[μ-1,1′-Bis(diphenyl­phosphino)ferrocene]bis­{[(Z)-O-ethyl N-phenyl­thio­carbamato-κS]gold(I)} dichloro­methane solvate

Ho, S.Y.; Tiekink, E.R.T.

doi:10.1107/S160053681001562X

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 6| June 2010| Pages m608-m609

https://doi.org/10.1107/S160053681001562X

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[μ-1,1′-Bis(diphenylphosphino)ferrocene]bis{[(Z)-O-ethyl N-phenylthiocarbamato-κS]gold(I)} dichloromethane solvate

Soo Yei Ho ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, National University of Singapore, Singapore 117543, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 21 April 2010; accepted 27 April 2010; online 8 May 2010)

The binuclear title compound, [Au₂Fe(C₉H₁₀NOS)₂(C₁₇H₁₄P)₂]·CH₂Cl₂, which has the Fe atom located on a crystallographic centre of inversion, crystallizes as a 1:1 dichloromethane solvate, which is disordered about a centre of inversion. There is a small deviation from linearity defined by the SP donor set [S1—Au—P1 angle is 175.35 (5) °] which is due to an intramolecular Au⋯O contact [3.080 (5) Å]. The primary intermolecular contacts between binuclear molecules are of the type C—H⋯π, and are arranged so as to form columns in the a-axis direction in which the disordered solvent molecules reside.

Related literature

For the structural systematics and luminescence properties of phosphinegold(I) carbonimidothioates, see: Ho et al. (2006 ); Ho & Tiekink (2007 ); Kuan et al. (2008 ). For the synthesis, see: Hall et al. (1993 ). For related structures, see: Ho & Tiekink (2009 ); Tadbuppa & Tiekink (2009 ).

Experimental

Crystal data

[Au₂Fe(C₉H₁₀NOS)₂(C₁₇H₁₄P)₂]·CH₂Cl₂
M_r = 1393.69
Triclinic, $[P \overline 1]$
a = 8.442 (3) Å
b = 12.957 (5) Å
c = 13.440 (5) Å
α = 108.045 (8)°
β = 103.177 (8)°
γ = 106.853 (8)°
V = 1253.5 (9) Å³
Z = 1
Mo Kα radiation
μ = 6.42 mm⁻¹
T = 223 K
0.49 × 0.04 × 0.04 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.577, T_max = 1
8618 measured reflections
5688 independent reflections
5025 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.106
S = 1.02
5688 reflections
307 parameters
13 restraints
H-atom parameters constrained
Δρ_max = 2.84 e Å⁻³
Δρ_min = −1.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Au—P1	2.2562 (15)
Au—S1	2.3029 (16)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9a⋯Cg1ⁱ	0.97	2.75	3.623 (9)	150
C11—H11⋯Cg2ⁱⁱ	0.94	2.78	3.619 (7)	150
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y, -z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SHELXTL (Sheldrick, 2008 ); program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681001562X/pk2245sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681001562X/pk2245Isup2.hkl

checkCIF report

Comment top

The dppf (where dppf is the bidentate phosphine, [Ph₂P(C₅H₄)]₂Fe) derivatives of phosphinegold(I) thiocarbamides, of interest owing to crystal engineering and luminescence studies (Ho et al. 2006; Ho & Tiekink, 2007; Kuan et al., 2008), are comparatively rare. Thus, only three examples of dppf{Au[SC(OR)═NR']}₂ have been described, i.e. R = Me & R' = PhNO₂-4 (Ho et al., 2006), R = iPr & R' = PhNO₂-4 (Ho & Tiekink, 2009), and R = iPr & R' = PhMe-4 (Tadbuppa & Tiekink, 2009). In the present report, the crystal structure of the R = Et & R' = H derivative, (I), is described.

The dinuclear molecule has crystallographic symmetry with the Fe atom lying on an inversion centre, Fig. 1. The dinuclear molecule crystallises with a solvent dichloromethane molecule which is disordered about a centre of inversion, Fig. 1. The gold atom exists in the expected linear geometry defined by a SP donor set, Table 1, and the deviation from linearity [S1–Au–P1 is 175.35 (5) °] is ascribed to the close approach of the O1 atom, Au···O = 3.080 (5) Å. The anion, with a Z configuration about the C1═N1 bond, shows the expected characteristics. The magnitudes of the C1—S1 and C1═N1 bond distances of 1.755 (6) and 1.277 (8) Å, respectively, confirm that the anion is coordinating as a thiolate ligand. The overall conformation of the molecule is "open" in that the thiocarbamate ligands are lying on either side of the molecule, as found in the structure of the R = iPr & R' = PhMe-4 derivative (Tadbuppa & Tiekink, 2009) but contrasts the situation in each of dppf{Au[SC(OR)═ NC₆H₄NO₂-p]}₂, for R = Me (Ho et al., 2006) and i-Pr (Ho & Tiekink, 2009), whereby the molecule has a U-shaped conformation allowing for the formation of intramolecular Au···Au interactions.

In the crystal structure of (I), the primary interactions between the dinuclear molecules are of the type C–H···π, Table 1. These are arranged so as to define columns along the a direction in which reside the solvent dichloromethane molecules.

Related literature top

For the structural systematics and luminescence properties of phosphinegold(I) carbonimidothioates, see: Ho et al. (2006); Ho & Tiekink (2007); Kuan et al. (2008). For the synthesis, see Hall et al. (1993). For related structures, see Ho & Tiekink (2009); Tadbuppa & Tiekink (2009).

Experimental top

Compound (I) was prepared following the standard literature procedure from the reaction of dppf(AuCl)₂ and EtOC(═S)N(H)Ph in the presence of base (Hall et al., 1993). Crystals were obtained from the slow evaporation of a dichloromethane solution.

Structure description top

For the structural systematics and luminescence properties of phosphinegold(I) carbonimidothioates, see: Ho et al. (2006); Ho & Tiekink (2007); Kuan et al. (2008). For the synthesis, see Hall et al. (1993). For related structures, see Ho & Tiekink (2009); Tadbuppa & Tiekink (2009).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SHELXTL (Sheldrick, 2008); program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structure of the dinuclear complex (I) showing atom-labelling scheme and displacement ellipsoids at the 50% probability level. The dinuclear molecule is located about a centre of inversion and unlabelled atoms are related by the symmetry operation -x, -y, -z. Also shown is the solvent dichloromethane molecule which is disordered about a centre of inversion. Unlabelled atoms are related by -x, 1-y, 1-z for this molecule.

Fig. 2. A view in projection down the a axis of the crystal packing in (I) highlighting the interactions between binuclear molecules mediated by C–H···π contacts (purple dashed lines). The binuclear molecules define columns in which reside the disordered dichloromethane molecules, shown in space filling mode. Colour code: Au, orange; Fe, olive green; S, yellow; P, pink; O, red; N, blue; C, grey; and H, green.

[µ-1,1'-Bis(diphenylphosphino)ferrocene]bis{[(Z)-O-ethyl N-phenylthiocarbamato-κS]gold(I)} dichloromethane solvate top

Crystal data top

[Au₂Fe(C₉H₁₀NOS)₂(C₁₇H₁₄P)₂]·CH₂Cl₂	Z = 1
M_r = 1393.69	F(000) = 678
Triclinic, P1	D_x = 1.846 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.442 (3) Å	Cell parameters from 4599 reflections
b = 12.957 (5) Å	θ = 2.6–30.1°
c = 13.440 (5) Å	µ = 6.42 mm⁻¹
α = 108.045 (8)°	T = 223 K
β = 103.177 (8)°	Needle, orange
γ = 106.853 (8)°	0.49 × 0.04 × 0.04 mm
V = 1253.5 (9) Å³

Data collection top

Bruker SMART CCD diffractometer	5688 independent reflections
Radiation source: fine-focus sealed tube	5025 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.5°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.577, T_max = 1	k = −16→11
8618 measured reflections	l = −16→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.106	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0684P)²] where P = (F_o² + 2F_c²)/3
5688 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 2.84 e Å⁻³
13 restraints	Δρ_min = −1.47 e Å⁻³

Crystal data top

[Au₂Fe(C₉H₁₀NOS)₂(C₁₇H₁₄P)₂]·CH₂Cl₂	γ = 106.853 (8)°
M_r = 1393.69	V = 1253.5 (9) Å³
Triclinic, P1	Z = 1
a = 8.442 (3) Å	Mo Kα radiation
b = 12.957 (5) Å	µ = 6.42 mm⁻¹
c = 13.440 (5) Å	T = 223 K
α = 108.045 (8)°	0.49 × 0.04 × 0.04 mm
β = 103.177 (8)°

Data collection top

Bruker SMART CCD diffractometer	5688 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	5025 reflections with I > 2σ(I)
T_min = 0.577, T_max = 1	R_int = 0.030
8618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	13 restraints
wR(F²) = 0.106	H-atom parameters constrained
S = 1.02	Δρ_max = 2.84 e Å⁻³
5688 reflections	Δρ_min = −1.47 e Å⁻³
307 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Au	0.54576 (2)	0.149128 (17)	0.224945 (16)	0.02842 (9)
Fe	0.0000	0.0000	0.0000	0.0234 (2)
S1	0.6884 (2)	0.11576 (15)	0.37230 (12)	0.0387 (3)
P1	0.42701 (17)	0.19357 (11)	0.08358 (11)	0.0240 (3)
O1	0.4392 (5)	0.1685 (4)	0.4324 (3)	0.0397 (10)
N1	0.6859 (6)	0.2200 (5)	0.5809 (4)	0.0368 (11)
C1	0.6054 (8)	0.1739 (5)	0.4754 (5)	0.0317 (11)
C2	0.8589 (8)	0.2308 (5)	0.6274 (5)	0.0344 (12)
C3	0.8983 (9)	0.1323 (6)	0.6232 (6)	0.0422 (14)
H3	0.8092	0.0561	0.5840	0.051*
C4	1.0693 (9)	0.1475 (6)	0.6769 (6)	0.0439 (14)
H4	1.0952	0.0810	0.6739	0.053*
C5	1.2007 (9)	0.2566 (6)	0.7341 (5)	0.0434 (15)
H5	1.3163	0.2649	0.7690	0.052*
C6	1.1636 (8)	0.3563 (6)	0.7409 (6)	0.0440 (15)
H6	1.2529	0.4323	0.7808	0.053*
C7	0.9909 (8)	0.3404 (6)	0.6873 (5)	0.0394 (13)
H7	0.9642	0.4070	0.6924	0.047*
C8	0.3614 (8)	0.2141 (7)	0.5128 (6)	0.0466 (16)
H8A	0.4412	0.2944	0.5658	0.056*
H8B	0.3408	0.1646	0.5546	0.056*
C9	0.1920 (10)	0.2139 (8)	0.4508 (6)	0.0551 (19)
H9A	0.1370	0.2436	0.5031	0.083*
H9B	0.1142	0.1342	0.3983	0.083*
H9C	0.2139	0.2640	0.4106	0.083*
C10	0.2261 (7)	0.0814 (4)	−0.0219 (4)	0.0255 (10)
C11	0.1892 (7)	−0.0416 (5)	−0.0552 (5)	0.0312 (11)
H11	0.2615	−0.0753	−0.0247	0.037*
C12	0.0209 (8)	−0.1038 (5)	−0.1443 (5)	0.0377 (14)
H12	−0.0363	−0.1860	−0.1833	0.045*
C13	−0.0434 (8)	−0.0202 (5)	−0.1629 (5)	0.0372 (13)
H13	−0.1520	−0.0377	−0.2161	0.045*
C14	0.0802 (7)	0.0937 (5)	−0.0894 (5)	0.0304 (11)
H14	0.0693	0.1650	−0.0853	0.036*
C15	0.5783 (7)	0.2270 (4)	0.0097 (5)	0.0268 (10)
C16	0.5327 (8)	0.1678 (5)	−0.1046 (5)	0.0320 (11)
H16	0.4185	0.1101	−0.1479	0.038*
C17	0.6581 (9)	0.1949 (6)	−0.1545 (5)	0.0395 (13)
H17	0.6282	0.1551	−0.2319	0.047*
C18	0.8269 (8)	0.2804 (6)	−0.0905 (6)	0.0426 (15)
H18	0.9102	0.2990	−0.1247	0.051*
C19	0.8716 (8)	0.3371 (6)	0.0215 (6)	0.0425 (14)
H19	0.9861	0.3945	0.0643	0.051*
C20	0.7489 (7)	0.3110 (5)	0.0738 (5)	0.0335 (12)
H20	0.7812	0.3498	0.1515	0.040*
C21	0.3847 (7)	0.3269 (5)	0.1315 (5)	0.0294 (11)
C22	0.3700 (7)	0.3903 (5)	0.0660 (5)	0.0321 (11)
H22	0.3774	0.3630	−0.0056	0.038*
C23	0.3444 (8)	0.4938 (5)	0.1063 (6)	0.0372 (13)
H23	0.3335	0.5363	0.0615	0.045*
C24	0.3348 (8)	0.5355 (5)	0.2118 (6)	0.0379 (13)
H24	0.3199	0.6068	0.2393	0.046*
C25	0.3471 (9)	0.4717 (6)	0.2762 (6)	0.0454 (15)
H25	0.3379	0.4988	0.3473	0.055*
C26	0.3728 (8)	0.3689 (5)	0.2371 (5)	0.0353 (12)
H26	0.3824	0.3265	0.2821	0.042*
Cl1	0.1902 (6)	0.5357 (4)	0.5501 (4)	0.1365 (14)
C27	0.0112 (19)	0.5715 (19)	0.548 (2)	0.085 (6)	0.50
H27A	0.0327	0.6434	0.5342	0.103*	0.50
H27B	0.0018	0.5900	0.6223	0.103*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au	0.02700 (12)	0.03400 (13)	0.02496 (13)	0.01353 (9)	0.00771 (8)	0.01222 (9)
Fe	0.0212 (4)	0.0246 (5)	0.0227 (5)	0.0075 (4)	0.0068 (4)	0.0093 (4)
S1	0.0421 (8)	0.0566 (9)	0.0265 (7)	0.0317 (7)	0.0117 (6)	0.0171 (6)
P1	0.0230 (6)	0.0252 (6)	0.0242 (6)	0.0100 (5)	0.0086 (5)	0.0098 (5)
O1	0.031 (2)	0.054 (3)	0.028 (2)	0.0181 (19)	0.0081 (17)	0.0088 (19)
N1	0.031 (2)	0.049 (3)	0.021 (2)	0.010 (2)	0.0066 (19)	0.009 (2)
C1	0.032 (3)	0.037 (3)	0.026 (3)	0.015 (2)	0.009 (2)	0.013 (2)
C2	0.033 (3)	0.049 (3)	0.023 (3)	0.016 (2)	0.011 (2)	0.016 (2)
C3	0.041 (3)	0.040 (3)	0.040 (3)	0.009 (3)	0.010 (3)	0.019 (3)
C4	0.051 (4)	0.048 (4)	0.042 (4)	0.025 (3)	0.013 (3)	0.027 (3)
C5	0.035 (3)	0.064 (4)	0.033 (3)	0.021 (3)	0.009 (3)	0.023 (3)
C6	0.030 (3)	0.051 (4)	0.038 (3)	0.007 (3)	0.007 (3)	0.015 (3)
C7	0.031 (3)	0.047 (3)	0.038 (3)	0.015 (3)	0.012 (3)	0.014 (3)
C8	0.037 (3)	0.061 (4)	0.036 (3)	0.022 (3)	0.014 (3)	0.007 (3)
C9	0.052 (4)	0.083 (5)	0.037 (4)	0.042 (4)	0.016 (3)	0.018 (4)
C10	0.026 (2)	0.026 (2)	0.025 (2)	0.0100 (19)	0.008 (2)	0.0101 (19)
C11	0.034 (3)	0.027 (3)	0.034 (3)	0.013 (2)	0.015 (2)	0.011 (2)
C12	0.033 (3)	0.032 (3)	0.035 (3)	0.003 (2)	0.018 (3)	0.002 (2)
C13	0.032 (3)	0.046 (3)	0.023 (3)	0.007 (2)	0.006 (2)	0.011 (2)
C14	0.026 (2)	0.041 (3)	0.027 (3)	0.012 (2)	0.010 (2)	0.019 (2)
C15	0.024 (2)	0.028 (2)	0.035 (3)	0.012 (2)	0.013 (2)	0.017 (2)
C16	0.032 (3)	0.033 (3)	0.034 (3)	0.013 (2)	0.012 (2)	0.015 (2)
C17	0.049 (3)	0.049 (3)	0.037 (3)	0.027 (3)	0.027 (3)	0.022 (3)
C18	0.038 (3)	0.053 (4)	0.065 (4)	0.028 (3)	0.033 (3)	0.040 (3)
C19	0.027 (3)	0.040 (3)	0.061 (4)	0.011 (2)	0.016 (3)	0.022 (3)
C20	0.027 (3)	0.032 (3)	0.038 (3)	0.008 (2)	0.010 (2)	0.013 (2)
C21	0.020 (2)	0.028 (2)	0.035 (3)	0.0059 (19)	0.008 (2)	0.010 (2)
C22	0.030 (3)	0.027 (3)	0.038 (3)	0.011 (2)	0.013 (2)	0.011 (2)
C23	0.028 (3)	0.035 (3)	0.048 (4)	0.012 (2)	0.011 (3)	0.019 (3)
C24	0.034 (3)	0.026 (3)	0.044 (3)	0.010 (2)	0.009 (3)	0.005 (2)
C25	0.048 (4)	0.047 (4)	0.032 (3)	0.019 (3)	0.016 (3)	0.003 (3)
C26	0.038 (3)	0.032 (3)	0.035 (3)	0.014 (2)	0.015 (3)	0.011 (2)
Cl1	0.1389 (16)	0.1335 (16)	0.1363 (16)	0.0487 (10)	0.0470 (10)	0.0583 (10)
Cl1'	0.1389 (16)	0.1335 (16)	0.1363 (16)	0.0487 (10)	0.0470 (10)	0.0583 (10)
C27	0.086 (6)	0.085 (6)	0.085 (6)	0.033 (2)	0.030 (2)	0.035 (2)

Geometric parameters (Å, º) top

Au—P1	2.2562 (15)	C9—H9C	0.9700
Au—S1	2.3029 (16)	C10—C11	1.429 (7)
Fe—C10	2.030 (5)	C10—C14	1.435 (7)
Fe—C10ⁱ	2.030 (5)	C11—C12	1.437 (8)
Fe—C14ⁱ	2.043 (5)	C11—H11	0.9400
Fe—C14	2.043 (5)	C12—C13	1.405 (9)
Fe—C11ⁱ	2.046 (5)	C12—H12	0.9400
Fe—C11	2.046 (5)	C13—C14	1.406 (8)
Fe—C13ⁱ	2.054 (6)	C13—H13	0.9400
Fe—C13	2.054 (6)	C14—H14	0.9400
Fe—C12	2.068 (5)	C15—C16	1.387 (8)
Fe—C12ⁱ	2.068 (5)	C15—C20	1.395 (7)
S1—C1	1.755 (6)	C16—C17	1.396 (8)
P1—C10	1.788 (5)	C16—H16	0.9400
P1—C21	1.817 (5)	C17—C18	1.391 (9)
P1—C15	1.824 (5)	C17—H17	0.9400
O1—C1	1.362 (7)	C18—C19	1.357 (10)
O1—C8	1.449 (7)	C18—H18	0.9400
N1—C1	1.277 (7)	C19—C20	1.399 (8)
N1—C2	1.398 (7)	C19—H19	0.9400
C2—C7	1.368 (9)	C20—H20	0.9400
C2—C3	1.398 (9)	C21—C22	1.387 (8)
C3—C4	1.384 (9)	C21—C26	1.393 (8)
C3—H3	0.9400	C22—C23	1.382 (8)
C4—C5	1.360 (10)	C22—H22	0.9400
C4—H4	0.9400	C23—C24	1.383 (9)
C5—C6	1.397 (10)	C23—H23	0.9400
C5—H5	0.9400	C24—C25	1.376 (10)
C6—C7	1.393 (9)	C24—H24	0.9400
C6—H6	0.9400	C25—C26	1.372 (9)
C7—H7	0.9400	C25—H25	0.9400
C8—C9	1.480 (9)	C26—H26	0.9400
C8—H8A	0.9800	Cl1—C27	1.701 (5)
C8—H8B	0.9800	Cl1—C27ⁱⁱ	1.74 (2)
C9—H9A	0.9700	C27—H27A	0.9800
C9—H9B	0.9700	C27—H27B	0.9800

P1—Au—S1	175.35 (5)	C9—C8—H8B	110.1
C10—Fe—C10ⁱ	180.0 (3)	H8A—C8—H8B	108.4
C10—Fe—C14ⁱ	138.7 (2)	C8—C9—H9A	109.5
C10ⁱ—Fe—C14ⁱ	41.3 (2)	C8—C9—H9B	109.5
C10—Fe—C14	41.3 (2)	H9A—C9—H9B	109.5
C10ⁱ—Fe—C14	138.7 (2)	C8—C9—H9C	109.5
C14ⁱ—Fe—C14	180.0 (3)	H9A—C9—H9C	109.5
C10—Fe—C11ⁱ	139.0 (2)	H9B—C9—H9C	109.5
C10ⁱ—Fe—C11ⁱ	41.0 (2)	C11—C10—C14	108.0 (5)
C14ⁱ—Fe—C11ⁱ	69.0 (2)	C11—C10—P1	122.9 (4)
C14—Fe—C11ⁱ	111.0 (2)	C14—C10—P1	129.0 (4)
C10—Fe—C11	41.0 (2)	C11—C10—Fe	70.1 (3)
C10ⁱ—Fe—C11	139.0 (2)	C14—C10—Fe	69.9 (3)
C14ⁱ—Fe—C11	111.0 (2)	P1—C10—Fe	127.3 (3)
C14—Fe—C11	69.0 (2)	C10—C11—C12	107.0 (5)
C11ⁱ—Fe—C11	180.0 (3)	C10—C11—Fe	68.9 (3)
C10—Fe—C13ⁱ	111.7 (2)	C12—C11—Fe	70.4 (3)
C10ⁱ—Fe—C13ⁱ	68.3 (2)	C10—C11—H11	126.5
C14ⁱ—Fe—C13ⁱ	40.1 (2)	C12—C11—H11	126.5
C14—Fe—C13ⁱ	139.9 (2)	Fe—C11—H11	125.8
C11ⁱ—Fe—C13ⁱ	68.3 (2)	C13—C12—C11	108.1 (5)
C11—Fe—C13ⁱ	111.7 (2)	C13—C12—Fe	69.5 (3)
C10—Fe—C13	68.3 (2)	C11—C12—Fe	68.7 (3)
C10ⁱ—Fe—C13	111.7 (2)	C13—C12—H12	126.0
C14ⁱ—Fe—C13	139.9 (2)	C11—C12—H12	126.0
C14—Fe—C13	40.1 (2)	Fe—C12—H12	127.4
C11ⁱ—Fe—C13	111.7 (2)	C14—C13—C12	109.3 (5)
C11—Fe—C13	68.3 (2)	C14—C13—Fe	69.5 (3)
C13ⁱ—Fe—C13	180.0 (3)	C12—C13—Fe	70.6 (4)
C10—Fe—C12	68.4 (2)	C14—C13—H13	125.3
C10ⁱ—Fe—C12	111.6 (2)	C12—C13—H13	125.3
C14ⁱ—Fe—C12	112.2 (2)	Fe—C13—H13	126.1
C14—Fe—C12	67.8 (2)	C13—C14—C10	107.5 (5)
C11ⁱ—Fe—C12	139.1 (2)	C13—C14—Fe	70.3 (3)
C11—Fe—C12	40.9 (2)	C10—C14—Fe	68.9 (3)
C13ⁱ—Fe—C12	140.1 (3)	C13—C14—H14	126.2
C13—Fe—C12	39.9 (3)	C10—C14—H14	126.2
C10—Fe—C12ⁱ	111.6 (2)	Fe—C14—H14	126.1
C10ⁱ—Fe—C12ⁱ	68.4 (2)	C16—C15—C20	120.0 (5)
C14ⁱ—Fe—C12ⁱ	67.8 (2)	C16—C15—P1	122.6 (4)
C14—Fe—C12ⁱ	112.2 (2)	C20—C15—P1	117.3 (4)
C11ⁱ—Fe—C12ⁱ	40.9 (2)	C15—C16—C17	119.3 (5)
C11—Fe—C12ⁱ	139.1 (2)	C15—C16—H16	120.3
C13ⁱ—Fe—C12ⁱ	39.9 (3)	C17—C16—H16	120.3
C13—Fe—C12ⁱ	140.1 (3)	C18—C17—C16	120.4 (6)
C12—Fe—C12ⁱ	180.0 (4)	C18—C17—H17	119.8
C1—S1—Au	102.6 (2)	C16—C17—H17	119.8
C10—P1—C21	106.8 (2)	C19—C18—C17	120.1 (5)
C10—P1—C15	105.4 (2)	C19—C18—H18	119.9
C21—P1—C15	103.4 (2)	C17—C18—H18	119.9
C10—P1—Au	115.79 (18)	C18—C19—C20	120.7 (6)
C21—P1—Au	112.8 (2)	C18—C19—H19	119.7
C15—P1—Au	111.77 (18)	C20—C19—H19	119.7
C1—O1—C8	116.2 (5)	C15—C20—C19	119.5 (6)
C1—N1—C2	121.6 (5)	C15—C20—H20	120.3
N1—C1—O1	120.3 (5)	C19—C20—H20	120.3
N1—C1—S1	126.6 (5)	C22—C21—C26	119.1 (5)
O1—C1—S1	113.1 (4)	C22—C21—P1	121.0 (4)
C7—C2—N1	119.6 (6)	C26—C21—P1	119.8 (5)
C7—C2—C3	118.6 (6)	C23—C22—C21	119.7 (6)
N1—C2—C3	121.5 (6)	C23—C22—H22	120.1
C4—C3—C2	119.6 (6)	C21—C22—H22	120.1
C4—C3—H3	120.2	C22—C23—C24	120.7 (6)
C2—C3—H3	120.2	C22—C23—H23	119.6
C5—C4—C3	121.4 (6)	C24—C23—H23	119.6
C5—C4—H4	119.3	C25—C24—C23	119.5 (6)
C3—C4—H4	119.3	C25—C24—H24	120.2
C4—C5—C6	119.9 (6)	C23—C24—H24	120.2
C4—C5—H5	120.1	C26—C25—C24	120.3 (6)
C6—C5—H5	120.1	C26—C25—H25	119.8
C7—C6—C5	118.4 (6)	C24—C25—H25	119.8
C7—C6—H6	120.8	C25—C26—C21	120.6 (6)
C5—C6—H6	120.8	C25—C26—H26	119.7
C2—C7—C6	122.1 (6)	C21—C26—H26	119.7
C2—C7—H7	119.0	Cl1ⁱⁱ—C27—Cl1	116.5 (11)
C6—C7—H7	119.0	Cl1—C27—H27A	108.2
O1—C8—C9	108.1 (5)	Cl1ⁱⁱ—C27—H27A	108.2
O1—C8—H8A	110.1	Cl1—C27—H27B	108.2
C9—C8—H8A	110.1	Cl1ⁱⁱ—C27—H27B	108.2
O1—C8—H8B	110.1	H27A—C27—H27B	107.3

P1—Au—S1—C1	106.4 (6)	C11ⁱ—Fe—C12—C13	59.9 (5)
S1—Au—P1—C10	160.4 (6)	C11—Fe—C12—C13	−120.1 (5)
S1—Au—P1—C21	−76.2 (6)	C13ⁱ—Fe—C12—C13	180.000 (1)
S1—Au—P1—C15	39.7 (6)	C12ⁱ—Fe—C12—C13	−49 (34)
C2—N1—C1—O1	−177.6 (5)	C10—Fe—C12—C11	38.5 (3)
C2—N1—C1—S1	1.0 (9)	C10ⁱ—Fe—C12—C11	−141.5 (3)
C8—O1—C1—N1	−1.7 (8)	C14ⁱ—Fe—C12—C11	−96.8 (3)
C8—O1—C1—S1	179.5 (5)	C14—Fe—C12—C11	83.2 (3)
Au—S1—C1—N1	−149.8 (5)	C11ⁱ—Fe—C12—C11	180.0
Au—S1—C1—O1	28.9 (5)	C13ⁱ—Fe—C12—C11	−59.9 (5)
C1—N1—C2—C7	115.8 (7)	C13—Fe—C12—C11	120.1 (5)
C1—N1—C2—C3	−70.2 (8)	C12ⁱ—Fe—C12—C11	71 (32)
C7—C2—C3—C4	−1.5 (9)	C11—C12—C13—C14	0.9 (6)
N1—C2—C3—C4	−175.5 (6)	Fe—C12—C13—C14	58.9 (4)
C2—C3—C4—C5	0.0 (10)	C11—C12—C13—Fe	−58.0 (4)
C3—C4—C5—C6	1.1 (10)	C10—Fe—C13—C14	−38.5 (3)
C4—C5—C6—C7	−0.6 (10)	C10ⁱ—Fe—C13—C14	141.5 (3)
N1—C2—C7—C6	176.1 (6)	C14ⁱ—Fe—C13—C14	180.0
C3—C2—C7—C6	2.0 (9)	C11ⁱ—Fe—C13—C14	97.2 (4)
C5—C6—C7—C2	−1.0 (10)	C11—Fe—C13—C14	−82.8 (4)
C1—O1—C8—C9	173.2 (6)	C13ⁱ—Fe—C13—C14	54 (58)
C21—P1—C10—C11	−160.4 (4)	C12—Fe—C13—C14	−120.4 (5)
C15—P1—C10—C11	90.1 (5)	C12ⁱ—Fe—C13—C14	59.6 (5)
Au—P1—C10—C11	−33.9 (5)	C10—Fe—C13—C12	81.9 (3)
C21—P1—C10—C14	22.0 (6)	C10ⁱ—Fe—C13—C12	−98.1 (3)
C15—P1—C10—C14	−87.4 (5)	C14ⁱ—Fe—C13—C12	−59.6 (5)
Au—P1—C10—C14	148.5 (4)	C14—Fe—C13—C12	120.4 (5)
C21—P1—C10—Fe	−71.4 (4)	C11ⁱ—Fe—C13—C12	−142.4 (3)
C15—P1—C10—Fe	179.2 (3)	C11—Fe—C13—C12	37.6 (3)
Au—P1—C10—Fe	55.1 (4)	C13ⁱ—Fe—C13—C12	174 (58)
C10ⁱ—Fe—C10—C11	−160 (45)	C12ⁱ—Fe—C13—C12	180.000 (1)
C14ⁱ—Fe—C10—C11	61.1 (5)	C12—C13—C14—C10	−0.5 (6)
C14—Fe—C10—C11	−118.9 (5)	Fe—C13—C14—C10	59.1 (4)
C11ⁱ—Fe—C10—C11	180.0	C12—C13—C14—Fe	−59.6 (4)
C13ⁱ—Fe—C10—C11	98.6 (4)	C11—C10—C14—C13	−0.1 (6)
C13—Fe—C10—C11	−81.4 (4)	P1—C10—C14—C13	177.8 (4)
C12—Fe—C10—C11	−38.4 (4)	Fe—C10—C14—C13	−60.0 (4)
C12ⁱ—Fe—C10—C11	141.6 (4)	C11—C10—C14—Fe	59.9 (4)
C10ⁱ—Fe—C10—C14	−41 (45)	P1—C10—C14—Fe	−122.2 (4)
C14ⁱ—Fe—C10—C14	180.0	C10—Fe—C14—C13	118.7 (5)
C11ⁱ—Fe—C10—C14	−61.1 (5)	C10ⁱ—Fe—C14—C13	−61.3 (5)
C11—Fe—C10—C14	118.9 (5)	C14ⁱ—Fe—C14—C13	−135 (100)
C13ⁱ—Fe—C10—C14	−142.5 (3)	C11ⁱ—Fe—C14—C13	−99.3 (4)
C13—Fe—C10—C14	37.5 (3)	C11—Fe—C14—C13	80.7 (4)
C12—Fe—C10—C14	80.5 (4)	C13ⁱ—Fe—C14—C13	180.0
C12ⁱ—Fe—C10—C14	−99.5 (4)	C12—Fe—C14—C13	36.7 (4)
C10ⁱ—Fe—C10—P1	83 (45)	C12ⁱ—Fe—C14—C13	−143.3 (4)
C14ⁱ—Fe—C10—P1	−55.7 (5)	C10ⁱ—Fe—C14—C10	180.0
C14—Fe—C10—P1	124.3 (5)	C14ⁱ—Fe—C14—C10	106 (100)
C11ⁱ—Fe—C10—P1	63.2 (5)	C11ⁱ—Fe—C14—C10	142.0 (3)
C11—Fe—C10—P1	−116.8 (5)	C11—Fe—C14—C10	−38.0 (3)
C13ⁱ—Fe—C10—P1	−18.3 (4)	C13ⁱ—Fe—C14—C10	61.3 (5)
C13—Fe—C10—P1	161.7 (4)	C13—Fe—C14—C10	−118.7 (5)
C12—Fe—C10—P1	−155.2 (4)	C12—Fe—C14—C10	−82.1 (3)
C12ⁱ—Fe—C10—P1	24.8 (4)	C12ⁱ—Fe—C14—C10	97.9 (3)
C14—C10—C11—C12	0.6 (6)	C10—P1—C15—C16	−2.2 (5)
P1—C10—C11—C12	−177.4 (4)	C21—P1—C15—C16	−114.1 (5)
Fe—C10—C11—C12	60.4 (4)	Au—P1—C15—C16	124.4 (4)
C14—C10—C11—Fe	−59.8 (4)	C10—P1—C15—C20	−178.4 (4)
P1—C10—C11—Fe	122.2 (4)	C21—P1—C15—C20	69.7 (5)
C10ⁱ—Fe—C11—C10	180.0	Au—P1—C15—C20	−51.9 (5)
C14ⁱ—Fe—C11—C10	−141.8 (3)	C20—C15—C16—C17	−1.2 (8)
C14—Fe—C11—C10	38.2 (3)	P1—C15—C16—C17	−177.3 (4)
C11ⁱ—Fe—C11—C10	8 (100)	C15—C16—C17—C18	−0.1 (9)
C13ⁱ—Fe—C11—C10	−98.6 (4)	C16—C17—C18—C19	0.8 (9)
C13—Fe—C11—C10	81.4 (4)	C17—C18—C19—C20	−0.3 (10)
C12—Fe—C11—C10	118.1 (5)	C16—C15—C20—C19	1.7 (8)
C12ⁱ—Fe—C11—C10	−61.9 (5)	P1—C15—C20—C19	178.1 (4)
C10—Fe—C11—C12	−118.1 (5)	C18—C19—C20—C15	−0.9 (9)
C10ⁱ—Fe—C11—C12	61.9 (5)	C10—P1—C21—C22	−73.8 (5)
C14ⁱ—Fe—C11—C12	100.1 (4)	C15—P1—C21—C22	37.1 (5)
C14—Fe—C11—C12	−79.9 (4)	Au—P1—C21—C22	157.9 (4)
C11ⁱ—Fe—C11—C12	−110 (100)	C10—P1—C21—C26	108.5 (5)
C13ⁱ—Fe—C11—C12	143.3 (4)	C15—P1—C21—C26	−140.7 (4)
C13—Fe—C11—C12	−36.7 (4)	Au—P1—C21—C26	−19.8 (5)
C12ⁱ—Fe—C11—C12	180.0	C26—C21—C22—C23	0.2 (8)
C10—C11—C12—C13	−0.9 (6)	P1—C21—C22—C23	−177.6 (4)
Fe—C11—C12—C13	58.5 (4)	C21—C22—C23—C24	0.6 (9)
C10—C11—C12—Fe	−59.4 (4)	C22—C23—C24—C25	−1.4 (9)
C10—Fe—C12—C13	−81.5 (4)	C23—C24—C25—C26	1.5 (10)
C10ⁱ—Fe—C12—C13	98.5 (4)	C24—C25—C26—C21	−0.7 (10)
C14ⁱ—Fe—C12—C13	143.1 (3)	C22—C21—C26—C25	−0.1 (9)
C14—Fe—C12—C13	−36.9 (3)	P1—C21—C26—C25	177.7 (5)

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9a···Cg1ⁱⁱⁱ	0.97	2.75	3.623 (9)	150
C11—H11···Cg2^iv	0.94	2.78	3.619 (7)	150

Symmetry codes: (iii) x−1, y, z; (iv) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	[Au₂Fe(C₉H₁₀NOS)₂(C₁₇H₁₄P)₂]·CH₂Cl₂
M_r	1393.69
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	8.442 (3), 12.957 (5), 13.440 (5)
α, β, γ (°)	108.045 (8), 103.177 (8), 106.853 (8)
V (Å³)	1253.5 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	6.42
Crystal size (mm)	0.49 × 0.04 × 0.04

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.577, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	8618, 5688, 5025
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.106, 1.02
No. of reflections	5688
No. of parameters	307
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.84, −1.47

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008), PATTY in DIRDIF92 (Beurskens et al., 1992), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Au—P1

2.2562 (15)

Au—S1

2.3029 (16)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C2–C7 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9a···Cg1ⁱ	0.97	2.75	3.623 (9)	150
C11—H11···Cg2ⁱⁱ	0.94	2.78	3.619 (7)	150

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

Acknowledgements

The National University of Singapore (grant No. R-143–000-213–112) is thanked for support.

References

Beurskens, P. T., Admiraal, G., Beurskens, G., Bosman, W. P., Garcia-Granda, S., Gould, R. O., Smits, J. M. M. & Smykalla, C. (1992). The DIRDIF Program System. Technical Report of the Crystallography Laboratory, University of Nijmegen, The Netherlands. Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U.S.A. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hall, V. J., Siasios, G. & Tiekink, E. R. T. (1993). Aust. J. Chem. 46, 561–570. CSD CrossRef CAS Google Scholar
Ho, S. Y., Cheng, E. C.-C., Tiekink, E. R. T. & Yam, V. W.-W. (2006). Inorg. Chem. 45, 8165–8174. Web of Science CSD CrossRef PubMed CAS Google Scholar
Ho, S. Y. & Tiekink, E. R. T. (2007). CrystEngComm, 9, 368–378. Web of Science CSD CrossRef CAS Google Scholar
Ho, S. Y. & Tiekink, E. R. T. (2009). Acta Cryst. E65, m1466–m1467. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Kuan, F. S., Ho, S. Y., Tadbuppa, P. P. & Tiekink, E. R. T. (2008). CrystEngComm, 10, 548–564. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tadbuppa, P. P. & Tiekink, E. R. T. (2009). Acta Cryst. E65, m1597. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43. Submitted. Google Scholar

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Volume 66| Part 6| June 2010| Pages m608-m609

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

[μ-1,1′-Bis(di­phenyl­phosphino)ferrocene]bis­­{[(Z)-O-ethyl N-phenyl­thio­carbamato-κS]gold(I)} di­chloro­methane solvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

[μ-1,1′-Bis(diphenylphosphino)ferrocene]bis{[(Z)-O-ethyl N-phenylthiocarbamato-κS]gold(I)} dichloromethane solvate