Bis{μ-4′-[4-(quinolin-8-yloxymeth­yl)phen­yl]-2,2′:6′,2′′-terpyridine}disilver(I) bis­(perchlorate) dimethyl­formamide disolvate

Chen, C.-J.; Liu, F.-N.; Zhang, A.-J.; Zhang, L.-W.; Liu, X.

doi:10.1107/S1600536809046832

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1674-m1675

doi:10.1107/S1600536809046832

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Bis{μ-4′-[4-(quinolin-8-yloxymethyl)phenyl]-2,2′:6′,2′′-terpyridine}disilver(I) bis(perchlorate) dimethylformamide disolvate

Chang-Juan Chen,^a Feng-Neng Liu,^a Ai-Jiang Zhang,^a Liang-Wei Zhang ^a and Xiang Liu ^a ^*

^aState Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, People's Republic of China
^*Correspondence e-mail: liuxiang@lzu.edu.cn

(Received 28 September 2009; accepted 6 November 2009; online 25 November 2009)

In the binuclear title complex, [Ag₂(C₃₁H₂₂N₄O)₂](ClO₄)₂·2C₃H₇NO, the Ag^I atom is pentacoordinated by three N atoms from the tridentate chelating terpyridyl group and by one N atom and one O atom from the quinolin-8-yloxy group in a distorted square-pyramidal geometry with the O atom at the apical position. The centrosymmetric complex cation involves intramolecular π–π stacking interactions [centroid–centroid distance = 3.862 (4) Å] between the central pyridine and benzene rings. In the crystal structure, intermolecular C—H⋯O hydrogen bonds result in the formation of a supramolecular network.

Related literature

For applications of 2,2′:6′,2′′-terpyridine in supramolecular frameworks and functional materials, see: Andres & Schubert (2004 ); Constable et al. (2005 ); Thompson (1997 ); Ziener et al. (2000 ). For the ligand synthesis, see: Chow et al. (2006 ). For related structures, see: Hou & Li (2005 ).

Experimental

Crystal data

[Ag₂(C₃₁H₂₂N₄O)₂](ClO₄)₂·2C₃H₇NO
M_r = 1493.88
Monoclinic, P 2₁ /c
a = 10.0552 (16) Å
b = 10.9548 (18) Å
c = 29.657 (5) Å
β = 96.767 (8)°
V = 3244.0 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 296 K
0.22 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.847, T_max = 0.860
20993 measured reflections
8077 independent reflections
5406 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.118
S = 1.03
8077 reflections
426 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—O1	2.5995 (19)
Ag1—N1	2.434 (3)
Ag1—N2	2.3572 (19)
Ag1—N3	2.414 (3)
Ag1—N4	2.275 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O3ⁱ	0.93	2.57	3.450 (5)	158
C12—H12⋯O5ⁱⁱ	0.93	2.60	3.344 (5)	138
C28—H28⋯O6ⁱⁱⁱ	0.93	2.37	3.250 (5)	158
C29—H29⋯O4	0.93	2.57	3.252 (6)	130
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z+1; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809046832/hy2238sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046832/hy2238Isup2.hkl

checkCIF report

Comment top

2,2':6',2''-Terpyridine is well known for its applications in the synthesis of supramolecular frameworks and functional materials (Andres & Schubert, 2004; Constable et al., 2005; Thompson, 1997; Ziener et al., 2000). Therefore, it is necessary to further widen the system of multifunctional terpyridyl derivates complexes. Herein we report the synthesis and structure of an Ag^I complex with a new ligand 4'-[4'-(8-oxyqulinoline)benzyl]-2,2':6',2''-terpyridine.

The complex cation of the title compound has a twisted box structure formed by two ligands bridging two Ag^I atoms. The asymmetric unit consists of a half of the cation, one perchlorate anion and one dimethylformamide solvent molecule. As shown Fig. 1, the two ligands are arranged in a head-to-tail fashion. The Ag^I atom is pentacoordinated by three N atoms of the tridentate chelating terpyridyl group and by one N and one O atoms from the quinolin-8-yloxy group [Ag—N = 2.275 (2)–2.434 (3) Å and Ag—O = 2.5995 (19) Å] (Table 1). The Ag···Ag distance is 10.744 (6) Å in the dimeric complex cation. The plane of the 4'-phenyl-2,2':6',2''-terpyridine group is almost perpendicular to that of the quinoline group, with a dihedral angel of 79.96 (1)°. The complex cation involves π–π stacking interactions [centroid–centroid distance = 3.862 (4) Å] between the central pyridine rings and the phenyl rings. In the crystal structure, intermolecular C—H···O hydrogen bonds result in the formation of a supramolecular network (Table 2 and Fig. 2).

Related literature top

For applications of 2,2':6',2''-terpyridine in supramolecular frameworks and functional materials, see: Andres & Schubert (2004); Constable et al. (2005); Thompson (1997); Ziener et al. (2000). For the ligand synthesis, see: Chow et al. (2006). For related structures, see: Hou & Li (2005).

Experimental top

The ligand was synthesized according to the literature (Chow et al., 2006). A solution of AgClO₄(23.72 mg, 0.10 mmol) in CH₃OH (10 ml) was added to a solution of the ligand (46.6 mg, 0.10 mmol) in CHCl₃ (10 ml) with stirring. The brown precipitate was collected by filtration and washed sequentially with 10 ml CH₃OH and CHCl₃. Brown crystals suitable for X-ray structure determination were obtained by slow diffusion of diethyl ether into the DMF solution of the product in several days.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted for clarity. [Symmetry code: (A) 2 - z, 1 - y, 1 - z.]
	Fig. 2. Packing diagram along the c axis of the title compound. Hydrogen bonds are shown as dashed lines.

Bis{µ-4'-[4-(quinolin-8-yloxymethyl)phenyl]-2,2':6',2''- terpyridine}disilver(I) bis(perchlorate) dimethylformamide disolvate top

Crystal data top

[Ag₂(C₃₁H₂₂N₄O)₂](ClO₄)₂·2C₃H₇NO	F(000) = 1520
M_r = 1493.88	D_x = 1.529 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6845 reflections
a = 10.0552 (16) Å	θ = 2.3–28.6°
b = 10.9548 (18) Å	µ = 0.76 mm⁻¹
c = 29.657 (5) Å	T = 296 K
β = 96.767 (8)°	Block, yellow
V = 3244.0 (9) Å³	0.22 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD diffractometer	8077 independent reflections
Radiation source: fine-focus sealed tube	5406 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 28.7°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.847, T_max = 0.860	k = −14→14
20993 measured reflections	l = −40→28

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0551P)² + 1.1422P] where P = (F_o² + 2F_c²)/3
8077 reflections	(Δ/σ)_max = 0.001
426 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.44 e Å⁻³

Crystal data top

[Ag₂(C₃₁H₂₂N₄O)₂](ClO₄)₂·2C₃H₇NO	V = 3244.0 (9) Å³
M_r = 1493.88	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0552 (16) Å	µ = 0.76 mm⁻¹
b = 10.9548 (18) Å	T = 296 K
c = 29.657 (5) Å	0.22 × 0.20 × 0.20 mm
β = 96.767 (8)°

Data collection top

Bruker APEXII CCD diffractometer	8077 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5406 reflections with I > 2σ(I)
T_min = 0.847, T_max = 0.860	R_int = 0.020
20993 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.03	Δρ_max = 0.67 e Å⁻³
8077 reflections	Δρ_min = −0.44 e Å⁻³
426 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.60078 (2)	0.42357 (2)	0.602143 (7)	0.06913 (11)
C1	0.6898 (5)	0.1295 (4)	0.61912 (13)	0.1029 (14)
H1	0.6456	0.1402	0.6447	0.123*
C2	0.7329 (5)	0.0155 (4)	0.60987 (14)	0.1074 (15)
H2	0.7210	−0.0493	0.6293	0.129*
C3	0.7939 (4)	−0.0024 (3)	0.57173 (14)	0.0904 (12)
H3	0.8235	−0.0795	0.5645	0.108*
C4	0.8109 (3)	0.0965 (3)	0.54406 (11)	0.0698 (9)
H4	0.8512	0.0863	0.5176	0.084*
C5	0.7678 (3)	0.2102 (2)	0.55580 (9)	0.0534 (6)
C6	0.7810 (2)	0.3201 (2)	0.52706 (8)	0.0463 (5)
C7	0.8646 (2)	0.3213 (2)	0.49286 (8)	0.0487 (6)
H7	0.9159	0.2530	0.4880	0.058*
C8	0.8716 (2)	0.4248 (2)	0.46597 (7)	0.0412 (5)
C9	0.7944 (2)	0.5249 (2)	0.47579 (8)	0.0459 (5)
H9	0.7971	0.5964	0.4590	0.055*
C10	0.7135 (2)	0.5180 (2)	0.51051 (8)	0.0432 (5)
C11	0.6290 (2)	0.6236 (2)	0.52240 (8)	0.0472 (6)
C12	0.6129 (3)	0.7268 (3)	0.49576 (11)	0.0631 (7)
H12	0.6549	0.7329	0.4695	0.076*
C13	0.5341 (3)	0.8211 (3)	0.50828 (13)	0.0785 (9)
H13	0.5232	0.8918	0.4909	0.094*
C14	0.4719 (3)	0.8092 (3)	0.54682 (13)	0.0810 (10)
H14	0.4186	0.8714	0.5563	0.097*
C15	0.4906 (3)	0.7035 (3)	0.57070 (12)	0.0805 (10)
H15	0.4477	0.6950	0.5966	0.097*
C16	0.9562 (2)	0.4271 (2)	0.42791 (8)	0.0442 (5)
C17	1.0168 (4)	0.3227 (3)	0.41471 (11)	0.0782 (10)
H17	1.0084	0.2507	0.4307	0.094*
C18	1.0903 (4)	0.3227 (3)	0.37802 (12)	0.0806 (10)
H18	1.1317	0.2510	0.3703	0.097*
C19	1.1035 (3)	0.4254 (3)	0.35296 (9)	0.0544 (6)
C20	1.0478 (3)	0.5310 (3)	0.36688 (10)	0.0680 (8)
H20	1.0580	0.6030	0.3510	0.082*
C21	0.9763 (3)	0.5325 (3)	0.40425 (10)	0.0601 (7)
H21	0.9415	0.6059	0.4134	0.072*
C22	1.1736 (3)	0.4222 (3)	0.31074 (10)	0.0654 (8)
H22A	1.1898	0.3384	0.3023	0.078*
H22B	1.1186	0.4611	0.2857	0.078*
C23	0.6229 (3)	0.5043 (3)	0.71396 (8)	0.0558 (7)
C24	0.6558 (4)	0.5487 (3)	0.75690 (10)	0.0733 (9)
H24	0.7364	0.5895	0.7645	0.088*
C25	0.5659 (4)	0.5321 (4)	0.78984 (11)	0.0891 (11)
H25	0.5892	0.5605	0.8192	0.107*
C26	0.4473 (4)	0.4757 (4)	0.77919 (11)	0.0804 (10)
H26	0.3892	0.4669	0.8012	0.097*
C27	0.4105 (3)	0.4299 (3)	0.73521 (10)	0.0609 (7)
C28	0.2875 (3)	0.3705 (3)	0.72234 (11)	0.0717 (9)
H28	0.2256	0.3621	0.7431	0.086*
C29	0.2598 (3)	0.3259 (3)	0.67989 (12)	0.0744 (9)
H29	0.1796	0.2853	0.6713	0.089*
C30	0.3534 (3)	0.3414 (3)	0.64886 (10)	0.0710 (8)
H30	0.3333	0.3094	0.6198	0.085*
C31	0.4993 (3)	0.4438 (2)	0.70169 (9)	0.0511 (6)
C32	0.1542 (7)	0.7098 (6)	0.7540 (3)	0.163 (2)
H32A	0.0821	0.7381	0.7698	0.244*
H32B	0.2378	0.7227	0.7726	0.244*
H32C	0.1429	0.6243	0.7475	0.244*
C33	0.2519 (5)	0.7433 (6)	0.6824 (2)	0.160 (3)
H33A	0.2429	0.7970	0.6566	0.241*
H33B	0.2373	0.6606	0.6723	0.241*
H33C	0.3403	0.7509	0.6983	0.241*
C34	0.0645 (5)	0.8613 (4)	0.70234 (18)	0.1072 (14)
H34	0.0688	0.9030	0.6752	0.129*
Cl1	0.17980 (9)	0.06784 (7)	0.58331 (3)	0.0737 (2)
N1	0.7077 (3)	0.2271 (2)	0.59336 (8)	0.0769 (8)
N2	0.7070 (2)	0.41714 (18)	0.53544 (7)	0.0451 (5)
N3	0.5667 (3)	0.6108 (2)	0.55944 (8)	0.0645 (6)
N4	0.4683 (2)	0.3990 (2)	0.65858 (7)	0.0567 (6)
N5	0.1541 (4)	0.7757 (4)	0.71246 (16)	0.1093 (11)
O1	0.70259 (19)	0.5143 (2)	0.67959 (6)	0.0649 (5)
O2	0.3231 (3)	0.0703 (3)	0.58888 (11)	0.1059 (9)
O3	0.1299 (4)	−0.0427 (3)	0.56646 (13)	0.1260 (12)
O4	0.1325 (5)	0.0871 (4)	0.62572 (16)	0.180 (2)
O5	0.1337 (3)	0.1632 (3)	0.55563 (17)	0.1655 (18)
O6	−0.0233 (4)	0.8916 (3)	0.72468 (14)	0.1380 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.08213 (18)	0.08620 (19)	0.04559 (13)	−0.00483 (12)	0.03491 (11)	−0.00590 (10)
C1	0.160 (4)	0.082 (2)	0.082 (2)	0.015 (3)	0.077 (3)	0.026 (2)
C2	0.158 (4)	0.078 (3)	0.100 (3)	0.021 (3)	0.076 (3)	0.040 (2)
C3	0.107 (3)	0.068 (2)	0.106 (3)	0.0214 (19)	0.055 (2)	0.028 (2)
C4	0.081 (2)	0.0640 (19)	0.0718 (19)	0.0146 (15)	0.0415 (17)	0.0185 (14)
C5	0.0590 (15)	0.0576 (16)	0.0474 (14)	0.0007 (12)	0.0221 (12)	0.0081 (12)
C6	0.0492 (13)	0.0519 (14)	0.0403 (12)	−0.0003 (11)	0.0156 (10)	0.0025 (10)
C7	0.0544 (14)	0.0475 (14)	0.0483 (13)	0.0059 (11)	0.0227 (11)	0.0026 (11)
C8	0.0407 (12)	0.0509 (13)	0.0337 (11)	−0.0011 (10)	0.0109 (9)	−0.0006 (9)
C9	0.0505 (14)	0.0482 (13)	0.0409 (12)	0.0029 (11)	0.0134 (10)	0.0034 (10)
C10	0.0427 (13)	0.0500 (14)	0.0383 (12)	−0.0016 (10)	0.0108 (10)	−0.0037 (10)
C11	0.0426 (13)	0.0541 (14)	0.0464 (13)	−0.0006 (11)	0.0120 (10)	−0.0076 (11)
C12	0.0659 (17)	0.0560 (17)	0.0712 (18)	0.0059 (14)	0.0245 (14)	−0.0010 (14)
C13	0.082 (2)	0.0589 (19)	0.100 (3)	0.0136 (16)	0.0305 (19)	−0.0012 (17)
C14	0.077 (2)	0.074 (2)	0.097 (3)	0.0214 (18)	0.0289 (19)	−0.0159 (19)
C15	0.081 (2)	0.092 (3)	0.076 (2)	0.0163 (19)	0.0429 (17)	−0.0136 (19)
C16	0.0448 (12)	0.0531 (14)	0.0370 (11)	0.0004 (11)	0.0143 (10)	−0.0004 (10)
C17	0.110 (3)	0.0582 (18)	0.078 (2)	0.0189 (17)	0.0595 (19)	0.0140 (15)
C18	0.111 (3)	0.0619 (19)	0.081 (2)	0.0178 (18)	0.062 (2)	0.0014 (16)
C19	0.0544 (15)	0.0674 (17)	0.0453 (13)	−0.0058 (13)	0.0220 (11)	−0.0067 (12)
C20	0.082 (2)	0.0683 (18)	0.0608 (17)	0.0028 (16)	0.0380 (16)	0.0150 (14)
C21	0.0707 (18)	0.0545 (15)	0.0611 (16)	0.0067 (13)	0.0331 (14)	0.0062 (13)
C22	0.0670 (18)	0.084 (2)	0.0498 (15)	−0.0139 (15)	0.0280 (13)	−0.0125 (14)
C23	0.0615 (16)	0.0705 (18)	0.0409 (13)	0.0039 (13)	0.0286 (12)	−0.0040 (12)
C24	0.081 (2)	0.094 (2)	0.0510 (16)	−0.0151 (17)	0.0307 (15)	−0.0187 (15)
C25	0.103 (3)	0.122 (3)	0.0496 (17)	−0.020 (2)	0.0410 (18)	−0.0262 (18)
C26	0.092 (2)	0.103 (3)	0.0559 (17)	−0.009 (2)	0.0482 (17)	−0.0122 (17)
C27	0.0656 (17)	0.0709 (18)	0.0523 (15)	0.0054 (14)	0.0329 (13)	0.0022 (13)
C28	0.070 (2)	0.083 (2)	0.069 (2)	0.0011 (16)	0.0406 (16)	0.0095 (17)
C29	0.0655 (19)	0.089 (2)	0.071 (2)	−0.0088 (17)	0.0203 (15)	0.0065 (17)
C30	0.072 (2)	0.094 (2)	0.0502 (16)	−0.0101 (17)	0.0173 (14)	−0.0025 (15)
C31	0.0598 (16)	0.0558 (15)	0.0426 (13)	0.0086 (12)	0.0269 (12)	0.0015 (10)
C32	0.172 (6)	0.138 (5)	0.174 (6)	0.005 (4)	0.000 (5)	0.008 (5)
C33	0.113 (4)	0.151 (5)	0.228 (7)	0.012 (4)	0.065 (4)	−0.052 (5)
C34	0.103 (3)	0.095 (3)	0.132 (4)	−0.008 (3)	0.045 (3)	−0.008 (3)
Cl1	0.0887 (6)	0.0615 (5)	0.0756 (5)	−0.0031 (4)	0.0286 (4)	−0.0032 (4)
N1	0.108 (2)	0.0706 (17)	0.0612 (15)	0.0056 (15)	0.0482 (15)	0.0132 (12)
N2	0.0458 (11)	0.0533 (12)	0.0384 (10)	−0.0010 (9)	0.0137 (8)	0.0005 (9)
N3	0.0684 (15)	0.0729 (16)	0.0570 (14)	0.0133 (12)	0.0274 (12)	−0.0021 (12)
N4	0.0608 (14)	0.0696 (15)	0.0431 (11)	−0.0014 (11)	0.0212 (10)	0.0008 (10)
N5	0.099 (3)	0.094 (3)	0.138 (3)	−0.003 (2)	0.024 (2)	−0.016 (2)
O1	0.0634 (12)	0.0923 (15)	0.0450 (10)	−0.0149 (10)	0.0314 (9)	−0.0126 (10)
O2	0.0906 (19)	0.113 (2)	0.115 (2)	0.0127 (15)	0.0156 (16)	0.0025 (16)
O3	0.158 (3)	0.0764 (18)	0.151 (3)	−0.0307 (19)	0.051 (2)	−0.0370 (19)
O4	0.185 (4)	0.239 (5)	0.130 (3)	−0.052 (3)	0.081 (3)	−0.081 (3)
O5	0.091 (2)	0.121 (3)	0.284 (5)	0.0051 (19)	0.021 (3)	0.105 (3)
O6	0.125 (3)	0.140 (3)	0.165 (3)	0.011 (2)	0.082 (2)	−0.011 (2)

Geometric parameters (Å, º) top

Ag1—O1	2.5995 (19)	C19—C20	1.370 (4)
Ag1—N1	2.434 (3)	C19—C22	1.508 (3)
Ag1—N2	2.3572 (19)	C20—C21	1.390 (4)
Ag1—N3	2.414 (3)	C20—H20	0.9300
Ag1—N4	2.275 (2)	C21—H21	0.9300
C1—N1	1.338 (4)	C22—O1ⁱ	1.426 (3)
C1—C2	1.361 (5)	C22—H22A	0.9700
C1—H1	0.9300	C22—H22B	0.9700
C2—C3	1.363 (5)	C23—C24	1.367 (4)
C2—H2	0.9300	C23—O1	1.373 (3)
C3—C4	1.382 (4)	C23—C31	1.418 (4)
C3—H3	0.9300	C24—C25	1.419 (4)
C4—C5	1.377 (4)	C24—H24	0.9300
C4—H4	0.9300	C25—C26	1.347 (5)
C5—N1	1.341 (3)	C25—H25	0.9300
C5—C6	1.489 (3)	C26—C27	1.406 (4)
C6—N2	1.338 (3)	C26—H26	0.9300
C6—C7	1.392 (3)	C27—C28	1.410 (5)
C7—C8	1.392 (3)	C27—C31	1.421 (3)
C7—H7	0.9300	C28—C29	1.348 (5)
C8—C9	1.395 (3)	C28—H28	0.9300
C8—C16	1.491 (3)	C29—C30	1.402 (4)
C9—C10	1.387 (3)	C29—H29	0.9300
C9—H9	0.9300	C30—N4	1.318 (4)
C10—N2	1.335 (3)	C30—H30	0.9300
C10—C11	1.501 (3)	C31—N4	1.371 (3)
C11—N3	1.335 (3)	C32—N5	1.428 (7)
C11—C12	1.378 (4)	C32—H32A	0.9600
C12—C13	1.380 (4)	C32—H32B	0.9600
C12—H12	0.9300	C32—H32C	0.9600
C13—C14	1.372 (5)	C33—N5	1.448 (6)
C13—H13	0.9300	C33—H33A	0.9600
C14—C15	1.359 (5)	C33—H33B	0.9600
C14—H14	0.9300	C33—H33C	0.9600
C15—N3	1.337 (4)	C34—O6	1.211 (5)
C15—H15	0.9300	C34—N5	1.310 (6)
C16—C17	1.374 (4)	C34—H34	0.9300
C16—C21	1.379 (4)	Cl1—O5	1.375 (3)
C17—C18	1.385 (4)	Cl1—O3	1.382 (3)
C17—H17	0.9300	Cl1—O4	1.412 (4)
C18—C19	1.363 (4)	Cl1—O2	1.432 (3)
C18—H18	0.9300	O1—C22ⁱ	1.426 (4)

N4—Ag1—N2	167.56 (8)	O1ⁱ—C22—C19	107.7 (2)
N4—Ag1—N3	115.30 (8)	O1ⁱ—C22—H22A	110.2
N2—Ag1—N3	68.62 (7)	C19—C22—H22A	110.2
N4—Ag1—N1	106.16 (8)	O1ⁱ—C22—H22B	110.2
N2—Ag1—N1	68.55 (7)	C19—C22—H22B	110.2
N3—Ag1—N1	137.12 (7)	H22A—C22—H22B	108.5
N4—Ag1—O1	66.35 (7)	C24—C23—O1	124.4 (3)
N2—Ag1—O1	125.64 (6)	C24—C23—C31	120.9 (2)
N3—Ag1—O1	98.95 (8)	O1—C23—C31	114.7 (2)
N1—Ag1—O1	107.45 (9)	C23—C24—C25	119.5 (3)
N1—C1—C2	123.4 (3)	C23—C24—H24	120.3
N1—C1—H1	118.3	C25—C24—H24	120.3
C2—C1—H1	118.3	C26—C25—C24	121.1 (3)
C1—C2—C3	118.9 (3)	C26—C25—H25	119.5
C1—C2—H2	120.5	C24—C25—H25	119.5
C3—C2—H2	120.5	C25—C26—C27	120.7 (3)
C2—C3—C4	118.7 (3)	C25—C26—H26	119.7
C2—C3—H3	120.7	C27—C26—H26	119.7
C4—C3—H3	120.7	C26—C27—C28	122.9 (3)
C5—C4—C3	119.6 (3)	C26—C27—C31	119.5 (3)
C5—C4—H4	120.2	C28—C27—C31	117.6 (3)
C3—C4—H4	120.2	C29—C28—C27	119.9 (3)
N1—C5—C4	121.4 (2)	C29—C28—H28	120.1
N1—C5—C6	116.3 (2)	C27—C28—H28	120.1
C4—C5—C6	122.3 (2)	C28—C29—C30	119.2 (3)
N2—C6—C7	121.6 (2)	C28—C29—H29	120.4
N2—C6—C5	116.5 (2)	C30—C29—H29	120.4
C7—C6—C5	121.8 (2)	N4—C30—C29	123.6 (3)
C6—C7—C8	120.1 (2)	N4—C30—H30	118.2
C6—C7—H7	120.0	C29—C30—H30	118.2
C8—C7—H7	120.0	N4—C31—C23	120.2 (2)
C7—C8—C9	117.0 (2)	N4—C31—C27	121.5 (3)
C7—C8—C16	121.3 (2)	C23—C31—C27	118.3 (2)
C9—C8—C16	121.7 (2)	N5—C32—H32A	109.5
C10—C9—C8	120.1 (2)	N5—C32—H32B	109.5
C10—C9—H9	119.9	H32A—C32—H32B	109.5
C8—C9—H9	119.9	N5—C32—H32C	109.5
N2—C10—C9	121.8 (2)	H32A—C32—H32C	109.5
N2—C10—C11	116.2 (2)	H32B—C32—H32C	109.5
C9—C10—C11	122.0 (2)	N5—C33—H33A	109.5
N3—C11—C12	121.5 (2)	N5—C33—H33B	109.5
N3—C11—C10	116.5 (2)	H33A—C33—H33B	109.5
C12—C11—C10	122.0 (2)	N5—C33—H33C	109.5
C11—C12—C13	119.5 (3)	H33A—C33—H33C	109.5
C11—C12—H12	120.2	H33B—C33—H33C	109.5
C13—C12—H12	120.2	O6—C34—N5	126.6 (5)
C14—C13—C12	119.1 (3)	O6—C34—H34	116.7
C14—C13—H13	120.5	N5—C34—H34	116.7
C12—C13—H13	120.5	O5—Cl1—O3	111.6 (3)
C15—C14—C13	117.8 (3)	O5—Cl1—O4	107.0 (3)
C15—C14—H14	121.1	O3—Cl1—O4	107.9 (2)
C13—C14—H14	121.1	O5—Cl1—O2	108.57 (19)
N3—C15—C14	124.4 (3)	O3—Cl1—O2	112.1 (2)
N3—C15—H15	117.8	O4—Cl1—O2	109.6 (2)
C14—C15—H15	117.8	C1—N1—C5	117.9 (3)
C17—C16—C21	117.1 (2)	C1—N1—Ag1	123.7 (2)
C17—C16—C8	120.9 (2)	C5—N1—Ag1	117.28 (18)
C21—C16—C8	122.0 (2)	C10—N2—C6	119.36 (19)
C16—C17—C18	121.3 (3)	C10—N2—Ag1	119.76 (15)
C16—C17—H17	119.3	C6—N2—Ag1	119.77 (15)
C18—C17—H17	119.3	C11—N3—C15	117.7 (3)
C19—C18—C17	121.6 (3)	C11—N3—Ag1	117.99 (18)
C19—C18—H18	119.2	C15—N3—Ag1	124.3 (2)
C17—C18—H18	119.2	C30—N4—C31	118.2 (2)
C18—C19—C20	117.6 (2)	C30—N4—Ag1	118.02 (19)
C18—C19—C22	121.2 (3)	C31—N4—Ag1	123.75 (18)
C20—C19—C22	121.2 (3)	C34—N5—C32	119.4 (5)
C19—C20—C21	121.2 (3)	C34—N5—C33	122.2 (5)
C19—C20—H20	119.4	C32—N5—C33	118.4 (5)
C21—C20—H20	119.4	C23—O1—C22ⁱ	117.5 (2)
C16—C21—C20	121.1 (3)	C23—O1—Ag1	114.95 (16)
C16—C21—H21	119.5	C22ⁱ—O1—Ag1	127.44 (14)
C20—C21—H21	119.5

N1—C1—C2—C3	−2.1 (8)	N4—Ag1—N1—C1	−1.9 (4)
C1—C2—C3—C4	0.6 (7)	N2—Ag1—N1—C1	−170.0 (4)
C2—C3—C4—C5	0.8 (6)	N3—Ag1—N1—C1	−166.9 (3)
C3—C4—C5—N1	−1.0 (5)	O1—Ag1—N1—C1	67.8 (4)
C3—C4—C5—C6	−178.9 (3)	N4—Ag1—N1—C5	165.8 (2)
N1—C5—C6—N2	−14.4 (4)	N2—Ag1—N1—C5	−2.3 (2)
C4—C5—C6—N2	163.7 (3)	N3—Ag1—N1—C5	0.9 (3)
N1—C5—C6—C7	166.4 (3)	O1—Ag1—N1—C5	−124.5 (2)
C4—C5—C6—C7	−15.5 (4)	C9—C10—N2—C6	0.5 (4)
N2—C6—C7—C8	−0.8 (4)	C11—C10—N2—C6	−179.2 (2)
C5—C6—C7—C8	178.4 (2)	C9—C10—N2—Ag1	168.45 (18)
C6—C7—C8—C9	1.4 (4)	C11—C10—N2—Ag1	−11.2 (3)
C6—C7—C8—C16	−177.6 (2)	C7—C6—N2—C10	−0.2 (4)
C7—C8—C9—C10	−1.1 (4)	C5—C6—N2—C10	−179.4 (2)
C16—C8—C9—C10	177.9 (2)	C7—C6—N2—Ag1	−168.13 (19)
C8—C9—C10—N2	0.2 (4)	C5—C6—N2—Ag1	12.7 (3)
C8—C9—C10—C11	179.8 (2)	N4—Ag1—N2—C10	119.3 (4)
N2—C10—C11—N3	6.6 (3)	N3—Ag1—N2—C10	8.49 (18)
C9—C10—C11—N3	−173.0 (2)	N1—Ag1—N2—C10	−173.8 (2)
N2—C10—C11—C12	−171.3 (2)	O1—Ag1—N2—C10	−77.2 (2)
C9—C10—C11—C12	9.0 (4)	N4—Ag1—N2—C6	−72.7 (4)
N3—C11—C12—C13	2.1 (5)	N3—Ag1—N2—C6	176.4 (2)
C10—C11—C12—C13	180.0 (3)	N1—Ag1—N2—C6	−5.86 (18)
C11—C12—C13—C14	−0.8 (5)	O1—Ag1—N2—C6	90.73 (19)
C12—C13—C14—C15	−0.5 (6)	C12—C11—N3—C15	−1.9 (4)
C13—C14—C15—N3	0.7 (6)	C10—C11—N3—C15	−179.9 (3)
C7—C8—C16—C17	8.0 (4)	C12—C11—N3—Ag1	178.9 (2)
C9—C8—C16—C17	−170.9 (3)	C10—C11—N3—Ag1	0.9 (3)
C7—C8—C16—C21	−172.5 (3)	C14—C15—N3—C11	0.5 (5)
C9—C8—C16—C21	8.6 (4)	C14—C15—N3—Ag1	179.7 (3)
C21—C16—C17—C18	−2.6 (5)	N4—Ag1—N3—C11	−171.7 (2)
C8—C16—C17—C18	176.9 (3)	N2—Ag1—N3—C11	−4.6 (2)
C16—C17—C18—C19	−1.3 (6)	N1—Ag1—N3—C11	−7.7 (3)
C17—C18—C19—C20	3.7 (6)	O1—Ag1—N3—C11	120.3 (2)
C17—C18—C19—C22	−174.7 (3)	N4—Ag1—N3—C15	9.1 (3)
C18—C19—C20—C21	−2.3 (5)	N2—Ag1—N3—C15	176.3 (3)
C22—C19—C20—C21	176.2 (3)	N1—Ag1—N3—C15	173.1 (3)
C17—C16—C21—C20	4.0 (5)	O1—Ag1—N3—C15	−58.9 (3)
C8—C16—C21—C20	−175.5 (3)	C29—C30—N4—C31	1.5 (5)
C19—C20—C21—C16	−1.6 (5)	C29—C30—N4—Ag1	−176.6 (3)
C18—C19—C22—O1ⁱ	−109.7 (3)	C23—C31—N4—C30	178.8 (3)
C20—C19—C22—O1ⁱ	72.0 (4)	C27—C31—N4—C30	−0.4 (4)
O1—C23—C24—C25	−179.4 (3)	C23—C31—N4—Ag1	−3.3 (3)
C31—C23—C24—C25	1.1 (5)	C27—C31—N4—Ag1	177.55 (19)
C23—C24—C25—C26	−1.5 (6)	N2—Ag1—N4—C30	−14.0 (5)
C24—C25—C26—C27	1.1 (6)	N3—Ag1—N4—C30	91.7 (2)
C25—C26—C27—C28	−179.8 (4)	N1—Ag1—N4—C30	−77.0 (2)
C25—C26—C27—C31	−0.2 (5)	O1—Ag1—N4—C30	−179.3 (3)
C26—C27—C28—C29	−178.3 (3)	N2—Ag1—N4—C31	168.1 (3)
C31—C27—C28—C29	2.1 (5)	N3—Ag1—N4—C31	−86.2 (2)
C27—C28—C29—C30	−1.2 (5)	N1—Ag1—N4—C31	105.0 (2)
C28—C29—C30—N4	−0.7 (6)	O1—Ag1—N4—C31	2.70 (19)
C24—C23—C31—N4	−179.5 (3)	O6—C34—N5—C32	−1.1 (8)
O1—C23—C31—N4	1.0 (4)	O6—C34—N5—C33	177.5 (5)
C24—C23—C31—C27	−0.3 (4)	C24—C23—O1—C22ⁱ	−1.6 (4)
O1—C23—C31—C27	−179.8 (2)	C31—C23—O1—C22ⁱ	178.0 (3)
C26—C27—C31—N4	179.0 (3)	C24—C23—O1—Ag1	−178.2 (3)
C28—C27—C31—N4	−1.3 (4)	C31—C23—O1—Ag1	1.3 (3)
C26—C27—C31—C23	−0.2 (4)	N4—Ag1—O1—C23	−2.03 (18)
C28—C27—C31—C23	179.4 (3)	N2—Ag1—O1—C23	−178.19 (17)
C2—C1—N1—C5	2.0 (7)	N3—Ag1—O1—C23	111.75 (19)
C2—C1—N1—Ag1	169.7 (4)	N1—Ag1—O1—C23	−102.4 (2)
C4—C5—N1—C1	−0.4 (5)	N4—Ag1—O1—C22ⁱ	−178.3 (3)
C6—C5—N1—C1	177.7 (3)	N2—Ag1—O1—C22ⁱ	5.5 (3)
C4—C5—N1—Ag1	−168.9 (2)	N3—Ag1—O1—C22ⁱ	−64.5 (2)
C6—C5—N1—Ag1	9.2 (3)	N1—Ag1—O1—C22ⁱ	81.3 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱⁱ	0.93	2.57	3.450 (5)	158
C12—H12···O5ⁱⁱⁱ	0.93	2.60	3.344 (5)	138
C28—H28···O6^iv	0.93	2.37	3.250 (5)	158
C29—H29···O4	0.93	2.57	3.252 (6)	130

Symmetry codes: (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Ag₂(C₃₁H₂₂N₄O)₂](ClO₄)₂·2C₃H₇NO
M_r	1493.88
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.0552 (16), 10.9548 (18), 29.657 (5)
β (°)	96.767 (8)
V (Å³)	3244.0 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.22 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.847, 0.860
No. of measured, independent and observed [I > 2σ(I)] reflections	20993, 8077, 5406
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.118, 1.03
No. of reflections	8077
No. of parameters	426
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.44

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ag1—O1	2.5995 (19)	Ag1—N3	2.414 (3)
Ag1—N1	2.434 (3)	Ag1—N4	2.275 (2)
Ag1—N2	2.3572 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O3ⁱ	0.93	2.57	3.450 (5)	158
C12—H12···O5ⁱⁱ	0.93	2.60	3.344 (5)	138
C28—H28···O6ⁱⁱⁱ	0.93	2.37	3.250 (5)	158
C29—H29···O4	0.93	2.57	3.252 (6)	130

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x, y−1/2, −z+3/2.

Acknowledgements

The authors acknowledge the Research Foundation for Young Teachers Possessing a Doctoral Degree of Lanzhou University for financial support.

References

Andres, P. R. & Schubert, U. S. (2004). Adv. Mater. 16, 1043–1068. Web of Science CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chow, H. S., Constable, E. C., Housecroft, C. E., Neuburger, M. & Schaffner, S. (2006). Dalton Trans. pp. 2881–2890. Web of Science CSD CrossRef Google Scholar
Constable, E. C., Housecroft, C. H., Neuburger, M., Schaffner, S. & Shardlow, E. J. (2005). CrystEngComm, 7, 599–602. Web of Science CSD CrossRef CAS Google Scholar
Hou, L. & Li, D. (2005). Inorg. Chem. Commun. 8, 128–130. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Ziener, U., Breuning, E., Lehn, J.-M., Wegelius, E., Rissanen, K., Baum, G., Fenske, D. & Vaughan, G. (2000). Chem. Eur. J. 6, 4132–4139. CrossRef PubMed CAS Google Scholar

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Volume 65| Part 12| December 2009| Pages m1674-m1675

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis{μ-4′-[4-(quinolin-8-yloxymeth­yl)phen­yl]-2,2′:6′,2′′-terpyridine}disilver(I) bis­­(perchlorate) di­methyl­formamide disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis{μ-4′-[4-(quinolin-8-yloxymethyl)phenyl]-2,2′:6′,2′′-terpyridine}disilver(I) bis(perchlorate) dimethylformamide disolvate