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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1674–m1675.
Published online 2009 November 25. doi:  10.1107/S1600536809046832
PMCID: PMC2972071

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

Abstract

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 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 [triangle]); Constable et al. (2005 [triangle]); Thompson (1997 [triangle]); Ziener et al. (2000 [triangle]). For the ligand synthesis, see: Chow et al. (2006 [triangle]). For related structures, see: Hou & Li (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1674-scheme1.jpg

Experimental

Crystal data

  • [Ag2(C31H22N4O)2](ClO4)2·2C3H7NO
  • M r = 1493.88
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1674-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.118
  • S = 1.03
  • 8077 reflections
  • 426 parameters
  • H-atom parameters constrained
  • Δρmax = 0.67 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

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.

Crystal data

[Ag2(C31H22N4O)2](ClO4)2·2C3H7NOF(000) = 1520
Mr = 1493.88Dx = 1.529 Mg m3
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 mm1
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

Bruker APEXII CCD diffractometer8077 independent reflections
Radiation source: fine-focus sealed tube5406 reflections with I > 2σ(I)
graphiteRint = 0.020
[var phi] 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

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 = 1.03w = 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 Å3
0 restraintsΔρmin = −0.44 e Å3

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2238).

References

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