Bis[5-(2-pyrid­yl)pyrazine-2-carbonitrile]­silver(I) tetra­fluorido­borate

In the title mononuclear complex, [Ag(C₁₀H₆N₄)₂]BF₄, the Ag^I atom adopts a square-planar N₄ coordination geometry and is surrounded by two 5-(2-pyrid­yl)pyrazine-2-carbonitrile ligands. The tetra­fluorido­borate anions link the mononuclear cations through inter­molecular C—H...F hydrogen-bonding inter­actions, forming an infinite tape structure along [110]. Other weak inter­actions occur: π–π stacking with centroid–centroid distances of 3.820 (2) and 3.898 (1) Å between pyridyl rings and 3.610 (2) and 3.926 (2) Å between pyrazinyl rings as well as F...π contacts involving the tetra­fluorido­borate anions and pyrazine rings [F...centroid = 2.999 (3) Å]; these combine with the hydrogen-bonding inter­actions to link the mononuclear cations into a three-dimensional supra­molecular architecture.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.111
• Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ag1    --  N4      ..       8.69 su
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         19
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of          B1
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600         81

Alert level G
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C1     -   C3     ...       1.45 Ang.
PLAT371_ALERT_2_G Long   C(sp2)-C(sp1) Bond  C20    -   C22    ...       1.45 Ang.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   4 ALERT level G = General alerts; check

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

During the past decades, coordination chemistry based on multidentate N-containing ligands has been widely developed and received intense interests (Peedikakkal et al., 2010). 2,2'-bipyridine is a popular member of the pyridine-based family and attracts a great of attentions because of the potential medicinal applications (Casini et al., 2006) and the fascinating framework structures (Li et al., 2010; Wang et al., 2009) of its divers metal complexes. Many 2,2'-bipyridine derivatives together with their various metal complexes have also been synthesized and well characterized (Berghian et al., 2005; Mathieu et al., 2001).

Herein, we present the structure of the new complex [Ag(C₁₀H₆N₄)₂]BF₄ derived from 5-(2-pyridyl)-2-cyanopyrazine ligand, a similar ligand to the 2,2'-bipyridine featuring a 2-cyanopyrazinyl group at the 2-pyridyl carbon atom (Scheme 1). In the mononuclear title complex, the two ligands surrounding the center Ag(I) ion are in an anti-relationship and almost in the same plane, thus each of them chelates the Ag(I) ion through one 2-pyridyl N atom and one 4-pyrazinyl N atom, leading to a square planar N4- coordination geometry. As shown in Fig.1, the Ag1—N1(pyridyl) and Ag1—N3(pyridyl) bonds equal to 2.196 (2) and 2.203 (2) Å, respectively, which are considerably shorter than the other two Ag—N(pyrazinyl) bonds with the distances of 2.659 (2) Å (Ag1—N4) and 2.685 (2) Å (Ag1—N2), respectively. The longer Ag—N(pyrazinyl) distance is comparable to that in [Ag(dafone)₂]NO₃.H₂O (dafone = 4,5-diazafluoren-9-one) (Biju et al., 2008). For the tetrafluoridoborate anions, each one links two neighbor [Ag(C₁₀H₆N₄)₂]⁺ cationic moieties arranged along the [110] direction through C—H···F (Denis et al., 2004) hydrogen bonding (C13···F2 3.015 (1) Å, C13—H13a···F2 120.8°; C11ⁱ···F4 3.132 (2) Å, C11ⁱ—H11aⁱ···F4 137.2°, i x-1, y-1, z), forming an infinite tape structure (Fig. 2). The tape arrays are arranged along [110] direction in a shoulder to shoulder mode and stack along [-110] direction via π-π and F(BF₄^-)···π(pyrazinyl) interactions (Fig. 3). The close centroid(pyridyl)···centroid(pyridyl)distances are 3.820 (2) and 3.898 (1) Å, while that of centroid(pyrazinyl)···centroid(pyrazinyl) are 3.610 (2) and 3.926 (2) Å. For the anion-π interaction, F4(BF₄^-)···centroid(pyrazinyl) distance is 2.999 (3) Å, comparable to that 3.097 (1) Å found in Cu[(2-C₄H₃N₂)₂C(OH)₂]₂(BF₄^-)₂ (Wan, et al., 2008).

Related literature

For coordination complexes with 2,2'-bipyridine, see: Casini et al. (2006); Li et al. (2010); Wang et al. (2009). For other related structures involving 2,2'-bipyridine derivatives, see: Berghian et al. (2005); Mathieu et al. (2001). For the coordination chemistry of multidentate N-containing ligands, see: Peedikakkal et al. (2010). For properties of pyridine-based ligands, see: Casini et al. (2006). For comparison Ag—N(pyrazinyl) distances, see: Biju et al. (2008). For C—H···F interactions ,see: Denis et al. (2004). For a comparable BF₄ anion–pyrazinyl interaction, see: Wan et al. (2008).

S2. Experimental

The ligand 5-(2-pyridyl)-2-cyanopyrazine was obtained commercially.The ligand (0.182 g, 0.1 mmol) was dissolved in a mixture of methanol, 2 ml, and acetonitrile, 2 ml was added to AgBF₄ (0.194g, 0.1mmol), with constantly stirring. After four hours, the clear solution was filtered and kept in air for one week at room temperature to yield colorless rod-like crystals (274 mg, 72% yeild).

S3. Refinement

The hydrogen atoms were placed in idealized positions and allowed to ride on the relevant carbon atoms, with C— H = 0.93 Å and Uĩso~(H) = 1.2Ueq(C).

Computing details

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and 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

	Fig. 1. The atom-numbering scheme of the title [Ag(C10H6N4)2]BF4. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as sticks of arbitrary radii.
	Fig. 2. The tetrafluoridoborate linkages between the [Ag(C10H6N4)2]^+moieties arranged along [110] direction. The red-dashed lines indicate the C—H···F hydrogen-bonding interactions. Symmetry code: i x-1, y-1, z.
	Fig. 3. Three-dimensional structure of the title complex. The red dashed lines represent π–π stacking interactions,while blue dashed lines indicate F(BF4^-)···π(pyrazinyl) interactions. A, B, C and D red lettering indicate Cg2···Cg2^i,Cg3···Cg3^ii,Cg4···Cg4^iii and Cg1···Cg1^iv distances, respectively, while E represents F4···Cg1^v distance. (See Table 2).

Bis[5-(2-pyridyl)pyrazine-2-carbonitrile]silver(I) tetrafluoridoborate

Crystal data

[Ag(C10H6N4)2]BF4	Z = 2
Mr = 559.06	F(000) = 552
Triclinic, P1	Dx = 1.815 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8144 (12) Å	Cell parameters from 255 reflections
b = 11.2492 (16) Å	θ = 1.9–28.2°
c = 12.2697 (18) Å	µ = 1.05 mm^−1
α = 104.168 (3)°	T = 293 K
β = 90.789 (2)°	Rod, colourless
γ = 101.429 (3)°	0.45 × 0.40 × 0.30 mm
V = 1022.8 (3) Å^3

Data collection

Bruker APEXII CCD area-detector diffractometer	4986 independent reflections
Radiation source: fine-focus sealed tube	3929 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.017
ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.615, Tmax = 0.783	k = −15→11
7178 measured reflections	l = −11→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0606P)^2 + 0.3679P] where P = (Fo^2 + 2Fc^2)/3
4986 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.95 e Å^−3
0 restraints	Δρmin = −0.73 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ag1	0.48906 (4)	0.75499 (2)	0.295313 (17)	0.05808 (11)
N1	0.6368 (3)	0.8859 (2)	0.44508 (18)	0.0413 (5)
C17	0.4863 (3)	0.7511 (2)	0.0256 (2)	0.0354 (5)
C8	0.7174 (4)	0.9522 (3)	0.6418 (2)	0.0488 (7)
H8A	0.7096	0.9362	0.7126	0.059*
C9	0.8161 (4)	1.0650 (3)	0.6289 (3)	0.0536 (7)
H9A	0.8757	1.1251	0.6908	0.064*
N3	0.3487 (3)	0.6200 (2)	0.14425 (19)	0.0440 (5)
N7	0.5870 (3)	0.8837 (2)	−0.09560 (19)	0.0448 (5)
C6	0.5258 (3)	0.7428 (2)	0.5588 (2)	0.0349 (5)
C13	0.1720 (4)	0.4170 (3)	0.0664 (3)	0.0552 (7)
H13A	0.1052	0.3437	0.0784	0.066*
C7	0.6308 (3)	0.8640 (2)	0.5475 (2)	0.0366 (5)
C10	0.8236 (4)	1.0857 (3)	0.5235 (3)	0.0525 (7)
H10A	0.8897	1.1596	0.5123	0.063*
C16	0.3722 (3)	0.6342 (2)	0.0397 (2)	0.0366 (5)
C3	0.3250 (4)	0.5376 (2)	0.5951 (2)	0.0396 (5)
C18	0.4773 (4)	0.7863 (3)	−0.0758 (2)	0.0437 (6)
H18A	0.3912	0.7396	−0.1314	0.052*
C11	0.7318 (4)	0.9954 (3)	0.4349 (3)	0.0507 (7)
H11A	0.7356	1.0108	0.3638	0.061*
C20	0.7024 (3)	0.9492 (2)	−0.0119 (2)	0.0403 (5)
C14	0.1954 (4)	0.4306 (3)	−0.0405 (3)	0.0511 (7)
H14A	0.1437	0.3670	−0.1025	0.061*
N5	0.9098 (4)	1.1363 (3)	−0.0604 (3)	0.0645 (7)
C22	0.8224 (4)	1.0544 (3)	−0.0359 (2)	0.0481 (6)
C21	0.7073 (4)	0.9214 (3)	0.0921 (2)	0.0475 (6)
H21A	0.7873	0.9725	0.1496	0.057*
C1	0.2107 (4)	0.4315 (3)	0.6209 (2)	0.0509 (7)
C15	0.2969 (4)	0.5401 (3)	−0.0547 (2)	0.0458 (6)
H15A	0.3150	0.5511	−0.1266	0.055*
C12	0.2491 (4)	0.5138 (3)	0.1556 (3)	0.0552 (7)
H12A	0.2307	0.5046	0.2281	0.066*
N6	0.1246 (5)	0.3511 (3)	0.6475 (3)	0.0784 (10)
F3	0.0390 (3)	0.1799 (2)	0.2096 (2)	0.0787 (6)
B1	−0.0554 (4)	0.2501 (3)	0.2781 (3)	0.0411 (6)
F1	0.0294 (4)	0.3082 (4)	0.3781 (3)	0.1278 (13)
F2	−0.0835 (4)	0.3504 (3)	0.2347 (3)	0.1227 (12)
F4	−0.2181 (3)	0.1894 (2)	0.2873 (2)	0.0778 (6)
N4	0.5982 (3)	0.8218 (2)	0.11044 (18)	0.0445 (5)
N8	0.4633 (3)	0.5922 (2)	0.66795 (19)	0.0418 (5)
C5	0.5636 (3)	0.6942 (2)	0.6495 (2)	0.0387 (5)
H5A	0.6617	0.7348	0.6980	0.046*
N2	0.3941 (3)	0.6827 (2)	0.48248 (18)	0.0402 (5)
C2	0.2927 (4)	0.5793 (2)	0.5009 (2)	0.0420 (6)
H2B	0.1992	0.5350	0.4498	0.050*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0852 (2)	0.05274 (16)	0.02856 (13)	0.00162 (12)	−0.00852 (11)	0.00651 (9)
N1	0.0523 (13)	0.0386 (11)	0.0313 (11)	0.0033 (10)	0.0040 (9)	0.0102 (9)
C17	0.0408 (13)	0.0365 (12)	0.0269 (11)	0.0062 (10)	0.0027 (9)	0.0059 (9)
C8	0.0643 (18)	0.0420 (14)	0.0336 (13)	0.0004 (13)	−0.0073 (12)	0.0064 (11)
C9	0.0606 (18)	0.0383 (14)	0.0524 (17)	−0.0031 (13)	−0.0108 (14)	0.0052 (12)
N3	0.0541 (13)	0.0412 (11)	0.0320 (11)	−0.0036 (10)	0.0019 (10)	0.0113 (9)
N7	0.0503 (13)	0.0492 (13)	0.0342 (11)	0.0025 (10)	0.0034 (10)	0.0155 (10)
C6	0.0424 (13)	0.0345 (11)	0.0263 (11)	0.0064 (10)	0.0051 (9)	0.0058 (9)
C13	0.0599 (18)	0.0445 (15)	0.0550 (18)	−0.0077 (13)	0.0015 (14)	0.0160 (13)
C7	0.0438 (13)	0.0359 (12)	0.0292 (11)	0.0054 (10)	0.0034 (10)	0.0089 (9)
C10	0.0558 (17)	0.0394 (14)	0.0601 (19)	−0.0012 (12)	0.0014 (14)	0.0176 (13)
C16	0.0418 (13)	0.0360 (12)	0.0305 (12)	0.0056 (10)	−0.0014 (10)	0.0079 (9)
C3	0.0489 (14)	0.0314 (11)	0.0354 (13)	0.0036 (10)	0.0089 (11)	0.0058 (10)
C18	0.0504 (15)	0.0468 (14)	0.0297 (12)	−0.0019 (12)	−0.0009 (11)	0.0116 (11)
C11	0.0628 (18)	0.0465 (15)	0.0433 (15)	0.0012 (13)	0.0054 (13)	0.0204 (12)
C20	0.0447 (14)	0.0376 (12)	0.0369 (13)	0.0053 (11)	0.0063 (11)	0.0086 (10)
C14	0.0587 (17)	0.0411 (14)	0.0456 (16)	−0.0001 (12)	−0.0081 (13)	0.0051 (12)
N5	0.0714 (18)	0.0531 (15)	0.0635 (18)	−0.0065 (14)	0.0085 (15)	0.0197 (14)
C22	0.0561 (17)	0.0450 (15)	0.0409 (15)	0.0056 (13)	0.0049 (13)	0.0104 (12)
C21	0.0573 (17)	0.0427 (14)	0.0341 (13)	−0.0036 (12)	−0.0031 (12)	0.0056 (11)
C1	0.0690 (19)	0.0373 (13)	0.0402 (15)	−0.0022 (13)	0.0027 (13)	0.0092 (11)
C15	0.0596 (17)	0.0411 (13)	0.0323 (13)	0.0027 (12)	−0.0034 (12)	0.0077 (11)
C12	0.0670 (19)	0.0540 (17)	0.0401 (15)	−0.0060 (14)	0.0060 (14)	0.0180 (13)
N6	0.102 (2)	0.0543 (16)	0.065 (2)	−0.0189 (16)	0.0047 (18)	0.0184 (15)
F3	0.0780 (14)	0.0826 (14)	0.0689 (14)	0.0290 (12)	0.0006 (11)	−0.0027 (11)
B1	0.0441 (16)	0.0402 (15)	0.0358 (14)	−0.0004 (12)	0.0024 (12)	0.0110 (12)
F1	0.0818 (17)	0.168 (3)	0.084 (2)	0.0053 (18)	−0.0150 (15)	−0.0426 (19)
F2	0.143 (3)	0.101 (2)	0.159 (3)	0.0464 (19)	0.077 (2)	0.079 (2)
F4	0.0647 (12)	0.0723 (13)	0.0895 (16)	−0.0018 (10)	0.0035 (11)	0.0202 (12)
N4	0.0574 (13)	0.0404 (11)	0.0293 (10)	−0.0027 (10)	−0.0018 (10)	0.0074 (9)
N8	0.0501 (12)	0.0392 (11)	0.0364 (11)	0.0061 (10)	0.0037 (9)	0.0129 (9)
C5	0.0427 (13)	0.0403 (12)	0.0323 (12)	0.0051 (10)	0.0012 (10)	0.0103 (10)
N2	0.0486 (12)	0.0394 (11)	0.0293 (10)	0.0030 (9)	0.0003 (9)	0.0078 (9)
C2	0.0491 (15)	0.0391 (13)	0.0321 (12)	−0.0005 (11)	−0.0017 (11)	0.0066 (10)

Geometric parameters (Å, º)

Ag1—N1	2.196 (2)	C16—C15	1.394 (4)
Ag1—N3	2.203 (2)	C3—N8	1.337 (4)
N1—C7	1.338 (3)	C3—C2	1.387 (4)
N1—C11	1.341 (4)	C3—C1	1.447 (4)
C17—N4	1.333 (3)	C18—H18A	0.9300
C17—C18	1.400 (3)	C11—H11A	0.9300
C17—C16	1.485 (3)	C20—C21	1.388 (4)
C8—C7	1.390 (4)	C20—C22	1.451 (4)
C8—C9	1.394 (4)	C14—C15	1.378 (4)
C8—H8A	0.9300	C14—H14A	0.9300
C9—C10	1.369 (5)	N5—C22	1.139 (4)
C9—H9A	0.9300	C21—N4	1.335 (4)
N3—C12	1.329 (4)	C21—H21A	0.9300
N3—C16	1.341 (3)	C1—N6	1.134 (4)
N7—C20	1.324 (4)	C15—H15A	0.9300
N7—C18	1.326 (4)	C12—H12A	0.9300
C6—N2	1.335 (3)	F3—B1	1.340 (4)
C6—C5	1.406 (3)	B1—F1	1.337 (4)
C6—C7	1.484 (3)	B1—F4	1.340 (4)
C13—C14	1.368 (4)	B1—F2	1.413 (4)
C13—C12	1.373 (4)	N8—C5	1.326 (3)
C13—H13A	0.9300	C5—H5A	0.9300
C10—C11	1.370 (4)	N2—C2	1.341 (3)
C10—H10A	0.9300	C2—H2B	0.9300
N1—Ag1—N3	177.92 (8)	C17—C18—H18A	118.8
C7—N1—C11	118.1 (2)	N1—C11—C10	123.6 (3)
C7—N1—Ag1	123.04 (17)	N1—C11—H11A	118.2
C11—N1—Ag1	118.76 (19)	C10—C11—H11A	118.2
N4—C17—C18	120.3 (2)	N7—C20—C21	122.9 (2)
N4—C17—C16	119.2 (2)	N7—C20—C22	115.0 (2)
C18—C17—C16	120.5 (2)	C21—C20—C22	122.1 (3)
C7—C8—C9	119.2 (3)	C13—C14—C15	118.9 (3)
C7—C8—H8A	120.4	C13—C14—H14A	120.6
C9—C8—H8A	120.4	C15—C14—H14A	120.6
C10—C9—C8	118.8 (3)	N5—C22—C20	175.8 (3)
C10—C9—H9A	120.6	N4—C21—C20	120.5 (2)
C8—C9—H9A	120.6	N4—C21—H21A	119.7
C12—N3—C16	118.1 (2)	C20—C21—H21A	119.7
C12—N3—Ag1	118.73 (19)	N6—C1—C3	176.1 (3)
C16—N3—Ag1	122.86 (17)	C14—C15—C16	119.4 (3)
C20—N7—C18	116.0 (2)	C14—C15—H15A	120.3
N2—C6—C5	121.1 (2)	C16—C15—H15A	120.3
N2—C6—C7	118.7 (2)	N3—C12—C13	123.7 (3)
C5—C6—C7	120.2 (2)	N3—C12—H12A	118.2
C14—C13—C12	118.6 (3)	C13—C12—H12A	118.2
C14—C13—H13A	120.7	F1—B1—F4	112.6 (3)
C12—C13—H13A	120.7	F1—B1—F3	112.4 (3)
N1—C7—C8	121.6 (2)	F4—B1—F3	114.0 (3)
N1—C7—C6	118.2 (2)	F1—B1—F2	103.0 (3)
C8—C7—C6	120.2 (2)	F4—B1—F2	103.0 (3)
C9—C10—C11	118.7 (3)	F3—B1—F2	110.8 (3)
C9—C10—H10A	120.7	C17—N4—C21	117.6 (2)
C11—C10—H10A	120.7	C5—N8—C3	116.3 (2)
N3—C16—C15	121.3 (2)	N8—C5—C6	121.8 (2)
N3—C16—C17	118.7 (2)	N8—C5—H5A	119.1
C15—C16—C17	120.0 (2)	C6—C5—H5A	119.1
N8—C3—C2	122.5 (2)	C6—N2—C2	116.9 (2)
N8—C3—C1	115.5 (2)	N2—C2—C3	121.0 (2)
C2—C3—C1	122.1 (3)	N2—C2—H2B	119.5
N7—C18—C17	122.4 (2)	C3—C2—H2B	119.5
N7—C18—H18A	118.8
C7—C8—C9—C10	0.4 (5)	C9—C10—C11—N1	−1.3 (5)
C11—N1—C7—C8	1.1 (4)	C18—N7—C20—C21	−1.8 (4)
Ag1—N1—C7—C8	−176.0 (2)	C18—N7—C20—C22	179.3 (3)
C11—N1—C7—C6	−180.0 (2)	C12—C13—C14—C15	0.7 (5)
Ag1—N1—C7—C6	3.0 (3)	N7—C20—C21—N4	3.1 (4)
C9—C8—C7—N1	−1.5 (4)	C22—C20—C21—N4	−178.1 (3)
C9—C8—C7—C6	179.6 (3)	C13—C14—C15—C16	−0.3 (5)
N2—C6—C7—N1	−24.8 (3)	N3—C16—C15—C14	0.4 (4)
C5—C6—C7—N1	156.3 (2)	C17—C16—C15—C14	178.1 (3)
N2—C6—C7—C8	154.2 (3)	C16—N3—C12—C13	1.3 (5)
C5—C6—C7—C8	−24.7 (4)	Ag1—N3—C12—C13	−172.3 (3)
C8—C9—C10—C11	0.9 (5)	C14—C13—C12—N3	−1.3 (5)
C12—N3—C16—C15	−0.9 (4)	C18—C17—N4—C21	−4.3 (4)
Ag1—N3—C16—C15	172.5 (2)	C16—C17—N4—C21	175.4 (2)
C12—N3—C16—C17	−178.6 (3)	C20—C21—N4—C17	0.2 (4)
Ag1—N3—C16—C17	−5.3 (3)	C2—C3—N8—C5	4.0 (4)
N4—C17—C16—N3	18.2 (4)	C1—C3—N8—C5	−176.0 (2)
C18—C17—C16—N3	−162.2 (3)	C3—N8—C5—C6	0.5 (4)
N4—C17—C16—C15	−159.6 (3)	N2—C6—C5—N8	−5.0 (4)
C18—C17—C16—C15	20.0 (4)	C7—C6—C5—N8	173.9 (2)
C20—N7—C18—C17	−2.4 (4)	C5—C6—N2—C2	4.6 (4)
N4—C17—C18—N7	5.7 (4)	C7—C6—N2—C2	−174.3 (2)
C16—C17—C18—N7	−174.0 (3)	C6—N2—C2—C3	−0.3 (4)
C7—N1—C11—C10	0.3 (5)	N8—C3—C2—N2	−4.3 (4)
Ag1—N1—C11—C10	177.5 (2)	C1—C3—C2—N2	175.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5a···F3^i	0.93	2.49	3.398 (3)	167
C13—H13a···F2	0.93	2.43	3.015 (5)	121
C11—H11a···F4^ii	0.93	2.39	3.132 (4)	137

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