[1,2-Bis(dimethyl­phosphino)ethane]carbon­yl(η5-cyclo­penta­dien­yl)iron(II) diphenyl­phosphinoylborate

Lee, K.; Lough, A.J.; Manners, I.

doi:10.1107/S1600536807068651

[1,2-Bis(dimethylphosphino)ethane]carbonyl(η⁵-cyclopentadienyl)iron(II) diphenylphosphinoylborate

In the title compound, [Fe(C₅H₅)(C₆H₁₆P₂)(CO)](C₁₂H₁₃BOP), the Fe^II ion adopts a three-legged piano-stool geometry, with Fe

Cg = 1.721 (5)Å (Cg = the centroid defined by the C atoms of the cyclopentadienyl ring). The 1,2-bis(dimethylphosphino)ethane (dmpe) ligand chelates to form a five-membered C₂P₂Fe ring which is in a pseudo-half-chair conformation. In the crystal structure, associations of one cation and two anions are formed via weak intermolecular C—H

O hydrogen bonds, giving rise to R₄²(9) rings.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807068651/hb2681sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807068651/hb2681Isup2.hkl Contains datablock I

CCDC reference: 677446

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.008 Å
R factor = 0.059
wR factor = 0.177
Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.521     0.943
            Tmin(prime) and Tmax expected:      0.850     0.909
            RR(prime) =      0.591
            Please check that your absorption correction is appropriate.
PLAT029_ALERT_3_B _diffrn_measured_fraction_theta_full Low .......       0.95

Author Response: The authors are aware the the precision of the structure may be slightly lowered since only 95% of the data is available to 25 degrees in theta. But, the precision of the structure is adequate to characterize the compound and give meaningful values for the geometric parameters.

PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.59

Author Response: ... This Alert is generated when the predicted transmission coefficients are different from the calculated ones. Since the multi-scan correction uses redundant data it corrects for more than just absorption: slight crystal alignment, poor crystal quality and maybe even sometimes partial twinning. When there are many kappa data sets within one collection, I have found the transmission factors appear larger than they should and this is sometimes to do with inter-set scaling. You would expect this Alert to appear more for low absorbers (organics) where the absorption is minimal but the multi-scan absorption correction has been used.


Alert level C
REFLT03_ALERT_3_C  Reflection count < 95% complete
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _diffrn_reflns_theta_full          25.00
           From the CIF: _reflns_number_total               4217
           TEST2: Reflns within _diffrn_reflns_theta_max
           Count of symmetry unique reflns         4483
           Completeness (_total/calc)             94.07%
PLAT022_ALERT_3_C Ratio Unique / Expected Reflections too Low ....       0.94
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.96
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          8

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

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

Comment top

The mechanism for the metal catalyzed dehydrocoupling of phosphine-borane adducts has been studied by investigating the synthesis and reactivity of model complexes. The P—H bond oxidative addition of RPhPH-BH₃ to Pt(PEt₃)₃ has been reported as well as the phosphine-borane ligand-exchange reaction at the Pt centre of cis-[PtH(PPh₂.BH₃) (depe)] (Jaska et al., 2003). Model complexes such as cis-[PtH(PPhH.BH₃)(dcype)] [dcype = 1,2-bis(dicyclohexylphosphino)ethane] have been synthesized via dehydrocoupling routes involving Pt—H and P—H bonds of cis-[PtH₂(dcype)] and PhPH₂.BH₃ respectively (Jaska et al., 2005). The reactivity of CpFe(CO)₂PPh₂.BH₃, (I), (Kuckmann et al., 2007) [see Fig. 3] was probed as a potential model complex in the study of the mechanism of the dehydrocoupling of phosphine-borane adducts: the CO ligands might dissociate to promote a reaction with phosphine-borane adducts. Before reacting (I) with phosphine-borane adducts, dmpe (1,2-bis(dimethylphosphino)ethane) was added in excess to (I) to observe the lability of the CO ligands. When adventitious air was also introduced to this reaction in THF, the title compound, (II), (Fig. 1), was formed. A similar complex, Cp*Fe(dmpe)X (X = H, CH₃ or Cl) was reported earlier (Paciello et al., 1990).

The Fe atom in (II) is bonded to a cyclopentadienyl (cp) ring with Fe···C_g = 1.721 (5)Å (C_g = the centroid of C1—C5), a carbonyl group and the bis-chelating (dimethylphosphino)ethane (dmpe) ligand (Table 1). In the crystal of (II), weak intermolecular C—H···O hydrogen bonds (Table 2) form rings with graph set assignment R²₄(9) (Bernstein et al., 1995) created in a three component cluster of two anions and one cation (Fig. 2).

Related literature top

For related literature, see: Jaska et al. (2003, 2005); Kuckmann et al. (2007); Paciello et al. (1990). For background on graph-set theory, see: Bernstein et al. (1995).

Experimental top

The complex CpFe(CO)₂PPh₂.BH₃ (200 mg, 0.532 mmol) was dissolved in 1.8 ml THF in a round bottom Schlenk flask. This yellow solution turned orange upon addition of dmpe (0.150 ml, 0.899 mmol). After 8 days of stirring at 293 K, orange precipitate was observed in the solution. The solution was filter cannulated into a new flask and then the volatile components of the reaction mixture were removed in vacuo overnight. The product was purified by chromatography with a column of celite (0.5 cm × 1.5 cm) supported on glass wool with hexanes (4 ml), Et₂O (5 ml) and then THF (4 ml). The product in THF afforded pale yellow needles of (II) due to adventitious air.

Computing details top

Data collection: Collect (Nonius, 1997-2002); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: PLATON (Spek, 2003) and SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of (II) with displacement ellipsoids drawn at the 30% probability level. H atoms bonded to C atoms are not shown.
	Fig. 2. Part of the crystal structure of (II) showing hydrogen bonds as thin lines. Only the H atoms bonded to B atoms and those involved in hydrogen bonding are shown.
	Fig. 3. The reaction scheme.

[1,2-Bis(dimethylphosphino)ethane]carbonyl(η⁵-cyclopentadienyl)iron(II) diphenylphosphinoylborate top

Crystal data top

[Fe(C₅H₅)(C₆H₁₆P₂)(CO)](C₁₂H₁₃BOP)	Z = 2
M_r = 514.08	F(000) = 540
Triclinic, P1	D_x = 1.341 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.0244 (5) Å	Cell parameters from 8558 reflections
b = 11.4671 (4) Å	θ = 2.6–25.0°
c = 14.0568 (7) Å	µ = 0.80 mm⁻¹
α = 67.491 (3)°	T = 150 K
β = 81.155 (2)°	Cut needle, pale yellow
γ = 71.497 (3)°	0.20 × 0.14 × 0.12 mm
V = 1273.50 (11) Å³

Data collection top

Nonius KappaCCD diffractometer	4217 independent reflections
Radiation source: fine-focus sealed tube	2935 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
Detector resolution: 9 pixels mm^-1	θ_max = 25.0°, θ_min = 2.6°
ϕ scans and ω scans with κ offsets	h = −10→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −12→13
T_min = 0.521, T_max = 0.943	l = −16→16
8558 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0844P)² + 1.3773P] where P = (F_o² + 2F_c²)/3
4217 reflections	(Δ/σ)_max = 0.002
296 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

[Fe(C₅H₅)(C₆H₁₆P₂)(CO)](C₁₂H₁₃BOP)	γ = 71.497 (3)°
M_r = 514.08	V = 1273.50 (11) Å³
Triclinic, P1	Z = 2
a = 9.0244 (5) Å	Mo Kα radiation
b = 11.4671 (4) Å	µ = 0.80 mm⁻¹
c = 14.0568 (7) Å	T = 150 K
α = 67.491 (3)°	0.20 × 0.14 × 0.12 mm
β = 81.155 (2)°

Data collection top

Nonius KappaCCD diffractometer	4217 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2935 reflections with I > 2σ(I)
T_min = 0.521, T_max = 0.943	R_int = 0.091
8558 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.176	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.81 e Å⁻³
4217 reflections	Δρ_min = −0.79 e Å⁻³
296 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
Fe1	0.22249 (8)	0.31967 (6)	0.79005 (5)	0.0227 (2)
P1	−0.03606 (15)	0.38455 (12)	0.78938 (10)	0.0256 (3)
P2	0.20337 (15)	0.11946 (11)	0.82546 (10)	0.0231 (3)
O1	0.2462 (5)	0.3727 (4)	0.5707 (3)	0.0444 (10)
C1	0.4180 (6)	0.3862 (5)	0.7772 (4)	0.0339 (13)
H1A	0.4862	0.4108	0.7139	0.041*
C2	0.4403 (6)	0.2587 (5)	0.8551 (4)	0.0294 (12)
H2A	0.5270	0.1779	0.8568	0.035*
C3	0.3203 (6)	0.2692 (5)	0.9321 (4)	0.0319 (13)
H3A	0.3063	0.1965	0.9974	0.038*
C4	0.2271 (6)	0.4001 (5)	0.9012 (4)	0.0305 (12)
H4A	0.1336	0.4357	0.9409	0.037*
C5	0.2834 (6)	0.4729 (5)	0.8063 (4)	0.0326 (13)
H5A	0.2400	0.5691	0.7674	0.039*
C6	−0.1017 (6)	0.2512 (5)	0.7849 (4)	0.0328 (12)
H6A	−0.2134	0.2631	0.8071	0.039*
H6B	−0.0893	0.2506	0.7138	0.039*
C7	−0.0015 (6)	0.1229 (5)	0.8573 (4)	0.0301 (12)
H7A	−0.0212	0.0471	0.8492	0.036*
H7B	−0.0275	0.1172	0.9297	0.036*
C8	−0.1254 (7)	0.5297 (5)	0.6827 (4)	0.0397 (14)
H8A	−0.2394	0.5477	0.6902	0.060*
H8B	−0.0891	0.5149	0.6178	0.060*
H8C	−0.0961	0.6052	0.6824	0.060*
C9	−0.1446 (6)	0.4183 (6)	0.9003 (4)	0.0372 (13)
H9A	−0.2544	0.4233	0.8977	0.056*
H9B	−0.1377	0.5022	0.8996	0.056*
H9C	−0.1003	0.3476	0.9636	0.056*
C10	0.2542 (6)	0.0595 (5)	0.7200 (4)	0.0337 (13)
H10A	0.2284	−0.0237	0.7398	0.051*
H10B	0.3665	0.0453	0.7031	0.051*
H10C	0.1952	0.1244	0.6596	0.051*
C11	0.3108 (6)	−0.0181 (5)	0.9308 (4)	0.0318 (12)
H11A	0.2859	−0.0984	0.9380	0.048*
H11B	0.2812	−0.0001	0.9950	0.048*
H11C	0.4233	−0.0300	0.9163	0.048*
C12	0.2342 (6)	0.3517 (4)	0.6586 (4)	0.0275 (12)
P3	0.21995 (16)	0.08074 (12)	0.22685 (10)	0.0265 (3)
O2	0.3092 (5)	0.0325 (4)	0.1455 (3)	0.0482 (11)
C13	0.3424 (6)	0.1487 (4)	0.2728 (4)	0.0246 (11)
C14	0.4211 (6)	0.2322 (5)	0.1986 (4)	0.0287 (12)
H14A	0.4080	0.2534	0.1276	0.034*
C15	0.5184 (6)	0.2844 (5)	0.2277 (4)	0.0346 (13)
H15A	0.5714	0.3412	0.1765	0.042*
C16	0.5383 (6)	0.2541 (5)	0.3308 (4)	0.0332 (12)
H16A	0.6064	0.2886	0.3505	0.040*
C17	0.4598 (6)	0.1742 (5)	0.4046 (4)	0.0328 (13)
H17A	0.4721	0.1550	0.4754	0.039*
C18	0.3619 (6)	0.1208 (5)	0.3767 (4)	0.0283 (12)
H18A	0.3082	0.0653	0.4285	0.034*
C20	0.2031 (6)	−0.0630 (4)	0.3411 (4)	0.0249 (11)
C21	0.0648 (6)	−0.0653 (5)	0.4012 (4)	0.0303 (12)
H21A	−0.0229	0.0107	0.3858	0.036*
C22	0.0560 (7)	−0.1787 (5)	0.4833 (4)	0.0355 (13)
H22A	−0.0384	−0.1800	0.5238	0.043*
C23	0.1819 (7)	−0.2897 (5)	0.5070 (4)	0.0348 (13)
H23A	0.1741	−0.3672	0.5631	0.042*
C24	0.3195 (6)	−0.2878 (5)	0.4489 (4)	0.0351 (13)
H24A	0.4072	−0.3637	0.4659	0.042*
C25	0.3308 (6)	−0.1761 (5)	0.3662 (4)	0.0310 (12)
H25A	0.4257	−0.1761	0.3262	0.037*
B1	0.0223 (8)	0.2119 (6)	0.1944 (5)	0.0338 (14)
H1	0.045 (6)	0.298 (5)	0.132 (4)	0.030 (13)*
H2	−0.037 (7)	0.166 (6)	0.160 (5)	0.062 (18)*
H3	−0.020 (6)	0.244 (5)	0.265 (4)	0.043 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Fe1	0.0241 (4)	0.0196 (4)	0.0260 (4)	−0.0091 (3)	−0.0030 (3)	−0.0068 (3)
P1	0.0240 (7)	0.0230 (7)	0.0301 (7)	−0.0048 (5)	−0.0049 (6)	−0.0097 (6)
P2	0.0233 (7)	0.0193 (7)	0.0280 (7)	−0.0083 (5)	−0.0021 (5)	−0.0077 (5)
O1	0.061 (3)	0.040 (2)	0.027 (2)	−0.012 (2)	−0.0033 (19)	−0.0081 (17)
C1	0.033 (3)	0.037 (3)	0.037 (3)	−0.023 (3)	−0.003 (2)	−0.007 (2)
C2	0.030 (3)	0.024 (3)	0.037 (3)	−0.008 (2)	−0.011 (2)	−0.009 (2)
C3	0.045 (3)	0.032 (3)	0.029 (3)	−0.024 (3)	−0.007 (3)	−0.008 (2)
C4	0.034 (3)	0.036 (3)	0.035 (3)	−0.015 (2)	0.001 (2)	−0.024 (2)
C5	0.034 (3)	0.026 (3)	0.046 (3)	−0.015 (2)	−0.007 (3)	−0.014 (2)
C6	0.018 (3)	0.039 (3)	0.052 (3)	−0.012 (2)	−0.002 (2)	−0.025 (3)
C7	0.025 (3)	0.028 (3)	0.045 (3)	−0.013 (2)	0.001 (2)	−0.017 (2)
C8	0.034 (3)	0.033 (3)	0.038 (3)	0.004 (2)	−0.011 (3)	−0.006 (2)
C9	0.029 (3)	0.050 (3)	0.038 (3)	−0.011 (3)	0.005 (2)	−0.024 (3)
C10	0.040 (3)	0.024 (3)	0.039 (3)	−0.010 (2)	−0.003 (3)	−0.013 (2)
C11	0.037 (3)	0.021 (3)	0.034 (3)	−0.009 (2)	−0.005 (2)	−0.004 (2)
C12	0.031 (3)	0.017 (3)	0.034 (3)	−0.008 (2)	−0.007 (2)	−0.005 (2)
P3	0.0302 (8)	0.0211 (7)	0.0302 (7)	−0.0117 (6)	−0.0063 (6)	−0.0059 (5)
O2	0.058 (3)	0.043 (2)	0.048 (3)	−0.021 (2)	0.001 (2)	−0.0176 (19)
C13	0.027 (3)	0.017 (3)	0.028 (3)	−0.003 (2)	−0.006 (2)	−0.007 (2)
C14	0.032 (3)	0.025 (3)	0.029 (3)	−0.012 (2)	−0.004 (2)	−0.006 (2)
C15	0.036 (3)	0.030 (3)	0.042 (3)	−0.017 (2)	−0.002 (3)	−0.011 (2)
C16	0.034 (3)	0.030 (3)	0.044 (3)	−0.016 (2)	−0.007 (3)	−0.014 (2)
C17	0.037 (3)	0.027 (3)	0.035 (3)	−0.007 (2)	−0.012 (2)	−0.009 (2)
C18	0.029 (3)	0.021 (3)	0.032 (3)	−0.009 (2)	0.002 (2)	−0.007 (2)
C20	0.028 (3)	0.027 (3)	0.028 (3)	−0.015 (2)	−0.008 (2)	−0.011 (2)
C21	0.025 (3)	0.029 (3)	0.038 (3)	−0.008 (2)	−0.003 (2)	−0.012 (2)
C22	0.032 (3)	0.037 (3)	0.038 (3)	−0.015 (3)	0.004 (2)	−0.012 (2)
C23	0.048 (4)	0.030 (3)	0.027 (3)	−0.021 (3)	0.002 (3)	−0.005 (2)
C24	0.036 (3)	0.028 (3)	0.038 (3)	−0.005 (2)	−0.011 (3)	−0.008 (2)
C25	0.031 (3)	0.029 (3)	0.033 (3)	−0.008 (2)	0.000 (2)	−0.012 (2)
B1	0.034 (4)	0.029 (3)	0.039 (4)	−0.010 (3)	−0.007 (3)	−0.010 (3)

Geometric parameters (Å, º) top

Fe1—C12	1.733 (5)	C10—H10A	0.9800
Fe1—P1	2.2129 (15)	C10—H10B	0.9800
Fe1—P2	2.2133 (13)	C10—H10C	0.9800
Fe1—C2	2.093 (5)	C11—H11A	0.9800
Fe1—C1	2.093 (5)	C11—H11B	0.9800
Fe1—C5	2.097 (5)	C11—H11C	0.9800
Fe1—C3	2.105 (5)	P3—O2	1.477 (4)
Fe1—C4	2.107 (5)	P3—C20	1.837 (5)
P1—C8	1.811 (5)	P3—C13	1.844 (5)
P1—C9	1.815 (5)	P3—B1	1.917 (6)
P1—C6	1.831 (5)	C13—C18	1.396 (7)
P2—C10	1.804 (5)	C13—C14	1.396 (7)
P2—C11	1.818 (5)	C14—C15	1.388 (7)
P2—C7	1.826 (5)	C14—H14A	0.9500
O1—C12	1.160 (6)	C15—C16	1.382 (7)
C1—C5	1.422 (7)	C15—H15A	0.9500
C1—C2	1.426 (7)	C16—C17	1.369 (7)
C1—H1A	1.0000	C16—H16A	0.9500
C2—C3	1.418 (7)	C17—C18	1.394 (7)
C2—H2A	1.0000	C17—H17A	0.9500
C3—C4	1.401 (7)	C18—H18A	0.9500
C3—H3A	1.0000	C20—C21	1.397 (7)
C4—C5	1.394 (7)	C20—C25	1.401 (7)
C4—H4A	1.0000	C21—C22	1.385 (7)
C5—H5A	1.0000	C21—H21A	0.9500
C6—C7	1.521 (7)	C22—C23	1.377 (8)
C6—H6A	0.9900	C22—H22A	0.9500
C6—H6B	0.9900	C23—C24	1.379 (7)
C7—H7A	0.9900	C23—H23A	0.9500
C7—H7B	0.9900	C24—C25	1.381 (7)
C8—H8A	0.9800	C24—H24A	0.9500
C8—H8B	0.9800	C25—H25A	0.9500
C8—H8C	0.9800	B1—H1	1.09 (5)
C9—H9A	0.9800	B1—H2	1.12 (6)
C9—H9B	0.9800	B1—H3	1.15 (5)
C9—H9C	0.9800

C12—Fe1—C2	113.6 (2)	P2—C7—H7A	110.1
C12—Fe1—C1	90.6 (2)	C6—C7—H7B	110.1
C2—Fe1—C1	39.84 (19)	P2—C7—H7B	110.1
C12—Fe1—C5	105.3 (2)	H7A—C7—H7B	108.4
C2—Fe1—C5	66.7 (2)	P1—C8—H8A	109.5
C1—Fe1—C5	39.7 (2)	P1—C8—H8B	109.5
C12—Fe1—C3	153.0 (2)	H8A—C8—H8B	109.5
C2—Fe1—C3	39.5 (2)	P1—C8—H8C	109.5
C1—Fe1—C3	66.1 (2)	H8A—C8—H8C	109.5
C5—Fe1—C3	65.9 (2)	H8B—C8—H8C	109.5
C12—Fe1—C4	143.2 (2)	P1—C9—H9A	109.5
C2—Fe1—C4	65.7 (2)	P1—C9—H9B	109.5
C1—Fe1—C4	65.4 (2)	H9A—C9—H9B	109.5
C5—Fe1—C4	38.7 (2)	P1—C9—H9C	109.5
C3—Fe1—C4	38.9 (2)	H9A—C9—H9C	109.5
C12—Fe1—P1	91.01 (17)	H9B—C9—H9C	109.5
C2—Fe1—P1	155.10 (15)	P2—C10—H10A	109.5
C1—Fe1—P1	142.78 (15)	P2—C10—H10B	109.5
C5—Fe1—P1	104.63 (15)	H10A—C10—H10B	109.5
C3—Fe1—P1	115.69 (16)	P2—C10—H10C	109.5
C4—Fe1—P1	92.67 (15)	H10A—C10—H10C	109.5
C12—Fe1—P2	91.92 (15)	H10B—C10—H10C	109.5
C2—Fe1—P2	95.99 (14)	P2—C11—H11A	109.5
C1—Fe1—P2	130.86 (15)	P2—C11—H11B	109.5
C5—Fe1—P2	159.26 (15)	H11A—C11—H11B	109.5
C3—Fe1—P2	93.58 (14)	P2—C11—H11C	109.5
C4—Fe1—P2	124.82 (15)	H11A—C11—H11C	109.5
P1—Fe1—P2	86.24 (5)	H11B—C11—H11C	109.5
C8—P1—C9	102.6 (3)	O1—C12—Fe1	178.2 (5)
C8—P1—C6	106.0 (3)	O2—P3—C20	107.9 (2)
C9—P1—C6	103.3 (3)	O2—P3—C13	108.6 (2)
C8—P1—Fe1	117.0 (2)	C20—P3—C13	101.9 (2)
C9—P1—Fe1	118.65 (19)	O2—P3—B1	118.6 (3)
C6—P1—Fe1	107.95 (17)	C20—P3—B1	111.6 (3)
C10—P2—C11	102.7 (2)	C13—P3—B1	106.9 (2)
C10—P2—C7	104.4 (2)	C18—C13—C14	118.5 (4)
C11—P2—C7	104.9 (2)	C18—C13—P3	124.1 (4)
C10—P2—Fe1	115.38 (18)	C14—C13—P3	117.5 (4)
C11—P2—Fe1	119.88 (17)	C15—C14—C13	120.6 (5)
C7—P2—Fe1	108.14 (16)	C15—C14—H14A	119.7
C5—C1—C2	108.0 (5)	C13—C14—H14A	119.7
C5—C1—Fe1	70.3 (3)	C16—C15—C14	120.2 (5)
C2—C1—Fe1	70.1 (3)	C16—C15—H15A	119.9
C5—C1—H1A	126.0	C14—C15—H15A	119.9
C2—C1—H1A	126.0	C17—C16—C15	120.0 (5)
Fe1—C1—H1A	126.0	C17—C16—H16A	120.0
C3—C2—C1	107.2 (5)	C15—C16—H16A	120.0
C3—C2—Fe1	70.7 (3)	C16—C17—C18	120.5 (5)
C1—C2—Fe1	70.1 (3)	C16—C17—H17A	119.7
C3—C2—H2A	126.4	C18—C17—H17A	119.7
C1—C2—H2A	126.4	C17—C18—C13	120.2 (5)
Fe1—C2—H2A	126.4	C17—C18—H18A	119.9
C4—C3—C2	107.8 (4)	C13—C18—H18A	119.9
C4—C3—Fe1	70.7 (3)	C21—C20—C25	118.8 (4)
C2—C3—Fe1	69.8 (3)	C21—C20—P3	122.2 (4)
C4—C3—H3A	126.1	C25—C20—P3	118.9 (4)
C2—C3—H3A	126.1	C22—C21—C20	119.7 (5)
Fe1—C3—H3A	126.1	C22—C21—H21A	120.1
C5—C4—C3	109.6 (5)	C20—C21—H21A	120.1
C5—C4—Fe1	70.3 (3)	C23—C22—C21	121.0 (5)
C3—C4—Fe1	70.5 (3)	C23—C22—H22A	119.5
C5—C4—H4A	125.2	C21—C22—H22A	119.5
C3—C4—H4A	125.2	C22—C23—C24	119.6 (5)
Fe1—C4—H4A	125.2	C22—C23—H23A	120.2
C4—C5—C1	107.3 (5)	C24—C23—H23A	120.2
C4—C5—Fe1	71.0 (3)	C23—C24—C25	120.5 (5)
C1—C5—Fe1	70.0 (3)	C23—C24—H24A	119.8
C4—C5—H5A	126.3	C25—C24—H24A	119.8
C1—C5—H5A	126.3	C24—C25—C20	120.4 (5)
Fe1—C5—H5A	126.3	C24—C25—H25A	119.8
C7—C6—P1	107.3 (3)	C20—C25—H25A	119.8
C7—C6—H6A	110.3	P3—B1—H1	107 (3)
P1—C6—H6A	110.3	P3—B1—H2	101 (3)
C7—C6—H6B	110.3	H1—B1—H2	107 (4)
P1—C6—H6B	110.3	P3—B1—H3	107 (3)
H6A—C6—H6B	108.5	H1—B1—H3	106 (4)
C6—C7—P2	108.1 (3)	H2—B1—H3	127 (4)
C6—C7—H7A	110.1

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2ⁱ	1.00	2.41	3.389 (7)	167
C3—H3A···O2ⁱⁱ	1.00	2.20	3.197 (7)	172
C11—H11B···O2ⁱⁱ	0.98	2.35	3.281 (7)	159
C11—H11C···O2ⁱ	0.98	2.43	3.403 (7)	171

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

Experimental details

Crystal data
Chemical formula	[Fe(C₅H₅)(C₆H₁₆P₂)(CO)](C₁₂H₁₃BOP)
M_r	514.08
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	9.0244 (5), 11.4671 (4), 14.0568 (7)
α, β, γ (°)	67.491 (3), 81.155 (2), 71.497 (3)
V (Å³)	1273.50 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.20 × 0.14 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.521, 0.943
No. of measured, independent and observed [I > 2σ(I)] reflections	8558, 4217, 2935
R_int	0.091
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.176, 1.05
No. of reflections	4217
No. of parameters	296
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.79

Computer programs: Collect (Nonius, 1997-2002), DENZO-SMN (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXTL (Sheldrick, 2001), PLATON (Spek, 2003) and SHELXTL (Sheldrick, 2001), SHELXTL (Sheldrick, 2001).

Selected bond lengths (Å) top

Fe1—C12	1.733 (5)	Fe1—P2	2.2133 (13)
Fe1—P1	2.2129 (15)