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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m168–m169.
Published online 2010 January 16. doi:  10.1107/S1600536810001418
PMCID: PMC2979891

[μ-1,1′-Bis(diphenyl­phosphino)ferro­cene-κ2 P:P′]bis­[chloridogold(I)]–chloro­form–hexane (2/2/1)

Abstract

In the title mixed solvate, [Au2Fe(C17H14P)2Cl2]·CHCl3·0.5CH3(CH2)4CH3, the hexane solvent mol­ecule is disposed about an inversion centre. The Au atoms exist within nearly ideal linear coordination defined by P,Cl-donor sets, and when viewed down the P(...)P axis the Au atoms are gauche to each other. In the crystal structure, the chloro­form solvent mol­ecule is associated with the complex via a C—H(...)Cl contact, and the hexane solvent mol­ecules occupy voids defined by the remaining components of the structure.

Related literature

For three polymorphs of the unsolvated title complex, see: Crespo et al. (2000 [triangle]); Constable et al. (2007 [triangle]); Segapelo et al. (2008 [triangle]). For solvated forms of the title complex, see: Hill et al. (1989 [triangle]); Canales et al. (1997 [triangle]). For a definition of a pseudo-polymorph, see: Nangia (2006 [triangle]). For background to related studies in gold chemistry, see: Gallenkamp et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m168-scheme1.jpg

Experimental

Crystal data

  • [Au2Fe(C17H14P)2Cl2]·CHCl3·0.5C6H14
  • M r = 1181.64
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m168-efi1.jpg
  • a = 11.631 (5) Å
  • b = 12.763 (5) Å
  • c = 14.530 (7) Å
  • α = 103.586 (7)°
  • β = 110.803 (9)°
  • γ = 92.802 (10)°
  • V = 1939.0 (15) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 8.37 mm−1
  • T = 98 K
  • 0.22 × 0.19 × 0.04 mm

Data collection

  • Rigaku AFC12/SATURN724 diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.222, T max = 1
  • 19988 measured reflections
  • 8010 independent reflections
  • 7541 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.099
  • S = 1.08
  • 8010 reflections
  • 433 parameters
  • H-atom parameters constrained
  • Δρmax = 2.53 e Å−3
  • Δρmin = −2.36 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810001418/hg2624sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001418/hg2624Isup2.hkl

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

Acknowledgments

The authors thank the German Research Foundation (DFG) for support of this work.

supplementary crystallographic information

Comment

In connection with on-going investigations of the biological activity of phosphinegold(I) thiolates (Gallenkamp et al., 2009), the title mixed solvate, (I), was isolated and characterized crystallographically. The asymmetric unit of (I) comprises a dinuclear (C34H28FeP2)(AuCl)2 molecule, Fig. 1, a chloroform molecule, and half an hexane molecule which is located about an inversion centre. Each gold atom exists within a linear geometry defined by phosphorus and chloride atoms, Table 1. Each of the pairs of Au–Cl and Au–P bond distances are equal within 5σ, and the deviations from the ideal linear geometry are minimal, Table 1. The relative disposition of the P–Au–Cl chromophores is best described in terms of the Au1–P1···P1–Au2 torsion angle of 79.5 (6) ° and so may be regarded as being gauche (see discussion below). In the crystal structure, the chloroform molecule forms a C–H···Cl interaction with the Cl2 atom, Table 2. The hexane molecules occupy voids defined by the remaining components of the structure, Fig. 2.

Unsolvated polymorphic forms of the title complex have been characterized previously, i.e. in monoclinic space groups P21/n (Crespo et al., 2000) and C2/c (Segapelo et al., 2008), and triclinic P1 (Constable et al., 2007). In each of these polymorphs, the iron atom is located on a centre of inversion so that, from symmetry, the Au–P···P–Au torsion angle is 180 °. Two pseudo-polymorphs (Nangia, 2006) of the title complex are also known. In the 1:2 dichloromethane solvate, the iron atom is again located on a centre of inversion (Canales et al., 1997). Finally, Hill et al. (1989) reported a chloroform solvate where the ratio of complex to chloroform was 3:2. One of the independent complex molecules was located about a centre of inversion. The second complex molecule adopted a gauche conformation with the Au–P···P–Au torsion angle being 117.78 (14) °.

Experimental

Crystals of Au2Cl2(dppf) were adventitiously isolated by layering hexane onto a CDCl3 solution containing stoichiometric amounts of Au2Cl2(dppf) with 1,8-(Me3Sn2) naphthalene in an NMR tube.

Refinement

The C-bound H atoms were geometrically placed (C–H = 0.95–1.00 Å) and refined as riding with Uiso(H) = 1.2–1.5Ueq(C). The maximum and minimum residual electron density peaks of 2.53 and -2.36 e Å-3, respectively, were located 1.50 Å and 0.84 Å from the Cl5 and Au2 atoms, respectively.

Figures

Fig. 1.
Molecular structure of the complex in (I), showing atom-labelling scheme and displacement ellipsoids at the 50% probability level.
Fig. 2.
A view of the crystal packing in (I). The C–H···Cl interactions are shown as blue dashed lines, and the solvent hexane molecules are represented in space filling mode. Color code: Au, orange; Fe, brown; Cl, cyan; P, pink; ...

Crystal data

[Au2Fe(C17H14P)2Cl2]·CHCl3·0.5C6H14Z = 2
Mr = 1181.64F(000) = 1126
Triclinic, P1Dx = 2.024 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71070 Å
a = 11.631 (5) ÅCell parameters from 7032 reflections
b = 12.763 (5) Åθ = 2.0–30.1°
c = 14.530 (7) ŵ = 8.37 mm1
α = 103.586 (7)°T = 98 K
β = 110.803 (9)°Block, orange
γ = 92.802 (10)°0.22 × 0.19 × 0.04 mm
V = 1939.0 (15) Å3

Data collection

Rigaku AFC12K/SATURN724 diffractometer8010 independent reflections
Radiation source: fine-focus sealed tube7541 reflections with I > 2σ(I)
graphiteRint = 0.041
ω scansθmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −14→14
Tmin = 0.222, Tmax = 1k = −13→16
19988 measured reflectionsl = −18→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0508P)2 + 6.3295P] where P = (Fo2 + 2Fc2)/3
8010 reflections(Δ/σ)max = 0.002
433 parametersΔρmax = 2.53 e Å3
0 restraintsΔρmin = −2.36 e Å3

Special details

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)

xyzUiso*/Ueq
Au10.581716 (18)0.161739 (17)0.103915 (15)0.01852 (8)
Au20.735621 (18)−0.075680 (16)0.585129 (15)0.01820 (8)
Fe0.74224 (7)0.14693 (6)0.41137 (6)0.01708 (16)
Cl10.37269 (12)0.10792 (13)0.00408 (10)0.0270 (3)
Cl20.73374 (14)−0.26065 (11)0.53407 (11)0.0265 (3)
Cl30.79521 (19)0.55203 (16)0.72594 (19)0.0530 (5)
Cl40.62630 (15)0.67474 (14)0.79754 (13)0.0349 (4)
Cl50.5292 (2)0.47710 (15)0.62931 (16)0.0477 (4)
P10.78213 (13)0.21388 (11)0.20723 (10)0.0179 (3)
P20.73597 (12)0.10415 (11)0.63297 (10)0.0168 (3)
C10.8941 (5)0.1834 (4)0.1473 (4)0.0187 (11)
C21.0085 (5)0.1529 (5)0.1977 (5)0.0255 (12)
H21.02770.14390.26440.031*
C31.0948 (6)0.1357 (6)0.1512 (5)0.0328 (14)
H31.17300.11650.18670.039*
C41.0667 (6)0.1466 (6)0.0532 (5)0.0314 (14)
H41.12400.13240.02030.038*
C50.9536 (6)0.1787 (6)0.0035 (5)0.0361 (15)
H50.93490.1880−0.06300.043*
C60.8673 (6)0.1974 (5)0.0497 (4)0.0283 (13)
H60.79060.21950.01500.034*
C70.8213 (6)0.3588 (4)0.2703 (4)0.0222 (12)
C80.7257 (6)0.4229 (5)0.2624 (5)0.0263 (13)
H80.64180.39020.22370.032*
C90.7524 (7)0.5335 (6)0.3104 (5)0.0355 (15)
H90.68720.57640.30630.043*
C100.8745 (7)0.5806 (5)0.3643 (5)0.0360 (16)
H100.89310.65690.39510.043*
C110.9705 (7)0.5189 (6)0.3743 (5)0.0354 (15)
H111.05390.55290.41350.042*
C120.9458 (6)0.4076 (5)0.3274 (5)0.0286 (13)
H121.01170.36510.33360.034*
C130.8234 (5)0.1463 (4)0.3073 (4)0.0191 (11)
C140.7668 (5)0.0387 (5)0.2938 (4)0.0216 (11)
H140.7026−0.00560.23370.026*
C150.8246 (6)0.0102 (5)0.3874 (4)0.0240 (12)
H150.8053−0.05690.40020.029*
C160.9153 (5)0.0984 (5)0.4582 (4)0.0267 (13)
H160.96670.10100.52640.032*
C170.9160 (5)0.1821 (5)0.4094 (4)0.0226 (12)
H170.96860.25030.43910.027*
C180.6783 (5)0.1609 (4)0.5259 (4)0.0167 (10)
C190.7099 (5)0.2673 (4)0.5177 (4)0.0204 (11)
H190.76940.32450.56960.024*
C200.6348 (5)0.2711 (5)0.4162 (4)0.0229 (12)
H200.63670.33190.38930.028*
C210.5572 (5)0.1694 (5)0.3625 (4)0.0232 (12)
H210.49860.15060.29400.028*
C220.5828 (5)0.1011 (5)0.4293 (4)0.0193 (11)
H220.54380.02850.41330.023*
C230.6329 (5)0.1383 (4)0.7019 (4)0.0188 (11)
C240.6470 (5)0.0969 (5)0.7854 (4)0.0223 (11)
H240.71150.05460.80660.027*
C250.5684 (6)0.1168 (5)0.8376 (4)0.0261 (12)
H250.57800.08730.89370.031*
C260.4740 (6)0.1807 (5)0.8078 (5)0.0261 (13)
H260.42170.19700.84510.031*
C270.4581 (6)0.2194 (5)0.7238 (5)0.0273 (13)
H270.39230.26030.70200.033*
C280.5369 (5)0.1997 (4)0.6704 (4)0.0209 (11)
H280.52560.22760.61310.025*
C290.8855 (5)0.1835 (5)0.7195 (4)0.0191 (11)
C300.8942 (6)0.2915 (5)0.7667 (5)0.0253 (12)
H300.82190.32610.75290.030*
C311.0095 (6)0.3513 (5)0.8356 (5)0.0306 (14)
H311.01580.42660.86740.037*
C321.1147 (6)0.2991 (6)0.8568 (5)0.0318 (14)
H321.19280.33930.90370.038*
C331.1069 (5)0.1903 (5)0.8108 (5)0.0280 (13)
H331.17890.15530.82690.034*
C340.9930 (5)0.1316 (5)0.7406 (4)0.0209 (11)
H340.98760.05700.70710.025*
C350.6456 (7)0.5917 (6)0.6900 (6)0.0385 (16)
H350.63850.63570.64010.046*
C360.5378 (6)0.4984 (6)0.9665 (5)0.0350 (15)
H36A0.56620.57390.96930.042*
H36B0.48380.46100.89470.042*
C370.6526 (7)0.4386 (6)0.9999 (5)0.0357 (15)
H37A0.70740.47711.07110.043*
H37B0.62420.36380.99880.043*
C380.7268 (7)0.4324 (6)0.9323 (6)0.0436 (18)
H38A0.75000.35930.91790.065*
H38B0.80210.48640.96730.065*
H38C0.67630.44750.86800.065*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Au10.01595 (12)0.02468 (13)0.01377 (12)0.00351 (9)0.00404 (9)0.00541 (9)
Au20.01883 (12)0.01858 (13)0.01681 (12)0.00345 (9)0.00594 (9)0.00520 (9)
Fe0.0152 (4)0.0221 (4)0.0148 (4)0.0046 (3)0.0054 (3)0.0068 (3)
Cl10.0172 (6)0.0406 (8)0.0188 (7)0.0039 (6)0.0032 (5)0.0058 (6)
Cl20.0301 (7)0.0217 (7)0.0253 (7)0.0048 (6)0.0073 (6)0.0066 (6)
Cl30.0501 (11)0.0430 (10)0.0916 (16)0.0231 (9)0.0479 (12)0.0288 (10)
Cl40.0350 (9)0.0389 (9)0.0388 (9)0.0144 (7)0.0194 (7)0.0147 (7)
Cl50.0600 (12)0.0370 (9)0.0527 (11)0.0106 (8)0.0284 (10)0.0124 (8)
P10.0172 (7)0.0220 (7)0.0137 (6)0.0022 (5)0.0053 (5)0.0044 (5)
P20.0155 (6)0.0196 (7)0.0145 (6)0.0028 (5)0.0044 (5)0.0052 (5)
C10.018 (3)0.017 (3)0.018 (3)−0.001 (2)0.005 (2)0.003 (2)
C20.024 (3)0.034 (3)0.021 (3)0.008 (2)0.009 (2)0.010 (2)
C30.024 (3)0.043 (4)0.035 (4)0.007 (3)0.012 (3)0.016 (3)
C40.029 (3)0.048 (4)0.023 (3)0.011 (3)0.015 (3)0.011 (3)
C50.029 (3)0.060 (5)0.021 (3)0.005 (3)0.010 (3)0.013 (3)
C60.022 (3)0.045 (4)0.019 (3)0.008 (3)0.006 (2)0.013 (3)
C70.030 (3)0.018 (3)0.020 (3)0.003 (2)0.010 (2)0.005 (2)
C80.027 (3)0.024 (3)0.024 (3)0.005 (2)0.007 (3)0.003 (2)
C90.041 (4)0.031 (3)0.028 (3)0.009 (3)0.007 (3)0.005 (3)
C100.052 (4)0.022 (3)0.031 (4)0.001 (3)0.016 (3)0.002 (3)
C110.035 (4)0.041 (4)0.029 (3)−0.004 (3)0.016 (3)0.003 (3)
C120.023 (3)0.033 (3)0.026 (3)−0.002 (2)0.009 (3)0.002 (3)
C130.020 (3)0.022 (3)0.015 (3)0.004 (2)0.006 (2)0.005 (2)
C140.025 (3)0.025 (3)0.017 (3)0.008 (2)0.012 (2)0.004 (2)
C150.029 (3)0.025 (3)0.027 (3)0.012 (2)0.017 (3)0.011 (2)
C160.022 (3)0.046 (4)0.017 (3)0.017 (3)0.008 (2)0.014 (3)
C170.012 (3)0.038 (3)0.017 (3)0.006 (2)0.002 (2)0.009 (2)
C180.013 (2)0.024 (3)0.012 (2)0.006 (2)0.004 (2)0.004 (2)
C190.024 (3)0.016 (3)0.019 (3)0.005 (2)0.009 (2)0.002 (2)
C200.022 (3)0.024 (3)0.028 (3)0.008 (2)0.012 (2)0.011 (2)
C210.016 (3)0.037 (3)0.018 (3)0.011 (2)0.005 (2)0.010 (2)
C220.015 (3)0.021 (3)0.018 (3)0.000 (2)0.004 (2)0.001 (2)
C230.021 (3)0.017 (3)0.017 (3)0.000 (2)0.007 (2)0.002 (2)
C240.022 (3)0.027 (3)0.016 (3)0.002 (2)0.006 (2)0.004 (2)
C250.027 (3)0.030 (3)0.019 (3)−0.001 (2)0.007 (2)0.007 (2)
C260.026 (3)0.026 (3)0.027 (3)−0.001 (2)0.014 (3)0.002 (2)
C270.027 (3)0.027 (3)0.031 (3)0.011 (2)0.014 (3)0.009 (3)
C280.022 (3)0.018 (3)0.019 (3)0.001 (2)0.004 (2)0.003 (2)
C290.018 (3)0.028 (3)0.008 (2)0.001 (2)0.003 (2)0.004 (2)
C300.022 (3)0.027 (3)0.023 (3)0.006 (2)0.010 (2)−0.002 (2)
C310.034 (3)0.023 (3)0.026 (3)−0.005 (3)0.008 (3)−0.003 (2)
C320.025 (3)0.042 (4)0.018 (3)−0.001 (3)0.002 (3)0.001 (3)
C330.015 (3)0.037 (4)0.024 (3)0.001 (2)0.002 (2)0.002 (3)
C340.022 (3)0.025 (3)0.015 (3)0.006 (2)0.006 (2)0.004 (2)
C350.048 (4)0.037 (4)0.043 (4)0.018 (3)0.025 (4)0.020 (3)
C360.033 (4)0.043 (4)0.027 (3)0.002 (3)0.011 (3)0.005 (3)
C370.041 (4)0.033 (4)0.030 (3)0.003 (3)0.010 (3)0.006 (3)
C380.046 (4)0.038 (4)0.046 (4)0.009 (3)0.020 (4)0.006 (3)

Geometric parameters (Å, °)

Au1—Cl12.3131 (17)C14—H140.9500
Au1—P12.2413 (17)C15—C161.417 (9)
Au2—Cl22.2988 (17)C15—H150.9500
Au2—P22.2357 (17)C16—C171.415 (8)
Fe—C182.026 (5)C16—H160.9500
Fe—C222.039 (5)C17—H170.9500
Fe—C142.045 (5)C18—C191.432 (8)
Fe—C132.046 (5)C18—C221.446 (7)
Fe—C152.049 (5)C19—C201.437 (8)
Fe—C192.059 (5)C19—H190.9500
Fe—C172.060 (6)C20—C211.420 (8)
Fe—C162.060 (6)C20—H200.9500
Fe—C202.069 (5)C21—C221.417 (8)
Fe—C212.071 (5)C21—H210.9500
Cl3—C351.767 (7)C22—H220.9500
Cl4—C351.764 (7)C23—C241.396 (8)
Cl5—C351.761 (8)C23—C281.399 (8)
P1—C131.795 (6)C24—C251.379 (8)
P1—C71.814 (6)C24—H240.9500
P1—C11.817 (5)C25—C261.404 (9)
P2—C181.798 (5)C25—H250.9500
P2—C291.819 (6)C26—C271.378 (9)
P2—C231.825 (5)C26—H260.9500
C1—C61.396 (8)C27—C281.393 (8)
C1—C21.397 (8)C27—H270.9500
C2—C31.396 (8)C28—H280.9500
C2—H20.9500C29—C301.369 (8)
C3—C41.386 (9)C29—C341.414 (8)
C3—H30.9500C30—C311.404 (9)
C4—C51.392 (9)C30—H300.9500
C4—H40.9500C31—C321.394 (9)
C5—C61.394 (9)C31—H310.9500
C5—H50.9500C32—C331.376 (9)
C6—H60.9500C32—H320.9500
C7—C81.401 (8)C33—C341.393 (8)
C7—C121.410 (8)C33—H330.9500
C8—C91.385 (9)C34—H340.9500
C8—H80.9500C35—H351.0000
C9—C101.377 (10)C36—C36i1.521 (13)
C9—H90.9500C36—C371.554 (9)
C10—C111.383 (10)C36—H36A0.9900
C10—H100.9500C36—H36B0.9900
C11—C121.391 (9)C37—C381.511 (10)
C11—H110.9500C37—H37A0.9900
C12—H120.9500C37—H37B0.9900
C13—C141.432 (8)C38—H38A0.9800
C13—C171.439 (8)C38—H38B0.9800
C14—C151.428 (8)C38—H38C0.9800
P1—Au1—Cl1177.27 (5)C16—C15—Fe70.3 (3)
P2—Au2—Cl2179.34 (5)C14—C15—Fe69.5 (3)
C18—Fe—C2241.7 (2)C16—C15—H15125.6
C18—Fe—C14144.2 (2)C14—C15—H15125.6
C22—Fe—C14112.3 (2)Fe—C15—H15126.3
C18—Fe—C13173.4 (2)C17—C16—C15108.0 (5)
C22—Fe—C13144.7 (2)C17—C16—Fe69.9 (3)
C14—Fe—C1341.0 (2)C15—C16—Fe69.4 (3)
C18—Fe—C15113.2 (2)C17—C16—H16126.0
C22—Fe—C15107.2 (2)C15—C16—H16126.0
C14—Fe—C1540.8 (2)Fe—C16—H16126.3
C13—Fe—C1568.5 (2)C16—C17—C13108.4 (5)
C18—Fe—C1941.0 (2)C16—C17—Fe69.9 (3)
C22—Fe—C1969.1 (2)C13—C17—Fe69.0 (3)
C14—Fe—C19173.1 (2)C16—C17—H17125.8
C13—Fe—C19134.4 (2)C13—C17—H17125.8
C15—Fe—C19145.9 (2)Fe—C17—H17126.9
C18—Fe—C17133.0 (2)C19—C18—C22107.6 (5)
C22—Fe—C17171.6 (2)C19—C18—P2129.7 (4)
C14—Fe—C1768.6 (2)C22—C18—P2122.6 (4)
C13—Fe—C1741.0 (2)C19—C18—Fe70.7 (3)
C15—Fe—C1767.8 (2)C22—C18—Fe69.6 (3)
C19—Fe—C17111.0 (2)P2—C18—Fe126.4 (3)
C18—Fe—C16108.3 (2)C18—C19—C20107.1 (5)
C22—Fe—C16131.8 (2)C18—C19—Fe68.2 (3)
C14—Fe—C1668.6 (2)C20—C19—Fe70.0 (3)
C13—Fe—C1668.6 (2)C18—C19—H19126.5
C15—Fe—C1640.3 (2)C20—C19—H19126.5
C19—Fe—C16115.9 (2)Fe—C19—H19126.8
C17—Fe—C1640.2 (2)C21—C20—C19109.1 (5)
C18—Fe—C2068.6 (2)C21—C20—Fe70.0 (3)
C22—Fe—C2067.8 (2)C19—C20—Fe69.3 (3)
C14—Fe—C20132.9 (2)C21—C20—H20125.5
C13—Fe—C20110.8 (2)C19—C20—H20125.5
C15—Fe—C20171.0 (2)Fe—C20—H20126.9
C19—Fe—C2040.7 (2)C22—C21—C20107.8 (5)
C17—Fe—C20118.1 (2)C22—C21—Fe68.6 (3)
C16—Fe—C20148.5 (3)C20—C21—Fe69.9 (3)
C18—Fe—C2169.0 (2)C22—C21—H21126.1
C22—Fe—C2140.3 (2)C20—C21—H21126.1
C14—Fe—C21107.8 (2)Fe—C21—H21127.0
C13—Fe—C21115.0 (2)C21—C22—C18108.4 (5)
C15—Fe—C21131.4 (3)C21—C22—Fe71.0 (3)
C19—Fe—C2168.6 (2)C18—C22—Fe68.7 (3)
C17—Fe—C21148.0 (2)C21—C22—H22125.8
C16—Fe—C21170.5 (3)C18—C22—H22125.8
C20—Fe—C2140.1 (2)Fe—C22—H22126.0
C13—P1—C7106.1 (3)C24—C23—C28119.5 (5)
C13—P1—C1104.4 (3)C24—C23—P2118.4 (4)
C7—P1—C1105.0 (3)C28—C23—P2122.1 (4)
C13—P1—Au1110.77 (19)C25—C24—C23120.7 (5)
C7—P1—Au1113.9 (2)C25—C24—H24119.7
C1—P1—Au1115.77 (19)C23—C24—H24119.7
C18—P2—C29107.8 (3)C24—C25—C26120.0 (6)
C18—P2—C23104.4 (2)C24—C25—H25120.0
C29—P2—C23104.2 (2)C26—C25—H25120.0
C18—P2—Au2112.56 (18)C27—C26—C25119.4 (5)
C29—P2—Au2115.27 (19)C27—C26—H26120.3
C23—P2—Au2111.73 (18)C25—C26—H26120.3
C6—C1—C2119.2 (5)C26—C27—C28121.1 (5)
C6—C1—P1118.4 (4)C26—C27—H27119.5
C2—C1—P1122.3 (4)C28—C27—H27119.5
C3—C2—C1120.6 (6)C27—C28—C23119.4 (5)
C3—C2—H2119.7C27—C28—H28120.3
C1—C2—H2119.7C23—C28—H28120.3
C4—C3—C2120.2 (6)C30—C29—C34119.9 (5)
C4—C3—H3119.9C30—C29—P2120.8 (4)
C2—C3—H3119.9C34—C29—P2119.3 (4)
C3—C4—C5119.2 (6)C29—C30—C31120.4 (6)
C3—C4—H4120.4C29—C30—H30119.8
C5—C4—H4120.4C31—C30—H30119.8
C4—C5—C6121.1 (6)C32—C31—C30119.3 (6)
C4—C5—H5119.4C32—C31—H31120.3
C6—C5—H5119.4C30—C31—H31120.3
C5—C6—C1119.7 (6)C33—C32—C31120.9 (6)
C5—C6—H6120.2C33—C32—H32119.6
C1—C6—H6120.2C31—C32—H32119.6
C8—C7—C12119.6 (5)C32—C33—C34119.8 (6)
C8—C7—P1119.1 (5)C32—C33—H33120.1
C12—C7—P1121.3 (5)C34—C33—H33120.1
C9—C8—C7120.6 (6)C33—C34—C29119.8 (5)
C9—C8—H8119.7C33—C34—H34120.1
C7—C8—H8119.7C29—C34—H34120.1
C10—C9—C8119.3 (6)Cl5—C35—Cl4111.4 (4)
C10—C9—H9120.4Cl5—C35—Cl3111.0 (4)
C8—C9—H9120.4Cl4—C35—Cl3110.2 (4)
C9—C10—C11121.3 (6)Cl5—C35—H35108.1
C9—C10—H10119.4Cl4—C35—H35108.1
C11—C10—H10119.4Cl3—C35—H35108.1
C10—C11—C12120.4 (6)C36i—C36—C37112.6 (7)
C10—C11—H11119.8C36i—C36—H36A109.1
C12—C11—H11119.8C37—C36—H36A109.1
C11—C12—C7118.8 (6)C36i—C36—H36B109.1
C11—C12—H12120.6C37—C36—H36B109.1
C7—C12—H12120.6H36A—C36—H36B107.8
C14—C13—C17107.5 (5)C38—C37—C36113.2 (6)
C14—C13—P1122.8 (4)C38—C37—H37A108.9
C17—C13—P1129.7 (4)C36—C37—H37A108.9
C14—C13—Fe69.5 (3)C38—C37—H37B108.9
C17—C13—Fe70.0 (3)C36—C37—H37B108.9
P1—C13—Fe127.4 (3)H37A—C37—H37B107.8
C15—C14—C13107.4 (5)C37—C38—H38A109.5
C15—C14—Fe69.7 (3)C37—C38—H38B109.5
C13—C14—Fe69.5 (3)H38A—C38—H38B109.5
C15—C14—H14126.3C37—C38—H38C109.5
C13—C14—H14126.3H38A—C38—H38C109.5
Fe—C14—H14126.0H38B—C38—H38C109.5
C16—C15—C14108.8 (5)
Cl1—Au1—P1—C1338.5 (11)C20—Fe—C17—C13−90.0 (4)
Cl1—Au1—P1—C7−81.1 (11)C21—Fe—C17—C13−51.5 (6)
Cl1—Au1—P1—C1157.1 (11)C29—P2—C18—C19−21.3 (5)
Cl2—Au2—P2—C18−16 (5)C23—P2—C18—C1989.1 (5)
Cl2—Au2—P2—C29−141 (4)Au2—P2—C18—C19−149.5 (4)
Cl2—Au2—P2—C23101 (4)C29—P2—C18—C22160.9 (4)
C13—P1—C1—C6162.1 (5)C23—P2—C18—C22−88.7 (4)
C7—P1—C1—C6−86.4 (5)Au2—P2—C18—C2232.6 (5)
Au1—P1—C1—C640.1 (5)C29—P2—C18—Fe73.3 (4)
C13—P1—C1—C2−21.8 (5)C23—P2—C18—Fe−176.4 (3)
C7—P1—C1—C289.7 (5)Au2—P2—C18—Fe−55.0 (4)
Au1—P1—C1—C2−143.8 (4)C22—Fe—C18—C19−118.2 (4)
C6—C1—C2—C3−0.5 (9)C14—Fe—C18—C19−172.7 (4)
P1—C1—C2—C3−176.6 (5)C13—Fe—C18—C1947.8 (19)
C1—C2—C3—C4−1.3 (10)C15—Fe—C18—C19151.6 (3)
C2—C3—C4—C52.3 (11)C17—Fe—C18—C1971.1 (4)
C3—C4—C5—C6−1.6 (11)C16—Fe—C18—C19108.7 (4)
C4—C5—C6—C1−0.2 (11)C20—Fe—C18—C19−37.9 (3)
C2—C1—C6—C51.3 (9)C21—Fe—C18—C19−81.1 (3)
P1—C1—C6—C5177.5 (5)C14—Fe—C18—C22−54.5 (5)
C13—P1—C7—C8−113.5 (5)C13—Fe—C18—C22166.0 (18)
C1—P1—C7—C8136.3 (5)C15—Fe—C18—C22−90.2 (4)
Au1—P1—C7—C88.6 (5)C19—Fe—C18—C22118.2 (4)
C13—P1—C7—C1266.1 (5)C17—Fe—C18—C22−170.8 (3)
C1—P1—C7—C12−44.1 (5)C16—Fe—C18—C22−133.1 (3)
Au1—P1—C7—C12−171.7 (4)C20—Fe—C18—C2280.3 (3)
C12—C7—C8—C9−0.3 (9)C21—Fe—C18—C2237.1 (3)
P1—C7—C8—C9179.4 (5)C22—Fe—C18—P2116.2 (5)
C7—C8—C9—C101.6 (10)C14—Fe—C18—P261.6 (5)
C8—C9—C10—C11−2.3 (10)C13—Fe—C18—P2−77.8 (19)
C9—C10—C11—C121.9 (11)C15—Fe—C18—P226.0 (4)
C10—C11—C12—C7−0.6 (10)C19—Fe—C18—P2−125.6 (5)
C8—C7—C12—C11−0.2 (9)C17—Fe—C18—P2−54.6 (5)
P1—C7—C12—C11−179.9 (5)C16—Fe—C18—P2−17.0 (4)
C7—P1—C13—C14155.6 (4)C20—Fe—C18—P2−163.5 (4)
C1—P1—C13—C14−93.8 (5)C21—Fe—C18—P2153.3 (4)
Au1—P1—C13—C1431.5 (5)C22—C18—C19—C20−0.6 (6)
C7—P1—C13—C17−26.9 (6)P2—C18—C19—C20−178.7 (4)
C1—P1—C13—C1783.7 (5)Fe—C18—C19—C2059.5 (4)
Au1—P1—C13—C17−151.1 (4)C22—C18—C19—Fe−60.1 (3)
C7—P1—C13—Fe67.4 (4)P2—C18—C19—Fe121.8 (4)
C1—P1—C13—Fe178.1 (3)C22—Fe—C19—C1838.9 (3)
Au1—P1—C13—Fe−56.7 (4)C14—Fe—C19—C18141.9 (19)
C18—Fe—C13—C14144.5 (18)C13—Fe—C19—C18−173.2 (3)
C22—Fe—C13—C14−51.6 (5)C15—Fe—C19—C18−51.1 (5)
C15—Fe—C13—C1438.1 (3)C17—Fe—C19—C18−132.2 (3)
C19—Fe—C13—C14−172.6 (3)C16—Fe—C19—C18−88.5 (4)
C17—Fe—C13—C14118.5 (5)C20—Fe—C19—C18118.8 (5)
C16—Fe—C13—C1481.6 (4)C21—Fe—C19—C1882.3 (3)
C20—Fe—C13—C14−132.2 (3)C18—Fe—C19—C20−118.8 (5)
C21—Fe—C13—C14−88.8 (4)C22—Fe—C19—C20−79.9 (4)
C18—Fe—C13—C1726 (2)C14—Fe—C19—C2023 (2)
C22—Fe—C13—C17−170.1 (4)C13—Fe—C19—C2068.0 (4)
C14—Fe—C13—C17−118.5 (5)C15—Fe—C19—C20−169.9 (4)
C15—Fe—C13—C17−80.4 (4)C17—Fe—C19—C20109.0 (4)
C19—Fe—C13—C1768.9 (4)C16—Fe—C19—C20152.7 (3)
C16—Fe—C13—C17−36.9 (4)C21—Fe—C19—C20−36.5 (3)
C20—Fe—C13—C17109.3 (4)C18—C19—C20—C210.4 (6)
C21—Fe—C13—C17152.8 (3)Fe—C19—C20—C2158.8 (4)
C18—Fe—C13—P1−99.3 (18)C18—C19—C20—Fe−58.4 (4)
C22—Fe—C13—P164.6 (6)C18—Fe—C20—C21−82.5 (3)
C14—Fe—C13—P1116.2 (5)C22—Fe—C20—C21−37.4 (3)
C15—Fe—C13—P1154.3 (4)C14—Fe—C20—C2163.0 (4)
C19—Fe—C13—P1−56.4 (5)C13—Fe—C20—C21104.5 (3)
C17—Fe—C13—P1−125.3 (5)C15—Fe—C20—C2120.6 (16)
C16—Fe—C13—P1−162.2 (4)C19—Fe—C20—C21−120.7 (5)
C20—Fe—C13—P1−16.0 (4)C17—Fe—C20—C21149.1 (3)
C21—Fe—C13—P127.4 (5)C16—Fe—C20—C21−172.8 (4)
C17—C13—C14—C150.3 (6)C18—Fe—C20—C1938.2 (3)
P1—C13—C14—C15178.2 (4)C22—Fe—C20—C1983.2 (4)
Fe—C13—C14—C15−59.7 (4)C14—Fe—C20—C19−176.3 (3)
C17—C13—C14—Fe60.0 (4)C13—Fe—C20—C19−134.8 (3)
P1—C13—C14—Fe−122.1 (4)C15—Fe—C20—C19141.2 (14)
C18—Fe—C14—C15−55.0 (5)C17—Fe—C20—C19−90.2 (4)
C22—Fe—C14—C15−90.8 (4)C16—Fe—C20—C19−52.1 (6)
C13—Fe—C14—C15118.5 (5)C21—Fe—C20—C19120.7 (5)
C19—Fe—C14—C15168.8 (18)C19—C20—C21—C220.0 (6)
C17—Fe—C14—C1580.3 (4)Fe—C20—C21—C2258.3 (4)
C16—Fe—C14—C1537.0 (4)C19—C20—C21—Fe−58.3 (4)
C20—Fe—C14—C15−170.7 (3)C18—Fe—C21—C22−38.3 (3)
C21—Fe—C14—C15−133.6 (4)C14—Fe—C21—C22103.8 (4)
C18—Fe—C14—C13−173.5 (3)C13—Fe—C21—C22147.3 (3)
C22—Fe—C14—C13150.7 (3)C15—Fe—C21—C2264.7 (4)
C15—Fe—C14—C13−118.5 (5)C19—Fe—C21—C22−82.5 (3)
C19—Fe—C14—C1350 (2)C17—Fe—C21—C22−178.2 (4)
C17—Fe—C14—C13−38.3 (3)C16—Fe—C21—C2237.2 (15)
C16—Fe—C14—C13−81.5 (4)C20—Fe—C21—C22−119.5 (5)
C20—Fe—C14—C1370.8 (4)C18—Fe—C21—C2081.2 (3)
C21—Fe—C14—C13107.9 (3)C22—Fe—C21—C20119.5 (5)
C13—C14—C15—C160.2 (6)C14—Fe—C21—C20−136.7 (3)
Fe—C14—C15—C16−59.4 (4)C13—Fe—C21—C20−93.1 (4)
C13—C14—C15—Fe59.6 (4)C15—Fe—C21—C20−175.8 (3)
C18—Fe—C15—C16−91.3 (4)C19—Fe—C21—C2037.1 (3)
C22—Fe—C15—C16−135.5 (3)C17—Fe—C21—C20−58.6 (6)
C14—Fe—C15—C16120.1 (5)C16—Fe—C21—C20156.8 (12)
C13—Fe—C15—C1681.8 (4)C20—C21—C22—C18−0.4 (6)
C19—Fe—C15—C16−57.6 (5)Fe—C21—C22—C1858.7 (4)
C17—Fe—C15—C1637.4 (3)C20—C21—C22—Fe−59.1 (4)
C20—Fe—C15—C16169.2 (13)C19—C18—C22—C210.6 (6)
C21—Fe—C15—C16−173.2 (3)P2—C18—C22—C21178.9 (4)
C18—Fe—C15—C14148.6 (3)Fe—C18—C22—C21−60.2 (4)
C22—Fe—C15—C14104.5 (4)C19—C18—C22—Fe60.8 (3)
C13—Fe—C15—C14−38.3 (3)P2—C18—C22—Fe−120.9 (4)
C19—Fe—C15—C14−177.6 (4)C18—Fe—C22—C21119.5 (5)
C17—Fe—C15—C14−82.6 (4)C14—Fe—C22—C21−91.6 (4)
C16—Fe—C15—C14−120.1 (5)C13—Fe—C22—C21−57.8 (5)
C20—Fe—C15—C1449.2 (16)C15—Fe—C22—C21−134.8 (3)
C21—Fe—C15—C1466.7 (4)C19—Fe—C22—C2181.2 (4)
C14—C15—C16—C17−0.6 (6)C17—Fe—C22—C21173.4 (15)
Fe—C15—C16—C17−59.5 (4)C16—Fe—C22—C21−172.3 (3)
C14—C15—C16—Fe58.9 (4)C20—Fe—C22—C2137.3 (3)
C18—Fe—C16—C17−136.2 (3)C14—Fe—C22—C18149.0 (3)
C22—Fe—C16—C17−176.8 (3)C13—Fe—C22—C18−177.3 (4)
C14—Fe—C16—C1781.8 (4)C15—Fe—C22—C18105.8 (3)
C13—Fe—C16—C1737.6 (3)C19—Fe—C22—C18−38.3 (3)
C15—Fe—C16—C17119.2 (5)C17—Fe—C22—C1853.9 (17)
C19—Fe—C16—C17−92.5 (4)C16—Fe—C22—C1868.3 (4)
C20—Fe—C16—C17−57.6 (6)C20—Fe—C22—C18−82.2 (3)
C21—Fe—C16—C17151.5 (12)C21—Fe—C22—C18−119.5 (5)
C18—Fe—C16—C15104.6 (3)C18—P2—C23—C24174.6 (4)
C22—Fe—C16—C1564.0 (4)C29—P2—C23—C24−72.5 (5)
C14—Fe—C16—C15−37.4 (3)Au2—P2—C23—C2452.6 (5)
C13—Fe—C16—C15−81.6 (3)C18—P2—C23—C28−2.1 (5)
C19—Fe—C16—C15148.3 (3)C29—P2—C23—C28110.9 (5)
C17—Fe—C16—C15−119.2 (5)Au2—P2—C23—C28−124.0 (4)
C20—Fe—C16—C15−176.8 (4)C28—C23—C24—C25−0.7 (8)
C21—Fe—C16—C1532.3 (15)P2—C23—C24—C25−177.4 (4)
C15—C16—C17—C130.7 (6)C23—C24—C25—C26−1.0 (9)
Fe—C16—C17—C13−58.4 (4)C24—C25—C26—C272.5 (9)
C15—C16—C17—Fe59.2 (4)C25—C26—C27—C28−2.4 (9)
C14—C13—C17—C16−0.6 (6)C26—C27—C28—C230.8 (9)
P1—C13—C17—C16−178.4 (4)C24—C23—C28—C270.8 (8)
Fe—C13—C17—C1659.0 (4)P2—C23—C28—C27177.4 (4)
C14—C13—C17—Fe−59.6 (4)C18—P2—C29—C3063.6 (5)
P1—C13—C17—Fe122.6 (5)C23—P2—C29—C30−46.9 (5)
C18—Fe—C17—C1664.0 (5)Au2—P2—C29—C30−169.7 (4)
C22—Fe—C17—C1616.7 (18)C18—P2—C29—C34−118.7 (4)
C14—Fe—C17—C16−81.7 (4)C23—P2—C29—C34130.8 (4)
C13—Fe—C17—C16−120.0 (5)Au2—P2—C29—C348.0 (5)
C15—Fe—C17—C16−37.6 (4)C34—C29—C30—C310.5 (9)
C19—Fe—C17—C16105.6 (4)P2—C29—C30—C31178.2 (5)
C20—Fe—C17—C16150.0 (4)C29—C30—C31—C32−1.2 (9)
C21—Fe—C17—C16−171.4 (4)C30—C31—C32—C330.3 (10)
C18—Fe—C17—C13−176.1 (3)C31—C32—C33—C341.2 (10)
C22—Fe—C17—C13136.6 (15)C32—C33—C34—C29−1.9 (9)
C14—Fe—C17—C1338.2 (3)C30—C29—C34—C331.1 (8)
C15—Fe—C17—C1382.4 (4)P2—C29—C34—C33−176.6 (4)
C19—Fe—C17—C13−134.4 (3)C36i—C36—C37—C38178.6 (7)
C16—Fe—C17—C13120.0 (5)

Symmetry codes: (i) −x+1, −y+1, −z+2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C35—H35···Cl2ii1.002.723.634 (8)153

Symmetry codes: (ii) x, y+1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2624).

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