(Nitrato-κO)bis­[5-(pyridin-2-yl)pyrazine-2-carbonitrile-κ2N4,N5]silver(I)

Zhang, F.; Yang, Y.-L.

doi:10.1107/S1600536811049221

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1863

https://doi.org/10.1107/S1600536811049221

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(Nitrato-κO)bis[5-(pyridin-2-yl)pyrazine-2-carbonitrile-κ²N⁴,N⁵]silver(I)

Fan Zhang ^a ^* and Yong-Li Yang ^a

^aDepartment of Chemistry, Capital Normal University, Beijing 100048, People's Republic of China
^*Correspondence e-mail: zhangfcnu@163.com

(Received 4 November 2011; accepted 18 November 2011; online 30 November 2011)

In the mononuclear title complex, [Ag(NO₃)(C₁₀H₆N₄)₂], two κ²N:N′-chelating 5-(pyridin-2-yl)pyrazine-2-carbonitrile ligands surround the Ag^I atom, forming an N₄O 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 interconnected along [010] through C—H⋯O(nitrate) and C—H⋯N(cyano) interactions, forming an infinite chain. The mononuclear units are stacked along the a axis and interconnected via intermolecular π–π stacking interactions between adjacent pyridine and pyrazine rings [centroid–centroid distances = 3.984 (2) and 3.595 (3) Å], thus forming a three-dimensional supramolecular 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_r = 534.26
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.099
S = 1.03
5029 reflections
298 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.28 e Å⁻³

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) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) x, y-1, z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811049221/zq2135sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811049221/zq2135Isup2.hkl

checkCIF report

Comment top

Pyridyl based ligands have attracted increasing attention because of their versatile linkage behavior and their artificial and controllable synthesis (Dunne et al., 1997; Wang et al., 2009). Recently, we reported a silver(I) complex derived from 5-(2-pyridyl)pyrazine-2-carbonitrile (Wang et al., 2010). To make a further insight into the coordination chemistry of such a ligand featuring a 2-cyanopyrazinyl group at the 2-pyridyl carbon atom (Scheme 1), herein we present the structure of the new complex [Ag(C₁₀H₆N₄)₂(NO₃)].

As shown in Fig. 1, in the mononuclear title complex two κ² N:N chelating 5-(2-pyridyl)pyrazine-2-carbonitrile ligands surround the Ag^I center to form a N4O-pyramidal coordination geometry with one nitrate bonding at the axial site. The Ag—N bond lengths lie within the range of 2.301 (2) - 2.579 (3) Å, with Ag1—N1 and Ag1—N4 slighty shorter than Ag1—N2 and Ag1—N5. These bond distances are comparable to those in [Ag(C₁₀H₆N₄)₂]BF₄ (2.196 (2) - 2.685 (2) Å) reported by us recently (Wang et al. 2010). Furthermore, in the present case, the nitrate binds to the silver center with Ag1—O1 = 2.547 (3) Å. It is worth to note that a second O atom of the nitrate interacts with the silver center as shown by the Ag1—O2 distance of 2.800 (2) Å. Along the b axis, the mononuclear moieties are arranged with two adjacent ones around an inversion center. Indeed, C—H···O(nitrate) and C—H···N(cyano) interactions (Table 1) are found to link the mononuclear units together to form an infinite chain structure along the b axis (Fig. 2). Along the a direction, intermolecular π–π stacking interactions between adjacent pyridyl rings and pyrazinyl rings connect the mononuclear units together, forming a three-dimensional framework (Fig. 3). The distance between Cg1 (N4-N11-C12-C13-C14-C15) and Cg2ⁱ(N5-N16-C17-N6-C18-C19) is 3.984 (2) Å, while that between Cg3 (N1-N5-C6-N7-C8-C9) and Cg4ⁱⁱ(N2-C1-C2-N3-C3-C4) equals to 3.595 (3) Å (symmetry codes: i = –x, –y-1, –z+1; ii = –x+0.5, –y+1, z+1.5).

Related literature top

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

Experimental top

The 5-(2-pyridyl)-2-cyanopyrazine ligand was obtained commercially. The ligand (18.1 mg, 0.1 mmol) and AgNO₃ (17 mg, 0.1mmol) were mixed and dissolved in 3 ml methanol, and then 1 ml acetonitrile was subsequently added to make the solution clear. After stirring at room temperature for 3 hours, the resulted solution was filtrated, and the clear solution was kept in air for about one week at room temperature to yield yellow block-like crystals (21.1.0 mg, 79% yield).

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: 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 compound. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The infinite chain structure with C—H···O(nitrate) and C—H···N(cyano) interactions between the mononuclear units.The nitrate are shown as thick bonds for clarity.
	Fig. 3. View down the b axis of the packing structure of the title complex. All non-covalent interactions are omitted for clarity.

(Nitrato-κO)bis[5-(pyridin-2-yl)pyrazine-2-carbonitrile- κ²N⁴,N⁵]silver(I) top

Crystal data top

[Ag(NO₃)(C₁₀H₆N₄)₂]	Z = 8
M_r = 534.26	F(000) = 2128
Orthorhombic, Pbca	D_x = 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

Data collection top

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

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0413P)² + 2.5136P] P = (F_o² + 2F_c²)/3
5029 reflections	(Δ/σ)_max = 0.002
298 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Ag(NO₃)(C₁₀H₆N₄)₂]	V = 4048.4 (13) Å³
M_r = 534.26	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.000 (3) Å	µ = 1.04 mm⁻¹
b = 12.133 (2) Å	T = 293 K
c = 23.832 (4) Å	0.44 × 0.35 × 0.25 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	5029 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3255 reflections with I > 2σ(I)
T_min = 0.631, T_max = 1.000	R_int = 0.037
27695 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.03	Δρ_max = 0.46 e Å⁻³
5029 reflections	Δρ_min = −0.28 e Å⁻³
298 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	0.15007 (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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, y+1/2, z; (ii) −x+1/2, y−1/2, z; (iii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Ag(NO₃)(C₁₀H₆N₄)₂]
M_r	534.26
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	14.000 (3), 12.133 (2), 23.832 (4)
V (Å³)	4048.4 (13)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.44 × 0.35 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.631, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	27695, 5029, 3255
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.099, 1.03
No. of reflections	5029
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.46, −0.28

Computer programs: APEX2 (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
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) −x+1/2, y+1/2, z; (ii) −x+1/2, y−1/2, z; (iii) x, y−1, z.

Acknowledgements

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

References

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