(Nitrato-κO)bis-[5-(pyridin-2-yl)pyrazine-2-carbonitrile-κN,N]silver(I).

In the mononuclear title complex, [Ag(NO(3))(C(10)H(6)N(4))(2)], two κ(2)N:N'-chelating 5-(pyridin-2-yl)pyrazine-2-carbonitrile ligands surround the Ag(I) atom, forming an N(4)O square-pyramidal coordination geometry with one nitrate anion bonding at the apical site. The two heterocyclic rings of the 5-(2-pyridin-2--yl)pyrazine-2-carbonitrile ligand are almost coplanar [dihedral angle = 5.63 (8)°], and the two chelating ligands are in an anti relationship. The mononuclear units are inter-connected along [010] through C-H⋯O(nitrate) and C-H⋯N(cyano) inter-actions, forming an infinite chain. The mononuclear units are stacked along the a axis and inter-connected via inter-molecular π-π stacking inter-actions between adjacent pyridine and pyrazine rings [centroid-centroid distances = 3.984 (2) and 3.595 (3) Å], thus forming a three-dimensional supra-molecular structure.

Related literature

For coordination complexes with pyridyl-based ligands, see: Dunne et al. (1997 ▶); Wang et al. (2009 ▶). For a related complex with 5-(2-pyridin-2-­yl)pyrazine-2-carbonitrile, see: Wang et al. (2010 ▶).

Experimental

Crystal data

[Ag(NO3)(C10H6N4)2]

M = 534.26

Orthorhombic,

a = 14.000 (3) Å

b = 12.133 (2) Å

c = 23.832 (4) Å

V = 4048.4 (13) Å3

Z = 8

Mo Kα radiation

μ = 1.04 mm−1

T = 293 K

0.44 × 0.35 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.631, T max = 1.000

27695 measured reflections

5029 independent reflections

3255 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.099

S = 1.03

5029 reflections

298 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: 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/S1600536811049221/zq2135sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049221/zq2135Isup2.hkl

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

[Ag(NO3)(C10H6N4)2]	Z = 8
Mr = 534.26	F(000) = 2128
Orthorhombic, Pbca	Dx = 1.753 Mg m−3
Hall symbol: -P 2ac 2ab	Mo Kα radiation, λ = 0.71073 Å
a = 14.000 (3) Å	µ = 1.04 mm−1
b = 12.133 (2) Å	T = 293 K
c = 23.832 (4) Å	Block, yellow
V = 4048.4 (13) Å3	0.44 × 0.35 × 0.25 mm

Bruker APEXII CCD area-detector diffractometer	5029 independent reflections
Radiation source: fine-focus sealed tube	3255 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 28.3°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −18→16
Tmin = 0.631, Tmax = 1.000	k = −12→16
27695 measured reflections	l = −31→31

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) = 0.099	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0413P)2 + 2.5136P] P = (Fo2 + 2Fc2)/3
5029 reflections	(Δ/σ)max = 0.002
298 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.28 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	0.15007 (2)	0.51787 (2)	0.601301 (9)	0.06172 (11)
N5	0.1257 (2)	0.6243 (2)	0.69391 (10)	0.0614 (7)
N2	0.14122 (18)	0.4141 (2)	0.50864 (9)	0.0578 (6)
C19	0.1326 (3)	0.7327 (3)	0.70324 (12)	0.0667 (9)
H19A	0.1353	0.7807	0.6729	0.080*
C16	0.1216 (2)	0.5589 (2)	0.73859 (11)	0.0483 (6)
N6	0.1332 (2)	0.7114 (2)	0.80173 (10)	0.0705 (8)
C15	0.1147 (2)	0.4379 (2)	0.72912 (11)	0.0462 (6)
C20	0.1401 (3)	0.8922 (3)	0.76683 (13)	0.0628 (8)
C18	0.1356 (2)	0.7745 (2)	0.75668 (12)	0.0539 (7)
C1	0.1550 (2)	0.3072 (3)	0.49880 (13)	0.0640 (8)
H1A	0.1696	0.2608	0.5286	0.077*
N4	0.11379 (19)	0.4031 (2)	0.67615 (9)	0.0540 (6)
N3	0.1261 (3)	0.3264 (3)	0.40160 (11)	0.0812 (9)
C4	0.1200 (2)	0.4781 (3)	0.46515 (11)	0.0538 (7)
C5	0.1057 (2)	0.5976 (3)	0.47527 (11)	0.0522 (7)
N8	0.1425 (3)	0.9830 (3)	0.77670 (15)	0.0860 (11)
C2	0.1481 (2)	0.2638 (3)	0.44573 (13)	0.0618 (8)
C13	0.1112 (3)	0.2529 (3)	0.76347 (13)	0.0649 (9)
H13A	0.1102	0.2027	0.7930	0.078*
N1	0.1064 (2)	0.6321 (2)	0.52862 (9)	0.0609 (7)
C17B	0.1266 (3)	0.6037 (3)	0.79202 (12)	0.0690 (10)
H17A	0.1252	0.5561	0.8226	0.083*
C11	0.1116 (3)	0.2943 (3)	0.66699 (12)	0.0643 (9)
H11A	0.1100	0.2694	0.6301	0.077*
C6	0.0916 (3)	0.6712 (3)	0.43157 (12)	0.0668 (9)
H6A	0.0907	0.6461	0.3947	0.080*
C14	0.1122 (3)	0.3652 (3)	0.77357 (12)	0.0606 (8)
H14A	0.1112	0.3915	0.8102	0.073*
C12	0.1117 (3)	0.2179 (3)	0.70918 (13)	0.0637 (8)
H12A	0.1120	0.1430	0.7009	0.076*
C10	0.1610 (3)	0.1471 (4)	0.43460 (15)	0.0709 (9)
C9	0.0938 (3)	0.7393 (3)	0.53821 (13)	0.0724 (10)
H9A	0.0941	0.7631	0.5753	0.087*
C7	0.0789 (3)	0.7812 (3)	0.44284 (13)	0.0761 (11)
H7A	0.0693	0.8311	0.4137	0.091*
C8	0.0805 (3)	0.8168 (3)	0.49718 (14)	0.0752 (10)
H8A	0.0728	0.8909	0.5060	0.090*
N7	0.1715 (3)	0.0567 (3)	0.42452 (16)	0.0910 (10)
C3	0.1130 (3)	0.4318 (3)	0.41204 (13)	0.0793 (11)
H3A	0.0981	0.4780	0.3821	0.095*
N9	0.3705 (3)	0.5055 (3)	0.60786 (12)	0.0663 (8)
O1	0.3136 (2)	0.4333 (3)	0.61980 (14)	0.0984 (9)
O2	0.3387 (3)	0.5884 (3)	0.58609 (14)	0.1118 (11)
O3	0.4546 (3)	0.4916 (3)	0.61817 (18)	0.1278 (13)

	U11	U22	U33	U12	U13	U23
Ag1	0.0916 (2)	0.06265 (17)	0.03086 (12)	0.00339 (13)	−0.00402 (10)	0.01006 (10)
N5	0.105 (2)	0.0443 (14)	0.0350 (12)	−0.0033 (13)	0.0086 (12)	0.0042 (10)
N2	0.0754 (17)	0.0645 (17)	0.0334 (11)	0.0054 (13)	−0.0044 (11)	0.0051 (11)
C19	0.114 (3)	0.0477 (18)	0.0387 (14)	−0.0044 (17)	0.0097 (16)	0.0058 (13)
C16	0.0663 (18)	0.0449 (15)	0.0339 (13)	0.0023 (13)	0.0041 (11)	0.0039 (11)
N6	0.124 (3)	0.0491 (15)	0.0385 (12)	0.0014 (15)	0.0042 (14)	−0.0024 (12)
C15	0.0623 (17)	0.0428 (15)	0.0334 (12)	0.0014 (13)	0.0018 (11)	−0.0008 (11)
C20	0.090 (2)	0.050 (2)	0.0479 (16)	−0.0007 (17)	0.0101 (16)	−0.0005 (14)
C18	0.072 (2)	0.0433 (16)	0.0464 (15)	0.0000 (14)	0.0079 (13)	−0.0014 (13)
C1	0.080 (2)	0.069 (2)	0.0432 (16)	0.0067 (17)	−0.0080 (15)	0.0051 (15)
N4	0.0842 (17)	0.0446 (14)	0.0332 (11)	0.0018 (12)	0.0021 (11)	0.0007 (10)
N3	0.127 (3)	0.077 (2)	0.0402 (14)	−0.0038 (19)	−0.0035 (15)	−0.0020 (14)
C4	0.0628 (18)	0.066 (2)	0.0320 (13)	−0.0044 (15)	0.0005 (12)	0.0074 (13)
C5	0.0596 (17)	0.0646 (19)	0.0322 (12)	−0.0027 (15)	−0.0009 (12)	0.0089 (12)
N8	0.139 (3)	0.0503 (18)	0.069 (2)	−0.0001 (18)	0.0090 (19)	−0.0048 (15)
C2	0.068 (2)	0.068 (2)	0.0493 (16)	−0.0040 (17)	−0.0014 (14)	−0.0036 (15)
C13	0.104 (3)	0.0476 (18)	0.0434 (15)	−0.0059 (17)	−0.0042 (16)	0.0107 (13)
N1	0.0833 (18)	0.0636 (17)	0.0358 (12)	−0.0005 (14)	−0.0047 (12)	0.0078 (12)
C17B	0.128 (3)	0.0420 (17)	0.0372 (15)	0.0015 (18)	0.0034 (16)	0.0044 (13)
C11	0.108 (3)	0.0482 (18)	0.0373 (15)	−0.0021 (17)	−0.0001 (15)	−0.0038 (13)
C6	0.087 (2)	0.078 (2)	0.0353 (14)	0.0091 (19)	0.0002 (14)	0.0127 (15)
C14	0.097 (2)	0.0517 (18)	0.0330 (14)	−0.0058 (17)	−0.0010 (14)	0.0045 (13)
C12	0.097 (2)	0.0418 (17)	0.0527 (17)	−0.0037 (16)	−0.0004 (16)	−0.0017 (14)
C10	0.074 (2)	0.080 (3)	0.059 (2)	0.000 (2)	−0.0075 (16)	−0.0096 (19)
C9	0.106 (3)	0.068 (2)	0.0438 (16)	0.003 (2)	−0.0050 (17)	0.0031 (16)
C7	0.104 (3)	0.075 (3)	0.0491 (18)	0.014 (2)	0.0014 (18)	0.0234 (17)
C8	0.102 (3)	0.066 (2)	0.0574 (19)	0.0054 (19)	−0.0033 (18)	0.0120 (17)
N7	0.097 (3)	0.078 (2)	0.098 (3)	0.004 (2)	−0.022 (2)	−0.021 (2)
C3	0.134 (3)	0.069 (2)	0.0357 (15)	−0.003 (2)	−0.0082 (18)	0.0084 (16)
N9	0.083 (2)	0.065 (2)	0.0509 (16)	−0.0066 (15)	0.0031 (14)	−0.0043 (13)
O1	0.093 (2)	0.084 (2)	0.118 (2)	−0.0032 (17)	−0.0003 (17)	0.0475 (18)
O2	0.175 (3)	0.0582 (17)	0.102 (2)	−0.0110 (18)	−0.027 (2)	0.0188 (17)
O3	0.078 (2)	0.156 (3)	0.150 (3)	−0.005 (2)	−0.008 (2)	−0.026 (2)

Ag1—N1	2.301 (2)	C4—C5	1.483 (4)
Ag1—N4	2.319 (2)	C5—N1	1.338 (4)
Ag1—N2	2.545 (3)	C5—C6	1.386 (4)
Ag1—O1	2.547 (3)	C2—C10	1.453 (6)
Ag1—N5	2.579 (2)	C13—C12	1.362 (4)
N5—C16	1.329 (3)	C13—C14	1.383 (4)
N5—C19	1.338 (4)	C13—H13A	0.9300
N2—C4	1.329 (4)	N1—C9	1.333 (4)
N2—C1	1.332 (4)	C17B—H17A	0.9300
C19—C18	1.371 (4)	C11—C12	1.368 (4)
C19—H19A	0.9300	C11—H11A	0.9300
C16—C17B	1.386 (4)	C6—C7	1.374 (5)
C16—C15	1.489 (4)	C6—H6A	0.9300
N6—C18	1.319 (4)	C14—H14A	0.9300
N6—C17B	1.331 (4)	C12—H12A	0.9300
C15—N4	1.331 (3)	C10—N7	1.132 (5)
C15—C14	1.379 (4)	C9—C8	1.369 (4)
C20—N8	1.128 (4)	C9—H9A	0.9300
C20—C18	1.450 (4)	C7—C8	1.365 (5)
C1—C2	1.373 (4)	C7—H7A	0.9300
C1—H1A	0.9300	C8—H8A	0.9300
N4—C11	1.338 (4)	C3—H3A	0.9300
N3—C3	1.317 (5)	N9—O3	1.215 (5)
N3—C2	1.333 (4)	N9—O2	1.216 (4)
C4—C3	1.388 (4)	N9—O1	1.218 (4)
N1—Ag1—N4	151.94 (10)	C6—C5—C4	121.8 (3)
N1—Ag1—N2	68.39 (9)	N3—C2—C1	121.7 (3)
N4—Ag1—N2	111.09 (9)	N3—C2—C10	116.1 (3)
N1—Ag1—O1	127.70 (10)	C1—C2—C10	122.2 (3)
N4—Ag1—O1	79.74 (9)	C12—C13—C14	118.2 (3)
N2—Ag1—O1	89.70 (10)	C12—C13—H13A	120.9
N1—Ag1—N5	107.92 (9)	C14—C13—H13A	120.9
N4—Ag1—N5	67.26 (8)	C9—N1—C5	117.8 (3)
N2—Ag1—N5	169.60 (9)	C9—N1—Ag1	119.6 (2)
O1—Ag1—N5	99.92 (10)	C5—N1—Ag1	121.9 (2)
C16—N5—C19	117.2 (3)	N6—C17B—C16	123.2 (3)
C16—N5—Ag1	113.13 (18)	N6—C17B—H17A	118.4
C19—N5—Ag1	128.68 (19)	C16—C17B—H17A	118.4
C4—N2—C1	117.6 (3)	N4—C11—C12	123.3 (3)
C4—N2—Ag1	113.5 (2)	N4—C11—H11A	118.4
C1—N2—Ag1	128.9 (2)	C12—C11—H11A	118.4
N5—C19—C18	121.4 (3)	C7—C6—C5	119.8 (3)
N5—C19—H19A	119.3	C7—C6—H6A	120.1
C18—C19—H19A	119.3	C5—C6—H6A	120.1
N5—C16—C17B	120.0 (3)	C15—C14—C13	119.8 (3)
N5—C16—C15	118.0 (2)	C15—C14—H14A	120.1
C17B—C16—C15	121.9 (2)	C13—C14—H14A	120.1
C18—N6—C17B	115.5 (3)	C13—C12—C11	119.1 (3)
N4—C15—C14	121.7 (3)	C13—C12—H12A	120.4
N4—C15—C16	117.2 (2)	C11—C12—H12A	120.4
C14—C15—C16	121.1 (2)	N7—C10—C2	178.2 (4)
N8—C20—C18	177.4 (4)	N1—C9—C8	124.5 (3)
N6—C18—C19	122.7 (3)	N1—C9—H9A	117.8
N6—C18—C20	115.9 (3)	C8—C9—H9A	117.8
C19—C18—C20	121.4 (3)	C8—C7—C6	119.4 (3)
N2—C1—C2	121.7 (3)	C8—C7—H7A	120.3
N2—C1—H1A	119.2	C6—C7—H7A	120.3
C2—C1—H1A	119.2	C7—C8—C9	117.5 (3)
C15—N4—C11	117.9 (2)	C7—C8—H8A	121.2
C15—N4—Ag1	122.46 (19)	C9—C8—H8A	121.2
C11—N4—Ag1	118.15 (19)	N3—C3—C4	123.7 (3)
C3—N3—C2	115.9 (3)	N3—C3—H3A	118.1
N2—C4—C3	119.4 (3)	C4—C3—H3A	118.1
N2—C4—C5	118.3 (2)	O3—N9—O2	123.7 (4)
C3—C4—C5	122.3 (3)	O3—N9—O1	119.2 (4)
N1—C5—C6	120.9 (3)	O2—N9—O1	117.0 (4)
N1—C5—C4	117.3 (2)	N9—O1—Ag1	105.0 (2)
N1—Ag1—N5—C16	161.6 (2)	Ag1—N2—C4—C5	0.6 (3)
N4—Ag1—N5—C16	11.1 (2)	N2—C4—C5—N1	−5.9 (4)
N2—Ag1—N5—C16	94.1 (5)	C3—C4—C5—N1	174.7 (3)
O1—Ag1—N5—C16	−63.2 (2)	N2—C4—C5—C6	174.4 (3)
N1—Ag1—N5—C19	−30.4 (3)	C3—C4—C5—C6	−5.0 (5)
N4—Ag1—N5—C19	179.1 (3)	C3—N3—C2—C1	0.9 (6)
N2—Ag1—N5—C19	−98.0 (5)	C3—N3—C2—C10	179.0 (4)
O1—Ag1—N5—C19	104.7 (3)	N2—C1—C2—N3	−0.8 (5)
N1—Ag1—N2—C4	2.6 (2)	N2—C1—C2—C10	−178.8 (3)
N4—Ag1—N2—C4	152.4 (2)	C6—C5—N1—C9	−0.5 (5)
O1—Ag1—N2—C4	−128.7 (2)	C4—C5—N1—C9	179.8 (3)
N5—Ag1—N2—C4	73.6 (5)	C6—C5—N1—Ag1	−171.4 (2)
N1—Ag1—N2—C1	−177.5 (3)	C4—C5—N1—Ag1	8.9 (4)
N4—Ag1—N2—C1	−27.7 (3)	N4—Ag1—N1—C9	88.5 (3)
O1—Ag1—N2—C1	51.2 (3)	N2—Ag1—N1—C9	−176.9 (3)
N5—Ag1—N2—C1	−106.5 (5)	O1—Ag1—N1—C9	−105.2 (3)
C16—N5—C19—C18	0.2 (5)	N5—Ag1—N1—C9	13.4 (3)
Ag1—N5—C19—C18	−167.3 (3)	N4—Ag1—N1—C5	−100.8 (3)
C19—N5—C16—C17B	−1.4 (5)	N2—Ag1—N1—C5	−6.2 (2)
Ag1—N5—C16—C17B	168.0 (3)	O1—Ag1—N1—C5	65.5 (3)
C19—N5—C16—C15	−179.5 (3)	N5—Ag1—N1—C5	−175.9 (2)
Ag1—N5—C16—C15	−10.1 (3)	C18—N6—C17B—C16	−0.6 (6)
N5—C16—C15—N4	0.4 (4)	N5—C16—C17B—N6	1.7 (6)
C17B—C16—C15—N4	−177.7 (3)	C15—C16—C17B—N6	179.7 (3)
N5—C16—C15—C14	178.7 (3)	C15—N4—C11—C12	−0.9 (5)
C17B—C16—C15—C14	0.6 (5)	Ag1—N4—C11—C12	165.4 (3)
C17B—N6—C18—C19	−0.7 (5)	N1—C5—C6—C7	0.5 (5)
C17B—N6—C18—C20	178.4 (3)	C4—C5—C6—C7	−179.8 (3)
N5—C19—C18—N6	0.9 (6)	N4—C15—C14—C13	1.8 (5)
N5—C19—C18—C20	−178.1 (3)	C16—C15—C14—C13	−176.4 (3)
C4—N2—C1—C2	0.3 (5)	C12—C13—C14—C15	−0.7 (6)
Ag1—N2—C1—C2	−179.6 (2)	C14—C13—C12—C11	−1.0 (6)
C14—C15—N4—C11	−0.9 (5)	N4—C11—C12—C13	1.9 (6)
C16—C15—N4—C11	177.3 (3)	C5—N1—C9—C8	−0.2 (6)
C14—C15—N4—Ag1	−166.7 (2)	Ag1—N1—C9—C8	170.9 (3)
C16—C15—N4—Ag1	11.5 (4)	C5—C6—C7—C8	0.1 (6)
N1—Ag1—N4—C15	−97.5 (3)	C6—C7—C8—C9	−0.7 (6)
N2—Ag1—N4—C15	179.1 (2)	N1—C9—C8—C7	0.8 (6)
O1—Ag1—N4—C15	93.5 (3)	C2—N3—C3—C4	−0.5 (6)
N5—Ag1—N4—C15	−11.9 (2)	N2—C4—C3—N3	0.0 (6)
N1—Ag1—N4—C11	96.8 (3)	C5—C4—C3—N3	179.4 (4)
N2—Ag1—N4—C11	13.4 (3)	O3—N9—O1—Ag1	172.5 (3)
O1—Ag1—N4—C11	−72.3 (3)	O2—N9—O1—Ag1	−7.3 (4)
N5—Ag1—N4—C11	−177.7 (3)	N1—Ag1—O1—N9	39.1 (3)
C1—N2—C4—C3	0.1 (5)	N4—Ag1—O1—N9	−147.4 (3)
Ag1—N2—C4—C3	180.0 (3)	N2—Ag1—O1—N9	101.1 (2)
C1—N2—C4—C5	−179.3 (3)	N5—Ag1—O1—N9	−82.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19A···O1i	0.93	2.35	3.233 (3)	157
C11—H11A···O2ii	0.93	2.54	3.232 (5)	132
C13—H13A···N8iii	0.93	2.73	3.319 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19A⋯O1i	0.93	2.35	3.233 (3)	157
C11—H11A⋯O2ii	0.93	2.54	3.232 (5)	132
C13—H13A⋯N8iii	0.93	2.73	3.319 (3)	122

Symmetry codes: (i) ; (ii) ; (iii) .