(Ferrocenyl­thio­phospho­nato-κS)(triphenyl­phosphane-κP)gold(I) dichloro­methane monosolvate

van der Walt, H.; Muller, A.; Staples, R.J.; Van Zyl, W.E.

doi:10.1107/S1600536810039255

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages m1364-m1365

https://doi.org/10.1107/S1600536810039255

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(Ferrocenylthiophosphonato-κS)(triphenylphosphane-κP)gold(I) dichloromethane monosolvate

Hendriette van der Walt,^a Alfred Muller,^a Richard J. Staples ^b and Werner E. Van Zyl ^c ^*

^aResearch Centre in Synthesis and Catalysis, Department of Chemistry, University of Johannesburg (APK Campus), PO Box 524, Auckland Park, Johannesburg 2006, South Africa, ^bDepartment of Chemistry, Michigan State University, East Lansing, MI 48824-1322, USA, and ^cSchool of Chemistry, University of KwaZulu-Natal, Westville Campus, Private Bag X54001, Durban 4000, South Africa
^*Correspondence e-mail: vanzylw@ukzn.ac.za

(Received 27 September 2010; accepted 30 September 2010; online 9 October 2010)

In the title compound, [AuFe(C₅H₅)(C₅H₅O₂PS)(C₁₈H₁₅P)]·CH₂Cl₂, the two-coordinate gold(I) atom shows a slightly distorted linear arrangement, with a P—Au—S bond angle of 176.81 (6)°. The difference in P=O and P—O(H) bond lengths, which are 1.503 (6) and 1.541 (5) Å, respectively, implies there is apparently no delocalization between the P—O bonds, and the proton appears to be localized on one O atom only. In the crystal structure, intermolecular O—H⋯O hydrogen bonds link dinuclear molecules into chains propagated in the [010] direction. The dichloromethane solvent molecule was disordered between two positions in a 0.63 (3):0.37 (3) ratio.

Related literature

For information on dithiophosphonate complexes of Group 11 metals, see: Van Zyl (2010 ). For the synthesis of dithiophosphonate salt derivatives, see: Van Zyl & Fackler (2000 ). For gold complexes with thiophosphoryl-based ligands, see: Crespo et al. (2004 ). For gold complexes with dithiophosphate phosphine gold(I) complexes, see: Preisenberger et al. (1998 ). For the synthesis of ferrocenyl (Fc) dimers of the type [PS₂(Fc)]₂, see: Foreman et al. (1996 ). For general background, see: Allen (2002 ).

Experimental

Crystal data

[AuFe(C₅H₅)(C₅H₅O₂PS)(C₁₈H₁₅P)]·CH₂Cl₂
M_r = 825.22
Monoclinic, P 2₁ /c
a = 15.122 (3) Å
b = 9.3157 (18) Å
c = 22.581 (3) Å
β = 112.831 (10)°
V = 2931.8 (9) Å³
Z = 4
Mo Kα radiation
μ = 5.88 mm⁻¹
T = 173 K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.386, T_max = 0.453
13808 measured reflections
4924 independent reflections
4348 reflections with I > 2σ(I)
R_int = 0.112

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.153
S = 1.10
4924 reflections
375 parameters
18 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 2.14 e Å⁻³
Δρ_min = −1.63 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1ⁱ	1.11 (11)	1.33 (11)	2.432 (7)	173 (9)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker 2006 ); cell refinement: SAINT-Plus (Bruker, 2001 ); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810039255/cv2770sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039255/cv2770Isup2.hkl

checkCIF report

Comment top

The dithiophosphonato dianion salt, (NH₄)₂[S₂P(Fc)OCH₂CH₂O(Fc)PS₂] (Fc = ferrocenyl) was used in this study. It was obtained from the reaction between the dimer [PS₂(Fc)]₂ (Foreman et al., 1996) and ethanediol, which formed a diacid. The diacid could be readily deprotonated by ammonia gas. The salt was then reacted with [Au(PPh₃)Cl] to yield the complex [(PPh₃)AuS₂(Fc)P(OC₂H₄O)P(Fc)S₂Au(PPh₃)] (I). The complex was fully characterized spectroscopically (see Experimental). During work-up for crystal growth, however, the ligand became oxidized, presumably as a result of water present in the solvent dichloromethane. This resulted in substitution of a terminal P═S bond with a P═O bond, a reaction that can readily occur with oxophilic phosphorus(V) in the presence of moisture. Additionally, it resulted in C—O bond cleavage to be replaced with H—O bond formation. A precise mechanism for the reaction is not proposed. The title compound I (see Fig 1) crystalizes in the P2₁/c space group with molecules lying on general positions in the unit cell. All geometrical data for the compound are within the normal limits (Allen, 2002). In the crystal packing, there is a hydrogen-bonding network along the b axis between the P═ O···H—O—P moieties (see Fig 2 and Table 1).

Related literature top

For information on dithiophosphonate complexes of Group 11 metals, see: Van Zyl (2010). For the synthesis of dithiophosphonate salt derivatives, see: Van Zyl et al. (2000). For gold complexes with thiophosphoryl-based ligands, see Crespo et al. (2004). For gold complexes with dithiophosphate phosphine gold(I) complexes, see: Preisenberger et al. (1998). For the synthesis of ferrocenyl (Fc) dimers of the type [PS₂(Fc)]₂, see: Foreman et al. (1996). For general background, see: Allen (2002).

Experimental top

The complex (I) was obtained as an oxidized product. The initial reaction was between the (NH₄)₂[S₂P(Fc)OCH₂CH₂O(Fc)PS₂] salt (Fc = ferrocenyl) (0.122 g, 0.206 mmol) and [Au(PPh₃)Cl] (0.200 g, 0.413 mmol) in a THF solution. The NH₄Cl was filtered off and the filtrate solvent removed under reduced pressure yielding a yellow colored powder. Yield: 0.127 g (41%). M.p.: 128°C. ¹H-NMR (CDCl₃) δ: 7.54 – 7.45 (m, 30H, PPh₃); 4.65 – 4.22 (d, 4H, Fc); 4.53 – 4.50 (d, 4H, Fc); 4.30 (s, 10H, Fc); 4.36 – 4.31 (t, 2H, CH₂); 3.99 – 3.93 (m, 2H, CH₂). ³¹P-NMR δ: 106.14 and 106.03 (d, 2P, P—S); 37.82 (s, 2P, PPh₃). ESI-MS: m/z 1539 (95%) for [(PPh₃)AuS₂(Fc)P(OC₂H₄O)P(Fc)S₂Au(PPh₃)].

Structure description top

Computing details top

Data collection: APEX2 (Bruker 2006); cell refinement: SAINT-Plus (Bruker, 2001); data reduction: SAINT-Plus (Bruker, 2001); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Brendt, 2001); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. View of (I) (30% probability displacement ellipsoids). Hydrogen atoms omitted for clarity.
	Fig. 2. Packing diagram of (I) showing the infinite hydrogen bonding interactions (dashed lines) along the b axis. Solvent molecules omitted for clarity.

(Ferrocenylthiophosphonato-κS)(triphenylphosphane-κP)gold(I) dichloromethane monosolvate top

Crystal data top

[AuFe(C₅H₅)(C₅H₅O₂PS)(C₁₈H₁₅P)]·CH₂Cl₂	F(000) = 1608
M_r = 825.22	D_x = 1.87 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9574 reflections
a = 15.122 (3) Å	θ = 2.2–27.9°
b = 9.3157 (18) Å	µ = 5.88 mm⁻¹
c = 22.581 (3) Å	T = 173 K
β = 112.831 (10)°	Block, orange-brown
V = 2931.8 (9) Å³	0.2 × 0.18 × 0.16 mm
Z = 4

Data collection top

Bruker CCD diffractometer	4348 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.112
φ scans	θ_max = 25°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −16→17
T_min = 0.386, T_max = 0.453	k = −11→11
13808 measured reflections	l = −26→20
4924 independent reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.095P)²] where P = (F_o² + 2F_c²)/3
4924 reflections	(Δ/σ)_max = 0.001
375 parameters	Δρ_max = 2.14 e Å⁻³
18 restraints	Δρ_min = −1.63 e Å⁻³

Crystal data top

[AuFe(C₅H₅)(C₅H₅O₂PS)(C₁₈H₁₅P)]·CH₂Cl₂	V = 2931.8 (9) Å³
M_r = 825.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.122 (3) Å	µ = 5.88 mm⁻¹
b = 9.3157 (18) Å	T = 173 K
c = 22.581 (3) Å	0.2 × 0.18 × 0.16 mm
β = 112.831 (10)°

Data collection top

Bruker CCD diffractometer	4924 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	4348 reflections with I > 2σ(I)
T_min = 0.386, T_max = 0.453	R_int = 0.112
13808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	18 restraints
wR(F²) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 2.14 e Å⁻³
4924 reflections	Δρ_min = −1.63 e Å⁻³
375 parameters

Special details top

Experimental. The intensity data was collected on a Bruker CCD based diffractometer equipped with an Oxford Cryostream low-temperature apparatus operating at 173 K diffractometer using an exposure time of 30 s/frame. A total of 1276 frames were collected with a frame width of 0.5° covering up to θ = 28.63% with 86.5% completeness accomplished. Due to decomposition and the weak diffracting nature of the title compound, refinement of data was restricted to θ = 25.0% to reach a completeness of 95.5%.

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Au1	0.227778 (18)	0.21410 (3)	0.709726 (13)	0.04416 (16)
Fe1	−0.15433 (8)	0.30798 (11)	0.60212 (6)	0.0463 (3)
S1	0.17770 (13)	0.35983 (19)	0.77340 (10)	0.0499 (4)
P1	0.28030 (12)	0.08231 (19)	0.64580 (9)	0.0407 (4)
P2	0.03846 (15)	0.29088 (17)	0.74410 (11)	0.0443 (5)
O1	0.0279 (4)	0.1480 (6)	0.7716 (3)	0.0528 (13)
O2	−0.0137 (4)	0.4034 (6)	0.7688 (3)	0.0502 (12)
C11	0.2290 (5)	0.1421 (7)	0.5625 (3)	0.0439 (15)
C12	0.2703 (5)	0.1110 (8)	0.5188 (4)	0.0515 (17)
H12	0.3305	0.0634	0.5326	0.062*
C13	0.2237 (6)	0.1493 (8)	0.4552 (4)	0.0544 (18)
H13	0.2521	0.1274	0.4254	0.065*
C14	0.1361 (7)	0.2190 (8)	0.4340 (5)	0.058 (2)
H14	0.1054	0.2476	0.3904	0.069*
C15	0.0933 (7)	0.2469 (10)	0.4779 (4)	0.058 (2)
H15	0.0317	0.2903	0.4639	0.069*
C16	0.1411 (6)	0.2112 (7)	0.5408 (4)	0.0514 (19)
H16	0.1132	0.2344	0.5707	0.062*
C21	0.4100 (5)	0.0891 (7)	0.6701 (3)	0.0435 (15)
C22	0.4526 (6)	0.2000 (8)	0.6510 (4)	0.0516 (19)
H22	0.4133	0.2703	0.6224	0.062*
C23	0.5507 (6)	0.2118 (7)	0.6723 (5)	0.055 (2)
H23	0.579	0.2881	0.6579	0.067*
C24	0.6073 (5)	0.1112 (9)	0.7150 (4)	0.0542 (18)
H24	0.6751	0.118	0.7295	0.065*
C25	0.5671 (5)	0.0007 (9)	0.7369 (4)	0.063 (2)
H25	0.6069	−0.0661	0.7674	0.075*
C26	0.4683 (5)	−0.0116 (8)	0.7141 (4)	0.0522 (17)
H26	0.44	−0.0884	0.7282	0.063*
C31	0.2488 (5)	−0.1068 (7)	0.6423 (3)	0.0428 (15)
C32	0.2881 (6)	−0.2077 (7)	0.6148 (4)	0.0499 (19)
H32	0.3353	−0.18	0.599	0.06*
C33	0.2582 (6)	−0.3508 (8)	0.6105 (4)	0.0540 (18)
H33	0.2868	−0.4213	0.5931	0.065*
C34	0.1871 (5)	−0.3890 (9)	0.6314 (4)	0.0559 (19)
H34	0.1657	−0.4858	0.6274	0.067*
C35	0.1471 (6)	−0.2889 (8)	0.6581 (5)	0.058 (2)
H35	0.0991	−0.3167	0.6732	0.07*
C36	0.1766 (5)	−0.1480 (8)	0.6628 (4)	0.0505 (17)
H36	0.1476	−0.0784	0.6803	0.061*
C41	−0.0125 (5)	0.2862 (7)	0.6583 (4)	0.0452 (18)
C42	−0.0462 (5)	0.1626 (8)	0.6188 (4)	0.0476 (17)
H42	−0.0448	0.0669	0.6336	0.057*
C43	−0.0826 (6)	0.2068 (8)	0.5530 (4)	0.0490 (18)
H43	−0.1094	0.1461	0.5166	0.059*
C44	−0.0713 (5)	0.3575 (8)	0.5522 (4)	0.0504 (17)
H44	−0.0896	0.4162	0.5149	0.061*
C45	−0.0278 (5)	0.4060 (8)	0.6169 (4)	0.0467 (16)
H45	−0.0117	0.5027	0.6302	0.056*
C51	−0.2328 (6)	0.4488 (10)	0.6316 (5)	0.070 (2)
H51	−0.2125	0.5385	0.6524	0.083*
C52	−0.2765 (6)	0.4242 (12)	0.5630 (5)	0.074 (3)
H52	−0.2884	0.4942	0.5302	0.089*
C53	−0.2981 (6)	0.2771 (10)	0.5542 (5)	0.069 (3)
H53	−0.329	0.2308	0.5139	0.082*
C54	−0.2672 (7)	0.2106 (10)	0.6135 (6)	0.066 (3)
H54	−0.2727	0.1112	0.6207	0.08*
C55	−0.2263 (6)	0.3149 (10)	0.6614 (5)	0.060 (2)
H55	−0.1988	0.2976	0.7064	0.072*
H1	−0.020 (7)	0.512 (12)	0.747 (4)	0.09 (3)*
C1A	0.539 (6)	−0.310 (3)	0.556 (4)	0.18 (4)	0.37 (3)
H1A1	0.5102	−0.3393	0.51	0.217*	0.37 (3)
H1A2	0.6083	−0.3287	0.5704	0.217*	0.37 (3)
Cl1A	0.528 (3)	−0.134 (3)	0.5549 (15)	0.094 (5)	0.37 (3)
Cl2A	0.4991 (7)	−0.427 (2)	0.5939 (16)	0.117 (8)	0.37 (3)
C1B	0.5793 (14)	−0.284 (2)	0.6005 (13)	0.093 (8)	0.63 (3)
H1B1	0.5783	−0.3424	0.5636	0.112*	0.63 (3)
H1B2	0.6472	−0.2746	0.6303	0.112*	0.63 (3)
Cl1B	0.5391 (15)	−0.1218 (16)	0.5733 (8)	0.081 (3)	0.63 (3)
Cl2B	0.5235 (9)	−0.3745 (11)	0.6373 (9)	0.106 (5)	0.63 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Au1	0.0426 (2)	0.0476 (2)	0.0452 (2)	−0.00013 (9)	0.02019 (16)	−0.00134 (11)
Fe1	0.0409 (6)	0.0511 (5)	0.0486 (7)	−0.0013 (4)	0.0191 (5)	−0.0046 (5)
S1	0.0459 (9)	0.0530 (10)	0.0529 (11)	−0.0054 (7)	0.0215 (8)	−0.0097 (9)
P1	0.0396 (9)	0.0443 (8)	0.0418 (10)	−0.0003 (7)	0.0196 (7)	0.0001 (8)
P2	0.0471 (11)	0.0430 (10)	0.0443 (11)	−0.0016 (7)	0.0192 (9)	−0.0016 (8)
O1	0.072 (3)	0.042 (3)	0.048 (3)	−0.005 (2)	0.028 (3)	0.001 (2)
O2	0.056 (3)	0.050 (3)	0.054 (3)	0.000 (2)	0.031 (3)	−0.002 (2)
C11	0.045 (4)	0.047 (4)	0.041 (4)	−0.003 (3)	0.018 (3)	−0.001 (3)
C12	0.049 (4)	0.054 (4)	0.051 (4)	0.003 (3)	0.019 (3)	0.000 (4)
C13	0.065 (5)	0.057 (4)	0.046 (4)	0.003 (4)	0.027 (4)	0.008 (4)
C14	0.060 (5)	0.059 (5)	0.047 (5)	−0.001 (3)	0.013 (4)	0.009 (4)
C15	0.060 (5)	0.064 (4)	0.050 (5)	0.013 (4)	0.022 (4)	0.010 (4)
C16	0.042 (4)	0.061 (5)	0.059 (5)	0.005 (3)	0.028 (4)	0.008 (4)
C21	0.036 (3)	0.048 (3)	0.047 (4)	−0.005 (3)	0.017 (3)	−0.009 (3)
C22	0.053 (5)	0.049 (4)	0.053 (5)	0.003 (3)	0.021 (4)	0.002 (3)
C23	0.046 (4)	0.056 (5)	0.070 (6)	−0.006 (3)	0.028 (4)	−0.004 (4)
C24	0.045 (4)	0.065 (4)	0.054 (5)	−0.003 (3)	0.020 (3)	−0.007 (4)
C25	0.046 (4)	0.068 (5)	0.071 (5)	0.009 (4)	0.019 (4)	0.007 (4)
C26	0.051 (4)	0.056 (4)	0.053 (5)	−0.003 (3)	0.023 (3)	0.006 (4)
C31	0.044 (4)	0.043 (3)	0.044 (4)	0.003 (3)	0.020 (3)	0.002 (3)
C32	0.056 (5)	0.053 (4)	0.050 (5)	−0.004 (3)	0.031 (4)	0.000 (3)
C33	0.056 (4)	0.047 (4)	0.059 (5)	0.000 (3)	0.022 (4)	−0.002 (4)
C34	0.062 (5)	0.053 (4)	0.054 (5)	−0.014 (3)	0.024 (4)	−0.002 (4)
C35	0.050 (5)	0.061 (5)	0.069 (6)	−0.009 (3)	0.028 (4)	0.001 (4)
C36	0.050 (4)	0.050 (4)	0.054 (5)	−0.002 (3)	0.024 (3)	0.001 (4)
C41	0.040 (4)	0.051 (4)	0.049 (5)	0.001 (3)	0.023 (3)	−0.004 (3)
C42	0.044 (4)	0.049 (4)	0.050 (4)	−0.003 (3)	0.019 (3)	−0.005 (4)
C43	0.045 (4)	0.060 (5)	0.042 (4)	0.000 (3)	0.017 (3)	−0.007 (3)
C44	0.049 (4)	0.060 (4)	0.045 (4)	0.003 (3)	0.021 (3)	0.009 (4)
C45	0.047 (4)	0.047 (4)	0.052 (4)	−0.003 (3)	0.026 (3)	0.000 (3)
C51	0.048 (4)	0.072 (5)	0.092 (7)	0.004 (4)	0.032 (5)	−0.020 (5)
C52	0.047 (4)	0.090 (6)	0.081 (7)	0.017 (4)	0.021 (4)	0.000 (6)
C53	0.039 (5)	0.094 (7)	0.072 (7)	−0.013 (4)	0.020 (4)	−0.030 (5)
C54	0.053 (5)	0.075 (6)	0.082 (7)	−0.009 (4)	0.039 (5)	−0.008 (5)
C55	0.054 (5)	0.082 (5)	0.055 (5)	−0.006 (4)	0.032 (4)	−0.006 (5)
C1A	0.19 (7)	0.101 (13)	0.34 (11)	0.00 (4)	0.20 (8)	0.00 (4)
Cl1A	0.070 (6)	0.100 (7)	0.098 (13)	−0.005 (6)	0.016 (10)	0.011 (8)
Cl2A	0.077 (5)	0.108 (9)	0.147 (17)	0.009 (5)	0.020 (7)	0.040 (12)
C1B	0.051 (10)	0.097 (12)	0.13 (2)	0.014 (8)	0.029 (11)	0.029 (13)
Cl1B	0.076 (6)	0.079 (3)	0.084 (7)	0.002 (3)	0.026 (6)	−0.008 (4)
Cl2B	0.098 (5)	0.090 (4)	0.149 (11)	0.016 (4)	0.068 (7)	0.034 (5)

Geometric parameters (Å, º) top

Au1—P1	2.2609 (18)	C32—H32	0.95
Au1—S1	2.3084 (19)	C33—C34	1.379 (11)
S1—P2	2.050 (3)	C33—H33	0.95
P1—C31	1.819 (7)	C34—C35	1.372 (12)
P1—C21	1.821 (6)	C34—H34	0.95
P1—C11	1.822 (7)	C35—C36	1.377 (11)
P2—O1	1.503 (6)	C35—H35	0.95
P2—O2	1.541 (5)	C36—H36	0.95
P2—C41	1.786 (9)	C41—C45	1.416 (10)
O2—H1	1.11 (11)	C41—C42	1.424 (11)
C11—C16	1.384 (10)	C42—C43	1.428 (11)
C11—C12	1.387 (10)	C42—H42	0.95
C12—C13	1.379 (11)	C43—C44	1.416 (11)
C12—H12	0.95	C43—H43	0.95
C13—C14	1.383 (12)	C44—C45	1.424 (11)
C13—H13	0.95	C44—H44	0.95
C14—C15	1.402 (13)	C45—H45	0.95
C14—H14	0.95	C51—C55	1.403 (13)
C15—C16	1.361 (12)	C51—C52	1.446 (13)
C15—H15	0.95	C51—H51	0.95
C16—H16	0.95	C52—C53	1.405 (14)
C21—C22	1.372 (10)	C52—H52	0.95
C21—C26	1.402 (10)	C53—C54	1.382 (15)
C22—C23	1.375 (12)	C53—H53	0.95
C22—H22	0.95	C54—C55	1.406 (13)
C23—C24	1.378 (12)	C54—H54	0.95
C23—H23	0.95	C55—H55	0.95
C24—C25	1.381 (11)	C1A—Cl2A	1.642 (17)
C24—H24	0.95	C1A—Cl1A	1.645 (17)
C25—C26	1.383 (10)	C1A—H1A1	0.99
C25—H25	0.95	C1A—H1A2	0.99
C26—H26	0.95	C1B—Cl2B	1.629 (14)
C31—C32	1.381 (10)	C1B—Cl1B	1.656 (14)
C31—C36	1.396 (10)	C1B—H1B1	0.99
C32—C33	1.399 (11)	C1B—H1B2	0.99

P1—Au1—S1	176.81 (6)	C33—C32—H32	120.1
P2—S1—Au1	99.14 (9)	C34—C33—C32	119.7 (8)
C31—P1—C21	106.3 (3)	C34—C33—H33	120.2
C31—P1—C11	104.6 (3)	C32—C33—H33	120.2
C21—P1—C11	106.1 (3)	C35—C34—C33	120.7 (7)
C31—P1—Au1	113.8 (2)	C35—C34—H34	119.6
C21—P1—Au1	113.1 (2)	C33—C34—H34	119.6
C11—P1—Au1	112.3 (2)	C34—C35—C36	119.8 (8)
O1—P2—O2	107.6 (3)	C34—C35—H35	120.1
O1—P2—C41	110.8 (3)	C36—C35—H35	120.1
O2—P2—C41	110.1 (3)	C35—C36—C31	120.5 (7)
O1—P2—S1	113.9 (3)	C35—C36—H36	119.7
O2—P2—S1	106.0 (2)	C31—C36—H36	119.7
C41—P2—S1	108.3 (3)	C45—C41—C42	107.2 (7)
P2—O2—H1	115 (5)	C45—C41—P2	126.0 (5)
C16—C11—C12	118.7 (7)	C42—C41—P2	126.8 (6)
C16—C11—P1	118.3 (6)	C41—C42—C43	108.6 (7)
C12—C11—P1	122.8 (5)	C41—C42—H42	125.7
C13—C12—C11	119.9 (7)	C43—C42—H42	125.7
C13—C12—H12	120.1	C44—C43—C42	107.5 (7)
C11—C12—H12	120.1	C44—C43—H43	126.3
C12—C13—C14	121.0 (8)	C42—C43—H43	126.3
C12—C13—H13	119.5	C43—C44—C45	108.1 (7)
C14—C13—H13	119.5	C43—C44—H44	125.9
C13—C14—C15	119.0 (8)	C45—C44—H44	125.9
C13—C14—H14	120.5	C41—C45—C44	108.6 (6)
C15—C14—H14	120.5	C41—C45—H45	125.7
C16—C15—C14	119.2 (8)	C44—C45—H45	125.7
C16—C15—H15	120.4	C55—C51—C52	106.9 (8)
C14—C15—H15	120.4	C55—C51—H51	126.5
C15—C16—C11	122.1 (8)	C52—C51—H51	126.5
C15—C16—H16	119	C53—C52—C51	106.9 (10)
C11—C16—H16	119	C53—C52—H52	126.5
C22—C21—C26	118.9 (6)	C51—C52—H52	126.5
C22—C21—P1	120.9 (6)	C54—C53—C52	109.1 (9)
C26—C21—P1	119.9 (5)	C54—C53—H53	125.5
C21—C22—C23	121.7 (8)	C52—C53—H53	125.5
C21—C22—H22	119.2	C53—C54—C55	108.6 (8)
C23—C22—H22	119.2	C53—C54—H54	125.7
C22—C23—C24	118.9 (7)	C55—C54—H54	125.7
C22—C23—H23	120.6	C51—C55—C54	108.5 (9)
C24—C23—H23	120.6	C51—C55—H55	125.8
C23—C24—C25	121.1 (7)	C54—C55—H55	125.8
C23—C24—H24	119.4	Cl2A—C1A—Cl1A	128 (3)
C25—C24—H24	119.4	Cl2A—C1A—H1A1	105.3
C24—C25—C26	119.4 (8)	Cl1A—C1A—H1A1	105.3
C24—C25—H25	120.3	Cl2A—C1A—H1A2	105.3
C26—C25—H25	120.3	Cl1A—C1A—H1A2	105.3
C25—C26—C21	120.0 (7)	H1A1—C1A—H1A2	106
C25—C26—H26	120	Cl2B—C1B—Cl1B	118.3 (16)
C21—C26—H26	120	Cl2B—C1B—H1B1	107.7
C32—C31—C36	119.4 (7)	Cl1B—C1B—H1B1	107.7
C32—C31—P1	121.9 (5)	Cl2B—C1B—H1B2	107.7
C36—C31—P1	118.5 (5)	Cl1B—C1B—H1B2	107.7
C31—C32—C33	119.8 (7)	H1B1—C1B—H1B2	107.1
C31—C32—H32	120.1

Au1—S1—P2—O1	76.2 (3)	C11—P1—C31—C32	68.3 (7)
Au1—S1—P2—O2	−165.7 (2)	Au1—P1—C31—C32	−168.8 (6)
Au1—S1—P2—C41	−47.6 (2)	C21—P1—C31—C36	142.1 (6)
C31—P1—C11—C16	97.8 (6)	C11—P1—C31—C36	−105.9 (6)
C21—P1—C11—C16	−150.0 (6)	Au1—P1—C31—C36	17.0 (7)
Au1—P1—C11—C16	−26.0 (6)	C36—C31—C32—C33	−2.8 (12)
C31—P1—C11—C12	−76.7 (7)	P1—C31—C32—C33	−176.9 (6)
C21—P1—C11—C12	35.4 (7)	C31—C32—C33—C34	2.4 (13)
Au1—P1—C11—C12	159.5 (5)	C32—C33—C34—C35	−1.7 (13)
C16—C11—C12—C13	0.2 (11)	C33—C34—C35—C36	1.3 (14)
P1—C11—C12—C13	174.7 (6)	C34—C35—C36—C31	−1.6 (13)
C11—C12—C13—C14	0.2 (12)	C32—C31—C36—C35	2.4 (12)
C12—C13—C14—C15	−1.9 (12)	P1—C31—C36—C35	176.8 (7)
C13—C14—C15—C16	3.2 (12)	O1—P2—C41—C45	170.2 (6)
C14—C15—C16—C11	−2.9 (13)	O2—P2—C41—C45	51.3 (7)
C12—C11—C16—C15	1.2 (11)	S1—P2—C41—C45	−64.2 (7)
P1—C11—C16—C15	−173.5 (7)	O1—P2—C41—C42	−9.0 (8)
C31—P1—C21—C22	150.7 (6)	O2—P2—C41—C42	−127.9 (6)
C11—P1—C21—C22	39.8 (7)	S1—P2—C41—C42	116.6 (6)
Au1—P1—C21—C22	−83.8 (7)	C45—C41—C42—C43	−0.2 (8)
C31—P1—C21—C26	−35.8 (7)	P2—C41—C42—C43	179.1 (6)
C11—P1—C21—C26	−146.7 (6)	C41—C42—C43—C44	−0.1 (8)
Au1—P1—C21—C26	89.7 (6)	C42—C43—C44—C45	0.3 (8)
C26—C21—C22—C23	2.1 (12)	C42—C41—C45—C44	0.4 (8)
P1—C21—C22—C23	175.7 (7)	P2—C41—C45—C44	−178.9 (5)
C21—C22—C23—C24	−1.4 (13)	C43—C44—C45—C41	−0.4 (8)
C22—C23—C24—C25	−0.7 (13)	C55—C51—C52—C53	2.3 (10)
C23—C24—C25—C26	2.0 (13)	C51—C52—C53—C54	−1.9 (10)
C24—C25—C26—C21	−1.3 (12)	C52—C53—C54—C55	0.7 (10)
C22—C21—C26—C25	−0.8 (11)	C52—C51—C55—C54	−1.9 (9)
P1—C21—C26—C25	−174.4 (6)	C53—C54—C55—C51	0.7 (10)
C21—P1—C31—C32	−43.7 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1ⁱ	1.11 (11)	1.33 (11)	2.432 (7)	173 (9)

Symmetry code: (i) −x, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[AuFe(C₅H₅)(C₅H₅O₂PS)(C₁₈H₁₅P)]·CH₂Cl₂
M_r	825.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	15.122 (3), 9.3157 (18), 22.581 (3)
β (°)	112.831 (10)
V (Å³)	2931.8 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	5.88
Crystal size (mm)	0.2 × 0.18 × 0.16

Data collection
Diffractometer	Bruker CCD
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.386, 0.453
No. of measured, independent and observed [I > 2σ(I)] reflections	13808, 4924, 4348
R_int	0.112
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.153, 1.10
No. of reflections	4924
No. of parameters	375
No. of restraints	18
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	2.14, −1.63

Computer programs: APEX2 (Bruker 2006), SAINT-Plus (Bruker, 2001), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Brendt, 2001), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1ⁱ	1.11 (11)	1.33 (11)	2.432 (7)	173 (9)

Symmetry code: (i) −x, y+1/2, −z+3/2.

Acknowledgements

The authors thank Mintek (Project AuTEK), South Africa, for financial support of this work.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Crespo, O., Brusko, V. V., Gimeno, M. C., Tornil, M. L., Laguna, A. & Zabirov, N. G. (2004). Eur. J. Inorg. Chem. 2, 423–430. Web of Science CSD CrossRef Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Foreman, M. R. S., Slawin, A. M. Z. & Woollins, J. D. (1996). J. Chem. Soc. Dalton Trans. pp. 3653–3657 CrossRef Google Scholar
Preisenberger, M., Schier, A. & Schmidbaur, H. (1998). Z. Naturforsch. Teil B, 53, 781–787. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Van Zyl, W. E. (2010). Comments Inorg. Chem. 31, 13–45. Web of Science CrossRef CAS Google Scholar
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Volume 66| Part 11| November 2010| Pages m1364-m1365

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

(Ferrocenyl­thio­phospho­nato-κS)(tri­phenyl­phosphane-κP)gold(I) di­chloro­methane monosolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(Ferrocenylthiophosphonato-κS)(triphenylphosphane-κP)gold(I) dichloromethane monosolvate