supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

hy2238 scheme

Acta Cryst. (2009). E65, m1674-m1675    [ doi:10.1107/S1600536809046832 ]

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

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

Abstract top

In the binuclear title complex, [Ag2(C31H22N4O)2](ClO4)2·2C3H7NO, the AgI 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 [pi]-[pi] 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.

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 AgI 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 AgI 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 AgI 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.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic), 0.97 (CH2) and 0.96 (CH3) Å and with Uiso = 1.2(1.5 for methyl)Ueq(C).

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
[Figure 1] 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.]
[Figure 2] 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)2·2C3H7NOF(000) = 1520
Mr = 1493.88Dx = 1.529 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6845 reflections
a = 10.0552 (16) Åθ = 2.3–28.6°
b = 10.9548 (18) ŵ = 0.76 mm−1
c = 29.657 (5) ÅT = 296 K
β = 96.767 (8)°Block, yellow
V = 3244.0 (9) Å30.22 × 0.20 × 0.20 mm
Z = 2
Data collection top
Bruker APEXII CCD
diffractometer		8077 independent reflections
Radiation source: fine-focus sealed tube5406 reflections with I > 2σ(I)
graphiteRint = 0.020
φ and ω scansθmax = 28.7°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.847, Tmax = 0.860k = −14→14
20993 measured reflectionsl = −40→28
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0551P)2 + 1.1422P]
where P = (Fo2 + 2Fc2)/3
8077 reflections(Δ/σ)max = 0.001
426 parametersΔρmax = 0.67 e Å−3
0 restraintsΔρmin = −0.44 e Å−3
Crystal data top
[Ag2(C31H22N4O)2](ClO4)2·2C3H7NOV = 3244.0 (9) Å3
Mr = 1493.88Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.0552 (16) ŵ = 0.76 mm−1
b = 10.9548 (18) ÅT = 296 K
c = 29.657 (5) Å0.22 × 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)
Tmin = 0.847, Tmax = 0.860Rint = 0.020
20993 measured reflectionsθmax = 28.7°
Refinement top
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.118Δρmax = 0.67 e Å−3
S = 1.03Δρmin = −0.44 e Å−3
8077 reflectionsAbsolute structure: ?
426 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.60078 (2)0.42357 (2)0.602143 (7)0.06913 (11)
C10.6898 (5)0.1295 (4)0.61912 (13)0.1029 (14)
H10.64560.14020.64470.123*
C20.7329 (5)0.0155 (4)0.60987 (14)0.1074 (15)
H20.7210−0.04930.62930.129*
C30.7939 (4)−0.0024 (3)0.57173 (14)0.0904 (12)
H30.8235−0.07950.56450.108*
C40.8109 (3)0.0965 (3)0.54406 (11)0.0698 (9)
H40.85120.08630.51760.084*
C50.7678 (3)0.2102 (2)0.55580 (9)0.0534 (6)
C60.7810 (2)0.3201 (2)0.52706 (8)0.0463 (5)
C70.8646 (2)0.3213 (2)0.49286 (8)0.0487 (6)
H70.91590.25300.48800.058*
C80.8716 (2)0.4248 (2)0.46597 (7)0.0412 (5)
C90.7944 (2)0.5249 (2)0.47579 (8)0.0459 (5)
H90.79710.59640.45900.055*
C100.7135 (2)0.5180 (2)0.51051 (8)0.0432 (5)
C110.6290 (2)0.6236 (2)0.52240 (8)0.0472 (6)
C120.6129 (3)0.7268 (3)0.49576 (11)0.0631 (7)
H120.65490.73290.46950.076*
C130.5341 (3)0.8211 (3)0.50828 (13)0.0785 (9)
H130.52320.89180.49090.094*
C140.4719 (3)0.8092 (3)0.54682 (13)0.0810 (10)
H140.41860.87140.55630.097*
C150.4906 (3)0.7035 (3)0.57070 (12)0.0805 (10)
H150.44770.69500.59660.097*
C160.9562 (2)0.4271 (2)0.42791 (8)0.0442 (5)
C171.0168 (4)0.3227 (3)0.41471 (11)0.0782 (10)
H171.00840.25070.43070.094*
C181.0903 (4)0.3227 (3)0.37802 (12)0.0806 (10)
H181.13170.25100.37030.097*
C191.1035 (3)0.4254 (3)0.35296 (9)0.0544 (6)
C201.0478 (3)0.5310 (3)0.36688 (10)0.0680 (8)
H201.05800.60300.35100.082*
C210.9763 (3)0.5325 (3)0.40425 (10)0.0601 (7)
H210.94150.60590.41340.072*
C221.1736 (3)0.4222 (3)0.31074 (10)0.0654 (8)
H22A1.18980.33840.30230.078*
H22B1.11860.46110.28570.078*
C230.6229 (3)0.5043 (3)0.71396 (8)0.0558 (7)
C240.6558 (4)0.5487 (3)0.75690 (10)0.0733 (9)
H240.73640.58950.76450.088*
C250.5659 (4)0.5321 (4)0.78984 (11)0.0891 (11)
H250.58920.56050.81920.107*
C260.4473 (4)0.4757 (4)0.77919 (11)0.0804 (10)
H260.38920.46690.80120.097*
C270.4105 (3)0.4299 (3)0.73521 (10)0.0609 (7)
C280.2875 (3)0.3705 (3)0.72234 (11)0.0717 (9)
H280.22560.36210.74310.086*
C290.2598 (3)0.3259 (3)0.67989 (12)0.0744 (9)
H290.17960.28530.67130.089*
C300.3534 (3)0.3414 (3)0.64886 (10)0.0710 (8)
H300.33330.30940.61980.085*
C310.4993 (3)0.4438 (2)0.70169 (9)0.0511 (6)
C320.1542 (7)0.7098 (6)0.7540 (3)0.163 (2)
H32A0.08210.73810.76980.244*
H32B0.23780.72270.77260.244*
H32C0.14290.62430.74750.244*
C330.2519 (5)0.7433 (6)0.6824 (2)0.160 (3)
H33A0.24290.79700.65660.241*
H33B0.23730.66060.67230.241*
H33C0.34030.75090.69830.241*
C340.0645 (5)0.8613 (4)0.70234 (18)0.1072 (14)
H340.06880.90300.67520.129*
Cl10.17980 (9)0.06784 (7)0.58331 (3)0.0737 (2)
N10.7077 (3)0.2271 (2)0.59336 (8)0.0769 (8)
N20.7070 (2)0.41714 (18)0.53544 (7)0.0451 (5)
N30.5667 (3)0.6108 (2)0.55944 (8)0.0645 (6)
N40.4683 (2)0.3990 (2)0.65858 (7)0.0567 (6)
N50.1541 (4)0.7757 (4)0.71246 (16)0.1093 (11)
O10.70259 (19)0.5143 (2)0.67959 (6)0.0649 (5)
O20.3231 (3)0.0703 (3)0.58888 (11)0.1059 (9)
O30.1299 (4)−0.0427 (3)0.56646 (13)0.1260 (12)
O40.1325 (5)0.0871 (4)0.62572 (16)0.180 (2)
O50.1337 (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
U11U22U33U12U13U23
Ag10.08213 (18)0.08620 (19)0.04559 (13)−0.00483 (12)0.03491 (11)−0.00590 (10)
C10.160 (4)0.082 (2)0.082 (2)0.015 (3)0.077 (3)0.026 (2)
C20.158 (4)0.078 (3)0.100 (3)0.021 (3)0.076 (3)0.040 (2)
C30.107 (3)0.068 (2)0.106 (3)0.0214 (19)0.055 (2)0.028 (2)
C40.081 (2)0.0640 (19)0.0718 (19)0.0146 (15)0.0415 (17)0.0185 (14)
C50.0590 (15)0.0576 (16)0.0474 (14)0.0007 (12)0.0221 (12)0.0081 (12)
C60.0492 (13)0.0519 (14)0.0403 (12)−0.0003 (11)0.0156 (10)0.0025 (10)
C70.0544 (14)0.0475 (14)0.0483 (13)0.0059 (11)0.0227 (11)0.0026 (11)
C80.0407 (12)0.0509 (13)0.0337 (11)−0.0011 (10)0.0109 (9)−0.0006 (9)
C90.0505 (14)0.0482 (13)0.0409 (12)0.0029 (11)0.0134 (10)0.0034 (10)
C100.0427 (13)0.0500 (14)0.0383 (12)−0.0016 (10)0.0108 (10)−0.0037 (10)
C110.0426 (13)0.0541 (14)0.0464 (13)−0.0006 (11)0.0120 (10)−0.0076 (11)
C120.0659 (17)0.0560 (17)0.0712 (18)0.0059 (14)0.0245 (14)−0.0010 (14)
C130.082 (2)0.0589 (19)0.100 (3)0.0136 (16)0.0305 (19)−0.0012 (17)
C140.077 (2)0.074 (2)0.097 (3)0.0214 (18)0.0289 (19)−0.0159 (19)
C150.081 (2)0.092 (3)0.076 (2)0.0163 (19)0.0429 (17)−0.0136 (19)
C160.0448 (12)0.0531 (14)0.0370 (11)0.0004 (11)0.0143 (10)−0.0004 (10)
C170.110 (3)0.0582 (18)0.078 (2)0.0189 (17)0.0595 (19)0.0140 (15)
C180.111 (3)0.0619 (19)0.081 (2)0.0178 (18)0.062 (2)0.0014 (16)
C190.0544 (15)0.0674 (17)0.0453 (13)−0.0058 (13)0.0220 (11)−0.0067 (12)
C200.082 (2)0.0683 (18)0.0608 (17)0.0028 (16)0.0380 (16)0.0150 (14)
C210.0707 (18)0.0545 (15)0.0611 (16)0.0067 (13)0.0331 (14)0.0062 (13)
C220.0670 (18)0.084 (2)0.0498 (15)−0.0139 (15)0.0280 (13)−0.0125 (14)
C230.0615 (16)0.0705 (18)0.0409 (13)0.0039 (13)0.0286 (12)−0.0040 (12)
C240.081 (2)0.094 (2)0.0510 (16)−0.0151 (17)0.0307 (15)−0.0187 (15)
C250.103 (3)0.122 (3)0.0496 (17)−0.020 (2)0.0410 (18)−0.0262 (18)
C260.092 (2)0.103 (3)0.0559 (17)−0.009 (2)0.0482 (17)−0.0122 (17)
C270.0656 (17)0.0709 (18)0.0523 (15)0.0054 (14)0.0329 (13)0.0022 (13)
C280.070 (2)0.083 (2)0.069 (2)0.0011 (16)0.0406 (16)0.0095 (17)
C290.0655 (19)0.089 (2)0.071 (2)−0.0088 (17)0.0203 (15)0.0065 (17)
C300.072 (2)0.094 (2)0.0502 (16)−0.0101 (17)0.0173 (14)−0.0025 (15)
C310.0598 (16)0.0558 (15)0.0426 (13)0.0086 (12)0.0269 (12)0.0015 (10)
C320.172 (6)0.138 (5)0.174 (6)0.005 (4)0.000 (5)0.008 (5)
C330.113 (4)0.151 (5)0.228 (7)0.012 (4)0.065 (4)−0.052 (5)
C340.103 (3)0.095 (3)0.132 (4)−0.008 (3)0.045 (3)−0.008 (3)
Cl10.0887 (6)0.0615 (5)0.0756 (5)−0.0031 (4)0.0286 (4)−0.0032 (4)
N10.108 (2)0.0706 (17)0.0612 (15)0.0056 (15)0.0482 (15)0.0132 (12)
N20.0458 (11)0.0533 (12)0.0384 (10)−0.0010 (9)0.0137 (8)0.0005 (9)
N30.0684 (15)0.0729 (16)0.0570 (14)0.0133 (12)0.0274 (12)−0.0021 (12)
N40.0608 (14)0.0696 (15)0.0431 (11)−0.0014 (11)0.0212 (10)0.0008 (10)
N50.099 (3)0.094 (3)0.138 (3)−0.003 (2)0.024 (2)−0.016 (2)
O10.0634 (12)0.0923 (15)0.0450 (10)−0.0149 (10)0.0314 (9)−0.0126 (10)
O20.0906 (19)0.113 (2)0.115 (2)0.0127 (15)0.0156 (16)0.0025 (16)
O30.158 (3)0.0764 (18)0.151 (3)−0.0307 (19)0.051 (2)−0.0370 (19)
O40.185 (4)0.239 (5)0.130 (3)−0.052 (3)0.081 (3)−0.081 (3)
O50.091 (2)0.121 (3)0.284 (5)0.0051 (19)0.021 (3)0.105 (3)
O60.125 (3)0.140 (3)0.165 (3)0.011 (2)0.082 (2)−0.011 (2)
Geometric parameters (Å, °) top
Ag1—O12.5995 (19)C19—C201.370 (4)
Ag1—N12.434 (3)C19—C221.508 (3)
Ag1—N22.3572 (19)C20—C211.390 (4)
Ag1—N32.414 (3)C20—H200.9300
Ag1—N42.275 (2)C21—H210.9300
C1—N11.338 (4)C22—O1i1.426 (3)
C1—C21.361 (5)C22—H22A0.9700
C1—H10.9300C22—H22B0.9700
C2—C31.363 (5)C23—C241.367 (4)
C2—H20.9300C23—O11.373 (3)
C3—C41.382 (4)C23—C311.418 (4)
C3—H30.9300C24—C251.419 (4)
C4—C51.377 (4)C24—H240.9300
C4—H40.9300C25—C261.347 (5)
C5—N11.341 (3)C25—H250.9300
C5—C61.489 (3)C26—C271.406 (4)
C6—N21.338 (3)C26—H260.9300
C6—C71.392 (3)C27—C281.410 (5)
C7—C81.392 (3)C27—C311.421 (3)
C7—H70.9300C28—C291.348 (5)
C8—C91.395 (3)C28—H280.9300
C8—C161.491 (3)C29—C301.402 (4)
C9—C101.387 (3)C29—H290.9300
C9—H90.9300C30—N41.318 (4)
C10—N21.335 (3)C30—H300.9300
C10—C111.501 (3)C31—N41.371 (3)
C11—N31.335 (3)C32—N51.428 (7)
C11—C121.378 (4)C32—H32A0.9600
C12—C131.380 (4)C32—H32B0.9600
C12—H120.9300C32—H32C0.9600
C13—C141.372 (5)C33—N51.448 (6)
C13—H130.9300C33—H33A0.9600
C14—C151.359 (5)C33—H33B0.9600
C14—H140.9300C33—H33C0.9600
C15—N31.337 (4)C34—O61.211 (5)
C15—H150.9300C34—N51.310 (6)
C16—C171.374 (4)C34—H340.9300
C16—C211.379 (4)Cl1—O51.375 (3)
C17—C181.385 (4)Cl1—O31.382 (3)
C17—H170.9300Cl1—O41.412 (4)
C18—C191.363 (4)Cl1—O21.432 (3)
C18—H180.9300O1—C22i1.426 (4)
N4—Ag1—N2167.56 (8)O1i—C22—C19107.7 (2)
N4—Ag1—N3115.30 (8)O1i—C22—H22A110.2
N2—Ag1—N368.62 (7)C19—C22—H22A110.2
N4—Ag1—N1106.16 (8)O1i—C22—H22B110.2
N2—Ag1—N168.55 (7)C19—C22—H22B110.2
N3—Ag1—N1137.12 (7)H22A—C22—H22B108.5
N4—Ag1—O166.35 (7)C24—C23—O1124.4 (3)
N2—Ag1—O1125.64 (6)C24—C23—C31120.9 (2)
N3—Ag1—O198.95 (8)O1—C23—C31114.7 (2)
N1—Ag1—O1107.45 (9)C23—C24—C25119.5 (3)
N1—C1—C2123.4 (3)C23—C24—H24120.3
N1—C1—H1118.3C25—C24—H24120.3
C2—C1—H1118.3C26—C25—C24121.1 (3)
C1—C2—C3118.9 (3)C26—C25—H25119.5
C1—C2—H2120.5C24—C25—H25119.5
C3—C2—H2120.5C25—C26—C27120.7 (3)
C2—C3—C4118.7 (3)C25—C26—H26119.7
C2—C3—H3120.7C27—C26—H26119.7
C4—C3—H3120.7C26—C27—C28122.9 (3)
C5—C4—C3119.6 (3)C26—C27—C31119.5 (3)
C5—C4—H4120.2C28—C27—C31117.6 (3)
C3—C4—H4120.2C29—C28—C27119.9 (3)
N1—C5—C4121.4 (2)C29—C28—H28120.1
N1—C5—C6116.3 (2)C27—C28—H28120.1
C4—C5—C6122.3 (2)C28—C29—C30119.2 (3)
N2—C6—C7121.6 (2)C28—C29—H29120.4
N2—C6—C5116.5 (2)C30—C29—H29120.4
C7—C6—C5121.8 (2)N4—C30—C29123.6 (3)
C6—C7—C8120.1 (2)N4—C30—H30118.2
C6—C7—H7120.0C29—C30—H30118.2
C8—C7—H7120.0N4—C31—C23120.2 (2)
C7—C8—C9117.0 (2)N4—C31—C27121.5 (3)
C7—C8—C16121.3 (2)C23—C31—C27118.3 (2)
C9—C8—C16121.7 (2)N5—C32—H32A109.5
C10—C9—C8120.1 (2)N5—C32—H32B109.5
C10—C9—H9119.9H32A—C32—H32B109.5
C8—C9—H9119.9N5—C32—H32C109.5
N2—C10—C9121.8 (2)H32A—C32—H32C109.5
N2—C10—C11116.2 (2)H32B—C32—H32C109.5
C9—C10—C11122.0 (2)N5—C33—H33A109.5
N3—C11—C12121.5 (2)N5—C33—H33B109.5
N3—C11—C10116.5 (2)H33A—C33—H33B109.5
C12—C11—C10122.0 (2)N5—C33—H33C109.5
C11—C12—C13119.5 (3)H33A—C33—H33C109.5
C11—C12—H12120.2H33B—C33—H33C109.5
C13—C12—H12120.2O6—C34—N5126.6 (5)
C14—C13—C12119.1 (3)O6—C34—H34116.7
C14—C13—H13120.5N5—C34—H34116.7
C12—C13—H13120.5O5—Cl1—O3111.6 (3)
C15—C14—C13117.8 (3)O5—Cl1—O4107.0 (3)
C15—C14—H14121.1O3—Cl1—O4107.9 (2)
C13—C14—H14121.1O5—Cl1—O2108.57 (19)
N3—C15—C14124.4 (3)O3—Cl1—O2112.1 (2)
N3—C15—H15117.8O4—Cl1—O2109.6 (2)
C14—C15—H15117.8C1—N1—C5117.9 (3)
C17—C16—C21117.1 (2)C1—N1—Ag1123.7 (2)
C17—C16—C8120.9 (2)C5—N1—Ag1117.28 (18)
C21—C16—C8122.0 (2)C10—N2—C6119.36 (19)
C16—C17—C18121.3 (3)C10—N2—Ag1119.76 (15)
C16—C17—H17119.3C6—N2—Ag1119.77 (15)
C18—C17—H17119.3C11—N3—C15117.7 (3)
C19—C18—C17121.6 (3)C11—N3—Ag1117.99 (18)
C19—C18—H18119.2C15—N3—Ag1124.3 (2)
C17—C18—H18119.2C30—N4—C31118.2 (2)
C18—C19—C20117.6 (2)C30—N4—Ag1118.02 (19)
C18—C19—C22121.2 (3)C31—N4—Ag1123.75 (18)
C20—C19—C22121.2 (3)C34—N5—C32119.4 (5)
C19—C20—C21121.2 (3)C34—N5—C33122.2 (5)
C19—C20—H20119.4C32—N5—C33118.4 (5)
C21—C20—H20119.4C23—O1—C22i117.5 (2)
C16—C21—C20121.1 (3)C23—O1—Ag1114.95 (16)
C16—C21—H21119.5C22i—O1—Ag1127.44 (14)
C20—C21—H21119.5
N1—C1—C2—C3−2.1 (8)N4—Ag1—N1—C1−1.9 (4)
C1—C2—C3—C40.6 (7)N2—Ag1—N1—C1−170.0 (4)
C2—C3—C4—C50.8 (6)N3—Ag1—N1—C1−166.9 (3)
C3—C4—C5—N1−1.0 (5)O1—Ag1—N1—C167.8 (4)
C3—C4—C5—C6−178.9 (3)N4—Ag1—N1—C5165.8 (2)
N1—C5—C6—N2−14.4 (4)N2—Ag1—N1—C5−2.3 (2)
C4—C5—C6—N2163.7 (3)N3—Ag1—N1—C50.9 (3)
N1—C5—C6—C7166.4 (3)O1—Ag1—N1—C5−124.5 (2)
C4—C5—C6—C7−15.5 (4)C9—C10—N2—C60.5 (4)
N2—C6—C7—C8−0.8 (4)C11—C10—N2—C6−179.2 (2)
C5—C6—C7—C8178.4 (2)C9—C10—N2—Ag1168.45 (18)
C6—C7—C8—C91.4 (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—C10177.9 (2)C7—C6—N2—Ag1−168.13 (19)
C8—C9—C10—N20.2 (4)C5—C6—N2—Ag112.7 (3)
C8—C9—C10—C11179.8 (2)N4—Ag1—N2—C10119.3 (4)
N2—C10—C11—N36.6 (3)N3—Ag1—N2—C108.49 (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—C129.0 (4)N4—Ag1—N2—C6−72.7 (4)
N3—C11—C12—C132.1 (5)N3—Ag1—N2—C6176.4 (2)
C10—C11—C12—C13180.0 (3)N1—Ag1—N2—C6−5.86 (18)
C11—C12—C13—C14−0.8 (5)O1—Ag1—N2—C690.73 (19)
C12—C13—C14—C15−0.5 (6)C12—C11—N3—C15−1.9 (4)
C13—C14—C15—N30.7 (6)C10—C11—N3—C15−179.9 (3)
C7—C8—C16—C178.0 (4)C12—C11—N3—Ag1178.9 (2)
C9—C8—C16—C17−170.9 (3)C10—C11—N3—Ag10.9 (3)
C7—C8—C16—C21−172.5 (3)C14—C15—N3—C110.5 (5)
C9—C8—C16—C218.6 (4)C14—C15—N3—Ag1179.7 (3)
C21—C16—C17—C18−2.6 (5)N4—Ag1—N3—C11−171.7 (2)
C8—C16—C17—C18176.9 (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—C203.7 (6)O1—Ag1—N3—C11120.3 (2)
C17—C18—C19—C22−174.7 (3)N4—Ag1—N3—C159.1 (3)
C18—C19—C20—C21−2.3 (5)N2—Ag1—N3—C15176.3 (3)
C22—C19—C20—C21176.2 (3)N1—Ag1—N3—C15173.1 (3)
C17—C16—C21—C204.0 (5)O1—Ag1—N3—C15−58.9 (3)
C8—C16—C21—C20−175.5 (3)C29—C30—N4—C311.5 (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—C30178.8 (3)
C20—C19—C22—O1i72.0 (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—C251.1 (5)C27—C31—N4—Ag1177.55 (19)
C23—C24—C25—C26−1.5 (6)N2—Ag1—N4—C30−14.0 (5)
C24—C25—C26—C271.1 (6)N3—Ag1—N4—C3091.7 (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—C31168.1 (3)
C31—C27—C28—C292.1 (5)N3—Ag1—N4—C31−86.2 (2)
C27—C28—C29—C30−1.2 (5)N1—Ag1—N4—C31105.0 (2)
C28—C29—C30—N4−0.7 (6)O1—Ag1—N4—C312.70 (19)
C24—C23—C31—N4−179.5 (3)O6—C34—N5—C32−1.1 (8)
O1—C23—C31—N41.0 (4)O6—C34—N5—C33177.5 (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—C22i178.0 (3)
C26—C27—C31—N4179.0 (3)C24—C23—O1—Ag1−178.2 (3)
C28—C27—C31—N4−1.3 (4)C31—C23—O1—Ag11.3 (3)
C26—C27—C31—C23−0.2 (4)N4—Ag1—O1—C23−2.03 (18)
C28—C27—C31—C23179.4 (3)N2—Ag1—O1—C23−178.19 (17)
C2—C1—N1—C52.0 (7)N3—Ag1—O1—C23111.75 (19)
C2—C1—N1—Ag1169.7 (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—C1177.7 (3)N2—Ag1—O1—C22i5.5 (3)
C4—C5—N1—Ag1−168.9 (2)N3—Ag1—O1—C22i−64.5 (2)
C6—C5—N1—Ag19.2 (3)N1—Ag1—O1—C22i81.3 (3)
Symmetry codes: (i) −x+2, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O3ii0.932.573.450 (5)158
C12—H12···O5iii0.932.603.344 (5)138
C28—H28···O6iv0.932.373.250 (5)158
C29—H29···O40.932.573.252 (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.
Table 1
Selected geometric parameters (Å) top
Ag1—O12.5995 (19)Ag1—N32.414 (3)
Ag1—N12.434 (3)Ag1—N42.275 (2)
Ag1—N22.3572 (19)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C4—H4···O3i0.932.573.450 (5)158
C12—H12···O5ii0.932.603.344 (5)138
C28—H28···O6iii0.932.373.250 (5)158
C29—H29···O40.932.573.252 (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 top

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

references
References top

Andres, P. R. & Schubert, U. S. (2004). Adv. Mater. 16, 1043–1068.

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Chow, H. S., Constable, E. C., Housecroft, C. E., Neuburger, M. & Schaffner, S. (2006). Dalton Trans. pp. 2881–2890.

Constable, E. C., Housecroft, C. H., Neuburger, M., Schaffner, S. & Shardlow, E. J. (2005). CrystEngComm, 7, 599–602.

Hou, L. & Li, D. (2005). Inorg. Chem. Commun. 8, 128–130.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Thompson, A. M. W. C. (1997). Coord. Chem. Rev. 160, 1–52.

Ziener, U., Breuning, E., Lehn, J.-M., Wegelius, E., Rissanen, K., Baum, G., Fenske, D. & Vaughan, G. (2000). Chem. Eur. J. 6, 4132–4139.