catena-Poly[[[[N′-(4-cyano­benzyl­idene)nicotinohydrazide]silver(I)]-μ-[N′-4-cyano­benzyl­idene)nicotinohydrazide]] hexa­fluoridoarsenate]

Niu, C.-Y.; Ning, A.-M.; Kou, C.-H.; He, Y.; Fen, Z.-Q.

doi:10.1107/S1600536809026907

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Pages m924-m925

doi:10.1107/S1600536809026907

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catena-Poly[[[[N′-(4-cyanobenzylidene)nicotinohydrazide]silver(I)]-μ-[N′-4-cyanobenzylidene)nicotinohydrazide]] hexafluoridoarsenate]

Cao-Yuan Niu,^a ^* Ai-Min Ning,^a Chun-Hong Kou,^a Yong He ^a and Zhi-Qiang Fen ^a

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

(Received 16 June 2009; accepted 9 July 2009; online 15 July 2009)

In the title compound, {[Ag(C₁₄H₁₀N₄O)₂]AsF₆}_n, the Ag^I ion is coordinated by two N atoms from two different pyridyl rings and one N atom from one carbonitrile group of three different N′-(4-cyanobenzylidene)nicotinohydrazide ligands in a distorted T-shaped geometry. The Ag—N_carbonitrile bond distance is significant longer than those of Ag—N_pyridyl. The bond angles around the Ag^I atom are also not in line with those in an ideal T-shaped geometry. One type of ligand acts as the bridge that connects Ag^I atoms into chains along [ $[\overline{1}]$ 01]. These chains are linked to each other via N—H⋯O hydrogen bonds and Ag⋯O interactions with an Ag⋯O separation of 2.869 (2) Å. In addition, the [AsF₆]⁻ counter-anions are linked to the hydrazone groups through N—H⋯F hydrogen bonds. Four of the F atoms of the [AsF₆]⁻ anion are disordered over two sets of sites with occupancies of 0.732 (9) and 0.268 (9).

Related literature

For background to silver coordination polymers, see: Dong et al. (2004 ); Niu et al. (2007 , 2008 ); Sumby & Hardie (2005 ); Vatsadze et al. (2004 ); Zheng et al. (2003 ).

Experimental

Crystal data

[Ag(C₁₄H₁₀N₄O)₂]AsF₆
M_r = 797.31
Monoclinic, C 2/c
a = 22.3785 (15) Å
b = 13.7662 (9) Å
c = 19.8482 (14) Å
β = 99.948 (1)°
V = 6022.6 (7) Å³
Z = 8
Mo Kα radiation
μ = 1.84 mm⁻¹
T = 173 K
0.52 × 0.12 × 0.11 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.448, T_max = 0.823
19207 measured reflections
6896 independent reflections
5017 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.02
6896 reflections
460 parameters
96 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—N5	2.183 (3)
Ag1—N1	2.204 (2)
Ag1—N4ⁱ	2.458 (3)

N5—Ag1—N1	156.68 (9)
N5—Ag1—N4ⁱ	108.09 (11)
N1—Ag1—N4ⁱ	92.87 (11)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H29⋯O1ⁱⁱ	0.868 (19)	2.13 (2)	2.976 (4)	165 (4)
N2—H28⋯F5	0.868 (19)	2.19 (2)	3.003 (4)	157 (3)
Symmetry code: (ii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (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/S1600536809026907/jh2084sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809026907/jh2084Isup2.hkl

checkCIF report

Comment top

In the title compound, (I), the central silver ion is coordinated by two nitrogen atoms from two pyridyl rings of two different ligands (N1, N5) and one nitrogen atom from one carbonitrile group of another ligand [N4ⁱ. Symmetry codes: (i) x - 1/2, -y + 1/2, z + 1/2] forming a slightly distorted T-shaped coordination enviroment (Fig. 1). The bond angle of N1—Ag1—N5 is shorter than 180 ° and bond angles of N1—Ag1—N4ⁱ and N5—Ag1—N4ⁱ are larger than the right angle (Table 1). The N—Ag bond distances for pyridyl rings are 2.183 (3) and 2.204 (2) Å, which are smaller than N—Ag bond distance for carbonitrile group.

The compound 4-Cyanobenzylidene nicotinohydrazide act as the µ₂-bridging ligands only by coordinations of pyridyl and carbonitrile nitrogen atoms. Each of these bridging ligands connects two silver atoms together by one pyridyl nitrogen atom N1 and one carbonitrile nitrogen atom N8 to form a one-dimensional chain along [-1,0,1] direction. The shortest distance between two silver atoms in one chain is about 16.28 Å. Meanwhile, the rest half of all ligands acting as terminal ligands are coordinated to silver atoms in chains only through pyridyl nitrogen atoms with the carbonitrile nitrogen atoms uncoordinating (Fig.2).

There are hydrogen bondings between uncoordinating groups, including pyridyl rings of terminal ligands and all hydrazone groups and counteranions. On one hand, counteranions AsF₆^- are attached to ligands of chains by N—H···F hydrogen bondings (Table 2). On the other hand, there are also N—H···O hydrogen bondings (Table 2) between two neighbouring antiparallel chains. In addition to these intermolecular hydrogen bondings, there are weak Ag···O interactions between one oxygen atom O1 of the terminal ligand in one chain and one silver atom in the neighbouring chain with the Ag···O separations of 2.876 (2) Å (Fig. 3).

Related literature top

For related literature, see: Dong et al. (2004); Niu et al. (2007, 2008); Sumby & Hardie (2005); Vatsadze et al. (2004); Zheng et al. (2003). It would be much more useful to readers if the "Related literature" section had some kind of simple sub-division, so that, instead of just "For related literature, see···" it said, for example, "For general background, see···. For related structures, see···.? etc. Please revise this section as indicated.

Experimental top

A solution of AgAsF₆ (0.032 g, 0.1 mmol) in CH₃OH (10 ml) was carefully layered on a CH₃OH/CHCl₃ solution (5 ml/10 ml) of 4-Cyanobenzylidene nicotinohydrazide (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 30%). One very strong bonds at 699 cm^-1 in the IR spectra was assigned to AsF₆^-.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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. 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 50% probability level and H atoms are omitted for clarity. [Symmetry codes: (i) x - 1/2, -y + 1/2, z + 1/2.]
	Fig. 2. A e llipsoid diagram at the 50% probability level showing the one-dimensional chain. All counteranions and H atoms have been omitted for clarity.
	Fig. 3. A diagram showing the intermolecular hydrogen bondings indicated by blue and red dashed lines and Ag···O interactions indicated by pink dashed lines.

catena-Poly[[[[N'-(4- cyanobenzylidene)nicotinohydrazide]silver(I)]-µ-[N'-4- cyanobenzylidene)nicotinohydrazide]] hexafluoridoarsenate] top

Crystal data top

[Ag(C₁₄H₁₀N₄O)₂]AsF₆	F(000) = 3152
M_r = 797.31	D_x = 1.759 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5377 reflections
a = 22.3785 (15) Å	θ = 2.1–27.5°
b = 13.7662 (9) Å	µ = 1.84 mm⁻¹
c = 19.8482 (14) Å	T = 173 K
β = 99.948 (1)°	Prism, colourless
V = 6022.6 (7) Å³	0.52 × 0.12 × 0.11 mm
Z = 8

Data collection top

Bruker APEXII CCD area-detector diffractometer	6896 independent reflections
Radiation source: fine-focus sealed tube	5017 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −29→18
T_min = 0.448, T_max = 0.823	k = −17→17
19207 measured reflections	l = −25→25

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0526P)² + 5.7237P] where P = (F_o² + 2F_c²)/3
6896 reflections	(Δ/σ)_max = 0.001
460 parameters	Δρ_max = 0.63 e Å⁻³
96 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Ag(C₁₄H₁₀N₄O)₂]AsF₆	V = 6022.6 (7) Å³
M_r = 797.31	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.3785 (15) Å	µ = 1.84 mm⁻¹
b = 13.7662 (9) Å	T = 173 K
c = 19.8482 (14) Å	0.52 × 0.12 × 0.11 mm
β = 99.948 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	6896 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5017 reflections with I > 2σ(I)
T_min = 0.448, T_max = 0.823	R_int = 0.028
19207 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	96 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.63 e Å⁻³
6896 reflections	Δρ_min = −0.47 e Å⁻³
460 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	0.183850 (14)	0.187891 (18)	0.197856 (15)	0.05547 (11)
N1	0.20655 (13)	0.32823 (17)	0.15519 (13)	0.0404 (6)
N2	0.33194 (14)	0.3474 (2)	0.02005 (14)	0.0471 (7)
N3	0.37007 (13)	0.3480 (2)	−0.02752 (14)	0.0480 (7)
N4	0.61376 (15)	0.2368 (3)	−0.23488 (16)	0.0667 (9)
N5	0.17227 (13)	0.03059 (19)	0.20139 (13)	0.0435 (6)
N6	0.26690 (13)	−0.16253 (19)	0.09119 (14)	0.0440 (6)
N7	0.30676 (13)	−0.2188 (2)	0.06251 (14)	0.0452 (6)
N8	0.5343 (2)	−0.4267 (3)	−0.1374 (2)	0.0990 (15)
O1	0.29409 (11)	0.49652 (17)	−0.01123 (12)	0.0540 (6)
O2	0.25137 (12)	−0.28036 (16)	0.16611 (13)	0.0569 (6)
C1	0.19143 (15)	0.4121 (2)	0.18267 (16)	0.0426 (7)
H1	0.1669	0.4098	0.2172	0.051*
C2	0.21021 (17)	0.5008 (2)	0.16271 (17)	0.0478 (8)
H2	0.1992	0.5585	0.1838	0.057*
C3	0.24503 (16)	0.5056 (2)	0.11201 (16)	0.0448 (8)
H3	0.2582	0.5665	0.0975	0.054*
C4	0.26041 (14)	0.4200 (2)	0.08263 (15)	0.0365 (7)
C5	0.24032 (15)	0.3332 (2)	0.10548 (16)	0.0389 (7)
H5	0.2508	0.2745	0.0852	0.047*
C6	0.29680 (15)	0.4257 (2)	0.02645 (15)	0.0400 (7)
C7	0.40093 (16)	0.2709 (3)	−0.02952 (17)	0.0513 (8)
H7	0.3955	0.2179	−0.0005	0.062*
C8	0.44496 (15)	0.2627 (3)	−0.07618 (16)	0.0461 (8)
C9	0.46234 (17)	0.3429 (3)	−0.11026 (18)	0.0499 (8)
H9	0.4440	0.4042	−0.1055	0.060*
C10	0.50556 (18)	0.3345 (3)	−0.15064 (18)	0.0528 (9)
H10	0.5178	0.3901	−0.1732	0.063*
C11	0.53175 (15)	0.2446 (3)	−0.15883 (16)	0.0476 (8)
C12	0.51410 (18)	0.1635 (3)	−0.1266 (2)	0.0594 (10)
H12	0.5312	0.1018	−0.1330	0.071*
C13	0.47112 (18)	0.1734 (3)	−0.0847 (2)	0.0588 (10)
H13	0.4594	0.1181	−0.0615	0.071*
C14	0.57804 (17)	0.2385 (3)	−0.20097 (18)	0.0527 (9)
C15	0.13563 (17)	−0.0091 (2)	0.24079 (17)	0.0491 (8)
H15	0.1117	0.0327	0.2633	0.059*
C16	0.13129 (18)	−0.1077 (3)	0.24988 (19)	0.0538 (9)
H16	0.1051	−0.1333	0.2784	0.065*
C17	0.16547 (17)	−0.1682 (2)	0.21708 (18)	0.0473 (8)
H17	0.1633	−0.2366	0.2228	0.057*
C18	0.20314 (14)	−0.1297 (2)	0.17564 (15)	0.0370 (7)
C19	0.20477 (15)	−0.0293 (2)	0.16906 (15)	0.0397 (7)
H19	0.2301	−0.0021	0.1402	0.048*
C20	0.24264 (15)	−0.1984 (2)	0.14389 (16)	0.0398 (7)
C21	0.33262 (17)	−0.1765 (2)	0.01809 (18)	0.0488 (8)
H21	0.3241	−0.1102	0.0072	0.059*
C22	0.37552 (16)	−0.2300 (3)	−0.01634 (17)	0.0473 (8)
C23	0.38639 (17)	−0.3282 (3)	−0.00388 (19)	0.0507 (8)
H23	0.3654	−0.3614	0.0269	0.061*
C24	0.42693 (18)	−0.3782 (3)	−0.03525 (19)	0.0552 (9)
H24	0.4341	−0.4453	−0.0260	0.066*
C25	0.45761 (17)	−0.3300 (3)	−0.0808 (2)	0.0556 (9)
C26	0.44726 (19)	−0.2317 (3)	−0.0942 (2)	0.0625 (10)
H26	0.4682	−0.1987	−0.1251	0.075*
C27	0.40629 (19)	−0.1822 (3)	−0.0622 (2)	0.0587 (10)
H27	0.3990	−0.1152	−0.0715	0.070*
C28	0.5002 (2)	−0.3825 (3)	−0.1133 (2)	0.0700 (12)
As1	0.377276 (19)	0.09939 (3)	0.14799 (2)	0.05697 (13)
F5	0.38907 (15)	0.21973 (18)	0.13618 (16)	0.1020 (9)
F6	0.36110 (16)	−0.01902 (19)	0.1542 (2)	0.1292 (13)
H28	0.3375 (17)	0.306 (2)	0.0537 (14)	0.056 (11)*
H29	0.2555 (17)	−0.1086 (19)	0.0702 (18)	0.061 (12)*
F1	0.3247 (3)	0.1084 (5)	0.0751 (3)	0.142 (3)	0.732 (9)
F2	0.3208 (3)	0.1242 (3)	0.1925 (3)	0.111 (2)	0.732 (9)
F3	0.4252 (4)	0.0990 (7)	0.2174 (5)	0.203 (4)	0.732 (9)
F4	0.4308 (3)	0.0776 (4)	0.1007 (5)	0.135 (3)	0.732 (9)
F1'	0.3034 (4)	0.1259 (9)	0.1417 (10)	0.111 (5)	0.268 (9)
F2'	0.3871 (8)	0.1196 (8)	0.2320 (4)	0.095 (5)	0.268 (9)
F3'	0.4516 (4)	0.0732 (7)	0.1563 (8)	0.084 (4)	0.268 (9)
F4'	0.3710 (9)	0.0775 (9)	0.0641 (5)	0.116 (5)	0.268 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0725 (2)	0.03016 (14)	0.0723 (2)	0.00011 (12)	0.03658 (16)	0.00469 (11)
N1	0.0519 (16)	0.0292 (13)	0.0455 (15)	−0.0014 (11)	0.0234 (13)	0.0001 (10)
N2	0.0587 (18)	0.0446 (15)	0.0450 (16)	0.0072 (14)	0.0290 (14)	0.0084 (13)
N3	0.0510 (17)	0.0533 (17)	0.0455 (15)	0.0038 (14)	0.0248 (13)	0.0021 (13)
N4	0.063 (2)	0.081 (2)	0.066 (2)	0.0065 (18)	0.0362 (18)	0.0071 (18)
N5	0.0556 (17)	0.0335 (14)	0.0455 (15)	0.0012 (12)	0.0209 (13)	0.0030 (11)
N6	0.0540 (17)	0.0341 (14)	0.0469 (16)	0.0066 (12)	0.0175 (14)	0.0016 (12)
N7	0.0505 (17)	0.0408 (14)	0.0466 (15)	0.0024 (13)	0.0150 (13)	−0.0058 (12)
N8	0.104 (3)	0.080 (3)	0.134 (4)	−0.010 (2)	0.081 (3)	−0.022 (3)
O1	0.0690 (17)	0.0442 (13)	0.0556 (14)	0.0016 (12)	0.0298 (13)	0.0130 (11)
O2	0.0758 (18)	0.0302 (11)	0.0705 (16)	0.0041 (11)	0.0285 (14)	0.0048 (11)
C1	0.0487 (19)	0.0373 (17)	0.0474 (18)	0.0036 (14)	0.0241 (15)	0.0002 (13)
C2	0.066 (2)	0.0305 (15)	0.0521 (19)	0.0043 (15)	0.0249 (17)	−0.0060 (14)
C3	0.058 (2)	0.0293 (15)	0.0505 (19)	−0.0016 (14)	0.0196 (16)	0.0020 (13)
C4	0.0427 (17)	0.0330 (15)	0.0356 (15)	−0.0004 (13)	0.0119 (13)	0.0004 (12)
C5	0.0505 (19)	0.0277 (14)	0.0429 (17)	−0.0005 (13)	0.0202 (15)	−0.0033 (12)
C6	0.0471 (19)	0.0370 (16)	0.0393 (16)	−0.0033 (14)	0.0169 (14)	−0.0004 (13)
C7	0.054 (2)	0.055 (2)	0.050 (2)	0.0019 (17)	0.0259 (17)	0.0060 (16)
C8	0.0439 (19)	0.056 (2)	0.0419 (17)	0.0036 (16)	0.0161 (15)	0.0004 (15)
C9	0.057 (2)	0.0452 (18)	0.053 (2)	0.0041 (16)	0.0240 (17)	−0.0017 (15)
C10	0.062 (2)	0.050 (2)	0.052 (2)	−0.0039 (17)	0.0267 (18)	0.0020 (16)
C11	0.0433 (19)	0.059 (2)	0.0446 (18)	0.0019 (16)	0.0179 (15)	−0.0010 (15)
C12	0.060 (2)	0.055 (2)	0.070 (2)	0.0133 (18)	0.031 (2)	0.0047 (18)
C13	0.062 (2)	0.053 (2)	0.070 (2)	0.0099 (18)	0.034 (2)	0.0157 (18)
C14	0.052 (2)	0.060 (2)	0.050 (2)	0.0052 (17)	0.0173 (17)	0.0032 (17)
C15	0.059 (2)	0.0436 (18)	0.0493 (19)	0.0054 (16)	0.0234 (17)	0.0022 (15)
C16	0.060 (2)	0.048 (2)	0.062 (2)	−0.0014 (17)	0.0319 (19)	0.0104 (16)
C17	0.056 (2)	0.0322 (16)	0.057 (2)	−0.0058 (14)	0.0179 (17)	0.0073 (14)
C18	0.0437 (18)	0.0300 (14)	0.0378 (16)	−0.0026 (13)	0.0086 (14)	0.0019 (12)
C19	0.0498 (19)	0.0324 (15)	0.0399 (16)	−0.0027 (13)	0.0164 (14)	0.0021 (12)
C20	0.0467 (19)	0.0278 (15)	0.0457 (17)	−0.0014 (13)	0.0099 (15)	−0.0021 (12)
C21	0.055 (2)	0.0429 (18)	0.0496 (19)	0.0016 (16)	0.0121 (17)	−0.0012 (15)
C22	0.0473 (19)	0.0509 (19)	0.0449 (18)	−0.0051 (16)	0.0113 (15)	−0.0066 (15)
C23	0.051 (2)	0.052 (2)	0.052 (2)	−0.0068 (16)	0.0190 (17)	−0.0040 (16)
C24	0.057 (2)	0.051 (2)	0.062 (2)	−0.0013 (17)	0.0216 (18)	−0.0078 (17)
C25	0.048 (2)	0.063 (2)	0.060 (2)	−0.0091 (18)	0.0211 (18)	−0.0159 (18)
C26	0.067 (3)	0.067 (3)	0.060 (2)	−0.013 (2)	0.029 (2)	−0.0030 (19)
C27	0.065 (3)	0.051 (2)	0.064 (2)	−0.0047 (18)	0.022 (2)	−0.0003 (17)
C28	0.066 (3)	0.068 (3)	0.084 (3)	−0.014 (2)	0.037 (2)	−0.014 (2)
As1	0.0619 (3)	0.03366 (19)	0.0799 (3)	−0.00267 (16)	0.0248 (2)	0.00097 (16)
F5	0.140 (3)	0.0476 (14)	0.123 (2)	−0.0164 (15)	0.034 (2)	0.0104 (14)
F6	0.139 (3)	0.0433 (14)	0.224 (4)	−0.0122 (16)	0.086 (3)	−0.0032 (19)
F1	0.126 (5)	0.177 (6)	0.109 (4)	−0.018 (4)	−0.025 (3)	−0.016 (4)
F2	0.147 (5)	0.084 (3)	0.127 (4)	−0.013 (3)	0.092 (4)	−0.024 (3)
F3	0.152 (6)	0.254 (8)	0.177 (7)	−0.023 (6)	−0.046 (5)	0.065 (6)
F4	0.125 (5)	0.092 (3)	0.219 (7)	0.009 (3)	0.115 (5)	0.000 (4)
F1'	0.075 (6)	0.096 (7)	0.162 (11)	0.008 (6)	0.021 (7)	0.017 (8)
F2'	0.161 (10)	0.079 (6)	0.054 (5)	0.020 (6)	0.043 (6)	−0.004 (4)
F3'	0.055 (5)	0.066 (6)	0.132 (9)	0.006 (4)	0.021 (6)	0.000 (6)
F4'	0.161 (11)	0.093 (7)	0.085 (7)	−0.017 (7)	−0.003 (7)	−0.018 (6)

Geometric parameters (Å, º) top

Ag1—N5	2.183 (3)	C11—C12	1.378 (5)
Ag1—N1	2.204 (2)	C11—C14	1.442 (4)
Ag1—N4ⁱ	2.458 (3)	C12—C13	1.382 (5)
N1—C5	1.344 (4)	C12—H12	0.9500
N1—C1	1.345 (4)	C13—H13	0.9500
N2—C6	1.353 (4)	C15—C16	1.374 (5)
N2—N3	1.378 (3)	C15—H15	0.9500
N2—H28	0.868 (19)	C16—C17	1.370 (5)
N3—C7	1.271 (5)	C16—H16	0.9500
N4—C14	1.131 (4)	C17—C18	1.382 (4)
N4—Ag1ⁱⁱ	2.458 (3)	C17—H17	0.9500
N5—C19	1.335 (4)	C18—C19	1.389 (4)
N5—C15	1.343 (4)	C18—C20	1.506 (4)
N6—C20	1.353 (4)	C19—H19	0.9500
N6—N7	1.376 (4)	C21—C22	1.468 (5)
N6—H29	0.868 (19)	C21—H21	0.9500
N7—C21	1.275 (4)	C22—C23	1.389 (5)
N8—C28	1.144 (5)	C22—C27	1.397 (5)
O1—C6	1.224 (4)	C23—C24	1.371 (5)
O2—C20	1.214 (4)	C23—H23	0.9500
C1—C2	1.372 (4)	C24—C25	1.394 (5)
C1—H1	0.9500	C24—H24	0.9500
C2—C3	1.377 (4)	C25—C26	1.391 (6)
C2—H2	0.9500	C25—C28	1.436 (5)
C3—C4	1.384 (4)	C26—C27	1.381 (5)
C3—H3	0.9500	C26—H26	0.9500
C4—C5	1.381 (4)	C27—H27	0.9500
C4—C6	1.492 (4)	As1—F3	1.593 (6)
C5—H5	0.9500	As1—F2'	1.667 (8)
C7—C8	1.468 (4)	As1—F4	1.671 (4)
C7—H7	0.9500	As1—F4'	1.674 (9)
C8—C13	1.384 (5)	As1—F1'	1.675 (10)
C8—C9	1.386 (5)	As1—F6	1.679 (3)
C9—C10	1.363 (5)	As1—F3'	1.682 (8)
C9—H9	0.9500	As1—F2	1.696 (4)
C10—C11	1.392 (5)	As1—F5	1.700 (2)
C10—H10	0.9500	As1—F1	1.704 (5)

N5—Ag1—N1	156.68 (9)	N5—C19—C18	123.0 (3)
N5—Ag1—N4ⁱ	108.09 (11)	N5—C19—H19	118.5
N1—Ag1—N4ⁱ	92.87 (11)	C18—C19—H19	118.5
C5—N1—C1	117.8 (3)	O2—C20—N6	124.0 (3)
C5—N1—Ag1	121.53 (19)	O2—C20—C18	120.1 (3)
C1—N1—Ag1	120.4 (2)	N6—C20—C18	115.9 (3)
C6—N2—N3	119.9 (3)	N7—C21—C22	120.3 (3)
C6—N2—H28	117 (2)	N7—C21—H21	119.8
N3—N2—H28	120 (3)	C22—C21—H21	119.8
C7—N3—N2	114.9 (3)	C23—C22—C27	118.9 (3)
C14—N4—Ag1ⁱⁱ	153.9 (3)	C23—C22—C21	120.9 (3)
C19—N5—C15	117.8 (3)	C27—C22—C21	120.2 (3)
C19—N5—Ag1	121.3 (2)	C24—C23—C22	121.2 (3)
C15—N5—Ag1	120.7 (2)	C24—C23—H23	119.4
C20—N6—N7	119.3 (3)	C22—C23—H23	119.4
C20—N6—H29	124 (3)	C23—C24—C25	119.6 (4)
N7—N6—H29	116 (3)	C23—C24—H24	120.2
C21—N7—N6	115.7 (3)	C25—C24—H24	120.2
N1—C1—C2	122.4 (3)	C26—C25—C24	120.2 (3)
N1—C1—H1	118.8	C26—C25—C28	120.3 (4)
C2—C1—H1	118.8	C24—C25—C28	119.5 (4)
C1—C2—C3	119.6 (3)	C27—C26—C25	119.6 (4)
C1—C2—H2	120.2	C27—C26—H26	120.2
C3—C2—H2	120.2	C25—C26—H26	120.2
C2—C3—C4	118.7 (3)	C26—C27—C22	120.6 (4)
C2—C3—H3	120.7	C26—C27—H27	119.7
C4—C3—H3	120.7	C22—C27—H27	119.7
C5—C4—C3	118.7 (3)	N8—C28—C25	177.5 (5)
C5—C4—C6	122.8 (3)	F3—As1—F4	92.5 (4)
C3—C4—C6	118.5 (3)	F2'—As1—F4	127.4 (6)
N1—C5—C4	122.8 (3)	F3—As1—F4'	142.0 (7)
N1—C5—H5	118.6	F2'—As1—F4'	177.2 (7)
C4—C5—H5	118.6	F4—As1—F4'	49.8 (6)
O1—C6—N2	123.1 (3)	F3—As1—F1'	125.0 (7)
O1—C6—C4	121.5 (3)	F2'—As1—F1'	89.8 (6)
N2—C6—C4	115.4 (3)	F4—As1—F1'	142.2 (6)
N3—C7—C8	120.7 (3)	F4'—As1—F1'	93.0 (7)
N3—C7—H7	119.6	F3—As1—F6	93.1 (3)
C8—C7—H7	119.6	F2'—As1—F6	94.7 (4)
C13—C8—C9	119.2 (3)	F4—As1—F6	92.9 (2)
C13—C8—C7	119.3 (3)	F4'—As1—F6	85.2 (4)
C9—C8—C7	121.5 (3)	F1'—As1—F6	89.7 (4)
C10—C9—C8	120.5 (3)	F3—As1—F3'	53.7 (5)
C10—C9—H9	119.8	F2'—As1—F3'	88.9 (6)
C8—C9—H9	119.8	F4'—As1—F3'	88.3 (6)
C9—C10—C11	120.0 (3)	F1'—As1—F3'	178.7 (7)
C9—C10—H10	120.0	F6—As1—F3'	90.4 (4)
C11—C10—H10	120.0	F3—As1—F2	90.1 (4)
C12—C11—C10	120.4 (3)	F2'—As1—F2	55.1 (5)
C12—C11—C14	121.0 (3)	F4—As1—F2	177.1 (3)
C10—C11—C14	118.6 (3)	F4'—As1—F2	127.7 (6)
C11—C12—C13	119.0 (3)	F6—As1—F2	88.16 (19)
C11—C12—H12	120.5	F3'—As1—F2	143.6 (5)
C13—C12—H12	120.5	F3—As1—F5	91.5 (3)
C12—C13—C8	120.9 (3)	F2'—As1—F5	88.8 (4)
C12—C13—H13	119.5	F4—As1—F5	87.4 (2)
C8—C13—H13	119.5	F4'—As1—F5	91.5 (4)
N4—C14—C11	177.6 (4)	F1'—As1—F5	87.3 (4)
N5—C15—C16	122.9 (3)	F6—As1—F5	175.38 (19)
N5—C15—H15	118.6	F3'—As1—F5	92.8 (4)
C16—C15—H15	118.6	F2—As1—F5	91.32 (19)
C17—C16—C15	118.7 (3)	F3—As1—F1	175.8 (4)
C17—C16—H16	120.6	F2'—As1—F1	142.2 (5)
C15—C16—H16	120.6	F4—As1—F1	89.6 (3)
C16—C17—C18	119.8 (3)	F1'—As1—F1	52.7 (6)
C16—C17—H17	120.1	F6—As1—F1	90.4 (3)
C18—C17—H17	120.1	F3'—As1—F1	128.6 (5)
C17—C18—C19	117.8 (3)	F2—As1—F1	87.7 (3)
C17—C18—C20	118.0 (3)	F5—As1—F1	85.0 (2)
C19—C18—C20	124.0 (3)

N5—Ag1—N1—C5	−17.9 (4)	C10—C11—C12—C13	−1.6 (6)
N4ⁱ—Ag1—N1—C5	−172.2 (3)	C14—C11—C12—C13	177.7 (4)
N5—Ag1—N1—C1	168.2 (3)	C11—C12—C13—C8	1.4 (6)
N4ⁱ—Ag1—N1—C1	13.8 (3)	C9—C8—C13—C12	0.0 (6)
C6—N2—N3—C7	−179.8 (3)	C7—C8—C13—C12	−178.0 (4)
N1—Ag1—N5—C19	27.0 (4)	C19—N5—C15—C16	1.2 (5)
N4ⁱ—Ag1—N5—C19	180.0 (2)	Ag1—N5—C15—C16	−173.6 (3)
N1—Ag1—N5—C15	−158.4 (3)	N5—C15—C16—C17	−0.4 (6)
N4ⁱ—Ag1—N5—C15	−5.4 (3)	C15—C16—C17—C18	−0.3 (6)
C20—N6—N7—C21	−172.9 (3)	C16—C17—C18—C19	0.1 (5)
C5—N1—C1—C2	−1.3 (5)	C16—C17—C18—C20	176.5 (3)
Ag1—N1—C1—C2	172.9 (3)	C15—N5—C19—C18	−1.4 (5)
N1—C1—C2—C3	1.1 (6)	Ag1—N5—C19—C18	173.4 (2)
C1—C2—C3—C4	−0.3 (5)	C17—C18—C19—N5	0.7 (5)
C2—C3—C4—C5	−0.1 (5)	C20—C18—C19—N5	−175.4 (3)
C2—C3—C4—C6	178.4 (3)	N7—N6—C20—O2	−3.8 (5)
C1—N1—C5—C4	0.9 (5)	N7—N6—C20—C18	175.7 (3)
Ag1—N1—C5—C4	−173.2 (2)	C17—C18—C20—O2	−16.5 (5)
C3—C4—C5—N1	−0.2 (5)	C19—C18—C20—O2	159.6 (3)
C6—C4—C5—N1	−178.7 (3)	C17—C18—C20—N6	164.0 (3)
N3—N2—C6—O1	4.6 (5)	C19—C18—C20—N6	−19.9 (5)
N3—N2—C6—C4	−176.0 (3)	N6—N7—C21—C22	−179.3 (3)
C5—C4—C6—O1	150.3 (3)	N7—C21—C22—C23	3.3 (5)
C3—C4—C6—O1	−28.2 (5)	N7—C21—C22—C27	−176.5 (3)
C5—C4—C6—N2	−29.0 (5)	C27—C22—C23—C24	0.6 (6)
C3—C4—C6—N2	152.4 (3)	C21—C22—C23—C24	−179.2 (3)
N2—N3—C7—C8	−177.9 (3)	C22—C23—C24—C25	−0.4 (6)
N3—C7—C8—C13	−170.4 (4)	C23—C24—C25—C26	0.2 (6)
N3—C7—C8—C9	11.7 (6)	C23—C24—C25—C28	179.8 (4)
C13—C8—C9—C10	−1.3 (6)	C24—C25—C26—C27	−0.2 (6)
C7—C8—C9—C10	176.7 (4)	C28—C25—C26—C27	−179.7 (4)
C8—C9—C10—C11	1.2 (6)	C25—C26—C27—C22	0.4 (6)
C9—C10—C11—C12	0.3 (6)	C23—C22—C27—C26	−0.6 (6)
C9—C10—C11—C14	−179.0 (4)	C21—C22—C27—C26	179.2 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H29···O1ⁱⁱⁱ	0.87 (2)	2.13 (2)	2.976 (4)	165 (4)
N2—H28···F5	0.87 (2)	2.19 (2)	3.003 (4)	157 (3)

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₄H₁₀N₄O)₂]AsF₆
M_r	797.31
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	22.3785 (15), 13.7662 (9), 19.8482 (14)
β (°)	99.948 (1)
V (Å³)	6022.6 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.84
Crystal size (mm)	0.52 × 0.12 × 0.11

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.448, 0.823
No. of measured, independent and observed [I > 2σ(I)] reflections	19207, 6896, 5017
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.02
No. of reflections	6896
No. of parameters	460
No. of restraints	96
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.47

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

Selected geometric parameters (Å, º) top

Ag1—N5	2.183 (3)	Ag1—N4ⁱ	2.458 (3)
Ag1—N1	2.204 (2)

N5—Ag1—N1	156.68 (9)	N1—Ag1—N4ⁱ	92.87 (11)
N5—Ag1—N4ⁱ	108.09 (11)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H29···O1ⁱⁱ	0.868 (19)	2.13 (2)	2.976 (4)	165 (4)
N2—H28···F5	0.868 (19)	2.19 (2)	3.003 (4)	157 (3)

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

Acknowledgements

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

References

Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. 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., Zhang, H.-Y., Li, Z.-J. & Hou, H.-W. (2007). Dalton Trans. pp. 5710–5713. Web of Science CSD CrossRef 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 (1996). SMART and 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
Vatsadze, S. Z., Kovalkina, M. A., Sviridenkova, N. V., Zyk, N. V., Churakov, A. V., Kuz'mina, L. G. & Howard, J. A. K. (2004). CrystEngComm, 6, 112–115. 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 8| August 2009| Pages m924-m925

doi:10.1107/S1600536809026907

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

catena-Poly[[[[N′-(4-cyano­benzyl­­idene)nicotinohydrazide]silver(I)]-μ-[N′-4-cyano­benzyl­­idene)nicotinohydrazide]] hexa­fluoridoarsenate]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[[[[N′-(4-cyanobenzylidene)nicotinohydrazide]silver(I)]-μ-[N′-4-cyanobenzylidene)nicotinohydrazide]] hexafluoridoarsenate]