Poly[[{μ3-1,2-bis­[(3-cyano­benzyl­idene)­hydrazono]-1,2-diphenyl­ethane}silver(I)] hexa­fluoridoantimonate]

Liu, L.-D.

doi:10.1107/S1600536807068432

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m363

doi:10.1107/S1600536807068432

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Poly[[{μ₃-1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane}silver(I)] hexafluoridoantimonate]

Lian-Dong Liu ^a ^*

^aDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: liandongliu1968@yahoo.com.cn

(Received 22 November 2007; accepted 26 December 2007; online 16 January 2008)

In the title compound, {[Ag(C₃₀H₂₀N₆)][SbF₆]}_n, the Ag⁺ cation has a three-coordinate environment completed by three N atoms of the 1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane ligand. The Ag⁺ cation coordination geometry is best described as distorted T-shaped. The crystal structure forms a three-dimensional structural polymer.

Related literature

For a related structure, see: Wei et al. (2007 ).

Experimental

Crystal data

[Ag(C₃₀H₂₀N₆)][SbF₆]
M_r = 808.14
Monoclinic, P 2₁ /c
a = 15.1652 (9) Å
b = 14.6022 (9) Å
c = 14.0711 (9) Å
β = 94.2570 (10)°
V = 3107.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.57 mm⁻¹
T = 298 (2) K
0.35 × 0.14 × 0.08 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.610, T_max = 0.885
15863 measured reflections
5885 independent reflections
4340 reflections with I > 2σ(I)
R_int = 0.032

Refinement

R[F² > 2σ(F²)] = 0.071
wR(F²) = 0.223
S = 1.05
5885 reflections
367 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 1.48 e Å⁻³
Δρ_min = −0.94 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—N5	2.287 (6)
Ag1—N3	2.334 (5)
Ag1—N1ⁱ	2.354 (9)

N5—Ag1—N3	145.2 (2)
N5—Ag1—N1ⁱ	107.5 (3)
N3—Ag1—N1ⁱ	97.9 (3)
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807068432/bx2129sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536807068432/bx2129Isup2.hkl

checkCIF report

Comment top

Silver complexes play a pivotal role in the area of self-assembly coordination chemistry (Wei et al., 2007). Here I report a new Ag(I) coordination polymer, (I) using 1,2-bis(benzene)-1,2-bis((3-cyanobenzylidene)hydrazone)ethane as bridge ligand.

The asymmetric unit of (I) is shown in Fig. 1. It reveals that Ag1 atom is coordinated by three N atoms which come from three ligands, respectively. The Ag1 atom is in a distorted T shape coordination environment (Table 1). In the crystal structure each 1,2-bis(benzene)-1,2-bis((3-cyanobenzylidene)hydrazone)ethane molecule function as tridentate bridge ligand with its two N atoms from two hydrazone groups, respectively, and a N atom from one of two cyanato groups, which resulted in the connections of three Ag(I) ions with separations of 7.0839 (5) Å (between the two Ag⁺ ions which are coordinated by two hydrazone groups) and 10.7616 (9) Å (between the two Ag⁺ ions which are coordinated by a hydrazone group and a cyanato group, respectively). In the crystal structure exist a weak π-π stacking intereaction, [Cg1···Cg1ⁱ = 3.788 (5) Å and Cg1···Cg1ⁱ_perp = 3.479 Å, symmetry codes: (i) 1 - x, 2 - y, 2 - z, Cg1 is the centroid of the the C1—C6 ring; Cg1···Cg1ⁱ_perp is the perpendicular distance from ring Cg1 to ring Cg1ⁱ]. In addition to the weak π-π stacking interaction there also exists the weak interaction between C15—H15 bond and the conjugated π bond, and the relevant distances are H15···Cg2 = 2.86 Å and H15···Cg2_perp = 2.826 Å [Cg2 is the centroid of the C9—C14 ring; H15···Cg2_perp is the perpendicular distance from H15 to ring Cg2]. The counter hexafluoroantimonate anions are inserted in the micropores of the polymer by electrostatic force.

Related literature top

For a related structure, see: Wei et al. (2007).

Experimental top

8 ml benzene solution of AgSbF₆ (0.0171 g, 0.05 mmol) was added very slowly on the 8 ml tetrahydrofuran solution of 1,2-bis(benzene)-1,2-bis((3-cyanobenzylidene)hydrazone)ethane (0.0093 g, 0.02 mmol). The colorless single crystals were obtained after the solution had been allowed to stand at room temperature for one week.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL (Bruker, 2001); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL (Bruker, 2001).

Figures top

Fig. 1. Part of the polymeric structure and the atom-numbering scheme of the title compound. Displacement ellipsoids are shown at the 30% probability level and H atoms and SbF^-₆ anion have been omitted for clarity. [Symmetry code: (i) -x + 1, y - 1/2, -z + 3/2]

Poly[[{µ₃-1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2- diphenylethane}silver(I)] hexafluoridoantimonate] top

Crystal data top

[Ag(C₃₀H₂₀N₆)][SbF₆]	F(000) = 1576
M_r = 808.14	D_x = 1.727 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3506 reflections
a = 15.1652 (9) Å	θ = 2.4–21.8°
b = 14.6022 (9) Å	µ = 1.57 mm⁻¹
c = 14.0711 (9) Å	T = 298 K
β = 94.257 (1)°	Block, colorless
V = 3107.4 (3) Å³	0.35 × 0.14 × 0.08 mm
Z = 4

Data collection top

Bruker SMART APEX CCD diffractometer	5885 independent reflections
Radiation source: fine-focus sealed tube	4340 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.032
ϕ and ω scans	θ_max = 25.7°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −18→13
T_min = 0.610, T_max = 0.885	k = −17→17
15863 measured reflections	l = −17→16

Refinement top

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.223	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.1282P)² + 7.595P] where P = (F_o² + 2F_c²)/3
5885 reflections	(Δ/σ)_max = 0.001
367 parameters	Δρ_max = 1.48 e Å⁻³
6 restraints	Δρ_min = −0.94 e Å⁻³

Crystal data top

[Ag(C₃₀H₂₀N₆)][SbF₆]	V = 3107.4 (3) Å³
M_r = 808.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.1652 (9) Å	µ = 1.57 mm⁻¹
b = 14.6022 (9) Å	T = 298 K
c = 14.0711 (9) Å	0.35 × 0.14 × 0.08 mm
β = 94.257 (1)°

Data collection top

Bruker SMART APEX CCD diffractometer	5885 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4340 reflections with I > 2σ(I)
T_min = 0.610, T_max = 0.885	R_int = 0.032
15863 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.071	6 restraints
wR(F²) = 0.223	H-atom parameters constrained
S = 1.05	Δρ_max = 1.48 e Å⁻³
5885 reflections	Δρ_min = −0.94 e Å⁻³
367 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ag1	0.26219 (4)	0.77830 (5)	0.61460 (4)	0.0554 (3)
C1	0.5013 (5)	0.9755 (6)	0.8609 (6)	0.0471 (17)
H1	0.4774	1.0223	0.8222	0.056*
C2	0.5826 (5)	0.9864 (6)	0.9087 (6)	0.0521 (19)
C3	0.6190 (6)	0.9176 (8)	0.9667 (7)	0.068 (2)
H3	0.6742	0.9253	0.9990	0.082*
C4	0.5731 (6)	0.8387 (7)	0.9760 (7)	0.069 (2)
H4	0.5970	0.7924	1.0152	0.082*
C5	0.4926 (5)	0.8267 (6)	0.9286 (6)	0.0534 (19)
H5	0.4622	0.7720	0.9353	0.064*
C6	0.4551 (5)	0.8952 (5)	0.8701 (5)	0.0447 (17)
C7	0.3681 (5)	0.8834 (6)	0.8173 (5)	0.0483 (18)
H7	0.3486	0.9279	0.7733	0.058*
C8	0.1698 (4)	0.8068 (4)	0.8094 (5)	0.0350 (14)
C9	0.0853 (4)	0.8073 (5)	0.7522 (5)	0.0400 (15)
C10	0.0724 (6)	0.8656 (6)	0.6764 (6)	0.056 (2)
H10	0.1173	0.9052	0.6613	0.067*
C11	−0.0095 (7)	0.8658 (8)	0.6211 (7)	0.081 (3)
H11	−0.0183	0.9059	0.5700	0.098*
C12	−0.0742 (7)	0.8087 (9)	0.6415 (8)	0.089 (3)
H12	−0.1278	0.8092	0.6048	0.107*
C13	−0.0613 (6)	0.7492 (9)	0.7174 (8)	0.083 (3)
H13	−0.1056	0.7076	0.7294	0.100*
C14	0.0160 (5)	0.7501 (7)	0.7760 (6)	0.061 (2)
H14	0.0220	0.7136	0.8303	0.073*
C15	0.1073 (5)	0.6282 (6)	0.5563 (5)	0.0505 (18)
H15	0.0979	0.6863	0.5806	0.061*
C16	0.0836 (6)	0.5516 (7)	0.6067 (6)	0.065 (3)
H16	0.0582	0.5586	0.6645	0.078*
C17	0.0973 (6)	0.4656 (7)	0.5719 (7)	0.068 (3)
H17	0.0823	0.4141	0.6060	0.082*
C18	0.1329 (6)	0.4568 (6)	0.4874 (9)	0.071 (3)
H18	0.1418	0.3983	0.4639	0.085*
C19	0.1569 (5)	0.5322 (5)	0.4337 (6)	0.0485 (18)
H19	0.1805	0.5244	0.3751	0.058*
C20	0.1444 (4)	0.6192 (5)	0.4706 (5)	0.0383 (15)
C21	0.1707 (4)	0.7000 (5)	0.4178 (4)	0.0348 (14)
C22	0.2843 (5)	0.8878 (5)	0.4167 (5)	0.0446 (17)
H22	0.3236	0.8636	0.4640	0.054*
C23	0.2510 (5)	1.0143 (6)	0.3026 (6)	0.0524 (19)
H23	0.1958	0.9887	0.2866	0.063*
C24	0.3115 (5)	0.9698 (5)	0.3671 (5)	0.0447 (17)
C25	0.3932 (5)	1.0076 (5)	0.3876 (6)	0.0499 (18)
H25	0.4338	0.9774	0.4294	0.060*
C26	0.2742 (6)	1.0966 (6)	0.2630 (7)	0.062 (2)
H26	0.2337	1.1269	0.2211	0.074*
C27	0.3561 (5)	1.1342 (5)	0.2845 (6)	0.0513 (18)
H27	0.3711	1.1894	0.2570	0.062*
C28	0.4167 (5)	1.0895 (5)	0.3478 (5)	0.0442 (16)
C29	0.5013 (5)	1.1297 (6)	0.3716 (6)	0.0519 (19)
C44	0.6304 (6)	1.0721 (7)	0.8957 (7)	0.062 (2)
F1	0.7216 (7)	0.8582 (8)	0.4958 (8)	0.166 (4)*
F2	0.6267 (14)	0.8795 (14)	0.3382 (15)	0.287 (8)*
F3	0.8623 (11)	0.9046 (13)	0.3989 (13)	0.249 (7)*
F4	0.7568 (6)	0.7731 (7)	0.3528 (7)	0.146 (3)*
F5	0.7664 (9)	0.9245 (9)	0.2583 (10)	0.200 (5)*
F6	0.7215 (7)	1.0152 (8)	0.3911 (7)	0.150 (3)*
N1	0.6676 (5)	1.1345 (6)	0.8850 (7)	0.076 (2)
N2	0.5688 (5)	1.1629 (5)	0.3896 (6)	0.068 (2)
N3	0.1969 (4)	0.7738 (4)	0.4591 (4)	0.0381 (13)
N4	0.2127 (4)	0.8481 (4)	0.4001 (4)	0.0415 (13)
N5	0.2418 (4)	0.8153 (4)	0.7693 (4)	0.0381 (13)
N6	0.3198 (4)	0.8160 (4)	0.8293 (4)	0.0425 (14)
Sb1	0.73809 (5)	0.89221 (4)	0.37378 (4)	0.0695 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0756 (5)	0.0607 (4)	0.0291 (3)	−0.0012 (3)	−0.0009 (3)	−0.0029 (2)
C1	0.035 (4)	0.058 (4)	0.049 (4)	−0.004 (3)	0.008 (3)	−0.004 (4)
C2	0.046 (4)	0.054 (5)	0.057 (5)	−0.003 (4)	0.006 (4)	−0.012 (4)
C3	0.040 (5)	0.095 (7)	0.068 (6)	0.002 (5)	−0.007 (4)	0.006 (5)
C4	0.048 (5)	0.076 (6)	0.080 (7)	0.003 (5)	−0.009 (4)	0.009 (5)
C5	0.045 (4)	0.056 (5)	0.058 (5)	−0.004 (4)	−0.001 (4)	0.005 (4)
C6	0.039 (4)	0.059 (5)	0.036 (4)	−0.001 (3)	0.005 (3)	−0.005 (3)
C7	0.039 (4)	0.066 (5)	0.040 (4)	0.003 (4)	0.004 (3)	0.002 (4)
C8	0.035 (4)	0.037 (3)	0.032 (3)	0.001 (3)	−0.001 (3)	0.001 (3)
C9	0.039 (4)	0.047 (4)	0.033 (3)	0.000 (3)	−0.002 (3)	−0.007 (3)
C10	0.057 (5)	0.063 (5)	0.047 (4)	0.001 (4)	−0.015 (4)	0.011 (4)
C11	0.070 (7)	0.101 (8)	0.069 (6)	0.019 (6)	−0.024 (5)	0.017 (6)
C12	0.047 (6)	0.131 (10)	0.087 (8)	0.014 (6)	−0.017 (5)	0.000 (7)
C13	0.035 (5)	0.129 (9)	0.085 (7)	−0.025 (5)	0.002 (5)	−0.010 (7)
C14	0.048 (5)	0.084 (6)	0.049 (5)	−0.009 (4)	0.002 (4)	0.008 (4)
C15	0.049 (4)	0.063 (5)	0.039 (4)	−0.009 (4)	0.002 (3)	0.003 (3)
C16	0.055 (5)	0.091 (8)	0.048 (5)	−0.012 (5)	−0.002 (4)	0.025 (5)
C17	0.054 (5)	0.079 (7)	0.068 (6)	−0.025 (5)	−0.016 (5)	0.037 (5)
C18	0.055 (5)	0.044 (5)	0.108 (9)	−0.003 (4)	−0.029 (6)	0.010 (5)
C19	0.046 (4)	0.043 (4)	0.055 (5)	−0.006 (3)	−0.007 (3)	0.001 (3)
C20	0.031 (3)	0.049 (4)	0.034 (3)	−0.006 (3)	−0.004 (3)	0.002 (3)
C21	0.028 (3)	0.046 (4)	0.030 (3)	−0.001 (3)	−0.001 (2)	0.002 (3)
C22	0.042 (4)	0.057 (5)	0.034 (4)	0.000 (3)	−0.008 (3)	0.006 (3)
C23	0.055 (5)	0.053 (4)	0.047 (4)	−0.008 (4)	−0.010 (4)	0.002 (4)
C24	0.056 (5)	0.042 (4)	0.036 (4)	−0.001 (3)	0.001 (3)	0.001 (3)
C25	0.050 (5)	0.048 (4)	0.050 (4)	0.002 (4)	−0.011 (3)	−0.001 (3)
C26	0.063 (5)	0.053 (5)	0.069 (6)	0.006 (4)	−0.001 (4)	0.022 (4)
C27	0.061 (5)	0.041 (4)	0.052 (5)	−0.004 (4)	0.006 (4)	0.010 (3)
C28	0.041 (4)	0.049 (4)	0.044 (4)	−0.002 (3)	0.004 (3)	−0.002 (3)
C29	0.051 (5)	0.056 (5)	0.047 (4)	−0.006 (4)	−0.003 (3)	−0.001 (4)
C44	0.041 (5)	0.075 (6)	0.071 (6)	−0.011 (4)	0.002 (4)	−0.015 (5)
N1	0.049 (4)	0.072 (5)	0.105 (7)	−0.013 (4)	−0.006 (4)	−0.006 (5)
N2	0.059 (5)	0.074 (5)	0.068 (5)	−0.014 (4)	−0.010 (4)	0.006 (4)
N3	0.038 (3)	0.041 (3)	0.035 (3)	0.000 (2)	0.000 (2)	0.001 (2)
N4	0.050 (4)	0.044 (3)	0.030 (3)	−0.001 (3)	0.002 (2)	0.002 (2)
N5	0.035 (3)	0.048 (3)	0.031 (3)	0.000 (2)	−0.002 (2)	0.001 (2)
N6	0.031 (3)	0.063 (4)	0.033 (3)	−0.004 (3)	−0.001 (2)	0.001 (3)
Sb1	0.1014 (6)	0.0518 (4)	0.0563 (4)	0.0034 (3)	0.0135 (3)	−0.0063 (3)

Geometric parameters (Å, º) top

Ag1—N5	2.287 (6)	C16—H16	0.9300
Ag1—N3	2.334 (5)	C17—C18	1.347 (15)
Ag1—N1ⁱ	2.354 (9)	C17—H17	0.9300
C1—C2	1.369 (11)	C18—C19	1.399 (12)
C1—C6	1.377 (11)	C18—H18	0.9300
C1—H1	0.9300	C19—C20	1.391 (10)
C2—C3	1.384 (13)	C19—H19	0.9300
C2—C44	1.465 (13)	C20—C21	1.465 (9)
C3—C4	1.357 (13)	C21—N3	1.273 (8)
C3—H3	0.9300	C21—C8ⁱⁱⁱ	1.527 (9)
C4—C5	1.359 (12)	C22—N4	1.238 (9)
C4—H4	0.9300	C22—C24	1.460 (10)
C5—C6	1.390 (11)	C22—H22	0.9300
C5—H5	0.9300	C23—C26	1.380 (12)
C6—C7	1.476 (10)	C23—C24	1.402 (10)
C7—N6	1.246 (10)	C23—H23	0.9300
C7—H7	0.9300	C24—C25	1.367 (11)
C8—N5	1.270 (8)	C25—C28	1.379 (11)
C8—C9	1.463 (9)	C25—H25	0.9300
C8—C21ⁱⁱ	1.527 (9)	C26—C27	1.371 (12)
C9—C10	1.367 (10)	C26—H26	0.9300
C9—C14	1.403 (11)	C27—C28	1.394 (11)
C10—C11	1.416 (12)	C27—H27	0.9300
C10—H10	0.9300	C28—C29	1.428 (11)
C11—C12	1.335 (16)	C29—N2	1.144 (10)
C11—H11	0.9300	C44—N1	1.088 (11)
C12—C13	1.379 (16)	F1—Sb1	1.822 (11)
C12—H12	0.9300	F2—Sb1	1.74 (2)
C13—C14	1.383 (12)	F3—Sb1	1.899 (17)
C13—H13	0.9300	F4—Sb1	1.791 (10)
C14—H14	0.9300	F5—Sb1	1.775 (14)
C15—C20	1.374 (10)	F6—Sb1	1.833 (12)
C15—C16	1.387 (11)	N1—Ag1^iv	2.354 (9)
C15—H15	0.9300	N3—N4	1.398 (8)
C16—C17	1.369 (14)	N5—N6	1.402 (8)

N5—Ag1—N3	145.2 (2)	C20—C19—C18	118.0 (8)
N5—Ag1—N1ⁱ	107.5 (3)	C20—C19—H19	121.0
N3—Ag1—N1ⁱ	97.9 (3)	C18—C19—H19	121.0
C2—C1—C6	119.9 (8)	C15—C20—C19	119.4 (7)
C2—C1—H1	120.0	C15—C20—C21	120.8 (7)
C6—C1—H1	120.0	C19—C20—C21	119.8 (7)
C1—C2—C3	120.6 (8)	N3—C21—C20	122.5 (6)
C1—C2—C44	118.3 (8)	N3—C21—C8ⁱⁱⁱ	119.4 (6)
C3—C2—C44	121.0 (8)	C20—C21—C8ⁱⁱⁱ	118.1 (6)
C4—C3—C2	119.3 (8)	N4—C22—C24	124.7 (6)
C4—C3—H3	120.4	N4—C22—H22	117.7
C2—C3—H3	120.4	C24—C22—H22	117.7
C5—C4—C3	120.7 (9)	C26—C23—C24	119.5 (7)
C5—C4—H4	119.6	C26—C23—H23	120.3
C3—C4—H4	119.6	C24—C23—H23	120.3
C4—C5—C6	120.7 (8)	C25—C24—C23	119.2 (7)
C4—C5—H5	119.7	C25—C24—C22	120.9 (7)
C6—C5—H5	119.7	C23—C24—C22	119.7 (7)
C1—C6—C5	118.7 (7)	C24—C25—C28	121.5 (7)
C1—C6—C7	119.6 (7)	C24—C25—H25	119.3
C5—C6—C7	121.7 (7)	C28—C25—H25	119.3
N6—C7—C6	122.4 (7)	C27—C26—C23	120.8 (8)
N6—C7—H7	118.8	C27—C26—H26	119.6
C6—C7—H7	118.8	C23—C26—H26	119.6
N5—C8—C9	120.1 (6)	C26—C27—C28	119.8 (7)
N5—C8—C21ⁱⁱ	120.4 (6)	C26—C27—H27	120.1
C9—C8—C21ⁱⁱ	119.5 (6)	C28—C27—H27	120.1
C10—C9—C14	119.4 (7)	C25—C28—C27	119.2 (7)
C10—C9—C8	120.1 (7)	C25—C28—C29	121.1 (7)
C14—C9—C8	120.4 (7)	C27—C28—C29	119.7 (7)
C9—C10—C11	119.9 (9)	N2—C29—C28	179.0 (9)
C9—C10—H10	120.0	N1—C44—C2	178.1 (11)
C11—C10—H10	120.0	C44—N1—Ag1^iv	170.3 (9)
C12—C11—C10	120.6 (10)	C21—N3—N4	116.5 (5)
C12—C11—H11	119.7	C21—N3—Ag1	123.2 (4)
C10—C11—H11	119.7	N4—N3—Ag1	117.1 (4)
C11—C12—C13	119.7 (9)	C22—N4—N3	116.0 (6)
C11—C12—H12	120.1	C8—N5—N6	116.6 (5)
C13—C12—H12	120.1	C8—N5—Ag1	125.5 (4)
C12—C13—C14	121.4 (10)	N6—N5—Ag1	114.0 (4)
C12—C13—H13	119.3	C7—N6—N5	113.7 (6)
C14—C13—H13	119.3	F2—Sb1—F5	93.5 (8)
C13—C14—C9	118.7 (8)	F2—Sb1—F4	90.6 (7)
C13—C14—H14	120.6	F5—Sb1—F4	93.1 (6)
C9—C14—H14	120.6	F2—Sb1—F1	92.5 (8)
C20—C15—C16	120.7 (8)	F5—Sb1—F1	173.9 (6)
C20—C15—H15	119.6	F4—Sb1—F1	85.7 (5)
C16—C15—H15	119.6	F2—Sb1—F6	90.2 (7)
C17—C16—C15	120.3 (9)	F5—Sb1—F6	84.6 (5)
C17—C16—H16	119.9	F4—Sb1—F6	177.7 (5)
C15—C16—H16	119.9	F1—Sb1—F6	96.4 (5)
C18—C17—C16	119.0 (8)	F2—Sb1—F3	173.9 (8)
C18—C17—H17	120.5	F5—Sb1—F3	80.9 (7)
C16—C17—H17	120.5	F4—Sb1—F3	87.5 (6)
C17—C18—C19	122.6 (9)	F1—Sb1—F3	93.1 (6)
C17—C18—H18	118.7	F6—Sb1—F3	91.5 (6)
C19—C18—H18	118.7

C6—C1—C2—C3	−0.3 (12)	N4—C22—C24—C25	−177.8 (8)
C6—C1—C2—C44	178.9 (7)	N4—C22—C24—C23	6.8 (12)
C1—C2—C3—C4	0.0 (14)	C23—C24—C25—C28	1.4 (12)
C44—C2—C3—C4	−179.2 (9)	C22—C24—C25—C28	−174.0 (7)
C2—C3—C4—C5	0.4 (15)	C24—C23—C26—C27	1.3 (14)
C3—C4—C5—C6	−0.5 (15)	C23—C26—C27—C28	−0.6 (14)
C2—C1—C6—C5	0.2 (11)	C24—C25—C28—C27	−0.6 (12)
C2—C1—C6—C7	−179.1 (7)	C24—C25—C28—C29	178.3 (7)
C4—C5—C6—C1	0.2 (12)	C26—C27—C28—C25	0.2 (12)
C4—C5—C6—C7	179.5 (8)	C26—C27—C28—C29	−178.8 (8)
C1—C6—C7—N6	−173.4 (7)	C25—C28—C29—N2	178 (100)
C5—C6—C7—N6	7.4 (12)	C27—C28—C29—N2	−3 (59)
N5—C8—C9—C10	−39.2 (10)	C1—C2—C44—N1	−114 (34)
C21ⁱⁱ—C8—C9—C10	138.3 (7)	C3—C2—C44—N1	65 (35)
N5—C8—C9—C14	142.7 (8)	C2—C44—N1—Ag1^iv	−150 (31)
C21ⁱⁱ—C8—C9—C14	−39.8 (10)	C20—C21—N3—N4	−174.7 (6)
C14—C9—C10—C11	−2.0 (13)	C8ⁱⁱⁱ—C21—N3—N4	7.9 (9)
C8—C9—C10—C11	179.9 (8)	C20—C21—N3—Ag1	26.0 (9)
C9—C10—C11—C12	−0.6 (16)	C8ⁱⁱⁱ—C21—N3—Ag1	−151.5 (5)
C10—C11—C12—C13	0.1 (18)	N5—Ag1—N3—C21	−105.2 (6)
C11—C12—C13—C14	3.2 (18)	N1ⁱ—Ag1—N3—C21	31.9 (6)
C12—C13—C14—C9	−5.8 (16)	N5—Ag1—N3—N4	95.6 (5)
C10—C9—C14—C13	5.1 (13)	N1ⁱ—Ag1—N3—N4	−127.2 (5)
C8—C9—C14—C13	−176.8 (8)	C24—C22—N4—N3	−176.3 (7)
C20—C15—C16—C17	0.3 (13)	C21—N3—N4—C22	−130.8 (7)
C15—C16—C17—C18	−1.0 (13)	Ag1—N3—N4—C22	29.8 (8)
C16—C17—C18—C19	0.4 (13)	C9—C8—N5—N6	178.7 (6)
C17—C18—C19—C20	1.0 (12)	C21ⁱⁱ—C8—N5—N6	1.2 (9)
C16—C15—C20—C19	1.1 (11)	C9—C8—N5—Ag1	−24.7 (9)
C16—C15—C20—C21	−179.1 (7)	C21ⁱⁱ—C8—N5—Ag1	157.7 (5)
C18—C19—C20—C15	−1.7 (10)	N3—Ag1—N5—C8	34.6 (7)
C18—C19—C20—C21	178.5 (6)	N1ⁱ—Ag1—N5—C8	−100.4 (6)
C15—C20—C21—N3	30.8 (10)	N3—Ag1—N5—N6	−168.3 (4)
C19—C20—C21—N3	−149.4 (7)	N1ⁱ—Ag1—N5—N6	56.6 (5)
C15—C20—C21—C8ⁱⁱⁱ	−151.7 (6)	C6—C7—N6—N5	−177.2 (6)
C19—C20—C21—C8ⁱⁱⁱ	28.1 (9)	C8—N5—N6—C7	−126.7 (7)
C26—C23—C24—C25	−1.7 (12)	Ag1—N5—N6—C7	74.1 (7)
C26—C23—C24—C22	173.8 (8)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, −y+3/2, z+1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Ag(C₃₀H₂₀N₆)][SbF₆]
M_r	808.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	15.1652 (9), 14.6022 (9), 14.0711 (9)
β (°)	94.257 (1)
V (Å³)	3107.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.57
Crystal size (mm)	0.35 × 0.14 × 0.08

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.610, 0.885
No. of measured, independent and observed [I > 2σ(I)] reflections	15863, 5885, 4340
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.071, 0.223, 1.05
No. of reflections	5885
No. of parameters	367
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.48, −0.94

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Bruker, 2001).

Selected geometric parameters (Å, º) top

Ag1—N5	2.287 (6)	Ag1—N1ⁱ	2.354 (9)
Ag1—N3	2.334 (5)

N5—Ag1—N3	145.2 (2)	N3—Ag1—N1ⁱ	97.9 (3)
N5—Ag1—N1ⁱ	107.5 (3)

Symmetry code: (i) −x+1, y−1/2, −z+3/2.

References

Bruker (1997). SMART (Version 5.6) and SAINT (Version 5.06A), Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2001). SHELXTL. Version 6.12. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. Version 2.10. University of Göttingen, Germany. Google Scholar
Wei, K.-J., Ni, J., Gao, J., Liu, Y.-Z. & Liu, Q.-L. (2007). Eur. J. Inorg. Chem. pp. 3868–3880. Web of Science CSD CrossRef Google Scholar

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