Crystal structure of an AgI inter­calation compound: catena-poly[[silver(I)-μ-N-(pyridin-3-ylmeth­yl)pyridin-3-amine-κ2N:N′] hexa­fluorido­phosphate aceto­nitrile disolvate]

Moon, S.-H.; Kang, Y.; Park, K.-M.

doi:10.1107/S2056989017013421

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 73| Part 10| October 2017| Pages 1542-1545

https://doi.org/10.1107/S2056989017013421

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Crystal structure of an Ag^I intercalation compound: catena-poly[[silver(I)-μ-N-(pyridin-3-ylmethyl)pyridin-3-amine-κ²N:N′] hexafluoridophosphate acetonitrile disolvate]

Suk-Hee Moon,^a Youngjin Kang ^b ^* and Ki-Min Park ^c ^*

^aDepartment of Food and Nutrition, Kyungnam College of Information and Technology, Busan 47011, Republic of Korea, ^bDivision of Science Education, Kangwon National University, Chuncheon 24341, Republic of Korea, and ^cResearch institute of Natural Science, Gyeongsang National University, Jinju 52828, Republic of Korea
^*Correspondence e-mail: kangy@kangwon.ac.kr, kmpark@gnu.ac.kr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 13 September 2017; accepted 19 September 2017; online 25 September 2017)

The asymmetric unit in the title compound, [Ag(C₁₁H₁₁N₃)]PF₆·2CH₃CN or {[AgL]·PF₆·2CH₃CN}_n, L = N-(pyridin-3-ylmethyl)pyridin-3-amine, comprises one Ag^I atom, one L ligand, two acetonitrile solvent molecules and one PF₆⁻ anion disordered over two orientations in a 0.567 (11):0.433 (11) ratio. Each Ag^I atom is coordinated by two pyridine N atoms from two L ligands in a slightly distorted linear coordination geometry [N—Ag—N = 170.55 (8)°]. Each L ligand bridges two Ag^I ions, resulting in the formation of a zigzag chain propagating along the [101] direction. In the crystal, Ag⋯Ag contacts [3.3023 (5) Å] and intermolecular π–π stacking interactions [centroid-to-centroid distance = 3.5922 (15) Å] between the pyridine rings link these chains into a corrugated layer parallel to the ( $[\overline{1}]$ 01) plane. The layers are stacked with a separation of 10.4532 (5) Å, and acetonitrile solvent molecules and PF₆⁻ anions as guests are intercalated between the layers. The layers are connected through several N/C—H⋯F hydrogen bonds and P—F⋯π interactions [F⋯ring centroid = 3.241 (8) Å] between the layer and the intercalated guests and between the intercalated guests, forming a three-dimensional supramolecular network.

Keywords: crystal structure; silver(I); dipyridyl-type ligand; intercalation; Ag⋯Ag interaction; hydrogen bonding; π–π interactions.

CCDC reference: 1575393

1. Chemical context

Silver coordination polymers based on dipyridyl-type ligands have been widely exploited due to the intriguing topologies and the fascinating properties caused by a variety of coordination geometries and d¹⁰ electronic configurations of the Ag^I ion (Leong & Vittal, 2011 ; Moulton & Zaworotko, 2001 ; Wang et al., 2012 ). In particular, Ag^I ions have a preference for a linear two-coordinate geometry and can serve to link bridging dipyridyl-type ligands to form polymeric chains. Based on this concept, we have focused our attention on the development of one-dimensional Ag^I coordination polymers with dipyridyl-type ligands. Up to date, we have reported several Ag^I coordination polymers with interesting topologies involving zigzag (Moon et al., 2016 ), helical (Moon et al., 2014 , 2015 ) and double helical (Lee et al., 2015 ) structures. In an extension of our research, the title compound was prepared by the reaction of silver(I) hexafluoridophosphate with a dipyridyl type-ligand, namely N-(pyridin-3-ylmethyl)pyridin-3-amine (L), synthesized according to a literature procedure (Lee et al., 2013 ). Herein, we report on the crystal structure of the title compound in which lattice solvent molecules and anions as guests are intercalated between the layers formed by intermolecular interactions between zigzag –(Ag–L)_n– chains.

2. Structural commentary

The molecular components of the title structure are shown in Fig. 1. The asymmetric unit comprises one Ag^I atom, one L ligand, two acetonitrile solvent molecules, and one hexafluoridophosphate anion disordered over two orientations in a 0.567 (11):0.433 (11) ratio. The silver(I) atom is coordinated by two pyridine N atoms (N1 and N2) from two symmetry-related L ligands, leading to the formation of an infinite zigzag chain propagating along the [101] direction. Thus, the Ag^I atom is two-coordinated in a slightly distorted linear coordination geometry [N1ⁱ—Ag1—N2 = 170.55 (8)°; symmetry code: (i) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ; Table 1]. This distortion from linear geometry may be caused by Ag⋯N interactions between the Ag^I ion and two acetonitrile N atoms [Ag1⋯N4 = 2.792 (4), Ag1⋯N5 = 2.815 (4) Å; black dashed lines in Fig. 1]. The two pyridine rings coordinated to the Ag^I center are tilted slightly, by 6.29 (15)° with respect to each other. In the chain, the Ag^I atoms are separated by 11.1009 (3) Å along the L linker which adopts a stretched trans conformation with the C2—N3—C6—C7 torsion angles being 174.7 (3)°.

Table 1
Selected geometric parameters (Å, °)

Ag1—N1ⁱ	2.163 (2)	Ag1—N2	2.166 (2)

N1ⁱ—Ag1—N2	170.55 (8)
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Figure 1
View of the molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Disordered F atoms of the PF₆⁻ anion have been omitted for clarity. Black and yellow dashed lines represent Ag⋯N interactions and intermolecular C/N—H⋯F hydrogen bonds, respectively. [Symmetry codes: (i) x + $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z + $[{1\over 2}]$ ; (ii) x − $[{1\over 2}]$ , −y + $[{1\over 2}]$ , z − $[{1\over 2}]$ .]

3. Supramolecular features

The neighbouring zigzag chains are connected by Ag⋯Ag contacts [Ag1⋯Ag1 = 3.3023 (5) Å; red dashed lines in Fig. 2] and intermolecular π-π-stacking interactions between the pyridine rings [Cg1⋯Cg2ⁱⁱ = 3.5922 (15) Å; yellow dashed lines in Fig. 2; Cg1 and Cg2 are the centroids of the N1/C1–C5 and N2/C7–C11 rings, respectively; symmetry code: (ii) −x + $[{1\over 2}]$ , y − $[{1\over 2}]$ , −z + $[{1\over 2}]$ ], resulting in the formation of a corrugated layer spreading out along the ( $[\overline{1}]$ 01) plane (Fig. 2). Adjacent layers are stacked on each other with a separation of 10.4532 (5) Å. Acetonitrile molecules and PF₆⁻ anions as guests are intercalated between the layers (Fig. 3). The layers are further connected by several intermolecular N/C—H⋯F hydrogen bonds (Table 2; yellow dashed lines in Figs. 1 and 3) and P—F⋯π interactions [F3⋯Cg2 = 3.241 (8) Å; sky-blue dashed line in Fig. 1] between the layer and the anions and between the acetonitrile solvent molecules and the anions, forming a three-dimensional supramolecular network.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯F3	0.84 (3)	2.49 (3)	3.208 (8)	144 (3)
N3—H3A⋯F5	0.84 (3)	2.46 (3)	3.273 (10)	162 (3)
N3—H3A⋯F5′	0.84 (3)	2.18 (3)	2.999 (10)	167 (3)
C8—H8⋯N4ⁱⁱ	0.95	2.63	3.478 (5)	149
C10—H10⋯F2ⁱⁱⁱ	0.95	2.39	3.176 (9)	140
C13—H13A⋯F2′ⁱⁱⁱ	0.98	2.54	3.487 (13)	163
C13—H13B⋯F6ⁱ	0.98	2.53	3.365 (10)	144
C13—H13B⋯F1′ⁱ	0.98	2.59	3.57 (2)	171
C15—H15A⋯F1	0.98	2.52	3.441 (9)	157
C15—H15A⋯F3′	0.98	2.42	3.356 (13)	160
C15—H15B⋯F2^iv	0.98	2.23	3.088 (10)	146
C15—H15B⋯F5′^iv	0.98	2.57	3.509 (11)	160
C15—H15C⋯F1ⁱⁱⁱ	0.98	2.36	3.329 (8)	168
C15—H15C⋯F1′ⁱⁱⁱ	0.98	2.09	3.037 (9)	161
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
The two-dimensional network formed through Ag⋯Ag contacts (red dashed lines) and intermolecular π–π stacking interactions (yellow dashed lines). Acetonitrile solvent molecules, the PF₆⁻ anions and H atoms have been omitted for clarity.

Figure 3
Interlayer stacking showing the intercalation of acetonitrile molecules and PF₆⁻ anions between the layers. Red, black and yellow dashed lines represent Ag⋯Ag contacts, Ag⋯N interactions and N/C—H⋯F hydrogen bonds, respectively. Disordered F atoms of the PF₆⁻ anions and H atoms not involved in intermolecular interactions have been omitted for clarity.

4. Synthesis and crystallization

The L ligand was synthesized according to a literature method (Lee et al., 2013). Slow evaporation of an acetonitrile solution of the L ligand with AgPF₆ in the molar ratio 1:1 afforded colourless block-like X-ray quality single crystals of the title compound.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The PF₆⁻ anion is disordered over two orientations in a 0.567 (11):0.433 (11) ratio. The amine H atom was located from a difference-Fourier map and freely refined [N—H = 0.84 (3) Å]. All other H atoms were positioned geometrically and refined as riding: C—H = 0.95 Å for Csp²—H, 0.99 Å for methylene C—H and 0.98 Å for methyl C—H with U_iso(H) = 1.5U_eq (C-methyl) and 1.2U_eq(C) for other C-bound H atoms.

Table 3
Experimental details

Crystal data
Chemical formula	[Ag(C₁₁H₁₁N₃)]PF₆·2C₂H₃N
M_r	520.17
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	12.8997 (4), 7.5361 (3), 20.9747 (7)
β (°)	102.9900 (6)
V (Å³)	1986.84 (12)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.16
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
T_min, T_max	0.666, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	11824, 4316, 3527
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.081, 1.10
No. of reflections	4316
No. of parameters	312
No. of restraints	18
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.12, −0.66
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXS97 and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), DIAMOND (Brandenburg, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1575393

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989017013421/su5393sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017013421/su5393Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

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

Crystal data top

[Ag(C₁₁H₁₁N₃)]PF₆·2C₂H₃N	F(000) = 1032
M_r = 520.17	D_x = 1.739 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 12.8997 (4) Å	Cell parameters from 5825 reflections
b = 7.5361 (3) Å	θ = 2.9–28.0°
c = 20.9747 (7) Å	µ = 1.16 mm⁻¹
β = 102.9900 (6)°	T = 173 K
V = 1986.84 (12) Å³	Block, colorless
Z = 4	0.35 × 0.25 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	3527 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.020
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 27.0°, θ_min = 1.7°
T_min = 0.666, T_max = 0.746	h = −10→16
11824 measured reflections	k = −9→9
4316 independent reflections	l = −26→26

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: mixed
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0297P)² + 2.2488P] where P = (F_o² + 2F_c²)/3
4316 reflections	(Δ/σ)_max = 0.001
312 parameters	Δρ_max = 1.12 e Å⁻³
18 restraints	Δρ_min = −0.66 e Å⁻³

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.57809 (2)	0.34509 (3)	0.48065 (2)	0.04382 (9)
N1	0.09170 (18)	0.3315 (3)	0.06343 (10)	0.0313 (5)
N2	0.55270 (18)	0.4849 (3)	0.38820 (10)	0.0317 (5)
N3	0.3023 (2)	0.4904 (4)	0.19724 (12)	0.0385 (6)
H3A	0.352 (3)	0.439 (4)	0.1850 (15)	0.035 (8)*
C1	0.1875 (2)	0.3614 (4)	0.10237 (12)	0.0305 (6)
H1	0.2478	0.3053	0.0924	0.037*
C2	0.2022 (2)	0.4724 (3)	0.15729 (12)	0.0282 (5)
C3	0.1127 (2)	0.5557 (4)	0.17056 (13)	0.0315 (6)
H3	0.1192	0.6331	0.2070	0.038*
C4	0.0141 (2)	0.5233 (4)	0.12960 (13)	0.0347 (6)
H4	−0.0477	0.5784	0.1379	0.042*
C5	0.0059 (2)	0.4111 (4)	0.07669 (13)	0.0328 (6)
H5	−0.0620	0.3897	0.0490	0.039*
C6	0.3223 (2)	0.6106 (4)	0.25170 (13)	0.0363 (6)
H6A	0.2721	0.5853	0.2800	0.044*
H6B	0.3097	0.7338	0.2354	0.044*
C7	0.4343 (2)	0.5940 (3)	0.29117 (12)	0.0288 (5)
C8	0.4549 (2)	0.5027 (3)	0.34988 (12)	0.0294 (5)
H8	0.3968	0.4500	0.3638	0.035*
C9	0.6343 (2)	0.5596 (4)	0.36808 (14)	0.0355 (6)
H9	0.7041	0.5474	0.3946	0.043*
C10	0.6207 (2)	0.6531 (4)	0.31048 (14)	0.0400 (7)
H10	0.6801	0.7041	0.2976	0.048*
C11	0.5193 (2)	0.6720 (4)	0.27147 (13)	0.0374 (6)
H11	0.5082	0.7374	0.2318	0.045*
P1	0.52792 (8)	0.16310 (12)	0.15620 (5)	0.0532 (2)
F1	0.6049 (5)	0.0241 (8)	0.2082 (3)	0.0812 (19)	0.567 (11)
F2	0.6355 (6)	0.2633 (12)	0.1590 (6)	0.106 (3)	0.567 (11)
F3	0.5178 (6)	0.2625 (10)	0.2228 (4)	0.106 (3)	0.567 (11)
F4	0.4273 (13)	0.060 (3)	0.1615 (8)	0.133 (6)	0.567 (11)
F5	0.4615 (6)	0.3036 (14)	0.1156 (4)	0.100 (3)	0.567 (11)
F6	0.5453 (8)	0.0508 (11)	0.0998 (4)	0.119 (3)	0.567 (11)
F1'	0.5583 (12)	−0.0286 (12)	0.1587 (9)	0.149 (7)	0.433 (11)
F2'	0.6253 (9)	0.2192 (19)	0.1252 (6)	0.106 (4)	0.433 (11)
F3'	0.5773 (14)	0.211 (2)	0.2223 (5)	0.184 (7)	0.433 (11)
F4'	0.4247 (14)	0.101 (3)	0.1739 (9)	0.128 (7)	0.433 (11)
F5'	0.4867 (8)	0.3671 (11)	0.1435 (6)	0.086 (3)	0.433 (11)
F6'	0.4650 (11)	0.1392 (17)	0.0770 (4)	0.125 (5)	0.433 (11)
N4	0.6922 (3)	0.6394 (5)	0.53962 (16)	0.0733 (10)
C12	0.7722 (3)	0.6996 (5)	0.53960 (16)	0.0538 (9)
C13	0.8750 (3)	0.7783 (6)	0.5397 (2)	0.0756 (12)
H13A	0.8918	0.7604	0.4969	0.113*
H13B	0.9298	0.7219	0.5736	0.113*
H13C	0.8727	0.9057	0.5487	0.113*
N5	0.7553 (3)	0.1622 (7)	0.45595 (18)	0.0922 (14)
C14	0.7749 (3)	0.1581 (5)	0.40711 (19)	0.0566 (9)
C15	0.7958 (4)	0.1556 (6)	0.3423 (2)	0.0749 (12)
H15A	0.7287	0.1410	0.3098	0.112*
H15B	0.8435	0.0566	0.3388	0.112*
H15C	0.8295	0.2675	0.3343	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.05358 (16)	0.04805 (15)	0.02636 (12)	0.01328 (11)	0.00167 (9)	0.01001 (10)
N1	0.0354 (12)	0.0327 (12)	0.0226 (10)	−0.0052 (10)	−0.0003 (9)	0.0008 (9)
N2	0.0343 (12)	0.0324 (12)	0.0246 (11)	0.0031 (10)	−0.0010 (9)	0.0005 (9)
N3	0.0288 (12)	0.0498 (15)	0.0335 (12)	0.0031 (11)	0.0000 (10)	−0.0170 (11)
C1	0.0309 (14)	0.0348 (14)	0.0245 (12)	0.0000 (11)	0.0037 (10)	−0.0022 (10)
C2	0.0296 (13)	0.0307 (13)	0.0227 (12)	−0.0005 (11)	0.0026 (10)	0.0000 (10)
C3	0.0349 (14)	0.0309 (14)	0.0273 (13)	0.0024 (11)	0.0039 (11)	−0.0011 (10)
C4	0.0310 (14)	0.0341 (14)	0.0373 (15)	0.0061 (11)	0.0040 (11)	0.0072 (12)
C5	0.0276 (13)	0.0356 (14)	0.0295 (13)	−0.0035 (11)	−0.0055 (10)	0.0081 (11)
C6	0.0337 (15)	0.0436 (16)	0.0268 (13)	0.0037 (12)	−0.0034 (11)	−0.0095 (11)
C7	0.0325 (14)	0.0291 (13)	0.0221 (12)	0.0020 (11)	0.0005 (10)	−0.0053 (10)
C8	0.0316 (14)	0.0283 (13)	0.0273 (12)	−0.0023 (11)	0.0042 (10)	−0.0036 (10)
C9	0.0292 (14)	0.0393 (16)	0.0347 (14)	0.0019 (12)	0.0005 (11)	−0.0060 (12)
C10	0.0355 (15)	0.0484 (17)	0.0369 (15)	−0.0087 (13)	0.0101 (12)	−0.0023 (13)
C11	0.0451 (16)	0.0419 (16)	0.0246 (13)	−0.0021 (13)	0.0066 (11)	0.0027 (11)
P1	0.0471 (5)	0.0444 (5)	0.0736 (6)	0.0043 (4)	0.0254 (5)	−0.0012 (4)
F1	0.086 (4)	0.064 (3)	0.087 (4)	0.018 (3)	0.007 (3)	0.016 (3)
F2	0.052 (3)	0.092 (5)	0.175 (8)	−0.015 (3)	0.027 (5)	0.043 (5)
F3	0.103 (5)	0.094 (4)	0.119 (5)	0.022 (4)	0.022 (4)	−0.057 (4)
F4	0.115 (10)	0.173 (10)	0.102 (7)	−0.101 (9)	0.007 (6)	−0.010 (6)
F5	0.069 (4)	0.118 (6)	0.110 (6)	0.038 (4)	0.014 (4)	0.051 (5)
F6	0.159 (7)	0.143 (7)	0.065 (4)	0.024 (6)	0.044 (4)	−0.022 (4)
F1'	0.171 (11)	0.056 (5)	0.24 (2)	0.039 (6)	0.097 (12)	0.046 (7)
F2'	0.049 (5)	0.153 (10)	0.123 (8)	0.030 (6)	0.036 (5)	0.007 (7)
F3'	0.183 (14)	0.256 (18)	0.076 (7)	0.038 (13)	−0.048 (8)	−0.028 (8)
F4'	0.083 (9)	0.215 (18)	0.105 (10)	−0.012 (9)	0.063 (8)	0.054 (10)
F5'	0.077 (5)	0.063 (4)	0.129 (7)	0.016 (3)	0.047 (5)	−0.005 (4)
F6'	0.154 (10)	0.152 (10)	0.059 (4)	−0.049 (8)	0.002 (5)	−0.006 (5)
N4	0.084 (3)	0.080 (3)	0.0521 (19)	−0.026 (2)	0.0085 (17)	−0.0043 (17)
C12	0.067 (2)	0.051 (2)	0.0397 (18)	−0.0057 (18)	0.0052 (16)	−0.0009 (15)
C13	0.068 (3)	0.068 (3)	0.088 (3)	−0.002 (2)	0.013 (2)	0.013 (2)
N5	0.067 (2)	0.156 (4)	0.057 (2)	0.044 (3)	0.0217 (18)	0.025 (2)
C14	0.0406 (18)	0.071 (2)	0.060 (2)	0.0125 (17)	0.0159 (16)	0.0091 (19)
C15	0.092 (3)	0.071 (3)	0.074 (3)	−0.001 (2)	0.044 (3)	0.003 (2)

Geometric parameters (Å, º) top

Ag1—N1ⁱ	2.163 (2)	C9—H9	0.9500
Ag1—N2	2.166 (2)	C10—C11	1.385 (4)
Ag1—Ag1ⁱⁱ	3.3023 (5)	C10—H10	0.9500
N1—C1	1.338 (3)	C11—H11	0.9500
N1—C5	1.341 (4)	P1—F3'	1.435 (10)
N1—Ag1ⁱⁱⁱ	2.163 (2)	P1—F1'	1.495 (8)
N2—C8	1.342 (3)	P1—F5	1.501 (6)
N2—C9	1.343 (4)	P1—F6	1.512 (5)
N3—C2	1.379 (3)	P1—F4'	1.532 (14)
N3—C6	1.435 (3)	P1—F4	1.539 (12)
N3—H3A	0.84 (3)	P1—F2	1.570 (7)
C1—C2	1.401 (3)	P1—F2'	1.596 (11)
C1—H1	0.9500	P1—F3	1.617 (6)
C2—C3	1.396 (4)	P1—F5'	1.629 (9)
C3—C4	1.387 (4)	P1—F1	1.669 (5)
C3—H3	0.9500	P1—F6'	1.687 (8)
C4—C5	1.380 (4)	N4—C12	1.127 (5)
C4—H4	0.9500	C12—C13	1.452 (6)
C5—H5	0.9500	C13—H13A	0.9800
C6—C7	1.500 (4)	C13—H13B	0.9800
C6—H6A	0.9900	C13—H13C	0.9800
C6—H6B	0.9900	N5—C14	1.110 (5)
C7—C8	1.383 (4)	C14—C15	1.445 (5)
C7—C11	1.387 (4)	C15—H15A	0.9800
C8—H8	0.9500	C15—H15B	0.9800
C9—C10	1.375 (4)	C15—H15C	0.9800

N1ⁱ—Ag1—N2	170.55 (8)	C10—C11—H11	120.5
N1ⁱ—Ag1—Ag1ⁱⁱ	100.46 (6)	C7—C11—H11	120.5
N2—Ag1—Ag1ⁱⁱ	84.17 (6)	F3'—P1—F1'	98.8 (9)
C1—N1—C5	119.3 (2)	F5—P1—F6	96.7 (5)
C1—N1—Ag1ⁱⁱⁱ	119.39 (18)	F3'—P1—F4'	93.7 (10)
C5—N1—Ag1ⁱⁱⁱ	121.31 (17)	F1'—P1—F4'	86.1 (10)
C8—N2—C9	117.9 (2)	F5—P1—F4	90.8 (9)
C8—N2—Ag1	121.18 (18)	F6—P1—F4	92.8 (7)
C9—N2—Ag1	120.91 (17)	F5—P1—F2	94.0 (5)
C2—N3—C6	121.4 (2)	F6—P1—F2	90.7 (5)
C2—N3—H3A	117 (2)	F4—P1—F2	173.7 (8)
C6—N3—H3A	121 (2)	F3'—P1—F2'	96.2 (8)
N1—C1—C2	122.6 (2)	F1'—P1—F2'	92.7 (6)
N1—C1—H1	118.7	F4'—P1—F2'	170.1 (8)
C2—C1—H1	118.7	F5—P1—F3	91.0 (4)
N3—C2—C3	122.6 (2)	F6—P1—F3	172.3 (4)
N3—C2—C1	119.6 (2)	F4—P1—F3	86.5 (6)
C3—C2—C1	117.8 (2)	F2—P1—F3	89.3 (5)
C4—C3—C2	118.8 (2)	F3'—P1—F5'	88.8 (8)
C4—C3—H3	120.6	F1'—P1—F5'	172.5 (8)
C2—C3—H3	120.6	F4'—P1—F5'	93.3 (11)
C5—C4—C3	120.0 (3)	F2'—P1—F5'	86.6 (6)
C5—C4—H4	120.0	F5—P1—F1	173.5 (4)
C3—C4—H4	120.0	F6—P1—F1	89.4 (4)
N1—C5—C4	121.5 (2)	F4—P1—F1	91.3 (9)
N1—C5—H5	119.2	F2—P1—F1	83.5 (4)
C4—C5—H5	119.2	F3—P1—F1	82.9 (3)
N3—C6—C7	111.4 (2)	F3'—P1—F6'	171.5 (8)
N3—C6—H6A	109.3	F1'—P1—F6'	89.8 (8)
C7—C6—H6A	109.3	F4'—P1—F6'	87.3 (8)
N3—C6—H6B	109.3	F2'—P1—F6'	82.9 (5)
C7—C6—H6B	109.3	F5'—P1—F6'	82.7 (5)
H6A—C6—H6B	108.0	N4—C12—C13	179.6 (5)
C8—C7—C11	118.0 (2)	C12—C13—H13A	109.5
C8—C7—C6	120.1 (3)	C12—C13—H13B	109.5
C11—C7—C6	121.9 (2)	H13A—C13—H13B	109.5
N2—C8—C7	123.4 (2)	C12—C13—H13C	109.5
N2—C8—H8	118.3	H13A—C13—H13C	109.5
C7—C8—H8	118.3	H13B—C13—H13C	109.5
N2—C9—C10	122.4 (3)	N5—C14—C15	177.5 (4)
N2—C9—H9	118.8	C14—C15—H15A	109.5
C10—C9—H9	118.8	C14—C15—H15B	109.5
C9—C10—C11	119.3 (3)	H15A—C15—H15B	109.5
C9—C10—H10	120.3	C14—C15—H15C	109.5
C11—C10—H10	120.3	H15A—C15—H15C	109.5
C10—C11—C7	119.0 (3)	H15B—C15—H15C	109.5

C5—N1—C1—C2	0.5 (4)	N3—C6—C7—C8	−102.6 (3)
Ag1ⁱⁱⁱ—N1—C1—C2	−179.21 (19)	N3—C6—C7—C11	79.0 (3)
C6—N3—C2—C3	−6.3 (4)	C9—N2—C8—C7	−0.1 (4)
C6—N3—C2—C1	176.2 (3)	Ag1—N2—C8—C7	178.53 (19)
N1—C1—C2—N3	176.7 (3)	C11—C7—C8—N2	−0.6 (4)
N1—C1—C2—C3	−0.9 (4)	C6—C7—C8—N2	−179.0 (2)
N3—C2—C3—C4	−176.8 (3)	C8—N2—C9—C10	0.3 (4)
C1—C2—C3—C4	0.7 (4)	Ag1—N2—C9—C10	−178.3 (2)
C2—C3—C4—C5	−0.3 (4)	N2—C9—C10—C11	0.1 (4)
C1—N1—C5—C4	0.0 (4)	C9—C10—C11—C7	−0.8 (4)
Ag1ⁱⁱⁱ—N1—C5—C4	179.7 (2)	C8—C7—C11—C10	1.0 (4)
C3—C4—C5—N1	−0.1 (4)	C6—C7—C11—C10	179.4 (3)
C2—N3—C6—C7	174.7 (3)

Symmetry codes: (i) x+1/2, −y+1/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x−1/2, −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—H3A···F3	0.84 (3)	2.49 (3)	3.208 (8)	144 (3)
N3—H3A···F5	0.84 (3)	2.46 (3)	3.273 (10)	162 (3)
N3—H3A···F5′	0.84 (3)	2.18 (3)	2.999 (10)	167 (3)
C8—H8···N4ⁱⁱ	0.95	2.63	3.478 (5)	149
C10—H10···F2^iv	0.95	2.39	3.176 (9)	140
C13—H13A···F2′^iv	0.98	2.54	3.487 (13)	163
C13—H13B···F6ⁱ	0.98	2.53	3.365 (10)	144
C13—H13B···F1′ⁱ	0.98	2.59	3.57 (2)	171
C15—H15A···F1	0.98	2.52	3.441 (9)	157
C15—H15A···F3′	0.98	2.42	3.356 (13)	160
C15—H15B···F2^v	0.98	2.23	3.088 (10)	146
C15—H15B···F5′^v	0.98	2.57	3.509 (11)	160
C15—H15C···F1^iv	0.98	2.36	3.329 (8)	168
C15—H15C···F1′^iv	0.98	2.09	3.037 (9)	161

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

Funding information

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (NRF-2015R1D1A3A01020410 and NRF-2016R1D1A1B01012630).

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