Download citation
Download citation
link to html
The absolute configuration of the title compound, [Fe(C5H5)(C36H29OP2)], is Sp at the ferrocene group and S at the asymmetric C atom. Both P atoms have a trigonal–pyramidal conformation. There is a short intra­molecular C—H...P contact with an H...P distance of 2.56 Å. The hydr­oxy group is involved in an intra­molecular O—H...πphen­yl inter­action. The crystal packing shows five very weak inter­molecular C—H...π contacts, with H...Cg distances between 3.26 and 3.39 Å (Cg is the centroid of a phenyl or cyclo­penta­dienyl ring).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808038294/nc2123sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808038294/nc2123Isup2.hkl
Contains datablock I

CCDC reference: 712328

Key indicators

  • Single-crystal X-ray study
  • T = 162 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.038
  • wR factor = 0.083
  • Data-to-parameter ratio = 22.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT420_ALERT_2_B D-H Without Acceptor O1 - H1A ... ?
Alert level C Value of measurement temperature given = 162.000 Value of melting point given = 0.000 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 30.50 From the CIF: _reflns_number_total 9131 Count of symmetry unique reflns 5301 Completeness (_total/calc) 172.25% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3830 Fraction of Friedel pairs measured 0.723 Are heavy atom types Z>Si present yes PLAT791_ALERT_4_G The Model has Chirality at C11 (Verify) .... S
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The structure originally published for the Taniaphos ligands, a chiral ligand technology owned by Umicore and sold via Solvias, recently had to be corrected. It was shown that these ligands do not have the (R,Sp) or (S,Rp) but the (R,Rp) or (S,Sp) configuration, respectively (Fukuzawa, Yamamoto, Hosaka & Kikuchi, et al., 2007; Ireland et al., 2008). The planar chirality of the 1,2-disubstituted ferrocene initially had been assigned incorrectly. Our present investigation confirms the configuration of a special member of this family, bearing a hydroxy group in the side-chain of the ferrocene ring (Lotz & Spindler, 2005).

The molecular structure of the title compound is shown in Fig. 1. The ferrocene group deviates only 4° from an eclipsed conformation. The angle between the planes of the two cyclopentadienyl rings is 4.2 (2)°. Both P atoms have a pyramidal conformation. The lone-pair lobe of atom P1 shows a short intramolecular contact distance of 2.56 Å with the H atom of C11 (Table 1). The hydroxy group is not involved in conventional inter- or intramolecular hydrogen bonding. It shows instead a short intramolecular O—H···πphenyl interaction with the phenyl ring labeled C18 through C23. The O—H group is not directed to the center of this phenyl ring, but points mainly to atom C23 (Table 1). There is an intramolecular π···π interaction between the benzene rings labeled C12 C17 and C36 C41. The angle between the planes of these rings is 4.8 (2)°. The shortest contact distance is 3.498 (3)Å between C12 and C37. The crystal packing shows five very weak intermolecular C—H···π interactions, with H···Cg distances between 3.26 and 3.39 Å (Cg is the centroid of a phenyl or cyclopentadienyl ring).

Related literature top

The preparation of the title compound has been reported by Lotz & Spindler (2005). The stereochemistry of the Taniaphos ligand has been discussed by Ireland et al. (2008). For the synthesis of related compounds, see: Ireland et al. (2002); Fukuzawa, Yamamoto, Hosaka & Kikuchi (2007). For the crystal structures of related compounds, see: Fukuzawa, Yamamoto & Kikuchi (2007); Ireland et al. (1999).

Experimental top

The preparation of the title compound has been reported by Lotz & Spindler (2005). Crystals were obtained from a solution of the title compound in a mixture of chloroform and n-hexane.

Refinement top

H atoms were geometrically positioned using distances: Cplanar—H=0.95 Å, Cprimary—H=1.00 Å, Uiso(H)=1.2Ueq(C). The H atom of the hydroxy group was taken from a difference Fourier synthesis and was refined with an isotropic thermal parameter. Friedel opposites were not averaged. The absolute configuration was determined from 4069 Friedel pairs.

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SMART (Siemens, 1995); data reduction: SAINT (Siemens, 1995); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound shown with 50% probability displacement ellipsoids. The H atoms are drawn as small spheres of arbitrary radius.
(Sp)-1-Diphenylphosphanyl-2-{(S)-[2- (diphenylphosphanyl)phenyl]hydroxymethyl}ferrocene top
Crystal data top
[Fe(C5H5)(C36H29OP2)]F(000) = 688
Mr = 660.47Dx = 1.343 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 239 reflections
a = 11.6111 (15) Åθ = 3–23°
b = 8.6154 (10) ŵ = 0.59 mm1
c = 16.481 (2) ÅT = 162 K
β = 97.807 (12)°Block, orange
V = 1633.4 (3) Å30.40 × 0.40 × 0.32 mm
Z = 2
Data collection top
Siemens SMART 1K CCD
diffractometer
9131 independent reflections
Radiation source: normal-focus sealed tube7926 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.051
ω scansθmax = 30.5°, θmin = 1.8°
Absorption correction: numerical
(SHELXTL; Sheldrick, 2008)
h = 1616
Tmin = 0.795, Tmax = 0.845k = 1212
25293 measured reflectionsl = 2323
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)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083 w = 1/[σ2(Fo2) + (0.03P)2 + 0.5P]
where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.003
9131 reflectionsΔρmax = 0.33 e Å3
410 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack (1983), 4069 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.023 (10)
Crystal data top
[Fe(C5H5)(C36H29OP2)]V = 1633.4 (3) Å3
Mr = 660.47Z = 2
Monoclinic, P21Mo Kα radiation
a = 11.6111 (15) ŵ = 0.59 mm1
b = 8.6154 (10) ÅT = 162 K
c = 16.481 (2) Å0.40 × 0.40 × 0.32 mm
β = 97.807 (12)°
Data collection top
Siemens SMART 1K CCD
diffractometer
9131 independent reflections
Absorption correction: numerical
(SHELXTL; Sheldrick, 2008)
7926 reflections with I > 2σ(I)
Tmin = 0.795, Tmax = 0.845Rint = 0.051
25293 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.083Δρmax = 0.33 e Å3
S = 1.07Δρmin = 0.23 e Å3
9131 reflectionsAbsolute structure: Flack (1983), 4069 Friedel pairs
410 parametersAbsolute structure parameter: 0.023 (10)
1 restraint
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
Fe10.19359 (2)0.01898 (3)0.741420 (18)0.02801 (7)
P10.62868 (4)0.27356 (6)0.85276 (3)0.02329 (11)
P20.32422 (4)0.33294 (6)0.71106 (3)0.02413 (11)
O10.47730 (15)0.14478 (19)0.81532 (11)0.0352 (4)
C10.35814 (16)0.0009 (2)0.71422 (12)0.0249 (4)
C20.30376 (19)0.1365 (3)0.67651 (15)0.0319 (5)
H2A0.33040.24020.68530.038*
C30.2027 (2)0.0890 (3)0.62352 (16)0.0360 (5)
H3A0.14990.15590.59130.043*
C40.19426 (19)0.0751 (3)0.62691 (14)0.0310 (5)
H4A0.13490.13670.59730.037*
C50.29067 (17)0.1323 (2)0.68279 (12)0.0244 (4)
C60.2085 (2)0.0518 (3)0.86549 (16)0.0466 (7)
H6A0.27900.05740.90210.056*
C70.1497 (3)0.1778 (4)0.8229 (2)0.0585 (9)
H7A0.17420.28310.82600.070*
C80.0498 (3)0.1210 (4)0.7757 (2)0.0567 (8)
H8A0.00530.18120.74130.068*
C90.0444 (2)0.0418 (4)0.78764 (17)0.0445 (6)
H9A0.01440.10980.76280.053*
C100.1430 (2)0.0839 (3)0.84353 (14)0.0365 (5)
H10A0.16190.18580.86300.044*
C110.46677 (16)0.0034 (2)0.77503 (12)0.0255 (4)
H11A0.45830.08570.81660.031*
C120.57475 (16)0.0380 (2)0.73482 (12)0.0232 (4)
C130.59482 (18)0.0521 (2)0.66787 (13)0.0306 (5)
H13A0.54150.13190.64890.037*
C140.69159 (18)0.0268 (3)0.62852 (13)0.0345 (5)
H14A0.70510.09050.58370.041*
C150.76792 (19)0.0911 (3)0.65477 (14)0.0341 (5)
H15A0.83300.11090.62710.041*
C160.74938 (18)0.1810 (3)0.72182 (13)0.0272 (4)
H16A0.80240.26210.73940.033*
C170.65449 (17)0.1546 (2)0.76401 (12)0.0224 (4)
C180.64664 (17)0.1267 (2)0.93453 (12)0.0247 (4)
C190.59727 (19)0.1590 (3)1.00546 (13)0.0309 (5)
H19A0.55890.25531.01020.037*
C200.6035 (2)0.0530 (3)1.06872 (14)0.0380 (5)
H20A0.57030.07741.11680.046*
C210.6582 (2)0.0893 (3)1.06242 (14)0.0345 (5)
H21A0.66090.16301.10550.041*
C220.70842 (19)0.1230 (3)0.99310 (13)0.0312 (5)
H22A0.74630.21980.98880.037*
C230.70385 (16)0.0159 (3)0.92957 (12)0.0284 (4)
H23A0.73970.03950.88250.034*
C240.76505 (18)0.3831 (3)0.87543 (13)0.0284 (4)
C250.8662 (2)0.3235 (3)0.91878 (17)0.0450 (6)
H25A0.86790.21870.93690.054*
C260.9648 (2)0.4150 (4)0.93611 (19)0.0574 (8)
H26A1.03320.37310.96630.069*
C270.9636 (3)0.5670 (4)0.90944 (17)0.0511 (8)
H27A1.03100.62980.92150.061*
C280.8645 (3)0.6274 (3)0.86535 (19)0.0492 (7)
H28A0.86420.73130.84600.059*
C290.7647 (2)0.5367 (3)0.84906 (16)0.0369 (5)
H29A0.69600.57980.81980.044*
C300.19045 (17)0.4249 (2)0.65968 (13)0.0268 (4)
C310.0981 (2)0.4392 (3)0.70517 (14)0.0334 (5)
H31A0.10850.40980.76120.040*
C320.00866 (19)0.4957 (3)0.66960 (15)0.0399 (5)
H32A0.07130.50270.70100.048*
C330.0244 (2)0.5420 (3)0.58854 (17)0.0431 (6)
H33A0.09750.58090.56420.052*
C340.0673 (2)0.5313 (4)0.54313 (16)0.0473 (7)
H34A0.05720.56350.48750.057*
C350.17429 (18)0.4734 (3)0.57875 (13)0.0367 (5)
H35A0.23690.46700.54730.044*
C360.43404 (17)0.3780 (2)0.64374 (12)0.0249 (4)
C370.45399 (18)0.2857 (3)0.57774 (13)0.0301 (4)
H37A0.40390.20060.56200.036*
C380.54639 (19)0.3165 (3)0.53441 (14)0.0348 (5)
H38A0.55950.25220.48980.042*
C390.6192 (2)0.4415 (3)0.55664 (15)0.0377 (6)
H39A0.68220.46300.52710.045*
C400.6003 (2)0.5345 (3)0.62161 (17)0.0378 (5)
H40A0.65010.62030.63650.045*
C410.50852 (17)0.5034 (2)0.66566 (14)0.0301 (4)
H41A0.49650.56750.71070.036*
H1A0.532 (2)0.146 (3)0.8487 (17)0.034 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02189 (13)0.02740 (15)0.03497 (16)0.00588 (13)0.00474 (11)0.00120 (13)
P10.0218 (2)0.0242 (2)0.0240 (2)0.00007 (19)0.00343 (19)0.0001 (2)
P20.0264 (2)0.0262 (3)0.0196 (2)0.0037 (2)0.00265 (18)0.0002 (2)
O10.0310 (8)0.0341 (9)0.0392 (9)0.0060 (7)0.0002 (7)0.0144 (7)
C10.0224 (8)0.0251 (10)0.0276 (9)0.0054 (8)0.0049 (7)0.0012 (8)
C20.0293 (11)0.0288 (11)0.0380 (12)0.0044 (9)0.0062 (9)0.0060 (9)
C30.0340 (12)0.0360 (12)0.0370 (13)0.0084 (10)0.0006 (10)0.0089 (10)
C40.0283 (11)0.0328 (12)0.0300 (11)0.0047 (9)0.0024 (9)0.0023 (9)
C50.0230 (9)0.0262 (10)0.0241 (10)0.0055 (8)0.0032 (7)0.0005 (8)
C60.0403 (12)0.063 (2)0.0393 (13)0.0053 (12)0.0143 (10)0.0198 (12)
C70.0666 (19)0.0405 (15)0.078 (2)0.0039 (14)0.0434 (17)0.0172 (15)
C80.0426 (15)0.0584 (19)0.074 (2)0.0285 (14)0.0247 (14)0.0143 (16)
C90.0246 (11)0.0599 (17)0.0501 (15)0.0002 (11)0.0098 (10)0.0011 (13)
C100.0364 (12)0.0422 (14)0.0328 (12)0.0073 (10)0.0113 (10)0.0005 (10)
C110.0260 (9)0.0249 (11)0.0262 (9)0.0024 (8)0.0053 (7)0.0023 (8)
C120.0219 (9)0.0245 (9)0.0230 (9)0.0006 (7)0.0022 (7)0.0039 (7)
C130.0302 (10)0.0309 (12)0.0304 (11)0.0023 (8)0.0031 (8)0.0042 (8)
C140.0369 (10)0.0417 (12)0.0267 (10)0.0016 (11)0.0103 (8)0.0050 (11)
C150.0276 (10)0.0458 (13)0.0311 (11)0.0004 (9)0.0120 (9)0.0007 (10)
C160.0238 (10)0.0305 (11)0.0280 (10)0.0031 (8)0.0058 (8)0.0013 (9)
C170.0206 (9)0.0258 (10)0.0206 (9)0.0028 (7)0.0018 (7)0.0031 (7)
C180.0213 (9)0.0288 (10)0.0233 (9)0.0035 (8)0.0008 (7)0.0009 (8)
C190.0348 (11)0.0328 (11)0.0265 (10)0.0005 (9)0.0092 (9)0.0043 (9)
C200.0468 (13)0.0450 (13)0.0246 (11)0.0002 (11)0.0140 (10)0.0016 (10)
C210.0383 (12)0.0403 (13)0.0248 (11)0.0008 (10)0.0045 (9)0.0090 (9)
C220.0314 (10)0.0345 (11)0.0269 (11)0.0053 (9)0.0008 (8)0.0033 (8)
C230.0285 (9)0.0334 (10)0.0241 (9)0.0056 (10)0.0066 (7)0.0033 (9)
C240.0297 (10)0.0302 (11)0.0257 (10)0.0069 (8)0.0056 (8)0.0048 (8)
C250.0334 (12)0.0499 (15)0.0488 (15)0.0136 (12)0.0047 (10)0.0138 (12)
C260.0378 (14)0.083 (2)0.0483 (16)0.0260 (15)0.0056 (12)0.0108 (15)
C270.0493 (16)0.0645 (19)0.0433 (15)0.0342 (14)0.0194 (13)0.0207 (14)
C280.0579 (17)0.0324 (13)0.0644 (18)0.0186 (12)0.0343 (15)0.0121 (12)
C290.0401 (12)0.0304 (11)0.0434 (13)0.0024 (9)0.0167 (10)0.0038 (10)
C300.0267 (9)0.0261 (10)0.0278 (10)0.0013 (8)0.0041 (8)0.0010 (8)
C310.0383 (12)0.0312 (12)0.0330 (11)0.0020 (9)0.0130 (9)0.0015 (9)
C320.0330 (11)0.0404 (13)0.0489 (14)0.0020 (11)0.0149 (10)0.0006 (12)
C330.0271 (11)0.0507 (15)0.0502 (15)0.0051 (10)0.0009 (10)0.0023 (12)
C340.0368 (13)0.071 (2)0.0337 (13)0.0077 (12)0.0017 (10)0.0095 (12)
C350.0302 (10)0.0532 (14)0.0276 (10)0.0050 (11)0.0068 (8)0.0037 (11)
C360.0249 (9)0.0246 (10)0.0247 (10)0.0011 (8)0.0016 (7)0.0041 (8)
C370.0311 (10)0.0330 (11)0.0256 (10)0.0017 (9)0.0018 (8)0.0027 (9)
C380.0355 (11)0.0439 (13)0.0258 (10)0.0052 (10)0.0070 (9)0.0047 (9)
C390.0322 (11)0.0399 (14)0.0432 (13)0.0044 (9)0.0136 (10)0.0164 (10)
C400.0315 (11)0.0270 (11)0.0553 (15)0.0037 (9)0.0073 (10)0.0118 (10)
C410.0283 (9)0.0239 (11)0.0379 (11)0.0009 (8)0.0042 (8)0.0041 (9)
Geometric parameters (Å, º) top
Fe1—C12.0269 (18)C16—C171.399 (3)
Fe1—C72.030 (3)C16—H16A0.9500
Fe1—C82.033 (3)C18—C191.398 (3)
Fe1—C22.044 (2)C18—C231.405 (3)
Fe1—C62.048 (3)C19—C201.380 (3)
Fe1—C52.049 (2)C19—H19A0.9500
Fe1—C32.051 (3)C20—C211.391 (3)
Fe1—C92.053 (2)C20—H20A0.9500
Fe1—C42.055 (2)C21—C221.382 (3)
Fe1—C102.057 (2)C21—H21A0.9500
P1—C241.837 (2)C22—C231.391 (3)
P1—C181.839 (2)C22—H22A0.9500
P1—C171.843 (2)C23—H23A0.9500
P2—C51.818 (2)C24—C251.387 (3)
P2—C361.842 (2)C24—C291.393 (3)
P2—C301.844 (2)C25—C261.388 (4)
O1—C111.437 (3)C25—H25A0.9500
O1—H1A0.78 (3)C26—C271.381 (4)
C1—C21.429 (3)C26—H26A0.9500
C1—C51.446 (3)C27—C281.376 (4)
C1—C111.501 (3)C27—H27A0.9500
C2—C31.424 (3)C28—C291.394 (3)
C2—H2A0.9500C28—H28A0.9500
C3—C41.419 (3)C29—H29A0.9500
C3—H3A0.9500C30—C351.386 (3)
C4—C51.437 (3)C30—C311.395 (3)
C4—H4A0.9500C31—C321.386 (3)
C6—C101.415 (4)C31—H31A0.9500
C6—C71.416 (5)C32—C331.382 (4)
C6—H6A0.9500C32—H32A0.9500
C7—C81.395 (5)C33—C341.385 (3)
C7—H7A0.9500C33—H33A0.9500
C8—C91.418 (4)C34—C351.392 (3)
C8—H8A0.9500C34—H34A0.9500
C9—C101.416 (4)C35—H35A0.9500
C9—H9A0.9500C36—C371.392 (3)
C10—H10A0.9500C36—C411.400 (3)
C11—C121.525 (3)C37—C381.393 (3)
C11—H11A1.0000C37—H37A0.9500
C12—C131.394 (3)C38—C391.387 (3)
C12—C171.406 (3)C38—H38A0.9500
C13—C141.389 (3)C39—C401.378 (4)
C13—H13A0.9500C39—H39A0.9500
C14—C151.379 (3)C40—C411.395 (3)
C14—H14A0.9500C40—H40A0.9500
C15—C161.390 (3)C41—H41A0.9500
C15—H15A0.9500
C1—Fe1—C7121.78 (11)C8—C9—H9A126.4
C1—Fe1—C8158.24 (11)Fe1—C9—H9A126.2
C7—Fe1—C840.16 (14)C6—C10—C9108.3 (2)
C1—Fe1—C241.10 (8)C6—C10—Fe169.50 (15)
C7—Fe1—C2104.11 (11)C9—C10—Fe169.69 (14)
C8—Fe1—C2121.82 (11)C6—C10—H10A125.9
C1—Fe1—C6106.09 (9)C9—C10—H10A125.9
C7—Fe1—C640.62 (13)Fe1—C10—H10A126.5
C8—Fe1—C667.92 (13)O1—C11—C1107.29 (16)
C2—Fe1—C6118.70 (10)O1—C11—C12110.55 (16)
C1—Fe1—C541.54 (8)C1—C11—C12112.37 (16)
C7—Fe1—C5160.76 (12)O1—C11—H11A108.9
C8—Fe1—C5158.57 (12)C1—C11—H11A108.9
C2—Fe1—C569.20 (9)C12—C11—H11A108.9
C6—Fe1—C5125.55 (10)C13—C12—C17119.70 (18)
C1—Fe1—C368.98 (9)C13—C12—C11118.09 (18)
C7—Fe1—C3118.61 (12)C17—C12—C11122.20 (17)
C8—Fe1—C3106.64 (12)C14—C13—C12121.0 (2)
C2—Fe1—C340.70 (10)C14—C13—H13A119.5
C6—Fe1—C3153.77 (11)C12—C13—H13A119.5
C5—Fe1—C368.76 (9)C15—C14—C13119.7 (2)
C1—Fe1—C9158.57 (10)C15—C14—H14A120.2
C7—Fe1—C968.04 (12)C13—C14—H14A120.2
C8—Fe1—C940.62 (12)C14—C15—C16119.85 (19)
C2—Fe1—C9160.10 (10)C14—C15—H15A120.1
C6—Fe1—C968.02 (11)C16—C15—H15A120.1
C5—Fe1—C9123.97 (10)C15—C16—C17121.5 (2)
C3—Fe1—C9125.55 (11)C15—C16—H16A119.3
C1—Fe1—C469.23 (9)C17—C16—H16A119.3
C7—Fe1—C4154.99 (12)C16—C17—C12118.18 (18)
C8—Fe1—C4122.09 (12)C16—C17—P1121.89 (16)
C2—Fe1—C468.54 (10)C12—C17—P1119.88 (14)
C6—Fe1—C4163.94 (10)C19—C18—C23118.26 (19)
C5—Fe1—C440.98 (8)C19—C18—P1117.21 (17)
C3—Fe1—C440.43 (9)C23—C18—P1124.51 (15)
C9—Fe1—C4110.42 (11)C20—C19—C18121.0 (2)
C1—Fe1—C10122.04 (9)C20—C19—H19A119.5
C7—Fe1—C1067.90 (12)C18—C19—H19A119.5
C8—Fe1—C1067.81 (11)C19—C20—C21120.3 (2)
C2—Fe1—C10155.54 (10)C19—C20—H20A119.8
C6—Fe1—C1040.32 (10)C21—C20—H20A119.8
C5—Fe1—C10110.38 (9)C22—C21—C20119.6 (2)
C3—Fe1—C10163.54 (10)C22—C21—H21A120.2
C9—Fe1—C1040.29 (10)C20—C21—H21A120.2
C4—Fe1—C10128.20 (10)C21—C22—C23120.4 (2)
C24—P1—C18101.26 (10)C21—C22—H22A119.8
C24—P1—C17102.60 (9)C23—C22—H22A119.8
C18—P1—C17100.64 (9)C22—C23—C18120.43 (18)
C5—P2—C36100.83 (9)C22—C23—H23A119.8
C5—P2—C3098.80 (10)C18—C23—H23A119.8
C36—P2—C30103.98 (9)C25—C24—C29118.6 (2)
C11—O1—H1A110 (2)C25—C24—P1124.09 (18)
C2—C1—C5107.90 (17)C29—C24—P1117.28 (18)
C2—C1—C11126.3 (2)C24—C25—C26120.8 (3)
C5—C1—C11125.77 (18)C24—C25—H25A119.6
C2—C1—Fe170.09 (11)C26—C25—H25A119.6
C5—C1—Fe170.06 (11)C27—C26—C25120.0 (3)
C11—C1—Fe1125.88 (13)C27—C26—H26A120.0
C3—C2—C1108.1 (2)C25—C26—H26A120.0
C3—C2—Fe169.92 (13)C28—C27—C26119.9 (3)
C1—C2—Fe168.82 (11)C28—C27—H27A120.0
C3—C2—H2A126.0C26—C27—H27A120.0
C1—C2—H2A126.0C27—C28—C29120.2 (3)
Fe1—C2—H2A126.9C27—C28—H28A119.9
C4—C3—C2108.5 (2)C29—C28—H28A119.9
C4—C3—Fe169.94 (15)C24—C29—C28120.4 (3)
C2—C3—Fe169.38 (14)C24—C29—H29A119.8
C4—C3—H3A125.7C28—C29—H29A119.8
C2—C3—H3A125.7C35—C30—C31118.5 (2)
Fe1—C3—H3A126.5C35—C30—P2124.53 (16)
C3—C4—C5108.4 (2)C31—C30—P2116.88 (17)
C3—C4—Fe169.63 (15)C32—C31—C30120.8 (2)
C5—C4—Fe169.30 (12)C32—C31—H31A119.6
C3—C4—H4A125.8C30—C31—H31A119.6
C5—C4—H4A125.8C33—C32—C31120.2 (2)
Fe1—C4—H4A126.8C33—C32—H32A119.9
C4—C5—C1107.12 (18)C31—C32—H32A119.9
C4—C5—P2127.69 (17)C32—C33—C34119.5 (2)
C1—C5—P2125.19 (15)C32—C33—H33A120.2
C4—C5—Fe169.72 (12)C34—C33—H33A120.2
C1—C5—Fe168.39 (11)C33—C34—C35120.2 (2)
P2—C5—Fe1126.60 (11)C33—C34—H34A119.9
C10—C6—C7107.5 (2)C35—C34—H34A119.9
C10—C6—Fe170.18 (14)C30—C35—C34120.7 (2)
C7—C6—Fe169.01 (16)C30—C35—H35A119.7
C10—C6—H6A126.2C34—C35—H35A119.7
C7—C6—H6A126.2C37—C36—C41118.68 (19)
Fe1—C6—H6A126.1C37—C36—P2123.54 (16)
C8—C7—C6108.4 (3)C41—C36—P2117.47 (16)
C8—C7—Fe170.03 (17)C36—C37—C38120.9 (2)
C6—C7—Fe170.37 (15)C36—C37—H37A119.6
C8—C7—H7A125.8C38—C37—H37A119.6
C6—C7—H7A125.8C39—C38—C37119.8 (2)
Fe1—C7—H7A125.4C39—C38—H38A120.1
C7—C8—C9108.6 (3)C37—C38—H38A120.1
C7—C8—Fe169.81 (15)C40—C39—C38120.0 (2)
C9—C8—Fe170.43 (15)C40—C39—H39A120.0
C7—C8—H8A125.7C38—C39—H39A120.0
C9—C8—H8A125.7C39—C40—C41120.4 (2)
Fe1—C8—H8A125.6C39—C40—H40A119.8
C10—C9—C8107.2 (3)C41—C40—H40A119.8
C10—C9—Fe170.02 (14)C40—C41—C36120.2 (2)
C8—C9—Fe168.95 (16)C40—C41—H41A119.9
C10—C9—H9A126.4C36—C41—H41A119.9
C7—Fe1—C1—C274.09 (18)C2—Fe1—C7—C8123.03 (18)
C8—Fe1—C1—C244.9 (3)C6—Fe1—C7—C8119.1 (3)
C6—Fe1—C1—C2115.44 (15)C5—Fe1—C7—C8170.0 (3)
C5—Fe1—C1—C2118.63 (17)C3—Fe1—C7—C881.9 (2)
C3—Fe1—C1—C237.34 (14)C9—Fe1—C7—C837.71 (18)
C9—Fe1—C1—C2173.9 (3)C4—Fe1—C7—C853.8 (3)
C4—Fe1—C1—C280.76 (14)C10—Fe1—C7—C881.33 (19)
C10—Fe1—C1—C2156.36 (14)C1—Fe1—C7—C677.20 (18)
C7—Fe1—C1—C5167.29 (15)C8—Fe1—C7—C6119.1 (3)
C8—Fe1—C1—C5163.5 (3)C2—Fe1—C7—C6117.87 (16)
C2—Fe1—C1—C5118.63 (17)C5—Fe1—C7—C650.9 (4)
C6—Fe1—C1—C5125.93 (13)C3—Fe1—C7—C6158.99 (15)
C3—Fe1—C1—C581.28 (13)C9—Fe1—C7—C681.39 (17)
C9—Fe1—C1—C555.3 (3)C4—Fe1—C7—C6172.8 (2)
C4—Fe1—C1—C537.87 (12)C10—Fe1—C7—C637.76 (15)
C10—Fe1—C1—C585.01 (14)C6—C7—C8—C90.2 (3)
C7—Fe1—C1—C1147.0 (2)Fe1—C7—C8—C960.0 (2)
C8—Fe1—C1—C1176.2 (4)C6—C7—C8—Fe160.16 (18)
C2—Fe1—C1—C11121.0 (2)C1—Fe1—C8—C740.0 (4)
C6—Fe1—C1—C115.6 (2)C2—Fe1—C8—C773.1 (2)
C5—Fe1—C1—C11120.3 (2)C6—Fe1—C8—C737.87 (19)
C3—Fe1—C1—C11158.4 (2)C5—Fe1—C8—C7171.0 (3)
C9—Fe1—C1—C1165.1 (4)C3—Fe1—C8—C7114.9 (2)
C4—Fe1—C1—C11158.2 (2)C9—Fe1—C8—C7119.4 (3)
C10—Fe1—C1—C1135.3 (2)C4—Fe1—C8—C7156.26 (18)
C5—C1—C2—C31.0 (2)C10—Fe1—C8—C781.6 (2)
C11—C1—C2—C3179.57 (19)C1—Fe1—C8—C9159.4 (2)
Fe1—C1—C2—C359.08 (16)C7—Fe1—C8—C9119.4 (3)
C5—C1—C2—Fe160.13 (13)C2—Fe1—C8—C9167.49 (16)
C11—C1—C2—Fe1120.49 (19)C6—Fe1—C8—C981.5 (2)
C1—Fe1—C2—C3119.74 (19)C5—Fe1—C8—C951.6 (4)
C7—Fe1—C2—C3117.71 (17)C3—Fe1—C8—C9125.72 (19)
C8—Fe1—C2—C378.19 (19)C4—Fe1—C8—C984.3 (2)
C6—Fe1—C2—C3158.71 (15)C10—Fe1—C8—C937.84 (17)
C5—Fe1—C2—C381.22 (15)C7—C8—C9—C100.2 (3)
C9—Fe1—C2—C353.7 (4)Fe1—C8—C9—C1059.81 (17)
C4—Fe1—C2—C337.14 (14)C7—C8—C9—Fe159.61 (19)
C10—Fe1—C2—C3174.9 (2)C1—Fe1—C9—C1040.6 (3)
C7—Fe1—C2—C1122.56 (16)C7—Fe1—C9—C1081.27 (19)
C8—Fe1—C2—C1162.07 (16)C8—Fe1—C9—C10118.6 (3)
C6—Fe1—C2—C181.55 (16)C2—Fe1—C9—C10151.3 (3)
C5—Fe1—C2—C138.52 (12)C6—Fe1—C9—C1037.31 (16)
C3—Fe1—C2—C1119.74 (19)C5—Fe1—C9—C1081.64 (17)
C9—Fe1—C2—C1173.5 (3)C3—Fe1—C9—C10168.46 (15)
C4—Fe1—C2—C182.59 (14)C4—Fe1—C9—C10125.54 (15)
C10—Fe1—C2—C155.2 (3)C1—Fe1—C9—C8159.1 (3)
C1—C2—C3—C40.7 (3)C7—Fe1—C9—C837.3 (2)
Fe1—C2—C3—C459.15 (18)C2—Fe1—C9—C832.7 (4)
C1—C2—C3—Fe158.40 (15)C6—Fe1—C9—C881.2 (2)
C1—Fe1—C3—C482.25 (15)C5—Fe1—C9—C8159.80 (19)
C7—Fe1—C3—C4162.08 (16)C3—Fe1—C9—C873.0 (2)
C8—Fe1—C3—C4120.29 (17)C4—Fe1—C9—C8115.9 (2)
C2—Fe1—C3—C4120.0 (2)C10—Fe1—C9—C8118.6 (3)
C6—Fe1—C3—C4166.0 (2)C7—C6—C10—C90.1 (3)
C5—Fe1—C3—C437.56 (14)Fe1—C6—C10—C959.08 (16)
C9—Fe1—C3—C479.76 (18)C7—C6—C10—Fe159.14 (17)
C10—Fe1—C3—C452.6 (4)C8—C9—C10—C60.2 (3)
C1—Fe1—C3—C237.70 (13)Fe1—C9—C10—C658.97 (16)
C7—Fe1—C3—C277.97 (17)C8—C9—C10—Fe159.13 (19)
C8—Fe1—C3—C2119.76 (16)C1—Fe1—C10—C676.58 (17)
C6—Fe1—C3—C246.1 (3)C7—Fe1—C10—C638.04 (17)
C5—Fe1—C3—C282.39 (14)C8—Fe1—C10—C681.55 (19)
C9—Fe1—C3—C2160.29 (14)C2—Fe1—C10—C637.0 (3)
C4—Fe1—C3—C2120.0 (2)C5—Fe1—C10—C6121.39 (15)
C10—Fe1—C3—C2172.5 (3)C3—Fe1—C10—C6154.8 (3)
C2—C3—C4—C50.2 (3)C9—Fe1—C10—C6119.7 (2)
Fe1—C3—C4—C558.64 (16)C4—Fe1—C10—C6164.29 (15)
C2—C3—C4—Fe158.80 (18)C1—Fe1—C10—C9163.73 (15)
C1—Fe1—C4—C381.58 (16)C7—Fe1—C10—C981.66 (19)
C7—Fe1—C4—C339.7 (3)C8—Fe1—C10—C938.14 (18)
C8—Fe1—C4—C377.59 (19)C2—Fe1—C10—C9156.7 (2)
C2—Fe1—C4—C337.38 (14)C6—Fe1—C10—C9119.7 (2)
C6—Fe1—C4—C3157.3 (3)C5—Fe1—C10—C9118.92 (16)
C5—Fe1—C4—C3120.0 (2)C3—Fe1—C10—C935.1 (4)
C9—Fe1—C4—C3121.32 (16)C4—Fe1—C10—C976.01 (18)
C10—Fe1—C4—C3163.36 (15)C2—C1—C11—O125.1 (3)
C1—Fe1—C4—C538.37 (12)C5—C1—C11—O1155.63 (18)
C7—Fe1—C4—C5159.7 (2)Fe1—C1—C11—O165.5 (2)
C8—Fe1—C4—C5162.46 (15)C2—C1—C11—C1296.6 (2)
C2—Fe1—C4—C582.57 (14)C5—C1—C11—C1282.7 (2)
C6—Fe1—C4—C537.4 (4)Fe1—C1—C11—C12172.79 (14)
C3—Fe1—C4—C5120.0 (2)O1—C11—C12—C1368.2 (2)
C9—Fe1—C4—C5118.72 (14)C1—C11—C12—C1351.7 (3)
C10—Fe1—C4—C576.69 (16)O1—C11—C12—C17110.6 (2)
C3—C4—C5—C10.5 (3)C1—C11—C12—C17129.5 (2)
Fe1—C4—C5—C158.36 (13)C17—C12—C13—C141.1 (3)
C3—C4—C5—P2179.97 (17)C11—C12—C13—C14179.9 (2)
Fe1—C4—C5—P2121.18 (17)C12—C13—C14—C151.4 (4)
C3—C4—C5—Fe158.85 (18)C13—C14—C15—C161.8 (4)
C2—C1—C5—C40.9 (2)C14—C15—C16—C170.1 (3)
C11—C1—C5—C4179.67 (18)C15—C16—C17—C122.5 (3)
Fe1—C1—C5—C459.20 (14)C15—C16—C17—P1179.75 (17)
C2—C1—C5—P2179.50 (16)C13—C12—C17—C163.0 (3)
C11—C1—C5—P20.1 (3)C11—C12—C17—C16178.27 (18)
Fe1—C1—C5—P2120.36 (16)C13—C12—C17—P1179.75 (16)
C2—C1—C5—Fe160.14 (13)C11—C12—C17—P11.0 (3)
C11—C1—C5—Fe1120.47 (18)C24—P1—C17—C1611.30 (19)
C36—P2—C5—C498.5 (2)C18—P1—C17—C16115.52 (17)
C30—P2—C5—C47.7 (2)C24—P1—C17—C12171.52 (16)
C36—P2—C5—C182.08 (18)C18—P1—C17—C1267.30 (17)
C30—P2—C5—C1171.75 (17)C24—P1—C18—C1995.15 (18)
C36—P2—C5—Fe1169.93 (13)C17—P1—C18—C19159.55 (17)
C30—P2—C5—Fe183.90 (14)C24—P1—C18—C2386.39 (19)
C1—Fe1—C5—C4118.94 (17)C17—P1—C18—C2318.90 (19)
C7—Fe1—C5—C4153.5 (3)C23—C18—C19—C200.6 (3)
C8—Fe1—C5—C444.3 (3)P1—C18—C19—C20177.94 (18)
C2—Fe1—C5—C480.82 (14)C18—C19—C20—C210.8 (4)
C6—Fe1—C5—C4168.09 (14)C19—C20—C21—C221.3 (4)
C3—Fe1—C5—C437.08 (14)C20—C21—C22—C230.5 (4)
C9—Fe1—C5—C482.29 (16)C21—C22—C23—C181.0 (3)
C10—Fe1—C5—C4125.33 (14)C19—C18—C23—C221.5 (3)
C7—Fe1—C5—C134.6 (4)P1—C18—C23—C22176.96 (16)
C8—Fe1—C5—C1163.3 (3)C18—P1—C24—C2523.5 (2)
C2—Fe1—C5—C138.12 (12)C17—P1—C24—C2580.3 (2)
C6—Fe1—C5—C172.98 (15)C18—P1—C24—C29154.66 (17)
C3—Fe1—C5—C181.86 (13)C17—P1—C24—C29101.60 (18)
C9—Fe1—C5—C1158.78 (13)C29—C24—C25—C260.4 (4)
C4—Fe1—C5—C1118.94 (17)P1—C24—C25—C26177.7 (2)
C10—Fe1—C5—C1115.73 (13)C24—C25—C26—C270.6 (4)
C1—Fe1—C5—P2118.55 (19)C25—C26—C27—C280.3 (4)
C7—Fe1—C5—P284.0 (4)C26—C27—C28—C291.4 (4)
C8—Fe1—C5—P278.2 (3)C25—C24—C29—C280.7 (3)
C2—Fe1—C5—P2156.66 (18)P1—C24—C29—C28178.92 (19)
C6—Fe1—C5—P245.57 (19)C27—C28—C29—C241.6 (4)
C3—Fe1—C5—P2159.59 (17)C5—P2—C30—C3587.0 (2)
C9—Fe1—C5—P240.23 (18)C36—P2—C30—C3516.6 (2)
C4—Fe1—C5—P2122.5 (2)C5—P2—C30—C3189.93 (18)
C10—Fe1—C5—P22.82 (17)C36—P2—C30—C31166.51 (17)
C1—Fe1—C6—C10120.89 (14)C35—C30—C31—C322.1 (3)
C7—Fe1—C6—C10118.7 (2)P2—C30—C31—C32174.96 (19)
C8—Fe1—C6—C1081.27 (17)C30—C31—C32—C331.4 (4)
C2—Fe1—C6—C10163.48 (14)C31—C32—C33—C340.1 (4)
C5—Fe1—C6—C1079.59 (16)C32—C33—C34—C350.4 (4)
C3—Fe1—C6—C10164.1 (2)C31—C30—C35—C341.6 (4)
C9—Fe1—C6—C1037.29 (15)P2—C30—C35—C34175.2 (2)
C4—Fe1—C6—C1050.3 (4)C33—C34—C35—C300.4 (4)
C1—Fe1—C6—C7120.38 (17)C5—P2—C36—C3714.0 (2)
C8—Fe1—C6—C737.46 (18)C30—P2—C36—C3788.04 (19)
C2—Fe1—C6—C777.79 (18)C5—P2—C36—C41159.45 (16)
C5—Fe1—C6—C7161.68 (16)C30—P2—C36—C4198.54 (17)
C3—Fe1—C6—C745.4 (3)C41—C36—C37—C380.3 (3)
C9—Fe1—C6—C781.44 (18)P2—C36—C37—C38173.05 (17)
C4—Fe1—C6—C7169.0 (3)C36—C37—C38—C390.5 (3)
C10—Fe1—C6—C7118.7 (2)C37—C38—C39—C400.2 (3)
C10—C6—C7—C80.1 (3)C38—C39—C40—C410.3 (4)
Fe1—C6—C7—C859.9 (2)C39—C40—C41—C360.6 (3)
C10—C6—C7—Fe159.88 (16)C37—C36—C41—C400.3 (3)
C1—Fe1—C7—C8163.71 (16)P2—C36—C41—C40174.00 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···P11.002.563.153 (2)118
O1—H1A···C230.78 (3)2.51 (3)3.217 (3)152 (2)

Experimental details

Crystal data
Chemical formula[Fe(C5H5)(C36H29OP2)]
Mr660.47
Crystal system, space groupMonoclinic, P21
Temperature (K)162
a, b, c (Å)11.6111 (15), 8.6154 (10), 16.481 (2)
β (°) 97.807 (12)
V3)1633.4 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.59
Crystal size (mm)0.40 × 0.40 × 0.32
Data collection
DiffractometerSiemens SMART 1K CCD
diffractometer
Absorption correctionNumerical
(SHELXTL; Sheldrick, 2008)
Tmin, Tmax0.795, 0.845
No. of measured, independent and
observed [I > 2σ(I)] reflections
25293, 9131, 7926
Rint0.051
(sin θ/λ)max1)0.714
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.083, 1.07
No. of reflections9131
No. of parameters410
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.23
Absolute structureFlack (1983), 4069 Friedel pairs
Absolute structure parameter0.023 (10)

Computer programs: SMART (Siemens, 1995), SAINT (Siemens, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···P11.002.563.153 (2)118
O1—H1A···C230.78 (3)2.51 (3)3.217 (3)152 (2)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds