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

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

doi:10.1107/S1600536807068651

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages m338-m339

doi:10.1107/S1600536807068651

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

Kajin Lee,^a Alan J. Lough ^b ^* and Ian Manners ^a

^aSchool of Chemistry, University of Bristol, Cantock's Close, Bristol BS8 1TS, England, and ^bDepartment of Chemistry, University of Toronto, Toronto, Ontario, Canada M5S 3H6
^*Correspondence e-mail: alough@chem.utoronto.ca

(Received 19 December 2007; accepted 28 December 2007; online 11 January 2008)

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.

Related literature

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

Crystal data

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

Data collection

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

Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.176
S = 1.05
4217 reflections
296 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Selected bond lengths (Å)

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

Table 2
Hydrogen-bond geometry (Å, °)

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.

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; 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; software used to prepare material for publication: SHELXTL

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807068651/hb2681sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068651/hb2681Isup2.hkl

checkCIF report

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)

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.

Acknowledgements

IM thanks the EPSRC, the University of Bristol for start-up funds, the European Union for a Marie Curie Chair and the Royal Society for a Wolfson Research Merit Award for financial support. AJL acknowledges NSERC Canada and the University of Toronto for funding.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Jaska, C. A., Dorn, H., Lough, A. J. & Manners, I. (2003). Chem. Eur. J. 9, 271–281. Web of Science CSD CrossRef PubMed CAS Google Scholar
Jaska, C. A., Lough, A. J. & Manners, I. (2005). J. Chem. Soc. Dalton Trans. pp. 326–331. CrossRef Google Scholar
Kuckmann, T. I., Dornhaus, F., Bolte, M., Lerner, H.-W., Holthausen, M. C. & Wagner, M. (2007). Eur. J. Inorg. Chem. pp. 1989–2003. Web of Science CSD CrossRef Google Scholar
Nonius (2002). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A edited by C. W. Carter & R. M. Sweet pp. 307–326. London: Academic Press. Google Scholar
Paciello, R. A., Manriquez, J. M. & Bercaw, J. E. (1990). Organometallics, 9, 260–265. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2001). SHELXTL/PC. Version 6.1, Windows NT version. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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