Bis[μ-bis­(diphenyl­phosphan­yl)methane-κ2P:P′]bis­[(isoquinoline-κN)silver(I)] bis­(trifluoro­methane­sulfonate)–isoquinoline (1/1)

Huang, X.; Li, J.; Qiu, Q.-M.; Liu, M.; Jin, Q.-H.

doi:10.1107/S1600536812029236

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages m1022-m1023

https://doi.org/10.1107/S1600536812029236

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Bis[μ-bis(diphenylphosphanyl)methane-κ²P:P′]bis[(isoquinoline-κN)silver(I)] bis(trifluoromethanesulfonate)–isoquinoline (1/1)

Xu Huang,^a Jing Li,^a Qi-Ming Qiu,^a Min Liu ^b and Qiong-Hua Jin ^a ^*

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, and ^bThe College of Materials Science and Engineering, Beijing University of Technology, Beijing 100022, People's Republic of China
^*Correspondence e-mail: jinqh204@163.com

(Received 3 May 2012; accepted 27 June 2012; online 4 July 2012)

The title complex, [Ag₂(C₂₅H₂₂P₂)₂(C₉H₇N)₂](CF₃SO₃)₂·C₉H₇N, was prepared by the reaction of silver(I) trifluoromethanesulfonate with isoquinoline and bis(diphenylphosphanyl)methane (dppm). The dinuclear molecule is located about a center of inversion and the Ag^I atom is coordinated by two dppm P atoms and one isoquinoline N atom, forming an eight-membered metalla ring. In addition, in the asymmetric unit, there is a half-molecule of isoquinoline located about a center of inversion. Since this molecule does not possess this symmetry, for one position in the ring there is superposition of both a C atom of a C—H group and the isoquinoline N atom. In the structure, the Ag—P distances [2.4296 (9) and 2.4368 (9) Å] agree with the corresponding distances in related structures, while the Ag—N bond length [2.489 (3) Å] is slightly longer than that in related structures. On the other hand, the P—Ag—P angle [156.44 (3)°] is much larger than the corresponding angles in related structures. The trifluoromethanesulfonate anions do not coordinate to Ag^I atoms. As is usually found for these anions, the –CF₃ group is disordered over two orientations [occupancies = 0.57 (12) and 0.43 (12)].

Related literature

For background to silver(I) complexes, see: Bowmaker et al. (1993 ); Cui et al. (2010a ,b ); Jin et al. (2010a ,b ); Meijboom et al. (2009 ); Mu et al. (2010 ). For related structures, see: Jin et al. (2008 ); Song et al. (2010 ); Wu et al. (2009 ).

Experimental

Crystal data

[Ag₂(C₂₅H₂₂P₂)₂(C₉H₇N)₂](CF₃O₃S)₂·C₉H₇N
M_r = 1670.08
Triclinic, $[P \overline 1]$
a = 11.7730 (11) Å
b = 11.9269 (12) Å
c = 15.4151 (17) Å
α = 106.696 (1)°
β = 100.382 (1)°
γ = 110.289 (2)°
V = 1847.9 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 298 K
0.48 × 0.39 × 0.35 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.717, T_max = 0.781
9230 measured reflections
6407 independent reflections
4969 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.03
6407 reflections
497 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; 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 global, I. DOI: https://doi.org/10.1107/S1600536812029236/bv2206sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812029236/bv2206Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of silver(I) is of considerable interest because of its luminescence properties and potential applications in catalysis, cyanide, photography antimicrobial activities and electrochemical processes (Bowmaker et al., 1993; Cui et al., 2010a, 2010b; Jin et al., 2010a, 2010b; Meijboom et al., 2009;). Nitrogen heterocyclic ligands play significant roles in the construction of d₁₀ metal complexes with phosphine ligands. For examples,[Ag₄(SCN)₄(dppm)₂] (Jin et al., 2008), [Ag(SCN)(dppm)]₂ (Song et al., 2010), [Ag(ClO₄₎(PPh₃)₃] (Cui et al., 2010a), [Ag(ClO₄₎(PPh₃)₃(MeOH)] (Cui et al., 2010b) and [Ag(PPh₃)(CH₃COO)]₂.H₂O.CH₃OH (Mu et al., 2010) were prepared under the catalysis of nitrogen heterocyclic ligands. Here we report the first silver (I) complex which combines isoquinoline and bis(diphenylphosphine)methane, [Ag₂(dppm)₂(C₉H₇N)₂](CF₃SO₃)₂.C₉H₇N

In the compound, C₇₉H₆₅Ag₂F₆N₃O₆P₄S₂, the molecule is located on a center of inversion and each silver atom is coordinated by two phosphorus atoms from dppm and one nitrogen from isoquinoline to form a eight-member ring. In addition, in the asymmetric unit there is half a molecule of isoquinoline located on a center of inversion. Since this molecule does not possess this symmetry, for one position in the ring there is superposition of both a C-H and N.

In the compound, Ag—P distances (2.4296 (2)–2.4368 (9) Å), agree with the corresponding distances in [Ag₄(SCN)₄(dppm)₂] (2.399 Å) and [Ag(SCN)(dppm)]₂ (2.450 (2),2.451 (2)). The Ag—N bond distance(2.489 (3) Å) is longer than that in [Ag(C₁₂H₈N₂)(C₁₈H₁₅P)(2.376 (8) Å) (Wu et al., 2009). The P—Ag—P angle (156.44°) is much larger than the corresponding angles in [Ag(SCN)(dppm)]₂ (120.0 and 120.8 (1)°). The trifluoromethanesulfonate anions do not coordinate to silver atoms. As is usually found for these anions, the CF₃ group is disordered over two orientations with occupancies of 0.57 (12)/0.43 (12).

Related literature top

For background to silver(I) complexes, see: Bowmaker et al. (1993); Cui et al. (2010a,b); Jin et al. (2010a,b); Meijboom et al. (2009); Mu et al. (2010). For related structures, see: Jin et al. (2008); Song et al. (2010); Wu et al. (2009).

Experimental top

A mixture of silver(I) trifluoromethanesulfonate, bis(diphenylphosphanyl)methane (molar ratio 1:1) and isoquinoline (0.5 ml) in the mixed solution of CH₃OH (5 ml) and CH₂Cl₂(5 ml) was stirred for 5 h at ambient temperature. The insoluble residues were removed by filtration, and the filtrate was evaporated slowly at room temperature for about one month to yield white crystals. Crystals suitable for single-crystal X-ray diffraction were selected directly from the sample as prepared.

Structure description top

For background to silver(I) complexes, see: Bowmaker et al. (1993); Cui et al. (2010a,b); Jin et al. (2010a,b); Meijboom et al. (2009); Mu et al. (2010). For related structures, see: Jin et al. (2008); Song et al. (2010); Wu et al. (2009).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (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. The ionic entities of the title compound, showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level.

Bis[µ-bis(diphenylphosphanyl)methane- κ²P:P']bis[(isoquinoline-κN)silver(I)] bis(trifluoromethanesulfonate)–isoquinoline (1/1) top

Crystal data top

[Ag₂(C₂₅H₂₂P₂)₂(C₉H₇N)₂](CF₃O₃S)₂·C₉H₇N	Z = 1
M_r = 1670.08	F(000) = 848
Triclinic, P1	D_x = 1.501 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 11.7730 (11) Å	Cell parameters from 4635 reflections
b = 11.9269 (12) Å	θ = 2.5–28.1°
c = 15.4151 (17) Å	µ = 0.74 mm⁻¹
α = 106.696 (1)°	T = 298 K
β = 100.382 (1)°	Prism, white
γ = 110.289 (2)°	0.48 × 0.39 × 0.35 mm
V = 1847.9 (3) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	6407 independent reflections
Radiation source: fine-focus sealed tube	4969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
phi and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→14
T_min = 0.717, T_max = 0.781	k = −13→14
9230 measured reflections	l = −18→16

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0425P)² + 1.3004P] where P = (F_o² + 2F_c²)/3
6407 reflections	(Δ/σ)_max = 0.001
497 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

[Ag₂(C₂₅H₂₂P₂)₂(C₉H₇N)₂](CF₃O₃S)₂·C₉H₇N	γ = 110.289 (2)°
M_r = 1670.08	V = 1847.9 (3) Å³
Triclinic, P1	Z = 1
a = 11.7730 (11) Å	Mo Kα radiation
b = 11.9269 (12) Å	µ = 0.74 mm⁻¹
c = 15.4151 (17) Å	T = 298 K
α = 106.696 (1)°	0.48 × 0.39 × 0.35 mm
β = 100.382 (1)°

Data collection top

Bruker SMART 1000 CCD diffractometer	6407 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	4969 reflections with I > 2σ(I)
T_min = 0.717, T_max = 0.781	R_int = 0.026
9230 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.03	Δρ_max = 0.63 e Å⁻³
6407 reflections	Δρ_min = −0.57 e Å⁻³
497 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	Occ. (<1)
Ag1	0.52538 (2)	0.63477 (3)	0.59947 (2)	0.04145 (11)
F1	0.401 (2)	0.509 (5)	0.1002 (15)	0.115 (8)	0.57 (12)
F2	0.194 (4)	0.430 (4)	0.0409 (18)	0.099 (6)	0.57 (12)
F3	0.283 (8)	0.305 (4)	0.0602 (16)	0.114 (11)	0.57 (12)
F1'	0.225 (5)	0.290 (3)	0.061 (2)	0.101 (7)	0.43 (12)
F2'	0.406 (3)	0.450 (9)	0.0954 (18)	0.123 (12)	0.43 (12)
F3'	0.233 (7)	0.462 (6)	0.037 (2)	0.095 (9)	0.43 (12)
N1	0.5661 (3)	0.8428 (3)	0.7245 (2)	0.0493 (8)
N2	0.641 (11)	0.001 (13)	0.139 (8)	0.12 (12)	0.50
O1	0.3089 (4)	0.6036 (3)	0.2444 (2)	0.0848 (11)
O2	0.3653 (4)	0.4369 (4)	0.2676 (2)	0.0887 (11)
O3	0.1465 (4)	0.3951 (4)	0.2050 (3)	0.1093 (15)
P1	0.73017 (8)	0.71398 (8)	0.57100 (6)	0.0300 (2)
P2	0.70533 (8)	0.45711 (8)	0.44043 (6)	0.0304 (2)
S1	0.27513 (11)	0.46881 (11)	0.21639 (7)	0.0556 (3)
C1	0.6518 (4)	0.8795 (4)	0.8064 (3)	0.0489 (10)
H1	0.6667	0.8162	0.8238	0.059*
C2	0.5452 (4)	0.9371 (4)	0.7002 (3)	0.0606 (12)
H2	0.4847	0.9123	0.6423	0.073*
C3	0.6075 (4)	1.0645 (4)	0.7555 (3)	0.0618 (12)
H3	0.5892	1.1247	0.7357	0.074*
C4	0.7006 (4)	1.1052 (4)	0.8437 (3)	0.0551 (11)
C5	0.7229 (4)	1.0103 (4)	0.8701 (3)	0.0499 (10)
C6	0.8170 (5)	1.0448 (5)	0.9551 (3)	0.0677 (13)
H6	0.8317	0.9814	0.9725	0.081*
C7	0.8866 (5)	1.1717 (6)	1.0119 (4)	0.0865 (18)
H7	0.9491	1.1948	1.0683	0.104*
C8	0.8658 (6)	1.2661 (6)	0.9871 (4)	0.0915 (19)
H8	0.9150	1.3523	1.0269	0.110*
C9	0.7745 (5)	1.2365 (5)	0.9052 (4)	0.0777 (16)
H9	0.7609	1.3018	0.8899	0.093*
C10	0.8032 (3)	0.5997 (3)	0.5509 (2)	0.0325 (8)
H10A	0.8122	0.5727	0.6044	0.039*
H10B	0.8876	0.6419	0.5465	0.039*
C11	0.8524 (3)	0.8601 (3)	0.6680 (2)	0.0356 (8)
C12	0.8431 (4)	0.9755 (4)	0.6772 (3)	0.0443 (9)
H12	0.7779	0.9761	0.6334	0.053*
C13	0.9295 (4)	1.0896 (4)	0.7509 (3)	0.0587 (12)
H13	0.9222	1.1664	0.7565	0.070*
C14	1.0252 (5)	1.0893 (5)	0.8153 (3)	0.0699 (15)
H14	1.0841	1.1662	0.8644	0.084*
C15	1.0349 (4)	0.9760 (5)	0.8078 (3)	0.0684 (14)
H15	1.0999	0.9766	0.8525	0.082*
C16	0.9488 (4)	0.8598 (4)	0.7342 (3)	0.0509 (10)
H16	0.9560	0.7833	0.7296	0.061*
C17	0.7319 (3)	0.7611 (3)	0.4689 (2)	0.0335 (8)
C18	0.8460 (3)	0.8180 (4)	0.4524 (3)	0.0412 (9)
H18	0.9223	0.8355	0.4953	0.049*
C19	0.8473 (4)	0.8488 (4)	0.3733 (3)	0.0530 (11)
H19	0.9244	0.8875	0.3630	0.064*
C20	0.7351 (5)	0.8226 (4)	0.3095 (3)	0.0579 (12)
H20	0.7362	0.8430	0.2557	0.069*
C21	0.6221 (5)	0.7669 (4)	0.3246 (3)	0.0588 (12)
H21	0.5462	0.7488	0.2808	0.071*
C22	0.6197 (4)	0.7370 (4)	0.4048 (3)	0.0439 (9)
H22	0.5425	0.7007	0.4156	0.053*
C23	0.7693 (3)	0.4931 (3)	0.3477 (2)	0.0335 (8)
C24	0.8969 (4)	0.5276 (4)	0.3545 (3)	0.0482 (10)
H24	0.9537	0.5361	0.4090	0.058*
C25	0.9397 (4)	0.5496 (4)	0.2798 (3)	0.0609 (12)
H25	1.0247	0.5706	0.2837	0.073*
C26	0.8566 (5)	0.5401 (4)	0.2009 (3)	0.0664 (14)
H26	0.8857	0.5556	0.1514	0.080*
C27	0.7308 (5)	0.5080 (4)	0.1941 (3)	0.0601 (12)
H27	0.6752	0.5028	0.1403	0.072*
C28	0.6864 (4)	0.4834 (4)	0.2666 (3)	0.0440 (9)
H28	0.6007	0.4602	0.2612	0.053*
C29	0.7519 (3)	0.3338 (3)	0.4608 (2)	0.0341 (8)
C30	0.7968 (3)	0.2631 (4)	0.3987 (3)	0.0419 (9)
H30	0.8126	0.2836	0.3470	0.050*
C31	0.8182 (4)	0.1615 (4)	0.4140 (3)	0.0517 (10)
H31	0.8483	0.1145	0.3723	0.062*
C32	0.7953 (4)	0.1303 (4)	0.4895 (3)	0.0565 (11)
H32	0.8093	0.0620	0.4990	0.068*
C33	0.7515 (4)	0.1998 (4)	0.5517 (3)	0.0553 (11)
H33	0.7370	0.1791	0.6036	0.066*
C34	0.7290 (4)	0.3006 (4)	0.5373 (3)	0.0433 (9)
H34	0.6982	0.3465	0.5791	0.052*
C35	0.2884 (7)	0.4224 (6)	0.0981 (4)	0.0783 (16)
C36	0.641 (14)	0.001 (15)	0.139 (10)	0.12 (14)	0.50
H36	0.7001	0.0233	0.1969	0.144*	0.50
C37	0.6164 (7)	0.0911 (10)	0.1179 (5)	0.118 (3)
H37	0.6571	0.1756	0.1623	0.142*
C38	0.5330 (5)	0.0643 (6)	0.0327 (4)	0.0837 (18)
C39	0.5054 (8)	0.1618 (8)	0.0075 (6)	0.115 (2)
H39	0.5456	0.2481	0.0487	0.137*
C40	0.4179 (8)	0.1228 (10)	−0.0790 (7)	0.115 (3)
H40	0.3988	0.1841	−0.0966	0.138*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03004 (16)	0.04394 (19)	0.04563 (19)	0.01163 (13)	0.01270 (12)	0.01485 (13)
F1	0.135 (9)	0.147 (18)	0.098 (6)	0.068 (10)	0.082 (6)	0.057 (8)
F2	0.128 (14)	0.105 (10)	0.051 (5)	0.035 (10)	0.003 (7)	0.045 (5)
F3	0.17 (3)	0.111 (11)	0.079 (5)	0.102 (18)	0.034 (11)	0.014 (5)
F1'	0.111 (17)	0.098 (9)	0.076 (7)	0.068 (10)	0.008 (8)	−0.007 (6)
F2'	0.116 (10)	0.16 (3)	0.110 (9)	0.069 (15)	0.063 (8)	0.034 (14)
F3'	0.14 (2)	0.099 (17)	0.055 (6)	0.057 (16)	0.026 (11)	0.039 (9)
N1	0.0474 (19)	0.041 (2)	0.046 (2)	0.0123 (16)	0.0156 (16)	0.0056 (16)
N2	0.10 (18)	0.2 (3)	0.1 (2)	0.06 (18)	0.03 (15)	0.03 (19)
O1	0.111 (3)	0.057 (2)	0.070 (2)	0.032 (2)	0.020 (2)	0.0112 (17)
O2	0.099 (3)	0.094 (3)	0.065 (2)	0.040 (2)	−0.0066 (19)	0.039 (2)
O3	0.077 (3)	0.116 (3)	0.101 (3)	0.003 (2)	0.025 (2)	0.044 (3)
P1	0.0269 (4)	0.0286 (5)	0.0297 (5)	0.0088 (4)	0.0092 (4)	0.0081 (4)
P2	0.0277 (4)	0.0300 (5)	0.0302 (5)	0.0111 (4)	0.0088 (4)	0.0081 (4)
S1	0.0579 (7)	0.0556 (7)	0.0409 (6)	0.0125 (5)	0.0092 (5)	0.0192 (5)
C1	0.058 (3)	0.040 (2)	0.046 (2)	0.017 (2)	0.024 (2)	0.0137 (19)
C2	0.046 (3)	0.060 (3)	0.060 (3)	0.019 (2)	0.011 (2)	0.010 (2)
C3	0.056 (3)	0.052 (3)	0.077 (3)	0.030 (2)	0.018 (2)	0.018 (2)
C4	0.054 (3)	0.040 (2)	0.060 (3)	0.017 (2)	0.024 (2)	0.005 (2)
C5	0.054 (2)	0.045 (2)	0.041 (2)	0.013 (2)	0.0222 (19)	0.0076 (19)
C6	0.076 (3)	0.061 (3)	0.049 (3)	0.015 (3)	0.018 (2)	0.015 (2)
C7	0.081 (4)	0.078 (4)	0.053 (3)	0.004 (3)	0.013 (3)	0.000 (3)
C8	0.089 (4)	0.054 (4)	0.077 (4)	0.004 (3)	0.019 (3)	−0.015 (3)
C9	0.077 (4)	0.046 (3)	0.089 (4)	0.019 (3)	0.027 (3)	0.003 (3)
C10	0.0318 (18)	0.0319 (19)	0.0309 (18)	0.0119 (15)	0.0092 (14)	0.0103 (15)
C11	0.0324 (18)	0.033 (2)	0.0344 (19)	0.0063 (15)	0.0166 (15)	0.0091 (15)
C12	0.043 (2)	0.038 (2)	0.042 (2)	0.0089 (18)	0.0196 (17)	0.0094 (17)
C13	0.061 (3)	0.037 (2)	0.054 (3)	0.002 (2)	0.026 (2)	0.002 (2)
C14	0.068 (3)	0.050 (3)	0.047 (3)	−0.009 (2)	0.020 (2)	−0.004 (2)
C15	0.054 (3)	0.080 (4)	0.038 (2)	0.008 (3)	0.000 (2)	0.012 (2)
C16	0.047 (2)	0.050 (3)	0.040 (2)	0.011 (2)	0.0058 (18)	0.0106 (19)
C17	0.0355 (19)	0.0293 (19)	0.0319 (18)	0.0119 (15)	0.0121 (15)	0.0073 (15)
C18	0.040 (2)	0.042 (2)	0.041 (2)	0.0151 (18)	0.0146 (17)	0.0155 (17)
C19	0.062 (3)	0.048 (3)	0.050 (2)	0.016 (2)	0.028 (2)	0.022 (2)
C20	0.080 (3)	0.051 (3)	0.043 (2)	0.023 (2)	0.018 (2)	0.024 (2)
C21	0.065 (3)	0.058 (3)	0.045 (2)	0.026 (2)	0.001 (2)	0.019 (2)
C22	0.039 (2)	0.043 (2)	0.048 (2)	0.0166 (18)	0.0090 (17)	0.0180 (18)
C23	0.0374 (19)	0.0305 (19)	0.0347 (19)	0.0159 (16)	0.0147 (15)	0.0110 (15)
C24	0.043 (2)	0.050 (2)	0.048 (2)	0.0163 (19)	0.0166 (18)	0.0155 (19)
C25	0.055 (3)	0.058 (3)	0.069 (3)	0.017 (2)	0.037 (2)	0.021 (2)
C26	0.090 (4)	0.058 (3)	0.046 (3)	0.020 (3)	0.037 (3)	0.017 (2)
C27	0.074 (3)	0.062 (3)	0.038 (2)	0.022 (2)	0.013 (2)	0.021 (2)
C28	0.046 (2)	0.045 (2)	0.038 (2)	0.0181 (19)	0.0117 (17)	0.0152 (17)
C29	0.0289 (17)	0.0313 (19)	0.0349 (19)	0.0094 (15)	0.0073 (15)	0.0085 (15)
C30	0.044 (2)	0.042 (2)	0.039 (2)	0.0192 (18)	0.0142 (17)	0.0125 (17)
C31	0.060 (3)	0.046 (2)	0.057 (3)	0.032 (2)	0.023 (2)	0.017 (2)
C32	0.068 (3)	0.047 (3)	0.063 (3)	0.033 (2)	0.018 (2)	0.023 (2)
C33	0.073 (3)	0.052 (3)	0.051 (2)	0.029 (2)	0.023 (2)	0.028 (2)
C34	0.048 (2)	0.043 (2)	0.044 (2)	0.0236 (19)	0.0178 (18)	0.0159 (18)
C35	0.109 (5)	0.082 (4)	0.051 (3)	0.049 (4)	0.022 (3)	0.026 (3)
C36	0.1 (2)	0.2 (4)	0.1 (3)	0.1 (2)	0.03 (18)	0.0 (2)
C37	0.095 (5)	0.150 (8)	0.081 (5)	0.041 (5)	0.030 (4)	0.017 (5)
C38	0.064 (3)	0.122 (5)	0.055 (3)	0.037 (3)	0.030 (3)	0.015 (3)
C39	0.115 (6)	0.118 (6)	0.099 (6)	0.046 (5)	0.049 (5)	0.020 (5)
C40	0.123 (7)	0.138 (8)	0.108 (7)	0.070 (6)	0.052 (6)	0.053 (6)

Geometric parameters (Å, º) top

Ag1—P2ⁱ	2.4296 (9)	C14—H14	0.9300
Ag1—P1	2.4368 (9)	C15—C16	1.394 (6)
Ag1—N1	2.489 (3)	C15—H15	0.9300
F1—C35	1.35 (2)	C16—H16	0.9300
F2—C35	1.34 (3)	C17—C22	1.381 (5)
F3—C35	1.33 (2)	C17—C18	1.386 (5)
F1'—C35	1.37 (3)	C18—C19	1.371 (6)
F2'—C35	1.32 (3)	C18—H18	0.9300
F3'—C35	1.33 (4)	C19—C20	1.371 (6)
N1—C1	1.312 (5)	C19—H19	0.9300
N1—C2	1.366 (6)	C20—C21	1.361 (6)
N2—C37	1.32 (13)	C20—H20	0.9300
N2—C40ⁱⁱ	1.33 (13)	C21—C22	1.385 (6)
O1—S1	1.423 (4)	C21—H21	0.9300
O2—S1	1.430 (3)	C22—H22	0.9300
O3—S1	1.411 (4)	C23—C24	1.388 (5)
P1—C17	1.818 (4)	C23—C28	1.388 (5)
P1—C11	1.825 (3)	C24—C25	1.392 (6)
P1—C10	1.833 (3)	C24—H24	0.9300
P2—C23	1.820 (4)	C25—C26	1.366 (7)
P2—C29	1.823 (4)	C25—H25	0.9300
P2—C10	1.841 (3)	C26—C27	1.371 (7)
P2—Ag1ⁱ	2.4296 (9)	C26—H26	0.9300
S1—C35	1.800 (5)	C27—C28	1.380 (6)
C1—C5	1.420 (5)	C27—H27	0.9300
C1—H1	0.9300	C28—H28	0.9300
C2—C3	1.353 (6)	C29—C34	1.388 (5)
C2—H2	0.9300	C29—C30	1.391 (5)
C3—C4	1.414 (6)	C30—C31	1.393 (5)
C3—H3	0.9300	C30—H30	0.9300
C4—C5	1.396 (6)	C31—C32	1.364 (6)
C4—C9	1.420 (6)	C31—H31	0.9300
C5—C6	1.401 (6)	C32—C33	1.374 (6)
C6—C7	1.360 (7)	C32—H32	0.9300
C6—H6	0.9300	C33—C34	1.386 (5)
C7—C8	1.371 (8)	C33—H33	0.9300
C7—H7	0.9300	C34—H34	0.9300
C8—C9	1.365 (8)	C36—C37	1.32 (15)
C8—H8	0.9300	C36—C40ⁱⁱ	1.33 (15)
C9—H9	0.9300	C36—H36	0.9300
C10—H10A	0.9700	C37—C38	1.367 (9)
C10—H10B	0.9700	C37—H37	0.9300
C11—C16	1.384 (5)	C38—C38ⁱⁱ	1.406 (12)
C11—C12	1.387 (5)	C38—C39	1.443 (10)
C12—C13	1.383 (5)	C39—C40	1.369 (10)
C12—H12	0.9300	C39—H39	0.9300
C13—C14	1.363 (7)	C40—N2ⁱⁱ	1.33 (13)
C13—H13	0.9300	C40—C36ⁱⁱ	1.33 (15)
C14—C15	1.369 (7)	C40—H40	0.9300

P2ⁱ—Ag1—P1	156.44 (3)	C21—C20—H20	119.9
P2ⁱ—Ag1—N1	96.13 (8)	C19—C20—H20	119.9
P1—Ag1—N1	95.55 (8)	C20—C21—C22	120.2 (4)
C1—N1—C2	117.3 (4)	C20—C21—H21	119.9
C1—N1—Ag1	116.6 (3)	C22—C21—H21	119.9
C2—N1—Ag1	120.8 (3)	C17—C22—C21	120.1 (4)
C37—N2—C40ⁱⁱ	122 (8)	C17—C22—H22	119.9
C17—P1—C11	101.96 (16)	C21—C22—H22	119.9
C17—P1—C10	102.83 (16)	C24—C23—C28	119.1 (3)
C11—P1—C10	104.74 (16)	C24—C23—P2	122.4 (3)
C17—P1—Ag1	116.50 (12)	C28—C23—P2	118.4 (3)
C11—P1—Ag1	114.01 (11)	C23—C24—C25	120.0 (4)
C10—P1—Ag1	115.11 (12)	C23—C24—H24	120.0
C23—P2—C29	105.89 (16)	C25—C24—H24	120.0
C23—P2—C10	105.53 (16)	C26—C25—C24	119.9 (4)
C29—P2—C10	102.69 (16)	C26—C25—H25	120.0
C23—P2—Ag1ⁱ	115.97 (12)	C24—C25—H25	120.0
C29—P2—Ag1ⁱ	105.64 (11)	C25—C26—C27	120.6 (4)
C10—P2—Ag1ⁱ	119.53 (11)	C25—C26—H26	119.7
O3—S1—O1	113.6 (3)	C27—C26—H26	119.7
O3—S1—O2	115.2 (3)	C26—C27—C28	120.2 (4)
O1—S1—O2	114.5 (2)	C26—C27—H27	119.9
O3—S1—C35	104.9 (3)	C28—C27—H27	119.9
O1—S1—C35	103.5 (3)	C27—C28—C23	120.2 (4)
O2—S1—C35	103.2 (3)	C27—C28—H28	119.9
N1—C1—C5	123.8 (4)	C23—C28—H28	119.9
N1—C1—H1	118.1	C34—C29—C30	118.6 (3)
C5—C1—H1	118.1	C34—C29—P2	117.6 (3)
C3—C2—N1	123.8 (4)	C30—C29—P2	123.4 (3)
C3—C2—H2	118.1	C29—C30—C31	120.1 (4)
N1—C2—H2	118.1	C29—C30—H30	120.0
C2—C3—C4	119.4 (4)	C31—C30—H30	120.0
C2—C3—H3	120.3	C32—C31—C30	120.5 (4)
C4—C3—H3	120.3	C32—C31—H31	119.7
C5—C4—C3	117.7 (4)	C30—C31—H31	119.7
C5—C4—C9	118.4 (5)	C31—C32—C33	120.0 (4)
C3—C4—C9	123.8 (5)	C31—C32—H32	120.0
C4—C5—C6	120.4 (4)	C33—C32—H32	120.0
C4—C5—C1	118.0 (4)	C32—C33—C34	120.2 (4)
C6—C5—C1	121.5 (4)	C32—C33—H33	119.9
C7—C6—C5	119.5 (5)	C34—C33—H33	119.9
C7—C6—H6	120.2	C33—C34—C29	120.5 (4)
C5—C6—H6	120.2	C33—C34—H34	119.7
C6—C7—C8	120.8 (6)	C29—C34—H34	119.7
C6—C7—H7	119.6	F2'—C35—F3	78.7 (12)
C8—C7—H7	119.6	F2'—C35—F3'	107.9 (18)
C9—C8—C7	121.5 (5)	F3—C35—F3'	115.2 (17)
C9—C8—H8	119.3	F2'—C35—F2	128.4 (16)
C7—C8—H8	119.3	F3—C35—F2	108 (2)
C8—C9—C4	119.3 (5)	F3'—C35—F2	22 (2)
C8—C9—H9	120.3	F2'—C35—F1	31.0 (17)
C4—C9—H9	120.3	F3—C35—F1	108.1 (12)
P1—C10—P2	110.79 (17)	F3'—C35—F1	86 (2)
P1—C10—H10A	109.5	F2—C35—F1	108.4 (12)
P2—C10—H10A	109.5	F2'—C35—F1'	106.4 (17)
P1—C10—H10B	109.5	F3—C35—F1'	27.7 (13)
P2—C10—H10B	109.5	F3'—C35—F1'	106 (2)
H10A—C10—H10B	108.1	F2—C35—F1'	90.4 (14)
C16—C11—C12	119.2 (3)	F1—C35—F1'	135.2 (10)
C16—C11—P1	123.3 (3)	F2'—C35—S1	114.4 (11)
C12—C11—P1	117.3 (3)	F3—C35—S1	116.3 (13)
C13—C12—C11	120.8 (4)	F3'—C35—S1	117.7 (18)
C13—C12—H12	119.6	F2—C35—S1	107.8 (17)
C11—C12—H12	119.6	F1—C35—S1	108.0 (13)
C14—C13—C12	119.8 (5)	F1'—C35—S1	104 (2)
C14—C13—H13	120.1	C37—C36—C40ⁱⁱ	122 (10)
C12—C13—H13	120.1	C37—C36—H36	119.2
C13—C14—C15	120.1 (4)	C40ⁱⁱ—C36—H36	119.2
C13—C14—H14	120.0	C36—C37—N2	0 (10)
C15—C14—H14	120.0	C36—C37—C38	122 (6)
C14—C15—C16	121.0 (5)	N2—C37—C38	122 (5)
C14—C15—H15	119.5	C36—C37—H37	119.0
C16—C15—H15	119.5	N2—C37—H37	119.1
C11—C16—C15	119.0 (4)	C38—C37—H37	119.1
C11—C16—H16	120.5	C37—C38—C38ⁱⁱ	119.1 (9)
C15—C16—H16	120.5	C37—C38—C39	123.0 (7)
C22—C17—C18	118.8 (3)	C38ⁱⁱ—C38—C39	117.9 (8)
C22—C17—P1	120.8 (3)	C40—C39—C38	117.7 (7)
C18—C17—P1	120.3 (3)	C40—C39—H39	121.2
C19—C18—C17	120.6 (4)	C38—C39—H39	121.2
C19—C18—H18	119.7	N2ⁱⁱ—C40—C36ⁱⁱ	0 (10)
C17—C18—H18	119.7	N2ⁱⁱ—C40—C39	122 (5)
C20—C19—C18	120.0 (4)	C36ⁱⁱ—C40—C39	122 (6)
C20—C19—H19	120.0	N2ⁱⁱ—C40—H40	119.0
C18—C19—H19	120.0	C36ⁱⁱ—C40—H40	119.1
C21—C20—C19	120.3 (4)	C39—C40—H40	119.0

P2ⁱ—Ag1—N1—C1	130.6 (3)	C18—C17—C22—C21	1.5 (6)
P1—Ag1—N1—C1	−69.9 (3)	P1—C17—C22—C21	−176.4 (3)
P2ⁱ—Ag1—N1—C2	−76.1 (3)	C20—C21—C22—C17	−1.4 (6)
P1—Ag1—N1—C2	83.4 (3)	C29—P2—C23—C24	−53.5 (3)
P2ⁱ—Ag1—P1—C17	20.80 (16)	C10—P2—C23—C24	55.0 (3)
N1—Ag1—P1—C17	−98.62 (15)	Ag1ⁱ—P2—C23—C24	−170.2 (3)
P2ⁱ—Ag1—P1—C11	139.21 (15)	C29—P2—C23—C28	125.5 (3)
N1—Ag1—P1—C11	19.79 (16)	C10—P2—C23—C28	−126.1 (3)
P2ⁱ—Ag1—P1—C10	−99.70 (14)	Ag1ⁱ—P2—C23—C28	8.7 (3)
N1—Ag1—P1—C10	140.87 (15)	C28—C23—C24—C25	−1.2 (6)
C2—N1—C1—C5	−0.1 (6)	P2—C23—C24—C25	177.7 (3)
Ag1—N1—C1—C5	154.2 (3)	C23—C24—C25—C26	1.6 (6)
C1—N1—C2—C3	0.0 (6)	C24—C25—C26—C27	−0.6 (7)
Ag1—N1—C2—C3	−153.2 (4)	C25—C26—C27—C28	−0.8 (7)
N1—C2—C3—C4	0.4 (7)	C26—C27—C28—C23	1.1 (6)
C2—C3—C4—C5	−0.7 (7)	C24—C23—C28—C27	−0.1 (6)
C2—C3—C4—C9	177.5 (4)	P2—C23—C28—C27	−179.1 (3)
C3—C4—C5—C6	177.8 (4)	C23—P2—C29—C34	171.9 (3)
C9—C4—C5—C6	−0.5 (6)	C10—P2—C29—C34	61.4 (3)
C3—C4—C5—C1	0.6 (6)	Ag1ⁱ—P2—C29—C34	−64.5 (3)
C9—C4—C5—C1	−177.7 (4)	C23—P2—C29—C30	−14.8 (3)
N1—C1—C5—C4	−0.2 (6)	C10—P2—C29—C30	−125.2 (3)
N1—C1—C5—C6	−177.4 (4)	Ag1ⁱ—P2—C29—C30	108.8 (3)
C4—C5—C6—C7	0.0 (7)	C34—C29—C30—C31	−0.1 (5)
C1—C5—C6—C7	177.1 (4)	P2—C29—C30—C31	−173.4 (3)
C5—C6—C7—C8	0.1 (8)	C29—C30—C31—C32	0.1 (6)
C6—C7—C8—C9	0.4 (9)	C30—C31—C32—C33	−0.4 (7)
C7—C8—C9—C4	−0.9 (9)	C31—C32—C33—C34	0.8 (7)
C5—C4—C9—C8	0.9 (7)	C32—C33—C34—C29	−0.9 (6)
C3—C4—C9—C8	−177.3 (5)	C30—C29—C34—C33	0.6 (5)
C17—P1—C10—P2	−63.0 (2)	P2—C29—C34—C33	174.2 (3)
C11—P1—C10—P2	−169.23 (18)	O3—S1—C35—F2'	−161 (5)
Ag1—P1—C10—P2	64.76 (19)	O1—S1—C35—F2'	80 (5)
C23—P2—C10—P1	93.0 (2)	O2—S1—C35—F2'	−40 (5)
C29—P2—C10—P1	−156.24 (18)	O3—S1—C35—F3	−72 (4)
Ag1ⁱ—P2—C10—P1	−39.8 (2)	O1—S1—C35—F3	169 (4)
C17—P1—C11—C16	−131.7 (3)	O2—S1—C35—F3	49 (4)
C10—P1—C11—C16	−24.8 (3)	O3—S1—C35—F3'	71 (4)
Ag1—P1—C11—C16	101.9 (3)	O1—S1—C35—F3'	−48 (4)
C17—P1—C11—C12	51.4 (3)	O2—S1—C35—F3'	−168 (4)
C10—P1—C11—C12	158.3 (3)	O3—S1—C35—F2	50 (2)
Ag1—P1—C11—C12	−75.0 (3)	O1—S1—C35—F2	−70 (2)
C16—C11—C12—C13	0.7 (5)	O2—S1—C35—F2	171 (2)
P1—C11—C12—C13	177.7 (3)	O3—S1—C35—F1	167 (3)
C11—C12—C13—C14	0.1 (6)	O1—S1—C35—F1	47 (3)
C12—C13—C14—C15	−0.9 (7)	O2—S1—C35—F1	−72 (3)
C13—C14—C15—C16	0.8 (7)	O3—S1—C35—F1'	−45 (2)
C12—C11—C16—C15	−0.8 (6)	O1—S1—C35—F1'	−165 (2)
P1—C11—C16—C15	−177.6 (3)	O2—S1—C35—F1'	76 (2)
C14—C15—C16—C11	0.0 (7)	C40ⁱⁱ—C36—C37—N2	−38 (100)
C11—P1—C17—C22	−132.8 (3)	C40ⁱⁱ—C36—C37—C38	−2 (16)
C10—P1—C17—C22	118.8 (3)	C40ⁱⁱ—N2—C37—C36	142 (100)
Ag1—P1—C17—C22	−8.0 (3)	C40ⁱⁱ—N2—C37—C38	−2 (13)
C11—P1—C17—C18	49.4 (3)	C36—C37—C38—C38ⁱⁱ	3 (8)
C10—P1—C17—C18	−59.0 (3)	N2—C37—C38—C38ⁱⁱ	3 (7)
Ag1—P1—C17—C18	174.2 (2)	C36—C37—C38—C39	−180 (8)
C22—C17—C18—C19	−0.6 (5)	N2—C37—C38—C39	−179 (6)
P1—C17—C18—C19	177.3 (3)	C37—C38—C39—C40	−178.5 (7)
C17—C18—C19—C20	−0.4 (6)	C38ⁱⁱ—C38—C39—C40	−0.9 (10)
C18—C19—C20—C21	0.5 (7)	C38—C39—C40—N2ⁱⁱ	0 (6)
C19—C20—C21—C22	0.4 (7)	C38—C39—C40—C36ⁱⁱ	0 (8)

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

Experimental details

Crystal data
Chemical formula	[Ag₂(C₂₅H₂₂P₂)₂(C₉H₇N)₂](CF₃O₃S)₂·C₉H₇N
M_r	1670.08
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	11.7730 (11), 11.9269 (12), 15.4151 (17)
α, β, γ (°)	106.696 (1), 100.382 (1), 110.289 (2)
V (Å³)	1847.9 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.48 × 0.39 × 0.35

Data collection
Diffractometer	Bruker SMART 1000 CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.717, 0.781
No. of measured, independent and observed [I > 2σ(I)] reflections	9230, 6407, 4969
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.03
No. of reflections	6407
No. of parameters	497
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.57

Computer programs: SMART (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by the National Science Foundation of China (grant No. 21171119), the Committee of Education of the Beijing Foundation of China (grant No. KM201210028020) and the National High Technology Research and Development Program 863 of China (2012 A A063201).

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