Bis[μ-1-(2-pyridylmeth-yl)-1H-benzo-triazole]disilver(I) bis-(perchlorate).

In the title centrosymmetric binuclear Ag(I )complex, [Ag(2)(C(12)H(10)N(4))(2)](ClO(4))(2), each Ag(I) center is two-coordinated by one pyridine and one benzotriazole N-donor atom of two inversion-related 1-(2-pyridylmeth-yl)-1H-benzotriazole (L) ligands. This forms a unique box-like cyclic dimer with an intra-molecular Ag⋯Ag separation of 4.479 (2) Å. Inter-molecular C-H⋯O hydrogen-bonding inter-actions, involving uncoordinated ClO(4) (-) ions, link the binuclear units, forming a two-dimensional network parallel to (10).

Related literature

Bis-heterocyclic chelating or bridging ligands have been used extensively to construct functional coordination complexes that contain different hetero-aromatic ring systems, see: Constable (1989 ▶); Constable & Steel (1989 ▶); Steel (2005 ▶). For related structures, see: Hu et al. (2008 ▶); Huang et al. (2008 ▶); Liu et al. (2006 ▶, 2007 ▶); Liu, Sun et al. (2008 ▶); Liu, Zhou et al. (2008 ▶); Richardson & Steel (2003 ▶). For the synthesis of ligand L, see: Liu, Sun et al. (2008 ▶).

Experimental

Crystal data

[Ag2(C12H10N4)2](ClO4)2

M = 835.12

Monoclinic,

a = 9.4273 (4) Å

b = 16.0863 (7) Å

c = 11.9152 (7) Å

β = 128.448 (3)°

V = 1415.15 (13) Å3

Z = 2

Mo Kα radiation

μ = 1.64 mm−1

T = 293 K

0.24 × 0.23 × 0.03 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.695, T max = 0.960

9388 measured reflections

2484 independent reflections

1658 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.137

S = 1.08

2484 reflections

199 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.53 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809043669/zq2014sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043669/zq2014Isup2.hkl

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

[Ag2(C12H10N4)2](ClO4)2	F(000) = 824
Mr = 835.12	Dx = 1.960 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3182 reflections
a = 9.4273 (4) Å	θ = 3.0–26.3°
b = 16.0863 (7) Å	µ = 1.64 mm−1
c = 11.9152 (7) Å	T = 293 K
β = 128.448 (3)°	Block, yellow
V = 1415.15 (13) Å3	0.24 × 0.23 × 0.03 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2484 independent reflections
Radiation source: fine-focus sealed tube	1658 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.695, Tmax = 0.960	k = −15→19
9388 measured reflections	l = −13→14

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) = 0.137	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0614P)2 + 2.0392P] where P = (Fo2 + 2Fc2)/3
2484 reflections	(Δ/σ)max = 0.001
199 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.53 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	0.42617 (7)	0.60201 (4)	0.58311 (7)	0.0599 (3)
N1	0.1418 (7)	0.6101 (3)	0.4978 (6)	0.0368 (13)
N2	0.3065 (6)	0.4519 (4)	0.2962 (5)	0.0385 (14)
N3	0.2868 (7)	0.5274 (4)	0.3285 (6)	0.0407 (14)
N4	0.1091 (6)	0.5452 (3)	0.2391 (5)	0.0347 (13)
C1	0.0453 (9)	0.6239 (4)	0.2566 (7)	0.0403 (17)
H11	0.1386	0.6658	0.2933	0.048*
H12	−0.0612	0.6425	0.1637	0.048*
C2	−0.0004 (9)	0.6159 (4)	0.3575 (7)	0.0325 (15)
C3	−0.1725 (9)	0.6158 (4)	0.3083 (8)	0.0435 (18)
H3	−0.2665	0.6190	0.2102	0.052*
C4	−0.2110 (10)	0.6110 (4)	0.4035 (9)	0.051 (2)
H4	−0.3297	0.6105	0.3711	0.062*
C5	−0.0673 (11)	0.6068 (4)	0.5464 (9)	0.052 (2)
H5	−0.0869	0.6050	0.6138	0.063*
C6	0.1070 (10)	0.6055 (4)	0.5901 (8)	0.0472 (18)
H6	0.2035	0.6012	0.6874	0.057*
C7	0.1415 (8)	0.4210 (4)	0.1852 (6)	0.0318 (15)
C8	0.0907 (9)	0.3446 (4)	0.1149 (7)	0.0400 (17)
H8	0.1757	0.3039	0.1390	0.048*
C9	−0.0903 (10)	0.3326 (5)	0.0089 (8)	0.0500 (19)
H9	−0.1290	0.2828	−0.0419	0.060*
C10	−0.2202 (10)	0.3928 (5)	−0.0261 (8)	0.052 (2)
H10	−0.3421	0.3811	−0.0980	0.062*
C11	−0.1737 (8)	0.4676 (5)	0.0417 (7)	0.0407 (17)
H1	−0.2595	0.5076	0.0183	0.049*
C12	0.0111 (8)	0.4803 (4)	0.1486 (6)	0.0310 (14)
Cl1	0.4844 (2)	0.21950 (12)	0.5792 (2)	0.0510 (5)
O1	0.4745 (9)	0.1317 (4)	0.5670 (7)	0.089 (2)
O2	0.3143 (9)	0.2532 (5)	0.4653 (7)	0.116 (3)
O3	0.6166 (13)	0.2454 (6)	0.5735 (14)	0.168 (5)
O4	0.5263 (10)	0.2432 (5)	0.7115 (7)	0.109 (3)

	U11	U22	U33	U12	U13	U23
Ag1	0.0348 (3)	0.0672 (5)	0.0583 (4)	0.0086 (3)	0.0195 (3)	−0.0078 (3)
N1	0.041 (3)	0.034 (3)	0.038 (3)	0.002 (2)	0.026 (3)	−0.003 (3)
N2	0.033 (3)	0.047 (4)	0.032 (3)	0.007 (3)	0.019 (2)	0.002 (3)
N3	0.037 (3)	0.045 (4)	0.035 (3)	0.004 (3)	0.019 (3)	−0.002 (3)
N4	0.037 (3)	0.036 (3)	0.034 (3)	0.006 (2)	0.023 (2)	0.000 (3)
C1	0.059 (4)	0.026 (4)	0.040 (4)	0.006 (3)	0.033 (4)	0.004 (3)
C2	0.044 (4)	0.017 (3)	0.032 (3)	0.003 (3)	0.021 (3)	−0.003 (3)
C3	0.039 (4)	0.046 (5)	0.038 (4)	0.008 (3)	0.020 (3)	0.004 (3)
C4	0.050 (4)	0.049 (5)	0.064 (5)	0.010 (3)	0.040 (4)	0.008 (4)
C5	0.074 (6)	0.046 (5)	0.061 (5)	0.012 (4)	0.054 (5)	0.012 (4)
C6	0.057 (4)	0.036 (4)	0.043 (4)	0.008 (3)	0.028 (4)	0.001 (3)
C7	0.036 (3)	0.034 (4)	0.026 (3)	0.004 (3)	0.020 (3)	0.006 (3)
C8	0.055 (4)	0.032 (4)	0.043 (4)	0.005 (3)	0.036 (4)	0.001 (3)
C9	0.058 (5)	0.036 (4)	0.052 (5)	−0.011 (4)	0.032 (4)	−0.009 (4)
C10	0.043 (4)	0.051 (5)	0.050 (4)	−0.011 (4)	0.023 (4)	−0.001 (4)
C11	0.033 (3)	0.050 (5)	0.037 (4)	0.005 (3)	0.021 (3)	0.008 (3)
C12	0.039 (3)	0.028 (4)	0.032 (4)	0.000 (3)	0.025 (3)	0.002 (3)
Cl1	0.0455 (9)	0.0446 (11)	0.0560 (12)	−0.0073 (8)	0.0281 (9)	−0.0116 (9)
O1	0.094 (4)	0.051 (4)	0.090 (5)	−0.012 (3)	0.041 (4)	−0.011 (3)
O2	0.098 (5)	0.117 (6)	0.066 (5)	0.042 (5)	0.018 (4)	−0.015 (4)
O3	0.171 (8)	0.115 (7)	0.317 (14)	−0.064 (6)	0.201 (10)	−0.063 (8)
O4	0.114 (5)	0.116 (6)	0.060 (4)	0.019 (5)	0.037 (4)	−0.028 (4)

Ag1—N2i	2.159 (5)	C5—C6	1.381 (11)
Ag1—N1	2.201 (5)	C5—H5	0.9300
N1—C6	1.332 (9)	C6—H6	0.9300
N1—C2	1.347 (8)	C7—C12	1.394 (8)
N2—N3	1.322 (8)	C7—C8	1.394 (9)
N2—C7	1.362 (8)	C8—C9	1.365 (9)
N2—Ag1i	2.159 (5)	C8—H8	0.9301
N3—N4	1.344 (7)	C9—C10	1.406 (10)
N4—C12	1.367 (8)	C9—H9	0.9300
N4—C1	1.470 (8)	C10—C11	1.361 (10)
C1—C2	1.514 (10)	C10—H10	0.9300
C1—H11	0.9698	C11—C12	1.393 (8)
C1—H12	0.9699	C11—H1	0.9300
C2—C3	1.339 (9)	Cl1—O3	1.355 (7)
C3—C4	1.392 (11)	Cl1—O2	1.414 (6)
C3—H3	0.9300	Cl1—O1	1.417 (6)
C4—C5	1.367 (11)	Cl1—O4	1.418 (7)
C4—H4	0.9299
N2i—Ag1—N1	155.9 (2)	C6—C5—H5	120.2
C6—N1—C2	117.5 (6)	N1—C6—C5	122.3 (7)
C6—N1—Ag1	118.1 (5)	N1—C6—H6	118.8
C2—N1—Ag1	124.3 (5)	C5—C6—H6	118.9
N3—N2—C7	109.6 (5)	N2—C7—C12	107.9 (6)
N3—N2—Ag1i	119.5 (4)	N2—C7—C8	131.5 (6)
C7—N2—Ag1i	131.0 (4)	C12—C7—C8	120.6 (6)
N2—N3—N4	107.3 (5)	C9—C8—C7	116.4 (6)
N3—N4—C12	111.1 (5)	C9—C8—H8	121.8
N3—N4—C1	119.3 (5)	C7—C8—H8	121.8
C12—N4—C1	129.4 (5)	C8—C9—C10	122.3 (7)
N4—C1—C2	112.5 (5)	C8—C9—H9	118.9
N4—C1—H11	109.0	C10—C9—H9	118.8
C2—C1—H11	109.1	C11—C10—C9	122.2 (6)
N4—C1—H12	109.2	C11—C10—H10	118.9
C2—C1—H12	109.1	C9—C10—H10	118.9
H11—C1—H12	107.8	C10—C11—C12	115.5 (6)
C3—C2—N1	123.0 (6)	C10—C11—H1	122.3
C3—C2—C1	121.2 (6)	C12—C11—H1	122.2
N1—C2—C1	115.9 (6)	N4—C12—C11	132.9 (6)
C2—C3—C4	120.1 (7)	N4—C12—C7	104.1 (5)
C2—C3—H3	119.9	C11—C12—C7	123.0 (6)
C4—C3—H3	119.9	O3—Cl1—O2	111.3 (7)
C5—C4—C3	117.3 (7)	O3—Cl1—O1	107.7 (5)
C5—C4—H4	121.4	O2—Cl1—O1	108.7 (4)
C3—C4—H4	121.2	O3—Cl1—O4	110.1 (6)
C4—C5—C6	119.7 (7)	O2—Cl1—O4	109.2 (4)
C4—C5—H5	120.1	O1—Cl1—O4	109.7 (5)
N2i—Ag1—N1—C6	53.0 (7)	C4—C5—C6—N1	1.5 (11)
N2i—Ag1—N1—C2	−124.0 (6)	N3—N2—C7—C12	−1.4 (7)
C7—N2—N3—N4	0.4 (7)	Ag1i—N2—C7—C12	178.4 (4)
Ag1i—N2—N3—N4	−179.4 (4)	N3—N2—C7—C8	−178.6 (7)
N2—N3—N4—C12	0.8 (7)	Ag1i—N2—C7—C8	1.1 (11)
N2—N3—N4—C1	176.1 (5)	N2—C7—C8—C9	178.0 (7)
N3—N4—C1—C2	−89.7 (7)	C12—C7—C8—C9	1.1 (10)
C12—N4—C1—C2	84.6 (8)	C7—C8—C9—C10	−1.5 (11)
C6—N1—C2—C3	−1.1 (9)	C8—C9—C10—C11	1.2 (12)
Ag1—N1—C2—C3	175.9 (5)	C9—C10—C11—C12	−0.3 (11)
C6—N1—C2—C1	178.0 (5)	N3—N4—C12—C11	177.9 (7)
Ag1—N1—C2—C1	−4.9 (7)	C1—N4—C12—C11	3.3 (11)
N4—C1—C2—C3	−106.9 (7)	N3—N4—C12—C7	−1.6 (7)
N4—C1—C2—N1	74.0 (7)	C1—N4—C12—C7	−176.2 (6)
N1—C2—C3—C4	1.1 (10)	C10—C11—C12—N4	−179.6 (7)
C1—C2—C3—C4	−178.0 (6)	C10—C11—C12—C7	−0.2 (10)
C2—C3—C4—C5	0.2 (11)	N2—C7—C12—N4	1.8 (7)
C3—C4—C5—C6	−1.4 (11)	C8—C7—C12—N4	179.4 (6)
C2—N1—C6—C5	−0.2 (10)	N2—C7—C12—C11	−177.8 (6)
Ag1—N1—C6—C5	−177.4 (5)	C8—C7—C12—C11	−0.2 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H11···O3i	0.97	2.31	3.264 (15)	168
C1—H12···O2ii	0.97	2.58	3.415 (11)	144
C3—H3···O1ii	0.93	2.60	3.512 (10)	168
C11—H1···O1ii	0.93	2.56	3.481 (11)	170

Ag1—N2i	2.159 (5)
Ag1—N1	2.201 (5)

N2i—Ag1—N1

155.9 (2)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H11⋯O3i	0.97	2.31	3.264 (15)	168
C1—H12⋯O2ii	0.97	2.58	3.415 (11)	144
C3—H3⋯O1ii	0.93	2.60	3.512 (10)	168
C11—H1⋯O1ii	0.93	2.56	3.481 (11)	170

Symmetry codes: (i) ; (ii) .