(μ-3,5,9,11-Tetra-oxo-4,10-diaza-tetra-cyclo-[5.5.2.0(2,6).0(8,12)]tetra-dec-13-ene-4,10-diido-κ(2)N:N')bis-[(2,2'-bipyridine-κ(2)N,N')silver(I)] dihydrate.

In the title complex, [Ag(2)(C(12)H(8)N(2)O(4))(C(10)H(8)N(2))(2)]·2H(2)O, 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 mol-ecules and the complex mol-ecules into a ribbon-like structure along [001]. π-π inter-actions 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 = 808.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.021

wR(F 2) = 0.051

S = 1.03

2923 reflections

214 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.32 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038640/hy2587sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038640/hy2587Isup2.hkl

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

[Ag2(C12H8N2O4)(C10H8N2)2]·2H2O	F(000) = 1616
Mr = 808.34	Dx = 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

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

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(Fo2) + (0.0222P)2 + 3.2161P] where P = (Fo2 + 2Fc2)/3
2923 reflections	(Δ/σ)max = 0.002
214 parameters	Δρmax = 0.30 e Å−3
2 restraints	Δρmin = −0.32 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .