Poly[4-(dimethyl­amino)pyridinium [(μ6-5-carboxy­benzene-1,2,4-tricarboxy­ato-κ6O1:O1′:O2:O4:O4′:O5)diargentate(I)]]

Zhu, X.-F.; Zhou, Y.-H.; Guan, L.; Zhang, H.

doi:10.1107/S1600536809028839

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages m994-m995

doi:10.1107/S1600536809028839

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Poly[4-(dimethylamino)pyridinium [(μ₆-5-carboxybenzene-1,2,4-tricarboxyato-κ⁶O¹:O^1′:O²:O⁴:O^4′:O⁵)diargentate(I)]]

Xiao-Fei Zhu,^a Yan-Hong Zhou,^a Li Guan ^a and Hong Zhang ^a ^*

^aFaculty of Chemistry, Northeast Normal University, Changchun 130024, People's Republic of China
^*Correspondence e-mail: zhangh@nenu.edu.cn

(Received 1 June 2009; accepted 21 July 2009; online 25 July 2009)

In the title compound, {(C₇H₁₁N₂)[Ag₂(C₁₀H₃O₈)]}_n, the polymeric anion consists of two Ag^I atoms and a Hbtc³⁻ ligand (H₄btc = benzene-1,2,4,5-tetracarboxylic acid). Each Ag^I atom is coordinated by four O atoms from three different Hbtc³⁻ ligands. The two Ag^I atoms are bridged by two bidentate carboxylate groups into an Ag₂O₄ cyclic unit, with an Ag⋯Ag distance of 2.8189 (3) Å. In this way, the Ag atoms are connected by the Hbtc³⁻ ligands into an extended two-dimensional layer structure. A three-dimensional network is accomplished through O—H⋯O hydrogen bonds between the anionic layers. The cationic guest Hdmap⁺ [dmap = 4-(dimethylamino)pyridine] is trapped in the network and adheres to the layer by an N—H⋯O hydrogen bond.

Related literature

For general background to metal-organic frameworks with 1,2,4,5-benzenetetracarboxylate liganda, see: Cao et al. (2002 ); Hu et al. (2004 ); Li et al. (2003 ). For related complexes, see: Chen (2008 ); Sun et al. (2003 ); Zheng et al. (2002 , 2003 ).

Experimental

Crystal data

(C₇H₁₁N₂)[Ag₂(C₁₀H₃O₈)]
M_r = 590.04
Triclinic, $[P \overline 1]$
a = 9.7192 (3) Å
b = 9.9936 (5) Å
c = 10.4968 (3) Å
α = 113.304 (4)°
β = 97.140 (3)°
γ = 103.260 (3)°
V = 884.65 (7) Å³
Z = 2
Mo Kα radiation
μ = 2.27 mm⁻¹
T = 293 K
0.24 × 0.18 × 0.14 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.611, T_max = 0.725
7226 measured reflections
3124 independent reflections
2808 reflections with I > 2σI)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.046
S = 1.06
3124 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—O1	2.5220 (15)
Ag1—O3ⁱ	2.1784 (15)
Ag1—O3	2.7573 (19)
Ag1—O6ⁱⁱ	2.1765 (15)
Ag2—O4	2.2091 (15)
Ag2—O5ⁱⁱⁱ	2.2224 (16)
Ag2—O5^iv	2.873 (2)
Ag2—O7^iv	2.4442 (15)
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+1; (iii) x, y+1, z+1; (iv) -x+1, -y, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H⋯O7^v	0.84	1.88	2.720 (2)	177
O2—H2⋯O8^vi	0.82	1.73	2.541 (2)	173
Symmetry codes: (v) x-1, y+1, z; (vi) x-1, y, z.

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 $[Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028839/hy2204sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028839/hy2204Isup2.hkl

checkCIF report

Comment top

More efforts have been made to construct MOFs (metal organic frameworks) materials by using 1,2,4,5-benzenetetracarboxylic acid (H₄btc) as molecular building block, owing to its complexed coordination modes to metal ions and various dimensionalities (Cao et al., 2002; Hu et al., 2004; Li et al., 2003). According to literature, the combination of H₄btc, as a polydentate ligand and silver(I) can produce various architectures, involving in [Ag₂(pbi)₂(H₂btc)]_n [pbi = 2-(3-pyridyl)-1H-benzimidazole] (Chen, 2008), [Ag(µ₃-hmt)]₂[Ag(NH₃)₂]₂(btc).3H₂O (hmt = hexamethylenetetramine) (Zheng et al., 2002), [Ag₈(µ₃-hmt)₂(µ₄-hmt)₂(µ-btc)₂(µ-H₂O)₃].18H₂O (Zheng et al., 2003), and [Ag(bipy)][H₂btc]_0.5.H₂O (Sun et al., 2003). Herein, the title complex, [Hdmap][Ag₂(Hbtc)] (dmap = 4-dimethylaminopyridine), with a layer structure is reported.

The structure of the title compound contains two crystallographically independent Ag^I atoms, one (Hbtc)^3- ligand and one (Hdmap)⁺ cantion. Each Ag^I atom is coordinated by four carboxylate O atoms from three different Hbtc ligands (Fig. 1), with three close bond distances [average Ag1—O = 2.2923 (15) and Ag2—O = 2.2919 (15) Å] and one long bond distance [Ag1—O = 2.7573 (19) and Ag2—O = 2.873 (2) Å] (Table 1). It is worth noting that two adjacent Ag1 and Ag2 atoms are bridged by two bidentate carboxylate groups into an Ag₂O₄ cyclic unit, with an Ag···Ag distance of 2.8189 (3) Å. The Hbtc ligand connects six Ag atoms, leading to a two-dimensional anionic layer (Fig. 2). The interlayer O—H···O hydrogen bonds hold adjacent layers together to bring out a supramolecular network. The cationic guest (Hdmap)⁺ is trapped in the network and adhere to the layer by an N—H···O hydrogen bond (Table 2).

Related literature top

For general background to metal-organic frameworks with 1,2,4,5-benzenetetracarboxylate liganda, see: Cao et al. (2002); Hu et al. (2004); Li et al. (2003). For related complexes, see: Chen (2008); Sun et al. (2003); Zheng et al. (2002, 2003).

Experimental top

A mixture of pyromelitic acid anhydride (0.218 g, 0.1 mmol) in distilled water (10 ml) was stirred at 333 K for 1 h until to get clear solution and then a DMF solution (2 ml) of AgNO₃ (0.169 g, 0.1 mmol) was added on stirring for 1 h under ambient condition. The resulting solution was allowed to stand in air at room temperature for 3 d. Colorless crystals were collected in 77.8% yield based on AgNO₃.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) 1 - x, 1 - y, 2 - z; (ii) 1 - x, -y, 1 - z; (iii) x, 1 + y, 1 + z; (iv) 1 - x, -y, 2 - z.]
	Fig. 2. A view of the two-dimensional layer in the title compound. H atoms are omitted for clarity.

Poly[4-(dimethylamino)pyridinium [(µ₆-5-carboxybenzene-1,2,4-tricarboxylato- κ⁶O¹:O^1':O²:O⁴:O^4': O⁵)diargentate(I)]] top

Crystal data top

(C₇H₁₁N₂)[Ag₂(C₁₀H₃O₈)]	Z = 2
M_r = 590.04	F(000) = 576
Triclinic, P1	D_x = 2.215 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7192 (3) Å	Cell parameters from 3901 reflections
b = 9.9936 (5) Å	θ = 4.4–25.0°
c = 10.4968 (3) Å	µ = 2.27 mm⁻¹
α = 113.304 (4)°	T = 293 K
β = 97.140 (3)°	Block, colorless
γ = 103.260 (3)°	0.24 × 0.18 × 0.14 mm
V = 884.65 (7) Å³

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	3124 independent reflections
Radiation source: fine-focus sealed tube	2808 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
Detector resolution: 10.0 pixels mm^-1	θ_max = 25.0°, θ_min = 4.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −11→11
T_min = 0.611, T_max = 0.725	l = −12→12
7226 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.018	H-atom parameters constrained
wR(F²) = 0.046	w = 1/[σ²(F_o²) + (0.0251P)² + 0.4969P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.003
3124 reflections	Δρ_max = 0.35 e Å⁻³
265 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0157 (6)

Crystal data top

(C₇H₁₁N₂)[Ag₂(C₁₀H₃O₈)]	γ = 103.260 (3)°
M_r = 590.04	V = 884.65 (7) Å³
Triclinic, P1	Z = 2
a = 9.7192 (3) Å	Mo Kα radiation
b = 9.9936 (5) Å	µ = 2.27 mm⁻¹
c = 10.4968 (3) Å	T = 293 K
α = 113.304 (4)°	0.24 × 0.18 × 0.14 mm
β = 97.140 (3)°

Data collection top

Oxford Diffraction Gemini R Ultra diffractometer	3124 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	2808 reflections with I > 2σ(I)
T_min = 0.611, T_max = 0.725	R_int = 0.012
7226 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.046	H-atom parameters constrained
S = 1.06	Δρ_max = 0.35 e Å⁻³
3124 reflections	Δρ_min = −0.47 e Å⁻³
265 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.421397 (19)	0.410977 (18)	0.802682 (17)	0.02690 (8)
Ag2	0.421385 (19)	0.385653 (19)	1.290598 (17)	0.02889 (9)
O1	0.22857 (16)	0.20334 (17)	0.81649 (18)	0.0277 (4)
O2	0.10698 (15)	−0.04467 (17)	0.71974 (19)	0.0329 (4)
H2	0.0364	−0.0126	0.7220	0.049*
O3	0.57621 (18)	0.37804 (17)	1.02125 (17)	0.0326 (4)
O4	0.4252 (2)	0.21751 (18)	1.07819 (17)	0.0344 (4)
O5	0.41174 (19)	−0.39642 (18)	0.45762 (18)	0.0357 (4)
O6	0.5636 (2)	−0.23946 (18)	0.39821 (17)	0.0341 (4)
O7	0.75751 (16)	−0.21312 (17)	0.65497 (17)	0.0251 (3)
O8	0.87465 (16)	0.03113 (17)	0.7214 (2)	0.0336 (4)
C1	0.2265 (2)	0.0702 (2)	0.7685 (2)	0.0178 (4)
C2	0.4977 (2)	0.2487 (2)	0.9985 (2)	0.0173 (4)
C3	0.4930 (2)	0.1181 (2)	0.8600 (2)	0.0160 (4)
C4	0.3628 (2)	−0.0996 (2)	0.6355 (2)	0.0177 (4)
H4	0.2755	−0.1617	0.5684	0.021*
C5	0.3627 (2)	0.0251 (2)	0.7570 (2)	0.0160 (4)
C6	0.6223 (2)	−0.0377 (2)	0.7128 (2)	0.0157 (4)
C7	0.4913 (2)	−0.1332 (2)	0.6121 (2)	0.0153 (4)
C8	0.6218 (2)	0.0862 (2)	0.8348 (2)	0.0185 (4)
H8	0.7093	0.1493	0.9012	0.022*
C9	0.4888 (2)	−0.2673 (2)	0.4775 (2)	0.0168 (4)
C10	0.7617 (2)	−0.0765 (2)	0.6939 (2)	0.0192 (4)
N1	0.0720 (2)	0.4030 (2)	0.1392 (2)	0.0333 (5)
N2	−0.1309 (2)	0.6318 (3)	0.4369 (2)	0.0378 (5)
H	−0.1683	0.6777	0.5021	0.045*
C11	0.0048 (2)	0.4765 (3)	0.2354 (2)	0.0271 (5)
C12	−0.0362 (3)	0.7091 (3)	0.3890 (3)	0.0354 (6)
H12	−0.0172	0.8144	0.4240	0.042*
C13	−0.1624 (3)	0.4795 (3)	0.3866 (3)	0.0375 (6)
H13	−0.2296	0.4279	0.4204	0.045*
C14	−0.0985 (3)	0.3988 (3)	0.2872 (3)	0.0343 (6)
H14	−0.1223	0.2931	0.2533	0.041*
C15	0.0325 (3)	0.6369 (3)	0.2906 (3)	0.0333 (6)
H15	0.0981	0.6930	0.2592	0.040*
C16	0.0426 (3)	0.2378 (3)	0.0780 (3)	0.0407 (6)
H16A	−0.0540	0.1883	0.0172	0.061*
H16B	0.0505	0.2065	0.1535	0.061*
H16C	0.1119	0.2095	0.0231	0.061*
C17	0.1797 (3)	0.4867 (4)	0.0902 (3)	0.0423 (7)
H17A	0.2588	0.5591	0.1700	0.063*
H17B	0.1351	0.5400	0.0473	0.063*
H17C	0.2160	0.4161	0.0210	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.03846 (13)	0.01606 (11)	0.01917 (11)	0.00464 (7)	0.01347 (8)	0.00093 (7)
Ag2	0.04268 (13)	0.01682 (11)	0.02185 (11)	0.00567 (8)	0.01695 (8)	0.00245 (8)
O1	0.0209 (8)	0.0163 (8)	0.0436 (10)	0.0084 (6)	0.0142 (7)	0.0076 (7)
O2	0.0123 (7)	0.0184 (8)	0.0581 (11)	0.0053 (6)	0.0090 (7)	0.0065 (8)
O3	0.0409 (10)	0.0154 (8)	0.0288 (9)	0.0006 (7)	0.0191 (7)	−0.0016 (7)
O4	0.0535 (11)	0.0211 (8)	0.0240 (8)	0.0075 (7)	0.0231 (8)	0.0037 (7)
O5	0.0431 (10)	0.0148 (8)	0.0356 (9)	−0.0001 (7)	0.0255 (8)	−0.0019 (7)
O6	0.0553 (11)	0.0201 (8)	0.0233 (8)	0.0081 (7)	0.0245 (8)	0.0034 (7)
O7	0.0233 (8)	0.0173 (8)	0.0361 (9)	0.0103 (6)	0.0155 (7)	0.0084 (7)
O8	0.0143 (8)	0.0191 (8)	0.0614 (12)	0.0046 (6)	0.0133 (7)	0.0108 (8)
C1	0.0168 (10)	0.0168 (11)	0.0191 (10)	0.0056 (8)	0.0084 (8)	0.0058 (9)
C2	0.0181 (10)	0.0166 (10)	0.0149 (9)	0.0087 (8)	0.0047 (8)	0.0027 (8)
C3	0.0185 (10)	0.0132 (10)	0.0154 (10)	0.0056 (8)	0.0061 (8)	0.0045 (8)
C4	0.0146 (10)	0.0155 (10)	0.0173 (10)	0.0036 (8)	0.0026 (8)	0.0026 (8)
C5	0.0151 (10)	0.0132 (10)	0.0199 (10)	0.0049 (7)	0.0079 (8)	0.0061 (8)
C6	0.0144 (10)	0.0132 (10)	0.0185 (10)	0.0047 (7)	0.0067 (8)	0.0050 (8)
C7	0.0173 (10)	0.0130 (9)	0.0160 (9)	0.0063 (8)	0.0073 (8)	0.0049 (8)
C8	0.0155 (10)	0.0143 (10)	0.0187 (10)	0.0028 (8)	0.0031 (8)	0.0016 (8)
C9	0.0168 (10)	0.0164 (10)	0.0150 (10)	0.0071 (8)	0.0035 (8)	0.0036 (8)
C10	0.0181 (10)	0.0173 (11)	0.0199 (10)	0.0063 (8)	0.0074 (8)	0.0045 (9)
N1	0.0372 (11)	0.0354 (11)	0.0322 (11)	0.0154 (9)	0.0194 (9)	0.0141 (9)
N2	0.0413 (12)	0.0458 (13)	0.0318 (11)	0.0272 (10)	0.0174 (10)	0.0123 (10)
C11	0.0270 (12)	0.0322 (13)	0.0235 (11)	0.0108 (10)	0.0076 (9)	0.0122 (10)
C12	0.0420 (14)	0.0289 (13)	0.0338 (13)	0.0143 (11)	0.0061 (11)	0.0113 (11)
C13	0.0364 (14)	0.0422 (15)	0.0414 (14)	0.0136 (11)	0.0216 (12)	0.0213 (13)
C14	0.0383 (14)	0.0280 (13)	0.0401 (14)	0.0111 (11)	0.0188 (12)	0.0150 (12)
C15	0.0369 (13)	0.0308 (13)	0.0344 (13)	0.0097 (10)	0.0128 (11)	0.0156 (11)
C16	0.0437 (15)	0.0410 (16)	0.0369 (14)	0.0218 (12)	0.0152 (12)	0.0102 (13)
C17	0.0371 (14)	0.0576 (18)	0.0399 (15)	0.0176 (13)	0.0225 (12)	0.0236 (14)

Geometric parameters (Å, º) top

Ag1—O1	2.5220 (15)	C6—C8	1.387 (3)
Ag1—O3ⁱ	2.1784 (15)	C6—C7	1.400 (3)
Ag1—O3	2.7573 (19)	C6—C10	1.507 (3)
Ag1—O6ⁱⁱ	2.1765 (15)	C7—C9	1.507 (3)
Ag2—O4	2.2091 (15)	C8—H8	0.9300
Ag2—O5ⁱⁱⁱ	2.2224 (16)	N1—C11	1.336 (3)
Ag2—O5^iv	2.873 (2)	N1—C16	1.455 (3)
Ag2—O7^iv	2.4442 (15)	N1—C17	1.460 (3)
Ag1—Ag2ⁱ	2.8189 (3)	N2—C12	1.339 (3)
O1—C1	1.216 (3)	N2—C13	1.341 (3)
O2—C1	1.306 (2)	N2—H	0.84
O2—H2	0.82	C11—C15	1.417 (3)
O3—C2	1.252 (3)	C11—C14	1.420 (3)
O4—C2	1.244 (3)	C12—C15	1.355 (3)
O5—C9	1.255 (3)	C12—H12	0.9300
O6—C9	1.240 (3)	C13—C14	1.361 (3)
O7—C10	1.249 (3)	C13—H13	0.9300
O8—C10	1.257 (2)	C14—H14	0.9300
C1—C5	1.496 (3)	C15—H15	0.9300
C2—C3	1.508 (3)	C16—H16A	0.9600
C3—C8	1.392 (3)	C16—H16B	0.9600
C3—C5	1.401 (3)	C16—H16C	0.9600
C4—C5	1.387 (3)	C17—H17A	0.9600
C4—C7	1.392 (3)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600

O6ⁱⁱ—Ag1—O3ⁱ	165.22 (6)	C4—C7—C6	118.95 (18)
O6ⁱⁱ—Ag1—O1	88.08 (6)	C4—C7—C9	120.01 (17)
O3ⁱ—Ag1—O1	104.84 (6)	C6—C7—C9	120.99 (17)
O6ⁱⁱ—Ag1—Ag2ⁱ	82.64 (4)	C6—C8—C3	121.33 (18)
O3ⁱ—Ag1—Ag2ⁱ	83.04 (4)	C6—C8—H8	119.3
O1—Ag1—Ag2ⁱ	162.98 (4)	C3—C8—H8	119.3
O3—Ag1—O1	80.23 (5)	O6—C9—O5	126.56 (19)
O3—Ag1—O3ⁱ	82.06 (6)	O6—C9—C7	117.07 (18)
O3—Ag1—O6ⁱⁱ	107.63 (5)	O5—C9—C7	116.36 (17)
O3—Ag1—Ag2ⁱ	116.16 (4)	O7—C10—O8	124.57 (19)
O4—Ag2—O5ⁱⁱⁱ	158.69 (7)	O7—C10—C6	117.63 (17)
O4—Ag2—O7^iv	97.68 (6)	O8—C10—C6	117.78 (18)
O5ⁱⁱⁱ—Ag2—O7^iv	97.08 (5)	C11—N1—C16	122.5 (2)
O4—Ag2—Ag1ⁱ	81.08 (4)	C11—N1—C17	120.8 (2)
O5ⁱⁱⁱ—Ag2—Ag1ⁱ	81.40 (4)	C16—N1—C17	116.8 (2)
O7^iv—Ag2—Ag1ⁱ	168.58 (4)	C12—N2—C13	120.7 (2)
O5^iv—Ag2—O4	119.23 (5)	C12—N2—H	120.9
O5^iv—Ag2—O5ⁱⁱⁱ	78.86 (6)	C13—N2—H	118.3
O5^iv—Ag2—O7^iv	78.31 (5)	N1—C11—C15	121.4 (2)
O5^iv—Ag2—Ag1ⁱ	112.29 (4)	N1—C11—C14	122.1 (2)
C1—O1—Ag1	123.41 (13)	C15—C11—C14	116.4 (2)
C1—O2—H2	109.5	N2—C12—C15	121.3 (2)
C2—O3—Ag1ⁱ	123.07 (13)	N2—C12—H12	119.3
C2—O4—Ag2	124.47 (14)	C15—C12—H12	119.3
C9—O5—Ag2^v	123.12 (13)	N2—C13—C14	121.5 (2)
C9—O6—Ag1ⁱⁱ	124.62 (14)	N2—C13—H13	119.3
C10—O7—Ag2^iv	121.06 (12)	C14—C13—H13	119.3
O1—C1—O2	123.50 (18)	C13—C14—C11	119.7 (2)
O1—C1—C5	122.02 (17)	C13—C14—H14	120.1
O2—C1—C5	114.46 (17)	C11—C14—H14	120.1
O4—C2—O3	126.86 (19)	C12—C15—C11	120.3 (2)
O4—C2—C3	117.34 (18)	C12—C15—H15	119.8
O3—C2—C3	115.79 (17)	C11—C15—H15	119.8
C8—C3—C5	118.74 (18)	N1—C16—H16A	109.5
C8—C3—C2	119.06 (17)	N1—C16—H16B	109.5
C5—C3—C2	122.18 (17)	H16A—C16—H16B	109.5
C5—C4—C7	121.14 (18)	N1—C16—H16C	109.5
C5—C4—H4	119.4	H16A—C16—H16C	109.5
C7—C4—H4	119.4	H16B—C16—H16C	109.5
C4—C5—C3	119.97 (18)	N1—C17—H17A	109.5
C4—C5—C1	119.38 (17)	N1—C17—H17B	109.5
C3—C5—C1	120.24 (17)	H17A—C17—H17B	109.5
C8—C6—C7	119.81 (18)	N1—C17—H17C	109.5
C8—C6—C10	120.10 (17)	H17A—C17—H17C	109.5
C7—C6—C10	119.93 (17)	H17B—C17—H17C	109.5

O6ⁱⁱ—Ag1—O1—C1	31.61 (18)	C10—C6—C7—C9	−5.6 (3)
O3ⁱ—Ag1—O1—C1	−155.65 (17)	C7—C6—C8—C3	0.1 (3)
Ag2ⁱ—Ag1—O1—C1	88.4 (2)	C10—C6—C8—C3	−175.26 (19)
O5ⁱⁱⁱ—Ag2—O4—C2	43.7 (3)	C5—C3—C8—C6	−2.1 (3)
O7^iv—Ag2—O4—C2	177.18 (18)	C2—C3—C8—C6	176.43 (19)
Ag1ⁱ—Ag2—O4—C2	8.66 (17)	Ag1ⁱⁱ—O6—C9—O5	1.1 (3)
Ag1—O1—C1—O2	−150.04 (16)	Ag1ⁱⁱ—O6—C9—C7	−179.62 (13)
Ag1—O1—C1—C5	28.3 (3)	Ag2^v—O5—C9—O6	11.0 (3)
Ag2—O4—C2—O3	−2.3 (3)	Ag2^v—O5—C9—C7	−168.32 (13)
Ag2—O4—C2—C3	177.08 (13)	C4—C7—C9—O6	120.2 (2)
Ag1ⁱ—O3—C2—O4	−9.4 (3)	C6—C7—C9—O6	−57.5 (3)
Ag1ⁱ—O3—C2—C3	171.21 (13)	C4—C7—C9—O5	−60.4 (3)
O4—C2—C3—C8	−119.5 (2)	C6—C7—C9—O5	121.9 (2)
O3—C2—C3—C8	60.0 (3)	Ag2^iv—O7—C10—O8	151.16 (17)
O4—C2—C3—C5	59.0 (3)	Ag2^iv—O7—C10—C6	−27.2 (2)
O3—C2—C3—C5	−121.6 (2)	C8—C6—C10—O7	132.8 (2)
C7—C4—C5—C3	−1.1 (3)	C7—C6—C10—O7	−42.6 (3)
C7—C4—C5—C1	171.50 (18)	C8—C6—C10—O8	−45.6 (3)
C8—C3—C5—C4	2.6 (3)	C7—C6—C10—O8	139.0 (2)
C2—C3—C5—C4	−175.89 (19)	C16—N1—C11—C15	−178.3 (2)
C8—C3—C5—C1	−170.00 (18)	C17—N1—C11—C15	1.6 (3)
C2—C3—C5—C1	11.5 (3)	C16—N1—C11—C14	1.2 (4)
O1—C1—C5—C4	−138.5 (2)	C17—N1—C11—C14	−178.8 (2)
O2—C1—C5—C4	39.9 (3)	C13—N2—C12—C15	−1.2 (4)
O1—C1—C5—C3	34.1 (3)	C12—N2—C13—C14	0.9 (4)
O2—C1—C5—C3	−147.48 (19)	N2—C13—C14—C11	0.3 (4)
C5—C4—C7—C6	−0.8 (3)	N1—C11—C14—C13	179.2 (2)
C5—C4—C7—C9	−178.56 (19)	C15—C11—C14—C13	−1.2 (3)
C8—C6—C7—C4	1.3 (3)	N2—C12—C15—C11	0.2 (4)
C10—C6—C7—C4	176.73 (18)	N1—C11—C15—C12	−179.5 (2)
C8—C6—C7—C9	179.04 (19)	C14—C11—C15—C12	0.9 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H···O7^vi	0.84	1.88	2.720 (2)	177
O2—H2···O8^vii	0.82	1.73	2.541 (2)	173

Symmetry codes: (vi) x−1, y+1, z; (vii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	(C₇H₁₁N₂)[Ag₂(C₁₀H₃O₈)]
M_r	590.04
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.7192 (3), 9.9936 (5), 10.4968 (3)
α, β, γ (°)	113.304 (4), 97.140 (3), 103.260 (3)
V (Å³)	884.65 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.27
Crystal size (mm)	0.24 × 0.18 × 0.14

Data collection
Diffractometer	Oxford Diffraction Gemini R Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2006)
T_min, T_max	0.611, 0.725
No. of measured, independent and observed [I > 2σ(I)] reflections	7226, 3124, 2808
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.046, 1.06
No. of reflections	3124
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.47

Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999).

Selected bond lengths (Å) top

Ag1—O1	2.5220 (15)	Ag2—O5ⁱⁱⁱ	2.2224 (16)
Ag1—O3ⁱ	2.1784 (15)	Ag2—O5^iv	2.873 (2)
Ag1—O3	2.7573 (19)	Ag2—O7^iv	2.4442 (15)
Ag1—O6ⁱⁱ	2.1765 (15)	Ag1—Ag2ⁱ	2.8189 (3)
Ag2—O4	2.2091 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H···O7^v	0.84	1.88	2.720 (2)	177
O2—H2···O8^vi	0.82	1.73	2.541 (2)	173

Symmetry codes: (v) x−1, y+1, z; (vi) x−1, y, z.

Acknowledgements

We gratefully acknowledge financial support from the NSF of China (grant No. 20771023), the 863 Program (grant No. 2007 A A03z218) and the Analysis and Testing Foundation of Northeast Normal University.

References

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