[(E)-Oxido(pyridin-2-yl­methyl­idene)amine-κ2N,N′][(E)-N-(pyridin-2-yl­methyl­idene)hydroxyl­amine-κ2N,N′]silver(I) perchlorate–bis­[(E)-N-(pyridin-2-yl­methyl­idene)hydroxyl­amine-κ2N,N′]silver(I) (1/1)

Xu, J.; Gao, S.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S160053681201625X

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Pages m639-m640

doi:10.1107/S160053681201625X

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[(E)-Oxido(pyridin-2-ylmethylidene)amine-κ²N,N′][(E)-N-(pyridin-2-ylmethylidene)hydroxylamine-κ²N,N′]silver(I) perchlorate–bis[(E)-N-(pyridin-2-ylmethylidene)hydroxylamine-κ²N,N′]silver(I) (1/1)

Jing Xu,^a Shan Gao,^a ‡ Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aKey Laboratory of Functional Inorganic Material Chemistry, Ministry of Education, Heilongjiang University, Harbin 150080, People's Republic of China, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 10 April 2012; accepted 14 April 2012; online 21 April 2012)

In the title salt co-crystal, [Ag(C₆H₅N₂O)(C₆H₆N₂O)]ClO₄·[Ag(C₆H₆N₂O)₂], the asymmetric unit comprises a [Ag(LH)₂]⁺ cation, a perchlorate anion and a neutral (LH)AgL molecule, where LH is pyridine-2-carboxaldoxime. Both silver-containing species feature N,N′-chelating LH and L ligands, which define an N₄ donor set that is highly distorted [dihedral angles between AgC₂N₂ chelate rings = 45.7 (3) and 44.3 (2)°, respectively] owing, in part, to the close approach of a neighbouring Ag atom, leading to an argentophilic interaction [Ag⋯Ag = 3.1868 (11) Å]. The molecular conformations are stabilized by intramolecular O—H⋯O hydrogen bonds. In the crystal, O—H⋯O interactions lead to supramolecular chains along [010]. Chains aggregate into layers in the ab plane, defining channels along [100] in which reside the perchlorate anions; the latter are disordered over two overlapped orientations in a 50:50 ratio.

Related literature

For structural diversity in the structures of silver salts, see: Kundu et al. (2010 ). For a related structure, see: Abu-Youssef et al. (2010 ).

Experimental

Crystal data

[Ag(C₆H₅N₂O)(C₆H₆N₂O)]ClO₄·[Ag(C₆H₆N₂O)₂]
M_r = 802.69
Triclinic, $[P \overline 1]$
a = 7.3925 (18) Å
b = 8.3419 (19) Å
c = 25.626 (6) Å
α = 90.226 (6)°
β = 92.753 (6)°
γ = 114.409 (6)°
V = 1436.9 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.52 mm⁻¹
T = 293 K
0.21 × 0.13 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.356, T_max = 1.000
11387 measured reflections
5042 independent reflections
3660 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.187
S = 1.09
5042 reflections
430 parameters
64 restraints
H-atom parameters constrained
Δρ_max = 1.19 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—N1	2.280 (5)
Ag1—N2	2.392 (5)
Ag1—N3	2.281 (5)
Ag1—N4	2.384 (5)
Ag2—N5	2.235 (5)
Ag2—N6	2.448 (4)
Ag2—N7	2.256 (5)
Ag2—N8	2.401 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯O4	0.84	1.91	2.673 (8)	151
O3—H3o⋯O2	0.84	1.81	2.610 (6)	160
O4—H4o⋯O2ⁱ	0.84	1.64	2.475 (6)	174
Symmetry code: (i) x, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC and Rigaku, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681201625X/hb6736sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681201625X/hb6736Isup2.hkl

checkCIF report

Comment top

Nitrogen adducts of silver salts are notorious for their structural diversity with very different coordination geometries let alone supramolecular architectures being observed by a simple change in counter-ion, for example (Kundu et al., 2010). A molecule that has yet to attract significant interest in terms of coordination chemistry towards silver is pyridine-2-carboxaldoxime (LH) with only the Ag(LH)NO₃ salt reported thus far (Abu-Youssef et al., 2010). Herein, the crystal structure determination of the perchlorate analogue (I) is described.

In (I), the asymmetric unit comprises a neutral (LH)AgL molecule, a [Ag(LH)₂]⁺ cation and a perchlorate anion, Fig. 1. In both silver-containing species, the pyridine-2-carboxaldoxime and the derived anion are N,N-chelating, Table 1. The Ag—N(pyridine) and Ag—N(oxime) bond lengths are systematically shorter and longer, respectively, in the neutral molecule than in the cation, Table 1, and the Ag—N4(oximate) distance is shorter compared with the Ag—N(oxime) bond lengths, Table 1. Each five-membered AgC₂N₂ chelate ring is essentially planar with r.m.s. deviations of 0.062, 0.049, 0.080 and 0.035 Å, respectively for the N1, N3, N4 and N6-containing rings. The dihedral between the chelate rings involving the Ag1 atom is 44.3 (2)° indicating a distorted coordination geometry; the comparable angle for the Ag2-containing molecule is 45.7 (3)°. The close approach of a neighbouring silver atom contributes to the distortion as the silver atoms are connected by an agentophilic Ag1···Ag2 interaction, Table 1.

The most prominent feature of the crystal packing is the formation of a supramolecular chain along [010] mediated by O—H···O interactions, Fig. 2 and Table 2. In both the neutral (LH)AgL molecule and in the [Ag(LH)₂]⁺ cation an intramolecular O—H···O interaction is formed. Links between molecules to form the chain are also of the type O—H···O and involve the formally anionic O2 atom which is bifurcated. A detailed analysis of the crystal packing is precluded owing to the disorder associated with the perchlorate anions. However, globally the Ag-containing molecules aggregate into layers in the ab plane to define channels along [100] in which reside the perchlorate anions, Fig. 3.

Related literature top

For structural diversity in the structures of silver salts, see: Kundu et al. (2010). For a related structure, see: Abu-Youssef et al. (2010).

Experimental top

Silver perchlorate (1 mmol) and picolinaldehyde oxime (1 mmol) was dissolved in methanol solution (10 ml). The solution was filtered and set aside, away from light, for the growth of crystals. Colourless prisms deposited after several days.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC and Rigaku, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 20% probability level. Each perchlorate anion has half-weight and for each, only one orientation is shown.
	Fig. 2. A view of the supramolecular chain along [010] in (I). The O—H···O hydrogen bonds are shown as orange dashed lines.
	Fig. 3. A view in projection down the a axis of the unit-cell contents for (I). The O—H···O interactions are shown as orange dashed lines. Only one orientation of the disordered perchlorate anions is shown.

[(E)-Oxido(pyridin-2-ylmethylidene)amine- κ²N,N'][(E)-N-(pyridin-2- ylmethylidene)hydroxylamine-κ²N,N']silver(I) perchlorate– bis[(E)-N-(pyridin-2-ylmethylidene)hydroxylamine- κ²N,N']silver(I) (1/1) top

Crystal data top

[Ag(C₆H₅N₂O)(C₆H₆N₂O)]ClO₄·[Ag(C₆H₆N₂O)₂]	Z = 2
M_r = 802.69	F(000) = 796
Triclinic, P1	D_x = 1.855 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3925 (18) Å	Cell parameters from 7282 reflections
b = 8.3419 (19) Å	θ = 3.0–27.4°
c = 25.626 (6) Å	µ = 1.52 mm⁻¹
α = 90.226 (6)°	T = 293 K
β = 92.753 (6)°	Prism, colourless
γ = 114.409 (6)°	0.21 × 0.13 × 0.13 mm
V = 1436.9 (6) Å³

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5042 independent reflections
Radiation source: fine-focus sealed tube	3660 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scan	θ_max = 25.0°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→8
T_min = 0.356, T_max = 1.000	k = −10→10
11387 measured reflections	l = −30→30

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.187	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0985P)² + 1.259P] where P = (F_o² + 2F_c²)/3
5042 reflections	(Δ/σ)_max = 0.001
430 parameters	Δρ_max = 1.19 e Å⁻³
64 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

[Ag(C₆H₅N₂O)(C₆H₆N₂O)]ClO₄·[Ag(C₆H₆N₂O)₂]	γ = 114.409 (6)°
M_r = 802.69	V = 1436.9 (6) Å³
Triclinic, P1	Z = 2
a = 7.3925 (18) Å	Mo Kα radiation
b = 8.3419 (19) Å	µ = 1.52 mm⁻¹
c = 25.626 (6) Å	T = 293 K
α = 90.226 (6)°	0.21 × 0.13 × 0.13 mm
β = 92.753 (6)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5042 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3660 reflections with I > 2σ(I)
T_min = 0.356, T_max = 1.000	R_int = 0.046
11387 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	64 restraints
wR(F²) = 0.187	H-atom parameters constrained
S = 1.09	Δρ_max = 1.19 e Å⁻³
5042 reflections	Δρ_min = −0.58 e Å⁻³
430 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.70514 (8)	0.49157 (7)	0.260394 (19)	0.0752 (2)
Ag2	0.27551 (9)	0.48831 (8)	0.23871 (2)	0.0791 (2)
Cl1	0.5000	0.0000	0.0000	0.0665 (6)
Cl2	0.0000	1.0000	0.5000	0.0662 (6)
O5	0.580 (3)	0.1840 (12)	0.0097 (9)	0.135 (5)	0.25
O6	0.597 (3)	−0.072 (3)	0.0356 (8)	0.135 (5)	0.25
O7	0.2954 (14)	−0.073 (3)	0.0089 (9)	0.135 (5)	0.25
O8	0.530 (4)	−0.037 (3)	−0.0512 (5)	0.135 (5)	0.25
O9	0.170 (2)	1.086 (2)	0.4738 (7)	0.110 (4)	0.25
O10	−0.089 (3)	0.8170 (12)	0.4851 (7)	0.110 (4)	0.25
O11	−0.143 (2)	1.069 (3)	0.4902 (8)	0.110 (4)	0.25
O12	0.043 (3)	1.008 (3)	0.5550 (3)	0.110 (4)	0.25
O5'	0.623 (3)	0.1818 (14)	−0.0045 (10)	0.151 (6)	0.25
O6'	0.433 (4)	−0.034 (3)	0.0503 (5)	0.151 (6)	0.25
O7'	0.336 (3)	−0.046 (4)	−0.0369 (8)	0.151 (6)	0.25
O8'	0.610 (3)	−0.097 (3)	−0.0124 (10)	0.151 (6)	0.25
O9'	0.040 (4)	1.033 (4)	0.4463 (4)	0.148 (6)	0.25
O10'	−0.136 (3)	0.8217 (16)	0.5034 (10)	0.148 (6)	0.25
O11'	−0.085 (4)	1.111 (3)	0.5179 (10)	0.148 (6)	0.25
O12'	0.178 (2)	1.031 (4)	0.5285 (10)	0.148 (6)	0.25
O1	0.7001 (8)	0.8834 (6)	0.3068 (2)	0.0852 (14)
H1o	0.7215	0.9063	0.2752	0.128*
O2	0.4335 (6)	0.0784 (5)	0.20609 (19)	0.0714 (12)
O3	0.2203 (8)	0.0720 (5)	0.2850 (2)	0.0771 (13)
H3o	0.2629	0.0680	0.2554	0.116*
O4	0.6262 (7)	0.8966 (5)	0.2041 (2)	0.0786 (13)
H4o	0.5628	0.9593	0.2071	0.118*
N1	0.6765 (7)	0.3991 (6)	0.3444 (2)	0.0591 (12)
N2	0.6812 (7)	0.7126 (6)	0.3159 (2)	0.0591 (12)
N3	0.8625 (7)	0.5765 (6)	0.18431 (19)	0.0549 (11)
N4	0.5644 (7)	0.2521 (5)	0.1986 (2)	0.0553 (11)
N5	0.1855 (7)	0.5423 (6)	0.3166 (2)	0.0574 (12)
N6	0.2256 (7)	0.2365 (6)	0.2941 (2)	0.0557 (11)
N7	0.2272 (7)	0.4018 (6)	0.1538 (2)	0.0590 (12)
N8	0.4962 (7)	0.7274 (6)	0.1894 (2)	0.0624 (13)
C1	0.6511 (10)	0.2356 (9)	0.3590 (3)	0.0764 (19)
H1A	0.6668	0.1610	0.3343	0.092*
C2	0.6039 (12)	0.1754 (12)	0.4076 (4)	0.102 (3)
H2	0.5821	0.0603	0.4156	0.122*
C3	0.5889 (12)	0.2856 (14)	0.4448 (4)	0.104 (3)
H3A	0.5595	0.2472	0.4786	0.125*
C4	0.6173 (11)	0.4529 (13)	0.4322 (3)	0.088 (2)
H4A	0.6096	0.5302	0.4573	0.106*
C5	0.6581 (8)	0.5058 (9)	0.3807 (3)	0.0591 (15)
C6	0.6811 (9)	0.6802 (8)	0.3638 (3)	0.0659 (16)
H6	0.6957	0.7673	0.3885	0.079*
C7	0.9996 (9)	0.7365 (8)	0.1739 (3)	0.0677 (17)
H7	1.0476	0.8197	0.2012	0.081*
C8	1.0742 (10)	0.7860 (9)	0.1258 (3)	0.0757 (19)
H8	1.1715	0.8984	0.1208	0.091*
C9	1.0014 (10)	0.6654 (10)	0.0853 (3)	0.0756 (19)
H9	1.0489	0.6943	0.0521	0.091*
C10	0.8557 (10)	0.4994 (10)	0.0943 (3)	0.0698 (17)
H10	0.8016	0.4169	0.0670	0.084*
C11	0.7920 (8)	0.4581 (7)	0.1443 (2)	0.0521 (13)
C12	0.6440 (8)	0.2828 (8)	0.1552 (2)	0.0579 (14)
H12	0.6081	0.1930	0.1299	0.070*
C13	0.1915 (10)	0.6977 (9)	0.3323 (3)	0.0738 (18)
H13	0.2120	0.7833	0.3074	0.089*
C14	0.1695 (10)	0.7387 (9)	0.3823 (3)	0.0776 (19)
H14	0.1757	0.8492	0.3911	0.093*
C15	0.1382 (10)	0.6140 (11)	0.4194 (3)	0.078 (2)
H15	0.1225	0.6385	0.4539	0.093*
C16	0.1301 (10)	0.4511 (10)	0.4051 (3)	0.0703 (18)
H16	0.1077	0.3644	0.4298	0.084*
C17	0.1556 (7)	0.4185 (7)	0.3538 (2)	0.0509 (13)
C18	0.1551 (9)	0.2518 (7)	0.3372 (2)	0.0577 (14)
H18	0.1026	0.1548	0.3585	0.069*
C19	0.1015 (12)	0.2427 (9)	0.1338 (3)	0.083 (2)
H19	0.0159	0.1619	0.1560	0.100*
C20	0.0939 (16)	0.1945 (12)	0.0825 (4)	0.109 (3)
H20	0.0058	0.0828	0.0704	0.130*
C21	0.2162 (19)	0.3111 (16)	0.0493 (4)	0.116 (3)
H21	0.2131	0.2792	0.0143	0.139*
C22	0.3443 (13)	0.4759 (12)	0.0674 (3)	0.086 (2)
H22	0.4271	0.5580	0.0449	0.103*
C23	0.3474 (11)	0.5172 (9)	0.1202 (3)	0.0662 (17)
C24	0.4803 (10)	0.6905 (8)	0.1411 (3)	0.0661 (16)
H24	0.5555	0.7762	0.1183	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0860 (4)	0.0851 (4)	0.0572 (4)	0.0386 (3)	0.0006 (3)	−0.0154 (3)
Ag2	0.0911 (4)	0.0918 (4)	0.0588 (4)	0.0408 (3)	0.0170 (3)	0.0185 (3)
Cl1	0.0764 (13)	0.0598 (12)	0.0535 (11)	0.0180 (10)	0.0091 (10)	−0.0010 (9)
Cl2	0.0880 (15)	0.0592 (12)	0.0552 (12)	0.0340 (11)	0.0075 (11)	0.0040 (9)
O5	0.145 (8)	0.127 (8)	0.126 (8)	0.046 (6)	0.015 (7)	−0.004 (7)
O6	0.145 (8)	0.127 (8)	0.126 (8)	0.046 (6)	0.015 (7)	−0.004 (7)
O7	0.145 (8)	0.127 (8)	0.126 (8)	0.046 (6)	0.015 (7)	−0.004 (7)
O8	0.145 (8)	0.127 (8)	0.126 (8)	0.046 (6)	0.015 (7)	−0.004 (7)
O9	0.124 (7)	0.113 (7)	0.091 (7)	0.048 (6)	0.015 (6)	−0.018 (6)
O10	0.124 (7)	0.113 (7)	0.091 (7)	0.048 (6)	0.015 (6)	−0.018 (6)
O11	0.124 (7)	0.113 (7)	0.091 (7)	0.048 (6)	0.015 (6)	−0.018 (6)
O12	0.124 (7)	0.113 (7)	0.091 (7)	0.048 (6)	0.015 (6)	−0.018 (6)
O5'	0.169 (9)	0.133 (9)	0.145 (10)	0.054 (8)	0.028 (8)	−0.012 (7)
O6'	0.169 (9)	0.133 (9)	0.145 (10)	0.054 (8)	0.028 (8)	−0.012 (7)
O7'	0.169 (9)	0.133 (9)	0.145 (10)	0.054 (8)	0.028 (8)	−0.012 (7)
O8'	0.169 (9)	0.133 (9)	0.145 (10)	0.054 (8)	0.028 (8)	−0.012 (7)
O9'	0.162 (9)	0.143 (9)	0.135 (9)	0.060 (8)	−0.001 (8)	−0.023 (7)
O10'	0.162 (9)	0.143 (9)	0.135 (9)	0.060 (8)	−0.001 (8)	−0.023 (7)
O11'	0.162 (9)	0.143 (9)	0.135 (9)	0.060 (8)	−0.001 (8)	−0.023 (7)
O12'	0.162 (9)	0.143 (9)	0.135 (9)	0.060 (8)	−0.001 (8)	−0.023 (7)
O1	0.104 (4)	0.050 (2)	0.107 (4)	0.039 (2)	−0.013 (3)	−0.011 (2)
O2	0.071 (3)	0.043 (2)	0.097 (3)	0.0182 (18)	0.019 (2)	−0.001 (2)
O3	0.093 (3)	0.041 (2)	0.102 (4)	0.029 (2)	0.028 (3)	0.010 (2)
O4	0.075 (3)	0.051 (2)	0.111 (4)	0.028 (2)	−0.006 (3)	0.000 (2)
N1	0.051 (2)	0.058 (3)	0.067 (3)	0.022 (2)	−0.003 (2)	−0.008 (2)
N2	0.060 (3)	0.051 (3)	0.069 (3)	0.027 (2)	−0.002 (2)	−0.010 (2)
N3	0.053 (2)	0.043 (2)	0.068 (3)	0.021 (2)	−0.004 (2)	−0.002 (2)
N4	0.055 (2)	0.037 (2)	0.071 (3)	0.0168 (19)	−0.003 (2)	−0.005 (2)
N5	0.057 (3)	0.048 (3)	0.071 (3)	0.024 (2)	0.014 (2)	0.010 (2)
N6	0.055 (2)	0.042 (2)	0.071 (3)	0.0211 (19)	0.001 (2)	0.004 (2)
N7	0.063 (3)	0.055 (3)	0.065 (3)	0.031 (2)	−0.009 (2)	0.003 (2)
N8	0.064 (3)	0.045 (3)	0.081 (4)	0.023 (2)	0.015 (3)	0.010 (2)
C1	0.067 (4)	0.065 (4)	0.097 (5)	0.029 (3)	−0.018 (4)	0.000 (4)
C2	0.078 (5)	0.086 (6)	0.126 (8)	0.020 (4)	−0.006 (5)	0.032 (6)
C3	0.074 (5)	0.120 (7)	0.101 (7)	0.023 (5)	0.003 (5)	0.046 (6)
C4	0.066 (4)	0.124 (7)	0.074 (5)	0.039 (4)	0.004 (4)	0.001 (5)
C5	0.050 (3)	0.072 (4)	0.058 (4)	0.028 (3)	−0.001 (3)	−0.008 (3)
C6	0.063 (3)	0.068 (4)	0.072 (4)	0.034 (3)	−0.010 (3)	−0.027 (3)
C7	0.067 (4)	0.050 (3)	0.087 (5)	0.028 (3)	−0.014 (3)	−0.013 (3)
C8	0.064 (4)	0.061 (4)	0.099 (5)	0.022 (3)	0.012 (4)	0.027 (4)
C9	0.068 (4)	0.080 (5)	0.083 (5)	0.034 (3)	0.017 (4)	0.031 (4)
C10	0.066 (4)	0.084 (5)	0.060 (4)	0.032 (3)	−0.001 (3)	−0.001 (3)
C11	0.050 (3)	0.050 (3)	0.058 (3)	0.024 (2)	−0.003 (3)	−0.002 (3)
C12	0.058 (3)	0.054 (3)	0.062 (4)	0.023 (3)	0.003 (3)	−0.016 (3)
C13	0.069 (4)	0.061 (4)	0.098 (5)	0.033 (3)	0.016 (4)	0.007 (4)
C14	0.062 (4)	0.066 (4)	0.106 (6)	0.029 (3)	0.005 (4)	−0.019 (4)
C15	0.062 (4)	0.102 (6)	0.076 (5)	0.041 (4)	0.000 (3)	−0.020 (4)
C16	0.060 (3)	0.089 (5)	0.068 (4)	0.036 (3)	0.006 (3)	0.010 (4)
C17	0.043 (3)	0.056 (3)	0.053 (3)	0.020 (2)	0.003 (2)	0.011 (3)
C18	0.061 (3)	0.049 (3)	0.065 (4)	0.025 (3)	0.013 (3)	0.019 (3)
C19	0.093 (5)	0.056 (4)	0.107 (6)	0.041 (4)	−0.020 (4)	−0.001 (4)
C20	0.143 (8)	0.089 (6)	0.110 (7)	0.072 (6)	−0.061 (6)	−0.040 (5)
C21	0.175 (10)	0.140 (9)	0.078 (6)	0.116 (8)	−0.038 (6)	−0.032 (6)
C22	0.102 (6)	0.110 (6)	0.065 (4)	0.064 (5)	−0.003 (4)	0.000 (4)
C23	0.081 (4)	0.080 (4)	0.059 (4)	0.054 (4)	0.006 (3)	0.012 (3)
C24	0.068 (4)	0.064 (4)	0.067 (4)	0.026 (3)	0.010 (3)	0.022 (3)

Geometric parameters (Å, º) top

Ag1—N1	2.280 (5)	N5—C13	1.338 (8)
Ag1—N2	2.392 (5)	N5—C17	1.365 (7)
Ag1—N3	2.281 (5)	N6—C18	1.274 (7)
Ag1—N4	2.384 (5)	N7—C19	1.348 (8)
Ag2—N5	2.235 (5)	N7—C23	1.353 (8)
Ag2—N6	2.448 (4)	N8—C24	1.263 (8)
Ag2—N7	2.256 (5)	C1—C2	1.352 (11)
Ag2—N8	2.401 (5)	C1—H1A	0.9300
Ag1—Ag2	3.1868 (11)	C2—C3	1.360 (13)
Cl1—O6'	1.392 (8)	C2—H2	0.9300
Cl1—O6'ⁱ	1.392 (8)	C3—C4	1.365 (12)
Cl1—O8ⁱ	1.395 (8)	C3—H3A	0.9300
Cl1—O8	1.395 (8)	C4—C5	1.399 (10)
Cl1—O8'	1.407 (9)	C4—H4A	0.9300
Cl1—O8'ⁱ	1.407 (9)	C5—C6	1.464 (9)
Cl1—O7	1.409 (8)	C6—H6	0.9300
Cl1—O7ⁱ	1.409 (8)	C7—C8	1.371 (10)
Cl1—O5	1.414 (8)	C7—H7	0.9300
Cl1—O5ⁱ	1.414 (8)	C8—C9	1.366 (10)
Cl1—O7'ⁱ	1.418 (9)	C8—H8	0.9300
Cl1—O7'	1.418 (9)	C9—C10	1.387 (10)
Cl2—O9	1.375 (8)	C9—H9	0.9300
Cl2—O9ⁱⁱ	1.375 (8)	C10—C11	1.382 (9)
Cl2—O11'ⁱⁱ	1.400 (9)	C10—H10	0.9300
Cl2—O11'	1.400 (9)	C11—C12	1.458 (8)
Cl2—O12'	1.400 (9)	C12—H12	0.9300
Cl2—O12'ⁱⁱ	1.400 (9)	C13—C14	1.359 (10)
Cl2—O11ⁱⁱ	1.410 (8)	C13—H13	0.9300
Cl2—O11	1.410 (8)	C14—C15	1.367 (10)
Cl2—O10'	1.415 (9)	C14—H14	0.9300
Cl2—O10'ⁱⁱ	1.415 (9)	C15—C16	1.383 (11)
Cl2—O12	1.424 (8)	C15—H15	0.9300
Cl2—O12ⁱⁱ	1.424 (8)	C16—C17	1.379 (9)
O1—N2	1.395 (6)	C16—H16	0.9300
O1—H1o	0.8400	C17—C18	1.450 (8)
O2—N4	1.391 (6)	C18—H18	0.9300
O3—N6	1.375 (6)	C19—C20	1.365 (12)
O3—H3o	0.8400	C19—H19	0.9300
O4—N8	1.378 (6)	C20—C21	1.357 (14)
O4—H4o	0.8400	C20—H20	0.9300
N1—C5	1.334 (8)	C21—C22	1.370 (13)
N1—C1	1.354 (8)	C21—H21	0.9300
N2—C6	1.257 (8)	C22—C23	1.392 (10)
N3—C7	1.338 (7)	C22—H22	0.9300
N3—C11	1.347 (7)	C23—C24	1.453 (10)
N4—C12	1.261 (7)	C24—H24	0.9300

N1—Ag1—N3	154.92 (17)	C2—C3—H3A	120.1
N1—Ag1—N4	112.19 (17)	C4—C3—H3A	120.1
N3—Ag1—N4	71.69 (16)	C3—C4—C5	118.7 (9)
N1—Ag1—N2	70.69 (18)	C3—C4—H4A	120.6
N3—Ag1—N2	118.35 (16)	C5—C4—H4A	120.6
N4—Ag1—N2	151.77 (17)	N1—C5—C4	121.6 (7)
N1—Ag1—Ag2	99.47 (12)	N1—C5—C6	116.6 (6)
N3—Ag1—Ag2	105.57 (12)	C4—C5—C6	121.8 (7)
N4—Ag1—Ag2	79.91 (11)	N2—C6—C5	120.1 (6)
N2—Ag1—Ag2	72.01 (12)	N2—C6—H6	119.9
N5—Ag2—N7	155.54 (18)	C5—C6—H6	119.9
N5—Ag2—N8	119.88 (17)	N3—C7—C8	124.4 (6)
N7—Ag2—N8	72.02 (18)	N3—C7—H7	117.8
N5—Ag2—N6	71.74 (16)	C8—C7—H7	117.8
N7—Ag2—N6	109.99 (17)	C9—C8—C7	118.0 (6)
N8—Ag2—N6	148.63 (16)	C9—C8—H8	121.0
N5—Ag2—Ag1	105.18 (13)	C7—C8—H8	121.0
N7—Ag2—Ag1	98.55 (12)	C8—C9—C10	119.3 (6)
N8—Ag2—Ag1	74.53 (12)	C8—C9—H9	120.4
N6—Ag2—Ag1	74.24 (11)	C10—C9—H9	120.4
O6'—Cl1—O8'	111.4 (8)	C11—C10—C9	119.1 (7)
O8—Cl1—O7	110.5 (8)	C11—C10—H10	120.4
O8—Cl1—O5	110.4 (8)	C9—C10—H10	120.4
O7—Cl1—O5	108.9 (8)	N3—C11—C10	121.9 (5)
O6'—Cl1—O7'	110.0 (8)	N3—C11—C12	117.8 (5)
O8'—Cl1—O7'	108.7 (8)	C10—C11—C12	120.3 (6)
O11'—Cl2—O12'	111.0 (8)	N4—C12—C11	120.4 (5)
O9—Cl2—O11	112.9 (8)	N4—C12—H12	119.8
O11'—Cl2—O10'	110.1 (8)	C11—C12—H12	119.8
O12'—Cl2—O10'	110.3 (8)	N5—C13—C14	124.4 (7)
O9—Cl2—O12	111.2 (8)	N5—C13—H13	117.8
N2—O1—H1o	109.5	C14—C13—H13	117.8
N6—O3—H3o	109.5	C13—C14—C15	118.6 (7)
N8—O4—H4o	109.5	C13—C14—H14	120.7
C5—N1—C1	117.5 (6)	C15—C14—H14	120.7
C5—N1—Ag1	117.3 (4)	C14—C15—C16	119.2 (7)
C1—N1—Ag1	124.6 (5)	C14—C15—H15	120.4
C6—N2—O1	112.4 (5)	C16—C15—H15	120.4
C6—N2—Ag1	114.2 (4)	C17—C16—C15	119.3 (7)
O1—N2—Ag1	132.4 (4)	C17—C16—H16	120.3
C7—N3—C11	117.2 (5)	C15—C16—H16	120.3
C7—N3—Ag1	126.8 (4)	N5—C17—C16	121.6 (6)
C11—N3—Ag1	115.6 (3)	N5—C17—C18	117.2 (5)
C12—N4—O2	115.8 (5)	C16—C17—C18	121.3 (5)
C12—N4—Ag1	113.9 (4)	N6—C18—C17	120.8 (5)
O2—N4—Ag1	129.4 (4)	N6—C18—H18	119.6
C13—N5—C17	116.9 (6)	C17—C18—H18	119.6
C13—N5—Ag2	124.8 (4)	N7—C19—C20	123.1 (8)
C17—N5—Ag2	117.3 (4)	N7—C19—H19	118.4
C18—N6—O3	113.6 (4)	C20—C19—H19	118.4
C18—N6—Ag2	111.1 (4)	C21—C20—C19	119.4 (8)
O3—N6—Ag2	133.8 (4)	C21—C20—H20	120.3
C19—N7—C23	116.9 (6)	C19—C20—H20	120.3
C19—N7—Ag2	126.6 (5)	C20—C21—C22	119.9 (9)
C23—N7—Ag2	116.3 (4)	C20—C21—H21	120.1
C24—N8—O4	115.8 (5)	C22—C21—H21	120.1
C24—N8—Ag2	112.5 (4)	C21—C22—C23	118.3 (9)
O4—N8—Ag2	131.6 (4)	C21—C22—H22	120.8
C2—C1—N1	123.3 (8)	C23—C22—H22	120.8
C2—C1—H1A	118.3	N7—C23—C22	122.4 (7)
N1—C1—H1A	118.3	N7—C23—C24	117.3 (6)
C1—C2—C3	119.0 (8)	C22—C23—C24	120.3 (7)
C1—C2—H2	120.5	N8—C24—C23	121.5 (6)
C3—C2—H2	120.5	N8—C24—H24	119.2
C2—C3—C4	119.8 (8)	C23—C24—H24	119.2

N1—Ag1—Ag2—N5	29.36 (18)	N6—Ag2—N7—C23	−143.4 (4)
N3—Ag1—Ag2—N5	−151.98 (17)	Ag1—Ag2—N7—C23	−67.1 (4)
N4—Ag1—Ag2—N5	140.41 (17)	N5—Ag2—N8—C24	−156.9 (4)
N2—Ag1—Ag2—N5	−36.65 (18)	N7—Ag2—N8—C24	−0.4 (4)
N1—Ag1—Ag2—N7	−144.67 (18)	N6—Ag2—N8—C24	98.7 (5)
N3—Ag1—Ag2—N7	34.00 (17)	Ag1—Ag2—N8—C24	104.2 (4)
N4—Ag1—Ag2—N7	−33.61 (17)	N5—Ag2—N8—O4	19.4 (5)
N2—Ag1—Ag2—N7	149.33 (17)	N7—Ag2—N8—O4	175.9 (5)
N1—Ag1—Ag2—N8	146.78 (19)	N6—Ag2—N8—O4	−85.0 (5)
N3—Ag1—Ag2—N8	−34.56 (18)	Ag1—Ag2—N8—O4	−79.5 (5)
N4—Ag1—Ag2—N8	−102.17 (18)	C5—N1—C1—C2	1.6 (9)
N2—Ag1—Ag2—N8	80.78 (19)	Ag1—N1—C1—C2	−169.4 (5)
N1—Ag1—Ag2—N6	−36.19 (17)	N1—C1—C2—C3	−2.8 (12)
N3—Ag1—Ag2—N6	142.47 (17)	C1—C2—C3—C4	1.4 (12)
N4—Ag1—Ag2—N6	74.86 (17)	C2—C3—C4—C5	1.0 (12)
N2—Ag1—Ag2—N6	−102.20 (18)	C1—N1—C5—C4	1.0 (8)
N3—Ag1—N1—C5	117.1 (5)	Ag1—N1—C5—C4	172.7 (5)
N4—Ag1—N1—C5	−148.8 (4)	C1—N1—C5—C6	−178.5 (5)
N2—Ag1—N1—C5	1.1 (4)	Ag1—N1—C5—C6	−6.8 (7)
Ag2—Ag1—N1—C5	−65.9 (4)	C3—C4—C5—N1	−2.3 (10)
N3—Ag1—N1—C1	−71.8 (6)	C3—C4—C5—C6	177.2 (7)
N4—Ag1—N1—C1	22.2 (5)	O1—N2—C6—C5	178.6 (5)
N2—Ag1—N1—C1	172.1 (5)	Ag1—N2—C6—C5	−11.2 (7)
Ag2—Ag1—N1—C1	105.1 (5)	N1—C5—C6—N2	12.6 (9)
N1—Ag1—N2—C6	5.5 (4)	C4—C5—C6—N2	−167.0 (6)
N3—Ag1—N2—C6	−148.9 (4)	C11—N3—C7—C8	−1.0 (9)
N4—Ag1—N2—C6	106.6 (5)	Ag1—N3—C7—C8	−172.7 (5)
Ag2—Ag1—N2—C6	112.8 (4)	N3—C7—C8—C9	1.3 (10)
N1—Ag1—N2—O1	173.1 (5)	C7—C8—C9—C10	0.3 (10)
N3—Ag1—N2—O1	18.8 (6)	C8—C9—C10—C11	−2.0 (10)
N4—Ag1—N2—O1	−85.7 (6)	C7—N3—C11—C10	−0.8 (8)
Ag2—Ag1—N2—O1	−79.6 (5)	Ag1—N3—C11—C10	171.8 (5)
N1—Ag1—N3—C7	−81.3 (6)	C7—N3—C11—C12	179.4 (5)
N4—Ag1—N3—C7	175.3 (5)	Ag1—N3—C11—C12	−8.0 (6)
N2—Ag1—N3—C7	24.1 (5)	C9—C10—C11—N3	2.3 (10)
Ag2—Ag1—N3—C7	101.8 (5)	C9—C10—C11—C12	−177.9 (6)
N1—Ag1—N3—C11	106.9 (5)	O2—N4—C12—C11	−176.6 (5)
N4—Ag1—N3—C11	3.5 (4)	Ag1—N4—C12—C11	−6.6 (7)
N2—Ag1—N3—C11	−147.7 (4)	N3—C11—C12—N4	10.1 (8)
Ag2—Ag1—N3—C11	−70.0 (4)	C10—C11—C12—N4	−169.6 (6)
N1—Ag1—N4—C12	−151.8 (4)	C17—N5—C13—C14	−0.1 (9)
N3—Ag1—N4—C12	1.7 (4)	Ag2—N5—C13—C14	−168.2 (5)
N2—Ag1—N4—C12	117.9 (5)	N5—C13—C14—C15	−0.3 (10)
Ag2—Ag1—N4—C12	112.0 (4)	C13—C14—C15—C16	0.1 (10)
N1—Ag1—N4—O2	16.5 (5)	C14—C15—C16—C17	0.6 (10)
N3—Ag1—N4—O2	170.0 (5)	C13—N5—C17—C16	0.9 (8)
N2—Ag1—N4—O2	−73.8 (6)	Ag2—N5—C17—C16	169.8 (4)
Ag2—Ag1—N4—O2	−79.7 (4)	C13—N5—C17—C18	−178.1 (5)
N7—Ag2—N5—C13	−91.9 (6)	Ag2—N5—C17—C18	−9.2 (6)
N8—Ag2—N5—C13	21.8 (6)	C15—C16—C17—N5	−1.1 (9)
N6—Ag2—N5—C13	169.8 (5)	C15—C16—C17—C18	177.9 (6)
Ag1—Ag2—N5—C13	102.5 (5)	O3—N6—C18—C17	177.9 (5)
N7—Ag2—N5—C17	100.0 (5)	Ag2—N6—C18—C17	−13.9 (7)
N8—Ag2—N5—C17	−146.2 (4)	N5—C17—C18—N6	16.3 (8)
N6—Ag2—N5—C17	1.7 (4)	C16—C17—C18—N6	−162.7 (6)
Ag1—Ag2—N5—C17	−65.6 (4)	C23—N7—C19—C20	1.1 (10)
N5—Ag2—N6—C18	6.4 (4)	Ag2—N7—C19—C20	−173.7 (6)
N7—Ag2—N6—C18	−147.7 (4)	N7—C19—C20—C21	−0.7 (12)
N8—Ag2—N6—C18	124.2 (4)	C19—C20—C21—C22	−0.6 (14)
Ag1—Ag2—N6—C18	118.7 (4)	C20—C21—C22—C23	1.3 (13)
N5—Ag2—N6—O3	171.5 (5)	C19—N7—C23—C22	−0.3 (9)
N7—Ag2—N6—O3	17.3 (5)	Ag2—N7—C23—C22	175.0 (5)
N8—Ag2—N6—O3	−70.7 (6)	C19—N7—C23—C24	178.7 (6)
Ag1—Ag2—N6—O3	−76.2 (5)	Ag2—N7—C23—C24	−6.0 (7)
N5—Ag2—N7—C19	−58.3 (7)	C21—C22—C23—N7	−0.9 (11)
N8—Ag2—N7—C19	178.2 (5)	C21—C22—C23—C24	−179.8 (7)
N6—Ag2—N7—C19	31.4 (5)	O4—N8—C24—C23	−179.6 (5)
Ag1—Ag2—N7—C19	107.6 (5)	Ag2—N8—C24—C23	−2.7 (8)
N5—Ag2—N7—C23	126.9 (5)	N7—C23—C24—N8	6.0 (9)
N8—Ag2—N7—C23	3.4 (4)	C22—C23—C24—N8	−175.0 (6)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O4	0.84	1.91	2.673 (8)	151
O3—H3o···O2	0.84	1.81	2.610 (6)	160
O4—H4o···O2ⁱⁱⁱ	0.84	1.64	2.475 (6)	174

Symmetry code: (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formula	[Ag(C₆H₅N₂O)(C₆H₆N₂O)]ClO₄·[Ag(C₆H₆N₂O)₂]
M_r	802.69
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.3925 (18), 8.3419 (19), 25.626 (6)
α, β, γ (°)	90.226 (6), 92.753 (6), 114.409 (6)
V (Å³)	1436.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.52
Crystal size (mm)	0.21 × 0.13 × 0.13

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.356, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	11387, 5042, 3660
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.187, 1.09
No. of reflections	5042
No. of parameters	430
No. of restraints	64
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.19, −0.58

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC and Rigaku, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ag1—N1	2.280 (5)	Ag2—N5	2.235 (5)
Ag1—N2	2.392 (5)	Ag2—N6	2.448 (4)
Ag1—N3	2.281 (5)	Ag2—N7	2.256 (5)
Ag1—N4	2.384 (5)	Ag2—N8	2.401 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···O4	0.84	1.91	2.673 (8)	151
O3—H3o···O2	0.84	1.81	2.610 (6)	160
O4—H4o···O2ⁱ	0.84	1.64	2.475 (6)	174

Symmetry code: (i) x, y+1, z.

Footnotes

‡Additional correspondence author, e-mail: shangao67@yahoo.com.

Acknowledgements

This work was supported by the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Key Project of the Education Bureau of Heilongjiang Province (Nos. 12511z023 and 2011CJHB006), the Innovation Team of the Education Bureau of Heilongjiang Province (No. 2010 t d03), Heilongjiang University (Hdtd2010–04) and the Ministry of Higher Education of Malaysia (grant No. UM.C/HIR/MOHE/SC/12).

References

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