cis-Bis(benzyl­methyl­phenyl­phosphine-κP)tetra­carbonyl­molybdenum(0)

Doddi, A.; Luiz, T.A.; Ramkumar, V.; Rao, M.N.S.

doi:10.1107/S1600536807048982

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cis-Bis(benzylmethylphenylphosphine-κP)tetracarbonylmolybdenum(0)

A. Doddi, T. A. Luiz, V. Ramkumar and M. N. S. Rao

In the title compound, [Mo(CO)₄(C₁₄H₁₅P)₂], the molybdenum center has a slightly distorted cis-MoP₂C₄ octahedral geometry. One of the phosphine ligands is disordered over two orientations in a 0.686 (3):0.314 (3) ratio. The packing may be stabilized by weak C—H

O and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807048982/hb2548sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807048982/hb2548Isup2.hkl Contains datablock I

CCDC reference: 667159

checkCIF report

Key indicators

Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.007 Å
Disorder in main residue
R factor = 0.046
wR factor = 0.141
Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.94

Author Response: The crystal weakly diffracted even after several attempts of recrystallisation.


Alert level C
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        200 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C31
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C30
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C23A
PLAT301_ALERT_3_C Main Residue  Disorder .........................      19.00 Perc.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C27    -   C28    ...       1.36 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C27    -   C32    ...       1.38 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         38
            C4  -MO1 -P1A -C26A   41.60  1.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         44
            C4  -MO1 -P1A -C19A  163.90  1.40   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         50
            C4  -MO1 -P1A -C27   -87.30  1.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         78
            C4  -MO1 -P1  -C27    77.60  1.10   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         84
            C4  -MO1 -P1  -C26   -46.50  1.20   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         90
            C4  -MO1 -P1  -C19  -167.10  1.10   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        119
            C2  -MO1 -P2  -C12    71.20  1.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        125
            C2  -MO1 -P2  -C13  -164.30  1.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #        131
            C2  -MO1 -P2  -C5    -45.10  1.60   1.555   1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      17.87 Deg.
              P1   -C27  -P1A     1.555   1.555   1.555

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           28.34
           From the CIF: _reflns_number_total               6531
           From the CIF: _diffrn_reflns_limit_ max hkl   13.   14.   17.
           From the CIF: _diffrn_reflns_limit_ min hkl  -12.  -14.  -16.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   13.   14.   19.
           Calculated minimum hkl  -13.  -14.  -19.
PLAT793_ALERT_1_G Check the Absolute Configuration of P2     = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  18 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   9 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Tertiary phosphines, PR₃, have been used to modify both the solubility and stability aspects of metal carbonyl compounds (Smith & Baird, 1982). Herein, we report the synthesis and structure of the title compound, (I). It is observed that the Mo atom sits at the center of a distorted octahedron and the two phosphine ligands are cis to each other (Fig. 1, Table 1).

The Mo—P bond distances are almost the same with corresponding Mo—C_trans bond distances of 1.973 (4) and 2.000 (5) Å respectively. The other two Mo—C bond distances are 2.021 (4) and 2.032 (5) Å. The relative shortening of the Mo—C_trans bond can be attributed to the greater back donation from metal center to CO than phosphine, the former being a better π-acceptor.

In the packing of (I), a weak C—H···O bond (Fig. 2) may help to establish the packing, as does a C—H···π interaction between two phenyl rings of adjacent molecules with H···π = 2.85 Å.

Related literature top

For related literature, see: Smith & Baird (1982).

Experimental top

To a stirred solution of Mo(CO)₆ (0.18 g, 0.70 mmol) in toluene (20 ml) at room temperature was added dropwise, benzyl(methyl)(phenyl)phosphine (0.29 g, 1.40 mmol) in toluene (5 ml) over 10 minutes. After complete addition, the reaction mixture was refluxed for 5 h and the resultant blackish brown solution was pumped off completely to get a brown residue. This was extracted with hot hexane (5 × 5 ml) and the light brown hexane extract was concentrated to half of its volume and cooled in a deep freezer for two days to isolate pale yellow blocks of (I).

Structure description top

For related literature, see: Smith & Baird (1982).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. View of the molecular structure of (I) with displacement ellipsoids drawn with 50% probability for the non-H atoms. The minor disorder component of the phosphine ligand is not shown.

cis-Bis(benzylmethylphenylphosphine-kP)tetracarbonylmolybdenum(0) top

Crystal data top

[Mo(CO)₄(C₁₄H₁₅P)₂]	Z = 2
M_r = 636.44	F(000) = 652
Triclinic, P1	D_x = 1.389 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9318 (4) Å	Cell parameters from 6018 reflections
b = 10.6434 (5) Å	θ = 2.4–25.0°
c = 14.9527 (7) Å	µ = 0.57 mm⁻¹
α = 88.643 (2)°	T = 173 K
β = 77.279 (2)°	Block, pale yellow
γ = 80.879 (2)°	0.20 × 0.18 × 0.15 mm
V = 1522.23 (12) Å³

Data collection top

Bruker APEX CCD diffractometer	6531 independent reflections
Radiation source: fine-focus sealed tube	4924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
φ and ω scans	θ_max = 28.3°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −12→13
T_min = 0.895, T_max = 0.919	k = −14→14
19662 measured reflections	l = −16→17

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0864P)²] where P = (F_o² + 2F_c²)/3
6531 reflections	(Δ/σ)_max = 0.001
408 parameters	Δρ_max = 0.97 e Å⁻³
4 restraints	Δρ_min = −0.63 e Å⁻³

Crystal data top

[Mo(CO)₄(C₁₄H₁₅P)₂]	γ = 80.879 (2)°
M_r = 636.44	V = 1522.23 (12) Å³
Triclinic, P1	Z = 2
a = 9.9318 (4) Å	Mo Kα radiation
b = 10.6434 (5) Å	µ = 0.57 mm⁻¹
c = 14.9527 (7) Å	T = 173 K
α = 88.643 (2)°	0.20 × 0.18 × 0.15 mm
β = 77.279 (2)°

Data collection top

Bruker APEX CCD diffractometer	6531 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	4924 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.919	R_int = 0.045
19662 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	4 restraints
wR(F²) = 0.141	H-atom parameters constrained
S = 1.04	Δρ_max = 0.97 e Å⁻³
6531 reflections	Δρ_min = −0.63 e Å⁻³
408 parameters

Special details top

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.

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 > σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	−0.1063 (4)	0.6468 (4)	0.8145 (3)	0.0384 (9)
C2	−0.2223 (5)	0.8344 (4)	0.7017 (3)	0.0471 (10)
C3	0.0285 (6)	0.8001 (4)	0.5665 (3)	0.0615 (13)
C4	−0.1078 (5)	0.5936 (4)	0.6319 (3)	0.0481 (10)
C5	0.1710 (4)	0.4053 (3)	0.6718 (3)	0.0441 (10)
H5A	0.1343	0.3826	0.7347	0.053*
H5B	0.1014	0.3962	0.6370	0.053*
C6	0.3005 (4)	0.3117 (3)	0.6341 (3)	0.0405 (9)
C7	0.3255 (5)	0.2625 (4)	0.5463 (3)	0.0485 (11)
H7	0.2610	0.2874	0.5102	0.058*
C8	0.4450 (5)	0.1767 (4)	0.5110 (3)	0.0533 (12)
H8	0.4600	0.1448	0.4517	0.064*
C9	0.5410 (5)	0.1387 (4)	0.5635 (3)	0.0542 (12)
H9	0.6207	0.0805	0.5403	0.065*
C10	0.5187 (5)	0.1875 (4)	0.6506 (4)	0.0587 (12)
H10	0.5840	0.1628	0.6862	0.070*
C11	0.3991 (5)	0.2735 (4)	0.6859 (3)	0.0516 (11)
H11	0.3850	0.3058	0.7450	0.062*
C12	0.3132 (4)	0.5864 (4)	0.5599 (3)	0.0440 (10)
H12A	0.2636	0.5860	0.5116	0.066*
H12B	0.3875	0.5152	0.5519	0.066*
H12C	0.3515	0.6640	0.5580	0.066*
C13	0.3038 (4)	0.5773 (3)	0.7537 (3)	0.0343 (8)
C14	0.4370 (4)	0.6103 (3)	0.7307 (3)	0.0428 (9)
H14	0.4745	0.6302	0.6704	0.051*
C15	0.5145 (5)	0.6139 (4)	0.7972 (3)	0.0544 (12)
H15	0.6039	0.6351	0.7813	0.065*
C16	0.4592 (5)	0.5861 (4)	0.8861 (3)	0.0576 (12)
H16	0.5112	0.5895	0.9305	0.069*
C17	0.3276 (5)	0.5532 (4)	0.9109 (3)	0.0524 (11)
H17	0.2909	0.5339	0.9715	0.063*
C18	0.2503 (4)	0.5491 (3)	0.8445 (3)	0.0428 (9)
H18	0.1612	0.5272	0.8611	0.051*
C27	−0.0769 (4)	1.0486 (3)	0.7858 (3)	0.0443 (10)
C28	−0.1767 (5)	1.0600 (5)	0.8649 (4)	0.0739 (16)
H28	−0.1819	0.9912	0.9044	0.089*
C29	−0.2703 (5)	1.1702 (5)	0.8885 (4)	0.0738 (15)
H29	−0.3359	1.1756	0.9438	0.089*
C30	−0.2674 (5)	1.2693 (4)	0.8323 (4)	0.0666 (14)
H30	−0.3307	1.3438	0.8483	0.080*
C31	−0.1726 (6)	1.2612 (6)	0.7523 (5)	0.095 (2)
H31	−0.1723	1.3295	0.7124	0.114*
C32	−0.0762 (6)	1.1530 (6)	0.7289 (4)	0.0801 (17)
H32	−0.0097	1.1500	0.6741	0.096*
Mo1	−0.03646 (3)	0.72449 (3)	0.69173 (2)	0.03031 (13)
O3	0.0614 (5)	0.8413 (4)	0.4955 (3)	0.1113 (16)
O1	−0.1525 (4)	0.5994 (3)	0.8822 (2)	0.0615 (9)
O4	−0.1519 (4)	0.5186 (3)	0.5977 (3)	0.0780 (11)
O2	−0.3300 (4)	0.8933 (3)	0.7044 (3)	0.0732 (10)
P1A	0.0361 (6)	0.8890 (5)	0.7858 (4)	0.0307 (11)	0.314 (3)
C19A	0.2040 (12)	0.9480 (12)	0.7392 (8)	0.046 (3)	0.314 (3)
H19A	0.2753	0.8761	0.7157	0.056*	0.314 (3)
H19B	0.1929	1.0038	0.6882	0.056*	0.314 (3)
C20A	0.2545 (10)	1.0207 (8)	0.8106 (6)	0.041 (3)	0.314 (3)
C21A	0.3667 (11)	0.9626 (10)	0.8461 (10)	0.067 (8)	0.314 (3)
H21A	0.4119	0.8818	0.8257	0.080*	0.314 (3)
C22A	0.4113 (12)	1.0254 (16)	0.9120 (11)	0.065 (7)	0.314 (3)
H22A	0.4864	0.9866	0.9357	0.079*	0.314 (3)
C23A	0.3438 (15)	1.1463 (16)	0.9424 (9)	0.041 (5)	0.314 (3)
H23A	0.3737	1.1884	0.9865	0.049*	0.314 (3)
C24A	0.2316 (14)	1.2044 (10)	0.9069 (9)	0.052 (6)	0.314 (3)
H24A	0.1864	1.2853	0.9272	0.063*	0.314 (3)
C25A	0.1870 (9)	1.1416 (8)	0.8410 (7)	0.048 (3)	0.314 (3)
H25A	0.1119	1.1805	0.8173	0.058*	0.314 (3)
C26A	0.0523 (13)	0.8431 (11)	0.9012 (7)	0.032 (3)	0.314 (3)
H26A	−0.0300	0.8103	0.9323	0.049*	0.314 (3)
H26B	0.0628	0.9160	0.9341	0.049*	0.314 (3)
H26C	0.1327	0.7786	0.8982	0.049*	0.314 (3)
P1	0.0560 (3)	0.9086 (2)	0.74968 (17)	0.0304 (5)	0.686 (3)
C19	0.1234 (6)	0.8853 (5)	0.8552 (4)	0.0364 (13)	0.686 (3)
H19C	0.0456	0.8766	0.9059	0.044*	0.686 (3)
H19D	0.1875	0.8056	0.8492	0.044*	0.686 (3)
C20	0.1982 (4)	0.9895 (3)	0.8801 (3)	0.0381 (13)	0.686 (3)
C21	0.3430 (5)	0.9666 (5)	0.8660 (5)	0.052 (3)	0.686 (3)
H21	0.3926	0.8888	0.8419	0.063*	0.686 (3)
C22	0.4139 (5)	1.0601 (8)	0.8880 (6)	0.061 (3)	0.686 (3)
H22	0.5108	1.0448	0.8786	0.074*	0.686 (3)
C23	0.3399 (7)	1.1764 (7)	0.9241 (6)	0.066 (4)	0.686 (3)
H23	0.3873	1.2389	0.9389	0.080*	0.686 (3)
C24	0.1950 (7)	1.1992 (4)	0.9382 (4)	0.054 (3)	0.686 (3)
H24	0.1455	1.2770	0.9623	0.065*	0.686 (3)
C25	0.1242 (4)	1.1058 (4)	0.9162 (3)	0.0444 (15)	0.686 (3)
H25	0.0272	1.1211	0.9256	0.053*	0.686 (3)
C26	0.2017 (6)	0.9632 (6)	0.6689 (4)	0.0465 (16)	0.686 (3)
H26D	0.2737	0.8920	0.6484	0.070*	0.686 (3)
H26E	0.2386	1.0245	0.6988	0.070*	0.686 (3)
H26F	0.1693	1.0017	0.6172	0.070*	0.686 (3)
P2	0.19348 (10)	0.57500 (8)	0.67027 (7)	0.0320 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.036 (2)	0.041 (2)	0.039 (2)	−0.0035 (16)	−0.0104 (17)	−0.0065 (17)
C2	0.057 (3)	0.034 (2)	0.056 (3)	−0.0087 (19)	−0.022 (2)	0.0012 (18)
C3	0.083 (4)	0.045 (3)	0.051 (3)	0.002 (2)	−0.011 (2)	0.010 (2)
C4	0.065 (3)	0.038 (2)	0.049 (3)	−0.0033 (19)	−0.033 (2)	0.0013 (18)
C5	0.046 (2)	0.0250 (18)	0.063 (3)	−0.0071 (16)	−0.014 (2)	0.0022 (17)
C6	0.048 (2)	0.0238 (17)	0.051 (3)	−0.0062 (16)	−0.0122 (19)	0.0006 (16)
C7	0.071 (3)	0.030 (2)	0.050 (3)	−0.0055 (19)	−0.027 (2)	−0.0006 (18)
C8	0.079 (3)	0.029 (2)	0.047 (3)	−0.009 (2)	−0.001 (2)	−0.0077 (18)
C9	0.055 (3)	0.028 (2)	0.073 (3)	0.0008 (18)	−0.005 (2)	−0.003 (2)
C10	0.062 (3)	0.039 (2)	0.077 (4)	0.007 (2)	−0.028 (3)	−0.004 (2)
C11	0.070 (3)	0.034 (2)	0.049 (3)	0.004 (2)	−0.019 (2)	−0.0047 (18)
C12	0.049 (2)	0.041 (2)	0.039 (2)	−0.0111 (18)	−0.0008 (18)	−0.0059 (17)
C13	0.038 (2)	0.0193 (16)	0.045 (2)	0.0006 (14)	−0.0123 (16)	−0.0009 (14)
C14	0.042 (2)	0.034 (2)	0.055 (3)	−0.0063 (16)	−0.0152 (19)	0.0045 (17)
C15	0.048 (2)	0.044 (2)	0.080 (4)	−0.0100 (19)	−0.032 (2)	0.009 (2)
C16	0.074 (3)	0.037 (2)	0.072 (4)	−0.001 (2)	−0.043 (3)	0.005 (2)
C17	0.074 (3)	0.038 (2)	0.045 (3)	0.000 (2)	−0.022 (2)	0.0053 (18)
C18	0.045 (2)	0.035 (2)	0.046 (3)	−0.0019 (17)	−0.0097 (19)	−0.0004 (17)
C27	0.043 (2)	0.0289 (19)	0.067 (3)	−0.0020 (16)	−0.026 (2)	−0.0148 (18)
C28	0.044 (3)	0.055 (3)	0.109 (4)	0.005 (2)	0.003 (3)	0.034 (3)
C29	0.052 (3)	0.082 (4)	0.072 (4)	0.021 (3)	−0.003 (3)	0.001 (3)
C30	0.054 (3)	0.036 (2)	0.110 (5)	0.009 (2)	−0.029 (3)	−0.010 (3)
C31	0.080 (4)	0.074 (4)	0.124 (5)	0.012 (3)	−0.030 (4)	0.054 (4)
C32	0.081 (4)	0.095 (4)	0.051 (3)	0.026 (3)	−0.017 (3)	0.015 (3)
Mo1	0.03718 (19)	0.02467 (17)	0.0308 (2)	−0.00361 (12)	−0.01183 (13)	−0.00042 (12)
O3	0.149 (4)	0.109 (3)	0.059 (3)	0.000 (3)	−0.007 (3)	0.045 (2)
O1	0.074 (2)	0.073 (2)	0.0398 (18)	−0.0291 (18)	−0.0062 (16)	0.0109 (16)
O4	0.113 (3)	0.0510 (19)	0.095 (3)	−0.0215 (19)	−0.071 (2)	−0.0036 (18)
O2	0.055 (2)	0.053 (2)	0.112 (3)	0.0126 (16)	−0.035 (2)	0.0015 (19)
P1A	0.033 (2)	0.029 (2)	0.030 (3)	−0.0027 (15)	−0.009 (2)	−0.002 (2)
C19A	0.040 (7)	0.044 (7)	0.048 (9)	−0.007 (6)	0.006 (6)	0.001 (6)
C20A	0.042 (7)	0.036 (6)	0.040 (8)	−0.015 (5)	0.008 (6)	−0.008 (5)
C21A	0.052 (11)	0.057 (15)	0.092 (17)	0.000 (10)	−0.024 (12)	0.006 (11)
C22A	0.042 (10)	0.082 (16)	0.073 (16)	−0.002 (9)	−0.020 (9)	0.009 (13)
C23A	0.043 (9)	0.060 (11)	0.031 (9)	−0.029 (8)	−0.015 (7)	−0.010 (9)
C24A	0.051 (10)	0.044 (9)	0.061 (14)	−0.013 (7)	−0.004 (10)	−0.008 (8)
C25A	0.052 (8)	0.035 (7)	0.057 (9)	−0.009 (6)	−0.007 (7)	0.008 (6)
C26A	0.054 (7)	0.033 (6)	0.015 (6)	−0.012 (5)	−0.013 (5)	−0.003 (4)
P1	0.0377 (10)	0.0243 (9)	0.0286 (14)	−0.0061 (7)	−0.0048 (10)	−0.0010 (9)
C19	0.048 (3)	0.026 (3)	0.034 (3)	0.001 (2)	−0.010 (3)	0.003 (2)
C20	0.053 (3)	0.035 (3)	0.027 (3)	−0.005 (2)	−0.012 (3)	0.000 (2)
C21	0.050 (5)	0.048 (6)	0.064 (5)	−0.007 (4)	−0.020 (5)	−0.019 (4)
C22	0.066 (6)	0.064 (6)	0.064 (6)	−0.019 (4)	−0.028 (5)	−0.008 (5)
C23	0.102 (9)	0.049 (5)	0.057 (6)	−0.032 (5)	−0.022 (6)	0.003 (5)
C24	0.087 (7)	0.036 (4)	0.042 (5)	−0.008 (4)	−0.018 (5)	−0.007 (3)
C25	0.065 (4)	0.034 (3)	0.032 (3)	−0.002 (3)	−0.010 (3)	−0.002 (2)
C26	0.056 (4)	0.047 (3)	0.036 (4)	−0.022 (3)	0.003 (3)	−0.005 (3)
P2	0.0352 (5)	0.0237 (4)	0.0367 (6)	−0.0047 (4)	−0.0066 (4)	−0.0024 (4)

Geometric parameters (Å, º) top

Mo1—C1	2.021 (4)	C28—H28	0.9300
Mo1—C2	2.000 (5)	C29—C30	1.333 (7)
Mo1—C3	2.032 (5)	C29—H29	0.9300
Mo1—C4	1.973 (4)	C30—C31	1.343 (8)
Mo1—P2	2.5297 (10)	C30—H30	0.9300
Mo1—P1	2.536 (3)	C31—C32	1.373 (8)
Mo1—P1A	2.555 (6)	C31—H31	0.9300
C1—O1	1.155 (5)	C32—H32	0.9300
C2—O2	1.144 (5)	P1A—C26A	1.816 (12)
C3—O3	1.139 (6)	P1A—C19A	1.860 (11)
C4—O4	1.149 (5)	C19A—C20A	1.546 (9)
C5—C6	1.505 (5)	C19A—H19A	0.9700
C5—P2	1.853 (3)	C19A—H19B	0.9700
C5—H5A	0.9700	C20A—C21A	1.3900
C5—H5B	0.9700	C20A—C25A	1.3900
C6—C7	1.380 (6)	C21A—C22A	1.3900
C6—C11	1.384 (6)	C21A—H21A	0.9300
C7—C8	1.387 (6)	C22A—C23A	1.3900
C7—H7	0.9300	C22A—H22A	0.9300
C8—C9	1.372 (7)	C23A—C24A	1.3900
C8—H8	0.9300	C23A—H23A	0.9300
C9—C10	1.371 (6)	C24A—C25A	1.3900
C9—H9	0.9300	C24A—H24A	0.9300
C10—C11	1.389 (6)	C25A—H25A	0.9300
C10—H10	0.9300	C26A—H26A	0.9600
C11—H11	0.9300	C26A—H26B	0.9600
C12—P2	1.823 (4)	C26A—H26C	0.9600
C12—H12A	0.9600	P1—C26	1.832 (6)
C12—H12B	0.9600	P1—C19	1.842 (6)
C12—H12C	0.9600	C19—C20	1.524 (6)
C13—C18	1.389 (5)	C19—H19C	0.9700
C13—C14	1.391 (5)	C19—H19D	0.9700
C13—P2	1.835 (4)	C20—C21	1.3900
C14—C15	1.389 (6)	C20—C25	1.3900
C14—H14	0.9300	C21—C22	1.3900
C15—C16	1.366 (6)	C21—H21	0.9300
C15—H15	0.9300	C22—C23	1.3900
C16—C17	1.377 (6)	C22—H22	0.9300
C16—H16	0.9300	C23—C24	1.3900
C17—C18	1.387 (6)	C23—H23	0.9300
C17—H17	0.9300	C24—C25	1.3900
C18—H18	0.9300	C24—H24	0.9300
C27—C28	1.361 (6)	C25—H25	0.9300
C27—C32	1.383 (7)	C26—H26D	0.9600
C27—P1	1.832 (4)	C26—H26E	0.9600
C27—P1A	1.882 (6)	C26—H26F	0.9600
C28—C29	1.376 (7)

O1—C1—Mo1	175.6 (3)	C3—Mo1—P1	84.01 (15)
O2—C2—Mo1	176.6 (4)	P2—Mo1—P1	94.45 (6)
O3—C3—Mo1	177.8 (5)	C4—Mo1—P1A	173.46 (17)
O4—C4—Mo1	178.7 (4)	C2—Mo1—P1A	89.50 (17)
C6—C5—P2	116.0 (3)	C1—Mo1—P1A	84.76 (16)
C6—C5—H5A	108.3	C3—Mo1—P1A	97.06 (19)
P2—C5—H5A	108.3	P2—Mo1—P1A	94.86 (12)
C6—C5—H5B	108.3	P1—Mo1—P1A	13.06 (9)
P2—C5—H5B	108.3	C26A—P1A—C19A	102.2 (6)
H5A—C5—H5B	107.4	C26A—P1A—C27	111.3 (5)
C7—C6—C11	117.9 (4)	C19A—P1A—C27	95.3 (5)
C7—C6—C5	121.0 (4)	C26A—P1A—Mo1	116.3 (4)
C11—C6—C5	121.1 (4)	C19A—P1A—Mo1	118.3 (4)
C6—C7—C8	121.3 (4)	C27—P1A—Mo1	111.4 (3)
C6—C7—H7	119.4	C20A—C19A—P1A	113.6 (8)
C8—C7—H7	119.4	C20A—C19A—H19A	108.8
C9—C8—C7	120.1 (4)	P1A—C19A—H19A	108.8
C9—C8—H8	119.9	C20A—C19A—H19B	108.8
C7—C8—H8	119.9	P1A—C19A—H19B	108.8
C10—C9—C8	119.5 (4)	H19A—C19A—H19B	107.7
C10—C9—H9	120.3	C21A—C20A—C25A	120.0
C8—C9—H9	120.3	C21A—C20A—C19A	119.2 (9)
C9—C10—C11	120.4 (5)	C25A—C20A—C19A	120.8 (9)
C9—C10—H10	119.8	C20A—C21A—C22A	120.0
C11—C10—H10	119.8	C20A—C21A—H21A	120.0
C6—C11—C10	120.8 (4)	C22A—C21A—H21A	120.0
C6—C11—H11	119.6	C23A—C22A—C21A	120.0
C10—C11—H11	119.6	C23A—C22A—H22A	120.0
P2—C12—H12A	109.5	C21A—C22A—H22A	120.0
P2—C12—H12B	109.5	C22A—C23A—C24A	120.0
H12A—C12—H12B	109.5	C22A—C23A—H23A	120.0
P2—C12—H12C	109.5	C24A—C23A—H23A	120.0
H12A—C12—H12C	109.5	C25A—C24A—C23A	120.0
H12B—C12—H12C	109.5	C25A—C24A—H24A	120.0
C18—C13—C14	118.3 (4)	C23A—C24A—H24A	120.0
C18—C13—P2	118.7 (3)	C24A—C25A—C20A	120.0
C14—C13—P2	122.9 (3)	C24A—C25A—H25A	120.0
C15—C14—C13	120.5 (4)	C20A—C25A—H25A	120.0
C15—C14—H14	119.8	P1A—C26A—H26A	109.5
C13—C14—H14	119.8	P1A—C26A—H26B	109.5
C16—C15—C14	120.0 (4)	H26A—C26A—H26B	109.5
C16—C15—H15	120.0	P1A—C26A—H26C	109.5
C14—C15—H15	120.0	H26A—C26A—H26C	109.5
C15—C16—C17	120.8 (4)	H26B—C26A—H26C	109.5
C15—C16—H16	119.6	C27—P1—C26	107.1 (3)
C17—C16—H16	119.6	C27—P1—C19	98.8 (2)
C16—C17—C18	119.3 (4)	C26—P1—C19	102.4 (3)
C16—C17—H17	120.4	C27—P1—Mo1	114.09 (17)
C18—C17—H17	120.4	C26—P1—Mo1	114.7 (2)
C17—C18—C13	121.1 (4)	C19—P1—Mo1	117.85 (19)
C17—C18—H18	119.5	C20—C19—P1	116.4 (4)
C13—C18—H18	119.5	C20—C19—H19C	108.2
C28—C27—C32	116.4 (4)	P1—C19—H19C	108.2
C28—C27—P1	125.6 (3)	C20—C19—H19D	108.2
C32—C27—P1	118.0 (4)	P1—C19—H19D	108.2
C28—C27—P1A	107.8 (4)	H19C—C19—H19D	107.3
C32—C27—P1A	135.7 (4)	C21—C20—C25	120.0
P1—C27—P1A	17.87 (13)	C21—C20—C19	118.8 (4)
C27—C28—C29	122.1 (4)	C25—C20—C19	121.2 (4)
C27—C28—H28	119.0	C20—C21—C22	120.0
C29—C28—H28	119.0	C20—C21—H21	120.0
C30—C29—C28	120.2 (5)	C22—C21—H21	120.0
C30—C29—H29	119.9	C23—C22—C21	120.0
C28—C29—H29	119.9	C23—C22—H22	120.0
C29—C30—C31	119.7 (5)	C21—C22—H22	120.0
C29—C30—H30	120.1	C22—C23—C24	120.0
C31—C30—H30	120.1	C22—C23—H23	120.0
C30—C31—C32	120.8 (5)	C24—C23—H23	120.0
C30—C31—H31	119.6	C25—C24—C23	120.0
C32—C31—H31	119.6	C25—C24—H24	120.0
C31—C32—C27	120.8 (5)	C23—C24—H24	120.0
C31—C32—H32	119.6	C24—C25—C20	120.0
C27—C32—H32	119.6	C24—C25—H25	120.0
C4—Mo1—C2	88.07 (17)	C20—C25—H25	120.0
C4—Mo1—C1	89.19 (16)	P1—C26—H26D	109.5
C2—Mo1—C1	90.28 (16)	P1—C26—H26E	109.5
C4—Mo1—C3	88.95 (19)	H26D—C26—H26E	109.5
C2—Mo1—C3	88.77 (19)	P1—C26—H26F	109.5
C1—Mo1—C3	177.94 (18)	H26D—C26—H26F	109.5
C4—Mo1—P2	87.67 (13)	H26E—C26—H26F	109.5
C2—Mo1—P2	175.58 (12)	C12—P2—C13	103.78 (18)
C1—Mo1—P2	90.82 (11)	C12—P2—C5	102.11 (18)
C3—Mo1—P2	89.99 (14)	C13—P2—C5	101.58 (18)
C4—Mo1—P1	172.65 (13)	C12—P2—Mo1	114.92 (15)
C2—Mo1—P1	89.64 (13)	C13—P2—Mo1	119.66 (11)
C1—Mo1—P1	97.81 (12)	C5—P2—Mo1	112.57 (13)

P2—C5—C6—C7	−100.2 (4)	C28—C27—P1—C26	−156.6 (5)
P2—C5—C6—C11	78.9 (4)	C32—C27—P1—C26	22.7 (5)
C11—C6—C7—C8	0.5 (6)	P1A—C27—P1—C26	−148.9 (10)
C5—C6—C7—C8	179.7 (3)	C28—C27—P1—C19	−50.6 (5)
C6—C7—C8—C9	0.2 (6)	C32—C27—P1—C19	128.6 (4)
C7—C8—C9—C10	−0.8 (6)	P1A—C27—P1—C19	−42.9 (8)
C8—C9—C10—C11	0.7 (7)	C28—C27—P1—Mo1	75.3 (5)
C7—C6—C11—C10	−0.5 (6)	C32—C27—P1—Mo1	−105.4 (4)
C5—C6—C11—C10	−179.7 (4)	P1A—C27—P1—Mo1	83.0 (8)
C9—C10—C11—C6	−0.1 (7)	C4—Mo1—P1—C27	77.6 (11)
C18—C13—C14—C15	0.5 (5)	C2—Mo1—P1—C27	5.8 (2)
P2—C13—C14—C15	178.2 (3)	C1—Mo1—P1—C27	−84.4 (2)
C13—C14—C15—C16	−0.7 (6)	C3—Mo1—P1—C27	94.6 (2)
C14—C15—C16—C17	0.7 (6)	P2—Mo1—P1—C27	−175.86 (19)
C15—C16—C17—C18	−0.4 (6)	P1A—Mo1—P1—C27	−83.5 (7)
C16—C17—C18—C13	0.2 (6)	C4—Mo1—P1—C26	−46.5 (12)
C14—C13—C18—C17	−0.2 (5)	C2—Mo1—P1—C26	−118.3 (3)
P2—C13—C18—C17	−178.1 (3)	C1—Mo1—P1—C26	151.5 (3)
C32—C27—C28—C29	−1.4 (8)	C3—Mo1—P1—C26	−29.5 (3)
P1—C27—C28—C29	177.9 (5)	P2—Mo1—P1—C26	60.0 (3)
P1A—C27—C28—C29	175.4 (5)	P1A—Mo1—P1—C26	152.4 (9)
C27—C28—C29—C30	1.6 (9)	C4—Mo1—P1—C19	−167.1 (11)
C28—C29—C30—C31	0.0 (9)	C2—Mo1—P1—C19	121.1 (3)
C29—C30—C31—C32	−1.7 (10)	C1—Mo1—P1—C19	30.8 (3)
C30—C31—C32—C27	1.8 (10)	C3—Mo1—P1—C19	−150.1 (3)
C28—C27—C32—C31	−0.3 (9)	P2—Mo1—P1—C19	−60.6 (2)
P1—C27—C32—C31	−179.6 (5)	P1A—Mo1—P1—C19	31.7 (7)
P1A—C27—C32—C31	−175.9 (5)	C27—P1—C19—C20	−65.7 (4)
C28—C27—P1A—C26A	−33.2 (6)	C26—P1—C19—C20	44.1 (5)
C32—C27—P1A—C26A	142.7 (7)	Mo1—P1—C19—C20	171.0 (3)
P1—C27—P1A—C26A	153.4 (11)	P1—C19—C20—C21	−105.0 (4)
C28—C27—P1A—C19A	−138.5 (5)	P1—C19—C20—C25	74.9 (5)
C32—C27—P1A—C19A	37.4 (7)	C25—C20—C21—C22	0.0
P1—C27—P1A—C19A	48.1 (8)	C19—C20—C21—C22	180.0 (5)
C28—C27—P1A—Mo1	98.4 (4)	C20—C21—C22—C23	0.0
C32—C27—P1A—Mo1	−85.7 (6)	C21—C22—C23—C24	0.0
P1—C27—P1A—Mo1	−75.1 (8)	C22—C23—C24—C25	0.0
C4—Mo1—P1A—C26A	41.6 (17)	C23—C24—C25—C20	0.0
C2—Mo1—P1A—C26A	109.8 (5)	C21—C20—C25—C24	0.0
C1—Mo1—P1A—C26A	19.4 (5)	C19—C20—C25—C24	−180.0 (5)
C3—Mo1—P1A—C26A	−161.5 (5)	C18—C13—P2—C12	−169.6 (3)
P2—Mo1—P1A—C26A	−70.9 (5)	C14—C13—P2—C12	12.7 (3)
P1—Mo1—P1A—C26A	−159.6 (10)	C18—C13—P2—C5	−63.9 (3)
C4—Mo1—P1A—C19A	163.9 (14)	C14—C13—P2—C5	118.4 (3)
C2—Mo1—P1A—C19A	−128.0 (6)	C18—C13—P2—Mo1	60.7 (3)
C1—Mo1—P1A—C19A	141.7 (6)	C14—C13—P2—Mo1	−117.0 (3)
C3—Mo1—P1A—C19A	−39.3 (6)	C6—C5—P2—C12	39.8 (4)
P2—Mo1—P1A—C19A	51.3 (6)	C6—C5—P2—C13	−67.2 (3)
P1—Mo1—P1A—C19A	−37.4 (7)	C6—C5—P2—Mo1	163.6 (3)
C4—Mo1—P1A—C27	−87.3 (15)	C4—Mo1—P2—C12	86.45 (19)
C2—Mo1—P1A—C27	−19.1 (3)	C2—Mo1—P2—C12	71.2 (16)
C1—Mo1—P1A—C27	−109.5 (3)	C1—Mo1—P2—C12	175.61 (17)
C3—Mo1—P1A—C27	69.6 (3)	C3—Mo1—P2—C12	−2.5 (2)
P2—Mo1—P1A—C27	160.2 (3)	P1—Mo1—P2—C12	−86.49 (15)
P1—Mo1—P1A—C27	71.4 (7)	P1A—Mo1—P2—C12	−99.58 (18)
C26A—P1A—C19A—C20A	−37.0 (10)	C4—Mo1—P2—C13	−149.02 (18)
C27—P1A—C19A—C20A	76.1 (9)	C2—Mo1—P2—C13	−164.3 (16)
Mo1—P1A—C19A—C20A	−166.1 (7)	C1—Mo1—P2—C13	−59.87 (17)
P1A—C19A—C20A—C21A	106.4 (9)	C3—Mo1—P2—C13	122.0 (2)
P1A—C19A—C20A—C25A	−72.0 (11)	P1—Mo1—P2—C13	38.03 (14)
C25A—C20A—C21A—C22A	0.0	P1A—Mo1—P2—C13	24.94 (17)
C19A—C20A—C21A—C22A	−178.4 (9)	C4—Mo1—P2—C5	−29.9 (2)
C20A—C21A—C22A—C23A	0.0	C2—Mo1—P2—C5	−45.1 (16)
C21A—C22A—C23A—C24A	0.0	C1—Mo1—P2—C5	59.27 (19)
C22A—C23A—C24A—C25A	0.0	C3—Mo1—P2—C5	−118.8 (2)
C23A—C24A—C25A—C20A	0.0	P1—Mo1—P2—C5	157.17 (17)
C21A—C20A—C25A—C24A	0.0	P1A—Mo1—P2—C5	144.1 (2)
C19A—C20A—C25A—C24A	178.4 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O4ⁱ	0.96	2.53	3.424 (6)	154

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Mo(CO)₄(C₁₄H₁₅P)₂]
M_r	636.44
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.9318 (4), 10.6434 (5), 14.9527 (7)
α, β, γ (°)	88.643 (2), 77.279 (2), 80.879 (2)
V (Å³)	1522.23 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.57
Crystal size (mm)	0.20 × 0.18 × 0.15

Data collection
Diffractometer	Bruker APEX CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.895, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	19662, 6531, 4924
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.141, 1.04
No. of reflections	6531
No. of parameters	408
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.63

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Selected bond lengths (Å) top

Mo1—C1	2.021 (4)	Mo1—C4	1.973 (4)
Mo1—C2	2.000 (5)	Mo1—P2	2.5297 (10)
Mo1—C3	2.032 (5)	Mo1—P1	2.536 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12A···O4ⁱ	0.96	2.53	3.424 (6)	154

Symmetry code: (i) −x, −y+1, −z+1.

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