[μ-1,2-Bis(4-pyrid­yl)ethane-κ2N:N′]bis­[(4′-phenyl-2,2′:6′,2′′-terpyridine-κ3N,N′,N′′)silver(I)] bis­(trifluoro­methane­sulfonate)

Ma, Y.; Liu, B.; Xue, C.

doi:10.1107/S1600536810031776

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 9| September 2010| Pages m1117-m1118

https://doi.org/10.1107/S1600536810031776

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[μ-1,2-Bis(4-pyridyl)ethane-κ²N:N′]bis[(4′-phenyl-2,2′:6′,2′′-terpyridine-κ³N,N′,N′′)silver(I)] bis(trifluoromethanesulfonate)

Yajun Ma,^a ^* Buming Liu ^a and Chenghu Xue ^a

^aSchool of Chemistry and Chemical Engineering, Yu Lin University, Yulin 719000, People's Republic of China
^*Correspondence e-mail: yulinmyj@126.com

(Received 25 July 2010; accepted 7 August 2010; online 18 August 2010)

In the title compound, [Ag₂(C₁₂H₁₂N₂)(C₂₁H₁₅N₃)₂](CF₃SO₃)₂, the Ag^I atom is coordinated by three N atoms of one 4′-phenyl-2,2′:6′,2′′-terpyridine (phtpy) ligand and one pyridyl N atom of the 1,2-bis(4-pyridyl)ethane (bpe) ligand, displaying a distorted square-planar geometry. Two Ag^I atoms are bridged by one trans-bpe ligand, generating a dinuclear cation. The dinuclear cation is located on a centre of inversion, which is in the middle of the ethylene fragment of the bpe ligand. In the crystal, the pyridyl rings of neighboring dinuclear units are stacked by π–π interactions with centroid–centroid distances of 3.667 (2) and 3.835 (2) Å. The F and O atoms of the CF₃SO₃⁻ anions are involved in intermolecular C—H⋯F and C—H⋯O hydrogen-bonding interactions, respectively, with –CH groups from the phtpy ligands.

Related literature

For related complexes with phtpy as a ligand, see: Chen et al. (2005 ); Constable et al. (1990 ); Hou & Li (2005 ); Rao et al. (1997 ); Shi et al. (2007 ); Tu et al. (2004 ); Xie et al. (2008 ).

Experimental

Crystal data

[Ag₂(C₁₂H₁₂N₂)(C₂₁H₁₅N₃)₂](CF₃O₃S)₂
M_r = 1316.86
Monoclinic, P 2₁ /c
a = 7.8345 (8) Å
b = 17.4048 (17) Å
c = 20.5608 (18) Å
β = 108.795 (3)°
V = 2654.1 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.90 mm⁻¹
T = 295 K
0.18 × 0.12 × 0.10 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.855, T_max = 0.916
14927 measured reflections
5194 independent reflections
4170 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.119
S = 1.08
5194 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.93	2.52	3.360 (4)	150
C20—H20⋯F1ⁱ	0.93	2.56	3.251 (5)	132
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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: https://doi.org/10.1107/S1600536810031776/zl2294sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810031776/zl2294Isup2.hkl

checkCIF report

Comment top

4'-Phenyl-2,2':6',2"-terpyridine (phtpy) is an excellent chelating ligand and arising from its good coordinating abilities with a broad variety of transition metal ions, such as Cu^I, Ag^I, Mn^II, Ni^II, Cu^II, Zn^II and Ru^II metal ions, it has recently been the focus of several investigations (Chen et al., 2005; Constable et al., 1990; Hou & Li, 2005; Rao et al., 1997; Shi et al., 2007; Tu et al., 2004; Xie et al., 2008). Some of the reported complexes exhibit interesting photoluminescent and magnetic properties. We report here the synthesis and crystal structure of a new Ag^I complex incorporating both phtpy and 1,2-bis(4-pyridy)ethane (bpe) as ligands.

In the title compound, [Ag₂(C₁₂H₁₂N₂)(C₂₁H₁₅N₃)₂] (CF₃SO₃)₂, the asymmetric unit is composed of one Ag atom, one phtpy ligand, one half bpe ligand and one CF₃SO₃^- anion, as shown in Fig. 1. The Ag^I centre is four-coordinated by three N atoms of one phtpy ligand and one pyridyl N atom of the bpe ligand, resulting in a distorted square-planar geometry. The sum of the angles about the Ag^I centre is 385.02°. The bpe ligand exhibits a trans-mode at the ethylene unit (C24/C27/C27ⁱⁱ/C24ⁱⁱ, symmetry code, ii = 2-x, 1-y, 1-z) and bridges the two Ag^I centres to generate a dinuclear structure, which is located on a center of inversion in the middle of the ethylene group of the bpe ligand. In the solid state, the phtpy ligands are π-stacking with phtpy units from neighboring complexes so as to form stacks along the a-axis of the cell. Alternating phtpy units in the stacks have opposite orientation with one phtpy unit of each dinuclear complex being part of one stack, while the other phtpy unit is part of the next neighboring stack. The interdigitating π-stacked columns thus form layers of connected stacks that stretch perpendicular to the c-axis of the unit cell. Closest entroid-to-centroid distances within the stacks are of 3.835 (2) Å and 3.667 (2) Å for the distances of the N3 pyridyl and the N1ⁱⁱⁱ and N2ⁱ pyridyl rings, respectively (Fig. 2). (Symmetry operators: i = 1-x, -y, 1-z, iii = 2-x, -y, 1-z). In addition, the F1 and O1 atoms of CF₃SO₃^- anions are involved in intermolecular C-H···F and C-H···O hydrogen bonding interactions, respectively, with -CH groups from the phtpy ligands (Fig. 3).

Related literature top

For related complexes with phtpy as a ligand, see: Chen et al. (2005); Constable et al. (1990); Hou & Li (2005); Rao et al. (1997); Shi et al. (2007); Tu et al. (2004); Xie et al. (2008).

Experimental top

The ligand 4'-phenyl-2,2':6',2"-terpyridine (phtpy) was synthesized according to the documented method (Constable et al., 1990). A mixture of silver trifluoromethanesulfonate (0.05 mmol, 12.8 mg), phtpy (0.1 mmol, 30.9 mg), 1,2-bis(4-pyridy)ethane (0.05 mmol, 9.2 mg) and 8 ml acetonitrile was stirred in a 25 ml beaker at room temperature for 3 h. After filtration, the filtrate was placed at room temperature for one week to give yellow prismatic crystals of the title compound. Yield: 22.4 mg (34 %). Mp: above 573 K. Anal. C, 51.08; H, 3.21; N, 8.51 %. Found: C, 51.12; H, 3.24; N, 8.46 %. IR (KBr, cm^-1): 3061, 2925, 1601, 1472, 1408, 1301, 1252, 1015, 875.

Structure description top

For related complexes with phtpy as a ligand, see: Chen et al. (2005); Constable et al. (1990); Hou & Li (2005); Rao et al. (1997); Shi et al. (2007); Tu et al. (2004); Xie et al. (2008).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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 the title compound, with displacement ellipsoids drawn at the 30% probability level, and H atoms were omitted for clarity; symmetry code, ii: 2-x, 1-y, 1-z.
	Fig. 2. Packing diagram of the title compound showing the intermolecular π–π stacking interactions. The H atoms and CF₃SO₃^- anions have been omitted for clarity.
	Fig. 3. Packing diagram of the title compound showing the intermolecular π–π and C-H···F and C-H···O hydrogen bonding interactions. The H atoms not involved in hydrogen bonding have been omitted for clarity.

[µ-1,2-Bis(4-pyridyl)ethane-κ²N:N']bis[(4'-phenyl- 2,2':6',2''-terpyridine-κ³N,N',N'')silver(I)] bis(trifluoromethanesulfonate) top

Crystal data top

[Ag₂(C₁₂H₁₂N₂)(C₂₁H₁₅N₃)₂](CF₃O₃S)₂	F(000) = 1324
M_r = 1316.86	D_x = 1.648 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4745 reflections
a = 7.8345 (8) Å	θ = 2.3–25.0°
b = 17.4048 (17) Å	µ = 0.90 mm⁻¹
c = 20.5608 (18) Å	T = 295 K
β = 108.795 (3)°	Prism, yellow
V = 2654.1 (4) Å³	0.18 × 0.12 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX area-detector diffractometer	5194 independent reflections
Radiation source: fine-focus sealed tube	4170 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 26.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.855, T_max = 0.916	k = −21→21
14927 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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0657P)² + 0.7584P] where P = (F_o² + 2F_c²)/3
5194 reflections	(Δ/σ)_max = 0.002
361 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.50 e Å⁻³

Crystal data top

[Ag₂(C₁₂H₁₂N₂)(C₂₁H₁₅N₃)₂](CF₃O₃S)₂	V = 2654.1 (4) Å³
M_r = 1316.86	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.8345 (8) Å	µ = 0.90 mm⁻¹
b = 17.4048 (17) Å	T = 295 K
c = 20.5608 (18) Å	0.18 × 0.12 × 0.10 mm
β = 108.795 (3)°

Data collection top

Bruker SMART APEX area-detector diffractometer	5194 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4170 reflections with I > 2σ(I)
T_min = 0.855, T_max = 0.916	R_int = 0.022
14927 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.08	Δρ_max = 0.54 e Å⁻³
5194 reflections	Δρ_min = −0.50 e Å⁻³
361 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
Ag1	0.83117 (4)	0.124375 (13)	0.540004 (13)	0.06447 (14)
N1	0.8764 (4)	0.10707 (15)	0.42457 (14)	0.0530 (6)
N2	0.7513 (3)	0.00035 (13)	0.49378 (11)	0.0402 (5)
N3	0.7565 (3)	0.04668 (14)	0.61909 (12)	0.0484 (6)
N4	0.8557 (4)	0.25065 (15)	0.54219 (14)	0.0568 (7)
C1	0.9334 (5)	0.1619 (2)	0.39122 (19)	0.0605 (8)
H1	0.9685	0.2087	0.4133	0.073*
C2	0.9433 (5)	0.1533 (2)	0.32641 (18)	0.0598 (8)
H2	0.9841	0.1930	0.3050	0.072*
C3	0.8911 (4)	0.0840 (2)	0.29400 (17)	0.0559 (8)
H3	0.8961	0.0759	0.2499	0.067*
C4	0.8311 (4)	0.02665 (18)	0.32742 (16)	0.0508 (7)
H4	0.7944	−0.0204	0.3060	0.061*
C5	0.8262 (4)	0.03988 (16)	0.39343 (14)	0.0420 (6)
C6	0.7646 (4)	−0.02060 (16)	0.43270 (14)	0.0400 (6)
C7	0.7215 (4)	−0.09458 (17)	0.40732 (14)	0.0434 (6)
H7	0.7368	−0.1086	0.3659	0.052*
C8	0.6551 (4)	−0.14803 (17)	0.44398 (14)	0.0416 (6)
C9	0.6437 (4)	−0.12466 (15)	0.50720 (15)	0.0428 (6)
H9	0.6012	−0.1585	0.5335	0.051*
C10	0.6957 (4)	−0.05081 (15)	0.53104 (13)	0.0392 (6)
C11	0.6937 (4)	−0.02467 (16)	0.60008 (14)	0.0413 (6)
C12	0.6375 (4)	−0.07108 (19)	0.64369 (15)	0.0508 (7)
H12	0.5959	−0.1205	0.6301	0.061*
C13	0.6430 (5)	−0.0442 (2)	0.70717 (16)	0.0605 (9)
H13	0.6055	−0.0751	0.7369	0.073*
C14	0.7046 (5)	0.0293 (2)	0.72631 (17)	0.0638 (9)
H14	0.7083	0.0492	0.7687	0.077*
C15	0.7597 (5)	0.0717 (2)	0.68126 (16)	0.0602 (8)
H15	0.8023	0.1211	0.6943	0.072*
C16	0.5957 (4)	−0.22547 (16)	0.41550 (14)	0.0445 (6)
C17	0.5324 (4)	−0.23678 (18)	0.34475 (16)	0.0529 (7)
H17	0.5290	−0.1957	0.3154	0.063*
C18	0.4746 (5)	−0.3084 (2)	0.31780 (18)	0.0636 (9)
H18	0.4324	−0.3151	0.2704	0.076*
C19	0.4789 (5)	−0.36933 (19)	0.3599 (2)	0.0645 (9)
H19	0.4401	−0.4174	0.3413	0.077*
C20	0.5409 (5)	−0.35943 (19)	0.43023 (18)	0.0620 (9)
H20	0.5436	−0.4009	0.4591	0.074*
C21	0.5990 (5)	−0.28787 (18)	0.45772 (16)	0.0549 (8)
H21	0.6408	−0.2815	0.5052	0.066*
C22	0.9687 (5)	0.2898 (2)	0.59487 (19)	0.0624 (9)
H22	1.0267	0.2636	0.6354	0.075*
C23	1.0020 (6)	0.3663 (2)	0.5915 (2)	0.0690 (10)
H23	1.0811	0.3910	0.6293	0.083*
C24	0.9185 (5)	0.40753 (19)	0.5317 (2)	0.0635 (9)
C25	0.8000 (5)	0.36723 (19)	0.4785 (2)	0.0642 (9)
H25	0.7381	0.3923	0.4378	0.077*
C26	0.7729 (5)	0.29046 (19)	0.48535 (18)	0.0595 (8)
H26	0.6926	0.2647	0.4485	0.071*
C27	0.9537 (7)	0.4920 (2)	0.5257 (2)	0.0888 (14)
H27A	0.8399	0.5194	0.5127	0.107*
H27B	1.0274	0.5111	0.5702	0.107*
S1	0.31230 (14)	0.32504 (6)	0.30585 (5)	0.0664 (3)
F1	0.3391 (4)	0.41393 (17)	0.41012 (12)	0.1064 (9)
F2	0.1381 (4)	0.44991 (16)	0.31985 (14)	0.1094 (9)
F3	0.0908 (5)	0.3532 (2)	0.37338 (19)	0.1285 (12)
O1	0.3771 (5)	0.26387 (17)	0.35204 (17)	0.1020 (10)
O2	0.4462 (6)	0.3727 (2)	0.2939 (2)	0.1197 (14)
O3	0.1655 (5)	0.3085 (2)	0.24617 (16)	0.1157 (13)
C28	0.2121 (6)	0.3884 (2)	0.35363 (19)	0.0699 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0906 (2)	0.03503 (16)	0.0624 (2)	−0.00525 (11)	0.01721 (15)	0.00040 (10)
N1	0.0587 (16)	0.0431 (13)	0.0574 (16)	−0.0039 (12)	0.0192 (13)	0.0038 (12)
N2	0.0405 (13)	0.0391 (12)	0.0383 (12)	0.0027 (10)	0.0087 (10)	0.0011 (10)
N3	0.0579 (15)	0.0387 (13)	0.0437 (13)	0.0068 (11)	0.0097 (12)	−0.0030 (10)
N4	0.0702 (18)	0.0383 (14)	0.0629 (18)	−0.0016 (12)	0.0229 (15)	0.0024 (12)
C1	0.069 (2)	0.0446 (18)	0.069 (2)	−0.0084 (16)	0.0233 (18)	0.0044 (16)
C2	0.058 (2)	0.0544 (19)	0.071 (2)	0.0026 (16)	0.0265 (18)	0.0187 (17)
C3	0.0556 (19)	0.063 (2)	0.0527 (18)	0.0014 (15)	0.0224 (15)	0.0094 (15)
C4	0.0536 (18)	0.0489 (17)	0.0503 (17)	0.0017 (14)	0.0175 (15)	0.0034 (13)
C5	0.0362 (14)	0.0428 (15)	0.0446 (15)	0.0033 (12)	0.0096 (12)	0.0051 (12)
C6	0.0350 (14)	0.0418 (15)	0.0405 (14)	0.0034 (11)	0.0082 (12)	0.0043 (11)
C7	0.0459 (16)	0.0438 (15)	0.0402 (14)	−0.0005 (13)	0.0133 (13)	−0.0010 (12)
C8	0.0417 (15)	0.0416 (14)	0.0409 (14)	0.0001 (11)	0.0125 (12)	−0.0007 (12)
C9	0.0418 (15)	0.0432 (16)	0.0415 (15)	−0.0010 (12)	0.0109 (12)	0.0018 (12)
C10	0.0356 (14)	0.0387 (14)	0.0398 (14)	0.0046 (11)	0.0076 (11)	0.0014 (11)
C11	0.0372 (15)	0.0444 (15)	0.0398 (14)	0.0090 (12)	0.0089 (12)	0.0022 (12)
C12	0.0510 (18)	0.0525 (17)	0.0503 (16)	−0.0020 (14)	0.0184 (14)	−0.0024 (14)
C13	0.059 (2)	0.080 (2)	0.0469 (17)	0.0030 (17)	0.0224 (16)	0.0042 (16)
C14	0.068 (2)	0.077 (2)	0.0449 (17)	0.0126 (18)	0.0164 (16)	−0.0142 (17)
C15	0.078 (2)	0.0487 (18)	0.0493 (18)	0.0056 (16)	0.0140 (17)	−0.0080 (14)
C16	0.0462 (16)	0.0434 (15)	0.0445 (15)	−0.0040 (12)	0.0156 (13)	−0.0028 (12)
C17	0.063 (2)	0.0490 (17)	0.0467 (17)	−0.0053 (15)	0.0183 (15)	−0.0011 (13)
C18	0.074 (2)	0.065 (2)	0.0492 (18)	−0.0133 (17)	0.0163 (17)	−0.0135 (16)
C19	0.078 (2)	0.0494 (19)	0.066 (2)	−0.0161 (16)	0.0222 (19)	−0.0162 (16)
C20	0.083 (3)	0.0430 (17)	0.063 (2)	−0.0105 (16)	0.0269 (19)	−0.0012 (15)
C21	0.071 (2)	0.0472 (17)	0.0462 (17)	−0.0063 (15)	0.0181 (15)	−0.0018 (13)
C22	0.076 (2)	0.0504 (19)	0.062 (2)	0.0000 (17)	0.0233 (18)	0.0037 (16)
C23	0.084 (3)	0.054 (2)	0.074 (2)	−0.0155 (18)	0.033 (2)	−0.0126 (18)
C24	0.087 (3)	0.0404 (17)	0.079 (2)	−0.0082 (17)	0.049 (2)	−0.0047 (16)
C25	0.076 (2)	0.0498 (19)	0.070 (2)	0.0067 (17)	0.028 (2)	0.0167 (16)
C26	0.060 (2)	0.0495 (18)	0.066 (2)	−0.0042 (15)	0.0171 (17)	0.0005 (16)
C27	0.140 (4)	0.043 (2)	0.111 (3)	−0.012 (2)	0.079 (3)	−0.002 (2)
S1	0.0776 (6)	0.0679 (6)	0.0576 (5)	−0.0045 (5)	0.0271 (5)	−0.0090 (4)
F1	0.135 (2)	0.109 (2)	0.0634 (14)	0.0154 (18)	0.0157 (15)	−0.0260 (14)
F2	0.151 (3)	0.0865 (18)	0.0858 (17)	0.0446 (17)	0.0304 (17)	0.0173 (14)
F3	0.143 (3)	0.121 (2)	0.168 (3)	−0.009 (2)	0.115 (3)	−0.007 (2)
O1	0.134 (3)	0.0624 (18)	0.104 (2)	0.0260 (18)	0.032 (2)	0.0056 (16)
O2	0.133 (3)	0.129 (3)	0.134 (3)	−0.035 (2)	0.094 (3)	−0.016 (2)
O3	0.108 (2)	0.154 (3)	0.0690 (19)	0.007 (2)	0.0062 (18)	−0.049 (2)
C28	0.097 (3)	0.064 (2)	0.050 (2)	0.003 (2)	0.026 (2)	0.0051 (17)

Geometric parameters (Å, º) top

Ag1—N4	2.205 (3)	C14—C15	1.360 (5)
Ag1—N3	2.330 (3)	C14—H14	0.9300
Ag1—N2	2.360 (2)	C15—H15	0.9300
Ag1—N1	2.528 (3)	C16—C21	1.386 (4)
N1—C5	1.331 (4)	C16—C17	1.391 (4)
N1—C1	1.333 (4)	C17—C18	1.379 (5)
N2—C10	1.336 (4)	C17—H17	0.9300
N2—C6	1.344 (4)	C18—C19	1.363 (5)
N3—C15	1.343 (4)	C18—H18	0.9300
N3—C11	1.346 (4)	C19—C20	1.380 (5)
N4—C26	1.334 (4)	C19—H19	0.9300
N4—C22	1.343 (4)	C20—C21	1.383 (4)
C1—C2	1.368 (5)	C20—H20	0.9300
C1—H1	0.9300	C21—H21	0.9300
C2—C3	1.374 (5)	C22—C23	1.363 (5)
C2—H2	0.9300	C22—H22	0.9300
C3—C4	1.377 (4)	C23—C24	1.392 (5)
C3—H3	0.9300	C23—H23	0.9300
C4—C5	1.389 (4)	C24—C25	1.376 (5)
C4—H4	0.9300	C24—C27	1.507 (5)
C5—C6	1.498 (4)	C25—C26	1.367 (5)
C6—C7	1.390 (4)	C25—H25	0.9300
C7—C8	1.399 (4)	C26—H26	0.9300
C7—H7	0.9300	C27—C27ⁱ	1.487 (8)
C8—C9	1.392 (4)	C27—H27A	0.9700
C8—C16	1.483 (4)	C27—H27B	0.9700
C9—C10	1.389 (4)	S1—O1	1.408 (3)
C9—H9	0.9300	S1—O3	1.415 (3)
C10—C11	1.496 (4)	S1—O2	1.420 (3)
C11—C12	1.380 (4)	S1—C28	1.815 (4)
C12—C13	1.374 (4)	F1—C28	1.338 (5)
C12—H12	0.9300	F2—C28	1.305 (4)
C13—C14	1.378 (5)	F3—C28	1.301 (5)
C13—H13	0.9300

N4—Ag1—N3	127.16 (9)	C15—C14—C13	117.9 (3)
N4—Ag1—N2	158.38 (9)	C15—C14—H14	121.0
N3—Ag1—N2	69.91 (8)	C13—C14—H14	121.0
N4—Ag1—N1	95.75 (9)	N3—C15—C14	124.0 (3)
N3—Ag1—N1	136.79 (8)	N3—C15—H15	118.0
N2—Ag1—N1	67.19 (8)	C14—C15—H15	118.0
C5—N1—C1	118.5 (3)	C21—C16—C17	118.2 (3)
C5—N1—Ag1	116.58 (19)	C21—C16—C8	121.7 (3)
C1—N1—Ag1	124.7 (2)	C17—C16—C8	120.1 (3)
C10—N2—C6	119.5 (2)	C18—C17—C16	120.5 (3)
C10—N2—Ag1	118.15 (17)	C18—C17—H17	119.7
C6—N2—Ag1	122.28 (18)	C16—C17—H17	119.7
C15—N3—C11	118.0 (3)	C19—C18—C17	120.7 (3)
C15—N3—Ag1	122.9 (2)	C19—C18—H18	119.7
C11—N3—Ag1	118.89 (18)	C17—C18—H18	119.7
C26—N4—C22	116.9 (3)	C18—C19—C20	119.8 (3)
C26—N4—Ag1	119.0 (2)	C18—C19—H19	120.1
C22—N4—Ag1	123.5 (2)	C20—C19—H19	120.1
N1—C1—C2	123.8 (3)	C19—C20—C21	120.0 (3)
N1—C1—H1	118.1	C19—C20—H20	120.0
C2—C1—H1	118.1	C21—C20—H20	120.0
C1—C2—C3	117.8 (3)	C20—C21—C16	120.8 (3)
C1—C2—H2	121.1	C20—C21—H21	119.6
C3—C2—H2	121.1	C16—C21—H21	119.6
C2—C3—C4	119.3 (3)	N4—C22—C23	122.8 (4)
C2—C3—H3	120.3	N4—C22—H22	118.6
C4—C3—H3	120.3	C23—C22—H22	118.6
C3—C4—C5	119.2 (3)	C22—C23—C24	120.4 (4)
C3—C4—H4	120.4	C22—C23—H23	119.8
C5—C4—H4	120.4	C24—C23—H23	119.8
N1—C5—C4	121.3 (3)	C25—C24—C23	116.3 (3)
N1—C5—C6	117.1 (3)	C25—C24—C27	121.8 (4)
C4—C5—C6	121.7 (3)	C23—C24—C27	121.9 (4)
N2—C6—C7	121.3 (3)	C26—C25—C24	120.3 (3)
N2—C6—C5	116.7 (2)	C26—C25—H25	119.9
C7—C6—C5	122.0 (3)	C24—C25—H25	119.9
C6—C7—C8	120.1 (3)	N4—C26—C25	123.4 (3)
C6—C7—H7	119.9	N4—C26—H26	118.3
C8—C7—H7	119.9	C25—C26—H26	118.3
C9—C8—C7	117.1 (3)	C27ⁱ—C27—C24	112.7 (4)
C9—C8—C16	121.9 (3)	C27ⁱ—C27—H27A	109.1
C7—C8—C16	121.0 (3)	C24—C27—H27A	109.1
C10—C9—C8	120.0 (3)	C27ⁱ—C27—H27B	109.1
C10—C9—H9	120.0	C24—C27—H27B	109.1
C8—C9—H9	120.0	H27A—C27—H27B	107.8
N2—C10—C9	121.8 (3)	O1—S1—O3	116.6 (2)
N2—C10—C11	116.5 (2)	O1—S1—O2	115.6 (3)
C9—C10—C11	121.7 (3)	O3—S1—O2	114.1 (3)
N3—C11—C12	121.0 (3)	O1—S1—C28	102.68 (18)
N3—C11—C10	116.2 (2)	O3—S1—C28	102.7 (2)
C12—C11—C10	122.8 (3)	O2—S1—C28	102.2 (2)
C13—C12—C11	119.9 (3)	F3—C28—F2	108.0 (4)
C13—C12—H12	120.0	F3—C28—F1	107.4 (3)
C11—C12—H12	120.0	F2—C28—F1	105.6 (3)
C12—C13—C14	119.2 (3)	F3—C28—S1	111.7 (3)
C12—C13—H13	120.4	F2—C28—S1	113.9 (3)
C14—C13—H13	120.4	F1—C28—S1	109.9 (3)

N4—Ag1—N1—C5	−163.1 (2)	Ag1—N2—C10—C11	−1.4 (3)
N3—Ag1—N1—C5	10.5 (3)	C8—C9—C10—N2	2.4 (4)
N2—Ag1—N1—C5	3.2 (2)	C8—C9—C10—C11	−177.1 (3)
N4—Ag1—N1—C1	11.7 (3)	C15—N3—C11—C12	−1.1 (4)
N3—Ag1—N1—C1	−174.7 (2)	Ag1—N3—C11—C12	−176.1 (2)
N2—Ag1—N1—C1	177.9 (3)	C15—N3—C11—C10	−178.9 (3)
N4—Ag1—N2—C10	−142.1 (3)	Ag1—N3—C11—C10	6.2 (3)
N3—Ag1—N2—C10	3.26 (19)	N2—C10—C11—N3	−3.1 (4)
N1—Ag1—N2—C10	177.9 (2)	C9—C10—C11—N3	176.4 (3)
N4—Ag1—N2—C6	39.7 (4)	N2—C10—C11—C12	179.2 (3)
N3—Ag1—N2—C6	−174.9 (2)	C9—C10—C11—C12	−1.2 (4)
N1—Ag1—N2—C6	−0.24 (19)	N3—C11—C12—C13	0.9 (5)
N4—Ag1—N3—C15	−14.9 (3)	C10—C11—C12—C13	178.5 (3)
N2—Ag1—N3—C15	−179.7 (3)	C11—C12—C13—C14	0.1 (5)
N1—Ag1—N3—C15	173.1 (2)	C12—C13—C14—C15	−0.8 (5)
N4—Ag1—N3—C11	159.7 (2)	C11—N3—C15—C14	0.4 (5)
N2—Ag1—N3—C11	−5.1 (2)	Ag1—N3—C15—C14	175.1 (3)
N1—Ag1—N3—C11	−12.3 (3)	C13—C14—C15—N3	0.5 (6)
N3—Ag1—N4—C26	−131.2 (2)	C9—C8—C16—C21	−27.9 (5)
N2—Ag1—N4—C26	6.7 (4)	C7—C8—C16—C21	153.6 (3)
N1—Ag1—N4—C26	43.2 (3)	C9—C8—C16—C17	151.3 (3)
N3—Ag1—N4—C22	57.8 (3)	C7—C8—C16—C17	−27.2 (4)
N2—Ag1—N4—C22	−164.2 (2)	C21—C16—C17—C18	0.0 (5)
N1—Ag1—N4—C22	−127.7 (3)	C8—C16—C17—C18	−179.1 (3)
C5—N1—C1—C2	0.1 (5)	C16—C17—C18—C19	−0.2 (6)
Ag1—N1—C1—C2	−174.6 (3)	C17—C18—C19—C20	0.2 (6)
N1—C1—C2—C3	0.1 (5)	C18—C19—C20—C21	−0.2 (6)
C1—C2—C3—C4	0.1 (5)	C19—C20—C21—C16	0.1 (6)
C2—C3—C4—C5	−0.5 (5)	C17—C16—C21—C20	0.0 (5)
C1—N1—C5—C4	−0.5 (4)	C8—C16—C21—C20	179.2 (3)
Ag1—N1—C5—C4	174.6 (2)	C26—N4—C22—C23	−1.0 (5)
C1—N1—C5—C6	179.4 (3)	Ag1—N4—C22—C23	170.1 (3)
Ag1—N1—C5—C6	−5.5 (3)	N4—C22—C23—C24	−0.3 (6)
C3—C4—C5—N1	0.7 (5)	C22—C23—C24—C25	1.6 (6)
C3—C4—C5—C6	−179.2 (3)	C22—C23—C24—C27	−179.2 (4)
C10—N2—C6—C7	0.1 (4)	C23—C24—C25—C26	−1.7 (6)
Ag1—N2—C6—C7	178.2 (2)	C27—C24—C25—C26	179.2 (4)
C10—N2—C6—C5	179.5 (2)	C22—N4—C26—C25	1.0 (5)
Ag1—N2—C6—C5	−2.4 (3)	Ag1—N4—C26—C25	−170.5 (3)
N1—C5—C6—N2	5.3 (4)	C24—C25—C26—N4	0.4 (6)
C4—C5—C6—N2	−174.8 (3)	C25—C24—C27—C27ⁱ	−66.6 (7)
N1—C5—C6—C7	−175.3 (3)	C23—C24—C27—C27ⁱ	114.3 (6)
C4—C5—C6—C7	4.7 (4)	O1—S1—C28—F3	−56.0 (4)
N2—C6—C7—C8	2.9 (4)	O3—S1—C28—F3	65.4 (4)
C5—C6—C7—C8	−176.5 (3)	O2—S1—C28—F3	−176.1 (3)
C6—C7—C8—C9	−3.1 (4)	O1—S1—C28—F2	−178.7 (3)
C6—C7—C8—C16	175.5 (3)	O3—S1—C28—F2	−57.3 (4)
C7—C8—C9—C10	0.5 (4)	O2—S1—C28—F2	61.2 (4)
C16—C8—C9—C10	−178.0 (3)	O1—S1—C28—F1	63.1 (3)
C6—N2—C10—C9	−2.7 (4)	O3—S1—C28—F1	−175.5 (3)
Ag1—N2—C10—C9	179.0 (2)	O2—S1—C28—F1	−57.1 (3)
C6—N2—C10—C11	176.8 (2)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱⁱ	0.93	2.52	3.360 (4)	150
C20—H20···F1ⁱⁱ	0.93	2.56	3.251 (5)	132

Symmetry code: (ii) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	[Ag₂(C₁₂H₁₂N₂)(C₂₁H₁₅N₃)₂](CF₃O₃S)₂
M_r	1316.86
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	7.8345 (8), 17.4048 (17), 20.5608 (18)
β (°)	108.795 (3)
V (Å³)	2654.1 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.18 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.855, 0.916
No. of measured, independent and observed [I > 2σ(I)] reflections	14927, 5194, 4170
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.119, 1.08
No. of reflections	5194
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.50

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
C12—H12···O1ⁱ	0.93	2.52	3.360 (4)	150.1
C20—H20···F1ⁱ	0.93	2.56	3.251 (5)	131.9

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

This work was supported by grants from the Natural Science Foundation of Shaanxi Province (Nos. 2010K14-02-23) and the Scientific Research Plan projects of Shaanxi Education Department (Nos. 09JK837).

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, H., Tagore, R., Das, S., Incarvito, C., Faller, J. W., Crabtree, R. H. & Brudvig, G. W. (2005). Inorg. Chem. 44, 7661–7670. Web of Science CSD CrossRef PubMed CAS Google Scholar
Constable, E. C., Lewis, J., Liptrot, M. C. & Raithby, P. R. (1990). Inorg. Chim. Acta, 178, 47–54. CSD CrossRef CAS Web of Science Google Scholar
Hou, L. & Li, D. (2005). Inorg. Chem. Commun. 8, 128–130. Web of Science CSD CrossRef CAS Google Scholar
Rao, K. M., Rao, C. R. K. & Zacharias, P. S. (1997). Polyhedron, 16, 2369–2374. CSD CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shi, W.-J., Hou, L., Li, D. & Yin, Y.-G. (2007). Inorg. Chim. Acta, 360, 588–598. Web of Science CSD CrossRef CAS Google Scholar
Tu, Q.-D., Li, D., Wu, T., Yin, Y.-G. & Ng, S. W. (2004). Acta Cryst. E60, m1403–m1404. Web of Science CSD CrossRef IUCr Journals Google Scholar
Xie, H.-Y., Zhang, L. & Shi, W.-J. (2008). Acta Cryst. E64, m42–m43. Web of Science CSD CrossRef IUCr Journals Google Scholar

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