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research papers
Synthesis and structure of two isomers of a molybdenum(II) 2-butyne complex stabilized by bioinspired S,N-bidentate ligands
aInstitute of Chemistry, Inorganic Chemistry, University of Graz, Schubertstrasse 1, 8010 Graz, Austria
*Correspondence e-mail: ferdinand.belaj@uni-graz.at
The synthesis and structural determination of two isomers of the molybdenum(II) complex (η2-but-2-yne)carbonylbis[2-(4,4-dimethyl-4,5-dihydro-1,3-oxazol-2-yl)benzenethiolato-κ2N,S]molybdenum(II), [Mo(C11H12NOS)2(C4H6)(CO)] or Mo(CO)(C2Me2)(S-Phoz)2, are presented. The N,N-cis–S,S-trans isomer 1 shows quite different bond lengths to the metal atom [Mo—N = 2.4715 (10) versus 2.3404 (11) Å; Mo—S = 2.4673 (3) versus 2.3665 (3) Å]. In the N,N-trans–S,S-cis isomer 2, which is isotypic with the corresponding W complex, the Mo—N bond lengths [2.236 (2) and 2.203 (2) Å], as well as the Mo—S bond lengths [2.5254 (8) and 2.5297 (8) Å], are almost the same.
Keywords: isomer; 2-butyne complex; molybdenum(II); benzenethiol; crystal structure.
1. Introduction
In order to explore the interaction of Mo and W centres with acetylene (C2H2), which is accepted as a substrate by the tungstoenzyme acetylene hydratase (Schink, 1985; Rosner & Schink, 1995
), our group has focused on the synthesis of WII and MoII complexes containing bioinspired S,N-bidentate ligands and their subsequent oxidation to the respective WIV and MoIV complexes. Although N-donor ligands are not the closest structural mimics of the dithiolene ligands in the active site of acetylene hydratase (Seiffert et al., 2007
) and other members of the dimethyl sulfoxide (DMSO) reductase enzyme family (Seelmann et al., 2020
), the use of these ligands has resulted in the discovery of new reactivities at W centres (Vidovič et al., 2019
; Ehweiner et al., 2021c
), the isolation of a so-far-elusive MoIV C2H2 complex (Ehweiner et al., 2021a
) and a detailed comparison of W and Mo complexes with a variety of coordinated (Ehweiner et al., 2021b
). One of the early publications of our group in this research field focused on the reversible activation of C2H2 at a WIV centre coordinated by two 2-(4,4-dimethyloxazolin-2-yl)thiophenolate (S-Phoz) ligands (Peschel et al., 2015a
). Thereafter, the reversible binding of C2Me2 and C2Ph2 (Peschel et al., 2019
) was investigated, with a particular focus on the flexibility of the S-Phoz ligand. The latter has also found application in Ni, Pd and Pt compounds (Peschel et al., 2015b
; Holzer et al., 2018
), as well as in Zn (Mugesh et al., 1999
) and Fe (Bottini et al., 2010
) complexes.
Herein we report an improved synthetic procedure for Mo(CO)2(S-Phoz)2 and the preparation and structural characterization of carbonyl(η2-1,2-dimethylethyne)[2-(4,4-dimethyloxazolin-2-yl)benzenethiolato-κ2N,S]molydbenum(II), Mo(CO)(C2Me2)(S-Phoz)2, which forms two isomers (1 and 2) in solution, as well as in the solid state (see Scheme 1). This behaviour is different from that observed for the W variant which crystallized solely as the N,N-trans isomer and showed the presence of a second isomer in solution only to a minor extent.
2. Experimental
Synthetic manipulations were performed under a nitrogen atmosphere using standard Schlenk and glove-box techniques. Solvents were purified via a Pure Solv Solvent Purification System. Chemicals were purchased from commercial sources and used without further purification. The precursor MoI2(CO)3(NCMe)2 was synthesized according to a literature procedure (Baker et al., 1986). For the synthesis of Mo(CO)2(S-Phoz)2, a slight modification of a published procedure was used (Peschel et al., 2013
). 1H NMR spectra were recorded on a Bruker Avance III 300 MHz spectrometer at ambient temperature and are referenced to residual protons in the solvent. The multiplicity of peaks is denoted as singlet (s), doublet (d), doublet of doublets (dd) or multiplet (m). NMR solvents were stored over molecular sieves. Solid-state IR spectra were measured on a Bruker ALPHA ATR–FT–IR spectrometer at a resolution of 2 cm−1. The relative intensity of signals is declared as strong (s), medium (m) and weak (w). Electron impact (EI–MS) measurements were performed with an Agilent 5973 MSD with a push rod.
2.1. Synthesis and crystallization
2.1.1. Preparation of Mo(CO)2(S-Phoz)2
A solution of Li(S-Phoz) (853 mg, 4.00 mmol) in MeCN (8 ml) was added dropwise to a solution of MoI2(CO)3(NCMe)2 (1.03 g, 2.00 mmol) in MeCN (8 ml). The resulting blood-red solution was stirred for 2 h at 35 °C, whereupon the solvent was removed by evaporation. The residue was suspended in toluene (20 ml) and the resulting suspension was filtered through Celite. The blood-red filtrate was then evaporated to dryness. After repeated recrystallization from CH2Cl2/heptane at −25 °C, Mo(CO)2(S-Phoz)2 (yield 790 mg, 70%) was obtained as dark red crystals. NMR and IR data are in agreement with previously published results (Peschel et al., 2013).
2.1.2. Preparation of Mo(CO)(C2Me2)(S-Phoz)2
Mo(CO)2(S-Phoz)2 (339 mg, 0.60 mmol) was dissolved in CH2Cl2 (20 ml), whereupon 2-butyne (0.38 ml, 4.80 mmol) was added to the solution at 0 °C under stirring. The cooling bath was removed and the solution was heated under reflux for 24 h. Evaporation of the solvent gave a dark brown powder. Single crystals suitable for X-ray diffraction were obtained from CH2Cl2/heptane solutions at −35 °C. Crystals of both isomers (green plates of 1 and yellow needles of 2) were obtained from the same batch. The product is very sensitive to air and should be stored in a glove-box.
2.1.3. Analytical data
1H NMR for 1 (CD2Cl2, 300 MHz, S,S-trans isomer, 34%): δ 8.07 (dd, J = 8.1, 1.1 Hz, 1H, PhH), 7.78–7.72 (m, 3H, PhH), 7.35 (dd, J = 7.8, 1.1 Hz, 1H, PhH), 7.32–7.27 (m, 2H, PhH), 7.21–7.01 (m, 1H, PhH), 4.46 (d, J = 8.2 Hz, 1H, CH2), 4.18 (d, J = 8.1 Hz, 1H, CH2), 4.11 (d, J = 8.3 Hz, 1H, CH2), 3.78 (d, J = 8.2 Hz, 1H, CH2), 2.70 (s, 3H, C≡CCH3), 2.55 (s, 3H, C≡CCH3), 1.89 (s, 3H, CH3), 1.81 (s, 3H, CH3), 1.57 (s, 3H, CH3), 1.44 (s, 3H, CH3); 1H NMR for 2 (CD2Cl2, 300 MHz, N,N-trans isomer, 66%): δ 7.67–7.62 (m, 2H, PhH), 7.43 (dd, J = 8.1, 1.4 Hz, 1H, PhH), 7.21–7.01 (m, 4H, PhH), 6.90–6.84 (m, 1H, PhH), 4.11 (d, J = 8.3 Hz, 1H, CH2), 3.93–3.90 (m, 3H, CH2), 2.90 (s, 3H, C≡CCH3), 2.46 (s, 3H, C≡CCH3), 1.63 (s, 3H, CH3), 1.34 (s, 3H, CH3), 0.77 (s, 3H, CH3), 0.58 (s, 3H, CH3). IR (cm−1): 2995 (w), 2962 (w), 2928 (w), 2916 (w), 2894 (w), 1898 (s, C≡O), 1856 (m, C≡O), 1590 (s), 1572 (s), 1539 (m, C=N), 1455 (m), 1357 (m), 1326 (m), 1280 (m), 1246 (m), 1208 (m), 1160 (m), 1139 (m), 1053 (s), 966 (m), 818 (m), 776 (m), 741 (s), 695 (m), 653 (m). EI–MS (70 eV) m/z: [M – 2CO + O]+ 526.1.
2.2. Refinement
Crystal data, data collection, and structure . The H atoms of the CH2 groups were placed at positions with approximately tetrahedral angles and C—H distances of 0.99 Å, and common isotropic displacement parameters were refined for the H atoms of the same group. The H atoms of the arene rings were placed at the external bisectors of the C—C—C angles at C—H distances of 0.95 Å, and common isotropic displacement parameters were refined for the H atoms of the same ring. The H atoms of the methyl groups were refined with common isotropic displacement parameters for the H atoms of the same group and idealized geometries with tetrahedral angles, enabling rotations around the C—C bonds, and with C—H distances of 0.98 Å.
|
3. Results and discussion
3.1. analysis
Isomers 1 and 2 crystallize without any solvent molecules in the monoclinic space groups P21/n and P21/c, respectively, and both have one metal complex in the In N,N-cis isomer 1 (Fig. 1), the Mo—N distance of the oxazole ring trans to the butyne ligand [Mo1—N13 = 2.4715 (10) Å] is much longer than that trans to the carbonyl ligand [Mo1—N33 = 2.3404 (11) Å]. In N,N-trans isomer 2 (Fig. 2
), these distances [Mo1—N13 = 2.236 (2) Å and Mo1—N33 = 2.203 (2) Å] are comparable to those observed in the dicarbonyl derivative [2.2333 (9) Å; Peschel et al., 2013
] or in the isotypic W compound [W1—N13 = 2.2153 (16) Å and W1—N33 = 2.1862 (16) Å; Peschel et al., 2019
]. In contrast to this, the Mo—S distances of the benzenethiolate residues in isomer 1 are significantly different, although they are trans to one another, and both are clearly shorter [Mo1—S1 = 2.4673 (3) Å and Mo1—S2 = 2.3665 (3) Å] than in isomer 2 [Mo1—S1 = 2.5254 (8) Å and Mo1—S2 = 2.5297 (8) Å] or in the W compound [W—S = 2.5232 (4)–2.5243 (4) Å]. On the other hand, in both isomers, the distances are almost the same between the central atom and the butyne ligands [2.0310 (12)–2.0664 (12) versus 2.024 (3)–2.059 (3) Å] and to the carbonyl ligands [1.9417 (13) versus 1.953 (3) Å], although both are arranged in trans positions with respect to the N atoms of the oxazole rings in 1, and trans to the S atoms of the benzenethiolate groups in 2. In both isomers, the CO ligands [C3—O3 = 1.1555 (16) and 1.157 (3) Å] lie roughly in the best planes through the butyne ligands [C1—C2 = 1.2965 (18) and 1.314 (4) Å] and the Mo atoms.
![]() | Figure 1 The molecular structure of isomer 1. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. The rather long Mo—N distance [Mo1—N13 = 2.4715 (10) Å] is indicated by a dashed line. |
![]() | Figure 2 The molecular structure of isomer 2. Displacement ellipsoids are drawn at the 50% probability level and H atoms have been omitted for clarity. |
Comparing all known structures of M(CO)(C2R2)(S-Phoz)2 complexes (Table 2), the following conclusions can be made: whereas N,N-trans conformations for R = H and CH3, and S,S-trans conformations for R = Ph were observed (Peschel et al., 2015a
, 2019
) for the W complexes, both conformations were found in the first two crystal structures of the analogous Mo complexes with R = CH3. In general, the Mo—N distances are clearly longer in the S,S-trans conformers, and slightly longer for the S-Phoz ligands trans to the alkyne ligands than those trans to the carbonyl ligand (e.g. M—N13 is larger than M—N33). In isomer 1, the Mo—N distance of the S-Phoz ligand trans to the butyne ligand is exceptionally large due to the wide C1—Mo1—N13 angle of 173.53 (4)° and large C—M—S1 angles. The Mo—S distances are the same in the N,N-trans conformers, but in the S,S-trans conformers, M—S1 is distinctly longer than M—S2. Therefore, the S-Phoz ligands whose oxazole rings are trans to the alkyne ligands are more weakly bound to the metal centre than the others. In all six complexes (Table 2
), the M—C1 distance is significantly shorter than M—C2, presumably due to the carbonyl ligand near atom C2.
|
3.2. NMR spectroscopy
1H NMR spectra recorded in CD2Cl2 and CD3CN show a 1:2 ratio of the two isomers of Mo(CO)(C2Me2)(S-Phoz)2, while a 1:1 ratio is observed in CDCl3. The NMR data of isomer 2, which presumably adopts the N,N-trans configuration, are almost identical with those of the W analogue (Peschel et al., 2019), of which only the N,N-trans isomer was crystallized. In CD2Cl2 solutions, the two isomers of W(CO)(C2Me2)(S-Phoz)2 exhibit a 95:5 ratio, with a clear preference for the N,N-trans configuration of isomer 2.
3.3. IR spectroscopy
The IR spectrum of an average sample of Mo(CO)(C2Me2)(S-Phoz)2 shows a very strong band at 1898 cm−1 which is attributed to the C≡O bond. Due to weaker π-backbonding of the Mo centre, this bond is stronger by 18 cm−1 compared to that in the respective W compound (Peschel et al., 2019), which is in accordance with previous observations on Mo and W carbonyl complexes (Ehweiner et al., 2021a
,b
,c
). Despite the existence of two isomers, only one C≡O bond is visible.
Supporting information
https://doi.org/10.1107/S2053229622002029/wv3008sup1.cif
contains datablocks 1, 2, global. DOI:Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2053229622002029/wv30081sup2.hkl
Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2053229622002029/wv30082sup3.hkl
For both structures, data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELX97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: modified ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).[Mo(C11H12NOS)2(C4H6)(CO)] | F(000) = 1216 |
Mr = 590.59 | Dx = 1.520 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.6159 (5) Å | Cell parameters from 9935 reflections |
b = 8.9300 (4) Å | θ = 2.4–35.8° |
c = 27.3801 (12) Å | µ = 0.70 mm−1 |
β = 96.189 (2)° | T = 100 K |
V = 2580.5 (2) Å3 | Plate, green |
Z = 4 | 0.18 × 0.18 × 0.10 mm |
Bruker APEXII CCD diffractometer | 11363 independent reflections |
Radiation source: Incoatec microfocus sealed tube | 9549 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.029 |
φ and ω scans | θmax = 35.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | h = −17→17 |
Tmin = 0.884, Tmax = 1.000 | k = −14→11 |
30042 measured reflections | l = −44→42 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.028 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.071 | Only H-atom displacement parameters refined |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0331P)2 + 0.5019P] where P = (Fo2 + 2Fc2)/3 |
11363 reflections | (Δ/σ)max = 0.008 |
332 parameters | Δρmax = 0.72 e Å−3 |
0 restraints | Δρmin = −0.64 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The non-hydrogen atoms were refined with anisotropic displacement parameters without any constraints. The H atoms of the CH2 groups were put at positions with approx. tetrahedral angles and C-H distances of 0.99 Å, and common isotropic displacement parameters were refined for the H atoms of the same group (AFIX 23 of SHELXL). The H atoms of the phenyl rings were put at the external bisectors of the C-C-C angles at C-H distances of 0.95 Å and common isotropic displacement parameters were refined for the H atoms of the same ring (AFIX 43 of SHELXL). The H atoms of the methyl groups were refined with common isotropic displacement parameters for the H atoms of the same group and idealized geometries with tetrahedral angles, enabling rotations around the C-C bonds, and C-H distances of 0.98 Å (AFIX 137 of SHELXL). |
x | y | z | Uiso*/Ueq | ||
Mo1 | 0.89263 (2) | 0.62618 (2) | 0.60957 (2) | 0.00748 (3) | |
C10 | 0.79768 (14) | 0.34484 (15) | 0.53122 (5) | 0.0169 (2) | |
H101 | 0.8405 | 0.3231 | 0.5020 | 0.032 (3)* | |
H102 | 0.7171 | 0.3954 | 0.5213 | 0.032 (3)* | |
H103 | 0.7816 | 0.2510 | 0.5480 | 0.032 (3)* | |
C1 | 0.87961 (12) | 0.44360 (14) | 0.56508 (4) | 0.0118 (2) | |
C2 | 0.99846 (12) | 0.46043 (14) | 0.58069 (4) | 0.0116 (2) | |
C20 | 1.12488 (14) | 0.39396 (16) | 0.57708 (6) | 0.0196 (3) | |
H201 | 1.1150 | 0.2896 | 0.5663 | 0.065 (5)* | |
H202 | 1.1748 | 0.3975 | 0.6093 | 0.065 (5)* | |
H203 | 1.1685 | 0.4507 | 0.5533 | 0.065 (5)* | |
C3 | 1.07172 (12) | 0.65704 (14) | 0.62980 (4) | 0.0117 (2) | |
O3 | 1.17882 (9) | 0.67813 (12) | 0.63972 (4) | 0.01788 (19) | |
O11 | 0.93259 (10) | 0.95082 (11) | 0.74208 (3) | 0.01669 (18) | |
C12 | 0.94202 (12) | 0.82783 (14) | 0.71368 (4) | 0.0116 (2) | |
N13 | 0.88974 (10) | 0.83507 (11) | 0.66865 (3) | 0.00967 (17) | |
C14 | 0.84945 (12) | 0.99714 (13) | 0.66127 (4) | 0.01058 (19) | |
C15 | 0.84074 (13) | 1.04622 (14) | 0.71414 (4) | 0.0151 (2) | |
H151 | 0.8632 | 1.1533 | 0.7188 | 0.015 (3)* | |
H152 | 0.7545 | 1.0296 | 0.7237 | 0.015 (3)* | |
C16 | 0.72358 (12) | 1.01441 (14) | 0.63024 (5) | 0.0140 (2) | |
H161 | 0.7321 | 0.9824 | 0.5965 | 0.024 (3)* | |
H162 | 0.6973 | 1.1196 | 0.6302 | 0.024 (3)* | |
H163 | 0.6597 | 0.9525 | 0.6439 | 0.024 (3)* | |
C17 | 0.95572 (13) | 1.08459 (15) | 0.64041 (5) | 0.0162 (2) | |
H171 | 0.9662 | 1.0476 | 0.6074 | 0.023 (3)* | |
H172 | 1.0350 | 1.0709 | 0.6618 | 0.023 (3)* | |
H173 | 0.9339 | 1.1912 | 0.6387 | 0.023 (3)* | |
S1 | 0.86588 (3) | 0.49578 (3) | 0.68722 (2) | 0.01150 (6) | |
C21 | 0.99285 (12) | 0.55484 (14) | 0.72917 (4) | 0.0120 (2) | |
C22 | 1.01709 (12) | 0.70709 (14) | 0.73914 (4) | 0.0122 (2) | |
C23 | 1.11465 (13) | 0.74917 (17) | 0.77533 (4) | 0.0175 (2) | |
H23 | 1.1303 | 0.8523 | 0.7821 | 0.028 (3)* | |
C24 | 1.18814 (15) | 0.64158 (18) | 0.80126 (5) | 0.0225 (3) | |
H24 | 1.2544 | 0.6707 | 0.8255 | 0.028 (3)* | |
C25 | 1.16465 (15) | 0.49087 (18) | 0.79168 (5) | 0.0225 (3) | |
H25 | 1.2149 | 0.4169 | 0.8095 | 0.028 (3)* | |
C26 | 1.06824 (14) | 0.44795 (16) | 0.75624 (5) | 0.0178 (2) | |
H26 | 1.0529 | 0.3445 | 0.7502 | 0.028 (3)* | |
O31 | 0.48698 (9) | 0.68836 (11) | 0.54235 (3) | 0.01576 (18) | |
C32 | 0.61444 (11) | 0.70736 (13) | 0.54906 (4) | 0.01009 (19) | |
N33 | 0.67394 (10) | 0.64237 (11) | 0.58729 (4) | 0.00932 (17) | |
C34 | 0.57211 (11) | 0.57021 (14) | 0.61487 (4) | 0.0110 (2) | |
C35 | 0.45570 (12) | 0.57671 (16) | 0.57686 (5) | 0.0154 (2) | |
H351 | 0.4402 | 0.4785 | 0.5605 | 0.022 (3)* | |
H352 | 0.3794 | 0.6060 | 0.5924 | 0.022 (3)* | |
C36 | 0.55298 (13) | 0.66662 (15) | 0.65962 (5) | 0.0155 (2) | |
H361 | 0.4919 | 0.6179 | 0.6788 | 0.019 (3)* | |
H362 | 0.5207 | 0.7652 | 0.6487 | 0.019 (3)* | |
H363 | 0.6341 | 0.6785 | 0.6800 | 0.019 (3)* | |
C37 | 0.59886 (13) | 0.40709 (14) | 0.62857 (5) | 0.0148 (2) | |
H371 | 0.6322 | 0.3555 | 0.6011 | 0.029 (3)* | |
H372 | 0.5202 | 0.3585 | 0.6358 | 0.029 (3)* | |
H373 | 0.6614 | 0.4023 | 0.6576 | 0.029 (3)* | |
S2 | 0.91487 (3) | 0.81414 (3) | 0.55017 (2) | 0.01031 (5) | |
C41 | 0.78108 (11) | 0.85979 (13) | 0.51004 (4) | 0.00942 (19) | |
C42 | 0.65755 (12) | 0.80444 (13) | 0.51052 (4) | 0.01027 (19) | |
C43 | 0.56414 (13) | 0.84871 (15) | 0.47232 (5) | 0.0155 (2) | |
H43 | 0.4802 | 0.8117 | 0.4722 | 0.020 (2)* | |
C44 | 0.59196 (14) | 0.94420 (16) | 0.43528 (5) | 0.0184 (2) | |
H44 | 0.5284 | 0.9694 | 0.4095 | 0.020 (2)* | |
C45 | 0.71325 (13) | 1.00322 (15) | 0.43593 (5) | 0.0159 (2) | |
H45 | 0.7324 | 1.0715 | 0.4112 | 0.020 (2)* | |
C46 | 0.80578 (13) | 0.96192 (14) | 0.47282 (4) | 0.0128 (2) | |
H46 | 0.8883 | 1.0033 | 0.4732 | 0.020 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.00739 (4) | 0.00758 (4) | 0.00757 (4) | 0.00003 (3) | 0.00130 (3) | −0.00047 (3) |
C10 | 0.0187 (6) | 0.0167 (6) | 0.0149 (5) | −0.0037 (5) | 0.0000 (4) | −0.0055 (4) |
C1 | 0.0156 (6) | 0.0095 (5) | 0.0105 (4) | −0.0010 (4) | 0.0020 (4) | −0.0013 (4) |
C2 | 0.0134 (5) | 0.0106 (5) | 0.0113 (4) | 0.0013 (4) | 0.0036 (4) | −0.0019 (4) |
C20 | 0.0141 (6) | 0.0183 (6) | 0.0274 (7) | 0.0035 (5) | 0.0063 (5) | −0.0073 (5) |
C3 | 0.0134 (5) | 0.0110 (5) | 0.0108 (4) | 0.0002 (4) | 0.0021 (4) | −0.0020 (4) |
O3 | 0.0106 (4) | 0.0223 (5) | 0.0205 (4) | −0.0016 (4) | 0.0008 (3) | −0.0043 (4) |
O11 | 0.0243 (5) | 0.0138 (4) | 0.0110 (4) | 0.0063 (4) | −0.0023 (3) | −0.0052 (3) |
C12 | 0.0127 (5) | 0.0112 (5) | 0.0109 (4) | 0.0016 (4) | 0.0015 (4) | −0.0021 (4) |
N13 | 0.0106 (4) | 0.0086 (4) | 0.0098 (4) | 0.0009 (3) | 0.0011 (3) | −0.0003 (3) |
C14 | 0.0123 (5) | 0.0082 (4) | 0.0112 (4) | 0.0011 (4) | 0.0011 (4) | −0.0010 (4) |
C15 | 0.0205 (6) | 0.0119 (5) | 0.0128 (5) | 0.0063 (5) | 0.0011 (4) | −0.0017 (4) |
C16 | 0.0137 (6) | 0.0118 (5) | 0.0163 (5) | 0.0027 (4) | 0.0003 (4) | 0.0010 (4) |
C17 | 0.0171 (6) | 0.0118 (5) | 0.0201 (6) | −0.0038 (5) | 0.0042 (5) | −0.0016 (4) |
S1 | 0.01297 (13) | 0.01097 (12) | 0.01060 (11) | −0.00069 (10) | 0.00153 (9) | 0.00193 (9) |
C21 | 0.0122 (5) | 0.0142 (5) | 0.0096 (4) | 0.0022 (4) | 0.0019 (4) | 0.0015 (4) |
C22 | 0.0125 (5) | 0.0143 (5) | 0.0096 (4) | 0.0031 (4) | 0.0007 (4) | 0.0000 (4) |
C23 | 0.0178 (6) | 0.0204 (6) | 0.0134 (5) | 0.0033 (5) | −0.0031 (4) | −0.0033 (4) |
C24 | 0.0200 (7) | 0.0277 (7) | 0.0179 (6) | 0.0063 (6) | −0.0065 (5) | −0.0030 (5) |
C25 | 0.0229 (7) | 0.0256 (7) | 0.0177 (6) | 0.0096 (6) | −0.0042 (5) | 0.0049 (5) |
C26 | 0.0204 (6) | 0.0161 (6) | 0.0165 (5) | 0.0041 (5) | −0.0003 (5) | 0.0038 (4) |
O31 | 0.0087 (4) | 0.0192 (5) | 0.0189 (4) | −0.0033 (3) | −0.0008 (3) | 0.0071 (3) |
C32 | 0.0088 (5) | 0.0101 (5) | 0.0114 (4) | −0.0017 (4) | 0.0012 (4) | −0.0012 (4) |
N33 | 0.0087 (4) | 0.0090 (4) | 0.0104 (4) | −0.0010 (3) | 0.0020 (3) | 0.0002 (3) |
C34 | 0.0090 (5) | 0.0118 (5) | 0.0127 (5) | −0.0022 (4) | 0.0028 (4) | 0.0011 (4) |
C35 | 0.0103 (5) | 0.0175 (6) | 0.0182 (5) | −0.0040 (5) | 0.0006 (4) | 0.0063 (4) |
C36 | 0.0167 (6) | 0.0152 (5) | 0.0156 (5) | −0.0013 (5) | 0.0070 (4) | 0.0005 (4) |
C37 | 0.0146 (6) | 0.0099 (5) | 0.0201 (5) | −0.0026 (4) | 0.0022 (4) | 0.0028 (4) |
S2 | 0.00911 (12) | 0.01204 (12) | 0.00983 (11) | −0.00215 (10) | 0.00123 (9) | 0.00168 (9) |
C41 | 0.0105 (5) | 0.0092 (5) | 0.0089 (4) | −0.0001 (4) | 0.0023 (4) | −0.0009 (3) |
C42 | 0.0112 (5) | 0.0099 (5) | 0.0096 (4) | −0.0012 (4) | 0.0006 (4) | 0.0003 (4) |
C43 | 0.0142 (6) | 0.0170 (6) | 0.0145 (5) | −0.0014 (4) | −0.0017 (4) | 0.0030 (4) |
C44 | 0.0177 (6) | 0.0207 (6) | 0.0157 (5) | −0.0007 (5) | −0.0030 (4) | 0.0066 (5) |
C45 | 0.0191 (6) | 0.0155 (6) | 0.0131 (5) | −0.0001 (5) | 0.0020 (4) | 0.0047 (4) |
C46 | 0.0147 (6) | 0.0126 (5) | 0.0116 (5) | −0.0009 (4) | 0.0030 (4) | 0.0019 (4) |
Mo1—C1 | 2.0310 (12) | C22—C23 | 1.4052 (18) |
Mo1—C2 | 2.0664 (12) | C23—C24 | 1.384 (2) |
Mo1—C3 | 1.9417 (13) | C23—H23 | 0.95 |
Mo1—N13 | 2.4715 (10) | C24—C25 | 1.389 (2) |
Mo1—N33 | 2.3404 (11) | C24—H24 | 0.95 |
Mo1—S1 | 2.4673 (3) | C25—C26 | 1.386 (2) |
Mo1—S2 | 2.3665 (3) | C25—H25 | 0.95 |
C1—C2 | 1.2965 (18) | C26—H26 | 0.95 |
C1—C10 | 1.4899 (17) | O31—C32 | 1.3564 (15) |
C10—H101 | 0.98 | O31—C35 | 1.4370 (15) |
C10—H102 | 0.98 | C32—N33 | 1.2996 (15) |
C10—H103 | 0.98 | C32—C42 | 1.4759 (16) |
C2—C20 | 1.4804 (19) | N33—C34 | 1.5264 (15) |
C20—H201 | 0.98 | C34—C37 | 1.5233 (18) |
C20—H202 | 0.98 | C34—C35 | 1.5285 (18) |
C20—H203 | 0.98 | C34—C36 | 1.5288 (17) |
C3—O3 | 1.1555 (16) | C35—H351 | 0.99 |
O11—C12 | 1.3558 (15) | C35—H352 | 0.99 |
O11—C15 | 1.4494 (16) | C36—H361 | 0.98 |
C12—N13 | 1.2978 (15) | C36—H362 | 0.98 |
C12—C22 | 1.4710 (17) | C36—H363 | 0.98 |
N13—C14 | 1.5166 (15) | C37—H371 | 0.98 |
C14—C16 | 1.5120 (18) | C37—H372 | 0.98 |
C14—C15 | 1.5247 (16) | C37—H373 | 0.98 |
C14—C17 | 1.5322 (18) | S2—C41 | 1.7477 (12) |
C15—H151 | 0.99 | C41—C42 | 1.4029 (17) |
C15—H152 | 0.99 | C41—C46 | 1.4131 (16) |
C16—H161 | 0.98 | C42—C43 | 1.4177 (17) |
C16—H162 | 0.98 | C43—C44 | 1.3811 (18) |
C16—H163 | 0.98 | C43—H43 | 0.95 |
C17—H171 | 0.98 | C44—C45 | 1.390 (2) |
C17—H172 | 0.98 | C44—H44 | 0.95 |
C17—H173 | 0.98 | C45—C46 | 1.3810 (18) |
S1—C21 | 1.7551 (13) | C45—H45 | 0.95 |
C21—C26 | 1.4046 (18) | C46—H46 | 0.95 |
C21—C22 | 1.4051 (18) | ||
N13—Mo1—N33 | 92.41 (3) | H172—C17—H173 | 109.5 |
S1—Mo1—S2 | 162.979 (11) | C21—S1—Mo1 | 105.69 (4) |
C1—Mo1—N13 | 173.53 (4) | C26—C21—C22 | 118.23 (12) |
C2—Mo1—N13 | 146.80 (4) | C26—C21—S1 | 119.66 (10) |
C3—Mo1—N33 | 168.19 (4) | C22—C21—S1 | 121.97 (9) |
C3—Mo1—C1 | 106.63 (5) | C21—C22—C23 | 120.09 (11) |
C3—Mo1—C2 | 69.81 (5) | C21—C22—C12 | 122.60 (11) |
C1—Mo1—C2 | 36.88 (5) | C23—C22—C12 | 117.30 (12) |
C1—Mo1—N33 | 83.79 (4) | C24—C23—C22 | 120.52 (13) |
C2—Mo1—N33 | 120.63 (4) | C24—C23—H23 | 119.7 |
C3—Mo1—S2 | 85.88 (4) | C22—C23—H23 | 119.7 |
C1—Mo1—S2 | 99.36 (3) | C23—C24—C25 | 119.73 (13) |
C2—Mo1—S2 | 98.42 (3) | C23—C24—H24 | 120.1 |
N33—Mo1—S2 | 86.95 (3) | C25—C24—H24 | 120.1 |
C3—Mo1—S1 | 91.22 (4) | C26—C25—C24 | 120.28 (13) |
C1—Mo1—S1 | 97.54 (3) | C26—C25—H25 | 119.9 |
C2—Mo1—S1 | 96.29 (3) | C24—C25—H25 | 119.9 |
N33—Mo1—S1 | 92.90 (2) | C25—C26—C21 | 121.14 (13) |
C3—Mo1—N13 | 77.70 (4) | C25—C26—H26 | 119.4 |
S2—Mo1—N13 | 85.62 (2) | C21—C26—H26 | 119.4 |
S1—Mo1—N13 | 77.38 (2) | C32—O31—C35 | 107.19 (9) |
C1—C10—H101 | 109.5 | N33—C32—O31 | 116.38 (10) |
C1—C10—H102 | 109.5 | N33—C32—C42 | 132.61 (11) |
H101—C10—H102 | 109.5 | O31—C32—C42 | 110.99 (10) |
C1—C10—H103 | 109.5 | C32—N33—C34 | 106.17 (10) |
H101—C10—H103 | 109.5 | C32—N33—Mo1 | 128.30 (8) |
H102—C10—H103 | 109.5 | C34—N33—Mo1 | 125.49 (7) |
C2—C1—C10 | 139.10 (12) | C37—C34—N33 | 113.73 (10) |
C2—C1—Mo1 | 73.04 (7) | C37—C34—C35 | 108.63 (10) |
C10—C1—Mo1 | 147.76 (10) | N33—C34—C35 | 102.17 (9) |
C1—C2—C20 | 142.05 (12) | C37—C34—C36 | 112.24 (10) |
C1—C2—Mo1 | 70.08 (7) | N33—C34—C36 | 108.73 (10) |
C20—C2—Mo1 | 147.87 (10) | C35—C34—C36 | 110.91 (11) |
C2—C20—H201 | 109.5 | O31—C35—C34 | 104.29 (10) |
C2—C20—H202 | 109.5 | O31—C35—H351 | 110.9 |
H201—C20—H202 | 109.5 | C34—C35—H351 | 110.9 |
C2—C20—H203 | 109.5 | O31—C35—H352 | 110.9 |
H201—C20—H203 | 109.5 | C34—C35—H352 | 110.9 |
H202—C20—H203 | 109.5 | H351—C35—H352 | 108.9 |
Mo1—C3—O3 | 176.84 (11) | C34—C36—H361 | 109.5 |
C12—O11—C15 | 105.09 (9) | C34—C36—H362 | 109.5 |
N13—C12—O11 | 117.01 (11) | H361—C36—H362 | 109.5 |
N13—C12—C22 | 129.87 (11) | C34—C36—H363 | 109.5 |
O11—C12—C22 | 113.06 (10) | H361—C36—H363 | 109.5 |
C12—N13—C14 | 105.05 (9) | H362—C36—H363 | 109.5 |
C12—N13—Mo1 | 123.36 (8) | C34—C37—H371 | 109.5 |
C14—N13—Mo1 | 131.02 (7) | C34—C37—H372 | 109.5 |
C16—C14—N13 | 113.06 (10) | H371—C37—H372 | 109.5 |
C16—C14—C15 | 111.33 (10) | C34—C37—H373 | 109.5 |
N13—C14—C15 | 101.12 (9) | H371—C37—H373 | 109.5 |
C16—C14—C17 | 112.34 (10) | H372—C37—H373 | 109.5 |
N13—C14—C17 | 109.12 (10) | C41—S2—Mo1 | 117.58 (4) |
C15—C14—C17 | 109.25 (10) | C42—C41—C46 | 118.72 (11) |
O11—C15—C14 | 103.06 (9) | C42—C41—S2 | 127.52 (9) |
O11—C15—H151 | 111.2 | C46—C41—S2 | 113.74 (9) |
C14—C15—H151 | 111.2 | C41—C42—C43 | 118.36 (11) |
O11—C15—H152 | 111.2 | C41—C42—C32 | 125.16 (11) |
C14—C15—H152 | 111.2 | C43—C42—C32 | 116.43 (11) |
H151—C15—H152 | 109.1 | C44—C43—C42 | 121.73 (12) |
C14—C16—H161 | 109.5 | C44—C43—H43 | 119.1 |
C14—C16—H162 | 109.5 | C42—C43—H43 | 119.1 |
H161—C16—H162 | 109.5 | C43—C44—C45 | 119.73 (12) |
C14—C16—H163 | 109.5 | C43—C44—H44 | 120.1 |
H161—C16—H163 | 109.5 | C45—C44—H44 | 120.1 |
H162—C16—H163 | 109.5 | C46—C45—C44 | 119.55 (12) |
C14—C17—H171 | 109.5 | C46—C45—H45 | 120.2 |
C14—C17—H172 | 109.5 | C44—C45—H45 | 120.2 |
H171—C17—H172 | 109.5 | C45—C46—C41 | 121.81 (12) |
C14—C17—H173 | 109.5 | C45—C46—H46 | 119.1 |
H171—C17—H173 | 109.5 | C41—C46—H46 | 119.1 |
C1—C2—Mo1—C3 | −176.82 (9) | C22—C21—C26—C25 | −0.4 (2) |
C10—C1—C2—C20 | −2.9 (3) | S1—C21—C26—C25 | −176.27 (11) |
Mo1—C1—C2—C20 | −179.67 (19) | C35—O31—C32—N33 | −9.48 (15) |
Mo1—C2—C1—C10 | 176.81 (17) | C35—O31—C32—C42 | 171.98 (10) |
C15—O11—C12—N13 | 11.37 (15) | O31—C32—N33—C34 | −3.53 (14) |
C15—O11—C12—C22 | −171.33 (11) | C42—C32—N33—C34 | 174.63 (12) |
O11—C12—N13—C14 | 8.08 (15) | O31—C32—N33—Mo1 | 174.03 (8) |
C22—C12—N13—C14 | −168.70 (13) | C42—C32—N33—Mo1 | −7.82 (19) |
O11—C12—N13—Mo1 | −179.70 (8) | C32—N33—C34—C37 | 130.83 (11) |
C22—C12—N13—Mo1 | 3.52 (19) | Mo1—N33—C34—C37 | −46.81 (13) |
C12—N13—C14—C16 | −141.83 (11) | C32—N33—C34—C35 | 13.97 (12) |
Mo1—N13—C14—C16 | 46.79 (14) | Mo1—N33—C34—C35 | −163.67 (8) |
C12—N13—C14—C15 | −22.71 (13) | C32—N33—C34—C36 | −103.33 (11) |
Mo1—N13—C14—C15 | 165.91 (8) | Mo1—N33—C34—C36 | 79.03 (11) |
C12—N13—C14—C17 | 92.37 (12) | C32—O31—C35—C34 | 17.70 (13) |
Mo1—N13—C14—C17 | −79.01 (12) | C37—C34—C35—O31 | −139.33 (11) |
C12—O11—C15—C14 | −25.04 (13) | N33—C34—C35—O31 | −18.86 (12) |
C16—C14—C15—O11 | 148.99 (11) | C36—C34—C35—O31 | 96.87 (12) |
N13—C14—C15—O11 | 28.64 (12) | Mo1—S2—C41—C42 | 4.37 (12) |
C17—C14—C15—O11 | −86.35 (12) | Mo1—S2—C41—C46 | −174.05 (7) |
Mo1—S1—C21—C26 | −129.28 (10) | C46—C41—C42—C43 | 2.65 (17) |
Mo1—S1—C21—C22 | 55.02 (10) | S2—C41—C42—C43 | −175.70 (9) |
C26—C21—C22—C23 | 0.06 (18) | C46—C41—C42—C32 | −174.71 (11) |
S1—C21—C22—C23 | 175.83 (10) | S2—C41—C42—C32 | 6.94 (18) |
C26—C21—C22—C12 | −178.65 (12) | N33—C32—C42—C41 | −5.9 (2) |
S1—C21—C22—C12 | −2.89 (16) | O31—C32—C42—C41 | 172.29 (11) |
N13—C12—C22—C21 | −34.6 (2) | N33—C32—C42—C43 | 176.66 (13) |
O11—C12—C22—C21 | 148.52 (12) | O31—C32—C42—C43 | −5.11 (15) |
N13—C12—C22—C23 | 146.65 (14) | C41—C42—C43—C44 | −0.19 (19) |
O11—C12—C22—C23 | −30.23 (16) | C32—C42—C43—C44 | 177.40 (12) |
C21—C22—C23—C24 | 0.4 (2) | C42—C43—C44—C45 | −2.2 (2) |
C12—C22—C23—C24 | 179.16 (13) | C43—C44—C45—C46 | 2.0 (2) |
C22—C23—C24—C25 | −0.5 (2) | C44—C45—C46—C41 | 0.5 (2) |
C23—C24—C25—C26 | 0.1 (2) | C42—C41—C46—C45 | −2.86 (18) |
C24—C25—C26—C21 | 0.3 (2) | S2—C41—C46—C45 | 175.71 (10) |
[Mo(C11H12NOS)2(C4H6)(CO)] | F(000) = 1216 |
Mr = 590.59 | Dx = 1.540 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1512 (4) Å | Cell parameters from 3132 reflections |
b = 21.3515 (12) Å | θ = 2.4–26.8° |
c = 13.1781 (7) Å | µ = 0.71 mm−1 |
β = 98.483 (3)° | T = 100 K |
V = 2546.7 (2) Å3 | Needle, yellow |
Z = 4 | 0.23 × 0.07 × 0.07 mm |
Bruker APEXII CCD diffractometer | 7415 independent reflections |
Radiation source: Incoatec microfocus sealed tube | 5339 reflections with I > 2σ(I) |
Multilayer monochromator | Rint = 0.068 |
φ and ω scans | θmax = 30.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | h = −9→12 |
Tmin = 0.776, Tmax = 1.000 | k = −23→30 |
22009 measured reflections | l = −18→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | Only H-atom displacement parameters refined |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0231P)2 + 1.0578P] where P = (Fo2 + 2Fc2)/3 |
7415 reflections | (Δ/σ)max = 0.001 |
332 parameters | Δρmax = 0.52 e Å−3 |
0 restraints | Δρmin = −0.83 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. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The non-hydrogen atoms were refined with anisotropic displacement parameters without any constraints. The H atoms of the CH2 groups were put at positions with approx. tetrahedral angles and C-H distances of 0.99 Å, and common isotropic displacement parameters were refined for the H atoms of the same group (AFIX 23 of SHELXL). The H atoms of the phenyl rings were put at the external bisectors of the C-C-C angles at C-H distances of 0.95 Å and common isotropic displacement parameters were refined for the H atoms of the same ring (AFIX 43 of SHELXL). The H atoms of the methyl groups were refined with common isotropic displacement parameters for the H atoms of the same group and idealized geometries with tetrahedral angles, enabling rotations around the C-C bonds, and C-H distances of 0.98 Å (AFIX 137 of SHELXL). |
x | y | z | Uiso*/Ueq | ||
Mo1 | 0.72006 (2) | 0.85241 (2) | 0.32592 (2) | 0.00779 (6) | |
C10 | 0.6039 (3) | 0.75606 (14) | 0.5024 (2) | 0.0153 (6) | |
H101 | 0.6362 | 0.7619 | 0.5760 | 0.029 (6)* | |
H102 | 0.6544 | 0.7197 | 0.4784 | 0.029 (6)* | |
H103 | 0.4969 | 0.7491 | 0.4899 | 0.029 (6)* | |
C1 | 0.6403 (3) | 0.81274 (14) | 0.4461 (2) | 0.0101 (6) | |
C2 | 0.6263 (3) | 0.87368 (14) | 0.4544 (2) | 0.0111 (6) | |
C20 | 0.5702 (3) | 0.92014 (14) | 0.5225 (2) | 0.0153 (6) | |
H201 | 0.4685 | 0.9315 | 0.4945 | 0.026 (5)* | |
H202 | 0.6326 | 0.9576 | 0.5270 | 0.026 (5)* | |
H203 | 0.5724 | 0.9021 | 0.5910 | 0.026 (5)* | |
C3 | 0.6944 (3) | 0.94287 (14) | 0.3361 (2) | 0.0111 (6) | |
O3 | 0.6808 (2) | 0.99615 (10) | 0.34780 (16) | 0.0158 (4) | |
O11 | 1.16158 (19) | 0.91979 (10) | 0.45152 (16) | 0.0163 (5) | |
C12 | 1.0293 (3) | 0.91404 (14) | 0.3892 (2) | 0.0129 (6) | |
N13 | 0.9525 (2) | 0.86506 (11) | 0.40345 (18) | 0.0111 (5) | |
C14 | 1.0531 (3) | 0.82224 (14) | 0.4740 (2) | 0.0134 (6) | |
C15 | 1.1612 (3) | 0.87050 (15) | 0.5275 (2) | 0.0159 (6) | |
H151 | 1.1270 | 0.8866 | 0.5904 | 0.018 (6)* | |
H152 | 1.2610 | 0.8522 | 0.5459 | 0.018 (6)* | |
C16 | 1.1309 (3) | 0.77888 (15) | 0.4072 (2) | 0.0174 (7) | |
H161 | 1.2006 | 0.7520 | 0.4510 | 0.019 (5)* | |
H162 | 1.1847 | 0.8040 | 0.3625 | 0.019 (5)* | |
H163 | 1.0575 | 0.7528 | 0.3650 | 0.019 (5)* | |
C17 | 0.9738 (3) | 0.78611 (16) | 0.5474 (2) | 0.0181 (7) | |
H171 | 0.9163 | 0.8151 | 0.5836 | 0.023 (5)* | |
H172 | 1.0461 | 0.7642 | 0.5973 | 0.023 (5)* | |
H173 | 0.9073 | 0.7555 | 0.5092 | 0.023 (5)* | |
S1 | 0.85728 (7) | 0.87267 (4) | 0.17639 (6) | 0.01253 (15) | |
C21 | 0.9358 (3) | 0.94634 (14) | 0.2090 (2) | 0.0119 (6) | |
C22 | 1.0035 (3) | 0.96176 (14) | 0.3094 (2) | 0.0123 (6) | |
C23 | 1.0611 (3) | 1.02195 (15) | 0.3305 (3) | 0.0174 (7) | |
H23 | 1.1063 | 1.0319 | 0.3981 | 0.022 (4)* | |
C24 | 1.0534 (3) | 1.06682 (15) | 0.2551 (3) | 0.0212 (7) | |
H24 | 1.0889 | 1.1080 | 0.2709 | 0.022 (4)* | |
C25 | 0.9933 (3) | 1.05120 (15) | 0.1556 (2) | 0.0187 (7) | |
H25 | 0.9914 | 1.0814 | 0.1025 | 0.022 (4)* | |
C26 | 0.9359 (3) | 0.99211 (15) | 0.1327 (2) | 0.0162 (6) | |
H26 | 0.8957 | 0.9823 | 0.0639 | 0.022 (4)* | |
O31 | 0.30893 (19) | 0.78898 (10) | 0.14341 (16) | 0.0149 (4) | |
C32 | 0.4389 (3) | 0.78648 (14) | 0.2073 (2) | 0.0115 (6) | |
N33 | 0.5126 (2) | 0.83815 (11) | 0.22034 (17) | 0.0091 (5) | |
C34 | 0.4180 (3) | 0.88879 (14) | 0.1625 (2) | 0.0115 (6) | |
C35 | 0.3001 (3) | 0.84988 (15) | 0.0959 (2) | 0.0187 (6) | |
H351 | 0.2008 | 0.8684 | 0.0954 | 0.020 (6)* | |
H352 | 0.3212 | 0.8472 | 0.0245 | 0.020 (6)* | |
C36 | 0.5039 (3) | 0.92864 (14) | 0.0960 (2) | 0.0145 (6) | |
H361 | 0.5788 | 0.9531 | 0.1400 | 0.017 (5)* | |
H362 | 0.4360 | 0.9571 | 0.0541 | 0.017 (5)* | |
H363 | 0.5523 | 0.9014 | 0.0512 | 0.017 (5)* | |
C37 | 0.3473 (3) | 0.92796 (14) | 0.2388 (2) | 0.0152 (6) | |
H371 | 0.2912 | 0.9006 | 0.2786 | 0.025 (5)* | |
H372 | 0.2806 | 0.9589 | 0.2015 | 0.025 (5)* | |
H373 | 0.4246 | 0.9496 | 0.2852 | 0.025 (5)* | |
S2 | 0.77527 (7) | 0.74136 (3) | 0.27649 (6) | 0.01212 (15) | |
C41 | 0.6123 (3) | 0.69967 (14) | 0.2814 (2) | 0.0113 (6) | |
C42 | 0.4687 (3) | 0.72389 (13) | 0.2520 (2) | 0.0105 (6) | |
C43 | 0.3449 (3) | 0.68583 (14) | 0.2601 (2) | 0.0122 (6) | |
H43 | 0.2486 | 0.7026 | 0.2409 | 0.020 (4)* | |
C44 | 0.3595 (3) | 0.62558 (15) | 0.2947 (2) | 0.0171 (6) | |
H44 | 0.2749 | 0.6010 | 0.3010 | 0.020 (4)* | |
C45 | 0.5018 (3) | 0.60073 (14) | 0.3209 (2) | 0.0175 (6) | |
H45 | 0.5140 | 0.5584 | 0.3430 | 0.020 (4)* | |
C46 | 0.6238 (3) | 0.63729 (14) | 0.3149 (2) | 0.0157 (6) | |
H46 | 0.7193 | 0.6197 | 0.3341 | 0.020 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.00742 (9) | 0.00788 (11) | 0.00833 (12) | 0.00024 (9) | 0.00205 (7) | −0.00025 (10) |
C10 | 0.0191 (13) | 0.0148 (15) | 0.0124 (16) | −0.0046 (11) | 0.0039 (11) | 0.0026 (12) |
C1 | 0.0082 (11) | 0.0157 (15) | 0.0061 (14) | −0.0007 (10) | 0.0003 (9) | 0.0018 (11) |
C2 | 0.0069 (11) | 0.0175 (15) | 0.0085 (14) | 0.0012 (10) | −0.0001 (10) | −0.0001 (11) |
C20 | 0.0174 (13) | 0.0158 (16) | 0.0143 (16) | 0.0014 (11) | 0.0076 (11) | −0.0044 (12) |
C3 | 0.0086 (11) | 0.0140 (14) | 0.0106 (15) | −0.0005 (10) | 0.0008 (10) | 0.0014 (12) |
O3 | 0.0153 (9) | 0.0126 (11) | 0.0199 (12) | 0.0009 (8) | 0.0038 (8) | −0.0017 (9) |
O11 | 0.0099 (8) | 0.0235 (12) | 0.0144 (12) | −0.0047 (8) | −0.0015 (7) | 0.0004 (9) |
C12 | 0.0098 (11) | 0.0157 (15) | 0.0137 (16) | 0.0025 (10) | 0.0033 (10) | −0.0024 (12) |
N13 | 0.0087 (9) | 0.0133 (13) | 0.0111 (13) | 0.0033 (8) | 0.0010 (8) | 0.0011 (10) |
C14 | 0.0090 (11) | 0.0184 (16) | 0.0119 (15) | 0.0034 (10) | −0.0010 (10) | 0.0043 (12) |
C15 | 0.0123 (12) | 0.0229 (17) | 0.0119 (16) | −0.0001 (11) | 0.0002 (10) | 0.0026 (13) |
C16 | 0.0117 (12) | 0.0212 (17) | 0.0192 (17) | 0.0048 (11) | 0.0016 (11) | 0.0052 (14) |
C17 | 0.0132 (12) | 0.0270 (18) | 0.0142 (17) | 0.0022 (12) | 0.0023 (11) | 0.0053 (14) |
S1 | 0.0135 (3) | 0.0140 (4) | 0.0107 (4) | −0.0017 (3) | 0.0041 (3) | −0.0009 (3) |
C21 | 0.0086 (11) | 0.0130 (14) | 0.0154 (16) | −0.0009 (10) | 0.0063 (10) | −0.0001 (12) |
C22 | 0.0083 (11) | 0.0137 (15) | 0.0159 (16) | −0.0006 (10) | 0.0054 (10) | 0.0011 (12) |
C23 | 0.0112 (12) | 0.0189 (17) | 0.0234 (18) | −0.0029 (11) | 0.0063 (11) | −0.0030 (13) |
C24 | 0.0203 (14) | 0.0123 (16) | 0.034 (2) | −0.0031 (12) | 0.0143 (13) | −0.0012 (14) |
C25 | 0.0180 (13) | 0.0178 (17) | 0.0227 (18) | −0.0003 (12) | 0.0107 (12) | 0.0065 (14) |
C26 | 0.0153 (13) | 0.0214 (17) | 0.0138 (16) | 0.0002 (11) | 0.0081 (11) | 0.0026 (13) |
O31 | 0.0130 (9) | 0.0117 (11) | 0.0176 (12) | −0.0015 (7) | −0.0059 (8) | 0.0037 (9) |
C32 | 0.0099 (11) | 0.0162 (15) | 0.0084 (15) | 0.0028 (10) | 0.0019 (10) | −0.0011 (12) |
N33 | 0.0090 (9) | 0.0074 (12) | 0.0105 (13) | 0.0005 (8) | −0.0002 (8) | 0.0011 (9) |
C34 | 0.0123 (11) | 0.0102 (14) | 0.0107 (15) | 0.0035 (10) | −0.0023 (10) | 0.0020 (11) |
C35 | 0.0189 (13) | 0.0135 (15) | 0.0211 (18) | −0.0005 (12) | −0.0055 (12) | 0.0023 (14) |
C36 | 0.0173 (13) | 0.0140 (15) | 0.0113 (16) | 0.0021 (11) | −0.0008 (11) | 0.0007 (12) |
C37 | 0.0119 (12) | 0.0166 (16) | 0.0169 (17) | 0.0021 (11) | 0.0013 (11) | 0.0001 (13) |
S2 | 0.0110 (3) | 0.0106 (3) | 0.0153 (4) | 0.0014 (2) | 0.0037 (2) | −0.0013 (3) |
C41 | 0.0152 (12) | 0.0127 (15) | 0.0067 (14) | 0.0007 (10) | 0.0036 (10) | −0.0012 (11) |
C42 | 0.0128 (12) | 0.0085 (14) | 0.0105 (15) | 0.0012 (10) | 0.0022 (10) | −0.0037 (11) |
C43 | 0.0141 (12) | 0.0129 (15) | 0.0096 (15) | −0.0021 (10) | 0.0015 (10) | −0.0022 (11) |
C44 | 0.0220 (14) | 0.0150 (15) | 0.0151 (17) | −0.0083 (12) | 0.0055 (12) | −0.0017 (13) |
C45 | 0.0319 (16) | 0.0080 (14) | 0.0131 (16) | 0.0002 (12) | 0.0049 (12) | 0.0004 (12) |
C46 | 0.0189 (13) | 0.0148 (16) | 0.0137 (16) | 0.0033 (11) | 0.0033 (11) | 0.0003 (12) |
Mo1—C1 | 2.024 (3) | C22—C23 | 1.401 (4) |
Mo1—C2 | 2.059 (3) | C23—C24 | 1.375 (4) |
Mo1—C3 | 1.953 (3) | C23—H23 | 0.95 |
Mo1—N13 | 2.236 (2) | C24—C25 | 1.386 (4) |
Mo1—N33 | 2.203 (2) | C24—H24 | 0.95 |
Mo1—S1 | 2.5254 (8) | C25—C26 | 1.383 (4) |
Mo1—S2 | 2.5297 (8) | C25—H25 | 0.95 |
C1—C2 | 1.314 (4) | C26—H26 | 0.95 |
C1—C10 | 1.483 (4) | O31—C32 | 1.353 (3) |
C10—H101 | 0.98 | O31—C35 | 1.440 (4) |
C10—H102 | 0.98 | C32—N33 | 1.291 (3) |
C10—H103 | 0.98 | C32—C42 | 1.469 (4) |
C2—C20 | 1.479 (4) | N33—C34 | 1.518 (3) |
C20—H201 | 0.98 | C34—C36 | 1.521 (4) |
C20—H202 | 0.98 | C34—C37 | 1.523 (4) |
C20—H203 | 0.98 | C34—C35 | 1.531 (4) |
C3—O3 | 1.157 (3) | C35—H351 | 0.99 |
O11—C12 | 1.364 (3) | C35—H352 | 0.99 |
O11—C15 | 1.453 (3) | C36—H361 | 0.98 |
C12—N13 | 1.289 (4) | C36—H362 | 0.98 |
C12—C22 | 1.459 (4) | C36—H363 | 0.98 |
N13—C14 | 1.515 (3) | C37—H371 | 0.98 |
C14—C17 | 1.505 (4) | C37—H372 | 0.98 |
C14—C16 | 1.525 (4) | C37—H373 | 0.98 |
C14—C15 | 1.527 (4) | S2—C41 | 1.746 (3) |
C15—H151 | 0.99 | C41—C46 | 1.402 (4) |
C15—H152 | 0.99 | C41—C42 | 1.412 (4) |
C16—H161 | 0.98 | C42—C43 | 1.411 (4) |
C16—H162 | 0.98 | C43—C44 | 1.365 (4) |
C16—H163 | 0.98 | C43—H43 | 0.95 |
C17—H171 | 0.98 | C44—C45 | 1.401 (4) |
C17—H172 | 0.98 | C44—H44 | 0.95 |
C17—H173 | 0.98 | C45—C46 | 1.374 (4) |
S1—C21 | 1.756 (3) | C45—H45 | 0.95 |
C21—C26 | 1.403 (4) | C46—H46 | 0.95 |
C21—C22 | 1.414 (4) | ||
N13—Mo1—N33 | 168.04 (8) | H172—C17—H173 | 109.5 |
S1—Mo1—S2 | 79.54 (3) | C21—S1—Mo1 | 101.22 (10) |
C1—Mo1—S1 | 163.76 (8) | C26—C21—C22 | 117.5 (3) |
C2—Mo1—S1 | 156.87 (8) | C26—C21—S1 | 119.5 (2) |
C3—Mo1—S2 | 167.27 (9) | C22—C21—S1 | 123.0 (2) |
C3—Mo1—C1 | 107.43 (12) | C23—C22—C21 | 120.0 (3) |
C3—Mo1—C2 | 69.91 (12) | C23—C22—C12 | 118.8 (3) |
C1—Mo1—C2 | 37.52 (11) | C21—C22—C12 | 120.9 (3) |
C3—Mo1—N33 | 94.51 (9) | C24—C23—C22 | 121.2 (3) |
C1—Mo1—N33 | 93.43 (9) | C24—C23—H23 | 119.4 |
C2—Mo1—N33 | 97.17 (9) | C22—C23—H23 | 119.4 |
C3—Mo1—N13 | 88.01 (9) | C23—C24—C25 | 119.2 (3) |
C1—Mo1—N13 | 96.97 (9) | C23—C24—H24 | 120.4 |
C2—Mo1—N13 | 94.67 (9) | C25—C24—H24 | 120.4 |
C3—Mo1—S1 | 87.86 (8) | C26—C25—C24 | 120.7 (3) |
N33—Mo1—S1 | 90.70 (6) | C26—C25—H25 | 119.6 |
N13—Mo1—S1 | 77.69 (6) | C24—C25—H25 | 119.6 |
C1—Mo1—S2 | 85.29 (9) | C25—C26—C21 | 121.3 (3) |
C2—Mo1—S2 | 122.81 (9) | C25—C26—H26 | 119.3 |
N33—Mo1—S2 | 83.92 (6) | C21—C26—H26 | 119.3 |
N13—Mo1—S2 | 91.04 (6) | C32—O31—C35 | 107.1 (2) |
C1—C10—H101 | 109.5 | N33—C32—O31 | 116.3 (2) |
C1—C10—H102 | 109.5 | N33—C32—C42 | 131.4 (2) |
H101—C10—H102 | 109.5 | O31—C32—C42 | 112.3 (2) |
C1—C10—H103 | 109.5 | C32—N33—C34 | 107.1 (2) |
H101—C10—H103 | 109.5 | C32—N33—Mo1 | 125.91 (18) |
H102—C10—H103 | 109.5 | C34—N33—Mo1 | 126.39 (17) |
C2—C1—C10 | 137.3 (3) | N33—C34—C36 | 112.5 (2) |
C2—C1—Mo1 | 72.66 (18) | N33—C34—C37 | 109.0 (2) |
C10—C1—Mo1 | 150.0 (2) | C36—C34—C37 | 112.3 (2) |
C1—C2—C20 | 139.6 (3) | N33—C34—C35 | 101.7 (2) |
C1—C2—Mo1 | 69.82 (18) | C36—C34—C35 | 110.7 (2) |
C20—C2—Mo1 | 150.5 (2) | C37—C34—C35 | 110.1 (2) |
C2—C20—H201 | 109.5 | O31—C35—C34 | 104.5 (2) |
C2—C20—H202 | 109.5 | O31—C35—H351 | 110.8 |
H201—C20—H202 | 109.5 | C34—C35—H351 | 110.8 |
C2—C20—H203 | 109.5 | O31—C35—H352 | 110.8 |
H201—C20—H203 | 109.5 | C34—C35—H352 | 110.8 |
H202—C20—H203 | 109.5 | H351—C35—H352 | 108.9 |
Mo1—C3—O3 | 176.3 (2) | C34—C36—H361 | 109.5 |
C12—O11—C15 | 104.9 (2) | C34—C36—H362 | 109.5 |
N13—C12—O11 | 116.1 (3) | H361—C36—H362 | 109.5 |
N13—C12—C22 | 129.6 (2) | C34—C36—H363 | 109.5 |
O11—C12—C22 | 114.0 (2) | H361—C36—H363 | 109.5 |
C12—N13—C14 | 106.5 (2) | H362—C36—H363 | 109.5 |
C12—N13—Mo1 | 122.26 (18) | C34—C37—H371 | 109.5 |
C14—N13—Mo1 | 131.18 (17) | C34—C37—H372 | 109.5 |
C17—C14—N13 | 113.4 (2) | H371—C37—H372 | 109.5 |
C17—C14—C16 | 111.8 (3) | C34—C37—H373 | 109.5 |
N13—C14—C16 | 107.7 (2) | H371—C37—H373 | 109.5 |
C17—C14—C15 | 113.0 (3) | H372—C37—H373 | 109.5 |
N13—C14—C15 | 99.8 (2) | C41—S2—Mo1 | 105.32 (10) |
C16—C14—C15 | 110.5 (2) | C46—C41—C42 | 117.3 (2) |
O11—C15—C14 | 103.8 (2) | C46—C41—S2 | 118.1 (2) |
O11—C15—H151 | 111.0 | C42—C41—S2 | 124.6 (2) |
C14—C15—H151 | 111.0 | C43—C42—C41 | 119.6 (3) |
O11—C15—H152 | 111.0 | C43—C42—C32 | 116.8 (2) |
C14—C15—H152 | 111.0 | C41—C42—C32 | 123.6 (2) |
H151—C15—H152 | 109.0 | C44—C43—C42 | 121.9 (3) |
C14—C16—H161 | 109.5 | C44—C43—H43 | 119.1 |
C14—C16—H162 | 109.5 | C42—C43—H43 | 119.1 |
H161—C16—H162 | 109.5 | C43—C44—C45 | 118.8 (3) |
C14—C16—H163 | 109.5 | C43—C44—H44 | 120.6 |
H161—C16—H163 | 109.5 | C45—C44—H44 | 120.6 |
H162—C16—H163 | 109.5 | C46—C45—C44 | 120.3 (3) |
C14—C17—H171 | 109.5 | C46—C45—H45 | 119.9 |
C14—C17—H172 | 109.5 | C44—C45—H45 | 119.9 |
H171—C17—H172 | 109.5 | C45—C46—C41 | 122.3 (3) |
C14—C17—H173 | 109.5 | C45—C46—H46 | 118.9 |
H171—C17—H173 | 109.5 | C41—C46—H46 | 118.9 |
C1—C2—Mo1—C3 | 178.5 (2) | C22—C21—C26—C25 | −3.2 (4) |
C10—C1—C2—C20 | 1.1 (6) | S1—C21—C26—C25 | 178.4 (2) |
Mo1—C1—C2—C20 | 179.2 (4) | C35—O31—C32—N33 | 7.8 (3) |
Mo1—C2—C1—C10 | −178.1 (3) | C35—O31—C32—C42 | −173.6 (2) |
C15—O11—C12—N13 | −8.7 (3) | O31—C32—N33—C34 | 4.4 (3) |
C15—O11—C12—C22 | 177.1 (2) | C42—C32—N33—C34 | −173.8 (3) |
O11—C12—N13—C14 | −11.2 (3) | O31—C32—N33—Mo1 | 175.82 (17) |
C22—C12—N13—C14 | 162.0 (3) | C42—C32—N33—Mo1 | −2.4 (5) |
O11—C12—N13—Mo1 | 171.36 (17) | C32—N33—C34—C36 | −132.2 (3) |
C22—C12—N13—Mo1 | −15.5 (4) | Mo1—N33—C34—C36 | 56.4 (3) |
C12—N13—C14—C17 | 145.1 (3) | C32—N33—C34—C37 | 102.6 (3) |
Mo1—N13—C14—C17 | −37.8 (4) | Mo1—N33—C34—C37 | −68.8 (3) |
C12—N13—C14—C16 | −90.7 (3) | C32—N33—C34—C35 | −13.7 (3) |
Mo1—N13—C14—C16 | 86.5 (3) | Mo1—N33—C34—C35 | 174.92 (18) |
C12—N13—C14—C15 | 24.7 (3) | C32—O31—C35—C34 | −16.0 (3) |
Mo1—N13—C14—C15 | −158.15 (19) | N33—C34—C35—O31 | 17.6 (3) |
C12—O11—C15—C14 | 24.1 (3) | C36—C34—C35—O31 | 137.4 (2) |
C17—C14—C15—O11 | −149.7 (2) | C37—C34—C35—O31 | −97.9 (3) |
N13—C14—C15—O11 | −29.0 (3) | Mo1—S2—C41—C46 | −144.6 (2) |
C16—C14—C15—O11 | 84.3 (3) | Mo1—S2—C41—C42 | 36.7 (3) |
Mo1—S1—C21—C26 | −138.2 (2) | C46—C41—C42—C43 | 1.8 (4) |
Mo1—S1—C21—C22 | 43.6 (2) | S2—C41—C42—C43 | −179.5 (2) |
C26—C21—C22—C23 | 3.1 (4) | C46—C41—C42—C32 | −174.7 (3) |
S1—C21—C22—C23 | −178.6 (2) | S2—C41—C42—C32 | 4.0 (4) |
C26—C21—C22—C12 | −170.1 (2) | N33—C32—C42—C43 | 152.4 (3) |
S1—C21—C22—C12 | 8.2 (4) | O31—C32—C42—C43 | −25.9 (4) |
N13—C12—C22—C23 | 153.7 (3) | N33—C32—C42—C41 | −31.0 (5) |
O11—C12—C22—C23 | −33.0 (4) | O31—C32—C42—C41 | 150.7 (3) |
N13—C12—C22—C21 | −33.0 (4) | C41—C42—C43—C44 | −0.7 (4) |
O11—C12—C22—C21 | 140.3 (3) | C32—C42—C43—C44 | 176.1 (3) |
C21—C22—C23—C24 | −0.1 (4) | C42—C43—C44—C45 | −1.3 (5) |
C12—C22—C23—C24 | 173.2 (2) | C43—C44—C45—C46 | 2.1 (5) |
C22—C23—C24—C25 | −2.8 (4) | C44—C45—C46—C41 | −1.0 (5) |
C23—C24—C25—C26 | 2.7 (4) | C42—C41—C46—C45 | −1.0 (4) |
C24—C25—C26—C21 | 0.4 (4) | S2—C41—C46—C45 | −179.8 (2) |
M, R | W, Ha | W, CH3b | Mo, CH3c | Mo, CH3c | W, Phb | W, Phb |
N,N-trans | N,N-trans | N,N-trans | S,S-trans | S,S-trans | S,S-trans | |
M—C1 | 2.0268 (17) | 2.0210 (17) | 2.024 (3) | 2.0310 (12) | 2.0510 (19) | 2.036 (4) |
M—C2 | 2.0548 (18) | 2.0565 (17) | 2.059 (3) | 2.0664 (12) | 2.078 (2) | 2.057 (4) |
M—C3 | 1.9623 (18) | 1.9535 (19) | 1.953 (3) | 1.9417 (13) | 1.949 (2) | 1.966 (4) |
C3—O3 | 1.160 (2) | 1.164 (2) | 1.157 (3) | 1.1555 (16) | 1.155 (3) | 1.154 (5) |
M—N13 | 2.2120 (14) | 2.2153 (16) | 2.236 (2) | 2.4715 (10) | 2.3087 (18) | 2.350 (3) |
M—N33 | 2.1987 (14) | 2.1862 (16) | 2.203 (2) | 2.3404 (11) | 2.2975 (17) | 2.304 (4) |
M—S1 | 2.5050 (4) | 2.5232 (4) | 2.5254 (8) | 2.4673 (3) | 2.4620 (5) | 2.4741 (12) |
M—S2 | 2.5067 (4) | 2.5243 (4) | 2.5297 (8) | 2.3665 (3) | 2.3698 (5) | 2.3773 (11) |
C1—C2 | 1.327 (3) | 1.314 (3) | 1.314 (4) | 1.2965 (18) | 1.309 (3) | 1.305 (6) |
N13—M—N33 | 169.58 (5) | 167.56 (6) | 168.04 (8) | 92.41 (3) | 83.29 (6) | 86.47 (13) |
S1—M—S2 | 78.869 (14) | 78.972 (15) | 79.54 (3) | 162.979 (11) | 175.564 (18) | 169.56 (4) |
C1—M—N13 | 92.88 (6) | 97.14 (7) | 96.97 (9) | 173.53 (4) | 165.94 (7) | 169.64 (15) |
C2—M—N13 | 93.66 (7) | 94.92 (6) | 94.67 (9) | 146.80 (4) | 150.09 (7) | 148.68 (15) |
C3—M—N33 | 94.24 (6) | 94.52 (7) | 94.51 (9) | 168.19 (4) | 159.92 (8) | 164.04 (15) |
C1—M—S1 | 164.79 (6) | 164.06 (5) | 163.76 (8) | 97.54 (3) | 85.61 (5) | 91.62 (13) |
C2—M—S1 | 153.79 (6) | 156.79 (5) | 156.87 (8) | 96.29 (3) | 87.98 (5) | 89.33 (12) |
C3—M—S2 | 163.06 (5) | 166.23 (5) | 167.27 (9) | 85.88 (4) | 87.58 (6) | 87.74 (14) |
The labels C1 and C2 of the alkyne ligand were choosen such that the torsion angle C2—C1—M—C3 is approximately 0°. The selected ligand containing atoms S1 and N13 was that in which one of these atoms is trans to the alkyne ligand. References: (a) Peschel et al. (2015a); (b) Peschel et al. (2019); (c) this work. |
Acknowledgements
Financial support by NAWI Graz is gratefully acknowledged.
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