Construction of a dinuclear silver(I) coordination complex with a Schiff base containing 4-amino-1,2,4-triazole ligands

Sun, Q.; Zheng, F.; Sun, X.; Wang, W.

doi:10.1107/S1600536809004760

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Pages m283-m284

doi:10.1107/S1600536809004760

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Construction of a dinuclear silver(I) coordination complex with a Schiff base containing 4-amino-1,2,4-triazole ligands

Qiaozhen Sun,^a ^* Feng Zheng,^a Xiaodan Sun ^a and Wei Wang ^a

^aDepartment of Materials Chemistry, School of Materials Science and Engineering, Key Laboratory of Non-ferrous Metals of the Ministry of Education, Central South University, Changsha 410083, People's Republic of China
^*Correspondence e-mail: rosesunqz@yahoo.com.cn

(Received 1 November 2008; accepted 10 February 2009; online 18 February 2009)

The new ligand 1-(1,2,4-triazol-4-yliminomethyl)-2-naphthol (L) and the title silver(I) complex, namely bis[μ-1-(1,2,4-triazol-4-yliminomethyl)-2-naphthol]bis{[1-(1,2,4-triazol-4-yliminomethyl)-2-naphthol]silver(I)} dinitrate monohydrate, [Ag₂(C₁₃H₁₀N₄O)₄](NO₃)₂·H₂O, were synthesized. Each silver center in the dimeric complex (related by an inversion centre) is coordinated by two bridging L ligands and one additional L ligand in a monodentate fashion, exhibiting a distorted trigonal-planar coordination. The discrete dimers are further linked through O—H⋯O hydrogen bonds and weak π–π stacking interactions [the shortest atom–atom separation is ca 3.46 Å between the parallel stacking pairs]. Intramolecular O—H⋯N hydrogen bonds are also present.

Related literature

For the structures of other triazole Schiff base compounds, see: Beckmann & Brooker (2003 ); Drabent et al. (2003 , 2004 ); Garcia et al. (1997 ); Klingele & Brooker (2003 ); Liu et al. (2003 , 2006 ); Wang et al. (2006 ); Yi et al. (2004 ); Zhai et al. (2006 ). For related literature, see: Han et al. (2004 ).

Experimental

Crystal data

[Ag₂(C₁₃H₁₀N₄O)₄](NO₃)₂·H₂O
M_r = 1310.78
Triclinic, $[P \overline 1]$
a = 9.8594 (15) Å
b = 10.7081 (15) Å
c = 12.8567 (19) Å
α = 82.391 (2)°
β = 81.155 (2)°
γ = 77.626 (2)°
V = 1303.1 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.83 mm⁻¹
T = 293 K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.826, T_max = 0.887
6610 measured reflections
4536 independent reflections
3137 reflections with I > 2σ(I)
R_int = 0.118

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.133
S = 1.00
4536 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.84 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.83	2.548 (4)	145
O2—H2B⋯N5	0.82	1.87	2.588 (5)	145
O1W—H1WA⋯O3ⁱ	0.85	1.85	2.594 (15)	145
Symmetry code: (i) x, y-1, z.

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004760/wk2097sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004760/wk2097Isup2.hkl

checkCIF report

Comment top

1,2,4-triazoles and their derivatives are interesting bridging ligands. 1,2,4-triazoles can coordinate with metals by bridging two adjacent nitrogen atoms (N1 and N2) or via the 4-positioned one (N4). It is also a readily available and inexpensive resource. In the past two decades, a variety of coordination compounds containing 1,2,4-triazoles, N4 substituted 1,2,4-triazoles and their derivatives as ligands coordinated to metal ions have been reported (Beckmann & Brooker, 2003; Garcia et al., 1997; Klingele & Brooker, 2003; Liu et al., 2006; Liu et al., 2003; Yi et al., 2004; Zhai et al., 2006). Relatively few structurally characterized compounds based on 4-amido-1,2,4-triazoles Schiff base ligands have been reported (Drabent et al., 2004 and 2003; Wang et al., 2006). Here we describe the synthesis of the Ag(I) metal complex with a Schiff-base containing triazole ligand.

The molecular structure of complex 1 is shown in Figure 1. It consists of a discrete binuclear complex of Ag(I) bridged by two N1,N2-coordinated triazole ligands and an additional triazole ligand is bound to the Ag(I) ion in a monodentate fashion. This coordination mode results in a trigonal planar coordination environment (the sum of the angles around Ag metal atom is equal to 360 °). The Ag—Ag distance is equal to 3.81 Å, which is over the summed van der Waals radii of two Ag(I) atoms (3.44 Å) (Han et al., 2004). The Ag—N bond distances are in the range of 2.18–2.33 Å. The six-membered Ag-[N—N]₂-Ag rings remain almost planar (the mean plane deviation is 0.06 Å) from planarity, which is similar withdinuclear Cu(I) complex (Drabent et al., 2004). The Ag—N—N—Ag dihedral angle is 15.1 °.

In this complex all the ligands L are coordinated in almost planar E configuration and the resulting binuclear units can be described as X-shaped dimers. Sheets formed through C-H···O hydrogen bonds are further aggregated into three-dimensions by weak π-π stacking interactions between the naphthyl rings of the neighbouring dimers in different sheets and the shortest atom···atom separation is ca 3.46 Å between the parallel stacking pairs. The anions and water molecules interact with one another through O—H···N, O—H···O hydrogen bonds.

Related literature top

For related compounds, see: Beckmann & Brooker (2003); Drabent et al. (2003, 2004); Garcia et al. (1997); Klingele & Brooker (2003); Liu et al. (2003, 2006); Wang et al. (2006); Yi et al. (2004); Zhai et al. (2006). For related literature, see: Han et al. (2004).

Experimental top

Preparation of complex 1: The ligand L (0.1 mmol, 0.024 g) and AgNO₃ (0.1 mmol, 0.017 g) were mixed in acetonitrile and stirred at room temperature for one hour, the yellow solution was filtered and evaporated at room temperature. A few days later orange block crystals were obtained.

Preparation of the ligand L: An ethanolic solution (20 ml) of 2-hydroxy-1-napthaldehyde (1.72 g, 10 mmol) was added to a warm ethanolic solution (10 ml) of 4-amino- 1,2,4-triazole (0.84 g, 10 mmol) and the resulting solution was refluxed for four hours. The reaction mixture was then cooled to room temperature. Upon standing overnight the resultant yellow solid was filtered off, washed with diethyl ether and dried under vacuum. Yield: 90%. ¹H NMR (500 MHz, DMSO, 298 K): 9.66 (s, 1H), 9.34 (s, 2H), 8.84–8.86 (d, 1H), 8.05–8.07 (d, 1H), 7.90–7.92 (d, 1H), 7.61–7.64 (t, 1H), 7.43–7.46 (t, 1H), 7.28–7.30 (d, 1H).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A perspective view of the molecular structure showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [symmetry code: (A) 2 - x, -y, 2 - z.]
	Fig. 2. A packing diagram for the crystal along b axis, the NO₃^-, H₂O and hydrogen atoms are omitted for clarity.

bis[µ-1-(1,2,4-triazol-4-yliminomethyl)-2-naphthol]bis{[1-(1,2,4-triazol-4- yliminomethyl)-2-naphthol]silver(I)} dinitrate monohydrate top

Crystal data top

[Ag₂(C₁₃H₁₀N₄O)₄](NO₃)₂·H₂O	Z = 1
M_r = 1310.78	F(000) = 662
Triclinic, P1	D_x = 1.670 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8594 (15) Å	Cell parameters from 2250 reflections
b = 10.7081 (15) Å	θ = 2.4–25.4°
c = 12.8567 (19) Å	µ = 0.83 mm⁻¹
α = 82.391 (2)°	T = 293 K
β = 81.155 (2)°	Block, orange
γ = 77.626 (2)°	0.2 × 0.18 × 0.16 mm
V = 1303.1 (3) Å³

Data collection top

Bruker APEX CCD area-detector diffractometer	4536 independent reflections
Radiation source: fine-focus sealed tube	3137 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.118
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→11
T_min = 0.826, T_max = 0.887	k = −12→8
6610 measured reflections	l = −15→14

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)] = 0.055	Hydrogen site location: geom, H2O from difmap
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0601P)²] where P = (F_o² + 2F_c²)/3
4536 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 0.85 e Å⁻³
0 restraints	Δρ_min = −0.84 e Å⁻³

Crystal data top

[Ag₂(C₁₃H₁₀N₄O)₄](NO₃)₂·H₂O	γ = 77.626 (2)°
M_r = 1310.78	V = 1303.1 (3) Å³
Triclinic, P1	Z = 1
a = 9.8594 (15) Å	Mo Kα radiation
b = 10.7081 (15) Å	µ = 0.83 mm⁻¹
c = 12.8567 (19) Å	T = 293 K
α = 82.391 (2)°	0.2 × 0.18 × 0.16 mm
β = 81.155 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	4536 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3137 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.887	R_int = 0.118
6610 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.00	Δρ_max = 0.85 e Å⁻³
4536 reflections	Δρ_min = −0.84 e Å⁻³
379 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.84563 (4)	0.12190 (4)	0.95202 (3)	0.0613 (2)
O1	0.3147 (4)	0.5935 (3)	0.5781 (2)	0.0564 (9)
H1A	0.3862	0.5514	0.6002	0.085*
O2	1.2327 (4)	0.0054 (4)	0.4026 (3)	0.0701 (11)
H2B	1.2018	0.0029	0.4656	0.105*
N1	0.4657 (4)	0.4732 (4)	0.7179 (3)	0.0488 (10)
N2	0.5888 (4)	0.3908 (4)	0.7472 (3)	0.0447 (10)
N3	0.7966 (4)	0.2720 (4)	0.7236 (3)	0.0590 (12)
N4	0.7427 (4)	0.2564 (4)	0.8288 (3)	0.0554 (11)
N5	1.2436 (4)	−0.0497 (4)	0.6037 (3)	0.0453 (9)
N6	1.1907 (4)	−0.0406 (3)	0.7095 (3)	0.0412 (9)
N7	1.0373 (4)	0.0221 (4)	0.8420 (3)	0.0489 (10)
N8	1.1554 (4)	−0.0524 (4)	0.8806 (3)	0.0447 (10)
C1	0.1290 (5)	0.6319 (4)	0.8481 (4)	0.0423 (11)
C2	0.1404 (6)	0.6048 (5)	0.9573 (4)	0.0530 (13)
H2A	0.2232	0.5561	0.9789	0.064*
C3	0.0338 (6)	0.6481 (6)	1.0306 (4)	0.0633 (15)
H3A	0.0449	0.6287	1.1019	0.076*
C4	−0.0937 (6)	0.7218 (6)	1.0028 (4)	0.0663 (15)
H4A	−0.1664	0.7506	1.0545	0.080*
C5	−0.1082 (6)	0.7501 (5)	0.8987 (5)	0.0650 (15)
H5A	−0.1922	0.7993	0.8794	0.078*
C6	−0.0002 (5)	0.7072 (5)	0.8189 (4)	0.0514 (12)
C7	−0.0158 (6)	0.7374 (5)	0.7109 (4)	0.0582 (14)
H7A	−0.1003	0.7859	0.6921	0.070*
C8	0.0863 (6)	0.6988 (5)	0.6352 (4)	0.0552 (14)
H8A	0.0722	0.7200	0.5646	0.066*
C9	0.2163 (5)	0.6255 (4)	0.6608 (4)	0.0442 (11)
C10	0.2382 (5)	0.5910 (4)	0.7651 (4)	0.0404 (11)
C11	0.3702 (5)	0.5102 (4)	0.7907 (4)	0.0419 (11)
H11A	0.3840	0.4858	0.8611	0.050*
C12	0.6178 (5)	0.3277 (5)	0.8406 (4)	0.0515 (13)
H12A	0.5582	0.3338	0.9040	0.062*
C13	0.7004 (5)	0.3530 (5)	0.6776 (4)	0.0548 (14)
H13A	0.7082	0.3809	0.6057	0.066*
C14	1.5717 (5)	−0.2019 (5)	0.4532 (4)	0.0459 (11)
C15	1.6506 (5)	−0.2714 (5)	0.5336 (4)	0.0570 (13)
H15A	1.6110	−0.2711	0.6041	0.068*
C16	1.7841 (6)	−0.3386 (6)	0.5089 (5)	0.0684 (16)
H16A	1.8327	−0.3846	0.5629	0.082*
C17	1.8483 (7)	−0.3395 (6)	0.4050 (6)	0.083 (2)
H17A	1.9405	−0.3821	0.3897	0.099*
C18	1.7744 (7)	−0.2771 (6)	0.3256 (5)	0.0719 (17)
H18A	1.8153	−0.2810	0.2556	0.086*
C19	1.6372 (6)	−0.2068 (5)	0.3479 (4)	0.0577 (14)
C20	1.5622 (7)	−0.1409 (6)	0.2656 (4)	0.0679 (17)
H20A	1.6040	−0.1457	0.1959	0.082*
C21	1.4303 (7)	−0.0703 (6)	0.2851 (4)	0.0673 (17)
H21A	1.3840	−0.0259	0.2294	0.081*
C22	1.3641 (6)	−0.0650 (5)	0.3907 (4)	0.0526 (13)
C23	1.4329 (5)	−0.1275 (4)	0.4742 (3)	0.0435 (11)
C24	1.3675 (5)	−0.1161 (5)	0.5824 (3)	0.0441 (11)
H24A	1.4163	−0.1578	0.6377	0.053*
C25	1.0619 (5)	0.0279 (5)	0.7388 (4)	0.0477 (12)
H25A	1.0000	0.0725	0.6926	0.057*
C26	1.2458 (5)	−0.0883 (4)	0.7999 (3)	0.0432 (11)
H26A	1.3346	−0.1390	0.8039	0.052*
N9	0.5609 (6)	0.7008 (7)	0.8823 (5)	0.0847 (17)
O3	0.5165 (10)	0.7921 (8)	0.9419 (6)	0.183 (4)
O4	0.5557 (6)	0.7361 (6)	0.7950 (4)	0.125 (2)
O5	0.5869 (6)	0.5986 (5)	0.9295 (5)	0.116 (2)
O1W	0.6044 (13)	−0.0162 (13)	0.9945 (10)	0.143 (5)	0.50
H1WA	0.6068	−0.0783	0.9589	0.171*	0.50
H1WB	0.5600	−0.0207	1.0566	0.171*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0486 (3)	0.0810 (4)	0.0381 (2)	0.0158 (2)	−0.00257 (16)	0.00200 (18)
O1	0.053 (2)	0.067 (2)	0.0399 (17)	0.0063 (18)	−0.0092 (16)	0.0002 (16)
O2	0.076 (3)	0.077 (3)	0.0453 (19)	0.013 (2)	−0.0091 (18)	−0.0055 (18)
N1	0.041 (2)	0.054 (3)	0.046 (2)	0.005 (2)	−0.0109 (19)	−0.0009 (19)
N2	0.037 (2)	0.051 (2)	0.039 (2)	0.0072 (18)	−0.0074 (17)	−0.0035 (17)
N3	0.046 (3)	0.076 (3)	0.041 (2)	0.011 (2)	−0.0012 (19)	−0.001 (2)
N4	0.048 (3)	0.073 (3)	0.037 (2)	0.009 (2)	−0.0116 (19)	−0.001 (2)
N5	0.047 (2)	0.046 (2)	0.0352 (19)	0.0018 (19)	0.0022 (17)	−0.0045 (16)
N6	0.038 (2)	0.041 (2)	0.0361 (19)	0.0033 (18)	0.0052 (16)	−0.0051 (16)
N7	0.038 (2)	0.054 (3)	0.043 (2)	0.0105 (19)	−0.0008 (17)	−0.0038 (18)
N8	0.037 (2)	0.053 (3)	0.036 (2)	0.0062 (18)	−0.0033 (17)	−0.0029 (17)
C1	0.036 (3)	0.039 (3)	0.051 (3)	−0.003 (2)	−0.010 (2)	−0.004 (2)
C2	0.045 (3)	0.061 (3)	0.052 (3)	−0.008 (3)	−0.011 (2)	−0.003 (2)
C3	0.058 (4)	0.087 (4)	0.044 (3)	−0.017 (3)	0.006 (2)	−0.013 (3)
C4	0.049 (3)	0.082 (4)	0.063 (3)	−0.004 (3)	0.009 (3)	−0.022 (3)
C5	0.041 (3)	0.060 (4)	0.089 (4)	0.001 (3)	−0.005 (3)	−0.012 (3)
C6	0.035 (3)	0.051 (3)	0.066 (3)	−0.002 (2)	−0.009 (2)	−0.008 (2)
C7	0.043 (3)	0.058 (3)	0.070 (4)	0.005 (3)	−0.024 (3)	−0.001 (3)
C8	0.056 (3)	0.056 (3)	0.049 (3)	0.006 (3)	−0.022 (3)	0.000 (2)
C9	0.046 (3)	0.041 (3)	0.045 (3)	−0.003 (2)	−0.011 (2)	−0.001 (2)
C10	0.034 (3)	0.036 (3)	0.051 (3)	−0.003 (2)	−0.011 (2)	−0.005 (2)
C11	0.037 (3)	0.046 (3)	0.039 (2)	0.000 (2)	−0.007 (2)	−0.005 (2)
C12	0.042 (3)	0.067 (3)	0.035 (2)	0.014 (2)	−0.008 (2)	−0.006 (2)
C13	0.045 (3)	0.071 (4)	0.036 (2)	0.009 (3)	−0.001 (2)	0.002 (2)
C14	0.048 (3)	0.043 (3)	0.048 (3)	−0.014 (2)	0.005 (2)	−0.014 (2)
C15	0.048 (3)	0.058 (3)	0.062 (3)	−0.004 (3)	0.006 (3)	−0.019 (3)
C16	0.041 (3)	0.076 (4)	0.086 (4)	−0.004 (3)	−0.001 (3)	−0.022 (3)
C17	0.053 (4)	0.079 (5)	0.109 (5)	−0.007 (3)	0.025 (4)	−0.040 (4)
C18	0.068 (4)	0.076 (4)	0.069 (4)	−0.024 (3)	0.031 (3)	−0.029 (3)
C19	0.062 (4)	0.056 (3)	0.055 (3)	−0.022 (3)	0.018 (3)	−0.020 (3)
C20	0.085 (5)	0.074 (4)	0.042 (3)	−0.027 (4)	0.022 (3)	−0.014 (3)
C21	0.097 (5)	0.068 (4)	0.033 (3)	−0.014 (4)	−0.002 (3)	−0.002 (2)
C22	0.063 (4)	0.048 (3)	0.043 (3)	−0.008 (3)	0.003 (2)	−0.008 (2)
C23	0.049 (3)	0.040 (3)	0.039 (2)	−0.010 (2)	0.005 (2)	−0.008 (2)
C24	0.042 (3)	0.048 (3)	0.039 (2)	−0.006 (2)	0.003 (2)	−0.003 (2)
C25	0.038 (3)	0.055 (3)	0.039 (2)	0.007 (2)	−0.002 (2)	0.001 (2)
C26	0.041 (3)	0.047 (3)	0.036 (2)	0.002 (2)	−0.005 (2)	−0.004 (2)
N9	0.076 (4)	0.099 (5)	0.081 (4)	−0.028 (4)	−0.029 (3)	0.021 (4)
O3	0.216 (9)	0.163 (7)	0.149 (6)	−0.041 (6)	0.080 (6)	−0.057 (6)
O4	0.101 (4)	0.177 (6)	0.076 (3)	−0.002 (4)	−0.015 (3)	0.031 (4)
O5	0.132 (5)	0.090 (4)	0.118 (4)	−0.007 (3)	−0.041 (4)	0.027 (3)
O1W	0.115 (10)	0.181 (12)	0.125 (9)	−0.003 (9)	0.005 (8)	−0.057 (8)

Geometric parameters (Å, º) top

Ag1—N8ⁱ	2.182 (3)	C7—H7A	0.9300
Ag1—N4	2.209 (4)	C8—C9	1.413 (6)
Ag1—N7	2.329 (4)	C8—H8A	0.9300
O1—C9	1.351 (6)	C9—C10	1.381 (6)
O1—H1A	0.8200	C10—C11	1.458 (6)
O2—C22	1.349 (7)	C11—H11A	0.9300
O2—H2B	0.8200	C12—H12A	0.9300
N1—C11	1.259 (6)	C13—H13A	0.9300
N1—N2	1.410 (5)	C14—C19	1.410 (6)
N2—C13	1.333 (6)	C14—C15	1.422 (7)
N2—C12	1.338 (5)	C14—C23	1.434 (7)
N3—C13	1.298 (6)	C15—C16	1.370 (8)
N3—N4	1.377 (5)	C15—H15A	0.9300
N4—C12	1.300 (6)	C16—C17	1.388 (9)
N5—C24	1.284 (6)	C16—H16A	0.9300
N5—N6	1.389 (5)	C17—C18	1.363 (9)
N6—C25	1.349 (6)	C17—H17A	0.9300
N6—C26	1.351 (5)	C18—C19	1.407 (8)
N7—C25	1.307 (6)	C18—H18A	0.9300
N7—N8	1.383 (5)	C19—C20	1.409 (8)
N8—C26	1.301 (6)	C20—C21	1.362 (9)
N8—Ag1ⁱ	2.182 (3)	C20—H20A	0.9300
C1—C2	1.412 (6)	C21—C22	1.416 (7)
C1—C6	1.428 (6)	C21—H21A	0.9300
C1—C10	1.435 (6)	C22—C23	1.378 (7)
C2—C3	1.346 (8)	C23—C24	1.450 (6)
C2—H2A	0.9300	C24—H24A	0.9300
C3—C4	1.403 (8)	C25—H25A	0.9300
C3—H3A	0.9300	C26—H26A	0.9300
C4—C5	1.355 (8)	N9—O4	1.141 (6)
C4—H4A	0.9300	N9—O5	1.176 (7)
C5—C6	1.406 (7)	N9—O3	1.284 (9)
C5—H5A	0.9300	O1W—H1WA	0.8499
C6—C7	1.408 (7)	O1W—H1WB	0.8500
C7—C8	1.326 (8)

N8ⁱ—Ag1—N4	147.87 (16)	N1—C11—C10	120.2 (4)
N8ⁱ—Ag1—N7	114.48 (13)	N1—C11—H11A	119.9
N4—Ag1—N7	97.64 (14)	C10—C11—H11A	119.9
C9—O1—H1A	109.5	N4—C12—N2	109.3 (4)
C22—O2—H2B	109.5	N4—C12—H12A	125.4
C11—N1—N2	117.8 (4)	N2—C12—H12A	125.4
C13—N2—C12	106.0 (4)	N3—C13—N2	111.0 (4)
C13—N2—N1	123.0 (4)	N3—C13—H13A	124.5
C12—N2—N1	130.8 (4)	N2—C13—H13A	124.5
C13—N3—N4	105.8 (4)	C19—C14—C15	116.7 (5)
C12—N4—N3	108.0 (4)	C19—C14—C23	119.6 (5)
C12—N4—Ag1	126.5 (3)	C15—C14—C23	123.7 (4)
N3—N4—Ag1	125.4 (3)	C16—C15—C14	121.1 (5)
C24—N5—N6	117.6 (4)	C16—C15—H15A	119.5
C25—N6—C26	106.3 (4)	C14—C15—H15A	119.5
C25—N6—N5	121.5 (4)	C15—C16—C17	121.4 (6)
C26—N6—N5	132.2 (4)	C15—C16—H16A	119.3
C25—N7—N8	106.9 (4)	C17—C16—H16A	119.3
C25—N7—Ag1	130.5 (3)	C18—C17—C16	119.1 (6)
N8—N7—Ag1	122.5 (3)	C18—C17—H17A	120.4
C26—N8—N7	107.8 (3)	C16—C17—H17A	120.4
C26—N8—Ag1ⁱ	129.5 (3)	C17—C18—C19	121.0 (6)
N7—N8—Ag1ⁱ	121.5 (3)	C17—C18—H18A	119.5
C2—C1—C6	117.2 (4)	C19—C18—H18A	119.5
C2—C1—C10	124.7 (4)	C18—C19—C20	120.7 (5)
C6—C1—C10	118.1 (4)	C18—C19—C14	120.6 (6)
C3—C2—C1	121.2 (5)	C20—C19—C14	118.7 (5)
C3—C2—H2A	119.4	C21—C20—C19	121.9 (5)
C1—C2—H2A	119.4	C21—C20—H20A	119.1
C2—C3—C4	121.9 (5)	C19—C20—H20A	119.1
C2—C3—H3A	119.0	C20—C21—C22	119.6 (5)
C4—C3—H3A	119.0	C20—C21—H21A	120.2
C5—C4—C3	118.5 (5)	C22—C21—H21A	120.2
C5—C4—H4A	120.8	O2—C22—C23	123.6 (5)
C3—C4—H4A	120.8	O2—C22—C21	115.6 (5)
C4—C5—C6	121.9 (5)	C23—C22—C21	120.8 (5)
C4—C5—H5A	119.0	C22—C23—C14	119.4 (4)
C6—C5—H5A	119.0	C22—C23—C24	120.6 (5)
C5—C6—C7	121.6 (5)	C14—C23—C24	120.0 (4)
C5—C6—C1	119.2 (5)	N5—C24—C23	121.5 (4)
C7—C6—C1	119.2 (5)	N5—C24—H24A	119.3
C8—C7—C6	121.9 (5)	C23—C24—H24A	119.3
C8—C7—H7A	119.0	N7—C25—N6	109.7 (4)
C6—C7—H7A	119.0	N7—C25—H25A	125.2
C7—C8—C9	120.6 (4)	N6—C25—H25A	125.2
C7—C8—H8A	119.7	N8—C26—N6	109.3 (4)
C9—C8—H8A	119.7	N8—C26—H26A	125.3
O1—C9—C10	123.3 (4)	N6—C26—H26A	125.3
O1—C9—C8	116.2 (4)	O4—N9—O5	134.0 (9)
C10—C9—C8	120.5 (5)	O4—N9—O3	112.1 (8)
C9—C10—C1	119.7 (4)	O5—N9—O3	113.6 (7)
C9—C10—C11	120.1 (4)	H1WA—O1W—H1WB	115.9
C1—C10—C11	120.2 (4)

C11—N1—N2—C13	−175.1 (5)	C1—C10—C11—N1	179.3 (4)
C11—N1—N2—C12	10.7 (8)	N3—N4—C12—N2	−0.9 (6)
C13—N3—N4—C12	0.2 (6)	Ag1—N4—C12—N2	−176.5 (3)
C13—N3—N4—Ag1	175.9 (4)	C13—N2—C12—N4	1.1 (6)
N8ⁱ—Ag1—N4—C12	−11.8 (6)	N1—N2—C12—N4	176.1 (5)
N7—Ag1—N4—C12	170.0 (5)	N4—N3—C13—N2	0.5 (6)
N8ⁱ—Ag1—N4—N3	173.4 (3)	C12—N2—C13—N3	−1.0 (6)
N7—Ag1—N4—N3	−4.9 (4)	N1—N2—C13—N3	−176.5 (4)
C24—N5—N6—C25	179.6 (4)	C19—C14—C15—C16	0.5 (8)
C24—N5—N6—C26	1.0 (7)	C23—C14—C15—C16	−178.6 (5)
N8ⁱ—Ag1—N7—C25	170.2 (4)	C14—C15—C16—C17	1.3 (9)
N4—Ag1—N7—C25	−10.8 (5)	C15—C16—C17—C18	−3.2 (10)
N8ⁱ—Ag1—N7—N8	−14.1 (4)	C16—C17—C18—C19	3.3 (9)
N4—Ag1—N7—N8	164.8 (3)	C17—C18—C19—C20	179.0 (6)
C25—N7—N8—C26	0.0 (5)	C17—C18—C19—C14	−1.5 (9)
Ag1—N7—N8—C26	−176.6 (3)	C15—C14—C19—C18	−0.3 (7)
C25—N7—N8—Ag1ⁱ	−168.3 (3)	C23—C14—C19—C18	178.7 (5)
Ag1—N7—N8—Ag1ⁱ	15.1 (5)	C15—C14—C19—C20	179.1 (5)
C6—C1—C2—C3	0.0 (7)	C23—C14—C19—C20	−1.8 (7)
C10—C1—C2—C3	179.0 (5)	C18—C19—C20—C21	−178.8 (6)
C1—C2—C3—C4	0.1 (9)	C14—C19—C20—C21	1.7 (9)
C2—C3—C4—C5	−0.4 (9)	C19—C20—C21—C22	−1.7 (9)
C3—C4—C5—C6	0.4 (9)	C20—C21—C22—O2	−178.9 (5)
C4—C5—C6—C7	−179.7 (5)	C20—C21—C22—C23	1.8 (9)
C4—C5—C6—C1	−0.2 (8)	O2—C22—C23—C14	178.8 (5)
C2—C1—C6—C5	0.0 (7)	C21—C22—C23—C14	−1.9 (8)
C10—C1—C6—C5	−179.1 (5)	O2—C22—C23—C24	−2.5 (8)
C2—C1—C6—C7	179.5 (5)	C21—C22—C23—C24	176.7 (5)
C10—C1—C6—C7	0.5 (7)	C19—C14—C23—C22	2.0 (7)
C5—C6—C7—C8	179.1 (5)	C15—C14—C23—C22	−179.0 (5)
C1—C6—C7—C8	−0.5 (8)	C19—C14—C23—C24	−176.7 (4)
C6—C7—C8—C9	−0.3 (9)	C15—C14—C23—C24	2.3 (7)
C7—C8—C9—O1	−178.4 (5)	N6—N5—C24—C23	−178.0 (4)
C7—C8—C9—C10	1.2 (8)	C22—C23—C24—N5	1.1 (7)
O1—C9—C10—C1	178.4 (4)	C14—C23—C24—N5	179.7 (5)
C8—C9—C10—C1	−1.2 (7)	N8—N7—C25—N6	0.4 (6)
O1—C9—C10—C11	−3.4 (7)	Ag1—N7—C25—N6	176.6 (3)
C8—C9—C10—C11	177.0 (4)	C26—N6—C25—N7	−0.7 (6)
C2—C1—C10—C9	−178.6 (5)	N5—N6—C25—N7	−179.5 (4)
C6—C1—C10—C9	0.3 (7)	N7—N8—C26—N6	−0.4 (5)
C2—C1—C10—C11	3.2 (7)	Ag1ⁱ—N8—C26—N6	166.7 (3)
C6—C1—C10—C11	−177.8 (4)	C25—N6—C26—N8	0.7 (6)
N2—N1—C11—C10	−177.4 (4)	N5—N6—C26—N8	179.4 (4)
C9—C10—C11—N1	1.2 (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
O1—H1A···N1	0.82	1.83	2.548 (4)	145
O2—H2B···N5	0.82	1.87	2.588 (5)	145
O1W—H1WA···O3ⁱⁱ	0.85	1.85	2.594 (15)	145

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Ag₂(C₁₃H₁₀N₄O)₄](NO₃)₂·H₂O
M_r	1310.78
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.8594 (15), 10.7081 (15), 12.8567 (19)
α, β, γ (°)	82.391 (2), 81.155 (2), 77.626 (2)
V (Å³)	1303.1 (3)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.83
Crystal size (mm)	0.2 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.826, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	6610, 4536, 3137
R_int	0.118
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.133, 1.00
No. of reflections	4536
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.84

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.83	2.548 (4)	145
O2—H2B···N5	0.82	1.87	2.588 (5)	145
O1W—H1WA···O3ⁱ	0.85	1.85	2.594 (15)	145

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors acknowledge the financial support from the Innovation Program for College Students of Central South University (grant No. 081053308).

References

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Volume 65| Part 3| March 2009| Pages m283-m284

doi:10.1107/S1600536809004760

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Construction of a dinuclear silver(I) coordination complex with a Schiff base containing 4-amino-1,2,4-triazole ligands

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds