Crystal structures of trans-acetyl­dicarbon­yl(η⁵-cyclo­penta­dien­yl)(di­methyl­phenyl­phosphane)molybdenum(II) and trans-acetyl­dicarbon­yl(η⁵-cyclo­penta­dien­yl)(ethyl­diphenyl­phosphane)molybdenum(II)

The crystal structures of the title compounds are compared, showing mol­ecular parameters that reflect the relative steric pressure of their respective phosphine ligands. Their supra­molecular properties are distinct but in both cases are organized around short C—H...O contacts involving the acetyl ligands.

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.021
• wR factor = 0.045
• Data-to-parameter ratio = 19.4

Structure: 2

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.028
• wR factor = 0.068
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

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Datablock: 1


Alert level C
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note

Alert level G
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Mo1    --  C1      ..        8.2 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Mo1    --  C2      ..        5.1 su
PLAT910_ALERT_3_G Missing # of FCF Reflections Below Th(Min) .....          3 Report

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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Datablock: 2


Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8     ..  O2      ..       2.63 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H13    ..  O2      ..       2.71 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22    ..  O3      ..       2.66 Ang.
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          6 Report
PLAT934_ALERT_3_C Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          1 Check

Alert level G
PLAT230_ALERT_2_G Hirshfeld Test Diff for    O1     --  C1      ..        6.4 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Mo1    --  C1      ..       10.0 su
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Mo1    --  C2      ..        7.7 su
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          4 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
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PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
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Author Response: LTJ and AN prepared and crystallized complex (1); CJH and SHK prepared and crystallized complex (2); MTW and GEH supervised and assisted with preparations as part of a curricular laboratory at Carleton College; DEJ assisted with data collection and analysis; MTW wrote the article with input from GEH and DEJ.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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S1. Chemical context

Cyclo­penta­dienylmolybdenum polycarbonyl complexes [Mo(C₅H₅)(CO)_n] with `piano-stool' geometries have been studied extensively for their fundamental organometallic reactivity. In particular, alkyl complexes of the form [Mo(C₅H₅)(CO)₃(R)] have been studied for their migratory insertion reactivity (Barnett & Treichel, 1967; Butler et al., 1967), affording [Mo(C₅H₅)(PR₃)(CO)₂(COR)] acetyl complexes on exposure to phosphine ligands. Although the insertion reaction shows little dependence on the nature of the phosphine, the corresponding deinsertion shows a strong dependence on steric bulk of the phosphine, with bulkier groups giving enhanced deinsertion rates (Barnett, 1969; Barnett & Pollmann, 1974).

We have developed an inter­est in the solid-state structural properties of a series of piano-stool molybdenum acetyl complexes derived from migratory insertion with various phosphines, with the goal of understanding how modification of the phosphine substituents affects ground-state structure as well as solid-state packing. Recently, we reported an unusual example where orientation of the acetyl group in the solid state can be changed by introduction of furyl substituents on the phosphine ligand (Whited et al., 2013). In this study, the structures obtained for di­methyl­phenyl­phosphine, [Mo(C₅H₅)(P(CH₃)₂(C₆H₅))(CO)₂(COCH₃)] (1), and ethyl­diphenyl­phosphine, [Mo(C₅H₅)(P(C₂H₅)(C₆H₅)₂))(CO)₂(COCH₃)] (2), derivatives are compared.

S2. Structural commentary

The molecular structures of (1) and (2) are illustrated in Figs. 1 and 2. In spite of the somewhat different steric environments provided by the phosphine ligands, the molecular structures are quite similar. Both complexes exhibit a trans disposition of carbonyl ligands common for compounds of this class. Complexes (1) and (2) both have structures where the oxygen atom of the acetyl group points toward the cyclo­penta­dienyl (Cp) ring. This orientation is also consistent with the majority of crystal structures of related complexes, with the exception of the recently reported tri(2-furyl)phosphine derivative, in which the acetyl group points away from the Cp ring, enabling inter­molecular O···H—C inter­actions with the furyl group of a neighboring molecule (Whited et al., 2013).

Selected geometric parameters for (1) and (2) are presented in Tables 1 and 2. The Mo1—P1 bond lengths [2.4535 (9) Å for di­methyl­phenyl­phosphine derivative (1) and 2.4813 (6) Å for ethyl­diphenyl­phosphine derivative (2)] track with the steric bulk of the ligands and are consistent with the previously reported methyl­diphenyl­phosphine complex (Whited et al., 2012), which exhibits an Mo—P bond length [2.4620 (14) Å] that is inter­mediate between those of (1) and (2). Along with a slightly longer Mo—P distance, the sterically bulkier derivative (2) exhibits a larger C3—Mo1—P1 angle [135.76 (6)°] relative to (1) [131.79 (9)°], again with the methyl­diphenyl­phosphine derivative inter­mediate [132.27 (2)°]. The steric effects of the phosphine ligands observed in the solid state are consistent with findings regarding de­carbonyl­ation rates for this class of complexes (Barnett & Pollmann, 1974), where the steric influence of bulkier phosphines enhances the rate of the de­carbonyl­ation reaction.

S3. Supra­molecular features

The extended structures of (1) and (2) are quite different, but the acetyl oxygen atom (O3) plays an important role in the packing of both structures. For di­methyl­phenyl­phosphine complex (1), there are C—H···O hydrogen-bonding inter­actions between O3 of the acetyl carbonyl on one Mo complex and H11C from a phosphine methyl substituent (2.45 Å) and H13 from a phenyl group (2.36 Å) on the same phosphine on a neighboring molecule (Table 3). These short contacts organize the molecules into chains parallel to [001] (Fig. 3). Additional short contacts (2.40 Å) between O1 of a carbonyl ligand and H15 of a phosphine phenyl substituent within the chains are present. The chains are arranged in layers parallel to (100). In contrast to the closely related methyl­diphenyl­phosphine derivative (Whited et al., 2012), (1) does not exhibit any π–π inter­actions between the Cp ring and a phosphine phenyl substituent. In contrast, the closest phenyl group is oriented perpendicular to the Cp ring with a distance of 3.00 Å between H17 of the phenyl group and the Cp centroid.

The supra­molecular organization of ethyl­diphenyl­phosphine derivative (2) is quite different, though it is still partly governed by hydrogen-bonding inter­actions involving O3 of the acetyl group. In this case, short contacts (2.66 Å) between O3 of the acetyl group and H22 of a phosphine phenyl substituent (Table 4) link the molecules into chains parallel to [010]. An additional set of short contacts between O2 of a carbonyl ligand and H8 from a Cp ring (2.63 Å) and H13 from a phenyl ring (2.71 Å) on an adjacent molecule organize the molecules into centrosymmetrical dimers, joining the unit cells along [010] (Fig. 4). Finally, another set of centrosymmetrical dimers is formed through short contacts between C8/H8 units on Cp rings of adjacent molecules (Fig. 5).

S4. Database survey

The current version of the Cambridge Structural Database (Version 5.35, updated November 2013; Allen, 2002) has nine entries corresponding to molybdenum acyl complexes of the general form [Mo(C₅H₅)(CO)₂(PR₃)(COR)], as well as five tungsten complexes with the same ligand types. No chromium complexes with the same ligand set are in the database. The trans-di­carbonyl structure, as observed for (1) and (2), 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). The preference for a trans geometry is likely at least partly steric in nature, since the only example with a cis-di­carbonyl geometry without linked phosphine and acyl ligands is for a molybdenum formyl with a small tri­methyl­phosphine ligand and a bulky penta­methyl­cyclo­penta­dienyl ligand (Asdar et al., 1989).

S5. Synthesis and crystallization

CpMo(CO)₃(CH₃). This compound was prepared by a modification of the method used of Gladysz et al. (1979), as previously reported by Whited & Hofmeister (2014).

CpMo(CO)₂(PMe₂Ph)(COCH₃) (1). In an inert-atmosphere glove box, CpMo(CO)₃(CH₃) (113 mg, 0.435 mmol) was dissolved in 2 ml aceto­nitrile. In a separate vial, di­methyl­phenyl­phosphine (97.0 mg, 0.702 mmol) was dissolved in 2 ml aceto­nitrile. The vials were combined and the resulting solution was stirred for 1 week. Solvent was removed in vacuo, leaving a yellow–orange solid that was triturated with pentane (5 ml) and isolated by filtration to afford the desired product in pure form as a yellow powder (112 mg, 65%). Crystalline material was obtained as yellow–orange prisms by chilling a concentrated di­ethyl ether solution at 233 K. ¹H NMR (400 MHz, CDCl₃): δ 7.67–7.58 (m, 2H, Ar–H), 7.50–7.41 (m, 3H, Ar–H), 4.97 (d, J = 1.1 Hz, 5H, Cp H), 2.58 (s, 3H, C(O)CH₃), 1.91 (d, ²J_PH = 8.9 Hz, 6H, P(CH₃)₂). ¹³C{¹H} NMR (101 MHz, CDCl₃): δ 267.3 (d, ²J_PC = 13 Hz, –COCH₃), 237.8 (d, ²J_PC = 24 Hz, –CO), 139.2 (d, ¹J_PC = 40 Hz, C_ipso from Ph–P), 130.3 (d, ⁴J_PC = 2 Hz, C_para from Ph–P), 129.6 (d, ²J_PC = 10 Hz, C_ortho from Ph–P), 128.9 (d, ²J_PC = 10 Hz, C_meta from Ph–P), 96.0 (s, Cp ring), 51.7 (s, –COCH₃), 20.0 (d, ¹J_PC = 33 Hz, P(CH₃)₂). ³¹P{¹H} NMR (162 MHz, CDCl₃): δ 33.1 (s). IR (CH₂Cl₂, NaCl, cm^–1) ν(CO): 1931, 1846, 1601 (acetyl).

CpMo(CO)₂(PEtPh₂)(COCH₃) (2). In an inert-atmosphere glove box, CpMo(CO)₃(CH₃) (105 mg, 0.404 mmol) was dissolved in 2 ml aceto­nitrile. Ethyl­diphenyl­phosphine (129 mg, 0.602 mmol) was added and the resulting solution was stirred for one week. Solvent was removed in vacuo, leaving a yellow solid that was triturated with pentane (5 ml) and isolated by filtration to afford the desired product in pure form as a yellow powder (106 mg, 55%). Crystalline material was obtained as yellow blocks by slow evaporation of di­ethyl ether from a concentrated solution at ambient temperature. ¹H NMR (400 MHz, CDCl₃): δ 7.50–7.42 (m, 10H, Ar–H), 4.92 (d, J = 1.2 Hz, 5H, Cp H), 2.68 (apparent quint, ²J_PH = ³J_HH = 7.8 Hz, 2H, PCH₂CH₃), 2.63 (s, 3H, C(O)CH₃), 1.17 (dt, ³J_PH = 18.0 Hz, ²J_PH = 7.5 Hz, 3H, PCH₂CH₃). ¹³C{¹H} NMR (101 MHz, CDCl₃): δ 266.4 (d, ²J_PC = 11 Hz, –COCH₃), 238.5 (d, ²J_PC = 23 Hz, –CO), 135.9 (d, ¹J_PC = 40 Hz, C_ipso from Ph–P), 132.1 (d, ²J_PC = 10 Hz, C_ortho from Ph–P), 130.4 (d, ⁴J_PC = 2 Hz, C_para from Ph–P), 128.7 (d, ²J_PC = 9 Hz, C_meta from Ph–P), 96.5 (s, Cp ring), 51.0 (s, –COCH₃), 26.3 (d, ¹J_PC = 32 Hz, PCH₂CH₃), 9.0 (d, ²J_PC = 2 Hz, PCH₂CH₃). ³¹P{¹H} NMR (162 MHz, CDCl₃): δ 59.3 (s). IR (CH₂Cl₂, NaCl, cm^–1) ν(CO): 1937, 1859, 1610 (acetyl).

S6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 5. 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 alkyl groups, respectively, and with U_iso(H) = k×U_eq(C), k = 1.2 for phenyl and cyclo­penta­dienyl groups and 1.5 for alkyl groups. Methyl group H atoms were allowed to rotate in order to find the best rotameric conformation.

A small number of low-angle reflections [three for (1); six for (2)] were rejected from these high-quality data sets due to the arrangement of the instrument with a conservatively sized beam stop and a fixed-position detector. The large number of reflections in the data sets (and the Fourier-transform relationship of intensities to atoms) ensures that no particular bias was thereby introduced.

Related literature

For related literature, see: Adams et al. (1991); Allen (2002); Asdar et al. (1989); Barnett (1969); Barnett & Pollmann (1974); Barnett & Treichel (1967); Butler et al. (1967); Gladysz et al. (1979); Mercier et al. (1993); Whited & Hofmeister (2014); Whited et al. (2012, 2013); Yan et al. (2009).

Computing details

For both compounds, data collection: CrystalClear (Rigaku, 2011); cell refinement: CrystalClear (Rigaku, 2011); data reduction: CrystalClear (Rigaku, 2011). Program(s) used to solve structure: SHELXS (Sheldrick, 2008) for (1); SIR2008 (Burla et al., 2007) for (2). For both compounds, program(s) used to refine structure: SHELXL (Sheldrick, 2008); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

Figures

	Fig. 1. Molecular structure of (1) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. Molecular structure of (2) with displacement ellipsoids drawn at the 50% probability level.
	Fig. 3. Crystal packing of (1) viewed along [010] showing the layered arrangement parallel to (100). Dashed lines indicate intermolecular C—H···O hydrogen-bonding interactions.
	Fig. 4. Crystal packing of (2) viewed along [100] showing chains of centrosymmetrical dimers.
	Fig. 5. Centrosymmetrical dimers of (2) connected through C8/H8 interactions of Cp rings on adjacent molecules.

(1) trans-Acetyldicarbonyl-(η⁵-cyclopentadienyl)-˘dimethylphenylphosphine)-molybdenum(II)

Crystal data

[Mo(C5H5)(C2H3O)(C8H11P)(CO)2]	F(000) = 808
Mr = 398.23	Dx = 1.542 Mg m^−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: P 2c -2n	Cell parameters from 16109 reflections
a = 16.374 (2) Å	θ = 3.2–27.6°
b = 6.8898 (10) Å	µ = 0.87 mm^−1
c = 15.208 (2) Å	T = 173 K
V = 1715.6 (4) Å^3	Prism, yellow
Z = 4	0.4 × 0.4 × 0.19 mm

Data collection

Rigaku XtaLAB mini diffractometer	3639 reflections with I > 2σ(I)
Detector resolution: 6.849 pixels mm^-1	Rint = 0.035
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −21→21
Tmin = 0.707, Tmax = 0.848	k = −8→8
17021 measured reflections	l = −19→19
3923 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.021	w = 1/[σ^2(Fo^2) + (0.0142P)^2 + 0.493P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.045	(Δ/σ)max = 0.002
S = 1.05	Δρmax = 0.21 e Å^−3
3923 reflections	Δρmin = −0.27 e Å^−3
202 parameters	Absolute structure: Flack x determined using 1649 quotients [(I^+)-(I^-)]/[(I^+)+(I^-)] (Parsons et al., 2013).
1 restraint	Absolute structure parameter: 0.007 (18)
Primary atom site location: heavy-atom method

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Mo1	0.79993 (2)	0.60128 (3)	0.24997 (2)	0.02038 (7)
P1	0.89764 (5)	0.44416 (12)	0.15052 (5)	0.02144 (17)
O1	0.95421 (15)	0.8609 (4)	0.26796 (19)	0.0403 (8)
O2	0.82922 (19)	0.2063 (4)	0.34585 (19)	0.0449 (7)
O3	0.7578 (2)	0.7896 (5)	0.4257 (2)	0.0533 (8)
C1	0.89797 (19)	0.7587 (4)	0.2637 (2)	0.0238 (7)
C2	0.8215 (2)	0.3542 (5)	0.3113 (2)	0.0278 (8)
C3	0.8089 (2)	0.6869 (5)	0.3925 (2)	0.0300 (8)
C4	0.8795 (3)	0.6224 (6)	0.4511 (3)	0.0439 (11)
H4A	0.8657	0.4984	0.4791	0.066*
H4B	0.8891	0.7206	0.4966	0.066*
H4C	0.9289	0.6067	0.4155	0.066*
C5	0.7040 (2)	0.8435 (6)	0.2268 (3)	0.0432 (13)
H5	0.7125	0.9674	0.2525	0.052*
C6	0.6620 (2)	0.6856 (7)	0.2659 (3)	0.0465 (11)
H6	0.6375	0.6850	0.3225	0.056*
C7	0.6631 (2)	0.5310 (7)	0.2065 (3)	0.0425 (10)
H7	0.6393	0.4069	0.2156	0.051*
C8	0.7056 (2)	0.5909 (6)	0.1309 (3)	0.0368 (9)
H8	0.7156	0.5137	0.0802	0.044*
C9	0.7308 (2)	0.7839 (6)	0.1427 (3)	0.0376 (9)
H9	0.7604	0.8604	0.1017	0.045*
C10	0.9940 (2)	0.3716 (6)	0.2006 (2)	0.0331 (8)
H10A	1.0193	0.4841	0.2292	0.050*
H10B	1.0308	0.3215	0.1551	0.050*
H10C	0.9839	0.2702	0.2444	0.050*
C11	0.8649 (3)	0.2188 (5)	0.0985 (3)	0.0373 (9)
H11A	0.8542	0.1210	0.1439	0.056*
H11B	0.9080	0.1720	0.0591	0.056*
H11C	0.8150	0.2421	0.0646	0.056*
C12	0.9282 (2)	0.5990 (5)	0.0594 (2)	0.0237 (7)
C13	0.8797 (2)	0.6100 (6)	−0.0161 (2)	0.0337 (9)
H13	0.8334	0.5280	−0.0220	0.040*
C14	0.8991 (3)	0.7407 (6)	−0.0823 (3)	0.0452 (10)
H14	0.8653	0.7487	−0.1329	0.054*
C15	0.9663 (3)	0.8582 (6)	−0.0759 (2)	0.0386 (10)
H15	0.9791	0.9467	−0.1218	0.046*
C16	1.0155 (2)	0.8471 (5)	−0.0018 (3)	0.0347 (9)
H16	1.0628	0.9266	0.0027	0.042*
C17	0.9959 (2)	0.7194 (5)	0.0662 (2)	0.0274 (7)
H17	1.0290	0.7148	0.1175	0.033*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mo1	0.01676 (11)	0.02175 (12)	0.02264 (12)	−0.00044 (9)	−0.00022 (16)	0.00141 (16)
P1	0.0228 (4)	0.0208 (4)	0.0207 (4)	0.0008 (3)	−0.0010 (4)	−0.0001 (3)
O1	0.0323 (13)	0.0419 (15)	0.047 (2)	−0.0136 (11)	0.0007 (12)	−0.0156 (13)
O2	0.0580 (18)	0.0296 (15)	0.0471 (18)	0.0000 (13)	−0.0037 (14)	0.0108 (14)
O3	0.056 (2)	0.065 (2)	0.0386 (16)	0.0241 (17)	0.0116 (14)	−0.0095 (16)
C1	0.0267 (15)	0.0265 (15)	0.0183 (19)	0.0055 (12)	0.0014 (14)	−0.0051 (13)
C2	0.0254 (18)	0.029 (2)	0.0285 (18)	−0.0025 (14)	−0.0001 (14)	−0.0009 (15)
C3	0.035 (2)	0.0295 (19)	0.0259 (18)	0.0013 (16)	0.0048 (15)	0.0024 (15)
C4	0.058 (3)	0.046 (3)	0.027 (2)	0.008 (2)	−0.006 (2)	−0.0063 (18)
C5	0.0278 (19)	0.039 (2)	0.063 (4)	0.0139 (16)	−0.0087 (18)	−0.0031 (18)
C6	0.0172 (16)	0.077 (3)	0.046 (3)	0.0088 (18)	−0.0001 (18)	−0.002 (2)
C7	0.020 (2)	0.053 (3)	0.054 (3)	−0.0112 (18)	−0.0108 (17)	0.013 (2)
C8	0.026 (2)	0.048 (2)	0.036 (2)	0.0003 (16)	−0.0141 (16)	0.0018 (17)
C9	0.0264 (19)	0.039 (2)	0.048 (2)	0.0015 (16)	−0.0110 (18)	0.0168 (19)
C10	0.028 (2)	0.040 (2)	0.031 (2)	0.0105 (16)	0.0008 (16)	0.0041 (15)
C11	0.052 (3)	0.0237 (19)	0.036 (2)	−0.0019 (17)	−0.0030 (18)	−0.0057 (17)
C12	0.0227 (17)	0.0273 (18)	0.0210 (16)	0.0045 (14)	0.0005 (14)	−0.0029 (14)
C13	0.032 (2)	0.043 (2)	0.026 (2)	−0.0112 (16)	−0.0042 (15)	0.0037 (16)
C14	0.050 (3)	0.062 (3)	0.025 (2)	−0.009 (2)	−0.0047 (18)	0.0115 (18)
C15	0.046 (2)	0.039 (2)	0.030 (2)	−0.0019 (18)	0.0108 (17)	0.0091 (17)
C16	0.032 (2)	0.031 (2)	0.042 (2)	−0.0065 (16)	0.0104 (17)	−0.0019 (17)
C17	0.0254 (18)	0.0292 (19)	0.0277 (18)	−0.0006 (15)	0.0010 (14)	−0.0034 (15)

Geometric parameters (Å, º)

Mo1—P1	2.4535 (9)	C6—C7	1.397 (6)
Mo1—C1	1.949 (3)	C7—H7	0.9500
Mo1—C2	1.973 (4)	C7—C8	1.406 (6)
Mo1—C3	2.251 (4)	C8—H8	0.9500
Mo1—C5	2.319 (4)	C8—C9	1.403 (5)
Mo1—C6	2.344 (3)	C9—H9	0.9500
Mo1—C7	2.385 (4)	C10—H10A	0.9800
Mo1—C8	2.382 (4)	C10—H10B	0.9800
Mo1—C9	2.351 (3)	C10—H10C	0.9800
P1—C10	1.822 (4)	C11—H11A	0.9800
P1—C11	1.823 (4)	C11—H11B	0.9800
P1—C12	1.819 (4)	C11—H11C	0.9800
O1—C1	1.161 (4)	C12—C13	1.397 (5)
O2—C2	1.153 (4)	C12—C17	1.388 (5)
O3—C3	1.208 (4)	C13—H13	0.9500
C3—C4	1.525 (5)	C13—C14	1.388 (5)
C4—H4A	0.9800	C14—H14	0.9500
C4—H4B	0.9800	C14—C15	1.370 (6)
C4—H4C	0.9800	C15—H15	0.9500
C5—H5	0.9500	C15—C16	1.387 (6)
C5—C6	1.417 (6)	C16—H16	0.9500
C5—C9	1.413 (6)	C16—C17	1.395 (5)
C6—H6	0.9500	C17—H17	0.9500
C1—Mo1—P1	76.95 (9)	C9—C5—H5	126.0
C1—Mo1—C2	106.40 (14)	C9—C5—C6	107.9 (4)
C1—Mo1—C3	72.37 (13)	Mo1—C6—H6	120.0
C1—Mo1—C5	100.01 (14)	C5—C6—Mo1	71.4 (2)
C1—Mo1—C6	130.12 (14)	C5—C6—H6	126.0
C1—Mo1—C7	156.39 (14)	C7—C6—Mo1	74.5 (2)
C1—Mo1—C8	129.21 (14)	C7—C6—C5	107.9 (4)
C1—Mo1—C9	99.96 (13)	C7—C6—H6	126.0
C2—Mo1—P1	78.13 (11)	Mo1—C7—H7	121.9
C2—Mo1—C3	76.05 (15)	C6—C7—Mo1	71.2 (2)
C2—Mo1—C5	144.49 (15)	C6—C7—H7	125.9
C2—Mo1—C6	109.72 (15)	C6—C7—C8	108.1 (4)
C2—Mo1—C7	97.13 (15)	C8—C7—Mo1	72.7 (2)
C2—Mo1—C8	116.74 (14)	C8—C7—H7	125.9
C2—Mo1—C9	151.18 (14)	Mo1—C8—H8	121.4
C3—Mo1—P1	131.79 (9)	C7—C8—Mo1	73.0 (2)
C3—Mo1—C5	90.13 (14)	C7—C8—H8	125.7
C3—Mo1—C6	84.19 (15)	C9—C8—Mo1	71.5 (2)
C3—Mo1—C7	112.45 (14)	C9—C8—C7	108.6 (4)
C3—Mo1—C8	141.51 (14)	C9—C8—H8	125.7
C3—Mo1—C9	124.02 (14)	Mo1—C9—H9	120.4
C5—Mo1—P1	131.72 (11)	C5—C9—Mo1	71.2 (2)
C5—Mo1—C6	35.38 (15)	C5—C9—H9	126.3
C5—Mo1—C7	57.84 (15)	C8—C9—Mo1	74.0 (2)
C5—Mo1—C8	57.75 (14)	C8—C9—C5	107.5 (4)
C5—Mo1—C9	35.21 (14)	C8—C9—H9	126.3
C6—Mo1—P1	143.25 (12)	P1—C10—H10A	109.5
C6—Mo1—C7	34.36 (15)	P1—C10—H10B	109.5
C6—Mo1—C8	57.40 (15)	P1—C10—H10C	109.5
C6—Mo1—C9	58.34 (15)	H10A—C10—H10B	109.5
C7—Mo1—P1	110.60 (12)	H10A—C10—H10C	109.5
C8—Mo1—P1	86.61 (11)	H10B—C10—H10C	109.5
C8—Mo1—C7	34.30 (14)	P1—C11—H11A	109.5
C9—Mo1—P1	97.03 (11)	P1—C11—H11B	109.5
C9—Mo1—C7	57.58 (14)	P1—C11—H11C	109.5
C9—Mo1—C8	34.49 (13)	H11A—C11—H11B	109.5
C10—P1—Mo1	115.36 (13)	H11A—C11—H11C	109.5
C10—P1—C11	101.66 (18)	H11B—C11—H11C	109.5
C11—P1—Mo1	116.85 (14)	C13—C12—P1	120.1 (3)
C12—P1—Mo1	112.96 (11)	C17—C12—P1	120.8 (3)
C12—P1—C10	103.97 (17)	C17—C12—C13	118.9 (3)
C12—P1—C11	104.47 (17)	C12—C13—H13	120.0
O1—C1—Mo1	175.6 (3)	C14—C13—C12	120.1 (3)
O2—C2—Mo1	175.7 (3)	C14—C13—H13	120.0
O3—C3—Mo1	120.7 (3)	C13—C14—H14	119.5
O3—C3—C4	116.8 (3)	C15—C14—C13	121.0 (4)
C4—C3—Mo1	122.4 (3)	C15—C14—H14	119.5
C3—C4—H4A	109.5	C14—C15—H15	120.3
C3—C4—H4B	109.5	C14—C15—C16	119.5 (4)
C3—C4—H4C	109.5	C16—C15—H15	120.3
H4A—C4—H4B	109.5	C15—C16—H16	119.9
H4A—C4—H4C	109.5	C15—C16—C17	120.2 (3)
H4B—C4—H4C	109.5	C17—C16—H16	119.9
Mo1—C5—H5	119.0	C12—C17—C16	120.3 (3)
C6—C5—Mo1	73.3 (2)	C12—C17—H17	119.8
C6—C5—H5	126.0	C16—C17—H17	119.8
C9—C5—Mo1	73.6 (2)
Mo1—P1—C12—C13	−84.0 (3)	C7—C8—C9—Mo1	64.1 (3)
Mo1—P1—C12—C17	90.8 (3)	C7—C8—C9—C5	0.3 (4)
Mo1—C5—C6—C7	−66.0 (3)	C9—C5—C6—Mo1	66.0 (2)
Mo1—C5—C9—C8	65.6 (2)	C9—C5—C6—C7	0.0 (4)
Mo1—C6—C7—C8	−63.8 (3)	C10—P1—C12—C13	150.3 (3)
Mo1—C7—C8—C9	−63.1 (2)	C10—P1—C12—C17	−35.0 (3)
Mo1—C8—C9—C5	−63.7 (2)	C11—P1—C12—C13	44.0 (3)
P1—C12—C13—C14	174.4 (3)	C11—P1—C12—C17	−141.2 (3)
P1—C12—C17—C16	−175.7 (3)	C12—C13—C14—C15	1.1 (6)
C5—C6—C7—Mo1	64.0 (2)	C13—C12—C17—C16	−0.8 (5)
C5—C6—C7—C8	0.2 (4)	C13—C14—C15—C16	−0.3 (6)
C6—C5—C9—Mo1	−65.8 (3)	C14—C15—C16—C17	−1.1 (6)
C6—C5—C9—C8	−0.2 (4)	C15—C16—C17—C12	1.6 (5)
C6—C7—C8—Mo1	62.8 (3)	C17—C12—C13—C14	−0.5 (6)
C6—C7—C8—C9	−0.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O3^i	0.98	2.45	3.344 (5)	152
C13—H13···O3^i	0.95	2.36	3.275 (5)	162

Symmetry code: (i) −x+3/2, y−1/2, z−1/2.

(2) trans-Acetyldicarbonyl(η⁵-cyclopentadienyl)(ethyldiphenylphosphane)molybdenum(II)

Crystal data

[Mo(C5H5)(C2H3O)(C14H15P)(CO)2]	Z = 2
Mr = 474.32	F(000) = 484
Triclinic, P1	Dx = 1.504 Mg m^−3
a = 8.2451 (8) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6132 (11) Å	Cell parameters from 10268 reflections
c = 12.5265 (12) Å	θ = 3.2–27.6°
α = 63.617 (4)°	µ = 0.72 mm^−1
β = 77.167 (5)°	T = 173 K
γ = 84.671 (6)°	Prism, yellow
V = 1047.65 (18) Å^3	0.32 × 0.26 × 0.21 mm

Data collection

Rigaku XtaLAB mini diffractometer	4365 reflections with I > 2σ(I)
Detector resolution: 6.849 pixels mm^-1	Rint = 0.029
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −10→10
Tmin = 0.712, Tmax = 0.859	k = −15→15
11081 measured reflections	l = −16→16
4797 independent reflections

Refinement

Refinement on F^2	Primary atom site location: heavy-atom method
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.028	H-atom parameters constrained
wR(F^2) = 0.068	w = 1/[σ^2(Fo^2) + (0.029P)^2 + 0.4738P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
4797 reflections	Δρmax = 0.30 e Å^−3
255 parameters	Δρmin = −0.82 e Å^−3
0 restraints

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Mo1	0.25391 (2)	0.22164 (2)	0.24017 (2)	0.01783 (6)
P1	0.15696 (6)	0.36677 (5)	0.33857 (5)	0.01874 (11)
O1	0.2231 (2)	0.48000 (14)	0.01116 (14)	0.0328 (4)
O2	−0.1013 (2)	0.10837 (16)	0.37595 (17)	0.0379 (4)
O3	0.2283 (2)	0.07548 (18)	0.09140 (19)	0.0459 (5)
C1	0.2279 (3)	0.3845 (2)	0.0971 (2)	0.0225 (4)
C2	0.0285 (3)	0.1541 (2)	0.3233 (2)	0.0248 (4)
C3	0.1579 (3)	0.1604 (2)	0.1164 (2)	0.0256 (5)
C4	0.0061 (3)	0.2187 (2)	0.0626 (2)	0.0361 (6)
H4A	−0.0914	0.1955	0.1265	0.054*
H4B	−0.0043	0.1869	0.0055	0.054*
H4C	0.0177	0.3106	0.0217	0.054*
C5	0.5510 (3)	0.2184 (2)	0.2032 (2)	0.0313 (5)
H5	0.6164	0.2873	0.1426	0.038*
C6	0.4935 (3)	0.1161 (2)	0.1898 (2)	0.0319 (5)
H6	0.5130	0.1063	0.1183	0.038*
C7	0.4005 (3)	0.0304 (2)	0.3044 (2)	0.0331 (5)
H7	0.3493	−0.0456	0.3213	0.040*
C8	0.4000 (3)	0.0813 (2)	0.3878 (2)	0.0321 (5)
H8	0.3485	0.0450	0.4696	0.039*
C9	0.4922 (3)	0.1978 (2)	0.3243 (2)	0.0309 (5)
H9	0.5107	0.2517	0.3575	0.037*
C10	−0.0688 (3)	0.3899 (2)	0.3745 (2)	0.0247 (4)
H10A	−0.1210	0.3075	0.4308	0.030*
H10B	−0.0899	0.4456	0.4151	0.030*
C11	−0.1500 (3)	0.4481 (2)	0.2632 (2)	0.0347 (5)
H11A	−0.1027	0.5316	0.2084	0.052*
H11B	−0.2675	0.4560	0.2887	0.052*
H11C	−0.1307	0.3934	0.2226	0.052*
C12	0.2069 (3)	0.30616 (19)	0.49000 (19)	0.0219 (4)
C13	0.1367 (3)	0.1892 (2)	0.5807 (2)	0.0273 (5)
H13	0.0644	0.1458	0.5636	0.033*
C14	0.1734 (3)	0.1371 (2)	0.6958 (2)	0.0317 (5)
H14	0.1254	0.0593	0.7554	0.038*
C15	0.2814 (3)	0.2006 (2)	0.7222 (2)	0.0338 (5)
H15	0.3055	0.1660	0.7996	0.041*
C16	0.3534 (3)	0.3154 (2)	0.6333 (2)	0.0347 (5)
H16	0.4268	0.3577	0.6508	0.042*
C17	0.3166 (3)	0.3686 (2)	0.5174 (2)	0.0284 (5)
H17	0.3656	0.4461	0.4580	0.034*
C18	0.2429 (3)	0.53126 (19)	0.26053 (19)	0.0216 (4)
C19	0.4009 (3)	0.5528 (2)	0.18706 (19)	0.0245 (4)
H19	0.4597	0.4851	0.1765	0.029*
C20	0.4719 (3)	0.6756 (2)	0.1291 (2)	0.0272 (5)
H20	0.5786	0.6889	0.0813	0.033*
C21	0.3841 (3)	0.7775 (2)	0.1424 (2)	0.0294 (5)
H21	0.4309	0.8595	0.1028	0.035*
C22	0.2268 (3)	0.7569 (2)	0.2148 (2)	0.0334 (5)
H22	0.1674	0.8253	0.2235	0.040*
C23	0.1566 (3)	0.6340 (2)	0.2749 (2)	0.0306 (5)
H23	0.0514	0.6205	0.3248	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Mo1	0.01765 (10)	0.01435 (9)	0.01900 (10)	0.00154 (6)	−0.00451 (7)	−0.00496 (7)
P1	0.0185 (2)	0.0163 (2)	0.0196 (3)	0.00010 (19)	−0.0039 (2)	−0.0062 (2)
O1	0.0459 (10)	0.0201 (8)	0.0262 (8)	0.0016 (7)	−0.0129 (8)	−0.0023 (7)
O2	0.0284 (9)	0.0325 (9)	0.0484 (11)	−0.0103 (7)	0.0027 (8)	−0.0168 (8)
O3	0.0520 (12)	0.0396 (10)	0.0655 (13)	0.0108 (9)	−0.0235 (10)	−0.0368 (10)
C1	0.0230 (10)	0.0208 (10)	0.0270 (11)	0.0015 (8)	−0.0070 (9)	−0.0126 (9)
C2	0.0264 (11)	0.0180 (10)	0.0297 (11)	0.0006 (8)	−0.0084 (9)	−0.0089 (9)
C3	0.0294 (11)	0.0214 (11)	0.0252 (11)	−0.0043 (9)	−0.0052 (9)	−0.0087 (9)
C4	0.0410 (14)	0.0355 (13)	0.0378 (14)	0.0009 (11)	−0.0194 (12)	−0.0161 (11)
C5	0.0166 (10)	0.0304 (12)	0.0373 (13)	0.0045 (9)	−0.0036 (9)	−0.0077 (10)
C6	0.0258 (12)	0.0348 (13)	0.0348 (13)	0.0148 (10)	−0.0068 (10)	−0.0173 (11)
C7	0.0329 (13)	0.0183 (11)	0.0421 (14)	0.0091 (9)	−0.0128 (11)	−0.0074 (10)
C8	0.0244 (11)	0.0354 (13)	0.0247 (11)	0.0100 (10)	−0.0098 (9)	−0.0022 (10)
C9	0.0190 (11)	0.0379 (13)	0.0396 (13)	0.0083 (9)	−0.0118 (10)	−0.0191 (11)
C10	0.0203 (10)	0.0230 (11)	0.0284 (11)	0.0009 (8)	−0.0025 (9)	−0.0105 (9)
C11	0.0265 (12)	0.0369 (13)	0.0442 (15)	0.0082 (10)	−0.0157 (11)	−0.0184 (12)
C12	0.0228 (10)	0.0208 (10)	0.0213 (10)	0.0024 (8)	−0.0051 (8)	−0.0086 (8)
C13	0.0321 (12)	0.0214 (11)	0.0272 (11)	−0.0026 (9)	−0.0069 (10)	−0.0086 (9)
C14	0.0400 (13)	0.0220 (11)	0.0260 (12)	0.0008 (10)	−0.0070 (10)	−0.0041 (9)
C15	0.0439 (14)	0.0332 (13)	0.0254 (12)	0.0074 (11)	−0.0163 (11)	−0.0110 (10)
C16	0.0403 (14)	0.0349 (13)	0.0348 (13)	−0.0014 (11)	−0.0171 (11)	−0.0157 (11)
C17	0.0320 (12)	0.0259 (11)	0.0267 (11)	−0.0045 (9)	−0.0063 (10)	−0.0100 (9)
C18	0.0246 (10)	0.0175 (10)	0.0215 (10)	−0.0004 (8)	−0.0073 (8)	−0.0062 (8)
C19	0.0267 (11)	0.0219 (11)	0.0255 (11)	−0.0002 (8)	−0.0046 (9)	−0.0111 (9)
C20	0.0281 (11)	0.0283 (12)	0.0234 (11)	−0.0072 (9)	−0.0003 (9)	−0.0105 (9)
C21	0.0398 (13)	0.0193 (11)	0.0269 (12)	−0.0065 (9)	−0.0080 (10)	−0.0063 (9)
C22	0.0392 (14)	0.0199 (11)	0.0418 (14)	0.0019 (10)	−0.0078 (11)	−0.0146 (10)
C23	0.0297 (12)	0.0240 (11)	0.0347 (13)	0.0004 (9)	−0.0020 (10)	−0.0118 (10)

Geometric parameters (Å, º)

Mo1—P1	2.4813 (6)	C10—H10A	0.9700
Mo1—C1	1.979 (2)	C10—H10B	0.9700
Mo1—C2	1.960 (2)	C10—C11	1.530 (3)
Mo1—C3	2.273 (2)	C11—H11A	0.9600
Mo1—C5	2.390 (2)	C11—H11B	0.9600
Mo1—C6	2.342 (2)	C11—H11C	0.9600
Mo1—C7	2.321 (2)	C12—C13	1.398 (3)
Mo1—C8	2.340 (2)	C12—C17	1.393 (3)
Mo1—C9	2.368 (2)	C13—H13	0.9300
P1—C10	1.839 (2)	C13—C14	1.386 (3)
P1—C12	1.836 (2)	C14—H14	0.9300
P1—C18	1.841 (2)	C14—C15	1.385 (3)
O1—C1	1.158 (3)	C15—H15	0.9300
O2—C2	1.158 (3)	C15—C16	1.380 (3)
O3—C3	1.223 (3)	C16—H16	0.9300
C3—C4	1.514 (3)	C16—C17	1.395 (3)
C4—H4A	0.9600	C17—H17	0.9300
C4—H4B	0.9600	C18—C19	1.389 (3)
C4—H4C	0.9600	C18—C23	1.392 (3)
C5—H5	0.9300	C19—H19	0.9300
C5—C6	1.408 (3)	C19—C20	1.396 (3)
C5—C9	1.403 (3)	C20—H20	0.9300
C6—H6	0.9300	C20—C21	1.384 (3)
C6—C7	1.422 (3)	C21—H21	0.9300
C7—H7	0.9300	C21—C22	1.379 (3)
C7—C8	1.410 (4)	C22—H22	0.9300
C8—H8	0.9300	C22—C23	1.395 (3)
C8—C9	1.417 (3)	C23—H23	0.9300
C9—H9	0.9300
C1—Mo1—P1	79.07 (6)	C6—C7—Mo1	73.06 (12)
C1—Mo1—C3	75.46 (8)	C6—C7—H7	126.2
C1—Mo1—C5	97.88 (8)	C8—C7—Mo1	73.12 (13)
C1—Mo1—C6	109.55 (9)	C8—C7—C6	107.7 (2)
C1—Mo1—C7	144.10 (9)	C8—C7—H7	126.2
C1—Mo1—C8	153.01 (9)	Mo1—C8—H8	120.3
C1—Mo1—C9	118.12 (9)	C7—C8—Mo1	71.68 (12)
C2—Mo1—P1	79.67 (6)	C7—C8—H8	126.2
C2—Mo1—C1	106.04 (9)	C7—C8—C9	107.6 (2)
C2—Mo1—C3	73.53 (9)	C9—C8—Mo1	73.60 (12)
C2—Mo1—C5	155.94 (9)	C9—C8—H8	126.2
C2—Mo1—C6	129.67 (9)	Mo1—C9—H9	121.0
C2—Mo1—C7	99.26 (9)	C5—C9—Mo1	73.70 (13)
C2—Mo1—C8	99.09 (9)	C5—C9—C8	108.7 (2)
C2—Mo1—C9	128.81 (9)	C5—C9—H9	125.7
C3—Mo1—P1	135.76 (6)	C8—C9—Mo1	71.38 (12)
C3—Mo1—C5	110.95 (8)	C8—C9—H9	125.7
C3—Mo1—C6	82.22 (8)	P1—C10—H10A	108.7
C3—Mo1—C7	88.08 (8)	P1—C10—H10B	108.7
C3—Mo1—C8	122.06 (9)	H10A—C10—H10B	107.6
C3—Mo1—C9	139.73 (8)	C11—C10—P1	114.02 (16)
C5—Mo1—P1	107.89 (6)	C11—C10—H10A	108.7
C6—Mo1—P1	140.94 (6)	C11—C10—H10B	108.7
C6—Mo1—C5	34.59 (8)	C10—C11—H11A	109.5
C6—Mo1—C9	57.61 (8)	C10—C11—H11B	109.5
C7—Mo1—P1	131.14 (7)	C10—C11—H11C	109.5
C7—Mo1—C5	58.24 (8)	H11A—C11—H11B	109.5
C7—Mo1—C6	35.51 (8)	H11A—C11—H11C	109.5
C7—Mo1—C8	35.20 (9)	H11B—C11—H11C	109.5
C7—Mo1—C9	58.20 (9)	C13—C12—P1	118.36 (16)
C8—Mo1—P1	96.21 (7)	C17—C12—P1	123.11 (16)
C8—Mo1—C5	57.94 (8)	C17—C12—C13	118.5 (2)
C8—Mo1—C6	58.45 (9)	C12—C13—H13	119.5
C8—Mo1—C9	35.03 (8)	C14—C13—C12	120.9 (2)
C9—Mo1—P1	84.34 (6)	C14—C13—H13	119.5
C9—Mo1—C5	34.29 (8)	C13—C14—H14	120.0
C10—P1—Mo1	117.10 (7)	C15—C14—C13	120.0 (2)
C10—P1—C18	103.97 (10)	C15—C14—H14	120.0
C12—P1—Mo1	112.60 (7)	C14—C15—H15	120.1
C12—P1—C10	100.72 (10)	C16—C15—C14	119.8 (2)
C12—P1—C18	102.90 (9)	C16—C15—H15	120.1
C18—P1—Mo1	117.35 (7)	C15—C16—H16	119.8
O1—C1—Mo1	175.79 (19)	C15—C16—C17	120.4 (2)
O2—C2—Mo1	176.56 (19)	C17—C16—H16	119.8
O3—C3—Mo1	120.13 (17)	C12—C17—C16	120.3 (2)
O3—C3—C4	116.7 (2)	C12—C17—H17	119.8
C4—C3—Mo1	123.19 (16)	C16—C17—H17	119.8
C3—C4—H4A	109.5	C19—C18—P1	118.76 (16)
C3—C4—H4B	109.5	C19—C18—C23	118.97 (19)
C3—C4—H4C	109.5	C23—C18—P1	122.26 (17)
H4A—C4—H4B	109.5	C18—C19—H19	119.8
H4A—C4—H4C	109.5	C18—C19—C20	120.4 (2)
H4B—C4—H4C	109.5	C20—C19—H19	119.8
Mo1—C5—H5	122.7	C19—C20—H20	119.9
C6—C5—Mo1	70.86 (12)	C21—C20—C19	120.2 (2)
C6—C5—H5	126.1	C21—C20—H20	119.9
C9—C5—Mo1	72.01 (13)	C20—C21—H21	120.2
C9—C5—H5	126.1	C22—C21—C20	119.7 (2)
C9—C5—C6	107.7 (2)	C22—C21—H21	120.2
Mo1—C6—H6	119.9	C21—C22—H22	119.8
C5—C6—Mo1	74.56 (13)	C21—C22—C23	120.3 (2)
C5—C6—H6	125.9	C23—C22—H22	119.8
C5—C6—C7	108.3 (2)	C18—C23—C22	120.4 (2)
C7—C6—Mo1	71.43 (12)	C18—C23—H23	119.8
C7—C6—H6	125.9	C22—C23—H23	119.8
Mo1—C7—H7	119.5
Mo1—P1—C10—C11	−60.67 (18)	C9—C5—C6—C7	−1.0 (2)
Mo1—P1—C12—C13	−62.49 (18)	C10—P1—C12—C13	63.03 (19)
Mo1—P1—C12—C17	114.86 (18)	C10—P1—C12—C17	−119.61 (19)
Mo1—P1—C18—C19	−28.34 (19)	C10—P1—C18—C19	−159.42 (17)
Mo1—P1—C18—C23	153.15 (17)	C10—P1—C18—C23	22.1 (2)
Mo1—C5—C6—C7	−63.95 (15)	C12—P1—C10—C11	176.90 (17)
Mo1—C5—C9—C8	63.24 (15)	C12—P1—C18—C19	95.88 (18)
Mo1—C6—C7—C8	−65.44 (15)	C12—P1—C18—C23	−82.6 (2)
Mo1—C7—C8—C9	−65.34 (15)	C12—C13—C14—C15	−0.3 (4)
Mo1—C8—C9—C5	−64.74 (16)	C13—C12—C17—C16	−0.6 (3)
P1—C12—C13—C14	178.29 (18)	C13—C14—C15—C16	−0.5 (4)
P1—C12—C17—C16	−177.99 (18)	C14—C15—C16—C17	0.6 (4)
P1—C18—C19—C20	−178.29 (17)	C15—C16—C17—C12	−0.1 (4)
P1—C18—C23—C22	179.50 (18)	C17—C12—C13—C14	0.8 (3)
C5—C6—C7—Mo1	66.00 (15)	C18—P1—C10—C11	70.56 (18)
C5—C6—C7—C8	0.6 (2)	C18—P1—C12—C13	170.22 (17)
C6—C5—C9—Mo1	−62.23 (15)	C18—P1—C12—C17	−12.4 (2)
C6—C5—C9—C8	1.0 (2)	C18—C19—C20—C21	−1.2 (3)
C6—C7—C8—Mo1	65.40 (15)	C19—C18—C23—C22	1.0 (3)
C6—C7—C8—C9	0.1 (2)	C19—C20—C21—C22	0.9 (3)
C7—C8—C9—Mo1	64.07 (15)	C20—C21—C22—C23	0.3 (4)
C7—C8—C9—C5	−0.7 (2)	C21—C22—C23—C18	−1.3 (4)
C9—C5—C6—Mo1	62.98 (15)	C23—C18—C19—C20	0.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2^i	0.93	2.63	3.414 (3)	142
C13—H13···O2^i	0.93	2.71	3.282 (3)	121
C22—H22···O3^ii	0.93	2.66	3.316 (3)	128

Symmetry codes: (i) −x, −y, −z+1; (ii) x, y+1, z.