Poly[(μ2-2,2′-bipyridine-κ2N:N′)bis­(μ3-2,2,2-trifluoro­acetato-κ3O:O:O′)disilver(I)]

Arman, H.D.; Miller, T.; Tiekink, E.R.T.

doi:10.1107/S1600536810035282

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages m1209-m1210

doi:10.1107/S1600536810035282

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Poly[(μ₂-2,2′-bipyridine-κ²N:N′)bis(μ₃-2,2,2-trifluoroacetato-κ³O:O:O′)disilver(I)]

Hadi D. Arman,^a Tyler Miller ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 25 August 2010; accepted 1 September 2010; online 4 September 2010)

In the title salt, [Ag₂(CF₃CO₂)₂(C₁₀H₈N₂)]_n, which may also be regarded as a coordination polymer if long Ag⋯O interactions are considered, each of the N atoms of the somewhat twisted 2,2′-bipyridine molecule [N—C—C—N = −27.5 (4)°] binds to an Ag atom, and each of the carboxylate ligands is tridentate, linking to three Ag atoms. The bidentate carboxylate O atoms bridge the same two Ag atoms, resulting in the formation of Ag₂O₂ rings. These rings are bridged by the 2,2′-bipyridine ligands, forming a chain along the b axis. The chains are linked into double chains via the remaining Ag—O bonds and Ag⋯Ag contacts. As a consequence of the Ag⋯Ag contacts, the NO₄ donor set about each Ag atom is heavily distorted. Finally, the chains are linked into a three-dimensional network by a combination of C—H⋯O and C—H⋯F interactions.

Related literature

For structural diversity in the supramolecular structures of silver salts, see: Kundu et al. (2010 ). For a related Ag salt, see: Arman et al. (2010 ).

Experimental

Crystal data

[Ag₂(C₂F₃O₂)₂(C₁₀H₈N₂)]
M_r = 597.96
Monoclinic, C 2/c
a = 24.597 (6) Å
b = 6.8474 (14) Å
c = 21.253 (5) Å
β = 116.029 (4)°
V = 3216.5 (13) Å³
Z = 8
Mo Kα radiation
μ = 2.53 mm⁻¹
T = 98 K
0.31 × 0.29 × 0.20 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.619, T_max = 1.000
10231 measured reflections
3662 independent reflections
3469 reflections with I > 2σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.091
S = 1.09
3661 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.66 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—O1	2.284 (2)
Ag1—N1	2.309 (3)
Ag1—O2ⁱ	2.323 (3)
Ag1—O3ⁱⁱ	2.844 (2)
Ag1—O2	2.993 (3)
Ag1⋯Ag1ⁱ	3.0675 (9)
Ag1⋯Ag2	3.1941 (7)
Ag2—O3	2.276 (2)
Ag2—O4ⁱⁱⁱ	2.280 (3)
Ag2—N2	2.326 (3)
Ag2—O1^iv	2.837 (2)
Ag2—O4	3.069 (3)
Ag2⋯Ag2ⁱⁱⁱ	2.9687 (8)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) x, y-1, z; (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iv) x, y+1, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1^v	0.95	2.50	3.410 (4)	159
C8—H8⋯O3^vi	0.95	2.58	3.287 (4)	132
C1—H1⋯F6ⁱⁱ	0.95	2.54	3.072 (4)	116
C2—H2⋯F4^vii	0.95	2.55	3.145 (4)	121
C10—H10⋯F3^iv	0.95	2.52	3.076 (4)	117
Symmetry codes: (ii) x, y-1, z; (iv) x, y+1, z; (v) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035282/hb5622sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035282/hb5622Isup2.hkl

checkCIF report

Comment top

Supramolecular structures of silver salts are highly dependent upon the nature of counter anions and the presence of solvent (Kundu et al., 2010). During the course of on-going crystal engineering studies on silver salts (Arman et al., 2010), the title salt was isolated and characterized.

The asymmetric unit of (I) comprises two Ag cations, a 2,2'-bipyridine molecule and two trifluoroacetate anions, Fig. 1. Each of the 2,2'-bipyridine-N atoms coordinates to a Ag atom bringing into close proximity the Ag1 and Ag2 atoms [Ag1···Ag2 = 3.1941 (7) Å]. In order to relive steric pressure, the 2,2'-bipyridine molecule is twisted as seen in the torsion angle [N1–C5–C6–N2 = -27.5 (4) °] and the dihedral angle formed between the pyridine rings of 26.93 (15) °. Each Ag atom forms a close Ag–O bond to a carboxylate-O, i.e. Ag1–O1 and Ag2–O3, Table 1, and each of the O1 and O3 atoms also bridges a neighbouring Ag atom to form a non-planar Ag₂O₂ ring. The second carboxylate-O atom in each case, i.e. O2 and O4, bridges to a different Ag atom so that each carboxylate ligand is tridentate. The supramolecular assembly is a double chain along the b axis whereby one row of Ag₂O₂ rings bridged by 2,2'-bipyridine molecules is connected to a second row via the Ag1–O2 and Ag2–O4 bonds and vice versa. Additional stability to the double chain is afforded by Ag1···Ag1 and Ag2···Ag2 interactions, Fig. 2 and Table 1. In terms of coordination geometry, each Ag atom exists within a NO₃ donor set which is grossly distorted owing to the presence of two close Ag···Ag contacts. Chains are consolidated in the crystal packing by a combination of C–H···O and C–H···F contacts, Table 2.

Related literature top

For structural diversity in the supramolecular structures of silver salts, see: Kundu et al. (2010). For a related Ag salt, see: Arman et al. (2010).

Experimental top

2,2'-Bipyridine (0.015 g, 0.1 mmol) was dissolved in 5 ml of methanol. Added to this was silver trifluoroacetate (0.044 g, 0.2 mmol) dissolved in 7 ml of methanol. The resulting solution was gently heated and allowed to stand for slow evaporation affording colourless blocks of (I) after five days.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Asymmetric unit in the structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. Portion of the supramolecular double chain aligned along the b axis in (I).

Poly[(µ₂-2,2'-bipyridine-κ²N:N')bis(µ₃-2,2,2- trifluoroacetato-κ³O:O:O')disilver(I)] top

Crystal data top

[Ag₂(C₂F₃O₂)₂(C₁₀H₈N₂)]	F(000) = 2288
M_r = 597.96	D_x = 2.470 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 8570 reflections
a = 24.597 (6) Å	θ = 1.8–40.5°
b = 6.8474 (14) Å	µ = 2.53 mm⁻¹
c = 21.253 (5) Å	T = 98 K
β = 116.029 (4)°	Block, colourless
V = 3216.5 (13) Å³	0.31 × 0.29 × 0.20 mm
Z = 8

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3662 independent reflections
Radiation source: fine-focus sealed tube	3469 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.037
ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −25→31
T_min = 0.619, T_max = 1.000	k = −8→8
10231 measured reflections	l = −27→27

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0473P)² + 8.2186P] where P = (F_o² + 2F_c²)/3
3661 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.66 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

[Ag₂(C₂F₃O₂)₂(C₁₀H₈N₂)]	V = 3216.5 (13) Å³
M_r = 597.96	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.597 (6) Å	µ = 2.53 mm⁻¹
b = 6.8474 (14) Å	T = 98 K
c = 21.253 (5) Å	0.31 × 0.29 × 0.20 mm
β = 116.029 (4)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3662 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3469 reflections with I > 2σ(I)
T_min = 0.619, T_max = 1.000	R_int = 0.037
10231 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.09	Δρ_max = 0.66 e Å⁻³
3661 reflections	Δρ_min = −0.65 e Å⁻³
253 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.270544 (11)	0.27690 (4)	0.078818 (12)	0.01708 (10)
Ag2	0.239869 (12)	0.73275 (4)	0.063674 (12)	0.01661 (10)
F1	0.05870 (11)	0.2464 (3)	0.01451 (13)	0.0250 (5)
F2	0.04349 (10)	0.0721 (4)	−0.07648 (10)	0.0313 (5)
F3	0.07622 (10)	−0.0612 (3)	0.02507 (11)	0.0243 (4)
F4	0.45993 (11)	0.7568 (3)	0.16884 (13)	0.0287 (5)
F5	0.45617 (9)	0.9732 (3)	0.09408 (11)	0.0298 (5)
F6	0.43891 (9)	1.0540 (3)	0.18104 (11)	0.0296 (5)
O1	0.18662 (10)	0.1008 (3)	0.06300 (11)	0.0186 (5)
O2	0.15108 (12)	0.2233 (3)	−0.04584 (13)	0.0207 (5)
O3	0.32741 (11)	0.9056 (3)	0.11732 (12)	0.0189 (5)
O4	0.35046 (13)	0.7790 (4)	0.03384 (13)	0.0234 (5)
N1	0.32454 (12)	0.4507 (4)	0.18047 (13)	0.0148 (5)
N2	0.20388 (13)	0.5665 (4)	0.13321 (13)	0.0161 (5)
C1	0.38483 (15)	0.4390 (5)	0.20200 (16)	0.0179 (6)
H1	0.3991	0.4009	0.1689	0.021*
C2	0.42676 (14)	0.4794 (5)	0.26943 (17)	0.0187 (6)
H2	0.4688	0.4668	0.2826	0.022*
C3	0.40639 (15)	0.5387 (5)	0.31752 (16)	0.0185 (6)
H3	0.4343	0.5682	0.3643	0.022*
C4	0.34421 (15)	0.5545 (4)	0.29617 (15)	0.0166 (6)
H4	0.3291	0.5951	0.3283	0.020*
C5	0.30455 (14)	0.5100 (4)	0.22711 (16)	0.0156 (6)
C6	0.23773 (14)	0.5279 (4)	0.20229 (16)	0.0147 (6)
C7	0.21148 (15)	0.5069 (4)	0.24806 (15)	0.0160 (6)
H7	0.2361	0.4826	0.2964	0.019*
C8	0.14863 (16)	0.5217 (5)	0.22253 (18)	0.0205 (6)
H8	0.1300	0.5092	0.2531	0.025*
C9	0.11430 (15)	0.5549 (5)	0.15166 (18)	0.0193 (6)
H9	0.0715	0.5625	0.1325	0.023*
C10	0.14338 (15)	0.5769 (4)	0.10896 (17)	0.0182 (6)
H10	0.1195	0.6004	0.0604	0.022*
C11	0.14613 (14)	0.1417 (4)	0.00329 (15)	0.0156 (6)
C12	0.08041 (15)	0.0970 (5)	−0.00906 (16)	0.0174 (6)
C13	0.36199 (14)	0.8644 (4)	0.09028 (15)	0.0149 (6)
C14	0.42956 (15)	0.9154 (5)	0.13331 (16)	0.0174 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.01380 (15)	0.02195 (15)	0.01404 (15)	−0.00357 (9)	0.00477 (11)	−0.00392 (8)
Ag2	0.01414 (15)	0.02253 (15)	0.01274 (15)	−0.00263 (8)	0.00552 (11)	0.00048 (8)
F1	0.0216 (12)	0.0243 (10)	0.0344 (12)	0.0023 (8)	0.0171 (10)	−0.0020 (8)
F2	0.0195 (10)	0.0516 (14)	0.0162 (10)	−0.0099 (10)	0.0017 (8)	−0.0047 (9)
F3	0.0235 (10)	0.0207 (9)	0.0324 (11)	−0.0027 (8)	0.0158 (9)	0.0038 (8)
F4	0.0181 (11)	0.0223 (10)	0.0330 (13)	0.0050 (8)	−0.0005 (10)	0.0093 (8)
F5	0.0195 (10)	0.0442 (13)	0.0257 (11)	−0.0064 (10)	0.0100 (9)	0.0057 (9)
F6	0.0182 (10)	0.0323 (11)	0.0288 (11)	−0.0015 (8)	0.0017 (9)	−0.0153 (9)
O1	0.0154 (11)	0.0236 (11)	0.0126 (10)	−0.0014 (9)	0.0024 (9)	−0.0004 (8)
O2	0.0187 (13)	0.0276 (12)	0.0190 (12)	0.0018 (9)	0.0112 (11)	0.0058 (9)
O3	0.0144 (11)	0.0240 (11)	0.0180 (10)	−0.0016 (9)	0.0068 (9)	−0.0030 (9)
O4	0.0192 (13)	0.0307 (13)	0.0158 (12)	0.0028 (10)	0.0035 (11)	−0.0065 (9)
N1	0.0164 (12)	0.0141 (11)	0.0121 (11)	−0.0021 (10)	0.0045 (10)	−0.0019 (9)
N2	0.0171 (13)	0.0170 (12)	0.0133 (12)	0.0010 (10)	0.0058 (10)	0.0029 (9)
C1	0.0185 (15)	0.0191 (14)	0.0156 (14)	−0.0022 (12)	0.0070 (13)	−0.0038 (11)
C2	0.0140 (14)	0.0221 (15)	0.0185 (15)	−0.0027 (13)	0.0058 (12)	−0.0019 (12)
C3	0.0196 (16)	0.0204 (14)	0.0112 (13)	0.0010 (12)	0.0027 (12)	−0.0015 (11)
C4	0.0206 (16)	0.0149 (13)	0.0117 (13)	0.0010 (11)	0.0048 (12)	−0.0013 (11)
C5	0.0196 (15)	0.0117 (13)	0.0163 (14)	−0.0001 (12)	0.0086 (12)	0.0012 (10)
C6	0.0174 (14)	0.0102 (12)	0.0173 (14)	0.0011 (11)	0.0083 (12)	−0.0011 (10)
C7	0.0243 (16)	0.0141 (13)	0.0110 (13)	0.0007 (13)	0.0091 (12)	0.0022 (10)
C8	0.0291 (18)	0.0154 (14)	0.0245 (16)	−0.0005 (13)	0.0185 (15)	−0.0012 (12)
C9	0.0162 (15)	0.0160 (13)	0.0268 (16)	−0.0010 (12)	0.0105 (13)	−0.0021 (12)
C10	0.0175 (15)	0.0162 (14)	0.0185 (14)	−0.0010 (12)	0.0057 (13)	0.0018 (11)
C11	0.0137 (14)	0.0162 (13)	0.0138 (13)	−0.0009 (12)	0.0031 (11)	−0.0016 (11)
C12	0.0154 (15)	0.0203 (15)	0.0155 (14)	−0.0012 (12)	0.0059 (12)	−0.0027 (11)
C13	0.0119 (14)	0.0150 (13)	0.0142 (13)	0.0000 (11)	0.0024 (11)	0.0008 (11)
C14	0.0152 (15)	0.0184 (14)	0.0171 (14)	0.0006 (12)	0.0057 (12)	0.0008 (11)

Geometric parameters (Å, º) top

Ag1—O1	2.284 (2)	O4—Ag2ⁱⁱⁱ	2.280 (3)
Ag1—N1	2.309 (3)	N1—C5	1.348 (4)
Ag1—O2ⁱ	2.323 (3)	N1—C1	1.349 (4)
Ag1—O3ⁱⁱ	2.844 (2)	N2—C10	1.346 (4)
Ag1—O2	2.993 (3)	N2—C6	1.359 (4)
Ag1—Ag1ⁱ	3.0675 (9)	C1—C2	1.377 (4)
Ag1—Ag2	3.1941 (7)	C1—H1	0.9500
Ag2—O3	2.276 (2)	C2—C3	1.382 (4)
Ag2—O4ⁱⁱⁱ	2.280 (3)	C2—H2	0.9500
Ag2—N2	2.326 (3)	C3—C4	1.396 (5)
Ag2—O1^iv	2.837 (2)	C3—H3	0.9500
Ag2—O4	3.069 (3)	C4—C5	1.394 (4)
Ag2—Ag2ⁱⁱⁱ	2.9687 (8)	C4—H4	0.9500
F1—C12	1.348 (4)	C5—C6	1.495 (4)
F2—C12	1.328 (4)	C6—C7	1.391 (4)
F3—C12	1.333 (4)	C7—C8	1.400 (5)
F4—C14	1.346 (4)	C7—H7	0.9500
F5—C14	1.326 (4)	C8—C9	1.385 (5)
F6—C14	1.333 (4)	C8—H8	0.9500
O1—C11	1.254 (4)	C9—C10	1.388 (4)
O2—C11	1.237 (4)	C9—H9	0.9500
O2—Ag1ⁱ	2.322 (3)	C10—H10	0.9500
O3—C13	1.250 (4)	C11—C12	1.550 (4)
O4—C13	1.250 (4)	C13—C14	1.545 (4)

O1—Ag1—N1	121.42 (9)	C5—C4—C3	119.1 (3)
O1—Ag1—O2ⁱ	140.48 (9)	C5—C4—H4	120.5
N1—Ag1—O2ⁱ	94.01 (9)	C3—C4—H4	120.5
O1—Ag1—Ag1ⁱ	86.13 (5)	N1—C5—C4	121.9 (3)
N1—Ag1—Ag1ⁱ	149.60 (7)	N1—C5—C6	117.7 (3)
O2ⁱ—Ag1—Ag1ⁱ	65.77 (7)	C4—C5—C6	120.4 (3)
O1—Ag1—Ag2	110.04 (6)	N2—C6—C7	121.6 (3)
N1—Ag1—Ag2	66.67 (7)	N2—C6—C5	117.0 (3)
O2ⁱ—Ag1—Ag2	99.26 (6)	C7—C6—C5	121.4 (3)
Ag1ⁱ—Ag1—Ag2	93.284 (12)	C6—C7—C8	119.6 (3)
O3—Ag2—O4ⁱⁱⁱ	143.51 (9)	C6—C7—H7	120.2
O3—Ag2—N2	118.43 (9)	C8—C7—H7	120.2
O4ⁱⁱⁱ—Ag2—N2	93.99 (10)	C9—C8—C7	118.4 (3)
O3—Ag2—Ag2ⁱⁱⁱ	85.12 (6)	C9—C8—H8	120.8
O4ⁱⁱⁱ—Ag2—Ag2ⁱⁱⁱ	70.16 (7)	C7—C8—H8	120.8
N2—Ag2—Ag2ⁱⁱⁱ	151.77 (7)	C8—C9—C10	119.1 (3)
O3—Ag2—Ag1	109.14 (6)	C8—C9—H9	120.5
O4ⁱⁱⁱ—Ag2—Ag1	98.63 (6)	C10—C9—H9	120.5
N2—Ag2—Ag1	66.22 (7)	N2—C10—C9	123.0 (3)
Ag2ⁱⁱⁱ—Ag2—Ag1	92.459 (12)	N2—C10—H10	118.5
C11—O1—Ag1	107.24 (19)	C9—C10—H10	118.5
C11—O2—Ag1ⁱ	131.1 (2)	O2—C11—O1	128.8 (3)
C13—O3—Ag2	109.72 (19)	O2—C11—C12	115.3 (3)
C13—O4—Ag2ⁱⁱⁱ	127.5 (2)	O1—C11—C12	115.7 (3)
C5—N1—C1	118.0 (3)	F2—C12—F3	107.7 (3)
C5—N1—Ag1	126.7 (2)	F2—C12—F1	107.7 (3)
C1—N1—Ag1	112.5 (2)	F3—C12—F1	106.1 (2)
C10—N2—C6	118.3 (3)	F2—C12—C11	112.1 (2)
C10—N2—Ag2	113.3 (2)	F3—C12—C11	113.1 (3)
C6—N2—Ag2	123.9 (2)	F1—C12—C11	109.9 (3)
N1—C1—C2	123.4 (3)	O4—C13—O3	129.3 (3)
N1—C1—H1	118.3	O4—C13—C14	114.0 (3)
C2—C1—H1	118.3	O3—C13—C14	116.7 (3)
C1—C2—C3	118.7 (3)	F5—C14—F6	107.3 (3)
C1—C2—H2	120.7	F5—C14—F4	106.7 (3)
C3—C2—H2	120.7	F6—C14—F4	106.2 (3)
C2—C3—C4	118.9 (3)	F5—C14—C13	113.3 (3)
C2—C3—H3	120.5	F6—C14—C13	113.1 (3)
C4—C3—H3	120.5	F4—C14—C13	109.7 (3)

O1—Ag1—Ag2—O3	159.39 (8)	C1—C2—C3—C4	0.3 (5)
N1—Ag1—Ag2—O3	42.84 (9)	C2—C3—C4—C5	0.1 (5)
O2ⁱ—Ag1—Ag2—O3	−47.55 (9)	C1—N1—C5—C4	−1.4 (4)
Ag1ⁱ—Ag1—Ag2—O3	−113.53 (6)	Ag1—N1—C5—C4	158.2 (2)
O1—Ag1—Ag2—O4ⁱⁱⁱ	−44.62 (9)	C1—N1—C5—C6	178.3 (3)
N1—Ag1—Ag2—O4ⁱⁱⁱ	−161.18 (10)	Ag1—N1—C5—C6	−22.1 (4)
O2ⁱ—Ag1—Ag2—O4ⁱⁱⁱ	108.43 (9)	C3—C4—C5—N1	0.5 (5)
Ag1ⁱ—Ag1—Ag2—O4ⁱⁱⁱ	42.45 (7)	C3—C4—C5—C6	−179.2 (3)
O1—Ag1—Ag2—N2	45.95 (9)	C10—N2—C6—C7	−2.5 (4)
N1—Ag1—Ag2—N2	−70.61 (11)	Ag2—N2—C6—C7	152.2 (2)
O2ⁱ—Ag1—Ag2—N2	−161.00 (10)	C10—N2—C6—C5	177.8 (3)
Ag1ⁱ—Ag1—Ag2—N2	133.03 (8)	Ag2—N2—C6—C5	−27.5 (4)
O1—Ag1—Ag2—Ag2ⁱⁱⁱ	−114.92 (6)	N1—C5—C6—N2	−27.5 (4)
N1—Ag1—Ag2—Ag2ⁱⁱⁱ	128.52 (7)	C4—C5—C6—N2	152.2 (3)
O2ⁱ—Ag1—Ag2—Ag2ⁱⁱⁱ	38.13 (7)	N1—C5—C6—C7	152.8 (3)
Ag1ⁱ—Ag1—Ag2—Ag2ⁱⁱⁱ	−27.845 (17)	C4—C5—C6—C7	−27.5 (4)
N1—Ag1—O1—C11	132.75 (19)	N2—C6—C7—C8	1.3 (4)
O2ⁱ—Ag1—O1—C11	−76.9 (2)	C5—C6—C7—C8	−179.0 (3)
Ag1ⁱ—Ag1—O1—C11	−33.61 (19)	C6—C7—C8—C9	0.7 (5)
Ag2—Ag1—O1—C11	58.5 (2)	C7—C8—C9—C10	−1.5 (5)
O4ⁱⁱⁱ—Ag2—O3—C13	−78.8 (2)	C6—N2—C10—C9	1.7 (5)
N2—Ag2—O3—C13	131.3 (2)	Ag2—N2—C10—C9	−155.6 (3)
Ag2ⁱⁱⁱ—Ag2—O3—C13	−32.30 (19)	C8—C9—C10—N2	0.3 (5)
Ag1—Ag2—O3—C13	58.6 (2)	Ag1ⁱ—O2—C11—O1	31.3 (5)
O1—Ag1—N1—C5	−20.2 (3)	Ag1ⁱ—O2—C11—C12	−153.5 (2)
O2ⁱ—Ag1—N1—C5	178.2 (2)	Ag1—O1—C11—O2	15.3 (4)
Ag1ⁱ—Ag1—N1—C5	132.1 (2)	Ag1—O1—C11—C12	−159.9 (2)
Ag2—Ag1—N1—C5	79.9 (2)	O2—C11—C12—F2	27.9 (4)
O1—Ag1—N1—C1	140.4 (2)	O1—C11—C12—F2	−156.2 (3)
O2ⁱ—Ag1—N1—C1	−21.3 (2)	O2—C11—C12—F3	149.9 (3)
Ag1ⁱ—Ag1—N1—C1	−67.4 (3)	O1—C11—C12—F3	−34.2 (4)
Ag2—Ag1—N1—C1	−119.6 (2)	O2—C11—C12—F1	−91.8 (3)
O3—Ag2—N2—C10	140.1 (2)	O1—C11—C12—F1	84.1 (3)
O4ⁱⁱⁱ—Ag2—N2—C10	−22.5 (2)	Ag2ⁱⁱⁱ—O4—C13—O3	26.8 (5)
Ag2ⁱⁱⁱ—Ag2—N2—C10	−76.4 (3)	Ag2ⁱⁱⁱ—O4—C13—C14	−156.6 (2)
Ag1—Ag2—N2—C10	−120.2 (2)	Ag2—O3—C13—O4	15.0 (4)
O3—Ag2—N2—C6	−15.7 (3)	Ag2—O3—C13—C14	−161.6 (2)
O4ⁱⁱⁱ—Ag2—N2—C6	−178.3 (2)	O4—C13—C14—F5	38.5 (4)
Ag2ⁱⁱⁱ—Ag2—N2—C6	127.8 (2)	O3—C13—C14—F5	−144.4 (3)
Ag1—Ag2—N2—C6	84.0 (2)	O4—C13—C14—F6	160.9 (3)
C5—N1—C1—C2	1.8 (5)	O3—C13—C14—F6	−22.0 (4)
Ag1—N1—C1—C2	−160.6 (3)	O4—C13—C14—F4	−80.7 (3)
N1—C1—C2—C3	−1.3 (5)	O3—C13—C14—F4	96.5 (3)

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x, y−1, z; (iii) −x+1/2, −y+3/2, −z; (iv) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^v	0.95	2.50	3.410 (4)	159
C8—H8···O3^vi	0.95	2.58	3.287 (4)	132
C1—H1···F6ⁱⁱ	0.95	2.54	3.072 (4)	116
C2—H2···F4^vii	0.95	2.55	3.145 (4)	121
C10—H10···F3^iv	0.95	2.52	3.076 (4)	117

Symmetry codes: (ii) x, y−1, z; (iv) x, y+1, z; (v) −x+1/2, y+1/2, −z+1/2; (vi) −x+1/2, y−1/2, −z+1/2; (vii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ag₂(C₂F₃O₂)₂(C₁₀H₈N₂)]
M_r	597.96
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	98
a, b, c (Å)	24.597 (6), 6.8474 (14), 21.253 (5)
β (°)	116.029 (4)
V (Å³)	3216.5 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.53
Crystal size (mm)	0.31 × 0.29 × 0.20

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.619, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10231, 3662, 3469
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.091, 1.09
No. of reflections	3661
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.65

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ag1—O1	2.284 (2)	Ag2—O3	2.276 (2)
Ag1—N1	2.309 (3)	Ag2—O4ⁱⁱⁱ	2.280 (3)
Ag1—O2ⁱ	2.323 (3)	Ag2—N2	2.326 (3)
Ag1—O3ⁱⁱ	2.844 (2)	Ag2—O1^iv	2.837 (2)
Ag1—O2	2.993 (3)	Ag2—O4	3.069 (3)
Ag1—Ag1ⁱ	3.0675 (9)	Ag2—Ag2ⁱⁱⁱ	2.9687 (8)
Ag1—Ag2	3.1941 (7)

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) x, y−1, z; (iii) −x+1/2, −y+3/2, −z; (iv) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1^v	0.95	2.50	3.410 (4)	159
C8—H8···O3^vi	0.95	2.58	3.287 (4)	132
C1—H1···F6ⁱⁱ	0.95	2.54	3.072 (4)	116
C2—H2···F4^vii	0.95	2.55	3.145 (4)	121
C10—H10···F3^iv	0.95	2.52	3.076 (4)	117

Symmetry codes: (ii) x, y−1, z; (iv) x, y+1, z; (v) −x+1/2, y+1/2, −z+1/2; (vi) −x+1/2, y−1/2, −z+1/2; (vii) −x+1, y, −z+1/2.

References

Arman, H. D., Miller, T., Poplaukhin, P. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m1167–m1168. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Kundu, N., Audhya, A., Towsif Abtab, Sk. Md., Ghosh, S., Tiekink, E. R. T. & Chaudhury, M. (2010). Cryst. Growth Des. 10, 1269–1282. Web of Science CSD CrossRef CAS Google Scholar
Molecular Structure Corporation & Rigaku (2005). CrystalClear. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 10| October 2010| Pages m1209-m1210

doi:10.1107/S1600536810035282

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