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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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[Van Zyl, W. E. (2010). Comments Inorg. Chem. 31, 13-45.]). For the synthesis of dithio­phospho­nate salt derivatives, see: Van Zyl & Fackler (2000[Van Zyl, W. E. & Fackler, J. P. (2000). Phosphorus Sulfur Silicon Relat. Elem. 167, 117-132.]). For gold complexes with thio­phosphoryl-based ligands, see: Crespo et al. (2004[Crespo, O., Brusko, V. V., Gimeno, M. C., Tornil, M. L., Laguna, A. & Zabirov, N. G. (2004). Eur. J. Inorg. Chem. 2, 423-430.]). For gold complexes with dithio­phosphate phosphine gold(I) complexes, see: Preisenberger et al. (1998[Preisenberger, M., Schier, A. & Schmidbaur, H. (1998). Z. Naturforsch. Teil B, 53, 781-787.]). For the synthesis of ferrocenyl (Fc) dimers of the type [PS2(Fc)]2, see: Foreman et al. (1996[Foreman, M. R. S., Slawin, A. M. Z. & Woollins, J. D. (1996). J. Chem. Soc. Dalton Trans. pp. 3653-3657]). For general background, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • [AuFe(C5H5)(C5H5O2PS)(C18H15P)]·CH2Cl2

  • Mr = 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[Bruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.386, Tmax = 0.453

  • 13808 measured reflections

  • 4924 independent reflections

  • 4348 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 2.14 e Å−3

  • Δρmin = −1.63 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2001[Bruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SIR2002 (Burla et al., 2003[Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


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 PS bond with a PO 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)].

Refinement top

The aromatic H atoms were placed in geometrically idealized positions (C—H = 0.95 Å) and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C). The hydroxyl H was located in a Fourier difference map and refined isotropically. The disorder of the solvent molecule was refined over two positions that adds to unity. The final refinement shows a ratio of 37:63 for the two components. The neccesary bond and Uij restraints were applied to keep the refinement stable.

Structure description 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 PS bond with a PO 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).

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).

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
[Figure 1] Fig. 1. View of (I) (30% probability displacement ellipsoids). Hydrogen atoms omitted for clarity.
[Figure 2] 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)]·CH2Cl2F(000) = 1608
Mr = 825.22Dx = 1.87 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9574 reflections
a = 15.122 (3) Åθ = 2.2–27.9°
b = 9.3157 (18) ŵ = 5.88 mm1
c = 22.581 (3) ÅT = 173 K
β = 112.831 (10)°Block, orange-brown
V = 2931.8 (9) Å30.2 × 0.18 × 0.16 mm
Z = 4
Data collection top
Bruker CCD
diffractometer
4348 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.112
φ scansθmax = 25°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 1617
Tmin = 0.386, Tmax = 0.453k = 1111
13808 measured reflectionsl = 2620
4924 independent 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)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.095P)2]
where P = (Fo2 + 2Fc2)/3
4924 reflections(Δ/σ)max = 0.001
375 parametersΔρmax = 2.14 e Å3
18 restraintsΔρmin = 1.63 e Å3
Crystal data top
[AuFe(C5H5)(C5H5O2PS)(C18H15P)]·CH2Cl2V = 2931.8 (9) Å3
Mr = 825.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 15.122 (3) ŵ = 5.88 mm1
b = 9.3157 (18) ÅT = 173 K
c = 22.581 (3) Å0.2 × 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)
Tmin = 0.386, Tmax = 0.453Rint = 0.112
13808 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05118 restraints
wR(F2) = 0.153H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 2.14 e Å3
4924 reflectionsΔρmin = 1.63 e Å3
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
xyzUiso*/UeqOcc. (<1)
Au10.227778 (18)0.21410 (3)0.709726 (13)0.04416 (16)
Fe10.15433 (8)0.30798 (11)0.60212 (6)0.0463 (3)
S10.17770 (13)0.35983 (19)0.77340 (10)0.0499 (4)
P10.28030 (12)0.08231 (19)0.64580 (9)0.0407 (4)
P20.03846 (15)0.29088 (17)0.74410 (11)0.0443 (5)
O10.0279 (4)0.1480 (6)0.7716 (3)0.0528 (13)
O20.0137 (4)0.4034 (6)0.7688 (3)0.0502 (12)
C110.2290 (5)0.1421 (7)0.5625 (3)0.0439 (15)
C120.2703 (5)0.1110 (8)0.5188 (4)0.0515 (17)
H120.33050.06340.53260.062*
C130.2237 (6)0.1493 (8)0.4552 (4)0.0544 (18)
H130.25210.12740.42540.065*
C140.1361 (7)0.2190 (8)0.4340 (5)0.058 (2)
H140.10540.24760.39040.069*
C150.0933 (7)0.2469 (10)0.4779 (4)0.058 (2)
H150.03170.29030.46390.069*
C160.1411 (6)0.2112 (7)0.5408 (4)0.0514 (19)
H160.11320.23440.57070.062*
C210.4100 (5)0.0891 (7)0.6701 (3)0.0435 (15)
C220.4526 (6)0.2000 (8)0.6510 (4)0.0516 (19)
H220.41330.27030.62240.062*
C230.5507 (6)0.2118 (7)0.6723 (5)0.055 (2)
H230.5790.28810.65790.067*
C240.6073 (5)0.1112 (9)0.7150 (4)0.0542 (18)
H240.67510.1180.72950.065*
C250.5671 (5)0.0007 (9)0.7369 (4)0.063 (2)
H250.60690.06610.76740.075*
C260.4683 (5)0.0116 (8)0.7141 (4)0.0522 (17)
H260.440.08840.72820.063*
C310.2488 (5)0.1068 (7)0.6423 (3)0.0428 (15)
C320.2881 (6)0.2077 (7)0.6148 (4)0.0499 (19)
H320.33530.180.5990.06*
C330.2582 (6)0.3508 (8)0.6105 (4)0.0540 (18)
H330.28680.42130.59310.065*
C340.1871 (5)0.3890 (9)0.6314 (4)0.0559 (19)
H340.16570.48580.62740.067*
C350.1471 (6)0.2889 (8)0.6581 (5)0.058 (2)
H350.09910.31670.67320.07*
C360.1766 (5)0.1480 (8)0.6628 (4)0.0505 (17)
H360.14760.07840.68030.061*
C410.0125 (5)0.2862 (7)0.6583 (4)0.0452 (18)
C420.0462 (5)0.1626 (8)0.6188 (4)0.0476 (17)
H420.04480.06690.63360.057*
C430.0826 (6)0.2068 (8)0.5530 (4)0.0490 (18)
H430.10940.14610.51660.059*
C440.0713 (5)0.3575 (8)0.5522 (4)0.0504 (17)
H440.08960.41620.51490.061*
C450.0278 (5)0.4060 (8)0.6169 (4)0.0467 (16)
H450.01170.50270.63020.056*
C510.2328 (6)0.4488 (10)0.6316 (5)0.070 (2)
H510.21250.53850.65240.083*
C520.2765 (6)0.4242 (12)0.5630 (5)0.074 (3)
H520.28840.49420.53020.089*
C530.2981 (6)0.2771 (10)0.5542 (5)0.069 (3)
H530.3290.23080.51390.082*
C540.2672 (7)0.2106 (10)0.6135 (6)0.066 (3)
H540.27270.11120.62070.08*
C550.2263 (6)0.3149 (10)0.6614 (5)0.060 (2)
H550.19880.29760.70640.072*
H10.020 (7)0.512 (12)0.747 (4)0.09 (3)*
C1A0.539 (6)0.310 (3)0.556 (4)0.18 (4)0.37 (3)
H1A10.51020.33930.510.217*0.37 (3)
H1A20.60830.32870.57040.217*0.37 (3)
Cl1A0.528 (3)0.134 (3)0.5549 (15)0.094 (5)0.37 (3)
Cl2A0.4991 (7)0.427 (2)0.5939 (16)0.117 (8)0.37 (3)
C1B0.5793 (14)0.284 (2)0.6005 (13)0.093 (8)0.63 (3)
H1B10.57830.34240.56360.112*0.63 (3)
H1B20.64720.27460.63030.112*0.63 (3)
Cl1B0.5391 (15)0.1218 (16)0.5733 (8)0.081 (3)0.63 (3)
Cl2B0.5235 (9)0.3745 (11)0.6373 (9)0.106 (5)0.63 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Au10.0426 (2)0.0476 (2)0.0452 (2)0.00013 (9)0.02019 (16)0.00134 (11)
Fe10.0409 (6)0.0511 (5)0.0486 (7)0.0013 (4)0.0191 (5)0.0046 (5)
S10.0459 (9)0.0530 (10)0.0529 (11)0.0054 (7)0.0215 (8)0.0097 (9)
P10.0396 (9)0.0443 (8)0.0418 (10)0.0003 (7)0.0196 (7)0.0001 (8)
P20.0471 (11)0.0430 (10)0.0443 (11)0.0016 (7)0.0192 (9)0.0016 (8)
O10.072 (3)0.042 (3)0.048 (3)0.005 (2)0.028 (3)0.001 (2)
O20.056 (3)0.050 (3)0.054 (3)0.000 (2)0.031 (3)0.002 (2)
C110.045 (4)0.047 (4)0.041 (4)0.003 (3)0.018 (3)0.001 (3)
C120.049 (4)0.054 (4)0.051 (4)0.003 (3)0.019 (3)0.000 (4)
C130.065 (5)0.057 (4)0.046 (4)0.003 (4)0.027 (4)0.008 (4)
C140.060 (5)0.059 (5)0.047 (5)0.001 (3)0.013 (4)0.009 (4)
C150.060 (5)0.064 (4)0.050 (5)0.013 (4)0.022 (4)0.010 (4)
C160.042 (4)0.061 (5)0.059 (5)0.005 (3)0.028 (4)0.008 (4)
C210.036 (3)0.048 (3)0.047 (4)0.005 (3)0.017 (3)0.009 (3)
C220.053 (5)0.049 (4)0.053 (5)0.003 (3)0.021 (4)0.002 (3)
C230.046 (4)0.056 (5)0.070 (6)0.006 (3)0.028 (4)0.004 (4)
C240.045 (4)0.065 (4)0.054 (5)0.003 (3)0.020 (3)0.007 (4)
C250.046 (4)0.068 (5)0.071 (5)0.009 (4)0.019 (4)0.007 (4)
C260.051 (4)0.056 (4)0.053 (5)0.003 (3)0.023 (3)0.006 (4)
C310.044 (4)0.043 (3)0.044 (4)0.003 (3)0.020 (3)0.002 (3)
C320.056 (5)0.053 (4)0.050 (5)0.004 (3)0.031 (4)0.000 (3)
C330.056 (4)0.047 (4)0.059 (5)0.000 (3)0.022 (4)0.002 (4)
C340.062 (5)0.053 (4)0.054 (5)0.014 (3)0.024 (4)0.002 (4)
C350.050 (5)0.061 (5)0.069 (6)0.009 (3)0.028 (4)0.001 (4)
C360.050 (4)0.050 (4)0.054 (5)0.002 (3)0.024 (3)0.001 (4)
C410.040 (4)0.051 (4)0.049 (5)0.001 (3)0.023 (3)0.004 (3)
C420.044 (4)0.049 (4)0.050 (4)0.003 (3)0.019 (3)0.005 (4)
C430.045 (4)0.060 (5)0.042 (4)0.000 (3)0.017 (3)0.007 (3)
C440.049 (4)0.060 (4)0.045 (4)0.003 (3)0.021 (3)0.009 (4)
C450.047 (4)0.047 (4)0.052 (4)0.003 (3)0.026 (3)0.000 (3)
C510.048 (4)0.072 (5)0.092 (7)0.004 (4)0.032 (5)0.020 (5)
C520.047 (4)0.090 (6)0.081 (7)0.017 (4)0.021 (4)0.000 (6)
C530.039 (5)0.094 (7)0.072 (7)0.013 (4)0.020 (4)0.030 (5)
C540.053 (5)0.075 (6)0.082 (7)0.009 (4)0.039 (5)0.008 (5)
C550.054 (5)0.082 (5)0.055 (5)0.006 (4)0.032 (4)0.006 (5)
C1A0.19 (7)0.101 (13)0.34 (11)0.00 (4)0.20 (8)0.00 (4)
Cl1A0.070 (6)0.100 (7)0.098 (13)0.005 (6)0.016 (10)0.011 (8)
Cl2A0.077 (5)0.108 (9)0.147 (17)0.009 (5)0.020 (7)0.040 (12)
C1B0.051 (10)0.097 (12)0.13 (2)0.014 (8)0.029 (11)0.029 (13)
Cl1B0.076 (6)0.079 (3)0.084 (7)0.002 (3)0.026 (6)0.008 (4)
Cl2B0.098 (5)0.090 (4)0.149 (11)0.016 (4)0.068 (7)0.034 (5)
Geometric parameters (Å, º) top
Au1—P12.2609 (18)C32—H320.95
Au1—S12.3084 (19)C33—C341.379 (11)
S1—P22.050 (3)C33—H330.95
P1—C311.819 (7)C34—C351.372 (12)
P1—C211.821 (6)C34—H340.95
P1—C111.822 (7)C35—C361.377 (11)
P2—O11.503 (6)C35—H350.95
P2—O21.541 (5)C36—H360.95
P2—C411.786 (9)C41—C451.416 (10)
O2—H11.11 (11)C41—C421.424 (11)
C11—C161.384 (10)C42—C431.428 (11)
C11—C121.387 (10)C42—H420.95
C12—C131.379 (11)C43—C441.416 (11)
C12—H120.95C43—H430.95
C13—C141.383 (12)C44—C451.424 (11)
C13—H130.95C44—H440.95
C14—C151.402 (13)C45—H450.95
C14—H140.95C51—C551.403 (13)
C15—C161.361 (12)C51—C521.446 (13)
C15—H150.95C51—H510.95
C16—H160.95C52—C531.405 (14)
C21—C221.372 (10)C52—H520.95
C21—C261.402 (10)C53—C541.382 (15)
C22—C231.375 (12)C53—H530.95
C22—H220.95C54—C551.406 (13)
C23—C241.378 (12)C54—H540.95
C23—H230.95C55—H550.95
C24—C251.381 (11)C1A—Cl2A1.642 (17)
C24—H240.95C1A—Cl1A1.645 (17)
C25—C261.383 (10)C1A—H1A10.99
C25—H250.95C1A—H1A20.99
C26—H260.95C1B—Cl2B1.629 (14)
C31—C321.381 (10)C1B—Cl1B1.656 (14)
C31—C361.396 (10)C1B—H1B10.99
C32—C331.399 (11)C1B—H1B20.99
P1—Au1—S1176.81 (6)C33—C32—H32120.1
P2—S1—Au199.14 (9)C34—C33—C32119.7 (8)
C31—P1—C21106.3 (3)C34—C33—H33120.2
C31—P1—C11104.6 (3)C32—C33—H33120.2
C21—P1—C11106.1 (3)C35—C34—C33120.7 (7)
C31—P1—Au1113.8 (2)C35—C34—H34119.6
C21—P1—Au1113.1 (2)C33—C34—H34119.6
C11—P1—Au1112.3 (2)C34—C35—C36119.8 (8)
O1—P2—O2107.6 (3)C34—C35—H35120.1
O1—P2—C41110.8 (3)C36—C35—H35120.1
O2—P2—C41110.1 (3)C35—C36—C31120.5 (7)
O1—P2—S1113.9 (3)C35—C36—H36119.7
O2—P2—S1106.0 (2)C31—C36—H36119.7
C41—P2—S1108.3 (3)C45—C41—C42107.2 (7)
P2—O2—H1115 (5)C45—C41—P2126.0 (5)
C16—C11—C12118.7 (7)C42—C41—P2126.8 (6)
C16—C11—P1118.3 (6)C41—C42—C43108.6 (7)
C12—C11—P1122.8 (5)C41—C42—H42125.7
C13—C12—C11119.9 (7)C43—C42—H42125.7
C13—C12—H12120.1C44—C43—C42107.5 (7)
C11—C12—H12120.1C44—C43—H43126.3
C12—C13—C14121.0 (8)C42—C43—H43126.3
C12—C13—H13119.5C43—C44—C45108.1 (7)
C14—C13—H13119.5C43—C44—H44125.9
C13—C14—C15119.0 (8)C45—C44—H44125.9
C13—C14—H14120.5C41—C45—C44108.6 (6)
C15—C14—H14120.5C41—C45—H45125.7
C16—C15—C14119.2 (8)C44—C45—H45125.7
C16—C15—H15120.4C55—C51—C52106.9 (8)
C14—C15—H15120.4C55—C51—H51126.5
C15—C16—C11122.1 (8)C52—C51—H51126.5
C15—C16—H16119C53—C52—C51106.9 (10)
C11—C16—H16119C53—C52—H52126.5
C22—C21—C26118.9 (6)C51—C52—H52126.5
C22—C21—P1120.9 (6)C54—C53—C52109.1 (9)
C26—C21—P1119.9 (5)C54—C53—H53125.5
C21—C22—C23121.7 (8)C52—C53—H53125.5
C21—C22—H22119.2C53—C54—C55108.6 (8)
C23—C22—H22119.2C53—C54—H54125.7
C22—C23—C24118.9 (7)C55—C54—H54125.7
C22—C23—H23120.6C51—C55—C54108.5 (9)
C24—C23—H23120.6C51—C55—H55125.8
C23—C24—C25121.1 (7)C54—C55—H55125.8
C23—C24—H24119.4Cl2A—C1A—Cl1A128 (3)
C25—C24—H24119.4Cl2A—C1A—H1A1105.3
C24—C25—C26119.4 (8)Cl1A—C1A—H1A1105.3
C24—C25—H25120.3Cl2A—C1A—H1A2105.3
C26—C25—H25120.3Cl1A—C1A—H1A2105.3
C25—C26—C21120.0 (7)H1A1—C1A—H1A2106
C25—C26—H26120Cl2B—C1B—Cl1B118.3 (16)
C21—C26—H26120Cl2B—C1B—H1B1107.7
C32—C31—C36119.4 (7)Cl1B—C1B—H1B1107.7
C32—C31—P1121.9 (5)Cl2B—C1B—H1B2107.7
C36—C31—P1118.5 (5)Cl1B—C1B—H1B2107.7
C31—C32—C33119.8 (7)H1B1—C1B—H1B2107.1
C31—C32—H32120.1
Au1—S1—P2—O176.2 (3)C11—P1—C31—C3268.3 (7)
Au1—S1—P2—O2165.7 (2)Au1—P1—C31—C32168.8 (6)
Au1—S1—P2—C4147.6 (2)C21—P1—C31—C36142.1 (6)
C31—P1—C11—C1697.8 (6)C11—P1—C31—C36105.9 (6)
C21—P1—C11—C16150.0 (6)Au1—P1—C31—C3617.0 (7)
Au1—P1—C11—C1626.0 (6)C36—C31—C32—C332.8 (12)
C31—P1—C11—C1276.7 (7)P1—C31—C32—C33176.9 (6)
C21—P1—C11—C1235.4 (7)C31—C32—C33—C342.4 (13)
Au1—P1—C11—C12159.5 (5)C32—C33—C34—C351.7 (13)
C16—C11—C12—C130.2 (11)C33—C34—C35—C361.3 (14)
P1—C11—C12—C13174.7 (6)C34—C35—C36—C311.6 (13)
C11—C12—C13—C140.2 (12)C32—C31—C36—C352.4 (12)
C12—C13—C14—C151.9 (12)P1—C31—C36—C35176.8 (7)
C13—C14—C15—C163.2 (12)O1—P2—C41—C45170.2 (6)
C14—C15—C16—C112.9 (13)O2—P2—C41—C4551.3 (7)
C12—C11—C16—C151.2 (11)S1—P2—C41—C4564.2 (7)
P1—C11—C16—C15173.5 (7)O1—P2—C41—C429.0 (8)
C31—P1—C21—C22150.7 (6)O2—P2—C41—C42127.9 (6)
C11—P1—C21—C2239.8 (7)S1—P2—C41—C42116.6 (6)
Au1—P1—C21—C2283.8 (7)C45—C41—C42—C430.2 (8)
C31—P1—C21—C2635.8 (7)P2—C41—C42—C43179.1 (6)
C11—P1—C21—C26146.7 (6)C41—C42—C43—C440.1 (8)
Au1—P1—C21—C2689.7 (6)C42—C43—C44—C450.3 (8)
C26—C21—C22—C232.1 (12)C42—C41—C45—C440.4 (8)
P1—C21—C22—C23175.7 (7)P2—C41—C45—C44178.9 (5)
C21—C22—C23—C241.4 (13)C43—C44—C45—C410.4 (8)
C22—C23—C24—C250.7 (13)C55—C51—C52—C532.3 (10)
C23—C24—C25—C262.0 (13)C51—C52—C53—C541.9 (10)
C24—C25—C26—C211.3 (12)C52—C53—C54—C550.7 (10)
C22—C21—C26—C250.8 (11)C52—C51—C55—C541.9 (9)
P1—C21—C26—C25174.4 (6)C53—C54—C55—C510.7 (10)
C21—P1—C31—C3243.7 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H1···O1i1.11 (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
Mr825.22
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)15.122 (3), 9.3157 (18), 22.581 (3)
β (°) 112.831 (10)
V3)2931.8 (9)
Z4
Radiation typeMo Kα
µ (mm1)5.88
Crystal size (mm)0.2 × 0.18 × 0.16
Data collection
DiffractometerBruker CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.386, 0.453
No. of measured, independent and
observed [I > 2σ(I)] reflections
13808, 4924, 4348
Rint0.112
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.051, 0.153, 1.10
No. of reflections4924
No. of parameters375
No. of restraints18
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O2—H1···O1i1.11 (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

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationBrandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (1998). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2001). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBurla, 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
First citationCrespo, 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
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationForeman, M. R. S., Slawin, A. M. Z. & Woollins, J. D. (1996). J. Chem. Soc. Dalton Trans. pp. 3653–3657  CrossRef Google Scholar
First citationPreisenberger, M., Schier, A. & Schmidbaur, H. (1998). Z. Naturforsch. Teil B, 53, 781–787.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationVan Zyl, W. E. (2010). Comments Inorg. Chem. 31, 13–45.  Web of Science CrossRef CAS Google Scholar
First citationVan Zyl, W. E. & Fackler, J. P. (2000). Phosphorus Sulfur Silicon Relat. Elem. 167, 117–132.  Web of Science CrossRef CAS Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds