catena-Poly[[bis­[μ-2-(3-pyrid­yl)-1H-benzimidazole]-κ2N2:N3;κ2N3:N2-disilver(I)]-μ-2,5-dicarboxy­benzene-1,4-dicarboxyl­ato-κ2O2:O5]

Chen, J.

doi:10.1107/S1600536808004984

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 3| March 2008| Pages m498-m499

doi:10.1107/S1600536808004984

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catena-Poly[[bis[μ-2-(3-pyridyl)-1H-benzimidazole]-κ²N²:N³;κ²N³:N²-disilver(I)]-μ-2,5-dicarboxybenzene-1,4-dicarboxylato-κ²O²:O⁵]

Jie Chen ^a ^*‡

^aDepartment of Civil Engineering, Fujian University of Technology, Fuzhou, Fujian 350002, People's Republic of China
^*Correspondence e-mail: yq014@163.com

(Received 24 December 2007; accepted 21 February 2008; online 27 February 2008)

The title coordination polymer, [Ag₂(C₁₀H₄O₈)(C₁₂H₉N₃)₂]_n, was prepared by a hydrothermal method. The Ag^I atom exists in a strongly distorted trigonal coordination environment. Two Ag^I ions related by an inversion centre are coordinated by two 2-(3-pyridyl)benzimidazole ligands, forming a centrosymmetric cyclic dimer. The bridging bidentate 2,5-dicarboxybenzene-1,4-dicarboxylate ligand is also located on an inversion centre and connects the binuclear units, generating a one-dimensional polymer. The almost-planar conformation of this ligand allows it to form a strong intramolecular O—H⋯O hydrogen bond. Finally, intermolecular N—H⋯O hydrogen bonds aggregate the chains into a three-dimensional framework.

Related literature

For related literature, see: Alcalde et al. (1992 ); Cao et al. (2002 ); Hu et al. (2004 ); Li et al. (2003 ); Xia et al. (2007 ).

Experimental

Crystal data

[Ag₂(C₁₀H₄O₈)(C₁₂H₉N₃)₂]
M_r = 858.32
Monoclinic, P 2₁ /n
a = 4.8940 (11) Å
b = 16.011 (4) Å
c = 19.077 (4) Å
β = 92.393 (3)°
V = 1493.6 (6) Å³
Z = 2
Mo Kα radiation
μ = 1.38 mm⁻¹
T = 293 (2) K
0.48 × 0.13 × 0.13 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 ) T_min = 0.806, T_max = 0.842
11420 measured reflections
3405 independent reflections
3079 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.075
S = 1.07
3405 reflections
230 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—N2	2.1663 (18)
Ag1—N1ⁱ	2.207 (2)
Ag1—O1	2.3889 (18)

N2—Ag1—N1ⁱ	150.61 (7)
N2—Ag1—O1	115.06 (7)
N1ⁱ—Ag1—O1	93.66 (7)
Symmetry code: (i) -x+2, -y, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O4	0.846 (19)	1.56 (2)	2.399 (3)	171 (4)
N3—H3A⋯O3ⁱⁱ	0.86	1.92	2.742 (3)	159
Symmetry code: (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2000); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004984/bh2158sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808004984/bh2158Isup2.hkl

checkCIF report

Comment top

1,2,4,5-Benzenetetracarboxylic acid (H₄BTEC) has been regarded as an excellent candidate for the construction of multi-dimensional coordination polymers for its versatile coordination modes and rich hydrogen bonding (Cao et al., 2002; Hu et al., 2004; Li et al., 2003). The coordination supramolecular architectures are controlled by the extent of the deprotonation of H₄BTEC, nature of the auxiliary ligands, and metal coordination centers.

In the title coordination polymer, (I), the Ag^I is three coordinated (Fig. 1). Two symmetry related Ag^I ions are bonded by four N atoms from two 2-(3-pyridyl)-1H-benzimidazole ligands in the head to end mode, forming a centrosymmetric cyclic dimer. The coordination sphere of the cyclic dimer is completed by the 2,5-dicarboxybenzene-1,4-dicarboxylate coordinating in a bis(monodentate) fashion, which is similar to the coordination mode reported by Xia et al. (2007). The centrosymmetric bridging 2,5-dicarboxybenzene-1,4-dicarboxylate ligands link the binuclear units into a one-dimensional polymeric chain (Fig. 2). Interestingly, the coordinating O atom is provided by the undeprotonated carboxylic group rather than the deprotonated one. The O2—H group in the undeprotonated carboxylic group forms a strong intramolecular hydrogen bond with the adjacent carboxylate group [O2···O4: 2.399 (3) Å]. This contact allows planarity for the bridging ligand, which may be related to the non-coordinating character of carboxylate functionalities. The uncoordinated carboxylate group also provides another O atom for the formation of intermolecular hydrogen bonds [N3···O3: 2.742 (3) Å], forming a three-dimensional framework (Fig. 3). Despite of the presence of aromatic rings, no apparent π···π stacking interactions are found in the crystal structure.

Related literature top

For related literature, see: Alcalde et al. (1992); Cao et al. (2002); Hu et al. (2004); Li et al. (2003); Xia et al. (2007).

Experimental top

A solution of Ag₂O (0.07 g, 0.30 mmol), 2-(3-pyridyl)-1H-benzimidazole (Alcalde et al., 1992) (0.14 g, 0.61 mmol), 1,2,4,5-benzenetetracarboxylic acid (0.066 g, 0.30 mmol) and H₂O (15 ml) was stirred under ambient conditions. The solution was sealed in a 25 ml Teflon-lined stainless steel vessel, heated at 413 K for 4 days and cooled to room temperature for 3 days. The resulting product was recovered by filtration, washed with distilled water and dried in air (65% yield).

Computing details top

Data collection: CrystalClear (Rigaku, 2000); cell refinement: CrystalClear (Rigaku, 2000); data reduction: CrystalClear (Rigaku, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The structure of (I), with the atomic labels and 30% probability displacement ellipsoids for non-H atoms. [Symmetry codes: (i) 2 - x, -y, 2 - z; (ii) 1 - x, 1 - y, 2 - z].
	Fig. 2. A view of the one-dimensional chain of (I). H atoms are omitted for clarity.
	Fig. 3. The crystal packing of (I). H atoms are omitted for clarity.

catena-Poly[[bis[µ-2-(3-pyridyl)-1H-benzimidazole]- κ²N²:N³;κ²N³:N²-disilver(I)]-µ-2,5-dicarboxybenzene-1,4- dicarboxylato-κ²O²:O⁵] top

Crystal data top

[Ag₂(C₁₀H₄O₈)(C₁₂H₉N₃)₂]	F(000) = 852
M_r = 858.32	D_x = 1.909 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3641 reflections
a = 4.8940 (11) Å	θ = 2.5–27.5°
b = 16.011 (4) Å	µ = 1.38 mm⁻¹
c = 19.077 (4) Å	T = 293 K
β = 92.393 (3)°	Prism, colourless
V = 1493.6 (6) Å³	0.48 × 0.13 × 0.13 mm
Z = 2

Data collection top

Rigaku Mercury CCD diffractometer	3405 independent reflections
Radiation source: fine-focus sealed tube	3079 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	h = −6→6
T_min = 0.806, T_max = 0.842	k = −20→20
11420 measured reflections	l = −18→24

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0366P)² + 0.9191P] where P = (F_o² + 2F_c²)/3
3405 reflections	(Δ/σ)_max = 0.005
230 parameters	Δρ_max = 0.50 e Å⁻³
1 restraint	Δρ_min = −0.85 e Å⁻³

Crystal data top

[Ag₂(C₁₀H₄O₈)(C₁₂H₉N₃)₂]	V = 1493.6 (6) Å³
M_r = 858.32	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.8940 (11) Å	µ = 1.38 mm⁻¹
b = 16.011 (4) Å	T = 293 K
c = 19.077 (4) Å	0.48 × 0.13 × 0.13 mm
β = 92.393 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	3405 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2000)	3079 reflections with I > 2σ(I)
T_min = 0.806, T_max = 0.842	R_int = 0.023
11420 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.50 e Å⁻³
3405 reflections	Δρ_min = −0.85 e Å⁻³
230 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.71244 (4)	0.134099 (11)	1.018347 (10)	0.04125 (9)
C1	1.1680 (5)	−0.15500 (14)	1.13812 (13)	0.0343 (5)
H1A	1.2997	−0.1963	1.1336	0.041*
C2	1.0649 (5)	−0.14053 (14)	1.20320 (14)	0.0359 (5)
H2A	1.1275	−0.1717	1.2418	0.043*
C3	0.8688 (5)	−0.07976 (15)	1.21087 (12)	0.0329 (5)
H3B	0.7980	−0.0695	1.2545	0.039*
C4	0.7781 (4)	−0.03380 (13)	1.15231 (12)	0.0265 (4)
C5	0.8913 (5)	−0.05275 (13)	1.08884 (12)	0.0324 (5)
H5A	0.8300	−0.0232	1.0493	0.039*
C6	0.5728 (4)	0.03242 (13)	1.15806 (11)	0.0264 (4)
C7	0.3021 (5)	0.13812 (13)	1.13776 (12)	0.0269 (4)
C8	0.1575 (5)	0.20687 (14)	1.11051 (13)	0.0347 (5)
H8A	0.1860	0.2269	1.0656	0.042*
C9	−0.0299 (5)	0.24392 (16)	1.15313 (14)	0.0386 (6)
H9A	−0.1287	0.2900	1.1365	0.046*
C10	−0.0745 (5)	0.21380 (16)	1.22058 (14)	0.0383 (6)
H10A	−0.2039	0.2399	1.2474	0.046*
C11	0.0682 (5)	0.14644 (15)	1.24842 (13)	0.0332 (5)
H11A	0.0396	0.1267	1.2934	0.040*
C12	0.2577 (4)	0.10963 (13)	1.20541 (11)	0.0264 (4)
C13	0.5075 (5)	0.32005 (13)	0.96973 (12)	0.0322 (5)
C14	0.4884 (5)	0.41435 (13)	0.98108 (11)	0.0271 (4)
C15	0.3175 (5)	0.47238 (13)	0.94531 (11)	0.0271 (4)
C16	0.1144 (5)	0.45603 (15)	0.88456 (12)	0.0320 (5)
C17	0.3352 (5)	0.55568 (14)	0.96571 (12)	0.0297 (5)
H17A	0.2214	0.5939	0.9422	0.036*
N1	1.0845 (4)	−0.11132 (12)	1.08101 (11)	0.0347 (4)
N2	0.5015 (4)	0.08847 (11)	1.10831 (9)	0.0273 (4)
N3	0.4299 (4)	0.04296 (11)	1.21627 (9)	0.0273 (4)
H3A	0.4443	0.0131	1.2537	0.033*
O1	0.6918 (4)	0.28180 (11)	1.00119 (11)	0.0484 (5)
O2	0.3341 (4)	0.28260 (11)	0.92949 (12)	0.0486 (5)
H2B	0.217 (7)	0.316 (2)	0.912 (2)	0.082 (13)*
O3	0.0298 (4)	0.51666 (11)	0.84962 (9)	0.0440 (4)
O4	0.0356 (4)	0.38153 (11)	0.87095 (10)	0.0456 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.05515 (15)	0.02899 (12)	0.04086 (13)	0.01185 (8)	0.01680 (9)	0.00789 (7)
C1	0.0358 (12)	0.0225 (10)	0.0449 (14)	0.0059 (9)	0.0042 (10)	0.0043 (9)
C2	0.0383 (13)	0.0301 (12)	0.0393 (13)	0.0058 (10)	0.0011 (10)	0.0093 (9)
C3	0.0362 (12)	0.0305 (12)	0.0320 (12)	0.0041 (10)	0.0018 (9)	0.0010 (9)
C4	0.0274 (11)	0.0187 (9)	0.0333 (11)	−0.0010 (8)	0.0010 (8)	−0.0001 (8)
C5	0.0411 (13)	0.0216 (10)	0.0347 (12)	0.0054 (9)	0.0037 (10)	0.0026 (8)
C6	0.0283 (11)	0.0205 (10)	0.0303 (11)	−0.0005 (8)	−0.0007 (8)	−0.0007 (8)
C7	0.0263 (11)	0.0219 (10)	0.0323 (11)	−0.0002 (8)	−0.0002 (8)	−0.0008 (8)
C8	0.0368 (13)	0.0280 (11)	0.0386 (13)	0.0034 (10)	−0.0037 (10)	0.0050 (9)
C9	0.0372 (13)	0.0284 (12)	0.0492 (15)	0.0097 (10)	−0.0073 (11)	−0.0006 (10)
C10	0.0324 (12)	0.0360 (13)	0.0463 (14)	0.0081 (10)	0.0001 (10)	−0.0107 (10)
C11	0.0319 (12)	0.0337 (12)	0.0339 (12)	0.0015 (9)	0.0014 (9)	−0.0027 (9)
C12	0.0259 (11)	0.0223 (10)	0.0307 (11)	0.0005 (8)	−0.0023 (8)	−0.0012 (8)
C13	0.0455 (14)	0.0189 (10)	0.0327 (12)	0.0017 (9)	0.0057 (10)	−0.0001 (8)
C14	0.0379 (12)	0.0173 (9)	0.0261 (10)	0.0030 (8)	0.0037 (9)	0.0002 (7)
C15	0.0347 (12)	0.0219 (10)	0.0249 (10)	0.0022 (9)	0.0035 (8)	0.0003 (8)
C16	0.0380 (13)	0.0309 (11)	0.0269 (11)	0.0029 (9)	0.0012 (9)	−0.0016 (9)
C17	0.0400 (13)	0.0207 (10)	0.0282 (11)	0.0055 (9)	−0.0013 (9)	0.0031 (8)
N1	0.0428 (12)	0.0208 (9)	0.0410 (11)	0.0040 (8)	0.0082 (9)	0.0028 (8)
N2	0.0303 (10)	0.0220 (9)	0.0297 (9)	0.0025 (7)	0.0020 (7)	0.0016 (7)
N3	0.0304 (10)	0.0244 (9)	0.0272 (9)	0.0038 (7)	0.0014 (7)	0.0023 (7)
O1	0.0691 (13)	0.0194 (8)	0.0554 (11)	0.0126 (8)	−0.0126 (10)	0.0003 (7)
O2	0.0545 (12)	0.0220 (8)	0.0680 (13)	0.0009 (8)	−0.0133 (10)	−0.0091 (8)
O3	0.0638 (12)	0.0335 (9)	0.0334 (9)	0.0062 (9)	−0.0137 (8)	−0.0009 (7)
O4	0.0538 (12)	0.0345 (9)	0.0471 (11)	−0.0065 (8)	−0.0147 (9)	−0.0035 (8)

Geometric parameters (Å, º) top

Ag1—N2	2.1663 (18)	C9—H9A	0.9300
Ag1—N1ⁱ	2.207 (2)	C10—C11	1.379 (3)
Ag1—O1	2.3889 (18)	C10—H10A	0.9300
C1—N1	1.344 (3)	C11—C12	1.394 (3)
C1—C2	1.379 (4)	C11—H11A	0.9300
C1—H1A	0.9300	C12—N3	1.370 (3)
C2—C3	1.379 (3)	C13—O1	1.226 (3)
C2—H2A	0.9300	C13—O2	1.271 (3)
C3—C4	1.395 (3)	C13—C14	1.529 (3)
C3—H3B	0.9300	C14—C17ⁱⁱ	1.390 (3)
C4—C5	1.386 (3)	C14—C15	1.407 (3)
C4—C6	1.468 (3)	C15—C17	1.391 (3)
C5—N1	1.344 (3)	C15—C16	1.518 (3)
C5—H5A	0.9300	C16—O3	1.239 (3)
C6—N3	1.347 (3)	C16—O4	1.277 (3)
C6—N2	1.342 (3)	C16—O4	1.277 (3)
C7—C8	1.397 (3)	C17—H17A	0.9300
C7—N2	1.395 (3)	N3—O3ⁱⁱⁱ	2.742 (3)
C7—C12	1.394 (3)	N3—H3A	0.8600
C8—C9	1.384 (4)	O2—O4	2.399 (3)
C8—H8A	0.9300	O2—H2B	0.846 (19)
C9—C10	1.400 (4)

N2—Ag1—N1ⁱ	150.61 (7)	C12—C11—H11A	121.9
N2—Ag1—O1	115.06 (7)	N3—C12—C11	131.3 (2)
N1ⁱ—Ag1—O1	93.66 (7)	N3—C12—C7	106.02 (18)
N1—C1—C2	122.1 (2)	C11—C12—C7	122.7 (2)
N1—C1—H1A	118.9	O1—C13—O2	121.3 (2)
C2—C1—H1A	118.9	O1—C13—C14	118.2 (2)
C3—C2—C1	119.8 (2)	O2—C13—C14	120.5 (2)
C3—C2—H2A	120.1	C17ⁱⁱ—C14—C15	117.68 (19)
C1—C2—H2A	120.1	C17ⁱⁱ—C14—C13	113.86 (19)
C2—C3—C4	119.1 (2)	C15—C14—C13	128.5 (2)
C2—C3—H3B	120.4	C17—C15—C14	117.9 (2)
C4—C3—H3B	120.4	C17—C15—C16	114.22 (19)
C5—C4—C3	117.3 (2)	C14—C15—C16	127.83 (19)
C5—C4—C6	121.6 (2)	O3—C16—O4	122.1 (2)
C3—C4—C6	121.1 (2)	O3—C16—O4	122.1 (2)
N1—C5—C4	124.0 (2)	O3—C16—C15	118.0 (2)
N1—C5—H5A	118.0	O4—C16—C15	119.9 (2)
C4—C5—H5A	118.0	O4—C16—C15	119.9 (2)
N3—C6—N2	111.75 (19)	C15—C17—C14ⁱⁱ	124.4 (2)
N3—C6—C4	122.18 (19)	C15—C17—H17A	117.8
N2—C6—C4	126.1 (2)	C14ⁱⁱ—C17—H17A	117.8
C8—C7—N2	130.6 (2)	C5—N1—C1	117.7 (2)
C8—C7—C12	120.4 (2)	C5—N1—Ag1ⁱ	123.69 (16)
N2—C7—C12	108.97 (19)	C1—N1—Ag1ⁱ	118.53 (16)
C9—C8—C7	117.2 (2)	C6—N2—C7	105.18 (18)
C9—C8—H8A	121.4	C6—N2—Ag1	131.88 (15)
C7—C8—H8A	121.4	C7—N2—Ag1	119.44 (14)
C8—C9—C10	121.7 (2)	C6—N3—C12	108.07 (18)
C8—C9—H9A	119.2	C6—N3—O3ⁱⁱⁱ	129.98 (14)
C10—C9—H9A	119.2	C12—N3—O3ⁱⁱⁱ	119.74 (14)
C11—C10—C9	121.9 (2)	C6—N3—H3A	126.0
C11—C10—H10A	119.1	C12—N3—H3A	126.0
C9—C10—H10A	119.1	C13—O1—Ag1	125.98 (17)
C10—C11—C12	116.3 (2)	C13—O2—O4	110.37 (15)
C10—C11—H11A	121.9	C13—O2—H2B	111 (3)

N1—C1—C2—C3	0.3 (4)	C14—C15—C17—C14ⁱⁱ	0.3 (4)
C1—C2—C3—C4	0.0 (4)	C16—C15—C17—C14ⁱⁱ	−178.4 (2)
C2—C3—C4—C5	0.4 (3)	C4—C5—N1—C1	1.3 (4)
C2—C3—C4—C6	−179.0 (2)	C4—C5—N1—Ag1ⁱ	−174.85 (17)
C3—C4—C5—N1	−1.1 (4)	C2—C1—N1—C5	−0.9 (4)
C6—C4—C5—N1	178.3 (2)	C2—C1—N1—Ag1ⁱ	175.50 (19)
C5—C4—C6—N3	169.4 (2)	N3—C6—N2—C7	0.7 (2)
C3—C4—C6—N3	−11.2 (3)	C4—C6—N2—C7	−179.8 (2)
C5—C4—C6—N2	−10.2 (3)	N3—C6—N2—Ag1	158.67 (15)
C3—C4—C6—N2	169.2 (2)	C4—C6—N2—Ag1	−21.7 (3)
N2—C7—C8—C9	−179.8 (2)	C8—C7—N2—C6	179.0 (2)
C12—C7—C8—C9	−0.6 (3)	C12—C7—N2—C6	−0.3 (2)
C7—C8—C9—C10	−0.3 (4)	C8—C7—N2—Ag1	17.7 (3)
C8—C9—C10—C11	0.9 (4)	C12—C7—N2—Ag1	−161.64 (14)
C9—C10—C11—C12	−0.5 (4)	N1ⁱ—Ag1—N2—C6	57.2 (3)
C10—C11—C12—N3	−179.8 (2)	O1—Ag1—N2—C6	−135.92 (19)
C10—C11—C12—C7	−0.4 (4)	N1ⁱ—Ag1—N2—C7	−147.28 (17)
C8—C7—C12—N3	−179.5 (2)	O1—Ag1—N2—C7	19.57 (18)
N2—C7—C12—N3	−0.1 (2)	N2—C6—N3—C12	−0.8 (2)
C8—C7—C12—C11	0.9 (4)	C4—C6—N3—C12	179.6 (2)
N2—C7—C12—C11	−179.7 (2)	N2—C6—N3—O3ⁱⁱⁱ	−163.40 (15)
O1—C13—C14—C17ⁱⁱ	−8.4 (3)	C4—C6—N3—O3ⁱⁱⁱ	17.0 (3)
O2—C13—C14—C17ⁱⁱ	170.6 (2)	C11—C12—N3—C6	−180.0 (2)
O1—C13—C14—C15	172.0 (2)	C7—C12—N3—C6	0.5 (2)
O2—C13—C14—C15	−9.0 (4)	C11—C12—N3—O3ⁱⁱⁱ	−15.2 (3)
C17ⁱⁱ—C14—C15—C17	−0.3 (4)	C7—C12—N3—O3ⁱⁱⁱ	165.26 (14)
C13—C14—C15—C17	179.3 (2)	O2—C13—O1—Ag1	−15.7 (4)
C17ⁱⁱ—C14—C15—C16	178.2 (2)	C14—C13—O1—Ag1	163.34 (15)
C13—C14—C15—C16	−2.1 (4)	N2—Ag1—O1—C13	−85.5 (2)
C17—C15—C16—O3	15.1 (3)	N1ⁱ—Ag1—O1—C13	88.1 (2)
C14—C15—C16—O3	−163.5 (2)	O1—C13—O2—O4	−175.0 (2)
C17—C15—C16—O4	−164.8 (2)	C14—C13—O2—O4	6.0 (3)
C14—C15—C16—O4	16.6 (4)	O3—C16—O4—O4	0.0 (4)
C17—C15—C16—O4	−164.8 (2)	C15—C16—O4—O4	0.0 (3)
C14—C15—C16—O4	16.6 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O4	0.85 (2)	1.56 (2)	2.399 (3)	171 (4)
N3—H3A···O3ⁱⁱⁱ	0.86	1.92	2.742 (3)	159

Symmetry code: (iii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Ag₂(C₁₀H₄O₈)(C₁₂H₉N₃)₂]
M_r	858.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	4.8940 (11), 16.011 (4), 19.077 (4)
β (°)	92.393 (3)
V (Å³)	1493.6 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.38
Crystal size (mm)	0.48 × 0.13 × 0.13

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2000)
T_min, T_max	0.806, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	11420, 3405, 3079
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.075, 1.07
No. of reflections	3405
No. of parameters	230
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.85

Computer programs: CrystalClear (Rigaku, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2000).

Selected geometric parameters (Å, º) top

Ag1—N2	2.1663 (18)	Ag1—O1	2.3889 (18)
Ag1—N1ⁱ	2.207 (2)

N2—Ag1—N1ⁱ	150.61 (7)	N1ⁱ—Ag1—O1	93.66 (7)
N2—Ag1—O1	115.06 (7)

Symmetry code: (i) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O4	0.846 (19)	1.56 (2)	2.399 (3)	171 (4)
N3—H3A···O3ⁱⁱ	0.86	1.92	2.742 (3)	159.4

Symmetry code: (ii) x+1/2, −y+1/2, z+1/2.

Footnotes

‡Alternative address: Fuzhou University, Fuzhou, Fujian 350002 People's Republic of China.

Acknowledgements

The author gratefully acknowledges the financial support of the Key Science and Technology Project of Fujian Province (grant No. 2005H045).

References

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