(1,10-Phenanthroline-κ2N,N′)(triphenyl­phosphine-κP)silver(I) trifluoro­methane­sulfonate

Wu, J.-Q.; Jin, Q.-H.; Hu, K.-Y.; Zhang, C.-L.

doi:10.1107/S1600536809032097

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages m1096-m1097

doi:10.1107/S1600536809032097

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(1,10-Phenanthroline-κ²N,N′)(triphenylphosphine-κP)silver(I) trifluoromethanesulfonate

Jie-Qiang Wu,^a Qiong-Hua Jin,^a ^* Ke-Yi Hu ^a and Cun-Lin Zhang ^b

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China, and ^bDepartment of Physics, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: jinqh204@163.com

(Received 17 June 2009; accepted 13 August 2009; online 19 August 2009)

The structure of the title complex, [Ag(C₁₂H₈N₂)(C₁₈H₁₅P)]CF₃SO₃, is based on a distorted trigonal–planar N₂P coordination of the Ag^I ion, provided by two N atoms of the bidentate phenanthroline ligand and one P atom of the triphenylphosphine ligand. The phenanthroline ligand and one phenyl ring of the triphenylphosphine ligand almost lie in one plane (maximum deviation = 0.014 Å from the best planes). The crystal structure may be stabilized by an intermolecular C—H⋯O hydrogen bond between the phenanthroline ligand and the O atom of the trifluoromethanesulfonate anion.

Related literature

For related structures, see: Di Nicola et al. (2007 ); Jin et al. (1999 , 2009 ); Effendy et al. (2007a ,b ); Awaleh et al. (2005a ,b ); Pettinari et al. (2007 ). For general background, see: Howells & Mccown (1977 ); Bowmaker et al. (2005 ); Lawrance (1986 ).

Experimental

Crystal data

[Ag(C₁₂H₈N₂)(C₁₈H₁₅P)]CF₃SO₃
M_r = 699.42
Triclinic, $[P \overline 1]$
a = 10.9832 (2) Å
b = 11.7533 (2) Å
c = 12.2642 (3) Å
α = 77.711 (1)°
β = 76.183 (1)°
γ = 73.440 (1)°
V = 1455.66 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.87 mm⁻¹
T = 293 K
0.4 × 0.3 × 0.2 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.735, T_max = 0.832
18629 measured reflections
9515 independent reflections
6777 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.133
S = 1.00
9515 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.59 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—N2	2.2798 (18)
Ag1—N1	2.292 (2)
Ag1—P1	2.3469 (5)

N2—Ag1—N1	73.53 (8)
N2—Ag1—P1	147.77 (6)
N1—Ag1—P1	138.03 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H16⋯O2	0.93	2.36	3.285 (6)	173

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: 10.1107/S1600536809032097/wm2241sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809032097/wm2241Isup2.hkl

checkCIF report

Comment top

A recent report (Di Nicola et al., 2007) describes complexes between silver nitrate, a tertiary phosphine ligand and oligodentate bases, L that are derivatives of 2,2'-bipyridyl, which resulted in adducts with general formula AgNO₃:PR₃:L(1:1:1). The silver coordination environment in these complexes is dominated by the quasi-planar N₂AgP or O₂AgP coordination. We have likewise studied mixed-ligand Ag(I) complexes of N-heterocyclic and PPh₃ ligands, viz [AgBr(phen)(PPh₃)] and [AgX(2-Apy)(PPh₃)]₂ (X = Br, Cl, NO₃; 2-Apy= 2-aminopyridine) (Jin et al., 1999, Jin et al., 2009) and have synthesized the title complex [Ag(phen)(PPh₃)](OTf). Furthermore, we have studied the role of several weakly coordinating anions (nitrate, nitrite, acetate, perchlorate trifluoroacetate and trifluoromethanesulfonate) in silver complexes.

The molecular structure of the title complex is depicted in Fig.1. The coordination polyhedron of the silver atom adopts a distorted trigonal-planar geometry, formed by two nitrogen atoms of phen with Ag—N distances of 2.3469 (5) Å and 2.2797 (19) Å, and by one phosphorus atom of the PPh₃ ligand with a Ag—P distance of 2.292 (2) Å. The trifluoromethanesulfonate anion is present as a counter anion and, as expected, shows no direct coordination to the metal center, in contrast to the complex [AgBr(phen)(PPh₃)] where the silver atom is coordinated to two nitrogen atoms of phen (Ag—N 2.376 (8) Å), one phosphorus atom of PPh₃ (Ag—P, 2.375 (3) Å) and in addition to one bromide anion (Jin et al., 1999), adopting a distorted tetrahedron as coordination polyhedron.

The molecular structure of the title complex shows little differences in comparison with the structures of compounds AgX:PPh₃:L, where X = nitrate (Di Nicola et al., 2007), nitrite (Pettinari et al., 2007), acetate (Effendy et al., 2007a), perchlorate (Effendy et al., 2007b) and trifluoroacetate (Awaleh et al., 2005a). Considering the large steric hindrance and the weak coordination ability (Awaleh et al., 2005b; Howells et al., 1977; Lawrance et al.,1986) of the trifluoromethanesulfonate anion, there is only one C—H···O hydrogen-bond between the phenanthroline ligand and the O atom of the anion with the distance O···H of 2.609Å and the angle C—H···O of 173°.

In the title complex, the P—Ag—N1, P—Ag—N2 and N1—Ag—N2 angles are 147.77 (6)°, 138.03 (6)° and 73.54 (8) ° with a sum of 359.54 °, which comfirms the trigonal-planar environment around the silver atom. In the silver nitrate complex, the P—Ag—N (132.66 (9)°, 131.76 (8)°) (Di Nicola et al., 2007) angles are similar. However, contributing to the role of the nitrate anion, the coordination environment of silver changes from distorted trigonal planar to tetrahedral. The P—Ag—N angles in the other complexes are: 136.94 (5)°, 139.60 (5)°, 71.40 (6)° in the perchlorate (Effendy et al., 2007b), 129.4 (1)°, 135.7 (1)°, 71.7 (2)° in trifluoroacetate (Awaleh et al., 2005a), 116.52 (6)°, 126.12 (7)°, 70.5 (1)° in acetate (Effendy et al., 2007a) and 126.72 (8)°, 127.18 (9)°, 70.77 (12)° in the nitrite (Pettinari et al.,2007) anion.

Hence, we should consider two types of anions in the complexes AgX:PR₃:L, viz tetrahedral or distorted trigonal-planar anions and planar or quasi-planar anions (Awaleh et al., 2005a; Awaleh et al., 2005b; Bowmaker et al., 2005). Nitrate, nitrite and acetate belong to the former type, whereas perchlorate, trifluoroacetate and trifluoromethanesulfonate can play a role in both of them because of large steric hindrance and the weak coordination ability.

Related literature top

For related structures, see: Di Nicola et al. (2007); Jin et al. (1999, 2009); Effendy et al. (2007a,b); Awaleh et al. (2005a,b); Pettinari et al. (2007). For general background, see: Howells & Mccown (1977); Bowmaker et al. (2005); Lawrance (1986).

Experimental top

A mixture of AgOTf, Ph₃P and phen in the molar ratio of 1:1:1 in MeOH was stirred for 1 h at ambient temperature, then filtered. Subsequent slow evaporation of the filtrate resulted in the formation of colorless crystals of the title complex. Crystals suitable for single-crystal X-ray diffraction were selected directly from the sample as prepared. Analysis found (percentage): C 53.22, H 3.29, N 4.01; calculated: C 53.19, H 3.29, N 4.02.

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. Perspective view of the molecule of the title complex; hydrogen atoms are omitted for clarity. Atoms are displayed as ellipsoids at the 35% probability level.

(1,10-Phenanthroline-κ²N,N')(triphenylphosphine- κP)silver(I) trifluoromethanesulfonate top

Crystal data top

[Ag(C₁₂H₈N₂)(C₁₈H₁₅P)]CF₃SO₃	Z = 2
M_r = 699.42	F(000) = 704
Triclinic, P1	D_x = 1.596 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.9832 (2) Å	Cell parameters from 5045 reflections
b = 11.7533 (2) Å	θ = 2.3–32.9°
c = 12.2642 (3) Å	µ = 0.87 mm⁻¹
α = 77.711 (1)°	T = 293 K
β = 76.183 (1)°	Block, colourless
γ = 73.440 (1)°	0.4 × 0.3 × 0.2 mm
V = 1455.66 (5) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	9515 independent reflections
Radiation source: fine-focus sealed tube	6777 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 32.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −15→15
T_min = 0.735, T_max = 0.832	k = −17→16
18629 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.075P)² + 0.38P] where P = (F_o² + 2F_c²)/3
9515 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.59 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

[Ag(C₁₂H₈N₂)(C₁₈H₁₅P)]CF₃SO₃	γ = 73.440 (1)°
M_r = 699.42	V = 1455.66 (5) Å³
Triclinic, P1	Z = 2
a = 10.9832 (2) Å	Mo Kα radiation
b = 11.7533 (2) Å	µ = 0.87 mm⁻¹
c = 12.2642 (3) Å	T = 293 K
α = 77.711 (1)°	0.4 × 0.3 × 0.2 mm
β = 76.183 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	9515 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	6777 reflections with I > 2σ(I)
T_min = 0.735, T_max = 0.832	R_int = 0.021
18629 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	Δρ_max = 0.59 e Å⁻³
9515 reflections	Δρ_min = −0.66 e Å⁻³
379 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	0.09032 (2)	0.931304 (15)	0.211327 (16)	0.05664 (9)
P1	0.18488 (6)	0.77307 (5)	0.10540 (5)	0.04241 (13)
C24	−0.0779 (3)	1.12309 (19)	0.36019 (18)	0.0491 (6)
C25	−0.3066 (4)	1.2209 (4)	0.3869 (4)	0.0981 (15)
H21	−0.3787	1.2746	0.4205	0.118*
S1	0.61400 (9)	0.77152 (8)	0.31032 (8)	0.0748 (2)
C1	0.0853 (2)	0.75012 (19)	0.01682 (19)	0.0455 (5)
C3	0.1327 (3)	0.6742 (3)	−0.0638 (3)	0.0631 (7)
H6	0.2207	0.6372	−0.0786	0.076*
C2	−0.0452 (3)	0.8068 (3)	0.0342 (3)	0.0644 (7)
H10	−0.0782	0.8614	0.0852	0.077*
C4	0.3400 (2)	0.77960 (19)	0.01460 (18)	0.0433 (4)
C6	0.4324 (3)	0.6788 (2)	−0.0199 (2)	0.0566 (6)
H5	0.4166	0.6031	0.0064	0.068*
C7	0.4818 (3)	0.9018 (3)	−0.0982 (3)	0.0707 (8)
H2	0.4979	0.9772	−0.1261	0.085*
C5	0.3678 (3)	0.8918 (2)	−0.0246 (2)	0.0562 (6)
H1	0.3088	0.9603	−0.0008	0.067*
C10	0.1297 (3)	0.5596 (3)	0.2319 (2)	0.0602 (7)
H15	0.0575	0.5801	0.1981	0.072*
C8	0.2170 (2)	0.63074 (19)	0.20106 (18)	0.0438 (5)
C11	0.1495 (4)	0.4583 (3)	0.3128 (3)	0.0778 (10)
H14	0.0894	0.4118	0.3342	0.093*
C9	0.3237 (3)	0.5981 (2)	0.2526 (2)	0.0544 (6)
H11	0.3828	0.6456	0.2335	0.065*
C12	0.5478 (3)	0.6894 (3)	−0.0929 (3)	0.0652 (7)
H4	0.6082	0.6213	−0.1158	0.078*
C13	0.5725 (3)	0.8001 (3)	−0.1309 (3)	0.0677 (8)
H3	0.6504	0.8071	−0.1789	0.081*
C14	−0.1276 (3)	0.7833 (3)	−0.0234 (3)	0.0766 (9)
H9	−0.2156	0.8201	−0.0094	0.092*
C16	0.0513 (3)	0.6529 (3)	−0.1223 (3)	0.0715 (8)
H7	0.0846	0.6022	−0.1768	0.086*
C15	−0.0786 (3)	0.7058 (3)	−0.1007 (3)	0.0714 (8)
H8	−0.1336	0.6889	−0.1388	0.086*
C18	0.3430 (4)	0.4952 (3)	0.3324 (3)	0.0685 (8)
H12	0.4153	0.4733	0.3662	0.082*
C17	0.2555 (4)	0.4256 (3)	0.3616 (3)	0.0763 (9)
H13	0.2688	0.3561	0.4148	0.092*
O1	0.5839 (4)	0.7776 (4)	0.4276 (3)	0.1266 (12)
O2	0.5105 (4)	0.7955 (3)	0.2518 (4)	0.1519 (17)
O3	0.7108 (4)	0.8336 (4)	0.2534 (4)	0.1455 (16)
C19	0.6933 (5)	0.6175 (4)	0.2985 (6)	0.1103 (17)
F1	0.7991 (3)	0.5804 (4)	0.3393 (4)	0.1752 (17)
F2	0.7172 (6)	0.5954 (4)	0.1989 (4)	0.218 (3)
C23	0.0474 (3)	1.1023 (2)	0.38492 (18)	0.0513 (6)
C21	0.0633 (4)	1.1640 (3)	0.4660 (2)	0.0763 (11)
C22	−0.0480 (7)	1.2472 (3)	0.5189 (3)	0.1041 (18)
H19	−0.0385	1.2879	0.5723	0.125*
C20	0.2638 (4)	1.0021 (3)	0.3561 (3)	0.0752 (9)
H16	0.3327	0.9473	0.3203	0.090*
N1	0.1478 (2)	1.02361 (18)	0.33127 (18)	0.0522 (5)
N2	−0.09368 (19)	1.06137 (17)	0.28528 (15)	0.0489 (5)
C26	−0.1838 (4)	1.2062 (2)	0.4146 (2)	0.0757 (10)
C27	−0.2110 (3)	1.0794 (3)	0.2637 (3)	0.0708 (8)
H23	−0.2217	1.0367	0.2123	0.085*
C28	−0.1636 (6)	1.2669 (3)	0.4930 (3)	0.1029 (17)
H20	−0.2329	1.3223	0.5277	0.124*
C29	−0.3190 (4)	1.1595 (4)	0.3146 (4)	0.0990 (14)
H22	−0.3996	1.1693	0.2972	0.119*
C31	0.2848 (6)	1.0623 (5)	0.4377 (4)	0.1018 (17)
H17	0.3670	1.0475	0.4536	0.122*
C30	0.1856 (6)	1.1398 (5)	0.4908 (3)	0.1008 (17)
H18	0.1988	1.1777	0.5448	0.121*
F3	0.6223 (5)	0.5475 (3)	0.3633 (5)	0.213 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.06687 (15)	0.04557 (11)	0.05563 (12)	−0.00722 (8)	−0.00064 (9)	−0.02543 (8)
P1	0.0462 (3)	0.0368 (2)	0.0428 (3)	−0.0074 (2)	−0.0011 (2)	−0.0152 (2)
C24	0.0684 (16)	0.0344 (9)	0.0358 (9)	−0.0065 (9)	0.0011 (9)	−0.0071 (7)
C25	0.072 (2)	0.074 (2)	0.094 (3)	0.0230 (17)	0.021 (2)	0.0052 (19)
S1	0.0677 (5)	0.0771 (5)	0.0829 (5)	−0.0120 (4)	−0.0169 (4)	−0.0249 (4)
C1	0.0490 (13)	0.0417 (10)	0.0443 (11)	−0.0082 (8)	−0.0041 (9)	−0.0133 (8)
C3	0.0536 (15)	0.0689 (16)	0.0681 (16)	−0.0009 (12)	−0.0068 (12)	−0.0380 (13)
C2	0.0545 (16)	0.0662 (16)	0.0732 (18)	−0.0011 (12)	−0.0090 (13)	−0.0345 (13)
C4	0.0472 (12)	0.0395 (9)	0.0426 (10)	−0.0110 (8)	−0.0056 (9)	−0.0077 (8)
C6	0.0523 (15)	0.0434 (11)	0.0633 (15)	−0.0094 (10)	0.0063 (11)	−0.0083 (10)
C7	0.075 (2)	0.0628 (16)	0.077 (2)	−0.0352 (15)	−0.0136 (16)	0.0069 (14)
C5	0.0613 (16)	0.0413 (11)	0.0690 (16)	−0.0161 (10)	−0.0162 (13)	−0.0062 (10)
C10	0.0700 (18)	0.0622 (15)	0.0540 (14)	−0.0303 (13)	−0.0077 (12)	−0.0061 (11)
C8	0.0538 (13)	0.0407 (9)	0.0377 (9)	−0.0145 (9)	−0.0004 (9)	−0.0133 (8)
C11	0.107 (3)	0.0724 (19)	0.0640 (18)	−0.0527 (19)	−0.0103 (18)	0.0020 (15)
C9	0.0615 (16)	0.0525 (12)	0.0524 (13)	−0.0168 (11)	−0.0113 (11)	−0.0106 (10)
C12	0.0510 (15)	0.0647 (16)	0.0652 (16)	−0.0060 (12)	0.0046 (12)	−0.0074 (13)
C13	0.0497 (16)	0.082 (2)	0.0651 (17)	−0.0229 (14)	−0.0056 (13)	0.0055 (14)
C14	0.0515 (17)	0.086 (2)	0.098 (2)	0.0036 (14)	−0.0254 (16)	−0.0410 (18)
C16	0.071 (2)	0.0799 (19)	0.0713 (18)	−0.0068 (15)	−0.0163 (15)	−0.0411 (15)
C15	0.071 (2)	0.0742 (18)	0.077 (2)	−0.0096 (15)	−0.0304 (16)	−0.0228 (15)
C18	0.093 (2)	0.0581 (15)	0.0577 (15)	−0.0160 (15)	−0.0278 (15)	−0.0039 (12)
C17	0.118 (3)	0.0585 (16)	0.0554 (16)	−0.0331 (17)	−0.0203 (17)	0.0037 (12)
O1	0.105 (2)	0.169 (4)	0.097 (2)	−0.019 (2)	0.0043 (18)	−0.050 (2)
O2	0.161 (3)	0.090 (2)	0.238 (5)	0.013 (2)	−0.143 (4)	−0.038 (2)
O3	0.148 (3)	0.117 (3)	0.172 (4)	−0.072 (3)	0.034 (3)	−0.043 (2)
C19	0.094 (3)	0.070 (2)	0.161 (5)	−0.011 (2)	−0.041 (3)	0.002 (3)
F1	0.092 (2)	0.166 (3)	0.236 (4)	0.038 (2)	−0.057 (2)	−0.031 (3)
F2	0.336 (7)	0.123 (3)	0.175 (4)	0.056 (3)	−0.082 (4)	−0.096 (3)
C23	0.0848 (19)	0.0382 (10)	0.0355 (10)	−0.0281 (11)	−0.0072 (10)	−0.0027 (8)
C21	0.146 (3)	0.0638 (16)	0.0408 (12)	−0.068 (2)	−0.0155 (16)	0.0002 (11)
C22	0.216 (6)	0.0626 (19)	0.0432 (15)	−0.068 (3)	0.011 (2)	−0.0225 (13)
C20	0.071 (2)	0.080 (2)	0.080 (2)	−0.0389 (17)	−0.0279 (17)	0.0172 (16)
N1	0.0608 (13)	0.0474 (10)	0.0525 (11)	−0.0202 (9)	−0.0160 (9)	−0.0014 (8)
N2	0.0510 (12)	0.0468 (10)	0.0441 (10)	−0.0026 (8)	−0.0093 (8)	−0.0096 (8)
C26	0.104 (3)	0.0428 (12)	0.0515 (14)	0.0004 (13)	0.0185 (15)	−0.0092 (10)
C27	0.0586 (18)	0.0790 (19)	0.0655 (17)	−0.0017 (14)	−0.0208 (14)	−0.0024 (14)
C28	0.173 (5)	0.0529 (16)	0.061 (2)	−0.023 (2)	0.029 (3)	−0.0266 (14)
C29	0.060 (2)	0.108 (3)	0.093 (3)	0.011 (2)	−0.0072 (19)	0.009 (2)
C31	0.120 (4)	0.131 (4)	0.089 (3)	−0.094 (3)	−0.059 (3)	0.040 (3)
C30	0.171 (5)	0.109 (3)	0.061 (2)	−0.103 (4)	−0.035 (3)	0.011 (2)
F3	0.209 (5)	0.103 (2)	0.335 (7)	−0.079 (3)	−0.087 (4)	0.042 (3)

Geometric parameters (Å, º) top

Ag1—N2	2.2798 (18)	C11—H14	0.9300
Ag1—N1	2.292 (2)	C9—C18	1.384 (4)
Ag1—P1	2.3469 (5)	C9—H11	0.9300
P1—C4	1.812 (2)	C12—C13	1.365 (4)
P1—C1	1.819 (3)	C12—H4	0.9300
P1—C8	1.823 (2)	C13—H3	0.9300
C24—N2	1.353 (3)	C14—C15	1.364 (5)
C24—C26	1.418 (3)	C14—H9	0.9300
C24—C23	1.422 (4)	C16—C15	1.370 (5)
C25—C29	1.308 (7)	C16—H7	0.9300
C25—C26	1.423 (7)	C15—H8	0.9300
C25—H21	0.9300	C18—C17	1.371 (5)
S1—O1	1.409 (3)	C18—H12	0.9300
S1—O2	1.417 (3)	C17—H13	0.9300
S1—O3	1.421 (4)	C19—F2	1.253 (7)
S1—C19	1.791 (5)	C19—F1	1.298 (6)
C1—C3	1.381 (3)	C19—F3	1.307 (6)
C1—C2	1.384 (4)	C23—N1	1.355 (3)
C3—C16	1.375 (4)	C23—C21	1.416 (3)
C3—H6	0.9300	C21—C30	1.385 (7)
C2—C14	1.387 (5)	C21—C22	1.442 (7)
C2—H10	0.9300	C22—C28	1.326 (7)
C4—C6	1.391 (3)	C22—H19	0.9300
C4—C5	1.397 (3)	C20—N1	1.323 (4)
C6—C12	1.387 (4)	C20—C31	1.435 (6)
C6—H5	0.9300	C20—H16	0.9300
C7—C5	1.376 (4)	N2—C27	1.327 (4)
C7—C13	1.385 (5)	C26—C28	1.403 (6)
C7—H2	0.9300	C27—C29	1.394 (5)
C5—H1	0.9300	C27—H23	0.9300
C10—C11	1.380 (4)	C28—H20	0.9300
C10—C8	1.382 (4)	C29—H22	0.9300
C10—H15	0.9300	C31—C30	1.337 (7)
C8—C9	1.384 (4)	C31—H17	0.9300
C11—C17	1.356 (5)	C30—H18	0.9300

N2—Ag1—N1	73.53 (8)	C7—C13—H3	119.9
N2—Ag1—P1	147.77 (6)	C15—C14—C2	119.6 (3)
N1—Ag1—P1	138.03 (6)	C15—C14—H9	120.2
C4—P1—C1	106.47 (11)	C2—C14—H9	120.2
C4—P1—C8	104.71 (10)	C15—C16—C3	120.4 (3)
C1—P1—C8	103.84 (10)	C15—C16—H7	119.8
C4—P1—Ag1	115.16 (7)	C3—C16—H7	119.8
C1—P1—Ag1	115.70 (7)	C14—C15—C16	120.1 (3)
C8—P1—Ag1	109.82 (7)	C14—C15—H8	119.9
N2—C24—C26	121.2 (3)	C16—C15—H8	119.9
N2—C24—C23	118.8 (2)	C17—C18—C9	120.1 (3)
C26—C24—C23	120.0 (3)	C17—C18—H12	120.0
C29—C25—C26	120.5 (3)	C9—C18—H12	120.0
C29—C25—H21	119.7	C11—C17—C18	119.9 (3)
C26—C25—H21	119.7	C11—C17—H13	120.0
O1—S1—O2	118.2 (3)	C18—C17—H13	120.0
O1—S1—O3	111.0 (3)	F2—C19—F1	109.1 (6)
O2—S1—O3	113.3 (3)	F2—C19—F3	108.5 (6)
O1—S1—C19	105.7 (3)	F1—C19—F3	102.2 (5)
O2—S1—C19	103.3 (2)	F2—C19—S1	113.4 (4)
O3—S1—C19	103.5 (3)	F1—C19—S1	112.9 (4)
C3—C1—C2	118.2 (3)	F3—C19—S1	110.1 (4)
C3—C1—P1	123.0 (2)	N1—C23—C21	121.9 (3)
C2—C1—P1	118.73 (18)	N1—C23—C24	119.3 (2)
C16—C3—C1	120.6 (3)	C21—C23—C24	118.8 (3)
C16—C3—H6	119.7	C30—C21—C23	117.7 (4)
C1—C3—H6	119.7	C30—C21—C22	123.6 (4)
C1—C2—C14	121.0 (3)	C23—C21—C22	118.7 (4)
C1—C2—H10	119.5	C28—C22—C21	121.5 (3)
C14—C2—H10	119.5	C28—C22—H19	119.2
C6—C4—C5	118.1 (2)	C21—C22—H19	119.2
C6—C4—P1	123.43 (18)	N1—C20—C31	120.8 (4)
C5—C4—P1	118.47 (19)	N1—C20—H16	119.6
C12—C6—C4	121.0 (2)	C31—C20—H16	119.6
C12—C6—H5	119.5	C20—N1—C23	119.3 (3)
C4—C6—H5	119.5	C20—N1—Ag1	126.7 (2)
C5—C7—C13	120.2 (3)	C23—N1—Ag1	113.81 (17)
C5—C7—H2	119.9	C27—N2—C24	118.7 (2)
C13—C7—H2	119.9	C27—N2—Ag1	126.7 (2)
C7—C5—C4	120.5 (3)	C24—N2—Ag1	114.57 (16)
C7—C5—H1	119.7	C28—C26—C24	119.4 (4)
C4—C5—H1	119.7	C28—C26—C25	123.8 (4)
C11—C10—C8	120.1 (3)	C24—C26—C25	116.9 (3)
C11—C10—H15	120.0	N2—C27—C29	122.8 (4)
C8—C10—H15	120.0	N2—C27—H23	118.6
C10—C8—C9	118.8 (2)	C29—C27—H23	118.6
C10—C8—P1	121.0 (2)	C22—C28—C26	121.6 (4)
C9—C8—P1	119.95 (18)	C22—C28—H20	119.2
C17—C11—C10	120.8 (3)	C26—C28—H20	119.2
C17—C11—H14	119.6	C25—C29—C27	119.9 (4)
C10—C11—H14	119.6	C25—C29—H22	120.1
C8—C9—C18	120.3 (3)	C27—C29—H22	120.1
C8—C9—H11	119.9	C30—C31—C20	119.8 (4)
C18—C9—H11	119.9	C30—C31—H17	120.1
C13—C12—C6	119.9 (3)	C20—C31—H17	120.1
C13—C12—H4	120.1	C31—C30—C21	120.4 (4)
C6—C12—H4	120.1	C31—C30—H18	119.8
C12—C13—C7	120.2 (3)	C21—C30—H18	119.8
C12—C13—H3	119.9

N2—Ag1—P1—C4	143.08 (12)	O1—S1—C19—F1	−60.6 (5)
N1—Ag1—P1—C4	−51.26 (12)	O2—S1—C19—F1	174.5 (5)
N2—Ag1—P1—C1	18.06 (13)	O3—S1—C19—F1	56.2 (5)
N1—Ag1—P1—C1	−176.27 (11)	O1—S1—C19—F3	52.9 (5)
N2—Ag1—P1—C8	−99.05 (13)	O2—S1—C19—F3	−71.9 (5)
N1—Ag1—P1—C8	66.61 (12)	O3—S1—C19—F3	169.7 (5)
C4—P1—C1—C3	40.1 (3)	N2—C24—C23—N1	1.4 (3)
C8—P1—C1—C3	−70.1 (3)	C26—C24—C23—N1	−179.3 (2)
Ag1—P1—C1—C3	169.5 (2)	N2—C24—C23—C21	−178.0 (2)
C4—P1—C1—C2	−142.9 (2)	C26—C24—C23—C21	1.3 (3)
C8—P1—C1—C2	106.9 (2)	N1—C23—C21—C30	−1.1 (4)
Ag1—P1—C1—C2	−13.6 (2)	C24—C23—C21—C30	178.3 (2)
C2—C1—C3—C16	−2.1 (5)	N1—C23—C21—C22	179.5 (2)
P1—C1—C3—C16	174.9 (3)	C24—C23—C21—C22	−1.1 (3)
C3—C1—C2—C14	3.3 (5)	C30—C21—C22—C28	−179.5 (3)
P1—C1—C2—C14	−173.8 (3)	C23—C21—C22—C28	−0.1 (5)
C1—P1—C4—C6	−75.7 (2)	C31—C20—N1—C23	−0.9 (4)
C8—P1—C4—C6	33.9 (2)	C31—C20—N1—Ag1	−176.6 (2)
Ag1—P1—C4—C6	154.6 (2)	C21—C23—N1—C20	1.0 (3)
C1—P1—C4—C5	103.2 (2)	C24—C23—N1—C20	−178.4 (2)
C8—P1—C4—C5	−147.2 (2)	C21—C23—N1—Ag1	177.19 (17)
Ag1—P1—C4—C5	−26.5 (2)	C24—C23—N1—Ag1	−2.2 (3)
C5—C4—C6—C12	−1.2 (4)	N2—Ag1—N1—C20	177.5 (2)
P1—C4—C6—C12	177.6 (2)	P1—Ag1—N1—C20	5.5 (3)
C13—C7—C5—C4	−2.4 (5)	N2—Ag1—N1—C23	1.63 (15)
C6—C4—C5—C7	2.1 (4)	P1—Ag1—N1—C23	−170.45 (11)
P1—C4—C5—C7	−176.8 (2)	C26—C24—N2—C27	−0.4 (3)
C11—C10—C8—C9	0.1 (4)	C23—C24—N2—C27	178.9 (2)
C11—C10—C8—P1	−173.6 (3)	C26—C24—N2—Ag1	−179.12 (18)
C4—P1—C8—C10	−140.7 (2)	C23—C24—N2—Ag1	0.2 (3)
C1—P1—C8—C10	−29.2 (2)	N1—Ag1—N2—C27	−179.6 (2)
Ag1—P1—C8—C10	95.1 (2)	P1—Ag1—N2—C27	−9.5 (3)
C4—P1—C8—C9	45.7 (2)	N1—Ag1—N2—C24	−0.94 (15)
C1—P1—C8—C9	157.17 (19)	P1—Ag1—N2—C24	169.11 (11)
Ag1—P1—C8—C9	−78.53 (19)	N2—C24—C26—C28	179.0 (3)
C8—C10—C11—C17	−1.3 (5)	C23—C24—C26—C28	−0.3 (4)
C10—C8—C9—C18	0.8 (4)	N2—C24—C26—C25	0.2 (4)
P1—C8—C9—C18	174.6 (2)	C23—C24—C26—C25	−179.1 (2)
C4—C6—C12—C13	0.7 (5)	C29—C25—C26—C28	−178.6 (4)
C6—C12—C13—C7	−1.0 (5)	C29—C25—C26—C24	0.1 (5)
C5—C7—C13—C12	1.9 (5)	C24—N2—C27—C29	0.2 (4)
C1—C2—C14—C15	−1.9 (6)	Ag1—N2—C27—C29	178.8 (3)
C1—C3—C16—C15	−0.6 (6)	C21—C22—C28—C26	1.2 (6)
C2—C14—C15—C16	−0.9 (6)	C24—C26—C28—C22	−1.0 (5)
C3—C16—C15—C14	2.1 (6)	C25—C26—C28—C22	177.7 (3)
C8—C9—C18—C17	−0.6 (5)	C26—C25—C29—C27	−0.3 (6)
C10—C11—C17—C18	1.5 (6)	N2—C27—C29—C25	0.1 (6)
C9—C18—C17—C11	−0.5 (5)	N1—C20—C31—C30	1.1 (5)
O1—S1—C19—F2	174.6 (5)	C20—C31—C30—C21	−1.2 (5)
O2—S1—C19—F2	49.8 (6)	C23—C21—C30—C31	1.2 (5)
O3—S1—C19—F2	−68.6 (6)	C22—C21—C30—C31	−179.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H16···O2	0.93	2.36	3.285 (6)	173

Experimental details

Crystal data
Chemical formula	[Ag(C₁₂H₈N₂)(C₁₈H₁₅P)]CF₃SO₃
M_r	699.42
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	10.9832 (2), 11.7533 (2), 12.2642 (3)
α, β, γ (°)	77.711 (1), 76.183 (1), 73.440 (1)
V (Å³)	1455.66 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.87
Crystal size (mm)	0.4 × 0.3 × 0.2

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.735, 0.832
No. of measured, independent and observed [I > 2σ(I)] reflections	18629, 9515, 6777
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.757

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.133, 1.00
No. of reflections	9515
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.66

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

Selected geometric parameters (Å, º) top

Ag1—N2	2.2798 (18)	Ag1—P1	2.3469 (5)
Ag1—N1	2.292 (2)

N2—Ag1—N1	73.53 (8)	N1—Ag1—P1	138.03 (6)
N2—Ag1—P1	147.77 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H16···O2	0.93	2.360	3.285 (6)	173

Acknowledgements

This work was supported by the National Science Foundation of China (grant No. 20871085), the Committee of Education of Beijing Foundation of China (grant No. KM200610028006), the Project sponsored by SRF for ROCS and SEM, the subsidy of Beijing Personnel Bureau, the National Keystone Basic Research Program (973 Program under grant Nos. 2007CB310408, No. 2006CB302901), the State Key Laboratory of Functional Materials for Informatics and the Shanghai Institute of Microsystems and Information Technology, Chinese Academy of Sciences.

References

Awaleh, M. O., Badia, A. & Brisse, F. (2005a). Inorg. Chem. 44, 7833–7845. Web of Science CSD CrossRef PubMed CAS Google Scholar
Awaleh, M. O., Badia, A. & Brisse, F. (2005b). Cryst. Growth Des. 5, 1897–1906. Web of Science CSD CrossRef CAS Google Scholar
Bowmaker, G. A., Effendy, Marfuah, S., Skelton, B. W. & White, A. H. (2005). Inorg. Chim. Acta, 358, 4371–4388. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2007). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Di Nicola, C., Effendy, Marchetti, F., Pettinari, C., Skelton, B. W. & White, A. H. (2007). Inorg. Chim. Acta, 360, 1433–1450. Web of Science CSD CrossRef CAS Google Scholar
Effendy, Marchetti, F., Pettinari, C., Pettinari, R., Skelton, B. W. & White, A. H. (2007b). Inorg. Chim. Acta, 360, 1451–1465. Web of Science CSD CrossRef CAS Google Scholar
Effendy, Marchetti, F., Pettinari, C., Skelton, B. W. & White, A. H. (2007a). Inorg. Chim. Acta, 360, 1424–1432. Web of Science CSD CrossRef CAS Google Scholar
Howells, R. D. & Mccown, J. D. (1977). Chem. Rev. 77, 19–92. CrossRef Web of Science Google Scholar
Jin, Q. H., Hu, K. Y. S. L. L., Wang, R., Zuo, X., Zhang, C. L. & Lu, X. M. (2009). Polyhedron, doi: 10.1016/j.poly.2009.06.036. Google Scholar
Jin, Q. H., Xin, X. L., Zhu, F. J. & Li, Y. (1999). Z. Kristallogr. New Cryst. Struct. 214, 503–504. CAS Google Scholar
Lawrance, G. A. (1986). Chem. Rev. 86, 17–33. CrossRef CAS Web of Science Google Scholar
Pettinari, C., Ngoune, J., Skelton, B. W. & White, A. H. (2007). Inorg. Chem. Commun. 10, 329–331. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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