Bis[N′-(3-cyano­benzyl­idene)isonicotino­hydrazide]silver(I) trifluoro­acetate

Niu, C.-Y.; Zhang, H.-Y.; Dang, Y.-L.; Kou, C.-H.

doi:10.1107/S1600536809029183

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page m1029

doi:10.1107/S1600536809029183

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Bis[N′-(3-cyanobenzylidene)isonicotinohydrazide]silver(I) trifluoroacetate

Cao-Yuan Niu,^a ^* Hai-Yan Zhang,^a Yu-Li Dang ^a and Chun-Hong Kou ^a

^aCollege of Sciences, Henan Agricultural University, Zhengzhou 450002, People's Republic of China
^*Correspondence e-mail: niu_cy2000@yahoo.com.cn

(Received 15 July 2009; accepted 23 July 2009; online 8 August 2009)

In the title compound, [Ag(C₁₄H₁₀N₄O)₂]CF₃CO₂, the Ag^I ion is coordinated by two N atoms of the pyridine rings of two N′-(3-cyanobenzylidene)isonicotinohydrazide ligands in a nearly linear geometry. In the crystal structure, a combination of close contacts formed via Ag⋯N interactions [Ag⋯N = 3.098 (2) and 3.261 (2) Å] from symmetry-related molecules and intermolecular N—H⋯O hydrogen bonds between CF₃CO₂⁻ anions and the hydrazone groups of two ligands give rise to chains. Furthermore, there are Ag⋯O interactions with a separation of 2.765 (2) Å between chains. The F atoms of the CF₃CO₂⁻ anion are disordered over two sites with refined occupancies of 0.593 (5) and 0.407 (5).

Related literature

For related silver complexes, see: Dong et al. (2004 ); Niu et al. (2008 , 2009 ); Sumby & Hardie (2005 ); Abu-Youssef et al. (2007 ); Zheng et al. (2003 ).

Experimental

Crystal data

[Ag(C₁₄H₁₀N₄O)₂]C₂F₃O₂
M_r = 721.41
Triclinic, $[P \overline 1]$
a = 7.5345 (14) Å
b = 13.744 (3) Å
c = 14.098 (3) Å
α = 86.562 (3)°
β = 88.126 (3)°
γ = 83.792 (3)°
V = 1448.2 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 173 K
0.32 × 0.22 × 0.17 mm

Data collection

Bruker APEXII CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.791, T_max = 0.881
8015 measured reflections
5306 independent reflections
4046 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.137
S = 1.03
5306 reflections
443 parameters
48 restraints
H-atom parameters constrained
Δρ_max = 0.95 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—N5	2.143 (3)
Ag1—N1	2.147 (3)

N5—Ag1—N1	174.20 (11)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H40⋯O4ⁱ	0.88	1.93	2.805 (4)	172
N6—H39⋯O3ⁱⁱ	0.90	2.13	2.936 (4)	149
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x, -y+1, -z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002 ); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029183/lh2867sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029183/lh2867Isup2.hkl

checkCIF report

Comment top

Silver coordination complexes with pyridyl organic ligands are of great interests for their utilities in fluorescent materials and antibiotic aspects (Dong et al., 2004; Abu-Youssef, et al., 2007). In the title compound, (I), the central Ag^I ion is coordinated by two nitrogen atoms from two pyridine rings of two different ligands, defining a slightly distorted linear coordination geometry (Fig. 1). Coordinating bond distances and angle around metal center are shown in Table 1. In the crystal structure, there are N—H···O hydrogen bonds between the hydrazone groups of 3-cyanobenzylidene isonicotinohydrazide ligands and CF₃CO₂^- anions (Table 2). In addition, there are weak Ag···N interactions between two neighbouring silver monomers with separations of 3.098 (2) and 3.261 (2) Å and Ag···O interactions between two neighbouring silver monomers with separations of 2.765 (2) Å. Hydrogen bonds and Ag···N interactions link parallel silver monomers together to construct one-dimensional chains (Fig. 2) and Ag···O interactions contribute to the three-dimensional structure.

Related literature top

For related silver complexes, see: Dong et al. (2004); Niu et al. (2008, 2009); Sumby & Hardie (2005); Abu-Youssef et al. (2007); Zheng et al. (2003).

Experimental top

A solution of AgCF₃CO₂ (0.022 g, 0.1 mmol) in CH₃OH (10 ml) was carefully layered on a CH₃OH/CHCl₃ solution (5 ml/10 ml) of 3-Cyanobenzylidene isonicotinohydrazide (0.025 g, 0.1 mmol) in a straight glass tube. About ten days later, colourless single crystals suitable for X-ray analysis were obtained (yield about 43%).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1994); data reduction: SAINT (Siemens, 1994); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. In the anion, the dashed lines indicate the minor component of disorder.
	Fig. 2. Part of the the one-dimensional chain formed via intermolecular hydrogen bonds indicated by green dashed lines and Ag···N interactions indicated by pink dashed lines.

Bis[N'-(3-cyanobenzylidene)isonicotinohydrazide]silver(I) trifluoroacetate top

Crystal data top

[Ag(C₁₄H₁₀N₄O)₂]C₂F₃O₂	Z = 2
M_r = 721.41	F(000) = 724
Triclinic, P1	D_x = 1.654 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5345 (14) Å	Cell parameters from 2885 reflections
b = 13.744 (3) Å	θ = 2.1–25.5°
c = 14.098 (3) Å	µ = 0.77 mm⁻¹
α = 86.562 (3)°	T = 173 K
β = 88.126 (3)°	Needle, yellow
γ = 83.792 (3)°	0.32 × 0.22 × 0.17 mm
V = 1448.2 (5) Å³

Data collection top

Bruker APEXII CCD detector diffractometer	5306 independent reflections
Radiation source: fine-focus sealed tube	4046 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.791, T_max = 0.881	k = −16→16
8015 measured reflections	l = −8→17

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0871P)² + 0.05P] where P = (F_o² + 2F_c²)/3
5306 reflections	(Δ/σ)_max = 0.001
443 parameters	Δρ_max = 0.95 e Å⁻³
48 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Ag(C₁₄H₁₀N₄O)₂]C₂F₃O₂	γ = 83.792 (3)°
M_r = 721.41	V = 1448.2 (5) Å³
Triclinic, P1	Z = 2
a = 7.5345 (14) Å	Mo Kα radiation
b = 13.744 (3) Å	µ = 0.77 mm⁻¹
c = 14.098 (3) Å	T = 173 K
α = 86.562 (3)°	0.32 × 0.22 × 0.17 mm
β = 88.126 (3)°

Data collection top

Bruker APEXII CCD detector diffractometer	5306 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4046 reflections with I > 2σ(I)
T_min = 0.791, T_max = 0.881	R_int = 0.025
8015 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	48 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.03	Δρ_max = 0.95 e Å⁻³
5306 reflections	Δρ_min = −0.83 e Å⁻³
443 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	Occ. (<1)
Ag1	0.07174 (4)	0.80139 (2)	0.31966 (2)	0.07153 (17)
N1	0.1905 (4)	0.8820 (2)	0.4222 (2)	0.0511 (7)
N2	0.4458 (4)	1.0110 (2)	0.71224 (19)	0.0467 (6)
H40	0.4975	0.9505	0.7165	0.056*
N3	0.4965 (4)	1.0684 (2)	0.78081 (19)	0.0499 (7)
N4	0.9740 (5)	0.9994 (3)	1.2069 (2)	0.0771 (10)
N5	−0.0205 (4)	0.7130 (2)	0.2151 (2)	0.0542 (7)
N6	−0.3086 (4)	0.5740 (2)	−0.06091 (19)	0.0499 (7)
H39	−0.3230	0.6397	−0.0717	0.060*
N7	−0.3701 (4)	0.5149 (2)	−0.12433 (19)	0.0473 (6)
N8	−0.8578 (6)	0.5997 (3)	−0.5468 (3)	0.0829 (11)
O1	0.2840 (4)	1.14121 (17)	0.63867 (18)	0.0630 (7)
O2	−0.2138 (4)	0.44400 (17)	0.03838 (17)	0.0601 (6)
O3	0.2518 (5)	0.2337 (2)	0.1519 (2)	0.0957 (11)
O4	0.3698 (5)	0.1775 (2)	0.2890 (2)	0.0950 (11)
C1	0.2540 (6)	0.8390 (3)	0.5037 (3)	0.0623 (10)
H28	0.2629	0.7695	0.5111	0.075*
C2	0.3069 (5)	0.8889 (3)	0.5766 (3)	0.0577 (9)
H29	0.3509	0.8547	0.6331	0.069*
C3	0.2955 (4)	0.9898 (2)	0.5673 (2)	0.0413 (7)
C4	0.2324 (4)	1.0347 (2)	0.4829 (2)	0.0480 (8)
H30	0.2240	1.1040	0.4733	0.058*
C5	0.1822 (4)	0.9791 (3)	0.4135 (2)	0.0492 (8)
H31	0.1392	1.0115	0.3560	0.059*
C6	0.3404 (4)	1.0549 (2)	0.6427 (2)	0.0470 (8)
C7	0.5898 (4)	1.0245 (3)	0.8475 (2)	0.0488 (8)
H32	0.6173	0.9553	0.8495	0.059*
C8	0.6539 (4)	1.0815 (2)	0.9204 (2)	0.0461 (7)
C9	0.6270 (5)	1.1842 (3)	0.9143 (3)	0.0606 (10)
H33	0.5639	1.2171	0.8623	0.073*
C10	0.6902 (6)	1.2380 (3)	0.9820 (3)	0.0748 (12)
H34	0.6709	1.3075	0.9768	0.090*
C11	0.7812 (6)	1.1916 (3)	1.0576 (3)	0.0672 (11)
H35	0.8269	1.2289	1.1040	0.081*
C12	0.8062 (5)	1.0904 (3)	1.0659 (3)	0.0545 (9)
C13	0.7428 (5)	1.0354 (3)	0.9974 (2)	0.0481 (8)
H36	0.7606	0.9658	1.0037	0.058*
C14	0.9005 (5)	1.0402 (3)	1.1449 (3)	0.0603 (9)
C15	−0.1106 (6)	0.7536 (3)	0.1400 (3)	0.0700 (11)
H22	−0.1284	0.8231	0.1327	0.084*
C16	−0.1786 (5)	0.7013 (3)	0.0732 (3)	0.0590 (9)
H21	−0.2389	0.7340	0.0203	0.071*
C17	−0.1585 (4)	0.6002 (2)	0.0834 (2)	0.0417 (7)
C18	−0.0668 (5)	0.5584 (2)	0.1616 (2)	0.0499 (8)
H20	−0.0499	0.4890	0.1715	0.060*
C19	−0.0005 (5)	0.6156 (3)	0.2244 (2)	0.0530 (8)
H19	0.0627	0.5847	0.2772	0.064*
C20	−0.2274 (4)	0.5316 (2)	0.0187 (2)	0.0442 (7)
C21	−0.4550 (5)	0.5585 (3)	−0.1937 (2)	0.0508 (8)
H23	−0.4746	0.6280	−0.1976	0.061*
C22	−0.5228 (4)	0.5035 (2)	−0.2675 (2)	0.0461 (7)
C23	−0.4960 (5)	0.4015 (3)	−0.2652 (3)	0.0542 (9)
H24	−0.4279	0.3667	−0.2161	0.065*
C24	−0.5667 (6)	0.3510 (3)	−0.3331 (3)	0.0628 (10)
H25	−0.5495	0.2813	−0.3297	0.075*
C25	−0.6625 (5)	0.3998 (3)	−0.4062 (3)	0.0591 (9)
H26	−0.7109	0.3643	−0.4532	0.071*
C26	−0.6874 (5)	0.5011 (3)	−0.4105 (2)	0.0533 (8)
C27	−0.6184 (5)	0.5528 (3)	−0.3409 (2)	0.0510 (8)
H27	−0.6372	0.6224	−0.3438	0.061*
C28	−0.7845 (5)	0.5554 (3)	−0.4867 (3)	0.0626 (10)
C29	0.2595 (5)	0.2239 (3)	0.2380 (3)	0.0611 (10)
C30	0.1058 (7)	0.2780 (3)	0.2934 (4)	0.0814 (13)
F1	0.1449 (15)	0.3562 (8)	0.3268 (9)	0.132 (5)	0.593 (15)
F2	0.0334 (14)	0.2268 (7)	0.3564 (11)	0.156 (6)	0.593 (15)
F3	−0.0247 (13)	0.3127 (8)	0.2334 (8)	0.144 (5)	0.593 (15)
F1'	0.141 (3)	0.2689 (11)	0.3907 (7)	0.145 (6)	0.407 (15)
F2'	−0.0425 (19)	0.2452 (15)	0.2912 (13)	0.153 (7)	0.407 (15)
F3'	0.093 (2)	0.3702 (7)	0.2843 (13)	0.132 (7)	0.407 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0812 (3)	0.0767 (3)	0.0630 (2)	−0.01527 (17)	−0.01994 (17)	−0.03412 (17)
N1	0.0622 (17)	0.0518 (17)	0.0435 (16)	−0.0139 (13)	−0.0157 (13)	−0.0136 (12)
N2	0.0567 (15)	0.0441 (15)	0.0412 (15)	−0.0050 (12)	−0.0149 (12)	−0.0128 (11)
N3	0.0594 (16)	0.0477 (16)	0.0452 (16)	−0.0078 (13)	−0.0152 (13)	−0.0137 (12)
N4	0.079 (2)	0.103 (3)	0.050 (2)	−0.011 (2)	−0.0193 (18)	−0.0021 (19)
N5	0.0699 (18)	0.0492 (18)	0.0460 (16)	−0.0064 (14)	−0.0174 (14)	−0.0158 (13)
N6	0.0672 (17)	0.0418 (15)	0.0435 (15)	−0.0091 (13)	−0.0175 (13)	−0.0097 (12)
N7	0.0606 (16)	0.0450 (15)	0.0390 (15)	−0.0093 (12)	−0.0137 (13)	−0.0115 (12)
N8	0.103 (3)	0.089 (3)	0.061 (2)	−0.019 (2)	−0.037 (2)	0.003 (2)
O1	0.0821 (17)	0.0408 (14)	0.0686 (17)	−0.0027 (12)	−0.0307 (13)	−0.0155 (11)
O2	0.0886 (18)	0.0389 (14)	0.0550 (15)	−0.0067 (12)	−0.0241 (13)	−0.0092 (10)
O3	0.162 (3)	0.074 (2)	0.0531 (18)	−0.024 (2)	−0.0202 (19)	0.0046 (15)
O4	0.110 (2)	0.078 (2)	0.093 (2)	0.0287 (18)	−0.046 (2)	−0.0184 (17)
C1	0.085 (3)	0.042 (2)	0.064 (2)	−0.0097 (18)	−0.029 (2)	−0.0104 (17)
C2	0.084 (2)	0.0413 (19)	0.051 (2)	−0.0106 (17)	−0.0296 (18)	−0.0026 (15)
C3	0.0457 (16)	0.0413 (17)	0.0390 (16)	−0.0081 (13)	−0.0106 (13)	−0.0088 (13)
C4	0.0597 (19)	0.0429 (18)	0.0431 (18)	−0.0100 (15)	−0.0137 (15)	−0.0017 (14)
C5	0.0581 (19)	0.054 (2)	0.0377 (17)	−0.0124 (16)	−0.0144 (15)	−0.0001 (14)
C6	0.0553 (18)	0.0424 (19)	0.0459 (19)	−0.0102 (15)	−0.0130 (15)	−0.0101 (14)
C7	0.0591 (19)	0.0445 (19)	0.0445 (18)	−0.0062 (15)	−0.0095 (15)	−0.0106 (14)
C8	0.0538 (18)	0.0478 (19)	0.0389 (17)	−0.0095 (14)	−0.0117 (14)	−0.0084 (14)
C9	0.081 (3)	0.045 (2)	0.057 (2)	−0.0056 (17)	−0.0252 (19)	−0.0060 (16)
C10	0.099 (3)	0.047 (2)	0.082 (3)	−0.012 (2)	−0.032 (2)	−0.0144 (19)
C11	0.081 (3)	0.061 (3)	0.065 (3)	−0.016 (2)	−0.023 (2)	−0.0222 (19)
C12	0.058 (2)	0.066 (2)	0.0423 (19)	−0.0110 (17)	−0.0096 (16)	−0.0090 (16)
C13	0.0570 (19)	0.0456 (19)	0.0430 (18)	−0.0064 (15)	−0.0093 (15)	−0.0058 (14)
C14	0.062 (2)	0.076 (3)	0.046 (2)	−0.0118 (19)	−0.0089 (18)	−0.0125 (18)
C15	0.106 (3)	0.041 (2)	0.066 (2)	−0.008 (2)	−0.035 (2)	−0.0093 (17)
C16	0.087 (3)	0.0405 (19)	0.051 (2)	−0.0024 (17)	−0.0313 (19)	−0.0053 (15)
C17	0.0482 (17)	0.0408 (17)	0.0362 (16)	−0.0028 (13)	−0.0035 (13)	−0.0059 (13)
C18	0.068 (2)	0.0406 (18)	0.0413 (18)	0.0011 (15)	−0.0147 (15)	−0.0067 (14)
C19	0.062 (2)	0.056 (2)	0.0422 (18)	−0.0019 (16)	−0.0168 (15)	−0.0095 (15)
C20	0.0528 (18)	0.0416 (19)	0.0394 (17)	−0.0034 (14)	−0.0096 (14)	−0.0105 (13)
C21	0.064 (2)	0.0436 (19)	0.047 (2)	−0.0095 (15)	−0.0115 (16)	−0.0071 (15)
C22	0.0551 (18)	0.0457 (19)	0.0403 (17)	−0.0137 (15)	−0.0080 (14)	−0.0072 (14)
C23	0.065 (2)	0.046 (2)	0.054 (2)	−0.0105 (16)	−0.0137 (17)	−0.0035 (15)
C24	0.077 (2)	0.047 (2)	0.068 (3)	−0.0150 (18)	−0.013 (2)	−0.0151 (17)
C25	0.071 (2)	0.057 (2)	0.054 (2)	−0.0169 (18)	−0.0123 (18)	−0.0179 (17)
C26	0.059 (2)	0.061 (2)	0.0434 (19)	−0.0170 (17)	−0.0117 (15)	−0.0073 (16)
C27	0.064 (2)	0.0462 (19)	0.0454 (19)	−0.0128 (16)	−0.0148 (16)	−0.0039 (14)
C28	0.077 (2)	0.064 (2)	0.052 (2)	−0.019 (2)	−0.0222 (19)	−0.0061 (18)
C29	0.086 (3)	0.0379 (19)	0.061 (2)	−0.0105 (18)	−0.021 (2)	0.0021 (16)
C30	0.094 (3)	0.052 (3)	0.095 (4)	−0.002 (2)	−0.009 (3)	0.010 (3)
F1	0.149 (7)	0.122 (9)	0.135 (8)	−0.021 (6)	0.023 (6)	−0.076 (7)
F2	0.131 (7)	0.126 (7)	0.189 (11)	0.019 (5)	0.075 (7)	0.075 (8)
F3	0.124 (6)	0.121 (7)	0.180 (8)	0.056 (5)	−0.066 (6)	−0.036 (6)
F1'	0.234 (14)	0.121 (10)	0.067 (5)	0.047 (9)	−0.009 (7)	−0.023 (6)
F2'	0.114 (8)	0.184 (15)	0.171 (13)	−0.061 (9)	0.031 (8)	−0.029 (11)
F3'	0.171 (12)	0.037 (5)	0.168 (13)	0.038 (6)	0.048 (9)	0.032 (7)

Geometric parameters (Å, º) top

Ag1—N5	2.143 (3)	C9—C10	1.369 (5)
Ag1—N1	2.147 (3)	C9—H33	0.9500
N1—C5	1.327 (4)	C10—C11	1.372 (6)
N1—C1	1.338 (5)	C10—H34	0.9500
N2—C6	1.353 (4)	C11—C12	1.381 (6)
N2—N3	1.372 (4)	C11—H35	0.9500
N2—H40	0.8793	C12—C13	1.388 (5)
N3—C7	1.275 (4)	C12—C14	1.440 (6)
N4—C14	1.136 (5)	C13—H36	0.9500
N5—C19	1.330 (5)	C15—C16	1.363 (5)
N5—C15	1.338 (5)	C15—H22	0.9500
N6—C20	1.364 (4)	C16—C17	1.381 (5)
N6—N7	1.367 (4)	C16—H21	0.9500
N6—H39	0.9025	C17—C18	1.383 (4)
N7—C21	1.270 (4)	C17—C20	1.493 (4)
N8—C28	1.135 (5)	C18—C19	1.360 (5)
O1—C6	1.215 (4)	C18—H20	0.9500
O2—C20	1.214 (4)	C19—H19	0.9500
O3—C29	1.216 (4)	C21—C22	1.458 (5)
O4—C29	1.218 (4)	C21—H23	0.9500
C1—C2	1.363 (5)	C22—C27	1.381 (5)
C1—H28	0.9500	C22—C23	1.393 (5)
C2—C3	1.378 (5)	C23—C24	1.369 (5)
C2—H29	0.9500	C23—H24	0.9500
C3—C4	1.381 (4)	C24—C25	1.376 (5)
C3—C6	1.500 (4)	C24—H25	0.9500
C4—C5	1.365 (5)	C25—C26	1.382 (5)
C4—H30	0.9500	C25—H26	0.9500
C5—H31	0.9500	C26—C27	1.391 (5)
C7—C8	1.454 (4)	C26—C28	1.443 (5)
C7—H32	0.9500	C27—H27	0.9500
C8—C13	1.380 (5)	C29—C30	1.526 (7)
C8—C9	1.402 (5)

N5—Ag1—N1	174.20 (11)	C11—C12—C14	120.6 (3)
C5—N1—C1	116.6 (3)	C13—C12—C14	118.9 (3)
C5—N1—Ag1	121.0 (2)	C8—C13—C12	120.1 (3)
C1—N1—Ag1	121.8 (2)	C8—C13—H36	119.9
C6—N2—N3	117.8 (3)	C12—C13—H36	119.9
C6—N2—H40	128.2	N4—C14—C12	179.0 (5)
N3—N2—H40	113.6	N5—C15—C16	123.9 (3)
C7—N3—N2	116.5 (3)	N5—C15—H22	118.0
C19—N5—C15	116.7 (3)	C16—C15—H22	118.0
C19—N5—Ag1	121.9 (2)	C15—C16—C17	119.2 (3)
C15—N5—Ag1	121.2 (2)	C15—C16—H21	120.4
C20—N6—N7	118.7 (3)	C17—C16—H21	120.4
C20—N6—H39	121.2	C16—C17—C18	116.8 (3)
N7—N6—H39	120.1	C16—C17—C20	126.4 (3)
C21—N7—N6	115.9 (3)	C18—C17—C20	116.8 (3)
N1—C1—C2	123.9 (3)	C19—C18—C17	120.6 (3)
N1—C1—H28	118.0	C19—C18—H20	119.7
C2—C1—H28	118.0	C17—C18—H20	119.7
C1—C2—C3	119.0 (3)	N5—C19—C18	122.8 (3)
C1—C2—H29	120.5	N5—C19—H19	118.6
C3—C2—H29	120.5	C18—C19—H19	118.6
C2—C3—C4	117.5 (3)	O2—C20—N6	123.2 (3)
C2—C3—C6	125.2 (3)	O2—C20—C17	120.8 (3)
C4—C3—C6	117.3 (3)	N6—C20—C17	115.9 (3)
C5—C4—C3	119.7 (3)	N7—C21—C22	121.1 (3)
C5—C4—H30	120.1	N7—C21—H23	119.5
C3—C4—H30	120.1	C22—C21—H23	119.5
N1—C5—C4	123.3 (3)	C27—C22—C23	118.7 (3)
N1—C5—H31	118.4	C27—C22—C21	119.8 (3)
C4—C5—H31	118.4	C23—C22—C21	121.5 (3)
O1—C6—N2	124.1 (3)	C24—C23—C22	120.7 (3)
O1—C6—C3	120.2 (3)	C24—C23—H24	119.6
N2—C6—C3	115.6 (3)	C22—C23—H24	119.6
N3—C7—C8	119.3 (3)	C23—C24—C25	120.8 (3)
N3—C7—H32	120.4	C23—C24—H25	119.6
C8—C7—H32	120.4	C25—C24—H25	119.6
C13—C8—C9	118.5 (3)	C24—C25—C26	119.3 (3)
C13—C8—C7	120.5 (3)	C24—C25—H26	120.4
C9—C8—C7	121.0 (3)	C26—C25—H26	120.4
C10—C9—C8	121.0 (3)	C25—C26—C27	120.2 (3)
C10—C9—H33	119.5	C25—C26—C28	121.2 (3)
C8—C9—H33	119.5	C27—C26—C28	118.6 (3)
C9—C10—C11	120.1 (4)	C22—C27—C26	120.3 (3)
C9—C10—H34	119.9	C22—C27—H27	119.8
C11—C10—H34	119.9	C26—C27—H27	119.8
C10—C11—C12	119.8 (3)	N8—C28—C26	178.3 (4)
C10—C11—H35	120.1	O3—C29—O4	131.0 (4)
C12—C11—H35	120.1	O3—C29—C30	115.8 (4)
C11—C12—C13	120.5 (3)	O4—C29—C30	113.3 (4)

N5—Ag1—N1—C5	122.8 (10)	C14—C12—C13—C8	−179.2 (3)
N5—Ag1—N1—C1	−66.4 (11)	C11—C12—C14—N4	166 (27)
C6—N2—N3—C7	177.3 (3)	C13—C12—C14—N4	−15 (28)
N1—Ag1—N5—C19	56.5 (11)	C19—N5—C15—C16	−1.2 (7)
N1—Ag1—N5—C15	−127.5 (10)	Ag1—N5—C15—C16	−177.4 (4)
C20—N6—N7—C21	175.5 (3)	N5—C15—C16—C17	1.6 (7)
C5—N1—C1—C2	1.0 (6)	C15—C16—C17—C18	−0.9 (6)
Ag1—N1—C1—C2	−170.2 (3)	C15—C16—C17—C20	178.6 (4)
N1—C1—C2—C3	−0.1 (7)	C16—C17—C18—C19	−0.1 (5)
C1—C2—C3—C4	−0.8 (6)	C20—C17—C18—C19	−179.6 (3)
C1—C2—C3—C6	177.1 (4)	C15—N5—C19—C18	0.1 (5)
C2—C3—C4—C5	0.9 (5)	Ag1—N5—C19—C18	176.3 (3)
C6—C3—C4—C5	−177.2 (3)	C17—C18—C19—N5	0.5 (6)
C1—N1—C5—C4	−0.9 (5)	N7—N6—C20—O2	−3.4 (5)
Ag1—N1—C5—C4	170.4 (3)	N7—N6—C20—C17	178.2 (3)
C3—C4—C5—N1	0.0 (5)	C16—C17—C20—O2	−174.3 (4)
N3—N2—C6—O1	−2.0 (5)	C18—C17—C20—O2	5.1 (5)
N3—N2—C6—C3	177.5 (3)	C16—C17—C20—N6	4.1 (5)
C2—C3—C6—O1	−160.7 (4)	C18—C17—C20—N6	−176.4 (3)
C4—C3—C6—O1	17.1 (5)	N6—N7—C21—C22	178.3 (3)
C2—C3—C6—N2	19.7 (5)	N7—C21—C22—C27	178.4 (3)
C4—C3—C6—N2	−162.4 (3)	N7—C21—C22—C23	−0.6 (5)
N2—N3—C7—C8	177.6 (3)	C27—C22—C23—C24	−1.6 (5)
N3—C7—C8—C13	174.7 (3)	C21—C22—C23—C24	177.4 (3)
N3—C7—C8—C9	−5.2 (5)	C22—C23—C24—C25	1.5 (6)
C13—C8—C9—C10	1.2 (6)	C23—C24—C25—C26	−0.2 (6)
C7—C8—C9—C10	−178.8 (4)	C24—C25—C26—C27	−0.9 (6)
C8—C9—C10—C11	−0.1 (7)	C24—C25—C26—C28	179.1 (4)
C9—C10—C11—C12	−1.1 (7)	C23—C22—C27—C26	0.5 (5)
C10—C11—C12—C13	1.2 (6)	C21—C22—C27—C26	−178.6 (3)
C10—C11—C12—C14	−179.6 (4)	C25—C26—C27—C22	0.8 (5)
C9—C8—C13—C12	−1.1 (5)	C28—C26—C27—C22	−179.2 (3)
C7—C8—C13—C12	178.9 (3)	C25—C26—C28—N8	−134 (17)
C11—C12—C13—C8	−0.1 (6)	C27—C26—C28—N8	46 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H40···O4ⁱ	0.88	1.93	2.805 (4)	172
N6—H39···O3ⁱⁱ	0.90	2.13	2.936 (4)	149

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₄H₁₀N₄O)₂]C₂F₃O₂
M_r	721.41
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	7.5345 (14), 13.744 (3), 14.098 (3)
α, β, γ (°)	86.562 (3), 88.126 (3), 83.792 (3)
V (Å³)	1448.2 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.32 × 0.22 × 0.17

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.791, 0.881
No. of measured, independent and observed [I > 2σ(I)] reflections	8015, 5306, 4046
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.137, 1.03
No. of reflections	5306
No. of parameters	443
No. of restraints	48
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.95, −0.83

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1994), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2005).

Selected geometric parameters (Å, º) top

Ag1—N5	2.143 (3)	Ag1—N1	2.147 (3)

N5—Ag1—N1	174.20 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H40···O4ⁱ	0.88	1.93	2.805 (4)	172.3
N6—H39···O3ⁱⁱ	0.90	2.13	2.936 (4)	148.8

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

Acknowledgements

We are grateful to Mrs Li (Wuhan University) for her assistance with the X-ray crystallographic analysis.

References

Abu-Youssef, M. A. M., Dey, R., Gohar, Y., Massoud, A. A., Ohrstrom, L. & Langer, V. (2007). Inorg. Chem.. 46, 5893–5903. Web of Science CSD CrossRef PubMed CAS Google Scholar
Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2002). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Dong, Y.-B., Zhao, X. & Huang, R.-Q. (2004). Inorg. Chem. 43, 5603–5612. Web of Science CSD CrossRef PubMed CAS Google Scholar
Niu, C.-Y., Wu, B.-L., Zheng, X.-F., Wan, X.-S., Zhang, H.-Y., Niu, Y.-Y. & Meng, L.-Y. (2009). CrystEngComm, 11, 1373–1382. Web of Science CSD CrossRef CAS Google Scholar
Niu, C.-Y., Zheng, X.-F., Bai, L.-L., Wu, X.-L. & Kou, C.-H. (2008). Acta Cryst. C64, m305–m307. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (1996). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1994). SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Sumby, C. J. & Hardie, M. J. (2005). Angew. Chem. Int. Ed. 44, 6395–6399. Web of Science CSD CrossRef CAS Google Scholar
Zheng, Y., Du, M., Li, J.-R., Zhang, R.-H. & Bu, X.-H. (2003). Dalton Trans. pp. 1509–1514. Web of Science CSD CrossRef Google Scholar

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Volume 65| Part 9| September 2009| Page m1029

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Bis[N′-(3-cyano­benzyl­­idene)isonicotino­hydrazide]silver(I) tri­fluoro­acetate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis[N′-(3-cyanobenzylidene)isonicotinohydrazide]silver(I) trifluoroacetate