PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): m1216.
Published online 2009 September 16. doi:  10.1107/S1600536809036654
PMCID: PMC2970334

Methyl (S p)-2-(diphenyl­phosphino)ferrocene-1-carboxyl­ate

Abstract

The title compound, [Fe(C5H5)(C19H16O2P)], obtained serendipitously during recrystallization of 1-hydroxy­benzotriazolyl (S p)-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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-m1216-scheme1.jpg

Experimental

Crystal data

  • [Fe(C5H5)(C19H16O2P)]
  • M r = 428.23
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1216-efi1.jpg
  • a = 10.6867 (2) Å
  • b = 12.9015 (3) Å
  • c = 14.1042 (2) Å
  • V = 1944.61 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.88 mm−1
  • T = 150 K
  • 0.40 × 0.40 × 0.28 mm

Data collection

  • Nonius KappaCCD diffractometer
  • Absorption correction: none
  • 15400 measured reflections
  • 4449 independent reflections
  • 4228 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.025
  • wR(F 2) = 0.060
  • S = 1.06
  • 4449 reflections
  • 254 parameters
  • H-atom parameters constrained
  • Δρmax = 0.51 e Å−3
  • Δρmin = −0.29 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1918 Friedel pairs
  • Flack parameter: 0.004 (11)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036654/su2145sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036654/su2145Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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).

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.

Crystal data

[Fe(C5H5)(C19H16O2P)]F(000) = 888
Mr = 428.23Dx = 1.463 Mg m3
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 mm1
c = 14.1042 (2) ÅT = 150 K
V = 1944.61 (6) Å3Block, orange
Z = 40.40 × 0.40 × 0.28 mm

Data collection

Nonius KappaCCD diffractometer4228 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

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) = 0.060w = 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 Å3
254 parametersΔρmin = −0.29 e Å3
0 restraintsAbsolute structure: Flack (1983), 1918 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.004 (11)

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2145).

References

  • 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. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • 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. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography