A grid-like two-dimensional Ag^I coordination polymer: poly[[[μ₃-N′-(4-cyano­benzyl­idene)­iso­nicotino­hydrazide]silver(I)] perchlorate]

This study presents new coordinating modes of a Schiff base with three coordinating groups and an inter­esting two-dimensional framework based on two types of constructing units. In the title compound, {[Ag(C₁₄H₁₀N₄O)]ClO₄}_n, the Ag^I ion is coordinated by three N atoms and one O atom from three different N′-(4-cyano­benzyl­idene)isonicotinohydrazide (L) ligands, forming a primary distorted square-planar coordination geometry. Two ligands each bridge two metal centres through one carbonitrile N atom in a monodentate mode and the hydrazide N and O atoms in a bidentate mode to form a small centrosymmetric (2+2)-Ag₂L₂ ring as a principal constructing unit. The pyridyl N atoms from four ligands in four of these small rings coordinate to Ag atoms in adjacent rings to form a large hexa­nuclear silver grid. A two-dimensional framework of rectangular grids is constructed from these small rings and large grids. Two perchlorate anions are located in each large grid and are bound to the grid by N—H...O hydrogen bonding. Crosslinking between the layers is achieved through long Ag...O inter­actions between the perchlorate anions and Ag atoms in adjacent layers.

S1. Comment

Silver coordination polymers have been studied widely not only for their utility in special functional materials, but also for their fascinating structures derived from variable coordination numbers (from 2 to 6) of Ag atoms and different conformations around silver metal centres (Sumby & Hardie, 2005; Dong et al., 2004). Multiple pyridyl, carbonitrile or pyridyl carbonitrile ligands are good bridging organic ligands in coordination interactions with Ag atoms (Antonioli et al., 2006; Bourlier et al., 2007).

Carbonitrile and pyridyl N atoms in the same organic ligand possess different coordinating properties. Taking advantage of these differences, chemists can design and construct novel silver metal–organic frameworks (Fernandez-Fernandez et al., 2006; Niu et al., 2007; Gonzalez et al., 2002). On the other hand, hydrazone groups in some organic ligands have been widely used as five-atom-ring chelates with some transition metal atoms such as Cu, Co and Zn (Iskander et al., 2001; Qiu et al., 2006; Gao et al., 2004). This group should coordinate in a bidentate fashion to Ag atoms. However, there are no reports in the literature concerning complexes derived from these components. We report here the structure of a two-dimensional silver coordination polymer, (I), of the bridging ligand N'-(4-cyanobenzylidene)isonicotinohydrazide, which contains carbonitrile, pyridyl and hydrazone groups. The variety of potential coordinating atoms in this ligand allows it to be used as a µ₂- or µ₃-bridging or a monodentate ligand.

In (I), the central silver ion is coordinated by one O atom and one N atom (O1 and N3) from the hydrazone chain and the pyridyl and carbonitrile N atoms of two other ligands [N1ⁱⁱ and N4ⁱ; symmetry codes: (i) -x + 1, -y + 1, -z; (ii) -x - 1/2, y + 1/2, -z + 1/2; Fig. 1]. Hydrazone atoms O1 and N3 are coordinated to one silver ion in a bidentate coordinating mode to form a planar five-membered chelate ring (Ag1/N3/N2/C6/O1) in which the maximum deviation from the plane is 0.010 (3) Å for atom O1. The coordination geometry about atom Ag1 is distorted square planar, with the distortion arising primarily from the bite angle imposed by the chelating hydrazone group. The length of the Ag—N bond involving the hydrazone N atom is about 0.1 Å longer than those involving the pyridyl and carbonitrile N atoms (Table 1). As is to be expected from the bite angle formed by the coordination of the hydrazone group, the geometry of this part of the ligand in (I) differs slightly from that of the free ligand (de Souza et al., 2007).

In (I), the N'-(4-cyanobenzylidene)isonicotinohydrazide ligand (L) acts as a µ₃-bridging ligand. Two ligands each bridge two Ag atoms through one carbonitrile N atom in a monodentate mode, and the hydrazone N and O atoms in a bidentate mode, to form a small centrosymmetric (2 + 2)-Ag₂L₂ ring. The Ag···Ag separation in one ring is 9.316 (3) Å. Four of these rings are linked to each other by the pyridyl atom N1, coordinating to Ag atoms in adjacent small rings to produce a large rectangular grid with Ag atoms at the corners of the rectangle. The large grid contains six Ag atoms (Fig. 2). Adjacent Ag atoms along the long side of the rectangle are bridged by the entire length of a ligand via the pyridyl and carbonitrile N atoms to give an Ag···Ag separation of 18.237 (3) Å. The short side of the rectangle involves two Ag atoms bridged via the bidentate hydrazone O1 and N3 atoms and the monodentate pyridyl atom N1 to give an Ag···Ag separation of 9.696 (3) Å. Two ClO₄^- counter-anions are located in the centrosymmetric nano-sized grid and interact with the rim of the rectangular grid by N—H···O hydrogen bonds, which involve the amine group of the ligand, N2, and atom O2 of a counter-anion (Table 2). As there is an Ag atom in the middle of each long side of the rectangular grid, and this Ag atom is also a corner of an adjacent rectangle, a brickwork lattice of two-dimensional layers is formed (Fig. 3). The layers lie approximately parallel to the (103) plane.

It is noteworthy that parallel two-dimensional layers stack together to form a nanometre-scale one-dimensional tunnel along the a axis. These nano-tunnels are filled with perchlorate counter-anions. Thus the crystals of (I) potentially have the ability to ion-exchange from perchlorate anions to other analogues such as BF₄^-. In addition to the above-mentioned hydrogen bonding between counter-anions and the ligands of the layer in which the counter-anions are located, there are weak Ag···O interactions between the two O atoms, O2 and O3, of one counter-anion and an Ag atom in a neighbouring layer, with Ag···O separations of 2.968 (3) and 3.016 (3) Å. Weak inter-layer π–π stacking, occurring between the benzene rings and pyridyl rings from neighbouring layers with a centroid-to-centroid distance of about 4 Å, also contribute somewhat to the supramolecular three-dimensional structure of (I).

The structures of some related silver(I)–pyridyl coordination polymers with perchlorate anions acting as both counter-anions and coordinating ligands have been reported. They are ({Ag₂[1,3-bis(4,5-dihydro-1H-imidazol-2- yl)benzene]₂}(ClO₄)₂)_n (Ren et al., 2004), {[Ag(2,4'-bipyridine)]ClO₄}_n (Tong et al., 1998), [Ag(di-2-pyridyl ketone)ClO₄]_n (Yang et al., 2000) and {Ag_2.5[2,5-bis(2-benzodiazine)-3,4-diaza-2,4-hexadiene]_1.5(ClO₄)_2.5(H₂O)₂}_n (Dong et al., 2005). The coordination modes of the perchlorate anions with the silver metal centre in the first of these compounds is very similar to that observed in (I). The silver ion has weak contacts with two O atoms from one perchlorate anion, with Ag···O separations of 2.83 and 3.11 Å. Another similarity is that the perchlorate anion forms weak hydrogen-bonding interactions with the uncoordinated N atoms from the organic ligand, with N···O (D···A) distances of 3.04 and 3.08 Å, which are longer than that in (I) (Ren et al., 2004). In the other three cited silver coordination polymers, the perchlorate O atoms are directly coordinated to the silver metal centers with Ag—O bond lengths less than 2.7 Å. Unlike the weak Ag···O contacts present in (I) and ({Ag₂[1,3-bis(4,5-dihydro-1H-imidazol-2-yl)benzene]₂}(ClO₄)₂)_n, which involve two O atoms of the anion, these strong Ag—O contacts form between just one perchlorate O atom and one Ag atom.

Related literature

For related literature, see: Antonioli et al. (2006); Bourlier et al. (2007); Dong et al. (2004, 2005); Fernandez-Fernandez, Bastida, Macias, Perez-Lourido & Valencia (2006); Gao et al. (2004); Gonzalez et al. (2002); Iskander et al. (2001); de Souza et al. (2007); Niu et al. (2007); Qiu et al. (2006); Ren et al. (2004); Sumby & Hardie (2005); Tong et al. (1998); Yang et al. (2000).

S2. Experimental

A solution of AgClO₄.H₂O (0.023 g, 0.1 mmol) in methanol (10 ml) was carefully layered on a methanol/chloroform solution (5 ml/10 ml) of N'-(4-cyanobenzylidene)isonicotinohydrazide (0.025 g, 0.1 mmol) in a straight glass tube. About ten days later, colourless single crystals of (I) suitable for X-ray analysis were obtained (yield 43%). Elemental analysis calculated for C₁₄H₁₀AgClN₄O₅: C 36.75, H 2.20, N 12.24%; found: C 36.86, H 2.11, N 12.09%.

S3. Refinement

C-bound H atoms were placed in calculated positions and refined using a riding model [C—H = 0.95 Å and U_iso(H) = 1.2U_eq(C)]. The N-bound H atom was first introduced in a calculated position, and then its position and displacement parameter were refined with the N—H bond distance restrained to 0.88 (2) Å. The final difference Fourier map had a highest peak at 0.94 Å from atom Ag1 and a deepest hole at 0.71 Å from atom Cl1, but was otherwise featureless.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT (Siemens, 1994); 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. A view of the Ag^I coordination environment in the polymeric structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry codes: (i) -x + 1, -y + 1, -z; (ii) -x - 1/2, y + 1/2, -z + 1/2.]
	Fig. 2. The octa-nuclear silver grid surrounding two counter-anions (dashed lines represent hydrogen bonds).
	Fig. 3. The two-dimensional layers in (I). All counter-anions and H atoms have been omitted for clarity.

poly[[[µ₃-N'-(4-cyanobenzylidene)isonicotinohydrazide]silver(I)] perchlorate]

Crystal data

[Ag(C14H10N4O)]ClO4	F(000) = 904
Mr = 457.58	Dx = 1.902 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5265 reflections
a = 8.5763 (5) Å	θ = 2.1–25.5°
b = 13.4913 (8) Å	µ = 1.46 mm^−1
c = 14.1944 (8) Å	T = 173 K
β = 103.370 (1)°	Block, colourless
V = 1597.86 (16) Å^3	0.46 × 0.34 × 0.32 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	2979 independent reflections
Radiation source: fine-focus sealed tube	2637 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
ϕ and ω scans	θmax = 25.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.553, Tmax = 0.652	k = −16→16
8730 measured reflections	l = −11→17

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0363P)^2 + 1.2063P] where P = (Fo^2 + 2Fc^2)/3
2979 reflections	(Δ/σ)max = 0.001
230 parameters	Δρmax = 0.52 e Å^−3
1 restraint	Δρmin = −0.43 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
Ag1	0.09040 (2)	0.430137 (15)	0.155600 (17)	0.05295 (10)
N1	−0.4511 (3)	0.04633 (17)	0.26960 (18)	0.0495 (5)
N2	0.0150 (3)	0.19362 (17)	0.15448 (17)	0.0464 (5)
N3	0.1302 (2)	0.25249 (16)	0.12916 (15)	0.0417 (5)
N4	0.8197 (4)	0.4510 (2)	−0.0608 (2)	0.0739 (8)
O1	−0.1160 (3)	0.32412 (14)	0.19687 (19)	0.0686 (6)
Cl1	0.38179 (9)	0.40439 (5)	0.37770 (5)	0.05339 (18)
O2	0.3786 (3)	0.48549 (18)	0.31283 (18)	0.0751 (6)
O3	0.2896 (4)	0.3265 (2)	0.32594 (19)	0.0926 (9)
O4	0.3203 (5)	0.4352 (2)	0.4560 (2)	0.1238 (14)
O5	0.5457 (4)	0.3734 (3)	0.4074 (3)	0.1160 (11)
C1	−0.3712 (3)	0.0163 (2)	0.2042 (2)	0.0534 (7)
H1	−0.3945	−0.0476	0.1765	0.064*
C2	−0.2573 (3)	0.07261 (18)	0.1747 (2)	0.0475 (6)
H2	−0.2028	0.0475	0.1286	0.057*
C3	−0.2238 (3)	0.16610 (18)	0.21319 (18)	0.0398 (5)
C4	−0.3106 (3)	0.1995 (2)	0.2781 (2)	0.0499 (6)
H4	−0.2943	0.2647	0.3040	0.060*
C5	−0.4202 (3)	0.1378 (2)	0.3046 (2)	0.0528 (7)
H5	−0.4770	0.1614	0.3502	0.063*
C6	−0.1037 (3)	0.23479 (19)	0.18746 (19)	0.0429 (6)
C7	0.2366 (3)	0.2056 (2)	0.09730 (19)	0.0455 (6)
H7	0.2303	0.1354	0.0924	0.055*
C8	0.3680 (3)	0.25715 (19)	0.06813 (18)	0.0425 (6)
C9	0.4365 (3)	0.2130 (2)	−0.0007 (2)	0.0519 (7)
H9	0.4015	0.1492	−0.0249	0.062*
C10	0.5553 (3)	0.2610 (2)	−0.0344 (2)	0.0546 (7)
H10	0.6003	0.2311	−0.0826	0.066*
C11	0.6079 (3)	0.3528 (2)	0.0027 (2)	0.0495 (6)
C12	0.5461 (3)	0.3959 (2)	0.0758 (2)	0.0510 (6)
H12	0.5861	0.4577	0.1033	0.061*
C13	0.4263 (3)	0.3477 (2)	0.1075 (2)	0.0467 (6)
H13	0.3831	0.3767	0.1569	0.056*
C14	0.7286 (4)	0.4057 (2)	−0.0326 (2)	0.0583 (8)
H14	0.023 (4)	0.1309 (14)	0.153 (2)	0.056 (9)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.04980 (14)	0.04061 (13)	0.08027 (18)	−0.00091 (8)	0.03922 (12)	0.00175 (10)
N1	0.0521 (13)	0.0422 (12)	0.0640 (14)	−0.0043 (10)	0.0337 (11)	−0.0017 (10)
N2	0.0449 (12)	0.0378 (12)	0.0651 (14)	−0.0058 (10)	0.0307 (10)	−0.0029 (10)
N3	0.0385 (10)	0.0433 (12)	0.0487 (12)	−0.0072 (9)	0.0212 (9)	−0.0005 (9)
N4	0.0662 (17)	0.0729 (18)	0.099 (2)	−0.0017 (14)	0.0531 (17)	0.0148 (16)
O1	0.0593 (12)	0.0396 (11)	0.1228 (19)	−0.0068 (9)	0.0537 (13)	−0.0067 (11)
Cl1	0.0681 (4)	0.0484 (4)	0.0477 (4)	−0.0109 (3)	0.0217 (3)	−0.0070 (3)
O2	0.0927 (17)	0.0563 (14)	0.0821 (15)	−0.0009 (12)	0.0318 (13)	0.0088 (12)
O3	0.117 (2)	0.0918 (19)	0.0802 (17)	−0.0578 (17)	0.0459 (15)	−0.0323 (14)
O4	0.189 (4)	0.121 (3)	0.090 (2)	−0.051 (2)	0.092 (2)	−0.0432 (18)
O5	0.098 (2)	0.102 (2)	0.127 (3)	0.0291 (18)	−0.0162 (19)	−0.001 (2)
C1	0.0660 (17)	0.0392 (14)	0.0652 (18)	−0.0110 (12)	0.0361 (14)	−0.0089 (13)
C2	0.0543 (15)	0.0424 (14)	0.0556 (16)	−0.0035 (11)	0.0325 (13)	−0.0055 (12)
C3	0.0361 (12)	0.0381 (13)	0.0491 (14)	0.0000 (10)	0.0178 (10)	0.0012 (10)
C4	0.0521 (15)	0.0398 (13)	0.0664 (17)	−0.0061 (12)	0.0311 (13)	−0.0097 (12)
C5	0.0541 (15)	0.0455 (15)	0.0705 (18)	−0.0015 (12)	0.0383 (14)	−0.0069 (13)
C6	0.0389 (12)	0.0400 (13)	0.0547 (15)	−0.0033 (10)	0.0213 (11)	−0.0006 (11)
C7	0.0454 (14)	0.0475 (14)	0.0490 (14)	−0.0050 (11)	0.0218 (11)	−0.0026 (12)
C8	0.0381 (12)	0.0480 (14)	0.0464 (14)	0.0029 (11)	0.0200 (11)	0.0038 (11)
C9	0.0503 (15)	0.0517 (16)	0.0597 (17)	−0.0015 (12)	0.0253 (13)	−0.0061 (13)
C10	0.0506 (15)	0.0673 (19)	0.0558 (17)	0.0066 (14)	0.0323 (13)	−0.0013 (14)
C11	0.0365 (13)	0.0587 (16)	0.0600 (16)	0.0043 (12)	0.0252 (12)	0.0129 (13)
C12	0.0453 (14)	0.0501 (15)	0.0636 (17)	−0.0042 (12)	0.0250 (13)	−0.0027 (13)
C13	0.0437 (14)	0.0497 (15)	0.0540 (15)	−0.0001 (11)	0.0265 (12)	−0.0037 (12)
C14	0.0493 (16)	0.0620 (17)	0.073 (2)	0.0083 (14)	0.0340 (15)	0.0144 (15)

Geometric parameters (Å, º)

Ag1—N4^i	2.336 (3)	C2—C3	1.378 (3)
Ag1—N1^ii	2.366 (2)	C2—H2	0.9500
Ag1—O1	2.4501 (19)	C3—C4	1.387 (4)
Ag1—N3	2.462 (2)	C3—C6	1.492 (3)
N1—C5	1.334 (3)	C4—C5	1.372 (4)
N1—C1	1.337 (3)	C4—H4	0.9500
N1—Ag1^iii	2.366 (2)	C5—H5	0.9500
N2—C6	1.336 (3)	C7—C8	1.464 (3)
N2—N3	1.378 (3)	C7—H7	0.9500
N2—H14	0.850 (18)	C8—C9	1.385 (4)
N3—C7	1.276 (3)	C8—C13	1.388 (4)
N4—C14	1.135 (4)	C9—C10	1.383 (4)
N4—Ag1^i	2.336 (3)	C9—H9	0.9500
O1—C6	1.220 (3)	C10—C11	1.380 (4)
Cl1—O4	1.399 (3)	C10—H10	0.9500
Cl1—O3	1.414 (2)	C11—C12	1.397 (4)
Cl1—O2	1.426 (2)	C11—C14	1.440 (4)
Cl1—O5	1.433 (3)	C12—C13	1.376 (4)
C1—C2	1.377 (4)	C12—H12	0.9500
C1—H1	0.9500	C13—H13	0.9500
N4^i—Ag1—N1^ii	94.11 (10)	C5—C4—C3	119.5 (3)
N4^i—Ag1—O1	153.07 (10)	C5—C4—H4	120.3
N1^ii—Ag1—O1	79.15 (7)	C3—C4—H4	120.3
N4^i—Ag1—N3	120.32 (9)	N1—C5—C4	123.3 (2)
N1^ii—Ag1—N3	144.64 (7)	N1—C5—H5	118.3
O1—Ag1—N3	66.51 (6)	C4—C5—H5	118.3
C5—N1—C1	116.7 (2)	O1—C6—N2	122.8 (2)
C5—N1—Ag1^iii	121.55 (18)	O1—C6—C3	120.3 (2)
C1—N1—Ag1^iii	120.25 (18)	N2—C6—C3	116.9 (2)
C6—N2—N3	120.1 (2)	N3—C7—C8	121.7 (2)
C6—N2—H14	120 (2)	N3—C7—H7	119.2
N3—N2—H14	120 (2)	C8—C7—H7	119.2
C7—N3—N2	114.9 (2)	C9—C8—C13	119.4 (2)
C7—N3—Ag1	132.26 (17)	C9—C8—C7	118.4 (2)
N2—N3—Ag1	112.85 (15)	C13—C8—C7	122.3 (2)
C14—N4—Ag1^i	156.7 (3)	C10—C9—C8	120.6 (3)
C6—O1—Ag1	117.70 (16)	C10—C9—H9	119.7
O4—Cl1—O3	111.40 (18)	C8—C9—H9	119.7
O4—Cl1—O2	109.32 (19)	C11—C10—C9	119.3 (3)
O3—Cl1—O2	108.05 (17)	C11—C10—H10	120.3
O4—Cl1—O5	112.2 (2)	C9—C10—H10	120.3
O3—Cl1—O5	109.16 (19)	C10—C11—C12	120.7 (2)
O2—Cl1—O5	106.55 (19)	C10—C11—C14	120.7 (3)
N1—C1—C2	123.9 (2)	C12—C11—C14	118.6 (3)
N1—C1—H1	118.1	C13—C12—C11	119.1 (3)
C2—C1—H1	118.1	C13—C12—H12	120.5
C1—C2—C3	118.8 (2)	C11—C12—H12	120.5
C1—C2—H2	120.6	C12—C13—C8	120.7 (2)
C3—C2—H2	120.6	C12—C13—H13	119.6
C2—C3—C4	117.8 (2)	C8—C13—H13	119.6
C2—C3—C6	124.3 (2)	N4—C14—C11	177.1 (3)
C4—C3—C6	117.9 (2)
C6—N2—N3—C7	−179.0 (2)	Ag1—O1—C6—C3	178.82 (18)
C6—N2—N3—Ag1	1.3 (3)	N3—N2—C6—O1	−0.2 (4)
N4^i—Ag1—N3—C7	28.5 (3)	N3—N2—C6—C3	179.9 (2)
N1^ii—Ag1—N3—C7	−166.1 (2)	C2—C3—C6—O1	155.3 (3)
O1—Ag1—N3—C7	179.2 (3)	C4—C3—C6—O1	−22.8 (4)
N4^i—Ag1—N3—N2	−151.90 (17)	C2—C3—C6—N2	−24.8 (4)
N1^ii—Ag1—N3—N2	13.5 (2)	C4—C3—C6—N2	157.1 (3)
O1—Ag1—N3—N2	−1.21 (16)	N2—N3—C7—C8	−179.4 (2)
N4^i—Ag1—O1—C6	112.3 (3)	Ag1—N3—C7—C8	0.1 (4)
N1^ii—Ag1—O1—C6	−170.2 (3)	N3—C7—C8—C9	−153.1 (3)
N3—Ag1—O1—C6	1.2 (2)	N3—C7—C8—C13	27.4 (4)
C5—N1—C1—C2	2.4 (5)	C13—C8—C9—C10	−3.9 (4)
Ag1^iii—N1—C1—C2	−163.7 (2)	C7—C8—C9—C10	176.6 (3)
N1—C1—C2—C3	−0.9 (5)	C8—C9—C10—C11	1.4 (4)
C1—C2—C3—C4	−1.7 (4)	C9—C10—C11—C12	2.0 (4)
C1—C2—C3—C6	−179.9 (3)	C9—C10—C11—C14	−178.5 (3)
C2—C3—C4—C5	2.8 (4)	C10—C11—C12—C13	−2.9 (4)
C6—C3—C4—C5	−179.0 (3)	C14—C11—C12—C13	177.6 (3)
C1—N1—C5—C4	−1.3 (5)	C11—C12—C13—C8	0.4 (4)
Ag1^iii—N1—C5—C4	164.7 (2)	C9—C8—C13—C12	2.9 (4)
C3—C4—C5—N1	−1.3 (5)	C7—C8—C13—C12	−177.6 (3)
Ag1—O1—C6—N2	−1.1 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H14···O2^iv	0.85 (2)	2.15 (2)	2.956 (3)	159 (3)

Symmetry code: (iv) −x+1/2, y−1/2, −z+1/2.