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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 10| October 2009| Page m1210
doi:10.1107/S1600536809036459

1-Bromo-1′-(di­phenyl­thio­phosphor­yl)­ferrocene

Petr Štěpnička,a* Jiří Schulza and Ivana Císařováa

aDepartment of Inorganic Chemistry, Faculty of Science, Charles University in Prague, Hlavova 2030, 12840 Prague 2, Czech Republic
*Correspondence e-mail: stepnic@natur.cuni.cz

(Received 8 September 2009; accepted 9 September 2009; online 12 September 2009)

The title compound, [Fe(C5H4Br)(C17H14PS)], crystallizes with two practically undistiguishable mol­ecules in the asymmetric unit, which are related by a non-space-group inversion. The ferrocene-1,1′-diyl units exhibit a regular geometry with negligible tilting and balanced Fe–ring centroid distances, and with the attached substituents assuming conformations close to ideal synclinal eclipsed.

Related literature

For an overview of the chemistry of ferrocene, see: Štěpnička (2008[Štěpnička, P. (2008). Ferrocenes: Ligands, Materials and Biomolecules. Wiley: Chichester.]); Butler & Davies (1996[Butler, I. R. & Davies, R. L. (1996). Synthesis, pp. 1350-1354.]). For related structures, see: Fang et al. (1995[Fang, Z.-G., Hor, T. S. A., Wen, Y.-S., Liu, L.-K. & Mak, T. C. W. (1995). Polyhedron, 14, 2403-2409.]); Hnetinka et al. (2004[Hnetinka, C. A., Hunter, A. D., Zeller, M. & Lesley, M. J. G. (2004). Acta Cryst. E60, m1806-m1807.]); Štěpnička & Císařová (2006a[Štěpnička, P. & Císařová, I. (2006a). Collect. Czech. Chem. Commun. 71, 215-236.],b[Štěpnička, P. & Císařová, I. (2006b). J. Organomet. Chem. 691, 2863-2871.]); Labande et al. (2007[Labande, A., Daran, J.-C., Manoury, E. & Poli, R. (2007). Eur. J. Inorg. Chem. pp. 1205-1209.]); Štěpnička et al. (2007[Štěpnička, P., Schulz, J., Císařová, I. & Fejfarová, K. (2007). Collect. Czech. Chem. Commun. 72, 453-467.]).

[Scheme 1]

Experimental

Crystal data

  • [Fe(C5H4Br)(C17H14PS)]

  • Mr = 481.15

  • Monoclinic, P 21 /n

  • a = 13.3590 (7) Å

  • b = 17.3446 (7) Å

  • c = 17.0297 (9) Å

  • β = 102.460 (2)°

  • V = 3853.0 (3) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 3.05 mm−1

  • T = 150 K

  • 0.25 × 0.18 × 0.02 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: integration (COLLECT; Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]) Tmin = 0.540, Tmax = 0.937

  • 53227 measured reflections

  • 6802 independent reflections

  • 4020 reflections with I > 2σ(I)

  • Rint = 0.122
Refinement

  • R[F2 > 2σ(F2)] = 0.077

  • wR(F2) = 0.232

  • S = 1.05

  • 6802 reflections

  • 469 parameters

  • H-atom parameters constrained

  • Δρmax = 2.19 e Å−3

  • Δρmin = −1.30 e Å−3

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997[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.]); data reduction: HKL DENZO (Otwinowski & Minor, 1997[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.]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809036459/dn2483sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809036459/dn2483Isup2.hkl

checkCIF report


Comment top

1'-(Diphenylthiophosphoryl)-1-bromoferrocene, readily accessible by the reaction of 1'-(diphenylphosphino)-1-bromoferrocene with elemental sulfur, can be regarded a protected intermediate suitable for the preparation of functionalized ferrocene phosphines via a sequence comprising lithiation, reaction with an appropriate electrophile (Štěpnička, 2008; Butler & Davies, 1996) and, finally, deprotection of the phosphorus group.

The title compound crystallizes with the symmetry of the monoclinic space group P21/n and two virtually identical molecules in the asymmetric unit (Fig. 1; see also an overlap in Fig. 2) that are related by non-space-group inversion operation. Ferrocene units in the independent molecules have regular geometries, showing negligible tilts (ca 2 °) and statistically insignificant variation in the Fe–Cg distances (Cg denotes a cyclopentadienyl ring centroid; cf. Fe–Cg: 1.648 (5), 1.643 (5), 1.645 (4), and 1.643 (4) Å for the rings C(1–5), C(6–10), C(31–35), and C(36–40), respectively). Likewise, both molecules assume similar synclinal eclipsed conformation as indicated by the torsion angles Br—Cg—Cg—P = +75° and -77°, for molecule 1 and 2, respectively. The C—Br and C—P bond lengths compare well with those reported for 1,1'-dibromoferrocene (Hnetinka et al., 2004) or 1'-(diphenylthiophosphoryl)-1-bromoferrocene (Štěpnička & Císařová, 2006b), and for 1,1'-bis(diphenylthiophosphoryl)ferrocene (Fang et al., 1995) and 1'-functionalized (diphenylthiophosphoryl)ferrocenes Ph2P(S)fcX (fc = ferrocene-1,1'-diyl), where X = CHCH2 (Štěpnička & Císařová, 2006a), CHO, CHCBr2 and C≡CH (Štěpnička & Císařová, 2006b), CO2H (Štěpnička et al., 2007), and CH2(C3H3N2Me)+ BF4- (Labande et al., 2007), respectively.

Related literature top

For an overview of the chemistry of ferrocene, see: Štěpnička (2008); Butler & Davies (1996). For related structures, see: Fang et al. (1995); Hnetinka et al. (2004); Štěpnička & Císařová (2006a,b); Labande et al. (2007); Štěpnička et al. (2007).

Experimental top

The title compound was synthesized from the corresponding phosphine and elemental sulfur as follows. 1'-(Diphenylphosphino)-1-bromoferrocene (629 mg, 1.4 mmol; prepared according to Butler & Davies, 1996) and sulfur (64 mg, 2.0 mmol) were mixed with dry toluene (25 ml), and the the resulting solution was heated at reflux under an argon atmosphere for 1 h. The reaction mixture was cooled, filtered and concentrated under reduced pressure to about a half of the initial volume. Slow cooling to -18°C afforded 1'-(diphenylthiophosphoryl)-1-bromoferrocene as an orange microcrystalline solid. Yield: 490 mg (73%).

Characterization data: 1H NMR (CDCl3): δ 4.16 and 4.38 (2× apparent t, J = 1.9 Hz, 2 H, C5H4Br); 4.49 and 4.53 (2× apparent q, J = 2.0 Hz, 2 H, C5H4P); 7.39–7.75 (m, 10 H, PPh2). 13C{1H} NMR (CDCl3): 69.76 and 71.80 (2× s, 2 C, CH of C5H4Br); 74.92 (d, JPC = 12 Hz, 2 C, CH of C5H4P), 75.37 (d, JPC = 10 Hz, 2 C, CH of C5H4P), 76.70 (d, 1JPC = 97 Hz, Cipso of C5H4P), 77.75 (s, Cipso of C5H4Br), 128.27 (d, 3JPC = 12 Hz, 4 C, CHmeta of PPh2), 131.31 (d, 4JPC = 3 Hz, 2 C, CHpara of PPh2), 131.59 (d, 2JPC = 11 Hz, 4 C, CHortho of PPh2), 134.28 (d, 1JPC = 87 Hz, 2 C, Cipso of PPh2). 31P{1H} NMR (CDCl3): δ 41.5 (s).

Refinement top

All H atoms were included in their calculated positions and refined as riding atoms with Uiso(H) = 1.2Ueq of their bonding carbon atom. The unusually high residual electron density can be attributed to an unfavourable crystal shape (thin plates) of the available crystals and their lamellated internal structure, which results in crystal defects (a lower periodicity of the crystal assembly) and, consequently, to the high residual electron density observed.

Computing details top

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

Figures top
[Figure 1] Fig. 1. Views of the two independent molecules of the title compound showing the atom numbering scheme and displacement ellipsoids for the non-H atoms at the 30% probability level. Mutual orientation of the molecules does not correspond with that encountered in the crystal.
[Figure 2] Fig. 2. (a) View of the two crystallographically independent molecules illustrating their mutual orientation in the cell (molecule 1 in black, molecule 2 in red). (b) An overlap plot of the independent molecules as generated by PLATON. Inverted molecule 2 (in red) was fitted onto molecule 1 (in black).
1-Bromo-1'-(diphenylthiophosphoryl)ferrocene top
Crystal data top
[Fe(C5H4Br)(C17H14PS)]F(000) = 1936
Mr = 481.15Dx = 1.659 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 74781 reflections
a = 13.3590 (7) Åθ = 1.0–25.0°
b = 17.3446 (7) ŵ = 3.05 mm−1
c = 17.0297 (9) ÅT = 150 K
β = 102.460 (2)°Plate, orange
V = 3853.0 (3) Å30.25 × 0.18 × 0.02 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer		6802 independent reflections
Radiation source: fine-focus sealed tube4020 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.122
Detector resolution: 9.091 pixels mm-1θmax = 25.1°, θmin = 1.7°
ω and π scans to fill the Ewald sphereh = −15→15
Absorption correction: integration
(COLLECT; Nonius, 2000)		k = −20→20
Tmin = 0.540, Tmax = 0.937l = −20→20
53227 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.077Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.232H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1118P)2 + 21.2954P]
where P = (Fo2 + 2Fc2)/3
6802 reflections(Δ/σ)max < 0.001
469 parametersΔρmax = 2.19 e Å−3
0 restraintsΔρmin = −1.30 e Å−3
Crystal data top
[Fe(C5H4Br)(C17H14PS)]V = 3853.0 (3) Å3
Mr = 481.15Z = 8
Monoclinic, P21/nMo Kα radiation
a = 13.3590 (7) ŵ = 3.05 mm−1
b = 17.3446 (7) ÅT = 150 K
c = 17.0297 (9) Å0.25 × 0.18 × 0.02 mm
β = 102.460 (2)°
Data collection top
Nonius KappaCCD
diffractometer		6802 independent reflections
Absorption correction: integration
(COLLECT; Nonius, 2000)		4020 reflections with I > 2σ(I)
Tmin = 0.540, Tmax = 0.937Rint = 0.122
53227 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0770 restraints
wR(F2) = 0.232H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1118P)2 + 21.2954P]
where P = (Fo2 + 2Fc2)/3
6802 reflectionsΔρmax = 2.19 e Å−3
469 parametersΔρmin = −1.30 e Å−3
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 diffractions. 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
Br10.85670 (9)0.54776 (7)0.15983 (7)0.0553 (4)
Fe10.80463 (9)0.57655 (7)0.35241 (8)0.0282 (3)
P10.72687 (16)0.39009 (12)0.36630 (14)0.0230 (5)
S10.84979 (17)0.35593 (13)0.44183 (14)0.0319 (6)
C10.8910 (7)0.5779 (6)0.2679 (6)0.040 (3)
C20.8859 (7)0.6525 (5)0.3000 (6)0.040 (2)
H20.85970.69660.27180.048*
C30.9281 (7)0.6474 (6)0.3827 (7)0.043 (3)
H30.93500.68810.41910.052*
C40.9582 (7)0.5711 (6)0.4016 (7)0.045 (3)
H40.98850.55270.45240.054*
C50.9349 (7)0.5267 (6)0.3305 (7)0.039 (2)
H50.94620.47410.32580.047*
C60.7056 (6)0.4930 (5)0.3685 (6)0.028 (2)
C70.6582 (6)0.5407 (5)0.3007 (6)0.030 (2)
H70.63290.52440.24810.036*
C80.6581 (8)0.6174 (5)0.3304 (7)0.043 (3)
H80.63520.66100.30010.051*
C90.6993 (8)0.6153 (5)0.4144 (7)0.040 (3)
H90.70480.65760.44860.048*
C100.7310 (7)0.5391 (5)0.4388 (6)0.031 (2)
H100.76200.52290.49040.038*
C110.6117 (6)0.3477 (5)0.3868 (5)0.0246 (19)
C120.5310 (7)0.3923 (5)0.4047 (5)0.028 (2)
H120.53660.44570.40690.033*
C130.4442 (6)0.3574 (6)0.4189 (6)0.033 (2)
H130.39160.38740.43050.039*
C140.4344 (7)0.2782 (6)0.4159 (6)0.039 (2)
H140.37550.25510.42560.046*
C150.5121 (7)0.2334 (6)0.3986 (6)0.040 (2)
H150.50520.18000.39620.048*
C160.6008 (7)0.2679 (5)0.3847 (5)0.033 (2)
H160.65340.23730.37390.039*
C170.7236 (7)0.3656 (4)0.2624 (5)0.026 (2)
C180.8128 (7)0.3432 (5)0.2390 (6)0.031 (2)
H180.87370.33910.27740.038*
C190.8121 (8)0.3271 (5)0.1601 (7)0.042 (3)
H190.87200.31220.14470.051*
C200.7211 (9)0.3333 (5)0.1037 (6)0.041 (3)
H200.72060.32350.04990.049*
C210.6317 (8)0.3535 (5)0.1252 (6)0.037 (2)
H210.57100.35660.08640.044*
C220.6322 (7)0.3691 (5)0.2049 (5)0.029 (2)
H220.57150.38210.22010.035*
Br20.15365 (8)0.37352 (6)0.34428 (7)0.0489 (3)
Fe20.20450 (9)0.34881 (7)0.15086 (8)0.0241 (3)
P20.27899 (16)0.53407 (12)0.12992 (14)0.0236 (5)
S20.15627 (18)0.56445 (14)0.05199 (16)0.0376 (6)
C310.1180 (7)0.3485 (5)0.2346 (6)0.031 (2)
C320.0746 (7)0.4003 (6)0.1723 (7)0.039 (3)
H320.06280.45260.17780.046*
C330.0526 (6)0.3575 (5)0.1003 (6)0.036 (2)
H330.02530.37760.04950.044*
C340.0784 (7)0.2796 (5)0.1170 (6)0.036 (2)
H340.07010.23970.07960.043*
C350.1194 (7)0.2727 (5)0.2008 (6)0.036 (2)
H350.14270.22780.22860.043*
C360.3034 (6)0.4324 (5)0.1337 (5)0.0251 (19)
C370.2800 (7)0.3822 (5)0.0653 (6)0.029 (2)
H370.24960.39720.01320.035*
C380.3102 (7)0.3067 (5)0.0895 (6)0.033 (2)
H380.30380.26330.05660.040*
C390.3531 (7)0.3090 (5)0.1747 (6)0.035 (2)
H390.37920.26710.20670.041*
C400.3487 (6)0.3862 (5)0.2016 (6)0.029 (2)
H400.37120.40370.25410.035*
C410.3951 (6)0.5776 (5)0.1109 (5)0.0230 (19)
C420.4756 (7)0.5350 (5)0.0960 (5)0.031 (2)
H420.47030.48150.09340.037*
C430.5660 (7)0.5709 (5)0.0846 (6)0.033 (2)
H430.62030.54180.07440.039*
C440.5721 (7)0.6503 (6)0.0891 (6)0.039 (2)
H440.63150.67500.08250.047*
C450.4915 (7)0.6933 (6)0.1031 (6)0.036 (2)
H450.49640.74680.10580.043*
C460.4034 (7)0.6572 (5)0.1131 (6)0.033 (2)
H460.34850.68670.12140.039*
C470.2813 (6)0.5609 (4)0.2336 (5)0.0241 (19)
C480.3725 (7)0.5582 (5)0.2893 (5)0.028 (2)
H480.43240.54380.27370.034*
C490.3748 (8)0.5771 (5)0.3698 (6)0.037 (2)
H490.43600.57410.40810.044*
C500.2868 (9)0.5999 (5)0.3918 (6)0.040 (3)
H500.28850.61400.44480.048*
C510.1952 (8)0.6020 (5)0.3356 (6)0.039 (2)
H510.13520.61510.35170.047*
C520.1918 (7)0.5852 (5)0.2564 (6)0.029 (2)
H520.13070.58980.21830.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0560 (7)0.0594 (8)0.0531 (8)0.0027 (6)0.0179 (6)0.0036 (6)
Fe10.0288 (7)0.0233 (7)0.0330 (8)−0.0023 (5)0.0082 (6)0.0025 (5)
P10.0245 (12)0.0226 (11)0.0227 (13)−0.0005 (9)0.0071 (10)−0.0012 (9)
S10.0292 (12)0.0336 (12)0.0319 (14)0.0014 (10)0.0042 (10)0.0021 (10)
C10.042 (6)0.042 (6)0.045 (7)−0.013 (5)0.029 (5)−0.009 (5)
C20.039 (6)0.031 (5)0.051 (7)−0.007 (4)0.012 (5)0.012 (5)
C30.031 (5)0.038 (6)0.058 (8)−0.009 (4)0.003 (5)−0.002 (5)
C40.029 (5)0.042 (6)0.058 (8)−0.005 (4)0.000 (5)0.021 (5)
C50.028 (5)0.031 (5)0.061 (8)0.003 (4)0.017 (5)0.007 (5)
C60.021 (4)0.027 (5)0.035 (6)0.002 (4)0.007 (4)0.002 (4)
C70.023 (5)0.030 (5)0.034 (6)0.006 (4)−0.002 (4)0.005 (4)
C80.046 (6)0.018 (5)0.073 (9)0.007 (4)0.032 (6)0.002 (5)
C90.057 (6)0.022 (5)0.048 (7)−0.005 (4)0.028 (6)−0.011 (4)
C100.033 (5)0.026 (5)0.037 (6)−0.006 (4)0.015 (4)−0.004 (4)
C110.033 (5)0.022 (4)0.020 (5)−0.005 (4)0.008 (4)0.002 (4)
C120.034 (5)0.026 (5)0.026 (5)−0.001 (4)0.013 (4)−0.001 (4)
C130.015 (4)0.054 (6)0.032 (6)0.004 (4)0.010 (4)0.003 (5)
C140.030 (5)0.050 (6)0.036 (6)−0.018 (5)0.008 (4)0.008 (5)
C150.045 (6)0.037 (6)0.039 (6)−0.012 (5)0.013 (5)0.002 (5)
C160.041 (5)0.037 (5)0.026 (5)−0.003 (4)0.017 (4)0.001 (4)
C170.036 (5)0.018 (4)0.025 (5)−0.002 (4)0.012 (4)−0.002 (4)
C180.031 (5)0.030 (5)0.035 (6)−0.002 (4)0.013 (4)−0.003 (4)
C190.047 (6)0.030 (5)0.057 (8)−0.002 (4)0.027 (6)−0.008 (5)
C200.072 (8)0.027 (5)0.027 (6)−0.003 (5)0.018 (6)−0.005 (4)
C210.047 (6)0.029 (5)0.030 (6)0.012 (4)−0.003 (5)0.001 (4)
C220.032 (5)0.029 (5)0.023 (5)0.008 (4)0.002 (4)0.002 (4)
Br20.0527 (7)0.0513 (7)0.0467 (7)−0.0014 (5)0.0192 (5)−0.0049 (5)
Fe20.0235 (7)0.0221 (7)0.0273 (8)−0.0006 (5)0.0070 (5)0.0010 (5)
P20.0236 (11)0.0238 (11)0.0244 (13)0.0009 (9)0.0074 (10)0.0022 (9)
S20.0301 (13)0.0393 (14)0.0406 (16)0.0027 (10)0.0013 (11)0.0100 (11)
C310.031 (5)0.030 (5)0.038 (6)−0.005 (4)0.021 (4)−0.002 (4)
C320.020 (5)0.033 (5)0.065 (8)−0.001 (4)0.014 (5)0.007 (5)
C330.019 (5)0.044 (6)0.045 (7)−0.004 (4)0.005 (4)0.010 (5)
C340.033 (5)0.030 (5)0.042 (6)−0.007 (4)0.006 (4)0.004 (4)
C350.033 (5)0.029 (5)0.049 (7)−0.007 (4)0.016 (5)0.002 (4)
C360.025 (4)0.027 (5)0.026 (5)−0.003 (4)0.012 (4)−0.001 (4)
C370.033 (5)0.035 (5)0.023 (5)0.000 (4)0.014 (4)−0.004 (4)
C380.034 (5)0.027 (5)0.043 (7)0.002 (4)0.017 (5)−0.005 (4)
C390.028 (5)0.024 (5)0.053 (7)0.003 (4)0.011 (5)0.007 (4)
C400.021 (5)0.033 (5)0.035 (6)0.003 (4)0.011 (4)0.000 (4)
C410.023 (4)0.025 (4)0.023 (5)−0.004 (4)0.007 (4)0.004 (4)
C420.042 (5)0.027 (5)0.027 (5)0.002 (4)0.016 (4)−0.001 (4)
C430.027 (5)0.045 (6)0.027 (6)0.001 (4)0.009 (4)0.003 (4)
C440.037 (6)0.044 (6)0.042 (6)−0.009 (5)0.020 (5)−0.005 (5)
C450.038 (5)0.035 (5)0.039 (6)−0.006 (4)0.015 (5)−0.002 (4)
C460.034 (5)0.027 (5)0.036 (6)0.003 (4)0.004 (4)−0.002 (4)
C470.032 (5)0.020 (4)0.024 (5)0.001 (4)0.015 (4)−0.008 (4)
C480.035 (5)0.021 (4)0.030 (6)0.002 (4)0.007 (4)−0.004 (4)
C490.053 (6)0.029 (5)0.030 (6)0.003 (4)0.013 (5)0.000 (4)
C500.073 (8)0.024 (5)0.032 (6)0.002 (5)0.031 (6)−0.001 (4)
C510.048 (6)0.029 (5)0.050 (7)−0.002 (4)0.032 (6)−0.003 (5)
C520.026 (5)0.028 (5)0.036 (6)−0.002 (4)0.014 (4)−0.001 (4)
Geometric parameters (Å, º) top
Br1—C11.872 (10)Br2—C311.877 (10)
Fe1—C62.020 (8)Fe2—C312.020 (9)
Fe1—C12.030 (9)Fe2—C362.024 (8)
Fe1—C32.033 (9)Fe2—C372.027 (9)
Fe1—C22.033 (9)Fe2—C332.032 (9)
Fe1—C82.038 (10)Fe2—C402.040 (9)
Fe1—C42.044 (10)Fe2—C352.043 (9)
Fe1—C102.045 (9)Fe2—C342.047 (9)
Fe1—C92.046 (10)Fe2—C322.053 (9)
Fe1—C52.049 (9)Fe2—C392.057 (9)
Fe1—C72.060 (9)Fe2—C382.064 (9)
P1—C111.806 (8)P2—C361.792 (8)
P1—C61.809 (9)P2—C411.815 (8)
P1—C171.811 (9)P2—C471.820 (8)
P1—S11.947 (3)P2—S21.946 (3)
C1—C21.413 (14)C31—C321.415 (13)
C1—C51.415 (14)C31—C351.437 (13)
C2—C31.402 (15)C32—C331.409 (14)
C2—H20.9300C32—H320.9300
C3—C41.401 (14)C33—C341.409 (13)
C3—H30.9300C33—H330.9300
C4—C51.412 (15)C34—C351.420 (14)
C4—H40.9300C34—H340.9300
C5—H50.9300C35—H350.9300
C6—C101.419 (13)C36—C401.429 (12)
C6—C71.451 (12)C36—C371.433 (12)
C7—C81.423 (13)C37—C381.406 (12)
C7—H70.9300C37—H370.9300
C8—C91.418 (15)C38—C391.441 (14)
C8—H80.9300C38—H380.9300
C9—C101.421 (13)C39—C401.421 (12)
C9—H90.9300C39—H390.9300
C10—H100.9300C40—H400.9300
C11—C161.390 (12)C41—C421.373 (12)
C11—C121.412 (12)C41—C461.385 (12)
C12—C131.374 (12)C42—C431.409 (12)
C12—H120.9300C42—H420.9300
C13—C141.379 (13)C43—C441.382 (13)
C13—H130.9300C43—H430.9300
C14—C151.378 (14)C44—C451.372 (13)
C14—H140.9300C44—H440.9300
C15—C161.394 (12)C45—C461.376 (13)
C15—H150.9300C45—H450.9300
C16—H160.9300C46—H460.9300
C17—C181.391 (12)C47—C481.374 (12)
C17—C221.392 (12)C47—C521.399 (12)
C18—C191.371 (14)C48—C491.405 (13)
C18—H180.9300C48—H480.9300
C19—C201.382 (14)C49—C501.368 (14)
C19—H190.9300C49—H490.9300
C20—C211.368 (14)C50—C511.381 (15)
C20—H200.9300C50—H500.9300
C21—C221.383 (13)C51—C521.371 (13)
C21—H210.9300C51—H510.9300
C22—H220.9300C52—H520.9300
C6—Fe1—C1126.4 (4)C31—Fe2—C36126.5 (3)
C6—Fe1—C3156.7 (4)C31—Fe2—C37163.2 (4)
C1—Fe1—C367.6 (4)C36—Fe2—C3741.4 (3)
C6—Fe1—C2162.2 (4)C31—Fe2—C3368.2 (4)
C1—Fe1—C240.7 (4)C36—Fe2—C33120.6 (4)
C3—Fe1—C240.3 (4)C37—Fe2—C33106.3 (4)
C6—Fe1—C869.1 (4)C31—Fe2—C40109.5 (4)
C1—Fe1—C8122.4 (4)C36—Fe2—C4041.2 (3)
C3—Fe1—C8122.1 (4)C37—Fe2—C4069.1 (4)
C2—Fe1—C8106.1 (4)C33—Fe2—C40157.1 (4)
C6—Fe1—C4122.7 (4)C31—Fe2—C3541.4 (4)
C1—Fe1—C467.5 (4)C36—Fe2—C35164.1 (4)
C3—Fe1—C440.2 (4)C37—Fe2—C35153.1 (4)
C2—Fe1—C468.0 (4)C33—Fe2—C3568.3 (4)
C8—Fe1—C4158.5 (4)C40—Fe2—C35126.0 (4)
C6—Fe1—C1040.9 (3)C31—Fe2—C3468.7 (4)
C1—Fe1—C10161.7 (4)C36—Fe2—C34154.4 (4)
C3—Fe1—C10120.0 (4)C37—Fe2—C34118.1 (4)
C2—Fe1—C10155.2 (4)C33—Fe2—C3440.4 (4)
C8—Fe1—C1069.5 (4)C40—Fe2—C34161.9 (4)
C4—Fe1—C10106.7 (4)C35—Fe2—C3440.6 (4)
C6—Fe1—C967.8 (3)C31—Fe2—C3240.7 (4)
C1—Fe1—C9157.1 (4)C36—Fe2—C32108.5 (4)
C3—Fe1—C9106.4 (4)C37—Fe2—C32125.0 (4)
C2—Fe1—C9120.4 (4)C33—Fe2—C3240.3 (4)
C8—Fe1—C940.6 (4)C40—Fe2—C32122.9 (4)
C4—Fe1—C9123.0 (5)C35—Fe2—C3268.9 (4)
C10—Fe1—C940.7 (4)C34—Fe2—C3268.3 (4)
C6—Fe1—C5109.2 (4)C31—Fe2—C39122.3 (4)
C1—Fe1—C540.6 (4)C36—Fe2—C3968.7 (3)
C3—Fe1—C568.1 (4)C37—Fe2—C3968.2 (4)
C2—Fe1—C568.8 (4)C33—Fe2—C39160.3 (4)
C8—Fe1—C5158.9 (5)C40—Fe2—C3940.6 (3)
C4—Fe1—C540.4 (4)C35—Fe2—C39107.5 (4)
C10—Fe1—C5123.8 (4)C34—Fe2—C39124.0 (4)
C9—Fe1—C5159.8 (4)C32—Fe2—C39158.0 (4)
C6—Fe1—C741.6 (3)C31—Fe2—C38156.2 (4)
C1—Fe1—C7109.4 (4)C36—Fe2—C3869.0 (3)
C3—Fe1—C7159.2 (4)C37—Fe2—C3840.2 (3)
C2—Fe1—C7123.8 (4)C33—Fe2—C38122.8 (4)
C8—Fe1—C740.6 (4)C40—Fe2—C3868.9 (4)
C4—Fe1—C7159.6 (4)C35—Fe2—C38119.0 (4)
C10—Fe1—C769.6 (4)C34—Fe2—C38105.1 (4)
C9—Fe1—C768.0 (4)C32—Fe2—C38160.2 (4)
C5—Fe1—C7124.0 (4)C39—Fe2—C3840.9 (4)
C11—P1—C6104.7 (4)C36—P2—C41105.1 (4)
C11—P1—C17104.6 (4)C36—P2—C47104.6 (4)
C6—P1—C17106.3 (4)C41—P2—C47103.3 (4)
C11—P1—S1112.4 (3)C36—P2—S2114.3 (3)
C6—P1—S1113.6 (3)C41—P2—S2113.1 (3)
C17—P1—S1114.4 (3)C47—P2—S2115.3 (3)
C2—C1—C5109.3 (9)C32—C31—C35108.6 (9)
C2—C1—Br1127.9 (8)C32—C31—Br2125.1 (7)
C5—C1—Br1122.7 (8)C35—C31—Br2126.0 (7)
C2—C1—Fe169.8 (6)C32—C31—Fe270.9 (5)
C5—C1—Fe170.4 (6)C35—C31—Fe270.2 (5)
Br1—C1—Fe1129.7 (5)Br2—C31—Fe2129.9 (5)
C3—C2—C1106.8 (9)C33—C32—C31107.1 (8)
C3—C2—Fe169.8 (6)C33—C32—Fe269.0 (5)
C1—C2—Fe169.5 (5)C31—C32—Fe268.4 (5)
C3—C2—H2126.6C33—C32—H32126.5
C1—C2—H2126.6C31—C32—H32126.5
Fe1—C2—H2125.6Fe2—C32—H32127.7
C4—C3—C2108.9 (10)C32—C33—C34109.5 (9)
C4—C3—Fe170.3 (5)C32—C33—Fe270.7 (5)
C2—C3—Fe169.8 (5)C34—C33—Fe270.4 (5)
C4—C3—H3125.6C32—C33—H33125.3
C2—C3—H3125.6C34—C33—H33125.3
Fe1—C3—H3125.9Fe2—C33—H33125.3
C3—C4—C5108.7 (9)C33—C34—C35107.9 (9)
C3—C4—Fe169.5 (5)C33—C34—Fe269.2 (5)
C5—C4—Fe170.0 (5)C35—C34—Fe269.5 (5)
C3—C4—H4125.7C33—C34—H34126.0
C5—C4—H4125.7C35—C34—H34126.0
Fe1—C4—H4126.4Fe2—C34—H34126.8
C4—C5—C1106.4 (9)C34—C35—C31106.9 (8)
C4—C5—Fe169.7 (6)C34—C35—Fe269.8 (5)
C1—C5—Fe169.0 (5)C31—C35—Fe268.4 (5)
C4—C5—H5126.8C34—C35—H35126.6
C1—C5—H5126.8C31—C35—H35126.6
Fe1—C5—H5126.1Fe2—C35—H35126.7
C10—C6—C7109.6 (8)C40—C36—C37107.3 (7)
C10—C6—P1124.3 (7)C40—C36—P2128.5 (7)
C7—C6—P1126.1 (7)C37—C36—P2124.2 (7)
C10—C6—Fe170.5 (5)C40—C36—Fe270.0 (5)
C7—C6—Fe170.7 (5)C37—C36—Fe269.4 (5)
P1—C6—Fe1126.5 (4)P2—C36—Fe2126.2 (4)
C8—C7—C6106.4 (9)C38—C37—C36109.2 (8)
C8—C7—Fe168.8 (5)C38—C37—Fe271.3 (5)
C6—C7—Fe167.7 (5)C36—C37—Fe269.2 (5)
C8—C7—H7126.8C38—C37—H37125.4
C6—C7—H7126.8C36—C37—H37125.4
Fe1—C7—H7128.2Fe2—C37—H37125.7
C9—C8—C7107.8 (8)C37—C38—C39107.2 (8)
C9—C8—Fe170.0 (6)C37—C38—Fe268.5 (5)
C7—C8—Fe170.5 (5)C39—C38—Fe269.3 (5)
C9—C8—H8126.1C37—C38—H38126.4
C7—C8—H8126.1C39—C38—H38126.4
Fe1—C8—H8125.0Fe2—C38—H38127.3
C8—C9—C10110.2 (8)C40—C39—C38108.5 (8)
C8—C9—Fe169.4 (5)C40—C39—Fe269.0 (5)
C10—C9—Fe169.6 (5)C38—C39—Fe269.8 (5)
C8—C9—H9124.9C40—C39—H39125.8
C10—C9—H9124.9C38—C39—H39125.8
Fe1—C9—H9127.7Fe2—C39—H39127.0
C6—C10—C9106.0 (9)C39—C40—C36107.8 (8)
C6—C10—Fe168.6 (5)C39—C40—Fe270.4 (5)
C9—C10—Fe169.7 (5)C36—C40—Fe268.8 (5)
C6—C10—H10127.0C39—C40—H40126.1
C9—C10—H10127.0C36—C40—H40126.1
Fe1—C10—H10126.2Fe2—C40—H40126.3
C16—C11—C12118.0 (8)C42—C41—C46118.7 (8)
C16—C11—P1119.3 (7)C42—C41—P2122.8 (6)
C12—C11—P1122.7 (6)C46—C41—P2118.5 (7)
C13—C12—C11120.6 (8)C41—C42—C43121.1 (8)
C13—C12—H12119.7C41—C42—H42119.5
C11—C12—H12119.7C43—C42—H42119.5
C12—C13—C14120.6 (8)C44—C43—C42118.4 (8)
C12—C13—H13119.7C44—C43—H43120.8
C14—C13—H13119.7C42—C43—H43120.8
C15—C14—C13120.0 (8)C45—C44—C43120.9 (9)
C15—C14—H14120.0C45—C44—H44119.6
C13—C14—H14120.0C43—C44—H44119.6
C14—C15—C16120.1 (9)C44—C45—C46119.8 (9)
C14—C15—H15120.0C44—C45—H45120.1
C16—C15—H15120.0C46—C45—H45120.1
C11—C16—C15120.7 (9)C45—C46—C41121.1 (9)
C11—C16—H16119.6C45—C46—H46119.4
C15—C16—H16119.6C41—C46—H46119.4
C18—C17—C22119.1 (8)C48—C47—C52120.2 (8)
C18—C17—P1120.3 (7)C48—C47—P2119.2 (6)
C22—C17—P1120.6 (7)C52—C47—P2120.7 (7)
C19—C18—C17120.9 (9)C47—C48—C49119.7 (9)
C19—C18—H18119.6C47—C48—H48120.2
C17—C18—H18119.6C49—C48—H48120.2
C18—C19—C20119.0 (9)C50—C49—C48119.7 (10)
C18—C19—H19120.5C50—C49—H49120.1
C20—C19—H19120.5C48—C49—H49120.1
C21—C20—C19121.5 (9)C49—C50—C51120.2 (9)
C21—C20—H20119.3C49—C50—H50119.9
C19—C20—H20119.3C51—C50—H50119.9
C20—C21—C22119.6 (9)C52—C51—C50120.9 (9)
C20—C21—H21120.2C52—C51—H51119.6
C22—C21—H21120.2C50—C51—H51119.6
C21—C22—C17120.0 (9)C51—C52—C47119.2 (9)
C21—C22—H22120.0C51—C52—H52120.4
C17—C22—H22120.0C47—C52—H52120.4
C6—Fe1—C1—C2163.2 (6)C36—Fe2—C31—C3275.2 (7)
C3—Fe1—C1—C2−38.3 (6)C37—Fe2—C31—C3236.2 (15)
C8—Fe1—C1—C276.5 (7)C33—Fe2—C31—C32−37.4 (6)
C4—Fe1—C1—C2−81.9 (6)C40—Fe2—C31—C32118.2 (6)
C10—Fe1—C1—C2−156.7 (11)C35—Fe2—C31—C32−118.9 (8)
C9—Fe1—C1—C240.5 (13)C34—Fe2—C31—C32−81.0 (6)
C5—Fe1—C1—C2−120.3 (9)C39—Fe2—C31—C32161.4 (5)
C7—Fe1—C1—C2119.6 (6)C38—Fe2—C31—C32−160.0 (9)
C6—Fe1—C1—C5−76.5 (7)C36—Fe2—C31—C35−165.9 (5)
C3—Fe1—C1—C582.0 (6)C37—Fe2—C31—C35155.1 (12)
C2—Fe1—C1—C5120.3 (9)C33—Fe2—C31—C3581.5 (6)
C8—Fe1—C1—C5−163.2 (6)C40—Fe2—C31—C35−122.9 (6)
C4—Fe1—C1—C538.3 (6)C34—Fe2—C31—C3537.9 (5)
C10—Fe1—C1—C5−36.4 (15)C32—Fe2—C31—C35118.9 (8)
C9—Fe1—C1—C5160.8 (10)C39—Fe2—C31—C35−79.7 (6)
C7—Fe1—C1—C5−120.1 (6)C38—Fe2—C31—C35−41.1 (12)
C6—Fe1—C1—Br140.1 (9)C36—Fe2—C31—Br2−45.0 (8)
C3—Fe1—C1—Br1−161.3 (8)C37—Fe2—C31—Br2−84.1 (15)
C2—Fe1—C1—Br1−123.0 (10)C33—Fe2—C31—Br2−157.7 (7)
C8—Fe1—C1—Br1−46.6 (8)C40—Fe2—C31—Br2−2.0 (7)
C4—Fe1—C1—Br1155.0 (8)C35—Fe2—C31—Br2120.8 (9)
C10—Fe1—C1—Br180.3 (15)C34—Fe2—C31—Br2158.7 (7)
C9—Fe1—C1—Br1−82.5 (12)C32—Fe2—C31—Br2−120.2 (9)
C5—Fe1—C1—Br1116.7 (9)C39—Fe2—C31—Br241.2 (7)
C7—Fe1—C1—Br1−3.4 (8)C38—Fe2—C31—Br279.8 (11)
C5—C1—C2—C30.7 (11)C35—C31—C32—C33−2.0 (10)
Br1—C1—C2—C3−174.7 (7)Br2—C31—C32—C33−175.8 (6)
Fe1—C1—C2—C360.2 (7)Fe2—C31—C32—C3358.4 (6)
C5—C1—C2—Fe1−59.5 (7)C35—C31—C32—Fe2−60.3 (6)
Br1—C1—C2—Fe1125.1 (8)Br2—C31—C32—Fe2125.9 (7)
C6—Fe1—C2—C3−167.5 (11)C31—Fe2—C32—C33−119.3 (8)
C1—Fe1—C2—C3−117.7 (9)C36—Fe2—C32—C33115.8 (6)
C8—Fe1—C2—C3121.0 (6)C37—Fe2—C32—C3372.7 (7)
C4—Fe1—C2—C3−37.1 (6)C40—Fe2—C32—C33159.0 (5)
C10—Fe1—C2—C345.1 (12)C35—Fe2—C32—C33−81.0 (6)
C9—Fe1—C2—C379.3 (7)C34—Fe2—C32—C33−37.2 (6)
C5—Fe1—C2—C3−80.7 (7)C39—Fe2—C32—C33−165.4 (9)
C7—Fe1—C2—C3161.7 (6)C38—Fe2—C32—C3336.6 (13)
C6—Fe1—C2—C1−49.8 (14)C36—Fe2—C32—C31−124.9 (5)
C3—Fe1—C2—C1117.7 (9)C37—Fe2—C32—C31−168.0 (5)
C8—Fe1—C2—C1−121.3 (7)C33—Fe2—C32—C31119.3 (8)
C4—Fe1—C2—C180.6 (7)C40—Fe2—C32—C31−81.7 (6)
C10—Fe1—C2—C1162.8 (9)C35—Fe2—C32—C3138.4 (5)
C9—Fe1—C2—C1−163.0 (6)C34—Fe2—C32—C3182.1 (6)
C5—Fe1—C2—C137.1 (6)C39—Fe2—C32—C31−46.1 (12)
C7—Fe1—C2—C1−80.5 (7)C38—Fe2—C32—C31155.9 (9)
C1—C2—C3—C4−0.3 (11)C31—C32—C33—C341.9 (10)
Fe1—C2—C3—C459.7 (7)Fe2—C32—C33—C3459.9 (6)
C1—C2—C3—Fe1−60.0 (6)C31—C32—C33—Fe2−58.0 (6)
C6—Fe1—C3—C450.6 (13)C31—Fe2—C33—C3237.7 (6)
C1—Fe1—C3—C4−81.2 (7)C36—Fe2—C33—C32−82.7 (6)
C2—Fe1—C3—C4−119.8 (9)C37—Fe2—C33—C32−125.5 (6)
C8—Fe1—C3—C4163.7 (7)C40—Fe2—C33—C32−50.8 (12)
C10—Fe1—C3—C480.2 (8)C35—Fe2—C33—C3282.5 (6)
C9—Fe1—C3—C4122.2 (7)C34—Fe2—C33—C32120.0 (8)
C5—Fe1—C3—C4−37.2 (7)C39—Fe2—C33—C32163.8 (10)
C7—Fe1—C3—C4−166.9 (11)C38—Fe2—C33—C32−166.1 (5)
C6—Fe1—C3—C2170.4 (8)C31—Fe2—C33—C34−82.3 (6)
C1—Fe1—C3—C238.6 (6)C36—Fe2—C33—C34157.2 (6)
C8—Fe1—C3—C2−76.5 (7)C37—Fe2—C33—C34114.5 (6)
C4—Fe1—C3—C2119.8 (9)C40—Fe2—C33—C34−170.8 (9)
C10—Fe1—C3—C2−159.9 (6)C35—Fe2—C33—C34−37.5 (6)
C9—Fe1—C3—C2−118.0 (6)C32—Fe2—C33—C34−120.0 (8)
C5—Fe1—C3—C282.6 (7)C39—Fe2—C33—C3443.8 (14)
C7—Fe1—C3—C2−47.1 (15)C38—Fe2—C33—C3473.9 (7)
C2—C3—C4—C5−0.2 (11)C32—C33—C34—C35−1.1 (10)
Fe1—C3—C4—C559.2 (7)Fe2—C33—C34—C3558.9 (6)
C2—C3—C4—Fe1−59.4 (7)C32—C33—C34—Fe2−60.1 (6)
C6—Fe1—C4—C3−158.8 (6)C31—Fe2—C34—C3381.0 (6)
C1—Fe1—C4—C381.4 (7)C36—Fe2—C34—C33−50.5 (11)
C2—Fe1—C4—C337.3 (7)C37—Fe2—C34—C33−82.1 (7)
C8—Fe1—C4—C3−40.5 (15)C40—Fe2—C34—C33168.5 (11)
C10—Fe1—C4—C3−117.0 (7)C35—Fe2—C34—C33119.6 (8)
C9—Fe1—C4—C3−75.6 (8)C32—Fe2—C34—C3337.1 (6)
C5—Fe1—C4—C3120.0 (9)C39—Fe2—C34—C33−163.6 (6)
C7—Fe1—C4—C3166.6 (11)C38—Fe2—C34—C33−123.2 (6)
C6—Fe1—C4—C581.3 (7)C31—Fe2—C34—C35−38.6 (6)
C1—Fe1—C4—C5−38.6 (6)C36—Fe2—C34—C35−170.0 (7)
C3—Fe1—C4—C5−120.0 (9)C37—Fe2—C34—C35158.4 (5)
C2—Fe1—C4—C5−82.7 (6)C33—Fe2—C34—C35−119.6 (8)
C8—Fe1—C4—C5−160.5 (10)C40—Fe2—C34—C3549.0 (15)
C10—Fe1—C4—C5123.0 (6)C32—Fe2—C34—C35−82.5 (6)
C9—Fe1—C4—C5164.5 (6)C39—Fe2—C34—C3576.8 (7)
C7—Fe1—C4—C546.7 (15)C38—Fe2—C34—C35117.2 (6)
C3—C4—C5—C10.6 (11)C33—C34—C35—C31−0.1 (10)
Fe1—C4—C5—C159.5 (6)Fe2—C34—C35—C3158.6 (6)
C3—C4—C5—Fe1−58.9 (7)C33—C34—C35—Fe2−58.7 (6)
C2—C1—C5—C4−0.8 (11)C32—C31—C35—C341.3 (10)
Br1—C1—C5—C4174.9 (7)Br2—C31—C35—C34175.0 (6)
Fe1—C1—C5—C4−59.9 (7)Fe2—C31—C35—C34−59.5 (6)
C2—C1—C5—Fe159.1 (7)C32—C31—C35—Fe260.8 (6)
Br1—C1—C5—Fe1−125.2 (7)Br2—C31—C35—Fe2−125.5 (7)
C6—Fe1—C5—C4−118.3 (6)C31—Fe2—C35—C34118.5 (8)
C1—Fe1—C5—C4117.7 (8)C36—Fe2—C35—C34164.2 (12)
C3—Fe1—C5—C437.0 (6)C37—Fe2—C35—C34−45.9 (11)
C2—Fe1—C5—C480.6 (6)C33—Fe2—C35—C3437.4 (6)
C8—Fe1—C5—C4160.2 (9)C40—Fe2—C35—C34−163.1 (5)
C10—Fe1—C5—C4−75.2 (7)C32—Fe2—C35—C3480.8 (6)
C9—Fe1—C5—C4−40.6 (13)C39—Fe2—C35—C34−122.2 (6)
C7—Fe1—C5—C4−162.2 (5)C38—Fe2—C35—C34−79.1 (6)
C6—Fe1—C5—C1124.0 (6)C36—Fe2—C35—C3145.7 (15)
C3—Fe1—C5—C1−80.7 (6)C37—Fe2—C35—C31−164.4 (7)
C2—Fe1—C5—C1−37.2 (6)C33—Fe2—C35—C31−81.2 (6)
C8—Fe1—C5—C142.5 (13)C40—Fe2—C35—C3178.4 (6)
C4—Fe1—C5—C1−117.7 (8)C34—Fe2—C35—C31−118.5 (8)
C10—Fe1—C5—C1167.1 (5)C32—Fe2—C35—C31−37.7 (6)
C9—Fe1—C5—C1−158.3 (10)C39—Fe2—C35—C31119.3 (6)
C7—Fe1—C5—C180.1 (6)C38—Fe2—C35—C31162.4 (5)
C11—P1—C6—C1088.7 (8)C41—P2—C36—C4089.0 (8)
C17—P1—C6—C10−161.0 (7)C47—P2—C36—C40−19.5 (9)
S1—P1—C6—C10−34.3 (8)S2—P2—C36—C40−146.5 (7)
C11—P1—C6—C7−89.5 (8)C41—P2—C36—C37−90.4 (8)
C17—P1—C6—C720.8 (8)C47—P2—C36—C37161.1 (7)
S1—P1—C6—C7147.5 (7)S2—P2—C36—C3734.1 (8)
C11—P1—C6—Fe1178.8 (5)C41—P2—C36—Fe2−178.7 (5)
C17—P1—C6—Fe1−70.8 (6)C47—P2—C36—Fe272.8 (6)
S1—P1—C6—Fe155.9 (6)S2—P2—C36—Fe2−54.2 (6)
C1—Fe1—C6—C10162.0 (6)C31—Fe2—C36—C4077.6 (6)
C3—Fe1—C6—C1041.0 (12)C37—Fe2—C36—C40−118.4 (7)
C2—Fe1—C6—C10−159.8 (11)C33—Fe2—C36—C40161.8 (5)
C8—Fe1—C6—C10−82.5 (6)C35—Fe2—C36—C4041.5 (15)
C4—Fe1—C6—C1077.3 (7)C34—Fe2—C36—C40−162.7 (8)
C9—Fe1—C6—C10−38.7 (6)C32—Fe2—C36—C40119.2 (6)
C5—Fe1—C6—C10119.9 (6)C39—Fe2—C36—C40−37.6 (5)
C7—Fe1—C6—C10−120.0 (7)C38—Fe2—C36—C40−81.6 (5)
C1—Fe1—C6—C7−78.0 (7)C31—Fe2—C36—C37−164.0 (5)
C3—Fe1—C6—C7161.0 (9)C33—Fe2—C36—C37−79.8 (6)
C2—Fe1—C6—C7−39.7 (14)C40—Fe2—C36—C37118.4 (7)
C8—Fe1—C6—C737.5 (6)C35—Fe2—C36—C37159.9 (12)
C4—Fe1—C6—C7−162.7 (6)C34—Fe2—C36—C37−44.3 (10)
C10—Fe1—C6—C7120.0 (7)C32—Fe2—C36—C37−122.4 (6)
C9—Fe1—C6—C781.3 (6)C39—Fe2—C36—C3780.8 (6)
C5—Fe1—C6—C7−120.0 (6)C38—Fe2—C36—C3736.8 (5)
C1—Fe1—C6—P143.2 (8)C31—Fe2—C36—P2−46.0 (8)
C3—Fe1—C6—P1−77.9 (12)C37—Fe2—C36—P2118.0 (8)
C2—Fe1—C6—P181.4 (13)C33—Fe2—C36—P238.2 (8)
C8—Fe1—C6—P1158.6 (7)C40—Fe2—C36—P2−123.6 (8)
C4—Fe1—C6—P1−41.6 (8)C35—Fe2—C36—P2−82.1 (14)
C10—Fe1—C6—P1−118.8 (8)C34—Fe2—C36—P273.7 (11)
C9—Fe1—C6—P1−157.5 (7)C32—Fe2—C36—P2−4.4 (7)
C5—Fe1—C6—P11.1 (7)C39—Fe2—C36—P2−161.2 (7)
C7—Fe1—C6—P1121.1 (9)C38—Fe2—C36—P2154.7 (7)
C10—C6—C7—C81.8 (10)C40—C36—C37—C38−0.3 (9)
P1—C6—C7—C8−179.8 (7)P2—C36—C37—C38179.2 (6)
Fe1—C6—C7—C8−58.2 (6)Fe2—C36—C37—C38−60.3 (6)
C10—C6—C7—Fe160.0 (6)C40—C36—C37—Fe260.0 (6)
P1—C6—C7—Fe1−121.6 (7)P2—C36—C37—Fe2−120.5 (6)
C6—Fe1—C7—C8119.1 (8)C31—Fe2—C37—C38170.0 (12)
C1—Fe1—C7—C8−117.5 (6)C36—Fe2—C37—C38120.0 (8)
C3—Fe1—C7—C8−39.7 (14)C33—Fe2—C37—C38−121.9 (6)
C2—Fe1—C7—C8−74.5 (7)C40—Fe2—C37—C3881.7 (6)
C4—Fe1—C7—C8165.1 (12)C35—Fe2—C37—C38−48.0 (10)
C10—Fe1—C7—C881.9 (6)C34—Fe2—C37—C38−79.9 (6)
C9—Fe1—C7—C838.2 (6)C32—Fe2—C37—C38−162.0 (6)
C5—Fe1—C7—C8−160.3 (6)C39—Fe2—C37—C3838.0 (5)
C1—Fe1—C7—C6123.4 (6)C31—Fe2—C37—C3649.9 (15)
C3—Fe1—C7—C6−158.8 (11)C33—Fe2—C37—C36118.0 (5)
C2—Fe1—C7—C6166.4 (5)C40—Fe2—C37—C36−38.3 (5)
C8—Fe1—C7—C6−119.1 (8)C35—Fe2—C37—C36−168.0 (8)
C4—Fe1—C7—C646.0 (14)C34—Fe2—C37—C36160.0 (5)
C10—Fe1—C7—C6−37.2 (5)C32—Fe2—C37—C3678.0 (6)
C9—Fe1—C7—C6−80.9 (6)C39—Fe2—C37—C36−82.0 (5)
C5—Fe1—C7—C680.6 (6)C38—Fe2—C37—C36−120.0 (8)
C6—C7—C8—C9−2.9 (10)C36—C37—C38—C390.3 (10)
Fe1—C7—C8—C9−60.3 (7)Fe2—C37—C38—C39−58.7 (6)
C6—C7—C8—Fe157.4 (6)C36—C37—C38—Fe259.0 (6)
C6—Fe1—C8—C979.8 (6)C31—Fe2—C38—C37−172.8 (8)
C1—Fe1—C8—C9−159.5 (5)C36—Fe2—C38—C37−37.9 (5)
C3—Fe1—C8—C9−77.3 (7)C33—Fe2—C38—C3775.7 (6)
C2—Fe1—C8—C9−118.2 (6)C40—Fe2—C38—C37−82.1 (6)
C4—Fe1—C8—C9−47.6 (13)C35—Fe2—C38—C37157.4 (5)
C10—Fe1—C8—C936.0 (5)C34—Fe2—C38—C37115.9 (6)
C5—Fe1—C8—C9169.2 (9)C32—Fe2—C38—C3748.4 (13)
C7—Fe1—C8—C9118.3 (8)C39—Fe2—C38—C37−119.2 (7)
C6—Fe1—C8—C7−38.4 (6)C31—Fe2—C38—C39−53.6 (11)
C1—Fe1—C8—C782.2 (7)C36—Fe2—C38—C3981.3 (5)
C3—Fe1—C8—C7164.5 (6)C37—Fe2—C38—C39119.2 (7)
C2—Fe1—C8—C7123.5 (6)C33—Fe2—C38—C39−165.0 (5)
C4—Fe1—C8—C7−165.9 (10)C40—Fe2—C38—C3937.1 (5)
C10—Fe1—C8—C7−82.2 (6)C35—Fe2—C38—C39−83.4 (6)
C9—Fe1—C8—C7−118.3 (8)C34—Fe2—C38—C39−124.9 (5)
C5—Fe1—C8—C750.9 (13)C32—Fe2—C38—C39167.6 (10)
C7—C8—C9—C103.0 (11)C37—C38—C39—C40−0.1 (10)
Fe1—C8—C9—C10−57.7 (7)Fe2—C38—C39—C40−58.3 (6)
C7—C8—C9—Fe160.7 (6)C37—C38—C39—Fe258.2 (6)
C6—Fe1—C9—C8−83.3 (6)C31—Fe2—C39—C40−82.4 (6)
C1—Fe1—C9—C849.6 (12)C36—Fe2—C39—C4038.1 (5)
C3—Fe1—C9—C8120.5 (6)C37—Fe2—C39—C4082.8 (6)
C2—Fe1—C9—C879.0 (6)C33—Fe2—C39—C40160.2 (10)
C4—Fe1—C9—C8161.2 (5)C35—Fe2—C39—C40−125.5 (6)
C10—Fe1—C9—C8−122.2 (8)C34—Fe2—C39—C40−167.1 (5)
C5—Fe1—C9—C8−168.7 (10)C32—Fe2—C39—C40−48.7 (12)
C7—Fe1—C9—C8−38.2 (5)C38—Fe2—C39—C40120.2 (8)
C6—Fe1—C9—C1038.9 (5)C31—Fe2—C39—C38157.4 (5)
C1—Fe1—C9—C10171.8 (9)C36—Fe2—C39—C38−82.0 (5)
C3—Fe1—C9—C10−117.3 (6)C37—Fe2—C39—C38−37.3 (5)
C2—Fe1—C9—C10−158.8 (6)C33—Fe2—C39—C3840.0 (13)
C8—Fe1—C9—C10122.2 (8)C40—Fe2—C39—C38−120.2 (8)
C4—Fe1—C9—C10−76.6 (6)C35—Fe2—C39—C38114.4 (6)
C5—Fe1—C9—C10−46.5 (13)C34—Fe2—C39—C3872.7 (6)
C7—Fe1—C9—C1084.0 (6)C32—Fe2—C39—C38−168.9 (9)
C7—C6—C10—C90.0 (10)C38—C39—C40—C36−0.1 (10)
P1—C6—C10—C9−178.5 (6)Fe2—C39—C40—C36−58.8 (6)
Fe1—C6—C10—C960.1 (6)C38—C39—C40—Fe258.8 (6)
C7—C6—C10—Fe1−60.1 (6)C37—C36—C40—C390.2 (9)
P1—C6—C10—Fe1121.5 (7)P2—C36—C40—C39−179.3 (6)
C8—C9—C10—C6−1.8 (10)Fe2—C36—C40—C3959.8 (6)
Fe1—C9—C10—C6−59.4 (6)C37—C36—C40—Fe2−59.6 (6)
C8—C9—C10—Fe157.5 (7)P2—C36—C40—Fe2120.9 (7)
C1—Fe1—C10—C6−52.5 (14)C31—Fe2—C40—C39117.3 (6)
C3—Fe1—C10—C6−162.6 (5)C36—Fe2—C40—C39−119.1 (8)
C2—Fe1—C10—C6165.4 (8)C37—Fe2—C40—C39−80.6 (6)
C8—Fe1—C10—C681.3 (6)C33—Fe2—C40—C39−162.8 (10)
C4—Fe1—C10—C6−121.0 (6)C35—Fe2—C40—C3973.9 (7)
C9—Fe1—C10—C6117.4 (8)C34—Fe2—C40—C3936.5 (15)
C5—Fe1—C10—C6−80.2 (6)C32—Fe2—C40—C39160.4 (6)
C7—Fe1—C10—C637.8 (5)C38—Fe2—C40—C39−37.4 (6)
C6—Fe1—C10—C9−117.4 (8)C31—Fe2—C40—C36−123.6 (5)
C1—Fe1—C10—C9−169.9 (12)C37—Fe2—C40—C3638.6 (5)
C3—Fe1—C10—C980.0 (7)C33—Fe2—C40—C36−43.7 (12)
C2—Fe1—C10—C948.1 (12)C35—Fe2—C40—C36−167.0 (5)
C8—Fe1—C10—C9−36.0 (6)C34—Fe2—C40—C36155.6 (11)
C4—Fe1—C10—C9121.6 (6)C32—Fe2—C40—C36−80.5 (6)
C5—Fe1—C10—C9162.4 (6)C39—Fe2—C40—C36119.1 (8)
C7—Fe1—C10—C9−79.5 (6)C38—Fe2—C40—C3681.7 (5)
C6—P1—C11—C16176.3 (7)C36—P2—C41—C425.4 (9)
C17—P1—C11—C1664.6 (8)C47—P2—C41—C42114.8 (8)
S1—P1—C11—C16−60.0 (8)S2—P2—C41—C42−119.9 (7)
C6—P1—C11—C12−3.4 (8)C36—P2—C41—C46−173.4 (7)
C17—P1—C11—C12−115.1 (8)C47—P2—C41—C46−64.0 (8)
S1—P1—C11—C12120.3 (7)S2—P2—C41—C4661.3 (8)
C16—C11—C12—C13−0.5 (13)C46—C41—C42—C431.3 (13)
P1—C11—C12—C13179.1 (7)P2—C41—C42—C43−177.5 (7)
C11—C12—C13—C140.1 (14)C41—C42—C43—C440.2 (14)
C12—C13—C14—C150.0 (14)C42—C43—C44—C45−0.9 (15)
C13—C14—C15—C160.5 (15)C43—C44—C45—C460.1 (15)
C12—C11—C16—C151.0 (13)C44—C45—C46—C411.4 (15)
P1—C11—C16—C15−178.7 (7)C42—C41—C46—C45−2.1 (14)
C14—C15—C16—C11−1.0 (14)P2—C41—C46—C45176.8 (7)
C11—P1—C17—C18−139.3 (7)C36—P2—C47—C4868.5 (7)
C6—P1—C17—C18110.3 (7)C41—P2—C47—C48−41.2 (8)
S1—P1—C17—C18−15.9 (8)S2—P2—C47—C48−165.1 (6)
C11—P1—C17—C2241.0 (8)C36—P2—C47—C52−112.4 (7)
C6—P1—C17—C22−69.4 (7)C41—P2—C47—C52137.9 (7)
S1—P1—C17—C22164.4 (6)S2—P2—C47—C5214.0 (8)
C22—C17—C18—C192.0 (13)C52—C47—C48—C492.3 (12)
P1—C17—C18—C19−177.7 (7)P2—C47—C48—C49−178.6 (6)
C17—C18—C19—C20−0.1 (14)C47—C48—C49—C50−1.6 (13)
C18—C19—C20—C21−1.4 (14)C48—C49—C50—C512.0 (13)
C19—C20—C21—C220.9 (14)C49—C50—C51—C52−3.2 (14)
C20—C21—C22—C171.1 (13)C50—C51—C52—C473.9 (13)
C18—C17—C22—C21−2.5 (12)C48—C47—C52—C51−3.5 (12)
P1—C17—C22—C21177.2 (7)P2—C47—C52—C51177.4 (7)

Experimental details

Crystal data
Chemical formula[Fe(C5H4Br)(C17H14PS)]
Mr481.15
Crystal system, space groupMonoclinic, P21/n
Temperature (K)150
a, b, c (Å)13.3590 (7), 17.3446 (7), 17.0297 (9)
β (°) 102.460 (2)
V (Å3)3853.0 (3)
Z8
Radiation typeMo Kα
µ (mm−1)3.05
Crystal size (mm)0.25 × 0.18 × 0.02
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionIntegration
(COLLECT; Nonius, 2000)
Tmin, Tmax0.540, 0.937
No. of measured, independent and
observed [I > 2σ(I)] reflections		53227, 6802, 4020
Rint0.122
(sin θ/λ)max (Å−1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.077, 0.232, 1.05
No. of reflections6802
No. of parameters469
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.1118P)2 + 21.2954P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å−3)2.19, −1.30

Computer programs: COLLECT (Nonius, 2000), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

 

Acknowledgements

This work was supported financially by the Grant Agency of Charles University in Prague (project No. 69309) and is a part of the long-term research project supported by the Ministry of Education, Youth and Sports of the Czech Republic (project No. MSM0021620857).

References

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ISSN: 2056-9890
Volume 65| Part 10| October 2009| Page m1210
doi:10.1107/S1600536809036459
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