Crystal structure of catena-poly[[silver(I)-μ-N-(pyridin-2-ylmeth­yl)pyridine-3-amine-κ2N:N′] tri­fluoro­methane­sulfonate]

Moon, S.-H.; Cho, S.; Park, K.-M.

doi:10.1107/S1600536814022922

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages 389-391

doi:10.1107/S1600536814022922

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Crystal structure of catena-poly[[silver(I)-μ-N-(pyridin-2-ylmethyl)pyridine-3-amine-κ²N:N′] trifluoromethanesulfonate]

Suk-Hee Moon,^a Seonghwa Cho ^b and Ki-Min Park ^c ^*

^aDepartment of Food & Nutrition, Kyungnam College of Information and Technology, Busan 617-701, Republic of Korea, ^bDepartment of Chemistry, Gyeongsang National University, Jinju 660-701, Republic of Korea, and ^cResearch Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: kmpark@gnu.ac.kr

Edited by G. Smith, Queensland University of Technology, Australia (Received 13 October 2014; accepted 19 October 2014; online 24 October 2014)

In the asymmetric unit of the title compound, {[Ag(C₁₁H₁₁N₃)]CF₃SO₃}_n, there are two Ag^I atoms, two N-(pyridine-2-ylmethyl)pyridine-3-amine ligands (A and B) and two CF₃SO₃⁻ anions. Both Ag^I atoms are bridged by two pyridine N atoms from two symmetry-related A or B ligands, forming right- or left-handed helical chains, respectively. The Ag^I atom of the right-handed helical chain adopts a slightly distorted linear coordination geometry [N—Ag—N = 170.69 (14)°], while that of the left-handed helical chain adopts a bent geometry [N—Ag—N = 149.42 (14)°]. Both helical chains have the same pitch length [10.8437 (5) Å], propagate along the b-axial direction and are alternately arranged via Ag⋯Ag [3.0814 (5) Å] and π–π stacking interactions [centroid–centroid distances = 3.514 (3) and 3.487 (3) Å], resulting in the formation of a two-dimensional supramolecular network extending parallel to the ab plane. Weak Ag⋯O [2.861 (4), 2.617 (3), and 2.624 (4) Å] and Ag⋯F [3.017 (3) Å] interactions as well as N—H⋯O and C—H⋯O, C—H⋯N and C—H⋯F hydrogen-bonding interactions occur between the helical chains and the anions.

Keywords: crystal structure; silver(I); unsymmetrical dipyridyl ligand; helical chain coordination polymer.

CCDC reference: 1029928

1. Chemical context

A few silver coordination polymers based on unsymmetrical dipyridyl ligands composed of two terminal pyridines with different substituted-nitrogen positions have been reported (Moon & Park, 2013 , 2014 ; Zhang et al., 2013 ). In an extension of investigations on Ag^I coordination polymers with unsymmetrical dipyridyl ligands, the title compound was prepared by the reaction of silver trifluorometanesulfonate with N-(pyridine-2-ylmethyl)pyridine-3-amine. The structure of title compound is related to that of the perchlorate salt (Moon & Park, 2014; Zhang et al., 2013).

2. Structural commentary

The molecular components of the title structure are shown in Fig. 1. The asymmetric unit contains two Ag^I atoms (Ag1 and Ag2), two N-(pyridine-2-ylmethyl)pyridine-3-amine (Lee et al., 2013 ) ligands (A and B) and two trifluoromethanesulfonate anions. The Ag1 atom is coordinated by two pyridine N atoms from two symmetry-related A ligands giving a geometry which is slightly distorted from linear [N1—Ag1—N2 = 170.69 (14)°], forming a right-handed helical chain, while the Ag2 atom is coordinated by two pyridine N atoms from two symmetry-related B ligands in a bent arrangement [N4—Ag2—N5 = 149.42 (14)°], forming a left-handed helical chain. Two pyridine rings coordinating to the Ag1 and Ag2 atoms are tilted by 14.1 (3) and 28.9 (2)°, respectively, with respect to each other.

Figure 1
A view of the molecular structure of the title compound, with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level and dashed lines represent Ag⋯Ag and Ag⋯O interactions [symmetry codes: (i) −x + 1, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (ii) −x, y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (iii) −x + 1, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ; (iv) −x, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ].

3. Supramolecular features

Both helical chains in the structure have the same pitch length [10.8437 (5) Å], propagate along the b-axial direction and are alternately arranged via Ag1⋯Ag2 interactions [3.0814 (5) Å], resulting in the formation of a two-dimensional supramolecular network extending parallel to the ab plane (Fig. 2). Furthermore, π–π stacking interactions [centroid–centroid distances = 3.514 (3) and 3.487 (3) Å] between pyridine rings of both helical chains contribute to the stabilization of the two-dimensional network. In the crystal structure, the two-dimensional networks are further stabilized by Ag⋯O and Ag⋯F interactions [Ag1⋯O1 2.861 (4), Ag1⋯O4 2.624 (4), Ag2⋯O2 2.617 (3), Ag2⋯F3^iv 3.017 (3) Å; symmetry code: (iv) −x, y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ] (Figs. 1 and 2) as well as N—H⋯O and N—H⋯O and C—H⋯O and C—H⋯F hydrogen-bonds (Table 1) between the helical chains and CF₃SO₃⁻ anions.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O6ⁱ	0.88	2.51	3.206 (6)	136
N6—H6⋯O3ⁱⁱ	0.88	2.43	3.217 (6)	149
C1—H1⋯O5ⁱⁱⁱ	0.95	2.55	3.339 (6)	141
C4—H4⋯O3ⁱⁱ	0.95	2.54	3.383 (6)	147
C6—H6A⋯O5ⁱ	0.99	2.57	3.471 (6)	151
C11—H11⋯F3ⁱⁱⁱ	0.95	2.49	3.311 (6)	145
C11—H11⋯O1ⁱⁱⁱ	0.95	2.54	3.350 (7)	143
C15—H15⋯O6ⁱⁱ	0.95	2.53	3.450 (6)	164
C16—H16⋯O6^iv	0.95	2.58	3.316 (6)	135
C17—H17B⋯O3	0.99	2.58	3.422 (6)	143
Symmetry codes: (i) x, y-1, z; (ii) -x, -y+1, -z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x-1, y-1, z.

Figure 2
The two-dimensional supramolecular network formed through Ag⋯Ag and Ag⋯O interactions (yellow dashed lines) and π–π stacking interactions (black dashed lines).

4. Synthesis and crystallization

The ligand (N-(pyridin-2-ylmethyl)pyridine-3-amine) was prepared according to a procedure described by Lee et al. (2013). Crystals of the title compound suitable for X-ray analysis were obtained by vapour diffusion of diethyl ether into a DMSO solution of the white precipitate afforded by the reaction of the ligand with silver(I) hexafluoridophosphate in the molar ratio 1:1 in methanol.

5. Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms were positioned geometrically and refined using a riding model, with d(C—H) = 0.95 Å for Csp²—H, 0.88 Å for amine N—H and 0.99 Å for methylene C—H. For all H atoms U_iso(H) = 1.2U_eq(C,N).

Table 2
Experimental details

Crystal data
Chemical formula	[Ag(C₁₁H₁₁N₃)]·CF₃SO₃
M_r	442.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.7529 (6), 10.8437 (5), 19.5795 (9)
β (°)	99.826 (1)
V (Å³)	2877.1 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	1.60
Crystal size (mm)	0.31 × 0.22 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2000 )
T_min, T_max	0.637, 0.857
No. of measured, independent and observed [I > 2σ(I)] reflections	15852, 5629, 4286
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.093, 1.06
No. of reflections	5629
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.04, −0.67
Computer programs: SMART and SAINT-Plus (Bruker, 2000), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ) and DIAMOND (Brandenburg, 2005 ).

Supporting information

CCDC reference: 1029928

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814022922/zs2318sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022922/zs2318Isup2.hkl

checkCIF report

Chemical context top

A few silver coordination polymers based on unsymmetrical dipyridyl ligands composed of two terminal pyridines with different substituted-nitrogen positions have been reported (Moon & Park, 2013, 2014; Zhang et al., 2013). In an extension of investigations on Ag^I coordination polymers with unsymmetrical dipyridyl ligands, the title compound was prepared by the reaction of silver trifluorometanesulfonate with N-(pyridine-2-ylmethyl)pyridine-3-amine. The structure of title compound is isostructural with the perchlorate salt (Moon & Park, 2014; Zhang et al., 2013).

Structural commentary top

The title compound is shown in Fig. 1. The asymmetric unit contains two Ag^I atoms (Ag1 and Ag2), two N-(pyridine-2-ylmethyl)pyridine-3-amine (Lee et al., 2013) ligands (A and B) and two trifluoromethanesulfonate anions. The Ag1 atom is coordinated by two pyridine N atoms from two symmetry-related A ligands giving a geometry which is slightly distorted from linear [N1—Ag1—N2 = 170.69 (14)°], forming a right-handed helical chain, while the Ag2 atom is coordinated by two pyridine N atoms from two symmetry-related B ligands in a bent arrangement [N4—Ag2—N5 = 149.42 (14)°], forming a left-handed helical chain. Two pyridine rings coordinated to the Ag1 and Ag2 centers are tilted by 14.1 (3) and 28.9 (2)°, respectively, with respect to each other.

Supramolecular features top

Both helical chains in the structure have the same pitch length [10.8437 (5) Å], propagate along the b-axial direction and are alternately arranged via Ag1···Ag2 interactions [3.0814 (5) Å], resulting in the formation of a two-dimensional supramolecular network extending parallel to the ab plane (Fig. 2). Furthermore, π–π stacking interactions [centroid–centroid distances = 3.514 (3) and 3.487 (3) Å] between pyridine rings of both helical chains contribute to the stabilization of the two-dimensional network. In the crystal structure, the two-dimensional networks are further stabilized by Ag···O and Ag···F interactions [Ag1···O1 2.861 (4), Ag1···O4 2.624 (4), Ag2···O2 2.617 (3), Ag2···F3^iv 3.017 (3) Å; symmetry code: (iv) -x, y - 1/2, -z + 1/2] (Figs. 1 and 2) as well as N—H···O and N—H···O and C—H···O, C—H···N and C—H···F hydrogen-bonds (Table 1) between the helical chains and CF₃SO₃^- anions.

Synthesis and crystallization top

Refinement details top

Related literature top

For related literature, see: Lee et al. (2013); Moon & Park (2013, 2014); Zhang et al. (2013).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Figure 1. A view of the molecular structure of the title compound, with the atom numbering. Displacement ellipsoids are drawn at the 50% probability level and dashed lines represent Ag···Ag and Ag···O interactions [symmetry codes: (i) -x + 1 , y + 1/2, -z + 1/2; (ii) -x, y + 1/2, -z + 1/2; (iii) -x + 1, y - 1/2, -z + 1/2; (iv) -x, y - 1/2, -z + 1/2].

Figure 2. The two-dimensional supramolecular network formed through Ag···Ag and Ag···O interactions (yellow dashed lines) and π–π stacking interactions (black dashed lines).

catena-Poly[[silver(I)-µ-N-(pyridin-2-ylmethyl)pyridine-3-amine-κ²N:N'] trifluoromethanesulfonate] top

Crystal data top

[Ag(C₁₁H₁₁N₃)]·CF₃SO₃	F(000) = 1744
M_r = 442.17	D_x = 2.042 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5639 reflections
a = 13.7529 (6) Å	θ = 2.4–28.2°
b = 10.8437 (5) Å	µ = 1.60 mm⁻¹
c = 19.5795 (9) Å	T = 173 K
β = 99.826 (1)°	Plate, colorless
V = 2877.1 (2) Å³	0.31 × 0.22 × 0.10 mm
Z = 8

Data collection top

Bruker SMART CCD area detector diffractometer	5629 independent reflections
Radiation source: fine-focus sealed tube	4286 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −16→16
T_min = 0.637, T_max = 0.857	k = −13→9
15852 measured reflections	l = −23→24

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0369P)² + 6.3774P] where P = (F_o² + 2F_c²)/3
5629 reflections	(Δ/σ)_max = 0.001
415 parameters	Δρ_max = 1.04 e Å⁻³
0 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Ag(C₁₁H₁₁N₃)]·CF₃SO₃	V = 2877.1 (2) Å³
M_r = 442.17	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 13.7529 (6) Å	µ = 1.60 mm⁻¹
b = 10.8437 (5) Å	T = 173 K
c = 19.5795 (9) Å	0.31 × 0.22 × 0.10 mm
β = 99.826 (1)°

Data collection top

Bruker SMART CCD area detector diffractometer	5629 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	4286 reflections with I > 2σ(I)
T_min = 0.637, T_max = 0.857	R_int = 0.038
15852 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.06	Δρ_max = 1.04 e Å⁻³
5629 reflections	Δρ_min = −0.67 e Å⁻³
415 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	0.30869 (3)	0.63691 (3)	0.192614 (19)	0.02491 (11)
Ag2	0.17632 (3)	0.43820 (3)	0.24204 (2)	0.02787 (11)
N1	0.3183 (3)	0.4818 (4)	0.1251 (2)	0.0220 (9)
N2	0.7006 (3)	0.2705 (3)	0.2265 (2)	0.0223 (9)
N3	0.4684 (3)	0.2087 (4)	0.1066 (2)	0.0284 (10)
H3	0.4727	0.1538	0.0742	0.034*
C1	0.3913 (3)	0.3969 (4)	0.1368 (2)	0.0231 (11)
H1	0.4428	0.4078	0.1753	0.028*
C2	0.3940 (3)	0.2938 (4)	0.0943 (2)	0.0228 (10)
C3	0.3168 (3)	0.2794 (5)	0.0383 (2)	0.0252 (11)
H3A	0.3152	0.2103	0.0083	0.030*
C4	0.2434 (4)	0.3662 (5)	0.0272 (3)	0.0275 (11)
H4	0.1904	0.3569	−0.0104	0.033*
C5	0.2462 (4)	0.4662 (5)	0.0701 (2)	0.0237 (11)
H5	0.1956	0.5265	0.0607	0.028*
C6	0.5398 (4)	0.2033 (5)	0.1695 (3)	0.0288 (12)
H6A	0.5618	0.1167	0.1774	0.035*
H6B	0.5071	0.2279	0.2087	0.035*
C7	0.6299 (4)	0.2836 (4)	0.1702 (3)	0.0234 (11)
C8	0.6403 (4)	0.3658 (5)	0.1181 (3)	0.0327 (12)
H8	0.5897	0.3735	0.0787	0.039*
C9	0.7247 (4)	0.4367 (5)	0.1237 (3)	0.0346 (13)
H9	0.7330	0.4928	0.0879	0.042*
C10	0.7964 (4)	0.4258 (5)	0.1812 (3)	0.0324 (12)
H10	0.8543	0.4751	0.1868	0.039*
C11	0.7815 (4)	0.3405 (5)	0.2307 (3)	0.0314 (12)
H11	0.8318	0.3310	0.2701	0.038*
N4	−0.1913 (3)	0.0415 (3)	0.1616 (2)	0.0218 (9)
N5	0.1834 (3)	0.2634 (4)	0.1887 (2)	0.0224 (9)
N6	−0.0542 (3)	0.2536 (4)	0.0675 (2)	0.0295 (10)
H6	−0.0559	0.2757	0.0241	0.035*
C12	−0.1212 (3)	0.1180 (4)	0.1464 (2)	0.0211 (10)
H12	−0.0651	0.1334	0.1810	0.025*
C13	−0.1267 (3)	0.1755 (4)	0.0824 (2)	0.0221 (10)
C14	−0.2106 (4)	0.1521 (4)	0.0325 (2)	0.0273 (11)
H14	−0.2181	0.1902	−0.0118	0.033*
C15	−0.2815 (4)	0.0739 (5)	0.0483 (3)	0.0306 (12)
H15	−0.3385	0.0570	0.0148	0.037*
C16	−0.2702 (4)	0.0194 (4)	0.1130 (3)	0.0261 (11)
H16	−0.3197	−0.0352	0.1233	0.031*
C17	0.0244 (3)	0.3012 (5)	0.1190 (3)	0.0271 (11)
H17A	−0.0031	0.3203	0.1614	0.033*
H17B	0.0475	0.3798	0.1016	0.033*
C18	0.1121 (4)	0.2185 (4)	0.1389 (2)	0.0227 (10)
C19	0.1216 (4)	0.1044 (5)	0.1089 (3)	0.0313 (12)
H19	0.0706	0.0738	0.0742	0.038*
C20	0.2063 (4)	0.0352 (5)	0.1301 (3)	0.0351 (13)
H20	0.2139	−0.0430	0.1098	0.042*
C21	0.2788 (4)	0.0807 (5)	0.1806 (3)	0.0340 (13)
H21	0.3372	0.0348	0.1961	0.041*
C22	0.2647 (4)	0.1953 (5)	0.2082 (3)	0.0281 (11)
H22	0.3152	0.2273	0.2428	0.034*
S1	0.03658 (9)	0.65963 (11)	0.12069 (6)	0.0230 (3)
O1	0.1266 (3)	0.7218 (3)	0.1137 (2)	0.0390 (9)
O2	0.0406 (3)	0.5931 (3)	0.18476 (18)	0.0343 (9)
O3	−0.0106 (3)	0.5974 (3)	0.05959 (18)	0.0369 (9)
C23	−0.0469 (4)	0.7861 (5)	0.1303 (3)	0.0289 (12)
F1	−0.0609 (3)	0.8570 (3)	0.07437 (17)	0.0480 (9)
F2	−0.1350 (2)	0.7440 (3)	0.13945 (17)	0.0439 (8)
F3	−0.0113 (2)	0.8558 (3)	0.18486 (16)	0.0381 (8)
S2	0.47697 (9)	0.84803 (12)	0.12529 (6)	0.0269 (3)
O4	0.3758 (3)	0.8093 (3)	0.1188 (2)	0.0380 (9)
O5	0.5228 (3)	0.8873 (3)	0.19320 (19)	0.0403 (10)
O6	0.4983 (3)	0.9245 (4)	0.07004 (19)	0.0410 (10)
C24	0.5413 (4)	0.7040 (5)	0.1142 (3)	0.0311 (12)
F4	0.5337 (2)	0.6255 (3)	0.16634 (16)	0.0347 (7)
F5	0.6375 (2)	0.7235 (3)	0.11623 (17)	0.0428 (8)
F6	0.5059 (3)	0.6481 (3)	0.05552 (17)	0.0539 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0246 (2)	0.0220 (2)	0.0286 (2)	−0.00393 (16)	0.00586 (15)	−0.00514 (16)
Ag2	0.0321 (2)	0.0252 (2)	0.0282 (2)	−0.00139 (17)	0.01060 (17)	−0.00680 (17)
N1	0.020 (2)	0.021 (2)	0.025 (2)	−0.0021 (17)	0.0048 (17)	0.0009 (17)
N2	0.022 (2)	0.016 (2)	0.029 (2)	0.0018 (16)	0.0050 (17)	−0.0032 (17)
N3	0.033 (2)	0.020 (2)	0.031 (2)	0.0039 (18)	0.0014 (19)	−0.0082 (18)
C1	0.022 (3)	0.027 (3)	0.021 (2)	−0.005 (2)	0.002 (2)	−0.001 (2)
C2	0.027 (3)	0.019 (2)	0.023 (3)	−0.002 (2)	0.006 (2)	0.001 (2)
C3	0.029 (3)	0.025 (3)	0.022 (3)	−0.005 (2)	0.005 (2)	−0.004 (2)
C4	0.025 (3)	0.032 (3)	0.024 (3)	−0.004 (2)	−0.001 (2)	0.002 (2)
C5	0.022 (3)	0.027 (3)	0.022 (3)	0.000 (2)	0.004 (2)	0.003 (2)
C6	0.024 (3)	0.024 (3)	0.038 (3)	0.004 (2)	0.007 (2)	0.002 (2)
C7	0.027 (3)	0.015 (2)	0.029 (3)	0.003 (2)	0.006 (2)	−0.004 (2)
C8	0.040 (3)	0.030 (3)	0.029 (3)	0.003 (2)	0.005 (2)	0.001 (2)
C9	0.046 (3)	0.023 (3)	0.038 (3)	0.004 (2)	0.018 (3)	0.009 (2)
C10	0.032 (3)	0.021 (3)	0.049 (3)	−0.002 (2)	0.018 (3)	−0.001 (2)
C11	0.024 (3)	0.029 (3)	0.040 (3)	0.001 (2)	0.002 (2)	−0.004 (2)
N4	0.025 (2)	0.016 (2)	0.025 (2)	0.0020 (16)	0.0047 (17)	−0.0005 (17)
N5	0.029 (2)	0.019 (2)	0.021 (2)	0.0012 (17)	0.0104 (17)	0.0035 (17)
N6	0.035 (2)	0.033 (2)	0.020 (2)	−0.006 (2)	0.0030 (18)	0.0102 (19)
C12	0.021 (2)	0.020 (2)	0.021 (2)	−0.0001 (19)	0.001 (2)	−0.0012 (19)
C13	0.026 (3)	0.016 (2)	0.025 (3)	0.0041 (19)	0.004 (2)	0.000 (2)
C14	0.038 (3)	0.023 (3)	0.017 (2)	0.005 (2)	−0.003 (2)	0.000 (2)
C15	0.027 (3)	0.028 (3)	0.033 (3)	0.000 (2)	−0.007 (2)	−0.009 (2)
C16	0.022 (3)	0.020 (3)	0.036 (3)	0.001 (2)	0.006 (2)	−0.001 (2)
C17	0.026 (3)	0.024 (3)	0.031 (3)	−0.003 (2)	0.005 (2)	0.003 (2)
C18	0.029 (3)	0.018 (2)	0.025 (3)	−0.003 (2)	0.013 (2)	0.001 (2)
C19	0.039 (3)	0.024 (3)	0.032 (3)	−0.006 (2)	0.011 (2)	−0.001 (2)
C20	0.051 (4)	0.023 (3)	0.035 (3)	0.002 (3)	0.019 (3)	−0.004 (2)
C21	0.035 (3)	0.031 (3)	0.038 (3)	0.004 (2)	0.011 (3)	0.004 (3)
C22	0.030 (3)	0.027 (3)	0.029 (3)	0.000 (2)	0.011 (2)	0.004 (2)
S1	0.0249 (6)	0.0222 (6)	0.0208 (6)	0.0063 (5)	0.0006 (5)	−0.0015 (5)
O1	0.029 (2)	0.037 (2)	0.054 (2)	0.0034 (17)	0.0158 (18)	−0.0033 (19)
O2	0.046 (2)	0.031 (2)	0.0251 (19)	0.0098 (17)	0.0012 (17)	0.0060 (16)
O3	0.044 (2)	0.033 (2)	0.030 (2)	0.0092 (17)	−0.0026 (17)	−0.0112 (17)
C23	0.029 (3)	0.028 (3)	0.028 (3)	0.004 (2)	−0.001 (2)	−0.006 (2)
F1	0.062 (2)	0.0397 (19)	0.0404 (19)	0.0274 (17)	0.0022 (16)	0.0099 (16)
F2	0.0218 (16)	0.052 (2)	0.058 (2)	0.0028 (15)	0.0059 (15)	−0.0139 (17)
F3	0.0315 (16)	0.0381 (18)	0.0420 (18)	0.0053 (14)	−0.0013 (14)	−0.0205 (15)
S2	0.0274 (7)	0.0256 (7)	0.0266 (7)	−0.0033 (5)	0.0018 (5)	0.0070 (5)
O4	0.030 (2)	0.031 (2)	0.055 (3)	0.0000 (16)	0.0120 (18)	0.0148 (19)
O5	0.061 (3)	0.028 (2)	0.030 (2)	−0.0019 (19)	0.0017 (19)	−0.0031 (17)
O6	0.035 (2)	0.048 (2)	0.036 (2)	−0.0173 (18)	−0.0061 (17)	0.0191 (19)
C24	0.031 (3)	0.038 (3)	0.027 (3)	−0.005 (2)	0.011 (2)	−0.005 (2)
F4	0.0365 (17)	0.0227 (15)	0.0456 (18)	0.0006 (13)	0.0087 (14)	0.0061 (14)
F5	0.0282 (17)	0.049 (2)	0.055 (2)	−0.0043 (15)	0.0179 (15)	−0.0013 (17)
F6	0.061 (2)	0.061 (2)	0.0378 (19)	−0.0073 (19)	0.0040 (17)	−0.0228 (18)

Geometric parameters (Å, º) top

Ag1—N1	2.156 (4)	N6—C13	1.377 (6)
Ag1—N2ⁱ	2.167 (4)	N6—C17	1.443 (6)
Ag1—Ag2	3.0814 (5)	N6—H6	0.8800
Ag2—N4ⁱⁱ	2.174 (4)	C12—C13	1.390 (7)
Ag2—N5	2.175 (4)	C12—H12	0.9500
N1—C5	1.344 (6)	C13—C14	1.402 (7)
N1—C1	1.353 (6)	C14—C15	1.367 (7)
N2—C11	1.338 (6)	C14—H14	0.9500
N2—C7	1.347 (6)	C15—C16	1.383 (7)
N2—Ag1ⁱⁱⁱ	2.167 (4)	C15—H15	0.9500
N3—C2	1.369 (6)	C16—H16	0.9500
N3—C6	1.439 (6)	C17—C18	1.500 (7)
N3—H3	0.8800	C17—H17A	0.9900
C1—C2	1.398 (7)	C17—H17B	0.9900
C1—H1	0.9500	C18—C19	1.385 (7)
C2—C3	1.398 (6)	C19—C20	1.389 (8)
C3—C4	1.369 (7)	C19—H19	0.9500
C3—H3A	0.9500	C20—C21	1.370 (8)
C4—C5	1.368 (7)	C20—H20	0.9500
C4—H4	0.9500	C21—C22	1.381 (7)
C5—H5	0.9500	C21—H21	0.9500
C6—C7	1.512 (7)	C22—H22	0.9500
C6—H6A	0.9900	S1—O3	1.429 (4)
C6—H6B	0.9900	S1—O1	1.436 (4)
C7—C8	1.380 (7)	S1—O2	1.440 (4)
C8—C9	1.382 (8)	S1—C23	1.819 (5)
C8—H8	0.9500	C23—F1	1.324 (6)
C9—C10	1.369 (8)	C23—F3	1.332 (5)
C9—H9	0.9500	C23—F2	1.336 (6)
C10—C11	1.379 (7)	S2—O6	1.433 (4)
C10—H10	0.9500	S2—O5	1.435 (4)
C11—H11	0.9500	S2—O4	1.438 (4)
N4—C16	1.336 (6)	S2—C24	1.826 (6)
N4—C12	1.343 (6)	C24—F6	1.317 (6)
N4—Ag2^iv	2.174 (4)	C24—F5	1.334 (6)
N5—C22	1.341 (6)	C24—F4	1.347 (6)
N5—C18	1.349 (6)

N1—Ag1—N2ⁱ	170.69 (14)	N4—C12—C13	123.1 (4)
N1—Ag1—Ag2	75.41 (10)	N4—C12—H12	118.4
N2ⁱ—Ag1—Ag2	97.25 (10)	C13—C12—H12	118.4
N4ⁱⁱ—Ag2—N5	149.42 (14)	N6—C13—C12	122.5 (4)
N4ⁱⁱ—Ag2—Ag1	86.49 (10)	N6—C13—C14	120.2 (4)
N5—Ag2—Ag1	112.41 (10)	C12—C13—C14	117.3 (4)
C5—N1—C1	118.3 (4)	C15—C14—C13	119.3 (5)
C5—N1—Ag1	118.4 (3)	C15—C14—H14	120.4
C1—N1—Ag1	123.3 (3)	C13—C14—H14	120.4
C11—N2—C7	117.9 (4)	C14—C15—C16	120.0 (5)
C11—N2—Ag1ⁱⁱⁱ	119.1 (3)	C14—C15—H15	120.0
C7—N2—Ag1ⁱⁱⁱ	122.9 (3)	C16—C15—H15	120.0
C2—N3—C6	124.0 (4)	N4—C16—C15	121.7 (5)
C2—N3—H3	118.0	N4—C16—H16	119.1
C6—N3—H3	118.0	C15—C16—H16	119.1
N1—C1—C2	122.6 (4)	N6—C17—C18	116.2 (4)
N1—C1—H1	118.7	N6—C17—H17A	108.2
C2—C1—H1	118.7	C18—C17—H17A	108.2
N3—C2—C1	121.9 (4)	N6—C17—H17B	108.2
N3—C2—C3	120.5 (4)	C18—C17—H17B	108.2
C1—C2—C3	117.5 (4)	H17A—C17—H17B	107.4
C4—C3—C2	119.2 (5)	N5—C18—C19	121.3 (5)
C4—C3—H3A	120.4	N5—C18—C17	115.1 (4)
C2—C3—H3A	120.4	C19—C18—C17	123.6 (5)
C5—C4—C3	120.3 (5)	C18—C19—C20	119.4 (5)
C5—C4—H4	119.8	C18—C19—H19	120.3
C3—C4—H4	119.8	C20—C19—H19	120.3
N1—C5—C4	122.1 (5)	C21—C20—C19	119.4 (5)
N1—C5—H5	119.0	C21—C20—H20	120.3
C4—C5—H5	119.0	C19—C20—H20	120.3
N3—C6—C7	115.1 (4)	C20—C21—C22	118.3 (5)
N3—C6—H6A	108.5	C20—C21—H21	120.9
C7—C6—H6A	108.5	C22—C21—H21	120.9
N3—C6—H6B	108.5	N5—C22—C21	123.3 (5)
C7—C6—H6B	108.5	N5—C22—H22	118.3
H6A—C6—H6B	107.5	C21—C22—H22	118.3
N2—C7—C8	121.4 (5)	O3—S1—O1	114.7 (2)
N2—C7—C6	115.0 (4)	O3—S1—O2	115.9 (2)
C8—C7—C6	123.6 (5)	O1—S1—O2	114.3 (2)
C7—C8—C9	119.5 (5)	O3—S1—C23	103.8 (2)
C7—C8—H8	120.3	O1—S1—C23	103.0 (2)
C9—C8—H8	120.3	O2—S1—C23	102.7 (2)
C10—C9—C8	119.7 (5)	F1—C23—F3	108.4 (4)
C10—C9—H9	120.2	F1—C23—F2	107.6 (4)
C8—C9—H9	120.2	F3—C23—F2	107.6 (4)
C9—C10—C11	117.6 (5)	F1—C23—S1	111.0 (4)
C9—C10—H10	121.2	F3—C23—S1	111.0 (3)
C11—C10—H10	121.2	F2—C23—S1	111.0 (4)
N2—C11—C10	123.9 (5)	O6—S2—O5	114.4 (2)
N2—C11—H11	118.0	O6—S2—O4	115.0 (2)
C10—C11—H11	118.0	O5—S2—O4	115.7 (2)
C16—N4—C12	118.7 (4)	O6—S2—C24	103.9 (2)
C16—N4—Ag2^iv	118.0 (3)	O5—S2—C24	102.6 (2)
C12—N4—Ag2^iv	123.0 (3)	O4—S2—C24	102.7 (2)
C22—N5—C18	118.4 (4)	F6—C24—F5	108.4 (4)
C22—N5—Ag2	116.5 (3)	F6—C24—F4	107.8 (4)
C18—N5—Ag2	125.1 (3)	F5—C24—F4	106.4 (4)
C13—N6—C17	123.7 (4)	F6—C24—S2	112.5 (4)
C13—N6—H6	118.2	F5—C24—S2	111.0 (4)
C17—N6—H6	118.2	F4—C24—S2	110.4 (3)

N1—Ag1—Ag2—N4ⁱⁱ	160.70 (15)	N4—C12—C13—N6	−179.9 (4)
N2ⁱ—Ag1—Ag2—N4ⁱⁱ	−13.47 (14)	N4—C12—C13—C14	0.6 (7)
N1—Ag1—Ag2—N5	5.50 (15)	N6—C13—C14—C15	179.7 (5)
N2ⁱ—Ag1—Ag2—N5	−168.67 (15)	C12—C13—C14—C15	−0.8 (7)
Ag2—Ag1—N1—C5	82.5 (3)	C13—C14—C15—C16	0.3 (7)
Ag2—Ag1—N1—C1	−95.0 (4)	C12—N4—C16—C15	−0.6 (7)
C5—N1—C1—C2	−0.6 (7)	Ag2^iv—N4—C16—C15	−174.9 (4)
Ag1—N1—C1—C2	177.0 (3)	C14—C15—C16—N4	0.4 (8)
C6—N3—C2—C1	11.5 (7)	C13—N6—C17—C18	83.2 (6)
C6—N3—C2—C3	−167.8 (5)	C22—N5—C18—C19	0.6 (7)
N1—C1—C2—N3	−180.0 (4)	Ag2—N5—C18—C19	−178.2 (3)
N1—C1—C2—C3	−0.6 (7)	C22—N5—C18—C17	−178.9 (4)
N3—C2—C3—C4	−180.0 (4)	Ag2—N5—C18—C17	2.3 (6)
C1—C2—C3—C4	0.6 (7)	N6—C17—C18—N5	−178.1 (4)
C2—C3—C4—C5	0.5 (7)	N6—C17—C18—C19	2.3 (7)
C1—N1—C5—C4	1.8 (7)	N5—C18—C19—C20	−0.4 (7)
Ag1—N1—C5—C4	−175.9 (4)	C17—C18—C19—C20	179.1 (5)
C3—C4—C5—N1	−1.8 (7)	C18—C19—C20—C21	0.3 (8)
C2—N3—C6—C7	−87.1 (6)	C19—C20—C21—C22	−0.4 (8)
C11—N2—C7—C8	0.5 (7)	C18—N5—C22—C21	−0.7 (7)
Ag1ⁱⁱⁱ—N2—C7—C8	−177.0 (4)	Ag2—N5—C22—C21	178.1 (4)
C11—N2—C7—C6	−179.0 (4)	C20—C21—C22—N5	0.7 (8)
Ag1ⁱⁱⁱ—N2—C7—C6	3.6 (6)	O3—S1—C23—F1	−57.7 (4)
N3—C6—C7—N2	−174.5 (4)	O1—S1—C23—F1	62.2 (4)
N3—C6—C7—C8	6.1 (7)	O2—S1—C23—F1	−178.8 (4)
N2—C7—C8—C9	−0.3 (8)	O3—S1—C23—F3	−178.4 (4)
C6—C7—C8—C9	179.1 (5)	O1—S1—C23—F3	−58.5 (4)
C7—C8—C9—C10	−0.8 (8)	O2—S1—C23—F3	60.5 (4)
C8—C9—C10—C11	1.7 (8)	O3—S1—C23—F2	61.9 (4)
C7—N2—C11—C10	0.5 (7)	O1—S1—C23—F2	−178.2 (3)
Ag1ⁱⁱⁱ—N2—C11—C10	178.1 (4)	O2—S1—C23—F2	−59.2 (4)
C9—C10—C11—N2	−1.6 (8)	O6—S2—C24—F6	−64.1 (4)
N4ⁱⁱ—Ag2—N5—C22	−48.9 (5)	O5—S2—C24—F6	176.4 (4)
Ag1—Ag2—N5—C22	75.7 (3)	O4—S2—C24—F6	56.0 (4)
N4ⁱⁱ—Ag2—N5—C18	129.9 (4)	O6—S2—C24—F5	57.6 (4)
Ag1—Ag2—N5—C18	−105.5 (3)	O5—S2—C24—F5	−61.9 (4)
C16—N4—C12—C13	0.1 (7)	O4—S2—C24—F5	177.7 (3)
Ag2^iv—N4—C12—C13	174.1 (3)	O6—S2—C24—F4	175.4 (3)
C17—N6—C13—C12	−11.8 (7)	O5—S2—C24—F4	56.0 (4)
C17—N6—C13—C14	167.7 (4)	O4—S2—C24—F4	−64.5 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O6^v	0.88	2.51	3.206 (6)	136
N6—H6···O3^vi	0.88	2.43	3.217 (6)	149
C1—H1···O5ⁱⁱⁱ	0.95	2.55	3.339 (6)	141
C4—H4···O3^vi	0.95	2.54	3.383 (6)	147
C6—H6A···O5^v	0.99	2.57	3.471 (6)	151
C8—H8···N3	0.95	2.57	2.891 (7)	100
C11—H11···F3ⁱⁱⁱ	0.95	2.49	3.311 (6)	145
C11—H11···O1ⁱⁱⁱ	0.95	2.54	3.350 (7)	143
C15—H15···O6^vi	0.95	2.53	3.450 (6)	164
C16—H16···O6^vii	0.95	2.58	3.316 (6)	135
C17—H17B···O3	0.99	2.58	3.422 (6)	143
C19—H19···N6	0.95	2.59	2.906 (7)	100

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O6ⁱ	0.88	2.51	3.206 (6)	136
N6—H6···O3ⁱⁱ	0.88	2.43	3.217 (6)	149
C1—H1···O5ⁱⁱⁱ	0.95	2.55	3.339 (6)	141
C4—H4···O3ⁱⁱ	0.95	2.54	3.383 (6)	147
C6—H6A···O5ⁱ	0.99	2.57	3.471 (6)	151
C11—H11···F3ⁱⁱⁱ	0.95	2.49	3.311 (6)	145
C11—H11···O1ⁱⁱⁱ	0.95	2.54	3.350 (7)	143
C15—H15···O6ⁱⁱ	0.95	2.53	3.450 (6)	164
C16—H16···O6^iv	0.95	2.58	3.316 (6)	135
C17—H17B···O3	0.99	2.58	3.422 (6)	143

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₁H₁₁N₃)]·CF₃SO₃
M_r	442.17
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	13.7529 (6), 10.8437 (5), 19.5795 (9)
β (°)	99.826 (1)
V (Å³)	2877.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.60
Crystal size (mm)	0.31 × 0.22 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.637, 0.857
No. of measured, independent and observed [I > 2σ(I)] reflections	15852, 5629, 4286
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.093, 1.06
No. of reflections	5629
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.04, −0.67

Computer programs: SMART (Bruker, 2000), SAINT-Plus (Bruker, 2000), SAINT-Plus (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2005), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by NRF (2010–0022675) projects.

References

Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Germany. Google Scholar
Bruker (2000). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lee, E., Ryu, H., Moon, S.-H. & Park, K.-M. (2013). Bull. Korean Chem. Soc. 34, 3477–3480. Web of Science CSD CrossRef CAS Google Scholar
Moon, S.-H. & Park, K.-M. (2013). Acta Cryst. E69, m414–m415. CSD CrossRef CAS IUCr Journals Google Scholar
Moon, S.-H. & Park, K.-M. (2014). Acta Cryst. E70, m233. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Z.-Y., Deng, Z.-P., Huo, L.-H., Zhao, H. & Gao, S. (2013). Inorg. Chem. 52, 5914–5923. Web of Science CSD CrossRef CAS PubMed Google Scholar

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