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Acta Cryst. (2008). E64, m1448    [ doi:10.1107/S1600536808033618 ]

(R,SP)-1-Diphenylphosphino-2-(1-ethoxyethyl)ferrocene

H. Yuan and Z.-M. Zhou

Abstract top

In the crystal structure of the title compound, [Fe(C5H5)(C21H22OP)], the cyclopentadienyl (Cp) rings are almost parallel and are essentially eclipsed. The absolute configuration was determined as S for the planar and R for the central chirality.

Comment top

Asymmetric metal catalysis is one of the most active areas in modern organic chemistry, and considerable efforts have been made to the development of novel ligands for catalytic asymmetric transformations (Ojima, 2000). In this context, ferrocene-based ligands incorporating both chirality are very important (Gomez Arrayas et al., 2006) and some of them have already been applied in industrial processes because of their stability, low price and unique structure (Blaser & Schmidt, 2004).

(S,Rp)-1-(diphenylphosphino)-2-(1-ethoxyethyl)-ferrocene, the enantiomorph of title compound, has been used to synthesize 1,1'-binaphthyls via asymmetric Ni-catalysed Grignard cross-coupling with up to 68% ee, and the (S,Rp)-1-(diphenylphosphino)-2-(1-methoxyethyl)-ferrocene provided axially chiral binaphthalenes in enantioselectivities up to 95% ee (Hayashi et al., 1988). In addition, the (R,Sp)-1-(diphenylphosphino)-2-(1-ethoxyethyl)-ferrocene was also used in asymmetric hydrosilyation (Ohmura et al., 1995).

The Fe—C bond distances within the ferrocene group are in the range of 2.038 (2)–2.050 (2) Å for the unsubstituted cyclopentadienyl (Cp) ring [C1–C5] and 2.025 (2)–2.046 (2) Å for the substituted Cp ring [C6–C10]. The Cp rings are almost parallel, the dihedral angle between the Cp ring planes is 1.80 (10)°. The Cp rings are essentially eclipsed and the Fe–centroid distances are 1.654 (9) (Cg1) and 1.639 (9) Å (Cg2) with Cg1 and Cg2 are the centroids of the [C1–C5] and [C6–C10] rings. The [Cg1—Fe1—Cg2] angle is 178.60 (18)°. The C11 atom is almost in the plane of their carrier Cp ring, while the P1 atom is tilted slightly out of the plane by 0.102 (10) Å.

The two phenyl rings are oriented almost perpendicular, with a dihedral angle of 90.90 (10)°. The O1—C11 and C10—C11 bonds lengths are in agreement with those in the related complex 1-(1-Ferrocenyl-1-methoxy-3-phenyl-2-propyl)-1H-1,2,4-triazole (Jin et al., 2004) and the geometric parameters of the PPh2 group are in agreement with those in the similar structure 1-carboxy-1'-(diphenylphosphino)-ferrocene (Podlaha et al., 1996).

The title compound has both central chirality and planar chirality with the configuration of C11 atom being R, and the configuration of planar chirality being S.

Related literature top

For background to ferrocene derivatives applied as catalysts, see: Blaser & Schmidt (2004); Gomez Arrayas et al. (2006); Hayashi et al. (1988); Ohmura et al. (1995); Ojima (2000). For the structures of closely related compounds, see: Jin et al. (2004); Cheelama & Knochel (2007); Podlaha et al. (1996).

Experimental top

The title compound was prepared from (R,Sp)-1-[1-(acetyloxy)ethyl]-2-(diphenylphosphino)-ferrocene according to literature procedures (Hayashi et al., 1988). Single crystals of the title compound suitable for X-ray diffraction analysis were obtained by slow evaporation of a hexane solution.

Refinement top

All H atoms were positioned with idealized geometry with C—H = 0.93 (aromatic), 0.96 (methyl), 0.97 (methylene) or 0.98 Å (cyclopentadienyl and Cp—CH) and were refined isotropic with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C) using a riding model. The absolute structure was determined on the basis of 1688 Friedel pairs.

Computing details top

Data collection: CrystalClear (Rigaku, 2001); cell refinement: CrystalClear (Rigaku, 2001); data reduction: CrystalClear (Rigaku, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A molecular view of the title compound, showing the atom-labelling scheme. Displacement ellipsoids are draw at the 30% probability level.
(R,SP)-1-Diphenylphosphino-2-(1-ethoxyethyl)ferrocene top
Crystal data top
[Fe(C5H5)(C21H22OP)]F(000) = 928
Mr = 442.30Dx = 1.319 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 7176 reflections
a = 11.003 (2) Åθ = 2.2–27.9°
b = 12.191 (2) ŵ = 0.76 mm−1
c = 16.599 (3) ÅT = 113 K
V = 2226.6 (8) Å3Block, red
Z = 40.12 × 0.10 × 0.08 mm
Data collection top
Rigaku Saturn
diffractometer		3929 independent reflections
Radiation source: rotating anode3847 reflections with I > 2σ(I)
confocalRint = 0.050
ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2001)		h = −13→12
Tmin = 0.914, Tmax = 0.942k = −14→14
22928 measured reflectionsl = −19→19
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.062 w = 1/[σ2(Fo2) + (0.0301P)2 + 0.2869P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
3929 reflectionsΔρmax = 0.18 e Å−3
262 parametersΔρmin = −0.28 e Å−3
0 restraintsAbsolute structure: Flack (1983), with 1688 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.019 (12)
Crystal data top
[Fe(C5H5)(C21H22OP)]V = 2226.6 (8) Å3
Mr = 442.30Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 11.003 (2) ŵ = 0.76 mm−1
b = 12.191 (2) ÅT = 113 K
c = 16.599 (3) Å0.12 × 0.10 × 0.08 mm
Data collection top
Rigaku Saturn
diffractometer		3847 reflections with I > 2σ(I)
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2001)		Rint = 0.050
Tmin = 0.914, Tmax = 0.942θmax = 25.0°
22928 measured reflectionsStandard reflections: 0
3929 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.062Δρmax = 0.18 e Å−3
S = 1.05Δρmin = −0.28 e Å−3
3929 reflectionsAbsolute structure: Flack (1983), with 1688 Friedel pairs
262 parametersFlack parameter: 0.019 (12)
0 restraints
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*/Ueq
Fe1−0.03864 (3)0.77799 (2)0.905322 (18)0.02169 (9)
P10.07707 (4)0.98992 (4)1.01327 (3)0.01930 (12)
O10.18641 (12)1.04499 (11)0.82901 (9)0.0230 (3)
C10.09790 (19)0.66545 (15)0.91286 (14)0.0272 (5)
H1A0.18150.67580.89410.033*
C20.0010 (2)0.62243 (18)0.86702 (16)0.0358 (6)
H2A0.00550.59800.81080.043*
C3−0.1039 (2)0.62123 (19)0.9163 (2)0.0513 (8)
H3A−0.18500.59580.90040.062*
C4−0.0708 (3)0.6634 (2)0.99241 (18)0.0517 (8)
H4A−0.12540.67241.03860.062*
C50.0538 (2)0.69041 (18)0.99089 (14)0.0373 (6)
H5A0.10110.72091.03560.045*
C6−0.01527 (17)0.94062 (15)0.93016 (11)0.0178 (4)
C7−0.14254 (18)0.91375 (16)0.92785 (12)0.0210 (4)
H7A−0.20040.92240.97230.025*
C8−0.16938 (19)0.87040 (17)0.84996 (13)0.0260 (5)
H8A−0.24890.84420.83150.031*
C9−0.06047 (19)0.87097 (17)0.80413 (12)0.0230 (4)
H9A−0.05190.84490.74860.028*
C100.03465 (19)0.91267 (15)0.85299 (11)0.0198 (4)
C110.16655 (19)0.92877 (16)0.83152 (12)0.0204 (4)
H11A0.21670.89750.87460.024*
C120.2039 (2)0.87699 (19)0.75210 (13)0.0306 (5)
H12A0.28870.89030.74280.046*
H12B0.15720.90860.70910.046*
H12C0.18940.79940.75420.046*
C130.3051 (2)1.07659 (18)0.85426 (15)0.0291 (5)
H13A0.36581.04190.82040.035*
H13B0.31881.05380.90950.035*
C140.3145 (2)1.19937 (17)0.84759 (15)0.0334 (5)
H14A0.39391.22250.86450.050*
H14B0.25411.23290.88130.050*
H14C0.30141.22100.79270.050*
C150.06768 (17)1.14024 (16)1.00256 (11)0.0189 (4)
C160.1436 (2)1.20172 (18)1.05214 (12)0.0253 (5)
H16A0.19451.16611.08850.030*
C170.1443 (2)1.31563 (18)1.04809 (13)0.0308 (5)
H17A0.19501.35581.08190.037*
C180.0702 (2)1.36905 (18)0.99405 (13)0.0300 (5)
H18A0.07021.44520.99130.036*
C19−0.0040 (2)1.30890 (18)0.94408 (14)0.0305 (5)
H19A−0.05401.34480.90740.037*
C20−0.00485 (19)1.19497 (17)0.94788 (13)0.0263 (5)
H20A−0.05471.15530.91330.032*
C21−0.02654 (17)0.96925 (15)1.09878 (11)0.0203 (4)
C22−0.13214 (18)1.03066 (16)1.10886 (12)0.0231 (5)
H22A−0.15241.08401.07110.028*
C23−0.2073 (2)1.01308 (18)1.17447 (13)0.0277 (5)
H23A−0.27721.05511.18090.033*
C24−0.1788 (2)0.93330 (19)1.23050 (13)0.0303 (5)
H24A−0.22970.92151.27440.036*
C25−0.0752 (2)0.8714 (2)1.22134 (13)0.0319 (5)
H25A−0.05620.81731.25880.038*
C260.0012 (2)0.88959 (18)1.15610 (12)0.0281 (5)
H26A0.07160.84811.15060.034*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02261 (15)0.01571 (14)0.02675 (16)−0.00025 (12)0.00374 (13)0.00058 (13)
P10.0201 (3)0.0192 (3)0.0186 (3)0.0020 (2)−0.0007 (2)0.0016 (2)
O10.0219 (7)0.0174 (7)0.0297 (8)−0.0010 (6)0.0016 (6)0.0015 (6)
C10.0283 (11)0.0154 (10)0.0378 (12)0.0046 (9)0.0035 (11)0.0019 (10)
C20.0387 (14)0.0162 (11)0.0525 (15)0.0022 (10)0.0012 (12)−0.0069 (10)
C30.0332 (14)0.0176 (12)0.103 (3)−0.0032 (10)0.0143 (17)0.0083 (16)
C40.066 (2)0.0258 (13)0.0637 (19)0.0156 (12)0.0410 (16)0.0200 (13)
C50.0570 (16)0.0207 (11)0.0343 (13)0.0130 (11)0.0039 (13)0.0061 (10)
C60.0184 (10)0.0137 (9)0.0212 (10)0.0026 (8)0.0010 (8)0.0027 (8)
C70.0203 (10)0.0186 (10)0.0240 (11)0.0018 (8)0.0014 (9)0.0005 (8)
C80.0229 (11)0.0258 (11)0.0292 (12)−0.0001 (10)−0.0050 (10)0.0000 (10)
C90.0275 (11)0.0218 (10)0.0196 (10)0.0000 (9)−0.0023 (9)−0.0007 (8)
C100.0247 (11)0.0148 (10)0.0198 (10)0.0011 (9)0.0010 (9)0.0004 (8)
C110.0243 (11)0.0159 (10)0.0209 (10)0.0003 (9)−0.0016 (9)0.0005 (8)
C120.0309 (12)0.0322 (12)0.0287 (12)0.0012 (10)0.0077 (10)−0.0052 (10)
C130.0230 (11)0.0258 (12)0.0386 (13)−0.0053 (9)0.0007 (11)0.0006 (10)
C140.0289 (12)0.0259 (12)0.0454 (14)−0.0053 (10)0.0065 (11)−0.0037 (11)
C150.0182 (11)0.0198 (10)0.0188 (10)−0.0007 (8)0.0048 (8)−0.0003 (8)
C160.0269 (11)0.0293 (12)0.0198 (10)−0.0029 (9)−0.0046 (9)0.0015 (9)
C170.0350 (13)0.0291 (12)0.0282 (12)−0.0125 (10)−0.0001 (11)−0.0055 (10)
C180.0364 (14)0.0188 (11)0.0349 (13)−0.0005 (9)0.0095 (11)0.0023 (10)
C190.0310 (12)0.0240 (12)0.0366 (12)0.0028 (9)−0.0037 (11)0.0091 (10)
C200.0267 (11)0.0229 (11)0.0292 (11)−0.0015 (9)−0.0055 (10)0.0005 (9)
C210.0235 (10)0.0193 (10)0.0181 (9)−0.0017 (8)−0.0012 (10)0.0015 (8)
C220.0309 (12)0.0192 (10)0.0190 (10)0.0000 (9)−0.0003 (9)0.0004 (8)
C230.0291 (12)0.0276 (12)0.0264 (11)−0.0029 (10)0.0045 (10)−0.0071 (10)
C240.0346 (13)0.0367 (13)0.0196 (11)−0.0114 (11)0.0040 (10)−0.0014 (10)
C250.0382 (14)0.0332 (13)0.0243 (12)−0.0045 (11)−0.0031 (10)0.0095 (10)
C260.0313 (12)0.0285 (12)0.0245 (11)0.0005 (10)−0.0039 (10)0.0038 (9)
Geometric parameters (Å, °) top
Fe1—C102.025 (2)C11—C121.518 (3)
Fe1—C12.038 (2)C11—H11A0.9800
Fe1—C92.041 (2)C12—H12A0.9600
Fe1—C62.041 (2)C12—H12B0.9600
Fe1—C42.042 (2)C12—H12C0.9600
Fe1—C82.045 (2)C13—C141.505 (3)
Fe1—C72.046 (2)C13—H13A0.9700
Fe1—C22.047 (2)C13—H13B0.9700
Fe1—C52.047 (2)C14—H14A0.9600
Fe1—C32.050 (2)C14—H14B0.9600
P1—C61.816 (2)C14—H14C0.9600
P1—C211.838 (2)C15—C201.381 (3)
P1—C151.844 (2)C15—C161.392 (3)
O1—C131.424 (3)C16—C171.390 (3)
O1—C111.434 (2)C16—H16A0.9300
C1—C21.411 (3)C17—C181.376 (3)
C1—C51.416 (3)C17—H17A0.9300
C1—H1A0.9800C18—C191.375 (3)
C2—C31.415 (4)C18—H18A0.9300
C2—H2A0.9800C19—C201.390 (3)
C3—C41.412 (4)C19—H19A0.9300
C3—H3A0.9800C20—H20A0.9300
C4—C51.410 (4)C21—C221.392 (3)
C4—H4A0.9800C21—C261.393 (3)
C5—H5A0.9800C22—C231.384 (3)
C6—C101.435 (3)C22—H22A0.9300
C6—C71.439 (3)C23—C241.382 (3)
C7—C81.428 (3)C23—H23A0.9300
C7—H7A0.9800C24—C251.376 (3)
C8—C91.419 (3)C24—H24A0.9300
C8—H8A0.9800C25—C261.388 (3)
C9—C101.418 (3)C25—H25A0.9300
C9—H9A0.9800C26—H26A0.9300
C10—C111.507 (3)
C10—Fe1—C1106.17 (9)C8—C7—C6108.05 (18)
C10—Fe1—C940.83 (8)C8—C7—Fe169.55 (12)
C1—Fe1—C9120.74 (9)C6—C7—Fe169.22 (11)
C10—Fe1—C641.32 (7)C8—C7—H7A126.0
C1—Fe1—C6123.26 (8)C6—C7—H7A126.0
C9—Fe1—C668.99 (8)Fe1—C7—H7A126.0
C10—Fe1—C4158.10 (11)C9—C8—C7107.99 (18)
C1—Fe1—C467.90 (9)C9—C8—Fe169.49 (12)
C9—Fe1—C4160.50 (11)C7—C8—Fe169.60 (12)
C6—Fe1—C4122.93 (10)C9—C8—H8A126.0
C10—Fe1—C868.94 (9)C7—C8—H8A126.0
C1—Fe1—C8156.45 (9)Fe1—C8—H8A126.0
C9—Fe1—C840.66 (8)C10—C9—C8108.57 (18)
C6—Fe1—C869.17 (8)C10—C9—Fe169.00 (11)
C4—Fe1—C8124.97 (10)C8—C9—Fe169.86 (12)
C10—Fe1—C769.21 (8)C10—C9—H9A125.7
C1—Fe1—C7160.92 (8)C8—C9—H9A125.7
C9—Fe1—C768.61 (8)Fe1—C9—H9A125.7
C6—Fe1—C741.22 (8)C9—C10—C6108.25 (18)
C4—Fe1—C7109.11 (9)C9—C10—C11128.47 (18)
C8—Fe1—C740.85 (8)C6—C10—C11123.28 (18)
C10—Fe1—C2122.21 (9)C9—C10—Fe170.17 (12)
C1—Fe1—C240.41 (9)C6—C10—Fe169.95 (11)
C9—Fe1—C2106.50 (9)C11—C10—Fe1126.19 (14)
C6—Fe1—C2159.33 (9)O1—C11—C10106.40 (16)
C4—Fe1—C267.84 (10)O1—C11—C12110.14 (17)
C8—Fe1—C2121.37 (10)C10—C11—C12114.32 (17)
C7—Fe1—C2157.70 (9)O1—C11—H11A108.6
C10—Fe1—C5121.51 (10)C10—C11—H11A108.6
C1—Fe1—C540.56 (9)C12—C11—H11A108.6
C9—Fe1—C5156.82 (9)C11—C12—H12A109.5
C6—Fe1—C5107.69 (9)C11—C12—H12B109.5
C4—Fe1—C540.35 (11)H12A—C12—H12B109.5
C8—Fe1—C5161.50 (9)C11—C12—H12C109.5
C7—Fe1—C5124.93 (9)H12A—C12—H12C109.5
C2—Fe1—C568.07 (10)H12B—C12—H12C109.5
C10—Fe1—C3158.99 (11)O1—C13—C14108.08 (18)
C1—Fe1—C368.00 (9)O1—C13—H13A110.1
C9—Fe1—C3123.33 (12)C14—C13—H13A110.1
C6—Fe1—C3158.72 (10)O1—C13—H13B110.1
C4—Fe1—C340.39 (12)C14—C13—H13B110.1
C8—Fe1—C3107.86 (10)H13A—C13—H13B108.4
C7—Fe1—C3122.83 (10)C13—C14—H14A109.5
C2—Fe1—C340.40 (10)C13—C14—H14B109.5
C5—Fe1—C368.07 (11)H14A—C14—H14B109.5
C6—P1—C21101.20 (9)C13—C14—H14C109.5
C6—P1—C15102.97 (9)H14A—C14—H14C109.5
C21—P1—C15100.13 (8)H14B—C14—H14C109.5
C13—O1—C11113.47 (16)C20—C15—C16118.39 (19)
C2—C1—C5108.3 (2)C20—C15—P1125.17 (15)
C2—C1—Fe170.13 (13)C16—C15—P1116.40 (15)
C5—C1—Fe170.05 (12)C17—C16—C15120.8 (2)
C2—C1—H1A125.9C17—C16—H16A119.6
C5—C1—H1A125.9C15—C16—H16A119.6
Fe1—C1—H1A125.9C18—C17—C16120.0 (2)
C1—C2—C3108.0 (2)C18—C17—H17A120.0
C1—C2—Fe169.47 (12)C16—C17—H17A120.0
C3—C2—Fe169.90 (13)C19—C18—C17119.5 (2)
C1—C2—H2A126.0C19—C18—H18A120.2
C3—C2—H2A126.0C17—C18—H18A120.2
Fe1—C2—H2A126.0C18—C19—C20120.6 (2)
C4—C3—C2107.6 (2)C18—C19—H19A119.7
C4—C3—Fe169.49 (14)C20—C19—H19A119.7
C2—C3—Fe169.70 (13)C15—C20—C19120.57 (19)
C4—C3—H3A126.2C15—C20—H20A119.7
C2—C3—H3A126.2C19—C20—H20A119.7
Fe1—C3—H3A126.2C22—C21—C26118.38 (19)
C5—C4—C3108.6 (2)C22—C21—P1122.46 (15)
C5—C4—Fe170.04 (14)C26—C21—P1119.16 (15)
C3—C4—Fe170.12 (15)C23—C22—C21120.66 (19)
C5—C4—H4A125.7C23—C22—H22A119.7
C3—C4—H4A125.7C21—C22—H22A119.7
Fe1—C4—H4A125.7C24—C23—C22120.2 (2)
C4—C5—C1107.4 (2)C24—C23—H23A119.9
C4—C5—Fe169.61 (15)C22—C23—H23A119.9
C1—C5—Fe169.39 (13)C25—C24—C23120.0 (2)
C4—C5—H5A126.3C25—C24—H24A120.0
C1—C5—H5A126.3C23—C24—H24A120.0
Fe1—C5—H5A126.3C24—C25—C26120.0 (2)
C10—C6—C7107.14 (18)C24—C25—H25A120.0
C10—C6—P1122.87 (15)C26—C25—H25A120.0
C7—C6—P1129.82 (15)C25—C26—C21120.8 (2)
C10—C6—Fe168.73 (11)C25—C26—H26A119.6
C7—C6—Fe169.57 (11)C21—C26—H26A119.6
P1—C6—Fe1123.06 (10)
C10—Fe1—C1—C2−121.03 (14)Fe1—C6—C7—C8−58.89 (14)
C9—Fe1—C1—C2−79.11 (16)C10—C6—C7—Fe158.67 (13)
C6—Fe1—C1—C2−162.88 (13)P1—C6—C7—Fe1−116.57 (17)
C4—Fe1—C1—C281.32 (16)C10—Fe1—C7—C881.47 (13)
C8—Fe1—C1—C2−46.7 (3)C1—Fe1—C7—C8160.7 (2)
C7—Fe1—C1—C2166.0 (2)C9—Fe1—C7—C837.56 (12)
C5—Fe1—C1—C2119.1 (2)C6—Fe1—C7—C8119.68 (17)
C3—Fe1—C1—C237.59 (16)C4—Fe1—C7—C8−121.79 (15)
C10—Fe1—C1—C5119.87 (14)C2—Fe1—C7—C8−43.7 (3)
C9—Fe1—C1—C5161.79 (14)C5—Fe1—C7—C8−163.90 (13)
C6—Fe1—C1—C578.03 (16)C3—Fe1—C7—C8−79.16 (17)
C4—Fe1—C1—C5−37.78 (16)C10—Fe1—C7—C6−38.21 (11)
C8—Fe1—C1—C5−165.8 (2)C1—Fe1—C7—C641.0 (3)
C7—Fe1—C1—C546.9 (3)C9—Fe1—C7—C6−82.12 (12)
C2—Fe1—C1—C5−119.1 (2)C4—Fe1—C7—C6118.53 (14)
C3—Fe1—C1—C5−81.51 (17)C8—Fe1—C7—C6−119.68 (17)
C5—C1—C2—C30.4 (2)C2—Fe1—C7—C6−163.4 (2)
Fe1—C1—C2—C3−59.49 (16)C5—Fe1—C7—C676.41 (15)
C5—C1—C2—Fe159.89 (14)C3—Fe1—C7—C6161.16 (15)
C10—Fe1—C2—C176.58 (16)C6—C7—C8—C9−0.4 (2)
C9—Fe1—C2—C1118.33 (14)Fe1—C7—C8—C9−59.09 (14)
C6—Fe1—C2—C144.2 (3)C6—C7—C8—Fe158.68 (13)
C4—Fe1—C2—C1−81.47 (16)C10—Fe1—C8—C937.24 (12)
C8—Fe1—C2—C1160.08 (13)C1—Fe1—C8—C9−44.9 (3)
C7—Fe1—C2—C1−167.9 (2)C6—Fe1—C8—C981.63 (13)
C5—Fe1—C2—C1−37.77 (14)C4—Fe1—C8—C9−162.03 (14)
C3—Fe1—C2—C1−119.2 (2)C7—Fe1—C8—C9119.40 (17)
C10—Fe1—C2—C3−164.18 (16)C2—Fe1—C8—C9−78.50 (15)
C1—Fe1—C2—C3119.2 (2)C5—Fe1—C8—C9165.2 (3)
C9—Fe1—C2—C3−122.42 (17)C3—Fe1—C8—C9−120.72 (15)
C6—Fe1—C2—C3163.5 (3)C10—Fe1—C8—C7−82.16 (12)
C4—Fe1—C2—C337.78 (18)C1—Fe1—C8—C7−164.33 (19)
C8—Fe1—C2—C3−80.68 (19)C9—Fe1—C8—C7−119.40 (17)
C7—Fe1—C2—C3−48.7 (3)C6—Fe1—C8—C7−37.77 (12)
C5—Fe1—C2—C381.48 (18)C4—Fe1—C8—C778.57 (16)
C1—C2—C3—C4−0.2 (3)C2—Fe1—C8—C7162.10 (12)
Fe1—C2—C3—C4−59.38 (16)C5—Fe1—C8—C745.8 (3)
C1—C2—C3—Fe159.22 (15)C3—Fe1—C8—C7119.88 (15)
C10—Fe1—C3—C4158.9 (2)C7—C8—C9—C100.9 (2)
C1—Fe1—C3—C481.29 (16)Fe1—C8—C9—C10−58.27 (14)
C9—Fe1—C3—C4−165.50 (15)C7—C8—C9—Fe159.16 (14)
C6—Fe1—C3—C4−45.1 (4)C1—Fe1—C9—C10−78.90 (14)
C8—Fe1—C3—C4−123.40 (15)C6—Fe1—C9—C1038.18 (11)
C7—Fe1—C3—C4−80.96 (18)C4—Fe1—C9—C10169.5 (3)
C2—Fe1—C3—C4118.9 (2)C8—Fe1—C9—C10120.27 (18)
C5—Fe1—C3—C437.39 (15)C7—Fe1—C9—C1082.54 (13)
C10—Fe1—C3—C240.1 (3)C2—Fe1—C9—C10−120.49 (13)
C1—Fe1—C3—C2−37.59 (15)C5—Fe1—C9—C10−47.8 (3)
C9—Fe1—C3—C275.63 (18)C3—Fe1—C9—C10−161.40 (12)
C6—Fe1—C3—C2−163.9 (2)C10—Fe1—C9—C8−120.27 (18)
C4—Fe1—C3—C2−118.9 (2)C1—Fe1—C9—C8160.83 (12)
C8—Fe1—C3—C2117.72 (16)C6—Fe1—C9—C8−82.09 (13)
C7—Fe1—C3—C2160.17 (14)C4—Fe1—C9—C849.2 (3)
C5—Fe1—C3—C2−81.48 (16)C7—Fe1—C9—C8−37.73 (12)
C2—C3—C4—C5−0.1 (3)C2—Fe1—C9—C8119.24 (13)
Fe1—C3—C4—C5−59.65 (16)C5—Fe1—C9—C8−168.1 (2)
C2—C3—C4—Fe159.51 (16)C3—Fe1—C9—C878.33 (16)
C10—Fe1—C4—C5−40.2 (3)C8—C9—C10—C6−1.0 (2)
C1—Fe1—C4—C537.97 (14)Fe1—C9—C10—C6−59.82 (13)
C9—Fe1—C4—C5158.4 (2)C8—C9—C10—C11179.80 (19)
C6—Fe1—C4—C5−78.28 (16)Fe1—C9—C10—C11121.0 (2)
C8—Fe1—C4—C5−164.60 (13)C8—C9—C10—Fe158.80 (15)
C7—Fe1—C4—C5−121.88 (14)C7—C6—C10—C90.8 (2)
C2—Fe1—C4—C581.75 (15)P1—C6—C10—C9176.41 (14)
C3—Fe1—C4—C5119.5 (2)Fe1—C6—C10—C959.96 (14)
C10—Fe1—C4—C3−159.8 (2)C7—C6—C10—C11179.99 (17)
C1—Fe1—C4—C3−81.58 (15)P1—C6—C10—C11−4.4 (3)
C9—Fe1—C4—C338.8 (3)Fe1—C6—C10—C11−120.81 (18)
C6—Fe1—C4—C3162.18 (14)C7—C6—C10—Fe1−59.20 (13)
C8—Fe1—C4—C375.85 (17)P1—C6—C10—Fe1116.45 (14)
C7—Fe1—C4—C3118.57 (15)C1—Fe1—C10—C9118.58 (13)
C2—Fe1—C4—C3−37.80 (15)C6—Fe1—C10—C9−119.07 (17)
C5—Fe1—C4—C3−119.5 (2)C4—Fe1—C10—C9−170.6 (2)
C3—C4—C5—C10.4 (3)C8—Fe1—C10—C9−37.08 (12)
Fe1—C4—C5—C1−59.31 (15)C7—Fe1—C10—C9−80.95 (13)
C3—C4—C5—Fe159.71 (17)C2—Fe1—C10—C977.55 (15)
C2—C1—C5—C4−0.5 (2)C5—Fe1—C10—C9159.99 (13)
Fe1—C1—C5—C459.45 (16)C3—Fe1—C10—C948.0 (3)
C2—C1—C5—Fe1−59.94 (15)C1—Fe1—C10—C6−122.34 (12)
C10—Fe1—C5—C4163.58 (15)C9—Fe1—C10—C6119.07 (17)
C1—Fe1—C5—C4−118.8 (2)C4—Fe1—C10—C6−51.5 (3)
C9—Fe1—C5—C4−161.8 (2)C8—Fe1—C10—C681.99 (12)
C6—Fe1—C5—C4120.39 (16)C7—Fe1—C10—C638.12 (11)
C8—Fe1—C5—C443.3 (4)C2—Fe1—C10—C6−163.37 (12)
C7—Fe1—C5—C478.15 (18)C5—Fe1—C10—C6−80.93 (14)
C2—Fe1—C5—C4−81.13 (16)C3—Fe1—C10—C6167.1 (2)
C3—Fe1—C5—C4−37.42 (16)C1—Fe1—C10—C11−5.16 (19)
C10—Fe1—C5—C1−77.66 (15)C9—Fe1—C10—C11−123.7 (2)
C9—Fe1—C5—C1−43.0 (3)C6—Fe1—C10—C11117.2 (2)
C6—Fe1—C5—C1−120.84 (13)C4—Fe1—C10—C1165.6 (3)
C4—Fe1—C5—C1118.8 (2)C8—Fe1—C10—C11−160.82 (19)
C8—Fe1—C5—C1162.1 (2)C7—Fe1—C10—C11155.30 (19)
C7—Fe1—C5—C1−163.08 (12)C2—Fe1—C10—C11−46.2 (2)
C2—Fe1—C5—C137.63 (13)C5—Fe1—C10—C1136.2 (2)
C3—Fe1—C5—C181.34 (15)C3—Fe1—C10—C11−75.7 (3)
C21—P1—C6—C10−163.25 (16)C13—O1—C11—C10146.74 (17)
C15—P1—C6—C1093.47 (17)C13—O1—C11—C12−88.9 (2)
C21—P1—C6—C711.3 (2)C9—C10—C11—O1111.4 (2)
C15—P1—C6—C7−91.94 (19)C6—C10—C11—O1−67.6 (2)
C21—P1—C6—Fe1−78.69 (12)Fe1—C10—C11—O1−156.03 (13)
C15—P1—C6—Fe1178.04 (11)C9—C10—C11—C12−10.4 (3)
C1—Fe1—C6—C1076.02 (14)C6—C10—C11—C12170.58 (18)
C9—Fe1—C6—C10−37.74 (12)Fe1—C10—C11—C1282.2 (2)
C4—Fe1—C6—C10159.63 (14)C11—O1—C13—C14179.14 (17)
C8—Fe1—C6—C10−81.41 (12)C6—P1—C15—C205.9 (2)
C7—Fe1—C6—C10−118.85 (17)C21—P1—C15—C20−98.16 (18)
C2—Fe1—C6—C1043.3 (3)C6—P1—C15—C16−171.67 (15)
C5—Fe1—C6—C10117.91 (13)C21—P1—C15—C1684.23 (16)
C3—Fe1—C6—C10−167.2 (3)C20—C15—C16—C171.5 (3)
C10—Fe1—C6—C7118.85 (16)P1—C15—C16—C17179.30 (17)
C1—Fe1—C6—C7−165.12 (12)C15—C16—C17—C18−0.6 (3)
C9—Fe1—C6—C781.11 (12)C16—C17—C18—C19−0.3 (3)
C4—Fe1—C6—C7−81.52 (15)C17—C18—C19—C200.2 (3)
C8—Fe1—C6—C737.44 (12)C16—C15—C20—C19−1.6 (3)
C2—Fe1—C6—C7162.1 (2)P1—C15—C20—C19−179.18 (17)
C5—Fe1—C6—C7−123.24 (13)C18—C19—C20—C150.8 (3)
C3—Fe1—C6—C7−48.4 (3)C6—P1—C21—C22−68.60 (17)
C10—Fe1—C6—P1−116.20 (17)C15—P1—C21—C2236.93 (18)
C1—Fe1—C6—P1−40.17 (16)C6—P1—C21—C26111.64 (17)
C9—Fe1—C6—P1−153.94 (14)C15—P1—C21—C26−142.83 (16)
C4—Fe1—C6—P143.43 (16)C26—C21—C22—C230.3 (3)
C8—Fe1—C6—P1162.39 (14)P1—C21—C22—C23−179.51 (16)
C7—Fe1—C6—P1124.95 (17)C21—C22—C23—C24−0.6 (3)
C2—Fe1—C6—P1−72.9 (3)C22—C23—C24—C250.3 (3)
C5—Fe1—C6—P11.71 (14)C23—C24—C25—C260.4 (3)
C3—Fe1—C6—P176.6 (3)C24—C25—C26—C21−0.8 (3)
C10—C6—C7—C8−0.2 (2)C22—C21—C26—C250.5 (3)
P1—C6—C7—C8−175.46 (15)P1—C21—C26—C25−179.76 (17)
Table 1
Selected geometric parameters (Å, °) top
P1—C61.816 (2)O1—C111.434 (2)
P1—C211.838 (2)C10—C111.507 (3)
P1—C151.844 (2)C11—C121.518 (3)
O1—C131.424 (3)
C6—P1—C21101.20 (9)C7—C6—P1129.82 (15)
C6—P1—C15102.97 (9)O1—C11—C10106.40 (16)
C13—O1—C11113.47 (16)C10—C11—C12114.32 (17)
C10—C6—P1122.87 (15)
C15—P1—C6—C1093.47 (17)C6—P1—C15—C16−171.67 (15)
Acknowledgements top

The authors thank the Natural Science Foundation of China (grant No. 20572009) and the Basic Research Fund of Beijing Institute of Technology (grant No. 000Y05) for financial support of this work.

references
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