Poly[[μ(2)-1,4-bis-(imidazol-1-ylmethyl)-benzene](μ(4)-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)disilver(I)].

In the title complex, [Ag(2)(C(12)H(8)N(2)O(4))(C(14)H(14)N(4))](n), one Ag(I) ion, lying on a twofold rotation axis, is coordinated by two N atoms from two 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-diide (L) ligands in a nearly linear arrangement. The other Ag(I) ion, lying on an inversion center, is coordinated by two O atoms from two L ligands and two N atoms from two 1,4-bis-(imidazol-1-ylmeth-yl)benzene ligands in a distorted square-planar geometry. An additional Ag⋯Ag [3.0119 (3) Å] inter-action links the Ag(I) ions into a chain along [010]. The two types of ligands have mirror symmetry and connect the Ag(I) ions into a layer parallel to (100).

Related literature

For the design and synthesis of coordination polymers, see: Liao et al. (2008 ▶); Song et al. (2012 ▶); Wang et al. (2009 ▶). For the van der Waals radius of the Ag atom, see: Bondi (1964 ▶).

Experimental

Crystal data

[Ag2(C12H8N2O4)(C14H14N4)]

M = 698.24

Orthorhombic,

a = 10.1480 (11) Å

b = 11.0016 (11) Å

c = 21.183 (2) Å

V = 2365.0 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.71 mm−1

T = 296 K

0.27 × 0.21 × 0.17 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.656, T max = 0.760

12177 measured reflections

2402 independent reflections

1454 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.00

2402 reflections

180 parameters

H-atom parameters constrained

Δρmax = 0.58 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT-Plus (Bruker, 2007 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL .

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812039669/ng5293sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039669/ng5293Isup2.hkl

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

[Ag2(C12H8N2O4)(C14H14N4)]	F(000) = 1384
Mr = 698.24	Dx = 1.961 Mg m−3
Orthorhombic, Pbcm	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2c 2b	Cell parameters from 3256 reflections
a = 10.1480 (11) Å	θ = 2.8–25.9°
b = 11.0016 (11) Å	µ = 1.71 mm−1
c = 21.183 (2) Å	T = 296 K
V = 2365.0 (4) Å3	Block, colorless
Z = 4	0.27 × 0.21 × 0.17 mm

Bruker APEXII CCD diffractometer	2402 independent reflections
Radiation source: fine-focus sealed tube	1454 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.056
φ and ω scans	θmax = 26.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.656, Tmax = 0.760	k = −6→13
12177 measured reflections	l = −26→24

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) = 0.094	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0389P)2 + 3.7137P] where P = (Fo2 + 2Fc2)/3
2402 reflections	(Δ/σ)max < 0.001
180 parameters	Δρmax = 0.58 e Å−3
0 restraints	Δρmin = −0.59 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
C1	−0.2448 (5)	0.2484 (5)	0.3711 (2)	0.0310 (10)
C2	−0.2537 (5)	0.1795 (4)	0.3080 (2)	0.0280 (11)
H2	−0.3320	0.1274	0.3076	0.034*
C3	−0.2545 (7)	0.2650 (6)	0.2500	0.0272 (16)
H3	−0.3315	0.3188	0.2500	0.033*
C4	−0.1301 (8)	0.3340 (7)	0.2500	0.0347 (18)
H4	−0.1280	0.4185	0.2500	0.042*
C5	−0.0208 (7)	0.2669 (7)	0.2500	0.0340 (19)
H5	0.0633	0.3006	0.2500	0.041*
C6	−0.0445 (7)	0.1334 (7)	0.2500	0.0281 (17)
H6	0.0385	0.0879	0.2500	0.034*
C7	−0.1291 (5)	0.1015 (4)	0.3074 (2)	0.0272 (11)
H7	−0.1521	0.0150	0.3070	0.033*
C8	−0.0604 (5)	0.1346 (5)	0.3690 (2)	0.0301 (12)
C9	0.1964 (5)	0.1716 (5)	0.5666 (2)	0.0318 (13)
H9	0.1268	0.2226	0.5772	0.038*
C10	0.3079 (5)	0.0219 (5)	0.5312 (3)	0.0331 (13)
H10	0.3296	−0.0512	0.5118	0.040*
C11	0.3947 (5)	0.0980 (5)	0.5586 (3)	0.0352 (13)
H11	0.4853	0.0874	0.5619	0.042*
C12	0.3719 (5)	0.3029 (5)	0.6131 (2)	0.0289 (11)
H12A	0.3208	0.3726	0.5994	0.035*
H12B	0.4625	0.3164	0.6003	0.035*
C13	0.3669 (4)	0.2965 (4)	0.6840 (2)	0.0236 (10)
C14	0.3774 (5)	0.1894 (5)	0.7176 (2)	0.0308 (12)
H14	0.3845	0.1161	0.6960	0.037*
C15	0.3563 (5)	0.4041 (4)	0.7176 (2)	0.0308 (12)
H15	0.3490	0.4774	0.6959	0.037*
N1	−0.1358 (4)	0.2134 (4)	0.40402 (18)	0.0290 (10)
N2	0.1828 (4)	0.0679 (4)	0.53608 (19)	0.0276 (10)
N3	0.3223 (4)	0.1942 (4)	0.58061 (18)	0.0267 (9)
O1	−0.3267 (4)	0.3211 (4)	0.38995 (17)	0.0445 (10)
O2	0.0466 (3)	0.0946 (3)	0.38487 (16)	0.0346 (9)
Ag1	−0.12096 (5)	0.2500	0.5000	0.02695 (15)
Ag2	0.0000	0.0000	0.5000	0.03030 (16)

	U11	U22	U33	U12	U13	U23
C1	0.030 (2)	0.043 (3)	0.020 (2)	−0.001 (3)	0.005 (2)	−0.005 (3)
C2	0.028 (3)	0.030 (3)	0.026 (3)	−0.005 (2)	−0.001 (2)	0.000 (2)
C3	0.029 (4)	0.038 (5)	0.015 (3)	0.014 (4)	0.000	0.000
C4	0.042 (5)	0.027 (4)	0.036 (5)	−0.005 (4)	0.000	0.000
C5	0.030 (4)	0.046 (6)	0.026 (4)	−0.006 (4)	0.000	0.000
C6	0.030 (4)	0.038 (5)	0.017 (4)	0.008 (4)	0.000	0.000
C7	0.035 (3)	0.022 (3)	0.024 (3)	0.000 (2)	−0.001 (2)	0.000 (2)
C8	0.040 (3)	0.035 (3)	0.015 (3)	0.000 (3)	0.001 (2)	0.006 (2)
C9	0.030 (3)	0.035 (3)	0.031 (3)	0.002 (2)	−0.010 (2)	0.001 (2)
C10	0.033 (3)	0.035 (3)	0.032 (3)	−0.005 (2)	0.003 (2)	−0.007 (2)
C11	0.020 (3)	0.044 (3)	0.042 (3)	−0.004 (2)	0.000 (2)	−0.008 (3)
C12	0.033 (3)	0.029 (3)	0.024 (3)	−0.008 (2)	−0.008 (2)	0.001 (2)
C13	0.018 (2)	0.029 (3)	0.024 (2)	−0.002 (2)	−0.003 (2)	0.000 (2)
C14	0.038 (3)	0.023 (3)	0.031 (3)	−0.002 (2)	0.004 (2)	−0.011 (2)
C15	0.041 (3)	0.022 (3)	0.029 (3)	0.004 (2)	0.000 (2)	0.003 (2)
N1	0.032 (2)	0.040 (3)	0.015 (2)	0.0025 (19)	0.0010 (18)	−0.0032 (17)
N2	0.031 (2)	0.029 (2)	0.022 (2)	−0.0052 (19)	−0.0065 (18)	0.0016 (19)
N3	0.030 (2)	0.029 (2)	0.020 (2)	−0.0038 (19)	−0.0018 (19)	−0.0005 (19)
O1	0.036 (2)	0.065 (3)	0.033 (2)	0.016 (2)	0.0056 (18)	−0.014 (2)
O2	0.033 (2)	0.047 (2)	0.0235 (19)	0.0068 (18)	−0.0057 (16)	0.0033 (17)
Ag1	0.0308 (3)	0.0334 (3)	0.0167 (3)	0.000	0.000	−0.0039 (2)
Ag2	0.0293 (3)	0.0300 (3)	0.0316 (3)	−0.0038 (2)	−0.0104 (3)	0.0022 (3)

C1—O1	1.221 (6)	C9—N3	1.334 (6)
C1—N1	1.363 (6)	C9—H9	0.9300
C1—C2	1.538 (6)	C10—C11	1.347 (7)
C2—C7	1.527 (7)	C10—N2	1.370 (6)
C2—C3	1.548 (6)	C10—H10	0.9300
C2—H2	0.9800	C11—N3	1.370 (6)
C3—C4	1.473 (10)	C11—H11	0.9300
C3—C2i	1.548 (6)	C12—N3	1.469 (6)
C3—H3	0.9800	C12—C13	1.505 (6)
C4—C5	1.333 (10)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.487 (9)	C13—C14	1.381 (7)
C5—H5	0.9300	C13—C15	1.385 (7)
C6—C7i	1.530 (6)	C14—C14ii	1.372 (10)
C6—C7	1.530 (6)	C14—H14	0.9300
C6—H6	0.9800	C15—C15ii	1.373 (10)
C7—C8	1.524 (7)	C15—H15	0.9300
C7—H7	0.9800	Ag1—N1	2.078 (4)
C8—O2	1.218 (6)	Ag2—N2	2.141 (4)
C8—N1	1.374 (6)	Ag2—O2	2.693 (3)
C9—N2	1.319 (6)	Ag1—Ag2	3.0119 (3)
O1—C1—N1	124.7 (4)	N2—C10—H10	124.9
O1—C1—C2	124.5 (5)	C10—C11—N3	106.0 (5)
N1—C1—C2	110.7 (4)	C10—C11—H11	127.0
C7—C2—C1	103.6 (4)	N3—C11—H11	127.0
C7—C2—C3	109.8 (4)	N3—C12—C13	114.7 (4)
C1—C2—C3	113.0 (4)	N3—C12—H12A	108.6
C7—C2—H2	110.1	C13—C12—H12A	108.6
C1—C2—H2	110.1	N3—C12—H12B	108.6
C3—C2—H2	110.1	C13—C12—H12B	108.6
C4—C3—C2i	108.0 (4)	H12A—C12—H12B	107.6
C4—C3—C2	108.0 (4)	C14—C13—C15	118.1 (5)
C2i—C3—C2	105.1 (5)	C14—C13—C12	123.5 (5)
C4—C3—H3	111.8	C15—C13—C12	118.4 (4)
C2i—C3—H3	111.8	C14ii—C14—C13	121.0 (3)
C2—C3—H3	111.8	C14ii—C14—H14	119.5
C5—C4—C3	115.3 (7)	C13—C14—H14	119.5
C5—C4—H4	122.3	C15ii—C15—C13	120.9 (3)
C3—C4—H4	122.3	C15ii—C15—H15	119.6
C4—C5—C6	114.3 (7)	C13—C15—H15	119.6
C4—C5—H5	122.8	C1—N1—C8	110.7 (4)
C6—C5—H5	122.8	C1—N1—Ag1	120.4 (3)
C5—C6—C7i	108.5 (4)	C8—N1—Ag1	127.6 (3)
C5—C6—C7	108.5 (4)	C9—N2—C10	105.0 (4)
C7i—C6—C7	105.4 (6)	C9—N2—Ag2	124.6 (3)
C5—C6—H6	111.4	C10—N2—Ag2	130.3 (3)
C7i—C6—H6	111.4	C9—N3—C11	107.1 (4)
C7—C6—H6	111.4	C9—N3—C12	125.8 (4)
C8—C7—C2	103.8 (4)	C11—N3—C12	127.2 (4)
C8—C7—C6	111.7 (4)	N1—Ag1—N1iii	171.7 (2)
C2—C7—C6	110.0 (4)	N1—Ag1—Ag2iii	101.91 (12)
C8—C7—H7	110.4	N1iii—Ag1—Ag2iii	81.53 (11)
C2—C7—H7	110.4	N1—Ag1—Ag2	81.53 (11)
C6—C7—H7	110.4	N1iii—Ag1—Ag2	101.91 (11)
O2—C8—N1	125.1 (5)	Ag2iii—Ag1—Ag2	131.898 (18)
O2—C8—C7	123.9 (5)	N2—Ag2—N2iv	180.00 (11)
N1—C8—C7	110.9 (4)	N2—Ag2—Ag1iv	88.01 (11)
N2—C9—N3	111.7 (5)	N2iv—Ag2—Ag1iv	91.99 (11)
N2—C9—H9	124.1	N2—Ag2—Ag1	91.99 (11)
N3—C9—H9	124.1	N2iv—Ag2—Ag1	88.01 (11)
C11—C10—N2	110.1 (5)	N2—Ag2—O2	92.08 (13)
C11—C10—H10	124.9	O2—Ag2—N2iv	87.92 (13)

Table 1

Selected bond lengths (Å)

Ag1—N1	2.078 (4)
Ag2—N2	2.141 (4)
Ag2—O2	2.693 (3)