A one-dimensional AgI coordination polymer: catena-poly[[[[N′-(4-cyano­benzyl­idene)nicotinohydrazide]silver(I)]-μ-N′-(4-cyano­benzyl­idene)nicotino­hydrazide] trifluoro­methane­sulfonate]

Niu, C.-Y.; Wan, X.-S.; Gui, X.-W.; Cao, Z.-G.; Kou, C.-H.

doi:10.1107/S1600536808034685

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Pages m1469-m1470

doi:10.1107/S1600536808034685

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A one-dimensional Ag^I coordination polymer: catena-poly[[[[N′-(4-cyanobenzylidene)nicotinohydrazide]silver(I)]-μ-N′-(4-cyanobenzylidene)nicotinohydrazide] trifluoromethanesulfonate]

Cao-Yuan Niu,^a ^* Xin-Sheng Wan,^a Xiao-Wei Gui,^a Zhan-Guo Cao ^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 10 October 2008; accepted 23 October 2008; online 31 October 2008)

In the title compound, {[Ag(C₁₄H₁₀N₄O)₂]CF₃SO₃}_n, the unique Ag^I ion is coordinated by two N atoms from two pyridine rings of two independent N′-(4-cyanobenzylidene)nicotinohydrazide ligands and one N atom of a carbonitrile group of a symmetry-related N′-(4-cyanobenzylidene)nicotinohydrazide ligand, forming a distorted T-shaped coordination environment. One of the independent ligands acts as a bridge connecting Ag^I ions, forming chains along the a axis. In the crystal structure, two neighbouring antiparallel chains are connected through N—H⋯O hydrogen bonds. In addition, there are relatively short Ag⋯O contacts of 2.723 (3) Å, which connect the chains into a three-dimensional structure.

Related literature

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

Experimental

Crystal data

[Ag(C₁₄H₁₀N₄O)₂]CF₃SO₃
M_r = 757.46
Monoclinic, C 2/c
a = 24.966 (2) Å
b = 13.9529 (13) Å
c = 17.6976 (16) Å
β = 98.437 (2)°
V = 6098.3 (10) Å³
Z = 8
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 173 (2) K
0.51 × 0.32 × 0.27 mm

Data collection

Siemens SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.685, T_max = 0.813
19396 measured reflections
6990 independent reflections
5059 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.148
S = 1.03
6990 reflections
432 parameters
22 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.47 e Å⁻³
Δρ_min = −0.79 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—N1	2.190 (3)
Ag1—N2	2.207 (3)
Ag1—N8ⁱ	2.518 (3)

N1—Ag1—N2	158.96 (11)
N1—Ag1—N8ⁱ	100.66 (12)
N2—Ag1—N8ⁱ	96.76 (12)
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
N3—H29⋯O2ⁱⁱ	0.869 (14)	2.18 (2)	2.999 (4)	156 (4)
N6—H28⋯O3	0.852 (18)	2.07 (2)	2.911 (5)	171 (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: DIAMOND (Brandenburg, 2005 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808034685/lh2709sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808034685/lh2709Isup2.hkl

checkCIF report

Comment top

In the title compound, (I), the unique Ag^I ion is coordinated by two nitrogen atoms from two pyridyl rings of two different ligands (N1, N2) and one nitrogen atom from one carbonitrile group of another ligand [N8ⁱ. symmetry code: (i) x - 1/2, -y + 1/2, z + 1/2,] forming a slightly distorted T-shaped coordination enviroment (Fig. 1). The N1—Ag1—N2 bond angle is 158.96 (11), indicating these three atoms are not exactly linear. Thus, the N1—Ag1—N8ⁱ and N2—Ag1—N8ⁱ bond angles are larger than 90°. The N—Ag bond distances involving the pyridine rings are in the range of 2.190 (3)–2.207 (3) Å, which are smaller than N—Ag bond distance involving the carbonitrile group, 2.518 (3) Å. This probably indicates that nitrogen atoms of carbonitrile groups possess a weaker coordinating ability with silver than the nitrogen atoms of the pyridine rings in one ligand. In the crystal structure, half of the 4-cyanobenzylidene nicotinohydrazide molecules act as bridging ligands, the other half coordinating only in the monodentate mode. Differences in bond distances between N_pyridine—Ag and N_carbonitrile—Ag bonds can also be found in {[Ag₂(1,6-Dihydro-2-methyl-6-oxo-(3,4'-bipyridine)-5-carbonitrile)₃] ₂(CH₃OH)₃(PF₆)₄}_n (Niu et al., 2007), where the N_carbonitrile—Ag bond distance of 2.529 (3) Å (similar to that in the title compound), is larger than the N_pyridine—Ag bond distance of 2.151 (3) Å.

The ligands acting as µ₂-bridging ligands coordinate through pyridine and carbonitrile nitrogen atoms. Each of these bridging ligands connects two silver atoms together by one pyridine nitrogen atom N1 and one carbonitrile nitrogen atom N8ⁱ to form a one-dimensional chain along the a axis. The separation of two neighbouring silver atoms in one chain is ca. 16 Å, which means 4-cyanobenzylidene nicotinohydrazide acts as a moderately long bridging ligand. Interestingly, the other half of all ligands act only as monodentate terminal ligands and are coordinated to silver atoms in chains only through pyridine nitrogen atoms with the carbonitrile nitrogen atoms remaining uncoordinated. Two terminal ligands connecting to two adjacent silver atoms in one chain are located in opposite directions away from the chain. Thus, these chains possess a unusual 'saw-like' structure with the terminal ligands acting like 'saw-teeth' (Fig. 2).

In the crystal structure, the CF₃SO₃^- counteranions are connected the ligands of chains by N—H···O hydrogen bonds (Table 2). In addition, there are also N—H···O hydrogen bondings between two neighbouring antiparallel chains (Fig. 3). Furthermore, 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 separation of 2.8760 (21) Å (Fig. 4). These noncovalent interactions have large contributions to the supramolecular three-dimensional framework of the compound.

Related literature top

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

Experimental top

A solution of AgCF₃SO₃ (0.026 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 35%). Elementary analysis, calculated for C₂₉H₂₀AgN₈O₅F₃S: C, 45.98, H, 2.66, N, 14.79%; found: C, 46.07, H, 2.53, N, 14.70%. One very strong bonds at 1262 cm^-1 in the IR spectra were assigned to CF₃SO₃^-.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (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 codes: (i) x - 1/2, -y + 1/2, z + 1/2.]
	Fig. 2. A space-filling 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. All counteranions and H atoms not involved in hydrogen bonds have been omitted for clarity.
	Fig. 4. A diagram showing the intermolecular Ag···O interactions indicated by dashed lines. All counteranions and H atoms have been omitted for clarity.

catena-poly[[[[N'-(4-cyanobenzylidene)nicotinohydrazide]silver(I)]-µ- N'-(4-cyanobenzylidene)nicotinohydrazide] trifluoromethanesulfonate] top

Crystal data top

[Ag(C₁₄H₁₀N₄O)₂]CF₃SO₃	F(000) = 3040
M_r = 757.46	D_x = 1.650 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5153 reflections
a = 24.966 (2) Å	θ = 2.1–27.5°
b = 13.9529 (13) Å	µ = 0.80 mm⁻¹
c = 17.6976 (16) Å	T = 173 K
β = 98.437 (2)°	Prism, colourless
V = 6098.3 (10) Å³	0.51 × 0.32 × 0.27 mm
Z = 8

Data collection top

Siemens SMART CCD diffractometer	6990 independent reflections
Radiation source: fine-focus sealed tube	5059 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→32
T_min = 0.685, T_max = 0.813	k = −18→17
19396 measured reflections	l = −22→15

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0766P)² + 8.964P] where P = (F_o² + 2F_c²)/3
6990 reflections	(Δ/σ)_max < 0.001
432 parameters	Δρ_max = 1.47 e Å⁻³
22 restraints	Δρ_min = −0.79 e Å⁻³

Crystal data top

[Ag(C₁₄H₁₀N₄O)₂]CF₃SO₃	V = 6098.3 (10) Å³
M_r = 757.46	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.966 (2) Å	µ = 0.80 mm⁻¹
b = 13.9529 (13) Å	T = 173 K
c = 17.6976 (16) Å	0.51 × 0.32 × 0.27 mm
β = 98.437 (2)°

Data collection top

Siemens SMART CCD diffractometer	6990 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5059 reflections with I > 2σ(I)
T_min = 0.685, T_max = 0.813	R_int = 0.031
19396 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	22 restraints
wR(F²) = 0.148	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 1.47 e Å⁻³
6990 reflections	Δρ_min = −0.79 e Å⁻³
432 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	0.177461 (13)	0.31617 (2)	0.21259 (2)	0.05965 (14)
N1	0.16489 (13)	0.4710 (2)	0.22045 (18)	0.0481 (7)
N2	0.19741 (12)	0.17730 (19)	0.16389 (17)	0.0421 (6)
N3	0.25625 (13)	0.6644 (2)	0.10836 (19)	0.0488 (7)
N4	0.29258 (12)	0.7215 (2)	0.07857 (19)	0.0497 (7)
N5	0.5169 (2)	0.9140 (4)	−0.1204 (3)	0.1027 (17)
N6	0.32032 (13)	0.1492 (2)	0.02428 (18)	0.0480 (7)
N7	0.35916 (12)	0.1432 (2)	−0.02381 (18)	0.0491 (7)
N8	0.60476 (14)	0.2456 (3)	−0.2154 (2)	0.0662 (10)
S1	0.35594 (5)	0.41766 (7)	0.11529 (6)	0.0575 (3)
O1	0.23222 (12)	0.78306 (19)	0.18438 (17)	0.0603 (7)
O2	0.28597 (11)	0.0026 (2)	−0.01063 (16)	0.0589 (7)
O3	0.33416 (17)	0.3230 (2)	0.1160 (2)	0.0852 (11)
O4	0.32654 (16)	0.4890 (3)	0.1495 (2)	0.0886 (11)
O5	0.37379 (17)	0.4448 (2)	0.04515 (19)	0.0852 (11)
F1	0.4489 (2)	0.3413 (5)	0.1600 (3)	0.180 (2)
F2	0.40950 (15)	0.3851 (3)	0.2507 (2)	0.1073 (11)
F3	0.4445 (2)	0.4874 (4)	0.1883 (3)	0.180 (2)
C1	0.12856 (16)	0.5082 (3)	0.2610 (2)	0.0548 (10)
H1	0.1059	0.4658	0.2839	0.066*
C2	0.12275 (17)	0.6049 (3)	0.2707 (3)	0.0611 (11)
H2	0.0966	0.6289	0.2998	0.073*
C3	0.15543 (18)	0.6664 (3)	0.2376 (3)	0.0562 (10)
H3	0.1524	0.7336	0.2444	0.067*
C4	0.19279 (14)	0.6307 (2)	0.19433 (19)	0.0410 (7)
C5	0.19597 (15)	0.5322 (3)	0.1878 (2)	0.0452 (8)
H5	0.2216	0.5065	0.1585	0.054*
C6	0.22824 (15)	0.6994 (2)	0.1618 (2)	0.0437 (8)
C7	0.32028 (16)	0.6787 (3)	0.0335 (2)	0.0497 (9)
H7	0.3143	0.6126	0.0226	0.060*
C8	0.36060 (15)	0.7304 (3)	−0.0009 (2)	0.0492 (9)
C9	0.39393 (18)	0.6808 (3)	−0.0440 (3)	0.0629 (11)
H9	0.3893	0.6137	−0.0514	0.075*
C10	0.43334 (18)	0.7280 (4)	−0.0756 (3)	0.0657 (11)
H10	0.4556	0.6936	−0.1054	0.079*
C11	0.44089 (18)	0.8263 (3)	−0.0643 (3)	0.0610 (11)
C12	0.40796 (18)	0.8751 (3)	−0.0220 (3)	0.0624 (11)
H12	0.4131	0.9420	−0.0139	0.075*
C13	0.36835 (17)	0.8298 (3)	0.0086 (2)	0.0549 (10)
H13	0.3455	0.8654	0.0367	0.066*
C14	0.4834 (2)	0.8750 (4)	−0.0962 (3)	0.0731 (13)
C15	0.18030 (14)	0.0956 (3)	0.1923 (2)	0.0434 (8)
H15	0.1556	0.0994	0.2283	0.052*
C16	0.19682 (16)	0.0068 (3)	0.1717 (2)	0.0496 (9)
H16	0.1842	−0.0494	0.1936	0.060*
C17	0.23172 (15)	0.0003 (2)	0.1192 (2)	0.0440 (8)
H17	0.2436	−0.0606	0.1042	0.053*
C18	0.24964 (13)	0.0833 (2)	0.08797 (19)	0.0390 (7)
C19	0.23178 (14)	0.1700 (2)	0.1127 (2)	0.0408 (7)
H19	0.2445	0.2273	0.0924	0.049*
C20	0.28677 (14)	0.0743 (2)	0.0289 (2)	0.0421 (8)
C21	0.38690 (16)	0.2191 (3)	−0.0263 (2)	0.0513 (9)
H21	0.3784	0.2739	0.0016	0.062*
C22	0.43167 (14)	0.2241 (3)	−0.0711 (2)	0.0470 (8)
C23	0.45139 (15)	0.1431 (3)	−0.1041 (2)	0.0496 (9)
H23	0.4343	0.0828	−0.1004	0.059*
C24	0.49545 (16)	0.1502 (3)	−0.1419 (2)	0.0516 (9)
H24	0.5091	0.0949	−0.1639	0.062*
C25	0.52007 (14)	0.2387 (3)	−0.1478 (2)	0.0481 (8)
C26	0.50079 (18)	0.3193 (3)	−0.1168 (3)	0.0615 (11)
H26	0.5176	0.3796	−0.1218	0.074*
C27	0.45664 (18)	0.3123 (3)	−0.0780 (3)	0.0590 (11)
H27	0.4433	0.3678	−0.0559	0.071*
C28	0.56767 (15)	0.2436 (3)	−0.1854 (2)	0.0524 (9)
C29	0.4169 (2)	0.4087 (4)	0.1813 (4)	0.0870 (16)
H28	0.3208 (14)	0.1991 (18)	0.0520 (17)	0.034 (9)*
H29	0.2522 (16)	0.6077 (15)	0.088 (2)	0.077 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0648 (2)	0.03572 (18)	0.0846 (3)	0.00461 (12)	0.03151 (17)	−0.00623 (14)
N1	0.0518 (17)	0.0365 (16)	0.0593 (18)	0.0005 (13)	0.0199 (14)	−0.0055 (13)
N2	0.0429 (15)	0.0342 (15)	0.0533 (17)	0.0026 (12)	0.0204 (13)	0.0006 (12)
N3	0.0516 (18)	0.0351 (17)	0.062 (2)	−0.0037 (13)	0.0157 (15)	−0.0009 (14)
N4	0.0453 (17)	0.0426 (17)	0.0613 (19)	−0.0032 (13)	0.0087 (14)	0.0035 (15)
N5	0.097 (3)	0.080 (3)	0.145 (5)	0.001 (3)	0.067 (3)	0.018 (3)
N6	0.0516 (18)	0.0436 (17)	0.0556 (18)	−0.0025 (14)	0.0308 (14)	−0.0074 (15)
N7	0.0481 (17)	0.0516 (18)	0.0530 (17)	0.0022 (14)	0.0257 (14)	0.0003 (15)
N8	0.055 (2)	0.083 (3)	0.067 (2)	−0.0100 (19)	0.0293 (17)	−0.003 (2)
S1	0.0696 (6)	0.0462 (5)	0.0620 (6)	0.0057 (5)	0.0276 (5)	−0.0020 (5)
O1	0.0777 (19)	0.0316 (13)	0.0750 (19)	−0.0016 (13)	0.0223 (15)	−0.0033 (13)
O2	0.0707 (18)	0.0435 (15)	0.0692 (18)	−0.0031 (13)	0.0324 (14)	−0.0152 (13)
O3	0.116 (3)	0.066 (2)	0.081 (2)	−0.0313 (19)	0.039 (2)	−0.0132 (17)
O4	0.107 (3)	0.085 (3)	0.078 (2)	0.038 (2)	0.029 (2)	−0.0101 (19)
O5	0.129 (3)	0.063 (2)	0.073 (2)	0.010 (2)	0.048 (2)	0.0106 (17)
F1	0.107 (3)	0.242 (6)	0.198 (5)	0.086 (3)	0.042 (3)	0.023 (4)
F2	0.105 (2)	0.118 (3)	0.094 (2)	−0.018 (2)	0.0007 (19)	0.033 (2)
F3	0.157 (4)	0.179 (5)	0.188 (4)	−0.111 (4)	−0.028 (3)	0.067 (4)
C1	0.051 (2)	0.047 (2)	0.072 (3)	−0.0022 (17)	0.0272 (19)	−0.0071 (19)
C2	0.061 (2)	0.050 (2)	0.080 (3)	0.0048 (19)	0.034 (2)	−0.014 (2)
C3	0.063 (2)	0.038 (2)	0.073 (3)	0.0095 (17)	0.024 (2)	−0.0100 (18)
C4	0.0428 (18)	0.0347 (18)	0.0459 (18)	0.0056 (14)	0.0082 (14)	−0.0045 (14)
C5	0.0493 (19)	0.0372 (18)	0.052 (2)	0.0074 (15)	0.0164 (16)	−0.0047 (15)
C6	0.0469 (19)	0.0330 (18)	0.051 (2)	0.0038 (14)	0.0069 (16)	−0.0007 (14)
C7	0.048 (2)	0.043 (2)	0.058 (2)	0.0004 (16)	0.0065 (17)	0.0016 (17)
C8	0.0431 (19)	0.053 (2)	0.051 (2)	−0.0008 (16)	0.0067 (16)	0.0048 (17)
C9	0.060 (3)	0.059 (3)	0.073 (3)	−0.001 (2)	0.020 (2)	−0.010 (2)
C10	0.061 (3)	0.072 (3)	0.069 (3)	0.004 (2)	0.027 (2)	−0.005 (2)
C11	0.052 (2)	0.067 (3)	0.065 (3)	0.0033 (19)	0.012 (2)	0.012 (2)
C12	0.066 (3)	0.049 (2)	0.076 (3)	−0.0001 (19)	0.025 (2)	0.011 (2)
C13	0.056 (2)	0.047 (2)	0.064 (2)	0.0069 (17)	0.0162 (19)	0.0032 (18)
C14	0.065 (3)	0.070 (3)	0.091 (3)	0.006 (2)	0.032 (3)	0.012 (3)
C15	0.0481 (19)	0.0362 (18)	0.0500 (19)	−0.0016 (14)	0.0212 (16)	−0.0007 (15)
C16	0.063 (2)	0.0335 (18)	0.057 (2)	−0.0047 (16)	0.0237 (18)	0.0053 (16)
C17	0.054 (2)	0.0294 (16)	0.052 (2)	−0.0002 (14)	0.0169 (16)	−0.0006 (14)
C18	0.0390 (17)	0.0349 (17)	0.0456 (18)	0.0005 (13)	0.0141 (14)	−0.0002 (14)
C19	0.0425 (18)	0.0305 (17)	0.053 (2)	−0.0001 (13)	0.0196 (15)	0.0028 (14)
C20	0.0427 (18)	0.0383 (18)	0.0485 (19)	0.0036 (14)	0.0172 (15)	0.0025 (15)
C21	0.054 (2)	0.050 (2)	0.056 (2)	−0.0010 (17)	0.0284 (18)	−0.0037 (18)
C22	0.0435 (19)	0.051 (2)	0.050 (2)	−0.0004 (16)	0.0188 (16)	0.0042 (17)
C23	0.047 (2)	0.047 (2)	0.058 (2)	−0.0052 (16)	0.0204 (17)	0.0013 (18)
C24	0.052 (2)	0.051 (2)	0.056 (2)	0.0028 (17)	0.0228 (17)	0.0001 (18)
C25	0.0424 (19)	0.059 (2)	0.0463 (19)	−0.0018 (16)	0.0185 (15)	0.0042 (17)
C26	0.059 (2)	0.057 (3)	0.076 (3)	−0.0119 (19)	0.033 (2)	0.001 (2)
C27	0.060 (2)	0.050 (2)	0.074 (3)	−0.0063 (18)	0.034 (2)	−0.0062 (19)
C28	0.047 (2)	0.065 (3)	0.048 (2)	−0.0058 (18)	0.0171 (16)	−0.0006 (18)
C29	0.071 (3)	0.080 (4)	0.115 (4)	−0.009 (3)	0.032 (3)	0.026 (3)

Geometric parameters (Å, º) top

Ag1—N1	2.190 (3)	C7—C8	1.444 (5)
Ag1—N2	2.207 (3)	C7—H7	0.9500
Ag1—N8ⁱ	2.518 (3)	C8—C9	1.392 (6)
N1—C5	1.341 (5)	C8—C13	1.407 (6)
N1—C1	1.341 (5)	C9—C10	1.370 (6)
N2—C19	1.340 (4)	C9—H9	0.9500
N2—C15	1.340 (4)	C10—C11	1.396 (7)
N3—C6	1.348 (5)	C10—H10	0.9500
N3—N4	1.370 (4)	C11—C12	1.372 (6)
N3—H29	0.869 (14)	C11—C14	1.442 (6)
N4—C7	1.278 (5)	C12—C13	1.351 (6)
N5—C14	1.133 (6)	C12—H12	0.9500
N6—C20	1.348 (5)	C13—H13	0.9500
N6—N7	1.383 (4)	C15—C16	1.372 (5)
N6—H28	0.852 (18)	C15—H15	0.9500
N7—C21	1.270 (5)	C16—C17	1.367 (5)
N8—C28	1.134 (5)	C16—H16	0.9500
N8—Ag1ⁱⁱ	2.518 (3)	C17—C18	1.385 (5)
S1—O4	1.424 (3)	C17—H17	0.9500
S1—O5	1.430 (3)	C18—C19	1.382 (5)
S1—O3	1.429 (3)	C18—C20	1.501 (4)
S1—C29	1.782 (6)	C19—H19	0.9500
O1—C6	1.232 (4)	C21—C22	1.464 (5)
O2—C20	1.220 (4)	C21—H21	0.9500
F1—C29	1.324 (8)	C22—C23	1.395 (6)
F2—C29	1.311 (6)	C22—C27	1.392 (5)
F3—C29	1.292 (7)	C23—C24	1.372 (5)
C1—C2	1.370 (6)	C23—H23	0.9500
C1—H1	0.9500	C24—C25	1.390 (6)
C2—C3	1.374 (6)	C24—H24	0.9500
C2—H2	0.9500	C25—C26	1.369 (6)
C3—C4	1.383 (5)	C25—C28	1.446 (5)
C3—H3	0.9500	C26—C27	1.385 (6)
C4—C5	1.382 (5)	C26—H26	0.9500
C4—C6	1.478 (5)	C27—H27	0.9500
C5—H5	0.9500

N1—Ag1—N2	158.96 (11)	C12—C11—C14	121.0 (4)
N1—Ag1—N8ⁱ	100.66 (12)	C10—C11—C14	119.9 (4)
N2—Ag1—N8ⁱ	96.76 (12)	C13—C12—C11	121.3 (4)
C5—N1—C1	117.6 (3)	C13—C12—H12	119.4
C5—N1—Ag1	120.3 (2)	C11—C12—H12	119.4
C1—N1—Ag1	122.1 (3)	C12—C13—C8	120.6 (4)
C19—N2—C15	117.4 (3)	C12—C13—H13	119.7
C19—N2—Ag1	122.3 (2)	C8—C13—H13	119.7
C15—N2—Ag1	119.8 (2)	N5—C14—C11	179.1 (6)
C6—N3—N4	120.0 (3)	N2—C15—C16	122.9 (3)
C6—N3—H29	125.3 (15)	N2—C15—H15	118.5
N4—N3—H29	114.6 (15)	C16—C15—H15	118.5
C7—N4—N3	114.7 (3)	C17—C16—C15	119.2 (3)
C20—N6—N7	119.3 (3)	C17—C16—H16	120.4
C20—N6—H28	124 (2)	C15—C16—H16	120.4
N7—N6—H28	117 (2)	C16—C17—C18	119.4 (3)
C21—N7—N6	114.0 (3)	C16—C17—H17	120.3
C28—N8—Ag1ⁱⁱ	158.1 (4)	C18—C17—H17	120.3
O4—S1—O5	115.5 (2)	C19—C18—C17	117.8 (3)
O4—S1—O3	115.0 (2)	C19—C18—C20	123.7 (3)
O5—S1—O3	114.8 (2)	C17—C18—C20	118.5 (3)
O4—S1—C29	102.4 (3)	N2—C19—C18	123.3 (3)
O5—S1—C29	104.0 (3)	N2—C19—H19	118.3
O3—S1—C29	102.7 (3)	C18—C19—H19	118.3
N1—C1—C2	122.8 (4)	O2—C20—N6	124.0 (3)
N1—C1—H1	118.6	O2—C20—C18	120.5 (3)
C2—C1—H1	118.6	N6—C20—C18	115.5 (3)
C1—C2—C3	118.7 (4)	N7—C21—C22	121.4 (4)
C1—C2—H2	120.6	N7—C21—H21	119.3
C3—C2—H2	120.6	C22—C21—H21	119.3
C2—C3—C4	120.1 (3)	C23—C22—C27	119.3 (3)
C2—C3—H3	119.9	C23—C22—C21	122.2 (4)
C4—C3—H3	119.9	C27—C22—C21	118.4 (4)
C3—C4—C5	117.1 (3)	C24—C23—C22	120.2 (4)
C3—C4—C6	118.2 (3)	C24—C23—H23	119.9
C5—C4—C6	124.6 (3)	C22—C23—H23	119.9
N1—C5—C4	123.6 (3)	C23—C24—C25	119.7 (4)
N1—C5—H5	118.2	C23—C24—H24	120.1
C4—C5—H5	118.2	C25—C24—H24	120.1
O1—C6—N3	123.1 (4)	C26—C25—C24	120.9 (3)
O1—C6—C4	120.8 (3)	C26—C25—C28	120.5 (4)
N3—C6—C4	116.1 (3)	C24—C25—C28	118.6 (4)
N4—C7—C8	120.3 (4)	C25—C26—C27	119.5 (4)
N4—C7—H7	119.9	C25—C26—H26	120.2
C8—C7—H7	119.9	C27—C26—H26	120.2
C9—C8—C13	118.2 (4)	C26—C27—C22	120.3 (4)
C9—C8—C7	119.5 (4)	C26—C27—H27	119.8
C13—C8—C7	122.3 (4)	C22—C27—H27	119.8
C10—C9—C8	120.5 (4)	N8—C28—C25	178.6 (5)
C10—C9—H9	119.7	F3—C29—F2	105.7 (6)
C8—C9—H9	119.7	F3—C29—F1	107.3 (6)
C9—C10—C11	120.2 (4)	F2—C29—F1	105.2 (5)
C9—C10—H10	119.9	F3—C29—S1	113.3 (4)
C11—C10—H10	119.9	F2—C29—S1	114.0 (4)
C12—C11—C10	119.1 (4)	F1—C29—S1	110.8 (5)

N2—Ag1—N1—C5	−34.0 (5)	C19—N2—C15—C16	0.6 (5)
N8ⁱ—Ag1—N1—C5	−179.4 (3)	Ag1—N2—C15—C16	−171.5 (3)
N2—Ag1—N1—C1	149.7 (3)	N2—C15—C16—C17	−0.9 (6)
N8ⁱ—Ag1—N1—C1	4.4 (3)	C15—C16—C17—C18	0.0 (6)
N1—Ag1—N2—C19	27.7 (5)	C16—C17—C18—C19	1.0 (5)
N8ⁱ—Ag1—N2—C19	173.4 (3)	C16—C17—C18—C20	−178.4 (3)
N1—Ag1—N2—C15	−160.7 (3)	C15—N2—C19—C18	0.6 (5)
N8ⁱ—Ag1—N2—C15	−14.9 (3)	Ag1—N2—C19—C18	172.4 (3)
C6—N3—N4—C7	174.1 (3)	C17—C18—C19—N2	−1.4 (5)
C20—N6—N7—C21	177.1 (4)	C20—C18—C19—N2	178.0 (3)
C5—N1—C1—C2	−0.9 (6)	N7—N6—C20—O2	−4.8 (6)
Ag1—N1—C1—C2	175.5 (3)	N7—N6—C20—C18	174.3 (3)
N1—C1—C2—C3	0.1 (7)	C19—C18—C20—O2	−153.1 (4)
C1—C2—C3—C4	1.0 (7)	C17—C18—C20—O2	26.3 (5)
C2—C3—C4—C5	−1.2 (6)	C19—C18—C20—N6	27.7 (5)
C2—C3—C4—C6	−178.1 (4)	C17—C18—C20—N6	−152.9 (3)
C1—N1—C5—C4	0.6 (6)	N6—N7—C21—C22	176.8 (3)
Ag1—N1—C5—C4	−175.8 (3)	N7—C21—C22—C23	−9.6 (6)
C3—C4—C5—N1	0.4 (6)	N7—C21—C22—C27	173.2 (4)
C6—C4—C5—N1	177.1 (3)	C27—C22—C23—C24	1.0 (6)
N4—N3—C6—O1	2.4 (6)	C21—C22—C23—C24	−176.2 (4)
N4—N3—C6—C4	−176.0 (3)	C22—C23—C24—C25	−0.6 (6)
C3—C4—C6—O1	14.1 (5)	C23—C24—C25—C26	−0.4 (6)
C5—C4—C6—O1	−162.6 (4)	C23—C24—C25—C28	177.7 (4)
C3—C4—C6—N3	−167.4 (4)	C24—C25—C26—C27	1.0 (7)
C5—C4—C6—N3	15.9 (5)	C28—C25—C26—C27	−177.0 (4)
N3—N4—C7—C8	−179.1 (3)	C25—C26—C27—C22	−0.6 (7)
N4—C7—C8—C9	173.9 (4)	C23—C22—C27—C26	−0.4 (7)
N4—C7—C8—C13	−4.9 (6)	C21—C22—C27—C26	176.9 (4)
C13—C8—C9—C10	0.4 (6)	O4—S1—C29—F3	−62.1 (6)
C7—C8—C9—C10	−178.4 (4)	O5—S1—C29—F3	58.4 (6)
C8—C9—C10—C11	0.7 (7)	O3—S1—C29—F3	178.4 (5)
C9—C10—C11—C12	−0.8 (7)	O4—S1—C29—F2	58.8 (5)
C9—C10—C11—C14	178.4 (4)	O5—S1—C29—F2	179.4 (4)
C10—C11—C12—C13	−0.3 (7)	O3—S1—C29—F2	−60.7 (5)
C14—C11—C12—C13	−179.4 (4)	O4—S1—C29—F1	177.3 (4)
C11—C12—C13—C8	1.5 (7)	O5—S1—C29—F1	−62.2 (5)
C9—C8—C13—C12	−1.5 (6)	O3—S1—C29—F1	57.8 (5)
C7—C8—C13—C12	177.3 (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
N3—H29···O2ⁱⁱⁱ	0.87 (1)	2.18 (2)	2.999 (4)	156 (4)
N6—H28···O3	0.85 (2)	2.07 (2)	2.911 (5)	171 (3)

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₄H₁₀N₄O)₂]CF₃SO₃
M_r	757.46
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	173
a, b, c (Å)	24.966 (2), 13.9529 (13), 17.6976 (16)
β (°)	98.437 (2)
V (Å³)	6098.3 (10)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.51 × 0.32 × 0.27

Data collection
Diffractometer	Siemens SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.685, 0.813
No. of measured, independent and observed [I > 2σ(I)] reflections	19396, 6990, 5059
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.148, 1.03
No. of reflections	6990
No. of parameters	432
No. of restraints	22
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.47, −0.79

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2005), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Ag1—N1	2.190 (3)	Ag1—N8ⁱ	2.518 (3)
Ag1—N2	2.207 (3)

N1—Ag1—N2	158.96 (11)	N2—Ag1—N8ⁱ	96.76 (12)
N1—Ag1—N8ⁱ	100.66 (12)

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
N3—H29···O2ⁱⁱ	0.869 (14)	2.18 (2)	2.999 (4)	156 (4)
N6—H28···O3	0.852 (18)	2.07 (2)	2.911 (5)	171 (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. 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
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
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SAINT and SMART. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar

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Volume 64| Part 11| November 2008| Pages m1469-m1470

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

A one-dimensional AgI coordination polymer: catena-poly[[[[N′-(4-cyano­benzyl­­idene)nicotinohydrazide]silver(I)]-μ-N′-(4-cyano­benzyl­­idene)nicotino­hydrazide] tri­fluoro­methane­sulfonate]

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

A one-dimensional Ag^I coordination polymer: catena-poly[[[[N′-(4-cyanobenzylidene)nicotinohydrazide]silver(I)]-μ-N′-(4-cyanobenzylidene)nicotinohydrazide] trifluoromethanesulfonate]