Bis[5-(2-pyrid-yl)pyrazine-2-carbonitrile]-silver(I) tetra-fluorido-borate.

In the title mononuclear complex, [Ag(C(10)H(6)N(4))(2)]BF(4), the Ag(I) atom adopts a square-planar N(4 )coordination geometry and is surrounded by two 5-(2-pyrid-yl)pyrazine-2-carbonitrile ligands. The tetra-fluorido-borate anions link the mononuclear cations through inter-molecular C-H⋯F hydrogen-bonding inter-actions, forming an infinite tape structure along [110]. Other weak inter-actions 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 tetra-fluorido-borate anions and pyrazine rings [F⋯centroid = 2.999 (3) Å]; these combine with the hydrogen-bonding inter-actions to link the mononuclear cations into a three-dimensional supra-molecular 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 = 559.06

Triclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.04

4986 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.95 e Å−3

Δρmin = −0.73 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[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) Å3

Bruker APEXII CCD area-detector diffractometer	4986 independent reflections
Radiation source: fine-focus sealed tube	3929 reflections with I > 2σ(I)
graphite	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 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(Fo2) + (0.0606P)2 + 0.3679P] where P = (Fo2 + 2Fc2)/3
4986 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.95 e Å−3
0 restraints	Δρmin = −0.73 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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.

	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*

	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)

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)

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

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	Cg4iv	3.898 (1)	25.89

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) ; (ii) .