research communications
Crystal structures of phosphine-supported (η5-cyclopentadienyl)molybdenum(II) propionyl complexes
aCarleton College, 1 N College St, Northfield, MN 55057, USA
*Correspondence e-mail: mwhited@carleton.edu
Three cyclopentadienylmolybdenum(II) propionyl complexes featuring triarylphosphine ligands with different para substituents, namely, dicarbonyl(η5-cyclopentadienyl)propionyl(triphenylphosphane-κP)molybdenum(II), [Mo(C5H5)(C3H5O)(C18H15P)(CO)2], (1), dicarbonyl(η5-cyclopentadienyl)propionyl[tris(4-fluorophenyl)phosphane-κP]molybdenum(II), [Mo(C5H5)(C3H5O)(C18H12F3P)(CO)2], (2), and dicarbonyl(η5-cyclopentadienyl)propionyl[tris(4-methoxyphenyl)phosphane-κP]molybdenum(II) dichloromethane solvate, [Mo(C5H5)(C3H5O)(C21H21O3P)(CO)2]·CH2Cl2, (3), have been prepared from the corresponding ethyl complexes via phosphine-induced migratory insertion. These complexes exhibit four-legged piano-stool geometries with molecular structures quite similar to each other and to related acetyl complexes. The extended structures of the three complexes differ somewhat, with the para substituent of the triarylphosphine of (2) (fluoro) or (3) (methoxy) engaging in non-classical C—H⋯F or C—H⋯O hydrogen-bonding interactions. The structure of (3) exhibits modest disorder in the position of one Cl atom of the dichloromethane solvent, which was modeled with two sites showing approximately equivalent occupancies [0.532 (15) and 0.478 (15)].
Keywords: crystal structure; phosphine; propionyl; piano-stool complex.
1. Chemical context
Cyclopentadienylmolybdenum(II) complexes featuring carbonyl ligands commonly adopt `four-legged piano-stool' geometries (Barnett & Slocum, 1972; Kubacek et al., 1982), and those featuring alkyl co-ligands readily undergo migratory insertion to afford MoII acyl complexes upon exposure to (Barnett & Treichel, 1967; Butler et al., 1967). The effect of changing phosphine substituents on this reaction is well established, with bulkier enhancing the rates of subsequent deinsertion from the acyl complexes, a net decarbonylation (Barnett, 1969; Barnett & Pollmann, 1974). Most complexes of the type Mo(C5H5)(CO)2(PR3)(COR) feature acetyl ligands, though there are limited examples of other acyl complexes that have been structurally characterized (Michelini-Rodriguez et al., 1993; Murshid et al., 2016).
We have previously reported synthetic details and solid-state structures for a number of MoII acetyl complexes of the type described above (Whited & Hofmeister, 2014; Whited et al., 2012, 2014), examining the effect of changing phosphine substituents on local and supramolecular features. Consistent with reports on decarbonylation reactivity, we have found that the primary impact on molecular structure is observed in the Mo—P bond lengths, with some changes in P—Mo—C bond angles as a result of sterics. Use of tri(2-furyl)phosphine, which features heteroatoms as potential hydrogen-bond acceptors, leads to an unusual structure with the acetyl oriented down, away from the cyclopentadienyl ring rather than up toward it as observed in other cases (Whited et al., 2013), and a similar effect was observed by incorporation of a Lewis-acidic manganese unit to interact with the acetyl ligand (Adatia et al., 1986). Recent use of other potentially hydrogen-bonding phosphine ligands did not lead to the same solid-state effect (Anstey et al., 2020).
We were interested in extending earlier studies to higher-order II propionyl complexes derived from an ethyl precursor and supported by triarylphosphine ligands differing in their para substitution (–H, –F, and –OCH3). Although substitution of phosphine with electron-withdrawing or -donating groups minimally affects local structure, the supramolecular organization is substantially affected by non-classical hydrogen-bonding to the fluoro and methoxy groups in (2) and (3), respectively.
at molybdenum, and in this report we describe the synthesis and solid-state structures of related Mo2. Structural commentary
The molecular structures of (1), (2), and (3) are illustrated in Figs. 1–3. All complexes exhibit an overall structure common for CpMo acetyl complexes of this type, with trans-disposed carbonyl ligands. As previously observed for most related acetyl complexes, the acyl C=O points up toward the Cp ring. In the case of (1), this phenomenon could be rationalized by presence of short C4—H4A⋯O1 (2.672 Å) and C4—H4B⋯O2 (2.639 Å) contacts involving the carbonyl ligands that are enabled when the acyl points up. However, the variation of the Mo1—C3—C4—C5 torsion angle across the series [175.31 (12)° for (1), 172.61 (18)° for (2), and 137.17 (10)° for (3)] argues against the general importance of such an interaction.
Selected geometric parameters for (1), (2), and (3) are presented in Tables 1–3. Complex (2) crystallized with two nearly equivalent molecules in the so geometric parameters are presented for both. In general, the three complexes are nearly identical, as might be expected based on the dominant role of sterics in determining structure and the fact that the steric profiles of the three triarylphosphine ligands are identical. The Mo—P bond length in (2) [2.4692 (4) Å (avg)] is slightly shorter than in (1) or (3) [2.4816 (4) and 2.4745 (3) Å, respectively], which may be related to stronger π-backbonding to the tris(4-fluorophenyl)phosphine ligand. Stronger backbonding is supported by the observation by infrared spectroscopy of slightly higher-energy carbonyl stretching vibrations for (2) [ν(CO)avg = 1897 cm−1] compared with (1) and (3) [ν(CO)avg = 1893 cm−1 for (1), 1890 cm−1 for (3)]. Geometric parameters for all complexes are quite similar to those for the related triphenylphosphine-supported CpMo acetyl complex (Churchill & Fennessey, 1968).
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3. Supramolecular features
In spite of the similarities among (1), (2), and (3) in their molecular structures, the para substituent of the triarylphosphine ligand [H for (1), F for (2), OCH3 for (3)] plays an important role in determining the extended structure. The extended structure of (1) is dominated by non-classical C—H⋯O interactions involving its carbonyl ligands. A short C—H⋯O interaction between O2 and H12 of a phenyl ring (2.36 Å) joins molecules of (1) into centrosymmetrical dimers that are organized into chains along [010] by intermolecular C15—H15⋯Cg4 (2.952 Å, where Cg4 represents the centroid of the C23–C28 ring) and intramolecular O2⋯Cg4 (3.295 Å) interactions (Fig. 4, Table 4). These chains are linked into sheets parallel to (10) through another set of non-classical C—H⋯O interactions (2.60 Å) between O1 of the other carbonyl ligand and H6 from a cyclopentadienyl ligand (Fig. 5).
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The tris(4-fluorophenyl)phosphine-supported derivative (2) features two nearly equivalent molecules in the exhibiting a non-classical C—H⋯O interaction between O6 of a propionyl ligand and H15 from a phenyl ring (2.59 Å) and a C—H⋯F close contact between F3 and H53 (2.60 Å). These pairs of molecules are joined into chains along [001] by C34—H34⋯O1 hydrogen bonding (2.38 Å, Fig. 6, Table 5)). The molecules are further organized parallel to (010) by C—H⋯F close contacts between F4 and H49 (2.55 Å) and C—H⋯O interactions between O3 and H55 (2.53 Å) (Fig. 7), then further joined along [010] by C—F⋯π interactions (F5⋯Cg4 = 3.17 Å, where Cg4 represents the centroid of the C23–C38 ring).
Like complex (1), complex (3) is joined into centrosymmetrical dimers by a C—H⋯O interaction involving a carbonyl ligand (C8—H8⋯O1, Table 6), and these are linked into chains along [110] through an additional C—H⋯O interaction between the propionyl oxygen and a cyclopentadienyl ligand (Fig. 8). Additional C31—H31B⋯O5 interactions along [110], involving a methoxy group from the phosphine ligand, join the molecules into a network parallel to (001). This further set of interactions involving methoxy groups, as well as important close contacts involving the dichloromethane solvent, are depicted in Fig. 9.
4. Database survey
The current version of the Cambridge Structural Database (Version 5.41, updated August 2020; Groom et al., 2016) has fourteen entries corresponding to molybdenum acyl complexes of the general form Mo(C5H5)(CO)2(PR3)(COR). The trans-dicarbonyl structure, as observed for (1)–(3), is preferred except in cases where the phosphine and acyl ligands are covalently linked, forcing them to be cis (Adams et al., 1991; Mercier et al., 1993; Yan et al., 2009).
5. Synthesis and crystallization
CpMo(CO)3(CH2CH3). This compound was prepared by modification of the method used of Gladysz et al. (1979), as previously reported by Whited & Hofmeister (2014) and Anstey et al. (2020). In a 20 ml scintillation vial equipped with a flea-sized stir bar, [CpMo(CO)3]2 (0.1908 g, 0.39 mmol) was dissolved in THF (10 ml). Sodium triethylborohydride (0.87 mL of 1.0 M solution in THF, 0.87 mmol) was added dropwise by syringe with vigorous stirring, leading to an immediate color change from purple to green–yellow with evolution of H2 gas. The reaction was allowed to proceed with stirring for 20 min, and an excess of iodoethane (0.098 ml, 1.2 mmol) was added dropwise with stirring and the reaction was allowed to proceed for 6 h. Volatiles were removed in vacuo to afford a yellow–brown film that was stored at 238 K for 1 week. The solid was extracted with pentane (4 × 10 ml) and filtered through a 1 cm pad of activated alumina to afford a yellow solution, and removal of solvent in vacuo afforded CpMo(CO)3(CH2CH3) as a pure yellow powder (0.131 g, 61%). 1H NMR (400 MHz, CDCl3): δ 5.28 (s, 5H, Cp ring), 1.72 (q, 3JHH = 7.4 Hz, 2H, –CH2CH3), 1.45 (t, 3JHH = 7.4 Hz, 3H, –CH2CH3). 13C{1H} NMR (101 MHz, CDCl3): δ 239.9 (Mo—CO), 227.8 (Mo—CO), 93.0 (Cp ring), 20.4 (Mo—CH2CH3) −3.7 (Mo—CH2CH3). IR (CH2Cl2, NaCl, cm−1) ν(CO): 2015, 1921 (split).
CpMo(CO)2(PPh3)(COCH2CH3) (1). In an inert-atmosphere CpMo(CO)3(CH2CH3) (0.0803 g, 0.293 mmol) and triphenylphosphine (0.115 g, 0.440 mmol, 1.5 equiv) were dissolved in acetonitrile (5 ml) in a 20 ml scintillation vial equipped with a flea-sized stir bar. The mixture was stirred for 1 week, during which time a bright-yellow precipitate formed. The yellow solid was isolated by filtration and washed with pentane (2 × 5 ml), then dried in vacuo to afford pure 1. Yellow crystals of 1 suitable for X-ray diffraction were obtained from a concentrated dichloromethane solution by vapor cross diffusion with pentane at 238 K. 1H NMR (400 MHz, CDCl3): δ 7.50–7.30 (m, 15H, PPh3), 5.00 (d, J = 1.2 Hz, 5H, C5H5), 3.03 (q, 3JHH = 7.2 Hz, 2H, C(O)CH2CH3), 0.90 (t, 3JHH = 7.2 Hz, 3H, C(O)CH2CH3). 13C{1H} NMR (101 MHz, CDCl3): δ 267.7 (d, 2JCP = 11 Hz, Mo—COEt), 238.8 (d, 2JCP = 24 Hz, Mo—CO), 135.7 (d, 1JCP = 44 Hz, ipso-C of PPh3), 133.2 (d, 2JCP = 11 Hz, ortho-C of PPh3), 130.5 (d, 4JCP = 2 Hz, para-C of PPh3), 128.6 (d, 3JCP = 11 Hz, meta-C of PPh3), 96.7 (Cp ring), 58.1 (Mo—COCH2CH3), 10.1 (Mo—COCH2CH3). 31P{1H} NMR (162 MHz, CDCl3): δ 68.4 (s). IR (CH2Cl2, NaCl, cm−1) ν(CO): 1935, 1851, 1614 (acetyl).
CpMo(CO)2(P(4-FPh)3)(COCH2CH3) (2). In an inert-atmosphere CpMo(CO)3(CH2CH3) (0.0997 g, 0.36 mmol) and tris(4-fluorophenyl)phosphine (0.17 g, 0.55 mmol, 1.5 equiv) were dissolved in acetonitrile (5 ml) in a 20 ml scintillation vial equipped with a flea-sized stir bar. The mixture was stirred for 1 week, causing a color change to orange, but without formation of any precipitate. Solvent was removed in vacuo, causing precipitation of a yellow solid that was isolated by filtration and washed with pentane (2 × 3 ml) to afford the desired product 2 (0.12 g, 56%). Yellow crystals of 2 suitable for X-ray diffraction were obtained from a concentrated dichloromethane solution by vapor cross diffusion with pentane at 238 K. 1H NMR (400 MHz, CDCl3): δ 7.41–7.30 (br m, 6H, ortho-C–H of phosphine), 7.14 (td, 3JHH ≃ 3JHF = 8.6 Hz, 4JHP = 1.5 Hz, 6H, meta-C—H of phosphine), 4.90 (d, J = 1.2 Hz, 5H, C5H5), 2.99 (q, 3JHH = 7.2 Hz, 2H, C(O)CH2CH3), 0.90 (t, 3JHH = 7.2 Hz, 3H, C(O)CH2CH3). 13C{1H} NMR (101 MHz, CDCl3): δ 265.4 (d, 2JCP = 11 Hz, Mo—COEt), 238.2 (d, 2JCP = 24 Hz, Mo—CO), 164.0 (dd, 1JCF = 253 Hz, 4JCP = 2 Hz, C—F of phosphine), 135.0 (dd, 2JCP = 13 Hz, 3JCF = 8 Hz, ortho-C of phosphine), 131.3 (dd, 1JCP = 46 Hz, 4JCF = 4 Hz, ipso-C of phosphine), 116.0 (dd, 2JCF = 21 Hz, 3JCP = 11 Hz, meta-C of phosphine), 96.5 (Cp ring), 58.2 (Mo—COCH2CH3), 10.9 (Mo—COCH2CH3). 31P{1H} NMR (162 MHz, CDCl3): δ 68.5 (s). IR (CH2Cl2, NaCl, cm−1) ν(CO): 1938, 1856, 1620 (acetyl).
CpMo(CO)2(P(4-MeOPh)3)(COCH2CH3) (3). In an inert-atmosphere CpMo(CO)3(CH2CH3) (0.113 g, 0.41 mmol) and tris(4-methoxyphenyl)phosphine (0.218 g, 0.61 mmol, 1.5 equiv) were dissolved in acetonitrile (5 ml) in a 20 nml scintillation vial equipped with a flea-sized stir bar. The mixture was stirred for 1 week, causing precipitation of 3 as a pure yellow powder that was isolated by filtration. Crystals of 3 suitable for X-ray diffraction were obtained from a concentrated dichloromethane solution by vapor cross diffusion with pentane at 238 K. 1H NMR (400 MHz, CDCl3): δ 7.37–7.23 (br m, 6H, ortho-C–H of phosphine), 7.14 (dd, 3JHH = 8.8 Hz, 4JHP = 1.7 Hz, meta-C—H of phosphine), 4.99 (d, J = 1.2 Hz, 5H, C5H5), 3.03 (q, 3JHH = 7.2 Hz, 2H, C(O)CH2CH3), 0.89 (t, 3JHH = 7.2 Hz, 3H, C(O)CH2CH3). 13C{1H} NMR (101 MHz, CDCl3): δ 268.6 (d, 2JCP = 11 Hz, Mo–COEt), 239.2 (d, 2JCP = 24 Hz, Mo—CO), 161.1 (C—OCH3 of phosphine), 134.6 (d, 2JCP = 12 Hz, ortho-C of phosphine), 127.4 (d, 1JCP = 50 Hz, ipso-C of phosphine), 114.0 (d, 3JCP = 11 Hz, meta-C of phosphine), 96.6 (Cp ring), 58.0 (Mo—COCH2CH3), 10.1 (Mo—COCH2CH3). 31P{1H} NMR (162 MHz, CDCl3): δ 62.3 (s). IR (CH2Cl2, NaCl, cm−1) ν(CO): 1933, 1847, 1605 (acetyl).
6. Refinement
Crystal data, data collection and structure . H atoms were placed in calculated positions and refined in the riding-model approximation with distances of C—H = 0.95, 0.98, 0.99, and 1.00 Å for the phenyl, methyl, methylene, and cyclopentadienyl groups, respectively, and with Uiso(H) = k×Ueq(C), k = 1.2 for cyclopentadienyl, phenyl, and methylene groups and 1.5 for methyl groups. Methyl group H atoms were allowed to rotate in order to find the best rotameric conformation.
details are summarized in Table 7
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A small number of intense low-angle reflections [three for (1); seven for (2); five for (3)] are missing from these high-quality data sets due to the arrangement of the instrument with a conservatively sized beam stop. The large number of reflections in the data sets (and the Fourier-transform relationship of intensities to atoms) ensures that no particular bias has been introduced.
The structure of (3) exhibits modest disorder in the position of Cl1 of the dichloromethane solvent, which was modeled with two sites showing approximately equivalent occupancies [0.532 (15) for Cl1A, 0.468 (15) for Cl1B].
Supporting information
https://doi.org/10.1107/S2056989021008008/jq2008sup1.cif
contains datablocks global, 1, 2, 3. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989021008008/jq20081sup2.hkl
Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989021008008/jq20082sup3.hkl
Structure factors: contains datablock 3. DOI: https://doi.org/10.1107/S2056989021008008/jq20083sup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989021008008/jq20081sup5.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2056989021008008/jq20082sup6.cdx
Supporting information file. DOI: https://doi.org/10.1107/S2056989021008008/jq20083sup7.cdx
For all structures, data collection: BIS (Bruker, 2019); cell
SAINT (Bruker, 2019); data reduction: SAINT (Bruker, 2019); program(s) used to solve structure: SHELXT2018/2 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae et al., 2020); software used to prepare material for publication: publCIF (Westrip, 2010).[Mo(C5H5)(C3H5O)(C18H15P)(CO)2] | Z = 2 |
Mr = 536.39 | F(000) = 548 |
Triclinic, P1 | Dx = 1.491 Mg m−3 |
a = 9.1719 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.7493 (7) Å | Cell parameters from 9085 reflections |
c = 12.6049 (7) Å | θ = 2.6–33.1° |
α = 113.083 (2)° | µ = 0.64 mm−1 |
β = 99.148 (2)° | T = 170 K |
γ = 99.380 (2)° | Prism, yellow |
V = 1195.14 (12) Å3 | 0.16 × 0.16 × 0.06 mm |
Bruker D8 QUEST ECO diffractometer | 5939 independent reflections |
Radiation source: sealed tube, Siemens KFFMO2K-90C | 5674 reflections with I > 2σ(I) |
Curved Graphite monochromator | Rint = 0.025 |
Detector resolution: 7.3910 pixels mm-1 | θmax = 28.3°, θmin = 2.3° |
φ and ω scans | h = −12→12 |
Absorption correction: multi-scan (Krause et al., 2015) | k = −15→15 |
Tmin = 0.89, Tmax = 0.96 | l = −16→16 |
49481 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.019 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.051 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.022P)2 + 0.6108P] where P = (Fo2 + 2Fc2)/3 |
5939 reflections | (Δ/σ)max = 0.001 |
299 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.40 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 | ||
Mo1 | 0.21851 (2) | 0.45813 (2) | 0.23960 (2) | 0.01978 (4) | |
P1 | 0.32246 (3) | 0.69322 (3) | 0.33370 (3) | 0.01786 (6) | |
O1 | 0.22653 (14) | 0.50413 (11) | 0.01296 (9) | 0.0343 (2) | |
O2 | 0.54687 (13) | 0.48265 (11) | 0.37404 (11) | 0.0391 (3) | |
O3 | 0.23712 (16) | 0.18616 (11) | 0.08762 (12) | 0.0459 (3) | |
C1 | 0.22950 (15) | 0.48927 (12) | 0.09861 (11) | 0.0233 (2) | |
C2 | 0.42735 (17) | 0.47555 (13) | 0.32222 (12) | 0.0267 (3) | |
C3 | 0.30515 (18) | 0.29556 (13) | 0.11888 (12) | 0.0288 (3) | |
C4 | 0.4478 (2) | 0.32080 (16) | 0.07449 (15) | 0.0390 (4) | |
H4A | 0.428632 | 0.366718 | 0.024555 | 0.047* | |
H4B | 0.533049 | 0.37787 | 0.144096 | 0.047* | |
C5 | 0.4970 (2) | 0.20261 (19) | 0.00328 (17) | 0.0504 (5) | |
H5A | 0.420288 | 0.151328 | −0.072025 | 0.076* | |
H5B | 0.507534 | 0.15204 | 0.048824 | 0.076* | |
H5C | 0.595154 | 0.227972 | −0.013045 | 0.076* | |
C6 | −0.05044 (17) | 0.42011 (17) | 0.21381 (16) | 0.0377 (4) | |
H6 | −0.121988 | 0.444525 | 0.162697 | 0.045* | |
C7 | 0.01630 (18) | 0.49182 (16) | 0.33645 (15) | 0.0356 (3) | |
H7 | 0.00108 | 0.576933 | 0.387033 | 0.043* | |
C8 | 0.09701 (19) | 0.41922 (16) | 0.37808 (14) | 0.0348 (3) | |
H8 | 0.146453 | 0.442892 | 0.463005 | 0.042* | |
C9 | 0.08355 (19) | 0.30236 (15) | 0.28055 (15) | 0.0354 (3) | |
H9 | 0.118582 | 0.227614 | 0.284712 | 0.042* | |
C10 | −0.00792 (19) | 0.30284 (16) | 0.17850 (15) | 0.0369 (3) | |
H10 | −0.047308 | 0.228557 | 0.098522 | 0.044* | |
C11 | 0.29484 (14) | 0.77386 (12) | 0.48373 (11) | 0.0209 (2) | |
C12 | 0.32519 (18) | 0.71890 (14) | 0.56225 (12) | 0.0296 (3) | |
H12 | 0.360821 | 0.643324 | 0.537306 | 0.035* | |
C13 | 0.30390 (19) | 0.77344 (15) | 0.67645 (13) | 0.0337 (3) | |
H13 | 0.325727 | 0.735596 | 0.729406 | 0.04* | |
C14 | 0.25087 (18) | 0.88295 (15) | 0.71309 (13) | 0.0329 (3) | |
H14 | 0.235238 | 0.919963 | 0.790907 | 0.039* | |
C15 | 0.22073 (17) | 0.93831 (14) | 0.63604 (13) | 0.0309 (3) | |
H15 | 0.1844 | 1.013525 | 0.661221 | 0.037* | |
C16 | 0.24327 (15) | 0.88454 (12) | 0.52163 (12) | 0.0238 (2) | |
H16 | 0.223316 | 0.923696 | 0.46953 | 0.029* | |
C17 | 0.25504 (14) | 0.78737 (12) | 0.25929 (11) | 0.0190 (2) | |
C18 | 0.10476 (15) | 0.74751 (13) | 0.19178 (12) | 0.0240 (2) | |
H18 | 0.041175 | 0.669342 | 0.180761 | 0.029* | |
C19 | 0.04765 (17) | 0.82174 (14) | 0.14056 (13) | 0.0302 (3) | |
H19 | −0.055523 | 0.795183 | 0.096435 | 0.036* | |
C20 | 0.14075 (18) | 0.93438 (14) | 0.15365 (13) | 0.0305 (3) | |
H20 | 0.101594 | 0.984707 | 0.118267 | 0.037* | |
C21 | 0.29082 (18) | 0.97327 (13) | 0.21836 (13) | 0.0287 (3) | |
H21 | 0.355199 | 1.049602 | 0.226151 | 0.034* | |
C22 | 0.34774 (15) | 0.90100 (12) | 0.27206 (12) | 0.0242 (3) | |
H22 | 0.450298 | 0.929118 | 0.317696 | 0.029* | |
C23 | 0.52909 (14) | 0.73720 (12) | 0.35437 (11) | 0.0207 (2) | |
C24 | 0.58606 (15) | 0.69609 (13) | 0.25280 (12) | 0.0258 (3) | |
H24 | 0.5177 | 0.656619 | 0.176174 | 0.031* | |
C25 | 0.74111 (16) | 0.71250 (15) | 0.26317 (14) | 0.0319 (3) | |
H25 | 0.779018 | 0.68406 | 0.1938 | 0.038* | |
C26 | 0.84183 (16) | 0.77070 (15) | 0.37523 (15) | 0.0331 (3) | |
H26 | 0.948349 | 0.781057 | 0.382243 | 0.04* | |
C27 | 0.78743 (16) | 0.81325 (14) | 0.47583 (13) | 0.0310 (3) | |
H27 | 0.856515 | 0.853859 | 0.552162 | 0.037* | |
C28 | 0.63068 (16) | 0.79681 (13) | 0.46591 (12) | 0.0264 (3) | |
H28 | 0.593438 | 0.826442 | 0.53553 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.02476 (6) | 0.01872 (6) | 0.01856 (6) | 0.00571 (4) | 0.00643 (4) | 0.01018 (4) |
P1 | 0.01821 (14) | 0.01985 (14) | 0.01678 (14) | 0.00582 (11) | 0.00409 (11) | 0.00879 (11) |
O1 | 0.0494 (6) | 0.0349 (6) | 0.0221 (5) | 0.0107 (5) | 0.0090 (4) | 0.0155 (4) |
O2 | 0.0397 (6) | 0.0413 (6) | 0.0407 (6) | 0.0187 (5) | 0.0014 (5) | 0.0220 (5) |
O3 | 0.0611 (8) | 0.0230 (5) | 0.0525 (7) | 0.0117 (5) | 0.0214 (6) | 0.0118 (5) |
C1 | 0.0263 (6) | 0.0203 (6) | 0.0214 (6) | 0.0053 (5) | 0.0048 (5) | 0.0078 (5) |
C2 | 0.0368 (7) | 0.0246 (6) | 0.0237 (6) | 0.0131 (5) | 0.0088 (5) | 0.0129 (5) |
C3 | 0.0399 (8) | 0.0254 (6) | 0.0231 (6) | 0.0133 (6) | 0.0073 (6) | 0.0105 (5) |
C4 | 0.0481 (9) | 0.0354 (8) | 0.0361 (8) | 0.0188 (7) | 0.0199 (7) | 0.0112 (7) |
C5 | 0.0631 (12) | 0.0475 (10) | 0.0411 (9) | 0.0299 (9) | 0.0218 (9) | 0.0097 (8) |
C6 | 0.0248 (7) | 0.0488 (9) | 0.0495 (9) | 0.0041 (6) | 0.0104 (6) | 0.0327 (8) |
C7 | 0.0338 (8) | 0.0335 (8) | 0.0460 (9) | 0.0091 (6) | 0.0235 (7) | 0.0183 (7) |
C8 | 0.0409 (8) | 0.0411 (8) | 0.0281 (7) | 0.0056 (7) | 0.0165 (6) | 0.0194 (6) |
C9 | 0.0462 (9) | 0.0290 (7) | 0.0416 (8) | 0.0071 (6) | 0.0193 (7) | 0.0236 (7) |
C10 | 0.0378 (8) | 0.0338 (8) | 0.0336 (8) | −0.0071 (6) | 0.0109 (6) | 0.0142 (6) |
C11 | 0.0198 (5) | 0.0229 (6) | 0.0189 (5) | 0.0043 (5) | 0.0048 (4) | 0.0083 (5) |
C12 | 0.0393 (8) | 0.0309 (7) | 0.0231 (6) | 0.0137 (6) | 0.0095 (6) | 0.0136 (6) |
C13 | 0.0438 (8) | 0.0366 (8) | 0.0220 (6) | 0.0064 (6) | 0.0086 (6) | 0.0149 (6) |
C14 | 0.0375 (8) | 0.0317 (7) | 0.0217 (6) | 0.0000 (6) | 0.0117 (6) | 0.0052 (5) |
C15 | 0.0332 (7) | 0.0243 (6) | 0.0296 (7) | 0.0057 (5) | 0.0120 (6) | 0.0050 (5) |
C16 | 0.0231 (6) | 0.0221 (6) | 0.0238 (6) | 0.0034 (5) | 0.0054 (5) | 0.0085 (5) |
C17 | 0.0209 (5) | 0.0210 (6) | 0.0176 (5) | 0.0069 (4) | 0.0057 (4) | 0.0096 (5) |
C18 | 0.0217 (6) | 0.0248 (6) | 0.0265 (6) | 0.0047 (5) | 0.0041 (5) | 0.0130 (5) |
C19 | 0.0272 (7) | 0.0330 (7) | 0.0308 (7) | 0.0092 (6) | −0.0002 (5) | 0.0163 (6) |
C20 | 0.0430 (8) | 0.0266 (7) | 0.0270 (7) | 0.0144 (6) | 0.0060 (6) | 0.0153 (6) |
C21 | 0.0382 (7) | 0.0215 (6) | 0.0279 (7) | 0.0054 (5) | 0.0083 (6) | 0.0127 (5) |
C22 | 0.0244 (6) | 0.0226 (6) | 0.0245 (6) | 0.0033 (5) | 0.0041 (5) | 0.0107 (5) |
C23 | 0.0192 (5) | 0.0212 (6) | 0.0223 (6) | 0.0064 (4) | 0.0043 (5) | 0.0096 (5) |
C24 | 0.0218 (6) | 0.0286 (7) | 0.0229 (6) | 0.0043 (5) | 0.0043 (5) | 0.0080 (5) |
C25 | 0.0255 (7) | 0.0342 (7) | 0.0335 (7) | 0.0090 (6) | 0.0119 (6) | 0.0097 (6) |
C26 | 0.0187 (6) | 0.0348 (7) | 0.0442 (8) | 0.0079 (5) | 0.0050 (6) | 0.0158 (7) |
C27 | 0.0250 (6) | 0.0325 (7) | 0.0302 (7) | 0.0037 (5) | −0.0029 (5) | 0.0132 (6) |
C28 | 0.0254 (6) | 0.0281 (6) | 0.0231 (6) | 0.0063 (5) | 0.0029 (5) | 0.0096 (5) |
Mo1—P1 | 2.4816 (4) | C11—C12 | 1.3951 (18) |
Mo1—C1 | 1.9640 (13) | C12—C13 | 1.388 (2) |
Mo1—C2 | 1.9662 (15) | C12—H12 | 0.95 |
Mo1—C3 | 2.2794 (14) | C13—C14 | 1.384 (2) |
Mo1—C9 | 2.3138 (14) | C13—H13 | 0.95 |
Mo1—C10 | 2.3216 (15) | C14—C15 | 1.382 (2) |
Mo1—C8 | 2.3612 (14) | C14—H14 | 0.95 |
Mo1—C6 | 2.3795 (15) | C15—C16 | 1.3945 (19) |
Mo1—C7 | 2.3805 (15) | C15—H15 | 0.95 |
P1—C17 | 1.8270 (12) | C16—H16 | 0.95 |
P1—C23 | 1.8289 (13) | C17—C18 | 1.3956 (17) |
P1—C11 | 1.8341 (13) | C17—C22 | 1.3961 (18) |
O1—C1 | 1.1563 (17) | C18—C19 | 1.3910 (18) |
O2—C2 | 1.1555 (18) | C18—H18 | 0.95 |
O3—C3 | 1.2083 (19) | C19—C20 | 1.387 (2) |
C3—C4 | 1.533 (2) | C19—H19 | 0.95 |
C4—C5 | 1.514 (2) | C20—C21 | 1.384 (2) |
C4—H4A | 0.99 | C20—H20 | 0.95 |
C4—H4B | 0.99 | C21—C22 | 1.3909 (19) |
C5—H5A | 0.98 | C21—H21 | 0.95 |
C5—H5B | 0.98 | C22—H22 | 0.95 |
C5—H5C | 0.98 | C23—C28 | 1.3907 (18) |
C6—C7 | 1.408 (2) | C23—C24 | 1.3984 (18) |
C6—C10 | 1.414 (3) | C24—C25 | 1.3814 (19) |
C6—H6 | 1.0 | C24—H24 | 0.95 |
C7—C8 | 1.409 (2) | C25—C26 | 1.392 (2) |
C7—H7 | 1.0 | C25—H25 | 0.95 |
C8—C9 | 1.409 (2) | C26—C27 | 1.376 (2) |
C8—H8 | 1.0 | C26—H26 | 0.95 |
C9—C10 | 1.422 (2) | C27—C28 | 1.398 (2) |
C9—H9 | 1.0 | C27—H27 | 0.95 |
C10—H10 | 1.0 | C28—H28 | 0.95 |
C11—C16 | 1.3886 (18) | ||
C1—Mo1—C2 | 107.83 (6) | C7—C8—Mo1 | 73.47 (8) |
C1—Mo1—C3 | 74.37 (5) | C9—C8—Mo1 | 70.63 (8) |
C2—Mo1—C3 | 72.47 (5) | C7—C8—H8 | 125.9 |
C1—Mo1—C9 | 136.85 (6) | C9—C8—H8 | 125.9 |
C2—Mo1—C9 | 100.67 (6) | Mo1—C8—H8 | 125.9 |
C3—Mo1—C9 | 84.47 (6) | C8—C9—C10 | 107.75 (14) |
C1—Mo1—C10 | 103.82 (6) | C8—C9—Mo1 | 74.31 (8) |
C2—Mo1—C10 | 133.28 (6) | C10—C9—Mo1 | 72.43 (8) |
C3—Mo1—C10 | 84.30 (6) | C8—C9—H9 | 125.8 |
C9—Mo1—C10 | 35.73 (6) | C10—C9—H9 | 125.8 |
C1—Mo1—C8 | 155.48 (6) | Mo1—C9—H9 | 125.8 |
C2—Mo1—C8 | 96.57 (6) | C6—C10—C9 | 108.10 (15) |
C3—Mo1—C8 | 116.63 (6) | C6—C10—Mo1 | 74.76 (9) |
C9—Mo1—C8 | 35.06 (6) | C9—C10—Mo1 | 71.83 (9) |
C10—Mo1—C8 | 58.45 (6) | C6—C10—H10 | 125.7 |
C1—Mo1—C6 | 97.82 (6) | C9—C10—H10 | 125.7 |
C2—Mo1—C6 | 154.34 (6) | Mo1—C10—H10 | 125.7 |
C3—Mo1—C6 | 116.12 (6) | C16—C11—C12 | 118.96 (12) |
C9—Mo1—C6 | 58.55 (6) | C16—C11—P1 | 123.40 (10) |
C10—Mo1—C6 | 34.97 (6) | C12—C11—P1 | 117.64 (10) |
C8—Mo1—C6 | 57.79 (6) | C13—C12—C11 | 120.73 (14) |
C1—Mo1—C7 | 123.06 (6) | C13—C12—H12 | 119.6 |
C2—Mo1—C7 | 123.54 (6) | C11—C12—H12 | 119.6 |
C3—Mo1—C7 | 140.20 (6) | C14—C13—C12 | 119.95 (14) |
C9—Mo1—C7 | 58.03 (6) | C14—C13—H13 | 120.0 |
C10—Mo1—C7 | 57.85 (6) | C12—C13—H13 | 120.0 |
C8—Mo1—C7 | 34.56 (6) | C15—C14—C13 | 119.77 (13) |
C6—Mo1—C7 | 34.42 (6) | C15—C14—H14 | 120.1 |
C1—Mo1—P1 | 79.34 (4) | C13—C14—H14 | 120.1 |
C2—Mo1—P1 | 78.28 (4) | C14—C15—C16 | 120.48 (14) |
C3—Mo1—P1 | 131.76 (4) | C14—C15—H15 | 119.8 |
C9—Mo1—P1 | 139.01 (4) | C16—C15—H15 | 119.8 |
C10—Mo1—P1 | 141.74 (5) | C11—C16—C15 | 120.10 (13) |
C8—Mo1—P1 | 103.97 (4) | C11—C16—H16 | 119.9 |
C6—Mo1—P1 | 106.91 (4) | C15—C16—H16 | 119.9 |
C7—Mo1—P1 | 88.01 (4) | C18—C17—C22 | 118.98 (12) |
C17—P1—C23 | 102.95 (6) | C18—C17—P1 | 119.14 (9) |
C17—P1—C11 | 102.96 (6) | C22—C17—P1 | 121.83 (10) |
C23—P1—C11 | 103.95 (6) | C19—C18—C17 | 120.29 (12) |
C17—P1—Mo1 | 119.32 (4) | C19—C18—H18 | 119.9 |
C23—P1—Mo1 | 111.87 (4) | C17—C18—H18 | 119.9 |
C11—P1—Mo1 | 114.09 (4) | C20—C19—C18 | 120.26 (13) |
O1—C1—Mo1 | 175.81 (12) | C20—C19—H19 | 119.9 |
O2—C2—Mo1 | 176.43 (13) | C18—C19—H19 | 119.9 |
O3—C3—C4 | 118.46 (14) | C21—C20—C19 | 119.83 (13) |
O3—C3—Mo1 | 119.78 (12) | C21—C20—H20 | 120.1 |
C4—C3—Mo1 | 121.76 (10) | C19—C20—H20 | 120.1 |
C5—C4—C3 | 115.02 (15) | C20—C21—C22 | 120.23 (13) |
C5—C4—H4A | 108.5 | C20—C21—H21 | 119.9 |
C3—C4—H4A | 108.5 | C22—C21—H21 | 119.9 |
C5—C4—H4B | 108.5 | C21—C22—C17 | 120.39 (12) |
C3—C4—H4B | 108.5 | C21—C22—H22 | 119.8 |
H4A—C4—H4B | 107.5 | C17—C22—H22 | 119.8 |
C4—C5—H5A | 109.5 | C28—C23—C24 | 119.14 (12) |
C4—C5—H5B | 109.5 | C28—C23—P1 | 122.88 (10) |
H5A—C5—H5B | 109.5 | C24—C23—P1 | 117.61 (10) |
C4—C5—H5C | 109.5 | C25—C24—C23 | 120.42 (13) |
H5A—C5—H5C | 109.5 | C25—C24—H24 | 119.8 |
H5B—C5—H5C | 109.5 | C23—C24—H24 | 119.8 |
C7—C6—C10 | 107.44 (14) | C24—C25—C26 | 120.02 (14) |
C7—C6—Mo1 | 72.83 (9) | C24—C25—H25 | 120.0 |
C10—C6—Mo1 | 70.27 (9) | C26—C25—H25 | 120.0 |
C7—C6—H6 | 126.2 | C27—C26—C25 | 120.14 (13) |
C10—C6—H6 | 126.2 | C27—C26—H26 | 119.9 |
Mo1—C6—H6 | 126.2 | C25—C26—H26 | 119.9 |
C6—C7—C8 | 108.81 (15) | C26—C27—C28 | 120.10 (13) |
C6—C7—Mo1 | 72.75 (9) | C26—C27—H27 | 120.0 |
C8—C7—Mo1 | 71.97 (8) | C28—C27—H27 | 120.0 |
C6—C7—H7 | 125.5 | C23—C28—C27 | 120.16 (13) |
C8—C7—H7 | 125.5 | C23—C28—H28 | 119.9 |
Mo1—C7—H7 | 125.5 | C27—C28—H28 | 119.9 |
C7—C8—C9 | 107.89 (14) | ||
O3—C3—C4—C5 | −5.3 (2) | C14—C15—C16—C11 | 0.7 (2) |
Mo1—C3—C4—C5 | 175.31 (12) | C23—P1—C17—C18 | 157.21 (10) |
C10—C6—C7—C8 | −1.24 (17) | C11—P1—C17—C18 | −94.93 (11) |
Mo1—C6—C7—C8 | −63.38 (11) | Mo1—P1—C17—C18 | 32.63 (12) |
C10—C6—C7—Mo1 | 62.13 (10) | C23—P1—C17—C22 | −25.50 (12) |
C6—C7—C8—C9 | 1.22 (17) | C11—P1—C17—C22 | 82.36 (11) |
Mo1—C7—C8—C9 | −62.66 (10) | Mo1—P1—C17—C22 | −150.08 (9) |
C6—C7—C8—Mo1 | 63.88 (11) | C22—C17—C18—C19 | −1.5 (2) |
C7—C8—C9—C10 | −0.72 (17) | P1—C17—C18—C19 | 175.84 (11) |
Mo1—C8—C9—C10 | −65.22 (10) | C17—C18—C19—C20 | 1.6 (2) |
C7—C8—C9—Mo1 | 64.51 (11) | C18—C19—C20—C21 | −0.3 (2) |
C7—C6—C10—C9 | 0.79 (17) | C19—C20—C21—C22 | −1.2 (2) |
Mo1—C6—C10—C9 | 64.59 (11) | C20—C21—C22—C17 | 1.3 (2) |
C7—C6—C10—Mo1 | −63.80 (10) | C18—C17—C22—C21 | 0.1 (2) |
C8—C9—C10—C6 | −0.05 (17) | P1—C17—C22—C21 | −177.21 (10) |
Mo1—C9—C10—C6 | −66.52 (10) | C17—P1—C23—C28 | 118.22 (11) |
C8—C9—C10—Mo1 | 66.48 (11) | C11—P1—C23—C28 | 11.11 (13) |
C17—P1—C11—C16 | −3.65 (12) | Mo1—P1—C23—C28 | −112.46 (11) |
C23—P1—C11—C16 | 103.45 (12) | C17—P1—C23—C24 | −68.86 (11) |
Mo1—P1—C11—C16 | −134.44 (10) | C11—P1—C23—C24 | −175.97 (10) |
C17—P1—C11—C12 | 175.23 (11) | Mo1—P1—C23—C24 | 60.46 (11) |
C23—P1—C11—C12 | −77.66 (12) | C28—C23—C24—C25 | 1.1 (2) |
Mo1—P1—C11—C12 | 44.44 (12) | P1—C23—C24—C25 | −172.08 (11) |
C16—C11—C12—C13 | 0.2 (2) | C23—C24—C25—C26 | −0.2 (2) |
P1—C11—C12—C13 | −178.74 (12) | C24—C25—C26—C27 | −0.7 (2) |
C11—C12—C13—C14 | 0.5 (2) | C25—C26—C27—C28 | 0.8 (2) |
C12—C13—C14—C15 | −0.6 (2) | C24—C23—C28—C27 | −1.1 (2) |
C13—C14—C15—C16 | 0.0 (2) | P1—C23—C28—C27 | 171.76 (11) |
C12—C11—C16—C15 | −0.8 (2) | C26—C27—C28—C23 | 0.1 (2) |
P1—C11—C16—C15 | 178.09 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···O2i | 0.95 | 2.36 | 3.1188 (18) | 137 |
C6—H6···O1ii | 1.00 | 2.60 | 3.545 (2) | 158 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z. |
[Mo(C5H5)(C3H5O)(C18H12F3P)(CO)2] | F(000) = 2384 |
Mr = 590.36 | Dx = 1.595 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.7991 (4) Å | Cell parameters from 9718 reflections |
b = 18.6907 (8) Å | θ = 2.3–30.5° |
c = 22.4744 (8) Å | µ = 0.65 mm−1 |
β = 97.256 (2)° | T = 170 K |
V = 4916.7 (3) Å3 | Prism, yellow |
Z = 8 | 0.05 × 0.05 × 0.05 mm |
Bruker D8 QUEST ECO diffractometer | 10047 independent reflections |
Radiation source: sealed tube, Siemens KFFMO2K-90C | 8547 reflections with I > 2σ(I) |
Curved Graphite monochromator | Rint = 0.042 |
Detector resolution: 7.3910 pixels mm-1 | θmax = 26.4°, θmin = 2.3° |
φ and ω scans | h = −14→14 |
Absorption correction: multi-scan (Krause et al., 2015) | k = −23→23 |
Tmin = 0.86, Tmax = 0.97 | l = −28→27 |
73758 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0211P)2 + 4.4865P] where P = (Fo2 + 2Fc2)/3 |
10047 reflections | (Δ/σ)max = 0.002 |
651 parameters | Δρmax = 0.37 e Å−3 |
0 restraints | Δρmin = −0.39 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 | ||
Mo1 | 0.68359 (2) | 0.16744 (2) | 0.31097 (2) | 0.01937 (5) | |
P1 | 0.50728 (5) | 0.18602 (3) | 0.35791 (3) | 0.01993 (12) | |
F1 | 0.54908 (16) | 0.08511 (12) | 0.61078 (7) | 0.0637 (6) | |
F2 | 0.08121 (14) | 0.03649 (10) | 0.25717 (8) | 0.0533 (5) | |
F3 | 0.36509 (14) | 0.49064 (7) | 0.35239 (8) | 0.0441 (4) | |
O1 | 0.51071 (16) | 0.18266 (10) | 0.19490 (8) | 0.0399 (5) | |
O2 | 0.74633 (16) | 0.31199 (10) | 0.37628 (8) | 0.0361 (4) | |
O3 | 0.88132 (15) | 0.22239 (10) | 0.24695 (8) | 0.0333 (4) | |
C1 | 0.5734 (2) | 0.18193 (12) | 0.23876 (11) | 0.0256 (5) | |
C2 | 0.71837 (19) | 0.25955 (13) | 0.35133 (10) | 0.0243 (5) | |
C3 | 0.7827 (2) | 0.23663 (13) | 0.25283 (10) | 0.0248 (5) | |
C4 | 0.7294 (2) | 0.30324 (14) | 0.22084 (12) | 0.0346 (6) | |
H4A | 0.66605 | 0.28786 | 0.190403 | 0.041* | |
H4B | 0.696117 | 0.333204 | 0.250547 | 0.041* | |
C5 | 0.8111 (3) | 0.34882 (15) | 0.19021 (13) | 0.0409 (7) | |
H5A | 0.84251 | 0.32037 | 0.159538 | 0.061* | |
H5B | 0.873425 | 0.365392 | 0.219977 | 0.061* | |
H5C | 0.77008 | 0.3902 | 0.171316 | 0.061* | |
C6 | 0.6987 (3) | 0.04365 (14) | 0.29401 (13) | 0.0414 (7) | |
H6 | 0.647429 | 0.014715 | 0.264404 | 0.05* | |
C7 | 0.6872 (2) | 0.05233 (13) | 0.35502 (13) | 0.0345 (6) | |
H7 | 0.625273 | 0.031156 | 0.376022 | 0.041* | |
C8 | 0.7818 (2) | 0.09086 (14) | 0.38260 (12) | 0.0345 (6) | |
H8 | 0.799791 | 0.100797 | 0.426502 | 0.041* | |
C9 | 0.8523 (2) | 0.10673 (15) | 0.33829 (12) | 0.0368 (6) | |
H9 | 0.930101 | 0.128742 | 0.345501 | 0.044* | |
C10 | 0.8008 (3) | 0.07731 (15) | 0.28325 (13) | 0.0421 (7) | |
H10 | 0.835835 | 0.075189 | 0.245032 | 0.05* | |
C11 | 0.5180 (2) | 0.15457 (12) | 0.43586 (10) | 0.0236 (5) | |
C12 | 0.6089 (2) | 0.17724 (15) | 0.47718 (12) | 0.0350 (6) | |
H12 | 0.664562 | 0.208646 | 0.464597 | 0.042* | |
C13 | 0.6194 (2) | 0.15470 (18) | 0.53629 (12) | 0.0435 (7) | |
H13 | 0.680534 | 0.171027 | 0.564616 | 0.052* | |
C14 | 0.5390 (2) | 0.10810 (17) | 0.55288 (12) | 0.0408 (7) | |
C15 | 0.4497 (2) | 0.08329 (14) | 0.51394 (12) | 0.0354 (6) | |
H15 | 0.395996 | 0.050678 | 0.526812 | 0.043* | |
C16 | 0.4392 (2) | 0.10706 (13) | 0.45480 (11) | 0.0278 (5) | |
H16 | 0.377406 | 0.090595 | 0.426987 | 0.033* | |
C17 | 0.3749 (2) | 0.14313 (12) | 0.32379 (10) | 0.0238 (5) | |
C18 | 0.3798 (2) | 0.07402 (13) | 0.30120 (11) | 0.0312 (6) | |
H18 | 0.451868 | 0.051639 | 0.300493 | 0.037* | |
C19 | 0.2808 (2) | 0.03741 (15) | 0.27971 (12) | 0.0363 (6) | |
H19 | 0.284022 | −0.010424 | 0.265731 | 0.044* | |
C20 | 0.1781 (2) | 0.07191 (16) | 0.27914 (12) | 0.0360 (6) | |
C21 | 0.1688 (2) | 0.14034 (15) | 0.29969 (11) | 0.0321 (6) | |
H21 | 0.096469 | 0.163162 | 0.297831 | 0.039* | |
C22 | 0.2682 (2) | 0.17545 (13) | 0.32338 (11) | 0.0275 (5) | |
H22 | 0.263447 | 0.222164 | 0.33953 | 0.033* | |
C23 | 0.46301 (18) | 0.27942 (12) | 0.36021 (10) | 0.0212 (5) | |
C24 | 0.4234 (2) | 0.31163 (12) | 0.30539 (11) | 0.0270 (5) | |
H24 | 0.421085 | 0.284722 | 0.269401 | 0.032* | |
C25 | 0.3877 (2) | 0.38197 (13) | 0.30282 (12) | 0.0318 (6) | |
H25 | 0.358032 | 0.403262 | 0.265723 | 0.038* | |
C26 | 0.3961 (2) | 0.42019 (12) | 0.35498 (13) | 0.0308 (6) | |
C27 | 0.4348 (2) | 0.39122 (13) | 0.40983 (12) | 0.0306 (6) | |
H27 | 0.439161 | 0.419233 | 0.445318 | 0.037* | |
C28 | 0.4673 (2) | 0.31977 (13) | 0.41208 (11) | 0.0255 (5) | |
H28 | 0.492908 | 0.298322 | 0.449712 | 0.031* | |
Mo2 | 0.13778 (2) | 0.20503 (2) | 0.57103 (2) | 0.01918 (5) | |
P2 | 0.07626 (5) | 0.32692 (3) | 0.53987 (3) | 0.01888 (12) | |
F4 | −0.41095 (12) | 0.38483 (9) | 0.56536 (7) | 0.0443 (4) | |
F5 | 0.36489 (13) | 0.55112 (8) | 0.67019 (7) | 0.0405 (4) | |
F6 | 0.08738 (15) | 0.40659 (9) | 0.28469 (7) | 0.0483 (4) | |
O4 | −0.11576 (15) | 0.17823 (10) | 0.51826 (9) | 0.0389 (4) | |
O5 | 0.28370 (16) | 0.23246 (10) | 0.46697 (9) | 0.0408 (5) | |
O6 | 0.1843 (2) | 0.04766 (10) | 0.54648 (9) | 0.0584 (6) | |
C29 | −0.0209 (2) | 0.18824 (12) | 0.53604 (11) | 0.0250 (5) | |
C30 | 0.2268 (2) | 0.22200 (12) | 0.50419 (11) | 0.0261 (5) | |
C31 | 0.1403 (2) | 0.09868 (12) | 0.52100 (11) | 0.0265 (5) | |
C32 | 0.0920 (3) | 0.08959 (15) | 0.45594 (12) | 0.0392 (7) | |
H32A | 0.008542 | 0.097943 | 0.452191 | 0.047* | |
H32B | 0.125178 | 0.127064 | 0.43224 | 0.047* | |
C33 | 0.1125 (3) | 0.01792 (15) | 0.42855 (13) | 0.0441 (7) | |
H33A | 0.073311 | 0.016208 | 0.387439 | 0.066* | |
H33B | 0.082777 | −0.02003 | 0.452393 | 0.066* | |
H33C | 0.194657 | 0.010948 | 0.428005 | 0.066* | |
C34 | 0.2910 (2) | 0.21959 (17) | 0.64802 (12) | 0.0412 (7) | |
H34 | 0.365723 | 0.243055 | 0.64373 | 0.049* | |
C35 | 0.1968 (3) | 0.25274 (16) | 0.66799 (11) | 0.0433 (7) | |
H35 | 0.192359 | 0.30424 | 0.679536 | 0.052* | |
C36 | 0.1135 (3) | 0.20086 (17) | 0.67425 (11) | 0.0408 (7) | |
H36 | 0.040367 | 0.208562 | 0.691483 | 0.049* | |
C37 | 0.1563 (2) | 0.13425 (15) | 0.65645 (11) | 0.0373 (6) | |
H37 | 0.120101 | 0.086396 | 0.660455 | 0.045* | |
C38 | 0.2670 (2) | 0.14677 (15) | 0.64067 (11) | 0.0358 (6) | |
H38 | 0.322423 | 0.109088 | 0.631453 | 0.043* | |
C39 | −0.07161 (19) | 0.35126 (12) | 0.54894 (10) | 0.0202 (5) | |
C40 | −0.1144 (2) | 0.33622 (13) | 0.60274 (11) | 0.0293 (5) | |
H40 | −0.064987 | 0.31691 | 0.63546 | 0.035* | |
C41 | −0.2281 (2) | 0.34908 (14) | 0.60907 (11) | 0.0314 (6) | |
H41 | −0.256614 | 0.339932 | 0.646011 | 0.038* | |
C42 | −0.2982 (2) | 0.37531 (13) | 0.56070 (12) | 0.0290 (5) | |
C43 | −0.2598 (2) | 0.39207 (14) | 0.50748 (11) | 0.0314 (6) | |
H43 | −0.309978 | 0.411534 | 0.475153 | 0.038* | |
C44 | −0.1453 (2) | 0.37987 (13) | 0.50190 (11) | 0.0264 (5) | |
H44 | −0.11709 | 0.391315 | 0.465296 | 0.032* | |
C45 | 0.16211 (19) | 0.39779 (12) | 0.57976 (10) | 0.0221 (5) | |
C46 | 0.1136 (2) | 0.45612 (12) | 0.60505 (10) | 0.0243 (5) | |
H46 | 0.032784 | 0.460151 | 0.601914 | 0.029* | |
C47 | 0.1819 (2) | 0.50884 (13) | 0.63496 (11) | 0.0279 (5) | |
H47 | 0.148881 | 0.548962 | 0.652204 | 0.034* | |
C48 | 0.2979 (2) | 0.50132 (13) | 0.63887 (11) | 0.0285 (5) | |
C49 | 0.3500 (2) | 0.44497 (13) | 0.61377 (11) | 0.0298 (6) | |
H49 | 0.430847 | 0.44186 | 0.616714 | 0.036* | |
C50 | 0.2813 (2) | 0.39324 (13) | 0.58426 (11) | 0.0274 (5) | |
H50 | 0.315441 | 0.35379 | 0.566651 | 0.033* | |
C51 | 0.08310 (18) | 0.35142 (12) | 0.46138 (10) | 0.0204 (5) | |
C52 | 0.1267 (2) | 0.41698 (12) | 0.44605 (11) | 0.0250 (5) | |
H52 | 0.155534 | 0.449472 | 0.476796 | 0.03* | |
C53 | 0.1287 (2) | 0.43575 (14) | 0.38613 (11) | 0.0297 (5) | |
H53 | 0.158918 | 0.480455 | 0.375637 | 0.036* | |
C54 | 0.0860 (2) | 0.38815 (15) | 0.34296 (11) | 0.0316 (6) | |
C55 | 0.0410 (2) | 0.32290 (14) | 0.35584 (11) | 0.0322 (6) | |
H55 | 0.011264 | 0.291174 | 0.324697 | 0.039* | |
C56 | 0.0404 (2) | 0.30477 (13) | 0.41563 (11) | 0.0269 (5) | |
H56 | 0.010257 | 0.259799 | 0.425552 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.02038 (10) | 0.01882 (10) | 0.01827 (10) | 0.00364 (8) | −0.00004 (7) | −0.00050 (7) |
P1 | 0.0203 (3) | 0.0190 (3) | 0.0200 (3) | 0.0007 (2) | 0.0005 (2) | 0.0010 (2) |
F1 | 0.0570 (12) | 0.1040 (16) | 0.0297 (9) | −0.0035 (11) | 0.0034 (8) | 0.0313 (10) |
F2 | 0.0360 (9) | 0.0682 (12) | 0.0554 (11) | −0.0274 (9) | 0.0049 (8) | −0.0178 (9) |
F3 | 0.0454 (10) | 0.0205 (7) | 0.0669 (11) | 0.0049 (7) | 0.0087 (8) | −0.0037 (7) |
O1 | 0.0374 (11) | 0.0506 (12) | 0.0284 (10) | 0.0065 (9) | −0.0093 (8) | −0.0035 (9) |
O2 | 0.0375 (10) | 0.0331 (10) | 0.0377 (10) | −0.0074 (8) | 0.0049 (8) | −0.0128 (8) |
O3 | 0.0276 (9) | 0.0392 (10) | 0.0341 (10) | 0.0025 (8) | 0.0079 (8) | 0.0000 (8) |
C1 | 0.0268 (12) | 0.0247 (12) | 0.0254 (12) | 0.0038 (10) | 0.0037 (10) | −0.0031 (10) |
C2 | 0.0199 (11) | 0.0290 (13) | 0.0243 (12) | −0.0001 (10) | 0.0042 (9) | 0.0002 (10) |
C3 | 0.0287 (13) | 0.0271 (12) | 0.0183 (11) | −0.0015 (10) | 0.0015 (10) | −0.0039 (9) |
C4 | 0.0399 (15) | 0.0330 (14) | 0.0316 (14) | 0.0057 (12) | 0.0075 (12) | 0.0039 (11) |
C5 | 0.0494 (17) | 0.0356 (15) | 0.0381 (16) | −0.0021 (13) | 0.0073 (13) | 0.0064 (12) |
C6 | 0.0561 (19) | 0.0191 (12) | 0.0470 (17) | 0.0114 (12) | −0.0009 (14) | −0.0039 (12) |
C7 | 0.0371 (15) | 0.0207 (12) | 0.0456 (16) | 0.0074 (11) | 0.0049 (12) | 0.0096 (11) |
C8 | 0.0336 (14) | 0.0354 (14) | 0.0326 (14) | 0.0134 (12) | −0.0024 (11) | 0.0123 (12) |
C9 | 0.0254 (13) | 0.0428 (15) | 0.0415 (16) | 0.0161 (12) | 0.0012 (12) | 0.0133 (13) |
C10 | 0.0544 (18) | 0.0326 (14) | 0.0414 (16) | 0.0265 (14) | 0.0146 (14) | 0.0023 (12) |
C11 | 0.0242 (12) | 0.0254 (12) | 0.0216 (11) | 0.0050 (10) | 0.0042 (9) | 0.0033 (9) |
C12 | 0.0266 (13) | 0.0496 (16) | 0.0284 (13) | −0.0042 (12) | 0.0019 (11) | 0.0058 (12) |
C13 | 0.0318 (15) | 0.071 (2) | 0.0255 (14) | −0.0025 (14) | −0.0042 (11) | 0.0077 (14) |
C14 | 0.0394 (16) | 0.0586 (19) | 0.0249 (14) | 0.0102 (14) | 0.0065 (12) | 0.0149 (13) |
C15 | 0.0370 (15) | 0.0355 (14) | 0.0356 (15) | 0.0022 (12) | 0.0118 (12) | 0.0130 (12) |
C16 | 0.0280 (13) | 0.0244 (12) | 0.0311 (13) | 0.0041 (10) | 0.0048 (10) | 0.0020 (10) |
C17 | 0.0244 (12) | 0.0249 (12) | 0.0215 (12) | −0.0048 (10) | 0.0007 (9) | 0.0028 (9) |
C18 | 0.0315 (14) | 0.0293 (13) | 0.0322 (14) | −0.0013 (11) | 0.0019 (11) | −0.0038 (11) |
C19 | 0.0417 (16) | 0.0345 (14) | 0.0324 (14) | −0.0108 (12) | 0.0038 (12) | −0.0077 (12) |
C20 | 0.0312 (14) | 0.0508 (17) | 0.0261 (13) | −0.0182 (13) | 0.0040 (11) | −0.0026 (12) |
C21 | 0.0244 (13) | 0.0432 (15) | 0.0292 (14) | −0.0054 (11) | 0.0052 (10) | 0.0013 (12) |
C22 | 0.0278 (13) | 0.0289 (13) | 0.0260 (12) | −0.0027 (10) | 0.0040 (10) | 0.0026 (10) |
C23 | 0.0159 (10) | 0.0212 (11) | 0.0263 (12) | −0.0006 (9) | 0.0014 (9) | 0.0002 (9) |
C24 | 0.0317 (13) | 0.0225 (12) | 0.0260 (12) | 0.0020 (10) | 0.0004 (10) | −0.0006 (10) |
C25 | 0.0342 (14) | 0.0243 (12) | 0.0355 (14) | 0.0018 (11) | −0.0012 (11) | 0.0053 (11) |
C26 | 0.0216 (12) | 0.0187 (11) | 0.0526 (17) | 0.0007 (10) | 0.0071 (11) | −0.0025 (11) |
C27 | 0.0273 (13) | 0.0311 (13) | 0.0345 (14) | −0.0038 (11) | 0.0084 (11) | −0.0106 (11) |
C28 | 0.0223 (12) | 0.0289 (12) | 0.0255 (12) | −0.0004 (10) | 0.0039 (10) | −0.0013 (10) |
Mo2 | 0.01832 (10) | 0.02103 (10) | 0.01787 (10) | 0.00077 (8) | 0.00110 (7) | 0.00333 (8) |
P2 | 0.0180 (3) | 0.0205 (3) | 0.0182 (3) | 0.0014 (2) | 0.0026 (2) | 0.0011 (2) |
F4 | 0.0207 (7) | 0.0672 (11) | 0.0468 (10) | 0.0075 (7) | 0.0113 (7) | −0.0050 (8) |
F5 | 0.0333 (8) | 0.0364 (8) | 0.0515 (10) | −0.0146 (7) | 0.0046 (7) | −0.0119 (7) |
F6 | 0.0641 (11) | 0.0604 (11) | 0.0221 (8) | 0.0108 (9) | 0.0129 (8) | 0.0110 (7) |
O4 | 0.0235 (10) | 0.0388 (11) | 0.0529 (12) | −0.0036 (8) | −0.0007 (9) | −0.0067 (9) |
O5 | 0.0381 (11) | 0.0421 (11) | 0.0470 (12) | 0.0118 (9) | 0.0244 (9) | 0.0136 (9) |
O6 | 0.0987 (19) | 0.0270 (10) | 0.0434 (12) | 0.0110 (11) | −0.0143 (12) | 0.0041 (9) |
C29 | 0.0267 (13) | 0.0209 (11) | 0.0277 (12) | 0.0018 (10) | 0.0050 (10) | 0.0014 (10) |
C30 | 0.0238 (12) | 0.0227 (12) | 0.0314 (13) | 0.0052 (10) | 0.0019 (11) | 0.0025 (10) |
C31 | 0.0251 (12) | 0.0227 (12) | 0.0316 (13) | −0.0020 (10) | 0.0035 (10) | 0.0035 (10) |
C32 | 0.0474 (17) | 0.0379 (15) | 0.0309 (14) | 0.0088 (13) | −0.0011 (12) | −0.0035 (12) |
C33 | 0.0590 (19) | 0.0355 (15) | 0.0383 (16) | −0.0063 (14) | 0.0078 (14) | −0.0056 (13) |
C34 | 0.0361 (15) | 0.0618 (19) | 0.0225 (13) | −0.0127 (14) | −0.0090 (11) | 0.0028 (13) |
C35 | 0.073 (2) | 0.0383 (15) | 0.0160 (12) | 0.0004 (15) | −0.0068 (13) | −0.0004 (11) |
C36 | 0.0420 (16) | 0.0634 (19) | 0.0181 (12) | 0.0140 (15) | 0.0072 (11) | 0.0112 (13) |
C37 | 0.0483 (17) | 0.0379 (15) | 0.0239 (13) | −0.0049 (13) | −0.0024 (12) | 0.0147 (11) |
C38 | 0.0373 (15) | 0.0450 (16) | 0.0229 (13) | 0.0143 (13) | −0.0048 (11) | 0.0066 (11) |
C39 | 0.0201 (11) | 0.0202 (11) | 0.0200 (11) | 0.0019 (9) | 0.0009 (9) | −0.0004 (9) |
C40 | 0.0292 (13) | 0.0348 (14) | 0.0243 (12) | 0.0049 (11) | 0.0045 (10) | 0.0052 (11) |
C41 | 0.0308 (13) | 0.0384 (14) | 0.0274 (13) | 0.0050 (11) | 0.0123 (11) | 0.0046 (11) |
C42 | 0.0196 (12) | 0.0323 (13) | 0.0363 (14) | 0.0009 (10) | 0.0082 (10) | −0.0070 (11) |
C43 | 0.0233 (12) | 0.0424 (15) | 0.0276 (13) | 0.0074 (11) | −0.0004 (10) | 0.0001 (11) |
C44 | 0.0233 (12) | 0.0347 (13) | 0.0216 (12) | 0.0027 (10) | 0.0044 (10) | 0.0017 (10) |
C45 | 0.0236 (12) | 0.0235 (11) | 0.0189 (11) | −0.0017 (9) | 0.0010 (9) | 0.0028 (9) |
C46 | 0.0210 (11) | 0.0263 (12) | 0.0248 (12) | 0.0019 (10) | 0.0005 (9) | 0.0010 (10) |
C47 | 0.0299 (13) | 0.0233 (12) | 0.0311 (13) | 0.0022 (10) | 0.0057 (11) | −0.0022 (10) |
C48 | 0.0283 (13) | 0.0256 (12) | 0.0305 (13) | −0.0086 (10) | −0.0003 (10) | 0.0010 (10) |
C49 | 0.0208 (12) | 0.0305 (13) | 0.0383 (15) | −0.0027 (10) | 0.0046 (11) | 0.0028 (11) |
C50 | 0.0223 (12) | 0.0277 (12) | 0.0329 (13) | 0.0021 (10) | 0.0063 (10) | −0.0027 (10) |
C51 | 0.0187 (11) | 0.0242 (11) | 0.0183 (11) | 0.0051 (9) | 0.0029 (9) | 0.0011 (9) |
C52 | 0.0250 (12) | 0.0252 (12) | 0.0254 (12) | 0.0026 (10) | 0.0053 (10) | 0.0015 (10) |
C53 | 0.0299 (13) | 0.0314 (13) | 0.0295 (13) | 0.0052 (11) | 0.0109 (11) | 0.0076 (11) |
C54 | 0.0319 (14) | 0.0434 (15) | 0.0215 (12) | 0.0143 (12) | 0.0115 (10) | 0.0088 (11) |
C55 | 0.0360 (14) | 0.0364 (14) | 0.0232 (12) | 0.0096 (12) | 0.0001 (11) | −0.0033 (11) |
C56 | 0.0307 (13) | 0.0244 (12) | 0.0253 (12) | 0.0033 (10) | 0.0023 (10) | 0.0014 (10) |
Mo1—P1 | 2.4730 (6) | Mo2—C29 | 1.962 (2) |
Mo1—C1 | 1.966 (2) | Mo2—C30 | 1.964 (3) |
Mo1—C2 | 1.965 (2) | Mo2—C31 | 2.286 (2) |
Mo1—C3 | 2.265 (2) | Mo2—C38 | 2.315 (2) |
Mo1—C9 | 2.306 (2) | Mo2—C37 | 2.319 (2) |
Mo1—C10 | 2.314 (2) | Mo2—C34 | 2.355 (3) |
Mo1—C8 | 2.348 (2) | Mo2—C36 | 2.374 (3) |
Mo1—C6 | 2.355 (3) | Mo2—C35 | 2.376 (3) |
Mo1—C7 | 2.366 (2) | Mo2—P2 | 2.4654 (6) |
P1—C23 | 1.825 (2) | P2—C45 | 1.832 (2) |
P1—C17 | 1.835 (2) | P2—C51 | 1.834 (2) |
P1—C11 | 1.837 (2) | P2—C39 | 1.839 (2) |
F1—C14 | 1.361 (3) | F4—C42 | 1.359 (3) |
F2—C20 | 1.359 (3) | F5—C48 | 1.359 (3) |
F3—C26 | 1.366 (3) | F6—C54 | 1.356 (3) |
O1—C1 | 1.155 (3) | O4—C29 | 1.155 (3) |
O2—C2 | 1.156 (3) | O5—C30 | 1.154 (3) |
O3—C3 | 1.218 (3) | O6—C31 | 1.196 (3) |
C3—C4 | 1.532 (3) | C31—C32 | 1.511 (3) |
C4—C5 | 1.515 (4) | C32—C33 | 1.506 (4) |
C4—H4A | 0.99 | C32—H32A | 0.99 |
C4—H4B | 0.99 | C32—H32B | 0.99 |
C5—H5A | 0.98 | C33—H33A | 0.98 |
C5—H5B | 0.98 | C33—H33B | 0.98 |
C5—H5C | 0.98 | C33—H33C | 0.98 |
C6—C7 | 1.404 (4) | C34—C35 | 1.396 (4) |
C6—C10 | 1.406 (4) | C34—C38 | 1.396 (4) |
C6—H6 | 1.0 | C34—H34 | 1.0 |
C7—C8 | 1.405 (4) | C35—C36 | 1.400 (4) |
C7—H7 | 1.0 | C35—H35 | 1.0 |
C8—C9 | 1.408 (4) | C36—C37 | 1.420 (4) |
C8—H8 | 1.0 | C36—H36 | 1.0 |
C9—C10 | 1.419 (4) | C37—C38 | 1.416 (4) |
C9—H9 | 1.0 | C37—H37 | 1.0 |
C10—H10 | 1.0 | C38—H38 | 1.0 |
C11—C16 | 1.391 (3) | C39—C44 | 1.388 (3) |
C11—C12 | 1.393 (3) | C39—C40 | 1.397 (3) |
C12—C13 | 1.384 (4) | C40—C41 | 1.388 (3) |
C12—H12 | 0.95 | C40—H40 | 0.95 |
C13—C14 | 1.373 (4) | C41—C42 | 1.371 (4) |
C13—H13 | 0.95 | C41—H41 | 0.95 |
C14—C15 | 1.364 (4) | C42—C43 | 1.368 (3) |
C15—C16 | 1.392 (3) | C43—C44 | 1.391 (3) |
C15—H15 | 0.95 | C43—H43 | 0.95 |
C16—H16 | 0.95 | C44—H44 | 0.95 |
C17—C18 | 1.392 (3) | C45—C46 | 1.386 (3) |
C17—C22 | 1.395 (3) | C45—C50 | 1.400 (3) |
C18—C19 | 1.387 (4) | C46—C47 | 1.391 (3) |
C18—H18 | 0.95 | C46—H46 | 0.95 |
C19—C20 | 1.371 (4) | C47—C48 | 1.367 (3) |
C19—H19 | 0.95 | C47—H47 | 0.95 |
C20—C21 | 1.369 (4) | C48—C49 | 1.376 (3) |
C21—C22 | 1.390 (3) | C49—C50 | 1.376 (3) |
C21—H21 | 0.95 | C49—H49 | 0.95 |
C22—H22 | 0.95 | C50—H50 | 0.95 |
C23—C28 | 1.384 (3) | C51—C52 | 1.389 (3) |
C23—C24 | 1.398 (3) | C51—C56 | 1.393 (3) |
C24—C25 | 1.379 (3) | C52—C53 | 1.395 (3) |
C24—H24 | 0.95 | C52—H52 | 0.95 |
C25—C26 | 1.366 (4) | C53—C54 | 1.365 (4) |
C25—H25 | 0.95 | C53—H53 | 0.95 |
C26—C27 | 1.371 (4) | C54—C55 | 1.375 (4) |
C27—C28 | 1.389 (3) | C55—C56 | 1.387 (3) |
C27—H27 | 0.95 | C55—H55 | 0.95 |
C28—H28 | 0.95 | C56—H56 | 0.95 |
C1—Mo1—C2 | 109.77 (10) | C29—Mo2—C30 | 107.12 (10) |
C1—Mo1—C3 | 77.34 (9) | C29—Mo2—C31 | 74.64 (9) |
C2—Mo1—C3 | 70.93 (9) | C30—Mo2—C31 | 73.89 (9) |
C2—Mo1—C9 | 100.67 (10) | C29—Mo2—C38 | 135.20 (10) |
C1—Mo1—C9 | 138.27 (10) | C30—Mo2—C38 | 102.87 (10) |
C3—Mo1—C9 | 86.76 (9) | C31—Mo2—C38 | 82.81 (9) |
C2—Mo1—C10 | 131.68 (11) | C29—Mo2—C37 | 103.05 (10) |
C1—Mo1—C10 | 103.50 (10) | C30—Mo2—C37 | 136.20 (10) |
C3—Mo1—C10 | 83.74 (10) | C31—Mo2—C37 | 84.57 (9) |
C9—Mo1—C10 | 35.76 (10) | C38—Mo2—C37 | 35.59 (10) |
C2—Mo1—C8 | 99.28 (10) | C29—Mo2—C34 | 156.64 (10) |
C1—Mo1—C8 | 150.20 (10) | C30—Mo2—C34 | 96.22 (10) |
C3—Mo1—C8 | 119.84 (9) | C31—Mo2—C34 | 113.90 (10) |
C9—Mo1—C8 | 35.20 (9) | C38—Mo2—C34 | 34.77 (10) |
C10—Mo1—C8 | 58.73 (10) | C37—Mo2—C34 | 58.30 (10) |
C2—Mo1—C6 | 156.88 (10) | C29—Mo2—C36 | 99.19 (10) |
C1—Mo1—C6 | 93.30 (10) | C30—Mo2—C36 | 153.46 (10) |
C3—Mo1—C6 | 114.34 (10) | C31—Mo2—C36 | 117.57 (10) |
C9—Mo1—C6 | 58.62 (11) | C38—Mo2—C36 | 58.30 (10) |
C10—Mo1—C6 | 35.04 (10) | C37—Mo2—C36 | 35.19 (10) |
C8—Mo1—C6 | 58.07 (10) | C34—Mo2—C36 | 57.46 (10) |
C2—Mo1—C7 | 127.71 (10) | C29—Mo2—C35 | 125.58 (11) |
C1—Mo1—C7 | 116.47 (10) | C30—Mo2—C35 | 121.19 (11) |
C3—Mo1—C7 | 140.99 (9) | C31—Mo2—C35 | 139.20 (9) |
C9—Mo1—C7 | 58.14 (10) | C38—Mo2—C35 | 57.64 (10) |
C10—Mo1—C7 | 58.07 (10) | C37—Mo2—C35 | 57.91 (10) |
C8—Mo1—C7 | 34.68 (9) | C34—Mo2—C35 | 34.31 (10) |
C6—Mo1—C7 | 34.61 (10) | C36—Mo2—C35 | 34.28 (10) |
C1—Mo1—P1 | 80.12 (7) | C29—Mo2—P2 | 78.59 (7) |
C2—Mo1—P1 | 79.50 (7) | C30—Mo2—P2 | 78.48 (7) |
C3—Mo1—P1 | 133.55 (6) | C31—Mo2—P2 | 133.28 (6) |
C9—Mo1—P1 | 134.42 (7) | C38—Mo2—P2 | 140.53 (7) |
C10—Mo1—P1 | 141.31 (8) | C37—Mo2—P2 | 139.10 (7) |
C8—Mo1—P1 | 99.33 (7) | C34—Mo2—P2 | 105.85 (8) |
C6—Mo1—P1 | 106.98 (8) | C36—Mo2—P2 | 103.91 (7) |
C7—Mo1—P1 | 85.46 (7) | C35—Mo2—P2 | 87.44 (7) |
C23—P1—C17 | 101.43 (10) | C45—P2—C51 | 101.62 (10) |
C23—P1—C11 | 105.34 (11) | C45—P2—C39 | 103.92 (10) |
C17—P1—C11 | 102.19 (11) | C51—P2—C39 | 101.68 (10) |
C23—P1—Mo1 | 113.94 (7) | C45—P2—Mo2 | 113.86 (7) |
C17—P1—Mo1 | 118.55 (8) | C51—P2—Mo2 | 117.18 (7) |
C11—P1—Mo1 | 113.67 (8) | C39—P2—Mo2 | 116.52 (7) |
O1—C1—Mo1 | 172.5 (2) | O4—C29—Mo2 | 176.6 (2) |
O2—C2—Mo1 | 175.3 (2) | O5—C30—Mo2 | 176.6 (2) |
O3—C3—C4 | 117.9 (2) | O6—C31—C32 | 117.5 (2) |
O3—C3—Mo1 | 120.52 (18) | O6—C31—Mo2 | 119.32 (19) |
C4—C3—Mo1 | 121.58 (17) | C32—C31—Mo2 | 123.17 (17) |
C5—C4—C3 | 115.1 (2) | C33—C32—C31 | 115.8 (2) |
C5—C4—H4A | 108.5 | C33—C32—H32A | 108.3 |
C3—C4—H4A | 108.5 | C31—C32—H32A | 108.3 |
C5—C4—H4B | 108.5 | C33—C32—H32B | 108.3 |
C3—C4—H4B | 108.5 | C31—C32—H32B | 108.3 |
H4A—C4—H4B | 107.5 | H32A—C32—H32B | 107.4 |
C4—C5—H5A | 109.5 | C32—C33—H33A | 109.5 |
C4—C5—H5B | 109.5 | C32—C33—H33B | 109.5 |
H5A—C5—H5B | 109.5 | H33A—C33—H33B | 109.5 |
C4—C5—H5C | 109.5 | C32—C33—H33C | 109.5 |
H5A—C5—H5C | 109.5 | H33A—C33—H33C | 109.5 |
H5B—C5—H5C | 109.5 | H33B—C33—H33C | 109.5 |
C7—C6—C10 | 107.9 (3) | C35—C34—C38 | 108.2 (3) |
C7—C6—Mo1 | 73.13 (14) | C35—C34—Mo2 | 73.66 (16) |
C10—C6—Mo1 | 70.88 (15) | C38—C34—Mo2 | 71.04 (14) |
C7—C6—H6 | 125.9 | C35—C34—H34 | 125.7 |
C10—C6—H6 | 125.9 | C38—C34—H34 | 125.7 |
Mo1—C6—H6 | 125.9 | Mo2—C34—H34 | 125.7 |
C6—C7—C8 | 108.7 (3) | C34—C35—C36 | 108.8 (3) |
C6—C7—Mo1 | 72.26 (14) | C34—C35—Mo2 | 72.03 (15) |
C8—C7—Mo1 | 71.94 (14) | C36—C35—Mo2 | 72.80 (15) |
C6—C7—H7 | 125.6 | C34—C35—H35 | 125.5 |
C8—C7—H7 | 125.6 | C36—C35—H35 | 125.5 |
Mo1—C7—H7 | 125.6 | Mo2—C35—H35 | 125.5 |
C7—C8—C9 | 107.7 (3) | C35—C36—C37 | 107.5 (3) |
C7—C8—Mo1 | 73.38 (14) | C35—C36—Mo2 | 72.92 (15) |
C9—C8—Mo1 | 70.80 (14) | C37—C36—Mo2 | 70.28 (14) |
C7—C8—H8 | 126.0 | C35—C36—H36 | 126.2 |
C9—C8—H8 | 126.0 | C37—C36—H36 | 126.2 |
Mo1—C8—H8 | 126.0 | Mo2—C36—H36 | 126.2 |
C8—C9—C10 | 108.0 (3) | C38—C37—C36 | 107.3 (3) |
C8—C9—Mo1 | 74.01 (14) | C38—C37—Mo2 | 72.04 (14) |
C10—C9—Mo1 | 72.42 (14) | C36—C37—Mo2 | 74.53 (14) |
C8—C9—H9 | 125.8 | C38—C37—H37 | 126.0 |
C10—C9—H9 | 125.8 | C36—C37—H37 | 126.0 |
Mo1—C9—H9 | 125.8 | Mo2—C37—H37 | 126.0 |
C6—C10—C9 | 107.8 (3) | C34—C38—C37 | 108.1 (3) |
C6—C10—Mo1 | 74.08 (15) | C34—C38—Mo2 | 74.19 (15) |
C9—C10—Mo1 | 71.82 (14) | C37—C38—Mo2 | 72.36 (14) |
C6—C10—H10 | 125.9 | C34—C38—H38 | 125.7 |
C9—C10—H10 | 125.9 | C37—C38—H38 | 125.7 |
Mo1—C10—H10 | 125.9 | Mo2—C38—H38 | 125.7 |
C16—C11—C12 | 118.6 (2) | C44—C39—C40 | 118.5 (2) |
C16—C11—P1 | 121.88 (18) | C44—C39—P2 | 121.51 (17) |
C12—C11—P1 | 119.53 (18) | C40—C39—P2 | 119.86 (17) |
C13—C12—C11 | 121.0 (2) | C41—C40—C39 | 120.9 (2) |
C13—C12—H12 | 119.5 | C41—C40—H40 | 119.5 |
C11—C12—H12 | 119.5 | C39—C40—H40 | 119.5 |
C14—C13—C12 | 118.2 (3) | C42—C41—C40 | 118.4 (2) |
C14—C13—H13 | 120.9 | C42—C41—H41 | 120.8 |
C12—C13—H13 | 120.9 | C40—C41—H41 | 120.8 |
F1—C14—C15 | 118.2 (3) | F4—C42—C43 | 118.2 (2) |
F1—C14—C13 | 118.7 (3) | F4—C42—C41 | 119.0 (2) |
C15—C14—C13 | 123.1 (2) | C43—C42—C41 | 122.8 (2) |
C14—C15—C16 | 118.2 (2) | C42—C43—C44 | 118.3 (2) |
C14—C15—H15 | 120.9 | C42—C43—H43 | 120.8 |
C16—C15—H15 | 120.9 | C44—C43—H43 | 120.8 |
C11—C16—C15 | 121.0 (2) | C39—C44—C43 | 121.1 (2) |
C11—C16—H16 | 119.5 | C39—C44—H44 | 119.5 |
C15—C16—H16 | 119.5 | C43—C44—H44 | 119.5 |
C18—C17—C22 | 118.6 (2) | C46—C45—C50 | 118.8 (2) |
C18—C17—P1 | 119.04 (18) | C46—C45—P2 | 122.54 (18) |
C22—C17—P1 | 122.22 (18) | C50—C45—P2 | 118.68 (18) |
C19—C18—C17 | 120.9 (2) | C45—C46—C47 | 120.7 (2) |
C19—C18—H18 | 119.6 | C45—C46—H46 | 119.6 |
C17—C18—H18 | 119.6 | C47—C46—H46 | 119.6 |
C20—C19—C18 | 118.4 (2) | C48—C47—C46 | 118.2 (2) |
C20—C19—H19 | 120.8 | C48—C47—H47 | 120.9 |
C18—C19—H19 | 120.8 | C46—C47—H47 | 120.9 |
F2—C20—C21 | 118.6 (3) | F5—C48—C47 | 118.4 (2) |
F2—C20—C19 | 118.4 (3) | F5—C48—C49 | 118.4 (2) |
C21—C20—C19 | 123.0 (2) | C47—C48—C49 | 123.2 (2) |
C20—C21—C22 | 118.1 (2) | C48—C49—C50 | 118.0 (2) |
C20—C21—H21 | 121.0 | C48—C49—H49 | 121.0 |
C22—C21—H21 | 121.0 | C50—C49—H49 | 121.0 |
C21—C22—C17 | 121.0 (2) | C49—C50—C45 | 121.1 (2) |
C21—C22—H22 | 119.5 | C49—C50—H50 | 119.4 |
C17—C22—H22 | 119.5 | C45—C50—H50 | 119.4 |
C28—C23—C24 | 118.7 (2) | C52—C51—C56 | 118.7 (2) |
C28—C23—P1 | 124.40 (18) | C52—C51—P2 | 121.43 (17) |
C24—C23—P1 | 116.89 (17) | C56—C51—P2 | 119.85 (17) |
C25—C24—C23 | 120.9 (2) | C51—C52—C53 | 120.9 (2) |
C25—C24—H24 | 119.5 | C51—C52—H52 | 119.6 |
C23—C24—H24 | 119.5 | C53—C52—H52 | 119.6 |
C26—C25—C24 | 118.3 (2) | C54—C53—C52 | 118.2 (2) |
C26—C25—H25 | 120.9 | C54—C53—H53 | 120.9 |
C24—C25—H25 | 120.9 | C52—C53—H53 | 120.9 |
C25—C26—F3 | 118.5 (2) | F6—C54—C53 | 118.2 (2) |
C25—C26—C27 | 123.0 (2) | F6—C54—C55 | 118.7 (2) |
F3—C26—C27 | 118.4 (2) | C53—C54—C55 | 123.1 (2) |
C26—C27—C28 | 118.1 (2) | C54—C55—C56 | 118.0 (2) |
C26—C27—H27 | 120.9 | C54—C55—H55 | 121.0 |
C28—C27—H27 | 120.9 | C56—C55—H55 | 121.0 |
C23—C28—C27 | 120.8 (2) | C55—C56—C51 | 121.1 (2) |
C23—C28—H28 | 119.6 | C55—C56—H56 | 119.4 |
C27—C28—H28 | 119.6 | C51—C56—H56 | 119.4 |
O3—C3—C4—C5 | −6.1 (3) | O6—C31—C32—C33 | −4.5 (4) |
Mo1—C3—C4—C5 | 172.61 (18) | Mo2—C31—C32—C33 | 173.63 (19) |
C10—C6—C7—C8 | −0.4 (3) | C38—C34—C35—C36 | 0.9 (3) |
Mo1—C6—C7—C8 | −63.15 (17) | Mo2—C34—C35—C36 | 63.96 (19) |
C10—C6—C7—Mo1 | 62.78 (18) | C38—C34—C35—Mo2 | −63.05 (18) |
C6—C7—C8—C9 | 0.4 (3) | C34—C35—C36—C37 | −1.3 (3) |
Mo1—C7—C8—C9 | −62.91 (17) | Mo2—C35—C36—C37 | 62.17 (18) |
C6—C7—C8—Mo1 | 63.36 (18) | C34—C35—C36—Mo2 | −63.47 (18) |
C7—C8—C9—C10 | −0.4 (3) | C35—C36—C37—C38 | 1.2 (3) |
Mo1—C8—C9—C10 | −64.96 (17) | Mo2—C36—C37—C38 | 65.08 (17) |
C7—C8—C9—Mo1 | 64.60 (17) | C35—C36—C37—Mo2 | −63.90 (18) |
C7—C6—C10—C9 | 0.1 (3) | C35—C34—C38—C37 | −0.2 (3) |
Mo1—C6—C10—C9 | 64.39 (17) | Mo2—C34—C38—C37 | −64.91 (17) |
C7—C6—C10—Mo1 | −64.24 (18) | C35—C34—C38—Mo2 | 64.75 (19) |
C8—C9—C10—C6 | 0.1 (3) | C36—C37—C38—C34 | −0.6 (3) |
Mo1—C9—C10—C6 | −65.88 (18) | Mo2—C37—C38—C34 | 66.12 (18) |
C8—C9—C10—Mo1 | 66.01 (18) | C36—C37—C38—Mo2 | −66.75 (17) |
C23—P1—C11—C16 | 108.3 (2) | C45—P2—C39—C44 | 105.6 (2) |
C17—P1—C11—C16 | 2.7 (2) | C51—P2—C39—C44 | 0.4 (2) |
Mo1—P1—C11—C16 | −126.24 (18) | Mo2—P2—C39—C44 | −128.27 (18) |
C23—P1—C11—C12 | −73.3 (2) | C45—P2—C39—C40 | −79.0 (2) |
C17—P1—C11—C12 | −178.9 (2) | C51—P2—C39—C40 | 175.70 (19) |
Mo1—P1—C11—C12 | 52.1 (2) | Mo2—P2—C39—C40 | 47.1 (2) |
C16—C11—C12—C13 | −1.7 (4) | C44—C39—C40—C41 | 0.4 (4) |
P1—C11—C12—C13 | 179.8 (2) | P2—C39—C40—C41 | −175.1 (2) |
C11—C12—C13—C14 | 1.4 (4) | C39—C40—C41—C42 | 1.6 (4) |
C12—C13—C14—F1 | 179.4 (3) | C40—C41—C42—F4 | 176.8 (2) |
C12—C13—C14—C15 | −0.1 (5) | C40—C41—C42—C43 | −2.8 (4) |
F1—C14—C15—C16 | 179.8 (2) | F4—C42—C43—C44 | −177.7 (2) |
C13—C14—C15—C16 | −0.7 (4) | C41—C42—C43—C44 | 1.9 (4) |
C12—C11—C16—C15 | 0.9 (4) | C40—C39—C44—C43 | −1.3 (4) |
P1—C11—C16—C15 | 179.29 (19) | P2—C39—C44—C43 | 174.10 (19) |
C14—C15—C16—C11 | 0.3 (4) | C42—C43—C44—C39 | 0.2 (4) |
C23—P1—C17—C18 | 164.88 (19) | C51—P2—C45—C46 | 101.2 (2) |
C11—P1—C17—C18 | −86.5 (2) | C39—P2—C45—C46 | −4.1 (2) |
Mo1—P1—C17—C18 | 39.3 (2) | Mo2—P2—C45—C46 | −131.89 (18) |
C23—P1—C17—C22 | −19.6 (2) | C51—P2—C45—C50 | −78.1 (2) |
C11—P1—C17—C22 | 89.0 (2) | C39—P2—C45—C50 | 176.65 (19) |
Mo1—P1—C17—C22 | −145.17 (17) | Mo2—P2—C45—C50 | 48.9 (2) |
C22—C17—C18—C19 | −1.2 (4) | C50—C45—C46—C47 | −0.7 (3) |
P1—C17—C18—C19 | 174.5 (2) | P2—C45—C46—C47 | −179.96 (18) |
C17—C18—C19—C20 | 2.4 (4) | C45—C46—C47—C48 | −0.2 (4) |
C18—C19—C20—F2 | 178.9 (2) | C46—C47—C48—F5 | −177.3 (2) |
C18—C19—C20—C21 | −1.1 (4) | C46—C47—C48—C49 | 1.2 (4) |
F2—C20—C21—C22 | 178.5 (2) | F5—C48—C49—C50 | 177.4 (2) |
C19—C20—C21—C22 | −1.5 (4) | C47—C48—C49—C50 | −1.2 (4) |
C20—C21—C22—C17 | 2.8 (4) | C48—C49—C50—C45 | 0.1 (4) |
C18—C17—C22—C21 | −1.5 (4) | C46—C45—C50—C49 | 0.8 (4) |
P1—C17—C22—C21 | −176.99 (19) | P2—C45—C50—C49 | −179.95 (19) |
C17—P1—C23—C28 | 121.0 (2) | C45—P2—C51—C52 | −10.9 (2) |
C11—P1—C23—C28 | 14.8 (2) | C39—P2—C51—C52 | 96.2 (2) |
Mo1—P1—C23—C28 | −110.42 (19) | Mo2—P2—C51—C52 | −135.61 (17) |
C17—P1—C23—C24 | −59.7 (2) | C45—P2—C51—C56 | 171.36 (19) |
C11—P1—C23—C24 | −165.84 (18) | C39—P2—C51—C56 | −81.6 (2) |
Mo1—P1—C23—C24 | 68.90 (19) | Mo2—P2—C51—C56 | 46.6 (2) |
C28—C23—C24—C25 | −0.9 (4) | C56—C51—C52—C53 | −0.5 (3) |
P1—C23—C24—C25 | 179.73 (19) | P2—C51—C52—C53 | −178.30 (18) |
C23—C24—C25—C26 | 2.5 (4) | C51—C52—C53—C54 | 0.4 (4) |
C24—C25—C26—F3 | 177.5 (2) | C52—C53—C54—F6 | 179.7 (2) |
C24—C25—C26—C27 | −2.2 (4) | C52—C53—C54—C55 | 0.2 (4) |
C25—C26—C27—C28 | 0.4 (4) | F6—C54—C55—C56 | 179.9 (2) |
F3—C26—C27—C28 | −179.3 (2) | C53—C54—C55—C56 | −0.6 (4) |
C24—C23—C28—C27 | −1.0 (3) | C54—C55—C56—C51 | 0.5 (4) |
P1—C23—C28—C27 | 178.31 (18) | C52—C51—C56—C55 | 0.1 (3) |
C26—C27—C28—C23 | 1.3 (4) | P2—C51—C56—C55 | 177.88 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15···O6 | 0.95 | 2.59 | 3.371 (4) | 139 |
C49—H49···F4i | 0.95 | 2.55 | 3.344 (3) | 141 |
C55—H55···O3ii | 0.95 | 2.53 | 3.450 (3) | 164 |
C34—H34···O1iii | 1.00 | 2.38 | 3.237 (3) | 143 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z; (iii) x, −y+1/2, z+1/2. |
[Mo(C5H5)(C3H5O)(C21H21O3P)(CO)2]·CH2Cl2 | Z = 2 |
Mr = 711.39 | F(000) = 728 |
Triclinic, P1 | Dx = 1.508 Mg m−3 |
a = 10.5308 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.1305 (7) Å | Cell parameters from 9554 reflections |
c = 13.6154 (8) Å | θ = 3.0–36.3° |
α = 97.660 (2)° | µ = 0.68 mm−1 |
β = 104.759 (2)° | T = 170 K |
γ = 107.081 (2)° | Block, pale yellow |
V = 1566.43 (16) Å3 | 0.23 × 0.21 × 0.12 mm |
Bruker D8 QUEST ECO diffractometer | 9578 independent reflections |
Radiation source: sealed tube, Siemens KFFMO2K-90C | 9053 reflections with I > 2σ(I) |
Curved Graphite monochromator | Rint = 0.029 |
Detector resolution: 7.3910 pixels mm-1 | θmax = 30.5°, θmin = 2.3° |
φ and ω scans | h = −15→15 |
Absorption correction: multi-scan (Krause et al., 2015) | k = −17→17 |
Tmin = 0.84, Tmax = 0.92 | l = −19→19 |
81820 measured reflections |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.054 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0226P)2 + 0.7135P] where P = (Fo2 + 2Fc2)/3 |
9578 reflections | (Δ/σ)max = 0.001 |
393 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.48 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) | |
Mo1 | 0.52042 (2) | 0.25393 (2) | 0.09427 (2) | 0.01619 (3) | |
P1 | 0.51816 (3) | 0.35557 (2) | 0.26360 (2) | 0.01580 (5) | |
O1 | 0.68635 (12) | 0.51311 (8) | 0.09342 (8) | 0.0368 (2) | |
O2 | 0.71687 (11) | 0.15626 (9) | 0.24292 (8) | 0.0355 (2) | |
O3 | 0.65766 (10) | 0.19845 (9) | −0.07044 (7) | 0.0330 (2) | |
O4 | 0.07178 (10) | 0.57231 (9) | 0.24125 (8) | 0.0335 (2) | |
O5 | 0.41490 (10) | 0.06671 (8) | 0.57748 (7) | 0.03008 (19) | |
O6 | 1.00779 (9) | 0.78117 (8) | 0.52048 (7) | 0.03004 (19) | |
C1 | 0.62823 (12) | 0.41791 (10) | 0.09761 (9) | 0.0227 (2) | |
C2 | 0.64709 (12) | 0.19679 (10) | 0.19028 (8) | 0.0220 (2) | |
C3 | 0.68821 (12) | 0.24759 (10) | 0.02074 (9) | 0.0233 (2) | |
C4 | 0.84445 (13) | 0.30859 (12) | 0.07936 (10) | 0.0301 (2) | |
H4A | 0.878597 | 0.383496 | 0.057367 | 0.036* | |
H4B | 0.857453 | 0.328655 | 0.154986 | 0.036* | |
C5 | 0.93197 (15) | 0.23248 (14) | 0.06042 (13) | 0.0385 (3) | |
H5A | 0.909437 | 0.164404 | 0.092354 | 0.058* | |
H5B | 1.031399 | 0.27963 | 0.091479 | 0.058* | |
H5C | 0.911323 | 0.204489 | −0.01474 | 0.058* | |
C6 | 0.32457 (13) | 0.07480 (10) | 0.03752 (10) | 0.0266 (2) | |
H6 | 0.313597 | 0.0047 | 0.069965 | 0.032* | |
C7 | 0.27424 (12) | 0.16854 (10) | 0.05911 (9) | 0.0246 (2) | |
H7 | 0.222345 | 0.176265 | 0.110302 | 0.03* | |
C8 | 0.29947 (13) | 0.24425 (11) | −0.00983 (10) | 0.0272 (2) | |
H8 | 0.266202 | 0.312821 | −0.017144 | 0.033* | |
C9 | 0.36793 (14) | 0.19845 (12) | −0.07342 (9) | 0.0309 (3) | |
H9 | 0.388632 | 0.227539 | −0.13493 | 0.037* | |
C10 | 0.38374 (14) | 0.09369 (11) | −0.04378 (10) | 0.0306 (3) | |
H10 | 0.418501 | 0.037449 | −0.080607 | 0.037* | |
C11 | 0.37443 (11) | 0.41395 (9) | 0.25087 (8) | 0.01780 (18) | |
C12 | 0.35998 (12) | 0.49063 (10) | 0.18422 (9) | 0.0226 (2) | |
H12 | 0.419737 | 0.505677 | 0.142103 | 0.027* | |
C13 | 0.26014 (12) | 0.54555 (11) | 0.17798 (9) | 0.0237 (2) | |
H13 | 0.252561 | 0.598157 | 0.132747 | 0.028* | |
C14 | 0.17141 (12) | 0.52242 (10) | 0.23893 (9) | 0.0227 (2) | |
C15 | 0.18237 (12) | 0.44423 (11) | 0.30402 (9) | 0.0248 (2) | |
H15 | 0.120263 | 0.426933 | 0.344156 | 0.03* | |
C16 | 0.28358 (12) | 0.39144 (10) | 0.31053 (9) | 0.02147 (19) | |
H16 | 0.291252 | 0.339271 | 0.356177 | 0.026* | |
C17 | 0.05341 (16) | 0.65233 (14) | 0.17571 (14) | 0.0397 (3) | |
H17A | 0.141582 | 0.718094 | 0.192016 | 0.06* | |
H17B | −0.018996 | 0.683173 | 0.187415 | 0.06* | |
H17C | 0.025013 | 0.610782 | 0.102594 | 0.06* | |
C18 | 0.49824 (11) | 0.26789 (9) | 0.36153 (8) | 0.01745 (17) | |
C19 | 0.40076 (12) | 0.15263 (10) | 0.33211 (9) | 0.0235 (2) | |
H19 | 0.351772 | 0.118227 | 0.26037 | 0.028* | |
C20 | 0.37468 (13) | 0.08818 (10) | 0.40562 (9) | 0.0253 (2) | |
H20 | 0.306101 | 0.011206 | 0.384356 | 0.03* | |
C21 | 0.44904 (12) | 0.13610 (10) | 0.51117 (8) | 0.02071 (19) | |
C22 | 0.54956 (12) | 0.24834 (10) | 0.54166 (8) | 0.02109 (19) | |
H22 | 0.602748 | 0.280472 | 0.612987 | 0.025* | |
C23 | 0.57210 (11) | 0.31379 (10) | 0.46696 (8) | 0.02006 (19) | |
H23 | 0.639338 | 0.391388 | 0.488536 | 0.024* | |
C24 | 0.48069 (19) | 0.11574 (13) | 0.68676 (10) | 0.0395 (3) | |
H24A | 0.443749 | 0.058545 | 0.725802 | 0.059* | |
H24B | 0.461623 | 0.188617 | 0.7061 | 0.059* | |
H24C | 0.581792 | 0.133654 | 0.703274 | 0.059* | |
C25 | 0.66885 (11) | 0.48601 (9) | 0.33776 (8) | 0.01716 (17) | |
C26 | 0.65268 (12) | 0.58564 (10) | 0.39084 (9) | 0.0221 (2) | |
H26 | 0.561347 | 0.586707 | 0.38549 | 0.027* | |
C27 | 0.76725 (12) | 0.68248 (10) | 0.45087 (9) | 0.0241 (2) | |
H27 | 0.75409 | 0.749483 | 0.485784 | 0.029* | |
C28 | 0.90179 (12) | 0.68197 (10) | 0.46023 (8) | 0.02111 (19) | |
C29 | 0.92037 (12) | 0.58325 (11) | 0.40946 (9) | 0.0246 (2) | |
H29 | 1.011851 | 0.581542 | 0.416595 | 0.03* | |
C30 | 0.80430 (12) | 0.48711 (10) | 0.34821 (9) | 0.0231 (2) | |
H30 | 0.817702 | 0.420618 | 0.312657 | 0.028* | |
C31 | 1.14412 (14) | 0.79549 (14) | 0.51248 (11) | 0.0366 (3) | |
H31A | 1.178982 | 0.737871 | 0.54421 | 0.055* | |
H31B | 1.207379 | 0.875805 | 0.548891 | 0.055* | |
H31C | 1.139505 | 0.782624 | 0.438867 | 0.055* | |
C32 | −0.0396 (2) | 0.01902 (17) | 0.26603 (16) | 0.0533 (4) | |
H32A | 0.017643 | 0.101022 | 0.305243 | 0.064* | 0.532 (15) |
H32B | −0.133229 | 0.018994 | 0.22801 | 0.064* | 0.532 (15) |
H32C | −0.117475 | 0.043473 | 0.229775 | 0.064* | 0.468 (15) |
H32D | 0.030037 | 0.088435 | 0.319629 | 0.064* | 0.468 (15) |
Cl1A | −0.0560 (9) | −0.0707 (4) | 0.3518 (4) | 0.0661 (11) | 0.532 (15) |
Cl1B | −0.1046 (5) | −0.0962 (5) | 0.3280 (3) | 0.0714 (6) | 0.468 (15) |
Cl2 | 0.03837 (4) | −0.02605 (4) | 0.17571 (4) | 0.05013 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.01913 (4) | 0.01478 (4) | 0.01330 (4) | 0.00475 (3) | 0.00476 (3) | 0.00160 (3) |
P1 | 0.01702 (11) | 0.01515 (11) | 0.01494 (11) | 0.00486 (9) | 0.00573 (9) | 0.00235 (8) |
O1 | 0.0471 (6) | 0.0231 (4) | 0.0411 (5) | 0.0065 (4) | 0.0188 (5) | 0.0125 (4) |
O2 | 0.0443 (6) | 0.0374 (5) | 0.0274 (4) | 0.0239 (5) | 0.0040 (4) | 0.0076 (4) |
O3 | 0.0351 (5) | 0.0415 (5) | 0.0210 (4) | 0.0113 (4) | 0.0121 (4) | −0.0003 (4) |
O4 | 0.0338 (5) | 0.0424 (5) | 0.0407 (5) | 0.0255 (4) | 0.0204 (4) | 0.0176 (4) |
O5 | 0.0403 (5) | 0.0263 (4) | 0.0217 (4) | 0.0052 (4) | 0.0110 (4) | 0.0102 (3) |
O6 | 0.0227 (4) | 0.0239 (4) | 0.0318 (5) | −0.0006 (3) | 0.0043 (3) | −0.0042 (3) |
C1 | 0.0274 (5) | 0.0218 (5) | 0.0199 (5) | 0.0083 (4) | 0.0093 (4) | 0.0050 (4) |
C2 | 0.0271 (5) | 0.0193 (5) | 0.0183 (4) | 0.0080 (4) | 0.0068 (4) | 0.0005 (4) |
C3 | 0.0272 (5) | 0.0224 (5) | 0.0216 (5) | 0.0083 (4) | 0.0104 (4) | 0.0039 (4) |
C4 | 0.0255 (6) | 0.0321 (6) | 0.0292 (6) | 0.0057 (5) | 0.0119 (5) | −0.0018 (5) |
C5 | 0.0319 (7) | 0.0378 (7) | 0.0445 (8) | 0.0145 (6) | 0.0096 (6) | 0.0034 (6) |
C6 | 0.0246 (5) | 0.0185 (5) | 0.0283 (6) | 0.0014 (4) | 0.0026 (4) | 0.0013 (4) |
C7 | 0.0198 (5) | 0.0247 (5) | 0.0238 (5) | 0.0035 (4) | 0.0037 (4) | 0.0029 (4) |
C8 | 0.0242 (5) | 0.0274 (6) | 0.0249 (5) | 0.0074 (4) | 0.0003 (4) | 0.0068 (4) |
C9 | 0.0310 (6) | 0.0369 (7) | 0.0157 (5) | 0.0044 (5) | 0.0017 (4) | 0.0027 (4) |
C10 | 0.0311 (6) | 0.0263 (6) | 0.0237 (5) | 0.0042 (5) | 0.0037 (5) | −0.0077 (4) |
C11 | 0.0175 (4) | 0.0184 (4) | 0.0171 (4) | 0.0056 (4) | 0.0060 (3) | 0.0027 (3) |
C12 | 0.0228 (5) | 0.0263 (5) | 0.0234 (5) | 0.0101 (4) | 0.0114 (4) | 0.0094 (4) |
C13 | 0.0248 (5) | 0.0258 (5) | 0.0250 (5) | 0.0113 (4) | 0.0102 (4) | 0.0097 (4) |
C14 | 0.0203 (5) | 0.0247 (5) | 0.0244 (5) | 0.0098 (4) | 0.0076 (4) | 0.0038 (4) |
C15 | 0.0238 (5) | 0.0309 (6) | 0.0254 (5) | 0.0115 (4) | 0.0133 (4) | 0.0091 (4) |
C16 | 0.0219 (5) | 0.0245 (5) | 0.0206 (5) | 0.0084 (4) | 0.0093 (4) | 0.0075 (4) |
C17 | 0.0368 (7) | 0.0399 (7) | 0.0557 (9) | 0.0245 (6) | 0.0182 (7) | 0.0213 (7) |
C18 | 0.0190 (4) | 0.0173 (4) | 0.0168 (4) | 0.0065 (4) | 0.0064 (3) | 0.0038 (3) |
C19 | 0.0270 (5) | 0.0197 (5) | 0.0178 (5) | 0.0029 (4) | 0.0035 (4) | 0.0027 (4) |
C20 | 0.0289 (6) | 0.0189 (5) | 0.0222 (5) | 0.0017 (4) | 0.0056 (4) | 0.0044 (4) |
C21 | 0.0249 (5) | 0.0210 (5) | 0.0202 (5) | 0.0098 (4) | 0.0099 (4) | 0.0073 (4) |
C22 | 0.0241 (5) | 0.0226 (5) | 0.0157 (4) | 0.0074 (4) | 0.0059 (4) | 0.0035 (4) |
C23 | 0.0213 (5) | 0.0188 (4) | 0.0181 (4) | 0.0046 (4) | 0.0062 (4) | 0.0029 (4) |
C24 | 0.0615 (10) | 0.0355 (7) | 0.0211 (6) | 0.0107 (7) | 0.0169 (6) | 0.0103 (5) |
C25 | 0.0182 (4) | 0.0158 (4) | 0.0169 (4) | 0.0044 (3) | 0.0069 (3) | 0.0020 (3) |
C26 | 0.0199 (5) | 0.0195 (5) | 0.0263 (5) | 0.0069 (4) | 0.0085 (4) | −0.0001 (4) |
C27 | 0.0245 (5) | 0.0179 (5) | 0.0276 (5) | 0.0066 (4) | 0.0082 (4) | −0.0013 (4) |
C28 | 0.0214 (5) | 0.0192 (5) | 0.0187 (4) | 0.0026 (4) | 0.0057 (4) | 0.0020 (4) |
C29 | 0.0182 (5) | 0.0273 (5) | 0.0252 (5) | 0.0062 (4) | 0.0068 (4) | −0.0010 (4) |
C30 | 0.0206 (5) | 0.0224 (5) | 0.0244 (5) | 0.0077 (4) | 0.0073 (4) | −0.0028 (4) |
C31 | 0.0217 (6) | 0.0409 (7) | 0.0324 (6) | −0.0034 (5) | 0.0045 (5) | −0.0004 (5) |
C32 | 0.0701 (12) | 0.0490 (10) | 0.0572 (11) | 0.0328 (9) | 0.0283 (9) | 0.0210 (8) |
Cl1A | 0.104 (3) | 0.0631 (13) | 0.0563 (13) | 0.0427 (15) | 0.0394 (16) | 0.0343 (11) |
Cl1B | 0.0648 (14) | 0.0990 (17) | 0.0501 (10) | 0.0193 (13) | 0.0146 (10) | 0.0415 (9) |
Cl2 | 0.03877 (19) | 0.0537 (2) | 0.0484 (2) | 0.00556 (17) | 0.01330 (16) | 0.00379 (18) |
Mo1—P1 | 2.4745 (3) | C13—C14 | 1.3942 (16) |
Mo1—C1 | 1.9675 (12) | C13—H13 | 0.95 |
Mo1—C2 | 1.9658 (12) | C14—C15 | 1.3908 (16) |
Mo1—C3 | 2.2564 (11) | C15—C16 | 1.3863 (16) |
Mo1—C9 | 2.3092 (12) | C15—H15 | 0.95 |
Mo1—C10 | 2.3210 (12) | C16—H16 | 0.95 |
Mo1—C8 | 2.3562 (12) | C17—H17A | 0.98 |
Mo1—C6 | 2.3833 (12) | C17—H17B | 0.98 |
Mo1—C7 | 2.3835 (11) | C17—H17C | 0.98 |
P1—C25 | 1.8232 (11) | C18—C23 | 1.3925 (14) |
P1—C18 | 1.8283 (11) | C18—C19 | 1.4026 (15) |
P1—C11 | 1.8307 (11) | C19—C20 | 1.3823 (16) |
O1—C1 | 1.1540 (15) | C19—H19 | 0.95 |
O2—C2 | 1.1547 (15) | C20—C21 | 1.3974 (16) |
O3—C3 | 1.2192 (14) | C20—H20 | 0.95 |
O4—C14 | 1.3612 (14) | C21—C22 | 1.3876 (15) |
O4—C17 | 1.4246 (17) | C22—C23 | 1.3959 (15) |
O5—C21 | 1.3576 (13) | C22—H22 | 0.95 |
O5—C24 | 1.4298 (16) | C23—H23 | 0.95 |
O6—C28 | 1.3595 (13) | C24—H24A | 0.98 |
O6—C31 | 1.4287 (16) | C24—H24B | 0.98 |
C3—C4 | 1.5329 (17) | C24—H24C | 0.98 |
C4—C5 | 1.5251 (19) | C25—C30 | 1.3928 (15) |
C4—H4A | 0.99 | C25—C26 | 1.4009 (14) |
C4—H4B | 0.99 | C26—C27 | 1.3830 (15) |
C5—H5A | 0.98 | C26—H26 | 0.95 |
C5—H5B | 0.98 | C27—C28 | 1.3917 (16) |
C5—H5C | 0.98 | C27—H27 | 0.95 |
C6—C10 | 1.4146 (18) | C28—C29 | 1.3914 (16) |
C6—C7 | 1.4159 (17) | C29—C30 | 1.3905 (16) |
C6—H6 | 1.0 | C29—H29 | 0.95 |
C7—C8 | 1.4172 (17) | C30—H30 | 0.95 |
C7—H7 | 1.0 | C31—H31A | 0.98 |
C8—C9 | 1.4153 (19) | C31—H31B | 0.98 |
C8—H8 | 1.0 | C31—H31C | 0.98 |
C9—C10 | 1.426 (2) | C32—Cl1A | 1.705 (3) |
C9—H9 | 1.0 | C32—Cl2 | 1.7561 (19) |
C10—H10 | 1.0 | C32—Cl1B | 1.783 (4) |
C11—C12 | 1.3963 (15) | C32—H32A | 0.99 |
C11—C16 | 1.3970 (14) | C32—H32B | 0.99 |
C12—C13 | 1.3920 (15) | C32—H32C | 0.99 |
C12—H12 | 0.95 | C32—H32D | 0.99 |
C1—Mo1—C2 | 106.36 (5) | C9—C10—Mo1 | 71.62 (7) |
C1—Mo1—C3 | 72.49 (4) | C6—C10—H10 | 125.7 |
C2—Mo1—C3 | 74.79 (4) | C9—C10—H10 | 125.7 |
C2—Mo1—C9 | 140.57 (5) | Mo1—C10—H10 | 125.7 |
C1—Mo1—C9 | 100.33 (5) | C12—C11—C16 | 118.13 (10) |
C3—Mo1—C9 | 86.50 (5) | C12—C11—P1 | 119.07 (8) |
C2—Mo1—C10 | 106.27 (5) | C16—C11—P1 | 122.64 (8) |
C1—Mo1—C10 | 131.51 (5) | C13—C12—C11 | 121.61 (10) |
C3—Mo1—C10 | 82.71 (5) | C13—C12—H12 | 119.2 |
C9—Mo1—C10 | 35.86 (5) | C11—C12—H12 | 119.2 |
C2—Mo1—C8 | 153.82 (5) | C12—C13—C14 | 119.18 (10) |
C1—Mo1—C8 | 99.03 (5) | C12—C13—H13 | 120.4 |
C3—Mo1—C8 | 120.03 (4) | C14—C13—H13 | 120.4 |
C9—Mo1—C8 | 35.30 (5) | O4—C14—C15 | 115.39 (10) |
C10—Mo1—C8 | 58.80 (5) | O4—C14—C13 | 124.68 (11) |
C2—Mo1—C6 | 96.95 (5) | C15—C14—C13 | 119.93 (10) |
C1—Mo1—C6 | 156.61 (5) | C16—C15—C14 | 120.25 (10) |
C3—Mo1—C6 | 112.97 (4) | C16—C15—H15 | 119.9 |
C9—Mo1—C6 | 58.69 (5) | C14—C15—H15 | 119.9 |
C10—Mo1—C6 | 34.97 (5) | C15—C16—C11 | 120.87 (10) |
C8—Mo1—C6 | 58.10 (4) | C15—C16—H16 | 119.6 |
C2—Mo1—C7 | 119.76 (5) | C11—C16—H16 | 119.6 |
C1—Mo1—C7 | 127.63 (5) | O4—C17—H17A | 109.5 |
C3—Mo1—C7 | 140.20 (4) | O4—C17—H17B | 109.5 |
C9—Mo1—C7 | 58.32 (4) | H17A—C17—H17B | 109.5 |
C10—Mo1—C7 | 58.06 (4) | O4—C17—H17C | 109.5 |
C8—Mo1—C7 | 34.79 (4) | H17A—C17—H17C | 109.5 |
C6—Mo1—C7 | 34.56 (4) | H17B—C17—H17C | 109.5 |
C1—Mo1—P1 | 79.97 (3) | C23—C18—C19 | 117.86 (10) |
C2—Mo1—P1 | 79.79 (3) | C23—C18—P1 | 122.10 (8) |
C3—Mo1—P1 | 134.90 (3) | C19—C18—P1 | 119.96 (8) |
C9—Mo1—P1 | 133.97 (4) | C20—C19—C18 | 121.19 (10) |
C10—Mo1—P1 | 140.75 (3) | C20—C19—H19 | 119.4 |
C8—Mo1—P1 | 98.76 (3) | C18—C19—H19 | 119.4 |
C6—Mo1—P1 | 106.54 (3) | C19—C20—C21 | 120.10 (10) |
C7—Mo1—P1 | 84.85 (3) | C19—C20—H20 | 120.0 |
C25—P1—C18 | 102.11 (5) | C21—C20—H20 | 120.0 |
C25—P1—C11 | 101.79 (5) | O5—C21—C22 | 124.58 (10) |
C18—P1—C11 | 102.80 (5) | O5—C21—C20 | 115.76 (10) |
C25—P1—Mo1 | 117.73 (3) | C22—C21—C20 | 119.66 (10) |
C18—P1—Mo1 | 117.30 (3) | C21—C22—C23 | 119.65 (10) |
C11—P1—Mo1 | 112.88 (3) | C21—C22—H22 | 120.2 |
C14—O4—C17 | 118.55 (10) | C23—C22—H22 | 120.2 |
C21—O5—C24 | 117.63 (10) | C18—C23—C22 | 121.48 (10) |
C28—O6—C31 | 117.18 (10) | C18—C23—H23 | 119.3 |
O1—C1—Mo1 | 175.82 (11) | C22—C23—H23 | 119.3 |
O2—C2—Mo1 | 175.76 (10) | O5—C24—H24A | 109.5 |
O3—C3—C4 | 116.42 (11) | O5—C24—H24B | 109.5 |
O3—C3—Mo1 | 120.75 (9) | H24A—C24—H24B | 109.5 |
C4—C3—Mo1 | 122.76 (8) | O5—C24—H24C | 109.5 |
C5—C4—C3 | 113.12 (11) | H24A—C24—H24C | 109.5 |
C5—C4—H4A | 109.0 | H24B—C24—H24C | 109.5 |
C3—C4—H4A | 109.0 | C30—C25—C26 | 117.80 (10) |
C5—C4—H4B | 109.0 | C30—C25—P1 | 120.87 (8) |
C3—C4—H4B | 109.0 | C26—C25—P1 | 121.23 (8) |
H4A—C4—H4B | 107.8 | C27—C26—C25 | 121.21 (10) |
C4—C5—H5A | 109.5 | C27—C26—H26 | 119.4 |
C4—C5—H5B | 109.5 | C25—C26—H26 | 119.4 |
H5A—C5—H5B | 109.5 | C26—C27—C28 | 120.13 (10) |
C4—C5—H5C | 109.5 | C26—C27—H27 | 119.9 |
H5A—C5—H5C | 109.5 | C28—C27—H27 | 119.9 |
H5B—C5—H5C | 109.5 | O6—C28—C29 | 124.40 (10) |
C10—C6—C7 | 107.57 (11) | O6—C28—C27 | 115.94 (10) |
C10—C6—Mo1 | 70.11 (7) | C29—C28—C27 | 119.66 (10) |
C7—C6—Mo1 | 72.73 (7) | C30—C29—C28 | 119.63 (10) |
C10—C6—H6 | 126.1 | C30—C29—H29 | 120.2 |
C7—C6—H6 | 126.1 | C28—C29—H29 | 120.2 |
Mo1—C6—H6 | 126.1 | C29—C30—C25 | 121.55 (10) |
C6—C7—C8 | 108.64 (11) | C29—C30—H30 | 119.2 |
C6—C7—Mo1 | 72.71 (7) | C25—C30—H30 | 119.2 |
C8—C7—Mo1 | 71.55 (7) | O6—C31—H31A | 109.5 |
C6—C7—H7 | 125.6 | O6—C31—H31B | 109.5 |
C8—C7—H7 | 125.6 | H31A—C31—H31B | 109.5 |
Mo1—C7—H7 | 125.6 | O6—C31—H31C | 109.5 |
C9—C8—C7 | 107.71 (11) | H31A—C31—H31C | 109.5 |
C9—C8—Mo1 | 70.54 (7) | H31B—C31—H31C | 109.5 |
C7—C8—Mo1 | 73.66 (7) | Cl1A—C32—Cl2 | 112.38 (13) |
C9—C8—H8 | 126.0 | Cl2—C32—Cl1B | 111.88 (16) |
C7—C8—H8 | 126.0 | Cl1A—C32—H32A | 109.1 |
Mo1—C8—H8 | 126.0 | Cl2—C32—H32A | 109.1 |
C8—C9—C10 | 107.85 (11) | Cl1A—C32—H32B | 109.1 |
C8—C9—Mo1 | 74.16 (7) | Cl2—C32—H32B | 109.1 |
C10—C9—Mo1 | 72.52 (7) | H32A—C32—H32B | 107.9 |
C8—C9—H9 | 125.8 | Cl2—C32—H32C | 109.2 |
C10—C9—H9 | 125.8 | Cl1B—C32—H32C | 109.2 |
Mo1—C9—H9 | 125.8 | Cl2—C32—H32D | 109.2 |
C6—C10—C9 | 108.20 (11) | Cl1B—C32—H32D | 109.2 |
C6—C10—Mo1 | 74.93 (7) | H32C—C32—H32D | 107.9 |
O3—C3—C4—C5 | −45.68 (17) | C11—P1—C18—C23 | −94.92 (9) |
Mo1—C3—C4—C5 | 137.17 (10) | Mo1—P1—C18—C23 | 140.61 (8) |
C10—C6—C7—C8 | 1.13 (13) | C25—P1—C18—C19 | −173.09 (9) |
Mo1—C6—C7—C8 | 62.95 (8) | C11—P1—C18—C19 | 81.66 (10) |
C10—C6—C7—Mo1 | −61.82 (8) | Mo1—P1—C18—C19 | −42.82 (10) |
C6—C7—C8—C9 | −0.97 (13) | C23—C18—C19—C20 | 2.47 (17) |
Mo1—C7—C8—C9 | 62.73 (8) | P1—C18—C19—C20 | −174.25 (10) |
C6—C7—C8—Mo1 | −63.70 (8) | C18—C19—C20—C21 | −2.02 (19) |
C7—C8—C9—C10 | 0.43 (14) | C24—O5—C21—C22 | 4.22 (18) |
Mo1—C8—C9—C10 | 65.20 (9) | C24—O5—C21—C20 | −175.32 (12) |
C7—C8—C9—Mo1 | −64.78 (8) | C19—C20—C21—O5 | 179.25 (11) |
C7—C6—C10—C9 | −0.86 (14) | C19—C20—C21—C22 | −0.32 (18) |
Mo1—C6—C10—C9 | −64.38 (8) | O5—C21—C22—C23 | −177.41 (11) |
C7—C6—C10—Mo1 | 63.52 (8) | C20—C21—C22—C23 | 2.11 (17) |
C8—C9—C10—C6 | 0.27 (14) | C19—C18—C23—C22 | −0.64 (16) |
Mo1—C9—C10—C6 | 66.56 (9) | P1—C18—C23—C22 | 176.00 (8) |
C8—C9—C10—Mo1 | −66.29 (9) | C21—C22—C23—C18 | −1.63 (17) |
C25—P1—C11—C12 | 71.91 (9) | C18—P1—C25—C30 | 86.31 (10) |
C18—P1—C11—C12 | 177.41 (9) | C11—P1—C25—C30 | −167.65 (9) |
Mo1—P1—C11—C12 | −55.25 (9) | Mo1—P1—C25—C30 | −43.70 (10) |
C25—P1—C11—C16 | −103.61 (10) | C18—P1—C25—C26 | −90.06 (10) |
C18—P1—C11—C16 | 1.89 (10) | C11—P1—C25—C26 | 15.98 (10) |
Mo1—P1—C11—C16 | 129.22 (8) | Mo1—P1—C25—C26 | 139.94 (8) |
C16—C11—C12—C13 | 1.21 (17) | C30—C25—C26—C27 | 0.61 (17) |
P1—C11—C12—C13 | −174.52 (9) | P1—C25—C26—C27 | 177.08 (9) |
C11—C12—C13—C14 | −0.71 (18) | C25—C26—C27—C28 | −0.54 (18) |
C17—O4—C14—C15 | −179.30 (12) | C31—O6—C28—C29 | 14.43 (17) |
C17—O4—C14—C13 | 1.31 (19) | C31—O6—C28—C27 | −165.75 (12) |
C12—C13—C14—O4 | 178.64 (11) | C26—C27—C28—O6 | 179.75 (11) |
C12—C13—C14—C15 | −0.72 (18) | C26—C27—C28—C29 | −0.42 (18) |
O4—C14—C15—C16 | −177.78 (11) | O6—C28—C29—C30 | −178.90 (11) |
C13—C14—C15—C16 | 1.64 (18) | C27—C28—C29—C30 | 1.28 (18) |
C14—C15—C16—C11 | −1.13 (18) | C28—C29—C30—C25 | −1.22 (19) |
C12—C11—C16—C15 | −0.28 (17) | C26—C25—C30—C29 | 0.27 (17) |
P1—C11—C16—C15 | 175.28 (9) | P1—C25—C30—C29 | −176.21 (9) |
C25—P1—C18—C23 | 10.34 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
C31—H31B···O5i | 0.98 | 2.58 | 3.4880 (16) | 155 |
C6—H6···O3ii | 1.00 | 2.57 | 3.4555 (16) | 148 |
C8—H8···O1iii | 1.00 | 2.45 | 3.2714 (16) | 139 |
C32—H32B···O2iv | 0.99 | 2.63 | 3.418 (2) | 137 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x+1, −y, −z; (iii) −x+1, −y+1, −z; (iv) x−1, y, z. |
Acknowledgements
Carleton College is acknowledged for partial funding to support purchase of the Bruker D8 Quest ECO diffractometer used to perform this work.
Funding information
Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (award No. CHE-1552591 to M. T. Whited); Camille and Henry Dreyfus Foundation (award No. TH-16-035 to M. T. Whited).
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