supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

Acta Cryst. (2009). E65, m1216    [ doi:10.1107/S1600536809036654 ]

Methyl (Sp)-2-(diphenylphosphino)ferrocene-1-carboxylate

P. Stepnicka, J. Tauchman and I. Císarová

Abstract top

The title compound, [Fe(C5H5)(C19H16O2P)], obtained serendipitously during recrystallization of 1-hydroxybenzotriazolyl (Sp)-2-(diphenylphosphino)ferrocene-1-carboxylate from methanol, crystallizes in the chiral space group P212121. Its crystal structure not only confirms the anticipated absolute configuration but also establishes a rather regular geometry for the ferrocene unit, devoid of any significant deformation due to the attached substituents. In the crystal, symmetry-related molecules are linked via weak C-H...O interactions.

Comment top

The crystal structure of the title compound was determined at 150 (2) K (Fig. 1). It crystallizes with the symmetry of the chiral space group P212121 and one molecule in the asymmetric unit. The molecular geometry of the title compound compares well with the data reported previously for (Sp)-2-(diphenylphosphinoyl)ferrocene-1-carboxylic acid (Štěpnička, 2002) and methyl (Rp)-1',2-bis(diphenylphosphino)ferrocene-1-carboxylate (Lamač et al., 2009). The geometry of the ferrocene moiety is quite regular, showing similar Fe—ring centroid distances (1.6471 (9) and 1.6567 (9) Å for the rings C(1–5) and C(6–10), respectively) and insignificant tilting (the dihedral angle of the cyclopentadienyl mean planes being 2.08 (12) °). The attached substituents do not seem to impose any pronounced deformation of the ferrocene core, as evidenced by the C11—C1—C2—P torsion angle of –5.5 (3) °. However, the diphenylphosphinyl group binds somewhat unsymmetrically as indicated by the differences in the C(1/3)—C2—P angles being ca 2.7 ° (cf. the difference of the C(2/5)—C1—C11 angles, which is below 0.1 °, and also the perpendicular distances from the C(1–5) ring mean-plane: 0.136 (1) Å for P and –0.018 (2) Å for C11). This is reflected also by the variation in the Fe–C distances (2.0283 (18)–2.0672 (18) Å) for the substituted cyclopentadienyl ring (C1–C5).

The crystal structure of the title compound is essentially molecular, with symmetry related molecules forming only soft C—H···O contacts (Table 1).

Related literature top

For an overview of the chemistry of ferrocene, see: Štěpnička (2008). For the NMR spectroscopic data of the title compound, see: You et al. (2002); Lamač et al. (2008). For the structure of similar compounds, see: Lamač et al. (2009); Štěpnička (2002).

Experimental top

The title compound was formed on recrystallization of 1-hydroxybenzotriazolyl (Sp)-2-(diphenylphosphino)ferrocene-1-carboxylate (Štěpnička & Tauchman, unpublished results) from warm methanol, apparently resulting from a trans-esterification reaction of the starting activated ester. Its formulation was established by NMR spectroscopy (You et al., 2002; Lamač et al., 2008).

Refinement top

The H-atoms were included in calculated positions and treated as riding atoms: C-H = 0.93 (aromatic CH) and 0.96 (CH3) Å, and Uiso(H) = k × Ueq(parent C-atom), where k = 1.2 for aromatic CH, and 1.5 for CH3.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of the title compound, showing the atom numbering scheme and displacement ellipsoids drawn at the 30% probability level.
Methyl (Sp)-2-(diphenylphosphino)ferrocene-1-carboxylate top
Crystal data top
[Fe(C5H5)(C19H16O2P)]F(000) = 888
Mr = 428.23Dx = 1.463 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 2517 reflections
a = 10.6867 (2) Åθ = 1.0–27.5°
b = 12.9015 (3) ŵ = 0.88 mm−1
c = 14.1042 (2) ÅT = 150 K
V = 1944.61 (6) Å3Block, orange
Z = 40.40 × 0.40 × 0.28 mm
Data collection top
Nonius KappaCCD
diffractometer		4228 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
horizontally mounted graphite crystalθmax = 27.5°, θmin = 2.1°
Detector resolution: 9.091 pixels mm-1h = −13→13
ω and π scans to fill the Ewald spherek = −16→16
15400 measured reflectionsl = −18→18
4449 independent reflections
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)] = 0.025H-atom parameters constrained
wR(F2) = 0.060 w = 1/[σ2(Fo2) + (0.0238P)2 + 0.8124P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
4449 reflectionsΔρmax = 0.51 e Å−3
254 parametersΔρmin = −0.29 e Å−3
0 restraintsAbsolute structure: Flack (1983), 1918 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.004 (11)
Crystal data top
[Fe(C5H5)(C19H16O2P)]V = 1944.61 (6) Å3
Mr = 428.23Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.6867 (2) ŵ = 0.88 mm−1
b = 12.9015 (3) ÅT = 150 K
c = 14.1042 (2) Å0.40 × 0.40 × 0.28 mm
Data collection top
Nonius KappaCCD
diffractometer		4228 reflections with I > 2σ(I)
15400 measured reflectionsRint = 0.036
4449 independent reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.060Δρmax = 0.51 e Å−3
S = 1.06Δρmin = −0.29 e Å−3
4449 reflectionsAbsolute structure: Flack (1983), 1918 Friedel pairs
254 parametersFlack parameter: 0.004 (11)
0 restraints
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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
Fe10.29965 (2)0.18843 (2)0.72459 (2)0.0181 (1)
P10.09939 (4)0.08083 (4)0.56683 (3)0.0184 (1)
O10.36618 (12)0.01291 (12)0.50125 (10)0.0306 (4)
O20.53342 (11)0.03569 (11)0.59516 (9)0.0268 (4)
C10.33684 (16)0.04902 (14)0.66438 (12)0.0188 (5)
C20.20328 (18)0.06630 (13)0.66896 (11)0.0184 (4)
C30.17351 (16)0.07818 (15)0.76755 (13)0.0224 (5)
C40.28491 (19)0.06905 (15)0.82171 (12)0.0252 (5)
C50.38563 (17)0.05158 (14)0.75918 (13)0.0224 (5)
C60.40940 (19)0.30253 (16)0.66633 (14)0.0273 (6)
C70.28422 (19)0.31090 (16)0.63399 (13)0.0284 (5)
C80.20585 (19)0.32594 (14)0.71400 (16)0.0318 (6)
C90.2832 (2)0.32638 (16)0.79572 (14)0.0322 (6)
C100.40893 (18)0.31174 (16)0.76638 (14)0.0284 (5)
C110.40972 (16)0.03148 (13)0.57782 (13)0.0192 (5)
C120.04477 (16)−0.05296 (14)0.54954 (12)0.0188 (5)
C13−0.04839 (17)−0.06903 (16)0.48155 (12)0.0221 (5)
C14−0.09729 (19)−0.16720 (16)0.46657 (13)0.0268 (5)
C15−0.0535 (2)−0.25121 (17)0.51784 (15)0.0304 (6)
C160.0408 (2)−0.23636 (16)0.58396 (15)0.0308 (6)
C170.08946 (18)−0.13788 (15)0.59981 (14)0.0249 (5)
C18−0.04185 (16)0.13315 (15)0.62459 (13)0.0215 (5)
C19−0.0773 (2)0.23452 (16)0.60378 (15)0.0305 (6)
C20−0.1852 (2)0.2765 (2)0.64381 (16)0.0438 (8)
C21−0.2570 (2)0.2184 (2)0.70388 (16)0.0431 (8)
C22−0.22483 (18)0.11714 (19)0.72475 (16)0.0371 (7)
C23−0.11703 (17)0.07494 (17)0.68559 (14)0.0278 (5)
C240.61344 (18)0.01350 (18)0.51607 (14)0.0309 (6)
H30.094000.090000.792000.0270*
H40.290500.073800.887400.0300*
H50.469000.043200.776300.0270*
H60.479600.292700.628400.0330*
H70.258000.307200.571200.0340*
H80.119400.334000.713000.0380*
H90.256100.334800.857900.0390*
H100.478600.308700.805800.0340*
H13−0.07780−0.013400.446000.0270*
H14−0.16000−0.176700.421700.0320*
H15−0.08690−0.316900.508000.0360*
H160.07170−0.292600.617900.0370*
H170.15250−0.128800.644500.0300*
H19−0.028700.274400.563000.0370*
H20−0.208400.344300.629600.0530*
H21−0.328300.247300.731000.0520*
H22−0.275000.077600.764700.0450*
H23−0.094700.007100.700200.0330*
H24A0.61180−0.059500.503100.0460*
H24B0.697500.034300.530800.0460*
H24C0.584600.050900.461400.0460*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.0169 (1)0.0204 (1)0.0170 (1)−0.0002 (1)0.0003 (1)−0.0020 (1)
P10.0167 (2)0.0190 (2)0.0196 (2)−0.0010 (2)−0.0012 (2)0.0012 (2)
O10.0238 (7)0.0435 (9)0.0244 (6)0.0042 (6)−0.0028 (6)−0.0110 (6)
O20.0157 (6)0.0392 (8)0.0256 (7)0.0010 (6)0.0011 (5)−0.0030 (6)
C10.0189 (8)0.0166 (9)0.0210 (8)0.0004 (7)−0.0013 (7)0.0004 (7)
C20.0173 (8)0.0189 (8)0.0190 (7)−0.0036 (8)−0.0004 (7)0.0007 (6)
C30.0190 (8)0.0273 (9)0.0208 (8)−0.0038 (7)0.0048 (7)0.0011 (8)
C40.0271 (9)0.0311 (10)0.0175 (8)−0.0027 (8)0.0000 (8)0.0052 (7)
C50.0217 (8)0.0231 (9)0.0225 (9)0.0013 (7)−0.0042 (7)0.0035 (7)
C60.0283 (10)0.0227 (10)0.0309 (9)−0.0052 (9)0.0065 (8)0.0011 (8)
C70.0367 (10)0.0191 (8)0.0293 (9)0.0027 (9)−0.0063 (8)0.0033 (8)
C80.0259 (9)0.0198 (9)0.0497 (12)0.0048 (8)−0.0013 (10)−0.0072 (9)
C90.0371 (11)0.0279 (10)0.0316 (10)−0.0041 (9)0.0078 (9)−0.0133 (8)
C100.0270 (9)0.0267 (9)0.0315 (9)−0.0060 (9)−0.0048 (8)−0.0047 (9)
C110.0181 (8)0.0152 (8)0.0244 (8)0.0025 (7)−0.0003 (7)0.0002 (7)
C120.0161 (8)0.0224 (9)0.0178 (8)0.0000 (7)0.0034 (6)−0.0025 (7)
C130.0232 (8)0.0250 (10)0.0181 (8)0.0009 (8)0.0009 (7)−0.0007 (7)
C140.0222 (8)0.0321 (11)0.0261 (9)−0.0021 (8)−0.0012 (8)−0.0074 (8)
C150.0297 (10)0.0238 (10)0.0376 (12)−0.0064 (8)0.0043 (9)−0.0061 (9)
C160.0337 (11)0.0218 (10)0.0370 (11)0.0019 (8)−0.0023 (9)0.0028 (9)
C170.0253 (9)0.0233 (9)0.0261 (9)−0.0001 (8)−0.0031 (8)−0.0003 (7)
C180.0160 (8)0.0236 (9)0.0250 (9)0.0000 (7)−0.0041 (7)−0.0048 (7)
C190.0332 (11)0.0276 (10)0.0307 (10)0.0077 (9)−0.0088 (9)−0.0023 (8)
C200.0474 (14)0.0429 (13)0.0412 (12)0.0272 (12)−0.0170 (11)−0.0124 (10)
C210.0252 (10)0.0666 (17)0.0374 (12)0.0200 (11)−0.0078 (9)−0.0214 (11)
C220.0213 (9)0.0546 (14)0.0354 (11)−0.0048 (9)0.0035 (9)−0.0135 (11)
C230.0193 (8)0.0300 (10)0.0342 (10)−0.0030 (8)0.0033 (8)−0.0073 (8)
C240.0201 (9)0.0393 (12)0.0332 (10)0.0027 (8)0.0069 (8)−0.0014 (9)
Geometric parameters (Å, °) top
Fe1—C12.0283 (18)C14—C151.384 (3)
Fe1—C22.0394 (17)C15—C161.386 (3)
Fe1—C32.0512 (18)C16—C171.391 (3)
Fe1—C42.0672 (18)C18—C191.393 (3)
Fe1—C52.0493 (18)C18—C231.396 (3)
Fe1—C62.054 (2)C19—C201.394 (3)
Fe1—C72.039 (2)C20—C211.367 (3)
Fe1—C82.0431 (19)C21—C221.383 (4)
Fe1—C92.051 (2)C22—C231.389 (3)
Fe1—C102.060 (2)C3—H30.9300
P1—C21.8283 (18)C4—H40.9300
P1—C121.8384 (19)C5—H50.9300
P1—C181.8433 (18)C6—H60.9300
O1—C111.200 (2)C7—H70.9300
O2—C111.346 (2)C8—H80.9300
O2—C241.434 (2)C9—H90.9300
C1—C21.446 (3)C10—H100.9300
C1—C51.436 (2)C13—H130.9300
C1—C111.466 (2)C14—H140.9300
C2—C31.435 (2)C15—H150.9300
C3—C41.419 (3)C16—H160.9300
C4—C51.410 (3)C17—H170.9300
C6—C71.418 (3)C19—H190.9300
C6—C101.416 (3)C20—H200.9300
C7—C81.419 (3)C21—H210.9300
C8—C91.418 (3)C22—H220.9300
C9—C101.419 (3)C23—H230.9300
C12—C131.398 (2)C24—H24A0.9600
C12—C171.390 (3)C24—H24B0.9600
C13—C141.386 (3)C24—H24C0.9600
C1—Fe1—C241.65 (7)Fe1—C8—C970.01 (12)
C1—Fe1—C368.75 (7)C7—C8—C9107.63 (18)
C1—Fe1—C468.39 (7)Fe1—C9—C869.45 (11)
C1—Fe1—C541.22 (7)Fe1—C9—C1070.15 (12)
C1—Fe1—C6110.87 (8)C8—C9—C10108.33 (17)
C1—Fe1—C7116.15 (7)Fe1—C10—C669.64 (12)
C1—Fe1—C8146.67 (8)Fe1—C10—C969.47 (11)
C1—Fe1—C9172.42 (8)C6—C10—C9107.77 (17)
C1—Fe1—C10133.92 (7)O1—C11—O2123.54 (16)
C2—Fe1—C341.06 (7)O1—C11—C1125.06 (16)
C2—Fe1—C468.95 (7)O2—C11—C1111.37 (15)
C2—Fe1—C569.66 (7)P1—C12—C13117.16 (14)
C2—Fe1—C6133.49 (7)P1—C12—C17124.29 (14)
C2—Fe1—C7108.47 (7)C13—C12—C17118.55 (17)
C2—Fe1—C8113.27 (8)C12—C13—C14120.57 (18)
C2—Fe1—C9144.64 (8)C13—C14—C15120.55 (18)
C2—Fe1—C10173.33 (7)C14—C15—C16119.3 (2)
C3—Fe1—C440.32 (7)C15—C16—C17120.41 (19)
C3—Fe1—C568.09 (7)C12—C17—C16120.64 (18)
C3—Fe1—C6172.11 (8)P1—C18—C19118.26 (14)
C3—Fe1—C7132.02 (8)P1—C18—C23123.13 (15)
C3—Fe1—C8107.54 (8)C19—C18—C23118.58 (17)
C3—Fe1—C9113.64 (8)C18—C19—C20120.3 (2)
C3—Fe1—C10145.46 (8)C19—C20—C21120.2 (2)
C4—Fe1—C540.05 (7)C20—C21—C22120.7 (2)
C4—Fe1—C6147.42 (8)C21—C22—C23119.5 (2)
C4—Fe1—C7170.60 (8)C18—C23—C22120.8 (2)
C4—Fe1—C8131.15 (8)Fe1—C3—H3127.00
C4—Fe1—C9108.42 (8)C2—C3—H3125.00
C4—Fe1—C10115.41 (8)C4—C3—H3125.00
C5—Fe1—C6117.18 (8)Fe1—C4—H4127.00
C5—Fe1—C7148.56 (8)C3—C4—H4126.00
C5—Fe1—C8170.22 (8)C5—C4—H4126.00
C5—Fe1—C9132.05 (8)Fe1—C5—H5126.00
C5—Fe1—C10110.07 (8)C1—C5—H5126.00
C6—Fe1—C740.53 (8)C4—C5—H5126.00
C6—Fe1—C868.20 (8)Fe1—C6—H6126.00
C6—Fe1—C967.83 (8)C7—C6—H6126.00
C6—Fe1—C1040.28 (8)C10—C6—H6126.00
C7—Fe1—C840.67 (8)Fe1—C7—H7126.00
C7—Fe1—C968.10 (8)C6—C7—H7126.00
C7—Fe1—C1068.08 (8)C8—C7—H7126.00
C8—Fe1—C940.54 (8)Fe1—C8—H8126.00
C8—Fe1—C1068.19 (8)C7—C8—H8126.00
C9—Fe1—C1040.38 (8)C9—C8—H8126.00
C2—P1—C12101.60 (8)Fe1—C9—H9126.00
C2—P1—C18100.75 (8)C8—C9—H9126.00
C12—P1—C1898.19 (8)C10—C9—H9126.00
C11—O2—C24115.87 (14)Fe1—C10—H10126.00
Fe1—C1—C269.59 (10)C6—C10—H10126.00
Fe1—C1—C570.17 (10)C9—C10—H10126.00
Fe1—C1—C11126.14 (13)C12—C13—H13120.00
C2—C1—C5108.26 (15)C14—C13—H13120.00
C2—C1—C11125.84 (15)C13—C14—H14120.00
C5—C1—C11125.90 (16)C15—C14—H14120.00
Fe1—C2—P1122.04 (9)C14—C15—H15120.00
Fe1—C2—C168.77 (10)C16—C15—H15120.00
Fe1—C2—C369.91 (10)C15—C16—H16120.00
P1—C2—C1125.45 (12)C17—C16—H16120.00
P1—C2—C3128.17 (14)C12—C17—H17120.00
C1—C2—C3106.18 (15)C16—C17—H17120.00
Fe1—C3—C269.03 (10)C18—C19—H19120.00
Fe1—C3—C470.45 (11)C20—C19—H19120.00
C2—C3—C4109.07 (15)C19—C20—H20120.00
Fe1—C4—C369.24 (11)C21—C20—H20120.00
Fe1—C4—C569.29 (10)C20—C21—H21120.00
C3—C4—C5108.48 (15)C22—C21—H21120.00
Fe1—C5—C168.61 (10)C21—C22—H22120.00
Fe1—C5—C470.66 (11)C23—C22—H22120.00
C1—C5—C4108.00 (16)C18—C23—H23120.00
Fe1—C6—C769.17 (12)C22—C23—H23120.00
Fe1—C6—C1070.09 (12)O2—C24—H24A109.00
C7—C6—C10108.11 (17)O2—C24—H24B109.00
Fe1—C7—C670.30 (12)O2—C24—H24C109.00
Fe1—C7—C869.83 (11)H24A—C24—H24B109.00
C6—C7—C8108.16 (17)H24A—C24—H24C110.00
Fe1—C8—C769.50 (11)H24B—C24—H24C109.00
C2—Fe1—C1—C5−119.32 (14)C2—Fe1—C8—C9149.66 (11)
C2—Fe1—C1—C11120.12 (19)C3—Fe1—C8—C7−135.19 (12)
C3—Fe1—C1—C238.73 (10)C3—Fe1—C8—C9106.12 (12)
C3—Fe1—C1—C5−80.58 (11)C4—Fe1—C8—C7−173.40 (11)
C3—Fe1—C1—C11158.85 (17)C4—Fe1—C8—C967.91 (15)
C4—Fe1—C1—C282.19 (11)C6—Fe1—C8—C737.77 (12)
C4—Fe1—C1—C5−37.13 (11)C6—Fe1—C8—C9−80.93 (13)
C4—Fe1—C1—C11−157.69 (17)C7—Fe1—C8—C9−118.70 (17)
C5—Fe1—C1—C2119.32 (14)C9—Fe1—C8—C7118.70 (17)
C5—Fe1—C1—C11−120.57 (19)C10—Fe1—C8—C781.30 (12)
C6—Fe1—C1—C2−132.83 (10)C10—Fe1—C8—C9−37.40 (12)
C6—Fe1—C1—C5107.86 (11)C2—Fe1—C9—C8−53.32 (18)
C6—Fe1—C1—C11−12.71 (17)C2—Fe1—C9—C10−172.81 (12)
C7—Fe1—C1—C2−88.80 (11)C3—Fe1—C9—C8−89.67 (13)
C7—Fe1—C1—C5151.88 (11)C3—Fe1—C9—C10150.84 (11)
C7—Fe1—C1—C1131.32 (17)C4—Fe1—C9—C8−132.66 (12)
C8—Fe1—C1—C2−51.10 (17)C4—Fe1—C9—C10107.85 (12)
C8—Fe1—C1—C5−170.41 (13)C5—Fe1—C9—C8−170.83 (12)
C8—Fe1—C1—C1169.0 (2)C5—Fe1—C9—C1069.68 (15)
C10—Fe1—C1—C2−172.79 (10)C6—Fe1—C9—C881.92 (13)
C10—Fe1—C1—C567.89 (14)C6—Fe1—C9—C10−37.58 (12)
C10—Fe1—C1—C11−52.67 (19)C7—Fe1—C9—C838.04 (12)
C1—Fe1—C2—P1−119.40 (15)C7—Fe1—C9—C10−81.46 (12)
C1—Fe1—C2—C3117.41 (14)C8—Fe1—C9—C10−119.49 (17)
C3—Fe1—C2—P1123.19 (16)C10—Fe1—C9—C8119.49 (17)
C3—Fe1—C2—C1−117.41 (14)C1—Fe1—C10—C668.19 (15)
C4—Fe1—C2—P1159.87 (13)C1—Fe1—C10—C9−172.69 (11)
C4—Fe1—C2—C1−80.73 (11)C3—Fe1—C10—C6−171.06 (13)
C4—Fe1—C2—C336.68 (11)C3—Fe1—C10—C9−51.93 (18)
C5—Fe1—C2—P1−157.19 (13)C4—Fe1—C10—C6151.95 (12)
C5—Fe1—C2—C1−37.79 (10)C4—Fe1—C10—C9−88.93 (13)
C5—Fe1—C2—C379.62 (11)C5—Fe1—C10—C6108.73 (12)
C6—Fe1—C2—P1−48.55 (16)C5—Fe1—C10—C9−132.15 (12)
C6—Fe1—C2—C170.85 (13)C6—Fe1—C10—C9119.12 (17)
C6—Fe1—C2—C3−171.74 (11)C7—Fe1—C10—C6−37.59 (12)
C7—Fe1—C2—P1−10.52 (13)C7—Fe1—C10—C981.53 (12)
C7—Fe1—C2—C1108.88 (11)C8—Fe1—C10—C6−81.57 (13)
C7—Fe1—C2—C3−133.71 (11)C8—Fe1—C10—C937.55 (12)
C8—Fe1—C2—P132.86 (13)C9—Fe1—C10—C6−119.12 (17)
C8—Fe1—C2—C1152.26 (11)C12—P1—C2—Fe1178.79 (10)
C8—Fe1—C2—C3−90.33 (12)C12—P1—C2—C193.31 (16)
C9—Fe1—C2—P167.43 (16)C12—P1—C2—C3−92.55 (17)
C9—Fe1—C2—C1−173.17 (12)C18—P1—C2—Fe1−80.43 (12)
C9—Fe1—C2—C3−55.76 (16)C18—P1—C2—C1−165.91 (15)
C1—Fe1—C3—C2−39.27 (10)C18—P1—C2—C38.23 (18)
C1—Fe1—C3—C481.23 (11)C2—P1—C12—C13173.55 (14)
C2—Fe1—C3—C4120.50 (15)C2—P1—C12—C17−6.04 (18)
C4—Fe1—C3—C2−120.50 (15)C18—P1—C12—C1370.72 (15)
C5—Fe1—C3—C2−83.75 (11)C18—P1—C12—C17−108.86 (16)
C5—Fe1—C3—C436.75 (11)C2—P1—C18—C19113.07 (16)
C7—Fe1—C3—C267.35 (14)C2—P1—C18—C23−69.12 (17)
C7—Fe1—C3—C4−172.15 (11)C12—P1—C18—C19−143.39 (16)
C8—Fe1—C3—C2105.54 (12)C12—P1—C18—C2334.41 (17)
C8—Fe1—C3—C4−133.96 (12)C24—O2—C11—O1−1.7 (3)
C9—Fe1—C3—C2148.52 (11)C24—O2—C11—C1176.49 (16)
C9—Fe1—C3—C4−90.98 (12)Fe1—C1—C2—P1114.97 (13)
C10—Fe1—C3—C2−177.65 (13)Fe1—C1—C2—C3−60.24 (12)
C10—Fe1—C3—C4−57.15 (17)C5—C1—C2—Fe159.74 (12)
C1—Fe1—C4—C3−82.20 (11)C5—C1—C2—P1174.71 (13)
C1—Fe1—C4—C538.18 (11)C5—C1—C2—C3−0.5 (2)
C2—Fe1—C4—C3−37.33 (11)C11—C1—C2—Fe1−120.49 (18)
C2—Fe1—C4—C583.05 (11)C11—C1—C2—P1−5.5 (3)
C3—Fe1—C4—C5120.38 (15)C11—C1—C2—C3179.27 (17)
C5—Fe1—C4—C3−120.38 (15)Fe1—C1—C5—C459.91 (13)
C6—Fe1—C4—C3−177.45 (14)C2—C1—C5—Fe1−59.37 (12)
C6—Fe1—C4—C5−57.07 (18)C2—C1—C5—C40.5 (2)
C8—Fe1—C4—C365.71 (14)C11—C1—C5—Fe1120.86 (18)
C8—Fe1—C4—C5−173.91 (11)C11—C1—C5—C4−179.23 (17)
C9—Fe1—C4—C3105.12 (12)Fe1—C1—C11—O1−102.1 (2)
C9—Fe1—C4—C5−134.50 (11)Fe1—C1—C11—O279.71 (18)
C10—Fe1—C4—C3148.17 (11)C2—C1—C11—O1−12.5 (3)
C10—Fe1—C4—C5−91.45 (12)C2—C1—C11—O2169.40 (16)
C1—Fe1—C5—C4−119.29 (15)C5—C1—C11—O1167.28 (19)
C2—Fe1—C5—C138.17 (10)C5—C1—C11—O2−10.9 (2)
C2—Fe1—C5—C4−81.13 (11)Fe1—C2—C3—C4−59.22 (13)
C3—Fe1—C5—C182.31 (11)P1—C2—C3—Fe1−115.54 (14)
C3—Fe1—C5—C4−36.99 (11)P1—C2—C3—C4−174.76 (14)
C4—Fe1—C5—C1119.29 (15)C1—C2—C3—Fe159.50 (12)
C6—Fe1—C5—C1−91.24 (12)C1—C2—C3—C40.3 (2)
C6—Fe1—C5—C4149.47 (11)Fe1—C3—C4—C5−58.30 (13)
C7—Fe1—C5—C1−54.20 (18)C2—C3—C4—Fe158.35 (13)
C7—Fe1—C5—C4−173.49 (14)C2—C3—C4—C50.1 (2)
C9—Fe1—C5—C1−175.02 (11)Fe1—C4—C5—C1−58.63 (13)
C9—Fe1—C5—C465.68 (14)C3—C4—C5—Fe158.27 (13)
C10—Fe1—C5—C1−134.72 (11)C3—C4—C5—C1−0.4 (2)
C10—Fe1—C5—C4105.98 (12)Fe1—C6—C7—C859.81 (14)
C1—Fe1—C6—C7106.25 (12)C10—C6—C7—Fe1−59.48 (14)
C1—Fe1—C6—C10−134.30 (11)C10—C6—C7—C80.3 (2)
C2—Fe1—C6—C764.04 (15)Fe1—C6—C10—C9−59.21 (14)
C2—Fe1—C6—C10−176.51 (11)C7—C6—C10—Fe158.91 (14)
C4—Fe1—C6—C7−171.54 (13)C7—C6—C10—C9−0.3 (2)
C4—Fe1—C6—C10−52.09 (19)Fe1—C7—C8—C959.88 (14)
C5—Fe1—C6—C7151.09 (11)C6—C7—C8—Fe1−60.11 (14)
C5—Fe1—C6—C10−89.47 (13)C6—C7—C8—C9−0.2 (2)
C7—Fe1—C6—C10119.45 (17)Fe1—C8—C9—C1059.59 (14)
C8—Fe1—C6—C7−37.90 (12)C7—C8—C9—Fe1−59.56 (13)
C8—Fe1—C6—C1081.55 (13)C7—C8—C9—C100.0 (2)
C9—Fe1—C6—C7−81.78 (12)Fe1—C9—C10—C659.32 (14)
C9—Fe1—C6—C1037.67 (12)C8—C9—C10—Fe1−59.15 (14)
C10—Fe1—C6—C7−119.45 (17)C8—C9—C10—C60.2 (2)
C1—Fe1—C7—C6−92.09 (12)P1—C12—C13—C14−177.91 (14)
C1—Fe1—C7—C8148.96 (11)C17—C12—C13—C141.7 (3)
C2—Fe1—C7—C6−136.55 (11)P1—C12—C17—C16178.41 (15)
C2—Fe1—C7—C8104.49 (12)C13—C12—C17—C16−1.2 (3)
C3—Fe1—C7—C6−176.28 (11)C12—C13—C14—C15−0.9 (3)
C3—Fe1—C7—C864.77 (15)C13—C14—C15—C16−0.6 (3)
C5—Fe1—C7—C6−55.55 (19)C14—C15—C16—C171.1 (3)
C5—Fe1—C7—C8−174.50 (14)C15—C16—C17—C12−0.2 (3)
C6—Fe1—C7—C8−118.95 (16)P1—C18—C19—C20178.32 (16)
C8—Fe1—C7—C6118.95 (16)C23—C18—C19—C200.4 (3)
C9—Fe1—C7—C681.04 (13)P1—C18—C23—C22−177.83 (16)
C9—Fe1—C7—C8−37.92 (12)C19—C18—C23—C220.0 (3)
C10—Fe1—C7—C637.36 (11)C18—C19—C20—C210.0 (3)
C10—Fe1—C7—C8−81.59 (12)C19—C20—C21—C22−0.9 (3)
C1—Fe1—C8—C7−57.39 (18)C20—C21—C22—C231.3 (3)
C1—Fe1—C8—C9−176.09 (13)C21—C22—C23—C18−0.8 (3)
C2—Fe1—C8—C7−91.65 (12)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.932.583.184 (2)123
C15—H15···O1ii0.932.583.494 (3)167
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) x−1/2, −y−1/2, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O1i0.932.583.184 (2)123
C15—H15···O1ii0.932.583.494 (3)167
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) x−1/2, −y−1/2, −z+1.
Acknowledgements top

This work was supported financially by the Grant Agency of Charles University in Prague (project No. 58009) and is a part of the long-term research project supported by the Ministry of Education, Youth and Sports of the Czech Republic (project No. MSM0021620857).

references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Flack, H. D. (1983). Acta Cryst. A39, 876–881.

Lamač, M., Císařová, I. & Štěpnička, P. (2009). New J. Chem. 33, 1549–1562.

Lamač, M., Cvačka, J. & Štěpnička, P. (2008). J. Organomet. Chem. 693, 3430–3434.

Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.

Štěpnička, P. (2002). New J. Chem. 26, 567–575.

Štěpnička, P. (2008). Ferrocenes: Ligands, Materials and Biomolecules. Wiley: Chichester.

You, S.-L., Hou, X.-L., Dai, L.-X., Yu, Y.-H. & Xia, W. (2002). J. Org. Chem. 67, 4684–4695.