Bis(μ2-3,5-diisopropyl-4H-1,2,4-triazole-κ2N1:N2)bis­[(nitrato-κO)silver(I)]

Wang, Z.-Y.; Wang, Y.-L.; Yang, G.; Ng, S.W.

doi:10.1107/S1600536809028384

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page m974

doi:10.1107/S1600536809028384

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Bis(μ₂-3,5-diisopropyl-4H-1,2,4-triazole-κ²N¹:N²)bis[(nitrato-κO)silver(I)]

Zhao-Yang Wang,^a Ying-Li Wang,^a Guang Yang ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 17 July 2009; accepted 17 July 2009; online 22 July 2009)

The neutral N-heterocycle in the title centrosymmetric dinuclear compound, [Ag₂(NO₃)₂(C₈H₁₅N₃)₂], bridges two metal atoms through its imino N atoms. The N—Ag—N skeleton is bent [N—Ag—N = 127.2 (3)°]; as one of two O atoms of the nitrate anion is nearly coplanar with this N—Ag—N skeleton [Ag—O = 2.63 (1) Å], the coordination geometry around the Ag^I atom is regarded as trigonal-planar. One of the two isopropyl groups is disordered over two positions in respect of the methyl groups in a 1:1 ratio. In the crystal structure, intermolecular N—H⋯O hydrogen bonding is observed between the nitrate groups and triazole ligands.

Related literature

For the background to such silver–triazole compounds, see: Yang et al. (2007 ).

Experimental

Crystal data

[Ag₂(NO₃)₂(C₈H₁₅N₃)₂]
M_r = 646.22
Monoclinic, P 2₁ /n
a = 5.791 (1) Å
b = 14.541 (1) Å
c = 14.578 (1) Å
β = 99.523 (2)°
V = 1210.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.66 mm⁻¹
T = 293 K
0.41 × 0.17 × 0.13 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.670, T_max = 1.000 (expected range = 0.540–0.805)
5562 measured reflections
2124 independent reflections
1389 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.078
wR(F²) = 0.240
S = 1.08
2124 reflections
151 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 0.91 e Å⁻³
Δρ_min = −0.96 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1ⁱ	0.89	2.06	2.93 (1)	167
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 1999 ); 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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028384/xu2560sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809028384/xu2560Isup2.hkl

checkCIF report

Related literature top

For the background to such silver–triazole compounds, see: Yang et al. (2007).

Experimental top

An acetonitrile solution (2 ml) of 3,5-diisopropyl-1H-1,2,4-triazole (0.1 mmol, 15 mg) was mixed with a acetoninitrile solution (1 ml) of silver nitrate (0.1 mmol, 17 mg). Ether was allowed to diffuse into the resulting solution. Colorless crystals were formed after a week in 50% yield. Calc. for C₁₆H₃₀N₈Ag₂O₆: C 29.7; H 4.6, N, 17.3%. Found: C 29.7, H 4.7, N, 17.6%.

Computing details top

Data collection: APEX2 (Bruker, 1999); 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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot of [Ag(C₈H₁₅N₃)(NO₃)]₂; ellipsoids are drawn at the 50% probability level. The disorder is not shown.

Bis(µ₂-3,5-diisopropyl-4H-1,2,4-triazole- κ²N¹:N²)bis[(nitrato-κO)silver(I)] top

Crystal data top

[Ag₂(NO₃)₂(C₈H₁₅N₃)₂]	F(000) = 648
M_r = 646.22	D_x = 1.773 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1859 reflections
a = 5.791 (1) Å	θ = 2.8–21.8°
b = 14.541 (1) Å	µ = 1.66 mm⁻¹
c = 14.578 (1) Å	T = 293 K
β = 99.523 (2)°	Prism, colorless
V = 1210.6 (2) Å³	0.41 × 0.17 × 0.13 mm
Z = 2

Data collection top

Bruker SMART diffractometer	2124 independent reflections
Radiation source: fine-focus sealed tube	1389 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.670, T_max = 1.000	k = −9→17
5562 measured reflections	l = −17→13

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)] = 0.078	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.240	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.1131P)² + 8.3674P] where P = (F_o² + 2F_c²)/3
2124 reflections	(Δ/σ)_max = 0.001
151 parameters	Δρ_max = 0.91 e Å⁻³
18 restraints	Δρ_min = −0.96 e Å⁻³

Crystal data top

[Ag₂(NO₃)₂(C₈H₁₅N₃)₂]	V = 1210.6 (2) Å³
M_r = 646.22	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.791 (1) Å	µ = 1.66 mm⁻¹
b = 14.541 (1) Å	T = 293 K
c = 14.578 (1) Å	0.41 × 0.17 × 0.13 mm
β = 99.523 (2)°

Data collection top

Bruker SMART diffractometer	2124 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1389 reflections with I > 2σ(I)
T_min = 0.670, T_max = 1.000	R_int = 0.063
5562 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.078	18 restraints
wR(F²) = 0.240	H-atom parameters constrained
S = 1.08	Δρ_max = 0.91 e Å⁻³
2124 reflections	Δρ_min = −0.96 e Å⁻³
151 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Ag1	0.6205 (2)	0.57863 (7)	0.43648 (7)	0.0682 (5)
O1	0.8666 (17)	0.6779 (7)	0.3367 (8)	0.080 (3)
O2	1.0702 (19)	0.5875 (8)	0.4336 (8)	0.094 (4)
O3	1.2426 (18)	0.6792 (9)	0.3497 (8)	0.096 (4)
N1	0.5362 (17)	0.4427 (6)	0.3705 (6)	0.047 (2)
N2	0.4403 (17)	0.3760 (7)	0.4232 (7)	0.054 (3)
N3	0.5156 (19)	0.3113 (7)	0.2993 (8)	0.061 (3)
H3	0.5270	0.2681	0.2570	0.074*
N4	1.061 (2)	0.6493 (8)	0.3760 (8)	0.067 (3)
C1	0.547 (3)	0.4325 (13)	0.1257 (10)	0.087 (5)
H1A	0.3891	0.4523	0.1263	0.130*
H1B	0.5473	0.3686	0.1093	0.130*
H1C	0.6133	0.4680	0.0809	0.130*
C2	0.692 (2)	0.4463 (9)	0.2217 (9)	0.058 (3)
H2	0.6933	0.5126	0.2339	0.070*
C3	0.946 (3)	0.4169 (15)	0.2284 (14)	0.104 (6)
H3A	1.0273	0.4274	0.2904	0.155*
H3B	1.0189	0.4520	0.1852	0.155*
H3C	0.9529	0.3527	0.2137	0.155*
C4	0.5824 (19)	0.4017 (7)	0.2966 (8)	0.044 (3)
C5	0.429 (2)	0.3010 (8)	0.3788 (9)	0.055 (3)
C6	0.342 (2)	0.2139 (8)	0.4109 (12)	0.085 (5)
H6	0.3262	0.2233	0.4761	0.102*	0.50
H6'	0.3460	0.1810	0.3525	0.102*	0.50
C7	0.097 (3)	0.192 (2)	0.359 (2)	0.087 (8)	0.50
H7A	0.0448	0.1347	0.3805	0.131*	0.50
H7B	0.1006	0.1882	0.2934	0.131*	0.50
H7C	−0.0092	0.2401	0.3700	0.131*	0.50
C8	0.503 (4)	0.1308 (18)	0.409 (3)	0.089 (7)	0.50
H8A	0.4306	0.0774	0.4308	0.134*	0.50
H8B	0.6496	0.1423	0.4490	0.134*	0.50
H8C	0.5300	0.1205	0.3468	0.134*	0.50
C7'	0.083 (2)	0.203 (2)	0.408 (2)	0.087 (8)	0.50
H7'1	0.0510	0.1425	0.4297	0.131*	0.50
H7'2	0.0038	0.2097	0.3446	0.131*	0.50
H7'3	0.0273	0.2484	0.4461	0.131*	0.50
C8'	0.490 (4)	0.144 (2)	0.471 (2)	0.089 (7)	0.50
H8'1	0.3938	0.0928	0.4820	0.134*	0.50
H8'2	0.5548	0.1720	0.5292	0.134*	0.50
H8'3	0.6138	0.1236	0.4399	0.134*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0868 (9)	0.0610 (7)	0.0623 (7)	−0.0294 (6)	0.0285 (5)	−0.0052 (5)
O1	0.051 (6)	0.080 (7)	0.107 (8)	0.001 (5)	0.007 (5)	0.031 (6)
O2	0.078 (7)	0.108 (9)	0.091 (7)	−0.021 (6)	0.003 (6)	0.066 (7)
O3	0.064 (6)	0.119 (9)	0.104 (8)	−0.015 (6)	0.016 (6)	0.057 (7)
N1	0.063 (6)	0.039 (5)	0.039 (5)	−0.016 (4)	0.009 (4)	0.003 (4)
N2	0.054 (6)	0.052 (6)	0.055 (6)	−0.018 (5)	0.009 (5)	0.007 (5)
N3	0.066 (7)	0.050 (6)	0.067 (7)	0.004 (5)	0.008 (6)	−0.009 (5)
N4	0.056 (7)	0.075 (8)	0.070 (7)	−0.001 (6)	0.016 (6)	0.018 (6)
C1	0.083 (10)	0.123 (14)	0.055 (8)	−0.004 (10)	0.013 (7)	0.012 (9)
C2	0.059 (8)	0.059 (8)	0.055 (7)	0.004 (6)	0.008 (6)	0.001 (6)
C3	0.056 (9)	0.146 (18)	0.112 (14)	0.007 (10)	0.027 (9)	0.040 (13)
C4	0.038 (6)	0.044 (6)	0.048 (6)	0.002 (4)	0.004 (5)	−0.001 (5)
C5	0.050 (7)	0.043 (7)	0.071 (8)	−0.010 (5)	0.005 (6)	0.001 (6)
C6	0.077 (10)	0.044 (7)	0.131 (14)	−0.003 (7)	0.011 (9)	0.021 (9)
C7	0.080 (9)	0.093 (10)	0.090 (12)	−0.017 (8)	0.020 (8)	0.011 (9)
C8	0.083 (10)	0.087 (10)	0.098 (12)	0.002 (8)	0.016 (9)	0.014 (9)
C7'	0.080 (9)	0.093 (10)	0.090 (12)	−0.017 (8)	0.020 (8)	0.011 (9)
C8'	0.083 (10)	0.087 (10)	0.098 (12)	0.002 (8)	0.016 (9)	0.014 (9)

Geometric parameters (Å, º) top

Ag1—N1	2.218 (9)	C3—H3B	0.9600
Ag1—N2ⁱ	2.232 (10)	C3—H3C	0.9600
Ag1—O2	2.615 (11)	C5—C6	1.469 (16)
Ag1—O1	2.630 (10)	C6—C7'	1.505 (10)
O1—N4	1.245 (14)	C6—C8'	1.508 (10)
O2—N4	1.224 (14)	C6—C7	1.529 (10)
O3—N4	1.258 (14)	C6—C8	1.529 (10)
N1—C4	1.297 (14)	C6—H6	0.9800
N1—N2	1.407 (12)	C6—H6'	0.9800
N2—C5	1.264 (15)	C7—H7A	0.9600
N2—Ag1ⁱ	2.232 (10)	C7—H7B	0.9600
N3—C5	1.342 (17)	C7—H7C	0.9600
N3—C4	1.373 (15)	C8—H8A	0.9600
N3—H3	0.8900	C8—H8B	0.9600
C1—C2	1.520 (19)	C8—H8C	0.9600
C1—H1A	0.9600	C7'—H7'1	0.9600
C1—H1B	0.9600	C7'—H7'2	0.9600
C1—H1C	0.9600	C7'—H7'3	0.9600
C2—C4	1.498 (18)	C8'—H8'1	0.9600
C2—C3	1.52 (2)	C8'—H8'2	0.9600
C2—H2	0.9800	C8'—H8'3	0.9600
C3—H3A	0.9600

N1—Ag1—N2ⁱ	127.2 (3)	N1—C4—C2	125.2 (10)
N1—Ag1—O2	100.7 (4)	N3—C4—C2	126.2 (11)
N2ⁱ—Ag1—O2	108.0 (4)	N2—C5—N3	110.6 (11)
N1—Ag1—O1	110.5 (4)	N2—C5—C6	124.8 (13)
N2ⁱ—Ag1—O1	121.8 (4)	N3—C5—C6	124.6 (13)
O2—Ag1—O1	48.0 (3)	C5—C6—C7'	118.6 (15)
N4—O1—Ag1	95.3 (7)	C5—C6—C8'	124.9 (15)
N4—O2—Ag1	96.6 (8)	C7'—C6—C8'	114.3 (10)
C4—N1—N2	106.9 (9)	C5—C6—C7	111.1 (17)
C4—N1—Ag1	135.2 (7)	C5—C6—C8	115.7 (17)
N2—N1—Ag1	117.1 (7)	C7'—C6—C8	121 (2)
C5—N2—N1	107.8 (10)	C7—C6—C8	110.4 (10)
C5—N2—Ag1ⁱ	136.3 (9)	C5—C6—H6	106.3
N1—N2—Ag1ⁱ	115.6 (7)	C7—C6—H6	106.3
C5—N3—C4	106.1 (10)	C8—C6—H6	106.3
C5—N3—H3	126.9	C6—C7—H7A	109.5
C4—N3—H3	126.9	C6—C7—H7B	109.5
O2—N4—O1	119.8 (11)	H7A—C7—H7B	109.5
O2—N4—O3	121.1 (12)	C6—C7—H7C	109.5
O1—N4—O3	118.8 (11)	H7A—C7—H7C	109.5
C2—C1—H1A	109.5	H7B—C7—H7C	109.5
C2—C1—H1B	109.5	C6—C8—H8A	109.5
H1A—C1—H1B	109.5	C6—C8—H8B	109.5
C2—C1—H1C	109.5	H8A—C8—H8B	109.5
H1A—C1—H1C	109.5	C6—C8—H8C	109.5
H1B—C1—H1C	109.5	H8A—C8—H8C	109.5
C4—C2—C1	112.3 (11)	H8B—C8—H8C	109.5
C4—C2—C3	110.7 (11)	C6—C7'—H7'1	109.5
C1—C2—C3	113.7 (13)	C6—C7'—H7'2	109.5
C4—C2—H2	106.6	H7'1—C7'—H7'2	109.5
C1—C2—H2	106.6	C6—C7'—H7'3	109.5
C3—C2—H2	106.6	H7'1—C7'—H7'3	109.5
C2—C3—H3A	109.5	H7'2—C7'—H7'3	109.5
C2—C3—H3B	109.5	C6—C8'—H8'1	109.5
H3A—C3—H3B	109.5	C6—C8'—H8'2	109.5
C2—C3—H3C	109.5	H8'1—C8'—H8'2	109.5
H3A—C3—H3C	109.5	C6—C8'—H8'3	109.5
H3B—C3—H3C	109.5	H8'1—C8'—H8'3	109.5
N1—C4—N3	108.5 (10)	H8'2—C8'—H8'3	109.5

N1—Ag1—O1—N4	−89.2 (9)	N2—N1—C4—C2	−178.6 (10)
N2ⁱ—Ag1—O1—N4	82.9 (9)	Ag1—N1—C4—C2	−9.6 (18)
O2—Ag1—O1—N4	−3.1 (8)	C5—N3—C4—N1	−0.4 (13)
N1—Ag1—O2—N4	111.2 (9)	C5—N3—C4—C2	179.2 (11)
N2ⁱ—Ag1—O2—N4	−113.7 (9)	C1—C2—C4—N1	−126.3 (14)
O1—Ag1—O2—N4	3.2 (8)	C3—C2—C4—N1	105.4 (15)
N2ⁱ—Ag1—N1—C4	−170.4 (10)	C1—C2—C4—N3	54.0 (16)
O2—Ag1—N1—C4	−47.8 (11)	C3—C2—C4—N3	−74.2 (17)
O1—Ag1—N1—C4	1.2 (12)	N1—N2—C5—N3	1.1 (14)
N2ⁱ—Ag1—N1—N2	−2.1 (11)	Ag1ⁱ—N2—C5—N3	−171.8 (9)
O2—Ag1—N1—N2	120.4 (8)	N1—N2—C5—C6	179.2 (11)
O1—Ag1—N1—N2	169.4 (7)	Ag1ⁱ—N2—C5—C6	6 (2)
C4—N1—N2—C5	−1.3 (13)	C4—N3—C5—N2	−0.4 (14)
Ag1—N1—N2—C5	−172.7 (8)	C4—N3—C5—C6	−178.5 (11)
C4—N1—N2—Ag1ⁱ	173.2 (7)	N2—C5—C6—C7'	74 (3)
Ag1—N1—N2—Ag1ⁱ	1.9 (10)	N3—C5—C6—C7'	−108 (2)
Ag1—O2—N4—O1	−5.8 (14)	N2—C5—C6—C8'	−88 (3)
Ag1—O2—N4—O3	−179.6 (12)	N3—C5—C6—C8'	90 (3)
Ag1—O1—N4—O2	5.8 (14)	N2—C5—C6—C7	104 (2)
Ag1—O1—N4—O3	179.7 (12)	N3—C5—C6—C7	−78 (2)
N2—N1—C4—N3	1.0 (12)	N2—C5—C6—C8	−128.8 (19)
Ag1—N1—C4—N3	170.1 (8)	N3—C5—C6—C8	49 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱⁱ	0.89	2.06	2.93 (1)	167

Symmetry code: (ii) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Ag₂(NO₃)₂(C₈H₁₅N₃)₂]
M_r	646.22
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.791 (1), 14.541 (1), 14.578 (1)
β (°)	99.523 (2)
V (Å³)	1210.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.66
Crystal size (mm)	0.41 × 0.17 × 0.13

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.670, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5562, 2124, 1389
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.078, 0.240, 1.08
No. of reflections	2124
No. of parameters	151
No. of restraints	18
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.91, −0.96

Computer programs: APEX2 (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1ⁱ	0.89	2.06	2.93 (1)	167

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

We thank the Education Department of Zhengzhou University, China and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (1999). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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