Poly[(μ4-tetra­zole-1-acetato-κ4N3:N4:O:O′)silver(I)]

Li, S.-J.; Wang, H.; Song, W.-D.; Hu, S.-W.; Qin, P.-W.

doi:10.1107/S1600536810001236

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m160

https://doi.org/10.1107/S1600536810001236

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Poly[(μ₄-tetrazole-1-acetato-κ⁴N³:N⁴:O:O′)silver(I)]

Shi-Jie Li,^a Hao Wang,^a Wen-Dong Song,^b ^* Shi-Wei Hu ^a and Pei-Wen Qin ^c

^aCollege of Food Science and Technology, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China, ^bCollege of Science, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China, and ^cCollege of Agriculture, Guang Dong Ocean University, Zhanjiang 524088, People's Republic of China
^*Correspondence e-mail: songwd60@126.com

(Received 29 December 2009; accepted 11 January 2010; online 16 January 2010)

In the title complex, [Ag(C₃H₃N₄O₂)]_n, the Ag^I atom is four-coordinated in a slightly distorted tetrahedral coordination geometry by two N atoms from two tetrazole-1-acetate (tza) ligands and two O atoms from the other two tza ligands. The tza ligand bridges two Ag atoms through the carboxylate O atoms and simultaneously binds to the other two Ag atoms through the tetrazole N atoms, forming a two-dimensional network parallel to (100).

Related literature

For the diverse coordination modes and potential applications of metal complexes with tetrazole derivatives, see: Stagni et al. (2006 ); Ye et al. (2006 ).

Experimental

Crystal data

[Ag(C₃H₃N₄O₂)]
M_r = 234.96
Triclinic, $[P \overline 1]$
a = 5.1584 (10) Å
b = 7.7805 (16) Å
c = 7.8711 (16) Å
α = 109.40 (3)°
β = 98.87 (3)°
γ = 104.85 (3)°
V = 277.92 (14) Å³
Z = 2
Mo Kα radiation
μ = 3.56 mm⁻¹
T = 293 K
0.25 × 0.23 × 0.21 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ) T_min = 0.470, T_max = 0.522
2722 measured reflections
1267 independent reflections
1150 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.177
S = 1.23
1267 reflections
92 parameters
H-atom parameters constrained
Δρ_max = 2.15 e Å⁻³
Δρ_min = −0.97 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—O1	2.330 (7)
Ag1—O2ⁱ	2.282 (7)
Ag1—N3ⁱⁱ	2.494 (9)
Ag1—N4ⁱⁱⁱ	2.442 (8)
Symmetry codes: (i) -x+1, -y, -z; (ii) x, y-1, z-1; (iii) -x+1, -y, -z+1.

Data collection: CrystalStructure (Rigaku/MSC, 2002 ); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ) and DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810001236/hy2270sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810001236/hy2270Isup2.hkl

checkCIF report

Comment top

In recent years, organic ligands with a tetrazole functional group have been greatly used in coordination chemistry for construction of metal-organic frameworks due to their diverse coordination modes and potential applications in varied fields (Stagni et al., 2006; Ye et al., 2006). The reaction of tetrazole-1-acetic acid (Htza) with AgNO₃ in an alkaline aqueous solution yielded a new Ag^I coordination polymer, whose crystal structure is reported here.

In the title complex, the Ag^I atom is four-coordinated in a slightly distorted tetrahedral coordination geometry by two N atoms and two O atoms from four different tza ligands (Table 1), as illustrated in Fig. 1. The adjacent Ag^I atoms are co-bridged by tza liands. The tza ligand acts as a tetradentate ligand, bridging two Ag atoms through its carboxylate O atoms, while simultaneously binding to the other two Ag atoms through two N atoms of the tetrazole group, forming a two-dimensional network parallel to (1 0 0).

Related literature top

For the diverse coordination modes and potential applications of metal complexes with tetrazole derivatives, see: Stagni et al. (2006); Ye et al. (2006).

Experimental top

A mixture of AgNO₃ (0.073 g, 0.5 mmol) and Htza (0.990 g, 0.5 mmol) in 15 ml of H₂O solution was sealed in an autoclave equipped with a Teflon liner (20 ml) and then heated at 373 K for 4 d. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.

Structure description top

For the diverse coordination modes and potential applications of metal complexes with tetrazole derivatives, see: Stagni et al. (2006); Ye et al. (2006).

Computing details top

Data collection: CrystalStructure (Rigaku/MSC, 2002); cell refinement: CrystalStructure (Rigaku/MSC, 2002); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, with symmetrically related atoms to complete the Ag coordination. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) 1-x, -y, -z; (ii) x, -1+y, -1+z; (iii) 1-x, -y, 1-z; (iv) 1-x, 1-y, 1-z; (v) x, y, -1+z.]
	Fig. 2. A view of the layer structure of the title compound.

Poly[(µ₄-tetrazole-1-acetato- κ⁴N³:N⁴:O:O')silver(I)] top

Crystal data top

[Ag(C₃H₃N₄O₂)]	Z = 2
M_r = 234.96	F(000) = 224
Triclinic, P1	D_x = 2.808 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.1584 (10) Å	Cell parameters from 3600 reflections
b = 7.7805 (16) Å	θ = 1.4–28°
c = 7.8711 (16) Å	µ = 3.56 mm⁻¹
α = 109.40 (3)°	T = 293 K
β = 98.87 (3)°	Block, blue
γ = 104.85 (3)°	0.25 × 0.23 × 0.21 mm
V = 277.92 (14) Å³

Data collection top

Rigaku/MSC Mercury CCD diffractometer	1267 independent reflections
Radiation source: fine-focus sealed tube	1150 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	h = −6→6
T_min = 0.470, T_max = 0.522	k = −9→10
2722 measured reflections	l = −10→9

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)] = 0.062	H-atom parameters constrained
wR(F²) = 0.177	w = 1/[σ²(F_o²) + (0.0519P)² + 3.2858P] where P = (F_o² + 2F_c²)/3
S = 1.23	(Δ/σ)_max < 0.001
1267 reflections	Δρ_max = 2.15 e Å⁻³
92 parameters	Δρ_min = −0.97 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: 0.052 (15)

Crystal data top

[Ag(C₃H₃N₄O₂)]	γ = 104.85 (3)°
M_r = 234.96	V = 277.92 (14) Å³
Triclinic, P1	Z = 2
a = 5.1584 (10) Å	Mo Kα radiation
b = 7.7805 (16) Å	µ = 3.56 mm⁻¹
c = 7.8711 (16) Å	T = 293 K
α = 109.40 (3)°	0.25 × 0.23 × 0.21 mm
β = 98.87 (3)°

Data collection top

Rigaku/MSC Mercury CCD diffractometer	1267 independent reflections
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	1150 reflections with I > 2σ(I)
T_min = 0.470, T_max = 0.522	R_int = 0.056
2722 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.23	Δρ_max = 2.15 e Å⁻³
1267 reflections	Δρ_min = −0.97 e Å⁻³
92 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.61189 (17)	−0.19436 (12)	−0.05077 (10)	0.0387 (5)
O1	0.9281 (15)	0.0639 (10)	0.2082 (10)	0.0365 (16)
O2	0.6195 (14)	0.1949 (12)	0.3227 (10)	0.0360 (16)
N1	0.9120 (16)	0.3243 (11)	0.6770 (10)	0.0277 (16)
N2	0.872 (2)	0.4946 (12)	0.7248 (12)	0.0376 (19)
N3	0.7161 (19)	0.4973 (12)	0.8396 (12)	0.0363 (19)
N4	0.656 (2)	0.3322 (13)	0.8697 (12)	0.0351 (18)
C1	0.8444 (18)	0.1645 (13)	0.3374 (12)	0.0265 (17)
C2	1.0509 (18)	0.2615 (13)	0.5323 (12)	0.0267 (17)
H2A	1.1368	0.1710	0.5545	0.032*
H2B	1.1964	0.3719	0.5373	0.032*
C3	0.781 (2)	0.2254 (15)	0.7646 (14)	0.034 (2)
H3	0.7775	0.1022	0.7545	0.041*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0430 (6)	0.0441 (6)	0.0259 (5)	0.0145 (4)	0.0071 (3)	0.0105 (3)
O1	0.033 (3)	0.031 (3)	0.034 (4)	0.013 (3)	0.010 (3)	−0.003 (3)
O2	0.028 (3)	0.055 (4)	0.029 (3)	0.020 (3)	0.008 (3)	0.016 (3)
N1	0.033 (4)	0.030 (4)	0.021 (3)	0.011 (3)	0.008 (3)	0.009 (3)
N2	0.051 (5)	0.027 (4)	0.033 (4)	0.013 (4)	0.017 (4)	0.008 (3)
N3	0.045 (5)	0.030 (4)	0.030 (4)	0.010 (4)	0.012 (4)	0.008 (3)
N4	0.048 (5)	0.034 (4)	0.030 (4)	0.020 (4)	0.017 (4)	0.014 (3)
C1	0.026 (4)	0.028 (4)	0.025 (4)	0.010 (3)	0.005 (3)	0.009 (3)
C2	0.023 (4)	0.032 (4)	0.022 (4)	0.010 (3)	0.003 (3)	0.007 (3)
C3	0.041 (5)	0.033 (5)	0.032 (5)	0.014 (4)	0.013 (4)	0.015 (4)

Geometric parameters (Å, º) top

Ag1—O1	2.330 (7)	N1—C2	1.453 (11)
Ag1—O2ⁱ	2.282 (7)	N2—N3	1.297 (12)
Ag1—N3ⁱⁱ	2.494 (9)	N3—N4	1.350 (12)
Ag1—N4ⁱⁱⁱ	2.442 (8)	N4—C3	1.331 (13)
O1—C1	1.270 (11)	C1—C2	1.540 (12)
O2—C1	1.238 (11)	C2—H2A	0.9700
N1—C3	1.324 (12)	C2—H2B	0.9700
N1—N2	1.331 (12)	C3—H3	0.9300

O2ⁱ—Ag1—O1	129.2 (3)	C3—N4—N3	105.1 (8)
O2ⁱ—Ag1—N4ⁱⁱⁱ	118.7 (3)	C3—N4—Ag1ⁱⁱⁱ	117.8 (6)
O1—Ag1—N4ⁱⁱⁱ	95.0 (3)	N3—N4—Ag1ⁱⁱⁱ	137.0 (6)
O2ⁱ—Ag1—N3ⁱⁱ	102.2 (3)	O2—C1—O1	127.3 (9)
O1—Ag1—N3ⁱⁱ	118.0 (3)	O2—C1—C2	117.2 (8)
N4ⁱⁱⁱ—Ag1—N3ⁱⁱ	86.0 (3)	O1—C1—C2	115.5 (8)
C1—O1—Ag1	120.6 (6)	N1—C2—C1	111.1 (7)
C1—O2—Ag1ⁱ	121.2 (6)	N1—C2—H2A	109
C3—N1—N2	109.2 (8)	C1—C2—H2A	109
C3—N1—C2	128.9 (8)	N1—C2—H2B	109
N2—N1—C2	121.4 (8)	C1—C2—H2B	109
N3—N2—N1	106.3 (8)	H2A—C2—H2B	108
N2—N3—N4	111.0 (8)	N1—C3—N4	108.4 (9)
N2—N3—Ag1^iv	112.1 (6)	N1—C3—H3	126
N4—N3—Ag1^iv	136.9 (6)	N4—C3—H3	126

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

Experimental details

Crystal data
Chemical formula	[Ag(C₃H₃N₄O₂)]
M_r	234.96
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	5.1584 (10), 7.7805 (16), 7.8711 (16)
α, β, γ (°)	109.40 (3), 98.87 (3), 104.85 (3)
V (Å³)	277.92 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.56
Crystal size (mm)	0.25 × 0.23 × 0.21

Data collection
Diffractometer	Rigaku/MSC Mercury CCD
Absorption correction	Multi-scan (REQAB; Jacobson, 1998)
T_min, T_max	0.470, 0.522
No. of measured, independent and observed [I > 2σ(I)] reflections	2722, 1267, 1150
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.177, 1.23
No. of reflections	1267
No. of parameters	92
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.15, −0.97

Computer programs: CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 1999).

Selected bond lengths (Å) top

Ag1—O1	2.330 (7)	Ag1—N3ⁱⁱ	2.494 (9)
Ag1—O2ⁱ	2.282 (7)	Ag1—N4ⁱⁱⁱ	2.442 (8)

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

Acknowledgements

The authors acknowledge Guang Dong Ocean University for supporting this work.

References

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