Bis[5-(pyridin-2-yl)pyrazine-2-carbo­nitrile-κ2N4,N5]silver hexa­fluorido­phosphate

Wang, Z.J.

doi:10.1107/S1600536811051403

Bis[5-(pyridin-2-yl)pyrazine-2-carbonitrile-κ²N⁴,N⁵]silver hexafluoridophosphate

In the mononuclear title complex, [Ag(C₁₀H₆N₄)₂]PF₆, two κ²N,N′-chelating 5-(pyridin-2-yl)pyrazine-2-carbonitrile ligands surround the Ag^I atom, forming a distorted N₄ tetrahedral coordination geometry. The mononuclear units are interconnected through π–π interactions [centroid–centroid distances = 3.801 (2) and 3.979 (3) Å] and the hexafluoridophosphate anions are embedded within the interstices. C [triple bond]

π interactions [N

centroid = 3.519 (2) Å] and C—H.

N hydrogen-bonding interactions also occur.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536811051403/bt5734sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536811051403/bt5734Isup2.hkl Contains datablock I

CCDC reference: 861671

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.032
wR factor = 0.090
Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Reported MoietyFormula Strings  Differ          ?
PLAT125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....          ?
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of          P1
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         18
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         92

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Deg.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Ag1    --  N5      ..       12.9 su
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C9     -   C10    ...       1.45 Ang.
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C19    -   C20    ...       1.45 Ang.
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         53
            N3  -C9  -C10 -N7     11.00 29.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         54
            C8  -C9  -C10 -N7     17.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         83
            N6  -C19 -C20 -N8     16.00  0.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         84
            C18 -C19 -C20 -N8      1.00  0.00   1.555   1.555   1.555   1.555
PLAT790_ALERT_4_G Centre of Gravity not Within Unit Cell: Resd.  #          2
              F6 P

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  12 ALERT level G = General information/check it is not something unexpected

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   8 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

The coordination chemistry of pyridyl based ligands has intensively developed in the passed decades (Boudalis et al., 2003; Dunne et al., 1997; Wang et al.,2009).The devious rigid and/or flexible pyridyl based ligands were designed and synthesized to construct many fancy coordination frameworks (Huang et al. 2007). Herein, we report the structure of one new silver(I) complex ([Ag(C₁₀H₆N₄)₂]PF₆) derived from 5-(2-pyridyl)pyrazine-2-carbonitrile, a rigid ligand featuring a 2-cyanopyrazinyl group at the 2-pyridyl carbon atom (Scheme 1).

As shown in Fig.1,two κ² N:N chelating 5-(2-pyridyl)pyrazine-2-carbonitrile ligands surround the Ag^I center to form a distorted N4-tetrahedral coordination geometry. The Ag—N bond lengthes lie within the range of 2.289 (2)-2.472 (2)Å, with the Ag1—N5 being slight longer than the others, comparable to these in [Ag(C₁₀H₆N₄)₂]BF₄ (2.196 (2)-2.685 (2) Å), a similar complex of 5-(2-pyridyl)pyrazine-2-carbonitrile reported (Wang et al. 2010). The two hetero rings of one 5-(2-pyridyl)pyrazine-2-carbonitrile exhibit a dihedral angle of 29.07 (1)°, while in the other one ligand the value is 5.50 (1)°. Such two chelating ligands are almost in an orthogonal orientation, which is remarkablely different from that an anti-relationship in [Ag(C₁₀H₆N₄)₂]BF₄ reported by us (Wang et al. 2010). Two mononuclear units arranged in an invert center are interconnected through π(pyrazinyl)···π(pyrazinyl) (Cg1···Cg1ⁱ = 3.453 (2) Å, Cg1 = N5-C16-C17-N6-C19-C18 ring, i: -x+1, -y+2, -z+1) and C20≡N8(cyano)···π(pyridyl) interactions (Table 2) to form a dimeric unit. Along the a axis, the dimeric units are stacked and interconnected via C11—H11A···N7^iv(cyano) interaction (Table 1), leading to a column motif. Along the [010] direction, the column motifs interconnect through π(pyridyl)···π(pyridyl) (Cg2···Cg2ⁱⁱ = 3.801 (2) Å, Cg2 = N4-C11-C12-C13-C14-C15 ring, ii: -x+1, -y+1, -z+1) interaction (Table 2), forming a lay in the abplane. Along [001] direction, the formed layers are stacked, and π(pyridyl)···π(pyridyl) interactions (Cg3···Cg3ⁱⁱⁱ = 3.979 (3) Å, Cg3 = N1-C1-C2-C3-C4-C5, iii -x+1, -x+2, -x+2) occur to help to stablize the whole supramolecular structure with the hexafluorophosphate embedded within the interstices.

Related literature top

For coordination complexes with pyridyl-based ligands, see: Boudalis et al. (2003); Dunne et al. (1997); Huang et al. (2007); Wang et al. (2009). For a complex with 5-(2-pyridyl)pyrazine-2-carbonitrile, see: Wang et al. (2010).

Experimental top

The ligand 5-(2-pyridyl)-2-cyanopyrazine ligand was obtained commercially. The ligand (18.1 mg, 0.2 mmol) and AgPF₆ (26 mg, 0.1mmol) were mixed and dissolved in 5 ml solvent of methanol (3 ml) and acetonitrile (2 ml). After stirring at room temperature for 4 hours, the resulted solution was filtrated, and the clear solution was kepted in air for slow evaporation. After about one week, the colorless block-like crystals were deposited (32.7 mg, 53% yeild).

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The atom-numbering scheme of the title compound with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The C≡N···π(pyridyl) and π–π interactions between the mononuclear units, forming the dimer in the title complex.
	Fig. 3. The packing structure of the title complex viewed down the a direction, a layer formed in the ab plane. All non-covalent interactions are omitted for clarity.

Bis[5-(pyridin-2-yl)pyrazine-2-carbonitrile-κ²N⁴,N⁵]silver hexafluoridophosphate top

Crystal data top

[Ag(C₁₀H₆N₄)₂]PF₆	Z = 2
M_r = 617.22	F(000) = 608
Triclinic, P1	D_x = 1.839 Mg m⁻³
a = 8.8989 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1711 (10) Å	Cell parameters from 252 reflections
c = 14.0804 (15) Å	θ = 2.3–28.3°
α = 77.023 (2)°	µ = 1.05 mm⁻¹
β = 86.926 (2)°	T = 293 K
γ = 84.809 (2)°	Block, colorless
V = 1114.5 (2) Å³	0.38 × 0.30 × 0.30 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5438 independent reflections
Radiation source: fine-focus sealed tube	4544 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 28.3°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
T_min = 0.861, T_max = 1.000	k = −12→11
8106 measured reflections	l = −14→18

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0427P)² + 0.4779P] P = (F_o² + 2F_c²)/3
5438 reflections	(Δ/σ)_max = 0.001
325 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Ag(C₁₀H₆N₄)₂]PF₆	γ = 84.809 (2)°
M_r = 617.22	V = 1114.5 (2) Å³
Triclinic, P1	Z = 2
a = 8.8989 (9) Å	Mo Kα radiation
b = 9.1711 (10) Å	µ = 1.05 mm⁻¹
c = 14.0804 (15) Å	T = 293 K
α = 77.023 (2)°	0.38 × 0.30 × 0.30 mm
β = 86.926 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	5438 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	4544 reflections with I > 2σ(I)
T_min = 0.861, T_max = 1.000	R_int = 0.017
8106 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.04	Δρ_max = 0.71 e Å⁻³
5438 reflections	Δρ_min = −0.37 e Å⁻³
325 parameters

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.

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
Ag1	0.48500 (2)	0.72149 (2)	0.719902 (13)	0.05876 (9)
N1	0.5186 (2)	0.8140 (2)	0.85560 (14)	0.0472 (4)
N2	0.2770 (2)	0.6575 (2)	0.83133 (14)	0.0488 (4)
N3	0.0214 (2)	0.6780 (2)	0.95255 (15)	0.0519 (5)
N4	0.6022 (2)	0.6137 (2)	0.60099 (14)	0.0421 (4)
N5	0.3774 (2)	0.8372 (2)	0.55962 (13)	0.0417 (4)
N6	0.3283 (2)	0.9988 (2)	0.37004 (15)	0.0512 (5)
N7	−0.2337 (3)	0.5344 (3)	0.8368 (2)	0.0701 (7)
N8	0.0293 (3)	1.2382 (3)	0.4069 (2)	0.0654 (6)
C1	0.6476 (3)	0.8679 (3)	0.8722 (2)	0.0577 (6)
H1A	0.7109	0.9045	0.8191	0.069*
C2	0.6908 (3)	0.8716 (4)	0.9636 (2)	0.0644 (7)
H2A	0.7806	0.9108	0.9722	0.077*
C3	0.5984 (4)	0.8163 (4)	1.0420 (2)	0.0747 (9)
H3A	0.6266	0.8143	1.1049	0.090*
C4	0.4630 (3)	0.7635 (4)	1.0269 (2)	0.0659 (7)
H4A	0.3982	0.7273	1.0793	0.079*
C5	0.4258 (3)	0.7655 (3)	0.93238 (17)	0.0471 (5)
C6	0.2814 (3)	0.7132 (3)	0.91130 (15)	0.0429 (5)
C7	0.1518 (3)	0.7245 (3)	0.97008 (17)	0.0494 (5)
H7A	0.1570	0.7666	1.0239	0.059*
C8	0.1461 (3)	0.6118 (3)	0.81258 (18)	0.0526 (6)
H8A	0.1394	0.5724	0.7577	0.063*
C9	0.0207 (3)	0.6218 (3)	0.87300 (18)	0.0478 (5)
C10	−0.1216 (3)	0.5724 (3)	0.8523 (2)	0.0555 (6)
C11	0.7058 (3)	0.4967 (3)	0.62202 (18)	0.0493 (5)
H11A	0.7194	0.4500	0.6871	0.059*
C12	0.7931 (3)	0.4422 (3)	0.5521 (2)	0.0531 (6)
H12A	0.8631	0.3601	0.5696	0.064*
C13	0.7749 (3)	0.5111 (3)	0.4566 (2)	0.0551 (6)
H13A	0.8345	0.4784	0.4080	0.066*
C14	0.6665 (3)	0.6305 (3)	0.43296 (18)	0.0474 (5)
H14A	0.6512	0.6779	0.3681	0.057*
C15	0.5814 (2)	0.6782 (2)	0.50681 (15)	0.0346 (4)
C16	0.4612 (2)	0.8042 (2)	0.48494 (15)	0.0345 (4)
C17	0.4369 (3)	0.8876 (3)	0.39062 (17)	0.0487 (5)
H17A	0.4991	0.8647	0.3398	0.058*
C18	0.2663 (2)	0.9470 (3)	0.53981 (18)	0.0453 (5)
H18A	0.2047	0.9712	0.5904	0.054*
C19	0.2421 (2)	1.0246 (2)	0.44564 (17)	0.0407 (4)
C20	0.1224 (3)	1.1448 (3)	0.4237 (2)	0.0494 (5)
P1	0.04799 (7)	1.12551 (7)	0.76794 (5)	0.04787 (15)
F5	0.0408 (3)	1.1620 (2)	0.65229 (13)	0.0903 (6)
F4	0.2221 (2)	1.0737 (3)	0.75732 (16)	0.0945 (7)
F3	−0.1266 (2)	1.1778 (3)	0.77714 (17)	0.0920 (6)
F6	0.0579 (3)	1.0844 (3)	0.88231 (14)	0.1011 (7)
F1	0.0880 (3)	1.2901 (2)	0.7634 (2)	0.1208 (9)
F2	0.0083 (3)	0.9602 (2)	0.77003 (17)	0.0918 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.06857 (14)	0.07215 (15)	0.03810 (11)	−0.00412 (10)	0.00886 (8)	−0.02065 (9)
N1	0.0422 (10)	0.0584 (12)	0.0420 (10)	0.0000 (8)	0.0002 (8)	−0.0152 (9)
N2	0.0525 (11)	0.0576 (12)	0.0382 (10)	−0.0042 (9)	0.0012 (8)	−0.0152 (8)
N3	0.0503 (11)	0.0603 (12)	0.0461 (11)	−0.0050 (9)	0.0022 (9)	−0.0146 (9)
N4	0.0423 (9)	0.0452 (10)	0.0400 (9)	0.0016 (8)	−0.0038 (7)	−0.0136 (8)
N5	0.0372 (9)	0.0492 (10)	0.0403 (9)	0.0015 (7)	0.0019 (7)	−0.0156 (8)
N6	0.0467 (10)	0.0569 (12)	0.0464 (11)	0.0084 (9)	−0.0023 (8)	−0.0088 (9)
N7	0.0617 (14)	0.0812 (17)	0.0726 (16)	−0.0124 (13)	−0.0100 (12)	−0.0234 (13)
N8	0.0524 (12)	0.0628 (14)	0.0816 (17)	0.0149 (11)	−0.0132 (12)	−0.0223 (12)
C1	0.0458 (13)	0.0699 (17)	0.0585 (15)	−0.0028 (12)	0.0013 (11)	−0.0181 (13)
C2	0.0472 (13)	0.083 (2)	0.0680 (18)	−0.0040 (13)	−0.0085 (12)	−0.0263 (15)
C3	0.0706 (18)	0.109 (3)	0.0515 (16)	−0.0126 (17)	−0.0169 (14)	−0.0258 (16)
C4	0.0655 (16)	0.096 (2)	0.0383 (13)	−0.0135 (15)	−0.0038 (11)	−0.0151 (13)
C5	0.0469 (12)	0.0547 (13)	0.0395 (11)	−0.0005 (10)	−0.0023 (9)	−0.0114 (10)
C6	0.0481 (11)	0.0473 (12)	0.0322 (10)	−0.0012 (9)	−0.0012 (8)	−0.0071 (9)
C7	0.0528 (13)	0.0593 (14)	0.0382 (11)	−0.0051 (11)	0.0016 (9)	−0.0156 (10)
C8	0.0591 (14)	0.0607 (14)	0.0415 (12)	−0.0079 (11)	−0.0018 (10)	−0.0175 (11)
C9	0.0507 (12)	0.0477 (12)	0.0437 (12)	−0.0036 (10)	−0.0045 (10)	−0.0064 (10)
C10	0.0570 (15)	0.0587 (15)	0.0513 (14)	−0.0068 (12)	−0.0052 (11)	−0.0116 (11)
C11	0.0507 (13)	0.0499 (13)	0.0471 (13)	0.0053 (10)	−0.0126 (10)	−0.0114 (10)
C12	0.0461 (12)	0.0479 (13)	0.0665 (16)	0.0111 (10)	−0.0114 (11)	−0.0189 (12)
C13	0.0518 (13)	0.0567 (14)	0.0570 (15)	0.0116 (11)	0.0060 (11)	−0.0214 (12)
C14	0.0487 (12)	0.0505 (13)	0.0420 (12)	0.0065 (10)	0.0043 (9)	−0.0134 (10)
C15	0.0311 (9)	0.0349 (9)	0.0395 (10)	−0.0028 (7)	0.0001 (7)	−0.0121 (8)
C16	0.0302 (9)	0.0368 (10)	0.0389 (10)	−0.0037 (7)	0.0001 (7)	−0.0137 (8)
C17	0.0461 (12)	0.0562 (13)	0.0402 (12)	0.0100 (10)	0.0041 (9)	−0.0098 (10)
C18	0.0372 (10)	0.0525 (13)	0.0480 (12)	0.0043 (9)	0.0032 (9)	−0.0194 (10)
C19	0.0310 (9)	0.0394 (10)	0.0540 (13)	−0.0015 (8)	−0.0045 (8)	−0.0148 (9)
C20	0.0384 (11)	0.0507 (13)	0.0610 (15)	0.0020 (10)	−0.0063 (10)	−0.0176 (11)
P1	0.0530 (3)	0.0482 (3)	0.0428 (3)	−0.0012 (3)	0.0021 (2)	−0.0128 (3)
F5	0.1156 (16)	0.0957 (14)	0.0469 (9)	0.0363 (12)	−0.0066 (10)	−0.0060 (9)
F4	0.0560 (10)	0.1330 (19)	0.0913 (15)	0.0151 (11)	−0.0017 (10)	−0.0271 (13)
F3	0.0626 (11)	0.1042 (15)	0.1056 (16)	0.0126 (10)	0.0113 (10)	−0.0262 (13)
F6	0.1187 (17)	0.140 (2)	0.0472 (10)	−0.0087 (15)	−0.0014 (10)	−0.0267 (11)
F1	0.146 (2)	0.0698 (13)	0.160 (2)	−0.0404 (14)	0.0392 (18)	−0.0522 (15)
F2	0.1197 (17)	0.0551 (10)	0.1022 (16)	−0.0126 (10)	−0.0138 (13)	−0.0163 (10)

Geometric parameters (Å, º) top

Ag1—N4	2.2887 (18)	C5—C6	1.478 (3)
Ag1—N1	2.301 (2)	C6—C7	1.393 (3)
Ag1—N2	2.389 (2)	C7—H7A	0.9300
Ag1—N5	2.4714 (19)	C8—C9	1.376 (4)
N1—C5	1.343 (3)	C8—H8A	0.9300
N1—C1	1.342 (3)	C9—C10	1.448 (4)
N2—C8	1.331 (3)	C11—C12	1.374 (4)
N2—C6	1.340 (3)	C11—H11A	0.9300
N3—C7	1.326 (3)	C12—C13	1.362 (4)
N3—C9	1.334 (3)	C12—H12A	0.9300
N4—C15	1.341 (3)	C13—C14	1.386 (3)
N4—C11	1.341 (3)	C13—H13A	0.9300
N5—C16	1.331 (3)	C14—C15	1.381 (3)
N5—C18	1.339 (3)	C14—H14A	0.9300
N6—C19	1.330 (3)	C15—C16	1.492 (3)
N6—C17	1.333 (3)	C16—C17	1.393 (3)
N7—C10	1.134 (4)	C17—H17A	0.9300
N8—C20	1.131 (3)	C18—C19	1.375 (3)
C1—C2	1.371 (4)	C18—H18A	0.9300
C1—H1A	0.9300	C19—C20	1.454 (3)
C2—C3	1.371 (5)	P1—F1	1.568 (2)
C2—H2A	0.9300	P1—F6	1.575 (2)
C3—C4	1.382 (4)	P1—F2	1.5812 (19)
C3—H3A	0.9300	P1—F4	1.5883 (19)
C4—C5	1.385 (3)	P1—F5	1.5906 (18)
C4—H4A	0.9300	P1—F3	1.5908 (19)

N4—Ag1—N1	145.43 (7)	C8—C9—C10	121.0 (2)
N4—Ag1—N2	133.18 (7)	N7—C10—C9	179.3 (3)
N1—Ag1—N2	72.30 (7)	N4—C11—C12	123.3 (2)
N4—Ag1—N5	69.52 (6)	N4—C11—H11A	118.4
N1—Ag1—N5	132.63 (7)	C12—C11—H11A	118.4
N2—Ag1—N5	106.77 (7)	C13—C12—C11	118.6 (2)
C5—N1—C1	118.0 (2)	C13—C12—H12A	120.7
C5—N1—Ag1	115.17 (16)	C11—C12—H12A	120.7
C1—N1—Ag1	123.14 (16)	C12—C13—C14	119.1 (2)
C8—N2—C6	117.4 (2)	C12—C13—H13A	120.4
C8—N2—Ag1	127.48 (16)	C14—C13—H13A	120.4
C6—N2—Ag1	112.57 (15)	C15—C14—C13	119.2 (2)
C7—N3—C9	115.6 (2)	C15—C14—H14A	120.4
C15—N4—C11	117.90 (19)	C13—C14—H14A	120.4
C15—N4—Ag1	119.88 (13)	N4—C15—C14	121.82 (19)
C11—N4—Ag1	121.75 (15)	N4—C15—C16	117.00 (17)
C16—N5—C18	117.68 (19)	C14—C15—C16	121.18 (19)
C16—N5—Ag1	113.32 (13)	N5—C16—C17	120.12 (19)
C18—N5—Ag1	127.61 (14)	N5—C16—C15	117.60 (18)
C19—N6—C17	115.7 (2)	C17—C16—C15	122.27 (18)
N1—C1—C2	123.2 (3)	N6—C17—C16	122.8 (2)
N1—C1—H1A	118.4	N6—C17—H17A	118.6
C2—C1—H1A	118.4	C16—C17—H17A	118.6
C1—C2—C3	118.5 (3)	N5—C18—C19	120.9 (2)
C1—C2—H2A	120.8	N5—C18—H18A	119.6
C3—C2—H2A	120.8	C19—C18—H18A	119.6
C2—C3—C4	119.6 (3)	N6—C19—C18	122.76 (19)
C2—C3—H3A	120.2	N6—C19—C20	116.0 (2)
C4—C3—H3A	120.2	C18—C19—C20	121.2 (2)
C3—C4—C5	118.7 (3)	N8—C20—C19	179.9 (3)
C3—C4—H4A	120.7	F1—P1—F6	91.37 (15)
C5—C4—H4A	120.7	F1—P1—F2	178.75 (15)
N1—C5—C4	122.0 (2)	F6—P1—F2	89.84 (13)
N1—C5—C6	116.7 (2)	F1—P1—F4	90.26 (15)
C4—C5—C6	121.3 (2)	F6—P1—F4	90.18 (13)
N2—C6—C7	120.2 (2)	F2—P1—F4	89.45 (13)
N2—C6—C5	117.8 (2)	F1—P1—F5	89.97 (15)
C7—C6—C5	121.9 (2)	F6—P1—F5	178.18 (13)
N3—C7—C6	122.9 (2)	F2—P1—F5	88.81 (12)
N3—C7—H7A	118.6	F4—P1—F5	88.57 (11)
C6—C7—H7A	118.6	F1—P1—F3	89.76 (14)
N2—C8—C9	121.1 (2)	F6—P1—F3	90.52 (13)
N2—C8—H8A	119.4	F2—P1—F3	90.52 (13)
C9—C8—H8A	119.4	F4—P1—F3	179.29 (12)
N3—C9—C8	122.9 (2)	F5—P1—F3	90.72 (12)
N3—C9—C10	116.1 (2)

N4—Ag1—N1—C5	−132.25 (17)	C4—C5—C6—C7	29.9 (4)
N2—Ag1—N1—C5	11.13 (16)	C9—N3—C7—C6	−1.4 (4)
N5—Ag1—N1—C5	107.90 (18)	N2—C6—C7—N3	2.1 (4)
N4—Ag1—N1—C1	25.6 (3)	C5—C6—C7—N3	−179.8 (2)
N2—Ag1—N1—C1	169.0 (2)	C6—N2—C8—C9	0.1 (4)
N5—Ag1—N1—C1	−94.3 (2)	Ag1—N2—C8—C9	−160.13 (19)
N4—Ag1—N2—C8	−43.4 (3)	C7—N3—C9—C8	0.2 (4)
N1—Ag1—N2—C8	164.3 (2)	C7—N3—C9—C10	−179.2 (2)
N5—Ag1—N2—C8	34.0 (2)	N2—C8—C9—N3	0.5 (4)
N4—Ag1—N2—C6	155.58 (14)	N2—C8—C9—C10	179.8 (2)
N1—Ag1—N2—C6	3.24 (16)	N3—C9—C10—N7	11 (29)
N5—Ag1—N2—C6	−127.02 (16)	C8—C9—C10—N7	−169 (100)
N1—Ag1—N4—C15	−124.46 (16)	C15—N4—C11—C12	1.3 (4)
N2—Ag1—N4—C15	106.73 (17)	Ag1—N4—C11—C12	−170.83 (19)
N5—Ag1—N4—C15	12.60 (15)	N4—C11—C12—C13	0.7 (4)
N1—Ag1—N4—C11	47.6 (2)	C11—C12—C13—C14	−1.9 (4)
N2—Ag1—N4—C11	−81.3 (2)	C12—C13—C14—C15	1.1 (4)
N5—Ag1—N4—C11	−175.4 (2)	C11—N4—C15—C14	−2.2 (3)
N4—Ag1—N5—C16	−14.09 (14)	Ag1—N4—C15—C14	170.13 (17)
N1—Ag1—N5—C16	134.22 (14)	C11—N4—C15—C16	177.62 (19)
N2—Ag1—N5—C16	−144.66 (14)	Ag1—N4—C15—C16	−10.1 (2)
N4—Ag1—N5—C18	179.8 (2)	C13—C14—C15—N4	1.0 (3)
N1—Ag1—N5—C18	−31.9 (2)	C13—C14—C15—C16	−178.8 (2)
N2—Ag1—N5—C18	49.2 (2)	C18—N5—C16—C17	3.1 (3)
C5—N1—C1—C2	1.9 (4)	Ag1—N5—C16—C17	−164.53 (17)
Ag1—N1—C1—C2	−155.3 (2)	C18—N5—C16—C15	−177.86 (18)
N1—C1—C2—C3	0.7 (5)	Ag1—N5—C16—C15	14.5 (2)
C1—C2—C3—C4	−2.2 (5)	N4—C15—C16—N5	−4.1 (3)
C2—C3—C4—C5	1.2 (5)	C14—C15—C16—N5	175.7 (2)
C1—N1—C5—C4	−3.0 (4)	N4—C15—C16—C17	174.9 (2)
Ag1—N1—C5—C4	156.0 (2)	C14—C15—C16—C17	−5.3 (3)
C1—N1—C5—C6	177.3 (2)	C19—N6—C17—C16	−0.9 (4)
Ag1—N1—C5—C6	−23.7 (3)	N5—C16—C17—N6	−2.1 (4)
C3—C4—C5—N1	1.5 (5)	C15—C16—C17—N6	178.9 (2)
C3—C4—C5—C6	−178.8 (3)	C16—N5—C18—C19	−1.2 (3)
C8—N2—C6—C7	−1.3 (3)	Ag1—N5—C18—C19	164.36 (16)
Ag1—N2—C6—C7	161.78 (18)	C17—N6—C19—C18	2.8 (3)
C8—N2—C6—C5	−179.5 (2)	C17—N6—C19—C20	−179.4 (2)
Ag1—N2—C6—C5	−16.4 (3)	N5—C18—C19—N6	−1.8 (4)
N1—C5—C6—N2	27.7 (3)	N5—C18—C19—C20	−179.5 (2)
C4—C5—C6—N2	−152.0 (3)	N6—C19—C20—N8	−163 (100)
N1—C5—C6—C7	−150.4 (2)	C18—C19—C20—N8	14 (100)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···N7ⁱ	0.93	2.47	3.201 (2)	135

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	[Ag(C₁₀H₆N₄)₂]PF₆
M_r	617.22
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.8989 (9), 9.1711 (10), 14.0804 (15)
α, β, γ (°)	77.023 (2), 86.926 (2), 84.809 (2)
V (Å³)	1114.5 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.38 × 0.30 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.861, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8106, 5438, 4544
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.090, 1.04
No. of reflections	5438
No. of parameters	325
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.37

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).