Poly[[{μ4-1,2-bis­[(3-cyano­benzyl­idene)hydrazono]-1,2-diphenyl­ethane}bis­(trifluoro­methane­sulfonato)disilver(I)] benzene solvate]

Hong Liang Li

doi:10.1107/S1600536808012853

. 2008 May 7;64(Pt 6):m785. doi: 10.1107/S1600536808012853

Poly[[{μ₄-1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane}bis(trifluoromethanesulfonato)disilver(I)] benzene solvate]

Hong Liang Li ^a,^*

PMCID: PMC2961533 PMID: 21202474

Abstract

In the title complex, {[Ag₂(CF₃O₃S)₂(C₃₀H₂₀N₆)]·C₆H₆}_n, the two independent Ag^I ions are each coordinated by two N atoms and one O atom in a ‘T-shaped’ geometry. In the crystal structure, 1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane ligands act as bridging ligands and each coordinates to four Ag^I ions, resulting in a one-dimensional chain structure. The crystal structure is stabilized by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For a related structure, see: Liu (2008 ▶).

Experimental

Crystal data

[Ag₂(CF₃O₃S)₂(C₃₀H₂₀N₆)]·C₆H₆
M _r = 1056.51
Monoclinic,
a = 10.8308 (9) Å
b = 22.0864 (18) Å
c = 17.0949 (13) Å
β = 90.420 (2)°
V = 4089.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.14 mm⁻¹
T = 298 (2) K
0.33 × 0.23 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.705, T _max = 0.875
23919 measured reflections
8891 independent reflections
6637 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.134
S = 1.04
8891 reflections
541 parameters
H-atom parameters constrained
Δρ_max = 1.16 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012853/lh2619sup1.cif

e-64-0m785-sup1.cif^{(30.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012853/lh2619Isup2.hkl

e-64-0m785-Isup2.hkl^{(434.9KB, hkl)}

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

Table 1. Selected geometric parameters (Å, °).

Ag1—N4ⁱ	2.196 (3)
Ag1—N5	2.249 (3)
Ag1—O1	2.568 (3)
Ag2—N3ⁱⁱ	2.169 (3)
Ag2—N1	2.217 (3)
Ag2—O4	2.592 (3)

Open in a new tab

N4ⁱ—Ag1—N5	165.35 (12)
N4ⁱ—Ag1—O1	85.26 (13)
N5—Ag1—O1	108.59 (11)
N3ⁱⁱ—Ag2—N1	157.73 (13)
N3ⁱⁱ—Ag2—O4	94.85 (11)
N1—Ag2—O4	103.97 (10)

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) .

Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C33—H33⋯O6ⁱ	0.93	2.57	3.486 (5)	168
C26—H26⋯O3ⁱⁱⁱ	0.93	2.52	3.406 (5)	159
C22—H22⋯O5ⁱ	0.93	2.56	3.382 (4)	148
C6—H6⋯O5^iv	0.93	2.47	3.178 (4)	133

Open in a new tab

Symmetry codes: (i) Inline graphic ; (iii) ; (iv) .

supplementary crystallographic information

Comment

1,2-Bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane is a useful multi-dentate ligand and a three-dimensional structure was recently obtained (Liu 2008) of the compound formed by the reaction of this ligand with AgSbF₆. The title one-dimensional chain structure (I) was formed when the ligand was reacted with silver(I)trifluoromethanesulfonate. It appears that the counter anions of Ag(I) complexes play a key role in the type of crystal structures formed with reactions of 1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane as a ligand. Herein the title crystal structure is reported.

Fig. 1 and Table 1 reveal that the coordination geometry for Ag1 and Ag2 is a 'T-shape' formed by two N atoms and a O atom, in which the two N atoms come from cyano and hydrazo groups, respectively, and the O atom is from trifluoromethanesulfonate ligand. In the crystal structure each 1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane ligand functions as tetradentate bridging ligand and coordinates to four Ag^I cations, which leads to the formation of a one-dimensional chain structure as shown in Fig. 2. In this one-dimensional chain there is 24-membered ring that includes two Ag^I ions. In addition, there are weak C—H···O non-classic hydrogen bonds in the chain and between neighboring chains (see Fig. 3 and Table 2).

Experimental

8 ml benzene solution of AgSO₃CF₃ (0.0128 g, 0.05 mmol) was added very slowly on the 8 ml dichloromethane solution of 1,2-bis[(3-cyanobenzylidene)hydrazono]-1,2-diphenylethane (0.0093 g, 0.02 mmol). Colorless single crystals were obtained after the solution had been allowed to stand at room temperature for one month.