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

Wang, Z.-J.; Zhang, F.; Wan, C.-Q.

doi:10.1107/S1600536810035178

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages m1232-m1233

doi:10.1107/S1600536810035178

Open

access

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

Zi-Jia Wang,^a Fan Zhang ^a and Chong-Qing Wan ^a ^*

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: wanchqing@yahoo.com.cn

(Received 12 July 2010; accepted 31 August 2010; online 8 September 2010)

In the title mononuclear complex, [Ag(C₁₀H₆N₄)₂]BF₄, the Ag^I atom adopts a square-planar N₄coordination 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.

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 & Vittal (2010 ). For properties of pyridine-based ligands, see: Casini et al. (2006). For comparison Ag—N(pyrazinyl) distances, see: Biju & Rajasekharan (2008 ). For C—H⋯F interactions, see: Denis et al. (2004 ). For a comparable BF₄ anion–pyrazinyl interaction, see: Wan et al. (2008 ).

Experimental

Crystal data

[Ag(C₁₀H₆N₄)₂]BF₄
M_r = 559.06
Triclinic, $[P \overline 1]$
a = 7.8144 (12) Å
b = 11.2492 (16) Å
c = 12.2697 (18) Å
α = 104.168 (3)°
β = 90.789 (2)°
γ = 101.429 (3)°
V = 1022.8 (3) Å³
Z = 2
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 293 K
0.45 × 0.40 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.615, T_max = 0.783
7178 measured reflections
4986 independent reflections
3929 reflections with I > 2σ(I)
R_int = 0.017

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.111
S = 1.04
4986 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.73 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5a⋯F3ⁱ	0.93	2.49	3.398 (3)	167
C13—H13a⋯F2	0.93	2.43	3.015 (5)	121
C11—H11a⋯F4ⁱⁱ	0.93	2.39	3.132 (4)	137
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y+1, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: APEX2 and SAINT (Bruker, 2007); data reduction: SAINT; 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810035178/bg2359sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035178/bg2359Isup2.hkl

checkCIF report

Comment top

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 top

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).

Experimental top

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).

Computing details top

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 top

	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···Cg2ⁱ,Cg3···Cg3ⁱⁱ,Cg4···Cg4ⁱⁱⁱ 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 top

Crystal data top

[Ag(C₁₀H₆N₄)₂]BF₄	Z = 2
M_r = 559.06	F(000) = 552
Triclinic, P1	D_x = 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) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4986 independent reflections
Radiation source: fine-focus sealed tube	3929 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.017
ω scans	θ_max = 28.3°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
T_min = 0.615, T_max = 0.783	k = −15→11
7178 measured reflections	l = −11→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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0606P)² + 0.3679P] where P = (F_o² + 2F_c²)/3
4986 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.95 e Å⁻³
0 restraints	Δρ_min = −0.73 e Å⁻³

Crystal data top

[Ag(C₁₀H₆N₄)₂]BF₄	γ = 101.429 (3)°
M_r = 559.06	V = 1022.8 (3) Å³
Triclinic, P1	Z = 2
a = 7.8144 (12) Å	Mo Kα radiation
b = 11.2492 (16) Å	µ = 1.05 mm⁻¹
c = 12.2697 (18) Å	T = 293 K
α = 104.168 (3)°	0.45 × 0.40 × 0.30 mm
β = 90.789 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4986 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3929 reflections with I > 2σ(I)
T_min = 0.615, T_max = 0.783	R_int = 0.017
7178 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.111	H-atom parameters constrained
S = 1.04	Δρ_max = 0.95 e Å⁻³
4986 reflections	Δρ_min = −0.73 e Å⁻³
307 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	0.48906 (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 (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
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) top

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) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5a···F3ⁱ	0.93	2.49	3.398 (3)	167
C13—H13a···F2	0.93	2.43	3.015 (5)	121
C11—H11a···F4ⁱⁱ	0.93	2.39	3.132 (4)	137

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₀H₆N₄)₂]BF₄
M_r	559.06
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.8144 (12), 11.2492 (16), 12.2697 (18)
α, β, γ (°)	104.168 (3), 90.789 (2), 101.429 (3)
V (Å³)	1022.8 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.45 × 0.40 × 0.30

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.615, 0.783
No. of measured, independent and observed [I > 2σ(I)] reflections	7178, 4986, 3929
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.111, 1.04
No. of reflections	4986
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.95, −0.73

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5a···F3ⁱ	0.93	2.49	3.398 (3)	167
C13—H13a···F2	0.93	2.43	3.015 (5)	121
C11—H11a···F4ⁱⁱ	0.93	2.39	3.132 (4)	137

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

π–π interactions top

Cg	Cg	Cg···Cg (Å)	Slippage angle
Cg1	Cg1ⁱ	3.610 (2)	20.71
Cg2	Cg2ⁱⁱ	3.926 (2)	33.28
Cg3	Cg3ⁱⁱⁱ	3.820 (2)	24.69
Cg4	Cg4^iv	3.898 (1)	25.89

Slippage angle = Angle Cg(I)-->Cg(J) normal to plane I Cg1,Cg2,Cg3,Cg4 are the centroids of C2-C3-N8-C5-C6-N2 (pyrazinyl) and C17-C18-N7-C20-C21-N4 (pyrazinyl), C7-C8-C9-C10-C11-N1(pyridyl) and C12-C13-C14-C15-C16-N3(pyridyl) respectively. Symmetry Codes: (i):-x+1, -y+1, -z+1; (ii): -x+1, -y+2, -z; (iii):-x+1, -y+2, -z+1; (iv): -x+1, -y+1, -z

Acknowledgements

The authors are grateful for financial support from the Science and Technology program, Beijing Municipal Education Commission.

References

Berghian, C., Mircea, D., Turck, A. & Plé, N. (2005). Tetrahedron, 61, 9637–9644. Web of Science CrossRef CAS Google Scholar
Biju, A. R. & Rajasekharan, M. V. (2008). Polyhedron, 27, 2065–2068. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casini, A., Cinellu, M. A., Minghetti, G., Gabbiani, C., Coronnello, M., Mini, E. & Messori, L. (2006). J. Med. Chem. 49, 5524–5531. Web of Science CrossRef PubMed CAS Google Scholar
Denis, G. G., Konstantin, A. L., Mikhail, Y. A., Yakov, S. V., Elena, I. L. & Alexander, S. S. (2004). CrystEngComm, 7, 53–56. Google Scholar
Li, H. H., Chen, Z. R., Sun, L. G., Lian, Z. X., Chen, X. B., Li, J. B. & Li, J. Q. (2010). Cryst. Growth Des. 10, 1068–1073. Web of Science CSD CrossRef CAS Google Scholar
Mathieu, J., Gros, P. & Fort, Y. (2001). Tetrahedron Lett. 42, 1879–1881. Web of Science CrossRef CAS Google Scholar
Peedikakkal, A. M. P. & Vittal, J. J. (2010). Inorg. Chem. 49, 10–12. Web of Science CSD 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
Wan, C. Q., Li, G. S., Chen, X. D. & Mak, T. C. W. (2008). Cryst. Growth Des. 8, 3897–3901. Web of Science CSD CrossRef CAS Google Scholar
Wang, R. M., Wang, X. M., Sundberg, E. B., Nguyen, P., Grant, G. P. G., Sheth, C., Zhao, Q., Herron, S., Kantardjieff, A. K. & Li, L. J. (2009). Inorg. Chem. 49, 9779–9785. Web of Science CSD CrossRef Google Scholar