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Acta Cryst. (2008). E64, m1585    [ doi:10.1107/S1600536808038294 ]

(Sp)-1-Diphenylphosphanyl-2-{(S)-[2-(diphenylphosphanyl)phenyl]hydroxymethyl}ferrocene

J. W. Bats, A. Doppiu, A. Rivas Nass and A. S. K. Hashmi

Abstract top

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...[pi]phenyl interaction. The crystal packing shows five very weak intermolecular C-H...[pi] contacts, with H...Cg distances between 3.26 and 3.39 Å (Cg is the centroid of a phenyl or cyclopentadienyl ring).

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 m−3
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 mm−1
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)
graphiteRint = 0.051
ω scansθmax = 30.5°, θmin = 1.8°
Absorption correction: numerical
(SHELXTL; Sheldrick, 2008)		h = −16→16
Tmin = 0.795, Tmax = 0.845k = −12→12
25293 measured reflectionsl = −23→23
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 Å−3
410 parametersΔρmin = −0.23 e Å−3
1 restraintAbsolute structure: Flack (1983), 4069 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack 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 mm−1
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 reflectionsθmax = 30.5°
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 Å−3
S = 1.07Δρmin = −0.23 e Å−3
9131 reflectionsAbsolute structure: Flack (1983), 4069 Friedel pairs
410 parametersFlack 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)
H2A0.3304−0.24020.68530.038*
C30.2027 (2)−0.0890 (3)0.62352 (16)0.0360 (5)
H3A0.1499−0.15590.59130.043*
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)
H6A0.2790−0.05740.90210.056*
C70.1497 (3)−0.1778 (4)0.8229 (2)0.0585 (9)
H7A0.1742−0.28310.82600.070*
C80.0498 (3)−0.1210 (4)0.7757 (2)0.0567 (8)
H8A−0.0053−0.18120.74130.068*
C90.0444 (2)0.0418 (4)0.78764 (17)0.0445 (6)
H9A−0.01440.10980.76280.053*
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)
H13A0.5415−0.13190.64890.037*
C140.69159 (18)−0.0268 (3)0.62852 (13)0.0345 (5)
H14A0.7051−0.09050.58370.041*
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)
H21A0.6609−0.16301.10550.041*
C220.70842 (19)−0.1230 (3)0.99310 (13)0.0312 (5)
H22A0.7463−0.21980.98880.037*
C230.70385 (16)−0.0159 (3)0.92957 (12)0.0284 (4)
H23A0.7397−0.03950.88250.034*
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*
C32−0.00866 (19)0.4957 (3)0.66960 (15)0.0399 (5)
H32A−0.07130.50270.70100.048*
C33−0.0244 (2)0.5420 (3)0.58854 (17)0.0431 (6)
H33A−0.09750.58090.56420.052*
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, °) 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—C8−123.03 (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—C2−118.63 (17)C3—Fe1—C7—C8−81.9 (2)
C3—Fe1—C1—C2−37.34 (14)C9—Fe1—C7—C837.71 (18)
C9—Fe1—C1—C2−173.9 (3)C4—Fe1—C7—C8−53.8 (3)
C4—Fe1—C1—C2−80.76 (14)C10—Fe1—C7—C881.33 (19)
C10—Fe1—C1—C2156.36 (14)C1—Fe1—C7—C677.20 (18)
C7—Fe1—C1—C5−167.29 (15)C8—Fe1—C7—C6−119.1 (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—C5−125.93 (13)C3—Fe1—C7—C6158.99 (15)
C3—Fe1—C1—C581.28 (13)C9—Fe1—C7—C6−81.39 (17)
C9—Fe1—C1—C5−55.3 (3)C4—Fe1—C7—C6−172.8 (2)
C4—Fe1—C1—C537.87 (12)C10—Fe1—C7—C6−37.76 (15)
C10—Fe1—C1—C5−85.01 (14)C6—C7—C8—C90.2 (3)
C7—Fe1—C1—C11−47.0 (2)Fe1—C7—C8—C9−60.0 (2)
C8—Fe1—C1—C11−76.2 (4)C6—C7—C8—Fe160.16 (18)
C2—Fe1—C1—C11−121.0 (2)C1—Fe1—C8—C740.0 (4)
C6—Fe1—C1—C11−5.6 (2)C2—Fe1—C8—C773.1 (2)
C5—Fe1—C1—C11120.3 (2)C6—Fe1—C8—C7−37.87 (19)
C3—Fe1—C1—C11−158.4 (2)C5—Fe1—C8—C7−171.0 (3)
C9—Fe1—C1—C1165.1 (4)C3—Fe1—C8—C7114.9 (2)
C4—Fe1—C1—C11158.2 (2)C9—Fe1—C8—C7−119.4 (3)
C10—Fe1—C1—C1135.3 (2)C4—Fe1—C8—C7156.26 (18)
C5—C1—C2—C3−1.0 (2)C10—Fe1—C8—C7−81.6 (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—Fe1−60.13 (13)C2—Fe1—C8—C9−167.49 (16)
C11—C1—C2—Fe1120.49 (19)C6—Fe1—C8—C981.5 (2)
C1—Fe1—C2—C3−119.74 (19)C5—Fe1—C8—C9−51.6 (4)
C7—Fe1—C2—C3117.71 (17)C3—Fe1—C8—C9−125.72 (19)
C8—Fe1—C2—C378.19 (19)C4—Fe1—C8—C9−84.3 (2)
C6—Fe1—C2—C3158.71 (15)C10—Fe1—C8—C937.84 (17)
C5—Fe1—C2—C3−81.22 (15)C7—C8—C9—C10−0.2 (3)
C9—Fe1—C2—C353.7 (4)Fe1—C8—C9—C10−59.81 (17)
C4—Fe1—C2—C3−37.14 (14)C7—C8—C9—Fe159.61 (19)
C10—Fe1—C2—C3−174.9 (2)C1—Fe1—C9—C10−40.6 (3)
C7—Fe1—C2—C1−122.56 (16)C7—Fe1—C9—C1081.27 (19)
C8—Fe1—C2—C1−162.07 (16)C8—Fe1—C9—C10118.6 (3)
C6—Fe1—C2—C1−81.55 (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—C10−81.64 (17)
C9—Fe1—C2—C1173.5 (3)C3—Fe1—C9—C10−168.46 (15)
C4—Fe1—C2—C182.59 (14)C4—Fe1—C9—C10−125.54 (15)
C10—Fe1—C2—C1−55.2 (3)C1—Fe1—C9—C8−159.1 (3)
C1—C2—C3—C40.7 (3)C7—Fe1—C9—C8−37.3 (2)
Fe1—C2—C3—C459.15 (18)C2—Fe1—C9—C832.7 (4)
C1—C2—C3—Fe1−58.40 (15)C6—Fe1—C9—C8−81.2 (2)
C1—Fe1—C3—C4−82.25 (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—C4−120.0 (2)C10—Fe1—C9—C8−118.6 (3)
C6—Fe1—C3—C4−166.0 (2)C7—C6—C10—C9−0.1 (3)
C5—Fe1—C3—C4−37.56 (14)Fe1—C6—C10—C959.08 (16)
C9—Fe1—C3—C479.76 (18)C7—C6—C10—Fe1−59.14 (17)
C10—Fe1—C3—C452.6 (4)C8—C9—C10—C60.2 (3)
C1—Fe1—C3—C237.70 (13)Fe1—C9—C10—C6−58.97 (16)
C7—Fe1—C3—C2−77.97 (17)C8—C9—C10—Fe159.13 (19)
C8—Fe1—C3—C2−119.76 (16)C1—Fe1—C10—C6−76.58 (17)
C6—Fe1—C3—C2−46.1 (3)C7—Fe1—C10—C638.04 (17)
C5—Fe1—C3—C282.39 (14)C8—Fe1—C10—C681.55 (19)
C9—Fe1—C3—C2−160.29 (14)C2—Fe1—C10—C6−37.0 (3)
C4—Fe1—C3—C2120.0 (2)C5—Fe1—C10—C6−121.39 (15)
C10—Fe1—C3—C2172.5 (3)C3—Fe1—C10—C6154.8 (3)
C2—C3—C4—C5−0.2 (3)C9—Fe1—C10—C6119.7 (2)
Fe1—C3—C4—C558.64 (16)C4—Fe1—C10—C6−164.29 (15)
C2—C3—C4—Fe1−58.80 (18)C1—Fe1—C10—C9163.73 (15)
C1—Fe1—C4—C381.58 (16)C7—Fe1—C10—C9−81.66 (19)
C7—Fe1—C4—C3−39.7 (3)C8—Fe1—C10—C9−38.14 (18)
C8—Fe1—C4—C3−77.59 (19)C2—Fe1—C10—C9−156.7 (2)
C2—Fe1—C4—C337.38 (14)C6—Fe1—C10—C9−119.7 (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—C3−121.32 (16)C4—Fe1—C10—C976.01 (18)
C10—Fe1—C4—C3−163.36 (15)C2—C1—C11—O1−25.1 (3)
C1—Fe1—C4—C5−38.37 (12)C5—C1—C11—O1155.63 (18)
C7—Fe1—C4—C5−159.7 (2)Fe1—C1—C11—O165.5 (2)
C8—Fe1—C4—C5162.46 (15)C2—C1—C11—C1296.6 (2)
C2—Fe1—C4—C5−82.57 (14)C5—C1—C11—C12−82.7 (2)
C6—Fe1—C4—C537.4 (4)Fe1—C1—C11—C12−172.79 (14)
C3—Fe1—C4—C5−120.0 (2)O1—C11—C12—C1368.2 (2)
C9—Fe1—C4—C5118.72 (14)C1—C11—C12—C13−51.7 (3)
C10—Fe1—C4—C576.69 (16)O1—C11—C12—C17−110.6 (2)
C3—C4—C5—C1−0.5 (3)C1—C11—C12—C17129.5 (2)
Fe1—C4—C5—C158.36 (13)C17—C12—C13—C14−1.1 (3)
C3—C4—C5—P2179.97 (17)C11—C12—C13—C14−179.9 (2)
Fe1—C4—C5—P2−121.18 (17)C12—C13—C14—C15−1.4 (4)
C3—C4—C5—Fe1−58.85 (18)C13—C14—C15—C161.8 (4)
C2—C1—C5—C40.9 (2)C14—C15—C16—C170.1 (3)
C11—C1—C5—C4−179.67 (18)C15—C16—C17—C12−2.5 (3)
Fe1—C1—C5—C4−59.20 (14)C15—C16—C17—P1−179.75 (17)
C2—C1—C5—P2−179.50 (16)C13—C12—C17—C163.0 (3)
C11—C1—C5—P2−0.1 (3)C11—C12—C17—C16−178.27 (18)
Fe1—C1—C5—P2120.36 (16)C13—C12—C17—P1−179.75 (16)
C2—C1—C5—Fe160.14 (13)C11—C12—C17—P1−1.0 (3)
C11—C1—C5—Fe1−120.47 (18)C24—P1—C17—C16−11.30 (19)
C36—P2—C5—C4−98.5 (2)C18—P1—C17—C16−115.52 (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—C1−171.75 (17)C24—P1—C18—C1995.15 (18)
C36—P2—C5—Fe1169.93 (13)C17—P1—C18—C19−159.55 (17)
C30—P2—C5—Fe1−83.90 (14)C24—P1—C18—C23−86.39 (19)
C1—Fe1—C5—C4118.94 (17)C17—P1—C18—C2318.90 (19)
C7—Fe1—C5—C4153.5 (3)C23—C18—C19—C20−0.6 (3)
C8—Fe1—C5—C4−44.3 (3)P1—C18—C19—C20177.94 (18)
C2—Fe1—C5—C480.82 (14)C18—C19—C20—C21−0.8 (4)
C6—Fe1—C5—C4−168.09 (14)C19—C20—C21—C221.3 (4)
C3—Fe1—C5—C437.08 (14)C20—C21—C22—C23−0.5 (4)
C9—Fe1—C5—C4−82.29 (16)C21—C22—C23—C18−1.0 (3)
C10—Fe1—C5—C4−125.33 (14)C19—C18—C23—C221.5 (3)
C7—Fe1—C5—C134.6 (4)P1—C18—C23—C22−176.96 (16)
C8—Fe1—C5—C1−163.3 (3)C18—P1—C24—C2523.5 (2)
C2—Fe1—C5—C1−38.12 (12)C17—P1—C24—C25−80.3 (2)
C6—Fe1—C5—C172.98 (15)C18—P1—C24—C29−154.66 (17)
C3—Fe1—C5—C1−81.86 (13)C17—P1—C24—C29101.60 (18)
C9—Fe1—C5—C1158.78 (13)C29—C24—C25—C260.4 (4)
C4—Fe1—C5—C1−118.94 (17)P1—C24—C25—C26−177.7 (2)
C10—Fe1—C5—C1115.73 (13)C24—C25—C26—C27−0.6 (4)
C1—Fe1—C5—P2−118.55 (19)C25—C26—C27—C28−0.3 (4)
C7—Fe1—C5—P2−84.0 (4)C26—C27—C28—C291.4 (4)
C8—Fe1—C5—P278.2 (3)C25—C24—C29—C280.7 (3)
C2—Fe1—C5—P2−156.66 (18)P1—C24—C29—C28178.92 (19)
C6—Fe1—C5—P2−45.57 (19)C27—C28—C29—C24−1.6 (4)
C3—Fe1—C5—P2159.59 (17)C5—P2—C30—C35−87.0 (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—P2−2.82 (17)C36—P2—C30—C31−166.51 (17)
C1—Fe1—C6—C10120.89 (14)C35—C30—C31—C322.1 (3)
C7—Fe1—C6—C10−118.7 (2)P2—C30—C31—C32−174.96 (19)
C8—Fe1—C6—C10−81.27 (17)C30—C31—C32—C33−1.4 (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—C10−164.1 (2)C31—C30—C35—C34−1.6 (4)
C9—Fe1—C6—C10−37.29 (15)P2—C30—C35—C34175.2 (2)
C4—Fe1—C6—C1050.3 (4)C33—C34—C35—C300.4 (4)
C1—Fe1—C6—C7−120.38 (17)C5—P2—C36—C3714.0 (2)
C8—Fe1—C6—C737.46 (18)C30—P2—C36—C37−88.04 (19)
C2—Fe1—C6—C7−77.79 (18)C5—P2—C36—C41−159.45 (16)
C5—Fe1—C6—C7−161.68 (16)C30—P2—C36—C4198.54 (17)
C3—Fe1—C6—C7−45.4 (3)C41—C36—C37—C380.3 (3)
C9—Fe1—C6—C781.44 (18)P2—C36—C37—C38−173.05 (17)
C4—Fe1—C6—C7169.0 (3)C36—C37—C38—C39−0.5 (3)
C10—Fe1—C6—C7118.7 (2)C37—C38—C39—C400.2 (3)
C10—C6—C7—C8−0.1 (3)C38—C39—C40—C410.3 (4)
Fe1—C6—C7—C8−59.9 (2)C39—C40—C41—C36−0.6 (3)
C10—C6—C7—Fe159.88 (16)C37—C36—C41—C400.3 (3)
C1—Fe1—C7—C8−163.71 (16)P2—C36—C41—C40174.00 (17)
Hydrogen-bond geometry (Å, °) 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)
Table 1
Hydrogen-bond geometry (Å, °) 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)
references
References top

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