Bis[μ2-bis­(diphenyl­phosphan­yl)methane-κ2P:P′]bis­(μ4-diphenyl­phosphinato-κ4O:O:O′:O′)bis­(μ2-trifluoro­acetato-κ2O:O′)tetra­silver(I) acetonitrile disolvate

Huang, L.-L.; Jia, C.; Tang, L.-P.; Jing, B.; Deng, Q.-H.

doi:10.1107/S1600536811045466

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1677-m1678

https://doi.org/10.1107/S1600536811045466

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Bis[μ₂-bis(diphenylphosphanyl)methane-κ²P:P′]bis(μ₄-diphenylphosphinato-κ⁴O:O:O′:O′)bis(μ₂-trifluoroacetato-κ²O:O′)tetrasilver(I) acetonitrile disolvate

Li-Li Huang,^a Chen Jia,^b Li-Ping Tang,^a Bai Jing ^a and Qi-Hua Deng ^a ^*

^aSichuan College of Chemical Technology, Luzhou 646005, People's Republic of China, and ^bSchool of Chemistry and Chemical Engineering, Guangxi Normal University, Guilin 541004, People's Republic of China
^*Correspondence e-mail: dengqihua_1@163.com

(Received 21 October 2011; accepted 29 October 2011; online 5 November 2011)

In the cation of the title compound, [Ag₄(C₂F₃O₂)₂(C₁₂H₁₀O₂P)₂(C₂₅H₂₂P₂)₂]·2CH₃CN, the two independent Ag⁺ cations are four-coordinated in a distorted tetrahedral geometry by one P atom from a bis(diphenylphosphanyl)methane (dppm) ligand, one O atom from a trifluoroacetate anion and two O atoms from two diphenylphosphinate (dpp) ligands. Two dppm ligands, two dpp ligands and two trifluoroacetate anions bridge four metal atoms, forming a centrosymmetric tetranuclear complex. Intramolecular C—H⋯O hydrogen bonds and a weak π–π interaction [centroid–centroid distance = 3.9804 (13) Å] are also observed.

Related literature

For applications of metals complexes with diphosphine ligands, see: Catalano & Malwitz (2004 ); Chiu & Lee (2005 ). For related structures, see: Kuang et al. (2002 ); Rudler et al. (1997 ); Zank et al. (1999 ).

Experimental

Crystal data

[Ag₄(C₂F₃O₂)₂(C₁₂H₁₀O₂P)₂(C₂₅H₂₂P₂)₂]·2C₂H₃N
M_r = 1942.70
Monoclinic, P 2₁ /n
a = 11.724 (5) Å
b = 14.777 (6) Å
c = 24.183 (10) Å
β = 102.254 (5)°
V = 4094 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.13 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009 ) T_min = 0.806, T_max = 0.806
34844 measured reflections
7192 independent reflections
6033 reflections with I > 2σ(I)
R_int = 0.057

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.117
S = 1.01
7192 reflections
480 parameters
60 restraints
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O3	0.93	2.46	3.380 (8)	169
C7—H7⋯O4ⁱ	0.93	2.45	3.368 (7)	171
Symmetry code: (i) -x+1, -y+2, -z.

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; 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: https://doi.org/10.1107/S1600536811045466/rz2658sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811045466/rz2658Isup2.hkl

checkCIF report

Comment top

Over the past three decades, metals complexes containing diphosphine ligands attract great interest for their importance in their potential applications in dye-sensitized solar cells and photochemical catalysts (Catalano & Malwitz, 2004; Chiu & Lee, 2005). A series of silver(I) complexes containing diphosphine ligands have been synthesized (Kuang et al., 2002). Synthetic tetranuclear silver(I) compounds have been widely reported (Rudler et al., 1997; Zank et al., 1999).

In the title compound (Fig. 1), the silver(I) atom adopts a distorted tetrahedral geometry through one P atom from a bis(diphenylphosphanyl)methane (dppm)ligand, one O atom from a trifluoroacetato anion and two O atoms from two diphenylphosphinate (dpp) ligands. Two dppm ligands, two dpp ligands and two trifluoroacetato anions bridge four metal atoms forming a centrosymmetric tetranuclear complex where the shortest Ag···Ag separation is 3.3655 (12) Å. The Ag—P and Ag—O bond distances are in the range 2.3685 (14)–2.3734 (14) and 2.278 (3)–2.505 (3) (14) Å, respectively. The O—Ag—P angles and O—Ag—O bond angles range from 80.56 (11) to 92.43 (14)° and from 106.90 (11) to 150.88 (8)°, respectively. In the crystal, intramolecular C—H···O hydrogen bonds are present (Table 1). In addition, a weak intramolecular π–π interaction of 3.9804 (13) Å between the centroids of the C8—C13 and C20—C25 phenyl rings is observed.

Related literature top

For applications of metals complexes of diphosphine ligands, see: Catalano & Malwitz (2004); Chiu & Lee (2005). For related structures, see: Kuang et al. (2002); Rudler et al. (1997); Zank et al. (1999).

Experimental top

The synthesis of the title compound was carried out by reacting silver trifluoroacetato (0.044 g, 0.2 mmol), diphenylphosphinic acid (0.022 g, 0.1 mmol) and bis(diphenylphosphine)methane (0.038 g, 0.1 mmol). The resulting mixture was allowed to stir for 1 h at room temperature. Colourless crystals of the title compound were obtained in 6 days by slow diffusion of diethyl ether into the solution (yield 15%).

Structure description top

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2009); cell refinement: CrystalClear-SM Expert (Rigaku, 2009); data reduction: CrystalClear-SM Expert (Rigaku, 2009); 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. The molecular structure of title complex with displacement ellipsoids drawn at 50% probability level. Unlabelled atoms are related to the labelled atom by the symmetry operation 1-x, 2-y, -z. Hydrogen atoms are omitted for clarity.

Bis[µ₂-bis(diphenylphosphanyl)methane-κ²P:P']bis(µ₄- diphenylphosphinato-κ⁴O:O:O':O')bis(µ₂- trifluoroacetato-κ²O:O')tetrasilver(I) acetonitrile disolvate top

Crystal data top

[Ag₄(C₂F₃O₂)₂(C₁₂H₁₀O₂P)₂(C₂₅H₂₂P₂)₂]·2C₂H₃N	F(000) = 1944
M_r = 1942.70	D_x = 1.576 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9421 reflections
a = 11.724 (5) Å	θ = 2.1–27.5°
b = 14.777 (6) Å	µ = 1.13 mm⁻¹
c = 24.183 (10) Å	T = 296 K
β = 102.254 (5)°	Prism, colourless
V = 4094 (3) Å³	0.20 × 0.20 × 0.20 mm
Z = 2

Data collection top

Rigaku Mercury CCD diffractometer	7192 independent reflections
Radiation source: fine-focus sealed tube	6033 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.057
Detector resolution: 13.6612 pixels mm^-1	θ_max = 25.0°, θ_min = 2.5°
ω scans	h = −13→13
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	k = −17→17
T_min = 0.806, T_max = 0.806	l = −28→28
34844 measured 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0503P)² + 7.4307P] where P = (F_o² + 2F_c²)/3
7192 reflections	(Δ/σ)_max = 0.001
480 parameters	Δρ_max = 1.08 e Å⁻³
60 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[Ag₄(C₂F₃O₂)₂(C₁₂H₁₀O₂P)₂(C₂₅H₂₂P₂)₂]·2C₂H₃N	V = 4094 (3) Å³
M_r = 1942.70	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.724 (5) Å	µ = 1.13 mm⁻¹
b = 14.777 (6) Å	T = 296 K
c = 24.183 (10) Å	0.20 × 0.20 × 0.20 mm
β = 102.254 (5)°

Data collection top

Rigaku Mercury CCD diffractometer	7192 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2009)	6033 reflections with I > 2σ(I)
T_min = 0.806, T_max = 0.806	R_int = 0.057
34844 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	60 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.01	Δρ_max = 1.08 e Å⁻³
7192 reflections	Δρ_min = −0.59 e Å⁻³
480 parameters

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 > 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
Ag1	0.54210 (3)	0.92166 (3)	0.087708 (16)	0.04807 (13)
Ag2	0.66296 (3)	0.91321 (2)	−0.026597 (15)	0.04551 (13)
C1	0.6904 (4)	0.7175 (3)	0.06180 (18)	0.0384 (10)
H1A	0.7435	0.6710	0.0803	0.046*
H1B	0.6232	0.6873	0.0389	0.046*
C2	0.7857 (4)	0.6966 (3)	−0.0368 (2)	0.0457 (11)
C3	0.8256 (6)	0.6101 (4)	−0.0213 (3)	0.0708 (17)
H3	0.8354	0.5916	0.0162	0.085*
C4	0.8511 (7)	0.5508 (5)	−0.0616 (3)	0.087 (2)
H4	0.8787	0.4930	−0.0508	0.104*
C5	0.8363 (6)	0.5760 (5)	−0.1163 (3)	0.083 (2)
H5	0.8561	0.5364	−0.1427	0.099*
C6	0.7922 (6)	0.6594 (5)	−0.1331 (3)	0.0785 (19)
H6	0.7787	0.6756	−0.1711	0.094*
C7	0.7674 (5)	0.7208 (4)	−0.0931 (2)	0.0618 (14)
H7	0.7384	0.7779	−0.1046	0.074*
C8	0.9111 (4)	0.8015 (3)	0.0557 (2)	0.0438 (11)
C9	0.9731 (5)	0.7357 (4)	0.0905 (3)	0.081 (2)
H9	0.9382	0.6805	0.0951	0.098*
C10	1.0871 (6)	0.7523 (5)	0.1185 (4)	0.106 (3)
H10	1.1290	0.7078	0.1414	0.128*
C11	1.1380 (5)	0.8335 (5)	0.1127 (3)	0.086 (2)
H11	1.2150	0.8435	0.1312	0.103*
C12	1.0781 (6)	0.8999 (5)	0.0803 (3)	0.0767 (18)
H12	1.1129	0.9557	0.0772	0.092*
C13	0.9638 (5)	0.8835 (4)	0.0518 (2)	0.0608 (14)
H13	0.9223	0.9290	0.0296	0.073*
C14	0.5474 (4)	0.7051 (3)	0.14380 (18)	0.0438 (11)
C15	0.5558 (6)	0.6126 (4)	0.1397 (2)	0.0673 (16)
H15	0.6127	0.5872	0.1230	0.081*
C16	0.4787 (7)	0.5568 (5)	0.1607 (3)	0.087 (2)
H16	0.4850	0.4942	0.1584	0.105*
C17	0.3939 (6)	0.5940 (6)	0.1848 (3)	0.085 (2)
H17	0.3410	0.5567	0.1976	0.102*
C18	0.3867 (5)	0.6852 (6)	0.1902 (3)	0.075 (2)
H18	0.3307	0.7098	0.2079	0.090*
C19	0.4623 (4)	0.7420 (4)	0.1696 (2)	0.0590 (14)
H19	0.4563	0.8044	0.1729	0.071*
C20	0.7694 (4)	0.7932 (3)	0.17396 (19)	0.0448 (11)
C21	0.8085 (5)	0.7232 (4)	0.2106 (3)	0.0722 (17)
H21	0.7679	0.6687	0.2071	0.087*
C22	0.9087 (6)	0.7338 (6)	0.2529 (3)	0.091 (2)
H22	0.9336	0.6863	0.2778	0.109*
C23	0.9698 (7)	0.8112 (6)	0.2584 (3)	0.100 (3)
H23	1.0357	0.8174	0.2873	0.120*
C24	0.9360 (7)	0.8798 (6)	0.2221 (4)	0.106 (3)
H24	0.9804	0.9324	0.2252	0.128*
C25	0.8344 (6)	0.8724 (4)	0.1798 (3)	0.0770 (18)
H25	0.8103	0.9208	0.1556	0.092*
C26	0.6109 (4)	1.2297 (3)	0.0284 (2)	0.0469 (12)
C27	0.5551 (6)	1.2773 (4)	0.0637 (3)	0.0758 (19)
H27	0.5217	1.2470	0.0900	0.091*
C28	0.5490 (8)	1.3714 (6)	0.0598 (4)	0.113 (3)
H28	0.5077	1.4036	0.0821	0.135*
C29	0.6024 (9)	1.4159 (5)	0.0238 (5)	0.126 (5)
H29	0.6035	1.4788	0.0242	0.152*
C30	0.6548 (8)	1.3706 (5)	−0.0131 (4)	0.109 (3)
H30	0.6870	1.4023	−0.0393	0.131*
C31	0.6599 (5)	1.2760 (4)	−0.0113 (3)	0.0732 (18)
H31	0.6955	1.2443	−0.0362	0.088*
C32	0.7743 (4)	1.1088 (3)	0.08724 (19)	0.0411 (10)
C33	0.8771 (4)	1.1165 (4)	0.0682 (3)	0.0623 (15)
H33	0.8753	1.1158	0.0295	0.075*
C34	0.9828 (5)	1.1255 (5)	0.1063 (3)	0.083 (2)
H34	1.0516	1.1303	0.0932	0.100*
C35	0.9864 (6)	1.1272 (5)	0.1625 (3)	0.083 (2)
H35	1.0577	1.1337	0.1878	0.099*
C36	0.8866 (6)	1.1196 (5)	0.1822 (3)	0.081 (2)
H36	0.8901	1.1208	0.2210	0.097*
C38	0.3389 (7)	1.0357 (6)	0.2187 (3)	0.0934 (15)
C39	0.3725 (6)	1.0221 (5)	0.1619 (3)	0.0804 (12)
C40	0.8585 (15)	0.3690 (11)	0.1793 (11)	0.393 (18)
H40A	0.9376	0.3619	0.1999	0.590*
H40B	0.8366	0.3177	0.1551	0.590*
H40C	0.8076	0.3734	0.2055	0.590*
C41	0.8488 (9)	0.4537 (7)	0.1442 (6)	0.150 (5)
C37O	0.7795 (3)	1.1099 (2)	0.14489 (10)	0.0608 (14)
H37O	0.7116	1.1042	0.1587	0.073*
F1	0.2990 (3)	1.1197 (2)	0.22513 (10)	0.1335 (18)
F2	0.4197 (3)	1.0317 (2)	0.26317 (10)	0.155 (2)
F3	0.2555 (3)	0.9843 (2)	0.22562 (10)	0.160 (2)
N1	0.8428 (7)	0.5182 (5)	0.1215 (4)	0.124 (3)
O1	0.5435 (3)	1.0716 (2)	0.06592 (14)	0.0466 (8)
O2	0.6484 (3)	1.0685 (2)	−0.01761 (13)	0.0440 (7)
O3	0.4545 (4)	0.9706 (3)	0.16520 (18)	0.0879 (12)
O4	0.3134 (4)	1.0629 (3)	0.12293 (16)	0.0762 (12)
P1	0.76367 (10)	0.78230 (8)	0.01470 (5)	0.0374 (3)
P2	0.64141 (10)	0.78438 (8)	0.11642 (5)	0.0375 (3)
P3	0.63580 (10)	1.10991 (8)	0.03764 (5)	0.0385 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0513 (2)	0.0492 (2)	0.0450 (2)	0.01425 (17)	0.01323 (17)	0.00685 (16)
Ag2	0.0429 (2)	0.0487 (2)	0.0454 (2)	0.01025 (16)	0.01052 (16)	0.00678 (15)
C1	0.039 (2)	0.041 (2)	0.036 (2)	0.0013 (19)	0.0084 (18)	0.0010 (18)
C2	0.040 (2)	0.051 (3)	0.050 (3)	−0.003 (2)	0.016 (2)	−0.005 (2)
C3	0.100 (5)	0.055 (3)	0.065 (4)	0.013 (3)	0.033 (3)	−0.006 (3)
C4	0.111 (6)	0.063 (4)	0.094 (5)	0.008 (4)	0.041 (4)	−0.023 (4)
C5	0.084 (5)	0.090 (5)	0.080 (5)	−0.007 (4)	0.029 (4)	−0.042 (4)
C6	0.086 (5)	0.103 (5)	0.049 (3)	−0.006 (4)	0.022 (3)	−0.024 (3)
C7	0.060 (3)	0.076 (4)	0.052 (3)	0.003 (3)	0.016 (3)	−0.010 (3)
C8	0.033 (2)	0.050 (3)	0.048 (3)	0.004 (2)	0.009 (2)	−0.005 (2)
C9	0.046 (3)	0.058 (4)	0.127 (6)	0.003 (3)	−0.012 (3)	0.002 (4)
C10	0.052 (4)	0.079 (5)	0.162 (8)	0.008 (4)	−0.035 (4)	0.005 (5)
C11	0.043 (3)	0.095 (5)	0.109 (6)	−0.002 (4)	−0.006 (3)	−0.021 (4)
C12	0.065 (4)	0.079 (4)	0.083 (5)	−0.028 (4)	0.009 (3)	−0.009 (4)
C13	0.059 (3)	0.062 (3)	0.059 (3)	−0.009 (3)	0.008 (3)	0.007 (3)
C14	0.042 (2)	0.056 (3)	0.033 (2)	−0.004 (2)	0.0079 (19)	0.003 (2)
C15	0.094 (5)	0.064 (4)	0.050 (3)	−0.018 (3)	0.030 (3)	−0.001 (3)
C16	0.134 (7)	0.074 (4)	0.062 (4)	−0.047 (4)	0.036 (4)	−0.004 (3)
C17	0.081 (5)	0.122 (6)	0.054 (4)	−0.048 (5)	0.019 (3)	0.013 (4)
C18	0.043 (3)	0.122 (6)	0.063 (4)	0.004 (4)	0.017 (3)	0.036 (4)
C19	0.048 (3)	0.079 (4)	0.052 (3)	0.009 (3)	0.014 (2)	0.022 (3)
C20	0.043 (3)	0.054 (3)	0.035 (2)	−0.001 (2)	0.0044 (19)	−0.002 (2)
C21	0.063 (4)	0.074 (4)	0.071 (4)	0.002 (3)	−0.005 (3)	0.010 (3)
C22	0.072 (4)	0.116 (6)	0.070 (4)	0.013 (4)	−0.017 (3)	0.020 (4)
C23	0.084 (5)	0.113 (6)	0.083 (5)	−0.004 (5)	−0.028 (4)	−0.005 (5)
C24	0.093 (6)	0.102 (6)	0.105 (6)	−0.029 (5)	−0.024 (5)	−0.024 (5)
C25	0.076 (4)	0.062 (4)	0.082 (4)	−0.001 (3)	−0.007 (3)	−0.007 (3)
C26	0.044 (3)	0.042 (3)	0.046 (3)	0.003 (2)	−0.009 (2)	−0.003 (2)
C27	0.074 (4)	0.064 (4)	0.080 (4)	0.024 (3)	−0.006 (3)	−0.022 (3)
C28	0.115 (7)	0.074 (5)	0.125 (8)	0.035 (5)	−0.030 (6)	−0.045 (5)
C29	0.131 (9)	0.043 (4)	0.162 (11)	0.012 (5)	−0.065 (8)	−0.015 (5)
C30	0.119 (7)	0.060 (5)	0.126 (7)	−0.023 (5)	−0.027 (6)	0.037 (5)
C31	0.072 (4)	0.053 (3)	0.083 (4)	−0.014 (3)	−0.010 (3)	0.017 (3)
C32	0.038 (2)	0.041 (2)	0.043 (3)	−0.001 (2)	0.0029 (19)	−0.0015 (19)
C33	0.041 (3)	0.086 (4)	0.061 (3)	−0.007 (3)	0.011 (2)	−0.008 (3)
C34	0.035 (3)	0.117 (6)	0.094 (5)	−0.010 (3)	0.008 (3)	−0.013 (4)
C35	0.051 (4)	0.101 (5)	0.080 (5)	0.001 (4)	−0.020 (3)	−0.009 (4)
C36	0.075 (4)	0.107 (5)	0.049 (3)	0.004 (4)	−0.015 (3)	−0.002 (3)
C38	0.108 (3)	0.123 (3)	0.062 (3)	0.014 (3)	0.047 (2)	0.003 (3)
C39	0.099 (3)	0.096 (3)	0.060 (2)	0.034 (2)	0.048 (2)	0.013 (2)
C40	0.195 (16)	0.238 (18)	0.68 (4)	−0.046 (14)	−0.05 (2)	0.32 (2)
C41	0.095 (7)	0.094 (7)	0.238 (14)	−0.001 (6)	−0.019 (8)	0.025 (8)
C37O	0.055 (3)	0.075 (4)	0.050 (3)	0.002 (3)	0.004 (2)	0.001 (3)
F1	0.157 (4)	0.148 (4)	0.111 (3)	0.031 (3)	0.061 (3)	−0.034 (3)
F2	0.164 (5)	0.242 (6)	0.056 (3)	0.039 (5)	0.018 (3)	0.006 (3)
F3	0.210 (5)	0.187 (5)	0.121 (4)	−0.077 (4)	0.121 (4)	−0.039 (3)
N1	0.138 (7)	0.076 (5)	0.142 (7)	0.013 (5)	−0.005 (5)	0.022 (4)
O1	0.0314 (16)	0.0489 (19)	0.059 (2)	−0.0002 (14)	0.0086 (14)	0.0036 (15)
O2	0.0459 (18)	0.0400 (17)	0.0433 (18)	0.0018 (14)	0.0030 (14)	−0.0048 (13)
O3	0.108 (3)	0.101 (3)	0.067 (2)	0.042 (2)	0.0471 (19)	0.013 (2)
O4	0.085 (3)	0.103 (3)	0.047 (2)	0.024 (3)	0.027 (2)	0.019 (2)
P1	0.0333 (6)	0.0411 (6)	0.0386 (6)	0.0049 (5)	0.0098 (5)	0.0001 (5)
P2	0.0355 (6)	0.0428 (6)	0.0348 (6)	0.0044 (5)	0.0086 (5)	0.0029 (5)
P3	0.0337 (6)	0.0376 (6)	0.0416 (6)	−0.0001 (5)	0.0021 (5)	−0.0008 (5)

Geometric parameters (Å, º) top

Ag1—O1	2.278 (3)	C20—P2	1.822 (5)
Ag1—P2	2.3685 (14)	C21—C22	1.393 (8)
Ag1—O3	2.430 (4)	C21—H21	0.9300
Ag1—O2ⁱ	2.505 (3)	C22—C23	1.342 (10)
Ag1—Ag2	3.3655 (12)	C22—H22	0.9300
Ag2—O2	2.314 (3)	C23—C24	1.343 (11)
Ag2—P1	2.3734 (14)	C23—H23	0.9300
Ag2—O1ⁱ	2.416 (3)	C24—C25	1.400 (9)
Ag2—O4ⁱ	2.429 (4)	C24—H24	0.9300
C1—P1	1.835 (4)	C25—H25	0.9300
C1—P2	1.837 (4)	C26—C27	1.375 (8)
C1—H1A	0.9700	C26—C31	1.396 (8)
C1—H1B	0.9700	C26—P3	1.800 (5)
C2—C7	1.380 (7)	C27—C28	1.394 (10)
C2—C3	1.386 (8)	C27—H27	0.9300
C2—P1	1.832 (5)	C28—C29	1.346 (14)
C3—C4	1.390 (8)	C28—H28	0.9300
C3—H3	0.9300	C29—C30	1.362 (14)
C4—C5	1.350 (10)	C29—H29	0.9300
C4—H4	0.9300	C30—C31	1.399 (9)
C5—C6	1.365 (10)	C30—H30	0.9300
C5—H5	0.9300	C31—H31	0.9300
C6—C7	1.399 (8)	C32—C37O	1.383 (5)
C6—H6	0.9300	C32—C33	1.384 (7)
C7—H7	0.9300	C32—P3	1.802 (5)
C8—C13	1.373 (7)	C33—C34	1.385 (8)
C8—C9	1.386 (8)	C33—H33	0.9300
C8—P1	1.823 (5)	C34—C35	1.350 (9)
C9—C10	1.386 (8)	C34—H34	0.9300
C9—H9	0.9300	C35—C36	1.359 (10)
C10—C11	1.360 (10)	C35—H35	0.9300
C10—H10	0.9300	C36—C37O	1.390 (7)
C11—C12	1.355 (9)	C36—H36	0.9300
C11—H11	0.9300	C38—F2	1.275 (8)
C12—C13	1.393 (8)	C38—F3	1.277 (9)
C12—H12	0.9300	C38—F1	1.347 (9)
C13—H13	0.9300	C38—C39	1.521 (8)
C14—C15	1.376 (7)	C39—O4	1.206 (7)
C14—C19	1.394 (7)	C39—O3	1.215 (7)
C14—P2	1.826 (5)	C40—C41	1.503 (16)
C15—C16	1.396 (8)	C40—H40A	0.9600
C15—H15	0.9300	C40—H40B	0.9600
C16—C17	1.370 (10)	C40—H40C	0.9600
C16—H16	0.9300	C41—N1	1.096 (11)
C17—C18	1.358 (10)	C37O—H37O	0.9300
C17—H17	0.9300	O1—P3	1.508 (3)
C18—C19	1.388 (8)	O1—Ag2ⁱ	2.416 (3)
C18—H18	0.9300	O2—P3	1.505 (3)
C19—H19	0.9300	O2—Ag1ⁱ	2.505 (3)
C20—C21	1.376 (7)	O4—Ag2ⁱ	2.429 (4)
C20—C25	1.387 (8)

O1—Ag1—P2	150.88 (8)	C21—C22—H22	119.4
O1—Ag1—O3	85.06 (14)	C22—C23—C24	120.1 (7)
P2—Ag1—O3	106.90 (11)	C22—C23—H23	120.0
O1—Ag1—O2ⁱ	80.56 (11)	C24—C23—H23	120.0
P2—Ag1—O2ⁱ	124.08 (8)	C23—C24—C25	120.4 (7)
O3—Ag1—O2ⁱ	92.43 (14)	C23—C24—H24	119.8
O1—Ag1—Ag2	79.70 (9)	C25—C24—H24	119.8
P2—Ag1—Ag2	86.71 (3)	C20—C25—C24	120.2 (7)
O3—Ag1—Ag2	164.76 (12)	C20—C25—H25	119.9
O2ⁱ—Ag1—Ag2	85.22 (8)	C24—C25—H25	119.9
O2—Ag2—P1	143.96 (8)	C27—C26—C31	119.6 (6)
O2—Ag2—O1ⁱ	81.77 (11)	C27—C26—P3	120.7 (5)
P1—Ag2—O1ⁱ	127.51 (8)	C31—C26—P3	119.3 (4)
O2—Ag2—O4ⁱ	88.39 (14)	C26—C27—C28	119.5 (8)
P1—Ag2—O4ⁱ	111.96 (11)	C26—C27—H27	120.2
O1ⁱ—Ag2—O4ⁱ	85.26 (13)	C28—C27—H27	120.2
O2—Ag2—Ag1	80.43 (8)	C29—C28—C27	120.5 (9)
P1—Ag2—Ag1	86.74 (3)	C29—C28—H28	119.8
O1ⁱ—Ag2—Ag1	76.03 (8)	C27—C28—H28	119.8
O4ⁱ—Ag2—Ag1	159.35 (10)	C28—C29—C30	121.3 (8)
P1—C1—P2	115.1 (2)	C28—C29—H29	119.4
P1—C1—H1A	108.5	C30—C29—H29	119.4
P2—C1—H1A	108.5	C29—C30—C31	119.5 (9)
P1—C1—H1B	108.5	C29—C30—H30	120.2
P2—C1—H1B	108.5	C31—C30—H30	120.2
H1A—C1—H1B	107.5	C26—C31—C30	119.4 (8)
C7—C2—C3	118.6 (5)	C26—C31—H31	120.3
C7—C2—P1	118.5 (4)	C30—C31—H31	120.3
C3—C2—P1	122.8 (4)	C37O—C32—C33	118.6 (4)
C2—C3—C4	120.2 (6)	C37O—C32—P3	120.8 (3)
C2—C3—H3	119.9	C33—C32—P3	120.2 (4)
C4—C3—H3	119.9	C32—C33—C34	120.3 (6)
C5—C4—C3	120.8 (7)	C32—C33—H33	119.8
C5—C4—H4	119.6	C34—C33—H33	119.8
C3—C4—H4	119.6	C35—C34—C33	120.3 (6)
C4—C5—C6	120.1 (6)	C35—C34—H34	119.8
C4—C5—H5	119.9	C33—C34—H34	119.8
C6—C5—H5	119.9	C34—C35—C36	120.4 (6)
C5—C6—C7	120.1 (6)	C34—C35—H35	119.8
C5—C6—H6	119.9	C36—C35—H35	119.8
C7—C6—H6	119.9	C35—C36—C37O	120.5 (6)
C2—C7—C6	120.1 (6)	C35—C36—H36	119.8
C2—C7—H7	119.9	C37O—C36—H36	119.8
C6—C7—H7	119.9	F2—C38—F3	108.4 (6)
C13—C8—C9	118.4 (5)	F2—C38—F1	99.1 (6)
C13—C8—P1	119.2 (4)	F3—C38—F1	103.8 (5)
C9—C8—P1	122.4 (4)	F2—C38—C39	117.9 (6)
C10—C9—C8	120.0 (6)	F3—C38—C39	113.1 (7)
C10—C9—H9	120.0	F1—C38—C39	112.9 (6)
C8—C9—H9	120.0	O4—C39—O3	132.8 (6)
C11—C10—C9	120.3 (7)	O4—C39—C38	115.1 (6)
C11—C10—H10	119.9	O3—C39—C38	112.1 (6)
C9—C10—H10	119.9	C41—C40—H40A	109.5
C12—C11—C10	120.9 (6)	C41—C40—H40B	109.5
C12—C11—H11	119.5	H40A—C40—H40B	109.5
C10—C11—H11	119.5	C41—C40—H40C	109.5
C11—C12—C13	119.1 (6)	H40A—C40—H40C	109.5
C11—C12—H12	120.4	H40B—C40—H40C	109.5
C13—C12—H12	120.4	N1—C41—C40	175.8 (18)
C8—C13—C12	121.3 (6)	C32—C37O—C36	119.8 (4)
C8—C13—H13	119.4	C32—C37O—H37O	120.1
C12—C13—H13	119.4	C36—C37O—H37O	120.1
C15—C14—C19	119.3 (5)	P3—O1—Ag1	120.75 (18)
C15—C14—P2	123.7 (4)	P3—O1—Ag2ⁱ	122.82 (19)
C19—C14—P2	117.1 (4)	Ag1—O1—Ag2ⁱ	97.24 (11)
C14—C15—C16	120.0 (6)	P3—O2—Ag2	120.65 (18)
C14—C15—H15	120.0	P3—O2—Ag1ⁱ	109.62 (17)
C16—C15—H15	120.0	Ag2—O2—Ag1ⁱ	93.85 (11)
C17—C16—C15	120.1 (7)	C39—O3—Ag1	126.4 (4)
C17—C16—H16	119.9	C39—O4—Ag2ⁱ	131.2 (4)
C15—C16—H16	119.9	C8—P1—C2	102.9 (2)
C18—C17—C16	120.3 (6)	C8—P1—C1	105.0 (2)
C18—C17—H17	119.8	C2—P1—C1	102.3 (2)
C16—C17—H17	119.8	C8—P1—Ag2	115.56 (16)
C17—C18—C19	120.5 (6)	C2—P1—Ag2	113.99 (17)
C17—C18—H18	119.7	C1—P1—Ag2	115.47 (15)
C19—C18—H18	119.7	C20—P2—C14	103.4 (2)
C18—C19—C14	119.8 (6)	C20—P2—C1	104.8 (2)
C18—C19—H19	120.1	C14—P2—C1	102.7 (2)
C14—C19—H19	120.1	C20—P2—Ag1	115.88 (17)
C21—C20—C25	118.0 (5)	C14—P2—Ag1	111.04 (16)
C21—C20—P2	123.0 (4)	C1—P2—Ag1	117.35 (15)
C25—C20—P2	118.9 (4)	O2—P3—O1	117.7 (2)
C20—C21—C22	120.1 (6)	O2—P3—C26	109.4 (2)
C20—C21—H21	120.0	O1—P3—C26	108.3 (2)
C22—C21—H21	120.0	O2—P3—C32	110.1 (2)
C23—C22—C21	121.2 (7)	O1—P3—C32	109.1 (2)
C23—C22—H22	119.4	C26—P3—C32	101.0 (2)

O1—Ag1—Ag2—O2	4.02 (11)	O4—C39—O3—Ag1	−0.8 (14)
P2—Ag1—Ag2—O2	−150.12 (8)	C38—C39—O3—Ag1	178.5 (5)
O3—Ag1—Ag2—O2	3.6 (5)	O1—Ag1—O3—C39	48.8 (6)
O2ⁱ—Ag1—Ag2—O2	85.27 (11)	P2—Ag1—O3—C39	−158.3 (6)
O1—Ag1—Ag2—P1	150.22 (9)	O2ⁱ—Ag1—O3—C39	−31.5 (7)
P2—Ag1—Ag2—P1	−3.92 (4)	Ag2—Ag1—O3—C39	49.2 (10)
O3—Ag1—Ag2—P1	149.8 (5)	O3—C39—O4—Ag2ⁱ	−10.2 (14)
O2ⁱ—Ag1—Ag2—P1	−128.54 (8)	C38—C39—O4—Ag2ⁱ	170.4 (5)
O1—Ag1—Ag2—O1ⁱ	−79.80 (12)	C13—C8—P1—C2	112.4 (4)
P2—Ag1—Ag2—O1ⁱ	126.07 (8)	C9—C8—P1—C2	−66.9 (5)
O3—Ag1—Ag2—O1ⁱ	−80.2 (5)	C13—C8—P1—C1	−140.9 (4)
O2ⁱ—Ag1—Ag2—O1ⁱ	1.45 (10)	C9—C8—P1—C1	39.8 (5)
O1—Ag1—Ag2—O4ⁱ	−54.1 (3)	C13—C8—P1—Ag2	−12.5 (5)
P2—Ag1—Ag2—O4ⁱ	151.8 (3)	C9—C8—P1—Ag2	168.2 (4)
O3—Ag1—Ag2—O4ⁱ	−54.5 (6)	C7—C2—P1—C8	−112.0 (4)
O2ⁱ—Ag1—Ag2—O4ⁱ	27.1 (3)	C3—C2—P1—C8	64.6 (5)
C7—C2—C3—C4	2.7 (9)	C7—C2—P1—C1	139.2 (4)
P1—C2—C3—C4	−173.9 (5)	C3—C2—P1—C1	−44.1 (5)
C2—C3—C4—C5	−0.7 (11)	C7—C2—P1—Ag2	13.9 (4)
C3—C4—C5—C6	−2.1 (11)	C3—C2—P1—Ag2	−169.5 (4)
C4—C5—C6—C7	2.9 (11)	P2—C1—P1—C8	78.2 (3)
C3—C2—C7—C6	−1.9 (8)	P2—C1—P1—C2	−174.7 (2)
P1—C2—C7—C6	174.9 (5)	P2—C1—P1—Ag2	−50.3 (3)
C5—C6—C7—C2	−0.9 (10)	O2—Ag2—P1—C8	−26.8 (2)
C13—C8—C9—C10	−2.6 (10)	O1ⁱ—Ag2—P1—C8	−165.19 (19)
P1—C8—C9—C10	176.7 (6)	O4ⁱ—Ag2—P1—C8	93.4 (2)
C8—C9—C10—C11	1.0 (13)	Ag1—Ag2—P1—C8	−95.58 (17)
C9—C10—C11—C12	1.0 (13)	O2—Ag2—P1—C2	−145.7 (2)
C10—C11—C12—C13	−1.4 (12)	O1ⁱ—Ag2—P1—C2	75.89 (19)
C9—C8—C13—C12	2.2 (9)	O4ⁱ—Ag2—P1—C2	−25.5 (2)
P1—C8—C13—C12	−177.1 (5)	Ag1—Ag2—P1—C2	145.50 (16)
C11—C12—C13—C8	−0.3 (10)	O2—Ag2—P1—C1	96.2 (2)
C19—C14—C15—C16	0.7 (9)	O1ⁱ—Ag2—P1—C1	−42.2 (2)
P2—C14—C15—C16	−178.6 (5)	O4ⁱ—Ag2—P1—C1	−143.6 (2)
C14—C15—C16—C17	0.8 (10)	Ag1—Ag2—P1—C1	27.41 (16)
C15—C16—C17—C18	−2.3 (11)	C21—C20—P2—C14	31.1 (5)
C16—C17—C18—C19	2.4 (10)	C25—C20—P2—C14	−152.1 (5)
C17—C18—C19—C14	−0.9 (9)	C21—C20—P2—C1	−76.2 (5)
C15—C14—C19—C18	−0.6 (8)	C25—C20—P2—C1	100.6 (5)
P2—C14—C19—C18	178.7 (4)	C21—C20—P2—Ag1	152.8 (4)
C25—C20—C21—C22	1.6 (9)	C25—C20—P2—Ag1	−30.4 (5)
P2—C20—C21—C22	178.5 (5)	C15—C14—P2—C20	−85.6 (5)
C20—C21—C22—C23	−1.0 (12)	C19—C14—P2—C20	95.1 (4)
C21—C22—C23—C24	−1.2 (14)	C15—C14—P2—C1	23.2 (5)
C22—C23—C24—C25	2.5 (14)	C19—C14—P2—C1	−156.1 (4)
C21—C20—C25—C24	−0.3 (10)	C15—C14—P2—Ag1	149.5 (4)
P2—C20—C25—C24	−177.3 (6)	C19—C14—P2—Ag1	−29.8 (4)
C23—C24—C25—C20	−1.8 (13)	P1—C1—P2—C20	−84.1 (3)
C31—C26—C27—C28	−0.5 (9)	P1—C1—P2—C14	168.1 (2)
P3—C26—C27—C28	172.6 (5)	P1—C1—P2—Ag1	46.0 (3)
C26—C27—C28—C29	−3.5 (12)	O1—Ag1—P2—C20	43.1 (3)
C27—C28—C29—C30	5.9 (14)	O3—Ag1—P2—C20	−68.0 (2)
C28—C29—C30—C31	−4.1 (13)	O2ⁱ—Ag1—P2—C20	−173.02 (19)
C27—C26—C31—C30	2.2 (8)	Ag2—Ag1—P2—C20	105.01 (17)
P3—C26—C31—C30	−171.0 (5)	O1—Ag1—P2—C14	160.7 (2)
C29—C30—C31—C26	0.0 (11)	O3—Ag1—P2—C14	49.6 (2)
C37O—C32—C33—C34	−0.1 (9)	O2ⁱ—Ag1—P2—C14	−55.46 (19)
P3—C32—C33—C34	173.0 (5)	Ag2—Ag1—P2—C14	−137.43 (16)
C32—C33—C34—C35	−0.4 (11)	O1—Ag1—P2—C1	−81.6 (3)
C33—C34—C35—C36	0.5 (12)	O3—Ag1—P2—C1	167.3 (2)
C34—C35—C36—C37O	0.0 (12)	O2ⁱ—Ag1—P2—C1	62.24 (19)
F2—C38—C39—O4	−148.7 (7)	Ag2—Ag1—P2—C1	−19.73 (16)
F3—C38—C39—O4	83.5 (9)	Ag2—O2—P3—O1	−49.7 (3)
F1—C38—C39—O4	−34.0 (10)	Ag1ⁱ—O2—P3—O1	57.4 (2)
F2—C38—C39—O3	31.8 (11)	Ag2—O2—P3—C26	−173.8 (2)
F3—C38—C39—O3	−96.0 (8)	Ag1ⁱ—O2—P3—C26	−66.7 (2)
F1—C38—C39—O3	146.5 (7)	Ag2—O2—P3—C32	76.0 (2)
C33—C32—C37O—C36	0.6 (7)	Ag1ⁱ—O2—P3—C32	−176.91 (18)
P3—C32—C37O—C36	−172.6 (4)	Ag1—O1—P3—O2	56.4 (3)
C35—C36—C37O—C32	−0.5 (9)	Ag2ⁱ—O1—P3—O2	−67.5 (3)
P2—Ag1—O1—P3	33.9 (3)	Ag1—O1—P3—C26	−178.9 (2)
O3—Ag1—O1—P3	150.2 (2)	Ag2ⁱ—O1—P3—C26	57.2 (3)
O2ⁱ—Ag1—O1—P3	−116.5 (2)	Ag1—O1—P3—C32	−69.8 (3)
Ag2—Ag1—O1—P3	−29.65 (19)	Ag2ⁱ—O1—P3—C32	166.3 (2)
P2—Ag1—O1—Ag2ⁱ	169.19 (9)	C27—C26—P3—O2	155.7 (4)
O3—Ag1—O1—Ag2ⁱ	−74.42 (15)	C31—C26—P3—O2	−31.1 (5)
O2ⁱ—Ag1—O1—Ag2ⁱ	18.88 (12)	C27—C26—P3—O1	26.3 (5)
Ag2—Ag1—O1—Ag2ⁱ	105.69 (10)	C31—C26—P3—O1	−160.6 (4)
P1—Ag2—O2—P3	−50.7 (3)	C27—C26—P3—C32	−88.2 (4)
O1ⁱ—Ag2—O2—P3	97.1 (2)	C31—C26—P3—C32	84.9 (4)
O4ⁱ—Ag2—O2—P3	−177.4 (2)	C37O—C32—P3—O2	−155.2 (3)
Ag1—Ag2—O2—P3	20.03 (18)	C33—C32—P3—O2	31.7 (5)
P1—Ag2—O2—Ag1ⁱ	−166.27 (7)	C37O—C32—P3—O1	−24.8 (4)
O1ⁱ—Ag2—O2—Ag1ⁱ	−18.40 (11)	C33—C32—P3—O1	162.2 (4)
O4ⁱ—Ag2—O2—Ag1ⁱ	67.05 (14)	C37O—C32—P3—C26	89.1 (4)
Ag1—Ag2—O2—Ag1ⁱ	−95.51 (9)	C33—C32—P3—C26	−83.9 (5)

Symmetry code: (i) −x+1, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O3	0.93	2.46	3.380 (8)	169
C7—H7···O4ⁱ	0.93	2.45	3.368 (7)	171

Symmetry code: (i) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[Ag₄(C₂F₃O₂)₂(C₁₂H₁₀O₂P)₂(C₂₅H₂₂P₂)₂]·2C₂H₃N
M_r	1942.70
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.724 (5), 14.777 (6), 24.183 (10)
β (°)	102.254 (5)
V (Å³)	4094 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.13
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku Mercury CCD
Absorption correction	Multi-scan (CrystalClear-SM Expert; Rigaku, 2009)
T_min, T_max	0.806, 0.806
No. of measured, independent and observed [I > 2σ(I)] reflections	34844, 7192, 6033
R_int	0.057
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.117, 1.01
No. of reflections	7192
No. of parameters	480
No. of restraints	60
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.08, −0.59

Computer programs: CrystalClear-SM Expert (Rigaku, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O3	0.93	2.46	3.380 (8)	169
C7—H7···O4ⁱ	0.93	2.45	3.368 (7)	171

Symmetry code: (i) −x+1, −y+2, −z.

References

Catalano, V. J. & Malwitz, M. A. (2004). J. Am. Chem. Soc. 126, 6560–6561. Web of Science CSD CrossRef PubMed CAS Google Scholar
Chiu, P. L. & Lee, H. M. (2005). Organometallics, 24, 1692–1702. Web of Science CSD CrossRef CAS Google Scholar
Kuang, S. M., Cuttell, D. G., McMillin, D. R., Fanwick, P. E. & Walton, R. A. (2002). Inorg. Chem. 41, 3313–3322. Web of Science CSD CrossRef PubMed CAS Google Scholar
Rigaku (2009). CrystalClear-SM Expert. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rudler, H., Denise, B. & Ribeiro Gregorio, J. (1997). Chem. Commun. pp. 2299–2300. CSD CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zank, J., Schier, A. & Schmidbaur, H. (1999). J. Chem. Soc. Dalton Trans. pp. 415–420. Web of Science CSD CrossRef Google Scholar

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Volume 67| Part 12| December 2011| Pages m1677-m1678

https://doi.org/10.1107/S1600536811045466

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