1,1'-[(Ethane-1,2-diyldi­oxy)di-o-phenyl­ene]bis­(indoline-2,3-dione) (L) and a novel [Ag₂L₂]²⁺ metallocycle based on coordination-driven Ag-O and Ag-[pi] bonds

1,1'-[(Ethane-1,2-diyldi­oxy)di-o-phenyl­ene]bis­(indoline-2,3-dione), C₃₂H₂₄N₂O₆, L or (I), adopts a trans conformation with the two terminal indoline-2,3-dione groups located on opposite sides of the central ether bridge, as required by a centre of inversion located at the mid-point of the ethane C-C bond. However, in the discrete binuclear Ag^I metallocycle complex salt bis­{[mu]-1,1'-[(ethane-1,2-diyldi­oxy)di-o-phenyl­ene]bis­(indoline-2,3-dione)}disilver(I) bis­(hexa­fluor­ido­antimonate), [Ag₂(C₃₂H₂₄N₂O₆)₂][SbF₆]₂, (II), synthesized by combination of L with AgSbF₆, L adopts a gauche conformation to bind Ag^I via the two indolinedione O atoms and two C atoms from the phen­oxy ring. One dione O atom from the opposite side of the ether bridge completes the irregular coordination environment of each Ag^I atom. The complex is on a centre of inversion located between the Ag^I atoms. In the solid state, these binuclear [Ag₂L₂]²⁺ metallocycles stack together via inter­molecular [pi]-[pi] inter­actions to generate a one-dimensional chain motif, with the [SbF₆]^- counter-ions, which are disordered, located between the chains.

S1. Comment

The design and construction of molecular architectures based on transition metals and organic spacers is currently attracting significant attention (Leininger et al., 2000; Moulton & Zaworotko, 2001; Kitagawa et al., 2004). Over the past decade, numerous supramolecular networks based on metal-containing molecular building blocks linked through weak intermolecular interactions have been successfully achieved (Liu et al., 2006; Reger et al., 2009). Compared with hydrogen bond-driven networks, supramolecular networks driven by π–π stacking have received less attention. The π–π interaction undoubtedly plays an important role in determining the arrangement of discrete molecular complexes in the solid state (Khavasi & Fard, 2010).

In order to investigate further how π–π interactions participate in the arrangement of molecular complexes in self-assembled aggregates, we synthesized a new ethylene glycol ether bridging ligand, 1,1'-[(ethane-1,2-diyldioxy)di-o-phenylene]bis(indoline-2,3-dione), L or (I), in which two large aromatic indoline-2,3-dione groups are introduced. The combination of (I) with AgSbF₆ afforded [Ag₂L₂][SbF₆]₂, (II), which features a π–π stacking driven one-dimensional chain consisting of novel dinuclear [Ag₂L₂]²⁺ complexes.

The molecule of compound (I) is on a centre of inversion located at the midpoint of the central C16—C16ⁱ bond [symmetry code: (i) -x, -y + 1, -z] (Fig. 1) and consequently adopts a trans conformation in the solid state, with the two terminal indoline-2,3-dione groups located on opposite sides of the central bridging ether group. The results are similar to previously reported ethylene glycol ether bridging molecules, which typically adopt trans conformations in the free state (Han & Zhen, 2005). In addition, the terminal indoline-2,3-dione group is nearly perpendicular to the adjacent phenoxy arene ring. The corresponding dihedral angle is 83.28 (5)°. In the crystal structure, the molecules of (I) are arranged in chains running along the a axis, with π–π interactions [3.655 (1) Å] between adjacent parallel indoline-2,3-dione groups (Fig. 2).

In (II), two L ligands connect to each of two Ag^I centres, leading to a discrete binuclear Ag^I metallocycle complex, [Ag₂L₂]²⁺, with a centre of inversion located between the Ag^I atoms [Ag1···Ag1ⁱ distance 4.749 (1) Å; symmetry code: (i) -x, -y + 1, -z + 1] (Fig. 3). Each Ag^I centre lies in a five-coordinated environment defined by three O-atom donors (O2ⁱ, O5 and O6) from two ligands and two π-donor C atoms from a phenoxy arene ring. The Ag—O [2.372 (4)–2.577 (4) Å] and Ag—C [2.458 (6) and 2.572 (6) Å] distances are consistent with what we have previously observed in related complexes (Dong et al., 2006). In the metallacycle formed by each Ag^I atom and its primary coordinating L ligand, an open rectangular-like loop of dimensions ca 4.74 (1) × 7.60 (4) Å is found.

Compared with (I), the torsion angle of the central ether group, O3—C16—C17—O4, has changed from 180 to 76.1 (5)° in (II). Thus, L adopts a trans conformation about its central core in the free state, (I), but a gauche conformation after coordinating to the Ag^I centre in (II). The freedom of rotation around the central C—C single bond gives rise to varied conformations which may be frozen by metal-directed interactions. It is well known that flexible ethylene glycol ether bridging ligands with two terminal coordination donors can adopt different conformations under different conditions. For example, we have reported previously a study of a flexible ethylene glycol ether bridging ligand adopting different conformations at different temperatures (Dong et al., 2007). The relationship of the indoline-2,3-dione rings to the adjacent phenoxy rings is similar to that observed in the free ligand, as the corresponding dihedral angles are 89.1 (1) and 81.9 (1)°.

In the solid state, the dinuclear complexes of (II) are linked to each other through π–π interactions between indoline-2,3-dione groups from two different [Ag₂L₂]²⁺ units [centroid-to-centroid distance 3.825 (5) Å], resulting in one-dimensional chains along the crystallographic c axis (Fig. 4). These π–π interaction-driven one-dimensional chains are stacked in an –AA– parallel fashion in the b direction. Although there appear to be π–π interactions between arene rings in different chains, the corresponding centroid-to-centroid distance is 5.503 (8) Å, which is far too long for such interactions. The uncoordinated SbF₆^- counterions, which are rotationally disordered, are located in the spaces between the chains (Fig. 4).

In summary, the flexible ligand L with terminal indoline-2,3-dione groups can be used as a polydentate or chelating ligand to coordinate transition metal ions. A novel one-dimensional supramolecular chain was obtained successfully based on such coordination. This study demonstrates that π–π interactions play an important role in constructing aggregate supramolecular compounds. We are currently extending this result by preparing new ligands of this type with different substituted functional groups. We anticipate this approach to be useful for constructing novel superamolecular complexes.

Related literature

For related literature, see: Dong et al. (2006, 2007); Han & Zhen (2005); Khavasi & Fard (2010); Kitagawa et al. (2004); Leininger et al. (2000); Liu et al. (2006); Moulton & Zaworotko (2001); Reger et al. (2009).

S2. Experimental

K₂CO₃ (6.91 g, 50 mmol) was added with stirring to a solution of 1,2-bis(2-bromomethylphenoxy)ethane (2.00 g, 5 mmol) and indoline-2,3-dione (1.47 g, 10 mmol) in anhydrous CH₃CN (50 ml). The mixture was stirred for 12 h at ambient temperature and monitored by thin-layer chromatography (TLC). After removal of the solvent under vacuum, the residue was purified on silica gel by column chromatography using CH₂Cl₂:MeOH (30:1 v/v) as eluent to afford (I) as a red crystalline solid (1.09 g, 2.05 mmol; yield 41%). Spectroscopic analysis: IR (KBr pellet, ν, cm^-1): 1737 (s), 1615 (s), 1471 (s), 1351 (s), 1256 (m), 1119 (w), 1055 (w), 752 (s), 630 (m), 469 (m); ¹H NMR (300 MHz, CDCl₃, 298 K, TMS, δ, p.p.m.): 7.51 (d, 2H, o-C₆H₄), 7.31 (m, 2H, m-C₆H₄), 7.28 (m, 2H, p-C₆H₄), 7.23–6.98 (aabb, 8H, –C₆H₄), 6.78 (d, 2H, m-C₆H₄), 4.91 (s, 4H, –CH₂–), 4.42 (s, 4H, –CH₂–). Elemental analysis, calculated for C₃₂H₂₄N₂O₆: C 72.18, H 4.51, N 5.26, O 18.05%; found: C 72.19, H 4.50, N 5.25, O 18.06%.

A solution of AgSbF₆ (6.46 mg, 0.019 mmol) in benzene (5 ml) was layered on a solution of (I) (10.0 mg, 0.019 mmol) in CH₂Cl₂ (7 ml). The system was left for about one week at room temperature and red crystals of (II) were obtained (7.90 mg, yield 48%). Spectroscopic analysis: IR (KBr pellet, ν, cm^-1): 1712 (s), 1611 (s), 1491 (s), 1343 (s), 1245 (m), 1119 (w), 1062 (w), 759 (s), 662 (s), 472 (m).

S3. Refinement

The H atoms in both structures were placed in idealized positions and treated as riding, with C—H = 0.93 (aromatic), 0.97 (CH₂) and, in (II), 0.98 Å (CH with C coordinated to Ag), and with U_iso(H) = 1.2U_eq(C). The [SbF₆]^- anion was statistically disordered over two orientations, with site-occupation factors set at 0.50:0.50. The Sb1—F3/Sb1—F3', Sb1—F6/Sb1—F6' and Sb1—F4/Sb1—F4' pairs of bond lengths were restrained to be the same within a standard deviation of 0.01 Å. Atom F2' was constrained to have the same anisotropic displacement parameters as atom F2.

Computing details

For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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 molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level. [Symmetry code: (i) -x, -y + 1, -z.]
	Fig. 2. The packing of (I), showing one-dimensional chains driven by π–π interactions (dashed lines).
	Fig. 3. The molecular structure of the [Ag2L2]^2+ cations in (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms have been omitted for clarity. [Symmetry code: (i) -x, -y + 1, -z + 1.]
	Fig. 4. The one-dimensional chains of [Ag2L2]^2+ cations in (II), driven by intermolecular π–π interactions (dashed lines). Both orientations of the rotationally disordered [SbF6]^- counterions, located in the space between the chains, are shown.

(I) 1,1'-[(Ethane-1,2-diyldioxy)di-o-phenylene]bis(indoline-2,3-dione)

Crystal data

C32H24N2O6	F(000) = 556
Mr = 532.53	Dx = 1.367 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P2yn	Cell parameters from 857 reflections
a = 4.8272 (17) Å	θ = 2.6–20.9°
b = 14.194 (5) Å	µ = 0.10 mm^−1
c = 18.883 (7) Å	T = 298 K
β = 91.472 (7)°	Bar, red
V = 1293.4 (8) Å^3	0.55 × 0.14 × 0.04 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	1506 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.046
Graphite monochromator	θmax = 25.5°, θmin = 1.8°
ϕ and ω scans	h = −5→5
6683 measured reflections	k = −17→17
2398 independent reflections	l = −22→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)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0677P)^2 + 0.1059P] where P = (Fo^2 + 2Fc^2)/3
2398 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.13 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	0.0460 (6)	0.34667 (18)	0.22697 (14)	0.0505 (7)
C2	−0.1003 (6)	0.2714 (2)	0.25147 (15)	0.0648 (8)
H2	−0.0792	0.2113	0.2328	0.078*
C3	−0.2851 (7)	0.2899 (3)	0.30652 (17)	0.0831 (11)
H3	−0.3859	0.2403	0.3252	0.100*
C4	−0.3202 (8)	0.3788 (3)	0.33323 (18)	0.0871 (11)
H4	−0.4466	0.3886	0.3688	0.105*
C5	−0.1735 (8)	0.4526 (3)	0.30853 (18)	0.0816 (11)
H5	−0.1965	0.5128	0.3269	0.098*
C6	0.0111 (6)	0.4361 (2)	0.25532 (15)	0.0604 (8)
C7	0.1959 (7)	0.4991 (2)	0.21878 (16)	0.0711 (9)
C8	0.3527 (7)	0.4360 (2)	0.16718 (16)	0.0621 (8)
C9	0.3228 (6)	0.26742 (19)	0.13121 (14)	0.0562 (8)
H9A	0.3734	0.2157	0.1626	0.067*
H9B	0.4857	0.2840	0.1049	0.067*
C10	0.1012 (6)	0.23380 (17)	0.07975 (13)	0.0471 (7)
C11	0.0150 (6)	0.14134 (19)	0.07931 (15)	0.0593 (8)
H11	0.0934	0.0997	0.1121	0.071*
C12	−0.1832 (7)	0.1087 (2)	0.03189 (18)	0.0701 (9)
H12	−0.2372	0.0459	0.0329	0.084*
C13	−0.3014 (7)	0.1690 (2)	−0.01692 (17)	0.0683 (9)
H13	−0.4379	0.1473	−0.0485	0.082*
C14	−0.2181 (6)	0.2615 (2)	−0.01915 (14)	0.0606 (8)
H14	−0.2956	0.3020	−0.0529	0.073*
C15	−0.0193 (6)	0.29457 (17)	0.02871 (14)	0.0480 (7)
C16	−0.0569 (7)	0.45357 (16)	−0.01211 (15)	0.0606 (8)
H16A	−0.2558	0.4513	−0.0061	0.073*
H16B	−0.0190	0.4433	−0.0617	0.073*
N1	0.2453 (5)	0.34815 (14)	0.17423 (11)	0.0510 (6)
O1	0.2339 (6)	0.58289 (16)	0.22527 (15)	0.1163 (10)
O2	0.5383 (5)	0.46048 (15)	0.12861 (13)	0.0868 (8)
O3	0.0785 (4)	0.38421 (12)	0.03087 (10)	0.0592 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0492 (18)	0.0577 (17)	0.0443 (15)	0.0053 (14)	−0.0080 (14)	0.0005 (13)
C2	0.066 (2)	0.0686 (19)	0.0592 (18)	−0.0006 (17)	0.0003 (17)	0.0024 (15)
C3	0.071 (2)	0.119 (3)	0.060 (2)	−0.013 (2)	0.0062 (18)	0.010 (2)
C4	0.073 (3)	0.131 (3)	0.058 (2)	0.014 (2)	0.0031 (19)	−0.021 (2)
C5	0.080 (3)	0.100 (3)	0.065 (2)	0.026 (2)	−0.007 (2)	−0.022 (2)
C6	0.060 (2)	0.0674 (19)	0.0529 (18)	0.0106 (16)	−0.0094 (16)	−0.0108 (15)
C7	0.085 (3)	0.0549 (19)	0.072 (2)	−0.0029 (18)	−0.0220 (19)	−0.0064 (16)
C8	0.067 (2)	0.066 (2)	0.0534 (19)	−0.0078 (17)	−0.0093 (17)	0.0048 (15)
C9	0.0537 (18)	0.0578 (17)	0.0570 (17)	0.0100 (14)	0.0017 (14)	0.0022 (13)
C10	0.0478 (17)	0.0470 (15)	0.0472 (15)	0.0074 (13)	0.0134 (13)	−0.0017 (12)
C11	0.068 (2)	0.0515 (17)	0.0592 (18)	0.0094 (15)	0.0079 (17)	0.0028 (14)
C12	0.087 (3)	0.0508 (18)	0.073 (2)	−0.0077 (17)	0.018 (2)	−0.0077 (16)
C13	0.072 (2)	0.072 (2)	0.060 (2)	−0.0107 (17)	0.0041 (17)	−0.0183 (17)
C14	0.069 (2)	0.0665 (19)	0.0462 (16)	0.0011 (16)	0.0016 (15)	−0.0010 (14)
C15	0.0511 (18)	0.0454 (15)	0.0482 (16)	0.0033 (13)	0.0133 (14)	−0.0020 (12)
C16	0.068 (2)	0.0561 (17)	0.0573 (18)	0.0048 (15)	−0.0027 (16)	0.0124 (14)
N1	0.0551 (15)	0.0532 (14)	0.0447 (13)	−0.0005 (11)	0.0030 (12)	0.0013 (10)
O1	0.152 (3)	0.0580 (16)	0.138 (3)	−0.0148 (16)	−0.016 (2)	−0.0214 (14)
O2	0.0849 (18)	0.0991 (18)	0.0763 (15)	−0.0311 (14)	−0.0021 (14)	0.0117 (13)
O3	0.0627 (14)	0.0505 (11)	0.0639 (13)	0.0010 (9)	−0.0089 (10)	0.0117 (9)

Geometric parameters (Å, º)

C1—C2	1.368 (4)	C9—H9A	0.9700
C1—C6	1.390 (3)	C9—H9B	0.9700
C1—N1	1.402 (3)	C10—C11	1.377 (4)
C2—C3	1.412 (4)	C10—C15	1.408 (3)
C2—H2	0.9300	C11—C12	1.374 (4)
C3—C4	1.372 (5)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.371 (4)
C4—C5	1.353 (5)	C12—H12	0.9300
C4—H4	0.9300	C13—C14	1.373 (4)
C5—C6	1.380 (5)	C13—H13	0.9300
C5—H5	0.9300	C14—C15	1.383 (4)
C6—C7	1.450 (4)	C14—H14	0.9300
C7—O1	1.209 (3)	C15—O3	1.357 (3)
C7—C8	1.537 (4)	C16—O3	1.424 (3)
C8—O2	1.219 (4)	C16—C16^i	1.495 (5)
C8—N1	1.358 (3)	C16—H16A	0.9700
C9—N1	1.459 (3)	C16—H16B	0.9700
C9—C10	1.504 (4)
C2—C1—C6	121.0 (3)	H9A—C9—H9B	107.5
C2—C1—N1	128.4 (3)	C11—C10—C15	117.4 (3)
C6—C1—N1	110.6 (2)	C11—C10—C9	121.1 (2)
C1—C2—C3	116.5 (3)	C15—C10—C9	121.5 (2)
C1—C2—H2	121.8	C12—C11—C10	122.0 (3)
C3—C2—H2	121.8	C12—C11—H11	119.0
C4—C3—C2	121.9 (3)	C10—C11—H11	119.0
C4—C3—H3	119.1	C13—C12—C11	119.9 (3)
C2—C3—H3	119.1	C13—C12—H12	120.0
C5—C4—C3	121.0 (4)	C11—C12—H12	120.0
C5—C4—H4	119.5	C12—C13—C14	120.0 (3)
C3—C4—H4	119.5	C12—C13—H13	120.0
C4—C5—C6	118.2 (3)	C14—C13—H13	120.0
C4—C5—H5	120.9	C13—C14—C15	120.2 (3)
C6—C5—H5	120.9	C13—C14—H14	119.9
C5—C6—C1	121.5 (3)	C15—C14—H14	119.9
C5—C6—C7	131.2 (3)	O3—C15—C14	124.9 (2)
C1—C6—C7	107.3 (3)	O3—C15—C10	114.6 (2)
O1—C7—C6	130.7 (3)	C14—C15—C10	120.4 (2)
O1—C7—C8	124.2 (3)	O3—C16—C16^i	106.0 (3)
C6—C7—C8	105.1 (3)	O3—C16—H16A	110.5
O2—C8—N1	127.5 (3)	C16^i—C16—H16A	110.5
O2—C8—C7	126.4 (3)	O3—C16—H16B	110.5
N1—C8—C7	106.1 (3)	C16^i—C16—H16B	110.5
N1—C9—C10	114.9 (2)	H16A—C16—H16B	108.7
N1—C9—H9A	108.6	C8—N1—C1	110.7 (2)
C10—C9—H9A	108.6	C8—N1—C9	124.2 (2)
N1—C9—H9B	108.6	C1—N1—C9	125.0 (2)
C10—C9—H9B	108.6	C15—O3—C16	118.5 (2)
C6—C1—C2—C3	−0.2 (4)	C10—C11—C12—C13	0.0 (4)
N1—C1—C2—C3	178.7 (3)	C11—C12—C13—C14	1.1 (5)
C1—C2—C3—C4	1.2 (5)	C12—C13—C14—C15	−1.4 (4)
C2—C3—C4—C5	−1.3 (5)	C13—C14—C15—O3	179.6 (3)
C3—C4—C5—C6	0.5 (5)	C13—C14—C15—C10	0.5 (4)
C4—C5—C6—C1	0.5 (5)	C11—C10—C15—O3	−178.6 (2)
C4—C5—C6—C7	−179.6 (3)	C9—C10—C15—O3	−0.7 (3)
C2—C1—C6—C5	−0.6 (4)	C11—C10—C15—C14	0.6 (4)
N1—C1—C6—C5	−179.7 (3)	C9—C10—C15—C14	178.5 (2)
C2—C1—C6—C7	179.4 (3)	O2—C8—N1—C1	176.4 (3)
N1—C1—C6—C7	0.4 (3)	C7—C8—N1—C1	−2.8 (3)
C5—C6—C7—O1	−0.7 (6)	O2—C8—N1—C9	−5.1 (5)
C1—C6—C7—O1	179.2 (3)	C7—C8—N1—C9	175.7 (2)
C5—C6—C7—C8	178.1 (3)	C2—C1—N1—C8	−177.3 (3)
C1—C6—C7—C8	−2.0 (3)	C6—C1—N1—C8	1.6 (3)
O1—C7—C8—O2	2.6 (5)	C2—C1—N1—C9	4.2 (4)
C6—C7—C8—O2	−176.2 (3)	C6—C1—N1—C9	−176.9 (2)
O1—C7—C8—N1	−178.2 (3)	C10—C9—N1—C8	−110.2 (3)
C6—C7—C8—N1	2.9 (3)	C10—C9—N1—C1	68.1 (3)
N1—C9—C10—C11	−125.7 (3)	C14—C15—O3—C16	9.3 (4)
N1—C9—C10—C15	56.5 (3)	C10—C15—O3—C16	−171.6 (2)
C15—C10—C11—C12	−0.8 (4)	C16^i—C16—O3—C15	168.8 (3)
C9—C10—C11—C12	−178.7 (3)

Symmetry code: (i) −x, −y+1, −z.

(II) bis{µ-1,1'-[(ethane-1,2-diyldioxy)di-o-phenylene]bis(indoline- 2,3-dione)}disilver(I) bis(hexafluoridoantimonate)

Crystal data

[Ag2(C32H24N2O6)2][SbF6]2	Z = 1
Mr = 1752.30	F(000) = 860
Triclinic, P1	Dx = 1.898 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.193 (2) Å	Cell parameters from 2230 reflections
b = 11.594 (3) Å	θ = 2.5–22.0°
c = 14.220 (3) Å	µ = 1.61 mm^−1
α = 111.121 (3)°	T = 298 K
β = 91.073 (3)°	Block, red
γ = 100.819 (3)°	0.30 × 0.17 × 0.10 mm
V = 1533.0 (6) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	5593 independent reflections
Radiation source: fine-focus sealed tube	4279 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ϕ and ω scans	θmax = 25.5°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→12
Tmin = 0.645, Tmax = 0.856	k = −13→14
8087 measured reflections	l = −17→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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.134	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0582P)^2 + 1.8707P] where P = (Fo^2 + 2Fc^2)/3
5593 reflections	(Δ/σ)max = 0.001
481 parameters	Δρmax = 1.07 e Å^−3
3 restraints	Δρmin = −1.02 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	Occ. (<1)
Ag1	−0.20269 (7)	0.35357 (5)	0.42128 (4)	0.0796 (2)
C1	0.3205 (6)	0.4053 (6)	0.4483 (4)	0.0485 (13)
C2	0.3631 (5)	0.2907 (5)	0.3880 (4)	0.0462 (13)
C3	0.4572 (6)	0.2677 (6)	0.3178 (5)	0.0564 (15)
H3	0.5081	0.3334	0.3029	0.068*
C4	0.4733 (6)	0.1456 (7)	0.2707 (5)	0.0652 (18)
H4	0.5343	0.1279	0.2223	0.078*
C5	0.3994 (7)	0.0490 (7)	0.2948 (6)	0.072 (2)
H5	0.4129	−0.0328	0.2628	0.086*
C6	0.3050 (6)	0.0708 (6)	0.3658 (5)	0.0637 (17)
H6	0.2558	0.0054	0.3818	0.076*
C7	0.2882 (6)	0.1932 (5)	0.4109 (4)	0.0490 (13)
C8	0.2091 (6)	0.3630 (5)	0.5067 (4)	0.0474 (13)
C9	0.1080 (6)	0.1641 (6)	0.5282 (4)	0.0538 (15)
H9A	0.1402	0.1903	0.5989	0.065*
H9B	0.1114	0.0757	0.4950	0.065*
C10	−0.0341 (6)	0.1780 (5)	0.5215 (4)	0.0489 (13)
C11	−0.1097 (6)	0.1270 (5)	0.4280 (4)	0.0457 (13)
C12	−0.2450 (6)	0.1377 (6)	0.4212 (5)	0.0545 (15)
H12	−0.3059	0.0717	0.3659	0.065*
C13	−0.3004 (7)	0.2012 (6)	0.5085 (6)	0.0663 (18)
H13	−0.3981	0.1807	0.5084	0.080*
C14	−0.2259 (8)	0.2535 (7)	0.6004 (6)	0.079 (2)
H14	−0.2633	0.2979	0.6582	0.095*
C15	−0.0950 (7)	0.2398 (6)	0.6064 (5)	0.0670 (18)
H15	−0.0458	0.2729	0.6694	0.080*
C16	−0.1128 (6)	0.0250 (6)	0.2483 (4)	0.0520 (14)
H16A	−0.1530	0.0908	0.2403	0.062*
H16B	−0.1831	−0.0491	0.2367	0.062*
C17	−0.0094 (6)	−0.0064 (5)	0.1752 (4)	0.0512 (14)
H17A	0.0473	−0.0537	0.1952	0.061*
H17B	−0.0525	−0.0576	0.1078	0.061*
C18	0.1676 (5)	0.1032 (5)	0.1116 (4)	0.0424 (12)
C19	0.1988 (6)	−0.0095 (5)	0.0491 (4)	0.0516 (14)
H19	0.1500	−0.0863	0.0481	0.062*
C20	0.3029 (7)	−0.0071 (6)	−0.0117 (5)	0.0622 (17)
H20	0.3266	−0.0822	−0.0513	0.075*
C21	0.3712 (7)	0.1053 (7)	−0.0139 (5)	0.0643 (17)
H21	0.4388	0.1064	−0.0567	0.077*
C22	0.3393 (6)	0.2162 (6)	0.0475 (5)	0.0540 (15)
H22	0.3871	0.2924	0.0465	0.065*
C23	0.2377 (5)	0.2176 (5)	0.1108 (4)	0.0429 (12)
C24	0.2107 (6)	0.3421 (5)	0.1799 (4)	0.0499 (14)
H24A	0.2366	0.3539	0.2493	0.060*
H24B	0.2666	0.4095	0.1648	0.060*
C25	−0.0144 (6)	0.3522 (5)	0.2435 (4)	0.0460 (13)
C26	−0.1544 (6)	0.3407 (5)	0.1955 (4)	0.0483 (13)
C27	−0.1344 (5)	0.3430 (5)	0.0945 (4)	0.0458 (13)
C28	0.0010 (5)	0.3467 (4)	0.0833 (4)	0.0407 (12)
C29	0.0543 (6)	0.3441 (5)	−0.0062 (4)	0.0500 (14)
H29	0.1450	0.3466	−0.0141	0.060*
C30	−0.0357 (7)	0.3376 (6)	−0.0835 (5)	0.0612 (17)
H30	−0.0037	0.3350	−0.1449	0.073*
C31	−0.1695 (8)	0.3348 (6)	−0.0733 (5)	0.0680 (19)
H31	−0.2259	0.3308	−0.1271	0.082*
C32	−0.2207 (6)	0.3381 (5)	0.0165 (5)	0.0574 (15)
H32	−0.3113	0.3370	0.0244	0.069*
N1	0.1959 (4)	0.2378 (4)	0.4823 (3)	0.0442 (10)
N2	0.0707 (4)	0.3528 (4)	0.1717 (3)	0.0439 (10)
O1	0.3549 (5)	0.5140 (4)	0.4556 (3)	0.0641 (11)
O2	0.1461 (5)	0.4326 (4)	0.5649 (3)	0.0619 (11)
O3	−0.0450 (4)	0.0677 (4)	0.3484 (3)	0.0510 (9)
O4	0.0687 (4)	0.1091 (3)	0.1757 (3)	0.0493 (9)
O5	0.0114 (4)	0.3543 (4)	0.3278 (3)	0.0572 (11)
O6	−0.2563 (4)	0.3242 (4)	0.2363 (3)	0.0633 (11)
Sb1	0.58932 (4)	0.65652 (4)	0.22306 (3)	0.05775 (17)
F1	0.5908 (17)	0.557 (2)	0.0941 (13)	0.173 (9)	0.50
F2	0.553 (3)	0.773 (3)	0.1718 (17)	0.213 (8)	0.50
F3	0.7705 (10)	0.7206 (18)	0.225 (2)	0.141 (8)	0.50
F4	0.5995 (16)	0.777 (2)	0.3467 (10)	0.154 (8)	0.50
F5	0.625 (2)	0.551 (3)	0.273 (3)	0.224 (10)	0.50
F6	0.4088 (10)	0.645 (3)	0.212 (3)	0.170 (12)	0.50
F3'	0.7694 (8)	0.6482 (18)	0.2339 (17)	0.132 (8)	0.50
F4'	0.606 (3)	0.8212 (9)	0.258 (3)	0.267 (16)	0.50
F1'	0.5596 (15)	0.4808 (10)	0.176 (2)	0.154 (7)	0.50
F5'	0.5852 (15)	0.656 (4)	0.3504 (12)	0.191 (12)	0.50
F2'	0.601 (3)	0.642 (3)	0.0948 (17)	0.213 (8)	0.50
F6'	0.4072 (7)	0.615 (2)	0.219 (2)	0.112 (7)	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.1191 (5)	0.0646 (3)	0.0787 (4)	0.0429 (3)	0.0489 (4)	0.0407 (3)
C1	0.050 (3)	0.051 (3)	0.049 (3)	0.011 (3)	−0.001 (3)	0.025 (3)
C2	0.040 (3)	0.049 (3)	0.051 (3)	0.011 (3)	0.001 (2)	0.019 (3)
C3	0.041 (3)	0.074 (4)	0.057 (4)	0.013 (3)	0.006 (3)	0.027 (3)
C4	0.047 (4)	0.094 (5)	0.058 (4)	0.031 (4)	0.011 (3)	0.023 (4)
C5	0.057 (4)	0.065 (4)	0.083 (5)	0.027 (4)	0.001 (4)	0.008 (4)
C6	0.053 (4)	0.049 (4)	0.083 (5)	0.009 (3)	0.002 (3)	0.018 (3)
C7	0.048 (3)	0.052 (3)	0.044 (3)	0.013 (3)	−0.004 (3)	0.013 (3)
C8	0.048 (3)	0.048 (3)	0.044 (3)	0.015 (3)	0.000 (3)	0.013 (3)
C9	0.060 (4)	0.059 (4)	0.048 (3)	0.008 (3)	0.000 (3)	0.029 (3)
C10	0.054 (3)	0.050 (3)	0.049 (3)	0.011 (3)	0.008 (3)	0.026 (3)
C11	0.053 (3)	0.040 (3)	0.048 (3)	0.007 (3)	0.010 (3)	0.021 (3)
C12	0.044 (3)	0.062 (4)	0.065 (4)	0.012 (3)	0.008 (3)	0.032 (3)
C13	0.053 (4)	0.074 (4)	0.085 (5)	0.019 (3)	0.028 (4)	0.041 (4)
C14	0.090 (6)	0.081 (5)	0.075 (5)	0.034 (4)	0.045 (4)	0.029 (4)
C15	0.075 (5)	0.078 (5)	0.046 (4)	0.015 (4)	0.016 (3)	0.020 (3)
C16	0.051 (3)	0.051 (3)	0.050 (3)	−0.002 (3)	0.001 (3)	0.021 (3)
C17	0.064 (4)	0.042 (3)	0.039 (3)	0.005 (3)	0.006 (3)	0.008 (2)
C18	0.043 (3)	0.050 (3)	0.035 (3)	0.015 (3)	0.007 (2)	0.014 (2)
C19	0.058 (4)	0.044 (3)	0.052 (3)	0.013 (3)	0.012 (3)	0.015 (3)
C20	0.069 (4)	0.063 (4)	0.055 (4)	0.029 (3)	0.016 (3)	0.013 (3)
C21	0.054 (4)	0.081 (5)	0.064 (4)	0.027 (4)	0.022 (3)	0.027 (4)
C22	0.044 (3)	0.062 (4)	0.061 (4)	0.013 (3)	0.011 (3)	0.028 (3)
C23	0.037 (3)	0.046 (3)	0.048 (3)	0.013 (2)	0.005 (2)	0.018 (3)
C24	0.046 (3)	0.047 (3)	0.055 (3)	0.010 (3)	0.002 (3)	0.016 (3)
C25	0.055 (3)	0.037 (3)	0.048 (3)	0.017 (3)	0.013 (3)	0.015 (3)
C26	0.050 (3)	0.040 (3)	0.055 (3)	0.017 (3)	0.014 (3)	0.013 (3)
C27	0.044 (3)	0.041 (3)	0.053 (3)	0.013 (2)	0.005 (3)	0.016 (3)
C28	0.050 (3)	0.029 (3)	0.045 (3)	0.012 (2)	0.005 (2)	0.014 (2)
C29	0.062 (4)	0.043 (3)	0.051 (3)	0.020 (3)	0.016 (3)	0.020 (3)
C30	0.085 (5)	0.057 (4)	0.052 (4)	0.028 (4)	0.014 (3)	0.025 (3)
C31	0.090 (5)	0.060 (4)	0.055 (4)	0.020 (4)	−0.011 (4)	0.022 (3)
C32	0.049 (3)	0.053 (4)	0.070 (4)	0.018 (3)	0.001 (3)	0.020 (3)
N1	0.045 (3)	0.044 (3)	0.046 (3)	0.009 (2)	0.004 (2)	0.020 (2)
N2	0.043 (3)	0.044 (2)	0.048 (3)	0.015 (2)	0.008 (2)	0.017 (2)
O1	0.071 (3)	0.054 (3)	0.073 (3)	0.014 (2)	0.014 (2)	0.029 (2)
O2	0.078 (3)	0.058 (3)	0.056 (3)	0.025 (2)	0.022 (2)	0.023 (2)
O3	0.049 (2)	0.061 (2)	0.045 (2)	0.0156 (19)	0.0097 (18)	0.0187 (19)
O4	0.059 (2)	0.038 (2)	0.048 (2)	0.0104 (18)	0.0190 (18)	0.0109 (17)
O5	0.076 (3)	0.061 (3)	0.046 (2)	0.034 (2)	0.019 (2)	0.023 (2)
O6	0.051 (3)	0.069 (3)	0.076 (3)	0.023 (2)	0.026 (2)	0.029 (2)
Sb1	0.0471 (3)	0.0648 (3)	0.0586 (3)	0.0053 (2)	0.00704 (19)	0.0227 (2)
F1	0.147 (12)	0.180 (16)	0.106 (10)	0.095 (13)	−0.045 (9)	−0.074 (11)
F2	0.284 (19)	0.28 (2)	0.189 (15)	0.124 (16)	0.108 (13)	0.180 (16)
F3	0.070 (8)	0.155 (17)	0.145 (12)	−0.032 (8)	0.042 (8)	0.019 (14)
F4	0.103 (11)	0.217 (18)	0.073 (9)	0.058 (13)	−0.005 (7)	−0.039 (10)
F5	0.25 (3)	0.22 (2)	0.32 (3)	0.11 (2)	0.05 (2)	0.21 (3)
F6	0.145 (17)	0.23 (3)	0.132 (17)	0.112 (16)	−0.017 (13)	0.036 (17)
F3'	0.045 (6)	0.181 (19)	0.114 (11)	0.009 (7)	0.007 (6)	−0.005 (14)
F4'	0.28 (3)	0.042 (6)	0.46 (4)	0.027 (10)	0.20 (3)	0.061 (15)
F1'	0.119 (11)	0.057 (6)	0.25 (2)	0.018 (6)	0.017 (12)	0.018 (9)
F5'	0.083 (8)	0.41 (4)	0.079 (9)	−0.004 (17)	−0.001 (7)	0.121 (17)
F2'	0.284 (19)	0.28 (2)	0.189 (15)	0.124 (16)	0.108 (13)	0.180 (16)
F6'	0.028 (5)	0.116 (10)	0.176 (19)	−0.009 (6)	0.011 (8)	0.046 (10)

Geometric parameters (Å, º)

Ag1—O2^i	2.372 (4)	C18—C23	1.387 (7)
Ag1—C12	2.458 (6)	C18—C19	1.389 (7)
Ag1—O6	2.562 (5)	C19—C20	1.384 (8)
Ag1—C13	2.572 (6)	C19—H19	0.9300
Ag1—O5	2.577 (4)	C20—C21	1.368 (9)
C1—O1	1.209 (7)	C20—H20	0.9300
C1—C2	1.448 (8)	C21—C22	1.372 (9)
C1—C8	1.529 (8)	C21—H21	0.9300
C2—C7	1.385 (8)	C22—C23	1.384 (7)
C2—C3	1.389 (8)	C22—H22	0.9300
C3—C4	1.374 (9)	C23—C24	1.504 (7)
C3—H3	0.9300	C24—N2	1.462 (7)
C4—C5	1.382 (10)	C24—H24A	0.9700
C4—H4	0.9300	C24—H24B	0.9700
C5—C6	1.398 (9)	C25—O5	1.213 (7)
C5—H5	0.9300	C25—N2	1.353 (7)
C6—C7	1.378 (8)	C25—C26	1.532 (8)
C6—H6	0.9300	C26—O6	1.217 (7)
C7—N1	1.422 (7)	C26—C27	1.464 (8)
C8—O2	1.217 (7)	C27—C32	1.381 (8)
C8—N1	1.344 (7)	C27—C28	1.386 (7)
C9—N1	1.448 (7)	C28—C29	1.386 (7)
C9—C10	1.492 (8)	C28—N2	1.406 (7)
C9—H9A	0.9700	C29—C30	1.390 (9)
C9—H9B	0.9700	C29—H29	0.9300
C10—C15	1.389 (8)	C30—C31	1.369 (9)
C10—C11	1.391 (8)	C30—H30	0.9300
C11—O3	1.351 (6)	C31—C32	1.380 (9)
C11—C12	1.412 (8)	C31—H31	0.9300
C12—C13	1.387 (9)	C32—H32	0.9300
C12—H12	0.9800	O2—Ag1^i	2.372 (4)
C13—C14	1.368 (10)	Sb1—F5	1.702 (15)
C13—H13	0.9800	Sb1—F4'	1.765 (9)
C14—C15	1.378 (10)	Sb1—F2'	1.777 (18)
C14—H14	0.9300	Sb1—F1	1.784 (12)
C15—H15	0.9300	Sb1—F4	1.793 (9)
C16—O3	1.441 (7)	Sb1—F5'	1.816 (12)
C16—C17	1.496 (8)	Sb1—F6	1.819 (9)
C16—H16A	0.9700	Sb1—F6'	1.824 (6)
C16—H16B	0.9700	Sb1—F2	1.84 (2)
C17—O4	1.421 (6)	Sb1—F3	1.854 (8)
C17—H17A	0.9700	Sb1—F1'	1.862 (11)
C17—H17B	0.9700	Sb1—F3'	1.863 (8)
C18—O4	1.367 (6)
O2^i—Ag1—C12	174.39 (18)	O5—C25—C26	125.7 (5)
O2^i—Ag1—O6	80.32 (14)	N2—C25—C26	106.3 (5)
C12—Ag1—O6	104.62 (18)	O6—C26—C27	131.2 (6)
O2^i—Ag1—C13	145.85 (19)	O6—C26—C25	123.1 (5)
C12—Ag1—C13	31.9 (2)	C27—C26—C25	105.5 (5)
O6—Ag1—C13	126.5 (2)	C32—C27—C28	120.8 (5)
O2^i—Ag1—O5	78.73 (14)	C32—C27—C26	133.1 (6)
C12—Ag1—O5	100.40 (16)	C28—C27—C26	106.1 (5)
O6—Ag1—O5	68.87 (13)	C29—C28—C27	121.6 (5)
C13—Ag1—O5	127.52 (17)	C29—C28—N2	126.9 (5)
O1—C1—C2	132.5 (6)	C27—C28—N2	111.5 (5)
O1—C1—C8	122.4 (5)	C28—C29—C30	116.1 (6)
C2—C1—C8	105.1 (5)	C28—C29—H29	122.0
C7—C2—C3	120.9 (5)	C30—C29—H29	122.0
C7—C2—C1	106.9 (5)	C31—C30—C29	123.0 (6)
C3—C2—C1	132.2 (5)	C31—C30—H30	118.5
C4—C3—C2	118.4 (6)	C29—C30—H30	118.5
C4—C3—H3	120.8	C30—C31—C32	120.2 (6)
C2—C3—H3	120.8	C30—C31—H31	119.9
C3—C4—C5	120.4 (6)	C32—C31—H31	119.9
C3—C4—H4	119.8	C31—C32—C27	118.4 (6)
C5—C4—H4	119.8	C31—C32—H32	120.8
C4—C5—C6	121.8 (6)	C27—C32—H32	120.8
C4—C5—H5	119.1	C8—N1—C7	109.2 (5)
C6—C5—H5	119.1	C8—N1—C9	124.4 (5)
C7—C6—C5	117.1 (6)	C7—N1—C9	126.3 (5)
C7—C6—H6	121.5	C25—N2—C28	110.4 (5)
C5—C6—H6	121.5	C25—N2—C24	124.3 (5)
C6—C7—C2	121.3 (6)	C28—N2—C24	124.6 (5)
C6—C7—N1	127.4 (6)	C8—O2—Ag1^i	114.6 (4)
C2—C7—N1	111.2 (5)	C11—O3—C16	118.0 (4)
O2—C8—N1	127.4 (5)	C18—O4—C17	118.1 (4)
O2—C8—C1	125.0 (5)	C25—O5—Ag1	109.9 (4)
N1—C8—C1	107.6 (5)	C26—O6—Ag1	111.3 (4)
N1—C9—C10	113.0 (5)	F5—Sb1—F4'	139.3 (16)
N1—C9—H9A	109.0	F5—Sb1—F2'	125.2 (12)
C10—C9—H9A	109.0	F4'—Sb1—F2'	89.5 (14)
N1—C9—H9B	109.0	F5—Sb1—F1	95.7 (12)
C10—C9—H9B	109.0	F4'—Sb1—F1	121.0 (15)
H9A—C9—H9B	107.8	F2'—Sb1—F1	31.5 (8)
C15—C10—C11	118.2 (6)	F5—Sb1—F4	91.6 (12)
C15—C10—C9	122.0 (6)	F4'—Sb1—F4	50.5 (10)
C11—C10—C9	119.7 (5)	F2'—Sb1—F4	139.9 (12)
O3—C11—C10	115.4 (5)	F1—Sb1—F4	171.0 (13)
O3—C11—C12	124.5 (5)	F5—Sb1—F5'	48.3 (11)
C10—C11—C12	120.1 (5)	F4'—Sb1—F5'	96.3 (14)
C13—C12—C11	119.2 (6)	F2'—Sb1—F5'	173.5 (13)
C13—C12—Ag1	78.6 (4)	F1—Sb1—F5'	142.6 (14)
C11—C12—Ag1	97.3 (4)	F4—Sb1—F5'	45.8 (9)
C13—C12—H12	117.5	F5—Sb1—F6	109.5 (14)
C11—C12—H12	117.5	F4'—Sb1—F6	86.9 (14)
Ag1—C12—H12	117.5	F2'—Sb1—F6	92.1 (14)
C14—C13—C12	121.0 (6)	F1—Sb1—F6	93.5 (12)
C14—C13—Ag1	101.9 (5)	F4—Sb1—F6	89.1 (11)
C12—C13—Ag1	69.5 (4)	F5'—Sb1—F6	91.1 (12)
C14—C13—H13	117.5	F5—Sb1—F6'	97.0 (11)
C12—C13—H13	117.5	F4'—Sb1—F6'	97.8 (11)
Ag1—C13—H13	117.5	F2'—Sb1—F6'	98.4 (12)
C13—C14—C15	119.2 (6)	F1—Sb1—F6'	93.2 (11)
C13—C14—H14	120.4	F4—Sb1—F6'	91.2 (11)
C15—C14—H14	120.4	F5'—Sb1—F6'	83.7 (10)
C14—C15—C10	122.2 (7)	F6—Sb1—F6'	12.6 (17)
C14—C15—H15	118.9	F5—Sb1—F2	178.8 (14)
C10—C15—H15	118.9	F4'—Sb1—F2	39.5 (12)
O3—C16—C17	106.8 (5)	F2'—Sb1—F2	55.7 (9)
O3—C16—H16A	110.4	F1—Sb1—F2	85.4 (10)
C17—C16—H16A	110.4	F4—Sb1—F2	87.3 (10)
O3—C16—H16B	110.4	F5'—Sb1—F2	130.8 (13)
C17—C16—H16B	110.4	F6—Sb1—F2	71.0 (13)
H16A—C16—H16B	108.6	F6'—Sb1—F2	83.5 (11)
O4—C17—C16	107.9 (4)	F5—Sb1—F3	91.1 (11)
O4—C17—H17A	110.1	F4'—Sb1—F3	74.3 (10)
C16—C17—H17A	110.1	F2'—Sb1—F3	78.7 (12)
O4—C17—H17B	110.1	F1—Sb1—F3	88.4 (11)
C16—C17—H17B	110.1	F4—Sb1—F3	86.1 (10)
H17A—C17—H17B	108.4	F5'—Sb1—F3	100.0 (10)
O4—C18—C23	116.5 (5)	F6—Sb1—F3	159.1 (12)
O4—C18—C19	123.3 (5)	F6'—Sb1—F3	171.6 (10)
C23—C18—C19	120.2 (5)	F2—Sb1—F3	88.4 (11)
C20—C19—C18	119.7 (6)	F5—Sb1—F1'	46.0 (9)
C20—C19—H19	120.2	F4'—Sb1—F1'	174.4 (15)
C18—C19—H19	120.2	F2'—Sb1—F1'	86.7 (10)
C21—C20—C19	120.3 (6)	F1—Sb1—F1'	55.3 (8)
C21—C20—H20	119.8	F4—Sb1—F1'	133.4 (12)
C19—C20—H20	119.8	F5'—Sb1—F1'	87.7 (12)
C20—C21—C22	119.6 (6)	F6—Sb1—F1'	89.0 (12)
C20—C21—H21	120.2	F6'—Sb1—F1'	78.6 (9)
C22—C21—H21	120.2	F2—Sb1—F1'	135.2 (11)
C21—C22—C23	121.6 (6)	F3—Sb1—F1'	108.9 (8)
C21—C22—H22	119.2	F5—Sb1—F3'	64.2 (10)
C23—C22—H22	119.2	F4'—Sb1—F3'	99.9 (11)
C22—C23—C18	118.5 (5)	F2'—Sb1—F3'	89.6 (11)
C22—C23—C24	119.5 (5)	F1—Sb1—F3'	84.5 (8)
C18—C23—C24	122.0 (5)	F4—Sb1—F3'	93.9 (8)
N2—C24—C23	114.0 (4)	F5'—Sb1—F3'	86.5 (10)
N2—C24—H24A	108.8	F6—Sb1—F3'	173.0 (12)
C23—C24—H24A	108.8	F6'—Sb1—F3'	160.6 (10)
N2—C24—H24B	108.8	F2—Sb1—F3'	115.5 (11)
C23—C24—H24B	108.8	F3—Sb1—F3'	27.8 (8)
H24A—C24—H24B	107.7	F1'—Sb1—F3'	84.3 (7)
O5—C25—N2	127.9 (6)
O1—C1—C2—C7	−180.0 (6)	C19—C18—C23—C24	−177.7 (5)
C8—C1—C2—C7	−1.7 (6)	C22—C23—C24—N2	127.6 (6)
O1—C1—C2—C3	−0.6 (11)	C18—C23—C24—N2	−55.4 (7)
C8—C1—C2—C3	177.7 (6)	O5—C25—C26—O6	−4.8 (9)
C7—C2—C3—C4	0.6 (9)	N2—C25—C26—O6	172.1 (5)
C1—C2—C3—C4	−178.7 (6)	O5—C25—C26—C27	179.7 (5)
C2—C3—C4—C5	−1.4 (9)	N2—C25—C26—C27	−3.3 (6)
C3—C4—C5—C6	1.0 (10)	O6—C26—C27—C32	6.1 (11)
C4—C5—C6—C7	0.2 (10)	C25—C26—C27—C32	−178.9 (6)
C5—C6—C7—C2	−1.0 (9)	O6—C26—C27—C28	−171.3 (6)
C5—C6—C7—N1	177.8 (6)	C25—C26—C27—C28	3.6 (6)
C3—C2—C7—C6	0.6 (9)	C32—C27—C28—C29	−0.7 (8)
C1—C2—C7—C6	−179.9 (5)	C26—C27—C28—C29	177.1 (5)
C3—C2—C7—N1	−178.3 (5)	C32—C27—C28—N2	179.4 (5)
C1—C2—C7—N1	1.1 (6)	C26—C27—C28—N2	−2.8 (6)
O1—C1—C8—O2	−0.4 (9)	C27—C28—C29—C30	0.0 (8)
C2—C1—C8—O2	−178.9 (5)	N2—C28—C29—C30	179.9 (5)
O1—C1—C8—N1	−179.8 (5)	C28—C29—C30—C31	0.5 (9)
C2—C1—C8—N1	1.7 (6)	C29—C30—C31—C32	−0.2 (10)
N1—C9—C10—C15	−111.3 (6)	C30—C31—C32—C27	−0.5 (9)
N1—C9—C10—C11	69.4 (7)	C28—C27—C32—C31	1.0 (9)
C15—C10—C11—O3	−179.8 (5)	C26—C27—C32—C31	−176.2 (6)
C9—C10—C11—O3	−0.4 (7)	O2—C8—N1—C7	179.6 (6)
C15—C10—C11—C12	−0.5 (8)	C1—C8—N1—C7	−1.1 (6)
C9—C10—C11—C12	178.9 (5)	O2—C8—N1—C9	−4.6 (9)
O3—C11—C12—C13	−179.9 (5)	C1—C8—N1—C9	174.8 (5)
C10—C11—C12—C13	1.0 (8)	C6—C7—N1—C8	−178.9 (6)
O3—C11—C12—Ag1	−98.9 (5)	C2—C7—N1—C8	0.0 (6)
C10—C11—C12—Ag1	81.9 (5)	C6—C7—N1—C9	5.4 (9)
O2^i—Ag1—C12—C13	70.6 (18)	C2—C7—N1—C9	−175.8 (5)
O6—Ag1—C12—C13	−138.1 (4)	C10—C9—N1—C8	54.9 (7)
O5—Ag1—C12—C13	151.2 (4)	C10—C9—N1—C7	−130.0 (6)
O2^i—Ag1—C12—C11	−47.8 (19)	O5—C25—N2—C28	178.6 (5)
O6—Ag1—C12—C11	103.5 (4)	C26—C25—N2—C28	1.7 (5)
C13—Ag1—C12—C11	−118.4 (6)	O5—C25—N2—C24	7.2 (9)
O5—Ag1—C12—C11	32.8 (4)	C26—C25—N2—C24	−169.7 (4)
C11—C12—C13—C14	0.2 (10)	C29—C28—N2—C25	−179.3 (5)
Ag1—C12—C13—C14	−91.9 (7)	C27—C28—N2—C25	0.6 (6)
C11—C12—C13—Ag1	92.1 (5)	C29—C28—N2—C24	−7.9 (8)
O2^i—Ag1—C13—C14	−51.6 (6)	C27—C28—N2—C24	172.0 (5)
C12—Ag1—C13—C14	118.9 (6)	C23—C24—N2—C25	108.7 (6)
O6—Ag1—C13—C14	172.4 (4)	C23—C24—N2—C28	−61.5 (7)
O5—Ag1—C13—C14	82.2 (5)	N1—C8—O2—Ag1^i	−178.3 (4)
O2^i—Ag1—C13—C12	−170.5 (3)	C1—C8—O2—Ag1^i	2.4 (7)
O6—Ag1—C13—C12	53.5 (5)	C10—C11—O3—C16	−173.4 (5)
O5—Ag1—C13—C12	−36.7 (5)	C12—C11—O3—C16	7.4 (8)
C12—C13—C14—C15	−1.7 (11)	C17—C16—O3—C11	166.1 (4)
Ag1—C13—C14—C15	−74.9 (7)	C23—C18—O4—C17	177.1 (5)
C13—C14—C15—C10	2.2 (11)	C19—C18—O4—C17	−2.7 (8)
C11—C10—C15—C14	−1.1 (10)	C16—C17—O4—C18	−178.0 (5)
C9—C10—C15—C14	179.5 (6)	N2—C25—O5—Ag1	179.4 (4)
O3—C16—C17—O4	−76.1 (6)	C26—C25—O5—Ag1	−4.3 (6)
O4—C18—C19—C20	−178.3 (5)	O2^i—Ag1—O5—C25	−77.5 (4)
C23—C18—C19—C20	1.9 (9)	C12—Ag1—O5—C25	108.1 (4)
C18—C19—C20—C21	−2.9 (10)	O6—Ag1—O5—C25	6.4 (3)
C19—C20—C21—C22	2.4 (10)	C13—Ag1—O5—C25	126.9 (4)
C20—C21—C22—C23	−1.1 (10)	C27—C26—O6—Ag1	−175.1 (5)
C21—C22—C23—C18	0.2 (9)	C25—C26—O6—Ag1	10.7 (6)
C21—C22—C23—C24	177.3 (6)	O2^i—Ag1—O6—C26	72.8 (4)
O4—C18—C23—C22	179.6 (5)	C12—Ag1—O6—C26	−104.5 (4)
C19—C18—C23—C22	−0.6 (8)	C13—Ag1—O6—C26	−130.5 (4)
O4—C18—C23—C24	2.5 (8)	O5—Ag1—O6—C26	−8.8 (4)

Symmetry code: (i) −x, −y+1, −z+1.