(m-Phenyl­enedimethyl­ene)bis­(triphenyl­phospho­nium) bis­[chlorido(penta­fluoro­phen­yl)aurate(I)] dichloro­methane disolvate

Strasser, C.E.; Coetzee, K.; Cronje, S.; Raubenheimer, H.G.

doi:10.1107/S1600536809045474

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1499

doi:10.1107/S1600536809045474

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(m-Phenylenedimethylene)bis(triphenylphosphonium) bis[chlorido(pentafluorophenyl)aurate(I)] dichloromethane disolvate

Christoph E. Strasser,^a Karolien Coetzee,^a Stephanie Cronje ^a and Helgard G. Raubenheimer ^a ^*

^aDepartment of Chemistry and Polymer Science, University of Stellenbosch, Private Bag X1, Matieland 7602, South Africa
^*Correspondence e-mail: hgr@sun.ac.za

(Received 17 September 2009; accepted 29 October 2009; online 4 November 2009)

The title compound, (C₄₄H₃₈P₂)[AuCl(C₆F₅)]₂·2CH₂Cl₂, crystallizes with a twofold rotation axis through the central benzene ring in the bis-phosphonium dication. In the crystal, the dications and anions are ordered into columns running parallel to the c axis by contacts of the pro-ylidic CH₂ groups with the Cl atom of one and an ortho-F atom of another anion. The space between the columns is occupied by CH₂Cl₂ solvent molecules.

Related literature

For related structures, see: Briggs et al. (1988 ); Phillips et al. (2008 ). For the synthesis of the [AuCl(C₆F₅)]⁻ anion, see: Usón et al. (1977 ). For synthetic details, see: Friedrich & Henning (1959 ); Horner et al. (1962 ); Usón et al. (1989 ).

Experimental

Crystal data

(C₄₄H₃₈P₂)[AuCl(C₆F₅)]₂·2CH₂Cl₂
M_r = 1597.5
Orthorhombic, P b a 2
a = 14.506 (3) Å
b = 22.083 (4) Å
c = 8.9439 (18) Å
V = 2865.1 (10) Å³
Z = 2
Mo Kα radiation
μ = 5.52 mm⁻¹
T = 203 K
0.35 × 0.12 × 0.12 mm

Data collection

Nonius Kappa CCD diffractometer
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997 ) T_min = 0.207, T_max = 0.516
60733 measured reflections
6565 independent reflections
5638 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.052
S = 1.03
6565 reflections
353 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.50 e Å⁻³
Absolute structure: Flack (1983 ), 3067 Friedel pairs
Flack parameter: 0.034 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯Cl1	0.98	2.60	3.579 (5)	174
C5—H5B⋯F1ⁱ	0.98	2.29	3.263 (4)	171
Symmetry code: (i) x, y, z+1.

Data collection: COLLECT (Nonius, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Atwood & Barbour, 2003 ; Barbour, 2001 ); software used to prepare material for publication: X-SEED.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045474/om2280sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045474/om2280Isup2.hkl

checkCIF report

Comment top

Only one half of the bisphosphonium dication in the title compound shown in Scheme 1 is unique, a twofold rotation axis passes through C1 and C4 of the central benzene ring (Figure 1). The pro-ylidic methylene group is engaged in two contacts directed towards the chloro ligand of one [AuCl(C₆F₅)]^- complex and the other to the ortho-fluoro substituent of another anion related by a unit cell translation along the crystallographic c axis, Table 1 shows the geometric parameters. The dication thus forms contacts to two anion pairs related by a 2-fold operation. Each pair forms contacts to another dication forming a one-dimensional polar chain illustrated in Scheme 2. The dichloromethane solvent molecules fill channels that run parallel to the anion-cation columns. Cl2 of the CH₂Cl₂ molecules is engaged in a Cl···π contact with an electron-withdrawing C₆F₅ group [Cl—C₆ (centroid) distance 3.364 Å)]

A crystal structure that contains the present dication has not been reported. The orientation of the triphenylphosphonium groups in opposite directions is most likely favoured due to steric requirements.

The present crystal structure is one of few that contains the [AuCl(C₆F₅)]^- anion. One has been reported by Briggs et al. (1988) with the (phenylmethyl)triphenylphosphonium cation and another one was reported by Phillips et al. (2008) with the tetrabutylammonium cation. The Au—Cl and Au—C bond lengths are comparable to the values found in the present structure, the Au—Cl distance in the structure of Phillips et al. is longer at 2.3194 (16) Å. No structure incorporating the [AuCl(C₆F₅)]^- anion exhibits aurophilic interactions. In the structure of Briggs et al., H···Cl interactions between the pro-ylidic methylene group and the anions also seem to be present, but no hydrogen atom coordinates are supplied for the respective carbon atoms. The [AuCl(C₆F₅)]^- anion is a valuable starting material for the synthesis of complexes containing the AuC₆F₅ fragment (Usón et al., 1977).

Related literature top

For related structures, see: Briggs et al. (1988); Phillips et al. (2008). For the synthesis of the [AuCl(C₆F₅)]^- anion, see: Usón et al. (1977). For synthetic details, see: Friedrich & Henning (1959); Horner et al. (1962); Usón et al. (1989).

Experimental top

The title compound was isolated during an attempted preparation of the bis-ylide complex with Au(C₆F₅) fragments. 1,3-Bis[(triphenylphosphonio)methyl]benzene(2+) dibromide was prepared according to a modified literature procedure (Friedrich et al., 1959; Horner et al., 1962). The bromide was exchanged by excess NaBF₄ in 50% aqueous ethanol. The bis(tetrafluoroborate) was suspended in dry thf and cooled to -45 °C. The mixture turned dark brown upon addition of 1.6 M n-butyllithium, was subsequently stirred for 10 min and [Au(C₆F₅)(tht)] (tht = tetrahydrothiophene; Usón et al., 1989) in thf was added. The dry residue after removal of solvent was extracted with diethyl ether and dichloromethane. Crystals of the title compound were obtained after two recrystallizations from dichloromethane/hexane.

The chloride in the title compound originates from incomplete reaction during the preparation of [Au(C₆F₅)(tht)], in which [AuCl(tht)] is used. Traces of LiCl are thought to have been carried over to form the title compound which crystallizes preferentially. The Au1—Cl1 bond length of 2.3051 (18) Å excludes the presence of bromide from the phosphonium salt.

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Atwood & Barbour, 2003; Barbour, 2001); software used to prepare material for publication: X-SEED (Atwood & Barbour, 2003; Barbour, 2001).

Figures top

	Fig. 1. The molecular structure omitting hydrogen atoms and non-covalent interactions. Ellipsoids are drawn at the 50% probability level; the part of the cation related by a twofold rotation is shown in stick representation with symmetry code: ii = -x + 1, -y, z.
	Fig. 2. The hydrogen-bonding scheme in (I).

(m-Phenylenedimethylene)bis(triphenylphosphonium) bis[chlorido(pentafluorophenyl)aurate(I)] dichloromethane disolvate top

Crystal data top

(C₄₄H₃₈P₂)[AuCl(C₆F₅)]₂·2CH₂Cl₂	Z = 2
M_r = 1597.5	F(000) = 1540
Orthorhombic, Pba2	D_x = 1.852 Mg m⁻³
Hall symbol: P 2 -2ab	Mo Kα radiation, λ = 0.71073 Å
a = 14.506 (3) Å	µ = 5.52 mm⁻¹
b = 22.083 (4) Å	T = 203 K
c = 8.9439 (18) Å	Needle, colourless
V = 2865.1 (10) Å³	0.35 × 0.12 × 0.12 mm

Data collection top

Nonius Kappa CCD diffractometer	6565 independent reflections
Radiation source: fine-focus sealed tube	5638 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 27.5°, θ_min = 3.7°
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997)	h = −18→18
T_min = 0.207, T_max = 0.516	k = −28→28
60733 measured reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.052	w = 1/[σ²(F_o²) + (0.0174P)² + 1.2785P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6565 reflections	Δρ_max = 0.50 e Å⁻³
353 parameters	Δρ_min = −0.50 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 3067 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.034 (5)

Crystal data top

(C₄₄H₃₈P₂)[AuCl(C₆F₅)]₂·2CH₂Cl₂	V = 2865.1 (10) Å³
M_r = 1597.5	Z = 2
Orthorhombic, Pba2	Mo Kα radiation
a = 14.506 (3) Å	µ = 5.52 mm⁻¹
b = 22.083 (4) Å	T = 203 K
c = 8.9439 (18) Å	0.35 × 0.12 × 0.12 mm

Data collection top

Nonius Kappa CCD diffractometer	6565 independent reflections
Absorption correction: multi-scan (DENZO; Otwinowski & Minor, 1997)	5638 reflections with I > 2σ(I)
T_min = 0.207, T_max = 0.516	R_int = 0.042
60733 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	H-atom parameters constrained
wR(F²) = 0.052	Δρ_max = 0.50 e Å⁻³
S = 1.03	Δρ_min = −0.50 e Å⁻³
6565 reflections	Absolute structure: Flack (1983), 3067 Friedel pairs
353 parameters	Absolute structure parameter: 0.034 (5)
1 restraint

Special details top

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

Refinement. Refinement of F² against ALL 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
P1	0.29554 (5)	0.10315 (3)	0.61705 (15)	0.02913 (17)
C1	0.5000	0.0000	0.9430 (6)	0.0381 (13)
C2	0.4610 (2)	0.04836 (16)	0.8664 (4)	0.0343 (8)
C3	0.4600 (2)	0.04836 (15)	0.7119 (4)	0.0277 (7)
C4	0.5000	0.0000	0.6346 (10)	0.0269 (9)
C5	0.42041 (17)	0.10111 (12)	0.6264 (6)	0.0302 (6)
C6	0.2517 (2)	0.03869 (15)	0.5151 (4)	0.0330 (8)
C7	0.3065 (3)	0.01043 (16)	0.4097 (4)	0.0387 (9)
C8	0.2733 (3)	−0.0392 (2)	0.3333 (5)	0.0518 (11)
C9	0.1845 (3)	−0.05876 (18)	0.3566 (5)	0.0536 (11)
C10	0.1293 (3)	−0.0300 (2)	0.4562 (5)	0.0597 (12)
C11	0.1620 (3)	0.0191 (2)	0.5372 (5)	0.0497 (10)
C12	0.2605 (2)	0.17233 (15)	0.5272 (4)	0.0319 (8)
C13	0.1674 (3)	0.1861 (2)	0.5250 (6)	0.0599 (12)
C14	0.1374 (3)	0.2384 (2)	0.4552 (6)	0.0643 (13)
C15	0.2002 (3)	0.2769 (2)	0.3882 (5)	0.0539 (11)
C16	0.2905 (3)	0.2621 (2)	0.3868 (6)	0.0643 (13)
C17	0.3224 (3)	0.20981 (19)	0.4564 (5)	0.0536 (12)
C18	0.2512 (2)	0.10380 (16)	0.8034 (4)	0.0341 (8)
C19	0.2495 (3)	0.1577 (2)	0.8821 (5)	0.0476 (10)
C20	0.2253 (3)	0.1578 (3)	1.0317 (6)	0.0675 (14)
C21	0.2029 (3)	0.1045 (3)	1.1023 (6)	0.0701 (14)
C22	0.2034 (3)	0.0508 (3)	1.0243 (5)	0.0650 (14)
C23	0.2284 (3)	0.04949 (19)	0.8757 (5)	0.0466 (10)
H1	0.5000	0.0000	1.0481	0.046*
H2	0.4354	0.0810	0.9196	0.041*
H4	0.5000	0.0000	0.5295	0.032*
H5A	0.4448	0.1000	0.5242	0.036*
H5B	0.4420	0.1387	0.6729	0.036*
H7	0.3661	0.0250	0.3902	0.046*
H8	0.3115	−0.0597	0.2651	0.062*
H9	0.1619	−0.0923	0.3031	0.064*
H10	0.0685	−0.0434	0.4705	0.072*
H11	0.1237	0.0389	0.6064	0.060*
H13	0.1247	0.1600	0.5708	0.072*
H14	0.0742	0.2478	0.4534	0.077*
H15	0.1801	0.3132	0.3438	0.065*
H16	0.3326	0.2876	0.3378	0.077*
H17	0.3856	0.2002	0.4551	0.064*
H19	0.2648	0.1942	0.8340	0.057*
H20	0.2241	0.1945	1.0853	0.081*
H21	0.1871	0.1047	1.2042	0.084*
H22	0.1866	0.0147	1.0728	0.078*
H23	0.2302	0.0126	0.8233	0.056*
Au1	0.488135 (8)	0.198870 (5)	0.12628 (4)	0.04045 (5)
Cl1	0.50324 (7)	0.10795 (5)	0.24986 (12)	0.0484 (3)
F1	0.4675 (2)	0.23148 (12)	−0.2198 (3)	0.0672 (7)
F2	0.45501 (18)	0.33720 (11)	−0.3633 (5)	0.0731 (7)
F3	0.4605 (2)	0.44303 (12)	−0.2066 (4)	0.0832 (9)
F4	0.47789 (18)	0.44033 (11)	0.0945 (5)	0.0713 (11)
F5	0.48874 (17)	0.33557 (15)	0.2410 (4)	0.0608 (8)
C24	0.4787 (3)	0.27811 (19)	0.0173 (5)	0.0419 (10)
C25	0.4702 (3)	0.28254 (19)	−0.1338 (6)	0.0474 (10)
C26	0.4645 (3)	0.3359 (2)	−0.2122 (6)	0.0548 (11)
C27	0.4675 (3)	0.38949 (19)	−0.1351 (6)	0.0551 (12)
C28	0.4747 (3)	0.3880 (2)	0.0179 (6)	0.0522 (12)
C29	0.4806 (3)	0.3329 (2)	0.0903 (5)	0.0452 (14)
Cl2	0.24384 (10)	0.33560 (10)	1.00079 (18)	0.1041 (6)
Cl3	0.20261 (13)	0.38659 (9)	0.71284 (19)	0.1085 (6)
C30	0.1618 (4)	0.3621 (3)	0.8821 (7)	0.103 (2)
H30B	0.1295	0.3957	0.9308	0.123*
H30A	0.1166	0.3299	0.8646	0.123*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0292 (4)	0.0248 (4)	0.0334 (4)	0.0028 (3)	0.0009 (6)	0.0018 (6)
C1	0.037 (3)	0.051 (4)	0.026 (3)	0.007 (2)	0.000	0.000
C2	0.0310 (18)	0.037 (2)	0.035 (2)	0.0065 (16)	−0.0015 (15)	−0.0067 (16)
C4	0.0248 (19)	0.030 (2)	0.026 (2)	0.0013 (15)	0.000	0.000
C3	0.0250 (17)	0.0260 (18)	0.0322 (19)	0.0016 (14)	−0.0016 (14)	−0.0007 (15)
C5	0.0280 (14)	0.0258 (14)	0.0369 (16)	0.0011 (11)	0.000 (3)	0.000 (3)
C6	0.036 (2)	0.0265 (18)	0.037 (2)	−0.0015 (15)	−0.0052 (16)	0.0040 (15)
C7	0.042 (2)	0.032 (2)	0.042 (2)	0.0031 (16)	−0.0067 (17)	0.0000 (17)
C8	0.060 (3)	0.047 (2)	0.048 (3)	0.011 (2)	−0.015 (2)	−0.010 (2)
C9	0.062 (3)	0.036 (2)	0.062 (3)	−0.004 (2)	−0.021 (2)	−0.008 (2)
C10	0.045 (3)	0.060 (3)	0.074 (3)	−0.025 (2)	−0.007 (2)	0.003 (3)
C11	0.041 (2)	0.050 (2)	0.057 (3)	−0.008 (2)	0.001 (2)	−0.003 (2)
C12	0.035 (2)	0.0254 (18)	0.035 (2)	0.0057 (15)	−0.0021 (16)	0.0020 (15)
C13	0.039 (3)	0.052 (3)	0.088 (3)	0.006 (2)	−0.002 (2)	0.029 (2)
C14	0.043 (3)	0.051 (3)	0.099 (4)	0.019 (2)	−0.009 (2)	0.016 (3)
C15	0.064 (3)	0.037 (2)	0.061 (3)	0.017 (2)	−0.004 (2)	0.009 (2)
C16	0.063 (3)	0.041 (3)	0.089 (4)	0.004 (2)	0.009 (3)	0.028 (2)
C17	0.039 (2)	0.042 (2)	0.080 (3)	0.0096 (18)	0.008 (2)	0.021 (2)
C18	0.0258 (18)	0.039 (2)	0.038 (2)	0.0060 (15)	−0.0003 (14)	0.0046 (17)
C19	0.044 (2)	0.051 (3)	0.048 (3)	0.0028 (19)	0.005 (2)	−0.009 (2)
C20	0.056 (3)	0.093 (4)	0.054 (3)	0.014 (3)	0.000 (2)	−0.034 (3)
C21	0.055 (3)	0.118 (4)	0.037 (3)	0.016 (3)	0.004 (2)	0.007 (3)
C22	0.056 (3)	0.090 (4)	0.049 (3)	0.005 (3)	0.002 (2)	0.026 (3)
C23	0.048 (2)	0.046 (3)	0.046 (3)	0.0036 (19)	0.0011 (19)	0.0130 (19)
Au1	0.03975 (8)	0.03337 (8)	0.04823 (9)	0.00044 (5)	0.0041 (2)	−0.00390 (14)
Cl1	0.0664 (7)	0.0379 (6)	0.0408 (6)	0.0042 (4)	0.0087 (5)	0.0024 (4)
F1	0.090 (2)	0.0504 (17)	0.0612 (17)	0.0021 (14)	−0.0002 (14)	−0.0054 (14)
F2	0.0798 (16)	0.0718 (15)	0.0676 (18)	0.0066 (13)	0.011 (2)	0.012 (2)
F3	0.085 (2)	0.0458 (16)	0.119 (3)	0.0025 (15)	0.0096 (19)	0.0261 (16)
F4	0.0790 (17)	0.0310 (12)	0.104 (3)	−0.0003 (10)	0.0047 (17)	−0.0101 (16)
F5	0.0653 (18)	0.0474 (19)	0.070 (2)	0.0042 (12)	−0.0004 (14)	−0.0151 (18)
C24	0.033 (2)	0.036 (2)	0.058 (3)	−0.0002 (16)	0.0033 (18)	0.000 (2)
C25	0.044 (2)	0.030 (2)	0.068 (3)	−0.0009 (18)	0.004 (2)	−0.006 (2)
C26	0.044 (3)	0.057 (3)	0.063 (3)	0.004 (2)	0.008 (2)	0.005 (2)
C27	0.040 (2)	0.033 (2)	0.093 (4)	−0.0023 (18)	0.007 (2)	0.008 (2)
C28	0.039 (2)	0.037 (3)	0.081 (4)	−0.0027 (18)	0.006 (2)	−0.006 (2)
C29	0.033 (2)	0.038 (2)	0.065 (4)	−0.0004 (15)	0.0047 (19)	−0.005 (2)
Cl2	0.0567 (9)	0.1708 (17)	0.0849 (11)	0.0179 (10)	−0.0005 (8)	0.0315 (11)
Cl3	0.1261 (14)	0.1259 (15)	0.0733 (9)	0.0085 (11)	0.0209 (9)	0.0275 (9)
C30	0.047 (3)	0.155 (6)	0.106 (5)	0.015 (4)	0.009 (3)	0.066 (4)

Geometric parameters (Å, º) top

P1—C5	1.814 (3)	C7—H7	0.9400
P1—C6	1.806 (3)	C8—H8	0.9400
P1—C12	1.799 (3)	C9—H9	0.9400
P1—C18	1.787 (4)	C10—H10	0.9400
C1—C2	1.389 (4)	C11—H11	0.9400
C1—C2ⁱ	1.389 (4)	C13—H13	0.9400
C3—C2	1.382 (5)	C14—H14	0.9400
C3—C4	1.399 (5)	C15—H15	0.9400
C3—C5	1.507 (5)	C16—H16	0.9400
C4—C3ⁱ	1.399 (5)	C17—H17	0.9400
C6—C7	1.382 (5)	C19—H19	0.9400
C6—C11	1.385 (5)	C20—H20	0.9400
C7—C8	1.378 (6)	C21—H21	0.9400
C8—C9	1.375 (6)	C22—H22	0.9400
C9—C10	1.356 (6)	C23—H23	0.9400
C10—C11	1.387 (6)	Au1—Cl1	2.3024 (12)
C12—C13	1.385 (6)	Au1—C24	2.008 (4)
C12—C17	1.376 (5)	F1—C25	1.365 (5)
C13—C14	1.382 (6)	F2—C26	1.359 (6)
C14—C15	1.383 (6)	F3—C27	1.348 (5)
C15—C16	1.351 (6)	F4—C28	1.343 (5)
C16—C17	1.391 (6)	F5—C29	1.354 (6)
C18—C19	1.383 (5)	C24—C25	1.361 (6)
C18—C23	1.402 (5)	C24—C29	1.375 (7)
C19—C20	1.384 (6)	C25—C26	1.373 (7)
C20—C21	1.376 (7)	C26—C27	1.371 (7)
C21—C22	1.375 (7)	C27—C28	1.373 (7)
C22—C23	1.378 (6)	C28—C29	1.382 (7)
C1—H1	0.9400	Cl2—C30	1.698 (5)
C2—H2	0.9400	Cl3—C30	1.714 (6)
C4—H4	0.9400	C30—H30B	0.9800
C5—H5A	0.9800	C30—H30A	0.9800
C5—H5B	0.9800

P1—C5—H5A	108.5	C9—C8—H8	120.0
P1—C5—H5B	108.5	C9—C10—H10	119.8
C6—P1—C5	110.82 (16)	C10—C9—H9	119.8
C12—P1—C5	108.89 (16)	C10—C11—H11	120.3
C12—P1—C6	110.12 (17)	C11—C10—H10	119.8
C18—P1—C5	108.5 (2)	C12—C13—H13	120.1
C18—P1—C6	110.52 (17)	C12—C17—H17	120.4
C18—P1—C12	107.94 (17)	C13—C14—H14	119.9
C3—C5—P1	115.0 (2)	C14—C13—H13	120.1
C7—C6—P1	119.8 (3)	C14—C15—H15	120.2
C11—C6—P1	120.3 (3)	C15—C14—H14	119.9
C13—C12—P1	117.9 (3)	C15—C16—H16	119.3
C17—C12—P1	122.1 (3)	C16—C15—H15	120.2
C19—C18—P1	119.2 (3)	C16—C17—H17	120.4
C23—C18—P1	120.5 (3)	C17—C16—H16	119.3
C2ⁱ—C1—C2	120.9 (5)	C18—C19—H19	120.1
C2—C3—C4	119.3 (4)	C18—C23—H23	120.4
C2—C3—C5	120.8 (3)	C19—C20—H20	119.9
C3—C2—C1	119.8 (4)	C20—C19—H19	120.1
C3ⁱ—C4—C3	120.7 (7)	C20—C21—H21	119.9
C4—C3—C5	119.8 (4)	C21—C20—H20	119.9
C6—C11—C10	119.4 (4)	C21—C22—H22	119.7
C7—C6—C11	119.8 (3)	C22—C21—H21	119.9
C8—C7—C6	119.8 (4)	C22—C23—H23	120.4
C9—C8—C7	120.1 (4)	C23—C22—H22	119.7
C9—C10—C11	120.5 (4)	H5A—C5—H5B	107.5
C10—C9—C8	120.4 (4)	F1—C25—C24	120.2 (4)
C12—C17—C16	119.2 (4)	F1—C25—C26	114.8 (4)
C13—C14—C15	120.2 (4)	F2—C26—C25	122.2 (4)
C14—C13—C12	119.8 (4)	F2—C26—C27	119.0 (4)
C15—C16—C17	121.3 (4)	F3—C27—C26	121.1 (5)
C16—C15—C14	119.6 (4)	F3—C27—C28	119.9 (4)
C17—C12—C13	119.9 (3)	F4—C28—C27	119.4 (4)
C19—C18—C23	119.9 (3)	F4—C28—C29	121.1 (5)
C20—C19—C18	119.9 (4)	F5—C29—C24	120.9 (5)
C21—C20—C19	120.1 (5)	F5—C29—C28	115.7 (5)
C22—C21—C20	120.3 (5)	C24—Au1—Cl1	178.43 (11)
C22—C23—C18	119.2 (4)	C25—C24—Au1	123.4 (3)
C23—C22—C21	120.6 (4)	C29—C24—Au1	122.3 (4)
C1—C2—H2	120.1	C24—C25—C26	125.0 (4)
C2—C1—H1	119.5	C24—C29—C28	123.5 (5)
C2ⁱ—C1—H1	119.5	C25—C24—C29	114.2 (4)
C3—C2—H2	120.1	C26—C27—C28	118.9 (4)
C3—C4—H4	119.7	C27—C26—C25	118.8 (5)
C3ⁱ—C4—H4	119.7	C27—C28—C29	119.5 (4)
C3—C5—H5A	108.5	Cl2—C30—Cl3	114.8 (3)
C3—C5—H5B	108.5	Cl2—C30—H30A	108.6
C6—C7—H7	120.1	Cl2—C30—H30B	108.6
C6—C11—H11	120.3	Cl3—C30—H30A	108.6
C7—C8—H8	120.0	Cl3—C30—H30B	108.6
C8—C7—H7	120.1	H30B—C30—H30A	107.6
C8—C9—H9	119.8

P1—C6—C7—C8	179.2 (3)	C9—C10—C11—C6	0.2 (7)
P1—C6—C11—C10	179.1 (3)	C11—C6—C7—C8	−3.6 (6)
P1—C12—C13—C14	−179.1 (4)	C12—C13—C14—C15	−0.2 (7)
P1—C12—C17—C16	178.8 (4)	C13—C12—C17—C16	1.7 (7)
P1—C18—C19—C20	−172.7 (3)	C13—C14—C15—C16	2.3 (7)
P1—C18—C23—C22	173.4 (3)	C14—C15—C16—C17	−2.4 (8)
C5—P1—C6—C7	−25.6 (3)	C15—C16—C17—C12	0.4 (8)
C5—P1—C6—C11	157.3 (3)	C17—C12—C13—C14	−1.8 (7)
C5—P1—C12—C13	−172.4 (3)	C18—C19—C20—C21	0.0 (7)
C5—P1—C12—C17	10.4 (4)	C19—C18—C23—C22	0.8 (6)
C5—P1—C18—C19	80.3 (3)	C19—C20—C21—C22	−0.7 (7)
C5—P1—C18—C23	−92.2 (3)	C20—C21—C22—C23	1.5 (7)
C6—P1—C5—C3	−64.2 (4)	C21—C22—C23—C18	−1.6 (7)
C6—P1—C12—C13	65.9 (4)	C23—C18—C19—C20	0.0 (6)
C6—P1—C12—C17	−111.3 (4)	Au1—C24—C25—F1	0.1 (6)
C6—P1—C18—C19	−158.0 (3)	Au1—C24—C29—F5	−0.2 (5)
C6—P1—C18—C23	29.4 (4)	Au1—C24—C25—C26	−179.3 (3)
C12—P1—C5—C3	174.5 (3)	Au1—C24—C29—C28	179.6 (3)
C12—P1—C6—C7	94.9 (3)	F1—C25—C26—F2	1.3 (6)
C12—P1—C6—C11	−82.2 (3)	F2—C26—C27—F3	0.5 (6)
C12—P1—C18—C19	−37.5 (3)	F3—C27—C28—F4	−2.2 (6)
C12—P1—C18—C23	149.9 (3)	F4—C28—C29—F5	0.5 (6)
C18—P1—C5—C3	57.3 (3)	F1—C25—C26—C27	−179.4 (4)
C18—P1—C6—C7	−145.9 (3)	F2—C26—C27—C28	178.4 (4)
C18—P1—C6—C11	37.0 (4)	F3—C27—C28—C29	179.1 (4)
C18—P1—C12—C13	−54.8 (4)	F4—C28—C29—C24	−179.3 (4)
C18—P1—C12—C17	128.0 (4)	C24—C25—C26—F2	−179.2 (4)
C2—C3—C5—P1	−78.2 (4)	C25—C24—C29—F5	180.0 (4)
C4—C3—C5—P1	104.8 (3)	C25—C26—C27—F3	−178.8 (4)
C2ⁱ—C1—C2—C3	0.7 (2)	C26—C27—C28—F4	179.9 (4)
C2—C3—C4—C3ⁱ	0.6 (2)	C27—C28—C29—F5	179.2 (4)
C4—C3—C2—C1	−1.3 (5)	C29—C24—C25—F1	179.9 (3)
C5—C3—C2—C1	−178.3 (3)	C24—C25—C26—C27	0.1 (7)
C5—C3—C4—C3ⁱ	177.7 (3)	C25—C24—C29—C28	−0.2 (6)
C6—C7—C8—C9	3.1 (6)	C25—C26—C27—C28	−1.0 (7)
C7—C6—C11—C10	2.0 (6)	C26—C27—C28—C29	1.2 (6)
C7—C8—C9—C10	−0.9 (6)	C27—C28—C29—C24	−0.6 (6)
C8—C9—C10—C11	−0.7 (7)	C29—C24—C25—C26	0.5 (6)

Symmetry code: (i) −x+1, −y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cl1	0.98	2.60	3.579 (5)	174
C5—H5B···F1ⁱⁱ	0.98	2.29	3.263 (4)	171

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

Experimental details

Crystal data
Chemical formula	(C₄₄H₃₈P₂)[AuCl(C₆F₅)]₂·2CH₂Cl₂
M_r	1597.5
Crystal system, space group	Orthorhombic, Pba2
Temperature (K)	203
a, b, c (Å)	14.506 (3), 22.083 (4), 8.9439 (18)
V (Å³)	2865.1 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	5.52
Crystal size (mm)	0.35 × 0.12 × 0.12

Data collection
Diffractometer	Nonius Kappa CCD diffractometer
Absorption correction	Multi-scan (DENZO; Otwinowski & Minor, 1997)
T_min, T_max	0.207, 0.516
No. of measured, independent and observed [I > 2σ(I)] reflections	60733, 6565, 5638
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.052, 1.03
No. of reflections	6565
No. of parameters	353
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.50
Absolute structure	Flack (1983), 3067 Friedel pairs
Absolute structure parameter	0.034 (5)

Computer programs: COLLECT (Nonius, 1998), DENZO (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Atwood & Barbour, 2003; Barbour, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···Cl1	0.98	2.60	3.579 (5)	174.4
C5—H5B···F1ⁱ	0.98	2.29	3.263 (4)	170.5

Symmetry code: (i) x, y, z+1.

Acknowledgements

We would like to thank the National Research Foundation (NRF) of South Africa and Mintek (KC) for financial support.

References

Atwood, J. L. & Barbour, L. J. (2003). Cryst. Growth Des. 3, 3–8. Web of Science CrossRef CAS Google Scholar
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Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
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Nonius (1998). COLLECT, Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Phillips, V., Doerrer, L. H. & Rheingold, A. L. (2008). Private communication (Refcode: PONGAB). CCDC, Cambridge, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 65| Part 12| December 2009| Page m1499

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

(m-Phenyl­enedi­methyl­ene)bis­­(tri­phenyl­phospho­nium) bis­­[chlorido(penta­fluoro­phen­yl)aurate(I)] di­chloro­methane disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

(m-Phenylenedimethylene)bis(triphenylphosphonium) bis[chlorido(pentafluorophenyl)aurate(I)] dichloromethane disolvate