A three-dimensional supra­molecular framework of silver(I), 2-phenyl­quinoline-4-carboxyl­ate and 4,4'-bi­pyridine

A novel supra­molecular framework, catena-poly[[[aqua(2-phenyl­quinoline-4-carboxyl­ato-[kappa]O)silver(I)]-[mu]-4,4'-bipyridine-[kappa]²N:N'] dihydrate], {[Ag(C₁₆H₁₀NO₂)(C₁₀H₈N₂)(H₂O)]·2H₂O}_n, has been synthesized and structurally characterized. The Ag^I centres are four-coordinated and bridged by 4,4'-bi­pyridine (4,4'-bipy) ligands to form a one-dimensional Ag-bipy chain. The Ag-bipy chains are further linked together by inter­molecular O-H...O and O-H...N hydrogen-bonding inter­actions between adjacent chains, resulting in a three-dimensional framework.

S1. Comment

In recent years, isonicotinic acid and its derivatives, bearing both neutral and anionic donor groups, have been widely used to construct metal–organic coordination polymers, not only from the viewpoint of structural interest (Xiong et al., 1999; Evans & Lin, 2000; Zheng et al., 2001; Lu & Babb, 2001), but also for targeting solid-state complexes with tailored properties such as nonlinear optical properties (Evans & Lin, 2002; Lin et al., 1998, 2000), inclusion behaviour (Aakeröy et al., 1999; Sekiya & Nishikiori, 2002; Sekiya et al., 2004; Zhang et al., 2001) and molecular magnetism (Chapman et al., 2001; Bu et al., 2005). However, as an analogue of isonicotinic acid, the use of 2-phenylquinoline-4-carboxylic acid (HL) to construct metal–organic frameworks has been less well investigated to date (Qin et al., 2002; Shen et al., 2007; Wang et al., 2010; Li et al., 2011; Zhang et al., 2009). The 2-phenylquinoline-4-carboxylate ligand, L, was selected based on the following considerations. It has larger conjugated π systems, and therefore π–π stacking and/or C—H···π interactions may play an important role in the formation of complexes, especially in the aspect of linking dinuclear or multinuclear discrete subunits or low-dimensional entities into higher-dimensional supramolecular frameworks. On the other hand, the coordination abilities of the quinoline N atoms may be weakened by adjacent larger groups, although the quinoline N atoms may still easily form hydrogen-bonding interactions with hydrogen-donor molecules. Besides, the introduction of an auxiliary ligand, such as 4,4'-bipyridyl-like linear bridging molecules, into the reaction system may generate interesting coordination architectures. In the present work, we report the synthesis and structure of the title silver(I) complex with 2-phenylquinoline-4-carboxylic acid, (I).

The crystal structure of (I) (Fig. 1) shows that the Ag^I centres are four-coordinated. Each Ag^I cation is coordinated by two N atoms of two different 4,4'-bipyridine (4,4'-bipy) ligands, one carboxylate O atom and one relatively weakly coordinated aqua ligand (Table 1 and Fig. 1). The Ag^I cations are bridged by 4,4'-bipy ligands to form a one-dimensional Ag–bipy chain running in the [101] direction (Fig. 2). Adjacent Ag–bipy chains are interconnected by hydrogen-bonding interactions to build up the two-dimensional crystal framework. The solvent water molecules are situated within the framework and stabilized by hydrogen-bonding interactions.

Seen from the [101] plane, there are four different orientations for L, two face-to-face and the other two back-to-back, and this arrangement is repeated thoughout the crystal structure (Fig. 3). Between two neighbouring back-to-back chains, coordinated water molecule O1W, as hydrogen-bond donor, interacts with noncoordinated carboxylate atom O2 in an intramolecular O1W—H1A···O2 hydrogen bond and an intermolecular O1W—H1B···O2ⁱ hydrogen bond (see Table 2 for geometric details and symmetry codes for all hydrogen bonds). Noncoordinated atoms O2 and O2ⁱ and two coordinated O1W water molecules in two adjacent polymeric chains are organized in an approximate quadrangle, with an O atom at each of the four corners. Between two neighbouring face-to-face polymeric chains, two solvent water molecules arrange themselves to form a hydrogen-bonded water dimer (O2W—H2B···O3Wⁱⁱ and O3W—H3A···O2Wⁱⁱⁱ), and this supramolecular water dimer is associated with the L ligand by hydrogen bonds through the coordinated O atom of the –COO^- group and the N atom of L.

Hydrogen-bonding data indicate that solvent water molecule O2W, acting as a donor, is hydrogen-bonded to atom N3 of ligand L in another adjacent polymeric chain (O2W—H2A···N3 [Symmetry code?]) and to water molecule O3Wⁱⁱ (O2W—H2B···O3Wⁱⁱ), which in turn acts as a hydrogen-bond acceptor interacting with water molecule O3W. Solvent water molecule (O3W), also acting as a hydrogen-bond donor, is bonded to the monodentate carboxylate (–COOAg) group in a neighbouring chain (O3W—H3B···O1 [Symmetry code?]) and to water molecule O2Wⁱⁱⁱ (O3W—H3A···O2Wⁱⁱⁱ), which in turn acts as a hydrogen-bond acceptor interacting with water molecule O2W. Both O2W and O3W thus behave as both acceptors and donors, while L behaves solely as an acceptor. The water molecules are all three-coordinated, as usual.

Due to the introduction of 4,4'-bipy as a second ligand into the Ag–L system, complex (I) displays a distinctly different structure from [Ag(C₁₆H_10.5NO₂)₂] [chemical name?] (Zhang et al., 2009). Although as a potential coordinating group, unlike [Ag(C₁₆H_10.5NO₂)₂], the quinoline group does not coordinate to the Ag^I cation in (I), it shows hydrogen-bonding interactions with solvent water molecule O2W. The solvent water molecules, the coordinated water molecule and the one-dimensional chains are bridged through O—H···O and O—H···N hydrogen bonds to form a three-dimensional architecture.

Related literature

For related literature, see: Aakeröy et al. (1999); Bu et al. (2005); Chapman et al. (2001); Evans & Lin (2000, 2002); Li et al. (2011); Lin et al. (1998, 2000); Lu & Babb (2001); Qin et al. (2002); Sekiya & Nishikiori (2002); Sekiya et al. (2004); Shen et al. (2007); Wang et al. (2010); Xiong et al. (1999); Zhang et al. (2001, 2009); Zheng et al. (2001).

S2. Experimental

To a mixture of HL (24.9 mg, 0.1 mmol) and NaOH (4.0 mg, 0.1 mmol) in water was added AgNO₃ (17.0 mg, 0.1 mmol) with constant stirring, followed by 4,4'-bipy (15.6 mg, 0.1 mmol) in water. After the sample had been stirred for 30 min, the precipitate which formed was dissolved by dropwise addition of aqueous NH₃ solution. Colourless block-shaped crystals of (I) were obtained from the filtrate by slow evaporation after standing in the dark for several days (yield 50%).

S3. Refinement

H atoms were placed in idealized positions and allowed to ride on their parent C atoms, with C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C). The water H atoms were located in a difference Fourier map and refined with a restraint of O—H = 0.84 (1) Å. They were refined as riding atoms in the final refinement, with U_iso(H) = 1.5U_eq(O).

Computing details

Data collection: SMART (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

	Fig. 1. The asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) x - 1, y, z - 1; (ii) x + 1, y, z + 1.]
	Fig. 2. A view of the one-dimensional assembly of Ag^I–bipy linear chains running in the [101] direction.
	Fig. 3. A crystal packing diagram for (I), in the [101] plane. Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) -x + 1, -y, -z + 1; (ii) x + 1, y, z; (iii) x - 1, -y + 1/2, z - 1/2.]

catena-Poly[[[aqua(2-phenylquinoline-4-carboxylato-κO)silver(I)]-µ-4,4'-bipyridine-κ²N:N'] dihydrate]

Crystal data

[Ag(C16H10NO2)(C10H8N2)(H2O)]·2H2O	F(000) = 1152
Mr = 566.35	Dx = 1.590 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybc	Cell parameters from 4054 reflections
a = 9.4006 (9) Å	θ = 2.3–26.0°
b = 27.461 (3) Å	µ = 0.90 mm^−1
c = 9.5349 (9) Å	T = 151 K
β = 105.987 (1)°	Block, colourless
V = 2366.3 (4) Å^3	0.28 × 0.22 × 0.15 mm
Z = 4

Data collection

Bruker APEX CCD area-detector diffractometer	4645 independent reflections
Radiation source: fine-focus sealed tube	3708 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
ϕ and ω scans	θmax = 26.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −11→11
Tmin = 0.788, Tmax = 0.877	k = −27→33
13019 measured reflections	l = −10→11

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0535P)^2 + 0.3783P] where P = (Fo^2 + 2Fc^2)/3
4645 reflections	(Δ/σ)max < 0.001
316 parameters	Δρmax = 0.98 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

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.

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

	x	y	z	Uiso*/Ueq
C1	0.6613 (3)	0.12837 (11)	0.4701 (3)	0.0256 (6)
C2	0.6926 (3)	0.17228 (11)	0.4059 (3)	0.0258 (6)
C3	0.8314 (3)	0.19522 (11)	0.4725 (3)	0.0264 (7)
C4	0.8992 (3)	0.13549 (10)	0.6497 (3)	0.0240 (6)
C5	0.7634 (3)	0.11086 (11)	0.5910 (3)	0.0260 (6)
H5	0.7430	0.0818	0.6362	0.031*
C6	0.5151 (3)	0.10155 (12)	0.4104 (3)	0.0298 (7)
C7	0.5962 (3)	0.19405 (12)	0.2805 (3)	0.0316 (7)
H7	0.5060	0.1783	0.2324	0.038*
C8	0.6315 (4)	0.23733 (12)	0.2281 (4)	0.0365 (8)
H8	0.5655	0.2517	0.1447	0.044*
C9	0.7653 (4)	0.26060 (13)	0.2976 (4)	0.0389 (8)
H9	0.7881	0.2911	0.2619	0.047*
C10	0.8631 (4)	0.24003 (12)	0.4154 (4)	0.0356 (8)
H10	0.9538	0.2561	0.4598	0.043*
C11	1.0075 (3)	0.11691 (12)	0.7843 (3)	0.0276 (7)
C12	1.0138 (3)	0.06776 (13)	0.8220 (4)	0.0356 (8)
H12	0.9505	0.0451	0.7594	0.043*
C13	1.1123 (4)	0.05178 (14)	0.9506 (4)	0.0427 (9)
H13	1.1158	0.0182	0.9750	0.051*
C14	1.2051 (4)	0.08406 (15)	1.0435 (4)	0.0436 (9)
H14	1.2720	0.0729	1.1315	0.052*
C15	1.1996 (3)	0.13277 (15)	1.0068 (3)	0.0394 (8)
H15	1.2634	0.1552	1.0701	0.047*
C16	1.1028 (3)	0.14938 (13)	0.8796 (3)	0.0322 (7)
H16	1.1005	0.1830	0.8561	0.039*
C17	−0.0046 (3)	0.13603 (12)	0.2579 (3)	0.0309 (7)
H17	0.0636	0.1623	0.2743	0.037*
C18	−0.1241 (3)	0.13736 (12)	0.1351 (3)	0.0315 (7)
H18	−0.1374	0.1643	0.0702	0.038*
C19	−0.2250 (3)	0.09890 (12)	0.1071 (3)	0.0282 (7)
C20	−0.1989 (3)	0.06115 (12)	0.2080 (3)	0.0337 (7)
H20	−0.2645	0.0342	0.1942	0.040*
C21	−0.0781 (4)	0.06300 (12)	0.3276 (3)	0.0361 (8)
H21	−0.0628	0.0368	0.3952	0.043*
C22	−0.5273 (4)	0.05631 (12)	−0.2163 (3)	0.0358 (8)
H22	−0.5607	0.0265	−0.2646	0.043*
C23	−0.4070 (3)	0.05535 (12)	−0.0952 (3)	0.0345 (7)
H23	−0.3603	0.0253	−0.0607	0.041*
C24	−0.3538 (3)	0.09850 (12)	−0.0234 (3)	0.0292 (7)
C25	−0.4279 (3)	0.14116 (12)	−0.0803 (3)	0.0331 (7)
H25	−0.3950	0.1717	−0.0363	0.040*
C26	−0.5487 (3)	0.13882 (13)	−0.2002 (3)	0.0341 (7)
H26	−0.5986	0.1683	−0.2358	0.041*
N1	0.0200 (3)	0.09981 (9)	0.3546 (3)	0.0287 (6)
N2	−0.6000 (3)	0.09750 (10)	−0.2698 (3)	0.0328 (6)
N3	0.9327 (3)	0.17626 (9)	0.5915 (3)	0.0265 (6)
O1	0.3988 (2)	0.12609 (8)	0.3870 (2)	0.0358 (5)
O2	0.5224 (2)	0.05672 (8)	0.3900 (3)	0.0398 (6)
O1W	0.2746 (2)	0.00869 (9)	0.4363 (3)	0.0461 (6)
H1A	0.3308	0.0250	0.3982	0.069*
H1B	0.3277	−0.0112	0.4968	0.069*
O2W	1.2085 (3)	0.23329 (9)	0.6600 (2)	0.0475 (7)
H2A	1.1397	0.2129	0.6506	0.071*
H2B	1.2376	0.2340	0.5843	0.071*
O3W	0.3189 (3)	0.22196 (10)	0.4276 (3)	0.0539 (7)
H3A	0.2826	0.2330	0.3420	0.081*
H3B	0.3271	0.1912	0.4218	0.081*
Ag1	0.21896 (2)	0.096573 (10)	0.53296 (3)	0.03692 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0251 (15)	0.0253 (17)	0.0278 (15)	0.0003 (12)	0.0096 (13)	−0.0026 (13)
C2	0.0255 (15)	0.0299 (17)	0.0235 (15)	0.0015 (13)	0.0093 (12)	−0.0003 (13)
C3	0.0274 (15)	0.0302 (17)	0.0255 (15)	−0.0019 (13)	0.0139 (13)	−0.0009 (13)
C4	0.0240 (15)	0.0239 (16)	0.0253 (15)	0.0007 (12)	0.0086 (12)	−0.0041 (12)
C5	0.0251 (15)	0.0246 (16)	0.0290 (16)	−0.0008 (12)	0.0084 (13)	−0.0006 (13)
C6	0.0245 (16)	0.038 (2)	0.0253 (16)	−0.0043 (14)	0.0040 (13)	0.0055 (14)
C7	0.0267 (16)	0.040 (2)	0.0288 (16)	0.0002 (14)	0.0096 (13)	0.0020 (14)
C8	0.0373 (19)	0.043 (2)	0.0291 (17)	0.0072 (15)	0.0099 (15)	0.0130 (15)
C9	0.042 (2)	0.035 (2)	0.044 (2)	−0.0054 (15)	0.0183 (17)	0.0078 (15)
C10	0.0341 (18)	0.037 (2)	0.0385 (19)	−0.0083 (14)	0.0146 (15)	0.0004 (15)
C11	0.0212 (15)	0.0352 (18)	0.0267 (16)	0.0014 (13)	0.0071 (12)	−0.0027 (13)
C12	0.0264 (17)	0.040 (2)	0.0369 (18)	0.0004 (14)	0.0033 (14)	−0.0027 (15)
C13	0.0359 (19)	0.046 (2)	0.043 (2)	0.0093 (16)	0.0052 (16)	0.0116 (17)
C14	0.0291 (19)	0.066 (3)	0.0312 (19)	0.0079 (17)	0.0014 (15)	0.0045 (17)
C15	0.0238 (17)	0.059 (3)	0.0319 (18)	−0.0049 (15)	0.0022 (14)	−0.0064 (16)
C16	0.0257 (16)	0.0400 (19)	0.0329 (17)	−0.0023 (14)	0.0116 (14)	−0.0047 (15)
C17	0.0214 (15)	0.0391 (19)	0.0302 (17)	−0.0013 (13)	0.0035 (13)	−0.0043 (14)
C18	0.0234 (16)	0.041 (2)	0.0284 (16)	0.0007 (14)	0.0031 (13)	0.0007 (14)
C19	0.0188 (14)	0.0425 (19)	0.0223 (15)	0.0040 (13)	0.0037 (12)	−0.0019 (14)
C20	0.0278 (17)	0.0357 (19)	0.0330 (17)	−0.0045 (14)	0.0004 (14)	0.0014 (14)
C21	0.0325 (18)	0.039 (2)	0.0308 (17)	0.0014 (15)	−0.0005 (14)	0.0049 (15)
C22	0.0307 (17)	0.038 (2)	0.0324 (18)	−0.0047 (15)	−0.0015 (14)	−0.0062 (15)
C23	0.0273 (17)	0.0359 (19)	0.0339 (17)	0.0022 (14)	−0.0025 (14)	0.0000 (15)
C24	0.0190 (15)	0.043 (2)	0.0247 (15)	0.0018 (13)	0.0047 (12)	−0.0014 (14)
C25	0.0273 (17)	0.038 (2)	0.0303 (17)	0.0002 (14)	0.0022 (13)	−0.0033 (14)
C26	0.0258 (16)	0.041 (2)	0.0312 (17)	0.0071 (14)	0.0011 (14)	0.0015 (15)
N1	0.0204 (13)	0.0393 (16)	0.0242 (13)	0.0027 (11)	0.0026 (10)	−0.0042 (12)
N2	0.0213 (13)	0.0478 (18)	0.0256 (14)	0.0007 (12)	0.0005 (11)	0.0008 (12)
N3	0.0234 (13)	0.0302 (15)	0.0270 (13)	−0.0020 (11)	0.0091 (11)	−0.0039 (11)
O1	0.0198 (11)	0.0412 (14)	0.0444 (13)	−0.0007 (10)	0.0056 (10)	0.0095 (11)
O2	0.0318 (13)	0.0314 (14)	0.0513 (15)	−0.0066 (10)	0.0029 (11)	−0.0004 (11)
O1W	0.0322 (13)	0.0349 (14)	0.0662 (17)	−0.0023 (10)	0.0051 (12)	−0.0001 (12)
O2W	0.0381 (14)	0.0678 (18)	0.0368 (14)	−0.0187 (12)	0.0109 (11)	−0.0052 (12)
O3W	0.0636 (18)	0.0591 (18)	0.0439 (15)	0.0132 (14)	0.0230 (14)	0.0070 (13)
Ag1	0.01974 (14)	0.0574 (2)	0.02758 (15)	0.00090 (11)	−0.00367 (10)	0.00003 (12)

Geometric parameters (Å, º)

C1—C5	1.369 (4)	C17—N1	1.332 (4)
C1—C2	1.419 (4)	C17—C18	1.381 (4)
C1—C6	1.525 (4)	C17—H17	0.9500
C2—C7	1.418 (4)	C18—C19	1.395 (4)
C2—C3	1.431 (4)	C18—H18	0.9500
C3—N3	1.368 (4)	C19—C20	1.389 (4)
C3—C10	1.410 (4)	C19—C24	1.478 (4)
C4—N3	1.326 (4)	C20—C21	1.371 (4)
C4—C5	1.417 (4)	C20—H20	0.9500
C4—C11	1.491 (4)	C21—N1	1.344 (4)
C5—H5	0.9500	C21—H21	0.9500
C6—O1	1.251 (4)	C22—N2	1.347 (4)
C6—O2	1.251 (4)	C22—C23	1.377 (4)
C7—C8	1.365 (4)	C22—H22	0.9500
C7—H7	0.9500	C23—C24	1.391 (4)
C8—C9	1.404 (5)	C23—H23	0.9500
C8—H8	0.9500	C24—C25	1.394 (4)
C9—C10	1.363 (5)	C25—C26	1.373 (4)
C9—H9	0.9500	C25—H25	0.9500
C10—H10	0.9500	C26—N2	1.336 (4)
C11—C12	1.393 (5)	C26—H26	0.9500
C11—C16	1.405 (4)	Ag1—N1	2.156 (2)
C12—C13	1.389 (4)	Ag1—N2^i	2.161 (3)
C12—H12	0.9500	Ag1—O1	2.598 (2)
C13—C14	1.381 (5)	Ag1—O1W	2.685 (2)
C13—H13	0.9500	O1W—H1A	0.8476
C14—C15	1.380 (6)	O1W—H1B	0.8494
C14—H14	0.9500	O2W—H2A	0.8418
C15—C16	1.378 (4)	O2W—H2B	0.8391
C15—H15	0.9500	O3W—H3A	0.8496
C16—H16	0.9500	O3W—H3B	0.8504
C5—C1—C2	118.8 (3)	N1—C17—H17	118.3
C5—C1—C6	119.7 (3)	C18—C17—H17	118.3
C2—C1—C6	121.5 (3)	C17—C18—C19	119.6 (3)
C7—C2—C1	124.2 (3)	C17—C18—H18	120.2
C7—C2—C3	118.8 (3)	C19—C18—H18	120.2
C1—C2—C3	117.1 (3)	C20—C19—C18	116.8 (3)
N3—C3—C10	118.7 (3)	C20—C19—C24	121.6 (3)
N3—C3—C2	122.8 (3)	C18—C19—C24	121.5 (3)
C10—C3—C2	118.5 (3)	C21—C20—C19	119.7 (3)
N3—C4—C5	122.0 (3)	C21—C20—H20	120.1
N3—C4—C11	117.7 (3)	C19—C20—H20	120.1
C5—C4—C11	120.2 (3)	N1—C21—C20	123.7 (3)
C1—C5—C4	120.8 (3)	N1—C21—H21	118.2
C1—C5—H5	119.6	C20—C21—H21	118.2
C4—C5—H5	119.6	N2—C22—C23	123.2 (3)
O1—C6—O2	125.8 (3)	N2—C22—H22	118.4
O1—C6—C1	117.4 (3)	C23—C22—H22	118.4
O2—C6—C1	116.8 (3)	C22—C23—C24	119.8 (3)
C8—C7—C2	120.8 (3)	C22—C23—H23	120.1
C8—C7—H7	119.6	C24—C23—H23	120.1
C2—C7—H7	119.6	C23—C24—C25	116.8 (3)
C7—C8—C9	120.0 (3)	C23—C24—C19	121.4 (3)
C7—C8—H8	120.0	C25—C24—C19	121.8 (3)
C9—C8—H8	120.0	C26—C25—C24	119.6 (3)
C10—C9—C8	120.9 (3)	C26—C25—H25	120.2
C10—C9—H9	119.6	C24—C25—H25	120.2
C8—C9—H9	119.6	N2—C26—C25	123.8 (3)
C9—C10—C3	120.9 (3)	N2—C26—H26	118.1
C9—C10—H10	119.5	C25—C26—H26	118.1
C3—C10—H10	119.5	C17—N1—C21	116.7 (3)
C12—C11—C16	118.3 (3)	C17—N1—Ag1	121.6 (2)
C12—C11—C4	121.6 (3)	C21—N1—Ag1	121.3 (2)
C16—C11—C4	120.1 (3)	C26—N2—C22	116.7 (3)
C13—C12—C11	120.3 (3)	C26—N2—Ag1^i	122.2 (2)
C13—C12—H12	119.9	C22—N2—Ag1^i	121.0 (2)
C11—C12—H12	119.9	C4—N3—C3	118.5 (2)
C14—C13—C12	120.9 (3)	C6—O1—Ag1	113.70 (19)
C14—C13—H13	119.6	Ag1—O1W—H1A	82.8
C12—C13—H13	119.6	Ag1—O1W—H1B	118.6
C15—C14—C13	119.1 (3)	H1A—O1W—H1B	108.2
C15—C14—H14	120.4	H2A—O2W—H2B	110.3
C13—C14—H14	120.4	H3A—O3W—H3B	108.1
C16—C15—C14	120.9 (3)	N1—Ag1—N2^ii	172.00 (9)
C16—C15—H15	119.5	N1—Ag1—O1	96.64 (8)
C14—C15—H15	119.5	N2^ii—Ag1—O1	89.43 (8)
C15—C16—C11	120.5 (3)	N1—Ag1—O1W	88.57 (8)
C15—C16—H16	119.7	N2^ii—Ag1—O1W	97.36 (9)
C11—C16—H16	119.7	O1—Ag1—O1W	83.08 (8)
N1—C17—C18	123.5 (3)
C5—C1—C2—C7	179.9 (3)	C17—C18—C19—C20	0.8 (4)
C6—C1—C2—C7	−2.2 (4)	C17—C18—C19—C24	−179.5 (3)
C5—C1—C2—C3	0.6 (4)	C18—C19—C20—C21	−0.2 (5)
C6—C1—C2—C3	178.5 (3)	C24—C19—C20—C21	−180.0 (3)
C7—C2—C3—N3	−178.4 (3)	C19—C20—C21—N1	−0.2 (5)
C1—C2—C3—N3	0.9 (4)	N2—C22—C23—C24	−1.0 (5)
C7—C2—C3—C10	3.5 (4)	C22—C23—C24—C25	0.0 (5)
C1—C2—C3—C10	−177.1 (3)	C22—C23—C24—C19	179.9 (3)
C2—C1—C5—C4	−1.2 (4)	C20—C19—C24—C23	−34.8 (5)
C6—C1—C5—C4	−179.1 (3)	C18—C19—C24—C23	145.5 (3)
N3—C4—C5—C1	0.4 (4)	C20—C19—C24—C25	145.2 (3)
C11—C4—C5—C1	178.1 (3)	C18—C19—C24—C25	−34.5 (4)
C5—C1—C6—O1	129.2 (3)	C23—C24—C25—C26	1.1 (5)
C2—C1—C6—O1	−48.7 (4)	C19—C24—C25—C26	−178.9 (3)
C5—C1—C6—O2	−50.4 (4)	C24—C25—C26—N2	−1.3 (5)
C2—C1—C6—O2	131.7 (3)	C18—C17—N1—C21	0.5 (4)
C1—C2—C7—C8	177.5 (3)	C18—C17—N1—Ag1	174.2 (2)
C3—C2—C7—C8	−3.2 (4)	C20—C21—N1—C17	0.1 (5)
C2—C7—C8—C9	0.7 (5)	C20—C21—N1—Ag1	−173.6 (2)
C7—C8—C9—C10	1.5 (5)	C25—C26—N2—C22	0.3 (5)
C8—C9—C10—C3	−1.1 (5)	C25—C26—N2—Ag1^i	−175.6 (2)
N3—C3—C10—C9	−179.6 (3)	C23—C22—N2—C26	0.9 (5)
C2—C3—C10—C9	−1.4 (5)	C23—C22—N2—Ag1^i	176.8 (2)
N3—C4—C11—C12	−155.1 (3)	C5—C4—N3—C3	1.0 (4)
C5—C4—C11—C12	27.2 (4)	C11—C4—N3—C3	−176.7 (2)
N3—C4—C11—C16	27.2 (4)	C10—C3—N3—C4	176.4 (3)
C5—C4—C11—C16	−150.5 (3)	C2—C3—N3—C4	−1.7 (4)
C16—C11—C12—C13	0.0 (4)	O2—C6—O1—Ag1	58.6 (4)
C4—C11—C12—C13	−177.7 (3)	C1—C6—O1—Ag1	−121.0 (2)
C11—C12—C13—C14	0.1 (5)	C17—N1—Ag1—O1	−39.8 (2)
C12—C13—C14—C15	−0.2 (5)	C21—N1—Ag1—O1	133.6 (2)
C13—C14—C15—C16	0.2 (5)	C17—N1—Ag1—O1W	−122.7 (2)
C14—C15—C16—C11	0.0 (5)	C21—N1—Ag1—O1W	50.7 (2)
C12—C11—C16—C15	−0.1 (4)	C6—O1—Ag1—N1	−134.9 (2)
C4—C11—C16—C15	177.7 (3)	C6—O1—Ag1—N2^ii	50.3 (2)
N1—C17—C18—C19	−0.9 (5)	C6—O1—Ag1—O1W	−47.2 (2)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1A···O2	0.85	2.02	2.816 (3)	156
O1W—H1B···O2^iii	0.85	1.97	2.805 (3)	168
O2W—H2A···N3	0.84	2.12	2.944 (3)	165
O2W—H2B···O3W^iv	0.84	1.89	2.711 (3)	167
O3W—H3A···O2W^v	0.85	1.92	2.764 (3)	172
O3W—H3B···O1	0.85	1.97	2.794 (3)	162

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