Potassium bis­[bis­(1-benzyl-3-methyl­imidazolium)silver(I)] tris­(hexa­fluoridophosphate)

Haque, R.A.; Salman, A.W.; Whai, C.K.; Quah, C.K.; Fun, H.-K.

doi:10.1107/S1600536810051925

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Pages m97-m98

https://doi.org/10.1107/S1600536810051925

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Potassium bis[bis(1-benzyl-3-methylimidazolium)silver(I)] tris(hexafluoridophosphate)

Rosenani A. Haque,^a Abbas Washeel Salman,^a Choong Kah Whai,^a Ching Kheng Quah ^b ‡ and Hoong-Kun Fun ^b ^*§

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 10 December 2010; accepted 11 December 2010; online 18 December 2010)

In the title compound, K[Ag(C₁₁H₁₂N₂)₂]₂(PF₆)₃, the 12-coordinate potassium cation lies on a crystallographic twofold axis and one of the hexafluorophosphate anions is generated by $[\overline{1}]$ symmetry. In the complex cation, the Ag^I ion is coordinated by two C atoms; the two imidazolium rings are orientated at a dihedral angle of 8.14 (14)°. In the 1-benzyl-3-methylimidazolium units, the dihedral angles between imidazolium and phenyl rings are 80.47 (15) and 76.53 (14)°. The F atoms of the general-position hexafluorophosphate anion are disordered over two sets of sites in a 0.767 (17):0.233 (17) ratio. In the crystal, the hexafluorophosphate anions link the cations into three-dimensional networks via intermolecular C—H⋯F hydrogen bonds and are further consolidated by π–π stacking [centroid–centroid distances = 3.5518 (15) Å] interactions.

Related literature

For general background to and the biological activity of carbene derivatives, see: Lee et al. (2001 ); Bourissou et al. (2000 ); Herrmann & Köcher (1997 ); Hermann et al. (1996 ); Zhou et al. (2008 ); Wang & Lin (1998 ); Lin & Vasam (2007 ); Ray et al. (2007 ); Özdemir et al. (2010 ); Medvetz et al. (2008 ). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ). For related structures, see: Haque et al. (2010a ,b ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

K[Ag(C₁₁H₁₂N₂)₂]₂(PF₆)₃
M_r = 1378.65
Monoclinic, C 2/c
a = 19.917 (2) Å
b = 23.047 (2) Å
c = 11.5787 (12) Å
β = 103.108 (3)°
V = 5176.4 (9) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 100 K
0.49 × 0.42 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.632, T_max = 0.847
66454 measured reflections
7528 independent reflections
7058 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.124
S = 1.11
7528 reflections
372 parameters
51 restraints
H-atom parameters constrained
Δρ_max = 1.68 e Å⁻³
Δρ_min = −0.91 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—C12	2.092 (2)
Ag1—C1	2.093 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14A⋯F1ⁱ	0.93	2.45	3.285 (5)	149
C15—H15A⋯F6	0.97	2.51	3.204 (5)	129
C15—H15B⋯F4ⁱ	0.97	2.51	3.415 (7)	156
C22—H22A⋯F6ⁱⁱ	0.96	2.42	3.171 (5)	135
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810051925/hb5767sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051925/hb5767Isup2.hkl

checkCIF report

Comment top

Metal complexes of carbenes based on imidazol-2-ylidene have received much attention in the past few years (Lee et al., 2001). A major reason is that these N-heterocyclic carbenes(NHCs) can stabilize both high and low oxidation state metal ions and form stable complexes with a wide range of metals (Bourissou et al., 2000; Herrmann & Köcher, 1997; Hermann et al., 1996). Among these complexes, the family of silver NHC complexes have been receiving continuous attention (Zhou et al., 2008). The in-situ deprotonation method using Ag₂O as a basic metal source developed by Lin and co-workers (Wang & Lin, 1998) has been widely employed to synthesise these Ag-NHC complexes. The silver complexes act as effective carbene transfer agents to other metals and are much more stable than the free carbene (Lin & Vasam, 2007). Biological activity of many Ag-NHC complexes as antimicrobial and antitumour agents has been confirmed (Ray et al., 2007; Özdemir et al., 2010; Medvetz et al., 2008).

The asymmetric unit of the title compound, (I), contains a bis(1-benzyl-3-methylimidazolium)silver(I) cation, a K cation and one and a half hexafluorophosphate anions (Fig. 1). The two imidazolium rings (N1/N2/C1-C3 and N3/N4/C12-C14) make a dihedral angle of 8.14 (14)°, indicating that they are almost parallel to each other. In the two 1-benzyl-3-methylimidazolium moieties [N1/N2/C1-C11 (A) and N3/N4/C12-C22 (B)], the dihedral angles between imidazolium and phenyl rings are 80.47 (15) and 76.53 (14)° in A and B, respectively. The P2 atom of the hexafluorophosphate anion is lying on a crystallographic inversion center (symmetry code: -x, -y, -z) whereas the 12-coordinate potassium cation (Fig. 2) lies on a crystallographic twofold axis (symmetry code: -x, y, -z+1/2). Six fluorine atoms (F1A-F6A) of the hexafluorophosphate anion are disordered over two positions with refined site-occupancies of 0.767 (17) : 0.233 (17). Bond lengths and angles are within normal ranges, and comparable to closely related structures (Haque et al., 2010a,b)

In the crystal structure, (Fig. 3), the hexafluorophosphate anions link the cations into three-dimensional networks via intermolecular C14–H14A···F1, C15–H15A···F6, C15–H15BA···F4 and C22–H22A···F6 hydrogen bonds (Table 2) and are further consolidated by π-π stacking interactions between N1/N2/C1-C3 (centroid Cg1) and N3/N4/C12-C14 (centroid Cg2) rings, with a Cg1···Cg2 distance of 3.5518 (15) Å.

Related literature top

For general background to and the biological activity of carbene derivatives, see: Lee et al. (2001); Bourissou et al. (2000); Herrmann & Köcher (1997); Hermann et al. (1996); Zhou et al. (2008); Wang & Lin (1998); Lin & Vasam (2007); Ray et al. (2007); Özdemir et al. (2010); Medvetz et al. (2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For related structures, see: Haque et al. (2010a,b).

For related literature, see: Allen et al. (1987).

Experimental top

To a stirred solution of 1-benzyl-3-methylimidazolium hexafluorophosphate (0.5 g, 1.57 mmol) in acetonitrile (40 ml), Ag₂O (0.37 g, 1.6 mmol) was added. The mixture was refluxed at 70 °C for 18 h in glassware wrapped in aluminum foil to exclude the light. The mixture was filtered through celite to remove excess Ag₂O and the solvent was evaporated under vacuum. The white residue was washed with diethyl ether (2 × 3 ml) to afford the complex as a white powder, the yield was 0.66 g, 70.3%, m. p. = 421-423 K. Colourless blocks of (I) were obtained by slow diffusion of diethyl ether into a solution of the complex in acetonitrile at ambient temperature.

Structure description top

For general background to and the biological activity of carbene derivatives, see: Lee et al. (2001); Bourissou et al. (2000); Herrmann & Köcher (1997); Hermann et al. (1996); Zhou et al. (2008); Wang & Lin (1998); Lin & Vasam (2007); Ray et al. (2007); Özdemir et al. (2010); Medvetz et al. (2008). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986). For related structures, see: Haque et al. (2010a,b).

For related literature, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids for non-H atoms. Both major and minor components of disorder are shown. Symmetry code: ($) -x, -y, -z. Coordination interactions between K cation and hexafluorophosphate anions have been omitted for clarity.
	Fig. 2. (a) Part of the crystal packing, highlighting the coordination environment for K cation. Displacement ellipsoids are drawn at the 30% probability level. Only major component of disorder is shown. (b) Extended coordination environment for K cations. Only major component of disorder is shown.
	Fig. 3. The crystal structure of (I), viewed along the c axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity. Only major component of disorder is shown.

Potassium bis[bis(1-benzyl-3-methylimidazolium)silver(I)] tris(hexafluoridophosphate) top

Crystal data top

K[Ag(C₁₁H₁₂N₂)₂]₂(PF₆)₃	F(000) = 2752
M_r = 1378.65	D_x = 1.769 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9934 reflections
a = 19.917 (2) Å	θ = 2.5–37.7°
b = 23.047 (2) Å	µ = 1.04 mm⁻¹
c = 11.5787 (12) Å	T = 100 K
β = 103.108 (3)°	Block, colourless
V = 5176.4 (9) Å³	0.49 × 0.42 × 0.17 mm
Z = 4

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	7528 independent reflections
Radiation source: fine-focus sealed tube	7058 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
φ and ω scans	θ_max = 30.0°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −28→27
T_min = 0.632, T_max = 0.847	k = −32→32
66454 measured reflections	l = −16→16

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.072P)² + 12.8353P] where P = (F_o² + 2F_c²)/3
7528 reflections	(Δ/σ)_max = 0.001
372 parameters	Δρ_max = 1.68 e Å⁻³
51 restraints	Δρ_min = −0.91 e Å⁻³

Crystal data top

K[Ag(C₁₁H₁₂N₂)₂]₂(PF₆)₃	V = 5176.4 (9) Å³
M_r = 1378.65	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 19.917 (2) Å	µ = 1.04 mm⁻¹
b = 23.047 (2) Å	T = 100 K
c = 11.5787 (12) Å	0.49 × 0.42 × 0.17 mm
β = 103.108 (3)°

Data collection top

Bruker SMART APEXII DUO CCD diffractometer	7528 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	7058 reflections with I > 2σ(I)
T_min = 0.632, T_max = 0.847	R_int = 0.050
66454 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	51 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.072P)² + 12.8353P] where P = (F_o² + 2F_c²)/3
7528 reflections	Δρ_max = 1.68 e Å⁻³
372 parameters	Δρ_min = −0.91 e Å⁻³

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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.

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 > 2sigma(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	Occ. (<1)
Ag1	0.313945 (8)	0.186742 (7)	0.040241 (15)	0.02197 (7)
N1	0.25175 (10)	0.13210 (9)	−0.20778 (18)	0.0220 (4)
N2	0.22372 (10)	0.08198 (8)	−0.07022 (18)	0.0219 (4)
N3	0.39227 (10)	0.29823 (9)	0.12655 (19)	0.0236 (4)
N4	0.37731 (10)	0.25291 (9)	0.27988 (18)	0.0227 (4)
C1	0.25902 (11)	0.13002 (10)	−0.0883 (2)	0.0205 (4)
C2	0.21334 (13)	0.08620 (10)	−0.2628 (2)	0.0250 (4)
H2A	0.2020	0.0785	−0.3437	0.030*
C3	0.19529 (12)	0.05430 (10)	−0.1766 (2)	0.0250 (4)
H3A	0.1690	0.0205	−0.1866	0.030*
C4	0.22223 (13)	0.05954 (11)	0.0474 (2)	0.0257 (4)
H4A	0.1822	0.0348	0.0414	0.031*
H4B	0.2180	0.0917	0.0994	0.031*
C5	0.28652 (13)	0.02546 (10)	0.1002 (2)	0.0240 (4)
C6	0.3103 (2)	−0.01707 (15)	0.0352 (3)	0.0424 (8)
H6A	0.2872	−0.0240	−0.0429	0.051*
C7	0.3684 (2)	−0.04945 (18)	0.0855 (3)	0.0580 (11)
H7A	0.3843	−0.0777	0.0409	0.070*
C8	0.40217 (19)	−0.04004 (17)	0.1999 (3)	0.0491 (9)
H8A	0.4405	−0.0624	0.2337	0.059*
C9	0.37995 (17)	0.00225 (15)	0.2653 (3)	0.0430 (7)
H9A	0.4035	0.0088	0.3432	0.052*
C10	0.32197 (15)	0.03570 (12)	0.2157 (2)	0.0310 (5)
H10A	0.3073	0.0647	0.2602	0.037*
C11	0.28146 (14)	0.17678 (12)	−0.2715 (2)	0.0288 (5)
H11A	0.2954	0.2095	−0.2203	0.043*
H11B	0.2476	0.1889	−0.3401	0.043*
H11C	0.3208	0.1612	−0.2957	0.043*
C12	0.36699 (11)	0.24814 (10)	0.1601 (2)	0.0210 (4)
C13	0.41715 (12)	0.33379 (11)	0.2217 (2)	0.0272 (5)
H13A	0.4363	0.3705	0.2196	0.033*
C14	0.40833 (14)	0.30508 (12)	0.3196 (2)	0.0281 (5)
H14A	0.4207	0.3179	0.3977	0.034*
C15	0.36321 (12)	0.20739 (12)	0.3596 (2)	0.0267 (5)
H15A	0.3339	0.1780	0.3138	0.032*
H15B	0.3389	0.2240	0.4154	0.032*
C16	0.42893 (13)	0.17983 (11)	0.4265 (2)	0.0242 (4)
C17	0.45994 (14)	0.19764 (13)	0.5417 (2)	0.0303 (5)
H17A	0.4396	0.2264	0.5786	0.036*
C18	0.52170 (15)	0.17182 (16)	0.6012 (3)	0.0367 (6)
H18A	0.5429	0.1843	0.6771	0.044*
C19	0.55127 (14)	0.12872 (14)	0.5493 (3)	0.0362 (6)
H19A	0.5918	0.1114	0.5906	0.043*
C20	0.52082 (16)	0.11032 (13)	0.4341 (3)	0.0364 (6)
H20A	0.5413	0.0812	0.3982	0.044*
C21	0.45960 (14)	0.13608 (12)	0.3739 (2)	0.0304 (5)
H21A	0.4390	0.1238	0.2976	0.036*
C22	0.39464 (16)	0.31203 (12)	0.0039 (3)	0.0310 (5)
H22A	0.3519	0.3009	−0.0483	0.046*
H22B	0.4319	0.2912	−0.0171	0.046*
H22C	0.4017	0.3530	−0.0032	0.046*
K1	0.0000	0.08540 (3)	0.2500	0.02658 (15)
P1	0.16091 (3)	0.15499 (3)	0.34572 (6)	0.02586 (13)
F1	0.1121 (3)	0.1369 (2)	0.4315 (4)	0.0663 (14)	0.767 (17)
F2	0.2272 (4)	0.1299 (3)	0.4279 (6)	0.079 (2)	0.767 (17)
F3	0.1443 (3)	0.0957 (2)	0.2724 (5)	0.0475 (11)	0.767 (17)
F4	0.1743 (3)	0.2155 (3)	0.4111 (6)	0.074 (2)	0.767 (17)
F5	0.09354 (17)	0.18170 (17)	0.2567 (5)	0.0448 (9)	0.767 (17)
F6	0.20487 (19)	0.1757 (3)	0.2508 (3)	0.0307 (8)	0.767 (17)
F1A	0.1259 (10)	0.1383 (9)	0.4538 (18)	0.065 (4)*	0.233 (17)
F2A	0.2363 (8)	0.1276 (6)	0.4325 (14)	0.035 (3)*	0.233 (17)
F3A	0.1448 (7)	0.0905 (6)	0.2965 (13)	0.027 (2)*	0.233 (17)
F4A	0.1841 (8)	0.2166 (5)	0.4153 (12)	0.029 (3)*	0.233 (17)
F5A	0.0936 (7)	0.1771 (6)	0.2895 (16)	0.043 (3)*	0.233 (17)
F6A	0.2099 (8)	0.1626 (7)	0.2645 (16)	0.045 (4)*	0.233 (17)
P2	0.0000	0.0000	0.0000	0.02900 (19)
F7	0.00552 (14)	0.06866 (9)	0.0087 (2)	0.0535 (5)
F8	−0.05948 (12)	0.00366 (12)	−0.1174 (2)	0.0589 (6)
F9	−0.05557 (11)	0.00116 (10)	0.0805 (2)	0.0524 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.02133 (11)	0.02546 (11)	0.01764 (11)	−0.00150 (5)	0.00131 (7)	−0.00177 (5)
N1	0.0217 (8)	0.0241 (9)	0.0194 (8)	0.0014 (7)	0.0034 (7)	0.0010 (7)
N2	0.0204 (8)	0.0223 (8)	0.0225 (9)	−0.0001 (7)	0.0039 (7)	−0.0005 (7)
N3	0.0211 (8)	0.0259 (9)	0.0222 (9)	0.0023 (7)	0.0014 (7)	0.0023 (7)
N4	0.0189 (8)	0.0283 (9)	0.0195 (9)	0.0010 (7)	0.0013 (7)	−0.0030 (7)
C1	0.0188 (9)	0.0221 (9)	0.0192 (9)	0.0011 (7)	0.0017 (7)	−0.0002 (7)
C2	0.0263 (10)	0.0251 (10)	0.0211 (10)	0.0029 (8)	0.0005 (8)	−0.0038 (8)
C3	0.0242 (10)	0.0233 (10)	0.0252 (11)	−0.0003 (8)	0.0009 (8)	−0.0034 (8)
C4	0.0250 (10)	0.0291 (11)	0.0250 (11)	0.0018 (8)	0.0100 (9)	0.0034 (9)
C5	0.0291 (11)	0.0210 (9)	0.0238 (10)	−0.0004 (8)	0.0100 (9)	0.0043 (8)
C6	0.067 (2)	0.0360 (15)	0.0256 (13)	0.0220 (14)	0.0136 (14)	0.0044 (10)
C7	0.086 (3)	0.053 (2)	0.0436 (18)	0.044 (2)	0.0335 (19)	0.0202 (16)
C8	0.0438 (16)	0.0560 (19)	0.0522 (19)	0.0212 (15)	0.0211 (15)	0.0304 (16)
C9	0.0385 (15)	0.0455 (16)	0.0392 (16)	−0.0030 (12)	−0.0034 (12)	0.0127 (13)
C10	0.0387 (13)	0.0263 (11)	0.0262 (12)	−0.0012 (10)	0.0034 (10)	0.0015 (9)
C11	0.0297 (12)	0.0323 (11)	0.0246 (11)	−0.0016 (9)	0.0066 (9)	0.0052 (9)
C12	0.0179 (9)	0.0263 (10)	0.0172 (9)	0.0019 (7)	0.0006 (7)	−0.0015 (7)
C13	0.0213 (10)	0.0249 (10)	0.0334 (12)	0.0011 (8)	0.0021 (9)	−0.0057 (9)
C14	0.0254 (11)	0.0308 (11)	0.0249 (11)	0.0011 (9)	−0.0009 (9)	−0.0081 (9)
C15	0.0203 (10)	0.0397 (13)	0.0199 (10)	−0.0002 (9)	0.0041 (8)	0.0011 (9)
C16	0.0216 (10)	0.0307 (11)	0.0197 (10)	−0.0015 (8)	0.0032 (8)	0.0039 (8)
C17	0.0277 (12)	0.0409 (13)	0.0209 (11)	0.0024 (10)	0.0029 (9)	0.0006 (10)
C18	0.0289 (12)	0.0556 (17)	0.0216 (12)	−0.0011 (12)	−0.0028 (10)	0.0072 (11)
C19	0.0235 (11)	0.0468 (15)	0.0384 (14)	0.0035 (10)	0.0071 (10)	0.0213 (12)
C20	0.0362 (14)	0.0366 (13)	0.0395 (15)	0.0091 (11)	0.0150 (12)	0.0105 (11)
C21	0.0306 (12)	0.0355 (13)	0.0256 (11)	−0.0010 (10)	0.0079 (9)	0.0004 (9)
C22	0.0321 (13)	0.0351 (13)	0.0261 (12)	0.0015 (9)	0.0073 (10)	0.0070 (9)
K1	0.0297 (3)	0.0282 (3)	0.0220 (3)	0.000	0.0061 (3)	0.000
P1	0.0312 (3)	0.0280 (3)	0.0191 (3)	−0.0048 (2)	0.0072 (2)	−0.0045 (2)
F1	0.100 (3)	0.076 (2)	0.0405 (19)	−0.052 (2)	0.053 (2)	−0.0271 (16)
F2	0.069 (3)	0.101 (4)	0.049 (2)	0.005 (2)	−0.023 (2)	0.026 (2)
F3	0.066 (2)	0.0377 (17)	0.047 (2)	−0.0194 (14)	0.0316 (19)	−0.0191 (17)
F4	0.079 (4)	0.066 (2)	0.092 (3)	−0.042 (2)	0.050 (3)	−0.057 (3)
F5	0.0300 (13)	0.065 (2)	0.0393 (19)	0.0101 (10)	0.0067 (13)	0.0182 (15)
F6	0.0294 (13)	0.0433 (19)	0.0212 (12)	−0.0078 (12)	0.0091 (9)	0.0043 (12)
P2	0.0251 (4)	0.0345 (5)	0.0291 (4)	−0.0088 (3)	0.0096 (3)	−0.0127 (3)
F7	0.0752 (15)	0.0358 (9)	0.0569 (13)	−0.0114 (9)	0.0306 (11)	−0.0140 (9)
F8	0.0468 (12)	0.0796 (16)	0.0428 (11)	0.0010 (11)	−0.0054 (9)	−0.0118 (11)
F9	0.0472 (11)	0.0645 (13)	0.0559 (12)	−0.0226 (10)	0.0333 (10)	−0.0300 (10)

Geometric parameters (Å, º) top

Ag1—C12	2.092 (2)	C17—H17A	0.9300
Ag1—C1	2.093 (2)	C18—C19	1.361 (5)
N1—C1	1.359 (3)	C18—H18A	0.9300
N1—C2	1.374 (3)	C19—C20	1.400 (5)
N1—C11	1.467 (3)	C19—H19A	0.9300
N2—C1	1.353 (3)	C20—C21	1.393 (4)
N2—C3	1.389 (3)	C20—H20A	0.9300
N2—C4	1.463 (3)	C21—H21A	0.9300
N3—C12	1.351 (3)	C22—H22A	0.9600
N3—C13	1.372 (3)	C22—H22B	0.9600
N3—C22	1.467 (3)	C22—H22C	0.9600
N4—C12	1.360 (3)	K1—F5Aⁱ	2.786 (14)
N4—C14	1.382 (3)	K1—F5A	2.786 (14)
N4—C15	1.466 (3)	K1—F9	2.803 (2)
C2—C3	1.352 (4)	K1—F9ⁱ	2.803 (2)
C2—H2A	0.9300	K1—F3Aⁱ	2.813 (13)
C3—H3A	0.9300	K1—F3A	2.813 (13)
C4—C5	1.509 (3)	K1—F3	2.836 (5)
C4—H4A	0.9700	K1—F3ⁱ	2.836 (5)
C4—H4B	0.9700	K1—F7ⁱ	2.848 (2)
C5—C6	1.383 (4)	K1—F7	2.848 (2)
C5—C10	1.384 (4)	K1—F5	2.887 (4)
C6—C7	1.390 (5)	K1—F5ⁱ	2.887 (4)
C6—H6A	0.9300	P1—F5A	1.444 (14)
C7—C8	1.359 (6)	P1—F6A	1.512 (16)
C7—H7A	0.9300	P1—F2	1.554 (5)
C8—C9	1.368 (6)	P1—F4	1.580 (5)
C8—H8A	0.9300	P1—F1	1.596 (3)
C9—C10	1.399 (4)	P1—F3A	1.597 (14)
C9—H9A	0.9300	P1—F3	1.604 (4)
C10—H10A	0.9300	P1—F1A	1.612 (17)
C11—H11A	0.9600	P1—F5	1.617 (4)
C11—H11B	0.9600	P1—F6	1.625 (3)
C11—H11C	0.9600	P1—F4A	1.646 (14)
C13—C14	1.358 (4)	P1—F2A	1.725 (16)
C13—H13A	0.9300	P2—F7	1.588 (2)
C14—H14A	0.9300	P2—F7ⁱⁱ	1.588 (2)
C15—C16	1.502 (3)	P2—F8	1.590 (2)
C15—H15A	0.9700	P2—F8ⁱⁱ	1.590 (2)
C15—H15B	0.9700	P2—F9	1.6010 (18)
C16—C21	1.389 (4)	P2—F9ⁱⁱ	1.6010 (18)
C16—C17	1.399 (4)	P2—K1ⁱⁱ	3.5004 (5)
C17—C18	1.399 (4)	F8—K1ⁱⁱ	2.966 (3)

C12—Ag1—C1	175.99 (9)	F5Aⁱ—K1—F7	96.6 (4)
C1—N1—C2	111.4 (2)	F5A—K1—F7	95.2 (4)
C1—N1—C11	125.1 (2)	F9—K1—F7	46.86 (6)
C2—N1—C11	123.6 (2)	F9ⁱ—K1—F7	119.74 (7)
C1—N2—C3	111.1 (2)	F3Aⁱ—K1—F7	94.8 (3)
C1—N2—C4	123.6 (2)	F3A—K1—F7	85.8 (3)
C3—N2—C4	124.9 (2)	F3—K1—F7	80.62 (12)
C12—N3—C13	111.7 (2)	F3ⁱ—K1—F7	100.69 (13)
C12—N3—C22	124.0 (2)	F7ⁱ—K1—F7	164.42 (9)
C13—N3—C22	124.3 (2)	F5Aⁱ—K1—F5	79.9 (2)
C12—N4—C14	111.2 (2)	F5A—K1—F5	7.7 (3)
C12—N4—C15	125.3 (2)	F9—K1—F5	134.50 (12)
C14—N4—C15	123.2 (2)	F9ⁱ—K1—F5	111.32 (10)
N2—C1—N1	104.30 (19)	F3Aⁱ—K1—F5	126.9 (3)
N2—C1—Ag1	127.39 (17)	F3A—K1—F5	48.3 (3)
N1—C1—Ag1	128.29 (17)	F3—K1—F5	45.51 (12)
C3—C2—N1	106.8 (2)	F3ⁱ—K1—F5	124.94 (13)
C3—C2—H2A	126.6	F7ⁱ—K1—F5	104.25 (12)
N1—C2—H2A	126.6	F7—K1—F5	87.83 (12)
C2—C3—N2	106.4 (2)	F5Aⁱ—K1—F5ⁱ	7.7 (3)
C2—C3—H3A	126.8	F5A—K1—F5ⁱ	79.9 (2)
N2—C3—H3A	126.8	F9—K1—F5ⁱ	111.32 (10)
N2—C4—C5	111.51 (19)	F9ⁱ—K1—F5ⁱ	134.51 (12)
N2—C4—H4A	109.3	F3Aⁱ—K1—F5ⁱ	48.3 (3)
C5—C4—H4A	109.3	F3A—K1—F5ⁱ	126.9 (3)
N2—C4—H4B	109.3	F3—K1—F5ⁱ	124.94 (13)
C5—C4—H4B	109.3	F3ⁱ—K1—F5ⁱ	45.51 (12)
H4A—C4—H4B	108.0	F7ⁱ—K1—F5ⁱ	87.83 (12)
C6—C5—C10	119.0 (3)	F7—K1—F5ⁱ	104.25 (12)
C6—C5—C4	120.8 (2)	F5—K1—F5ⁱ	79.54 (13)
C10—C5—C4	120.2 (2)	F5A—P1—F6A	110.1 (11)
C5—C6—C7	120.5 (3)	F5A—P1—F2	168.8 (7)
C5—C6—H6A	119.8	F6A—P1—F2	81.1 (8)
C7—C6—H6A	119.8	F5A—P1—F4	86.8 (6)
C8—C7—C6	120.3 (3)	F6A—P1—F4	97.7 (7)
C8—C7—H7A	119.9	F2—P1—F4	90.4 (4)
C6—C7—H7A	119.9	F5A—P1—F1	74.8 (7)
C7—C8—C9	120.2 (3)	F6A—P1—F1	171.4 (7)
C7—C8—H8A	119.9	F2—P1—F1	94.3 (4)
C9—C8—H8A	119.9	F4—P1—F1	89.6 (3)
C8—C9—C10	120.4 (3)	F5A—P1—F3A	94.3 (7)
C8—C9—H9A	119.8	F6A—P1—F3A	89.5 (8)
C10—C9—H9A	119.8	F2—P1—F3A	87.0 (6)
C5—C10—C9	119.7 (3)	F4—P1—F3A	171.9 (6)
C5—C10—H10A	120.1	F1—P1—F3A	83.0 (6)
C9—C10—H10A	120.1	F5A—P1—F3	90.2 (6)
N1—C11—H11A	109.5	F6A—P1—F3	81.6 (7)
N1—C11—H11B	109.5	F2—P1—F3	93.0 (4)
H11A—C11—H11B	109.5	F4—P1—F3	176.4 (4)
N1—C11—H11C	109.5	F1—P1—F3	91.4 (2)
H11A—C11—H11C	109.5	F5A—P1—F1A	85.1 (8)
H11B—C11—H11C	109.5	F6A—P1—F1A	164.8 (11)
N3—C12—N4	104.1 (2)	F2—P1—F1A	83.9 (8)
N3—C12—Ag1	123.54 (16)	F4—P1—F1A	83.9 (8)
N4—C12—Ag1	131.89 (17)	F3A—P1—F1A	88.1 (8)
C14—C13—N3	106.7 (2)	F3—P1—F1A	97.7 (8)
C14—C13—H13A	126.6	F6A—P1—F5	96.8 (8)
N3—C13—H13A	126.6	F2—P1—F5	177.9 (3)
C13—C14—N4	106.2 (2)	F4—P1—F5	89.7 (3)
C13—C14—H14A	126.9	F1—P1—F5	87.8 (3)
N4—C14—H14A	126.9	F3A—P1—F5	93.2 (5)
N4—C15—C16	110.98 (19)	F3—P1—F5	86.9 (3)
N4—C15—H15A	109.4	F1A—P1—F5	98.3 (7)
C16—C15—H15A	109.4	F5A—P1—F6	100.3 (8)
N4—C15—H15B	109.4	F2—P1—F6	90.6 (4)
C16—C15—H15B	109.4	F4—P1—F6	90.4 (3)
H15A—C15—H15B	108.0	F1—P1—F6	175.1 (4)
C21—C16—C17	119.2 (2)	F3A—P1—F6	97.3 (5)
C21—C16—C15	120.0 (2)	F3—P1—F6	88.3 (2)
C17—C16—C15	120.8 (2)	F1A—P1—F6	172.0 (8)
C18—C17—C16	119.6 (3)	F5—P1—F6	87.3 (3)
C18—C17—H17A	120.2	F5A—P1—F4A	92.6 (7)
C16—C17—H17A	120.2	F6A—P1—F4A	93.2 (8)
C19—C18—C17	120.9 (3)	F2—P1—F4A	85.2 (5)
C19—C18—H18A	119.6	F1—P1—F4A	93.6 (6)
C17—C18—H18A	119.6	F3A—P1—F4A	171.2 (7)
C18—C19—C20	120.3 (3)	F3—P1—F4A	174.7 (6)
C18—C19—H19A	119.9	F1A—P1—F4A	87.1 (9)
C20—C19—H19A	119.9	F5—P1—F4A	94.8 (4)
C21—C20—C19	119.2 (3)	F6—P1—F4A	86.8 (6)
C21—C20—H20A	120.4	F5A—P1—F2A	171.1 (9)
C19—C20—H20A	120.4	F6A—P1—F2A	78.8 (8)
C16—C21—C20	120.8 (3)	F4—P1—F2A	90.8 (5)
C16—C21—H21A	119.6	F1—P1—F2A	96.6 (6)
C20—C21—H21A	119.6	F3A—P1—F2A	86.9 (6)
N3—C22—H22A	109.5	F3—P1—F2A	92.5 (5)
N3—C22—H22B	109.5	F1A—P1—F2A	86.2 (8)
H22A—C22—H22B	109.5	F5—P1—F2A	175.6 (5)
N3—C22—H22C	109.5	F6—P1—F2A	88.3 (5)
H22A—C22—H22C	109.5	F4A—P1—F2A	85.4 (6)
H22B—C22—H22C	109.5	P1—F1—K1	97.5 (2)
F5Aⁱ—K1—F5A	81.3 (6)	P1—F3—K1	101.7 (2)
F5Aⁱ—K1—F9	105.5 (3)	P1—F5—K1	99.30 (19)
F5A—K1—F9	141.6 (4)	P1—F1A—K1	85.7 (9)
F5Aⁱ—K1—F9ⁱ	141.6 (4)	P1—F3A—K1	102.8 (6)
F5A—K1—F9ⁱ	105.5 (3)	P1—F5A—K1	108.9 (7)
F9—K1—F9ⁱ	92.34 (12)	F7—P2—F7ⁱⁱ	180.0
F5Aⁱ—K1—F3Aⁱ	47.0 (4)	F7—P2—F8	91.64 (14)
F5A—K1—F3Aⁱ	128.2 (4)	F7ⁱⁱ—P2—F8	88.36 (14)
F9—K1—F3Aⁱ	70.8 (3)	F7—P2—F8ⁱⁱ	88.36 (14)
F9ⁱ—K1—F3Aⁱ	112.8 (3)	F7ⁱⁱ—P2—F8ⁱⁱ	91.64 (14)
F5Aⁱ—K1—F3A	128.2 (4)	F8—P2—F8ⁱⁱ	180.0
F5A—K1—F3A	47.0 (4)	F7—P2—F9	89.64 (12)
F9—K1—F3A	112.8 (3)	F7ⁱⁱ—P2—F9	90.36 (12)
F9ⁱ—K1—F3A	70.8 (3)	F8—P2—F9	91.02 (13)
F3Aⁱ—K1—F3A	175.2 (5)	F8ⁱⁱ—P2—F9	88.99 (13)
F5Aⁱ—K1—F3	125.3 (3)	F7—P2—F9ⁱⁱ	90.36 (12)
F5A—K1—F3	45.2 (3)	F7ⁱⁱ—P2—F9ⁱⁱ	89.64 (12)
F9—K1—F3	110.65 (9)	F8—P2—F9ⁱⁱ	88.98 (13)
F9ⁱ—K1—F3	76.28 (14)	F8ⁱⁱ—P2—F9ⁱⁱ	91.02 (13)
F3Aⁱ—K1—F3	170.9 (3)	F9—P2—F9ⁱⁱ	179.999 (1)
F3A—K1—F3	6.1 (3)	F7—P2—K1ⁱⁱ	126.84 (8)
F5Aⁱ—K1—F3ⁱ	45.2 (3)	F7ⁱⁱ—P2—K1ⁱⁱ	53.16 (8)
F5A—K1—F3ⁱ	125.3 (3)	F8—P2—K1ⁱⁱ	57.49 (9)
F9—K1—F3ⁱ	76.28 (14)	F8ⁱⁱ—P2—K1ⁱⁱ	122.51 (9)
F9ⁱ—K1—F3ⁱ	110.65 (9)	F9—P2—K1ⁱⁱ	128.37 (7)
F3Aⁱ—K1—F3ⁱ	6.1 (3)	F9ⁱⁱ—P2—K1ⁱⁱ	51.63 (7)
F3A—K1—F3ⁱ	170.9 (3)	F7—P2—K1	53.16 (8)
F3—K1—F3ⁱ	170.4 (2)	F7ⁱⁱ—P2—K1	126.84 (8)
F5Aⁱ—K1—F7ⁱ	95.2 (4)	F8—P2—K1	122.51 (9)
F5A—K1—F7ⁱ	96.6 (4)	F8ⁱⁱ—P2—K1	57.49 (9)
F9—K1—F7ⁱ	119.74 (7)	F9—P2—K1	51.63 (7)
F9ⁱ—K1—F7ⁱ	46.87 (6)	F9ⁱⁱ—P2—K1	128.37 (7)
F3Aⁱ—K1—F7ⁱ	85.8 (3)	K1ⁱⁱ—P2—K1	180.0
F3A—K1—F7ⁱ	94.8 (3)	P2—F7—K1	100.34 (11)
F3—K1—F7ⁱ	100.69 (13)	P2—F8—K1ⁱⁱ	95.64 (11)
F3ⁱ—K1—F7ⁱ	80.62 (12)	P2—F9—K1	101.77 (9)

C3—N2—C1—N1	0.4 (2)	F5—P1—F3A—K1	−36.3 (6)
C4—N2—C1—N1	174.6 (2)	F6—P1—F3A—K1	−124.0 (4)
C3—N2—C1—Ag1	−178.37 (16)	F2A—P1—F3A—K1	148.1 (7)
C4—N2—C1—Ag1	−4.2 (3)	F5Aⁱ—K1—F3A—P1	22.0 (8)
C2—N1—C1—N2	−0.5 (2)	F5A—K1—F3A—P1	16.0 (7)
C11—N1—C1—N2	−179.7 (2)	F9—K1—F3A—P1	156.4 (5)
C2—N1—C1—Ag1	178.26 (16)	F9ⁱ—K1—F3A—P1	−119.4 (7)
C11—N1—C1—Ag1	−1.0 (3)	F3—K1—F3A—P1	86 (3)
C1—N1—C2—C3	0.4 (3)	F7ⁱ—K1—F3A—P1	−78.5 (6)
C11—N1—C2—C3	179.6 (2)	F7—K1—F3A—P1	117.1 (6)
N1—C2—C3—N2	−0.1 (3)	F5—K1—F3A—P1	26.3 (5)
C1—N2—C3—C2	−0.2 (3)	F5ⁱ—K1—F3A—P1	12.4 (8)
C4—N2—C3—C2	−174.3 (2)	F6A—P1—F5A—K1	115.1 (10)
C1—N2—C4—C5	−79.8 (3)	F2—P1—F5A—K1	−72 (3)
C3—N2—C4—C5	93.6 (3)	F4—P1—F5A—K1	−147.9 (7)
N2—C4—C5—C6	−48.9 (3)	F1—P1—F5A—K1	−57.5 (6)
N2—C4—C5—C10	132.3 (2)	F3A—P1—F5A—K1	24.0 (10)
C10—C5—C6—C7	0.8 (5)	F3—P1—F5A—K1	34.0 (7)
C4—C5—C6—C7	−178.1 (3)	F1A—P1—F5A—K1	−63.7 (11)
C5—C6—C7—C8	0.6 (6)	F5—P1—F5A—K1	109 (3)
C6—C7—C8—C9	−1.4 (6)	F6—P1—F5A—K1	122.2 (7)
C7—C8—C9—C10	0.7 (6)	F4A—P1—F5A—K1	−150.6 (8)
C6—C5—C10—C9	−1.4 (4)	F5Aⁱ—K1—F5A—P1	166.3 (13)
C4—C5—C10—C9	177.5 (3)	F9—K1—F5A—P1	−89.6 (10)
C8—C9—C10—C5	0.7 (5)	F9ⁱ—K1—F5A—P1	25.1 (9)
C13—N3—C12—N4	−0.6 (3)	F3Aⁱ—K1—F5A—P1	162.0 (8)
C22—N3—C12—N4	177.7 (2)	F3—K1—F5A—P1	−26.5 (6)
C13—N3—C12—Ag1	172.52 (16)	F3ⁱ—K1—F5A—P1	155.2 (7)
C22—N3—C12—Ag1	−9.2 (3)	F7ⁱ—K1—F5A—P1	72.1 (9)
C14—N4—C12—N3	0.1 (3)	F7—K1—F5A—P1	−97.8 (9)
C15—N4—C12—N3	−175.1 (2)	F5—K1—F5A—P1	−115 (3)
C14—N4—C12—Ag1	−172.17 (18)	F5ⁱ—K1—F5A—P1	158.7 (10)
C15—N4—C12—Ag1	12.6 (3)	F5Aⁱ—K1—P2—F7	50.6 (3)
C12—N3—C13—C14	0.8 (3)	F5A—K1—P2—F7	−41.6 (4)
C22—N3—C13—C14	−177.4 (2)	F9—K1—P2—F7	125.66 (18)
N3—C13—C14—N4	−0.7 (3)	F9ⁱ—K1—P2—F7	−152.39 (13)
C12—N4—C14—C13	0.4 (3)	F3Aⁱ—K1—P2—F7	94.2 (3)
C15—N4—C14—C13	175.7 (2)	F3A—K1—P2—F7	−81.8 (3)
C12—N4—C15—C16	105.0 (3)	F3—K1—P2—F7	−76.70 (18)
C14—N4—C15—C16	−69.7 (3)	F3ⁱ—K1—P2—F7	95.36 (15)
N4—C15—C16—C21	−82.8 (3)	F7ⁱ—K1—P2—F7	−178.38 (4)
N4—C15—C16—C17	97.3 (3)	F5—K1—P2—F7	−36.96 (14)
C21—C16—C17—C18	1.0 (4)	F5ⁱ—K1—P2—F7	52.71 (15)
C15—C16—C17—C18	−179.0 (3)	F5Aⁱ—K1—P2—F7ⁱⁱ	−129.4 (3)
C16—C17—C18—C19	−1.4 (4)	F5A—K1—P2—F7ⁱⁱ	138.4 (4)
C17—C18—C19—C20	1.3 (5)	F9—K1—P2—F7ⁱⁱ	−54.34 (18)
C18—C19—C20—C21	−0.8 (4)	F9ⁱ—K1—P2—F7ⁱⁱ	27.61 (13)
C17—C16—C21—C20	−0.6 (4)	F3Aⁱ—K1—P2—F7ⁱⁱ	−85.8 (3)
C15—C16—C21—C20	179.5 (2)	F3A—K1—P2—F7ⁱⁱ	98.2 (3)
C19—C20—C21—C16	0.4 (4)	F3—K1—P2—F7ⁱⁱ	103.30 (18)
F5A—P1—F1—K1	49.5 (6)	F3ⁱ—K1—P2—F7ⁱⁱ	−84.64 (15)
F2—P1—F1—K1	−133.3 (3)	F7ⁱ—K1—P2—F7ⁱⁱ	1.62 (4)
F4—P1—F1—K1	136.3 (3)	F7—K1—P2—F7ⁱⁱ	180.0
F3A—P1—F1—K1	−46.9 (5)	F5—K1—P2—F7ⁱⁱ	143.03 (14)
F3—P1—F1—K1	−40.2 (3)	F5ⁱ—K1—P2—F7ⁱⁱ	−127.29 (15)
F1A—P1—F1—K1	−162 (4)	F5Aⁱ—K1—P2—F8	−13.6 (3)
F5—P1—F1—K1	46.6 (2)	F5A—K1—P2—F8	−105.8 (4)
F4A—P1—F1—K1	141.2 (4)	F9—K1—P2—F8	61.46 (18)
F2A—P1—F1—K1	−133.0 (5)	F3Aⁱ—K1—P2—F8	30.0 (3)
F5Aⁱ—K1—F1—P1	−99.2 (5)	F3A—K1—P2—F8	−146.0 (3)
F5A—K1—F1—P1	−38.6 (5)	F3—K1—P2—F8	−140.91 (18)
F9—K1—F1—P1	67.2 (4)	F3ⁱ—K1—P2—F8	31.15 (15)
F9ⁱ—K1—F1—P1	119.6 (3)	F7ⁱ—K1—P2—F8	117.41 (15)
F3Aⁱ—K1—F1—P1	−137.2 (5)	F7—K1—P2—F8	−64.20 (17)
F3A—K1—F1—P1	37.1 (5)	F5—K1—P2—F8	−101.17 (15)
F3—K1—F1—P1	30.2 (3)	F5ⁱ—K1—P2—F8	−11.50 (15)
F3ⁱ—K1—F1—P1	−139.1 (2)	F5Aⁱ—K1—P2—F8ⁱⁱ	166.4 (3)
F7ⁱ—K1—F1—P1	170.3 (3)	F5A—K1—P2—F8ⁱⁱ	74.2 (4)
F7—K1—F1—P1	6.3 (4)	F9—K1—P2—F8ⁱⁱ	−118.54 (18)
F5—K1—F1—P1	−35.15 (18)	F9ⁱ—K1—P2—F8ⁱⁱ	−36.60 (13)
F5ⁱ—K1—F1—P1	−104.8 (3)	F3Aⁱ—K1—P2—F8ⁱⁱ	−150.0 (3)
F5A—P1—F3—K1	−32.0 (8)	F3A—K1—P2—F8ⁱⁱ	34.0 (3)
F6A—P1—F3—K1	−142.3 (6)	F3—K1—P2—F8ⁱⁱ	39.09 (18)
F2—P1—F3—K1	137.2 (4)	F3ⁱ—K1—P2—F8ⁱⁱ	−148.85 (15)
F1—P1—F3—K1	42.8 (4)	F7ⁱ—K1—P2—F8ⁱⁱ	−62.59 (15)
F3A—P1—F3—K1	81 (3)	F7—K1—P2—F8ⁱⁱ	115.79 (17)
F1A—P1—F3—K1	53.0 (8)	F5—K1—P2—F8ⁱⁱ	78.83 (15)
F5—P1—F3—K1	−44.9 (3)	F5ⁱ—K1—P2—F8ⁱⁱ	168.50 (15)
F6—P1—F3—K1	−132.3 (2)	F5A—K1—P2—F9	−167.2 (4)
F2A—P1—F3—K1	139.5 (5)	F9ⁱ—K1—P2—F9	81.94 (16)
F5Aⁱ—K1—F3—P1	38.3 (4)	F3Aⁱ—K1—P2—F9	−31.5 (3)
F5A—K1—F3—P1	22.8 (6)	F3A—K1—P2—F9	152.5 (3)
F9—K1—F3—P1	166.4 (2)	F3—K1—P2—F9	157.63 (19)
F9ⁱ—K1—F3—P1	−106.3 (3)	F3ⁱ—K1—P2—F9	−30.31 (15)
F3A—K1—F3—P1	−82 (3)	F7ⁱ—K1—P2—F9	55.95 (15)
F7ⁱ—K1—F3—P1	−65.9 (3)	F7—K1—P2—F9	−125.66 (18)
F7—K1—F3—P1	129.8 (3)	F5—K1—P2—F9	−162.63 (15)
F5—K1—F3—P1	33.6 (3)	F5ⁱ—K1—P2—F9	−72.96 (16)
F5ⁱ—K1—F3—P1	28.9 (3)	F5Aⁱ—K1—P2—F9ⁱⁱ	105.0 (3)
F5A—P1—F5—K1	−61 (3)	F5A—K1—P2—F9ⁱⁱ	12.8 (4)
F6A—P1—F5—K1	124.6 (7)	F9—K1—P2—F9ⁱⁱ	180.0
F4—P1—F5—K1	−137.7 (3)	F9ⁱ—K1—P2—F9ⁱⁱ	−98.06 (16)
F1—P1—F5—K1	−48.1 (2)	F3Aⁱ—K1—P2—F9ⁱⁱ	148.5 (3)
F3A—P1—F5—K1	34.7 (6)	F3A—K1—P2—F9ⁱⁱ	−27.5 (3)
F3—P1—F5—K1	43.5 (3)	F3—K1—P2—F9ⁱⁱ	−22.37 (19)
F1A—P1—F5—K1	−53.8 (8)	F3ⁱ—K1—P2—F9ⁱⁱ	149.69 (15)
F6—P1—F5—K1	131.9 (3)	F7ⁱ—K1—P2—F9ⁱⁱ	−124.05 (15)
F4A—P1—F5—K1	−141.6 (6)	F7—K1—P2—F9ⁱⁱ	54.33 (18)
F5Aⁱ—K1—F5—P1	150.9 (5)	F5—K1—P2—F9ⁱⁱ	17.37 (15)
F5A—K1—F5—P1	51 (2)	F5ⁱ—K1—P2—F9ⁱⁱ	107.04 (16)
F9—K1—F5—P1	−107.2 (2)	F8—P2—F7—K1	130.58 (12)
F9ⁱ—K1—F5—P1	9.2 (2)	F8ⁱⁱ—P2—F7—K1	−49.43 (12)
F3Aⁱ—K1—F5—P1	153.6 (4)	F9—P2—F7—K1	39.57 (12)
F3A—K1—F5—P1	−25.6 (5)	F9ⁱⁱ—P2—F7—K1	−140.43 (12)
F3—K1—F5—P1	−33.0 (2)	K1ⁱⁱ—P2—F7—K1	180.0
F3ⁱ—K1—F5—P1	146.5 (2)	F5Aⁱ—K1—F7—P2	−135.0 (3)
F7ⁱ—K1—F5—P1	58.1 (2)	F5A—K1—F7—P2	143.2 (3)
F7—K1—F5—P1	−112.0 (2)	F9—K1—F7—P2	−29.90 (10)
F5ⁱ—K1—F5—P1	143.1 (3)	F9ⁱ—K1—F7—P2	32.02 (15)
F5A—P1—F1A—K1	46.5 (6)	F3Aⁱ—K1—F7—P2	−87.7 (3)
F6A—P1—F1A—K1	−129 (4)	F3A—K1—F7—P2	97.1 (3)
F2—P1—F1A—K1	−135.1 (5)	F3—K1—F7—P2	100.23 (16)
F4—P1—F1A—K1	133.8 (4)	F3ⁱ—K1—F7—P2	−89.39 (15)
F1—P1—F1A—K1	16 (4)	F7ⁱ—K1—F7—P2	4.04 (10)
F3A—P1—F1A—K1	−48.0 (5)	F5—K1—F7—P2	145.43 (13)
F3—P1—F1A—K1	−43.0 (4)	F5ⁱ—K1—F7—P2	−135.93 (12)
F5—P1—F1A—K1	45.0 (4)	F7—P2—F8—K1ⁱⁱ	133.87 (11)
F4A—P1—F1A—K1	139.4 (5)	F7ⁱⁱ—P2—F8—K1ⁱⁱ	−46.13 (11)
F2A—P1—F1A—K1	−135.0 (6)	F9—P2—F8—K1ⁱⁱ	−136.46 (11)
F5Aⁱ—K1—F1A—P1	−95.8 (7)	F9ⁱⁱ—P2—F8—K1ⁱⁱ	43.54 (11)
F5A—K1—F1A—P1	−36.6 (6)	K1—P2—F8—K1ⁱⁱ	180.0
F9—K1—F1A—P1	72.8 (10)	F7—P2—F9—K1	−40.56 (13)
F9ⁱ—K1—F1A—P1	123.3 (7)	F7ⁱⁱ—P2—F9—K1	139.44 (13)
F3Aⁱ—K1—F1A—P1	−135.3 (6)	F8—P2—F9—K1	−132.19 (13)
F3A—K1—F1A—P1	38.8 (6)	F8ⁱⁱ—P2—F9—K1	47.81 (13)
F3—K1—F1A—P1	32.0 (4)	K1ⁱⁱ—P2—F9—K1	180.0
F3ⁱ—K1—F1A—P1	−136.9 (5)	F5Aⁱ—K1—F9—P2	114.3 (4)
F7ⁱ—K1—F1A—P1	174.7 (8)	F5A—K1—F9—P2	18.6 (5)
F7—K1—F1A—P1	11.1 (9)	F9ⁱ—K1—F9—P2	−100.15 (13)
F5—K1—F1A—P1	−32.8 (4)	F3Aⁱ—K1—F9—P2	146.5 (3)
F5ⁱ—K1—F1A—P1	−101.3 (7)	F3A—K1—F9—P2	−30.1 (3)
F5A—P1—F3A—K1	−23.0 (10)	F3—K1—F9—P2	−23.9 (2)
F6A—P1—F3A—K1	−133.1 (7)	F3ⁱ—K1—F9—P2	149.16 (15)
F2—P1—F3A—K1	145.8 (6)	F7ⁱ—K1—F9—P2	−140.27 (11)
F1—P1—F3A—K1	51.1 (6)	F7—K1—F9—P2	29.79 (10)
F3—P1—F3A—K1	−90 (3)	F5—K1—F9—P2	23.24 (19)
F1A—P1—F3A—K1	61.9 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···F1ⁱⁱⁱ	0.93	2.45	3.285 (5)	149
C15—H15A···F6	0.97	2.51	3.204 (5)	129
C15—H15B···F4ⁱⁱⁱ	0.97	2.51	3.415 (7)	156
C22—H22A···F6^iv	0.96	2.42	3.171 (5)	135

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

Experimental details

Crystal data
Chemical formula	K[Ag(C₁₁H₁₂N₂)₂]₂(PF₆)₃
M_r	1378.65
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	19.917 (2), 23.047 (2), 11.5787 (12)
β (°)	103.108 (3)
V (Å³)	5176.4 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.49 × 0.42 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.632, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	66454, 7528, 7058
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.124, 1.11
No. of reflections	7528
No. of parameters	372
No. of restraints	51
H-atom treatment	H-atom parameters constrained
	w = 1/[σ²(F_o²) + (0.072P)² + 12.8353P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.68, −0.91

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected bond lengths (Å) top

Ag1—C12

2.092 (2)

Ag1—C1

2.093 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14A···F1ⁱ	0.93	2.45	3.285 (5)	149
C15—H15A···F6	0.97	2.51	3.204 (5)	129
C15—H15B···F4ⁱ	0.97	2.51	3.415 (7)	156
C22—H22A···F6ⁱⁱ	0.96	2.42	3.171 (5)	135

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

Footnotes

‡Thomson Reuters ResearcherID: A-5525-2009.

§Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

RAH, AWS and CKW thank Universiti Sains Malaysia (USM) for the FRGS fund (203/PKIMIA/671115), short term grant (304/PKIMIA/639001) and RU grant (1001/PKIMIA/813023 and 1001/PKIMIA/811157). HKF and CKQ thank USM for the Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for the award of a USM fellowship.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–S19. CSD CrossRef Web of Science Google Scholar
Bourissou, D., Guerret, O., Gabbaï, F. P. & Bertrand, G. (2000). Chem. Rev. 100, 39–91. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105–107. CrossRef CAS Web of Science IUCr Journals Google Scholar
Haque, R. A., Ghdhayeb, M. Z., Abdallah, H. H., Quah, C. K. & Fun, H.-K. (2010b). Acta Cryst. E66, o80–o81. Google Scholar
Haque, R. A., Washeel, A., Teoh, S. G., Quah, C. K. & Fun, H.-K. (2010a). Acta Cryst. E66, o2797–o2798. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hermann, W. A., Köcher, C., Gooben, L. J. & Artus, G. R. J. (1996). Chem. Eur. J. 2, 1627–1636. Google Scholar
Herrmann, W. A. & Köcher, C. (1997). Angew. Chem. Int. Ed. Engl. 36, 2162–2187. CrossRef CAS Web of Science Google Scholar
Lee, K.-M., Chen, J. C. C. & Lin, I. L. J. (2001). J. Organomet. Chem. 617–618, 364–375. Web of Science CSD CrossRef CAS Google Scholar
Lin, I. J. B. & Vasam, C. S. (2007). Coord. Chem. Rev, 251, 642–670. Web of Science CrossRef CAS Google Scholar
Medvetz, D. A., Hindi, K. M., Panzner, M. J., Ditto, A. J., Yun, Y. H. & Young, W. J. (2008). Met. Based Drugs, pp. 384010–384016. Google Scholar
Özdemir, İ., Özcan, E. Ö., Günal, S. & Gürbüz, N. (2010). Molecules, 15, 2499–2508. Web of Science PubMed Google Scholar
Ray, S., Mohan, R., Singh, J. K., Samantaray, M. K., Shaikh, M. M., Panda, D. & Ghosh, P. (2007). J. Am. Chem. Soc. 129, 15042–15053. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H. M. J. & Lin, I. J. B. (1998). Organometallics, 17, 972–975. Web of Science CSD CrossRef CAS Google Scholar
Zhou, Y., Zhang, X., Chen, W. & Qiu, H. (2008). J. Organomet. Chem. 693, 205–215. Web of Science CSD CrossRef CAS Google Scholar

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