Bis[5-(pyridin-2-yl)pyrazine-2-carbo-nitrile-κN,N]silver(I) perchlorate.

In the mononuclear title complex, [Ag(C(10)H(6)N(4))(2)]ClO(4), the Ag(I) ion is surrounded by two 5-(pyridin-2-yl)pyrazine-2-carbonitrile ligands, forming a considerably distorted square-planar N(4)-coordination geometry, with two short and two long Ag-N distances. Each perchlorate anion links two mononuclear coordination units through C-H⋯O(perchlorate) hydrogen bonding, forming an infinite tape structure along [110]. Inter-molecular π-π stacking inter-actions between adjacent pyridine and pyrazine rings [centroid-centroid distances of 3.777 (3) and 3.879 (2) Å] further assemble the tape motifs into a three-dimensional supra-molecular structure.

Related literature

For coordination complexes with cyano, carboxyl­ate, pyridyl and triazole groups, see: Wang et al. (2009 ▶); Manriquez et al. (1991 ▶). For these involving 2,2′-bipyridine derivatives, see: Berghian et al. (2005 ▶); Mathieu et al. (2001 ▶). For comparable structures, see: Biju & Rajasekharan (2008 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

[Ag(C10H6N4)2]ClO4

M = 571.70

Triclinic,

a = 7.8804 (10) Å

b = 11.3152 (14) Å

c = 12.3317 (14) Å

α = 104.015 (2)°

β = 92.015 (2)°

γ = 101.171 (2)°

V = 1042.8 (2) Å3

Z = 2

Mo Kα radiation

μ = 1.14 mm−1

T = 293 K

0.30 × 0.20 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.577, T max = 0.755

7304 measured reflections

5075 independent reflections

3882 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.092

S = 1.03

5075 reflections

307 parameters

10 restraints

H-atom parameters constrained

Δρmax = 0.54 e Å−3

Δρmin = −0.31 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 datablock(s) I, global. DOI: 10.1107/S1600536811046708/ez2265sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046708/ez2265Isup2.hkl

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

[Ag(C10H6N4)2]ClO4	Z = 2
Mr = 571.70	F(000) = 568
Triclinic, P1	Dx = 1.821 Mg m−3
a = 7.8804 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3152 (14) Å	Cell parameters from 233 reflections
c = 12.3317 (14) Å	θ = 1.7–28.2°
α = 104.015 (2)°	µ = 1.14 mm−1
β = 92.015 (2)°	T = 293 K
γ = 101.171 (2)°	Rod, colorless
V = 1042.8 (2) Å3	0.30 × 0.20 × 0.12 mm

Bruker APEXII CCD area-detector diffractometer	5075 independent reflections
Radiation source: fine-focus sealed tube	3882 reflections with I > 2σ(I)
graphite	Rint = 0.021
ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −10→10
Tmin = 0.577, Tmax = 0.755	k = −15→10
7304 measured reflections	l = −16→15

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.4461P] where P = (Fo2 + 2Fc2)/3
5075 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.54 e Å−3
10 restraints	Δρmin = −0.31 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	0.50428 (3)	0.75075 (2)	0.705977 (16)	0.05505 (10)
C1	0.3777 (3)	0.6399 (2)	0.45026 (19)	0.0332 (5)
C2	0.2969 (4)	0.5507 (3)	0.3561 (2)	0.0460 (6)
H2A	0.3090	0.5652	0.2854	0.055*
C3	0.1978 (4)	0.4399 (3)	0.3670 (3)	0.0519 (7)
H3A	0.1420	0.3794	0.3042	0.062*
C4	0.1834 (4)	0.4209 (3)	0.4728 (3)	0.0519 (7)
H4A	0.1166	0.3478	0.4832	0.062*
C5	0.2700 (4)	0.5124 (3)	0.5623 (2)	0.0490 (7)
H5A	0.2616	0.4985	0.6334	0.059*
N1	0.3662 (3)	0.6209 (2)	0.55367 (17)	0.0380 (5)
C6	0.7085 (3)	0.9257 (2)	0.5006 (2)	0.0392 (6)
H6A	0.8006	0.9708	0.5527	0.047*
C7	0.6760 (3)	0.9659 (2)	0.4053 (2)	0.0369 (5)
N3	0.5409 (3)	0.9082 (2)	0.32982 (17)	0.0391 (5)
C9	0.4813 (3)	0.7606 (2)	0.43988 (19)	0.0323 (5)
N2	0.6093 (3)	0.8232 (2)	0.51831 (16)	0.0371 (5)
C8	0.4446 (3)	0.8066 (2)	0.3479 (2)	0.0367 (5)
H8A	0.3490	0.7641	0.2977	0.044*
C11	0.6248 (3)	0.8669 (2)	0.96211 (18)	0.0329 (5)
C12	0.7024 (4)	0.9591 (3)	1.0561 (2)	0.0411 (6)
H12A	0.6862	0.9473	1.1274	0.049*
C13	0.8034 (4)	1.0681 (3)	1.0438 (2)	0.0451 (6)
H13A	0.8560	1.1306	1.1063	0.054*
C14	0.8250 (4)	1.0828 (3)	0.9377 (2)	0.0500 (7)
H14A	0.8927	1.1552	0.9266	0.060*
C15	0.7445 (4)	0.9883 (3)	0.8481 (2)	0.0519 (7)
H15A	0.7598	0.9990	0.7764	0.062*
N5	0.6457 (3)	0.8821 (2)	0.85757 (17)	0.0410 (5)
C16	0.2892 (4)	0.5835 (2)	0.9077 (2)	0.0435 (6)
H16A	0.2074	0.5338	0.8504	0.052*
C17	0.2979 (3)	0.5534 (2)	1.0099 (2)	0.0372 (5)
C18	0.5251 (3)	0.7139 (3)	1.0743 (2)	0.0400 (6)
H18A	0.6126	0.7593	1.1296	0.048*
C19	0.5123 (3)	0.7507 (2)	0.97452 (18)	0.0322 (5)
N6	0.3962 (3)	0.6827 (2)	0.89007 (17)	0.0408 (5)
N7	0.4176 (3)	0.6168 (2)	1.09313 (17)	0.0418 (5)
C10	0.7861 (4)	1.0716 (3)	0.3789 (2)	0.0464 (6)
N4	0.8670 (4)	1.1518 (3)	0.3512 (2)	0.0716 (8)
C20	0.1815 (4)	0.4486 (3)	1.0339 (2)	0.0443 (6)
N8	0.0976 (4)	0.3679 (3)	1.0585 (2)	0.0603 (7)
Cl1	0.94869 (8)	0.75080 (6)	0.28153 (5)	0.03921 (15)
O3	1.0442 (3)	0.6770 (2)	0.20672 (19)	0.0635 (6)
O4	0.7780 (3)	0.6817 (2)	0.28566 (19)	0.0590 (5)
O1	1.0367 (3)	0.7906 (3)	0.39031 (19)	0.0854 (9)
O2	0.9306 (4)	0.8567 (2)	0.2423 (3)	0.0870 (9)

	U11	U22	U33	U12	U13	U23
Ag1	0.07966 (19)	0.05148 (15)	0.02647 (11)	0.00307 (12)	−0.00799 (10)	0.00575 (9)
C1	0.0370 (12)	0.0342 (12)	0.0289 (11)	0.0064 (10)	0.0016 (9)	0.0099 (10)
C2	0.0593 (17)	0.0446 (15)	0.0304 (12)	0.0041 (13)	−0.0068 (11)	0.0091 (11)
C3	0.0600 (18)	0.0374 (15)	0.0489 (16)	−0.0027 (13)	−0.0132 (13)	0.0056 (12)
C4	0.0540 (17)	0.0401 (15)	0.0598 (18)	−0.0018 (13)	−0.0004 (14)	0.0193 (14)
C5	0.0591 (17)	0.0481 (16)	0.0400 (14)	0.0006 (14)	0.0055 (13)	0.0193 (13)
N1	0.0451 (12)	0.0390 (12)	0.0289 (10)	0.0022 (9)	0.0030 (9)	0.0117 (9)
C6	0.0460 (14)	0.0367 (13)	0.0292 (12)	−0.0005 (11)	−0.0004 (10)	0.0050 (10)
C7	0.0488 (14)	0.0298 (12)	0.0313 (12)	0.0067 (11)	0.0096 (10)	0.0066 (10)
N3	0.0446 (12)	0.0408 (12)	0.0325 (10)	0.0070 (10)	0.0033 (9)	0.0121 (9)
C9	0.0372 (12)	0.0334 (12)	0.0262 (11)	0.0077 (10)	0.0068 (9)	0.0065 (9)
N2	0.0467 (12)	0.0356 (11)	0.0253 (9)	0.0030 (9)	0.0006 (8)	0.0059 (8)
C8	0.0366 (13)	0.0405 (14)	0.0332 (12)	0.0054 (11)	0.0011 (10)	0.0120 (10)
C11	0.0368 (12)	0.0357 (12)	0.0254 (11)	0.0056 (10)	0.0014 (9)	0.0082 (9)
C12	0.0528 (15)	0.0419 (14)	0.0263 (11)	0.0048 (12)	−0.0005 (10)	0.0088 (10)
C13	0.0519 (16)	0.0398 (14)	0.0368 (13)	0.0011 (12)	−0.0043 (11)	0.0046 (11)
C14	0.0541 (16)	0.0428 (15)	0.0477 (16)	−0.0068 (13)	0.0048 (13)	0.0148 (13)
C15	0.0649 (18)	0.0529 (17)	0.0338 (14)	−0.0052 (14)	0.0080 (13)	0.0169 (13)
N5	0.0500 (12)	0.0434 (12)	0.0256 (10)	−0.0018 (10)	0.0025 (9)	0.0105 (9)
C16	0.0543 (16)	0.0384 (14)	0.0308 (12)	−0.0020 (12)	−0.0032 (11)	0.0057 (11)
C17	0.0410 (13)	0.0353 (13)	0.0347 (12)	0.0074 (11)	0.0080 (10)	0.0078 (10)
C18	0.0428 (14)	0.0448 (15)	0.0299 (12)	−0.0008 (11)	−0.0004 (10)	0.0133 (11)
C19	0.0373 (12)	0.0346 (12)	0.0239 (10)	0.0075 (10)	0.0030 (9)	0.0059 (9)
N6	0.0534 (13)	0.0370 (12)	0.0271 (10)	−0.0004 (10)	−0.0008 (9)	0.0070 (9)
N7	0.0473 (12)	0.0455 (13)	0.0320 (11)	0.0027 (10)	0.0029 (9)	0.0140 (10)
C10	0.0627 (17)	0.0367 (14)	0.0330 (13)	−0.0002 (13)	0.0008 (12)	0.0051 (11)
N4	0.104 (2)	0.0470 (16)	0.0509 (16)	−0.0174 (16)	0.0052 (15)	0.0140 (13)
C20	0.0489 (15)	0.0419 (15)	0.0389 (14)	0.0029 (12)	0.0045 (12)	0.0092 (12)
N8	0.0701 (17)	0.0492 (15)	0.0560 (16)	−0.0049 (13)	0.0054 (13)	0.0166 (13)
Cl1	0.0416 (3)	0.0371 (3)	0.0345 (3)	0.0008 (3)	0.0034 (2)	0.0066 (2)
O3	0.0616 (13)	0.0711 (15)	0.0531 (13)	0.0254 (12)	0.0021 (10)	−0.0022 (11)
O4	0.0473 (11)	0.0565 (13)	0.0687 (14)	−0.0064 (10)	0.0009 (10)	0.0215 (11)
O1	0.0658 (15)	0.121 (2)	0.0418 (12)	−0.0060 (15)	−0.0094 (11)	−0.0089 (14)
O2	0.0997 (19)	0.0640 (16)	0.126 (2)	0.0313 (14)	0.0595 (18)	0.0591 (17)

Ag1—N1	2.184 (2)	C11—C12	1.387 (3)
Ag1—N5	2.193 (2)	C11—C19	1.481 (3)
Ag1—N6	2.683 (2)	C12—C13	1.378 (4)
Ag1—N2	2.739 (2)	C12—H12A	0.9300
C1—N1	1.347 (3)	C13—C14	1.371 (4)
C1—C2	1.379 (4)	C13—H13A	0.9300
C1—C9	1.486 (3)	C14—C15	1.372 (4)
C2—C3	1.382 (4)	C14—H14A	0.9300
C2—H2A	0.9300	C15—N5	1.333 (3)
C3—C4	1.378 (4)	C15—H15A	0.9300
C3—H3A	0.9300	C16—N6	1.335 (3)
C4—C5	1.369 (4)	C16—C17	1.386 (3)
C4—H4A	0.9300	C16—H16A	0.9300
C5—N1	1.342 (3)	C17—N7	1.331 (3)
C5—H5A	0.9300	C17—C20	1.450 (4)
C6—N2	1.337 (3)	C18—N7	1.325 (3)
C6—C7	1.392 (3)	C18—C19	1.397 (3)
C6—H6A	0.9300	C18—H18A	0.9300
C7—N3	1.339 (3)	C19—N6	1.336 (3)
C7—C10	1.447 (4)	C10—N4	1.135 (4)
N3—C8	1.321 (3)	C20—N8	1.131 (4)
C9—N2	1.333 (3)	Cl1—O1	1.416 (2)
C9—C8	1.401 (3)	Cl1—O2	1.426 (2)
C8—H8A	0.9300	Cl1—O3	1.426 (2)
C11—N5	1.353 (3)	Cl1—O4	1.428 (2)
N1—Ag1—N5	179.23 (7)	C13—C12—H12A	120.0
N1—C1—C2	121.7 (2)	C11—C12—H12A	120.0
N1—C1—C9	117.9 (2)	C14—C13—C12	118.7 (3)
C2—C1—C9	120.4 (2)	C14—C13—H13A	120.7
C1—C2—C3	119.9 (2)	C12—C13—H13A	120.7
C1—C2—H2A	120.1	C13—C14—C15	118.6 (3)
C3—C2—H2A	120.1	C13—C14—H14A	120.7
C4—C3—C2	118.7 (3)	C15—C14—H14A	120.7
C4—C3—H3A	120.7	N5—C15—C14	124.0 (2)
C2—C3—H3A	120.7	N5—C15—H15A	118.0
C5—C4—C3	118.3 (3)	C14—C15—H15A	118.0
C5—C4—H4A	120.9	C15—N5—C11	117.7 (2)
C3—C4—H4A	120.9	C15—N5—Ag1	118.68 (17)
N1—C5—C4	124.0 (3)	C11—N5—Ag1	123.31 (17)
N1—C5—H5A	118.0	N6—C16—C17	121.1 (2)
C4—C5—H5A	118.0	N6—C16—H16A	119.5
C5—N1—C1	117.5 (2)	C17—C16—H16A	119.5
C5—N1—Ag1	118.25 (17)	N7—C17—C16	122.4 (2)
C1—N1—Ag1	124.21 (17)	N7—C17—C20	114.5 (2)
N2—C6—C7	121.0 (2)	C16—C17—C20	123.0 (2)
N2—C6—H6A	119.5	N7—C18—C19	122.6 (2)
C7—C6—H6A	119.5	N7—C18—H18A	118.7
N3—C7—C6	122.3 (2)	C19—C18—H18A	118.7
N3—C7—C10	114.7 (2)	N6—C19—C18	120.4 (2)
C6—C7—C10	123.0 (2)	N6—C19—C11	119.3 (2)
C8—N3—C7	116.1 (2)	C18—C19—C11	120.3 (2)
N2—C9—C8	120.9 (2)	C16—N6—C19	117.3 (2)
N2—C9—C1	119.2 (2)	C18—N7—C17	116.1 (2)
C8—C9—C1	119.9 (2)	N4—C10—C7	175.5 (3)
C9—N2—C6	117.1 (2)	N8—C20—C17	175.7 (3)
N3—C8—C9	122.4 (2)	O1—Cl1—O2	109.5 (2)
N3—C8—H8A	118.8	O1—Cl1—O3	109.86 (16)
C9—C8—H8A	118.8	O2—Cl1—O3	109.58 (15)
N5—C11—C12	121.1 (2)	O1—Cl1—O4	109.76 (14)
N5—C11—C19	118.5 (2)	O2—Cl1—O4	107.38 (15)
C12—C11—C19	120.4 (2)	O3—Cl1—O4	110.68 (14)
C13—C12—C11	120.0 (2)
N1—C1—C2—C3	1.5 (4)	C11—C12—C13—C14	0.0 (4)
C9—C1—C2—C3	−178.6 (3)	C12—C13—C14—C15	0.2 (5)
C1—C2—C3—C4	−0.5 (5)	C13—C14—C15—N5	0.0 (5)
C2—C3—C4—C5	−0.8 (5)	C14—C15—N5—C11	−0.4 (5)
C3—C4—C5—N1	1.2 (5)	C14—C15—N5—Ag1	173.3 (2)
C4—C5—N1—C1	−0.2 (4)	C12—C11—N5—C15	0.6 (4)
C4—C5—N1—Ag1	−177.0 (2)	C19—C11—N5—C15	178.6 (2)
C2—C1—N1—C5	−1.2 (4)	C12—C11—N5—Ag1	−172.76 (19)
C9—C1—N1—C5	178.9 (2)	C19—C11—N5—Ag1	5.3 (3)
C2—C1—N1—Ag1	175.5 (2)	N1—Ag1—N5—C15	28 (6)
C9—C1—N1—Ag1	−4.4 (3)	N1—Ag1—N5—C11	−159 (6)
N5—Ag1—N1—C5	151 (6)	N6—C16—C17—N7	−3.6 (4)
N5—Ag1—N1—C1	−26 (6)	N6—C16—C17—C20	178.4 (3)
N2—C6—C7—N3	3.0 (4)	N7—C18—C19—N6	−4.7 (4)
N2—C6—C7—C10	−176.0 (2)	N7—C18—C19—C11	174.1 (2)
C6—C7—N3—C8	−3.3 (4)	N5—C11—C19—N6	−19.7 (3)
C10—C7—N3—C8	175.8 (2)	C12—C11—C19—N6	158.4 (2)
N1—C1—C9—N2	26.0 (3)	N5—C11—C19—C18	161.5 (2)
C2—C1—C9—N2	−153.9 (2)	C12—C11—C19—C18	−20.5 (4)
N1—C1—C9—C8	−154.5 (2)	C17—C16—N6—C19	0.5 (4)
C2—C1—C9—C8	25.6 (4)	C18—C19—N6—C16	3.4 (4)
C8—C9—N2—C6	−5.1 (3)	C11—C19—N6—C16	−175.4 (2)
C1—C9—N2—C6	174.4 (2)	C19—C18—N7—C17	1.6 (4)
C7—C6—N2—C9	1.4 (4)	C16—C17—N7—C18	2.4 (4)
C7—N3—C8—C9	−0.5 (4)	C20—C17—N7—C18	−179.4 (2)
N2—C9—C8—N3	4.9 (4)	N3—C7—C10—N4	−14 (4)
C1—C9—C8—N3	−174.6 (2)	C6—C7—C10—N4	165 (4)
N5—C11—C12—C13	−0.4 (4)	N7—C17—C20—N8	−11 (4)
C19—C11—C12—C13	−178.4 (2)	C16—C17—C20—N8	167 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···O2i	0.93	2.71	3.203 (2)	114
C14—H14A···O2i	0.93	2.54	3.103 (2)	119
C5—H5A···O4ii	0.93	2.45	3.193 (3)	137

Table 1

Selected bond lengths (Å)

Ag1—N1	2.184 (2)
Ag1—N5	2.193 (2)
Ag1—N6	2.683 (2)
Ag1—N2	2.739 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯O2i	0.93	2.71	3.203 (2)	114
C14—H14A⋯O2i	0.93	2.54	3.103 (2)	119
C5—H5A⋯O4ii	0.93	2.45	3.193 (3)	137

Symmetry codes: (i) ; (ii) .