Bis[μ-1,2-bis­(1H-imidazol-1-ylmeth­yl)benzene-κ2N3:N3′]disilver(I) bis­(4-carb­oxy­naphthalene-1-carboxyl­ate) tetra­hydrate

Yang, Y.; Yuan, G.

doi:10.1107/S1600536811018691

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m802

doi:10.1107/S1600536811018691

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Bis[μ-1,2-bis(1H-imidazol-1-ylmethyl)benzene-κ²N³:N^3′]disilver(I) bis(4-carboxynaphthalene-1-carboxylate) tetrahydrate

Yan Yang ^a ^* and Guohui Yuan ^b

^aDepartment of Chemistry, Tonghua Normal University, Tonghua 134001, People's Republic of China, and ^bSchool of Chemical Engineering and Technology, Harbin Institute of Technology, Harbin 150001, People's Republic of China
^*Correspondence e-mail: yangyantonghua@yahoo.com.cn

(Received 18 April 2011; accepted 17 May 2011; online 25 May 2011)

In the title compound, [Ag₂(C₁₄H₁₄N₄)₂](C₁₂H₇O₄)₂·4H₂O, the dinuclear dication has crystallographically imposed inversion symmetry. Each Ag^I ion is bicoordinated in a slightly distorted linear coordination geometry by the N atoms of two ligands, resulting in the formation of a 22-membered metallamacrocycle. In the dication, π–π interactions are observed between the imidazole rings, with centroid–centroid distances of 3.528 (3) Å and dihedral angles of 9.92 (9)°. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds and π–π interactions involving the benzene rings of adjacent dications, with centroid–centroid distances of 3.651 (2) Å.

Related literature

For the synthesis and structures of related compounds, see: Tan et al. (2004 ); Liu et al. (2007 ); Liu, Ma et al. (2008 ); Liu, Chi & Wang (2008 ); Sun et al. (2009 ).

Experimental

Crystal data

[Ag₂(C₁₄H₁₄N₄)₂](C₁₂H₇O₄)₂·4H₂O
M_r = 1194.74
Triclinic, $[P \overline 1]$
a = 9.6644 (5) Å
b = 11.3769 (12) Å
c = 11.8255 (5) Å
α = 109.376 (8)°
β = 95.783 (3)°
γ = 94.442 (4)°
V = 1211.79 (15) Å³
Z = 1
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 293 K
0.15 × 0.12 × 0.11 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.35, T_max = 0.59
8572 measured reflections
4904 independent reflections
3384 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.069
S = 0.89
4904 reflections
346 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.82	1.69	2.496 (2)	166
O1W—HW11⋯O4	0.87 (2)	1.96 (2)	2.814 (3)	166 (3)
O1W—HW12⋯O2Wⁱⁱ	0.83 (2)	2.12 (2)	2.902 (3)	158 (3)
O2W—HW21⋯O1	0.84 (2)	1.99 (2)	2.810 (3)	164 (4)
O2W—HW22⋯O3ⁱ	0.88 (2)	2.13 (3)	2.841 (3)	138 (3)
Symmetry codes: (i) x-1, y, z; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018691/rz2589sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018691/rz2589Isup2.hkl

checkCIF report

Comment top

The design and synthesis of silver(I) complexes have attracted intense interests of chemists (Liu, Chi & Wang, 2008; Tan et al., 2004) because of the versatility of their coordination geometry (Sun et al., 2009). So far, some complexes, modified by secondary nitrogen-based ligands, have been reported (Liu et al., 2007). In this work, the combination of 1,2-bis(1H-imidazol-1-ylmethyl)benzene (1,2-bix) with naphthalene-1,4-dicarboxylic acid (1,4-H₂ndc) and silver(I) ions resulted in the title compound, whose synthesis and structure are reported herein.

The contents of the asymmetric unit of the title compound is shown in Fig. 1. The complex, which has crystallographically imposed inversion symmetry, shows a binuclear structure, where each of silver(I) atom has a slightly distorted linear geometry and is coordinated by the N atoms from two 1,2-bix ligands. The Ag-N bond distances are within the normal range and are comparable to those observed in related N-containing compounds (Liu, Ma et al., 2008). Notably, the 1,4-Hndc anion does not coordinate to the metal and acts as a counter-anion. In the dication, π-π interactions are observed between the imidazole rings (N1/N2/C1–C3 and N3/N4/C12–C14), with centroid-centroid distance of 3.528 (3) Å and dihedral angles of 9.92 (9)°. The crystal structure is stabilized by a three-dimensional network of intermolecular O—H···O hydrogen bonds (Table 1) and π-π interactions involving the benzene rings of adjacent dications, with centroid-to-centroid distances Cg1···Cg1ⁱ = 3.651 (2) Å [Cg1 is the centroid of the C5–C10 ring; symmetry code: (i) 1-x, -y, 1-z].

Related literature top

For the synthesis and structures of related compounds, see: Tan et al. (2004); Liu et al. (2007); Liu, Ma et al. (2008); Liu, Chi & Wang (2008); Sun et al. (2009).

Experimental top

A mixture of AgNO₃^.2H₂O (0.5 mmol), naphthalene-1,4-dicarboxylic acid (0.5 mmol), 1,2-bis(1H-imidazol-1-ylmethyl)benzene (0.5 mmol) in H₂O (12 ml) was adjusted to pH = 5-6 by addition of aqueous NaOH solution, and heated at 145°C for 2 days. After the mixture was slowly cooled to room temperature, crystals of the title compound suitable for X-ray analysis were obtained (yield 33%).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level. Symmetry code: (i) 2-x, -y, -z.

Bis[µ-1,2-bis(1H-imidazol-1-ylmethyl)benzene- κ²N³:N^3']disilver(I) bis(4-carboxynaphthalene-1-carboxylate) tetrahydrate top

Crystal data top

[Ag₂(C₁₄H₁₄N₄)₂](C₁₂H₇O₄)₂·4H₂O	Z = 1
M_r = 1194.74	F(000) = 608
Triclinic, P1	D_x = 1.637 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6644 (5) Å	Cell parameters from 4904 reflections
b = 11.3769 (12) Å	θ = 1.8–26.4°
c = 11.8255 (5) Å	µ = 0.88 mm⁻¹
α = 109.376 (8)°	T = 293 K
β = 95.783 (3)°	Block, pale yellow
γ = 94.442 (4)°	0.15 × 0.12 × 0.11 mm
V = 1211.79 (15) Å³

Data collection top

Bruker APEX diffractometer	4904 independent reflections
Radiation source: fine-focus sealed tube	3384 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ϕ and ω scans	θ_max = 26.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −11→12
T_min = 0.35, T_max = 0.59	k = −14→12
8572 measured reflections	l = −14→11

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	w = 1/[σ²(F_o²) + (0.0385P)²] where P = (F_o² + 2F_c²)/3
4904 reflections	(Δ/σ)_max = 0.001
346 parameters	Δρ_max = 0.30 e Å⁻³
6 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ag₂(C₁₄H₁₄N₄)₂](C₁₂H₇O₄)₂·4H₂O	γ = 94.442 (4)°
M_r = 1194.74	V = 1211.79 (15) Å³
Triclinic, P1	Z = 1
a = 9.6644 (5) Å	Mo Kα radiation
b = 11.3769 (12) Å	µ = 0.88 mm⁻¹
c = 11.8255 (5) Å	T = 293 K
α = 109.376 (8)°	0.15 × 0.12 × 0.11 mm
β = 95.783 (3)°

Data collection top

Bruker APEX diffractometer	4904 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3384 reflections with I > 2σ(I)
T_min = 0.35, T_max = 0.59	R_int = 0.023
8572 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	6 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 0.89	Δρ_max = 0.30 e Å⁻³
4904 reflections	Δρ_min = −0.43 e Å⁻³
346 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.6791 (3)	−0.0550 (2)	0.0091 (2)	0.0501 (6)
H1	0.6710	−0.1140	−0.0684	0.060*
C2	0.6045 (3)	−0.0634 (2)	0.0974 (2)	0.0458 (6)
H2	0.5361	−0.1279	0.0919	0.055*
C3	0.7469 (2)	0.1091 (2)	0.1643 (2)	0.0424 (6)
H3	0.7937	0.1857	0.2157	0.051*
C4	0.5997 (3)	0.0755 (2)	0.3151 (2)	0.0442 (6)
H4A	0.5347	0.1374	0.3205	0.053*
H4B	0.6790	0.1137	0.3774	0.053*
C5	0.5284 (2)	−0.0355 (2)	0.33815 (18)	0.0341 (5)
C6	0.3839 (2)	−0.0568 (2)	0.3188 (2)	0.0434 (6)
H6	0.3335	−0.0034	0.2905	0.052*
C7	0.3121 (2)	−0.1558 (3)	0.3405 (2)	0.0479 (6)
H7	0.2147	−0.1685	0.3266	0.058*
C8	0.3846 (3)	−0.2340 (2)	0.3823 (2)	0.0460 (6)
H8	0.3371	−0.3008	0.3968	0.055*
C9	0.5289 (3)	−0.2138 (2)	0.4032 (2)	0.0420 (6)
H9	0.5780	−0.2673	0.4324	0.050*
C10	0.6025 (2)	−0.1153 (2)	0.38161 (18)	0.0329 (5)
C11	0.7610 (2)	−0.0995 (2)	0.4061 (2)	0.0443 (6)
H11A	0.7950	−0.0110	0.4437	0.053*
H11B	0.7903	−0.1418	0.4618	0.053*
C12	0.9213 (2)	−0.0917 (2)	0.2549 (2)	0.0402 (6)
H12	0.9636	−0.0104	0.2967	0.048*
C13	0.7869 (2)	−0.2677 (2)	0.2088 (2)	0.0465 (6)
H13	0.7210	−0.3304	0.2117	0.056*
C14	0.8654 (3)	−0.2743 (2)	0.1202 (2)	0.0510 (7)
H14	0.8624	−0.3432	0.0500	0.061*
C15	1.0338 (2)	0.4758 (2)	0.2815 (2)	0.0376 (5)
C16	0.87617 (19)	0.45208 (19)	0.27283 (19)	0.0296 (5)
C17	0.8186 (2)	0.4650 (2)	0.3765 (2)	0.0392 (6)
H17	0.8761	0.4916	0.4503	0.047*
C18	0.6738 (2)	0.4386 (2)	0.3729 (2)	0.0385 (5)
H18	0.6374	0.4426	0.4438	0.046*
C19	0.58560 (19)	0.40728 (19)	0.26764 (19)	0.0294 (5)
C20	0.4319 (2)	0.3805 (2)	0.2734 (2)	0.0353 (5)
C21	0.64007 (19)	0.39844 (18)	0.15716 (18)	0.0255 (4)
C22	0.78814 (19)	0.41758 (18)	0.16013 (18)	0.0246 (4)
C23	0.8428 (2)	0.40779 (19)	0.05138 (19)	0.0314 (5)
H23	0.9393	0.4196	0.0527	0.038*
C24	0.7584 (2)	0.3816 (2)	−0.0548 (2)	0.0386 (5)
H24	0.7967	0.3765	−0.1251	0.046*
C25	0.6131 (2)	0.3624 (2)	−0.0577 (2)	0.0417 (6)
H25	0.5551	0.3439	−0.1306	0.050*
C26	0.5555 (2)	0.3705 (2)	0.04427 (19)	0.0357 (5)
H26	0.4587	0.3575	0.0400	0.043*
O1	0.39354 (17)	0.3166 (2)	0.3301 (2)	0.0755 (7)
O2	0.35024 (15)	0.43133 (18)	0.21712 (17)	0.0592 (5)
H2A	0.2689	0.4124	0.2246	0.089*
O1W	1.0555 (2)	0.7995 (2)	0.5309 (2)	0.0790 (6)
HW11	1.053 (4)	0.725 (2)	0.477 (3)	0.119*
HW12	0.991 (3)	0.788 (3)	0.569 (3)	0.119*
O3	1.09219 (15)	0.38750 (17)	0.21193 (16)	0.0525 (4)
O2W	0.1287 (2)	0.1769 (2)	0.2855 (3)	0.0908 (7)
HW21	0.204 (3)	0.224 (3)	0.313 (4)	0.136*
HW22	0.086 (4)	0.210 (4)	0.237 (3)	0.136*
O4	1.09571 (17)	0.57350 (19)	0.35306 (17)	0.0630 (5)
Ag1	0.91046 (2)	0.11314 (2)	−0.04497 (2)	0.05935 (10)
N1	0.64894 (18)	0.04051 (16)	0.19530 (16)	0.0346 (4)
N2	0.7687 (2)	0.05428 (19)	0.05184 (18)	0.0461 (5)
N3	0.82247 (17)	−0.15126 (17)	0.29391 (16)	0.0350 (4)
N4	0.95103 (19)	−0.16342 (18)	0.14922 (18)	0.0443 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0624 (17)	0.0469 (16)	0.0398 (14)	0.0010 (14)	0.0177 (12)	0.0115 (12)
C2	0.0520 (15)	0.0433 (15)	0.0415 (14)	−0.0066 (12)	0.0128 (11)	0.0145 (12)
C3	0.0452 (14)	0.0336 (13)	0.0498 (16)	−0.0008 (11)	0.0144 (12)	0.0151 (12)
C4	0.0566 (15)	0.0378 (14)	0.0404 (14)	0.0063 (12)	0.0215 (12)	0.0118 (11)
C5	0.0379 (13)	0.0377 (13)	0.0275 (12)	0.0048 (10)	0.0158 (10)	0.0089 (10)
C6	0.0396 (13)	0.0542 (16)	0.0362 (13)	0.0137 (12)	0.0109 (11)	0.0118 (12)
C7	0.0315 (13)	0.0632 (18)	0.0379 (14)	−0.0060 (12)	0.0124 (11)	0.0029 (13)
C8	0.0487 (15)	0.0441 (15)	0.0401 (14)	−0.0110 (13)	0.0201 (12)	0.0073 (12)
C9	0.0525 (15)	0.0419 (14)	0.0365 (13)	0.0076 (12)	0.0177 (11)	0.0162 (11)
C10	0.0337 (12)	0.0372 (13)	0.0272 (11)	0.0032 (10)	0.0134 (9)	0.0080 (10)
C11	0.0362 (13)	0.0569 (16)	0.0398 (14)	0.0055 (12)	0.0122 (11)	0.0143 (12)
C12	0.0309 (12)	0.0368 (13)	0.0545 (16)	0.0030 (10)	0.0133 (11)	0.0156 (12)
C13	0.0425 (14)	0.0290 (13)	0.0708 (18)	0.0033 (11)	0.0266 (13)	0.0157 (13)
C14	0.0514 (15)	0.0351 (14)	0.0646 (17)	0.0075 (12)	0.0272 (13)	0.0084 (13)
C15	0.0227 (11)	0.0521 (15)	0.0397 (14)	−0.0015 (11)	0.0024 (10)	0.0198 (12)
C16	0.0181 (10)	0.0340 (12)	0.0381 (13)	0.0033 (9)	0.0047 (9)	0.0138 (10)
C17	0.0228 (11)	0.0583 (16)	0.0344 (13)	0.0021 (11)	−0.0020 (9)	0.0155 (12)
C18	0.0269 (11)	0.0567 (15)	0.0342 (13)	0.0049 (11)	0.0103 (10)	0.0166 (11)
C19	0.0186 (10)	0.0339 (12)	0.0369 (13)	0.0056 (9)	0.0070 (9)	0.0122 (10)
C20	0.0224 (11)	0.0426 (14)	0.0408 (13)	0.0032 (10)	0.0089 (10)	0.0131 (11)
C21	0.0194 (10)	0.0240 (11)	0.0330 (12)	0.0043 (8)	0.0046 (9)	0.0090 (9)
C22	0.0191 (10)	0.0214 (10)	0.0321 (12)	0.0019 (8)	0.0042 (8)	0.0076 (9)
C23	0.0212 (10)	0.0320 (12)	0.0413 (13)	0.0025 (9)	0.0105 (10)	0.0114 (10)
C24	0.0377 (13)	0.0426 (14)	0.0344 (13)	0.0022 (11)	0.0095 (10)	0.0109 (11)
C25	0.0385 (13)	0.0503 (15)	0.0303 (13)	0.0017 (11)	−0.0035 (10)	0.0092 (11)
C26	0.0216 (11)	0.0423 (14)	0.0393 (13)	0.0015 (10)	0.0028 (10)	0.0095 (11)
O1	0.0282 (9)	0.1157 (17)	0.1216 (18)	0.0090 (10)	0.0207 (10)	0.0889 (15)
O2	0.0200 (8)	0.0928 (14)	0.0906 (14)	0.0163 (9)	0.0166 (9)	0.0605 (12)
O1W	0.0747 (15)	0.0615 (14)	0.0900 (17)	−0.0045 (12)	0.0228 (12)	0.0110 (12)
O3	0.0211 (8)	0.0636 (12)	0.0697 (12)	0.0109 (8)	0.0091 (8)	0.0167 (10)
O2W	0.0619 (14)	0.0779 (17)	0.146 (2)	−0.0041 (12)	0.0282 (14)	0.0553 (16)
O4	0.0303 (9)	0.0721 (13)	0.0657 (12)	−0.0156 (9)	0.0044 (9)	0.0014 (11)
Ag1	0.05254 (14)	0.07269 (17)	0.07007 (17)	0.00896 (11)	0.03247 (11)	0.03988 (13)
N1	0.0398 (11)	0.0306 (10)	0.0364 (11)	0.0028 (9)	0.0122 (8)	0.0139 (9)
N2	0.0498 (12)	0.0460 (13)	0.0540 (14)	0.0089 (10)	0.0240 (10)	0.0268 (11)
N3	0.0284 (10)	0.0357 (11)	0.0442 (11)	0.0057 (8)	0.0121 (8)	0.0155 (9)
N4	0.0412 (11)	0.0414 (12)	0.0590 (14)	0.0097 (10)	0.0258 (10)	0.0221 (10)

Geometric parameters (Å, º) top

C1—C2	1.351 (3)	C14—H14	0.9300
C1—N2	1.371 (3)	C15—O4	1.217 (3)
C1—H1	0.9300	C15—O3	1.279 (3)
C2—N1	1.355 (3)	C15—C16	1.513 (3)
C2—H2	0.9300	C16—C17	1.365 (3)
C3—N2	1.315 (3)	C16—C22	1.424 (3)
C3—N1	1.336 (3)	C17—C18	1.402 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—N1	1.477 (3)	C18—C19	1.360 (3)
C4—C5	1.508 (3)	C18—H18	0.9300
C4—H4A	0.9700	C19—C21	1.433 (3)
C4—H4B	0.9700	C19—C20	1.506 (3)
C5—C6	1.381 (3)	C20—O1	1.203 (3)
C5—C10	1.393 (3)	C20—O2	1.273 (3)
C6—C7	1.387 (3)	C21—C26	1.417 (3)
C6—H6	0.9300	C21—C22	1.426 (3)
C7—C8	1.359 (4)	C22—C23	1.413 (3)
C7—H7	0.9300	C23—C24	1.356 (3)
C8—C9	1.379 (3)	C23—H23	0.9300
C8—H8	0.9300	C24—C25	1.400 (3)
C9—C10	1.389 (3)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.357 (3)
C10—C11	1.515 (3)	C25—H25	0.9300
C11—N3	1.468 (3)	C26—H26	0.9300
C11—H11A	0.9700	O2—H2A	0.8200
C11—H11B	0.9700	O1W—HW11	0.874 (17)
C12—N4	1.320 (3)	O1W—HW12	0.833 (17)
C12—N3	1.334 (3)	O2W—HW21	0.838 (18)
C12—H12	0.9300	O2W—HW22	0.882 (18)
C13—C14	1.340 (3)	Ag1—N2	2.0783 (17)
C13—N3	1.364 (3)	Ag1—N4ⁱ	2.0787 (17)
C13—H13	0.9300	N4—Ag1ⁱ	2.0787 (17)
C14—N4	1.373 (3)

C2—C1—N2	109.2 (2)	O3—C15—C16	115.7 (2)
C2—C1—H1	125.4	C17—C16—C22	119.93 (18)
N2—C1—H1	125.4	C17—C16—C15	118.49 (18)
C1—C2—N1	106.6 (2)	C22—C16—C15	121.58 (17)
C1—C2—H2	126.7	C16—C17—C18	120.8 (2)
N1—C2—H2	126.7	C16—C17—H17	119.6
N2—C3—N1	111.2 (2)	C18—C17—H17	119.6
N2—C3—H3	124.4	C19—C18—C17	121.12 (19)
N1—C3—H3	124.4	C19—C18—H18	119.4
N1—C4—C5	112.57 (18)	C17—C18—H18	119.4
N1—C4—H4A	109.1	C18—C19—C21	120.19 (17)
C5—C4—H4A	109.1	C18—C19—C20	117.02 (18)
N1—C4—H4B	109.1	C21—C19—C20	122.78 (18)
C5—C4—H4B	109.1	O1—C20—O2	124.30 (19)
H4A—C4—H4B	107.8	O1—C20—C19	120.2 (2)
C6—C5—C10	118.62 (19)	O2—C20—C19	115.45 (18)
C6—C5—C4	118.8 (2)	C26—C21—C22	117.74 (17)
C10—C5—C4	122.5 (2)	C26—C21—C19	123.92 (17)
C5—C6—C7	121.6 (2)	C22—C21—C19	118.34 (17)
C5—C6—H6	119.2	C23—C22—C16	121.85 (17)
C7—C6—H6	119.2	C23—C22—C21	118.69 (18)
C8—C7—C6	119.7 (2)	C16—C22—C21	119.38 (17)
C8—C7—H7	120.2	C24—C23—C22	121.85 (19)
C6—C7—H7	120.2	C24—C23—H23	119.1
C7—C8—C9	119.7 (2)	C22—C23—H23	119.1
C7—C8—H8	120.2	C23—C24—C25	119.4 (2)
C9—C8—H8	120.2	C23—C24—H24	120.3
C8—C9—C10	121.4 (2)	C25—C24—H24	120.3
C8—C9—H9	119.3	C26—C25—C24	121.0 (2)
C10—C9—H9	119.3	C26—C25—H25	119.5
C9—C10—C5	119.0 (2)	C24—C25—H25	119.5
C9—C10—C11	118.4 (2)	C25—C26—C21	121.34 (19)
C5—C10—C11	122.57 (19)	C25—C26—H26	119.3
N3—C11—C10	111.23 (18)	C21—C26—H26	119.3
N3—C11—H11A	109.4	C20—O2—H2A	109.5
C10—C11—H11A	109.4	HW11—O1W—HW12	101 (2)
N3—C11—H11B	109.4	HW21—O2W—HW22	103 (2)
C10—C11—H11B	109.4	N2—Ag1—N4ⁱ	177.04 (8)
H11A—C11—H11B	108.0	C3—N1—C2	107.41 (18)
N4—C12—N3	111.1 (2)	C3—N1—C4	124.93 (19)
N4—C12—H12	124.5	C2—N1—C4	127.65 (18)
N3—C12—H12	124.5	C3—N2—C1	105.65 (18)
C14—C13—N3	106.6 (2)	C3—N2—Ag1	128.88 (16)
C14—C13—H13	126.7	C1—N2—Ag1	125.46 (16)
N3—C13—H13	126.7	C12—N3—C13	107.32 (19)
C13—C14—N4	109.5 (2)	C12—N3—C11	126.2 (2)
C13—C14—H14	125.3	C13—N3—C11	126.49 (18)
N4—C14—H14	125.3	C12—N4—C14	105.53 (18)
O4—C15—O3	124.9 (2)	C12—N4—Ag1ⁱ	126.65 (15)
O4—C15—C16	119.4 (2)	C14—N4—Ag1ⁱ	127.71 (16)

Symmetry code: (i) −x+2, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱⁱ	0.82	1.69	2.496 (2)	166
O1W—HW11···O4	0.87 (2)	1.96 (2)	2.814 (3)	166 (3)
O1W—HW12···O2Wⁱⁱⁱ	0.83 (2)	2.12 (2)	2.902 (3)	158 (3)
O2W—HW21···O1	0.84 (2)	1.99 (2)	2.810 (3)	164 (4)
O2W—HW22···O3ⁱⁱ	0.88 (2)	2.13 (3)	2.841 (3)	138 (3)

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

Experimental details

Crystal data
Chemical formula	[Ag₂(C₁₄H₁₄N₄)₂](C₁₂H₇O₄)₂·4H₂O
M_r	1194.74
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.6644 (5), 11.3769 (12), 11.8255 (5)
α, β, γ (°)	109.376 (8), 95.783 (3), 94.442 (4)
V (Å³)	1211.79 (15)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.15 × 0.12 × 0.11

Data collection
Diffractometer	Bruker APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.35, 0.59
No. of measured, independent and observed [I > 2σ(I)] reflections	8572, 4904, 3384
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 0.89
No. of reflections	4904
No. of parameters	346
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.43

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.82	1.69	2.496 (2)	166
O1W—HW11···O4	0.874 (17)	1.959 (18)	2.814 (3)	166 (3)
O1W—HW12···O2Wⁱⁱ	0.833 (17)	2.115 (19)	2.902 (3)	158 (3)
O2W—HW21···O1	0.838 (18)	1.99 (2)	2.810 (3)	164 (4)
O2W—HW22···O3ⁱ	0.882 (18)	2.13 (3)	2.841 (3)	138 (3)

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

Acknowledgements

The authors thank Tonghua Normal University for financial support.

References

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