research communications
[μ2-Bis(diphenylphosphanyl)hexane]bis[undecacarbonyl-triangulo-triruthenium(3 Ru—Ru)] hexane monosolvate: and Hirshfeld surface analysis
aChemical Sciences Programme, School of Distance Education, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, bDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat 380001, India, and cResearch Centre for Crystalline Materials, School of Science and Technology, Sunway University, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia
*Correspondence e-mail: edwardt@sunway.edu.my
In the title cluster complex hexane solvate, [Ru6(C30H32P2)(CO)22]·C6H14, two Ru3(CO)11 fragments are linked by a Ph2P(CH2)6PPh2 bridge with the P atoms equatorially disposed with respect to the Ru3 triangle in each case; the hexane solvent molecule is statistically disordered. The Ru⋯Ru distances span a relatively narrow range, i.e. 2.8378 (4) to 2.8644 (4) Å. The hexyl chain within the bridge has an all-trans conformation. In the molecular packing, C—H⋯O interactions between cluster molecules, and between cluster and hexane solvent molecules lead to a three-dimensional architecture. In addition, there are a large number of C≡O⋯π(arene) interactions in the crystal. The importance of the carbonyl groups in establishing the packing is emphasized by the contribution of 53.4% to the Hirshfeld surface by O⋯H/H⋯O contacts.
Keywords: crystal structure; ruthenium; cluster; carbonyl; Hirshfeld surface analysis.
CCDC reference: 975445
1. Chemical context
In the realm of cluster chemistry, diphosphane ligands are known to maintain the integrity of the metal core during chemical reactions (Kabir & Hogarth, 2009). In the solid state, diphosphane ligands are known to adopt a variety of bonding modes towards triruthenium clusters, including monodentate, chelating, edge-bridging and linking two clusters (Bruce et al., 1982; Lozano Diz et al., 2001; Shawkataly et al., 2012). The motivation for studying triruthenium cluster complexes containing diphosphane ligands arises primarily due to these complexes making attractive starting materials for further reactivity studies (Kabir & Hogarth, 2009; Rajbangshi et al., 2015, Shawkataly et al., 2016). Despite this, only relatively few compounds with diphosphane ligands connecting two triruthenium clusters have been structurally characterized (Bruce et al., 1982; Van Calcar et al., 1998; O'Connor et al., 2003; Kakizawa et al., 2015). Our interest in synthesizing the title [Ru3(CO)11]2[Ph2P(CH2)6PPh2] cluster is to enable a comparison of the structural variations that arise from lengthening of the organic backbone in the diphosphane ligand. Furthermore, the joining of smaller cluster units with such spacer ligands is a useful method for the construction of larger aggregates (Bruce et al., 1985; Kakizawa et al., 2015). In the present study, two triruthenium cluster units were successfully connected through a bidentate bridging Ph2P(CH2)6PPh2 ligand in the compound [Ru3(CO)11]2[Ph2P(CH2)6PPh2], which was isolated as a 1:1 n-hexane solvate, (I). Herein, the crystal and molecular structures of (I) are described, as well as an analysis of the calculated Hirshfeld surface.
2. Structural commentary
The molecular structure of the cluster molecule in (I) is shown in Fig. 1. The comprises two Ru3(CO)11 cluster molecules linked by a Ph2P(CH2)6PPh2 bridge and a hexane molecule which is statistically disordered over two sets of sites. The phosphane P atom occupies a position effectively coplanar with the Ru3 core in each case, i.e. an equatorial site. The two Ru3 cluster residues are each constructed about a triangular Ru3 core, and the Ru–Ru edges span a relatively narrow range of distances, i.e. 2.8378 (4) Å for Ru2⋯Ru3 to 2.8644 (4) Å, for Ru1⋯Ru3. Each of the carbonyl ligands occupies a terminal position, with the Ru—C≡O angles ranging from 169.7 (4)° for Ru—C10≡O10 to 179.4 (4)° for Ru5—C18≡O18. The hexyl chain in the diphosphane ligand has an all-trans conformation, with the P1/P2—C—C—C torsion angles being −177.8 (3) and 175.5 (2)°, respectively, and the C—C—C—C torsion angles ranging from 173.7 (3)° for C33—C34—C35—C36 to −177.4 (3)° for C32—C33—C34—C35. The consequence of this is that the pairs of P-bound phenyl rings lie to either side of the chain.
3. Supramolecular features
The molecular packing of (I) comprises a complex network of C—H⋯O and C≡O⋯π interactions. The C—H donors for the C—H⋯O interactions are either methylene- or phenyl-H, Table 1, and by themselves define a three-dimensional architecture, Fig. 2. Additional stability to the crystal is provided by a number of C≡O⋯π(arene) interactions, either with end-on or side-on approaches. Further discussion and details of the identified C≡O⋯π(arene) interactions are found below in Analysis of the Hirshfeld surface (§4). The closest interactions between the cluster molecule and the solvent hexane molecule are of the type solvent-methylene-C—H⋯O(carbonyl), Table 1. The solvent molecules reside in cavities defined by the cluster molecules.
4. Analysis of the Hirshfeld surface
The Hirshfeld surface calculations of (I) were performed in accord with a recent publication on a related heavy-atom complex and its dioxane solvate (Jotani et al., 2017). The presence of the carbonyl groups in (I) lead to their participation in C—H⋯O, C≡O⋯π and C⋯O/O⋯C interactions, and the Hirshfeld surfaces mapped over dnorm, Fig. 3, indicate the influence of these in the crystal. Of the C—H⋯O interactions summarized in Table 1, the donors and acceptors of more influential contacts are viewed as bright-red spots near the phenyl-H52 and C55, diphosphane-hexyl-H32B and C82X, and carbonyl-O4, O8, O14 and O19 atoms, whereas the comparatively weak C—H⋯O contacts are viewed as faint-red spots near the phenyl-C42, hexane-C81X and C82X, and carbonyl-O7, O11 and O17 atoms in Fig. 3. In addition, the presence of bright-red spots near the O2, O13, O21 and C21 atoms and the diminutive-red spots near the O1, O4, O19 and C15 atoms in Fig. 3, are also indicative of short inter-atomic O⋯O and C⋯O/O⋯C contacts effective in the crystal. The donors and acceptors of intermolecular interactions can also be viewed as blue and red regions, respectively, on the Hirshfeld surface mapped over electrostatic potential for the cluster molecule in Fig. 4a, and for the hexane molecule in Fig. 4b. Two intramolecular C—O⋯π contacts, i.e. one between carbonyl-O9 and the phenyl C51–C56 ring, and the other between carbonyl-O21 and the phenyl C71–C76 ring are also illustrated through black, dotted lines in Fig. 4a. The cavity occupied by the hexane molecule, showing the relevant C—H⋯O contacts, Table 1, is highlighted in Fig. 5.
The overall two-dimensional fingerprint plots for the cluster molecule alone and for (I) are shown in Fig. 6a and clearly indicate the significance of the solvent molecule on the packing. This is also evident from the percentage contribution from the different surface contacts summarized in Table 2 and from the fingerprint plots delineated into H⋯H, O⋯H/H⋯O, C⋯H/H⋯C, C⋯O/O⋯C and O⋯O contacts (McKinnon et al., 2007) in Figs. 6b–f, respectively. The inclusion of the hexane molecule in the Hirshfeld surface calculations increases the relative contributions from O⋯H/H⋯O, H⋯H and C⋯H/H⋯C contacts but decreases those contributed by O⋯O and C⋯O/O⋯C contacts. This observations arises as a result of the participation of the solvent molecule in interatomic H⋯H and C⋯H/H⋯C contacts, Table 3, and in the intermolecular C—H⋯O interactions listed in Table 1.
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The two pairs of short peaks at de + di ∼ 2.3 and 2.4 Å in the fingerprint plot for (I) delineated into H⋯H contacts, Fig. 6b (right-column) indicate the presence of short interatomic contacts involving phenyl- and hexane-hydrogen atoms. The greatest contribution of 53.4% to the Hirshfeld surface of (I) is from O⋯H/H⋯O contacts and these are characterized as two specific types of interactions leading to two distinct distributions of points in the delineated fingerprint plot of Fig. 6c. The pair of sharp spikes having green aligned points within the plot and with tips at de + di ∼ 2.5 Å are the result of C—H⋯O interactions involving cluster-bound atoms as donors and acceptors; the points corresponding to short interatomic weak C—H⋯O contacts (Table 1) and O⋯H/H⋯O contacts (Table 3) are merged within the plot. On the other hand, the exterior portion with broad tips at de + di ∼ 2.6 Å are due to C—H⋯O interactions involving hexane-bound atoms as donors and carbonyl- oxygen atoms as acceptors. The comparison of O⋯H/H⋯O delineated fingerprint plots for in Fig. 6c confirm this observation.
The involvement of hexane-H83A and H83B atoms in the short interatomic C⋯H/H⋯C contacts (Table 3) results in forceps-like peaks at de + di ∼ 2.9 Å in the delineated fingerprint, Fig. 6d. The 7.8% contribution from C⋯O/O⋯C contacts to the Hirshfeld surface of (I) is due to the involvement of all carbonyl-O atoms (except O5) either in short interatomic C⋯O/O⋯C contacts, Table 3, or in end-on or side-on C≡O⋯π interactions, summarized in Table 4. The impact of end-on metal-C≡O⋯π(arene) interactions upon supramolecular aggregation patterns has been addressed in the recent literature (Zukerman-Schpector et al., 2011, 2012). The pair of sharp, forceps-like tips at de + di ∼ 3.0 Å in the fingerprint plots delineated into C⋯O/O⋯C contacts, Fig. 6e, represent short C⋯O/O⋯C contacts involving carbonyl-O1, O13, C15 and C21 atoms while the points distributed in adjoining parabolic form around (de, di) = (1.8, 2.0 Å) and (2.0, 1.8 Å) represent C≡O⋯π interactions, Table 4. The fingerprint plot delineated into O⋯O contacts, Fig. 6f, has a distribution of points within the rocket-shape with the tip at de + di ∼ 2.9 Å, extending up to 3.0 Å, and is the result of significant short O⋯O contacts summarized in Table 3. The small contribution from C⋯C contacts on the Hirshfeld surfaces of (I) has a negligible effect on the packing.
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5. Database survey
The most closely related structure in the literature is that of the dppe (Ph2PCH2CH2PPh2) analogue, i.e. Ru3(CO)11(dppe)Ru3(CO)11 (Van Calcar et al., 1998). The centrosymmetric molecule presents the same key features as described above for the cluster molecule in (I). There are only a handful of structures whereby two triangular clusters are bridged by a Ph2P(CH2)6PPh2 ligand as in (I). The most closely related of these to the present report is formulated as Fe3(CO)11(Ph2P(CH2)6PPh2)Fe3(CO)11 (Ferguson et al., 1991). The difference in this centrosymmetric molecule, cf. (I), is that there are two μ2-bridging carbonyls connecting the Fe atom bonded to P to one of the other Fe atoms of the triangle; the remaining Fe atom is bound to four terminal carbonyl ligands as in (I).
6. Synthesis and crystallization
The reagents Ru3(CO)12 (200.0 mg, 0.0003 mol) and Ph2P(CH2)6PPh2 (70.0 mg, 0.0002 mol) were mixed in distilled tetrahydrofuran (25 ml). The reaction mixture was treated dropwise with sodium diphenylketyl solution until the colour of the mixture turned from orange to dark-red followed by stirring for 30 min. The reaction was monitored by (TLC). The solvent was removed under reduced pressure and the product was separated by preparative TLC (2:3 dichloromethane:n-hexane) to afford three bands. The second band was characterized as [Ru3(CO)11]2(Ph2P(CH2)6PPh2). Orange laths were grown by solvent/solvent diffusion of CH2Cl2/n-hexane at 283 K. Analysis calculated for C52H32O22P2Ru6·C6H14: C 39.51, H 2.63%; found: C 38.45, H 1.53%. ATR–IR [cm−1]: ν(CO) 2093 (s), 2038 (m), 1957 (br). 1H NMR (CDCl3): δ 7.52–7.41 (m, 20H, Ph), 2.37–2.33 (m, 4H, CH2), 1.26–1.13 (m, 8H, CH2). 31P{1H} (CDCl3): δ 26.83 (s).
7. Refinement
Crystal data, data collection and structure . The carbon-bound H atoms were placed in calculated positions (C—H = 0.95–0.99 Å) and were included in the in the riding model approximation, with Uiso(H) set to 1.2–1.5Ueq(C). The hexane molecule was statistically disordered over two sites and the atomic positions of each were refined independently but, the C—C bond lengths for each component were refined with the distance restraint C—C = 1.50±0.005 Å. The anisotropic displacement parameters were restrained to be almost isotropic and those for matching atoms to be similar. Owing to poor agreement, one reflection, i.e. 54, was omitted from the final cycles of The maximum and minimum residual electron density peaks of 2.43 and 1.32 e Å−3, respectively, were located 1.34 and 0.50 Å from the C22 and Ru6 atoms, respectively.
details are summarized in Table 5
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Supporting information
CCDC reference: 975445
https://doi.org/10.1107/S2056989017014517/hb7713sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017014517/hb7713Isup2.hkl
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).[Ru6(C30H32P2)(CO)22]·C6H14 | F(000) = 3456 |
Mr = 1763.31 | Dx = 1.801 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 14.5323 (4) Å | Cell parameters from 9961 reflections |
b = 23.3731 (6) Å | θ = 2.3–30.5° |
c = 19.1883 (4) Å | µ = 1.48 mm−1 |
β = 93.653 (1)° | T = 100 K |
V = 6504.3 (3) Å3 | Lath, orange |
Z = 4 | 0.61 × 0.48 × 0.09 mm |
Bruker SMART APEXII CCD area-detector diffractometer | 19875 independent reflections |
Radiation source: fine-focus sealed tube | 14916 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 30.6°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −20→20 |
Tmin = 0.466, Tmax = 0.880 | k = −33→24 |
78116 measured reflections | l = −27→27 |
Refinement on F2 | 232 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0336P)2 + 15.8643P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.003 |
19875 reflections | Δρmax = 2.43 e Å−3 |
851 parameters | Δρmin = −1.32 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 | Occ. (<1) | |
Ru1 | 1.00620 (2) | 0.55309 (2) | 0.32612 (2) | 0.01502 (6) | |
Ru2 | 1.03733 (2) | 0.43753 (2) | 0.28780 (2) | 0.01907 (6) | |
Ru3 | 1.02396 (2) | 0.52319 (2) | 0.18283 (2) | 0.01861 (6) | |
Ru4 | 0.44772 (2) | 0.73619 (2) | 0.66392 (2) | 0.01666 (6) | |
Ru5 | 0.43523 (2) | 0.85302 (2) | 0.70390 (2) | 0.02018 (7) | |
Ru6 | 0.45413 (2) | 0.76646 (2) | 0.80837 (2) | 0.02177 (7) | |
P1 | 0.95575 (6) | 0.64831 (4) | 0.33370 (4) | 0.01513 (17) | |
P2 | 0.49391 (6) | 0.64017 (4) | 0.66137 (4) | 0.01546 (17) | |
O1 | 1.19315 (19) | 0.60410 (11) | 0.29484 (15) | 0.0285 (6) | |
O2 | 1.0800 (2) | 0.52828 (12) | 0.47441 (13) | 0.0290 (6) | |
O3 | 0.8119 (2) | 0.50828 (13) | 0.35164 (16) | 0.0366 (7) | |
O4 | 1.22972 (19) | 0.47647 (12) | 0.34408 (15) | 0.0292 (6) | |
O5 | 0.9991 (2) | 0.38167 (12) | 0.42725 (15) | 0.0364 (7) | |
O6 | 0.8389 (2) | 0.41183 (14) | 0.22927 (17) | 0.0411 (8) | |
O7 | 1.1266 (3) | 0.33838 (13) | 0.21263 (18) | 0.0459 (9) | |
O8 | 0.9924 (3) | 0.43736 (14) | 0.06391 (17) | 0.0514 (9) | |
O9 | 1.0394 (2) | 0.62774 (12) | 0.08849 (14) | 0.0345 (7) | |
O10 | 0.8182 (2) | 0.54838 (13) | 0.19471 (16) | 0.0360 (7) | |
O11 | 1.2344 (2) | 0.50741 (15) | 0.18357 (16) | 0.0408 (8) | |
O12 | 0.2536 (2) | 0.69344 (13) | 0.69138 (17) | 0.0369 (7) | |
O13 | 0.3899 (3) | 0.75663 (14) | 0.51156 (15) | 0.0439 (8) | |
O14 | 0.6441 (2) | 0.77508 (14) | 0.63612 (18) | 0.0406 (8) | |
O15 | 0.23144 (19) | 0.82740 (12) | 0.66258 (15) | 0.0322 (7) | |
O16 | 0.6403 (2) | 0.87491 (14) | 0.74621 (18) | 0.0433 (8) | |
O17 | 0.4574 (3) | 0.90584 (15) | 0.56021 (16) | 0.0492 (9) | |
O18 | 0.3902 (2) | 0.95585 (13) | 0.79409 (16) | 0.0361 (7) | |
O19 | 0.2442 (2) | 0.77232 (14) | 0.81832 (17) | 0.0412 (8) | |
O20 | 0.4848 (3) | 0.85964 (15) | 0.91846 (16) | 0.0458 (8) | |
O21 | 0.4486 (3) | 0.66222 (14) | 0.90389 (17) | 0.0498 (9) | |
O22 | 0.6593 (2) | 0.74167 (15) | 0.79230 (17) | 0.0432 (8) | |
C1 | 1.1235 (3) | 0.58298 (15) | 0.30176 (18) | 0.0203 (7) | |
C2 | 1.0482 (3) | 0.53920 (15) | 0.41972 (19) | 0.0207 (7) | |
C3 | 0.8833 (3) | 0.52326 (16) | 0.34013 (19) | 0.0244 (8) | |
C4 | 1.1568 (3) | 0.46479 (15) | 0.32219 (18) | 0.0221 (8) | |
C5 | 1.0143 (3) | 0.40244 (16) | 0.3759 (2) | 0.0264 (8) | |
C6 | 0.9118 (3) | 0.42326 (17) | 0.2501 (2) | 0.0286 (9) | |
C7 | 1.0891 (3) | 0.37462 (17) | 0.2386 (2) | 0.0304 (9) | |
C8 | 1.0043 (3) | 0.46885 (17) | 0.1088 (2) | 0.0319 (9) | |
C9 | 1.0320 (3) | 0.59062 (16) | 0.12569 (19) | 0.0241 (8) | |
C10 | 0.8953 (3) | 0.53866 (17) | 0.1970 (2) | 0.0282 (8) | |
C11 | 1.1571 (3) | 0.51251 (17) | 0.18660 (19) | 0.0265 (8) | |
C12 | 0.3258 (3) | 0.71177 (16) | 0.6847 (2) | 0.0238 (8) | |
C13 | 0.4142 (3) | 0.74812 (16) | 0.5685 (2) | 0.0254 (8) | |
C14 | 0.5708 (3) | 0.76263 (17) | 0.6500 (2) | 0.0278 (8) | |
C15 | 0.3077 (3) | 0.83411 (16) | 0.6796 (2) | 0.0253 (8) | |
C16 | 0.5653 (3) | 0.86347 (17) | 0.7305 (2) | 0.0292 (9) | |
C17 | 0.4476 (3) | 0.88626 (17) | 0.6131 (2) | 0.0298 (9) | |
C18 | 0.4064 (3) | 0.91780 (17) | 0.7609 (2) | 0.0270 (8) | |
C19 | 0.3214 (3) | 0.77160 (17) | 0.8105 (2) | 0.0280 (8) | |
C20 | 0.4736 (3) | 0.82438 (19) | 0.8778 (2) | 0.0317 (9) | |
C21 | 0.4514 (3) | 0.69921 (18) | 0.8662 (2) | 0.0322 (9) | |
C22 | 0.5825 (3) | 0.75258 (19) | 0.7934 (2) | 0.0323 (9) | |
C31 | 0.8391 (2) | 0.65704 (16) | 0.36328 (17) | 0.0198 (7) | |
H31A | 0.8187 | 0.6970 | 0.3544 | 0.024* | |
H31B | 0.7965 | 0.6316 | 0.3354 | 0.024* | |
C32 | 0.8319 (2) | 0.64348 (16) | 0.44098 (17) | 0.0200 (7) | |
H32A | 0.8540 | 0.6040 | 0.4505 | 0.024* | |
H32B | 0.8721 | 0.6700 | 0.4693 | 0.024* | |
C33 | 0.7331 (2) | 0.64916 (16) | 0.46227 (18) | 0.0205 (7) | |
H33A | 0.6943 | 0.6202 | 0.4368 | 0.025* | |
H33B | 0.7093 | 0.6874 | 0.4482 | 0.025* | |
C34 | 0.7245 (2) | 0.64145 (15) | 0.54074 (17) | 0.0187 (7) | |
H34A | 0.7609 | 0.6716 | 0.5662 | 0.022* | |
H34B | 0.7508 | 0.6039 | 0.5553 | 0.022* | |
C35 | 0.6248 (2) | 0.64463 (16) | 0.56047 (18) | 0.0206 (7) | |
H35A | 0.6009 | 0.6837 | 0.5505 | 0.025* | |
H35B | 0.5873 | 0.6176 | 0.5309 | 0.025* | |
C36 | 0.6130 (2) | 0.63060 (15) | 0.63721 (18) | 0.0192 (7) | |
H36A | 0.6541 | 0.6556 | 0.6669 | 0.023* | |
H36B | 0.6320 | 0.5905 | 0.6464 | 0.023* | |
C41 | 1.0235 (2) | 0.69543 (15) | 0.39386 (17) | 0.0178 (7) | |
C42 | 0.9948 (3) | 0.75128 (16) | 0.4016 (2) | 0.0293 (9) | |
H42 | 0.9420 | 0.7649 | 0.3750 | 0.035* | |
C43 | 1.0428 (3) | 0.78771 (18) | 0.4483 (2) | 0.0368 (11) | |
H43 | 1.0233 | 0.8263 | 0.4525 | 0.044* | |
C44 | 1.1183 (3) | 0.76827 (17) | 0.4884 (2) | 0.0305 (9) | |
H44 | 1.1500 | 0.7930 | 0.5211 | 0.037* | |
C45 | 1.1476 (3) | 0.71272 (17) | 0.4806 (2) | 0.0315 (9) | |
H45 | 1.2004 | 0.6992 | 0.5074 | 0.038* | |
C46 | 1.1000 (3) | 0.67627 (15) | 0.4335 (2) | 0.0228 (8) | |
H46 | 1.1204 | 0.6379 | 0.4286 | 0.027* | |
C51 | 0.9510 (2) | 0.68938 (14) | 0.25241 (17) | 0.0173 (7) | |
C52 | 1.0284 (2) | 0.71912 (15) | 0.23321 (18) | 0.0188 (7) | |
H52 | 1.0830 | 0.7191 | 0.2631 | 0.023* | |
C53 | 1.0260 (3) | 0.74909 (16) | 0.17011 (19) | 0.0230 (8) | |
H53 | 1.0791 | 0.7691 | 0.1571 | 0.028* | |
C54 | 0.9466 (3) | 0.74960 (16) | 0.12667 (19) | 0.0224 (8) | |
H54 | 0.9450 | 0.7699 | 0.0837 | 0.027* | |
C55 | 0.8700 (3) | 0.72062 (17) | 0.1459 (2) | 0.0264 (8) | |
H55 | 0.8153 | 0.7214 | 0.1160 | 0.032* | |
C56 | 0.8712 (3) | 0.69031 (16) | 0.20788 (19) | 0.0227 (7) | |
H56 | 0.8177 | 0.6702 | 0.2201 | 0.027* | |
C61 | 0.4299 (3) | 0.59277 (15) | 0.59983 (18) | 0.0195 (7) | |
C62 | 0.4556 (3) | 0.53561 (17) | 0.5971 (2) | 0.0305 (9) | |
H62 | 0.5057 | 0.5221 | 0.6268 | 0.037* | |
C63 | 0.4089 (4) | 0.49828 (18) | 0.5516 (2) | 0.0394 (11) | |
H63 | 0.4276 | 0.4594 | 0.5500 | 0.047* | |
C64 | 0.3367 (4) | 0.51669 (19) | 0.5091 (2) | 0.0433 (12) | |
H64 | 0.3044 | 0.4907 | 0.4784 | 0.052* | |
C65 | 0.3106 (4) | 0.5728 (2) | 0.5107 (3) | 0.0520 (15) | |
H65 | 0.2606 | 0.5859 | 0.4806 | 0.062* | |
C66 | 0.3571 (3) | 0.61109 (18) | 0.5565 (2) | 0.0351 (10) | |
H66 | 0.3382 | 0.6500 | 0.5575 | 0.042* | |
C71 | 0.4879 (3) | 0.59843 (15) | 0.74115 (18) | 0.0205 (7) | |
C72 | 0.5653 (3) | 0.58703 (18) | 0.78570 (19) | 0.0272 (8) | |
H72 | 0.6237 | 0.6023 | 0.7758 | 0.033* | |
C73 | 0.5570 (3) | 0.55321 (19) | 0.8449 (2) | 0.0353 (10) | |
H73 | 0.6099 | 0.5454 | 0.8750 | 0.042* | |
C74 | 0.4733 (3) | 0.53110 (18) | 0.8601 (2) | 0.0370 (11) | |
H74 | 0.4681 | 0.5083 | 0.9006 | 0.044* | |
C75 | 0.3964 (3) | 0.54226 (19) | 0.8160 (2) | 0.0366 (10) | |
H75 | 0.3384 | 0.5268 | 0.8263 | 0.044* | |
C76 | 0.4031 (3) | 0.57533 (18) | 0.7575 (2) | 0.0290 (9) | |
H76 | 0.3496 | 0.5827 | 0.7278 | 0.035* | |
C81 | 0.239 (2) | 0.5739 (10) | 0.972 (2) | 0.118 (7) | 0.5 |
H81A | 0.2892 | 0.6013 | 0.9653 | 0.176* | 0.5 |
H81B | 0.1992 | 0.5885 | 1.0066 | 0.176* | 0.5 |
H81C | 0.2034 | 0.5687 | 0.9270 | 0.176* | 0.5 |
C82 | 0.2797 (11) | 0.5176 (7) | 0.9954 (10) | 0.090 (4) | 0.5 |
H82A | 0.3293 | 0.5065 | 0.9650 | 0.108* | 0.5 |
H82B | 0.3070 | 0.5214 | 1.0438 | 0.108* | 0.5 |
C83 | 0.2068 (10) | 0.4723 (5) | 0.9928 (8) | 0.080 (3) | 0.5 |
H83A | 0.1752 | 0.4716 | 0.9455 | 0.096* | 0.5 |
H83B | 0.1604 | 0.4819 | 1.0265 | 0.096* | 0.5 |
C84 | 0.2456 (14) | 0.4140 (6) | 1.0095 (12) | 0.070 (4) | 0.5 |
H84A | 0.2467 | 0.4148 | 1.0611 | 0.084* | 0.5 |
H84B | 0.1916 | 0.3899 | 0.9954 | 0.084* | 0.5 |
C85 | 0.3221 (10) | 0.3725 (6) | 0.9994 (11) | 0.084 (4) | 0.5 |
H85A | 0.3805 | 0.3878 | 1.0212 | 0.101* | 0.5 |
H85B | 0.3297 | 0.3675 | 0.9488 | 0.101* | 0.5 |
C86 | 0.3012 (11) | 0.3156 (5) | 1.0314 (7) | 0.071 (3) | 0.5 |
H86A | 0.3370 | 0.2856 | 1.0099 | 0.106* | 0.5 |
H86B | 0.2353 | 0.3073 | 1.0236 | 0.106* | 0.5 |
H86C | 0.3178 | 0.3169 | 1.0817 | 0.106* | 0.5 |
C81X | 0.2458 (16) | 0.5839 (7) | 0.9660 (14) | 0.070 (5) | 0.5 |
H81D | 0.2084 | 0.6148 | 0.9839 | 0.105* | 0.5 |
H81E | 0.2325 | 0.5802 | 0.9155 | 0.105* | 0.5 |
H81F | 0.3113 | 0.5926 | 0.9756 | 0.105* | 0.5 |
C82X | 0.2231 (11) | 0.5287 (5) | 1.0012 (7) | 0.079 (4) | 0.5 |
H82C | 0.2327 | 0.5342 | 1.0523 | 0.094* | 0.5 |
H82D | 0.1568 | 0.5206 | 0.9908 | 0.094* | 0.5 |
C83X | 0.2770 (6) | 0.4768 (4) | 0.9814 (4) | 0.0384 (19) | 0.5 |
H83C | 0.3430 | 0.4814 | 0.9963 | 0.046* | 0.5 |
H83D | 0.2712 | 0.4709 | 0.9302 | 0.046* | 0.5 |
C84X | 0.2368 (13) | 0.4269 (4) | 1.0182 (8) | 0.066 (4) | 0.5 |
H84C | 0.2507 | 0.4307 | 1.0692 | 0.079* | 0.5 |
H84D | 0.1689 | 0.4268 | 1.0093 | 0.079* | 0.5 |
C85X | 0.2750 (12) | 0.3718 (5) | 0.9938 (7) | 0.076 (4) | 0.5 |
H85C | 0.3429 | 0.3718 | 1.0025 | 0.091* | 0.5 |
H85D | 0.2608 | 0.3677 | 0.9429 | 0.091* | 0.5 |
C86X | 0.2345 (13) | 0.3222 (7) | 1.0313 (9) | 0.091 (5) | 0.5 |
H86D | 0.2399 | 0.2873 | 1.0035 | 0.137* | 0.5 |
H86E | 0.1693 | 0.3298 | 1.0380 | 0.137* | 0.5 |
H86F | 0.2679 | 0.3171 | 1.0769 | 0.137* | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ru1 | 0.01666 (13) | 0.01424 (12) | 0.01453 (12) | −0.00087 (10) | 0.00393 (10) | −0.00007 (10) |
Ru2 | 0.02584 (15) | 0.01404 (13) | 0.01748 (13) | −0.00170 (11) | 0.00262 (11) | −0.00060 (10) |
Ru3 | 0.02418 (15) | 0.01772 (14) | 0.01422 (12) | −0.00099 (11) | 0.00340 (11) | −0.00010 (10) |
Ru4 | 0.01601 (13) | 0.01746 (13) | 0.01674 (12) | 0.00162 (10) | 0.00289 (10) | −0.00148 (10) |
Ru5 | 0.01922 (14) | 0.01841 (14) | 0.02283 (14) | 0.00088 (11) | 0.00067 (11) | −0.00223 (11) |
Ru6 | 0.02241 (15) | 0.02536 (15) | 0.01751 (13) | 0.00297 (12) | 0.00093 (11) | −0.00131 (11) |
P1 | 0.0144 (4) | 0.0167 (4) | 0.0145 (4) | 0.0015 (3) | 0.0025 (3) | 0.0008 (3) |
P2 | 0.0139 (4) | 0.0185 (4) | 0.0141 (4) | 0.0029 (3) | 0.0019 (3) | −0.0010 (3) |
O1 | 0.0216 (14) | 0.0248 (14) | 0.0404 (16) | −0.0032 (11) | 0.0120 (12) | −0.0031 (12) |
O2 | 0.0314 (16) | 0.0342 (16) | 0.0212 (13) | −0.0039 (12) | 0.0010 (12) | 0.0042 (11) |
O3 | 0.0275 (16) | 0.0411 (18) | 0.0425 (17) | −0.0113 (13) | 0.0120 (14) | −0.0024 (14) |
O4 | 0.0256 (15) | 0.0254 (14) | 0.0358 (15) | 0.0038 (11) | −0.0036 (12) | 0.0049 (12) |
O5 | 0.054 (2) | 0.0303 (16) | 0.0262 (15) | 0.0020 (14) | 0.0114 (14) | 0.0054 (12) |
O6 | 0.0350 (18) | 0.0390 (18) | 0.0484 (19) | −0.0153 (14) | −0.0042 (15) | 0.0028 (15) |
O7 | 0.060 (2) | 0.0301 (17) | 0.049 (2) | 0.0015 (16) | 0.0112 (17) | −0.0189 (15) |
O8 | 0.074 (3) | 0.0392 (19) | 0.0406 (18) | −0.0099 (18) | 0.0030 (18) | −0.0195 (15) |
O9 | 0.049 (2) | 0.0286 (15) | 0.0264 (14) | 0.0004 (14) | 0.0090 (14) | 0.0064 (12) |
O10 | 0.0250 (16) | 0.0443 (18) | 0.0386 (17) | 0.0007 (13) | 0.0007 (13) | 0.0064 (14) |
O11 | 0.0322 (18) | 0.060 (2) | 0.0309 (16) | 0.0070 (16) | 0.0089 (14) | −0.0048 (15) |
O12 | 0.0198 (15) | 0.0328 (16) | 0.059 (2) | −0.0018 (12) | 0.0098 (14) | −0.0007 (14) |
O13 | 0.066 (2) | 0.0432 (19) | 0.0221 (15) | −0.0032 (17) | −0.0021 (15) | 0.0055 (13) |
O14 | 0.0258 (16) | 0.0427 (18) | 0.055 (2) | −0.0092 (14) | 0.0167 (15) | −0.0095 (15) |
O15 | 0.0211 (14) | 0.0338 (16) | 0.0414 (17) | 0.0017 (12) | −0.0020 (13) | −0.0043 (13) |
O16 | 0.0240 (16) | 0.0417 (18) | 0.063 (2) | −0.0034 (14) | −0.0036 (15) | −0.0047 (16) |
O17 | 0.071 (3) | 0.046 (2) | 0.0303 (17) | −0.0151 (18) | 0.0022 (17) | 0.0059 (15) |
O18 | 0.0316 (17) | 0.0302 (16) | 0.0464 (18) | 0.0020 (13) | 0.0010 (14) | −0.0147 (14) |
O19 | 0.0272 (17) | 0.052 (2) | 0.0455 (19) | 0.0074 (15) | 0.0094 (14) | 0.0025 (15) |
O20 | 0.059 (2) | 0.047 (2) | 0.0305 (16) | −0.0028 (17) | −0.0030 (16) | −0.0131 (15) |
O21 | 0.082 (3) | 0.0366 (18) | 0.0331 (17) | 0.0175 (18) | 0.0206 (18) | 0.0088 (14) |
O22 | 0.0216 (16) | 0.060 (2) | 0.0481 (19) | 0.0081 (15) | 0.0000 (14) | 0.0062 (16) |
C1 | 0.0236 (19) | 0.0161 (16) | 0.0219 (17) | 0.0051 (14) | 0.0086 (14) | 0.0005 (13) |
C2 | 0.0226 (18) | 0.0166 (16) | 0.0233 (17) | −0.0038 (14) | 0.0043 (15) | −0.0003 (13) |
C3 | 0.025 (2) | 0.0247 (19) | 0.0236 (18) | −0.0047 (16) | 0.0045 (15) | −0.0038 (15) |
C4 | 0.033 (2) | 0.0137 (16) | 0.0198 (17) | 0.0041 (15) | 0.0036 (15) | 0.0025 (13) |
C5 | 0.036 (2) | 0.0178 (18) | 0.0256 (19) | −0.0004 (16) | 0.0028 (17) | −0.0005 (15) |
C6 | 0.034 (2) | 0.026 (2) | 0.0257 (19) | −0.0055 (17) | 0.0029 (17) | 0.0018 (16) |
C7 | 0.040 (2) | 0.022 (2) | 0.029 (2) | −0.0044 (17) | 0.0042 (18) | −0.0033 (16) |
C8 | 0.045 (3) | 0.024 (2) | 0.027 (2) | −0.0050 (18) | 0.0054 (19) | −0.0004 (16) |
C9 | 0.028 (2) | 0.0231 (19) | 0.0209 (17) | −0.0001 (15) | 0.0024 (15) | −0.0022 (15) |
C10 | 0.029 (2) | 0.030 (2) | 0.0259 (19) | −0.0018 (17) | 0.0042 (17) | 0.0068 (16) |
C11 | 0.033 (2) | 0.031 (2) | 0.0168 (17) | 0.0048 (17) | 0.0058 (16) | −0.0040 (15) |
C12 | 0.0221 (19) | 0.0218 (18) | 0.0279 (19) | 0.0035 (15) | 0.0040 (16) | −0.0027 (15) |
C13 | 0.028 (2) | 0.0223 (18) | 0.0261 (19) | 0.0011 (15) | 0.0039 (16) | −0.0007 (15) |
C14 | 0.023 (2) | 0.030 (2) | 0.031 (2) | −0.0002 (16) | 0.0042 (16) | −0.0046 (16) |
C15 | 0.026 (2) | 0.0242 (19) | 0.0261 (19) | −0.0027 (15) | 0.0028 (16) | −0.0002 (15) |
C16 | 0.026 (2) | 0.027 (2) | 0.035 (2) | −0.0002 (16) | −0.0009 (17) | −0.0044 (17) |
C17 | 0.034 (2) | 0.024 (2) | 0.031 (2) | −0.0045 (17) | −0.0021 (18) | −0.0025 (16) |
C18 | 0.0218 (19) | 0.027 (2) | 0.032 (2) | −0.0015 (16) | −0.0003 (16) | −0.0021 (17) |
C19 | 0.029 (2) | 0.030 (2) | 0.0258 (19) | 0.0023 (17) | 0.0006 (17) | 0.0018 (16) |
C20 | 0.033 (2) | 0.037 (2) | 0.0249 (19) | −0.0011 (18) | −0.0023 (17) | −0.0025 (17) |
C21 | 0.042 (3) | 0.032 (2) | 0.0234 (19) | 0.0124 (19) | 0.0073 (18) | −0.0016 (17) |
C22 | 0.030 (2) | 0.036 (2) | 0.031 (2) | 0.0017 (18) | −0.0011 (18) | 0.0030 (17) |
C31 | 0.0165 (17) | 0.0271 (19) | 0.0161 (16) | 0.0026 (14) | 0.0035 (13) | 0.0013 (13) |
C32 | 0.0168 (17) | 0.0274 (19) | 0.0163 (15) | 0.0020 (14) | 0.0053 (13) | −0.0005 (14) |
C33 | 0.0193 (17) | 0.0253 (18) | 0.0175 (16) | 0.0034 (14) | 0.0058 (14) | 0.0026 (14) |
C34 | 0.0175 (17) | 0.0211 (17) | 0.0181 (16) | 0.0013 (13) | 0.0059 (13) | 0.0008 (13) |
C35 | 0.0186 (17) | 0.0252 (18) | 0.0186 (16) | 0.0027 (14) | 0.0055 (14) | −0.0007 (14) |
C36 | 0.0168 (17) | 0.0226 (18) | 0.0187 (16) | 0.0024 (13) | 0.0042 (13) | −0.0012 (13) |
C41 | 0.0194 (17) | 0.0185 (16) | 0.0158 (15) | −0.0005 (13) | 0.0031 (13) | 0.0011 (13) |
C42 | 0.040 (2) | 0.0215 (19) | 0.0254 (19) | 0.0076 (17) | −0.0045 (18) | −0.0027 (15) |
C43 | 0.054 (3) | 0.020 (2) | 0.035 (2) | 0.0061 (19) | −0.006 (2) | −0.0058 (17) |
C44 | 0.038 (2) | 0.023 (2) | 0.030 (2) | −0.0081 (17) | 0.0004 (18) | −0.0085 (16) |
C45 | 0.024 (2) | 0.029 (2) | 0.040 (2) | −0.0003 (16) | −0.0081 (18) | −0.0049 (17) |
C46 | 0.0200 (18) | 0.0179 (17) | 0.0302 (19) | 0.0019 (14) | −0.0001 (15) | −0.0024 (14) |
C51 | 0.0190 (17) | 0.0146 (15) | 0.0186 (15) | 0.0039 (13) | 0.0047 (13) | −0.0007 (13) |
C52 | 0.0175 (17) | 0.0207 (17) | 0.0184 (16) | −0.0010 (13) | 0.0016 (13) | 0.0015 (13) |
C53 | 0.0207 (18) | 0.0220 (18) | 0.0270 (18) | 0.0010 (14) | 0.0056 (15) | 0.0029 (15) |
C54 | 0.0242 (19) | 0.0231 (18) | 0.0205 (17) | 0.0049 (15) | 0.0051 (15) | 0.0073 (14) |
C55 | 0.0211 (19) | 0.033 (2) | 0.0246 (18) | 0.0023 (16) | −0.0009 (15) | 0.0076 (16) |
C56 | 0.0167 (17) | 0.0284 (19) | 0.0231 (17) | 0.0008 (15) | 0.0019 (14) | 0.0046 (15) |
C61 | 0.0219 (18) | 0.0198 (17) | 0.0172 (16) | −0.0006 (14) | 0.0040 (14) | −0.0013 (13) |
C62 | 0.037 (2) | 0.0216 (19) | 0.032 (2) | 0.0038 (17) | −0.0040 (18) | −0.0050 (16) |
C63 | 0.051 (3) | 0.022 (2) | 0.044 (3) | −0.0002 (19) | 0.002 (2) | −0.0108 (18) |
C64 | 0.054 (3) | 0.032 (2) | 0.043 (3) | −0.013 (2) | −0.012 (2) | −0.011 (2) |
C65 | 0.054 (3) | 0.037 (3) | 0.060 (3) | −0.006 (2) | −0.034 (3) | −0.003 (2) |
C66 | 0.035 (2) | 0.022 (2) | 0.046 (2) | 0.0008 (17) | −0.015 (2) | −0.0016 (18) |
C71 | 0.0217 (18) | 0.0206 (17) | 0.0194 (16) | 0.0045 (14) | 0.0044 (14) | −0.0022 (13) |
C72 | 0.0234 (19) | 0.036 (2) | 0.0227 (18) | 0.0101 (17) | 0.0040 (15) | 0.0029 (16) |
C73 | 0.039 (2) | 0.045 (3) | 0.0228 (19) | 0.020 (2) | 0.0064 (18) | 0.0086 (18) |
C74 | 0.054 (3) | 0.030 (2) | 0.029 (2) | 0.015 (2) | 0.018 (2) | 0.0111 (17) |
C75 | 0.041 (3) | 0.037 (2) | 0.033 (2) | −0.004 (2) | 0.015 (2) | 0.0049 (19) |
C76 | 0.027 (2) | 0.034 (2) | 0.0267 (19) | −0.0002 (17) | 0.0054 (16) | 0.0040 (16) |
C81 | 0.120 (11) | 0.107 (8) | 0.125 (11) | −0.002 (8) | 0.005 (9) | 0.011 (8) |
C82 | 0.087 (6) | 0.094 (5) | 0.089 (6) | −0.004 (4) | 0.008 (4) | 0.008 (4) |
C83 | 0.086 (5) | 0.083 (4) | 0.071 (5) | 0.001 (4) | −0.003 (4) | −0.002 (4) |
C84 | 0.077 (6) | 0.069 (5) | 0.063 (6) | 0.003 (4) | 0.000 (4) | 0.000 (4) |
C85 | 0.089 (6) | 0.082 (5) | 0.082 (6) | −0.007 (4) | 0.008 (5) | −0.007 (4) |
C86 | 0.094 (8) | 0.059 (5) | 0.056 (6) | 0.009 (6) | −0.012 (6) | −0.003 (5) |
C81X | 0.074 (8) | 0.073 (6) | 0.065 (7) | 0.023 (6) | 0.024 (6) | 0.014 (6) |
C82X | 0.083 (9) | 0.091 (7) | 0.066 (7) | 0.045 (7) | 0.036 (7) | 0.047 (7) |
C83X | 0.038 (5) | 0.053 (5) | 0.023 (4) | −0.016 (4) | −0.008 (4) | −0.005 (4) |
C84X | 0.101 (10) | 0.059 (6) | 0.035 (6) | −0.001 (6) | −0.016 (6) | −0.015 (5) |
C85X | 0.123 (13) | 0.063 (6) | 0.044 (6) | 0.007 (8) | 0.017 (8) | −0.018 (5) |
C86X | 0.112 (9) | 0.083 (7) | 0.079 (8) | −0.023 (7) | 0.013 (7) | −0.004 (6) |
Ru1—C2 | 1.888 (4) | C43—C44 | 1.377 (6) |
Ru1—C1 | 1.927 (4) | C43—H43 | 0.9500 |
Ru1—C3 | 1.951 (4) | C44—C45 | 1.377 (6) |
Ru1—P1 | 2.3506 (9) | C44—H44 | 0.9500 |
Ru1—Ru2 | 2.8431 (4) | C45—C46 | 1.393 (5) |
Ru1—Ru3 | 2.8644 (4) | C45—H45 | 0.9500 |
Ru2—C4 | 1.926 (4) | C46—H46 | 0.9500 |
Ru2—C7 | 1.926 (4) | C51—C52 | 1.392 (5) |
Ru2—C5 | 1.927 (4) | C51—C56 | 1.396 (5) |
Ru2—C6 | 1.948 (4) | C52—C53 | 1.397 (5) |
Ru2—Ru3 | 2.8378 (4) | C52—H52 | 0.9500 |
Ru3—C8 | 1.913 (4) | C53—C54 | 1.379 (5) |
Ru3—C9 | 1.928 (4) | C53—H53 | 0.9500 |
Ru3—C10 | 1.941 (4) | C54—C55 | 1.374 (5) |
Ru3—C11 | 1.948 (4) | C54—H54 | 0.9500 |
Ru4—C13 | 1.885 (4) | C55—C56 | 1.384 (5) |
Ru4—C14 | 1.927 (4) | C55—H55 | 0.9500 |
Ru4—C12 | 1.928 (4) | C56—H56 | 0.9500 |
Ru4—P2 | 2.3439 (9) | C61—C66 | 1.372 (5) |
Ru4—Ru5 | 2.8454 (4) | C61—C62 | 1.389 (5) |
Ru4—Ru6 | 2.8564 (4) | C62—C63 | 1.381 (6) |
Ru5—C17 | 1.926 (4) | C62—H62 | 0.9500 |
Ru5—C18 | 1.929 (4) | C63—C64 | 1.356 (7) |
Ru5—C15 | 1.933 (4) | C63—H63 | 0.9500 |
Ru5—C16 | 1.942 (4) | C64—C65 | 1.367 (7) |
Ru5—Ru6 | 2.8490 (4) | C64—H64 | 0.9500 |
Ru6—C20 | 1.908 (4) | C65—C66 | 1.396 (6) |
Ru6—C22 | 1.933 (5) | C65—H65 | 0.9500 |
Ru6—C21 | 1.926 (4) | C66—H66 | 0.9500 |
Ru6—C19 | 1.936 (4) | C71—C72 | 1.395 (5) |
P1—C51 | 1.829 (3) | C71—C76 | 1.399 (5) |
P1—C31 | 1.834 (4) | C72—C73 | 1.396 (5) |
P1—C41 | 1.836 (3) | C72—H72 | 0.9500 |
P2—C71 | 1.822 (4) | C73—C74 | 1.370 (7) |
P2—C61 | 1.830 (4) | C73—H73 | 0.9500 |
P2—C36 | 1.834 (4) | C74—C75 | 1.383 (7) |
O1—C1 | 1.141 (4) | C74—H74 | 0.9500 |
O2—C2 | 1.148 (4) | C75—C76 | 1.370 (6) |
O3—C3 | 1.131 (5) | C75—H75 | 0.9500 |
O4—C4 | 1.148 (5) | C76—H76 | 0.9500 |
O5—C5 | 1.133 (5) | C81—C82 | 1.499 (5) |
O6—C6 | 1.140 (5) | C81—H81A | 0.9800 |
O7—C7 | 1.139 (5) | C81—H81B | 0.9800 |
O8—C8 | 1.138 (5) | C81—H81C | 0.9800 |
O9—C9 | 1.133 (5) | C82—C83 | 1.496 (5) |
O10—C10 | 1.142 (5) | C82—H82A | 0.9900 |
O11—C11 | 1.135 (5) | C82—H82B | 0.9900 |
O12—C12 | 1.148 (5) | C83—C84 | 1.502 (5) |
O13—C13 | 1.144 (5) | C83—H83A | 0.9900 |
O14—C14 | 1.151 (5) | C83—H83B | 0.9900 |
O15—C15 | 1.147 (5) | C84—C85 | 1.497 (5) |
O16—C16 | 1.143 (5) | C84—H84A | 0.9900 |
O17—C17 | 1.131 (5) | C84—H84B | 0.9900 |
O18—C18 | 1.128 (5) | C85—C86 | 1.504 (5) |
O19—C19 | 1.141 (5) | C85—H85A | 0.9900 |
O20—C20 | 1.139 (5) | C85—H85B | 0.9900 |
O21—C21 | 1.130 (5) | C86—H86A | 0.9800 |
O22—C22 | 1.146 (5) | C86—H86B | 0.9800 |
C31—C32 | 1.534 (5) | C86—H86C | 0.9800 |
C31—H31A | 0.9900 | C81X—C82X | 1.503 (5) |
C31—H31B | 0.9900 | C81X—H81D | 0.9800 |
C32—C33 | 1.524 (5) | C81X—H81E | 0.9800 |
C32—H32A | 0.9900 | C81X—H81F | 0.9800 |
C32—H32B | 0.9900 | C82X—C83X | 1.506 (5) |
C33—C34 | 1.529 (5) | C82X—H82C | 0.9900 |
C33—H33A | 0.9900 | C82X—H82D | 0.9900 |
C33—H33B | 0.9900 | C83X—C84X | 1.501 (5) |
C34—C35 | 1.523 (5) | C83X—H83C | 0.9900 |
C34—H34A | 0.9900 | C83X—H83D | 0.9900 |
C34—H34B | 0.9900 | C84X—C85X | 1.489 (5) |
C35—C36 | 1.529 (5) | C84X—H84C | 0.9900 |
C35—H35A | 0.9900 | C84X—H84D | 0.9900 |
C35—H35B | 0.9900 | C85X—C86X | 1.505 (5) |
C36—H36A | 0.9900 | C85X—H85C | 0.9900 |
C36—H36B | 0.9900 | C85X—H85D | 0.9900 |
C41—C42 | 1.381 (5) | C86X—H86D | 0.9800 |
C41—C46 | 1.381 (5) | C86X—H86E | 0.9800 |
C42—C43 | 1.390 (6) | C86X—H86F | 0.9800 |
C42—H42 | 0.9500 | ||
C2—Ru1—C1 | 93.19 (15) | C34—C35—H35B | 108.9 |
C2—Ru1—C3 | 92.90 (16) | H35A—C35—H35B | 107.7 |
C1—Ru1—C3 | 173.85 (15) | C35—C36—P2 | 112.5 (2) |
C2—Ru1—P1 | 100.79 (11) | C35—C36—H36A | 109.1 |
C1—Ru1—P1 | 87.47 (10) | P2—C36—H36A | 109.1 |
C3—Ru1—P1 | 92.18 (12) | C35—C36—H36B | 109.1 |
C2—Ru1—Ru2 | 92.04 (11) | P2—C36—H36B | 109.1 |
C1—Ru1—Ru2 | 97.12 (10) | H36A—C36—H36B | 107.8 |
C3—Ru1—Ru2 | 81.85 (11) | C42—C41—C46 | 119.0 (3) |
P1—Ru1—Ru2 | 166.14 (2) | C42—C41—P1 | 118.8 (3) |
C2—Ru1—Ru3 | 145.87 (11) | C46—C41—P1 | 122.2 (3) |
C1—Ru1—Ru3 | 73.77 (11) | C41—C42—C43 | 120.4 (4) |
C3—Ru1—Ru3 | 100.62 (11) | C41—C42—H42 | 119.8 |
P1—Ru1—Ru3 | 109.75 (2) | C43—C42—H42 | 119.8 |
Ru2—Ru1—Ru3 | 59.630 (9) | C44—C43—C42 | 120.4 (4) |
C4—Ru2—C7 | 92.79 (17) | C44—C43—H43 | 119.8 |
C4—Ru2—C5 | 92.47 (16) | C42—C43—H43 | 119.8 |
C7—Ru2—C5 | 101.53 (17) | C45—C44—C43 | 119.4 (4) |
C4—Ru2—C6 | 170.51 (16) | C45—C44—H44 | 120.3 |
C7—Ru2—C6 | 94.20 (18) | C43—C44—H44 | 120.3 |
C5—Ru2—C6 | 92.43 (17) | C44—C45—C46 | 120.2 (4) |
C4—Ru2—Ru3 | 91.68 (10) | C44—C45—H45 | 119.9 |
C7—Ru2—Ru3 | 101.66 (12) | C46—C45—H45 | 119.9 |
C5—Ru2—Ru3 | 156.20 (12) | C41—C46—C45 | 120.5 (3) |
C6—Ru2—Ru3 | 80.62 (12) | C41—C46—H46 | 119.7 |
C4—Ru2—Ru1 | 75.64 (11) | C45—C46—H46 | 119.7 |
C7—Ru2—Ru1 | 157.76 (13) | C52—C51—C56 | 119.0 (3) |
C5—Ru2—Ru1 | 97.94 (11) | C52—C51—P1 | 120.0 (3) |
C6—Ru2—Ru1 | 95.63 (12) | C56—C51—P1 | 121.0 (3) |
Ru3—Ru2—Ru1 | 60.559 (10) | C51—C52—C53 | 120.3 (3) |
C8—Ru3—C9 | 97.59 (16) | C51—C52—H52 | 119.9 |
C8—Ru3—C10 | 97.34 (19) | C53—C52—H52 | 119.9 |
C9—Ru3—C10 | 91.23 (17) | C54—C53—C52 | 120.1 (3) |
C8—Ru3—C11 | 92.51 (18) | C54—C53—H53 | 119.9 |
C9—Ru3—C11 | 91.69 (17) | C52—C53—H53 | 119.9 |
C10—Ru3—C11 | 169.27 (16) | C55—C54—C53 | 119.7 (3) |
C8—Ru3—Ru2 | 93.38 (12) | C55—C54—H54 | 120.2 |
C9—Ru3—Ru2 | 167.57 (11) | C53—C54—H54 | 120.2 |
C10—Ru3—Ru2 | 93.16 (11) | C54—C55—C56 | 121.1 (4) |
C11—Ru3—Ru2 | 81.97 (12) | C54—C55—H55 | 119.4 |
C8—Ru3—Ru1 | 148.89 (13) | C56—C55—H55 | 119.4 |
C9—Ru3—Ru1 | 111.03 (11) | C55—C56—C51 | 119.9 (3) |
C10—Ru3—Ru1 | 70.94 (12) | C55—C56—H56 | 120.1 |
C11—Ru3—Ru1 | 98.38 (11) | C51—C56—H56 | 120.1 |
Ru2—Ru3—Ru1 | 59.811 (9) | C66—C61—C62 | 118.4 (3) |
C13—Ru4—C14 | 90.16 (18) | C66—C61—P2 | 122.9 (3) |
C13—Ru4—C12 | 93.49 (17) | C62—C61—P2 | 118.7 (3) |
C14—Ru4—C12 | 175.82 (16) | C63—C62—C61 | 120.6 (4) |
C13—Ru4—P2 | 100.25 (12) | C63—C62—H62 | 119.7 |
C14—Ru4—P2 | 91.98 (12) | C61—C62—H62 | 119.7 |
C12—Ru4—P2 | 89.38 (11) | C64—C63—C62 | 120.6 (4) |
C13—Ru4—Ru5 | 95.90 (12) | C64—C63—H63 | 119.7 |
C14—Ru4—Ru5 | 78.78 (12) | C62—C63—H63 | 119.7 |
C12—Ru4—Ru5 | 98.80 (11) | C63—C64—C65 | 119.8 (4) |
P2—Ru4—Ru5 | 161.41 (2) | C63—C64—H64 | 120.1 |
C13—Ru4—Ru6 | 153.66 (12) | C65—C64—H64 | 120.1 |
C14—Ru4—Ru6 | 94.70 (12) | C64—C65—C66 | 120.4 (4) |
C12—Ru4—Ru6 | 81.13 (11) | C64—C65—H65 | 119.8 |
P2—Ru4—Ru6 | 105.42 (2) | C66—C65—H65 | 119.8 |
Ru5—Ru4—Ru6 | 59.956 (10) | C61—C66—C65 | 120.3 (4) |
C17—Ru5—C18 | 103.41 (17) | C61—C66—H66 | 119.9 |
C17—Ru5—C15 | 91.02 (17) | C65—C66—H66 | 119.9 |
C18—Ru5—C15 | 94.36 (17) | C72—C71—C76 | 118.4 (4) |
C17—Ru5—C16 | 92.36 (18) | C72—C71—P2 | 122.5 (3) |
C18—Ru5—C16 | 89.77 (17) | C76—C71—P2 | 119.1 (3) |
C15—Ru5—C16 | 173.92 (17) | C73—C72—C71 | 119.9 (4) |
C17—Ru5—Ru4 | 97.59 (12) | C73—C72—H72 | 120.0 |
C18—Ru5—Ru4 | 157.80 (12) | C71—C72—H72 | 120.0 |
C15—Ru5—Ru4 | 78.01 (12) | C74—C73—C72 | 120.7 (4) |
C16—Ru5—Ru4 | 96.53 (12) | C74—C73—H73 | 119.6 |
C17—Ru5—Ru6 | 155.84 (13) | C72—C73—H73 | 119.6 |
C18—Ru5—Ru6 | 99.99 (12) | C73—C74—C75 | 119.5 (4) |
C15—Ru5—Ru6 | 93.16 (11) | C73—C74—H74 | 120.3 |
C16—Ru5—Ru6 | 81.72 (13) | C75—C74—H74 | 120.3 |
Ru4—Ru5—Ru6 | 60.213 (10) | C76—C75—C74 | 120.7 (4) |
C20—Ru6—C22 | 96.98 (19) | C76—C75—H75 | 119.6 |
C20—Ru6—C21 | 100.63 (18) | C74—C75—H75 | 119.6 |
C22—Ru6—C21 | 90.24 (19) | C75—C76—C71 | 120.7 (4) |
C20—Ru6—C19 | 92.56 (18) | C75—C76—H76 | 119.6 |
C22—Ru6—C19 | 170.42 (18) | C71—C76—H76 | 119.6 |
C21—Ru6—C19 | 88.92 (18) | C82—C81—H81A | 109.5 |
C20—Ru6—Ru5 | 89.47 (13) | C82—C81—H81B | 109.5 |
C22—Ru6—Ru5 | 93.73 (13) | H81A—C81—H81B | 109.5 |
C21—Ru6—Ru5 | 168.62 (13) | C82—C81—H81C | 109.5 |
C19—Ru6—Ru5 | 85.39 (12) | H81A—C81—H81C | 109.5 |
C20—Ru6—Ru4 | 147.96 (13) | H81B—C81—H81C | 109.5 |
C22—Ru6—Ru4 | 77.65 (12) | C83—C82—C81 | 110.4 (17) |
C21—Ru6—Ru4 | 110.86 (12) | C83—C82—H82A | 109.6 |
C19—Ru6—Ru4 | 93.74 (12) | C81—C82—H82A | 109.6 |
Ru5—Ru6—Ru4 | 59.831 (10) | C83—C82—H82B | 109.6 |
C51—P1—C31 | 102.71 (16) | C81—C82—H82B | 109.6 |
C51—P1—C41 | 102.18 (16) | H82A—C82—H82B | 108.1 |
C31—P1—C41 | 102.02 (16) | C82—C83—C84 | 112.4 (15) |
C51—P1—Ru1 | 116.05 (11) | C82—C83—H83A | 109.1 |
C31—P1—Ru1 | 115.00 (12) | C84—C83—H83A | 109.1 |
C41—P1—Ru1 | 116.74 (11) | C82—C83—H83B | 109.1 |
C71—P2—C61 | 99.68 (16) | C84—C83—H83B | 109.1 |
C71—P2—C36 | 104.11 (16) | H83A—C83—H83B | 107.9 |
C61—P2—C36 | 102.27 (16) | C85—C84—C83 | 146.3 (16) |
C71—P2—Ru4 | 117.77 (12) | C85—C84—H84A | 100.3 |
C61—P2—Ru4 | 117.29 (12) | C83—C84—H84A | 100.3 |
C36—P2—Ru4 | 113.47 (12) | C85—C84—H84B | 100.3 |
O1—C1—Ru1 | 171.7 (3) | C83—C84—H84B | 100.3 |
O2—C2—Ru1 | 174.1 (3) | H84A—C84—H84B | 104.2 |
O3—C3—Ru1 | 175.7 (3) | C84—C85—C86 | 110.4 (11) |
O4—C4—Ru2 | 174.4 (3) | C84—C85—H85A | 109.6 |
O5—C5—Ru2 | 178.7 (4) | C86—C85—H85A | 109.6 |
O6—C6—Ru2 | 176.2 (4) | C84—C85—H85B | 109.6 |
O7—C7—Ru2 | 174.2 (4) | C86—C85—H85B | 109.6 |
O8—C8—Ru3 | 178.7 (4) | H85A—C85—H85B | 108.1 |
O9—C9—Ru3 | 174.9 (3) | C85—C86—H86A | 109.5 |
O10—C10—Ru3 | 169.7 (4) | C85—C86—H86B | 109.5 |
O11—C11—Ru3 | 174.8 (3) | H86A—C86—H86B | 109.5 |
O12—C12—Ru4 | 172.9 (3) | C85—C86—H86C | 109.5 |
O13—C13—Ru4 | 176.6 (4) | H86A—C86—H86C | 109.5 |
O14—C14—Ru4 | 173.4 (4) | H86B—C86—H86C | 109.5 |
O15—C15—Ru5 | 174.1 (3) | C82X—C81X—H81D | 109.5 |
O16—C16—Ru5 | 173.7 (4) | C82X—C81X—H81E | 109.5 |
O17—C17—Ru5 | 178.1 (4) | H81D—C81X—H81E | 109.5 |
O18—C18—Ru5 | 179.4 (4) | C82X—C81X—H81F | 109.5 |
O19—C19—Ru6 | 173.2 (4) | H81D—C81X—H81F | 109.5 |
O20—C20—Ru6 | 178.9 (4) | H81E—C81X—H81F | 109.5 |
O21—C21—Ru6 | 175.2 (4) | C83X—C82X—C81X | 116.5 (12) |
O22—C22—Ru6 | 171.9 (4) | C83X—C82X—H82C | 108.2 |
C32—C31—P1 | 113.5 (2) | C81X—C82X—H82C | 108.2 |
C32—C31—H31A | 108.9 | C83X—C82X—H82D | 108.2 |
P1—C31—H31A | 108.9 | C81X—C82X—H82D | 108.2 |
C32—C31—H31B | 108.9 | H82C—C82X—H82D | 107.3 |
P1—C31—H31B | 108.9 | C82X—C83X—C84X | 106.5 (9) |
H31A—C31—H31B | 107.7 | C82X—C83X—H83C | 110.4 |
C33—C32—C31 | 111.5 (3) | C84X—C83X—H83C | 110.4 |
C33—C32—H32A | 109.3 | C82X—C83X—H83D | 110.4 |
C31—C32—H32A | 109.3 | C84X—C83X—H83D | 110.4 |
C33—C32—H32B | 109.3 | H83C—C83X—H83D | 108.6 |
C31—C32—H32B | 109.3 | C85X—C84X—C83X | 111.0 (10) |
H32A—C32—H32B | 108.0 | C85X—C84X—H84C | 109.4 |
C32—C33—C34 | 113.0 (3) | C83X—C84X—H84C | 109.4 |
C32—C33—H33A | 109.0 | C85X—C84X—H84D | 109.4 |
C34—C33—H33A | 109.0 | C83X—C84X—H84D | 109.4 |
C32—C33—H33B | 109.0 | H84C—C84X—H84D | 108.0 |
C34—C33—H33B | 109.0 | C84X—C85X—C86X | 110.5 (12) |
H33A—C33—H33B | 107.8 | C84X—C85X—H85C | 109.6 |
C33—C34—C35 | 112.2 (3) | C86X—C85X—H85C | 109.6 |
C33—C34—H34A | 109.2 | C84X—C85X—H85D | 109.6 |
C35—C34—H34A | 109.2 | C86X—C85X—H85D | 109.6 |
C33—C34—H34B | 109.2 | H85C—C85X—H85D | 108.1 |
C35—C34—H34B | 109.2 | C85X—C86X—H86D | 109.5 |
H34A—C34—H34B | 107.9 | C85X—C86X—H86E | 109.5 |
C36—C35—C34 | 113.3 (3) | H86D—C86X—H86E | 109.5 |
C36—C35—H35A | 108.9 | C85X—C86X—H86F | 109.5 |
C34—C35—H35A | 108.9 | H86D—C86X—H86F | 109.5 |
C36—C35—H35B | 108.9 | H86E—C86X—H86F | 109.5 |
C51—P1—C31—C32 | −161.5 (3) | C52—C51—C56—C55 | −0.1 (5) |
C41—P1—C31—C32 | −55.9 (3) | P1—C51—C56—C55 | −178.5 (3) |
Ru1—P1—C31—C32 | 71.5 (3) | C71—P2—C61—C66 | 127.9 (4) |
P1—C31—C32—C33 | −177.8 (3) | C36—P2—C61—C66 | −125.2 (4) |
C31—C32—C33—C34 | −174.6 (3) | Ru4—P2—C61—C66 | −0.4 (4) |
C32—C33—C34—C35 | −177.4 (3) | C71—P2—C61—C62 | −51.7 (3) |
C33—C34—C35—C36 | 173.7 (3) | C36—P2—C61—C62 | 55.2 (3) |
C34—C35—C36—P2 | 175.5 (2) | Ru4—P2—C61—C62 | −180.0 (3) |
C71—P2—C36—C35 | 160.6 (3) | C66—C61—C62—C63 | 0.2 (6) |
C61—P2—C36—C35 | 57.2 (3) | P2—C61—C62—C63 | 179.8 (4) |
Ru4—P2—C36—C35 | −70.1 (3) | C61—C62—C63—C64 | −0.5 (7) |
C51—P1—C41—C42 | 54.3 (3) | C62—C63—C64—C65 | 0.9 (8) |
C31—P1—C41—C42 | −51.8 (3) | C63—C64—C65—C66 | −0.9 (9) |
Ru1—P1—C41—C42 | −178.0 (3) | C62—C61—C66—C65 | −0.2 (7) |
C51—P1—C41—C46 | −128.3 (3) | P2—C61—C66—C65 | −179.8 (4) |
C31—P1—C41—C46 | 125.7 (3) | C64—C65—C66—C61 | 0.5 (8) |
Ru1—P1—C41—C46 | −0.6 (4) | C61—P2—C71—C72 | 131.1 (3) |
C46—C41—C42—C43 | 0.5 (6) | C36—P2—C71—C72 | 25.7 (4) |
P1—C41—C42—C43 | 178.0 (3) | Ru4—P2—C71—C72 | −100.9 (3) |
C41—C42—C43—C44 | −1.4 (7) | C61—P2—C71—C76 | −46.9 (3) |
C42—C43—C44—C45 | 1.7 (7) | C36—P2—C71—C76 | −152.2 (3) |
C43—C44—C45—C46 | −1.2 (7) | Ru4—P2—C71—C76 | 81.1 (3) |
C42—C41—C46—C45 | 0.0 (6) | C76—C71—C72—C73 | 0.1 (6) |
P1—C41—C46—C45 | −177.5 (3) | P2—C71—C72—C73 | −177.9 (3) |
C44—C45—C46—C41 | 0.4 (6) | C71—C72—C73—C74 | −0.2 (6) |
C31—P1—C51—C52 | 145.4 (3) | C72—C73—C74—C75 | 0.3 (7) |
C41—P1—C51—C52 | 39.9 (3) | C73—C74—C75—C76 | −0.3 (7) |
Ru1—P1—C51—C52 | −88.3 (3) | C74—C75—C76—C71 | 0.2 (7) |
C31—P1—C51—C56 | −36.3 (3) | C72—C71—C76—C75 | −0.1 (6) |
C41—P1—C51—C56 | −141.8 (3) | P2—C71—C76—C75 | 178.0 (3) |
Ru1—P1—C51—C56 | 90.1 (3) | C81—C82—C83—C84 | 174 (2) |
C56—C51—C52—C53 | −0.4 (5) | C82—C83—C84—C85 | −42 (4) |
P1—C51—C52—C53 | 178.0 (3) | C83—C84—C85—C86 | −174 (3) |
C51—C52—C53—C54 | 0.4 (5) | C81X—C82X—C83X—C84X | −175.3 (17) |
C52—C53—C54—C55 | 0.1 (6) | C82X—C83X—C84X—C85X | 171.2 (13) |
C53—C54—C55—C56 | −0.7 (6) | C83X—C84X—C85X—C86X | 179.7 (14) |
C54—C55—C56—C51 | 0.7 (6) |
Hydrogen-bond geometry (Å, °) for (I). Cg1 and Cg2 the ring centroids of the C41–C46 and C51–C56 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C35—H35B···O20i | 0.99 | 2.60 | 3.297 (5) | 128 |
C36—H36B···O4ii | 0.99 | 2.54 | 3.393 (4) | 144 |
C42—H42···O7iii | 0.95 | 2.56 | 3.401 (5) | 148 |
C52—H52···O19iv | 0.95 | 2.52 | 3.448 (4) | 167 |
C55—H55···O14i | 0.95 | 2.54 | 3.278 (5) | 134 |
C62—H62···O18v | 0.95 | 2.59 | 3.501 (5) | 161 |
C82X—H82D···O8vi | 0.99 | 2.55 | 3.391 (16) | 143 |
C81X—H81F···O17vii | 0.98 | 2.59 | 3.48 (2) | 150 |
C82X—H82C···O11viii | 0.99 | 2.59 | 3.528 (14) | 157 |
Symmetry codes: (i) x, −y+1/2, z−3/2; (ii) −x+2, −y+1, −z+1; (iii) −x+2, y+1/2, −z+1/2; (iv) x+1, −y+1/2, z−3/2; (v) −x+1, y−1/2, −z+3/2; (vi) −x+1, −y+1, −z+1; (vii) x, −y+1/2, z−1/2; (viii) x−1, y, z+1. |
Contact | Distance | Symmetry operation |
O1···C15 | 3.196 (5) | 1 + x, 1 1/2 - y, - 1/2 + z |
O1···O19 | 3.009 (4) | 1 + x, 1 1/2 - y, - 1/2 + z |
O2···O2 | 2.900 (4) | 2 - x, 1 - y, 1 - z |
O4···O18 | 3.024 (4) | 1 + x, 1 1/2 - y, - 1/2 + z |
O7···H42 | 2.62 | 2 - x, - 1/2 + y, 1/2 - z |
O8···H43 | 2.62 | 2 - x, - 1/2 + y, 1/2 - z |
O13···O21 | 2.970 (5) | x, 1 1/2 - y, - 1/2 + z |
O13···C21 | 3.156 (5) | x, 1 1/2 - y, - 1/2 + z |
C8···H83B | 2.86 | 1 + x, y, -1 + z |
C10···H83A | 2.87 | 1 - x, 1 - y, 1 - z |
H35B···H63 | 2.38 | 1 - x, 1 - y, 1 - z |
H55···H86D | 2.39 | 1 - x, 1 - y, 1 - z |
H73···H84C | 2.30 | 1 - x, 1 - y, 2 - z |
Percentage contribution | ||
Contact | (I) without hexane | (I) |
O···H/H···O | 52.8 | 53.4 |
H···H | 18.3 | 19.9 |
O···O | 11.8 | 10.3 |
C···O/O···C | 8.9 | 7.8 |
C···H/H···C | 6.9 | 7.4 |
C···C | 1.3 | 1.2 |
C | O | Cg | O···Cg | C—O···Cg | C···Cg | Symmetry operation |
C3 | O3 | Cg3 | 3.756 (4) | 161.0 (3) | 4.839 (5) | 1 - x, 1 - y, 1 - z |
C7 | O7 | Cg2 | 3.564 (4) | 100.1 (3) | 3.928 (4) | 2 - x, - 1/2 + y, 1/2 - z |
C9 | O9 | Cg2 | 3.228 (3) | 94.2 (2) | 3.499 (4) | x, y, z |
C18 | O18 | Cg4 | 3.707 (3) | 97.6 (3) | 4.015 (5) | 1 - x, 1/2 + y, 1 1/2 - z |
C19 | O19 | Cg1 | 3.554 (3) | 146.0 (3) | 4.546 (5) | -1 + x, 1 1/2 - y, 1/2 + z |
C20 | O20 | Cg3 | 3.671 (4) | 146.6 (4) | 4.664 (4) | x, 1 1/2 - y, 1/2 + z |
C21 | O21 | Cg4 | 3.074 (4) | 98.3 (3) | 3.424 (4) | x, y, z |
Summary of short inter-atomic C≡O···π contacts (Å, °) in (I). Cg1–Cg4 the ring centroids of the C41–C46, C51–C56, C61–C66 and C71–C76 rings, respectively. |
Footnotes
‡Additional correspondence author: omarsa@usm.my
Acknowledgements
OBS wishes to thank Universiti Sains Malaysia (USM) for the Research University Grant No. 1001/PJJAUH/8011002. SSS also thanks Universiti Teknologi Mara (UiTM) for a PhD sponsorship. The X-ray Crystallography Unit, School of Physics (USM), is thanked for the data collection.
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