
C40 | 0.2691 (3) | 0.8659 (2) | 0.50738 (16) | 0.0348 (9) | |
H40 | 0.3234 | 0.8937 | 0.5279 | 0.042* | |
C45 | 0.6480 (3) | 0.8063 (2) | 0.62011 (16) | 0.0334 (8) | |
C23 | 0.1108 (3) | 0.2303 (2) | 0.48932 (13) | 0.0253 (7) | |
H23 | 0.0730 | 0.2520 | 0.4591 | 0.030* | |
C46 | 0.6026 (3) | 0.7985 (3) | 0.56931 (16) | 0.0396 (9) | |
H46 | 0.6456 | 0.8039 | 0.5422 | 0.048* | |
C43 | 0.4768 (3) | 0.7806 (3) | 0.64735 (15) | 0.0397 (10) | |
H43 | 0.4345 | 0.7735 | 0.6746 | 0.048* | |
C20 | 0.7412 (3) | 0.2254 (3) | 0.67495 (17) | 0.0424 (10) | |
H20A | 0.7688 | 0.2518 | 0.7070 | 0.064* | |
H20B | 0.7809 | 0.2429 | 0.6471 | 0.064* | |
H20C | 0.7490 | 0.1685 | 0.6793 | 0.064* | |
C41 | 0.0788 (4) | 0.9010 (3) | 0.38623 (17) | 0.0426 (10) | |
H41A | 0.0493 | 0.8607 | 0.3619 | 0.064* | |
H41B | 0.1272 | 0.9347 | 0.3696 | 0.064* | |
H41C | 0.0211 | 0.9328 | 0.3970 | 0.064* | |
C26 | 0.2254 (3) | 0.1689 (2) | 0.57566 (14) | 0.0306 (8) | |
H26 | 0.2660 | 0.1472 | 0.6050 | 0.037* | |
C18 | 0.5747 (3) | 0.2341 (2) | 0.61253 (16) | 0.0358 (9) | |
H18 | 0.6132 | 0.2133 | 0.5866 | 0.043* | |
C39 | 0.2188 (3) | 0.9006 (2) | 0.46349 (17) | 0.0389 (9) | |
H39 | 0.2394 | 0.9518 | 0.4542 | 0.047* | |
C31 | 0.1127 (3) | 0.9229 (2) | 0.68301 (14) | 0.0319 (8) | |
C38 | 0.1385 (3) | 0.8618 (2) | 0.43278 (15) | 0.0327 (8) | |
C48 | 0.7645 (3) | 0.8245 (3) | 0.63302 (19) | 0.0437 (10) | |
H48A | 0.7767 | 0.8804 | 0.6274 | 0.066* | |
H48B | 0.8056 | 0.7933 | 0.6109 | 0.066* | |
H48C | 0.7867 | 0.8114 | 0.6691 | 0.066* | |
C33 | 0.2633 (4) | 0.8923 (3) | 0.6380 (3) | 0.0705 (19) | |
H33 | 0.3290 | 0.9083 | 0.6274 | 0.085* | |
C34 | 0.0505 (3) | 0.9778 (3) | 0.71285 (18) | 0.0422 (10) | |
H34A | −0.0248 | 0.9742 | 0.6998 | 0.063* | |
H34B | 0.0752 | 1.0317 | 0.7089 | 0.063* | |
H34C | 0.0605 | 0.9632 | 0.7493 | 0.063* | |
C32 | 0.2065 (5) | 0.9446 (3) | 0.6649 (3) | 0.076 (2) | |
H32 | 0.2327 | 0.9963 | 0.6710 | 0.091* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Os2 | 0.01309 (8) | 0.01962 (9) | 0.01877 (8) | −0.00181 (5) | 0.00478 (5) | −0.00414 (5) |
Os1 | 0.01328 (8) | 0.02051 (8) | 0.01932 (8) | −0.00221 (5) | 0.00641 (5) | −0.00143 (5) |
P2 | 0.0186 (4) | 0.0222 (4) | 0.0242 (4) | −0.0045 (3) | 0.0059 (3) | −0.0036 (3) |
P1 | 0.0172 (4) | 0.0220 (4) | 0.0222 (4) | 0.0000 (3) | 0.0059 (3) | 0.0006 (3) |
O5 | 0.0147 (11) | 0.0282 (13) | 0.0231 (12) | −0.0018 (9) | 0.0034 (9) | 0.0019 (9) |
O7 | 0.0165 (11) | 0.0224 (12) | 0.0214 (11) | 0.0011 (8) | 0.0034 (9) | −0.0022 (9) |
O8 | 0.0226 (11) | 0.0217 (12) | 0.0205 (11) | −0.0022 (9) | 0.0084 (9) | −0.0025 (9) |
O6 | 0.0114 (10) | 0.0246 (12) | 0.0298 (12) | −0.0033 (9) | 0.0058 (9) | −0.0060 (10) |
O4 | 0.0179 (13) | 0.0280 (13) | 0.0428 (15) | 0.0003 (10) | 0.0025 (10) | −0.0016 (11) |
O3 | 0.0432 (15) | 0.0413 (16) | 0.0176 (13) | 0.0019 (12) | 0.0031 (10) | −0.0092 (11) |
O2 | 0.0154 (14) | 0.0328 (14) | 0.067 (2) | −0.0014 (11) | 0.0043 (12) | −0.0038 (13) |
O1 | 0.068 (2) | 0.0454 (18) | 0.0316 (15) | −0.0182 (14) | 0.0294 (15) | −0.0102 (13) |
C6 | 0.0091 (14) | 0.0246 (17) | 0.0200 (15) | −0.0028 (12) | 0.0025 (11) | −0.0029 (13) |
C49 | 0.0145 (15) | 0.0237 (16) | 0.0173 (15) | −0.0032 (13) | 0.0032 (11) | −0.0023 (13) |
C51 | 0.0166 (16) | 0.0322 (19) | 0.0237 (17) | −0.0056 (14) | 0.0010 (12) | −0.0089 (15) |
C50 | 0.0179 (16) | 0.0292 (18) | 0.0185 (15) | −0.0041 (13) | 0.0019 (12) | −0.0074 (14) |
C28 | 0.0244 (17) | 0.0239 (18) | 0.0279 (17) | −0.0025 (14) | 0.0046 (14) | −0.0055 (14) |
C54 | 0.0218 (17) | 0.0294 (18) | 0.0183 (15) | 0.0000 (14) | 0.0033 (13) | 0.0002 (13) |
C4 | 0.0126 (16) | 0.0195 (16) | 0.0275 (17) | 0.0003 (12) | 0.0071 (12) | −0.0022 (13) |
C58 | 0.0139 (15) | 0.0222 (16) | 0.0165 (15) | −0.0015 (12) | 0.0013 (11) | −0.0027 (12) |
C8 | 0.0204 (17) | 0.032 (2) | 0.0280 (18) | 0.0026 (14) | 0.0052 (13) | 0.0035 (15) |
C1 | 0.027 (2) | 0.0269 (19) | 0.034 (2) | −0.0057 (14) | 0.0150 (16) | −0.0028 (15) |
C56 | 0.0123 (14) | 0.0248 (17) | 0.0183 (15) | −0.0017 (13) | 0.0022 (11) | −0.0038 (13) |
C53 | 0.0190 (17) | 0.0348 (19) | 0.0189 (16) | 0.0041 (14) | 0.0008 (12) | 0.0031 (14) |
C5 | 0.0140 (15) | 0.0249 (17) | 0.0153 (14) | −0.0017 (12) | 0.0020 (11) | −0.0039 (12) |
C36 | 0.0328 (19) | 0.0258 (18) | 0.0284 (18) | −0.0039 (15) | 0.0068 (14) | −0.0032 (15) |
C2 | 0.0155 (18) | 0.0221 (17) | 0.039 (2) | −0.0012 (13) | 0.0092 (14) | −0.0005 (15) |
C29 | 0.0299 (19) | 0.0235 (18) | 0.051 (2) | −0.0059 (15) | 0.0149 (17) | −0.0109 (17) |
C42 | 0.0217 (17) | 0.0261 (18) | 0.0306 (18) | −0.0049 (14) | 0.0082 (14) | −0.0056 (14) |
C55 | 0.0132 (15) | 0.0274 (18) | 0.0232 (16) | −0.0066 (13) | 0.0028 (12) | −0.0073 (14) |
C10 | 0.0251 (17) | 0.0256 (17) | 0.0253 (17) | −0.0045 (14) | 0.0063 (13) | −0.0019 (14) |
C16 | 0.0259 (18) | 0.046 (2) | 0.0278 (18) | −0.0002 (16) | 0.0027 (14) | 0.0137 (17) |
C52 | 0.0163 (16) | 0.046 (2) | 0.0220 (17) | −0.0009 (15) | −0.0013 (13) | −0.0053 (16) |
C47 | 0.0267 (19) | 0.046 (2) | 0.034 (2) | −0.0009 (17) | 0.0079 (15) | 0.0026 (17) |
C7 | 0.0209 (16) | 0.0224 (17) | 0.0249 (16) | −0.0044 (13) | 0.0075 (13) | 0.0022 (13) |
C25 | 0.038 (2) | 0.0196 (18) | 0.039 (2) | 0.0009 (15) | 0.0068 (17) | 0.0000 (15) |
C9 | 0.0272 (18) | 0.031 (2) | 0.0299 (18) | −0.0001 (15) | 0.0024 (14) | 0.0080 (15) |
C12 | 0.0238 (17) | 0.0259 (18) | 0.0302 (18) | 0.0001 (14) | 0.0027 (14) | 0.0033 (15) |
C3 | 0.0173 (16) | 0.0211 (17) | 0.039 (2) | 0.0014 (13) | 0.0054 (14) | −0.0002 (15) |
C22 | 0.0245 (17) | 0.0196 (16) | 0.0295 (17) | 0.0024 (13) | 0.0078 (13) | 0.0026 (14) |
C30 | 0.0288 (19) | 0.029 (2) | 0.052 (2) | −0.0015 (16) | 0.0183 (17) | −0.0027 (18) |
C35 | 0.0224 (17) | 0.0265 (18) | 0.0296 (18) | 0.0018 (14) | 0.0099 (14) | −0.0003 (14) |
C44 | 0.0270 (19) | 0.059 (3) | 0.035 (2) | −0.0132 (18) | 0.0044 (16) | −0.0151 (19) |
C57 | 0.0128 (15) | 0.0266 (18) | 0.0243 (17) | −0.0007 (13) | 0.0017 (12) | −0.0029 (14) |
C14 | 0.0216 (16) | 0.0226 (17) | 0.0256 (17) | 0.0020 (13) | 0.0051 (13) | 0.0057 (14) |
C37 | 0.035 (2) | 0.039 (2) | 0.0240 (18) | −0.0037 (17) | 0.0035 (15) | −0.0061 (16) |
C21 | 0.0181 (16) | 0.0254 (17) | 0.0280 (17) | 0.0019 (13) | 0.0086 (13) | 0.0017 (14) |
C11 | 0.0181 (16) | 0.0250 (18) | 0.0363 (19) | 0.0000 (13) | 0.0089 (14) | 0.0007 (15) |
C13 | 0.0289 (19) | 0.0284 (19) | 0.040 (2) | 0.0021 (15) | 0.0118 (16) | 0.0084 (16) |
C24 | 0.0261 (17) | 0.0286 (19) | 0.0294 (18) | −0.0009 (15) | 0.0071 (14) | −0.0024 (15) |
C15 | 0.0219 (17) | 0.0334 (19) | 0.0266 (17) | −0.0012 (14) | 0.0095 (13) | 0.0066 (15) |
C27 | 0.037 (2) | 0.0273 (19) | 0.040 (2) | −0.0048 (16) | 0.0055 (17) | −0.0051 (17) |
C19 | 0.0241 (18) | 0.042 (2) | 0.0326 (19) | 0.0046 (16) | 0.0052 (15) | −0.0028 (17) |
C17 | 0.0240 (18) | 0.034 (2) | 0.038 (2) | 0.0064 (15) | 0.0113 (15) | 0.0152 (17) |
C40 | 0.0285 (19) | 0.0262 (19) | 0.049 (2) | −0.0065 (16) | −0.0002 (17) | 0.0035 (17) |
C45 | 0.0255 (18) | 0.034 (2) | 0.041 (2) | −0.0063 (16) | 0.0047 (15) | −0.0042 (17) |
C23 | 0.0234 (17) | 0.0245 (18) | 0.0276 (17) | 0.0010 (14) | 0.0014 (13) | 0.0006 (14) |
C46 | 0.0238 (19) | 0.057 (3) | 0.040 (2) | −0.0041 (18) | 0.0115 (16) | 0.008 (2) |
C43 | 0.0272 (19) | 0.062 (3) | 0.031 (2) | −0.0157 (19) | 0.0108 (16) | −0.0126 (19) |
C20 | 0.027 (2) | 0.053 (3) | 0.050 (2) | 0.0137 (18) | 0.0124 (17) | 0.023 (2) |
C41 | 0.052 (3) | 0.037 (2) | 0.038 (2) | 0.0079 (19) | 0.0030 (19) | 0.0016 (18) |
C26 | 0.036 (2) | 0.0274 (19) | 0.0283 (18) | 0.0040 (15) | 0.0015 (15) | 0.0041 (15) |
C18 | 0.0268 (19) | 0.041 (2) | 0.042 (2) | 0.0074 (16) | 0.0121 (16) | −0.0013 (18) |
C39 | 0.039 (2) | 0.028 (2) | 0.049 (2) | −0.0021 (17) | 0.0030 (18) | 0.0074 (18) |
C31 | 0.0299 (19) | 0.034 (2) | 0.0311 (19) | 0.0033 (16) | 0.0013 (15) | −0.0105 (16) |
C38 | 0.035 (2) | 0.033 (2) | 0.0301 (19) | 0.0071 (16) | 0.0070 (15) | 0.0001 (16) |
C48 | 0.0242 (19) | 0.050 (3) | 0.058 (3) | −0.0117 (18) | 0.0101 (18) | −0.008 (2) |
C33 | 0.050 (3) | 0.044 (3) | 0.128 (5) | −0.023 (2) | 0.054 (3) | −0.044 (3) |
C34 | 0.039 (2) | 0.041 (2) | 0.047 (2) | 0.0045 (18) | 0.0052 (19) | −0.019 (2) |
C32 | 0.071 (4) | 0.043 (3) | 0.123 (5) | −0.026 (3) | 0.051 (4) | −0.050 (3) |
Os2—Os1 | 2.7398 (2) | C52—H52B | 0.9900 |
Os2—P2 | 2.3964 (9) | C47—H47 | 0.9500 |
Os2—O8i | 2.124 (2) | C47—C46 | 1.401 (5) |
Os2—O6 | 2.119 (2) | C7—C12 | 1.398 (5) |
Os2—C4 | 1.850 (3) | C25—H25 | 0.9500 |
Os2—C3 | 1.848 (4) | C25—C24 | 1.391 (5) |
Os1—P1 | 2.4028 (9) | C25—C26 | 1.377 (5) |
Os1—O5 | 2.114 (2) | C9—H9 | 0.9500 |
Os1—O7i | 2.136 (2) | C12—H12 | 0.9500 |
Os1—C1 | 1.852 (4) | C12—C11 | 1.381 (5) |
Os1—C2 | 1.858 (4) | C22—H22 | 0.9500 |
P2—C28 | 1.846 (3) | C22—C21 | 1.386 (5) |
P2—C42 | 1.821 (3) | C22—C23 | 1.382 (5) |
P2—C35 | 1.825 (4) | C30—H30 | 0.9500 |
P1—C7 | 1.840 (3) | C30—C31 | 1.353 (5) |
P1—C14 | 1.815 (3) | C35—C40 | 1.396 (5) |
P1—C21 | 1.832 (4) | C44—H44 | 0.9500 |
O5—C5 | 1.261 (4) | C44—C45 | 1.383 (6) |
O7—Os1i | 2.136 (2) | C44—C43 | 1.385 (5) |
O7—C6 | 1.268 (4) | C57—H57A | 0.9900 |
O8—Os2i | 2.124 (2) | C57—H57B | 0.9900 |
O8—C6 | 1.265 (4) | C14—C15 | 1.395 (5) |
O6—C5 | 1.261 (4) | C14—C19 | 1.399 (5) |
O4—C4 | 1.150 (4) | C37—H37 | 0.9500 |
O3—C3 | 1.164 (4) | C37—C38 | 1.389 (6) |
O2—C2 | 1.152 (4) | C21—C26 | 1.393 (5) |
O1—C1 | 1.155 (5) | C11—H11 | 0.9500 |
C6—C56 | 1.518 (4) | C13—H13A | 0.9800 |
C49—C50 | 1.539 (4) | C13—H13B | 0.9800 |
C49—C54 | 1.530 (5) | C13—H13C | 0.9800 |
C49—C58 | 1.545 (4) | C24—C27 | 1.503 (5) |
C49—C5 | 1.525 (4) | C24—C23 | 1.396 (5) |
C51—H51 | 1.0000 | C15—H15 | 0.9500 |
C51—C50 | 1.532 (4) | C27—H27A | 0.9800 |
C51—C55 | 1.524 (5) | C27—H27B | 0.9800 |
C51—C52 | 1.531 (5) | C27—H27C | 0.9800 |
C50—H50A | 0.9900 | C19—H19 | 0.9500 |
C50—H50B | 0.9900 | C19—C18 | 1.390 (5) |
C28—C29 | 1.371 (5) | C17—C20 | 1.506 (5) |
C28—C33 | 1.371 (5) | C17—C18 | 1.389 (6) |
C54—H54A | 0.9900 | C40—H40 | 0.9500 |
C54—H54B | 0.9900 | C40—C39 | 1.382 (6) |
C54—C53 | 1.536 (5) | C45—C46 | 1.393 (6) |
C58—H58A | 0.9900 | C45—C48 | 1.513 (5) |
C58—H58B | 0.9900 | C23—H23 | 0.9500 |
C58—C56 | 1.543 (4) | C46—H46 | 0.9500 |
C8—H8 | 0.9500 | C43—H43 | 0.9500 |
C8—C7 | 1.389 (5) | C20—H20A | 0.9800 |
C8—C9 | 1.390 (5) | C20—H20B | 0.9800 |
C56—C55 | 1.546 (4) | C20—H20C | 0.9800 |
C56—C57 | 1.537 (5) | C41—H41A | 0.9800 |
C53—H53 | 1.0000 | C41—H41B | 0.9800 |
C53—C52 | 1.530 (5) | C41—H41C | 0.9800 |
C53—C57 | 1.532 (4) | C41—C38 | 1.513 (5) |
C36—H36 | 0.9500 | C26—H26 | 0.9500 |
C36—C35 | 1.392 (5) | C18—H18 | 0.9500 |
C36—C37 | 1.387 (5) | C39—H39 | 0.9500 |
C29—H29 | 0.9500 | C39—C38 | 1.391 (6) |
C29—C30 | 1.386 (5) | C31—C34 | 1.501 (5) |
C42—C47 | 1.386 (5) | C31—C32 | 1.384 (7) |
C42—C43 | 1.389 (5) | C48—H48A | 0.9800 |
C55—H55A | 0.9900 | C48—H48B | 0.9800 |
C55—H55B | 0.9900 | C48—H48C | 0.9800 |
C10—C9 | 1.395 (5) | C33—H33 | 0.9500 |
C10—C11 | 1.385 (5) | C33—C32 | 1.389 (7) |
C10—C13 | 1.507 (5) | C34—H34A | 0.9800 |
C16—H16 | 0.9500 | C34—H34B | 0.9800 |
C16—C15 | 1.389 (5) | C34—H34C | 0.9800 |
C16—C17 | 1.394 (5) | C32—H32 | 0.9500 |
C52—H52A | 0.9900 | ||
P2—Os2—Os1 | 170.60 (2) | C42—C47—H47 | 119.7 |
O8i—Os2—Os1 | 82.86 (6) | C42—C47—C46 | 120.5 (4) |
O8i—Os2—P2 | 91.84 (6) | C46—C47—H47 | 119.7 |
O6—Os2—Os1 | 82.76 (6) | C8—C7—P1 | 123.7 (3) |
O6—Os2—P2 | 88.83 (7) | C8—C7—C12 | 118.0 (3) |
O6—Os2—O8i | 81.95 (9) | C12—C7—P1 | 118.0 (3) |
C4—Os2—Os1 | 91.75 (10) | C24—C25—H25 | 119.4 |
C4—Os2—P2 | 96.40 (10) | C26—C25—H25 | 119.4 |
C4—Os2—O8i | 94.28 (12) | C26—C25—C24 | 121.3 (3) |
C4—Os2—O6 | 173.67 (11) | C8—C9—C10 | 121.2 (3) |
C3—Os2—Os1 | 93.86 (11) | C8—C9—H9 | 119.4 |
C3—Os2—P2 | 90.67 (11) | C10—C9—H9 | 119.4 |
C3—Os2—O8i | 173.78 (12) | C7—C12—H12 | 119.6 |
C3—Os2—O6 | 92.41 (12) | C11—C12—C7 | 120.8 (3) |
C3—Os2—C4 | 91.09 (15) | C11—C12—H12 | 119.6 |
P1—Os1—Os2 | 170.20 (2) | O3—C3—Os2 | 178.8 (3) |
O5—Os1—Os2 | 82.59 (6) | C21—C22—H22 | 119.7 |
O5—Os1—P1 | 88.23 (6) | C23—C22—H22 | 119.7 |
O5—Os1—O7i | 81.97 (9) | C23—C22—C21 | 120.7 (3) |
O7i—Os1—Os2 | 82.46 (6) | C29—C30—H30 | 119.1 |
O7i—Os1—P1 | 92.92 (6) | C31—C30—C29 | 121.8 (3) |
C1—Os1—Os2 | 92.49 (11) | C31—C30—H30 | 119.1 |
C1—Os1—P1 | 91.92 (11) | C36—C35—P2 | 119.6 (3) |
C1—Os1—O5 | 96.48 (14) | C36—C35—C40 | 117.7 (3) |
C1—Os1—O7i | 174.86 (12) | C40—C35—P2 | 122.2 (3) |
C1—Os1—C2 | 90.83 (17) | C45—C44—H44 | 119.6 |
C2—Os1—Os2 | 94.00 (11) | C45—C44—C43 | 120.9 (4) |
C2—Os1—P1 | 94.68 (11) | C43—C44—H44 | 119.6 |
C2—Os1—O5 | 172.05 (13) | C56—C57—H57A | 109.7 |
C2—Os1—O7i | 90.49 (13) | C56—C57—H57B | 109.7 |
C28—P2—Os2 | 113.79 (12) | C53—C57—C56 | 109.7 (3) |
C42—P2—Os2 | 113.16 (12) | C53—C57—H57A | 109.7 |
C42—P2—C28 | 103.44 (15) | C53—C57—H57B | 109.7 |
C42—P2—C35 | 106.27 (16) | H57A—C57—H57B | 108.2 |
C35—P2—Os2 | 118.98 (12) | C15—C14—P1 | 120.1 (3) |
C35—P2—C28 | 99.30 (16) | C15—C14—C19 | 118.4 (3) |
C7—P1—Os1 | 112.26 (11) | C19—C14—P1 | 121.2 (3) |
C14—P1—Os1 | 114.78 (11) | C36—C37—H37 | 119.4 |
C14—P1—C7 | 104.90 (15) | C36—C37—C38 | 121.2 (4) |
C14—P1—C21 | 104.75 (15) | C38—C37—H37 | 119.4 |
C21—P1—Os1 | 119.79 (11) | C22—C21—P1 | 121.0 (3) |
C21—P1—C7 | 98.22 (15) | C22—C21—C26 | 118.2 (3) |
C5—O5—Os1 | 122.2 (2) | C26—C21—P1 | 120.4 (3) |
C6—O7—Os1i | 123.3 (2) | C10—C11—H11 | 119.2 |
C6—O8—Os2i | 123.9 (2) | C12—C11—C10 | 121.7 (3) |
C5—O6—Os2 | 123.0 (2) | C12—C11—H11 | 119.2 |
O7—C6—C56 | 118.0 (3) | C10—C13—H13A | 109.5 |
O8—C6—O7 | 124.2 (3) | C10—C13—H13B | 109.5 |
O8—C6—C56 | 117.7 (3) | C10—C13—H13C | 109.5 |
C50—C49—C58 | 108.9 (3) | H13A—C13—H13B | 109.5 |
C54—C49—C50 | 110.1 (3) | H13A—C13—H13C | 109.5 |
C54—C49—C58 | 109.3 (3) | H13B—C13—H13C | 109.5 |
C5—C49—C50 | 111.2 (3) | C25—C24—C27 | 121.0 (3) |
C5—C49—C54 | 111.4 (3) | C25—C24—C23 | 117.4 (3) |
C5—C49—C58 | 105.9 (2) | C23—C24—C27 | 121.6 (3) |
C50—C51—H51 | 109.2 | C16—C15—C14 | 120.5 (3) |
C55—C51—H51 | 109.2 | C16—C15—H15 | 119.8 |
C55—C51—C50 | 109.3 (3) | C14—C15—H15 | 119.8 |
C55—C51—C52 | 109.7 (3) | C24—C27—H27A | 109.5 |
C52—C51—H51 | 109.2 | C24—C27—H27B | 109.5 |
C52—C51—C50 | 110.2 (3) | C24—C27—H27C | 109.5 |
C49—C50—H50A | 109.9 | H27A—C27—H27B | 109.5 |
C49—C50—H50B | 109.9 | H27A—C27—H27C | 109.5 |
C51—C50—C49 | 109.0 (3) | H27B—C27—H27C | 109.5 |
C51—C50—H50A | 109.9 | C14—C19—H19 | 119.7 |
C51—C50—H50B | 109.9 | C18—C19—C14 | 120.6 (4) |
H50A—C50—H50B | 108.3 | C18—C19—H19 | 119.7 |
C29—C28—P2 | 119.8 (3) | C16—C17—C20 | 120.5 (4) |
C33—C28—P2 | 123.4 (3) | C18—C17—C16 | 118.3 (3) |
C33—C28—C29 | 116.6 (3) | C18—C17—C20 | 121.2 (3) |
C49—C54—H54A | 109.7 | C35—C40—H40 | 119.4 |
C49—C54—H54B | 109.7 | C39—C40—C35 | 121.3 (4) |
C49—C54—C53 | 109.7 (3) | C39—C40—H40 | 119.4 |
H54A—C54—H54B | 108.2 | C44—C45—C46 | 118.3 (3) |
C53—C54—H54A | 109.7 | C44—C45—C48 | 120.5 (4) |
C53—C54—H54B | 109.7 | C46—C45—C48 | 121.2 (4) |
O4—C4—Os2 | 178.9 (3) | C22—C23—C24 | 121.4 (3) |
C49—C58—H58A | 109.7 | C22—C23—H23 | 119.3 |
C49—C58—H58B | 109.7 | C24—C23—H23 | 119.3 |
H58A—C58—H58B | 108.2 | C47—C46—H46 | 119.6 |
C56—C58—C49 | 109.6 (2) | C45—C46—C47 | 120.7 (4) |
C56—C58—H58A | 109.7 | C45—C46—H46 | 119.6 |
C56—C58—H58B | 109.7 | C42—C43—H43 | 119.3 |
C7—C8—H8 | 119.6 | C44—C43—C42 | 121.3 (3) |
C7—C8—C9 | 120.7 (3) | C44—C43—H43 | 119.3 |
C9—C8—H8 | 119.6 | C17—C20—H20A | 109.5 |
O1—C1—Os1 | 178.5 (4) | C17—C20—H20B | 109.5 |
C6—C56—C58 | 109.5 (2) | C17—C20—H20C | 109.5 |
C6—C56—C55 | 108.8 (3) | H20A—C20—H20B | 109.5 |
C6—C56—C57 | 111.3 (3) | H20A—C20—H20C | 109.5 |
C58—C56—C55 | 108.1 (3) | H20B—C20—H20C | 109.5 |
C57—C56—C58 | 109.2 (3) | H41A—C41—H41B | 109.5 |
C57—C56—C55 | 109.9 (3) | H41A—C41—H41C | 109.5 |
C54—C53—H53 | 109.5 | H41B—C41—H41C | 109.5 |
C52—C53—C54 | 109.7 (3) | C38—C41—H41A | 109.5 |
C52—C53—H53 | 109.5 | C38—C41—H41B | 109.5 |
C52—C53—C57 | 109.7 (3) | C38—C41—H41C | 109.5 |
C57—C53—C54 | 109.0 (3) | C25—C26—C21 | 121.0 (3) |
C57—C53—H53 | 109.5 | C25—C26—H26 | 119.5 |
O5—C5—O6 | 125.6 (3) | C21—C26—H26 | 119.5 |
O5—C5—C49 | 117.5 (3) | C19—C18—H18 | 119.5 |
O6—C5—C49 | 116.8 (3) | C17—C18—C19 | 121.0 (3) |
C35—C36—H36 | 119.5 | C17—C18—H18 | 119.5 |
C37—C36—H36 | 119.5 | C40—C39—H39 | 119.5 |
C37—C36—C35 | 120.9 (3) | C40—C39—C38 | 120.9 (4) |
O2—C2—Os1 | 177.1 (3) | C38—C39—H39 | 119.5 |
C28—C29—H29 | 119.0 | C30—C31—C34 | 120.5 (4) |
C28—C29—C30 | 122.0 (3) | C30—C31—C32 | 116.8 (4) |
C30—C29—H29 | 119.0 | C32—C31—C34 | 122.7 (4) |
C47—C42—P2 | 122.9 (3) | C37—C38—C41 | 120.6 (4) |
C47—C42—C43 | 118.2 (3) | C37—C38—C39 | 118.0 (4) |
C43—C42—P2 | 118.6 (3) | C39—C38—C41 | 121.4 (4) |
C51—C55—C56 | 109.8 (3) | C45—C48—H48A | 109.5 |
C51—C55—H55A | 109.7 | C45—C48—H48B | 109.5 |
C51—C55—H55B | 109.7 | C45—C48—H48C | 109.5 |
C56—C55—H55A | 109.7 | H48A—C48—H48B | 109.5 |
C56—C55—H55B | 109.7 | H48A—C48—H48C | 109.5 |
H55A—C55—H55B | 108.2 | H48B—C48—H48C | 109.5 |
C9—C10—C13 | 121.2 (3) | C28—C33—H33 | 119.4 |
C11—C10—C9 | 117.5 (3) | C28—C33—C32 | 121.2 (4) |
C11—C10—C13 | 121.2 (3) | C32—C33—H33 | 119.4 |
C15—C16—H16 | 119.4 | C31—C34—H34A | 109.5 |
C15—C16—C17 | 121.2 (4) | C31—C34—H34B | 109.5 |
C17—C16—H16 | 119.4 | C31—C34—H34C | 109.5 |
C51—C52—H52A | 109.8 | H34A—C34—H34B | 109.5 |
C51—C52—H52B | 109.8 | H34A—C34—H34C | 109.5 |
C53—C52—C51 | 109.6 (3) | H34B—C34—H34C | 109.5 |
C53—C52—H52A | 109.8 | C31—C32—C33 | 121.5 (4) |
C53—C52—H52B | 109.8 | C31—C32—H32 | 119.2 |
H52A—C52—H52B | 108.2 | C33—C32—H32 | 119.2 |
Os2—P2—C28—C29 | −30.9 (3) | C29—C28—C33—C32 | −1.5 (9) |
Os2—P2—C28—C33 | 154.6 (4) | C29—C30—C31—C34 | 179.6 (4) |
Os2—P2—C42—C47 | 100.1 (3) | C29—C30—C31—C32 | 1.1 (7) |
Os2—P2—C42—C43 | −72.8 (3) | C42—P2—C28—C29 | −154.1 (3) |
Os2—P2—C35—C36 | 17.1 (3) | C42—P2—C28—C33 | 31.4 (5) |
Os2—P2—C35—C40 | −171.8 (3) | C42—P2—C35—C36 | 146.1 (3) |
Os2i—O8—C6—O7 | −5.1 (4) | C42—P2—C35—C40 | −42.7 (3) |
Os2i—O8—C6—C56 | 174.87 (19) | C42—C47—C46—C45 | 0.8 (7) |
Os2—O6—C5—O5 | −1.4 (4) | C55—C51—C50—C49 | 61.3 (4) |
Os2—O6—C5—C49 | 175.01 (19) | C55—C51—C52—C53 | −60.5 (3) |
Os1—P1—C7—C8 | −140.9 (3) | C55—C56—C57—C53 | 58.2 (3) |
Os1—P1—C7—C12 | 45.3 (3) | C16—C17—C18—C19 | −1.6 (6) |
Os1—P1—C14—C15 | 71.3 (3) | C52—C51—C50—C49 | −59.4 (3) |
Os1—P1—C14—C19 | −102.8 (3) | C52—C51—C55—C56 | 59.4 (3) |
Os1—P1—C21—C22 | −1.6 (3) | C52—C53—C57—C56 | −59.3 (3) |
Os1—P1—C21—C26 | −173.8 (2) | C47—C42—C43—C44 | 2.9 (6) |
Os1—O5—C5—O6 | 18.7 (4) | C7—P1—C14—C15 | −52.4 (3) |
Os1—O5—C5—C49 | −157.7 (2) | C7—P1—C14—C19 | 133.6 (3) |
Os1i—O7—C6—O8 | −12.3 (4) | C7—P1—C21—C22 | 120.0 (3) |
Os1i—O7—C6—C56 | 167.69 (19) | C7—P1—C21—C26 | −52.2 (3) |
P2—C28—C29—C30 | −174.7 (3) | C7—C8—C9—C10 | 1.1 (6) |
P2—C28—C33—C32 | 173.2 (6) | C7—C12—C11—C10 | −0.3 (6) |
P2—C42—C47—C46 | −176.2 (3) | C25—C24—C23—C22 | −3.3 (5) |
P2—C42—C43—C44 | 176.2 (4) | C9—C8—C7—P1 | −174.2 (3) |
P2—C35—C40—C39 | −169.5 (3) | C9—C8—C7—C12 | −0.5 (5) |
P1—C7—C12—C11 | 174.2 (3) | C9—C10—C11—C12 | 0.9 (5) |
P1—C14—C15—C16 | −177.0 (3) | C22—C21—C26—C25 | −2.6 (5) |
P1—C14—C19—C18 | 175.6 (3) | C30—C31—C32—C33 | −2.5 (10) |
P1—C21—C26—C25 | 169.9 (3) | C35—P2—C28—C29 | 96.6 (3) |
O7—C6—C56—C58 | 76.0 (3) | C35—P2—C28—C33 | −77.9 (5) |
O7—C6—C56—C55 | −42.0 (4) | C35—P2—C42—C47 | −32.3 (4) |
O7—C6—C56—C57 | −163.3 (3) | C35—P2—C42—C43 | 154.8 (3) |
O8—C6—C56—C58 | −104.0 (3) | C35—C36—C37—C38 | 0.9 (6) |
O8—C6—C56—C55 | 138.0 (3) | C35—C40—C39—C38 | 0.4 (6) |
O8—C6—C56—C57 | 16.7 (4) | C44—C45—C46—C47 | 2.0 (7) |
C6—C56—C55—C51 | 179.4 (3) | C57—C56—C55—C51 | −58.4 (3) |
C6—C56—C57—C53 | 178.8 (3) | C57—C53—C52—C51 | 60.3 (4) |
C49—C54—C53—C52 | 59.3 (3) | C14—P1—C7—C8 | −15.7 (3) |
C49—C54—C53—C57 | −60.9 (4) | C14—P1—C7—C12 | 170.6 (3) |
C49—C58—C56—C6 | −178.6 (3) | C14—P1—C21—C22 | −132.1 (3) |
C49—C58—C56—C55 | −60.2 (3) | C14—P1—C21—C26 | 55.7 (3) |
C49—C58—C56—C57 | 59.3 (3) | C14—C19—C18—C17 | 0.8 (6) |
C50—C49—C54—C53 | −59.3 (3) | C37—C36—C35—P2 | 169.1 (3) |
C50—C49—C58—C56 | 60.8 (3) | C37—C36—C35—C40 | −2.4 (5) |
C50—C49—C5—O5 | −143.5 (3) | C21—P1—C7—C8 | 92.1 (3) |
C50—C49—C5—O6 | 39.9 (4) | C21—P1—C7—C12 | −81.7 (3) |
C50—C51—C55—C56 | −61.6 (4) | C21—P1—C14—C15 | −155.3 (3) |
C50—C51—C52—C53 | 60.0 (4) | C21—P1—C14—C19 | 30.7 (3) |
C28—P2—C42—C47 | −136.3 (3) | C21—C22—C23—C24 | 0.4 (5) |
C28—P2—C42—C43 | 50.8 (4) | C11—C10—C9—C8 | −1.3 (5) |
C28—P2—C35—C36 | −106.9 (3) | C13—C10—C9—C8 | 177.9 (4) |
C28—P2—C35—C40 | 64.3 (3) | C13—C10—C11—C12 | −178.3 (3) |
C28—C29—C30—C31 | 0.0 (7) | C24—C25—C26—C21 | −0.3 (6) |
C28—C33—C32—C31 | 2.7 (12) | C15—C16—C17—C20 | 178.6 (4) |
C54—C49—C50—C51 | 59.1 (3) | C15—C16—C17—C18 | 0.2 (6) |
C54—C49—C58—C56 | −59.5 (3) | C15—C14—C19—C18 | 1.4 (6) |
C54—C49—C5—O5 | −20.2 (4) | C27—C24—C23—C22 | 174.5 (3) |
C54—C49—C5—O6 | 163.1 (3) | C19—C14—C15—C16 | −2.8 (5) |
C54—C53—C52—C51 | −59.4 (4) | C17—C16—C15—C14 | 2.0 (6) |
C54—C53—C57—C56 | 60.8 (3) | C40—C39—C38—C37 | −2.0 (6) |
C58—C49—C50—C51 | −60.6 (3) | C40—C39—C38—C41 | 176.6 (4) |
C58—C49—C54—C53 | 60.2 (3) | C45—C44—C43—C42 | −0.1 (7) |
C58—C49—C5—O5 | 98.4 (3) | C23—C22—C21—P1 | −169.9 (3) |
C58—C49—C5—O6 | −78.2 (3) | C23—C22—C21—C26 | 2.5 (5) |
C58—C56—C55—C51 | 60.6 (3) | C43—C42—C47—C46 | −3.2 (6) |
C58—C56—C57—C53 | −60.2 (3) | C43—C44—C45—C46 | −2.4 (7) |
C8—C7—C12—C11 | 0.1 (5) | C43—C44—C45—C48 | 178.7 (4) |
C5—C49—C50—C51 | −176.9 (3) | C20—C17—C18—C19 | 180.0 (4) |
C5—C49—C54—C53 | 176.8 (3) | C26—C25—C24—C27 | −174.6 (4) |
C5—C49—C58—C56 | −179.5 (3) | C26—C25—C24—C23 | 3.2 (5) |
C36—C35—C40—C39 | 1.8 (6) | C48—C45—C46—C47 | −179.1 (4) |
C36—C37—C38—C41 | −177.3 (4) | C33—C28—C29—C30 | 0.1 (7) |
C36—C37—C38—C39 | 1.4 (6) | C34—C31—C32—C33 | 179.1 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Acknowledgements
We are thankful for the support of the Abilene Christian University Scholars Lab.
Funding information
Funding for this research was provided by: Welch Foundation (grant No. R-0021).
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