Construction of a dinuclear silver(I) coordination complex with a Schiff base containing 4-amino-1,2,4-triazole ligands.

The new ligand 1-(1,2,4-triazol-4-ylimino-meth-yl)-2-naphthol (L) and the title silver(I) complex, namely bis-[μ-1-(1,2,4-triazol-4-ylimino-meth-yl)-2-naphthol]bis-{[1-(1,2,4-triazol-4-yl-imino-meth-yl)-2-naphthol]silver(I)} dinitrate monohydrate, [Ag(2)(C(13)H(10)N(4)O)(4)](NO(3))(2)·H(2)O, were synthesized. Each silver center in the dimeric complex (related by an inversion centre) is coordinated by two bridging L ligands and one additional L ligand in a monodentate fashion, exhibiting a distorted trigonal-planar coordination. The discrete dimers are further linked through O-H⋯O hydrogen bonds and weak π-π stacking inter-actions [the shortest atom-atom separation is ca 3.46 Å between the parallel stacking pairs]. Intramolecular O-H⋯N hydrogen bonds are also present.

Related literature

For the structures of other triazole Schiff base compounds, see: Beckmann & Brooker (2003 ▶); Drabent et al. (2003 ▶, 2004 ▶); Garcia et al. (1997 ▶); Klingele & Brooker (2003 ▶); Liu et al. (2003 ▶, 2006 ▶); Wang et al. (2006 ▶); Yi et al. (2004 ▶); Zhai et al. (2006 ▶). For related literature, see: Han et al. (2004 ▶).

Experimental

Crystal data

[Ag2(C13H10N4O)4](NO3)2·H2O

M = 1310.78

Triclinic,

a = 9.8594 (15) Å

b = 10.7081 (15) Å

c = 12.8567 (19) Å

α = 82.391 (2)°

β = 81.155 (2)°

γ = 77.626 (2)°

V = 1303.1 (3) Å3

Z = 1

Mo Kα radiation

μ = 0.83 mm−1

T = 293 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.826, T max = 0.887

6610 measured reflections

4536 independent reflections

3137 reflections with I > 2σ(I)

R int = 0.118

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.133

S = 1.00

4536 reflections

379 parameters

H-atom parameters constrained

Δρmax = 0.85 e Å−3

Δρmin = −0.84 e Å−3

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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004760/wk2097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004760/wk2097Isup2.hkl

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

[Ag2(C13H10N4O)4](NO3)2·H2O	Z = 1
Mr = 1310.78	F(000) = 662
Triclinic, P1	Dx = 1.670 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8594 (15) Å	Cell parameters from 2250 reflections
b = 10.7081 (15) Å	θ = 2.4–25.4°
c = 12.8567 (19) Å	µ = 0.83 mm−1
α = 82.391 (2)°	T = 293 K
β = 81.155 (2)°	Block, orange
γ = 77.626 (2)°	0.2 × 0.18 × 0.16 mm
V = 1303.1 (3) Å3

Bruker APEX CCD area-detector diffractometer	4536 independent reflections
Radiation source: fine-focus sealed tube	3137 reflections with I > 2σ(I)
graphite	Rint = 0.118
φ and ω scans	θmax = 25.0°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→11
Tmin = 0.826, Tmax = 0.887	k = −12→8
6610 measured reflections	l = −15→14

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)] = 0.055	Hydrogen site location: geom, H2O from difmap
wR(F2) = 0.133	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0601P)2] where P = (Fo2 + 2Fc2)/3
4536 reflections	(Δ/σ)max = 0.001
379 parameters	Δρmax = 0.85 e Å−3
0 restraints	Δρmin = −0.84 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	Occ. (<1)
Ag1	0.84563 (4)	0.12190 (4)	0.95202 (3)	0.0613 (2)
O1	0.3147 (4)	0.5935 (3)	0.5781 (2)	0.0564 (9)
H1A	0.3862	0.5514	0.6002	0.085*
O2	1.2327 (4)	0.0054 (4)	0.4026 (3)	0.0701 (11)
H2B	1.2018	0.0029	0.4656	0.105*
N1	0.4657 (4)	0.4732 (4)	0.7179 (3)	0.0488 (10)
N2	0.5888 (4)	0.3908 (4)	0.7472 (3)	0.0447 (10)
N3	0.7966 (4)	0.2720 (4)	0.7236 (3)	0.0590 (12)
N4	0.7427 (4)	0.2564 (4)	0.8288 (3)	0.0554 (11)
N5	1.2436 (4)	−0.0497 (4)	0.6037 (3)	0.0453 (9)
N6	1.1907 (4)	−0.0406 (3)	0.7095 (3)	0.0412 (9)
N7	1.0373 (4)	0.0221 (4)	0.8420 (3)	0.0489 (10)
N8	1.1554 (4)	−0.0524 (4)	0.8806 (3)	0.0447 (10)
C1	0.1290 (5)	0.6319 (4)	0.8481 (4)	0.0423 (11)
C2	0.1404 (6)	0.6048 (5)	0.9573 (4)	0.0530 (13)
H2A	0.2232	0.5561	0.9789	0.064*
C3	0.0338 (6)	0.6481 (6)	1.0306 (4)	0.0633 (15)
H3A	0.0449	0.6287	1.1019	0.076*
C4	−0.0937 (6)	0.7218 (6)	1.0028 (4)	0.0663 (15)
H4A	−0.1664	0.7506	1.0545	0.080*
C5	−0.1082 (6)	0.7501 (5)	0.8987 (5)	0.0650 (15)
H5A	−0.1922	0.7993	0.8794	0.078*
C6	−0.0002 (5)	0.7072 (5)	0.8189 (4)	0.0514 (12)
C7	−0.0158 (6)	0.7374 (5)	0.7109 (4)	0.0582 (14)
H7A	−0.1003	0.7859	0.6921	0.070*
C8	0.0863 (6)	0.6988 (5)	0.6352 (4)	0.0552 (14)
H8A	0.0722	0.7200	0.5646	0.066*
C9	0.2163 (5)	0.6255 (4)	0.6608 (4)	0.0442 (11)
C10	0.2382 (5)	0.5910 (4)	0.7651 (4)	0.0404 (11)
C11	0.3702 (5)	0.5102 (4)	0.7907 (4)	0.0419 (11)
H11A	0.3840	0.4858	0.8611	0.050*
C12	0.6178 (5)	0.3277 (5)	0.8406 (4)	0.0515 (13)
H12A	0.5582	0.3338	0.9040	0.062*
C13	0.7004 (5)	0.3530 (5)	0.6776 (4)	0.0548 (14)
H13A	0.7082	0.3809	0.6057	0.066*
C14	1.5717 (5)	−0.2019 (5)	0.4532 (4)	0.0459 (11)
C15	1.6506 (5)	−0.2714 (5)	0.5336 (4)	0.0570 (13)
H15A	1.6110	−0.2711	0.6041	0.068*
C16	1.7841 (6)	−0.3386 (6)	0.5089 (5)	0.0684 (16)
H16A	1.8327	−0.3846	0.5629	0.082*
C17	1.8483 (7)	−0.3395 (6)	0.4050 (6)	0.083 (2)
H17A	1.9405	−0.3821	0.3897	0.099*
C18	1.7744 (7)	−0.2771 (6)	0.3256 (5)	0.0719 (17)
H18A	1.8153	−0.2810	0.2556	0.086*
C19	1.6372 (6)	−0.2068 (5)	0.3479 (4)	0.0577 (14)
C20	1.5622 (7)	−0.1409 (6)	0.2656 (4)	0.0679 (17)
H20A	1.6040	−0.1457	0.1959	0.082*
C21	1.4303 (7)	−0.0703 (6)	0.2851 (4)	0.0673 (17)
H21A	1.3840	−0.0259	0.2294	0.081*
C22	1.3641 (6)	−0.0650 (5)	0.3907 (4)	0.0526 (13)
C23	1.4329 (5)	−0.1275 (4)	0.4742 (3)	0.0435 (11)
C24	1.3675 (5)	−0.1161 (5)	0.5824 (3)	0.0441 (11)
H24A	1.4163	−0.1578	0.6377	0.053*
C25	1.0619 (5)	0.0279 (5)	0.7388 (4)	0.0477 (12)
H25A	1.0000	0.0725	0.6926	0.057*
C26	1.2458 (5)	−0.0883 (4)	0.7999 (3)	0.0432 (11)
H26A	1.3346	−0.1390	0.8039	0.052*
N9	0.5609 (6)	0.7008 (7)	0.8823 (5)	0.0847 (17)
O3	0.5165 (10)	0.7921 (8)	0.9419 (6)	0.183 (4)
O4	0.5557 (6)	0.7361 (6)	0.7950 (4)	0.125 (2)
O5	0.5869 (6)	0.5986 (5)	0.9295 (5)	0.116 (2)
O1W	0.6044 (13)	−0.0162 (13)	0.9945 (10)	0.143 (5)	0.50
H1WA	0.6068	−0.0783	0.9589	0.171*	0.50
H1WB	0.5600	−0.0207	1.0566	0.171*	0.50

	U11	U22	U33	U12	U13	U23
Ag1	0.0486 (3)	0.0810 (4)	0.0381 (2)	0.0158 (2)	−0.00257 (16)	0.00200 (18)
O1	0.053 (2)	0.067 (2)	0.0399 (17)	0.0063 (18)	−0.0092 (16)	0.0002 (16)
O2	0.076 (3)	0.077 (3)	0.0453 (19)	0.013 (2)	−0.0091 (18)	−0.0055 (18)
N1	0.041 (2)	0.054 (3)	0.046 (2)	0.005 (2)	−0.0109 (19)	−0.0009 (19)
N2	0.037 (2)	0.051 (2)	0.039 (2)	0.0072 (18)	−0.0074 (17)	−0.0035 (17)
N3	0.046 (3)	0.076 (3)	0.041 (2)	0.011 (2)	−0.0012 (19)	−0.001 (2)
N4	0.048 (3)	0.073 (3)	0.037 (2)	0.009 (2)	−0.0116 (19)	−0.001 (2)
N5	0.047 (2)	0.046 (2)	0.0352 (19)	0.0018 (19)	0.0022 (17)	−0.0045 (16)
N6	0.038 (2)	0.041 (2)	0.0361 (19)	0.0033 (18)	0.0052 (16)	−0.0051 (16)
N7	0.038 (2)	0.054 (3)	0.043 (2)	0.0105 (19)	−0.0008 (17)	−0.0038 (18)
N8	0.037 (2)	0.053 (3)	0.036 (2)	0.0062 (18)	−0.0033 (17)	−0.0029 (17)
C1	0.036 (3)	0.039 (3)	0.051 (3)	−0.003 (2)	−0.010 (2)	−0.004 (2)
C2	0.045 (3)	0.061 (3)	0.052 (3)	−0.008 (3)	−0.011 (2)	−0.003 (2)
C3	0.058 (4)	0.087 (4)	0.044 (3)	−0.017 (3)	0.006 (2)	−0.013 (3)
C4	0.049 (3)	0.082 (4)	0.063 (3)	−0.004 (3)	0.009 (3)	−0.022 (3)
C5	0.041 (3)	0.060 (4)	0.089 (4)	0.001 (3)	−0.005 (3)	−0.012 (3)
C6	0.035 (3)	0.051 (3)	0.066 (3)	−0.002 (2)	−0.009 (2)	−0.008 (2)
C7	0.043 (3)	0.058 (3)	0.070 (4)	0.005 (3)	−0.024 (3)	−0.001 (3)
C8	0.056 (3)	0.056 (3)	0.049 (3)	0.006 (3)	−0.022 (3)	0.000 (2)
C9	0.046 (3)	0.041 (3)	0.045 (3)	−0.003 (2)	−0.011 (2)	−0.001 (2)
C10	0.034 (3)	0.036 (3)	0.051 (3)	−0.003 (2)	−0.011 (2)	−0.005 (2)
C11	0.037 (3)	0.046 (3)	0.039 (2)	0.000 (2)	−0.007 (2)	−0.005 (2)
C12	0.042 (3)	0.067 (3)	0.035 (2)	0.014 (2)	−0.008 (2)	−0.006 (2)
C13	0.045 (3)	0.071 (4)	0.036 (2)	0.009 (3)	−0.001 (2)	0.002 (2)
C14	0.048 (3)	0.043 (3)	0.048 (3)	−0.014 (2)	0.005 (2)	−0.014 (2)
C15	0.048 (3)	0.058 (3)	0.062 (3)	−0.004 (3)	0.006 (3)	−0.019 (3)
C16	0.041 (3)	0.076 (4)	0.086 (4)	−0.004 (3)	−0.001 (3)	−0.022 (3)
C17	0.053 (4)	0.079 (5)	0.109 (5)	−0.007 (3)	0.025 (4)	−0.040 (4)
C18	0.068 (4)	0.076 (4)	0.069 (4)	−0.024 (3)	0.031 (3)	−0.029 (3)
C19	0.062 (4)	0.056 (3)	0.055 (3)	−0.022 (3)	0.018 (3)	−0.020 (3)
C20	0.085 (5)	0.074 (4)	0.042 (3)	−0.027 (4)	0.022 (3)	−0.014 (3)
C21	0.097 (5)	0.068 (4)	0.033 (3)	−0.014 (4)	−0.002 (3)	−0.002 (2)
C22	0.063 (4)	0.048 (3)	0.043 (3)	−0.008 (3)	0.003 (2)	−0.008 (2)
C23	0.049 (3)	0.040 (3)	0.039 (2)	−0.010 (2)	0.005 (2)	−0.008 (2)
C24	0.042 (3)	0.048 (3)	0.039 (2)	−0.006 (2)	0.003 (2)	−0.003 (2)
C25	0.038 (3)	0.055 (3)	0.039 (2)	0.007 (2)	−0.002 (2)	0.001 (2)
C26	0.041 (3)	0.047 (3)	0.036 (2)	0.002 (2)	−0.005 (2)	−0.004 (2)
N9	0.076 (4)	0.099 (5)	0.081 (4)	−0.028 (4)	−0.029 (3)	0.021 (4)
O3	0.216 (9)	0.163 (7)	0.149 (6)	−0.041 (6)	0.080 (6)	−0.057 (6)
O4	0.101 (4)	0.177 (6)	0.076 (3)	−0.002 (4)	−0.015 (3)	0.031 (4)
O5	0.132 (5)	0.090 (4)	0.118 (4)	−0.007 (3)	−0.041 (4)	0.027 (3)
O1W	0.115 (10)	0.181 (12)	0.125 (9)	−0.003 (9)	0.005 (8)	−0.057 (8)

Ag1—N8i	2.182 (3)	C7—H7A	0.9300
Ag1—N4	2.209 (4)	C8—C9	1.413 (6)
Ag1—N7	2.329 (4)	C8—H8A	0.9300
O1—C9	1.351 (6)	C9—C10	1.381 (6)
O1—H1A	0.8200	C10—C11	1.458 (6)
O2—C22	1.349 (7)	C11—H11A	0.9300
O2—H2B	0.8200	C12—H12A	0.9300
N1—C11	1.259 (6)	C13—H13A	0.9300
N1—N2	1.410 (5)	C14—C19	1.410 (6)
N2—C13	1.333 (6)	C14—C15	1.422 (7)
N2—C12	1.338 (5)	C14—C23	1.434 (7)
N3—C13	1.298 (6)	C15—C16	1.370 (8)
N3—N4	1.377 (5)	C15—H15A	0.9300
N4—C12	1.300 (6)	C16—C17	1.388 (9)
N5—C24	1.284 (6)	C16—H16A	0.9300
N5—N6	1.389 (5)	C17—C18	1.363 (9)
N6—C25	1.349 (6)	C17—H17A	0.9300
N6—C26	1.351 (5)	C18—C19	1.407 (8)
N7—C25	1.307 (6)	C18—H18A	0.9300
N7—N8	1.383 (5)	C19—C20	1.409 (8)
N8—C26	1.301 (6)	C20—C21	1.362 (9)
N8—Ag1i	2.182 (3)	C20—H20A	0.9300
C1—C2	1.412 (6)	C21—C22	1.416 (7)
C1—C6	1.428 (6)	C21—H21A	0.9300
C1—C10	1.435 (6)	C22—C23	1.378 (7)
C2—C3	1.346 (8)	C23—C24	1.450 (6)
C2—H2A	0.9300	C24—H24A	0.9300
C3—C4	1.403 (8)	C25—H25A	0.9300
C3—H3A	0.9300	C26—H26A	0.9300
C4—C5	1.355 (8)	N9—O4	1.141 (6)
C4—H4A	0.9300	N9—O5	1.176 (7)
C5—C6	1.406 (7)	N9—O3	1.284 (9)
C5—H5A	0.9300	O1W—H1WA	0.8499
C6—C7	1.408 (7)	O1W—H1WB	0.8500
C7—C8	1.326 (8)
N8i—Ag1—N4	147.87 (16)	N1—C11—C10	120.2 (4)
N8i—Ag1—N7	114.48 (13)	N1—C11—H11A	119.9
N4—Ag1—N7	97.64 (14)	C10—C11—H11A	119.9
C9—O1—H1A	109.5	N4—C12—N2	109.3 (4)
C22—O2—H2B	109.5	N4—C12—H12A	125.4
C11—N1—N2	117.8 (4)	N2—C12—H12A	125.4
C13—N2—C12	106.0 (4)	N3—C13—N2	111.0 (4)
C13—N2—N1	123.0 (4)	N3—C13—H13A	124.5
C12—N2—N1	130.8 (4)	N2—C13—H13A	124.5
C13—N3—N4	105.8 (4)	C19—C14—C15	116.7 (5)
C12—N4—N3	108.0 (4)	C19—C14—C23	119.6 (5)
C12—N4—Ag1	126.5 (3)	C15—C14—C23	123.7 (4)
N3—N4—Ag1	125.4 (3)	C16—C15—C14	121.1 (5)
C24—N5—N6	117.6 (4)	C16—C15—H15A	119.5
C25—N6—C26	106.3 (4)	C14—C15—H15A	119.5
C25—N6—N5	121.5 (4)	C15—C16—C17	121.4 (6)
C26—N6—N5	132.2 (4)	C15—C16—H16A	119.3
C25—N7—N8	106.9 (4)	C17—C16—H16A	119.3
C25—N7—Ag1	130.5 (3)	C18—C17—C16	119.1 (6)
N8—N7—Ag1	122.5 (3)	C18—C17—H17A	120.4
C26—N8—N7	107.8 (3)	C16—C17—H17A	120.4
C26—N8—Ag1i	129.5 (3)	C17—C18—C19	121.0 (6)
N7—N8—Ag1i	121.5 (3)	C17—C18—H18A	119.5
C2—C1—C6	117.2 (4)	C19—C18—H18A	119.5
C2—C1—C10	124.7 (4)	C18—C19—C20	120.7 (5)
C6—C1—C10	118.1 (4)	C18—C19—C14	120.6 (6)
C3—C2—C1	121.2 (5)	C20—C19—C14	118.7 (5)
C3—C2—H2A	119.4	C21—C20—C19	121.9 (5)
C1—C2—H2A	119.4	C21—C20—H20A	119.1
C2—C3—C4	121.9 (5)	C19—C20—H20A	119.1
C2—C3—H3A	119.0	C20—C21—C22	119.6 (5)
C4—C3—H3A	119.0	C20—C21—H21A	120.2
C5—C4—C3	118.5 (5)	C22—C21—H21A	120.2
C5—C4—H4A	120.8	O2—C22—C23	123.6 (5)
C3—C4—H4A	120.8	O2—C22—C21	115.6 (5)
C4—C5—C6	121.9 (5)	C23—C22—C21	120.8 (5)
C4—C5—H5A	119.0	C22—C23—C14	119.4 (4)
C6—C5—H5A	119.0	C22—C23—C24	120.6 (5)
C5—C6—C7	121.6 (5)	C14—C23—C24	120.0 (4)
C5—C6—C1	119.2 (5)	N5—C24—C23	121.5 (4)
C7—C6—C1	119.2 (5)	N5—C24—H24A	119.3
C8—C7—C6	121.9 (5)	C23—C24—H24A	119.3
C8—C7—H7A	119.0	N7—C25—N6	109.7 (4)
C6—C7—H7A	119.0	N7—C25—H25A	125.2
C7—C8—C9	120.6 (4)	N6—C25—H25A	125.2
C7—C8—H8A	119.7	N8—C26—N6	109.3 (4)
C9—C8—H8A	119.7	N8—C26—H26A	125.3
O1—C9—C10	123.3 (4)	N6—C26—H26A	125.3
O1—C9—C8	116.2 (4)	O4—N9—O5	134.0 (9)
C10—C9—C8	120.5 (5)	O4—N9—O3	112.1 (8)
C9—C10—C1	119.7 (4)	O5—N9—O3	113.6 (7)
C9—C10—C11	120.1 (4)	H1WA—O1W—H1WB	115.9
C1—C10—C11	120.2 (4)
C11—N1—N2—C13	−175.1 (5)	C1—C10—C11—N1	179.3 (4)
C11—N1—N2—C12	10.7 (8)	N3—N4—C12—N2	−0.9 (6)
C13—N3—N4—C12	0.2 (6)	Ag1—N4—C12—N2	−176.5 (3)
C13—N3—N4—Ag1	175.9 (4)	C13—N2—C12—N4	1.1 (6)
N8i—Ag1—N4—C12	−11.8 (6)	N1—N2—C12—N4	176.1 (5)
N7—Ag1—N4—C12	170.0 (5)	N4—N3—C13—N2	0.5 (6)
N8i—Ag1—N4—N3	173.4 (3)	C12—N2—C13—N3	−1.0 (6)
N7—Ag1—N4—N3	−4.9 (4)	N1—N2—C13—N3	−176.5 (4)
C24—N5—N6—C25	179.6 (4)	C19—C14—C15—C16	0.5 (8)
C24—N5—N6—C26	1.0 (7)	C23—C14—C15—C16	−178.6 (5)
N8i—Ag1—N7—C25	170.2 (4)	C14—C15—C16—C17	1.3 (9)
N4—Ag1—N7—C25	−10.8 (5)	C15—C16—C17—C18	−3.2 (10)
N8i—Ag1—N7—N8	−14.1 (4)	C16—C17—C18—C19	3.3 (9)
N4—Ag1—N7—N8	164.8 (3)	C17—C18—C19—C20	179.0 (6)
C25—N7—N8—C26	0.0 (5)	C17—C18—C19—C14	−1.5 (9)
Ag1—N7—N8—C26	−176.6 (3)	C15—C14—C19—C18	−0.3 (7)
C25—N7—N8—Ag1i	−168.3 (3)	C23—C14—C19—C18	178.7 (5)
Ag1—N7—N8—Ag1i	15.1 (5)	C15—C14—C19—C20	179.1 (5)
C6—C1—C2—C3	0.0 (7)	C23—C14—C19—C20	−1.8 (7)
C10—C1—C2—C3	179.0 (5)	C18—C19—C20—C21	−178.8 (6)
C1—C2—C3—C4	0.1 (9)	C14—C19—C20—C21	1.7 (9)
C2—C3—C4—C5	−0.4 (9)	C19—C20—C21—C22	−1.7 (9)
C3—C4—C5—C6	0.4 (9)	C20—C21—C22—O2	−178.9 (5)
C4—C5—C6—C7	−179.7 (5)	C20—C21—C22—C23	1.8 (9)
C4—C5—C6—C1	−0.2 (8)	O2—C22—C23—C14	178.8 (5)
C2—C1—C6—C5	0.0 (7)	C21—C22—C23—C14	−1.9 (8)
C10—C1—C6—C5	−179.1 (5)	O2—C22—C23—C24	−2.5 (8)
C2—C1—C6—C7	179.5 (5)	C21—C22—C23—C24	176.7 (5)
C10—C1—C6—C7	0.5 (7)	C19—C14—C23—C22	2.0 (7)
C5—C6—C7—C8	179.1 (5)	C15—C14—C23—C22	−179.0 (5)
C1—C6—C7—C8	−0.5 (8)	C19—C14—C23—C24	−176.7 (4)
C6—C7—C8—C9	−0.3 (9)	C15—C14—C23—C24	2.3 (7)
C7—C8—C9—O1	−178.4 (5)	N6—N5—C24—C23	−178.0 (4)
C7—C8—C9—C10	1.2 (8)	C22—C23—C24—N5	1.1 (7)
O1—C9—C10—C1	178.4 (4)	C14—C23—C24—N5	179.7 (5)
C8—C9—C10—C1	−1.2 (7)	N8—N7—C25—N6	0.4 (6)
O1—C9—C10—C11	−3.4 (7)	Ag1—N7—C25—N6	176.6 (3)
C8—C9—C10—C11	177.0 (4)	C26—N6—C25—N7	−0.7 (6)
C2—C1—C10—C9	−178.6 (5)	N5—N6—C25—N7	−179.5 (4)
C6—C1—C10—C9	0.3 (7)	N7—N8—C26—N6	−0.4 (5)
C2—C1—C10—C11	3.2 (7)	Ag1i—N8—C26—N6	166.7 (3)
C6—C1—C10—C11	−177.8 (4)	C25—N6—C26—N8	0.7 (6)
N2—N1—C11—C10	−177.4 (4)	N5—N6—C26—N8	179.4 (4)
C9—C10—C11—N1	1.2 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.83	2.548 (4)	145
O2—H2B···N5	0.82	1.87	2.588 (5)	145
O1W—H1WA···O3ii	0.85	1.85	2.594 (15)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.83	2.548 (4)	145
O2—H2B⋯N5	0.82	1.87	2.588 (5)	145
O1W—H1WA⋯O3i	0.85	1.85	2.594 (15)	145

Symmetry code: (i) .