metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(Aceto­nitrile-κN)[2-(di­phenylphosphan­yl)ethanamine-κ2N,P][(1,2,3,4,5-η)-1,2,3,4,5-penta­methylcyclo­pentadienyl]iron(II) hexa­fluoridophosphate tetra­hydro­furan monosolvate

aCaRLa - Catalysis Research Laboratory, Im Neuenheimer Feld 584, 69120 Heidelberg, Germany, and bOrganisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, Germany
*Correspondence e-mail: michael.limbach@basf.com

(Received 9 June 2011; accepted 18 July 2011; online 23 July 2011)

In the title cationic Cp*Fe(II) complex, [Fe(C10H15)(CH3CN)(C14H16NP)]PF6·C4H8O, the metal ion is coordinated by the η5-Cp* ring as well as the P and N atoms of the chelating 2-(diphenyl­phosphino)ethyl­amine ligand and an additional acetonitrile mol­ecule in a piano-chair conformation. The PF6 anion is disordered over two sets of sites with occupancies of 0.779 (7) and 0.221 (7).

Related literature

For related ruthenium complexes, see: Ito et al. (2003[Ito, M., Hirakawa, M., Osaku, A. & Ikariya, T. (2003). Organometallics, 22, 4190-4192.], 2005[Ito, M., Kitahara, S. & Ikariya, T. (2005). J. Am. Chem. Soc. 127, 6172-6173.], 2007[Ito, M., Sakaguchi, A., Kobayashi, C. & Ikariya, T. (2007). J. Am. Chem. Soc. 129, 290-291.], 2009[Ito, M., Koo, L. W., Himizu, A., Kobayashi, C., Sakaguchi, A. & Ikariya, T. (2009). Angew. Chem. Int. Ed. 48, 1324-1327.], 2011[Ito, M., Ootsuka, T., Watari, R., Shiibashi, A., Himizu, A. & Ikariya, T. (2011). J. Am. Chem. Soc. 133, 4240-4242.]). For corresponding Fe(II) complexes, see: Davies et al. (1994[Davies, D. L., Fawcett, J., Neild, J. & Russell, D. R. (1994). Polyhedron, 13, 2923-2928.]); Lagaditis et al. (2010[Lagaditis, P. O., Mikhailine, A. A., Lough, A. J. & Morris, R. H. (2010). Inorg. Chem. 49, 1094-1102.]). For the structure of a similar iron complex, see: Barbier et al. (1979[Barbier, J. P., Dapporto, P., Sacconi, L. & Stoppioni, P. (1979). J. Organomet. Chem. 171, 185-193.]).

[Scheme 1]

Experimental

Crystal data
  • [Fe(C10H15)(C2H3N)(C14H16NP)]PF6·C4H8O

  • Mr = 678.45

  • Monoclinic, P 21 /c

  • a = 11.9241 (2) Å

  • b = 12.9272 (1) Å

  • c = 21.4018 (4) Å

  • β = 103.790 (1)°

  • V = 3203.89 (8) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.63 mm−1

  • T = 200 K

  • 0.36 × 0.22 × 0.12 mm

Data collection
  • Siemens SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.]) Tmin = 0.804, Tmax = 0.928

  • 32150 measured reflections

  • 7357 independent reflections

  • 5518 reflections with I > 2σ(I)

  • Rint = 0.047

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 0.115

  • S = 1.03

  • 7357 reflections

  • 410 parameters

  • 357 restraints

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.52 e Å−3

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

There are numerous reports on well defined Cp*Ru(II) complexes bearing a 2-(diphenylphosphino)ethylamine ligand e.g. by Ito et al. (2011), Ito et al. (2009), Ito et al. (2007), Ito et al. (2005), Ito et al. (2003). Surprisingly, only a scarce number of corresponding Fe(II) complexes has been reported, e.g. by Davies et al. (1994) and Lagaditis et al. (2010), although both elements are homologues in group 8. The only reported structural analysis of an iron complex with this type of P,N-coordination has been published by Barbier et al. (1979).

Related literature top

For related ruthenium complexes, see: Ito et al. (2003, 2005, 2007, 2009, 2011). For corresponding Fe(II) complexes, see: Davies et al. (1994); Lagaditis et al. (2010). For the structure of a similar iron complex, see: Barbier et al. (1979).

Experimental top

To a solution of [Cp*Fe(MeCN)3]PF6 (40 mg, 0.087 mmol) in dry MeCN was added PPh2(CH2)2NH2 (20 mg, 0.087 mmol) and the solution was stirred at 20 °C for 16 h. The solvent was removed in vacuo, the residue was fractionally washed with dry hexane, Et2O, Et2O/THF (1:1), THF and THF/MeCN (3:1) over a plug of celite. The last purple fraction was kept and stored at -40 °C to give purple prismatic crystals of {Cp*Fe(MeCN)[Ph2P(CH2)2NH2]}PF6.THF (14 mg, 36% yield).

Refinement top

For all hydrogen atoms the positions were calculated according to geometrical criteria. During the refinement the hydrogen atoms were allowed to shift with the preceding atoms. In the case of the methyl groups the torsion angles were allowed to refine. The isotropic displacement parameters were set as 1.2 times (1.5 for methyl) the equivalent isotropic displacement parameters of the preceding atoms. The PF6 anion was refined with two alternative orientations with occupancies 0.779 (7) and 0.221 (7). In order to stabilize the octahedral geometry during the refinement all equivalent bonding or nonbondig interatomic distances were restrained to be equal within a standard deviation of 0.03 Å.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXTL (Sheldrick, 2008b); program(s) used to refine structure: SHELXTL (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid representation of the title compound with displacement ellipsoids plotted at 50% probability level.
(Acetonitrile-κN)[2-(diphenylphosphanyl)ethanamine- κ2N,P][(1,2,3,4,5-η)-1,2,3,4,5- pentamethylcyclopentadienyl]iron(II) hexafluoridophosphate tetrahydrofuran monosolvate top
Crystal data top
[Fe(C10H15)(C2H3N)(C14H16NP)]PF6·C4H8OF(000) = 1416
Mr = 678.45Dx = 1.407 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 11.9241 (2) ÅCell parameters from 6488 reflections
b = 12.9272 (1) ŵ = 0.63 mm1
c = 21.4018 (4) ÅT = 200 K
β = 103.790 (1)°Polyhedron, red
V = 3203.89 (8) Å30.36 × 0.22 × 0.12 mm
Z = 4
Data collection top
Siemens SMART CCD
diffractometer
7357 independent reflections
Radiation source: fine-focus sealed tube5518 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)
h = 1515
Tmin = 0.804, Tmax = 0.928k = 1616
32150 measured reflectionsl = 2727
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0463P)2 + 3.1534P]
where P = (Fo2 + 2Fc2)/3
7357 reflections(Δ/σ)max = 0.001
410 parametersΔρmax = 0.48 e Å3
357 restraintsΔρmin = 0.52 e Å3
Crystal data top
[Fe(C10H15)(C2H3N)(C14H16NP)]PF6·C4H8OV = 3203.89 (8) Å3
Mr = 678.45Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.9241 (2) ŵ = 0.63 mm1
b = 12.9272 (1) ÅT = 200 K
c = 21.4018 (4) Å0.36 × 0.22 × 0.12 mm
β = 103.790 (1)°
Data collection top
Siemens SMART CCD
diffractometer
7357 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008a)
5518 reflections with I > 2σ(I)
Tmin = 0.804, Tmax = 0.928Rint = 0.047
32150 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045357 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.03Δρmax = 0.48 e Å3
7357 reflectionsΔρmin = 0.52 e Å3
410 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
xyzUiso*/UeqOcc. (<1)
Fe10.34034 (3)0.71766 (3)0.027123 (16)0.02129 (10)
P10.15826 (6)0.76600 (5)0.01156 (3)0.02342 (15)
C10.1704 (2)0.9068 (2)0.02448 (14)0.0326 (6)
H1A0.16580.92100.07050.039*
H1B0.10660.94390.01190.039*
C20.2854 (2)0.9428 (2)0.01627 (14)0.0323 (6)
H2A0.30361.01250.00230.039*
H2B0.28190.94690.06200.039*
N30.37661 (19)0.86804 (17)0.00906 (11)0.0288 (5)
H3A0.44520.88670.03670.035*
H3B0.38650.87250.03220.035*
N40.3414 (2)0.76209 (17)0.11228 (11)0.0293 (5)
C50.3538 (3)0.7830 (2)0.16497 (14)0.0383 (7)
C60.3723 (4)0.8075 (3)0.23345 (16)0.0673 (12)
H6A0.42010.75360.25900.101*
H6B0.29770.81080.24500.101*
H6C0.41150.87440.24220.101*
C110.0710 (2)0.7202 (2)0.08884 (12)0.0266 (5)
C120.0186 (3)0.6496 (2)0.09300 (14)0.0348 (6)
H120.03930.62750.05490.042*
C130.0779 (3)0.6111 (3)0.15224 (16)0.0449 (8)
H130.13900.56310.15440.054*
C140.0491 (3)0.6418 (3)0.20778 (15)0.0484 (8)
H140.09000.61530.24820.058*
C150.0397 (3)0.7114 (3)0.20442 (15)0.0454 (8)
H150.06030.73240.24270.055*
C160.0989 (3)0.7509 (2)0.14581 (13)0.0347 (6)
H160.15930.79950.14430.042*
C210.0576 (2)0.7543 (2)0.04064 (12)0.0263 (5)
C220.0415 (2)0.8155 (2)0.03221 (14)0.0329 (6)
H220.05920.86400.00210.040*
C230.1139 (2)0.8057 (2)0.07362 (15)0.0376 (7)
H230.18020.84860.06810.045*
C240.0909 (3)0.7344 (2)0.12287 (15)0.0381 (7)
H240.14070.72870.15140.046*
C250.0048 (3)0.6711 (2)0.13068 (14)0.0373 (7)
H250.01980.62050.16380.045*
C260.0793 (2)0.6815 (2)0.09000 (14)0.0329 (6)
H260.14570.63860.09600.040*
C310.3973 (3)0.5719 (2)0.06174 (13)0.0313 (6)
C320.3277 (2)0.5634 (2)0.00160 (14)0.0302 (6)
C330.3808 (2)0.6228 (2)0.04312 (12)0.0282 (6)
C340.4835 (2)0.6666 (2)0.00464 (13)0.0283 (6)
C350.4940 (2)0.6366 (2)0.06001 (13)0.0310 (6)
C360.3765 (4)0.5195 (3)0.12082 (18)0.0594 (11)
H36A0.29350.50890.11570.089*
H36B0.40660.56310.15860.089*
H36C0.41610.45250.12660.089*
C370.2230 (3)0.4958 (2)0.0221 (2)0.0565 (10)
H37A0.24720.42440.02690.085*
H37B0.17570.52060.06330.085*
H37C0.17770.49840.01050.085*
C380.3459 (3)0.6250 (3)0.11505 (14)0.0511 (9)
H38A0.36330.69310.13040.077*
H38B0.26290.61140.12950.077*
H38C0.38870.57180.13230.077*
C390.5669 (3)0.7336 (3)0.0293 (2)0.0525 (9)
H39A0.60550.78120.00470.079*
H39B0.52480.77330.06650.079*
H39C0.62480.68980.04210.079*
C400.5907 (3)0.6656 (3)0.11617 (17)0.0556 (10)
H40A0.65330.61500.12060.083*
H40B0.56220.66630.15550.083*
H40C0.61960.73450.10900.083*
P20.63861 (8)0.00286 (7)0.17490 (4)0.0446 (2)
F10.5407 (4)0.0479 (5)0.2052 (3)0.134 (2)0.779 (7)
F20.7248 (4)0.0511 (3)0.23735 (15)0.0982 (17)0.779 (7)
F30.6417 (6)0.1097 (3)0.13894 (19)0.0665 (12)0.779 (7)
F40.7482 (5)0.0333 (5)0.1531 (3)0.131 (2)0.779 (7)
F50.5555 (7)0.0414 (4)0.1165 (3)0.190 (4)0.779 (7)
F60.6392 (6)0.0983 (4)0.2154 (3)0.123 (2)0.779 (7)
F1B0.6358 (15)0.0549 (9)0.2346 (5)0.084 (5)*0.221 (7)
F2B0.7666 (8)0.0134 (10)0.1792 (6)0.072 (4)*0.221 (7)
F3B0.610 (2)0.1033 (13)0.1345 (11)0.138 (14)*0.221 (7)
F4B0.6307 (10)0.0545 (9)0.1052 (5)0.060 (4)*0.221 (7)
F5B0.5069 (9)0.0190 (12)0.1607 (8)0.088 (5)*0.221 (7)
F6B0.6688 (14)0.1091 (9)0.2030 (7)0.064 (4)*0.221 (7)
O400.1488 (3)0.0416 (3)0.11782 (16)0.1004 (12)
C410.2249 (4)0.1228 (3)0.1411 (2)0.0727 (12)
H41A0.18740.19030.12810.087*
H41B0.29480.11770.12380.087*
C420.2565 (5)0.1126 (4)0.2133 (2)0.0900 (16)
H42A0.26380.18140.23410.108*
H42B0.33020.07470.22800.108*
C430.1566 (4)0.0520 (4)0.2283 (2)0.0813 (14)
H43A0.18490.00050.26270.098*
H43B0.10120.09880.24190.098*
C440.1025 (4)0.0001 (4)0.1664 (2)0.0770 (13)
H44A0.11770.07520.17000.092*
H44B0.01790.01100.15590.092*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02332 (19)0.02244 (18)0.01780 (18)0.00291 (14)0.00426 (13)0.00082 (14)
P10.0240 (3)0.0225 (3)0.0237 (3)0.0033 (3)0.0057 (3)0.0008 (2)
C10.0343 (15)0.0261 (13)0.0375 (15)0.0056 (12)0.0087 (12)0.0044 (12)
C20.0411 (16)0.0203 (13)0.0356 (15)0.0015 (12)0.0096 (13)0.0019 (11)
N30.0288 (12)0.0283 (12)0.0282 (12)0.0022 (9)0.0046 (10)0.0017 (9)
N40.0336 (13)0.0313 (12)0.0230 (12)0.0054 (10)0.0067 (9)0.0002 (9)
C50.0507 (19)0.0382 (16)0.0272 (15)0.0074 (14)0.0114 (13)0.0018 (13)
C60.114 (4)0.065 (3)0.0252 (17)0.002 (2)0.021 (2)0.0095 (16)
C110.0245 (13)0.0273 (13)0.0266 (13)0.0056 (11)0.0032 (10)0.0005 (11)
C120.0360 (16)0.0324 (15)0.0353 (16)0.0007 (12)0.0070 (13)0.0026 (12)
C130.0369 (17)0.0409 (18)0.052 (2)0.0064 (14)0.0012 (15)0.0105 (15)
C140.0444 (19)0.059 (2)0.0334 (17)0.0031 (16)0.0064 (14)0.0120 (15)
C150.0471 (19)0.060 (2)0.0260 (15)0.0073 (16)0.0032 (13)0.0034 (14)
C160.0319 (15)0.0409 (16)0.0294 (15)0.0028 (12)0.0038 (12)0.0033 (12)
C210.0262 (13)0.0265 (13)0.0267 (13)0.0015 (10)0.0070 (11)0.0028 (10)
C220.0295 (14)0.0347 (15)0.0333 (15)0.0051 (12)0.0050 (12)0.0001 (12)
C230.0259 (14)0.0448 (17)0.0431 (17)0.0055 (13)0.0102 (13)0.0091 (14)
C240.0323 (15)0.0493 (18)0.0366 (16)0.0071 (13)0.0157 (13)0.0110 (14)
C250.0408 (17)0.0401 (16)0.0340 (16)0.0002 (13)0.0147 (13)0.0041 (13)
C260.0320 (15)0.0327 (15)0.0357 (15)0.0052 (12)0.0113 (12)0.0018 (12)
C310.0398 (16)0.0273 (14)0.0302 (14)0.0126 (12)0.0152 (12)0.0071 (11)
C320.0261 (14)0.0228 (13)0.0416 (16)0.0044 (10)0.0080 (12)0.0042 (11)
C330.0324 (14)0.0295 (14)0.0218 (13)0.0098 (11)0.0047 (11)0.0034 (11)
C340.0266 (14)0.0269 (13)0.0336 (14)0.0051 (11)0.0114 (11)0.0019 (11)
C350.0313 (14)0.0324 (14)0.0262 (14)0.0100 (11)0.0009 (11)0.0038 (11)
C360.086 (3)0.049 (2)0.056 (2)0.033 (2)0.043 (2)0.0283 (17)
C370.0350 (18)0.0300 (16)0.103 (3)0.0025 (14)0.0126 (19)0.0165 (18)
C380.070 (2)0.057 (2)0.0232 (15)0.0316 (18)0.0048 (15)0.0046 (14)
C390.0405 (19)0.0425 (18)0.085 (3)0.0074 (15)0.0354 (19)0.0111 (18)
C400.0446 (19)0.061 (2)0.047 (2)0.0201 (17)0.0171 (16)0.0155 (17)
P20.0493 (5)0.0409 (5)0.0442 (5)0.0023 (4)0.0122 (4)0.0065 (4)
F10.079 (3)0.193 (6)0.154 (5)0.046 (3)0.075 (3)0.035 (4)
F20.105 (4)0.111 (3)0.058 (2)0.002 (2)0.021 (2)0.0099 (19)
F30.098 (3)0.0446 (18)0.058 (2)0.0049 (17)0.0198 (18)0.0229 (14)
F40.167 (5)0.140 (4)0.114 (4)0.091 (4)0.090 (4)0.020 (3)
F50.222 (8)0.135 (5)0.133 (5)0.076 (5)0.114 (6)0.017 (4)
F60.166 (6)0.076 (3)0.139 (5)0.004 (3)0.057 (4)0.057 (3)
O400.113 (3)0.129 (3)0.066 (2)0.039 (2)0.036 (2)0.045 (2)
C410.087 (3)0.065 (3)0.065 (3)0.008 (2)0.014 (2)0.013 (2)
C420.091 (4)0.100 (4)0.062 (3)0.014 (3)0.016 (3)0.014 (3)
C430.096 (4)0.091 (3)0.054 (3)0.024 (3)0.013 (2)0.001 (2)
C440.074 (3)0.093 (4)0.058 (3)0.012 (3)0.004 (2)0.001 (2)
Geometric parameters (Å, º) top
Fe1—N41.908 (2)C31—C361.506 (4)
Fe1—N32.048 (2)C32—C331.431 (4)
Fe1—C312.079 (3)C32—C371.501 (4)
Fe1—C322.082 (3)C33—C341.421 (4)
Fe1—C352.082 (3)C33—C381.496 (4)
Fe1—C332.084 (2)C34—C351.413 (4)
Fe1—C342.090 (3)C34—C391.507 (4)
Fe1—P12.2209 (7)C35—C401.501 (4)
P1—C111.830 (3)C36—H36A0.9800
P1—C211.831 (3)C36—H36B0.9800
P1—C11.851 (3)C36—H36C0.9800
C1—C21.512 (4)C37—H37A0.9800
C1—H1A0.9900C37—H37B0.9800
C1—H1B0.9900C37—H37C0.9800
C2—N31.490 (3)C38—H38A0.9800
C2—H2A0.9900C38—H38B0.9800
C2—H2B0.9900C38—H38C0.9800
N3—H3A0.9200C39—H39A0.9800
N3—H3B0.9200C39—H39B0.9800
N4—C51.135 (4)C39—H39C0.9800
C5—C61.464 (4)C40—H40A0.9800
C6—H6A0.9800C40—H40B0.9800
C6—H6B0.9800C40—H40C0.9800
C6—H6C0.9800P2—F11.576 (4)
C11—C121.392 (4)P2—F21.605 (3)
C11—C161.396 (4)P2—F31.586 (3)
C12—C131.388 (4)P2—F41.561 (4)
C12—H120.9500P2—F51.511 (4)
C13—C141.372 (5)P2—F61.569 (4)
C13—H130.9500P2—F1B1.451 (9)
C14—C151.378 (5)P2—F2B1.513 (10)
C14—H140.9500P2—F3B1.553 (12)
C15—C161.382 (4)P2—F4B1.647 (9)
C15—H150.9500P2—F5B1.553 (10)
C16—H160.9500P2—F6B1.576 (11)
C21—C261.392 (4)O40—C441.394 (5)
C21—C221.397 (4)O40—C411.400 (5)
C22—C231.382 (4)C41—C421.506 (6)
C22—H220.9500C41—H41A0.9900
C23—C241.378 (4)C41—H41B0.9900
C23—H230.9500C42—C431.523 (7)
C24—C251.382 (4)C42—H42A0.9900
C24—H240.9500C42—H42B0.9900
C25—C261.390 (4)C43—C441.489 (6)
C25—H250.9500C43—H43A0.9900
C26—H260.9500C43—H43B0.9900
C31—C321.415 (4)C44—H44A0.9900
C31—C351.433 (4)C44—H44B0.9900
N4—Fe1—N386.62 (9)C33—C32—Fe169.97 (15)
N4—Fe1—C3190.30 (10)C37—C32—Fe1129.8 (2)
N3—Fe1—C31149.53 (11)C34—C33—C32107.6 (2)
N4—Fe1—C32123.64 (11)C34—C33—C38125.3 (3)
N3—Fe1—C32149.00 (10)C32—C33—C38126.4 (3)
C31—Fe1—C3239.76 (11)C34—C33—Fe170.32 (14)
N4—Fe1—C3591.36 (10)C32—C33—Fe169.84 (14)
N3—Fe1—C35109.44 (10)C38—C33—Fe1132.53 (19)
C31—Fe1—C3540.28 (11)C35—C34—C33108.8 (2)
C32—Fe1—C3567.29 (11)C35—C34—C39126.0 (3)
N4—Fe1—C33156.39 (10)C33—C34—C39125.2 (3)
N3—Fe1—C33109.08 (10)C35—C34—Fe169.93 (15)
C31—Fe1—C3367.13 (10)C33—C34—Fe169.87 (14)
C32—Fe1—C3340.18 (11)C39—C34—Fe1126.2 (2)
C35—Fe1—C3367.14 (10)C34—C35—C31107.5 (2)
N4—Fe1—C34125.88 (10)C34—C35—C40126.0 (3)
N3—Fe1—C3490.75 (10)C31—C35—C40126.5 (3)
C31—Fe1—C3466.83 (10)C34—C35—Fe170.47 (15)
C32—Fe1—C3466.94 (11)C31—C35—Fe169.73 (15)
C35—Fe1—C3439.60 (10)C40—C35—Fe1126.2 (2)
C33—Fe1—C3439.81 (11)C31—C36—H36A109.5
N4—Fe1—P193.13 (7)C31—C36—H36B109.5
N3—Fe1—P183.93 (7)H36A—C36—H36B109.5
C31—Fe1—P1126.53 (9)C31—C36—H36C109.5
C32—Fe1—P199.44 (8)H36A—C36—H36C109.5
C35—Fe1—P1166.14 (8)H36B—C36—H36C109.5
C33—Fe1—P1105.69 (8)C32—C37—H37A109.5
C34—Fe1—P1140.31 (8)C32—C37—H37B109.5
C11—P1—C21102.13 (12)H37A—C37—H37B109.5
C11—P1—C1103.34 (13)C32—C37—H37C109.5
C21—P1—C1104.98 (12)H37A—C37—H37C109.5
C11—P1—Fe1122.73 (9)H37B—C37—H37C109.5
C21—P1—Fe1118.32 (9)C33—C38—H38A109.5
C1—P1—Fe1103.18 (9)C33—C38—H38B109.5
C2—C1—P1107.98 (18)H38A—C38—H38B109.5
C2—C1—H1A110.1C33—C38—H38C109.5
P1—C1—H1A110.1H38A—C38—H38C109.5
C2—C1—H1B110.1H38B—C38—H38C109.5
P1—C1—H1B110.1C34—C39—H39A109.5
H1A—C1—H1B108.4C34—C39—H39B109.5
N3—C2—C1108.9 (2)H39A—C39—H39B109.5
N3—C2—H2A109.9C34—C39—H39C109.5
C1—C2—H2A109.9H39A—C39—H39C109.5
N3—C2—H2B109.9H39B—C39—H39C109.5
C1—C2—H2B109.9C35—C40—H40A109.5
H2A—C2—H2B108.3C35—C40—H40B109.5
C2—N3—Fe1113.80 (17)H40A—C40—H40B109.5
C2—N3—H3A108.8C35—C40—H40C109.5
Fe1—N3—H3A108.8H40A—C40—H40C109.5
C2—N3—H3B108.8H40B—C40—H40C109.5
Fe1—N3—H3B108.8F5—P2—F194.4 (4)
H3A—N3—H3B107.7F6—P2—F189.2 (3)
C5—N4—Fe1172.2 (2)F4—P2—F1171.6 (3)
N4—C5—C6178.3 (4)F4—P2—F287.1 (3)
C5—C6—H6A109.5F6—P2—F286.9 (3)
C5—C6—H6B109.5F1—P2—F284.5 (3)
H6A—C6—H6B109.5F3—P2—F288.9 (3)
C5—C6—H6C109.5F5—P2—F2178.9 (4)
H6A—C6—H6C109.5F5—P2—F390.8 (3)
H6B—C6—H6C109.5F4—P2—F389.9 (3)
C12—C11—C16118.0 (3)F1—P2—F389.0 (3)
C12—C11—P1122.2 (2)F6—P2—F3175.6 (3)
C16—C11—P1119.6 (2)F5—P2—F494.0 (4)
C13—C12—C11120.6 (3)F5—P2—F693.3 (3)
C13—C12—H12119.7F4—P2—F691.3 (3)
C11—C12—H12119.7F1B—P2—F2B98.0 (7)
C14—C13—C12120.6 (3)F1B—P2—F3B93.1 (10)
C14—C13—H13119.7F2B—P2—F3B92.6 (10)
C12—C13—H13119.7F5B—P2—F4B84.4 (7)
C13—C14—C15119.4 (3)F6B—P2—F4B83.7 (7)
C13—C14—H14120.3F2B—P2—F4B86.3 (6)
C15—C14—H14120.3F3B—P2—F4B85.1 (10)
C14—C15—C16120.6 (3)F1B—P2—F4B175.4 (8)
C14—C15—H15119.7F1B—P2—F5B91.3 (8)
C16—C15—H15119.7F3B—P2—F5B87.9 (10)
C15—C16—C11120.7 (3)F2B—P2—F5B170.6 (8)
C15—C16—H16119.6F1B—P2—F6B98.2 (7)
C11—C16—H16119.6F2B—P2—F6B85.6 (7)
C26—C21—C22118.6 (2)F5B—P2—F6B92.1 (7)
C26—C21—P1119.2 (2)F3B—P2—F6B168.7 (11)
C22—C21—P1122.1 (2)C44—O40—C41111.2 (3)
C23—C22—C21120.2 (3)O40—C41—C42106.3 (4)
C23—C22—H22119.9O40—C41—H41A110.5
C21—C22—H22119.9C42—C41—H41A110.5
C24—C23—C22120.7 (3)O40—C41—H41B110.5
C24—C23—H23119.6C42—C41—H41B110.5
C22—C23—H23119.6H41A—C41—H41B108.7
C23—C24—C25119.8 (3)C41—C42—C43104.2 (4)
C23—C24—H24120.1C41—C42—H42A110.9
C25—C24—H24120.1C43—C42—H42A110.9
C24—C25—C26120.0 (3)C41—C42—H42B110.9
C24—C25—H25120.0C43—C42—H42B110.9
C26—C25—H25120.0H42A—C42—H42B108.9
C25—C26—C21120.6 (3)C44—C43—C42103.7 (4)
C25—C26—H26119.7C44—C43—H43A111.0
C21—C26—H26119.7C42—C43—H43A111.0
C32—C31—C35108.2 (2)C44—C43—H43B111.0
C32—C31—C36126.4 (3)C42—C43—H43B111.0
C35—C31—C36125.4 (3)H43A—C43—H43B109.0
C32—C31—Fe170.23 (15)O40—C44—C43109.0 (4)
C35—C31—Fe169.99 (15)O40—C44—H44A109.9
C36—C31—Fe1127.0 (2)C43—C44—H44A109.9
C31—C32—C33107.9 (2)O40—C44—H44B109.9
C31—C32—C37125.6 (3)C43—C44—H44B109.9
C33—C32—C37126.2 (3)H44A—C44—H44B108.3
C31—C32—Fe170.01 (15)
N4—Fe1—P1—C11163.17 (13)N4—Fe1—C32—C3782.4 (3)
N3—Fe1—P1—C11110.57 (12)N3—Fe1—C32—C37111.7 (3)
C31—Fe1—P1—C1170.48 (14)C31—Fe1—C32—C37120.2 (4)
C32—Fe1—P1—C1138.32 (13)C35—Fe1—C32—C37158.0 (3)
C35—Fe1—P1—C1154.5 (4)C33—Fe1—C32—C37121.0 (4)
C33—Fe1—P1—C112.41 (13)C34—Fe1—C32—C37158.8 (3)
C34—Fe1—P1—C1126.75 (16)P1—Fe1—C32—C3717.8 (3)
N4—Fe1—P1—C2134.11 (12)C31—C32—C33—C340.5 (3)
N3—Fe1—P1—C21120.37 (12)C37—C32—C33—C34174.2 (3)
C31—Fe1—P1—C2158.58 (14)Fe1—C32—C33—C3460.50 (17)
C32—Fe1—P1—C2190.74 (13)C31—C32—C33—C38171.4 (3)
C35—Fe1—P1—C2174.6 (3)C37—C32—C33—C383.3 (4)
C33—Fe1—P1—C21131.47 (12)Fe1—C32—C33—C38128.6 (3)
C34—Fe1—P1—C21155.81 (15)C31—C32—C33—Fe159.97 (18)
N4—Fe1—P1—C181.21 (12)C37—C32—C33—Fe1125.3 (3)
N3—Fe1—P1—C15.05 (12)N4—Fe1—C33—C3462.6 (3)
C31—Fe1—P1—C1173.91 (13)N3—Fe1—C33—C3466.82 (16)
C32—Fe1—P1—C1153.94 (13)C31—Fe1—C33—C3480.73 (17)
C35—Fe1—P1—C1170.1 (3)C32—Fe1—C33—C34118.2 (2)
C33—Fe1—P1—C1113.20 (13)C35—Fe1—C33—C3436.85 (16)
C34—Fe1—P1—C188.87 (15)P1—Fe1—C33—C34155.73 (13)
C11—P1—C1—C2148.80 (19)N4—Fe1—C33—C3255.6 (3)
C21—P1—C1—C2104.5 (2)N3—Fe1—C33—C32174.97 (15)
Fe1—P1—C1—C220.0 (2)C31—Fe1—C33—C3237.47 (16)
P1—C1—C2—N344.9 (3)C35—Fe1—C33—C3281.36 (17)
C1—C2—N3—Fe153.3 (3)C34—Fe1—C33—C32118.2 (2)
N4—Fe1—N3—C261.81 (18)P1—Fe1—C33—C3286.07 (15)
C31—Fe1—N3—C2146.6 (2)N4—Fe1—C33—C38177.0 (3)
C32—Fe1—N3—C2129.9 (2)N3—Fe1—C33—C3853.5 (3)
C33—Fe1—N3—C2136.24 (18)C31—Fe1—C33—C38158.9 (3)
C34—Fe1—N3—C2172.29 (19)C32—Fe1—C33—C38121.4 (4)
P1—Fe1—N3—C231.71 (17)C35—Fe1—C33—C38157.2 (3)
C35—Fe1—N4—C53.7 (19)C34—Fe1—C33—C38120.4 (4)
P1—Fe1—N4—C5170.6 (19)P1—Fe1—C33—C3835.4 (3)
C21—P1—C11—C1227.8 (3)C32—C33—C34—C350.9 (3)
C1—P1—C11—C12136.6 (2)C38—C33—C34—C35171.9 (3)
Fe1—P1—C11—C12107.9 (2)Fe1—C33—C34—C3559.30 (18)
C21—P1—C11—C16156.7 (2)C32—C33—C34—C39179.0 (3)
C1—P1—C11—C1647.8 (2)C38—C33—C34—C398.0 (4)
Fe1—P1—C11—C1667.7 (2)Fe1—C33—C34—C39120.8 (3)
C16—C11—C12—C130.0 (4)C32—C33—C34—Fe160.20 (17)
P1—C11—C12—C13175.6 (2)C38—C33—C34—Fe1128.8 (3)
C11—C12—C13—C140.2 (5)N4—Fe1—C34—C3534.1 (2)
C12—C13—C14—C150.0 (5)N3—Fe1—C34—C35120.42 (17)
C13—C14—C15—C160.5 (5)C31—Fe1—C34—C3538.33 (17)
C14—C15—C16—C110.8 (5)C32—Fe1—C34—C3581.74 (18)
C12—C11—C16—C150.5 (4)C33—Fe1—C34—C35119.9 (2)
P1—C11—C16—C15175.2 (2)P1—Fe1—C34—C35158.20 (13)
C11—P1—C21—C26112.6 (2)N4—Fe1—C34—C33153.96 (15)
C1—P1—C21—C26139.8 (2)N3—Fe1—C34—C33119.67 (16)
Fe1—P1—C21—C2625.5 (3)C31—Fe1—C34—C3381.57 (17)
C11—P1—C21—C2266.8 (2)C32—Fe1—C34—C3338.17 (16)
C1—P1—C21—C2240.8 (3)C35—Fe1—C34—C33119.9 (2)
Fe1—P1—C21—C22155.1 (2)P1—Fe1—C34—C3338.3 (2)
C26—C21—C22—C232.1 (4)N4—Fe1—C34—C3986.5 (3)
P1—C21—C22—C23178.5 (2)N3—Fe1—C34—C390.2 (3)
C21—C22—C23—C241.3 (4)C31—Fe1—C34—C39158.9 (3)
C22—C23—C24—C250.6 (5)C32—Fe1—C34—C39157.7 (3)
C23—C24—C25—C261.8 (5)C35—Fe1—C34—C39120.6 (3)
C24—C25—C26—C211.0 (5)C33—Fe1—C34—C39119.5 (3)
C22—C21—C26—C251.0 (4)P1—Fe1—C34—C3981.2 (3)
P1—C21—C26—C25179.6 (2)C33—C34—C35—C310.9 (3)
N4—Fe1—C31—C32149.28 (17)C39—C34—C35—C31179.0 (3)
N3—Fe1—C31—C32126.9 (2)Fe1—C34—C35—C3160.17 (18)
C35—Fe1—C31—C32119.0 (2)C33—C34—C35—C40179.6 (3)
C33—Fe1—C31—C3237.86 (16)C39—C34—C35—C400.3 (5)
C34—Fe1—C31—C3281.28 (17)Fe1—C34—C35—C40121.2 (3)
P1—Fe1—C31—C3255.17 (18)C33—C34—C35—Fe159.27 (18)
N4—Fe1—C31—C3591.74 (16)C39—C34—C35—Fe1120.8 (3)
N3—Fe1—C31—C357.9 (3)C32—C31—C35—C340.6 (3)
C32—Fe1—C31—C35119.0 (2)C36—C31—C35—C34177.6 (3)
C33—Fe1—C31—C3581.11 (16)Fe1—C31—C35—C3460.64 (18)
C34—Fe1—C31—C3537.70 (15)C32—C31—C35—C40179.2 (3)
P1—Fe1—C31—C35174.14 (12)C36—C31—C35—C401.1 (5)
N4—Fe1—C31—C3628.0 (3)Fe1—C31—C35—C40120.7 (3)
N3—Fe1—C31—C36111.9 (3)C32—C31—C35—Fe160.08 (18)
C32—Fe1—C31—C36121.2 (4)C36—C31—C35—Fe1121.8 (3)
C35—Fe1—C31—C36119.8 (4)N4—Fe1—C35—C34153.01 (17)
C33—Fe1—C31—C36159.1 (3)N3—Fe1—C35—C3466.11 (17)
C34—Fe1—C31—C36157.5 (3)C31—Fe1—C35—C34118.1 (2)
P1—Fe1—C31—C3666.1 (3)C32—Fe1—C35—C3480.78 (17)
C35—C31—C32—C330.0 (3)C33—Fe1—C35—C3437.03 (16)
C36—C31—C32—C33178.1 (3)P1—Fe1—C35—C3498.1 (4)
Fe1—C31—C32—C3359.94 (18)N4—Fe1—C35—C3188.87 (16)
C35—C31—C32—C37174.8 (3)N3—Fe1—C35—C31175.76 (15)
C36—C31—C32—C373.3 (4)C32—Fe1—C35—C3137.34 (16)
Fe1—C31—C32—C37125.3 (3)C33—Fe1—C35—C3181.10 (17)
C35—C31—C32—Fe159.93 (18)C34—Fe1—C35—C31118.1 (2)
C36—C31—C32—Fe1121.9 (3)P1—Fe1—C35—C3120.0 (4)
N4—Fe1—C32—C3137.8 (2)N4—Fe1—C35—C4032.1 (3)
N3—Fe1—C32—C31128.0 (2)N3—Fe1—C35—C4054.8 (3)
C35—Fe1—C32—C3137.82 (16)C31—Fe1—C35—C40121.0 (4)
C33—Fe1—C32—C31118.8 (2)C32—Fe1—C35—C40158.3 (3)
C34—Fe1—C32—C3180.96 (17)C33—Fe1—C35—C40157.9 (3)
P1—Fe1—C32—C31138.04 (15)C34—Fe1—C35—C40120.9 (4)
N4—Fe1—C32—C33156.62 (15)P1—Fe1—C35—C40141.0 (3)
N3—Fe1—C32—C339.3 (3)C44—O40—C41—C4217.5 (5)
C31—Fe1—C32—C33118.8 (2)O40—C41—C42—C4323.4 (5)
C35—Fe1—C32—C3380.96 (16)C41—C42—C43—C4420.5 (5)
C34—Fe1—C32—C3337.82 (15)C41—O40—C44—C433.9 (6)
P1—Fe1—C32—C33103.18 (14)C42—C43—C44—O4011.0 (5)

Experimental details

Crystal data
Chemical formula[Fe(C10H15)(C2H3N)(C14H16NP)]PF6·C4H8O
Mr678.45
Crystal system, space groupMonoclinic, P21/c
Temperature (K)200
a, b, c (Å)11.9241 (2), 12.9272 (1), 21.4018 (4)
β (°) 103.790 (1)
V3)3203.89 (8)
Z4
Radiation typeMo Kα
µ (mm1)0.63
Crystal size (mm)0.36 × 0.22 × 0.12
Data collection
DiffractometerSiemens SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008a)
Tmin, Tmax0.804, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections
32150, 7357, 5518
Rint0.047
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.115, 1.03
No. of reflections7357
No. of parameters410
No. of restraints357
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.52

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXTL (Sheldrick, 2008b).

 

Acknowledgements

CaRLa at Heidelberg University is co-financed by the University of Heidelberg, the state of Baden-Württemberg and BASF SE. The support of these institutions is gratefully acknowledged.

References

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First citationIto, M., Ootsuka, T., Watari, R., Shiibashi, A., Himizu, A. & Ikariya, T. (2011). J. Am. Chem. Soc. 133, 4240–4242.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationIto, M., Sakaguchi, A., Kobayashi, C. & Ikariya, T. (2007). J. Am. Chem. Soc. 129, 290–291.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationLagaditis, P. O., Mikhailine, A. A., Lough, A. J. & Morris, R. H. (2010). Inorg. Chem. 49, 1094–1102.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationSheldrick, G. M. (2008a). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008b). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSiemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc. Madison, Wisconsin, USA.  Google Scholar

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