(μ-3,5,9,11-Tetra­oxo-4,10-diaza­tetra­cyclo­[5.5.2.02,6.08,12]tetra­dec-13-ene-4,10-diido-κ2N:N′)bis­[(2,2′-bipyridine-κ2N,N′)silver(I)] dihydrate

Zhang, Y.

doi:10.1107/S1600536812038640

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1275

https://doi.org/10.1107/S1600536812038640

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(μ-3,5,9,11-Tetraoxo-4,10-diazatetracyclo[5.5.2.0^2,6.0^8,12]tetradec-13-ene-4,10-diido-κ²N:N′)bis[(2,2′-bipyridine-κ²N,N′)silver(I)] dihydrate

Yongmei Zhang ^a ^*

^aSchool of Chemistry and Life Science, Anshan Normal University, Anshan, Liaoning 114000, People's Republic of China
^*Correspondence e-mail: chemzhangym@163.com

(Received 3 September 2012; accepted 9 September 2012; online 15 September 2012)

In the title complex, [Ag₂(C₁₂H₈N₂O₄)(C₁₀H₈N₂)₂]·2H₂O, the Ag^I ion is three-coordinated by two N atoms from a chelating 2,2′-bipyridine ligand and one N atom from an imide ligand in a Y-shaped fashion. The imide ligand and the complex lie on a twofold rotation axis. The ligand bridges two Ag^I ions, forming a dinuclear complex. In the crystal, O—H⋯O hydrogen bonds link the lattice water molecules and the complex molecules into a ribbon-like structure along [001]. π–π interactions are observed between the pyridine rings [centroid–centroid distance = 3.8289 (14) Å].

Related literature

For structures and properties of mixed-ligand coordination polymers, see: Song et al. (2012 ); Wang (2010 ). For the use of molecular building blocks associated with polydentate carboxylic acids, see: Liao et al. (2008 ); Wang et al. (2009 ).

Experimental

Crystal data

[Ag₂(C₁₂H₈N₂O₄)(C₁₀H₈N₂)₂]·2H₂O
M_r = 808.34
Monoclinic, C 2/c
a = 22.2720 (12) Å
b = 7.1013 (4) Å
c = 19.6329 (11) Å
β = 108.376 (1)°
V = 2946.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.39 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.712, T_max = 0.758
7869 measured reflections
2923 independent reflections
2588 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.051
S = 1.03
2923 reflections
214 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1A⋯O2	0.81 (3)	2.07 (2)	2.839 (2)	159 (3)
O1W—H1B⋯O2ⁱ	0.82 (3)	2.13 (3)	2.952 (3)	175 (2)
Symmetry code: (i) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812038640/hy2587sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038640/hy2587Isup2.hkl

checkCIF report

Comment top

The assembly of mixed-ligand coordination polymers has attracted great attention due to their intriguingly complicated architectures and potential applications in adsorption, separation and magnetism (Song et al., 2012; Wang, 2010). Molecular building blocks associated with polydentate carboxylic acids are widely used in chiral catalysis, optoelectronic materials, hematopathology and medicine (Liao et al., 2008; Wang et al., 2009). In our laboratory, we synthesized a new silver(I) complex constructed by an amide molecule in combination with 2,2-bipyridine as ancillary ligand.

In the title complex, the amide ligand lies on a twofold rotation axis and bridges two 2,2'-bipyridine-chelated Ag^I atoms. The Ag^I atom is three-coordinated by two N atoms of a 2,2'-bipyridine ligand [Ag—N distances = 2.3510 (18) and 2.2380 (18) Å] and one N atom from an amide ligand [Ag—N distance = 2.1123 (17) Å]. In the crystal, O—H···O hydrogen bonds link the uncoordinated water molecules and the complex molecules into a ribbon-like structure. π–π interactions between the pyridine rings are observed [centroid–centroid distance = 3.8289 (14) Å].

Related literature top

For structures and properties of mixed-ligand coordination polymers, see: Song et al. (2012); Wang (2010). For the use of molecular building blocks associated with polydentate carboxylic acids, see: Liao et al. (2008); Wang et al. (2009).

Experimental top

A mixture of bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride (0.1 mmol, 0.025 g), 2,2'-bipyridine (0.2 mmol, 0.080 g), silver nitrate (0.2 mmol, 0.034 g) and H₂O (15 ml) was stirred for ten minutes. Dilute ammonia was dropwised into the mixture until the mixture turned to transparent. Colorless block crystals of the title compound were isolated after the evaporation of ammonia.

Structure description top

For structures and properties of mixed-ligand coordination polymers, see: Song et al. (2012); Wang (2010). For the use of molecular building blocks associated with polydentate carboxylic acids, see: Liao et al. (2008); Wang et al. (2009).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) 1-x, y, 1/2-z.]
	Fig. 2. View of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines.

(µ-3,5,9,11-Tetraoxo-4,10-diazatetracyclo[5.5.2.0^2,6.0^8,12]tetradec- 13-ene-4,10-diido-κ²N:N')bis[(2,2'-bipyridine- κ²N,N')silver(I)] dihydrate top

Crystal data top

[Ag₂(C₁₂H₈N₂O₄)(C₁₀H₈N₂)₂]·2H₂O	F(000) = 1616
M_r = 808.34	D_x = 1.822 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2928 reflections
a = 22.2720 (12) Å	θ = 1.0–26.1°
b = 7.1013 (4) Å	µ = 1.39 mm⁻¹
c = 19.6329 (11) Å	T = 293 K
β = 108.376 (1)°	Block, colorless
V = 2946.8 (3) Å³	0.24 × 0.22 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	2923 independent reflections
Radiation source: fine-focus sealed tube	2588 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 26.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −27→14
T_min = 0.712, T_max = 0.758	k = −8→7
7869 measured reflections	l = −24→23

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0222P)² + 3.2161P] where P = (F_o² + 2F_c²)/3
2923 reflections	(Δ/σ)_max = 0.002
214 parameters	Δρ_max = 0.30 e Å⁻³
2 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Ag₂(C₁₂H₈N₂O₄)(C₁₀H₈N₂)₂]·2H₂O	V = 2946.8 (3) Å³
M_r = 808.34	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.2720 (12) Å	µ = 1.39 mm⁻¹
b = 7.1013 (4) Å	T = 293 K
c = 19.6329 (11) Å	0.24 × 0.22 × 0.21 mm
β = 108.376 (1)°

Data collection top

Bruker APEXII CCD diffractometer	2923 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2588 reflections with I > 2σ(I)
T_min = 0.712, T_max = 0.758	R_int = 0.020
7869 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	2 restraints
wR(F²) = 0.051	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.30 e Å⁻³
2923 reflections	Δρ_min = −0.32 e Å⁻³
214 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.301043 (8)	0.57692 (2)	0.020063 (9)	0.02934 (7)
C1	0.37168 (10)	0.7372 (3)	0.16827 (11)	0.0247 (5)
C2	0.43266 (10)	0.8225 (3)	0.21718 (11)	0.0232 (4)
H2	0.4254	0.9535	0.2282	0.028*
C3	0.47747 (10)	0.8155 (3)	0.17171 (11)	0.0241 (5)
H3	0.4875	0.9436	0.1601	0.029*
C4	0.43841 (10)	0.7149 (3)	0.10388 (11)	0.0236 (4)
C5	0.46134 (9)	0.7102 (3)	0.28753 (11)	0.0229 (4)
H5	0.4321	0.7026	0.3157	0.027*
C6	0.47997 (9)	0.5181 (3)	0.26895 (11)	0.0224 (4)
H6	0.4646	0.4077	0.2829	0.027*
C7	0.17622 (12)	0.5344 (3)	0.07607 (13)	0.0352 (6)
H11	0.2008	0.6046	0.1149	0.042*
C8	0.11778 (13)	0.4724 (4)	0.07644 (15)	0.0419 (6)
H12	0.1026	0.5036	0.1140	0.050*
C9	0.08256 (12)	0.3642 (4)	0.02055 (15)	0.0437 (7)
H13	0.0432	0.3190	0.0200	0.052*
C10	0.10585 (11)	0.3222 (3)	−0.03534 (14)	0.0346 (5)
H14	0.0826	0.2478	−0.0735	0.041*
C11	0.16472 (10)	0.3932 (3)	−0.03348 (12)	0.0248 (5)
C12	0.19220 (10)	0.3621 (3)	−0.09278 (12)	0.0254 (5)
C13	0.16013 (11)	0.2632 (3)	−0.15462 (12)	0.0308 (5)
H17	0.1206	0.2113	−0.1596	0.037*
C14	0.18683 (12)	0.2423 (4)	−0.20821 (13)	0.0375 (6)
H18	0.1655	0.1769	−0.2499	0.045*
C15	0.24567 (12)	0.3190 (4)	−0.19984 (13)	0.0376 (6)
H19	0.2647	0.3071	−0.2355	0.045*
C16	0.27537 (11)	0.4139 (3)	−0.13678 (13)	0.0328 (5)
H20	0.3151	0.4652	−0.1307	0.039*
N1	0.19911 (9)	0.4976 (3)	0.02200 (10)	0.0282 (4)
N2	0.25001 (8)	0.4358 (2)	−0.08404 (10)	0.0263 (4)
N3	0.37858 (8)	0.6828 (2)	0.10383 (9)	0.0239 (4)
O1	0.32354 (7)	0.7175 (2)	0.18440 (8)	0.0329 (4)
O2	0.45990 (7)	0.6671 (3)	0.05599 (8)	0.0349 (4)
O1W	0.43224 (10)	0.5971 (3)	−0.09313 (10)	0.0525 (5)
H1A	0.4321 (17)	0.635 (5)	−0.0542 (13)	0.079*
H1B	0.4609 (14)	0.519 (4)	−0.0847 (19)	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.02316 (10)	0.03214 (11)	0.02658 (10)	−0.00518 (7)	−0.00091 (7)	0.00260 (7)
C1	0.0213 (11)	0.0274 (11)	0.0226 (11)	0.0055 (9)	0.0029 (9)	0.0072 (9)
C2	0.0231 (10)	0.0225 (11)	0.0217 (11)	0.0036 (9)	0.0036 (9)	0.0005 (9)
C3	0.0217 (10)	0.0265 (11)	0.0217 (11)	−0.0047 (9)	0.0035 (9)	0.0031 (9)
C4	0.0239 (11)	0.0263 (11)	0.0187 (10)	−0.0007 (9)	0.0039 (9)	0.0054 (9)
C5	0.0185 (10)	0.0311 (11)	0.0185 (10)	0.0023 (9)	0.0051 (8)	0.0007 (9)
C6	0.0194 (10)	0.0236 (10)	0.0197 (11)	−0.0024 (9)	−0.0002 (8)	0.0025 (9)
C7	0.0360 (13)	0.0386 (14)	0.0319 (13)	0.0003 (11)	0.0119 (11)	0.0047 (11)
C8	0.0434 (15)	0.0446 (15)	0.0464 (16)	0.0039 (12)	0.0265 (13)	0.0081 (13)
C9	0.0305 (13)	0.0442 (15)	0.0609 (18)	−0.0012 (12)	0.0209 (13)	0.0115 (14)
C10	0.0236 (11)	0.0329 (13)	0.0448 (15)	−0.0022 (10)	0.0075 (11)	0.0057 (11)
C11	0.0213 (11)	0.0225 (11)	0.0272 (12)	0.0007 (9)	0.0029 (9)	0.0070 (9)
C12	0.0217 (10)	0.0220 (10)	0.0286 (12)	0.0022 (9)	0.0024 (9)	0.0068 (9)
C13	0.0263 (12)	0.0278 (12)	0.0333 (13)	−0.0018 (10)	0.0021 (10)	0.0034 (10)
C14	0.0417 (14)	0.0345 (13)	0.0311 (13)	0.0000 (11)	0.0042 (11)	−0.0043 (11)
C15	0.0434 (14)	0.0402 (14)	0.0297 (13)	0.0053 (12)	0.0124 (11)	0.0003 (11)
C16	0.0276 (12)	0.0361 (13)	0.0349 (13)	−0.0011 (10)	0.0102 (10)	0.0036 (11)
N1	0.0256 (10)	0.0296 (10)	0.0285 (11)	−0.0012 (8)	0.0071 (8)	0.0045 (8)
N2	0.0215 (9)	0.0280 (10)	0.0264 (10)	−0.0010 (8)	0.0034 (8)	0.0027 (8)
N3	0.0208 (9)	0.0278 (10)	0.0202 (9)	−0.0011 (8)	0.0024 (7)	0.0031 (7)
O1	0.0215 (8)	0.0475 (10)	0.0298 (8)	0.0024 (7)	0.0081 (7)	0.0030 (8)
O2	0.0268 (8)	0.0563 (11)	0.0216 (8)	−0.0040 (8)	0.0076 (7)	−0.0017 (8)
O1W	0.0568 (13)	0.0680 (14)	0.0300 (10)	0.0172 (11)	0.0099 (10)	−0.0080 (10)

Geometric parameters (Å, º) top

Ag1—N3	2.1123 (17)	C7—H11	0.9300
Ag1—N2	2.2380 (18)	C8—C9	1.367 (4)
Ag1—N1	2.3510 (18)	C8—H12	0.9300
Ag1—Ag1ⁱ	3.2716 (4)	C9—C10	1.386 (4)
C1—O1	1.218 (2)	C9—H13	0.9300
C1—N3	1.377 (3)	C10—C11	1.394 (3)
C1—C2	1.520 (3)	C10—H14	0.9300
C2—C3	1.535 (3)	C11—N1	1.341 (3)
C2—C5	1.548 (3)	C11—C12	1.493 (3)
C2—H2	0.9800	C12—N2	1.350 (3)
C3—C4	1.520 (3)	C12—C13	1.390 (3)
C3—C5ⁱⁱ	1.539 (3)	C13—C14	1.370 (3)
C3—H3	0.9800	C13—H17	0.9300
C4—O2	1.230 (3)	C14—C15	1.380 (4)
C4—N3	1.352 (3)	C14—H18	0.9300
C5—C6	1.504 (3)	C15—C16	1.381 (3)
C5—C3ⁱⁱ	1.539 (3)	C15—H19	0.9300
C5—H5	0.9800	C16—N2	1.336 (3)
C6—C6ⁱⁱ	1.330 (4)	C16—H20	0.9300
C6—H6	0.9300	O1W—H1A	0.81 (3)
C7—N1	1.340 (3)	O1W—H1B	0.82 (3)
C7—C8	1.376 (3)

N3—Ag1—N2	157.77 (7)	C9—C8—H12	120.6
N3—Ag1—N1	129.00 (7)	C7—C8—H12	120.6
N2—Ag1—N1	72.09 (7)	C8—C9—C10	119.6 (2)
N3—Ag1—Ag1ⁱ	104.80 (5)	C8—C9—H13	120.2
N2—Ag1—Ag1ⁱ	90.12 (5)	C10—C9—H13	120.2
N1—Ag1—Ag1ⁱ	65.33 (5)	C9—C10—C11	119.0 (2)
O1—C1—N3	124.7 (2)	C9—C10—H14	120.5
O1—C1—C2	124.46 (19)	C11—C10—H14	120.5
N3—C1—C2	110.86 (17)	N1—C11—C10	120.9 (2)
C1—C2—C3	103.58 (16)	N1—C11—C12	116.48 (18)
C1—C2—C5	113.16 (18)	C10—C11—C12	122.6 (2)
C3—C2—C5	109.94 (17)	N2—C12—C13	120.9 (2)
C1—C2—H2	110.0	N2—C12—C11	116.92 (19)
C3—C2—H2	110.0	C13—C12—C11	122.1 (2)
C5—C2—H2	110.0	C14—C13—C12	119.9 (2)
C4—C3—C2	103.13 (16)	C14—C13—H17	120.1
C4—C3—C5ⁱⁱ	113.28 (18)	C12—C13—H17	120.1
C2—C3—C5ⁱⁱ	110.16 (16)	C13—C14—C15	119.4 (2)
C4—C3—H3	110.0	C13—C14—H18	120.3
C2—C3—H3	110.0	C15—C14—H18	120.3
C5ⁱⁱ—C3—H3	110.0	C14—C15—C16	117.9 (2)
O2—C4—N3	125.1 (2)	C14—C15—H19	121.1
O2—C4—C3	123.12 (19)	C16—C15—H19	121.1
N3—C4—C3	111.81 (18)	N2—C16—C15	123.5 (2)
C6—C5—C3ⁱⁱ	107.48 (16)	N2—C16—H20	118.3
C6—C5—C2	108.60 (16)	C15—C16—H20	118.3
C3ⁱⁱ—C5—C2	105.19 (17)	C7—N1—C11	119.3 (2)
C6—C5—H5	111.8	C7—N1—Ag1	125.20 (16)
C3ⁱⁱ—C5—H5	111.8	C11—N1—Ag1	115.26 (14)
C2—C5—H5	111.8	C16—N2—C12	118.4 (2)
C6ⁱⁱ—C6—C5	114.88 (11)	C16—N2—Ag1	122.89 (15)
C6ⁱⁱ—C6—H6	122.6	C12—N2—Ag1	118.63 (15)
C5—C6—H6	122.6	C4—N3—C1	110.35 (17)
N1—C7—C8	122.6 (2)	C4—N3—Ag1	128.63 (14)
N1—C7—H11	118.7	C1—N3—Ag1	120.98 (14)
C8—C7—H11	118.7	H1A—O1W—H1B	105 (4)
C9—C8—C7	118.7 (2)

O1—C1—C2—C3	−179.7 (2)	C12—C11—N1—C7	178.35 (19)
N3—C1—C2—C3	1.2 (2)	C10—C11—N1—Ag1	174.03 (16)
O1—C1—C2—C5	61.3 (3)	C12—C11—N1—Ag1	−7.3 (2)
N3—C1—C2—C5	−117.83 (19)	N3—Ag1—N1—C7	9.0 (2)
C1—C2—C3—C4	−3.7 (2)	N2—Ag1—N1—C7	−179.1 (2)
C5—C2—C3—C4	117.52 (18)	Ag1ⁱ—Ag1—N1—C7	−80.37 (18)
C1—C2—C3—C5ⁱⁱ	−124.88 (18)	N3—Ag1—N1—C11	−164.88 (14)
C5—C2—C3—C5ⁱⁱ	−3.7 (2)	N2—Ag1—N1—C11	7.03 (15)
C2—C3—C4—O2	−173.5 (2)	Ag1ⁱ—Ag1—N1—C11	105.71 (16)
C5ⁱⁱ—C3—C4—O2	−54.5 (3)	C15—C16—N2—C12	−0.2 (3)
C2—C3—C4—N3	5.4 (2)	C15—C16—N2—Ag1	176.70 (18)
C5ⁱⁱ—C3—C4—N3	124.47 (19)	C13—C12—N2—C16	1.0 (3)
C1—C2—C5—C6	64.1 (2)	C11—C12—N2—C16	−178.63 (19)
C3—C2—C5—C6	−51.2 (2)	C13—C12—N2—Ag1	−176.10 (16)
C1—C2—C5—C3ⁱⁱ	178.93 (17)	C11—C12—N2—Ag1	4.3 (2)
C3—C2—C5—C3ⁱⁱ	63.66 (18)	N3—Ag1—N2—C16	−19.6 (3)
C3ⁱⁱ—C5—C6—C6ⁱⁱ	−56.6 (3)	N1—Ag1—N2—C16	177.18 (19)
C2—C5—C6—C6ⁱⁱ	56.7 (3)	Ag1ⁱ—Ag1—N2—C16	113.25 (17)
N1—C7—C8—C9	2.1 (4)	N3—Ag1—N2—C12	157.30 (17)
C7—C8—C9—C10	−1.0 (4)	N1—Ag1—N2—C12	−5.89 (15)
C8—C9—C10—C11	−0.6 (4)	Ag1ⁱ—Ag1—N2—C12	−69.82 (15)
C9—C10—C11—N1	1.2 (3)	O2—C4—N3—C1	174.0 (2)
C9—C10—C11—C12	−177.3 (2)	C3—C4—N3—C1	−4.9 (2)
N1—C11—C12—N2	2.3 (3)	O2—C4—N3—Ag1	−8.5 (3)
C10—C11—C12—N2	−179.1 (2)	C3—C4—N3—Ag1	172.56 (13)
N1—C11—C12—C13	−177.2 (2)	O1—C1—N3—C4	−176.8 (2)
C10—C11—C12—C13	1.4 (3)	C2—C1—N3—C4	2.3 (2)
N2—C12—C13—C14	−1.1 (3)	O1—C1—N3—Ag1	5.4 (3)
C11—C12—C13—C14	178.5 (2)	C2—C1—N3—Ag1	−175.45 (13)
C12—C13—C14—C15	0.4 (4)	N2—Ag1—N3—C4	15.3 (3)
C13—C14—C15—C16	0.3 (4)	N1—Ag1—N3—C4	174.54 (16)
C14—C15—C16—N2	−0.4 (4)	Ag1ⁱ—Ag1—N3—C4	−115.44 (17)
C8—C7—N1—C11	−1.4 (4)	N2—Ag1—N3—C1	−167.45 (16)
C8—C7—N1—Ag1	−175.12 (18)	N1—Ag1—N3—C1	−8.19 (19)
C10—C11—N1—C7	−0.3 (3)	Ag1ⁱ—Ag1—N3—C1	61.83 (16)

Symmetry codes: (i) −x+1/2, −y+3/2, −z; (ii) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2	0.81 (3)	2.07 (2)	2.839 (2)	159 (3)
O1W—H1B···O2ⁱⁱⁱ	0.82 (3)	2.13 (3)	2.952 (3)	175 (2)

Symmetry code: (iii) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	[Ag₂(C₁₂H₈N₂O₄)(C₁₀H₈N₂)₂]·2H₂O
M_r	808.34
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	22.2720 (12), 7.1013 (4), 19.6329 (11)
β (°)	108.376 (1)
V (Å³)	2946.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.39
Crystal size (mm)	0.24 × 0.22 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.712, 0.758
No. of measured, independent and observed [I > 2σ(I)] reflections	7869, 2923, 2588
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.051, 1.03
No. of reflections	2923
No. of parameters	214
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2	0.81 (3)	2.07 (2)	2.839 (2)	159 (3)
O1W—H1B···O2ⁱ	0.82 (3)	2.13 (3)	2.952 (3)	175 (2)

Symmetry code: (i) −x+1, −y+1, −z.

Acknowledgements

The author thanks Anshan Normal University, Liaoning, China, for supporting this work.

References

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