catena-Poly[[(nitrato-κ2O,O′)silver(I)]-μ3-4-pyridone-κ3O:O:O]

Wu, X.-G.; Xiao, J.-X.; Qin, L.

doi:10.1107/S1600536809019138

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Pages m685-m686

doi:10.1107/S1600536809019138

Open

access

catena-Poly[[(nitrato-κ²O,O′)silver(I)]-μ₃-4-pyridone-κ³O:O:O]

Xian-Ge Wu,^a ^* Jun-Xia Xiao ^a and Liang Qin ^a

^aSchool of Chemistry and Chemical Engineering, Zhao Qing University, Zhaoqing 526061, People's Republic of China
^*Correspondence e-mail: xgwu69@yahoo.com.cn

(Received 8 May 2009; accepted 20 May 2009; online 29 May 2009)

In the title complex, [Ag(NO₃)(C₅H₅NO)]_n, the Ag^I atom is coordinated by two O atoms from two different 4-pyridone ligands and two O atoms from one nitrate anion, displaying a nearly planar coordination geometry. The O atoms of two 4-pyridone ligands bridge two symmetrically related AgNO₃ units, forming a dimer, with an Ag⋯Ag separation of 3.680 (2) Å. Neighbouring dimers are linked into an infinite chain through weak Ag⋯O interactions [2.765 (2) Å], Ag⋯Ag interactions [3.1511 (4) Å] and π–π stacking interactions [centroid–centroid distance = 3.623 (4) Å]. N—H⋯O and C—H⋯O hydrogen bonds assemble these chains into a three-dimensional network.

Related literature

For general background to hydroxypyridines, see: Deng et al. (2005 ); Holis & Lippard (1983 ); John & Urland (2006 ); Klausmeyer & Beckles (2007 ). For related structures, see: Deisenhofer & Michel (1998 ); Gao et al. (2004 ); Leng & Ng (2007 ); Li, Yan et al. (2005 ); Li, Yin et al. (2005 ); Pan & Xu (2004 ); Wu et al. (2003 ).

Experimental

Crystal data

[Ag(NO₃)(C₅H₅NO)]
M_r = 264.98
Monoclinic, C 2/c
a = 19.3509 (7) Å
b = 3.6232 (1) Å
c = 21.2600 (8) Å
β = 102.174 (2)°
V = 1457.06 (9) Å³
Z = 8
Mo Kα radiation
μ = 2.74 mm⁻¹
T = 296 K
0.26 × 0.23 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.508, T_max = 0.575
11458 measured reflections
1678 independent reflections
1557 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.054
S = 1.07
1678 reflections
112 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag1—O1ⁱ	2.3259 (15)
Ag1—O1	2.3493 (16)
Ag1—O1ⁱⁱ	2.7652 (18)
Ag1—O2	2.4132 (19)
Ag1—O3	2.5437 (18)
Ag1—Ag1ⁱⁱⁱ	3.1511 (4)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y-1, z; (iii) -x, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2^iv	0.93	2.46	3.343 (3)	160
N1—H1⋯O4^v	0.89 (3)	2.21 (2)	2.965 (3)	143 (3)
N1—H1⋯O4^iv	0.89 (3)	2.45 (2)	3.121 (3)	133 (3)
Symmetry codes: (iv) $[x+{\script{1\over 2}}, y+{\script{3\over 2}}, z]$ ; (v) $[-x, y+1, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019138/hy2199sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019138/hy2199Isup2.hkl

checkCIF report

Comment top

Hydroxypyridines (PyOH), such as 2-, 3- and 4-PyOH, have attracted great attention in the field of crystal engineering as good candidates for the construction of supramolecular systems because they are bifunctional ligands that are not only capable of coordinating to metal ions but can also form classical hydrogen bonds as both donors and acceptors (Holis & Lippard, 1983; Klausmeyer & Beckles, 2007). 4-PyOH has two tautomers, dominated by the presence of keto form in polar solvents (Deng et al., 2005; John & Urland, 2006). Thus, the protonated N atom can act as hydrogen bond donor and the PyOH uses O atom to coordinate to metal. However, the coordination chemistry of 4-PyOH ligand is still underveloped and only a few complexes have been structurally characterized in recent years (Gao et al., 2004; Leng & Ng, 2007; Li, Yan et al., 2005). In order to gain further insight into the metal-binding modes of the 4-PyOH ligand, we introduced Ag^I ion into the coordination system of the 4-PyOH ligand. In the present paper, the Ag^I ion only coordinates via the unfavoured O atom of 4-pyridone ligand, producing the title one-dimensional coordination polymer, which exhibits a three-dimensional hydrogen-bonded architecture.

The coordination environment of Ag^I centre is shown in Fig. 1. Each Ag^I atom is coordinated by two O atoms from two different 4-pyridone ligands and two O atoms from one nitrate anion (Table 1), displaying a nearly planar coordination geometry. Two 1H-pyridin-4-one ligands use their O atoms to bridge two symmetrically related AgNO₃ units to form a dimer, with an Ag···Ag separation of 3.680 (2)Å. The adjacent dimers are linked through weak Ag···Ag interactions [3.1511 (4)Å] into a one-dimensional polymeric chain, which is also stabilized by weak Ag···O interactions [2.765 (2)Å] and intrachain π–π interactions (Fig. 2). The centroid–centroid and interplanar distances between adjacent pyridyl rings are 3.623 (4) and 3.301 (4)Å, respectively, thus indicating a weak π–π contact (Deisenhofer & Michel, 1998; Li, Yin et al., 2005; Pan & Xu, 2004; Wu et al., 2003). The polymeric chain shows a staircase-like array, with an Ag···Ag···Ag angle of 63.51 (4)° between three successive Ag atoms along the chain. Such an array in the chain may be explained to avoid steric hindrance. N—H···O hydrogen bonds between the ligand N atoms and the nitrate O atoms (Table 2) link adjacent chains to furnish a lamellar layer. The interlayer N—H···O and C—H···O hydrogen bonds (Table 2) further assemble the neighbouring layers, giving rise to a three-dimensional supramolecular network (Fig. 3).

Related literature top

For general background to hydroxypyridines, see: Deng et al. (2005); Holis & Lippard (1983); John & Urland (2006); Klausmeyer & Beckles (2007). For related structures, see: Deisenhofer & Michel (1998); Gao et al. (2004); Leng & Ng (2007); Li, Yan et al. (2005); Li, Yin et al. (2005); Pan & Xu (2004); Wu et al. (2003).

Experimental top

A mixture of silver nitrate (0.17 g, 1 mmol), 4-hydroxypyridine (0.095 g, 1 mmol), NaOH (0.02 g, 0.5 mmol) and H₂O (12 ml) was placed in a 23 ml Teflon-lined reactor, which was heated to 433 K for 3 d and then cooled to room temperature at a rate of 10 K h^-1. The crystals obtained were washed with water and dried in air (yield 0.18 g, 69.2%).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound. H atoms have been omitted for clarity. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) -x, 1-y, 1-z.]
	Fig. 2. View of one-dimensional infinite chain. Dashed lines denote Ag···Ag and π–π interactions.
	Fig. 3. A packing view of the title compound. Hydrogen bonds are shown as dashed lines.

catena-Poly[[(nitrato-κ²O,O')silver(I)]- µ₃-4-pyridone-κ³O:O:O] top

Crystal data top

[Ag(NO₃)(C₅H₅NO)]	F(000) = 1024
M_r = 264.98	D_x = 2.416 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3600 reflections
a = 19.3509 (7) Å	θ = 1.4–28°
b = 3.6232 (1) Å	µ = 2.74 mm⁻¹
c = 21.2600 (8) Å	T = 296 K
β = 102.174 (2)°	Block, colorless
V = 1457.06 (9) Å³	0.26 × 0.23 × 0.21 mm
Z = 8

Data collection top

Bruker APEXII CCD diffractometer	1678 independent reflections
Radiation source: fine-focus sealed tube	1557 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→24
T_min = 0.508, T_max = 0.575	k = −4→4
11458 measured reflections	l = −26→27

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0276P)² + 1.8757P] where P = (F_o² + 2F_c²)/3
1678 reflections	(Δ/σ)_max = 0.001
112 parameters	Δρ_max = 0.50 e Å⁻³
1 restraint	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Ag(NO₃)(C₅H₅NO)]	V = 1457.06 (9) Å³
M_r = 264.98	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 19.3509 (7) Å	µ = 2.74 mm⁻¹
b = 3.6232 (1) Å	T = 296 K
c = 21.2600 (8) Å	0.26 × 0.23 × 0.21 mm
β = 102.174 (2)°

Data collection top

Bruker APEXII CCD diffractometer	1678 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1557 reflections with I > 2σ(I)
T_min = 0.508, T_max = 0.575	R_int = 0.022
11458 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	1 restraint
wR(F²) = 0.054	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.50 e Å⁻³
1678 reflections	Δρ_min = −0.52 e Å⁻³
112 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	−0.054927 (10)	0.18113 (6)	0.443081 (9)	0.04893 (9)
C1	0.08175 (11)	0.6362 (6)	0.41324 (10)	0.0342 (4)
C2	0.15034 (12)	0.7888 (6)	0.43328 (12)	0.0411 (5)
H2	0.1661	0.8620	0.4758	0.049*
C3	0.19321 (13)	0.8286 (7)	0.39055 (14)	0.0471 (6)
H3	0.2380	0.9306	0.4040	0.057*
C4	0.10736 (14)	0.5710 (7)	0.30792 (11)	0.0469 (5)
H4	0.0939	0.4967	0.2652	0.056*
C5	0.06220 (12)	0.5262 (7)	0.34795 (10)	0.0394 (4)
H5	0.0179	0.4222	0.3325	0.047*
H1	0.1981 (15)	0.767 (8)	0.3009 (12)	0.059*
N1	0.17149 (12)	0.7221 (6)	0.32924 (11)	0.0486 (5)
N2	−0.15451 (10)	−0.1759 (5)	0.34244 (9)	0.0362 (4)
O1	0.03930 (9)	0.6001 (5)	0.45201 (7)	0.0445 (4)
O2	−0.15517 (10)	−0.2094 (6)	0.40146 (8)	0.0543 (5)
O3	−0.10437 (9)	−0.0108 (6)	0.32724 (9)	0.0542 (4)
O4	−0.20310 (8)	−0.3092 (5)	0.30118 (8)	0.0480 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.04508 (12)	0.05614 (14)	0.04269 (12)	−0.01218 (8)	0.00275 (8)	−0.01404 (8)
C1	0.0356 (10)	0.0325 (10)	0.0360 (10)	−0.0024 (8)	0.0111 (8)	−0.0017 (8)
C2	0.0382 (11)	0.0412 (11)	0.0439 (12)	−0.0048 (9)	0.0085 (9)	−0.0019 (9)
C3	0.0353 (11)	0.0423 (13)	0.0658 (16)	−0.0008 (9)	0.0156 (11)	0.0055 (11)
C4	0.0583 (14)	0.0479 (13)	0.0378 (11)	0.0046 (11)	0.0173 (10)	0.0005 (10)
C5	0.0424 (11)	0.0417 (12)	0.0351 (10)	−0.0032 (9)	0.0101 (8)	−0.0029 (9)
N1	0.0523 (12)	0.0485 (11)	0.0532 (12)	0.0062 (9)	0.0299 (10)	0.0065 (9)
N2	0.0312 (8)	0.0395 (10)	0.0358 (9)	0.0001 (7)	0.0022 (7)	−0.0047 (7)
O1	0.0443 (8)	0.0547 (10)	0.0382 (8)	−0.0146 (7)	0.0175 (7)	−0.0098 (7)
O2	0.0548 (10)	0.0734 (12)	0.0336 (8)	−0.0131 (9)	0.0069 (8)	−0.0082 (8)
O3	0.0461 (9)	0.0610 (12)	0.0567 (10)	−0.0179 (9)	0.0132 (8)	−0.0042 (9)
O4	0.0377 (9)	0.0678 (11)	0.0360 (9)	−0.0126 (8)	0.0022 (7)	−0.0091 (8)

Geometric parameters (Å, º) top

Ag1—O1ⁱ	2.3259 (15)	C3—N1	1.339 (4)
Ag1—O1	2.3493 (16)	C3—H3	0.9300
Ag1—O1ⁱⁱ	2.7652 (18)	C4—N1	1.344 (4)
Ag1—O2	2.4132 (19)	C4—C5	1.352 (3)
Ag1—O3	2.5437 (18)	C4—H4	0.9300
Ag1—Ag1ⁱⁱⁱ	3.1511 (4)	C5—H5	0.9300
C1—O1	1.287 (2)	N1—H1	0.89 (3)
C1—C5	1.417 (3)	N2—O3	1.239 (2)
C1—C2	1.418 (3)	N2—O4	1.240 (2)
C2—C3	1.361 (3)	N2—O2	1.263 (3)
C2—H2	0.9300	O1—Ag1ⁱ	2.3259 (15)

O1ⁱ—Ag1—O1	76.15 (6)	C2—C3—H3	119.7
O1ⁱ—Ag1—O2	118.90 (6)	N1—C4—C5	120.7 (2)
O1—Ag1—O2	163.46 (6)	N1—C4—H4	119.7
O1ⁱ—Ag1—O3	165.44 (6)	C5—C4—H4	119.7
O1—Ag1—O3	112.45 (5)	C4—C5—C1	120.6 (2)
O2—Ag1—O3	51.36 (5)	C4—C5—H5	119.7
O1ⁱ—Ag1—Ag1ⁱⁱⁱ	58.35 (5)	C1—C5—H5	119.7
O1—Ag1—Ag1ⁱⁱⁱ	79.67 (4)	C3—N1—C4	121.6 (2)
O2—Ag1—Ag1ⁱⁱⁱ	113.41 (5)	C3—N1—H1	120 (2)
O3—Ag1—Ag1ⁱⁱⁱ	133.22 (5)	C4—N1—H1	118 (2)
O1—C1—C5	121.62 (19)	O3—N2—O4	121.46 (19)
O1—C1—C2	122.0 (2)	O3—N2—O2	118.54 (19)
C5—C1—C2	116.34 (19)	O4—N2—O2	120.00 (19)
C3—C2—C1	120.3 (2)	C1—O1—Ag1ⁱ	127.44 (14)
C3—C2—H2	119.9	C1—O1—Ag1	127.10 (13)
C1—C2—H2	119.9	Ag1ⁱ—O1—Ag1	103.85 (6)
N1—C3—C2	120.6 (2)	N2—O2—Ag1	97.60 (13)
N1—C3—H3	119.7	N2—O3—Ag1	91.99 (13)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2^iv	0.93	2.46	3.343 (3)	160
N1—H1···O4^v	0.89 (3)	2.21 (2)	2.965 (3)	143 (3)
N1—H1···O4^iv	0.89 (3)	2.45 (2)	3.121 (3)	133 (3)

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

Experimental details

Crystal data
Chemical formula	[Ag(NO₃)(C₅H₅NO)]
M_r	264.98
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	19.3509 (7), 3.6232 (1), 21.2600 (8)
β (°)	102.174 (2)
V (Å³)	1457.06 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	2.74
Crystal size (mm)	0.26 × 0.23 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.508, 0.575
No. of measured, independent and observed [I > 2σ(I)] reflections	11458, 1678, 1557
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.054, 1.07
No. of reflections	1678
No. of parameters	112
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.52

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Ag1—O1ⁱ	2.3259 (15)	Ag1—O2	2.4132 (19)
Ag1—O1	2.3493 (16)	Ag1—O3	2.5437 (18)
Ag1—O1ⁱⁱ	2.7652 (18)	Ag1—Ag1ⁱⁱⁱ	3.1511 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2^iv	0.93	2.46	3.343 (3)	160
N1—H1···O4^v	0.89 (3)	2.21 (2)	2.965 (3)	143 (3)
N1—H1···O4^iv	0.89 (3)	2.45 (2)	3.121 (3)	133 (3)

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

Acknowledgements

The authors acknowledge the Guangdong Natural Science Foundation (SN. 8452606101000739) for supporting this work.

References

Bruker (2007). APEX2 and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Deisenhofer, J. & Michel, H. (1998). EMBO J. 8, 2149–2170. Google Scholar
Deng, Z.-P., Gao, S., Huo, L.-H. & Zhao, H. (2005). Acta Cryst. E61, m2523–m2525. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gao, S., Lu, Z.-Z., Huo, L.-H. & Zhao, H. (2004). Acta Cryst. C60, m651–m653. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Holis, L. S. & Lippard, S. J. (1983). Inorg. Chem. 22, 2708–2713. CSD CrossRef Web of Science Google Scholar
John, D. & Urland, W. (2006). Eur. J. Inorg. Chem. pp. 3503–3509. Web of Science CSD CrossRef Google Scholar
Klausmeyer, K. K. & Beckles, F. R. (2007). Inorg. Chim. Acta, 360, 3241–3249. Web of Science CSD CrossRef CAS Google Scholar
Leng, X. B. & Ng, D. K. P. (2007). Eur. J. Inorg. Chem. pp. 4615–4620. Web of Science CSD CrossRef Google Scholar
Li, G. M., Yan, P. F., Sato, O. & Einaga, Y. (2005). J. Solid State Chem. 178, 36–40. Web of Science CSD CrossRef CAS Google Scholar
Li, H., Yin, K.-L. & Xu, D.-J. (2005). Acta Cryst. C61, m19–m21. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pan, T.-T. & Xu, D.-J. (2004). Acta Cryst. E60, m56–m58. CSD CrossRef IUCr Journals 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
Wu, Z.-Y., Xue, Y.-H. & Xu, D.-J. (2003). Acta Cryst. E59, m809–m811. Web of Science CSD CrossRef IUCr Journals Google Scholar