Crystal structure of an AgI inter-calation compound: catena-poly[[silver(I)-μ-N-(pyridin-3-ylmeth-yl)pyridin-3-amine-κ2N:N'] hexa-fluorido-phosphate aceto-nitrile disolvate].

The asymmetric unit in the title compound, [Ag(C11H11N3)]PF6·2CH3CN or {[AgL]·PF6·2CH3CN} n , L = N-(pyridin-3-ylmeth-yl)pyridin-3-amine, comprises one AgI atom, one L ligand, two aceto-nitrile solvent mol-ecules and one PF6- anion disordered over two orientations in a 0.567 (11):0.433 (11) ratio. Each AgI 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 AgI 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 inter-molecular π-π stacking inter-actions [centroid-to-centroid distance = 3.5922 (15) Å] between the pyridine rings link these chains into a corrugated layer parallel to the ([Formula: see text]01) plane. The layers are stacked with a separation of 10.4532 (5) Å, and aceto-nitrile solvent mol-ecules and PF6- anions as guests are inter-calated between the layers. The layers are connected through several N/C-H⋯F hydrogen bonds and P-F⋯π inter-actions [F⋯ring centroid = 3.241 (8) Å] between the layer and the inter-calated guests and between the inter-calated guests, forming a three-dimensional supra-molecular network.

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 d 10 electronic configurations of the AgI ion (Leong & Vittal, 2011 ▸; Moulton & Zaworotko, 2001 ▸; Wang et al., 2012 ▸). In particular, AgI 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 AgI coordination polymers with dipyridyl-type ligands. Up to date, we have reported several AgI 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)– chains.

Structural commentary

The mol­ecular components of the title structure are shown in Fig. 1 ▸. The asymmetric unit comprises one AgI 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 AgI atom is two-coordinated in a slightly distorted linear coordination geometry [N1i—Ag1—N2 = 170.55 (8)°; symmetry code: (i) x + , −y + , z + ; Table 1 ▸]. This distortion from linear geometry may be caused by Ag⋯N inter­actions between the AgI 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 AgI center are tilted slightly, by 6.29 (15)° with respect to each other. In the chain, the AgI 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)°.

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 + , −y + , z + ; (ii) x − , −y + , z − .]

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) .

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 + , y − , −z + ], resulting in the formation of a corrugated layer spreading out along the (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.

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.

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⋯F2iv	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) ; (ii) ; (iii) ; (iv) .

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.

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 Csp 2—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[F 2 > 2σ(F 2)], wR(F 2), 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
Δρmax, Δρmin (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 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989017013421/su5393sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989017013421/su5393Isup2.hkl

CCDC reference: 1575393

Additional supporting information: crystallographic information; 3D view; checkCIF report

[Ag(C11H11N3)]PF6·2C2H3N	F(000) = 1032
Mr = 520.17	Dx = 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

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

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(Fo2) + (0.0297P)2 + 2.2488P] where P = (Fo2 + 2Fc2)/3
4316 reflections	(Δ/σ)max = 0.001
312 parameters	Δρmax = 1.12 e Å−3
18 restraints	Δρmin = −0.66 e Å−3

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.

	x	y	z	Uiso*/Ueq	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*

	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)

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)

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···F2iv	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···F2v	0.98	2.23	3.088 (10)	146
C15—H15B···F5′v	0.98	2.57	3.509 (11)	160
C15—H15C···F1iv	0.98	2.36	3.329 (8)	168
C15—H15C···F1′iv	0.98	2.09	3.037 (9)	161