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Acta Cryst. (2008). E64, m1639    [ doi:10.1107/S160053680803955X ]

(Rp)-1-{(R)-(Dimethylamino)[2-(diphenylphosphanyl)phenyl]methyl}-2-(diphenylphosphanyl)ferrocene chloroform solvate

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

Abstract top

The absolute configuration of the title molecule, [Fe(C5H5)(C38H34NP2)]·CHCl3, is R,Rp. The molecular structure is similar to the structure of the solvent-free compound [Fukuzawa, Yamamoto & Kikuchi (2007). J. Org. Chem. 72, 1514-1517], but some torsion angles about the P-Cphenyl bonds differ by up to 25°. The P atoms and the N atom have a distorted trigonal-pyramidal geometry. The chloroform solvate group donates a C-H...[pi] bond to the central benzene ring and is also involved in six intermolecular C-H...Cl contacts with H...Cl distances between 2.96 and 3.13 Å.

Comment top

The Taniaphos ligand (Ireland et al., 1999), a broadly used chiral ligand technology owned by Umicore and sold by Solvias, is a well known diphosphane ligand for catalytic asymmetric synthesis. Quite recently, the crystal structure of the solvent-free compound has been reported by Fukuzawa, Yamamoto & Kikuchi (2007). They showed that the planar chirality of the ligand formed by a classical ortho-directed metallation procedure (Fukuzawa, Yamamoto, Hosaka & Kikuchi, 2007) of a ferrocene with a chiral center configurated (R) in the side chain is (Rp) and not (Sp) as presumed previously. This was confirmed by comment of Ireland et al. (2008) on the crystal structure of a rhodium(I) complex of Taniaphos.

The molecular structure of the title compound is shown in Fig. 1. The absolute configuration of the molecule is Rp at the ferrocene group and R at the asymmetric carbon atom C11. The crystal structure of the solvent-free compound reported by Fukuzawa, Yamamoto & Kikuchi (2007) has two independent molecules in the asymmetric unit. The conformation of the three molecules is rather similar, but corresponding torsion angles about some P—Cphenyl bonds differ up to 25°.

The ferrocene group deviates 14° from an eclipsed conformation. The angle between the planes of the two cyclopentadienyl rings is 3.6 (1)°. Both P atoms have a pyramidal geometry with C—P—C angles between 99.7 (1) and 102.4 (1)°. The lone-pair lobe of atom P1 shows a short intramolecular contact distance of 2.57Å with the H atom of C11 (Table 1). There also is an intramolecular π···π contact with a distance of 3.333 (3)Å between C15 and C37. The N atom also has a pyramidal geometry. The N lone-pair is not involved in short intra- or intermolecular interactions. The crystal packing shows three intermolecular C—H···πphenyl interactions (Table 1) with H···Cg distances shorter than 3Å (Cg represents the centroid of a phenyl ring). In one of them the chloroform C—H bond acts as a donor. There also are six intermolecular C—H···Clchloroform contacts with H···Cl distances between 2.96 and 3.13 Å.

Related literature top

The crystal structure of the solvent-free compound has been reported by Fukuzawa, Yamamoto & Kikuchi (2007) and the structures of related molecules by Ireland et al. (1999) and Bats et al. (2008). For the synthesis of related compounds, see: Ireland et al. (2002); Fukuzawa, Yamamoto, Hosaka & Kikuchi (2007). For the stereochemistry of Taniaphos ligands, see: Ireland et al. (2008). [Scheme should show solvent]

Experimental top

Crystals were obtained by slow diffusion of diethyl ether into a chloroform solution of the commercially available Taniaphos ligand SL—T001–1. We have also performed a crystal structure determination of the commercially available Taniaphos ligand SL—T001–2, crystallized under similar conditions. The resulting crystal structure is enantiomorphous to the structure of the title compound. Thus the SL—T001–2 ligand has the S,Sp configuration.

Refinement top

H atoms were geometrically positioned using distances: Cplanar—H=0.95 Å, Cmethyl—H=0.98 Å, Cprimary—H=1.00 Å, Uiso(H)=1.2Ueq(Cnon-methyl) and Uiso(H)=1.5Ueq(Cmethyl). The torsion angles about the N—C bonds were varied for the methyl groups. Friedel opposites were not averaged. The absolute configuration was determined from 4811 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 molecule, without the solvate group, shown with 50% probability displacement ellipsoids. The H atoms are drawn as small spheres of arbitrary radius.
(Rp)-1-{(R)-(Dimethylamino)[2- (diphenylphosphanyl)phenyl]methyl-2-(diphenylphosphanyl)ferrocene chloroform solvate top
Crystal data top
[Fe(C5H5)(C38H34NP2)]·CHCl3F(000) = 1672
Mr = 806.91Dx = 1.388 Mg m−3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 347 reflections
a = 10.6051 (11) Åθ = 3–23°
b = 11.8922 (10) ŵ = 0.71 mm−1
c = 30.625 (3) ÅT = 163 K
V = 3862.3 (6) Å3Block, yellow
Z = 40.60 × 0.40 × 0.37 mm
Data collection top
Siemens SMART 1K CCD
diffractometer		11202 independent reflections
Radiation source: normal-focus sealed tube9851 reflections with I > 2σ(I)
graphiteRint = 0.061
ω scansθmax = 30.8°, θmin = 1.8°
Absorption correction: numerical
(SHELXTL; Sheldrick, 2008)		h = −15→15
Tmin = 0.664, Tmax = 0.786k = −16→16
59511 measured reflectionsl = −43→44
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.03P)2 + 1.6P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max = 0.003
11202 reflectionsΔρmax = 0.50 e Å−3
462 parametersΔρmin = −0.39 e Å−3
0 restraintsAbsolute structure: Flack (1983), 4811 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.021 (11)
Crystal data top
[Fe(C5H5)(C38H34NP2)]·CHCl3V = 3862.3 (6) Å3
Mr = 806.91Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.6051 (11) ŵ = 0.71 mm−1
b = 11.8922 (10) ÅT = 163 K
c = 30.625 (3) Å0.60 × 0.40 × 0.37 mm
Data collection top
Siemens SMART 1K CCD
diffractometer		11202 independent reflections
Absorption correction: numerical
(SHELXTL; Sheldrick, 2008)		9851 reflections with I > 2σ(I)
Tmin = 0.664, Tmax = 0.786Rint = 0.061
59511 measured reflectionsθmax = 30.8°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.088Δρmax = 0.50 e Å−3
S = 1.18Δρmin = −0.39 e Å−3
11202 reflectionsAbsolute structure: Flack (1983), 4811 Friedel pairs
462 parametersFlack parameter: −0.021 (11)
0 restraints
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Fe10.74190 (3)0.91368 (2)0.919111 (9)0.02233 (7)
Cl10.95787 (8)0.23821 (6)0.77926 (3)0.05234 (19)
Cl21.06842 (7)0.42876 (6)0.73474 (2)0.04212 (15)
Cl31.16205 (7)0.36270 (8)0.81940 (3)0.0571 (2)
P10.70451 (5)0.46648 (4)0.915738 (17)0.02029 (10)
P20.53683 (5)0.73476 (4)0.867406 (17)0.02087 (10)
N10.98418 (17)0.68727 (16)0.88942 (6)0.0253 (4)
C10.79849 (19)0.80313 (16)0.87204 (6)0.0190 (4)
C20.66789 (19)0.83355 (16)0.86593 (7)0.0197 (4)
C30.6636 (2)0.95373 (17)0.85998 (7)0.0217 (4)
H3A0.58970.99710.85520.026*
C40.7886 (2)0.99631 (17)0.86250 (7)0.0246 (4)
H4A0.81281.07290.85970.029*
C50.87145 (19)0.90374 (17)0.86993 (7)0.0228 (4)
H5A0.96050.90830.87300.027*
C60.7954 (3)0.8415 (2)0.97653 (8)0.0382 (6)
H6A0.84620.77610.97930.046*
C70.6625 (3)0.8439 (2)0.97341 (8)0.0388 (6)
H7A0.60830.78030.97390.047*
C80.6239 (3)0.9581 (2)0.96934 (8)0.0395 (6)
H8A0.53960.98400.96660.047*
C90.7330 (3)1.0258 (2)0.97010 (8)0.0419 (6)
H9A0.73501.10540.96790.050*
C100.8396 (3)0.9541 (2)0.97474 (8)0.0398 (6)
H10A0.92520.97740.97640.048*
C110.84687 (19)0.68498 (17)0.88138 (6)0.0200 (4)
H11A0.80700.66130.90950.024*
C121.0266 (2)0.59513 (19)0.91705 (9)0.0349 (5)
H12A1.11380.60880.92620.052*
H12B1.02240.52450.90070.052*
H12C0.97230.59010.94290.052*
C131.0644 (2)0.6962 (2)0.85103 (8)0.0326 (5)
H13A1.06020.62600.83430.049*
H13B1.15160.70990.86020.049*
H13C1.03530.75870.83270.049*
C140.80052 (18)0.60161 (16)0.84674 (6)0.0184 (4)
C150.81624 (19)0.62834 (18)0.80262 (7)0.0228 (4)
H15A0.85710.69660.79500.027*
C160.7737 (2)0.55772 (18)0.76967 (7)0.0258 (4)
H16A0.78590.57750.73990.031*
C170.7132 (2)0.45805 (18)0.78045 (7)0.0258 (4)
H17A0.68420.40890.75810.031*
C180.6953 (2)0.43071 (18)0.82410 (7)0.0232 (4)
H18A0.65270.36290.83120.028*
C190.73836 (19)0.50010 (16)0.85791 (6)0.0195 (4)
C200.56331 (19)0.37755 (17)0.91069 (6)0.0215 (4)
C210.4471 (2)0.43019 (18)0.91673 (8)0.0290 (4)
H21A0.44450.50840.92290.035*
C220.3352 (2)0.3702 (2)0.91386 (9)0.0355 (5)
H22A0.25660.40700.91830.043*
C230.3388 (2)0.2556 (2)0.90449 (8)0.0336 (5)
H23A0.26240.21440.90180.040*
C240.4527 (2)0.2020 (2)0.89907 (8)0.0295 (5)
H24A0.45460.12360.89320.035*
C250.5648 (2)0.26153 (18)0.90216 (7)0.0251 (4)
H25A0.64290.22360.89850.030*
C260.82714 (19)0.36238 (17)0.92864 (7)0.0219 (4)
C270.8919 (2)0.29840 (19)0.89740 (7)0.0255 (4)
H27A0.87040.30530.86740.031*
C280.9872 (2)0.22503 (19)0.90990 (8)0.0296 (5)
H28A1.03030.18170.88850.036*
C291.0194 (2)0.2150 (2)0.95356 (8)0.0337 (5)
H29A1.08540.16570.96210.040*
C300.9560 (3)0.2763 (2)0.98461 (8)0.0368 (5)
H30A0.97740.26811.01460.044*
C310.8607 (2)0.3506 (2)0.97247 (8)0.0297 (5)
H31A0.81820.39350.99410.036*
C320.50410 (19)0.71228 (17)0.80926 (7)0.0232 (4)
C330.4184 (2)0.6265 (2)0.79871 (9)0.0343 (5)
H33A0.38120.58280.82130.041*
C340.3877 (3)0.6052 (2)0.75526 (10)0.0446 (7)
H34A0.32820.54810.74840.054*
C350.4428 (3)0.6658 (2)0.72231 (8)0.0394 (6)
H35A0.42170.65030.69280.047*
C360.5285 (2)0.7493 (2)0.73197 (8)0.0335 (5)
H36A0.56710.79070.70910.040*
C370.5589 (2)0.77295 (19)0.77527 (7)0.0269 (4)
H37A0.61750.83110.78170.032*
C380.4032 (2)0.82758 (17)0.88152 (7)0.0232 (4)
C390.3490 (2)0.90539 (19)0.85289 (7)0.0268 (4)
H39A0.38210.91450.82430.032*
C400.2458 (2)0.96965 (18)0.86647 (8)0.0311 (5)
H40A0.20901.02210.84690.037*
C410.1974 (2)0.9581 (2)0.90739 (9)0.0356 (6)
H41A0.12841.00360.91630.043*
C420.2483 (2)0.8804 (2)0.93601 (8)0.0377 (5)
H42A0.21420.87190.96450.045*
C430.3507 (2)0.8141 (2)0.92268 (8)0.0320 (5)
H43A0.38450.75940.94200.038*
C441.0275 (2)0.3716 (2)0.78598 (8)0.0334 (5)
H44A0.96500.42260.80030.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Fe10.02823 (14)0.02016 (13)0.01861 (13)−0.00058 (12)−0.00085 (12)−0.00220 (11)
Cl10.0706 (5)0.0357 (3)0.0507 (4)−0.0085 (3)0.0253 (4)−0.0095 (3)
Cl20.0541 (4)0.0381 (3)0.0341 (3)−0.0010 (3)0.0077 (3)0.0013 (3)
Cl30.0390 (4)0.0811 (6)0.0512 (4)0.0087 (4)−0.0017 (3)0.0119 (4)
P10.0234 (2)0.0190 (2)0.0185 (2)−0.00097 (19)0.00134 (19)−0.0001 (2)
P20.0202 (2)0.0194 (2)0.0230 (2)−0.0004 (2)−0.00033 (19)0.0015 (2)
N10.0227 (9)0.0215 (8)0.0316 (9)−0.0020 (7)−0.0068 (7)0.0011 (8)
C10.0215 (9)0.0176 (8)0.0180 (9)−0.0012 (7)0.0002 (7)−0.0020 (7)
C20.0222 (10)0.0164 (9)0.0204 (9)−0.0007 (7)−0.0007 (7)0.0002 (7)
C30.0273 (10)0.0186 (9)0.0193 (9)0.0014 (8)−0.0017 (8)0.0010 (7)
C40.0312 (11)0.0168 (9)0.0257 (10)−0.0042 (8)0.0012 (8)0.0009 (8)
C50.0234 (9)0.0211 (9)0.0239 (10)−0.0042 (8)−0.0003 (7)−0.0016 (8)
C60.0582 (16)0.0380 (13)0.0185 (10)0.0055 (12)−0.0065 (10)0.0003 (9)
C70.0519 (15)0.0478 (15)0.0166 (10)−0.0112 (13)0.0064 (10)0.0019 (10)
C80.0448 (15)0.0508 (16)0.0228 (11)0.0083 (12)0.0079 (10)−0.0078 (11)
C90.0684 (19)0.0326 (12)0.0247 (11)0.0027 (13)−0.0013 (12)−0.0111 (9)
C100.0492 (15)0.0473 (15)0.0229 (11)−0.0112 (12)−0.0081 (10)−0.0067 (11)
C110.0201 (9)0.0195 (9)0.0203 (9)−0.0005 (7)−0.0017 (7)−0.0004 (8)
C120.0297 (11)0.0295 (11)0.0456 (13)0.0008 (9)−0.0154 (11)0.0083 (11)
C130.0205 (11)0.0325 (11)0.0447 (13)−0.0007 (9)0.0003 (9)−0.0039 (10)
C140.0182 (8)0.0171 (9)0.0198 (9)0.0007 (7)−0.0007 (7)0.0001 (7)
C150.0235 (10)0.0212 (9)0.0237 (10)−0.0005 (8)0.0016 (8)0.0017 (8)
C160.0297 (11)0.0286 (10)0.0189 (9)0.0027 (8)0.0013 (8)0.0016 (8)
C170.0292 (10)0.0261 (10)0.0220 (9)−0.0017 (8)−0.0034 (8)−0.0037 (8)
C180.0263 (10)0.0204 (10)0.0230 (10)−0.0028 (8)−0.0001 (8)−0.0007 (8)
C190.0188 (9)0.0198 (8)0.0199 (9)0.0020 (7)−0.0007 (7)0.0014 (7)
C200.0230 (9)0.0230 (9)0.0186 (9)−0.0014 (7)0.0025 (7)0.0021 (7)
C210.0288 (10)0.0238 (10)0.0343 (11)0.0036 (8)0.0008 (9)0.0013 (9)
C220.0214 (10)0.0358 (12)0.0494 (15)0.0070 (9)0.0011 (10)0.0010 (12)
C230.0230 (10)0.0383 (13)0.0396 (13)−0.0071 (10)−0.0020 (9)0.0006 (10)
C240.0298 (11)0.0264 (10)0.0323 (11)−0.0044 (9)0.0033 (9)−0.0027 (9)
C250.0248 (10)0.0249 (10)0.0256 (10)−0.0005 (8)0.0033 (8)−0.0022 (8)
C260.0229 (9)0.0198 (9)0.0229 (10)−0.0043 (7)0.0007 (7)0.0020 (7)
C270.0272 (11)0.0269 (10)0.0225 (10)−0.0001 (8)−0.0001 (8)0.0003 (8)
C280.0250 (10)0.0289 (11)0.0349 (12)0.0019 (9)0.0021 (9)−0.0001 (9)
C290.0265 (11)0.0344 (13)0.0400 (13)0.0031 (10)−0.0068 (10)0.0059 (10)
C300.0401 (13)0.0448 (14)0.0254 (11)0.0045 (12)−0.0081 (10)0.0059 (10)
C310.0298 (11)0.0350 (12)0.0243 (11)0.0005 (9)−0.0013 (9)0.0031 (9)
C320.0208 (9)0.0224 (10)0.0263 (10)0.0014 (8)−0.0021 (8)−0.0037 (8)
C330.0334 (12)0.0294 (11)0.0402 (13)−0.0075 (10)−0.0029 (10)−0.0029 (10)
C340.0460 (15)0.0355 (14)0.0524 (17)−0.0076 (12)−0.0146 (13)−0.0137 (12)
C350.0511 (16)0.0360 (13)0.0310 (12)0.0098 (12)−0.0162 (11)−0.0105 (10)
C360.0355 (12)0.0387 (13)0.0261 (11)0.0057 (10)−0.0041 (9)−0.0012 (10)
C370.0251 (10)0.0276 (10)0.0279 (11)0.0010 (9)−0.0039 (8)0.0001 (9)
C380.0196 (9)0.0226 (10)0.0273 (10)−0.0010 (8)−0.0002 (8)−0.0033 (8)
C390.0244 (9)0.0273 (10)0.0288 (10)0.0002 (8)−0.0014 (8)−0.0001 (9)
C400.0274 (10)0.0227 (10)0.0432 (12)0.0032 (9)−0.0100 (10)−0.0012 (9)
C410.0235 (10)0.0307 (11)0.0526 (16)0.0028 (9)0.0006 (10)−0.0118 (11)
C420.0324 (12)0.0464 (14)0.0344 (12)0.0011 (12)0.0123 (10)0.0000 (10)
C430.0235 (10)0.0410 (12)0.0314 (12)0.0041 (9)0.0045 (9)0.0073 (11)
C440.0357 (12)0.0342 (12)0.0302 (12)0.0036 (10)0.0067 (10)−0.0018 (9)
Geometric parameters (Å, °) top
Fe1—C62.037 (2)C15—H15A0.9500
Fe1—C72.040 (2)C16—C171.388 (3)
Fe1—C12.041 (2)C16—H16A0.9500
Fe1—C52.042 (2)C17—C181.389 (3)
Fe1—C22.044 (2)C17—H17A0.9500
Fe1—C32.048 (2)C18—C191.400 (3)
Fe1—C102.051 (2)C18—H18A0.9500
Fe1—C82.052 (2)C20—C211.395 (3)
Fe1—C42.053 (2)C20—C251.404 (3)
Fe1—C92.055 (2)C21—C221.388 (3)
Cl1—C441.762 (3)C21—H21A0.9500
Cl2—C441.765 (2)C22—C231.393 (4)
Cl3—C441.759 (3)C22—H22A0.9500
P1—C261.839 (2)C23—C241.376 (3)
P1—C201.840 (2)C23—H23A0.9500
P1—C191.851 (2)C24—C251.386 (3)
P2—C21.820 (2)C24—H24A0.9500
P2—C321.834 (2)C25—H25A0.9500
P2—C381.847 (2)C26—C311.395 (3)
N1—C131.455 (3)C26—C271.402 (3)
N1—C121.456 (3)C27—C281.389 (3)
N1—C111.477 (3)C27—H27A0.9500
C1—C51.426 (3)C28—C291.385 (3)
C1—C21.444 (3)C28—H28A0.9500
C1—C111.523 (3)C29—C301.374 (4)
C2—C31.441 (3)C29—H29A0.9500
C3—C41.421 (3)C30—C311.394 (3)
C3—H3A0.9500C30—H30A0.9500
C4—C51.427 (3)C31—H31A0.9500
C4—H4A0.9500C32—C371.393 (3)
C5—H5A0.9500C32—C331.404 (3)
C6—C71.413 (4)C33—C341.393 (4)
C6—C101.420 (4)C33—H33A0.9500
C6—H6A0.9500C34—C351.371 (4)
C7—C81.423 (4)C34—H34A0.9500
C7—H7A0.9500C35—C361.378 (4)
C8—C91.410 (4)C35—H35A0.9500
C8—H8A0.9500C36—C371.393 (3)
C9—C101.423 (4)C36—H36A0.9500
C9—H9A0.9500C37—H37A0.9500
C10—H10A0.9500C38—C431.388 (3)
C11—C141.533 (3)C38—C391.399 (3)
C11—H11A1.0000C39—C401.398 (3)
C12—H12A0.9800C39—H39A0.9500
C12—H12B0.9800C40—C411.361 (4)
C12—H12C0.9800C40—H40A0.9500
C13—H13A0.9800C41—C421.384 (4)
C13—H13B0.9800C41—H41A0.9500
C13—H13C0.9800C42—C431.402 (3)
C14—C151.398 (3)C42—H42A0.9500
C14—C191.417 (3)C43—H43A0.9500
C15—C161.388 (3)C44—H44A1.0000
C6—Fe1—C740.54 (12)N1—C11—C1110.27 (17)
C6—Fe1—C1104.86 (10)N1—C11—C14116.32 (17)
C7—Fe1—C1115.79 (10)C1—C11—C14111.02 (16)
C6—Fe1—C5115.15 (10)N1—C11—H11A106.2
C7—Fe1—C5148.79 (11)C1—C11—H11A106.2
C1—Fe1—C540.89 (8)C14—C11—H11A106.2
C6—Fe1—C2126.76 (10)N1—C12—H12A109.5
C7—Fe1—C2107.55 (9)N1—C12—H12B109.5
C1—Fe1—C241.39 (8)H12A—C12—H12B109.5
C5—Fe1—C269.12 (8)N1—C12—H12C109.5
C6—Fe1—C3166.89 (10)H12A—C12—H12C109.5
C7—Fe1—C3130.39 (11)H12B—C12—H12C109.5
C1—Fe1—C369.17 (8)N1—C13—H13A109.5
C5—Fe1—C368.53 (8)N1—C13—H13B109.5
C2—Fe1—C341.25 (8)H13A—C13—H13B109.5
C6—Fe1—C1040.63 (11)N1—C13—H13C109.5
C7—Fe1—C1068.09 (11)H13A—C13—H13C109.5
C1—Fe1—C10126.08 (11)H13B—C13—H13C109.5
C5—Fe1—C10106.63 (10)C15—C14—C19118.85 (18)
C2—Fe1—C10164.84 (10)C15—C14—C11118.92 (17)
C3—Fe1—C10152.20 (10)C19—C14—C11122.20 (17)
C6—Fe1—C868.35 (12)C16—C15—C14121.75 (19)
C7—Fe1—C840.70 (12)C16—C15—H15A119.1
C1—Fe1—C8150.97 (10)C14—C15—H15A119.1
C5—Fe1—C8167.98 (11)C17—C16—C15119.61 (19)
C2—Fe1—C8118.89 (10)C17—C16—H16A120.2
C3—Fe1—C8110.85 (10)C15—C16—H16A120.2
C10—Fe1—C867.99 (12)C16—C17—C18119.5 (2)
C6—Fe1—C4149.67 (11)C16—C17—H17A120.3
C7—Fe1—C4169.20 (11)C18—C17—H17A120.3
C1—Fe1—C468.96 (8)C17—C18—C19121.97 (19)
C5—Fe1—C440.77 (8)C17—C18—H18A119.0
C2—Fe1—C469.08 (8)C19—C18—H18A119.0
C3—Fe1—C440.54 (8)C18—C19—C14118.35 (18)
C10—Fe1—C4117.85 (10)C18—C19—P1121.13 (15)
C8—Fe1—C4131.07 (10)C14—C19—P1120.35 (14)
C6—Fe1—C968.30 (11)C21—C20—C25118.39 (19)
C7—Fe1—C968.00 (11)C21—C20—P1116.76 (16)
C1—Fe1—C9165.43 (11)C25—C20—P1124.84 (16)
C5—Fe1—C9128.97 (11)C22—C21—C20121.1 (2)
C2—Fe1—C9152.90 (11)C22—C21—H21A119.4
C3—Fe1—C9120.15 (10)C20—C21—H21A119.4
C10—Fe1—C940.56 (12)C21—C22—C23119.5 (2)
C8—Fe1—C940.14 (12)C21—C22—H22A120.2
C4—Fe1—C9110.01 (10)C23—C22—H22A120.2
C26—P1—C20101.93 (9)C24—C23—C22120.1 (2)
C26—P1—C19102.35 (9)C24—C23—H23A119.9
C20—P1—C19101.64 (9)C22—C23—H23A119.9
C2—P2—C32102.38 (10)C23—C24—C25120.6 (2)
C2—P2—C38101.87 (9)C23—C24—H24A119.7
C32—P2—C3899.73 (10)C25—C24—H24A119.7
C13—N1—C12110.10 (19)C24—C25—C20120.3 (2)
C13—N1—C11116.29 (18)C24—C25—H25A119.9
C12—N1—C11112.82 (18)C20—C25—H25A119.9
C5—C1—C2107.72 (17)C31—C26—C27118.5 (2)
C5—C1—C11126.85 (18)C31—C26—P1117.03 (17)
C2—C1—C11125.36 (17)C27—C26—P1124.42 (16)
C5—C1—Fe169.58 (11)C28—C27—C26120.6 (2)
C2—C1—Fe169.40 (11)C28—C27—H27A119.7
C11—C1—Fe1124.09 (14)C26—C27—H27A119.7
C3—C2—C1107.15 (18)C29—C28—C27119.9 (2)
C3—C2—P2128.26 (16)C29—C28—H28A120.0
C1—C2—P2124.57 (14)C27—C28—H28A120.0
C3—C2—Fe169.54 (12)C30—C29—C28120.2 (2)
C1—C2—Fe169.21 (11)C30—C29—H29A119.9
P2—C2—Fe1125.05 (11)C28—C29—H29A119.9
C4—C3—C2108.50 (18)C29—C30—C31120.4 (2)
C4—C3—Fe169.92 (12)C29—C30—H30A119.8
C2—C3—Fe169.21 (12)C31—C30—H30A119.8
C4—C3—H3A125.7C30—C31—C26120.3 (2)
C2—C3—H3A125.7C30—C31—H31A119.8
Fe1—C3—H3A126.7C26—C31—H31A119.8
C3—C4—C5107.94 (17)C37—C32—C33118.3 (2)
C3—C4—Fe169.54 (12)C37—C32—P2124.82 (16)
C5—C4—Fe169.19 (12)C33—C32—P2116.86 (18)
C3—C4—H4A126.0C34—C33—C32120.2 (2)
C5—C4—H4A126.0C34—C33—H33A119.9
Fe1—C4—H4A126.8C32—C33—H33A119.9
C1—C5—C4108.69 (17)C35—C34—C33120.5 (2)
C1—C5—Fe169.53 (11)C35—C34—H34A119.7
C4—C5—Fe170.04 (12)C33—C34—H34A119.7
C1—C5—H5A125.7C34—C35—C36120.1 (2)
C4—C5—H5A125.7C34—C35—H35A119.9
Fe1—C5—H5A126.4C36—C35—H35A119.9
C7—C6—C10107.9 (3)C35—C36—C37120.1 (2)
C7—C6—Fe169.84 (15)C35—C36—H36A119.9
C10—C6—Fe170.21 (15)C37—C36—H36A119.9
C7—C6—H6A126.0C32—C37—C36120.7 (2)
C10—C6—H6A126.0C32—C37—H37A119.7
Fe1—C6—H6A125.5C36—C37—H37A119.7
C6—C7—C8108.2 (3)C43—C38—C39118.7 (2)
C6—C7—Fe169.61 (15)C43—C38—P2116.83 (17)
C8—C7—Fe170.10 (15)C39—C38—P2124.35 (17)
C6—C7—H7A125.9C40—C39—C38119.8 (2)
C8—C7—H7A125.9C40—C39—H39A120.1
Fe1—C7—H7A126.0C38—C39—H39A120.1
C9—C8—C7107.9 (3)C41—C40—C39120.9 (2)
C9—C8—Fe170.05 (14)C41—C40—H40A119.5
C7—C8—Fe169.20 (14)C39—C40—H40A119.5
C9—C8—H8A126.1C40—C41—C42120.2 (2)
C7—C8—H8A126.1C40—C41—H41A119.9
Fe1—C8—H8A126.3C42—C41—H41A119.9
C8—C9—C10108.2 (2)C41—C42—C43119.6 (2)
C8—C9—Fe169.81 (14)C41—C42—H42A120.2
C10—C9—Fe169.57 (14)C43—C42—H42A120.2
C8—C9—H9A125.9C38—C43—C42120.7 (2)
C10—C9—H9A125.9C38—C43—H43A119.7
Fe1—C9—H9A126.3C42—C43—H43A119.7
C6—C10—C9107.8 (3)Cl3—C44—Cl1110.73 (14)
C6—C10—Fe169.15 (14)Cl3—C44—Cl2109.94 (14)
C9—C10—Fe169.87 (14)Cl1—C44—Cl2110.26 (14)
C6—C10—H10A126.1Cl3—C44—H44A108.6
C9—C10—H10A126.1Cl1—C44—H44A108.6
Fe1—C10—H10A126.5Cl2—C44—H44A108.6
C6—Fe1—C1—C5−111.42 (14)C3—Fe1—C7—C6166.56 (14)
C7—Fe1—C1—C5−153.26 (14)C10—Fe1—C7—C6−37.99 (17)
C2—Fe1—C1—C5119.14 (16)C8—Fe1—C7—C6−119.3 (2)
C3—Fe1—C1—C580.85 (13)C4—Fe1—C7—C6−163.4 (5)
C10—Fe1—C1—C5−72.51 (16)C9—Fe1—C7—C6−81.88 (18)
C8—Fe1—C1—C5176.55 (19)C6—Fe1—C7—C8119.3 (2)
C4—Fe1—C1—C537.31 (12)C1—Fe1—C7—C8−158.02 (15)
C9—Fe1—C1—C5−51.4 (4)C5—Fe1—C7—C8167.33 (17)
C6—Fe1—C1—C2129.45 (13)C2—Fe1—C7—C8−114.17 (17)
C7—Fe1—C1—C287.60 (14)C3—Fe1—C7—C8−74.2 (2)
C5—Fe1—C1—C2−119.14 (16)C10—Fe1—C7—C881.27 (18)
C3—Fe1—C1—C2−38.28 (12)C4—Fe1—C7—C8−44.1 (6)
C10—Fe1—C1—C2168.36 (13)C9—Fe1—C7—C837.38 (17)
C8—Fe1—C1—C257.4 (2)C6—C7—C8—C9−0.2 (3)
C4—Fe1—C1—C2−81.82 (12)Fe1—C7—C8—C9−59.59 (17)
C9—Fe1—C1—C2−170.5 (4)C6—C7—C8—Fe159.41 (18)
C6—Fe1—C1—C119.96 (19)C6—Fe1—C8—C981.58 (18)
C7—Fe1—C1—C11−31.9 (2)C7—Fe1—C8—C9119.2 (2)
C5—Fe1—C1—C11121.4 (2)C1—Fe1—C8—C9163.15 (18)
C2—Fe1—C1—C11−119.5 (2)C5—Fe1—C8—C9−27.8 (6)
C3—Fe1—C1—C11−157.77 (18)C2—Fe1—C8—C9−157.33 (15)
C10—Fe1—C1—C1148.9 (2)C3—Fe1—C8—C9−112.47 (16)
C8—Fe1—C1—C11−62.1 (3)C10—Fe1—C8—C937.65 (16)
C4—Fe1—C1—C11158.69 (19)C4—Fe1—C8—C9−70.8 (2)
C9—Fe1—C1—C1170.0 (4)C6—Fe1—C8—C7−37.60 (17)
C5—C1—C2—C30.2 (2)C1—Fe1—C8—C744.0 (3)
C11—C1—C2—C3177.32 (18)C5—Fe1—C8—C7−146.9 (4)
Fe1—C1—C2—C359.44 (14)C2—Fe1—C8—C783.49 (18)
C5—C1—C2—P2−178.22 (15)C3—Fe1—C8—C7128.36 (16)
C11—C1—C2—P2−1.1 (3)C10—Fe1—C8—C7−81.53 (18)
Fe1—C1—C2—P2−118.97 (16)C4—Fe1—C8—C7170.04 (15)
C5—C1—C2—Fe1−59.24 (14)C9—Fe1—C8—C7−119.2 (2)
C11—C1—C2—Fe1117.87 (19)C7—C8—C9—C10−0.1 (3)
C32—P2—C2—C381.2 (2)Fe1—C8—C9—C10−59.20 (17)
C38—P2—C2—C3−21.7 (2)C7—C8—C9—Fe159.06 (17)
C32—P2—C2—C1−100.70 (18)C6—Fe1—C9—C8−81.72 (18)
C38—P2—C2—C1156.42 (18)C7—Fe1—C9—C8−37.89 (17)
C32—P2—C2—Fe1171.77 (12)C1—Fe1—C9—C8−146.0 (4)
C38—P2—C2—Fe168.89 (14)C5—Fe1—C9—C8172.83 (15)
C6—Fe1—C2—C3172.74 (15)C2—Fe1—C9—C847.8 (3)
C7—Fe1—C2—C3132.08 (15)C3—Fe1—C9—C887.11 (18)
C1—Fe1—C2—C3−118.57 (17)C10—Fe1—C9—C8−119.4 (2)
C5—Fe1—C2—C3−80.84 (13)C4—Fe1—C9—C8130.74 (16)
C10—Fe1—C2—C3−157.2 (4)C6—Fe1—C9—C1037.71 (17)
C8—Fe1—C2—C389.27 (15)C7—Fe1—C9—C1081.55 (18)
C4—Fe1—C2—C3−37.05 (13)C1—Fe1—C9—C10−26.6 (5)
C9—Fe1—C2—C356.2 (3)C5—Fe1—C9—C10−67.73 (19)
C6—Fe1—C2—C1−68.69 (16)C2—Fe1—C9—C10167.21 (19)
C7—Fe1—C2—C1−109.35 (14)C3—Fe1—C9—C10−153.45 (15)
C5—Fe1—C2—C137.73 (11)C8—Fe1—C9—C10119.4 (2)
C3—Fe1—C2—C1118.57 (17)C4—Fe1—C9—C10−109.82 (16)
C10—Fe1—C2—C1−38.6 (4)C7—C6—C10—C9−0.5 (3)
C8—Fe1—C2—C1−152.16 (13)Fe1—C6—C10—C959.39 (17)
C4—Fe1—C2—C181.52 (12)C7—C6—C10—Fe1−59.91 (18)
C9—Fe1—C2—C1174.8 (2)C8—C9—C10—C60.4 (3)
C6—Fe1—C2—P249.67 (18)Fe1—C9—C10—C6−58.94 (17)
C7—Fe1—C2—P29.02 (16)C8—C9—C10—Fe159.35 (16)
C1—Fe1—C2—P2118.37 (17)C7—Fe1—C10—C637.91 (18)
C5—Fe1—C2—P2156.10 (15)C1—Fe1—C10—C6−68.8 (2)
C3—Fe1—C2—P2−123.06 (19)C5—Fe1—C10—C6−109.44 (17)
C10—Fe1—C2—P279.8 (4)C2—Fe1—C10—C6−38.1 (5)
C8—Fe1—C2—P2−33.79 (17)C3—Fe1—C10—C6175.2 (2)
C4—Fe1—C2—P2−160.12 (15)C8—Fe1—C10—C681.96 (18)
C9—Fe1—C2—P2−66.8 (3)C4—Fe1—C10—C6−152.04 (16)
C1—C2—C3—C4−0.2 (2)C9—Fe1—C10—C6119.2 (2)
P2—C2—C3—C4178.16 (16)C6—Fe1—C10—C9−119.2 (2)
Fe1—C2—C3—C459.05 (15)C7—Fe1—C10—C9−81.32 (19)
C1—C2—C3—Fe1−59.23 (14)C1—Fe1—C10—C9171.99 (15)
P2—C2—C3—Fe1119.10 (18)C5—Fe1—C10—C9131.33 (16)
C6—Fe1—C3—C4−146.5 (4)C2—Fe1—C10—C9−157.3 (3)
C7—Fe1—C3—C4171.69 (14)C3—Fe1—C10—C956.0 (3)
C1—Fe1—C3—C4−81.60 (13)C8—Fe1—C10—C9−37.27 (17)
C5—Fe1—C3—C4−37.61 (12)C4—Fe1—C10—C988.73 (18)
C2—Fe1—C3—C4−120.01 (17)C13—N1—C11—C1−78.0 (2)
C10—Fe1—C3—C447.4 (3)C12—N1—C11—C1153.44 (19)
C8—Fe1—C3—C4129.51 (14)C13—N1—C11—C1449.6 (3)
C9—Fe1—C3—C485.97 (16)C12—N1—C11—C14−79.0 (2)
C6—Fe1—C3—C2−26.5 (5)C5—C1—C11—N11.4 (3)
C7—Fe1—C3—C2−68.30 (17)C2—C1—C11—N1−175.17 (19)
C1—Fe1—C3—C238.41 (12)Fe1—C1—C11—N1−87.5 (2)
C5—Fe1—C3—C282.40 (13)C5—C1—C11—C14−129.0 (2)
C10—Fe1—C3—C2167.4 (2)C2—C1—C11—C1454.4 (3)
C8—Fe1—C3—C2−110.48 (14)Fe1—C1—C11—C14142.10 (15)
C4—Fe1—C3—C2120.01 (17)N1—C11—C14—C15−77.1 (2)
C9—Fe1—C3—C2−154.02 (14)C1—C11—C14—C1550.1 (2)
C2—C3—C4—C50.1 (2)N1—C11—C14—C19105.1 (2)
Fe1—C3—C4—C558.71 (15)C1—C11—C14—C19−127.73 (19)
C2—C3—C4—Fe1−58.62 (14)C19—C14—C15—C16−0.6 (3)
C6—Fe1—C4—C3165.66 (18)C11—C14—C15—C16−178.46 (19)
C7—Fe1—C4—C3−36.0 (6)C14—C15—C16—C170.4 (3)
C1—Fe1—C4—C382.16 (12)C15—C16—C17—C180.4 (3)
C5—Fe1—C4—C3119.58 (17)C16—C17—C18—C19−1.0 (3)
C2—Fe1—C4—C337.68 (12)C17—C18—C19—C140.7 (3)
C10—Fe1—C4—C3−157.14 (14)C17—C18—C19—P1176.02 (17)
C8—Fe1—C4—C3−72.99 (17)C15—C14—C19—C180.1 (3)
C9—Fe1—C4—C3−113.37 (14)C11—C14—C19—C18177.84 (18)
C6—Fe1—C4—C546.1 (2)C15—C14—C19—P1−175.28 (15)
C7—Fe1—C4—C5−155.6 (5)C11—C14—C19—P12.5 (3)
C1—Fe1—C4—C5−37.42 (12)C26—P1—C19—C1881.89 (18)
C2—Fe1—C4—C5−81.90 (13)C20—P1—C19—C18−23.25 (19)
C3—Fe1—C4—C5−119.58 (17)C26—P1—C19—C14−102.91 (17)
C10—Fe1—C4—C583.28 (15)C20—P1—C19—C14151.95 (16)
C8—Fe1—C4—C5167.43 (14)C26—P1—C20—C21157.26 (17)
C9—Fe1—C4—C5127.05 (14)C19—P1—C20—C21−97.27 (17)
C2—C1—C5—C4−0.1 (2)C26—P1—C20—C25−21.4 (2)
C11—C1—C5—C4−177.21 (19)C19—P1—C20—C2584.06 (19)
Fe1—C1—C5—C4−59.27 (15)C25—C20—C21—C22−0.8 (3)
C2—C1—C5—Fe159.13 (14)P1—C20—C21—C22−179.6 (2)
C11—C1—C5—Fe1−117.9 (2)C20—C21—C22—C23−0.4 (4)
C3—C4—C5—C10.0 (2)C21—C22—C23—C241.4 (4)
Fe1—C4—C5—C158.96 (14)C22—C23—C24—C25−1.0 (4)
C3—C4—C5—Fe1−58.92 (14)C23—C24—C25—C20−0.3 (3)
C6—Fe1—C5—C183.73 (14)C21—C20—C25—C241.2 (3)
C7—Fe1—C5—C151.4 (2)P1—C20—C25—C24179.85 (17)
C2—Fe1—C5—C1−38.18 (11)C20—P1—C26—C31−99.02 (18)
C3—Fe1—C5—C1−82.56 (13)C19—P1—C26—C31156.06 (17)
C10—Fe1—C5—C1126.44 (13)C20—P1—C26—C2783.79 (19)
C8—Fe1—C5—C1−171.9 (4)C19—P1—C26—C27−21.1 (2)
C4—Fe1—C5—C1−119.97 (17)C31—C26—C27—C280.0 (3)
C9—Fe1—C5—C1165.35 (14)P1—C26—C27—C28177.18 (17)
C6—Fe1—C5—C4−156.31 (13)C26—C27—C28—C29−0.3 (3)
C7—Fe1—C5—C4171.40 (18)C27—C28—C29—C300.9 (4)
C1—Fe1—C5—C4119.97 (17)C28—C29—C30—C31−1.2 (4)
C2—Fe1—C5—C481.79 (13)C29—C30—C31—C260.9 (4)
C3—Fe1—C5—C437.40 (12)C27—C26—C31—C30−0.3 (3)
C10—Fe1—C5—C4−113.59 (14)P1—C26—C31—C30−177.69 (19)
C8—Fe1—C5—C4−52.0 (5)C2—P2—C32—C37−8.3 (2)
C9—Fe1—C5—C4−74.69 (17)C38—P2—C32—C3796.3 (2)
C1—Fe1—C6—C7−112.48 (17)C2—P2—C32—C33170.98 (17)
C5—Fe1—C6—C7−154.79 (16)C38—P2—C32—C33−84.46 (19)
C2—Fe1—C6—C7−72.88 (19)C37—C32—C33—C34−1.4 (4)
C3—Fe1—C6—C7−51.3 (5)P2—C32—C33—C34179.3 (2)
C10—Fe1—C6—C7118.7 (2)C32—C33—C34—C351.4 (4)
C8—Fe1—C6—C737.74 (17)C33—C34—C35—C36−0.5 (4)
C4—Fe1—C6—C7173.90 (17)C34—C35—C36—C37−0.5 (4)
C9—Fe1—C6—C781.09 (19)C33—C32—C37—C360.4 (3)
C7—Fe1—C6—C10−118.7 (2)P2—C32—C37—C36179.62 (18)
C1—Fe1—C6—C10128.79 (17)C35—C36—C37—C320.6 (4)
C5—Fe1—C6—C1086.48 (18)C2—P2—C38—C43−110.84 (19)
C2—Fe1—C6—C10168.38 (16)C32—P2—C38—C43144.19 (18)
C3—Fe1—C6—C10−170.1 (4)C2—P2—C38—C3972.4 (2)
C8—Fe1—C6—C10−80.99 (18)C32—P2—C38—C39−32.6 (2)
C4—Fe1—C6—C1055.2 (3)C43—C38—C39—C401.6 (3)
C9—Fe1—C6—C10−37.64 (18)P2—C38—C39—C40178.31 (17)
C10—C6—C7—C80.4 (3)C38—C39—C40—C410.3 (3)
Fe1—C6—C7—C8−59.71 (18)C39—C40—C41—C42−1.4 (4)
C10—C6—C7—Fe160.14 (18)C40—C41—C42—C430.5 (4)
C1—Fe1—C7—C682.72 (17)C39—C38—C43—C42−2.5 (4)
C5—Fe1—C7—C648.1 (3)P2—C38—C43—C42−179.47 (19)
C2—Fe1—C7—C6126.58 (16)C41—C42—C43—C381.5 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···P11.002.573.184 (2)120
C13—H13B···Cg(C38->C43)i0.982.883.663138
C30—H30A···Cg(C20->C25)ii0.952.593.473154
C44—H44A···Cg(C14->C19)1.002.593.537159
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C11—H11A···P11.002.573.184 (2)120
C13—H13B···Cg(C38->C43)i0.982.883.663138
C30—H30A···Cg(C20->C25)ii0.952.593.473154
C44—H44A···Cg(C14->C19)1.002.593.537159
Symmetry codes: (i) x+1, y, z; (ii) x+1/2, −y+1/2, −z+2.
references
References top

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