A new Ag complex based on 1-[(1H-benzimidazol-1-yl)meth-yl]-1H-1,2,4-triazole.

In the title complex, bis-{μ-1-[(1H-benzimidazol-1-yl)meth-yl]-1H-1,2,4-triazole}disilver(I) dinitrate, [Ag(2)(C(10)H(9)N(5))(2)](NO(3))(2), the Ag(I) ion is nearly linearly coordinated [N-Ag-N angle is 155.72 (14)°] by two 1-[(1H-benzimidazole-1-yl)meth-yl]-1H-1,2,4-triazole (bmt) ligands. In addition, two bmt ligands link two Ag(I) ions, forming a dinuclear unit with an Ag⋯Ag distance of 5.0179 (15) Å. The whole complex is generated by an inversion centre. The dinuclear units and the NO(3) (-) counter-ions are connected by N-H⋯O hydrogen bonds and weak Ag⋯O inter-actions [2.831 (5), 2.887 (5) and 2.908 (5) Å], leading to a three-dimensional structure.

Related literature

For background to complexes based on benzimidazole or triazole and their derivatives, see: Yang et al. (2010 ▶); Li et al. (2010 ▶); Tian et al. (2011 ▶); Zhang et al. (2011 ▶).

Experimental

Crystal data

[Ag2(C10H9N5)2](NO3)2

M = 738.20

Monoclinic,

a = 9.4947 (19) Å

b = 13.569 (3) Å

c = 10.174 (2) Å

β = 114.56 (3)°

V = 1192.1 (4) Å3

Z = 2

Mo Kα radiation

μ = 1.71 mm−1

T = 293 K

0.19 × 0.17 × 0.14 mm

Data collection

Rigaku Saturn diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006 ▶) T min = 0.737, T max = 0.796

9572 measured reflections

2158 independent reflections

1952 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.095

S = 1.09

2158 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.70 e Å−3

Δρmin = −0.28 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2006 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048501/vm2136sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048501/vm2136Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ag2(C10H9N5)2](NO3)2	F(000) = 728
Mr = 738.20	Dx = 2.057 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3140 reflections
a = 9.4947 (19) Å	θ = 2.4–27.9°
b = 13.569 (3) Å	µ = 1.71 mm−1
c = 10.174 (2) Å	T = 293 K
β = 114.56 (3)°	Prism, colourless
V = 1192.1 (4) Å3	0.19 × 0.17 × 0.14 mm
Z = 2

Rigaku Saturn diffractometer	2158 independent reflections
Radiation source: fine-focus sealed tube	1952 reflections with I > 2σ(I)
graphite	Rint = 0.034
Detector resolution: 28.5714 pixels mm-1	θmax = 25.3°, θmin = 2.4°
ω scans	h = −11→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2006)	k = −16→16
Tmin = 0.737, Tmax = 0.796	l = −12→11
9572 measured reflections

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0419P)2 + 1.7006P] where P = (Fo2 + 2Fc2)/3
2158 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.70 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

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.

	x	y	z	Uiso*/Ueq
Ag1	−0.34103 (4)	0.89095 (3)	0.20814 (4)	0.04938 (17)
N1	−0.0927 (4)	0.9097 (2)	0.3164 (4)	0.0326 (8)
N2	0.1479 (4)	0.9666 (3)	0.3996 (4)	0.0354 (8)
H2B	0.2248	1.0035	0.4080	0.043*
N3	−0.1878 (4)	1.0476 (2)	0.0747 (4)	0.0320 (8)
N4	−0.1943 (5)	0.9813 (3)	−0.0280 (4)	0.0449 (10)
N5	−0.4205 (4)	1.0613 (3)	−0.0931 (4)	0.0374 (8)
N6	0.3779 (5)	1.1840 (3)	0.4722 (5)	0.0470 (10)
O1	0.3112 (6)	1.1880 (4)	0.3398 (4)	0.0877 (14)
O2	0.3944 (6)	1.1033 (3)	0.5326 (5)	0.0818 (14)
O3	0.4245 (5)	1.2605 (3)	0.5397 (5)	0.0801 (13)
C1	0.0033 (5)	0.8484 (3)	0.4281 (4)	0.0320 (9)
C2	−0.0334 (6)	0.7641 (3)	0.4866 (5)	0.0387 (10)
H2A	−0.1339	0.7396	0.4515	0.046*
C3	0.0871 (6)	0.7193 (3)	0.5989 (5)	0.0446 (12)
H3A	0.0670	0.6633	0.6409	0.054*
C4	0.2383 (6)	0.7552 (3)	0.6518 (5)	0.0454 (12)
H4A	0.3158	0.7223	0.7277	0.055*
C5	0.2760 (5)	0.8380 (3)	0.5946 (5)	0.0415 (11)
H5A	0.3769	0.8618	0.6295	0.050*
C6	0.1542 (5)	0.8840 (3)	0.4813 (5)	0.0345 (10)
C7	−0.0011 (5)	0.9789 (3)	0.3042 (4)	0.0306 (9)
C8	−0.0451 (5)	1.0643 (3)	0.2027 (4)	0.0352 (10)
H8A	−0.0574	1.1222	0.2528	0.042*
H8B	0.0379	1.0774	0.1732	0.042*
C9	−0.3227 (5)	1.0931 (3)	0.0341 (5)	0.0353 (10)
H9A	−0.3452	1.1409	0.0881	0.042*
C10	−0.3371 (6)	0.9929 (4)	−0.1265 (5)	0.0450 (11)
H10A	−0.3772	0.9569	−0.2120	0.054*

	U11	U22	U33	U12	U13	U23
Ag1	0.0295 (2)	0.0625 (3)	0.0471 (3)	0.00013 (17)	0.00685 (17)	0.00857 (18)
N1	0.0290 (19)	0.0329 (19)	0.0328 (19)	0.0005 (16)	0.0098 (16)	−0.0039 (15)
N2	0.030 (2)	0.038 (2)	0.036 (2)	−0.0027 (16)	0.0114 (16)	−0.0009 (16)
N3	0.0292 (19)	0.0302 (17)	0.0335 (19)	0.0019 (15)	0.0100 (16)	0.0020 (15)
N4	0.040 (2)	0.046 (2)	0.047 (2)	0.0002 (19)	0.016 (2)	−0.0166 (19)
N5	0.030 (2)	0.041 (2)	0.036 (2)	0.0014 (17)	0.0097 (17)	0.0027 (17)
N6	0.036 (2)	0.056 (3)	0.047 (3)	−0.007 (2)	0.015 (2)	−0.004 (2)
O1	0.103 (4)	0.097 (3)	0.048 (2)	0.023 (3)	0.016 (2)	−0.003 (2)
O2	0.089 (3)	0.060 (3)	0.088 (3)	−0.008 (2)	0.029 (3)	0.028 (2)
O3	0.067 (3)	0.064 (3)	0.094 (3)	−0.025 (2)	0.019 (2)	−0.029 (2)
C1	0.033 (2)	0.032 (2)	0.028 (2)	0.0053 (18)	0.0098 (18)	−0.0064 (18)
C2	0.040 (3)	0.034 (2)	0.040 (2)	0.000 (2)	0.014 (2)	−0.0028 (19)
C3	0.060 (3)	0.033 (2)	0.037 (3)	0.004 (2)	0.018 (2)	0.000 (2)
C4	0.055 (3)	0.041 (3)	0.034 (2)	0.018 (2)	0.012 (2)	0.001 (2)
C5	0.034 (3)	0.049 (3)	0.035 (2)	0.005 (2)	0.008 (2)	−0.007 (2)
C6	0.036 (3)	0.035 (2)	0.031 (2)	0.0020 (19)	0.013 (2)	−0.0054 (18)
C7	0.030 (2)	0.031 (2)	0.028 (2)	−0.0005 (18)	0.0106 (18)	−0.0052 (17)
C8	0.031 (2)	0.034 (2)	0.036 (2)	−0.0011 (19)	0.0093 (19)	−0.0042 (19)
C9	0.037 (3)	0.037 (2)	0.032 (2)	0.003 (2)	0.015 (2)	0.0031 (19)
C10	0.040 (3)	0.049 (3)	0.043 (3)	−0.007 (2)	0.014 (2)	−0.010 (2)

Ag1—N1	2.163 (4)	N6—O2	1.233 (5)
Ag1—N5i	2.171 (4)	C1—C6	1.390 (6)
N1—C7	1.321 (5)	C1—C2	1.399 (6)
N1—C1	1.397 (5)	C2—C3	1.377 (6)
N2—C7	1.353 (5)	C2—H2A	0.9300
N2—C6	1.382 (5)	C3—C4	1.395 (7)
N2—H2B	0.8600	C3—H3A	0.9300
N3—C9	1.325 (5)	C4—C5	1.380 (7)
N3—N4	1.361 (5)	C4—H4A	0.9300
N3—C8	1.454 (5)	C5—C6	1.396 (6)
N4—C10	1.318 (6)	C5—H5A	0.9300
N5—C9	1.313 (6)	C7—C8	1.492 (6)
N5—C10	1.352 (6)	C8—H8A	0.9700
N5—Ag1i	2.171 (4)	C8—H8B	0.9700
N6—O3	1.222 (5)	C9—H9A	0.9300
N6—O1	1.229 (5)	C10—H10A	0.9300
N1—Ag1—N5i	155.72 (14)	C4—C3—H3A	118.9
C7—N1—C1	105.5 (4)	C5—C4—C3	121.9 (4)
C7—N1—Ag1	131.1 (3)	C5—C4—H4A	119.1
C1—N1—Ag1	123.3 (3)	C3—C4—H4A	119.1
C7—N2—C6	107.6 (4)	C4—C5—C6	116.2 (4)
C7—N2—H2B	126.2	C4—C5—H5A	121.9
C6—N2—H2B	126.2	C6—C5—H5A	121.9
C9—N3—N4	109.8 (4)	N2—C6—C1	105.5 (4)
C9—N3—C8	128.8 (4)	N2—C6—C5	132.3 (4)
N4—N3—C8	121.2 (3)	C1—C6—C5	122.2 (4)
C10—N4—N3	102.1 (4)	N1—C7—N2	112.2 (4)
C9—N5—C10	103.0 (4)	N1—C7—C8	127.7 (4)
C9—N5—Ag1i	125.8 (3)	N2—C7—C8	120.1 (4)
C10—N5—Ag1i	131.1 (3)	N3—C8—C7	112.8 (3)
O3—N6—O1	118.6 (5)	N3—C8—H8A	109.0
O3—N6—O2	122.2 (5)	C7—C8—H8A	109.0
O1—N6—O2	119.1 (5)	N3—C8—H8B	109.0
C6—C1—N1	109.2 (4)	C7—C8—H8B	109.0
C6—C1—C2	121.1 (4)	H8A—C8—H8B	107.8
N1—C1—C2	129.7 (4)	N5—C9—N3	110.5 (4)
C3—C2—C1	116.5 (4)	N5—C9—H9A	124.8
C3—C2—H2A	121.8	N3—C9—H9A	124.8
C1—C2—H2A	121.8	N4—C10—N5	114.6 (4)
C2—C3—C4	122.2 (4)	N4—C10—H10A	122.7
C2—C3—H3A	118.9	N5—C10—H10A	122.7
N5i—Ag1—N1—C7	−24.9 (5)	C4—C5—C6—N2	179.8 (4)
N5i—Ag1—N1—C1	149.8 (3)	C4—C5—C6—C1	−0.4 (6)
C9—N3—N4—C10	0.5 (5)	C1—N1—C7—N2	0.3 (4)
C8—N3—N4—C10	−176.4 (4)	Ag1—N1—C7—N2	175.7 (3)
C7—N1—C1—C6	0.1 (4)	C1—N1—C7—C8	−178.8 (4)
Ag1—N1—C1—C6	−175.7 (3)	Ag1—N1—C7—C8	−3.3 (6)
C7—N1—C1—C2	179.6 (4)	C6—N2—C7—N1	−0.7 (5)
Ag1—N1—C1—C2	3.7 (6)	C6—N2—C7—C8	178.5 (3)
C6—C1—C2—C3	0.2 (6)	C9—N3—C8—C7	114.0 (5)
N1—C1—C2—C3	−179.2 (4)	N4—N3—C8—C7	−69.8 (5)
C1—C2—C3—C4	−0.4 (6)	N1—C7—C8—N3	−23.6 (6)
C2—C3—C4—C5	0.1 (7)	N2—C7—C8—N3	157.4 (4)
C3—C4—C5—C6	0.3 (6)	C10—N5—C9—N3	0.7 (5)
C7—N2—C6—C1	0.7 (4)	Ag1i—N5—C9—N3	178.7 (3)
C7—N2—C6—C5	−179.5 (4)	N4—N3—C9—N5	−0.8 (5)
N1—C1—C6—N2	−0.5 (4)	C8—N3—C9—N5	175.8 (4)
C2—C1—C6—N2	180.0 (4)	N3—N4—C10—N5	0.0 (5)
N1—C1—C6—C5	179.6 (4)	C9—N5—C10—N4	−0.4 (5)
C2—C1—C6—C5	0.1 (6)	Ag1i—N5—C10—N4	−178.3 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2	0.86	2.08	2.849 (6)	148.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2	0.86	2.08	2.849 (6)	148