Bis[μ-N-(pyridin-2-ylmeth-yl)pyridin-3-amine-κ(2) N:N']disilver(I) bis-(perchlorate) dimethyl sulfoxide disolvate.

In the binuclear title compound, [Ag2(C11H11N3)2](ClO4)2·2C2H6SO, the complex cation is centrosymmetric, with the unique Ag(I) cation coordinated by two pyridine N atoms from two symmetry-related N-(pyridine-2-ylmeth-yl)pyridine-3-amine ligands in a geometry slightly distorted from linear [N-Ag-N = 170.78 (9)°], resulting in the formation of a 16-membered cyclic dimer. The two pyridine rings coordinating to the Ag(I) atom are almost perpendicular to each other [dihedral angle = 87.73 (10)°]. Inter-molecular Ag⋯O inter-actions [3.149 (3) and 2.686 (3) Å], N-H⋯O and C-H⋯O hydrogen bonds and C-H⋯π inter-actions between the cyclic dimers and the anions or the solvent mol-ecules lead to the formation of a three-dimensional supra-molecular network.

Related literature

For structures of AgI coordination polymers with symmetrical dipyridyl ligands, see: Lee et al. (2012 ▶); Leong & Vittal (2011 ▶); Park et al. (2010 ▶) and of AgI coordination polymers with unsymmetrical dipyridyl ligands, see: Moon & Park (2013 ▶); Zhang et al. (2013 ▶). For the synthesis of the ligand, see: Foxon et al. (2002 ▶); Lee et al. (2008 ▶).

Experimental

Crystal data

[Ag2(C11H11N3)2](ClO4)2·2C2H6OS

M = 941.35

Monoclinic,

a = 7.3620 (3) Å

b = 11.1227 (5) Å

c = 21.1248 (10) Å

β = 95.328 (1)°

V = 1722.34 (13) Å3

Z = 2

Mo Kα radiation

μ = 1.48 mm−1

T = 173 K

0.45 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD area-detector diffractometer

9537 measured reflections

3367 independent reflections

3096 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.086

S = 1.02

3367 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.65 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2000 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2005 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813026585/sj5353sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026585/sj5353Isup2.hkl

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

[Ag2(C11H11N3)2](ClO4)2·2C2H6OS	F(000) = 944
Mr = 941.35	Dx = 1.815 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7360 reflections
a = 7.3620 (3) Å	θ = 2.7–28.3°
b = 11.1227 (5) Å	µ = 1.48 mm−1
c = 21.1248 (10) Å	T = 173 K
β = 95.328 (1)°	Block, colorless
V = 1722.34 (13) Å3	0.45 × 0.20 × 0.20 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	3096 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.049
Graphite monochromator	θmax = 26.0°, θmin = 1.9°
φ and ω scans	h = −9→8
9537 measured reflections	k = −13→13
3367 independent reflections	l = −25→18

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0399P)2 + 3.5438P] where P = (Fo2 + 2Fc2)/3
3367 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.65 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	0.50109 (3)	0.25805 (2)	0.484406 (11)	0.02344 (10)
N1	0.3332 (3)	0.3841 (2)	0.53484 (12)	0.0200 (5)
N2	0.3266 (3)	−0.1183 (2)	0.55086 (12)	0.0200 (5)
N3	0.1611 (3)	0.1670 (2)	0.48358 (12)	0.0224 (5)
H3	0.2056	0.1604	0.4465	0.027*
C1	0.4183 (4)	0.4681 (3)	0.57264 (14)	0.0229 (6)
H1	0.5437	0.4832	0.5686	0.028*
C2	0.3334 (4)	0.5334 (3)	0.61688 (15)	0.0269 (7)
H2	0.3984	0.5924	0.6424	0.032*
C3	0.1510 (5)	0.5108 (3)	0.62316 (16)	0.0305 (7)
H3A	0.0886	0.5533	0.6536	0.037*
C4	0.0616 (4)	0.4257 (3)	0.58450 (17)	0.0288 (7)
H4	−0.0639	0.4096	0.5879	0.035*
C5	0.1546 (4)	0.3632 (3)	0.54062 (14)	0.0201 (6)
C6	0.0546 (4)	0.2732 (3)	0.49703 (16)	0.0240 (6)
H6A	−0.0562	0.2469	0.5164	0.029*
H6B	0.0145	0.3135	0.4563	0.029*
C7	0.1930 (4)	0.0766 (3)	0.52826 (14)	0.0186 (6)
C8	0.1501 (4)	0.0853 (3)	0.59090 (15)	0.0231 (6)
H8	0.0907	0.1548	0.6051	0.028*
C9	0.1955 (5)	−0.0089 (3)	0.63220 (15)	0.0275 (7)
H9	0.1657	−0.0049	0.6750	0.033*
C10	0.2841 (4)	−0.1091 (3)	0.61127 (15)	0.0265 (7)
H10	0.3156	−0.1727	0.6402	0.032*
C11	0.2807 (4)	−0.0285 (3)	0.51076 (14)	0.0187 (6)
H11	0.3090	−0.0362	0.4680	0.022*
Cl1	0.22314 (10)	0.27926 (7)	0.31521 (4)	0.02713 (18)
O1	0.1356 (6)	0.1764 (3)	0.33725 (17)	0.0789 (13)
O2	0.2542 (4)	0.3637 (3)	0.36785 (14)	0.0448 (7)
O3	0.1082 (5)	0.3355 (4)	0.26650 (16)	0.0698 (10)
O4	0.3925 (5)	0.2503 (3)	0.2927 (2)	0.0716 (12)
S1	0.60059 (11)	0.23249 (7)	0.65444 (4)	0.02617 (18)
O5	0.7044 (3)	0.2308 (2)	0.59577 (12)	0.0329 (5)
C12	0.7185 (5)	0.3371 (3)	0.70810 (17)	0.0378 (8)
H12A	0.6999	0.4189	0.6915	0.045*
H12B	0.8491	0.3184	0.7123	0.045*
H12C	0.6709	0.3312	0.7498	0.045*
C13	0.6627 (6)	0.0977 (4)	0.6968 (2)	0.0435 (9)
H13A	0.6077	0.0285	0.6736	0.052*
H13B	0.6187	0.1013	0.7392	0.052*
H13C	0.7958	0.0893	0.7011	0.052*

	U11	U22	U33	U12	U13	U23
Ag1	0.02007 (14)	0.02377 (15)	0.02746 (16)	0.00319 (8)	0.00743 (10)	−0.00257 (9)
N1	0.0173 (12)	0.0213 (12)	0.0218 (13)	0.0015 (9)	0.0038 (9)	0.0011 (10)
N2	0.0171 (12)	0.0227 (12)	0.0201 (12)	0.0000 (9)	0.0017 (9)	−0.0040 (10)
N3	0.0251 (13)	0.0213 (13)	0.0214 (13)	0.0007 (10)	0.0055 (10)	−0.0009 (10)
C1	0.0199 (14)	0.0255 (15)	0.0236 (15)	−0.0021 (12)	0.0026 (11)	0.0025 (12)
C2	0.0298 (17)	0.0243 (15)	0.0261 (16)	0.0005 (13)	0.0006 (13)	−0.0054 (13)
C3	0.0281 (17)	0.0325 (18)	0.0313 (17)	0.0059 (13)	0.0056 (13)	−0.0069 (14)
C4	0.0165 (14)	0.0332 (17)	0.0375 (18)	0.0030 (12)	0.0069 (13)	−0.0017 (15)
C5	0.0169 (13)	0.0212 (14)	0.0221 (15)	0.0008 (11)	0.0013 (11)	0.0061 (12)
C6	0.0170 (14)	0.0236 (15)	0.0310 (17)	0.0014 (11)	0.0010 (12)	−0.0006 (13)
C7	0.0134 (13)	0.0206 (14)	0.0216 (14)	−0.0032 (10)	0.0004 (10)	−0.0035 (11)
C8	0.0237 (15)	0.0227 (15)	0.0237 (15)	−0.0005 (12)	0.0064 (12)	−0.0050 (12)
C9	0.0332 (18)	0.0316 (17)	0.0187 (14)	0.0039 (13)	0.0077 (12)	−0.0018 (13)
C10	0.0292 (16)	0.0281 (16)	0.0221 (15)	0.0026 (13)	0.0016 (12)	0.0026 (13)
C11	0.0145 (13)	0.0238 (14)	0.0183 (14)	−0.0020 (11)	0.0041 (10)	−0.0031 (11)
Cl1	0.0197 (4)	0.0316 (4)	0.0305 (4)	−0.0007 (3)	0.0042 (3)	0.0034 (3)
O1	0.127 (3)	0.064 (2)	0.0482 (19)	−0.056 (2)	0.023 (2)	−0.0070 (17)
O2	0.0408 (15)	0.0491 (16)	0.0449 (16)	−0.0090 (12)	0.0067 (12)	−0.0133 (13)
O3	0.067 (2)	0.082 (3)	0.055 (2)	0.0250 (19)	−0.0210 (16)	0.0001 (18)
O4	0.0364 (18)	0.107 (3)	0.073 (3)	0.0121 (17)	0.0135 (17)	−0.029 (2)
S1	0.0257 (4)	0.0319 (4)	0.0210 (4)	0.0002 (3)	0.0030 (3)	−0.0023 (3)
O5	0.0330 (13)	0.0431 (14)	0.0235 (12)	0.0003 (10)	0.0071 (10)	−0.0045 (10)
C12	0.046 (2)	0.041 (2)	0.0263 (17)	−0.0081 (17)	0.0023 (15)	−0.0101 (15)
C13	0.051 (2)	0.036 (2)	0.043 (2)	−0.0006 (17)	0.0024 (18)	0.0077 (17)

Ag1—N2i	2.181 (2)	C7—C8	1.392 (4)
Ag1—N1	2.208 (2)	C7—C11	1.402 (4)
N1—C1	1.345 (4)	C8—C9	1.385 (4)
N1—C5	1.352 (4)	C8—H8	0.9500
N2—C11	1.332 (4)	C9—C10	1.384 (4)
N2—C10	1.346 (4)	C9—H9	0.9500
N2—Ag1i	2.181 (2)	C10—H10	0.9500
N3—C7	1.384 (4)	C11—H11	0.9500
N3—C6	1.460 (4)	Cl1—O4	1.412 (3)
N3—H3	0.8800	Cl1—O1	1.413 (3)
C1—C2	1.379 (4)	Cl1—O3	1.416 (3)
C1—H1	0.9500	Cl1—O2	1.457 (3)
C2—C3	1.385 (5)	S1—O5	1.515 (3)
C2—H2	0.9500	S1—C13	1.784 (4)
C3—C4	1.377 (5)	S1—C12	1.791 (4)
C3—H3A	0.9500	C12—H12A	0.9800
C4—C5	1.389 (4)	C12—H12B	0.9800
C4—H4	0.9500	C12—H12C	0.9800
C5—C6	1.506 (4)	C13—H13A	0.9800
C6—H6A	0.9900	C13—H13B	0.9800
C6—H6B	0.9900	C13—H13C	0.9800
N2i—Ag1—N1	170.78 (9)	C9—C8—C7	118.9 (3)
C1—N1—C5	118.0 (3)	C9—C8—H8	120.5
C1—N1—Ag1	118.47 (19)	C7—C8—H8	120.5
C5—N1—Ag1	121.8 (2)	C10—C9—C8	120.1 (3)
C11—N2—C10	118.6 (3)	C10—C9—H9	120.0
C11—N2—Ag1i	115.99 (18)	C8—C9—H9	120.0
C10—N2—Ag1i	124.9 (2)	N2—C10—C9	121.5 (3)
C7—N3—C6	121.0 (3)	N2—C10—H10	119.3
C7—N3—H3	119.5	C9—C10—H10	119.3
C6—N3—H3	119.5	N2—C11—C7	123.6 (3)
N1—C1—C2	123.6 (3)	N2—C11—H11	118.2
N1—C1—H1	118.2	C7—C11—H11	118.2
C2—C1—H1	118.2	O4—Cl1—O1	111.7 (3)
C1—C2—C3	118.3 (3)	O4—Cl1—O3	110.0 (3)
C1—C2—H2	120.8	O1—Cl1—O3	109.7 (3)
C3—C2—H2	120.8	O4—Cl1—O2	108.8 (2)
C4—C3—C2	118.8 (3)	O1—Cl1—O2	108.34 (19)
C4—C3—H3A	120.6	O3—Cl1—O2	108.1 (2)
C2—C3—H3A	120.6	O5—S1—C13	105.98 (17)
C3—C4—C5	120.1 (3)	O5—S1—C12	105.90 (16)
C3—C4—H4	119.9	C13—S1—C12	98.13 (19)
C5—C4—H4	119.9	S1—C12—H12A	109.5
N1—C5—C4	121.2 (3)	S1—C12—H12B	109.5
N1—C5—C6	119.0 (3)	H12A—C12—H12B	109.5
C4—C5—C6	119.8 (3)	S1—C12—H12C	109.5
N3—C6—C5	114.6 (2)	H12A—C12—H12C	109.5
N3—C6—H6A	108.6	H12B—C12—H12C	109.5
C5—C6—H6A	108.6	S1—C13—H13A	109.5
N3—C6—H6B	108.6	S1—C13—H13B	109.5
C5—C6—H6B	108.6	H13A—C13—H13B	109.5
H6A—C6—H6B	107.6	S1—C13—H13C	109.5
N3—C7—C8	124.0 (3)	H13A—C13—H13C	109.5
N3—C7—C11	118.6 (3)	H13B—C13—H13C	109.5
C8—C7—C11	117.3 (3)
C5—N1—C1—C2	0.2 (4)	C4—C5—C6—N3	−143.6 (3)
Ag1—N1—C1—C2	−165.1 (2)	C6—N3—C7—C8	−9.0 (4)
N1—C1—C2—C3	0.5 (5)	C6—N3—C7—C11	173.9 (3)
C1—C2—C3—C4	−0.9 (5)	N3—C7—C8—C9	−177.2 (3)
C2—C3—C4—C5	0.7 (5)	C11—C7—C8—C9	0.0 (4)
C1—N1—C5—C4	−0.4 (4)	C7—C8—C9—C10	0.8 (5)
Ag1—N1—C5—C4	164.3 (2)	C11—N2—C10—C9	−0.3 (4)
C1—N1—C5—C6	177.6 (3)	Ag1i—N2—C10—C9	170.8 (2)
Ag1—N1—C5—C6	−17.7 (4)	C8—C9—C10—N2	−0.7 (5)
C3—C4—C5—N1	0.0 (5)	C10—N2—C11—C7	1.2 (4)
C3—C4—C5—C6	−178.0 (3)	Ag1i—N2—C11—C7	−170.7 (2)
C7—N3—C6—C5	75.8 (3)	N3—C7—C11—N2	176.4 (3)
N1—C5—C6—N3	38.4 (4)	C8—C7—C11—N2	−1.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O1	0.88	2.32	3.081 (4)	144
C1—H1···O2ii	0.95	2.56	3.214 (4)	126
C6—H6A···O5iii	0.99	2.55	3.495 (4)	160
C11—H11···O5i	0.95	2.55	3.191 (4)	125
C12—H12C···O4iv	0.98	2.49	3.270 (5)	137
C13—H13A···Cg	0.98	3.36	4.116 (5)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N2/C7–C11 pyridine ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O1	0.88	2.32	3.081 (4)	144
C1—H1⋯O2i	0.95	2.56	3.214 (4)	126
C6—H6A⋯O5ii	0.99	2.55	3.495 (4)	160
C11—H11⋯O5iii	0.95	2.55	3.191 (4)	125
C12—H12C⋯O4iv	0.98	2.49	3.270 (5)	137
C13—H13A⋯Cg	0.98	3.36	4.116 (5)	136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .