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

Wan, X.-S.; Dang, Y.-L.; Kou, C.-H.; Zhou, Z.-F.; Niu, C.-Y.

doi:10.1107/S1600536808038907

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Pages m1618-m1619

doi:10.1107/S1600536808038907

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

Xin-Sheng Wan,^a Yu-Li Dang,^a Chun-Hong Kou,^a Zhan-Fang Zhou ^a and Cao-Yuan Niu ^a ^*

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

(Received 11 October 2008; accepted 20 November 2008; online 26 November 2008)

In the title polymer, {[Ag(C₁₄H₁₀N₄O)₂]PF₆}_n, each Ag^I ion is coordinated by two N atoms from two pyridyl rings of independent N′-(4-cyanobenzylidene)nicotinohydrazide ligands, and one N atom from one carbonitrile group of a symmetry-related ligand in a distorted T-shaped geometry. The ligands exhibit two modes of coordination. One acts as a bridge connecting Ag atoms to form one-dimensional chains along [ $[\overline{1}]$ 01]. The other acts as a terminal monodentate ligand, coordinating to Ag through its pyridyl N atom. Two neighbouring antiparallel chains in the crystal are connected through N—H⋯O hydrogen bonds. Other adjacent chains are packed via Ag⋯O interactions, with Ag⋯O separations of 2.876 (2) Å. In addition, PF₆⁻ counter-anions interact with the hydrazone groups through N—H⋯F hydrogen bonds. The PF₆⁻ anion is disordered over two sites, with occupancies of 0.773 (8) and 0.227 (8).

Related literature

For background on fluorescent silver coordination complexes, see: Dong et al. (2004 ); Sumby & Hardie (2005 ). For related structures, see: Niu et al. (2007 , 2008 ); Vatsadze et al. (2004 ); Zheng et al. (2003 ).

Experimental

Crystal data

[Ag(C₁₄H₁₀N₄O)₂]PF₆
M_r = 753.36
Monoclinic, C 2/c
a = 22.3252 (17) Å
b = 13.6939 (11) Å
c = 19.8523 (16) Å
β = 99.9770 (10)°
V = 5977.4 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 173 (2) K
0.44 × 0.32 × 0.29 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Siemens, 1996 ) T_min = 0.718, T_max = 0.799
19020 measured reflections
6823 independent reflections
5105 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.099
S = 1.03
6823 reflections
460 parameters
96 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.67 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—N1	2.172 (2)
Ag1—N2	2.199 (2)
Ag1—N8ⁱ	2.456 (3)

N1—Ag1—N2	156.22 (8)
N1—Ag1—N8ⁱ	109.53 (9)
N2—Ag1—N8ⁱ	92.22 (9)
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H28⋯O2ⁱⁱ	0.865 (18)	2.15 (2)	2.990 (3)	162 (3)
N6—H29⋯F5	0.853 (18)	2.21 (2)	3.001 (4)	155 (3)
Symmetry code: (ii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038907/bh2203sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808038907/bh2203Isup2.hkl

checkCIF report

Comment top

Pyridyl organic ligands with carbonitrile groups can be used to construct silver coordination complexes with fascinating structures and good fluorescent properties (Sumby & Hardie, 2005; Dong et al., 2004). We also synthesized one-dimensional and two-dimensional silver coordination polymers using this kind of ligands (Niu et al., 2007, 2008). Herein, a one-dimensional silver coordination polymer constructed with a new bridging ligand of this type, 4-cyanobenzylidene nicotinohydrazide, is reported.

In the title compound, (I), the central Ag^I ion is coordinated by two N atoms from two pyridyl rings of two different ligands (N1, N2) and one N atom from one carbonitrile group of another ligand [N8ⁱ, symmetry code: (i) x - 1/2, -y + 3/2, z + 1/2], forming a slightly distorted T-shaped coordination environment (Fig. 1). The N1—Ag1—N2 bond angle is 156.22 (8)°, indicating these three atoms are not exactly in one line. Bond angles N1—Ag1—N8ⁱ and N2—Ag1—N8ⁱ are larger than 90° (Table 1). The Ag—N bond distances for pyridyl rings are in the range 2.172 (2)–2.199 (2) Å, which is smaller than N—Ag bond distance for the carbonitrile group (Table 1).

One 4-cyanobenzylidene nicotinohydrazide molecule acts as a µ₂-bridging ligand, by coordinating pyridyl and carbonitrile N atoms. Each bridging ligand connects two silver atoms together by one pyridyl N atom (N1) and one carbonitrile N atom (N8) to form a one-dimensional chain along the [-1 0 1] direction. The separation between two neighbouring Ag atoms in one chain is about 16 Å. Meanwhile, the other independent ligand is acting as a terminal ligand, being coordinated to Ag only through a pyridyl N atom. Two terminal ligands connected to two adjacent Ag atoms in one chain are located at the opposite positions away from the chain (Fig. 2).

There are hydrogen bonds between uncoordinating groups, including pyridyl rings of terminal ligands and all hydrazone groups, as well as other groups like counteranions. On one hand, counteranions PF₆^- interact with the ligands in the polymer through N—H···F hydrogen bonds (Table 2). Four F atoms (F1 to F4) of the PF₆^- anion are disordered over two sites, with occupancies 0.773 (8) and 0.227 (8). On the other hand, there are also N—H···O hydrogen bonds between two neighbouring antiparallel chains in the crystal (Fig. 3). In addition to these intermolecular contacts, there are weak Ag···O interactions between one O atom (O1) of the terminal ligand and one Ag atom in the neighbouring chain, with Ag···O separations of 2.876 (2) Å. These noncovalent interactions have large contributions to the supramolecular three-dimensional framework.

One-dimensional Ag^I coordination polymers with T-shaped coordination geometry were previously described in a few compounds: {[Ag(2,6-di(3-pyridylmethylidene) cyclohexanone)](NO₃)}_n (Vatsadze et al., 2004) and {[Ag(2,2'-(methylenebis(thio)) bis(pyrimidine))](NO₃)}_n(Zheng et al., 2003). The N—Ag—N bond angles in these two compounds deviate from 180° (ca. 158 and 131°, respectively), which are close to that observed in (I).

Related literature top

For background on fluorescent silver coordination complexes, see: Dong et al. (2004); Sumby & Hardie (2005). For related structures, see: Niu et al. (2007, 2008); Vatsadze et al. (2004); Zheng et al. (2003).

Experimental top

A solution of AgPF₆ (0.025 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: ca. 50%). Analysis, calculated for C₂₈H₂₀AgN₈O₂F₆P: C 44.64, H 2.68, N 14.87%; found: C 44.79, H 2.69, N 14.99%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXL97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXL97 (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 30% probability level and H atoms are shown as small spheres of arbitrary radii [Symmetry code: (i) x - 1/2, -y + 3/2, z + 1/2].
	Fig. 2. A ball and stick diagram showing the one-dimensional chain. All counteranions and H atoms have been omitted for clarity.
	Fig. 3. A diagram showing the intermolecular hydrogen bonds, indicated by dashed lines.

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

Crystal data top

[Ag(C₁₄H₁₀N₄O)₂]PF₆	F(000) = 3008
M_r = 753.36	D_x = 1.674 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5745 reflections
a = 22.3252 (17) Å	θ = 2.1–27.5°
b = 13.6939 (11) Å	µ = 0.81 mm⁻¹
c = 19.8523 (16) Å	T = 173 K
β = 99.977 (1)°	Prism, colourless
V = 5977.4 (8) Å³	0.44 × 0.32 × 0.29 mm
Z = 8

Data collection top

Siemens SMART CCD area-detector diffractometer	6823 independent reflections
Radiation source: fine-focus sealed tube	5105 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −28→25
T_min = 0.718, T_max = 0.800	k = −16→17
19020 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0457P)² + 5.9377P] where P = (F_o² + 2F_c²)/3
6823 reflections	(Δ/σ)_max = 0.001
460 parameters	Δρ_max = 0.92 e Å⁻³
96 restraints	Δρ_min = −0.67 e Å⁻³

Crystal data top

[Ag(C₁₄H₁₀N₄O)₂]PF₆	V = 5977.4 (8) Å³
M_r = 753.36	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 22.3252 (17) Å	µ = 0.81 mm⁻¹
b = 13.6939 (11) Å	T = 173 K
c = 19.8523 (16) Å	0.44 × 0.32 × 0.29 mm
β = 99.977 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	6823 independent reflections
Absorption correction: multi-scan (SADABS; Siemens, 1996)	5105 reflections with I > 2σ(I)
T_min = 0.718, T_max = 0.800	R_int = 0.022
19020 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	96 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.92 e Å⁻³
6823 reflections	Δρ_min = −0.67 e Å⁻³
460 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N8	0.61351 (13)	0.7668 (2)	−0.23514 (14)	0.0680 (8)
C28	0.57801 (14)	0.7655 (3)	−0.20064 (15)	0.0538 (7)
C25	0.53188 (13)	0.7592 (2)	−0.15834 (14)	0.0478 (7)
C24	0.50609 (14)	0.6686 (2)	−0.14987 (15)	0.0531 (7)
H24	0.5184	0.6128	−0.1724	0.064*
C26	0.51433 (15)	0.8411 (3)	−0.12646 (17)	0.0601 (8)
H26	0.5315	0.9031	−0.1330	0.072*
C27	0.47114 (15)	0.8310 (2)	−0.08462 (18)	0.0601 (8)
H27	0.4592	0.8868	−0.0618	0.072*
C23	0.46282 (14)	0.6602 (2)	−0.10881 (15)	0.0510 (7)
H23	0.4449	0.5985	−0.1032	0.061*
C22	0.44513 (13)	0.7418 (2)	−0.07544 (14)	0.0477 (7)
C21	0.40138 (14)	0.7334 (2)	−0.02860 (15)	0.0520 (7)
H21	0.3960	0.7864	0.0006	0.062*
N7	0.37061 (11)	0.6556 (2)	−0.02684 (12)	0.0494 (6)
N6	0.33253 (11)	0.6554 (2)	0.02109 (12)	0.0486 (6)
Ag1	0.182725 (12)	0.812121 (16)	0.197931 (13)	0.05723 (10)
C12	0.44862 (16)	1.2299 (3)	−0.09411 (17)	0.0643 (9)
H12	0.4699	1.1967	−0.1248	0.077*
C19	0.24057 (13)	0.66761 (18)	0.10608 (13)	0.0401 (6)
H19	0.2509	0.7270	0.0862	0.048*
C15	0.19185 (13)	0.5876 (2)	0.18284 (14)	0.0429 (6)
H15	0.1673	0.5897	0.2174	0.052*
C6	0.24333 (13)	1.19804 (19)	0.14358 (14)	0.0416 (6)
C18	0.26109 (12)	0.58116 (18)	0.08291 (12)	0.0367 (5)
C9	0.38638 (14)	1.3271 (2)	−0.00520 (16)	0.0532 (7)
H9	0.3651	1.3608	0.0253	0.064*
C7	0.33364 (14)	1.1743 (2)	0.01789 (15)	0.0502 (7)
H7	0.3256	1.1073	0.0076	0.060*
C4	0.20356 (12)	1.13009 (19)	0.17502 (13)	0.0380 (6)
C17	0.24587 (13)	0.49446 (19)	0.11196 (14)	0.0449 (6)
H17	0.2594	0.4336	0.0971	0.054*
C16	0.21082 (14)	0.4979 (2)	0.16270 (14)	0.0486 (7)
H16	0.1999	0.4396	0.1834	0.058*
C1	0.13502 (14)	1.0108 (2)	0.24051 (14)	0.0507 (7)
H1	0.1108	0.9695	0.2634	0.061*
C3	0.16615 (14)	1.1703 (2)	0.21661 (15)	0.0482 (7)
H3	0.1647	1.2390	0.2226	0.058*
C5	0.20473 (13)	1.02969 (19)	0.16908 (13)	0.0410 (6)
H5	0.2304	1.0018	0.1408	0.049*
C13	0.40755 (16)	1.1802 (2)	−0.06192 (17)	0.0606 (8)
H13	0.4006	1.1126	−0.0708	0.073*
C11	0.45847 (15)	1.3286 (3)	−0.08112 (17)	0.0575 (8)
C8	0.37610 (13)	1.2281 (2)	−0.01660 (14)	0.0485 (7)
C14	0.50138 (17)	1.3823 (3)	−0.1134 (2)	0.0713 (10)
C2	0.13130 (14)	1.1097 (2)	0.24891 (16)	0.0535 (8)
H2	0.1048	1.1361	0.2769	0.064*
C10	0.42664 (15)	1.3771 (2)	−0.03712 (17)	0.0576 (8)
H10	0.4328	1.4450	−0.0291	0.069*
N3	0.26781 (11)	1.16107 (18)	0.09093 (12)	0.0452 (5)
N2	0.20658 (11)	0.67179 (15)	0.15560 (11)	0.0417 (5)
N4	0.30732 (11)	1.21732 (18)	0.06194 (12)	0.0474 (6)
N1	0.17155 (11)	0.96955 (16)	0.20120 (11)	0.0443 (5)
N5	0.53463 (17)	1.4260 (3)	−0.1381 (2)	0.1005 (13)
P1	0.37466 (4)	0.89969 (6)	0.14663 (5)	0.0599 (2)
O2	0.29542 (10)	0.50513 (15)	−0.01052 (10)	0.0563 (5)
O1	0.25284 (10)	1.28063 (15)	0.16533 (11)	0.0584 (6)
C20	0.29779 (12)	0.57604 (19)	0.02673 (13)	0.0409 (6)
F5	0.38656 (13)	0.78661 (16)	0.13688 (14)	0.1030 (8)
F6	0.35972 (14)	1.01041 (16)	0.15169 (18)	0.1254 (11)
F1	0.3229 (3)	0.8764 (3)	0.1891 (3)	0.1111 (19)	0.773 (8)
F2	0.4206 (3)	0.9026 (5)	0.2114 (4)	0.182 (3)	0.773 (8)
F3	0.4237 (2)	0.9205 (3)	0.1009 (4)	0.129 (2)	0.773 (8)
F4	0.3249 (2)	0.8894 (4)	0.0790 (2)	0.1269 (19)	0.773 (8)
F1'	0.3816 (8)	0.8806 (8)	0.2243 (5)	0.096 (5)	0.227 (8)
F2'	0.4440 (4)	0.9236 (7)	0.1569 (9)	0.082 (4)	0.227 (8)
F3'	0.3702 (9)	0.9217 (9)	0.0687 (5)	0.112 (5)	0.227 (8)
F4'	0.3055 (4)	0.8774 (9)	0.1384 (11)	0.109 (5)	0.227 (8)
H28	0.2574 (13)	1.1069 (16)	0.0696 (14)	0.050 (9)*
H29	0.3373 (14)	0.7020 (18)	0.0501 (13)	0.048 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N8	0.0642 (18)	0.082 (2)	0.0669 (17)	−0.0083 (15)	0.0370 (15)	−0.0052 (15)
C28	0.0488 (17)	0.067 (2)	0.0496 (16)	−0.0054 (15)	0.0193 (14)	−0.0023 (15)
C25	0.0400 (15)	0.0643 (19)	0.0425 (15)	−0.0035 (13)	0.0168 (12)	−0.0011 (13)
C24	0.0556 (18)	0.0592 (19)	0.0508 (16)	0.0032 (14)	0.0264 (14)	0.0007 (14)
C26	0.060 (2)	0.0591 (19)	0.068 (2)	−0.0163 (15)	0.0323 (17)	−0.0065 (16)
C27	0.061 (2)	0.057 (2)	0.070 (2)	−0.0081 (15)	0.0337 (17)	−0.0143 (16)
C23	0.0533 (18)	0.0538 (17)	0.0513 (16)	−0.0046 (13)	0.0241 (14)	0.0040 (13)
C22	0.0434 (16)	0.0615 (19)	0.0422 (14)	−0.0043 (13)	0.0185 (13)	0.0001 (13)
C21	0.0528 (18)	0.0588 (19)	0.0508 (16)	−0.0022 (14)	0.0266 (14)	−0.0057 (14)
N7	0.0492 (14)	0.0615 (15)	0.0438 (13)	−0.0014 (12)	0.0254 (11)	−0.0007 (11)
N6	0.0535 (15)	0.0522 (15)	0.0478 (13)	−0.0051 (11)	0.0304 (12)	−0.0071 (11)
Ag1	0.07322 (19)	0.03326 (13)	0.07451 (18)	0.00004 (10)	0.03887 (14)	−0.00591 (10)
C12	0.064 (2)	0.075 (2)	0.062 (2)	0.0135 (18)	0.0322 (17)	0.0016 (18)
C19	0.0487 (16)	0.0332 (13)	0.0431 (14)	−0.0006 (11)	0.0210 (12)	0.0034 (11)
C15	0.0494 (16)	0.0379 (14)	0.0468 (14)	−0.0020 (11)	0.0230 (13)	−0.0003 (11)
C6	0.0461 (15)	0.0332 (14)	0.0469 (15)	0.0052 (11)	0.0122 (12)	0.0029 (11)
C18	0.0411 (14)	0.0351 (13)	0.0366 (13)	0.0005 (10)	0.0145 (11)	−0.0020 (10)
C9	0.0540 (18)	0.0563 (19)	0.0534 (17)	0.0099 (14)	0.0210 (14)	0.0056 (14)
C7	0.0539 (18)	0.0480 (17)	0.0508 (16)	−0.0006 (13)	0.0151 (14)	0.0028 (13)
C4	0.0431 (15)	0.0345 (13)	0.0377 (13)	0.0032 (11)	0.0107 (11)	−0.0017 (10)
C17	0.0579 (18)	0.0308 (13)	0.0502 (15)	0.0018 (12)	0.0210 (13)	−0.0012 (11)
C16	0.0652 (19)	0.0339 (14)	0.0519 (16)	−0.0052 (13)	0.0246 (14)	0.0049 (12)
C1	0.0609 (19)	0.0464 (16)	0.0517 (16)	−0.0040 (13)	0.0294 (15)	−0.0037 (13)
C3	0.0550 (17)	0.0375 (15)	0.0556 (16)	0.0041 (12)	0.0194 (14)	−0.0086 (12)
C5	0.0520 (16)	0.0349 (14)	0.0396 (13)	0.0029 (11)	0.0176 (12)	−0.0028 (11)
C13	0.069 (2)	0.054 (2)	0.063 (2)	0.0052 (15)	0.0251 (17)	−0.0041 (15)
C11	0.0524 (18)	0.067 (2)	0.0578 (18)	0.0096 (15)	0.0222 (15)	0.0139 (16)
C8	0.0455 (16)	0.0573 (18)	0.0444 (15)	0.0042 (13)	0.0123 (13)	0.0069 (13)
C14	0.072 (2)	0.070 (2)	0.082 (2)	0.0147 (18)	0.041 (2)	0.0162 (19)
C2	0.0587 (19)	0.0492 (17)	0.0604 (18)	0.0035 (14)	0.0321 (15)	−0.0082 (14)
C10	0.0587 (19)	0.0539 (19)	0.0648 (19)	0.0017 (14)	0.0238 (16)	0.0081 (15)
N3	0.0534 (15)	0.0370 (13)	0.0491 (13)	−0.0059 (10)	0.0197 (11)	−0.0014 (10)
N2	0.0493 (13)	0.0349 (12)	0.0466 (12)	0.0005 (9)	0.0247 (11)	0.0001 (9)
N4	0.0512 (14)	0.0456 (13)	0.0482 (13)	−0.0036 (11)	0.0163 (11)	0.0063 (11)
N1	0.0579 (15)	0.0331 (12)	0.0463 (12)	−0.0004 (10)	0.0215 (11)	−0.0037 (9)
N5	0.105 (3)	0.084 (3)	0.134 (3)	0.009 (2)	0.083 (3)	0.021 (2)
P1	0.0625 (5)	0.0379 (4)	0.0841 (6)	0.0022 (4)	0.0261 (5)	−0.0005 (4)
O2	0.0716 (14)	0.0488 (12)	0.0551 (12)	0.0005 (10)	0.0296 (11)	−0.0130 (10)
O1	0.0766 (15)	0.0328 (10)	0.0723 (14)	−0.0048 (10)	0.0310 (12)	−0.0021 (10)
C20	0.0463 (15)	0.0397 (14)	0.0403 (14)	0.0051 (11)	0.0179 (12)	0.0000 (11)
F5	0.139 (2)	0.0483 (12)	0.125 (2)	0.0164 (13)	0.0331 (17)	−0.0072 (13)
F6	0.142 (2)	0.0447 (13)	0.208 (3)	0.0124 (13)	0.083 (2)	0.0042 (16)
F1	0.141 (4)	0.087 (2)	0.128 (4)	0.010 (2)	0.085 (3)	0.026 (2)
F2	0.143 (5)	0.219 (6)	0.156 (5)	0.022 (4)	−0.051 (4)	−0.062 (4)
F3	0.112 (4)	0.094 (3)	0.207 (6)	−0.018 (2)	0.105 (4)	−0.012 (3)
F4	0.110 (3)	0.157 (4)	0.101 (3)	0.006 (3)	−0.017 (3)	0.017 (3)
F1'	0.149 (10)	0.085 (7)	0.064 (6)	−0.010 (7)	0.041 (7)	0.010 (5)
F2'	0.056 (5)	0.065 (6)	0.125 (9)	−0.004 (4)	0.020 (6)	−0.001 (6)
F3'	0.146 (11)	0.099 (8)	0.085 (7)	0.012 (8)	0.000 (7)	0.021 (6)
F4'	0.075 (7)	0.097 (8)	0.156 (11)	−0.012 (5)	0.020 (7)	−0.009 (8)

Geometric parameters (Å, º) top

N8—C28	1.134 (4)	C9—C8	1.387 (4)
N8—Ag1ⁱ	2.456 (3)	C9—H9	0.9500
C28—C25	1.440 (4)	C7—N4	1.279 (4)
C25—C26	1.378 (4)	C7—C8	1.461 (4)
C25—C24	1.389 (4)	C7—H7	0.9500
C24—C23	1.372 (4)	C4—C5	1.381 (4)
C24—H24	0.9500	C4—C3	1.386 (4)
C26—C27	1.384 (4)	C17—C16	1.379 (4)
C26—H26	0.9500	C17—H17	0.9500
C27—C22	1.379 (4)	C16—H16	0.9500
C27—H27	0.9500	C1—N1	1.347 (3)
C23—C22	1.390 (4)	C1—C2	1.369 (4)
C23—H23	0.9500	C1—H1	0.9500
C22—C21	1.465 (4)	C3—C2	1.370 (4)
C21—N7	1.271 (4)	C3—H3	0.9500
C21—H21	0.9500	C5—N1	1.341 (3)
N7—N6	1.382 (3)	C5—H5	0.9500
N6—C20	1.351 (4)	C13—C8	1.397 (4)
N6—H29	0.853 (18)	C13—H13	0.9500
Ag1—N1	2.172 (2)	C11—C10	1.387 (4)
Ag1—N2	2.199 (2)	C11—C14	1.443 (5)
Ag1—N8ⁱⁱ	2.456 (3)	C14—N5	1.130 (4)
C12—C13	1.384 (5)	C2—H2	0.9500
C12—C11	1.387 (5)	C10—H10	0.9500
C12—H12	0.9500	N3—N4	1.371 (3)
C19—N2	1.343 (3)	N3—H28	0.865 (18)
C19—C18	1.377 (3)	P1—F2	1.500 (5)
C19—H19	0.9500	P1—F1'	1.545 (9)
C15—N2	1.338 (3)	P1—F4'	1.555 (10)
C15—C16	1.381 (4)	P1—F6	1.559 (2)
C15—H15	0.9500	P1—F2'	1.560 (8)
C6—O1	1.216 (3)	P1—F3'	1.562 (9)
C6—N3	1.358 (3)	P1—F3	1.564 (4)
C6—C4	1.495 (4)	P1—F1	1.577 (3)
C18—C17	1.388 (4)	P1—F5	1.589 (2)
C18—C20	1.496 (3)	P1—F4	1.594 (4)
C9—C10	1.369 (4)	O2—C20	1.216 (3)

C28—N8—Ag1ⁱ	153.0 (3)	C12—C13—H13	119.6
N8—C28—C25	177.1 (4)	C8—C13—H13	119.6
C26—C25—C24	120.9 (3)	C10—C11—C12	120.1 (3)
C26—C25—C28	120.5 (3)	C10—C11—C14	119.2 (3)
C24—C25—C28	118.5 (3)	C12—C11—C14	120.7 (3)
C23—C24—C25	119.7 (3)	C9—C8—C13	118.5 (3)
C23—C24—H24	120.1	C9—C8—C7	121.3 (3)
C25—C24—H24	120.1	C13—C8—C7	120.3 (3)
C25—C26—C27	118.5 (3)	N5—C14—C11	178.6 (4)
C25—C26—H26	120.7	C1—C2—C3	119.4 (3)
C27—C26—H26	120.7	C1—C2—H2	120.3
C22—C27—C26	121.4 (3)	C3—C2—H2	120.3
C22—C27—H27	119.3	C9—C10—C11	120.1 (3)
C26—C27—H27	119.3	C9—C10—H10	119.9
C24—C23—C22	120.2 (3)	C11—C10—H10	119.9
C24—C23—H23	119.9	C6—N3—N4	119.2 (2)
C22—C23—H23	119.9	C6—N3—H28	126 (2)
C27—C22—C23	119.2 (3)	N4—N3—H28	114 (2)
C27—C22—C21	119.7 (3)	C15—N2—C19	117.9 (2)
C23—C22—C21	121.0 (3)	C15—N2—Ag1	120.36 (17)
N7—C21—C22	120.4 (3)	C19—N2—Ag1	121.45 (17)
N7—C21—H21	119.8	C7—N4—N3	115.7 (2)
C22—C21—H21	119.8	C5—N1—C1	117.3 (2)
C21—N7—N6	114.8 (3)	C5—N1—Ag1	121.31 (17)
C20—N6—N7	119.3 (2)	C1—N1—Ag1	121.18 (18)
C20—N6—H29	123 (2)	F2—P1—F4'	127.9 (7)
N7—N6—H29	116 (2)	F1'—P1—F4'	89.8 (7)
N1—Ag1—N2	156.22 (8)	F2—P1—F6	92.4 (3)
N1—Ag1—N8ⁱⁱ	109.53 (9)	F1'—P1—F6	94.9 (5)
N2—Ag1—N8ⁱⁱ	92.22 (9)	F4'—P1—F6	88.7 (5)
C13—C12—C11	119.3 (3)	F2—P1—F2'	50.8 (5)
C13—C12—H12	120.3	F1'—P1—F2'	88.9 (7)
C11—C12—H12	120.3	F4'—P1—F2'	178.3 (8)
N2—C19—C18	123.0 (2)	F6—P1—F2'	90.3 (4)
N2—C19—H19	118.5	F2—P1—F3'	139.5 (7)
C18—C19—H19	118.5	F1'—P1—F3'	177.5 (8)
N2—C15—C16	122.7 (2)	F4'—P1—F3'	92.5 (8)
N2—C15—H15	118.7	F6—P1—F3'	84.2 (4)
C16—C15—H15	118.7	F2'—P1—F3'	88.8 (7)
O1—C6—N3	123.4 (3)	F2—P1—F3	92.8 (4)
O1—C6—C4	120.7 (2)	F1'—P1—F3	130.6 (6)
N3—C6—C4	115.9 (2)	F4'—P1—F3	139.2 (7)
C19—C18—C17	118.5 (2)	F6—P1—F3	92.24 (19)
C19—C18—C20	123.1 (2)	F3'—P1—F3	47.2 (6)
C17—C18—C20	118.4 (2)	F2—P1—F1	90.2 (4)
C10—C9—C8	121.1 (3)	F1'—P1—F1	52.3 (6)
C10—C9—H9	119.5	F6—P1—F1	88.72 (18)
C8—C9—H9	119.5	F2'—P1—F1	140.8 (6)
N4—C7—C8	120.0 (3)	F3'—P1—F1	129.9 (7)
N4—C7—H7	120.0	F3—P1—F1	176.8 (3)
C8—C7—H7	120.0	F2—P1—F5	91.5 (3)
C5—C4—C3	117.9 (2)	F1'—P1—F5	88.1 (4)
C5—C4—C6	124.2 (2)	F4'—P1—F5	88.8 (5)
C3—C4—C6	117.7 (2)	F6—P1—F5	176.14 (19)
C16—C17—C18	119.0 (2)	F2'—P1—F5	92.2 (4)
C16—C17—H17	120.5	F3'—P1—F5	92.9 (4)
C18—C17—H17	120.5	F3—P1—F5	87.63 (19)
C17—C16—C15	118.9 (2)	F1—P1—F5	91.21 (18)
C17—C16—H16	120.5	F2—P1—F4	176.3 (4)
C15—C16—H16	120.5	F1'—P1—F4	139.5 (6)
N1—C1—C2	122.8 (3)	F4'—P1—F4	50.2 (7)
N1—C1—H1	118.6	F6—P1—F4	90.8 (2)
C2—C1—H1	118.6	F2'—P1—F4	131.2 (6)
C2—C3—C4	119.2 (3)	F3—P1—F4	89.0 (3)
C2—C3—H3	120.4	F1—P1—F4	87.9 (3)
C4—C3—H3	120.4	F5—P1—F4	85.3 (2)
N1—C5—C4	123.4 (2)	O2—C20—N6	123.8 (2)
N1—C5—H5	118.3	O2—C20—C18	121.3 (2)
C4—C5—H5	118.3	N6—C20—C18	114.9 (2)
C12—C13—C8	120.9 (3)

C26—C25—C24—C23	−0.5 (5)	C12—C13—C8—C7	−179.0 (3)
C28—C25—C24—C23	178.8 (3)	N4—C7—C8—C9	−3.3 (5)
C24—C25—C26—C27	1.2 (5)	N4—C7—C8—C13	176.4 (3)
C28—C25—C26—C27	−178.1 (3)	N1—C1—C2—C3	−0.4 (5)
C25—C26—C27—C22	−1.0 (5)	C4—C3—C2—C1	1.2 (5)
C25—C24—C23—C22	−0.4 (5)	C8—C9—C10—C11	−0.7 (5)
C26—C27—C22—C23	0.2 (5)	C12—C11—C10—C9	1.4 (5)
C26—C27—C22—C21	177.6 (3)	C14—C11—C10—C9	−179.0 (3)
C24—C23—C22—C27	0.6 (5)	O1—C6—N3—N4	2.7 (4)
C24—C23—C22—C21	−176.8 (3)	C4—C6—N3—N4	−176.6 (2)
C27—C22—C21—N7	169.9 (3)	C16—C15—N2—C19	0.9 (4)
C23—C22—C21—N7	−12.7 (5)	C16—C15—N2—Ag1	−173.5 (2)
C22—C21—N7—N6	177.8 (3)	C18—C19—N2—C15	−0.6 (4)
C21—N7—N6—C20	179.8 (3)	C18—C19—N2—Ag1	173.8 (2)
N2—C19—C18—C17	0.1 (4)	N1—Ag1—N2—C15	−169.9 (2)
N2—C19—C18—C20	178.6 (3)	N8ⁱⁱ—Ag1—N2—C15	−13.3 (2)
O1—C6—C4—C5	−159.2 (3)	N1—Ag1—N2—C19	15.9 (4)
N3—C6—C4—C5	20.1 (4)	N8ⁱⁱ—Ag1—N2—C19	172.5 (2)
O1—C6—C4—C3	16.2 (4)	C8—C7—N4—N3	179.3 (3)
N3—C6—C4—C3	−164.5 (3)	C6—N3—N4—C7	172.6 (3)
C19—C18—C17—C16	0.1 (4)	C4—C5—N1—C1	0.7 (4)
C20—C18—C17—C16	−178.5 (3)	C4—C5—N1—Ag1	−173.5 (2)
C18—C17—C16—C15	0.2 (4)	C2—C1—N1—C5	−0.6 (4)
N2—C15—C16—C17	−0.7 (5)	C2—C1—N1—Ag1	173.6 (2)
C5—C4—C3—C2	−1.1 (4)	N2—Ag1—N1—C5	−25.6 (4)
C6—C4—C3—C2	−176.9 (3)	N8ⁱⁱ—Ag1—N1—C5	179.3 (2)
C3—C4—C5—N1	0.2 (4)	N2—Ag1—N1—C1	160.4 (2)
C6—C4—C5—N1	175.6 (3)	N8ⁱⁱ—Ag1—N1—C1	5.3 (2)
C11—C12—C13—C8	−0.1 (5)	N7—N6—C20—O2	−3.9 (4)
C13—C12—C11—C10	−1.0 (5)	N7—N6—C20—C18	176.5 (2)
C13—C12—C11—C14	179.5 (3)	C19—C18—C20—O2	−150.7 (3)
C10—C9—C8—C13	−0.4 (5)	C17—C18—C20—O2	27.8 (4)
C10—C9—C8—C7	179.4 (3)	C19—C18—C20—N6	29.0 (4)
C12—C13—C8—C9	0.8 (5)	C17—C18—C20—N6	−152.5 (3)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H28···O2ⁱⁱⁱ	0.87 (2)	2.15 (2)	2.990 (3)	162 (3)
N6—H29···F5	0.85 (2)	2.21 (2)	3.001 (4)	155 (3)

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₄H₁₀N₄O)₂]PF₆
M_r	753.36
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	22.3252 (17), 13.6939 (11), 19.8523 (16)
β (°)	99.977 (1)
V (Å³)	5977.4 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.44 × 0.32 × 0.29

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Siemens, 1996)
T_min, T_max	0.718, 0.800
No. of measured, independent and observed [I > 2σ(I)] reflections	19020, 6823, 5105
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.03
No. of reflections	6823
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)	0.92, −0.67

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

Selected geometric parameters (Å, º) top

Ag1—N1	2.172 (2)	Ag1—N8ⁱ	2.456 (3)
Ag1—N2	2.199 (2)

N1—Ag1—N2	156.22 (8)	N2—Ag1—N8ⁱ	92.22 (9)
N1—Ag1—N8ⁱ	109.53 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H28···O2ⁱⁱ	0.865 (18)	2.15 (2)	2.990 (3)	162 (3)
N6—H29···F5	0.853 (18)	2.21 (2)	3.001 (4)	155 (3)

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

Acknowledgements

We are grateful to Mrs Li (Wuhan University) for her assistance with the X-ray crystallographic analysis. We also gratefully acknowledge financial support from the Natural Science Foundation of Henan Province (2008B150008) and the Science and Technology Key Task of Henan Province (0624040011).

References

Brandenburg, K. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Dong, Y.-B., Zhao, X., Huang, R.-Q., Smith, M. D. & zur Loye, H.-C. (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. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART, SAINT and SADABS. 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 64| Part 12| December 2008| Pages m1618-m1619

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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] hexa­fluorido­phosphate]

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] hexafluoridophosphate]