Bis[(diphenyl­phosphanylmeth­yl)diphenyl­phosphane sulfide-κ2P,S]copper(I) hexa­fluoridophosphate

Zhang, J.-J.; Hu, F.; Duan, T.-K.; Chen, Q.; Zhang, Q.-F.

doi:10.1107/S160053681202346X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page m841

doi:10.1107/S160053681202346X

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Bis[(diphenylphosphanylmethyl)diphenylphosphane sulfide-κ²P,S]copper(I) hexafluoridophosphate

Jing-Jing Zhang,^a Feng Hu,^a Tai-Ke Duan,^a Qun Chen ^b and Qian-Feng Zhang ^a,^b ^*

^aInstitute of Molecular Engineering and Applied Chemistry, Anhui University of Technology, Ma'anshan, Anhui 243002, People's Republic of China, and ^bDepartment of Applied Chemistry, School of Petrochemical Engineering, Changzhou University, Jiangsu 213164, People's Republic of China
^*Correspondence e-mail: zhangqf@ahut.edu.cn

(Received 15 May 2012; accepted 22 May 2012; online 31 May 2012)

In the title compound, [Cu(C₂₅H₂₂P₂S)₂]PF₆, the Cu^I atom, lying on a twofold rotation axis, adopts a distorted tetrahedral geometry. The (diphenylphosphanylmethyl)diphenylphosphane sulfide ligand coordinates to the Cu^I atom through one S and one P atom, forming a stable five-membered chelate ring. The P atom of the PF₆⁻ anion also lies on a twofold rotation axis.

Related literature

For background to copper(I) phosphane compounds, see: Bownaker et al. (1995 ); Comba et al. (1999 ); Liaw et al. (2005 ); Lobana et al. (2009 ); Nicola et al. (2005 ); Zhang et al. (2005 ). For related structures, see: Bera et al. (1999 ); Sivasankar et al. (2004 ).

Experimental

Crystal data

[Cu(C₂₅H₂₂P₂S)₂]PF₆
M_r = 1041.39
Orthorhombic, P c c a
a = 20.73 (3) Å
b = 12.004 (18) Å
c = 19.83 (3) Å
V = 4935 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.75 mm⁻¹
T = 296 K
0.26 × 0.22 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.830, T_max = 0.884
27988 measured reflections
5535 independent reflections
3424 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.152
S = 1.03
5535 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—P2	2.300 (3)
Cu1—S1	2.411 (3)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681202346X/hy2551sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681202346X/hy2551Isup2.hkl

checkCIF report

Comment top

The chemistry of copper(I) remains on the forefront in binding to soft Lewis bases such as phosphorous and sulfur donors (Liaw et al., 2005; Zhang et al., 2005). For examples, there are a number of published studies of structures that involve copper(I) complexes with phosphane ligands in variable copper(I)-to-ligand ratios (Bownaker et al., 1995; Comba et al., 1999). Mononuclear and dinuclear phosphane-copper(I) complexes with coordinated and bridging halide anions and phosphane ligands in various coordination modes have been well isolated and structurally characterized (Lobana et al., 2009). Quite a few copper(I) complexes with mixed phosphane and sulfide ligands have been synthesized and structurally measured by X-ray crystallography (Lobana et al., 2009; Nicola et al., 2005). Although adducts of bis(diphenylphosphanyl)methane (dppm), structurally defined complexes of the form CuX:dppm (1:1) (X = Cl, Br, I, CN, SCN), have been well documented (Nicola et al., 2005), only one example of mononuclear copper(I) complex with (diphenylphosphanylmethyl)diphenylphosphane sulfide (dppmS) that involves in oxidation of one phosphorus atom of the dppm ligand to P=S moiety has been reported (Sivasankar et al., 2004). The second example of mononuclear copper(I) complex with dppmS ligands is described in this paper.

The title compound consists of a cationic [Cu(dppmS)₂]⁺ unit and a PF₆^- anion (Fig. 1). The dppmS ligand coordinates to the Cu^I atom with one S and one P atoms, forming a stable five-membered chelating ring. The coordinating environment around the Cu^I atom is distorted tetrahedral. The Cu—P bond length (Table 1) is similar to those found in [Cu(dppmS)₂][ClO₄] (Sivasankar et al., 2004) and in the copper(I)-dppm complexes (Bera et al., 1999). The Cu—S bond length of 2.411 (3) Å agrees well with that of 2.395 (3) Å in [Cu(dppmS)₂][ClO₄] (Sivasankar et al., 2004). The P—Cu—P bond angle of 127.60 (11)° is obviously larger than the S—Cu—S bond angle of 101.63 (11)°, due to the bulky PPh₂ moiety directly binding to the Cu atom. The P—Cu—S bond angle of 97.37 (6)° in the five-membered ring of the dppmS ligand is more acute than that of 115.45 (5)° between two dppmS ligands. The PF₆^- anion has its expected structure as well as normal distances and angles.

Related literature top

For background to copper(I) phosphane compounds, see: Bownaker et al. (1995); Comba et al. (1999); Liaw et al. (2005); Lobana et al. (2009); Nicola et al. (2005); Zhang et al. (2005). For related structures, see: Bera et al. (1999); Sivasankar et al. (2004).

Experimental top

To a solution of [Cu(CH₃CN)₄][PF₆] (373 mg, 1.0 mmol) in CH₃CN (10 ml) was added with a dppm (796 mg, 2.0 mmol) solution in CH₂Cl₂ (5 ml) and S₈ powder (64 mg, 2.0 mmol). After the mixture was stirred for 4 h at room temperature, the colorless solution with a little brown precipitate was obtained. After filtration, colorless block crystals were formed by slow evaporation of the filtrate at room temperature in three days. Analysis, calculated for C₅₀H₄₄CuF₆P₅S₂: C 57.66, H 4.26%; found: C 57.53, H 4.23%.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. Molecular structure of the title compound, with displacement ellipsoids at the 50% probability level. [Symmetry codes: (A) 1/2-x, 1-y, z; (B) 1-x, y, 1/2-z.]

Bis[(diphenylphosphanylmethyl)diphenylphosphane sulfide-κ²P,S]copper(I) hexafluoridophosphate top

Crystal data top

[Cu(C₂₅H₂₂P₂S)₂]PF₆	F(000) = 2136
M_r = 1041.39	D_x = 1.402 Mg m⁻³
Orthorhombic, Pcca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2ac	Cell parameters from 2469 reflections
a = 20.73 (3) Å	θ = 1.0–24.6°
b = 12.004 (18) Å	µ = 0.75 mm⁻¹
c = 19.83 (3) Å	T = 296 K
V = 4935 (13) Å³	Block, colorless
Z = 4	0.26 × 0.22 × 0.17 mm

Data collection top

Bruker APEXII CCD diffractometer	5535 independent reflections
Radiation source: fine-focus sealed tube	3424 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
ϕ and ω scans	θ_max = 27.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −26→26
T_min = 0.830, T_max = 0.884	k = −15→7
27988 measured reflections	l = −25→25

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.152	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0663P)² + 1.7941P] where P = (F_o² + 2F_c²)/3
5535 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

[Cu(C₂₅H₂₂P₂S)₂]PF₆	V = 4935 (13) Å³
M_r = 1041.39	Z = 4
Orthorhombic, Pcca	Mo Kα radiation
a = 20.73 (3) Å	µ = 0.75 mm⁻¹
b = 12.004 (18) Å	T = 296 K
c = 19.83 (3) Å	0.26 × 0.22 × 0.17 mm

Data collection top

Bruker APEXII CCD diffractometer	5535 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3424 reflections with I > 2σ(I)
T_min = 0.830, T_max = 0.884	R_int = 0.070
27988 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.152	H-atom parameters constrained
S = 1.03	Δρ_max = 0.41 e Å⁻³
5535 reflections	Δρ_min = −0.55 e Å⁻³
290 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cu1	0.2500	0.5000	0.08447 (3)	0.0570 (2)
S1	0.25626 (4)	0.34472 (9)	0.00764 (4)	0.0673 (3)
P1	0.30722 (4)	0.25355 (8)	0.07262 (4)	0.0545 (2)
P2	0.34846 (4)	0.47449 (8)	0.13570 (4)	0.0571 (3)
P3	0.5000	0.08241 (18)	0.2500	0.1137 (7)
F1	0.42534 (14)	0.0827 (3)	0.2603 (2)	0.1813 (17)
F2	0.49237 (19)	−0.0099 (3)	0.1934 (2)	0.1708 (17)
F3	0.49046 (19)	0.1782 (3)	0.1953 (2)	0.1685 (15)
C1	0.37539 (13)	0.3349 (3)	0.10528 (16)	0.0591 (8)
H1A	0.4073	0.3444	0.0699	0.071*
H1B	0.3955	0.2947	0.1421	0.071*
C11	0.34201 (15)	0.1313 (3)	0.03184 (16)	0.0602 (8)
C12	0.3884 (2)	0.0687 (4)	0.0633 (2)	0.0860 (13)
H12	0.4014	0.0875	0.1068	0.103*
C13	0.4165 (2)	−0.0224 (4)	0.0314 (3)	0.1030 (15)
H13	0.4476	−0.0642	0.0538	0.124*
C14	0.3990 (3)	−0.0504 (5)	−0.0318 (3)	0.1114 (16)
H14	0.4176	−0.1117	−0.0529	0.134*
C15	0.3543 (4)	0.0107 (5)	−0.0643 (3)	0.157 (3)
H15	0.3424	−0.0085	−0.1080	0.188*
C16	0.3256 (3)	0.1031 (4)	−0.0330 (2)	0.1212 (19)
H16	0.2953	0.1454	−0.0563	0.145*
C21	0.25957 (15)	0.2067 (3)	0.14369 (17)	0.0640 (9)
C22	0.19323 (17)	0.1912 (4)	0.1354 (2)	0.0852 (12)
H22	0.1741	0.2056	0.0939	0.102*
C23	0.1559 (2)	0.1545 (4)	0.1891 (3)	0.1142 (17)
H23	0.1119	0.1432	0.1832	0.137*
C24	0.1833 (3)	0.1347 (5)	0.2504 (3)	0.122 (2)
H24	0.1577	0.1117	0.2863	0.146*
C25	0.2485 (3)	0.1485 (5)	0.2599 (2)	0.120 (2)
H25	0.2667	0.1338	0.3018	0.144*
C26	0.2877 (2)	0.1846 (4)	0.20634 (18)	0.0879 (13)
H26	0.3318	0.1938	0.2125	0.105*
C31	0.35556 (17)	0.4728 (4)	0.22775 (17)	0.0714 (10)
C32	0.3949 (3)	0.4004 (5)	0.2639 (2)	0.1215 (19)
H32	0.4197	0.3472	0.2418	0.146*
C33	0.3962 (4)	0.4097 (8)	0.3352 (3)	0.175 (3)
H33	0.4208	0.3609	0.3609	0.211*
C34	0.3596 (4)	0.4936 (8)	0.3663 (3)	0.165 (3)
H34	0.3600	0.4988	0.4131	0.198*
C35	0.3239 (3)	0.5671 (6)	0.3308 (2)	0.122 (2)
H35	0.3017	0.6239	0.3527	0.147*
C36	0.32075 (18)	0.5565 (4)	0.26102 (18)	0.0862 (13)
H36	0.2953	0.6055	0.2362	0.103*
C41	0.41620 (14)	0.5644 (3)	0.10968 (17)	0.0621 (9)
C42	0.42341 (17)	0.5905 (4)	0.0432 (2)	0.0885 (13)
H42	0.3951	0.5599	0.0119	0.106*
C43	0.4723 (2)	0.6623 (5)	0.0204 (3)	0.1042 (16)
H43	0.4765	0.6773	−0.0254	0.125*
C44	0.5129 (2)	0.7090 (4)	0.0646 (3)	0.1016 (15)
H44	0.5459	0.7550	0.0494	0.122*
C45	0.5059 (2)	0.6893 (5)	0.1319 (3)	0.1221 (19)
H45	0.5330	0.7245	0.1626	0.146*
C46	0.45783 (19)	0.6157 (5)	0.1550 (2)	0.1002 (16)
H46	0.4539	0.6013	0.2009	0.120*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0448 (3)	0.0748 (5)	0.0513 (3)	−0.0022 (3)	0.000	0.000
S1	0.0792 (6)	0.0684 (7)	0.0544 (5)	−0.0009 (5)	−0.0183 (4)	0.0036 (4)
P1	0.0491 (4)	0.0655 (6)	0.0490 (4)	−0.0057 (4)	−0.0055 (3)	0.0063 (4)
P2	0.0434 (4)	0.0800 (7)	0.0480 (4)	−0.0053 (4)	−0.0010 (3)	−0.0079 (4)
P3	0.0781 (10)	0.1068 (16)	0.1562 (19)	0.000	−0.0655 (11)	0.000
F1	0.0818 (19)	0.185 (4)	0.278 (5)	0.002 (2)	−0.058 (2)	−0.012 (3)
F2	0.152 (3)	0.140 (3)	0.220 (4)	−0.010 (2)	−0.064 (3)	−0.045 (3)
F3	0.186 (3)	0.137 (3)	0.182 (3)	0.008 (2)	−0.090 (3)	0.026 (3)
C1	0.0446 (15)	0.073 (2)	0.0595 (18)	−0.0040 (15)	−0.0001 (13)	−0.0038 (17)
C11	0.0624 (18)	0.058 (2)	0.0598 (19)	−0.0064 (16)	−0.0009 (15)	0.0016 (16)
C12	0.088 (3)	0.102 (4)	0.068 (2)	0.028 (2)	−0.0006 (19)	−0.007 (2)
C13	0.095 (3)	0.112 (4)	0.102 (4)	0.036 (3)	0.005 (3)	−0.002 (3)
C14	0.143 (5)	0.085 (4)	0.106 (4)	0.021 (3)	0.017 (3)	−0.010 (3)
C15	0.270 (9)	0.107 (5)	0.094 (4)	0.055 (5)	−0.060 (5)	−0.035 (3)
C16	0.181 (5)	0.083 (4)	0.100 (3)	0.031 (3)	−0.067 (3)	−0.019 (3)
C21	0.0567 (18)	0.072 (3)	0.0632 (19)	−0.0018 (16)	0.0013 (14)	0.0155 (18)
C22	0.057 (2)	0.098 (3)	0.100 (3)	−0.015 (2)	0.0021 (19)	0.022 (3)
C23	0.071 (3)	0.118 (4)	0.154 (5)	−0.021 (3)	0.021 (3)	0.042 (4)
C24	0.113 (4)	0.132 (5)	0.121 (4)	0.001 (3)	0.045 (3)	0.055 (4)
C25	0.121 (4)	0.154 (6)	0.085 (3)	0.015 (4)	0.013 (3)	0.058 (3)
C26	0.075 (2)	0.121 (4)	0.068 (2)	0.008 (2)	0.0031 (19)	0.036 (2)
C31	0.0624 (19)	0.101 (3)	0.0513 (18)	−0.010 (2)	−0.0058 (16)	−0.0060 (19)
C32	0.143 (4)	0.154 (5)	0.068 (3)	0.013 (4)	−0.036 (3)	−0.001 (3)
C33	0.244 (8)	0.206 (9)	0.076 (4)	0.028 (7)	−0.068 (5)	0.011 (4)
C34	0.229 (8)	0.217 (9)	0.049 (3)	0.004 (6)	−0.013 (4)	−0.013 (4)
C35	0.126 (4)	0.182 (6)	0.060 (3)	−0.004 (4)	0.005 (3)	−0.031 (3)
C36	0.074 (2)	0.125 (4)	0.060 (2)	−0.006 (2)	0.0007 (17)	−0.021 (2)
C41	0.0447 (15)	0.075 (3)	0.066 (2)	0.0004 (16)	0.0017 (14)	−0.0104 (18)
C42	0.070 (2)	0.127 (4)	0.068 (2)	−0.026 (2)	0.0032 (18)	−0.001 (2)
C43	0.079 (3)	0.139 (5)	0.095 (3)	−0.015 (3)	0.021 (2)	0.010 (3)
C44	0.071 (3)	0.101 (4)	0.132 (4)	−0.018 (2)	0.031 (3)	−0.005 (3)
C45	0.083 (3)	0.146 (5)	0.137 (5)	−0.055 (3)	−0.002 (3)	−0.034 (4)
C46	0.077 (2)	0.143 (5)	0.081 (3)	−0.043 (3)	−0.005 (2)	−0.013 (3)

Geometric parameters (Å, º) top

Cu1—P2	2.300 (3)	C22—H22	0.9300
Cu1—S1	2.411 (3)	C23—C24	1.363 (7)
S1—P1	1.993 (2)	C23—H23	0.9300
P1—C21	1.810 (4)	C24—C25	1.374 (7)
P1—C11	1.824 (4)	C24—H24	0.9300
P1—C1	1.836 (4)	C25—C26	1.405 (6)
P2—C31	1.831 (4)	C25—H25	0.9300
P2—C41	1.845 (4)	C26—H26	0.9300
P2—C1	1.866 (4)	C31—C32	1.390 (6)
P3—F1	1.561 (4)	C31—C36	1.403 (6)
P3—F1ⁱ	1.561 (4)	C32—C33	1.418 (7)
P3—F2	1.585 (4)	C32—H32	0.9300
P3—F2ⁱ	1.585 (4)	C33—C34	1.403 (10)
P3—F3ⁱ	1.593 (4)	C33—H33	0.9300
P3—F3	1.593 (4)	C34—C35	1.351 (9)
C1—H1A	0.9700	C34—H34	0.9300
C1—H1B	0.9700	C35—C36	1.391 (6)
C11—C12	1.371 (5)	C35—H35	0.9300
C11—C16	1.373 (6)	C36—H36	0.9300
C12—C13	1.392 (6)	C41—C42	1.364 (5)
C12—H12	0.9300	C41—C46	1.390 (5)
C13—C14	1.347 (7)	C42—C43	1.405 (6)
C13—H13	0.9300	C42—H42	0.9300
C14—C15	1.345 (8)	C43—C44	1.337 (7)
C14—H14	0.9300	C43—H43	0.9300
C15—C16	1.404 (7)	C44—C45	1.361 (7)
C15—H15	0.9300	C44—H44	0.9300
C16—H16	0.9300	C45—C46	1.409 (6)
C21—C26	1.397 (5)	C45—H45	0.9300
C21—C22	1.397 (5)	C46—H46	0.9300
C22—C23	1.388 (6)

P2ⁱⁱ—Cu1—P2	127.60 (11)	C11—C16—H16	119.9
P2ⁱⁱ—Cu1—S1	115.45 (5)	C15—C16—H16	119.9
P2—Cu1—S1	97.37 (6)	C26—C21—C22	119.3 (3)
P2ⁱⁱ—Cu1—S1ⁱⁱ	97.37 (6)	C26—C21—P1	121.5 (3)
P2—Cu1—S1ⁱⁱ	115.45 (5)	C22—C21—P1	119.1 (3)
S1—Cu1—S1ⁱⁱ	101.63 (13)	C23—C22—C21	120.0 (4)
P1—S1—Cu1	92.55 (4)	C23—C22—H22	120.0
C21—P1—C11	108.11 (19)	C21—C22—H22	120.0
C21—P1—C1	108.11 (18)	C24—C23—C22	120.5 (4)
C11—P1—C1	106.27 (17)	C24—C23—H23	119.8
C21—P1—S1	112.60 (15)	C22—C23—H23	119.8
C11—P1—S1	111.40 (15)	C23—C24—C25	120.7 (4)
C1—P1—S1	110.10 (15)	C23—C24—H24	119.6
C31—P2—C41	102.94 (16)	C25—C24—H24	119.6
C31—P2—C1	106.73 (18)	C24—C25—C26	120.2 (5)
C41—P2—C1	101.95 (17)	C24—C25—H25	119.9
C31—P2—Cu1	120.86 (12)	C26—C25—H25	119.9
C41—P2—Cu1	118.30 (14)	C21—C26—C25	119.3 (4)
C1—P2—Cu1	104.02 (10)	C21—C26—H26	120.4
F1—P3—F1ⁱ	179.7 (4)	C25—C26—H26	120.4
F1—P3—F2	89.8 (2)	C32—C31—C36	120.5 (4)
F1ⁱ—P3—F2	90.4 (2)	C32—C31—P2	124.6 (3)
F1—P3—F2ⁱ	90.4 (2)	C36—C31—P2	114.8 (3)
F1ⁱ—P3—F2ⁱ	89.8 (2)	C31—C32—C33	118.4 (6)
F2—P3—F2ⁱ	91.3 (4)	C31—C32—H32	120.8
F1—P3—F3ⁱ	91.8 (2)	C33—C32—H32	120.8
F1ⁱ—P3—F3ⁱ	88.0 (2)	C34—C33—C32	118.9 (6)
F2—P3—F3ⁱ	177.5 (3)	C34—C33—H33	120.5
F2ⁱ—P3—F3ⁱ	90.6 (3)	C32—C33—H33	120.5
F1—P3—F3	88.0 (2)	C35—C34—C33	122.5 (5)
F1ⁱ—P3—F3	91.8 (2)	C35—C34—H34	118.8
F2—P3—F3	90.6 (3)	C33—C34—H34	118.8
F2ⁱ—P3—F3	177.5 (3)	C34—C35—C36	118.9 (6)
F3ⁱ—P3—F3	87.6 (3)	C34—C35—H35	120.5
P1—C1—P2	111.18 (17)	C36—C35—H35	120.5
P1—C1—H1A	109.4	C35—C36—C31	120.6 (5)
P2—C1—H1A	109.4	C35—C36—H36	119.7
P1—C1—H1B	109.4	C31—C36—H36	119.7
P2—C1—H1B	109.4	C42—C41—C46	117.1 (4)
H1A—C1—H1B	108.0	C42—C41—P2	119.2 (3)
C12—C11—C16	117.8 (4)	C46—C41—P2	123.4 (3)
C12—C11—P1	121.1 (3)	C41—C42—C43	122.0 (4)
C16—C11—P1	121.0 (3)	C41—C42—H42	119.0
C11—C12—C13	121.1 (4)	C43—C42—H42	119.0
C11—C12—H12	119.4	C44—C43—C42	120.1 (5)
C13—C12—H12	119.4	C44—C43—H43	120.0
C14—C13—C12	120.4 (5)	C42—C43—H43	120.0
C14—C13—H13	119.8	C43—C44—C45	120.1 (4)
C12—C13—H13	119.8	C43—C44—H44	119.9
C15—C14—C13	119.7 (5)	C45—C44—H44	119.9
C15—C14—H14	120.2	C44—C45—C46	120.2 (4)
C13—C14—H14	120.2	C44—C45—H45	119.9
C14—C15—C16	120.8 (5)	C46—C45—H45	119.9
C14—C15—H15	119.6	C41—C46—C45	120.4 (4)
C16—C15—H15	119.6	C41—C46—H46	119.8
C11—C16—C15	120.2 (5)	C45—C46—H46	119.8

Symmetry codes: (i) −x+1, y, −z+1/2; (ii) −x+1/2, −y+1, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₂₅H₂₂P₂S)₂]PF₆
M_r	1041.39
Crystal system, space group	Orthorhombic, Pcca
Temperature (K)	296
a, b, c (Å)	20.73 (3), 12.004 (18), 19.83 (3)
V (Å³)	4935 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.75
Crystal size (mm)	0.26 × 0.22 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.830, 0.884
No. of measured, independent and observed [I > 2σ(I)] reflections	27988, 5535, 3424
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.646

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.152, 1.03
No. of reflections	5535
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.55

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Cu1—P2

2.300 (3)

Cu1—S1

2.411 (3)

Acknowledgements

This project was supported by the Program for New Century Excellent Talents in Universities of China (NCET-08–0618).

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