metal-organic compounds
trans-Acetyldicarbonyl(η5-cyclopentadienyl)(methyldiphenylphosphane)molybdenum(II)
aDepartment of Chemistry, Carleton College, 1 N. College Street, Northfield, MN 55057, USA, and bDepartment of Chemistry, St Catherine University, 2004 Randolph Avenue, St. Paul, MN 55105, USA
*Correspondence e-mail: mwhited@carleton.edu
The title compound, [Mo(C5H5)(C2H3O)(C13H13P)(CO)2], was prepared by reaction of [Mo(CH3)(C5H5)(CO)3] with methyldiphenylphosphane. The MoII atom exhibits a four-legged piano-stool coordination geometry with the acetyl and phosphane ligands trans to each other. There are several intermolecular C—H⋯O hydrogen-bonding interactions involving carbonyl and acetyl O atoms as acceptors. A close nearly parallel π–π interaction between the cyclopentadienyl plane and the phenyl ring of the phosphane ligand is present, with an angle of 6.4 (1)° between the two least-squares planes. The centroid-to-centroid distance between these groups is 3.772 (3) Å, and the closest distance between two atoms of these groups is 3.449 (4) Å. Since each Mo complex is engaged in two of these interactions, the complexes form an infinite π-stack coincident with the a axis.
Related literature
The synthesis of the title compound has been reported previously and its reactivity studied, though no structural information was provided (Adams et al., 1997; Barnett et al., 1972). A related structure has been reported for the triphenylphosphane-substituted version of the title compound (Churchill & Fennessey, 1968). For synthetic details, see: Gladysz et al. (1979).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku Americas and Rigaku, 2011); cell CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku Americas and Rigaku, 2010); software used to prepare material for publication: CrystalStructure.
Supporting information
10.1107/S1600536812034307/wm2666sup1.cif
contains datablocks global, I. DOI:Supporting information file. DOI: 10.1107/S1600536812034307/wm2666Isup2.cdx
Structure factors: contains datablock I. DOI: 10.1107/S1600536812034307/wm2666Isup3.hkl
CpMo(CO)3(CH3). This compound was prepared by a modification of the method used by Gladysz et al. (1979) for the synthesis of a related iron compound. In an inert atmosphere
[CpMo(CO)3]2 (181 mg, 0.370 mmol) was dissolved in THF (10 ml). LiEt3BH (0.87 ml, 1M in THF) was added dropwise by syringe with stirring, causing the evolution of H2 and a color change from purple to yellow. The solution was stirred for 30 min, then CH3I (75 µl, 1.2 mmol) was slowly added to the solution by micropipette, and the resulting solution was stirred for 2 h, causing a green–yellow precipitate to form. The solvent was removed in vacuo and the residues were extracted into pentane (2 × 15 ml) and filtered through a 2 cm plug of Al2O3 on a 30 ml fritted funnel, leaving a clear pale-yellow liquid. The Al2O3 was washed with about 10 ml of pentane, and the solvent was removed in vacuo to afford a solid yellow product (87 mg, 45%). IR and NMR (1H and 13C) spectral analyses confirmed the formation of the desired product.CpMo(CO)2(PMePh2)(COCH3), (I). In an inert-atmosphere
CpMo(CO)3(CH3) (87.2 mg, 0.335 mmol) was dissolved in 10 ml acetonitrile. PMePh2 (93 µl, 0.50 mmol) was added with stirring, and the resulting solution was stirred for 48 h. Solvent was removed in vacuo, leaving an orange oil, which was dissolved in diethyl ether and dried in vacuo to a yellow powder. The powder was triturated with pentane (5 ml) and isolated by filtration to afford the desired product in pure form as a yellow powder (79 mg, 51%), as confirmed by IR and NMR (1H, 13C, and 31P) spectral analyses. Crystalline material was obtained as yellow prisms by chilling a concentrated solution of (I) in diethyl ether.H atoms were treated in calculated positions and refined in the riding model approximation with distances of C—H = 0.95, 1.00 and 0.98 Å for the phenyl, cyclopentadienyl and methyl groups, respectively, and with Uiso(H) = kUeq(C), k = 1.2 for phenyl and cyclopentadienyl groups and 1.5 for methyl groups. Methyl group H atoms were allowed to rotate in order to find the best rotameric conformation. The maximum and minimum electron densities in the final difference Fourier map are located 0.87 and 0.75 Å, respectively, from atom Mo1.
Data collection: CrystalClear (Rigaku Americas and Rigaku, 2011); cell
CrystalClear (Rigaku Americas and Rigaku, 2011); data reduction: CrystalClear (Rigaku Americas and Rigaku, 2011); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku Americas and Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku Americas and Rigaku, 2010).[Mo(C5H5)(C2H3O)(C13H13P)(CO)2] | F(000) = 1872.00 |
Mr = 460.32 | Dx = 1.453 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71075 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 1664 reflections |
a = 11.482 (7) Å | θ = 5.8–27.4° |
b = 17.648 (10) Å | µ = 0.72 mm−1 |
c = 20.771 (12) Å | T = 193 K |
V = 4209 (4) Å3 | Prism, yellow |
Z = 8 | 0.44 × 0.24 × 0.24 mm |
Rigaku XtaLAB mini diffractometer | 4311 reflections with F2 > 2σ(F2) |
Detector resolution: 6.849 pixels mm-1 | Rint = 0.037 |
ω scans | θmax = 27.5° |
Absorption correction: multi-scan (REQAB; Rigaku, 1998) | h = −14→14 |
Tmin = 0.687, Tmax = 0.842 | k = −22→22 |
40944 measured reflections | l = −26→26 |
4809 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.13 | w = 1/[σ2(Fo2) + (0.0289P)2 + 2.9563P] where P = (Fo2 + 2Fc2)/3 |
4809 reflections | (Δ/σ)max < 0.001 |
246 parameters | Δρmax = 0.63 e Å−3 |
0 restraints | Δρmin = −0.67 e Å−3 |
Primary atom site location: structure-invariant direct methods |
[Mo(C5H5)(C2H3O)(C13H13P)(CO)2] | V = 4209 (4) Å3 |
Mr = 460.32 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.482 (7) Å | µ = 0.72 mm−1 |
b = 17.648 (10) Å | T = 193 K |
c = 20.771 (12) Å | 0.44 × 0.24 × 0.24 mm |
Rigaku XtaLAB mini diffractometer | 4809 independent reflections |
Absorption correction: multi-scan (REQAB; Rigaku, 1998) | 4311 reflections with F2 > 2σ(F2) |
Tmin = 0.687, Tmax = 0.842 | Rint = 0.037 |
40944 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 1.13 | Δρmax = 0.63 e Å−3 |
4809 reflections | Δρmin = −0.67 e Å−3 |
246 parameters |
Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
Mo1 | 0.060442 (15) | 0.126963 (10) | 0.104324 (8) | 0.02232 (7) | |
P1 | 0.10879 (5) | 0.26230 (3) | 0.09372 (2) | 0.02307 (11) | |
O1 | 0.13079 (18) | −0.03933 (9) | 0.11872 (8) | 0.0440 (5) | |
O2 | 0.26219 (18) | 0.11759 (12) | 0.00363 (10) | 0.0571 (6) | |
O3 | 0.16580 (19) | 0.16063 (12) | 0.23997 (8) | 0.0519 (5) | |
C1 | −0.1051 (3) | 0.06501 (17) | 0.14181 (14) | 0.0472 (7) | |
C2 | −0.0856 (3) | 0.03902 (16) | 0.07757 (16) | 0.0483 (7) | |
C3 | −0.1018 (3) | 0.09998 (17) | 0.03529 (13) | 0.0435 (6) | |
C4 | −0.12974 (19) | 0.16438 (16) | 0.07247 (13) | 0.0401 (6) | |
C5 | −0.1332 (2) | 0.14285 (16) | 0.13805 (13) | 0.0433 (6) | |
C6 | 0.1703 (2) | 0.02414 (13) | 0.12514 (10) | 0.0318 (5) | |
C7 | 0.2962 (3) | 0.02999 (15) | 0.14855 (15) | 0.0490 (7) | |
C8 | 0.1896 (2) | 0.12249 (13) | 0.04171 (11) | 0.0325 (5) | |
C9 | 0.1317 (2) | 0.14872 (13) | 0.18841 (10) | 0.0308 (5) | |
C10 | 0.2599 (2) | 0.28503 (13) | 0.11366 (11) | 0.0335 (5) | |
C11 | 0.0223 (2) | 0.32333 (12) | 0.14697 (10) | 0.0287 (5) | |
C12 | 0.0544 (3) | 0.33488 (14) | 0.21134 (12) | 0.0393 (6) | |
C13 | −0.0172 (4) | 0.37648 (16) | 0.25232 (13) | 0.0545 (8) | |
C14 | −0.1206 (3) | 0.40696 (19) | 0.22946 (14) | 0.0626 (9) | |
C15 | −0.1530 (3) | 0.39641 (18) | 0.16607 (15) | 0.0573 (8) | |
C16 | −0.0814 (3) | 0.35472 (15) | 0.12501 (12) | 0.0403 (6) | |
C17 | 0.09086 (18) | 0.30855 (13) | 0.01478 (10) | 0.0278 (5) | |
C18 | 0.06705 (19) | 0.26664 (15) | −0.04063 (11) | 0.0340 (5) | |
C19 | 0.0595 (3) | 0.30314 (18) | −0.10050 (11) | 0.0430 (7) | |
C20 | 0.0746 (3) | 0.38056 (17) | −0.10492 (12) | 0.0456 (7) | |
C21 | 0.0974 (3) | 0.42270 (16) | −0.05024 (13) | 0.0442 (7) | |
C22 | 0.1062 (3) | 0.38683 (14) | 0.00936 (12) | 0.0379 (6) | |
H1 | −0.1100 | 0.0326 | 0.1812 | 0.0566* | |
H2 | −0.0722 | −0.0148 | 0.0646 | 0.0580* | |
H3 | −0.0998 | 0.0974 | −0.0128 | 0.0522* | |
H4 | −0.1517 | 0.2152 | 0.0551 | 0.0481* | |
H5 | −0.1600 | 0.1754 | 0.1746 | 0.0519* | |
H7A | 0.3302 | −0.0208 | 0.1512 | 0.0588* | |
H7B | 0.2977 | 0.0537 | 0.1912 | 0.0588* | |
H7C | 0.3413 | 0.0608 | 0.1183 | 0.0588* | |
H10A | 0.2717 | 0.3399 | 0.1105 | 0.0402* | |
H10B | 0.3121 | 0.2591 | 0.0835 | 0.0402* | |
H10C | 0.2768 | 0.2682 | 0.1576 | 0.0402* | |
H12 | 0.1253 | 0.3143 | 0.2271 | 0.0471* | |
H13 | 0.0047 | 0.3840 | 0.2960 | 0.0654* | |
H14 | −0.1694 | 0.4352 | 0.2576 | 0.0751* | |
H15 | −0.2238 | 0.4174 | 0.1505 | 0.0688* | |
H16 | −0.1038 | 0.3477 | 0.0814 | 0.0483* | |
H18 | 0.0560 | 0.2134 | −0.0378 | 0.0408* | |
H19 | 0.0439 | 0.2744 | −0.1382 | 0.0516* | |
H20 | 0.0693 | 0.4049 | −0.1456 | 0.0547* | |
H21 | 0.1071 | 0.4760 | −0.0533 | 0.0530* | |
H22 | 0.1229 | 0.4159 | 0.0467 | 0.0455* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Mo1 | 0.02136 (10) | 0.02484 (10) | 0.02077 (10) | −0.00183 (6) | 0.00309 (6) | −0.00097 (7) |
P1 | 0.0228 (3) | 0.0254 (3) | 0.0211 (3) | 0.0007 (2) | −0.00052 (19) | 0.0007 (2) |
O1 | 0.0625 (13) | 0.0279 (9) | 0.0418 (10) | 0.0008 (8) | −0.0040 (9) | 0.0023 (8) |
O2 | 0.0538 (13) | 0.0667 (14) | 0.0508 (12) | 0.0067 (10) | 0.0315 (10) | 0.0057 (10) |
O3 | 0.0704 (14) | 0.0585 (12) | 0.0267 (9) | 0.0002 (10) | −0.0137 (9) | 0.0010 (9) |
C1 | 0.0326 (14) | 0.0555 (17) | 0.0535 (16) | −0.0186 (12) | 0.0053 (12) | 0.0097 (13) |
C2 | 0.0282 (13) | 0.0434 (15) | 0.073 (2) | −0.0121 (11) | −0.0024 (13) | −0.0167 (14) |
C3 | 0.0286 (13) | 0.0616 (17) | 0.0403 (14) | −0.0073 (12) | −0.0052 (11) | −0.0111 (13) |
C4 | 0.0175 (11) | 0.0498 (15) | 0.0529 (15) | −0.0005 (10) | −0.0043 (10) | −0.0022 (12) |
C5 | 0.0222 (12) | 0.0583 (17) | 0.0494 (15) | −0.0056 (11) | 0.0118 (11) | −0.0113 (13) |
C6 | 0.0408 (13) | 0.0289 (11) | 0.0257 (11) | 0.0031 (10) | 0.0073 (9) | 0.0023 (9) |
C7 | 0.0369 (15) | 0.0408 (14) | 0.0693 (19) | 0.0089 (11) | −0.0017 (13) | 0.0096 (14) |
C8 | 0.0320 (12) | 0.0313 (12) | 0.0342 (12) | 0.0011 (9) | 0.0052 (10) | 0.0034 (10) |
C9 | 0.0339 (12) | 0.0301 (11) | 0.0284 (11) | 0.0012 (9) | 0.0015 (10) | 0.0026 (9) |
C10 | 0.0264 (12) | 0.0325 (12) | 0.0415 (13) | −0.0055 (9) | −0.0056 (10) | 0.0041 (10) |
C11 | 0.0340 (12) | 0.0265 (11) | 0.0257 (11) | 0.0019 (9) | 0.0016 (9) | −0.0007 (9) |
C12 | 0.0521 (16) | 0.0354 (13) | 0.0303 (12) | 0.0054 (11) | −0.0040 (11) | −0.0045 (10) |
C13 | 0.080 (3) | 0.0530 (17) | 0.0304 (13) | 0.0117 (16) | 0.0023 (14) | −0.0119 (12) |
C14 | 0.077 (3) | 0.064 (2) | 0.0466 (17) | 0.0237 (18) | 0.0154 (16) | −0.0158 (15) |
C15 | 0.0537 (18) | 0.068 (2) | 0.0500 (17) | 0.0300 (15) | 0.0059 (14) | −0.0058 (15) |
C16 | 0.0398 (14) | 0.0490 (15) | 0.0321 (13) | 0.0147 (11) | 0.0003 (10) | −0.0046 (11) |
C17 | 0.0244 (11) | 0.0352 (12) | 0.0238 (10) | 0.0036 (9) | 0.0034 (8) | 0.0051 (9) |
C18 | 0.0307 (12) | 0.0444 (14) | 0.0270 (11) | −0.0010 (10) | −0.0014 (9) | 0.0036 (10) |
C19 | 0.0343 (13) | 0.0688 (19) | 0.0259 (12) | −0.0019 (12) | −0.0027 (10) | 0.0049 (12) |
C20 | 0.0321 (14) | 0.0682 (19) | 0.0364 (14) | 0.0097 (12) | 0.0043 (10) | 0.0256 (13) |
C21 | 0.0418 (15) | 0.0444 (15) | 0.0462 (15) | 0.0108 (12) | 0.0094 (12) | 0.0185 (12) |
C22 | 0.0455 (15) | 0.0342 (13) | 0.0340 (13) | 0.0049 (11) | 0.0047 (11) | 0.0051 (10) |
Mo1—P1 | 2.4619 (15) | C17—C18 | 1.395 (4) |
Mo1—C1 | 2.327 (3) | C17—C22 | 1.397 (4) |
Mo1—C2 | 2.352 (3) | C18—C19 | 1.403 (4) |
Mo1—C3 | 2.399 (3) | C19—C20 | 1.380 (5) |
Mo1—C4 | 2.375 (3) | C20—C21 | 1.383 (4) |
Mo1—C5 | 2.348 (3) | C21—C22 | 1.394 (4) |
Mo1—C6 | 2.252 (3) | C1—H1 | 1.000 |
Mo1—C8 | 1.974 (3) | C2—H2 | 1.000 |
Mo1—C9 | 1.966 (3) | C3—H3 | 1.000 |
P1—C10 | 1.828 (3) | C4—H4 | 1.000 |
P1—C11 | 1.836 (3) | C5—H5 | 1.000 |
P1—C17 | 1.843 (3) | C7—H7A | 0.980 |
O1—C6 | 1.216 (3) | C7—H7B | 0.980 |
O2—C8 | 1.153 (4) | C7—H7C | 0.980 |
O3—C9 | 1.160 (3) | C10—H10A | 0.980 |
C1—C2 | 1.429 (5) | C10—H10B | 0.980 |
C1—C5 | 1.413 (5) | C10—H10C | 0.980 |
C2—C3 | 1.401 (5) | C12—H12 | 0.950 |
C3—C4 | 1.411 (4) | C13—H13 | 0.950 |
C4—C5 | 1.415 (4) | C14—H14 | 0.950 |
C6—C7 | 1.529 (4) | C15—H15 | 0.950 |
C11—C12 | 1.402 (4) | C16—H16 | 0.950 |
C11—C16 | 1.390 (4) | C18—H18 | 0.950 |
C12—C13 | 1.393 (4) | C19—H19 | 0.950 |
C13—C14 | 1.387 (5) | C20—H20 | 0.950 |
C14—C15 | 1.381 (5) | C21—H21 | 0.950 |
C15—C16 | 1.395 (4) | C22—H22 | 0.950 |
P1···O3 | 3.588 (3) | C2···H21vii | 3.5742 |
O1···C1 | 3.310 (4) | C3···H2i | 3.2486 |
O1···C2 | 2.969 (4) | C3···H10Avii | 3.5224 |
O1···C8 | 3.342 (4) | C4···H10Bvii | 3.5725 |
O2···C6 | 3.194 (4) | C5···H20vii | 3.5218 |
O2···C7 | 3.406 (4) | C6···H3i | 3.2715 |
O2···C18 | 3.576 (4) | C6···H10Aii | 3.3327 |
O3···C6 | 3.390 (4) | C6···H13iii | 3.5838 |
O3···C7 | 3.341 (4) | C6···H14iii | 2.8981 |
O3···C10 | 3.588 (4) | C6···H22ii | 3.4551 |
O3···C12 | 3.383 (4) | C7···H10Aii | 3.5336 |
C4···C16 | 3.575 (5) | C7···H14iii | 2.9531 |
C7···C8 | 3.015 (4) | C7···H20iv | 3.3399 |
C7···C9 | 2.940 (4) | C7···H22ii | 3.0641 |
C8···C10 | 3.334 (4) | C8···H2i | 3.2094 |
C8···C17 | 3.518 (4) | C8···H16iv | 3.5279 |
C8···C18 | 3.373 (4) | C10···H3iv | 3.3599 |
C9···C10 | 3.220 (4) | C10···H19iv | 3.4630 |
C9···C11 | 3.437 (4) | C11···H7Aix | 3.2309 |
C9···C12 | 3.436 (4) | C12···H7Aix | 3.1301 |
C10···C12 | 3.234 (4) | C13···H1x | 3.4102 |
C10···C22 | 3.322 (4) | C13···H7Aix | 3.5078 |
C11···C14 | 2.794 (4) | C13···H10Cviii | 3.5690 |
C11···C22 | 3.218 (4) | C13···H19vi | 3.5713 |
C12···C15 | 2.782 (5) | C14···H10Cviii | 3.5888 |
C13···C16 | 2.772 (4) | C14···H12viii | 3.4638 |
C16···C17 | 3.133 (4) | C15···H21xiii | 3.2914 |
C16···C22 | 3.276 (4) | C16···H21xiii | 3.3506 |
C17···C20 | 2.798 (4) | C17···H4iv | 3.3192 |
C18···C21 | 2.783 (5) | C18···H4iv | 3.2589 |
C19···C22 | 2.771 (4) | C18···H10Bvii | 3.0935 |
O1···C3i | 3.390 (4) | C19···H4iv | 3.4631 |
O1···C10ii | 3.346 (4) | C19···H5iv | 3.5902 |
O1···C13iii | 3.329 (4) | C19···H7Cvii | 3.4892 |
O1···C14iii | 3.295 (4) | C19···H10Bvii | 3.0662 |
O2···C16iv | 3.256 (4) | C20···H5iv | 3.5154 |
O3···C5v | 3.441 (4) | C20···H7Cvii | 2.8845 |
O3···C19vi | 3.589 (4) | C21···H7Cvii | 3.2752 |
O3···C20vi | 3.465 (4) | C22···H3iv | 3.3875 |
C3···O1i | 3.390 (4) | C22···H4iv | 3.5719 |
C3···C21vii | 3.491 (4) | C22···H7Aix | 3.4448 |
C3···C22vii | 3.486 (4) | C22···H21xiii | 3.5620 |
C4···C20vii | 3.551 (4) | H1···C13iii | 3.4102 |
C4···C21vii | 3.520 (4) | H1···H7Bviii | 2.8790 |
C4···C22vii | 3.591 (4) | H1···H13iii | 2.9263 |
C5···O3viii | 3.441 (4) | H1···H14xii | 3.4470 |
C5···C20vii | 3.449 (4) | H1···H15xii | 2.8593 |
C10···O1ix | 3.346 (4) | H2···O2i | 3.1709 |
C13···O1x | 3.329 (4) | H2···C2i | 3.4907 |
C14···O1x | 3.295 (4) | H2···C3i | 3.2486 |
C16···O2vii | 3.256 (4) | H2···C8i | 3.2094 |
C19···O3xi | 3.589 (4) | H2···H2i | 3.1975 |
C20···O3xi | 3.465 (4) | H2···H3i | 2.6799 |
C20···C4iv | 3.551 (4) | H2···H13iii | 3.4899 |
C20···C5iv | 3.449 (4) | H2···H15xii | 3.1778 |
C21···C3iv | 3.491 (4) | H2···H18i | 3.5528 |
C21···C4iv | 3.520 (4) | H3···O1i | 2.4532 |
C22···C3iv | 3.486 (4) | H3···C2i | 3.4843 |
C22···C4iv | 3.591 (4) | H3···C6i | 3.2715 |
Mo1···H7B | 3.5141 | H3···C10vii | 3.3599 |
Mo1···H7C | 3.4422 | H3···C22vii | 3.3875 |
Mo1···H18 | 3.3238 | H3···H2i | 2.6799 |
P1···H4 | 3.2066 | H3···H10Avii | 2.7424 |
P1···H12 | 2.9240 | H3···H10Bvii | 3.0966 |
P1···H16 | 2.8797 | H3···H22vii | 3.2696 |
P1···H18 | 2.9289 | H4···O2vii | 3.3418 |
P1···H22 | 2.8864 | H4···C17vii | 3.3192 |
O1···H1 | 3.3073 | H4···C18vii | 3.2589 |
O1···H2 | 2.6237 | H4···C19vii | 3.4631 |
O1···H7A | 2.4098 | H4···C22vii | 3.5719 |
O1···H7B | 2.9389 | H4···H10Bvii | 2.9426 |
O1···H7C | 2.9947 | H5···O3viii | 2.6865 |
O2···H7C | 2.7383 | H5···C19vii | 3.5902 |
O2···H10B | 3.0530 | H5···C20vii | 3.5154 |
O2···H18 | 3.0344 | H5···H7Bviii | 3.5515 |
O3···H7B | 2.6231 | H5···H19vii | 3.5945 |
O3···H10C | 2.8558 | H5···H20vii | 3.4692 |
O3···H12 | 2.7637 | H7A···C11ii | 3.2309 |
C1···H3 | 3.2623 | H7A···C12ii | 3.1301 |
C1···H4 | 3.2499 | H7A···C13ii | 3.5078 |
C2···H4 | 3.2350 | H7A···C22ii | 3.4448 |
C2···H5 | 3.2528 | H7A···H10Aii | 2.8504 |
C3···H1 | 3.2570 | H7A···H12ii | 3.3486 |
C3···H5 | 3.2543 | H7A···H14iii | 2.7577 |
C3···H18 | 3.0975 | H7A···H20iv | 3.4250 |
C4···H1 | 3.2500 | H7A···H22ii | 2.4989 |
C4···H2 | 3.2352 | H7B···H1v | 2.8790 |
C4···H16 | 3.2540 | H7B···H5v | 3.5515 |
C4···H18 | 3.2472 | H7B···H14iii | 2.7710 |
C5···H2 | 3.2502 | H7B···H20iv | 3.3394 |
C5···H3 | 3.2568 | H7C···C19iv | 3.4892 |
C6···H1 | 3.4260 | H7C···C20iv | 2.8845 |
C6···H2 | 3.1320 | H7C···C21iv | 3.2752 |
C8···H3 | 3.5380 | H7C···H20iv | 2.7456 |
C8···H7B | 3.5574 | H7C···H21iv | 3.3995 |
C8···H7C | 2.5979 | H7C···H22ii | 2.9857 |
C8···H10B | 2.9238 | H10A···O1ix | 2.4134 |
C8···H18 | 2.7671 | H10A···C3iv | 3.5224 |
C9···H1 | 3.4534 | H10A···C6ix | 3.3327 |
C9···H5 | 3.3938 | H10A···C7ix | 3.5336 |
C9···H7B | 2.5395 | H10A···H3iv | 2.7424 |
C9···H7C | 3.2132 | H10A···H7Aix | 2.8504 |
C9···H10B | 3.5830 | H10A···H13v | 3.3963 |
C9···H10C | 2.7631 | H10A···H14v | 3.2858 |
C9···H12 | 3.0307 | H10B···C4iv | 3.5725 |
C10···H12 | 2.8641 | H10B···C18iv | 3.0935 |
C10···H22 | 3.1218 | H10B···C19iv | 3.0662 |
C11···H4 | 3.3578 | H10B···H3iv | 3.0966 |
C11···H5 | 3.3952 | H10B···H4iv | 2.9426 |
C11···H10A | 2.9772 | H10B···H18iv | 2.9960 |
C11···H10C | 3.0888 | H10B···H19iv | 2.9537 |
C11···H13 | 3.2807 | H10C···C13v | 3.5690 |
C11···H15 | 3.2782 | H10C···C14v | 3.5888 |
C11···H22 | 2.8885 | H10C···H13v | 3.4564 |
C12···H10A | 3.2587 | H10C···H14v | 3.4887 |
C12···H10C | 3.0251 | H10C···H19iv | 3.1828 |
C12···H14 | 3.2652 | H12···C14v | 3.4638 |
C12···H16 | 3.2612 | H12···H7Aix | 3.3486 |
C13···H15 | 3.2590 | H12···H14v | 3.1961 |
C14···H12 | 3.2645 | H12···H15v | 3.5750 |
C14···H16 | 3.2543 | H12···H19vi | 3.3397 |
C15···H13 | 3.2571 | H13···O1x | 2.7191 |
C16···H4 | 2.9705 | H13···C6x | 3.5838 |
C16···H5 | 3.4489 | H13···H1x | 2.9263 |
C16···H12 | 3.2617 | H13···H2x | 3.4899 |
C16···H14 | 3.2587 | H13···H10Aviii | 3.3963 |
C16···H22 | 3.0519 | H13···H10Cviii | 3.4564 |
C17···H4 | 3.3421 | H13···H15v | 3.3619 |
C17···H10A | 2.9281 | H13···H19vi | 3.1440 |
C17···H10B | 3.0416 | H14···O1x | 2.6463 |
C17···H16 | 2.7176 | H14···C6x | 2.8981 |
C17···H19 | 3.2788 | H14···C7x | 2.9531 |
C17···H21 | 3.2819 | H14···H1xiv | 3.4470 |
C18···H3 | 3.5950 | H14···H7Ax | 2.7577 |
C18···H4 | 3.3290 | H14···H7Bx | 2.7710 |
C18···H16 | 3.5094 | H14···H10Aviii | 3.2858 |
C18···H20 | 3.2726 | H14···H10Cviii | 3.4887 |
C18···H22 | 3.2626 | H14···H12viii | 3.1961 |
C19···H21 | 3.2515 | H15···O2vii | 3.2645 |
C20···H18 | 3.2696 | H15···C1xiv | 3.2673 |
C20···H22 | 3.2584 | H15···C2xiv | 3.4187 |
C21···H19 | 3.2503 | H15···H1xiv | 2.8593 |
C22···H10A | 2.9516 | H15···H2xiv | 3.1778 |
C22···H16 | 2.9206 | H15···H12viii | 3.5750 |
C22···H18 | 3.2652 | H15···H13viii | 3.3619 |
C22···H20 | 3.2620 | H15···H21xiii | 3.0672 |
H1···H2 | 2.5988 | H16···O2vii | 2.4214 |
H1···H5 | 2.5882 | H16···C8vii | 3.5279 |
H2···H3 | 2.5706 | H16···H21xiii | 3.1651 |
H3···H4 | 2.5815 | H18···H2i | 3.5528 |
H3···H18 | 2.7676 | H18···H10Bvii | 2.9960 |
H4···H5 | 2.5829 | H19···O3xi | 3.1109 |
H4···H16 | 2.4631 | H19···C10vii | 3.4630 |
H4···H18 | 3.0675 | H19···C13xi | 3.5713 |
H7C···H10B | 3.5893 | H19···H5iv | 3.5945 |
H10A···H12 | 2.9819 | H19···H10Bvii | 2.9537 |
H10A···H22 | 2.5452 | H19···H10Cvii | 3.1828 |
H10C···H12 | 2.4015 | H19···H12xi | 3.3397 |
H12···H13 | 2.3407 | H19···H13xi | 3.1440 |
H13···H14 | 2.3348 | H20···O3xi | 2.8666 |
H14···H15 | 2.3309 | H20···C5iv | 3.5218 |
H15···H16 | 2.3400 | H20···C7vii | 3.3399 |
H16···H22 | 2.9569 | H20···H5iv | 3.4692 |
H18···H19 | 2.3505 | H20···H7Avii | 3.4250 |
H19···H20 | 2.3268 | H20···H7Bvii | 3.3394 |
H20···H21 | 2.3324 | H20···H7Cvii | 2.7456 |
H21···H22 | 2.3392 | H21···O2ix | 3.1448 |
O1···H3i | 2.4532 | H21···C2iv | 3.5742 |
O1···H10Aii | 2.4134 | H21···C15xiii | 3.2914 |
O1···H13iii | 2.7191 | H21···C16xiii | 3.3506 |
O1···H14iii | 2.6463 | H21···C22xiii | 3.5620 |
O1···H22ii | 3.2953 | H21···H7Cvii | 3.3995 |
O2···H2i | 3.1709 | H21···H15xiii | 3.0672 |
O2···H4iv | 3.3418 | H21···H16xiii | 3.1651 |
O2···H15iv | 3.2645 | H21···H21xiii | 3.4149 |
O2···H16iv | 2.4214 | H21···H22xiii | 3.2597 |
O2···H21ii | 3.1448 | H22···O1ix | 3.2953 |
O3···H5v | 2.6865 | H22···C6ix | 3.4551 |
O3···H19vi | 3.1109 | H22···C7ix | 3.0641 |
O3···H20vi | 2.8666 | H22···H3iv | 3.2696 |
C1···H15xii | 3.2673 | H22···H7Aix | 2.4989 |
C2···H2i | 3.4907 | H22···H7Cix | 2.9857 |
C2···H3i | 3.4843 | H22···H21xiii | 3.2597 |
C2···H15xii | 3.4187 | ||
P1—Mo1—C1 | 132.06 (8) | P1—C11—C16 | 119.97 (17) |
P1—Mo1—C2 | 141.25 (8) | C12—C11—C16 | 118.7 (3) |
P1—Mo1—C3 | 108.32 (8) | C11—C12—C13 | 120.2 (3) |
P1—Mo1—C4 | 84.99 (8) | C12—C13—C14 | 120.0 (3) |
P1—Mo1—C5 | 97.15 (8) | C13—C14—C15 | 120.3 (3) |
P1—Mo1—C6 | 132.27 (7) | C14—C15—C16 | 119.7 (3) |
P1—Mo1—C8 | 79.07 (7) | C11—C16—C15 | 121.0 (3) |
P1—Mo1—C9 | 78.24 (7) | P1—C17—C18 | 121.40 (19) |
C1—Mo1—C2 | 35.55 (11) | P1—C17—C22 | 119.70 (17) |
C1—Mo1—C3 | 58.15 (11) | C18—C17—C22 | 118.8 (2) |
C1—Mo1—C4 | 58.19 (11) | C17—C18—C19 | 120.0 (3) |
C1—Mo1—C5 | 35.19 (11) | C18—C19—C20 | 120.4 (3) |
C1—Mo1—C6 | 90.84 (10) | C19—C20—C21 | 120.1 (3) |
C1—Mo1—C8 | 144.62 (10) | C20—C21—C22 | 119.9 (3) |
C1—Mo1—C9 | 97.72 (11) | C17—C22—C21 | 120.8 (3) |
C2—Mo1—C3 | 34.29 (11) | Mo1—C1—H1 | 126.077 |
C2—Mo1—C4 | 57.45 (10) | C2—C1—H1 | 126.080 |
C2—Mo1—C5 | 58.26 (10) | C5—C1—H1 | 126.073 |
C2—Mo1—C6 | 85.01 (10) | Mo1—C2—H2 | 125.537 |
C2—Mo1—C8 | 110.71 (11) | C1—C2—H2 | 125.531 |
C2—Mo1—C9 | 129.45 (11) | C3—C2—H2 | 125.541 |
C3—Mo1—C4 | 34.38 (10) | Mo1—C3—H3 | 126.038 |
C3—Mo1—C5 | 57.76 (10) | C2—C3—H3 | 126.024 |
C3—Mo1—C6 | 112.95 (10) | C4—C3—H3 | 126.038 |
C3—Mo1—C8 | 100.46 (11) | Mo1—C4—H4 | 125.605 |
C3—Mo1—C9 | 153.22 (10) | C3—C4—H4 | 125.604 |
C4—Mo1—C5 | 34.85 (10) | C5—C4—H4 | 125.610 |
C4—Mo1—C6 | 142.42 (9) | Mo1—C5—H5 | 125.855 |
C4—Mo1—C8 | 121.21 (10) | C1—C5—H5 | 125.863 |
C4—Mo1—C9 | 125.13 (10) | C4—C5—H5 | 125.858 |
C5—Mo1—C6 | 124.71 (10) | C6—C7—H7A | 109.468 |
C5—Mo1—C8 | 155.88 (10) | C6—C7—H7B | 109.471 |
C5—Mo1—C9 | 96.06 (10) | C6—C7—H7C | 109.470 |
C6—Mo1—C8 | 70.94 (9) | H7A—C7—H7B | 109.475 |
C6—Mo1—C9 | 75.75 (9) | H7A—C7—H7C | 109.467 |
C8—Mo1—C9 | 106.30 (11) | H7B—C7—H7C | 109.475 |
Mo1—P1—C10 | 113.99 (8) | P1—C10—H10A | 109.466 |
Mo1—P1—C11 | 113.15 (8) | P1—C10—H10B | 109.470 |
Mo1—P1—C17 | 118.95 (8) | P1—C10—H10C | 109.464 |
C10—P1—C11 | 104.38 (11) | H10A—C10—H10B | 109.472 |
C10—P1—C17 | 102.14 (10) | H10A—C10—H10C | 109.489 |
C11—P1—C17 | 102.46 (11) | H10B—C10—H10C | 109.467 |
Mo1—C1—C2 | 73.17 (16) | C11—C12—H12 | 119.888 |
Mo1—C1—C5 | 73.24 (16) | C13—C12—H12 | 119.863 |
C2—C1—C5 | 107.2 (3) | C12—C13—H13 | 119.974 |
Mo1—C2—C1 | 71.28 (16) | C14—C13—H13 | 119.977 |
Mo1—C2—C3 | 74.69 (16) | C13—C14—H14 | 119.842 |
C1—C2—C3 | 108.6 (3) | C15—C14—H14 | 119.849 |
Mo1—C3—C2 | 71.02 (16) | C14—C15—H15 | 120.161 |
Mo1—C3—C4 | 71.91 (15) | C16—C15—H15 | 120.160 |
C2—C3—C4 | 107.8 (3) | C11—C16—H16 | 119.517 |
Mo1—C4—C3 | 73.71 (15) | C15—C16—H16 | 119.501 |
Mo1—C4—C5 | 71.53 (14) | C17—C18—H18 | 120.007 |
C3—C4—C5 | 108.5 (3) | C19—C18—H18 | 120.002 |
Mo1—C5—C1 | 71.57 (15) | C18—C19—H19 | 119.816 |
Mo1—C5—C4 | 73.62 (14) | C20—C19—H19 | 119.814 |
C1—C5—C4 | 107.9 (3) | C19—C20—H20 | 119.951 |
Mo1—C6—O1 | 120.81 (19) | C21—C20—H20 | 119.945 |
Mo1—C6—C7 | 122.44 (17) | C20—C21—H21 | 120.036 |
O1—C6—C7 | 116.7 (3) | C22—C21—H21 | 120.032 |
Mo1—C8—O2 | 177.0 (2) | C17—C22—H22 | 119.627 |
Mo1—C9—O3 | 175.0 (2) | C21—C22—H22 | 119.622 |
P1—C11—C12 | 121.15 (18) | ||
P1—Mo1—C1—C2 | 122.96 (9) | C3—Mo1—C5—C1 | 79.16 (13) |
P1—Mo1—C1—C5 | 8.48 (17) | C3—Mo1—C5—C4 | −36.69 (11) |
C1—Mo1—P1—C10 | 141.40 (10) | C5—Mo1—C3—C2 | −79.68 (13) |
C1—Mo1—P1—C11 | 22.32 (10) | C5—Mo1—C3—C4 | 37.20 (11) |
C1—Mo1—P1—C17 | −97.99 (11) | C3—Mo1—C6—O1 | −21.07 (19) |
P1—Mo1—C2—C1 | −95.59 (15) | C3—Mo1—C6—C7 | 159.70 (13) |
P1—Mo1—C2—C3 | 20.6 (2) | C6—Mo1—C3—C2 | 37.97 (14) |
C2—Mo1—P1—C10 | −167.39 (13) | C6—Mo1—C3—C4 | 154.85 (10) |
C2—Mo1—P1—C11 | 73.54 (14) | C8—Mo1—C3—C2 | 111.56 (12) |
C2—Mo1—P1—C17 | −46.77 (13) | C8—Mo1—C3—C4 | −131.55 (12) |
P1—Mo1—C3—C2 | −166.59 (8) | C9—Mo1—C3—C2 | −66.2 (3) |
P1—Mo1—C3—C4 | −49.71 (12) | C9—Mo1—C3—C4 | 50.6 (3) |
C3—Mo1—P1—C10 | −155.34 (7) | C4—Mo1—C5—C1 | 115.9 (2) |
C3—Mo1—P1—C11 | 85.58 (9) | C4—Mo1—C5—C4 | 0.00 (12) |
C3—Mo1—P1—C17 | −34.73 (8) | C5—Mo1—C4—C3 | −116.5 (2) |
P1—Mo1—C4—C3 | 133.37 (11) | C5—Mo1—C4—C5 | −0.00 (12) |
P1—Mo1—C4—C5 | −110.15 (10) | C4—Mo1—C6—O1 | 2.1 (3) |
C4—Mo1—P1—C10 | 179.04 (7) | C4—Mo1—C6—C7 | −177.14 (12) |
C4—Mo1—P1—C11 | 59.96 (8) | C6—Mo1—C4—C3 | −39.91 (19) |
C4—Mo1—P1—C17 | −60.34 (7) | C6—Mo1—C4—C5 | 76.57 (17) |
P1—Mo1—C5—C1 | −173.66 (9) | C8—Mo1—C4—C3 | 59.37 (15) |
P1—Mo1—C5—C4 | 70.48 (11) | C8—Mo1—C4—C5 | 175.85 (10) |
C5—Mo1—P1—C10 | 146.31 (8) | C9—Mo1—C4—C3 | −154.79 (10) |
C5—Mo1—P1—C11 | 27.24 (7) | C9—Mo1—C4—C5 | −38.31 (16) |
C5—Mo1—P1—C17 | −93.07 (8) | C5—Mo1—C6—O1 | 44.6 (2) |
P1—Mo1—C6—O1 | −168.84 (11) | C5—Mo1—C6—C7 | −134.60 (14) |
P1—Mo1—C6—C7 | 11.92 (18) | C6—Mo1—C5—C1 | −17.96 (16) |
C6—Mo1—P1—C10 | −6.49 (8) | C6—Mo1—C5—C4 | −133.81 (10) |
C6—Mo1—P1—C11 | −125.57 (8) | C8—Mo1—C5—C1 | 107.1 (3) |
C6—Mo1—P1—C17 | 114.13 (8) | C8—Mo1—C5—C4 | −8.7 (3) |
C8—Mo1—P1—C10 | −57.82 (8) | C9—Mo1—C5—C1 | −94.80 (12) |
C8—Mo1—P1—C11 | −176.90 (8) | C9—Mo1—C5—C4 | 149.35 (12) |
C8—Mo1—P1—C17 | 62.79 (8) | C8—Mo1—C6—O1 | −114.64 (18) |
C9—Mo1—P1—C10 | 51.58 (7) | C8—Mo1—C6—C7 | 66.12 (15) |
C9—Mo1—P1—C11 | −67.50 (8) | C9—Mo1—C6—O1 | 132.15 (18) |
C9—Mo1—P1—C17 | 172.19 (8) | C9—Mo1—C6—C7 | −47.08 (14) |
C1—Mo1—C2—C1 | −0.00 (13) | Mo1—P1—C11—C12 | 83.56 (16) |
C1—Mo1—C2—C3 | 116.2 (2) | Mo1—P1—C11—C16 | −91.91 (15) |
C2—Mo1—C1—C2 | −0.00 (12) | Mo1—P1—C17—C18 | −9.41 (18) |
C2—Mo1—C1—C5 | −114.5 (2) | Mo1—P1—C17—C22 | 173.40 (10) |
C1—Mo1—C3—C2 | −37.90 (11) | C10—P1—C11—C12 | −40.92 (18) |
C1—Mo1—C3—C4 | 78.99 (13) | C10—P1—C11—C16 | 143.61 (15) |
C3—Mo1—C1—C2 | 36.53 (11) | C10—P1—C17—C18 | 117.05 (16) |
C3—Mo1—C1—C5 | −77.95 (13) | C10—P1—C17—C22 | −60.14 (17) |
C1—Mo1—C4—C3 | −78.87 (14) | C11—P1—C17—C18 | −135.02 (15) |
C1—Mo1—C4—C5 | 37.61 (11) | C11—P1—C17—C22 | 47.78 (17) |
C4—Mo1—C1—C2 | 77.24 (13) | C17—P1—C11—C12 | −147.13 (15) |
C4—Mo1—C1—C5 | −37.24 (11) | C17—P1—C11—C16 | 37.40 (18) |
C1—Mo1—C5—C1 | 0.00 (13) | Mo1—C1—C2—Mo1 | −0.0 |
C1—Mo1—C5—C4 | −115.9 (2) | Mo1—C1—C2—C3 | −65.93 (16) |
C5—Mo1—C1—C2 | 114.5 (2) | Mo1—C1—C5—Mo1 | 0.0 |
C5—Mo1—C1—C5 | 0.00 (12) | Mo1—C1—C5—C4 | 65.15 (14) |
C1—Mo1—C6—O1 | 34.40 (17) | C2—C1—C5—Mo1 | −65.80 (18) |
C1—Mo1—C6—C7 | −144.83 (15) | C2—C1—C5—C4 | −0.6 (3) |
C6—Mo1—C1—C2 | −80.21 (12) | C5—C1—C2—Mo1 | 65.84 (19) |
C6—Mo1—C1—C5 | 165.32 (12) | C5—C1—C2—C3 | −0.1 (3) |
C8—Mo1—C1—C2 | −23.1 (3) | Mo1—C2—C3—Mo1 | 0.0 |
C8—Mo1—C1—C5 | −137.59 (14) | Mo1—C2—C3—C4 | −62.93 (15) |
C9—Mo1—C1—C2 | −155.94 (12) | C1—C2—C3—Mo1 | 63.71 (19) |
C9—Mo1—C1—C5 | 89.59 (13) | C1—C2—C3—C4 | 0.8 (3) |
C2—Mo1—C3—C2 | 0.00 (13) | Mo1—C3—C4—Mo1 | −0.0 |
C2—Mo1—C3—C4 | 116.9 (2) | Mo1—C3—C4—C5 | −63.53 (13) |
C3—Mo1—C2—C1 | −116.2 (2) | C2—C3—C4—Mo1 | 62.35 (18) |
C3—Mo1—C2—C3 | 0.00 (12) | C2—C3—C4—C5 | −1.2 (3) |
C2—Mo1—C4—C3 | −36.59 (12) | Mo1—C4—C5—Mo1 | −0.0 |
C2—Mo1—C4—C5 | 79.89 (14) | Mo1—C4—C5—C1 | −63.81 (14) |
C4—Mo1—C2—C1 | −79.49 (13) | C3—C4—C5—Mo1 | 64.94 (17) |
C4—Mo1—C2—C3 | 36.69 (11) | C3—C4—C5—C1 | 1.1 (3) |
C2—Mo1—C5—C1 | 38.48 (12) | P1—C11—C12—C13 | −174.91 (15) |
C2—Mo1—C5—C4 | −77.37 (14) | P1—C11—C16—C15 | 175.00 (15) |
C5—Mo1—C2—C1 | −38.08 (11) | C12—C11—C16—C15 | −0.6 (4) |
C5—Mo1—C2—C3 | 78.10 (13) | C16—C11—C12—C13 | 0.6 (4) |
C2—Mo1—C6—O1 | −0.71 (17) | C11—C12—C13—C14 | −0.3 (4) |
C2—Mo1—C6—C7 | −179.94 (16) | C12—C13—C14—C15 | −0.1 (5) |
C6—Mo1—C2—C1 | 98.48 (12) | C13—C14—C15—C16 | 0.2 (5) |
C6—Mo1—C2—C3 | −145.34 (13) | C14—C15—C16—C11 | 0.2 (5) |
C8—Mo1—C2—C1 | 165.94 (10) | P1—C17—C18—C19 | −176.91 (13) |
C8—Mo1—C2—C3 | −77.89 (14) | P1—C17—C22—C21 | 177.60 (15) |
C9—Mo1—C2—C1 | 31.55 (17) | C18—C17—C22—C21 | 0.3 (4) |
C9—Mo1—C2—C3 | 147.72 (12) | C22—C17—C18—C19 | 0.3 (3) |
C3—Mo1—C4—C3 | −0.00 (12) | C17—C18—C19—C20 | −0.5 (4) |
C3—Mo1—C4—C5 | 116.5 (2) | C18—C19—C20—C21 | 0.1 (4) |
C4—Mo1—C3—C2 | −116.9 (2) | C19—C20—C21—C22 | 0.6 (4) |
C4—Mo1—C3—C4 | −0.00 (12) | C20—C21—C22—C17 | −0.8 (4) |
Symmetry codes: (i) −x, −y, −z; (ii) −x+1/2, y−1/2, z; (iii) −x, y−1/2, −z+1/2; (iv) x+1/2, −y+1/2, −z; (v) x+1/2, y, −z+1/2; (vi) x, −y+1/2, z+1/2; (vii) x−1/2, −y+1/2, −z; (viii) x−1/2, y, −z+1/2; (ix) −x+1/2, y+1/2, z; (x) −x, y+1/2, −z+1/2; (xi) x, −y+1/2, z−1/2; (xii) −x−1/2, y−1/2, z; (xiii) −x, −y+1, −z; (xiv) −x−1/2, y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O1ix | 0.98 | 2.41 | 3.346 (3) | 159 |
C16—H16···O2vii | 0.95 | 2.42 | 3.256 (3) | 147 |
C3—H3···O1i | 1.00 | 2.45 | 3.390 (4) | 156 |
Symmetry codes: (i) −x, −y, −z; (vii) x−1/2, −y+1/2, −z; (ix) −x+1/2, y+1/2, z. |
Experimental details
Crystal data | |
Chemical formula | [Mo(C5H5)(C2H3O)(C13H13P)(CO)2] |
Mr | 460.32 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 193 |
a, b, c (Å) | 11.482 (7), 17.648 (10), 20.771 (12) |
V (Å3) | 4209 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.72 |
Crystal size (mm) | 0.44 × 0.24 × 0.24 |
Data collection | |
Diffractometer | Rigaku XtaLAB mini diffractometer |
Absorption correction | Multi-scan (REQAB; Rigaku, 1998) |
Tmin, Tmax | 0.687, 0.842 |
No. of measured, independent and observed [F2 > 2σ(F2)] reflections | 40944, 4809, 4311 |
Rint | 0.037 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.072, 1.13 |
No. of reflections | 4809 |
No. of parameters | 246 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.63, −0.67 |
Computer programs: CrystalClear (Rigaku Americas and Rigaku, 2011), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku Americas and Rigaku, 2010).
Mo1—P1 | 2.4619 (15) | Mo1—C6 | 2.252 (3) |
Mo1—C1 | 2.327 (3) | Mo1—C8 | 1.974 (3) |
Mo1—C2 | 2.352 (3) | Mo1—C9 | 1.966 (3) |
Mo1—C3 | 2.399 (3) | O1—C6 | 1.216 (3) |
Mo1—C4 | 2.375 (3) | O2—C8 | 1.153 (4) |
Mo1—C5 | 2.348 (3) | O3—C9 | 1.160 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···O1i | 0.98 | 2.41 | 3.346 (3) | 158.8 |
C16—H16···O2ii | 0.95 | 2.42 | 3.256 (3) | 146.6 |
C3—H3···O1iii | 1.00 | 2.45 | 3.390 (4) | 155.7 |
Symmetry codes: (i) −x+1/2, y+1/2, z; (ii) x−1/2, −y+1/2, −z; (iii) −x, −y, −z. |
Acknowledgements
The authors gratefully acknowledge St Catherine University and NSF–MRI Award No. 1125975 `MRI Consortium: Acquisition of a Single-Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility'. Additional funding was provided by the Department of Chemistry at Carleton College.
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Synthesis of the title complex, [Mo(C5H5)(C2H3O)(CO)2(C13H13P)], (I), has been previously reported and its reactivity studied, though no structural information was provided (Adams et al., 1997; Barnett et al., 1972).
The molecular structure of (Fig. 1), consists of a Mo(II) atom coordinated to a cyclopentadienyl ring in an η5 fashion, two CO ligands, one PMePh2 ligand, and one acetyl ligand. The orientation of the CO ligands can be described as trans. A view of the trans CO ligand orientation is shown in Fig. 2. The Mo—Cp centroid distance is 2.02959 (17) Å. The methyl group of the acetyl group is oriented in a syn fashion relative to the orientation of the methyl group of the PMePh2 ligand. A unit cell packing diagram is shown in Fig. 3.
There are several particularly short intermolecular distances involving H atoms. One short contact (2.421 Å) is present between O2 of a carbonyl ligand and H16 of a phenyl group (symmetry code: x - 1/2, -y + 1/2, -z). Another short contact (2.414 Å) involves O1 of the acetyl group and H10A of the methyl group of a PMePh2 ligand (symmetry code: -x + 1/2, y + 1/2,z). A third short contact (2.453 Å) is present between O1 of the acetyl group and H3 of a Cp ring (symmetry code: -x, -y, -z).
A close nearly parallel π—π intermolecular interaction between the Cp plane and the phenyl ring of a PMePh2 ligand is present. The angle between the least-squares planes of these close π systems is 6.4 (1)° (Cp ring plane composed of atoms C1–C5; phenyl ring plane composed of atoms C17–C22). While the Cp centroid–phenyl ring centroid distance is 3.772 (3) Å, the closest distance between these groups is 3.449 (4) Å between C20 and C5 (symmetry code: 1/2 + x, 1/2 - y, -z). Each Mo complex is engaged in two of these interactions, forming an infinite stack that is coincident with the a-axis. Fig. 4 shows the π overlap of neighboring molecules. Fig. 5 shows the infinite π-stacking interaction.
A related structure has been reported for the triphenylphosphane-substituted version of (I) (Churchill & Fennessey, 1968).