catena-Poly[[silver(I)-μ-4,4′-bipyridine-κ2N:N′] 4-[2-(4-carb­oxy­phen­yl)-1,1,1,3,3,3-hexa­fluoro­propan-2-yl]benzoate]

Jiang, X.-J.

doi:10.1107/S1600536812015322

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m613-m614

doi:10.1107/S1600536812015322

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catena-Poly[[silver(I)-μ-4,4′-bipyridine-κ²N:N′] 4-[2-(4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoate]

Xiu-Juan Jiang ^a ^*

^aCollege of Biological, Chemical Sciences and Engineering, Jiaxing University, Zhejiang Jiaxing 314001, People's Republic of China
^*Correspondence e-mail: jiangjxj@yahoo.cn

(Received 23 March 2012; accepted 7 April 2012; online 18 April 2012)

Assembly of the flexible dicarboxylic ligand 4-[2-(4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoate and 4,4′-bipyridine as co-ligand with Ag^I ions resulted in the formation of the polymeric title compound, {[Ag(C₁₀H₈N₂)](C₁₇H₉F₆O₄)}_n, in which the metal atoms are bridged by the 4,4′-bipyridine ligands, generating cationic chains extending along [010]. The dihedral angles between the benzene rings in the anion and the pyridine rings in the cation are 72.42 (9) and 9.36 (10)°, respectively. The molecular conformation of the anion is stabilized by intramolecular C—H⋯F hydrogen bonds. In the crystal, the anions interact with the cationic chains via C—H⋯O hydrogen bonds, forming layers parallel to (001), in which weak π–π stacking interactions [centroid–centroid distances = 3.975 (3)–4.047 (3) Å] involving the pyridine rings of adjacent 4,4′-bipyridine ligands are present. The planes are further assembled into a three-dimensional network by O—H⋯O hydrogen bonds.

Related literature

For background to metal-organic frameworks, see: Du et al. (2007 ); Li & Du (2011 ); Hosseini (2005 ). For metallosupramolecular architectures, see: Brammer (2004 ); Peedikakkal & Vittal (2011 ). For coordination frameworks constructed from pyridyl and carboxylate spacers, see: Li et al. (2012 ). For weak cooperative intermolecular interactions, see: Ye et al. (2005 ). For flexible polycarboxyl ligands, see: Liu et al. (2011 ). For the structures of metal complexes derived from 4-[2-(4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoate, see: Jiang et al. (2009 ); Ji et al. (2010 ).

Experimental

Crystal data

[Ag(C₁₀H₈N₂)](C₁₇H₉F₆O₄)
M_r = 655.30
Monoclinic, P 2₁ /c
a = 16.434 (7) Å
b = 11.436 (5) Å
c = 14.320 (6) Å
β = 104.310 (7)°
V = 2607.9 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.85 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.817, T_max = 0.862
12604 measured reflections
4604 independent reflections
3593 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.080
S = 1.06
4604 reflections
362 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2ⁱ	0.82	1.72	2.538 (2)	174
C4—H4A⋯O1ⁱⁱ	0.93	2.52	3.366 (4)	152
C7—H7⋯O1ⁱⁱ	0.93	2.54	3.297 (4)	138
C8—H8⋯O3	0.93	2.53	3.312 (4)	142
C9—H9⋯O2ⁱⁱⁱ	0.93	2.48	3.242 (4)	139
C16—H16⋯F4	0.93	2.35	2.992 (4)	126
C26—H26⋯F3	0.93	2.33	2.941 (4)	123
Symmetry codes: (i) -x, -y+2, -z+1; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x+1, y, z.

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2001); 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: 10.1107/S1600536812015322/rz2731sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015322/rz2731Isup2.hkl

checkCIF report

Comment top

Research on metal-organic frameworks (MOFs) has been rapidly developed to produce new materials with fascinating structural topologies and potential applications (Du et al., 2007; Li & Du, 2011; Hosseini et al., 2005). Generally, the diversity of the network structures of such materials greatly depends on the selection of the well designed organic ligands and metal centers, and a variety of novel metallosupramolecular architectures have been obtained so far (Brammer et al., 2004; Peedikakkal et al., 2011). Accordingly, ligands with certain functional groups, such as pyridyl and carboxylate have been widely explored to construct such coordination frameworks (Li et al., 2012). In addition, aside from the fundamental coordination driven force, other weak cooperative intermolecular interactions such as hydrogen bonding and aromatic stacking are also useful tools in the construction of such crystalline solids (Ye et al., 2005). Among the versatile dicarboxylate tectons, the conformational freedom nature of the flexible polycarboxyl modules may provide more possibility for the construction of unusual coordination frameworks compared with rigid ligands (Liu et al., 2011). 4,4'-(Hexafluoroisopropylidene)bis(benzoic acid) (H₂L) as a V-shaped flexible dicarboxyl ligand has been investigated for its bent geometry, which can induce novel topological motifs and potential functional materials (Jiang et al., 2009; Ji et al., 2010). Herein the synthesis and structure of a new crystalline complex is reported, generated from the incorporation of the V-shaped dicarboxyl spacer H₂L with 4,4'-bipyridine (bipy) as co-ligand and Ag^I ion, which displays a one-dimensional polymeric chain motif.

The asymmetric unit of the title compound consists of one silver(I) cation, one bipy molecule and one HL anion (Fig. 1). Each metal atom is coordinated in a nearly linear geometry (N2—Ag1—N1ⁱ = 171.36 (9)°; symmetry code: (i) x, -1+y, z) by a pair of nitrogen donors from two bipy molecules, forming one-dimensional polymeric chain motifs along the [010] direction with Ag···Ag separations of 11.436 (5) Å. If the Ag···O separations with the monoprotonated carboxylate anion are considered (Ag1···O2, 2.680 (2) Å; Ag1···O1, 2.701 (2) Å), the HL ligands can be seen as pendants of the Ag-bipy chains. In the cation, the dihedral angle formed by the pyridine rings is 72.42 (9)°, while the dihedral angle formed by the benzene rings in the anion is 9.36 (10)°. The molecular conformation of the anion is enforced by intramolecular C—H···F hydrogen bonds (Table 1). In the crystal packing, anions and cationic chains interact through C—H···O hydrogen bonds to generate layers parallel to the ab plane. In each layer, weak π–π stacking interactions (centroid-to-centroid distances = 3.975 (3)–4.047 (3) Å) involving the pyridine rings of adjacent bipy ligands are observed (Fig. 2). Interplanar O—H···O hydrogen bond involving the carboxylic and carboxylate groups further assemble the layers in a three-dimensional network.

Related literature top

For background to metal-organic frameworks, see: Du et al. (2007); Li & Du (2011); Hosseini (2005). For metallosupramolecular architectures, see: Brammer (2004); Peedikakkal & Vittal (2011). For coordination frameworks constructed from pyridyl and carboxylate spacers, see: Li et al. (2012). For weak cooperative intermolecular interactions, see: Ye et al. (2005). For flexible polycarboxyl ligands, see: Liu et al. (2011). For the structures of 4,4'-(hexafluoroisopropylidene)bis(benzoic acid) complexes, see: Jiang et al. (2009); Ji et al. (2010).

Experimental top

A mixture of H₂L (20.2 mg, 0.05 mmol), silver acetate (16.8 mg, 0.10 mmol), 4,4'-bipyridine (15.4 mg, 0.10 mmol) and water (10 ml) was sealed in a Teflon-lined stainless steel vessel (20 ml), which was heated at 433°C for three days and then cooled to room temperature. Colourless needle-like crystals of title compound were obtained in 61% yield (20.0 mg, based on H₂L).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2001); 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 asymmetric unit of title compound with 30% probability displacement ellipsoids [symmetry codes: (i) x, -1+y, z; (ii) = x, 1+y,z).
	Fig. 2. View of the 3-D supramolecular organization of the title compound constructed from π–π stacking interactions (green dotted lines) and hydrogen bonds (dotted lines). Overlapping layers parallel to the ab plane are coloured in blue and magenta.

catena-Poly[[silver(I)-µ-4,4'-bipyridine-κ²N:N'] 4-[2-(4-carboxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]benzoate] top

Crystal data top

[Ag(C₁₀H₈N₂)](C₁₇H₉F₆O₄)	F(000) = 1304
M_r = 655.30	D_x = 1.669 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3592 reflections
a = 16.434 (7) Å	θ = 2.6–25.0°
b = 11.436 (5) Å	µ = 0.85 mm⁻¹
c = 14.320 (6) Å	T = 296 K
β = 104.310 (7)°	Block, colourless
V = 2607.9 (19) Å³	0.24 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4604 independent reflections
Radiation source: fine-focus sealed tube	3593 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
phi and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −19→18
T_min = 0.817, T_max = 0.862	k = −13→11
12604 measured reflections	l = −13→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0345P)² + 0.8598P] where P = (F_o² + 2F_c²)/3
4604 reflections	(Δ/σ)_max = 0.001
362 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Ag(C₁₀H₈N₂)](C₁₇H₉F₆O₄)	V = 2607.9 (19) Å³
M_r = 655.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.434 (7) Å	µ = 0.85 mm⁻¹
b = 11.436 (5) Å	T = 296 K
c = 14.320 (6) Å	0.24 × 0.20 × 0.18 mm
β = 104.310 (7)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4604 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3593 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.862	R_int = 0.029
12604 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.06	Δρ_max = 0.32 e Å⁻³
4604 reflections	Δρ_min = −0.47 e Å⁻³
362 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	0.530651 (16)	−0.082641 (18)	0.622126 (19)	0.04658 (10)
F1	0.02974 (15)	0.6454 (2)	0.92201 (18)	0.0909 (8)
F2	0.06031 (13)	0.61728 (17)	0.78671 (18)	0.0684 (6)
F3	0.15860 (14)	0.6401 (2)	0.91554 (16)	0.0829 (7)
F4	0.09383 (15)	0.8354 (2)	1.01974 (14)	0.0868 (8)
F5	0.10424 (14)	0.9881 (2)	0.93702 (15)	0.0757 (7)
F6	0.20357 (13)	0.8623 (3)	0.96704 (15)	0.0886 (8)
O1	−0.32135 (14)	0.9301 (2)	0.75562 (17)	0.0601 (7)
O2	−0.31043 (12)	0.90448 (18)	0.60650 (15)	0.0447 (5)
O3	0.33356 (15)	0.9023 (2)	0.56863 (18)	0.0608 (7)
O4	0.24921 (14)	1.05711 (19)	0.53684 (16)	0.0484 (6)
H4	0.2713	1.0657	0.4919	0.073*
N1	0.52282 (16)	0.7266 (2)	0.62575 (17)	0.0404 (6)
N2	0.51817 (15)	0.1071 (2)	0.61686 (17)	0.0368 (6)
C1	0.58883 (19)	0.2880 (2)	0.6165 (2)	0.0423 (8)
H1	0.6375	0.3270	0.6123	0.051*
C2	0.5861 (2)	0.1688 (2)	0.6116 (2)	0.0424 (8)
H2	0.6334	0.1288	0.6043	0.051*
C3	0.4518 (2)	0.1674 (3)	0.6274 (2)	0.0449 (8)
H3	0.4039	0.1262	0.6306	0.054*
C4	0.45017 (19)	0.2870 (2)	0.6337 (2)	0.0412 (8)
H4A	0.4023	0.3247	0.6421	0.049*
C5	0.52023 (17)	0.3515 (2)	0.62763 (19)	0.0314 (7)
C6	0.52118 (18)	0.4813 (2)	0.63058 (19)	0.0331 (7)
C7	0.44988 (19)	0.5469 (2)	0.6263 (2)	0.0398 (7)
H7	0.3993	0.5096	0.6251	0.048*
C8	0.4531 (2)	0.6668 (2)	0.6239 (2)	0.0416 (8)
H8	0.4038	0.7083	0.6207	0.050*
C9	0.5923 (2)	0.6642 (3)	0.6312 (3)	0.0568 (10)
H9	0.6421	0.7040	0.6331	0.068*
C10	0.5941 (2)	0.5440 (3)	0.6341 (3)	0.0545 (9)
H10	0.6445	0.5046	0.6385	0.065*
C11	−0.27936 (19)	0.9090 (2)	0.6968 (2)	0.0399 (7)
C12	−0.18662 (18)	0.8837 (3)	0.7344 (2)	0.0385 (7)
C13	−0.13701 (19)	0.8418 (3)	0.6766 (2)	0.0410 (7)
H13	−0.1609	0.8275	0.6117	0.049*
C14	−0.05230 (19)	0.8210 (3)	0.7143 (2)	0.0430 (8)
H14	−0.0199	0.7935	0.6741	0.052*
C15	−0.01503 (19)	0.8405 (3)	0.8103 (2)	0.0396 (7)
C16	−0.0646 (2)	0.8806 (3)	0.8685 (2)	0.0558 (9)
H16	−0.0410	0.8934	0.9337	0.067*
C17	−0.1491 (2)	0.9019 (3)	0.8306 (2)	0.0538 (9)
H17	−0.1814	0.9291	0.8710	0.065*
C18	0.07922 (19)	0.8103 (3)	0.8496 (2)	0.0434 (8)
C19	0.0819 (2)	0.6771 (4)	0.8687 (3)	0.0611 (10)
C20	0.1197 (2)	0.8734 (4)	0.9440 (3)	0.0638 (10)
C21	0.13085 (18)	0.8446 (3)	0.7768 (2)	0.0389 (7)
C22	0.1201 (2)	0.9558 (3)	0.7381 (2)	0.0479 (8)
H22	0.0809	1.0055	0.7542	0.057*
C23	0.1665 (2)	0.9947 (3)	0.6759 (2)	0.0472 (8)
H23	0.1586	1.0702	0.6512	0.057*
C24	0.22482 (18)	0.9221 (3)	0.6502 (2)	0.0387 (7)
C25	0.2352 (2)	0.8112 (3)	0.6884 (2)	0.0461 (8)
H25	0.2740	0.7615	0.6716	0.055*
C26	0.18943 (19)	0.7715 (3)	0.7511 (2)	0.0452 (8)
H26	0.1978	0.6962	0.7761	0.054*
C27	0.27476 (19)	0.9585 (3)	0.5814 (2)	0.0408 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.04784 (17)	0.02023 (13)	0.06987 (19)	0.00120 (10)	0.01111 (12)	−0.00107 (11)
F1	0.0822 (18)	0.0897 (17)	0.116 (2)	0.0119 (14)	0.0525 (16)	0.0463 (15)
F2	0.0601 (14)	0.0440 (11)	0.1002 (17)	0.0030 (10)	0.0179 (12)	0.0053 (12)
F3	0.0614 (15)	0.0972 (17)	0.0862 (16)	0.0294 (13)	0.0110 (12)	0.0452 (14)
F4	0.0702 (16)	0.150 (2)	0.0394 (12)	0.0082 (15)	0.0126 (11)	0.0089 (13)
F5	0.0730 (16)	0.0876 (17)	0.0653 (14)	−0.0097 (13)	0.0145 (11)	−0.0295 (13)
F6	0.0400 (13)	0.155 (2)	0.0620 (13)	0.0041 (14)	−0.0043 (10)	−0.0173 (15)
O1	0.0368 (14)	0.0868 (19)	0.0628 (15)	0.0103 (12)	0.0241 (12)	−0.0029 (13)
O2	0.0298 (12)	0.0521 (14)	0.0524 (14)	−0.0024 (10)	0.0106 (10)	0.0057 (11)
O3	0.0441 (15)	0.0664 (17)	0.0788 (17)	0.0175 (12)	0.0285 (13)	0.0164 (13)
O4	0.0456 (14)	0.0492 (13)	0.0532 (14)	0.0041 (11)	0.0173 (11)	0.0054 (11)
N1	0.0398 (16)	0.0243 (13)	0.0561 (16)	0.0021 (11)	0.0095 (12)	−0.0007 (11)
N2	0.0363 (16)	0.0247 (13)	0.0467 (15)	0.0017 (10)	0.0050 (12)	−0.0012 (10)
C1	0.0346 (18)	0.0278 (15)	0.066 (2)	−0.0027 (13)	0.0154 (16)	0.0025 (14)
C2	0.0369 (19)	0.0289 (15)	0.064 (2)	0.0056 (13)	0.0182 (16)	0.0020 (15)
C3	0.038 (2)	0.0294 (16)	0.066 (2)	−0.0050 (14)	0.0113 (16)	0.0012 (15)
C4	0.0319 (18)	0.0280 (15)	0.065 (2)	0.0019 (12)	0.0147 (15)	0.0002 (14)
C5	0.0338 (18)	0.0251 (15)	0.0343 (15)	0.0030 (12)	0.0064 (13)	0.0000 (12)
C6	0.0368 (18)	0.0236 (15)	0.0393 (17)	−0.0010 (12)	0.0102 (13)	−0.0002 (12)
C7	0.0333 (18)	0.0265 (15)	0.063 (2)	0.0005 (12)	0.0177 (15)	0.0014 (14)
C8	0.038 (2)	0.0272 (15)	0.063 (2)	0.0080 (13)	0.0193 (16)	0.0023 (14)
C9	0.038 (2)	0.0297 (17)	0.101 (3)	−0.0049 (14)	0.0131 (19)	−0.0053 (18)
C10	0.0336 (19)	0.0281 (16)	0.100 (3)	0.0026 (14)	0.0124 (18)	−0.0043 (17)
C11	0.0321 (17)	0.0323 (16)	0.057 (2)	−0.0007 (13)	0.0138 (16)	0.0050 (15)
C12	0.0308 (17)	0.0368 (16)	0.0505 (19)	−0.0014 (13)	0.0150 (14)	0.0009 (14)
C13	0.0338 (18)	0.0466 (18)	0.0408 (17)	0.0034 (14)	0.0060 (14)	−0.0029 (15)
C14	0.0350 (19)	0.0513 (19)	0.0442 (18)	0.0081 (15)	0.0129 (15)	−0.0053 (15)
C15	0.0303 (18)	0.0459 (18)	0.0423 (18)	0.0006 (14)	0.0087 (14)	0.0027 (14)
C16	0.040 (2)	0.088 (3)	0.0399 (19)	0.0051 (19)	0.0112 (15)	−0.0084 (18)
C17	0.038 (2)	0.077 (3)	0.051 (2)	0.0028 (18)	0.0194 (16)	−0.0100 (18)
C18	0.0349 (19)	0.055 (2)	0.0395 (18)	0.0039 (15)	0.0073 (14)	0.0052 (15)
C19	0.045 (2)	0.069 (3)	0.071 (3)	0.0093 (19)	0.018 (2)	0.027 (2)
C20	0.043 (2)	0.098 (3)	0.049 (2)	0.006 (2)	0.0063 (18)	−0.004 (2)
C21	0.0263 (17)	0.0460 (18)	0.0414 (17)	0.0026 (13)	0.0028 (13)	0.0007 (14)
C22	0.041 (2)	0.0462 (19)	0.062 (2)	0.0112 (15)	0.0232 (17)	0.0015 (16)
C23	0.042 (2)	0.0393 (18)	0.063 (2)	0.0063 (15)	0.0182 (17)	0.0059 (16)
C24	0.0271 (16)	0.0458 (18)	0.0406 (17)	0.0006 (14)	0.0033 (13)	−0.0029 (15)
C25	0.039 (2)	0.049 (2)	0.052 (2)	0.0141 (15)	0.0130 (16)	0.0012 (16)
C26	0.0374 (19)	0.0458 (19)	0.052 (2)	0.0113 (15)	0.0110 (15)	0.0051 (15)
C27	0.0292 (18)	0.0460 (18)	0.0438 (18)	−0.0028 (14)	0.0025 (14)	−0.0025 (15)

Geometric parameters (Å, º) top

Ag1—N2	2.179 (2)	C8—H8	0.9300
Ag1—N1ⁱ	2.186 (2)	C9—C10	1.376 (4)
F1—C19	1.332 (4)	C9—H9	0.9300
F2—C19	1.329 (4)	C10—H10	0.9300
F3—C19	1.342 (4)	C11—C12	1.514 (4)
F4—C20	1.332 (4)	C12—C17	1.380 (4)
F5—C20	1.335 (5)	C12—C13	1.383 (4)
F6—C20	1.341 (4)	C13—C14	1.384 (4)
O1—C11	1.238 (4)	C13—H13	0.9300
O2—C11	1.268 (4)	C14—C15	1.378 (4)
O3—C27	1.212 (4)	C14—H14	0.9300
O4—C27	1.312 (4)	C15—C16	1.380 (4)
O4—H4	0.8200	C15—C18	1.551 (4)
N1—C8	1.330 (4)	C16—C17	1.381 (5)
N1—C9	1.332 (4)	C16—H16	0.9300
N1—Ag1ⁱⁱ	2.186 (2)	C17—H17	0.9300
N2—C3	1.330 (4)	C18—C20	1.532 (5)
N2—C2	1.338 (4)	C18—C19	1.546 (5)
C1—C2	1.365 (4)	C18—C21	1.549 (4)
C1—C5	1.383 (4)	C21—C22	1.382 (4)
C1—H1	0.9300	C21—C26	1.391 (4)
C2—H2	0.9300	C22—C23	1.381 (4)
C3—C4	1.371 (4)	C22—H22	0.9300
C3—H3	0.9300	C23—C24	1.384 (4)
C4—C5	1.388 (4)	C23—H23	0.9300
C4—H4A	0.9300	C24—C25	1.375 (4)
C5—C6	1.485 (4)	C24—C27	1.490 (4)
C6—C7	1.380 (4)	C25—C26	1.383 (4)
C6—C10	1.387 (4)	C25—H25	0.9300
C7—C8	1.373 (4)	C26—H26	0.9300
C7—H7	0.9300

N2—Ag1—N1ⁱ	171.36 (9)	C13—C14—H14	119.4
C27—O4—H4	109.5	C14—C15—C16	118.2 (3)
C8—N1—C9	116.6 (3)	C14—C15—C18	118.9 (3)
C8—N1—Ag1ⁱⁱ	124.66 (19)	C16—C15—C18	122.8 (3)
C9—N1—Ag1ⁱⁱ	118.7 (2)	C15—C16—C17	120.5 (3)
C3—N2—C2	116.8 (3)	C15—C16—H16	119.7
C3—N2—Ag1	125.8 (2)	C17—C16—H16	119.7
C2—N2—Ag1	117.01 (19)	C12—C17—C16	121.5 (3)
C2—C1—C5	120.8 (3)	C12—C17—H17	119.2
C2—C1—H1	119.6	C16—C17—H17	119.2
C5—C1—H1	119.6	C20—C18—C19	108.8 (3)
N2—C2—C1	122.8 (3)	C20—C18—C21	106.5 (3)
N2—C2—H2	118.6	C19—C18—C21	111.8 (3)
C1—C2—H2	118.6	C20—C18—C15	113.1 (3)
N2—C3—C4	123.7 (3)	C19—C18—C15	105.4 (3)
N2—C3—H3	118.1	C21—C18—C15	111.3 (2)
C4—C3—H3	118.1	F2—C19—F1	107.3 (3)
C3—C4—C5	119.7 (3)	F2—C19—F3	107.0 (3)
C3—C4—H4A	120.1	F1—C19—F3	106.6 (3)
C5—C4—H4A	120.1	F2—C19—C18	111.2 (3)
C1—C5—C4	116.1 (3)	F1—C19—C18	112.0 (3)
C1—C5—C6	121.7 (3)	F3—C19—C18	112.4 (3)
C4—C5—C6	122.2 (3)	F4—C20—F5	106.8 (3)
C7—C6—C10	116.0 (3)	F4—C20—F6	106.5 (3)
C7—C6—C5	122.6 (3)	F5—C20—F6	106.1 (3)
C10—C6—C5	121.4 (3)	F4—C20—C18	114.1 (3)
C8—C7—C6	120.4 (3)	F5—C20—C18	111.3 (3)
C8—C7—H7	119.8	F6—C20—C18	111.6 (3)
C6—C7—H7	119.8	C22—C21—C26	118.3 (3)
N1—C8—C7	123.5 (3)	C22—C21—C18	117.8 (3)
N1—C8—H8	118.2	C26—C21—C18	123.8 (3)
C7—C8—H8	118.2	C23—C22—C21	121.3 (3)
N1—C9—C10	123.3 (3)	C23—C22—H22	119.4
N1—C9—H9	118.4	C21—C22—H22	119.4
C10—C9—H9	118.4	C22—C23—C24	120.4 (3)
C9—C10—C6	120.2 (3)	C22—C23—H23	119.8
C9—C10—H10	119.9	C24—C23—H23	119.8
C6—C10—H10	119.9	C25—C24—C23	118.3 (3)
O1—C11—O2	123.4 (3)	C25—C24—C27	119.1 (3)
O1—C11—C12	118.5 (3)	C23—C24—C27	122.6 (3)
O2—C11—C12	118.1 (3)	C24—C25—C26	121.8 (3)
C17—C12—C13	117.8 (3)	C24—C25—H25	119.1
C17—C12—C11	119.3 (3)	C26—C25—H25	119.1
C13—C12—C11	123.0 (3)	C25—C26—C21	119.9 (3)
C12—C13—C14	120.8 (3)	C25—C26—H26	120.1
C12—C13—H13	119.6	C21—C26—H26	120.1
C14—C13—H13	119.6	O3—C27—O4	123.7 (3)
C15—C14—C13	121.2 (3)	O3—C27—C24	122.8 (3)
C15—C14—H14	119.4	O4—C27—C24	113.5 (3)

C3—N2—C2—C1	−0.1 (5)	C16—C15—C18—C19	95.2 (4)
Ag1—N2—C2—C1	−174.0 (2)	C14—C15—C18—C21	40.0 (4)
C5—C1—C2—N2	0.2 (5)	C16—C15—C18—C21	−143.4 (3)
C2—N2—C3—C4	−0.5 (5)	C20—C18—C19—F2	−169.7 (3)
Ag1—N2—C3—C4	172.8 (2)	C21—C18—C19—F2	−52.4 (4)
N2—C3—C4—C5	1.0 (5)	C15—C18—C19—F2	68.7 (3)
C2—C1—C5—C4	0.2 (4)	C20—C18—C19—F1	70.2 (4)
C2—C1—C5—C6	−178.4 (3)	C21—C18—C19—F1	−172.5 (3)
C3—C4—C5—C1	−0.8 (4)	C15—C18—C19—F1	−51.4 (4)
C3—C4—C5—C6	177.8 (3)	C20—C18—C19—F3	−49.8 (4)
C1—C5—C6—C7	169.5 (3)	C21—C18—C19—F3	67.5 (4)
C4—C5—C6—C7	−9.0 (4)	C15—C18—C19—F3	−171.4 (3)
C1—C5—C6—C10	−8.0 (4)	C19—C18—C20—F4	−46.5 (4)
C4—C5—C6—C10	173.4 (3)	C21—C18—C20—F4	−167.1 (3)
C10—C6—C7—C8	1.3 (4)	C15—C18—C20—F4	70.3 (4)
C5—C6—C7—C8	−176.3 (3)	C19—C18—C20—F5	−167.4 (3)
C9—N1—C8—C7	−0.6 (5)	C21—C18—C20—F5	72.0 (3)
Ag1ⁱⁱ—N1—C8—C7	−179.9 (2)	C15—C18—C20—F5	−50.6 (4)
C6—C7—C8—N1	−0.3 (5)	C19—C18—C20—F6	74.3 (4)
C8—N1—C9—C10	0.5 (5)	C21—C18—C20—F6	−46.4 (4)
Ag1ⁱⁱ—N1—C9—C10	179.8 (3)	C15—C18—C20—F6	−168.9 (3)
N1—C9—C10—C6	0.6 (6)	C20—C18—C21—C22	−74.4 (4)
C7—C6—C10—C9	−1.4 (5)	C19—C18—C21—C22	166.9 (3)
C5—C6—C10—C9	176.2 (3)	C15—C18—C21—C22	49.3 (4)
O1—C11—C12—C17	−9.6 (4)	C20—C18—C21—C26	103.1 (4)
O2—C11—C12—C17	172.1 (3)	C19—C18—C21—C26	−15.6 (4)
O1—C11—C12—C13	169.8 (3)	C15—C18—C21—C26	−133.2 (3)
O2—C11—C12—C13	−8.4 (4)	C26—C21—C22—C23	−0.5 (5)
C17—C12—C13—C14	−1.1 (5)	C18—C21—C22—C23	177.1 (3)
C11—C12—C13—C14	179.4 (3)	C21—C22—C23—C24	0.5 (5)
C12—C13—C14—C15	0.5 (5)	C22—C23—C24—C25	−0.2 (5)
C13—C14—C15—C16	0.4 (5)	C22—C23—C24—C27	178.2 (3)
C13—C14—C15—C18	177.2 (3)	C23—C24—C25—C26	−0.2 (5)
C14—C15—C16—C17	−0.8 (5)	C27—C24—C25—C26	−178.6 (3)
C18—C15—C16—C17	−177.4 (3)	C24—C25—C26—C21	0.2 (5)
C13—C12—C17—C16	0.8 (5)	C22—C21—C26—C25	0.1 (5)
C11—C12—C17—C16	−179.7 (3)	C18—C21—C26—C25	−177.3 (3)
C15—C16—C17—C12	0.1 (6)	C25—C24—C27—O3	−12.0 (4)
C14—C15—C18—C20	159.8 (3)	C23—C24—C27—O3	169.6 (3)
C16—C15—C18—C20	−23.6 (5)	C25—C24—C27—O4	168.5 (3)
C14—C15—C18—C19	−81.5 (4)	C23—C24—C27—O4	−9.9 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2ⁱⁱⁱ	0.82	1.72	2.538 (2)	174
C4—H4A···O1^iv	0.93	2.52	3.366 (4)	152
C7—H7···O1^iv	0.93	2.54	3.297 (4)	138
C8—H8···O3	0.93	2.53	3.312 (4)	142
C9—H9···O2^v	0.93	2.48	3.242 (4)	139
C16—H16···F4	0.93	2.35	2.992 (4)	126
C26—H26···F3	0.93	2.33	2.941 (4)	123

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₀H₈N₂)](C₁₇H₉F₆O₄)
M_r	655.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.434 (7), 11.436 (5), 14.320 (6)
β (°)	104.310 (7)
V (Å³)	2607.9 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.817, 0.862
No. of measured, independent and observed [I > 2σ(I)] reflections	12604, 4604, 3593
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.080, 1.06
No. of reflections	4604
No. of parameters	362
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.47

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SAINT (Bruker, 2001), 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
O4—H4···O2ⁱ	0.82	1.72	2.538 (2)	174
C4—H4A···O1ⁱⁱ	0.93	2.52	3.366 (4)	152
C7—H7···O1ⁱⁱ	0.93	2.54	3.297 (4)	138
C8—H8···O3	0.93	2.53	3.312 (4)	142
C9—H9···O2ⁱⁱⁱ	0.93	2.48	3.242 (4)	139
C16—H16···F4	0.93	2.35	2.992 (4)	126
C26—H26···F3	0.93	2.33	2.941 (4)	123

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

Acknowledgements

This work was supported by the Scientific Research Foundation of Jiaxing University (grant No. 70509014) and the Key Project of Jiaxing University (grant No. 70110X13BL).

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