catena-Poly[[[(2-pyridone-κO)silver(I)]-μ-2-pyridone-κ2O:O] hexa­fluorido­phosphate]

Arman, H.D.; Miller, T.; Tiekink, E.R.T.

doi:10.1107/S1600536810035348

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Page m1212

doi:10.1107/S1600536810035348

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catena-Poly[[[(2-pyridone-κO)silver(I)]-μ-2-pyridone-κ²O:O] hexafluoridophosphate]

Hadi D. Arman,^a Tyler Miller ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 27 August 2010; accepted 1 September 2010; online 4 September 2010)

The asymmetric unit of the polymeric title salt, {[Ag(C₅H₅NO)₂]PF₆}_n, comprises an Ag^I cation (located on a twofold axis), two 2-pyridone ligands (with distinct coordination modes), and half a PF₆⁻ anion (situated on a centre of inversion). The Ag^I atom is in an approximately octahedral AgO₆ coordination geometry, which is stabilized by intramolecular N—H⋯O hydrogen bonds. The result of the bridging mode of the 2-pyridone ligand is the formation of a supramolecular chain along the c axis; these are consolidated in the crystal by C—H⋯F interactions.

Related literature

For structural diversity in the supramolecular structures of silver salts, see: Kundu et al. (2010 ). For a related Ag structure, see: Arman et al. (2010 ).

Experimental

Crystal data

[Ag(C₅H₅NO)₂]PF₆
M_r = 633.24
Monoclinic, C 2/c
a = 13.519 (5) Å
b = 24.187 (9) Å
c = 7.301 (3) Å
β = 96.918 (5)°
V = 2369.9 (16) Å³
Z = 4
Mo Kα radiation
μ = 1.00 mm⁻¹
T = 293 K
0.48 × 0.40 × 0.14 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.535, T_max = 1.000
8382 measured reflections
2703 independent reflections
2573 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.080
S = 1.14
2703 reflections
165 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Ag—O1	2.3543 (19)
Ag—O2	2.5055 (18)
Ag—O2ⁱ	2.6278 (19)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.91	2.765 (2)	171
N2—H2⋯O1ⁱⁱ	0.86	1.90	2.754 (3)	174
C3—H3⋯F1ⁱⁱⁱ	0.93	2.48	3.353 (3)	157
C5—H5⋯F3^iv	0.93	2.51	3.398 (3)	159
Symmetry codes: (ii) -x, -y, -z; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[-x-1, y, -z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035348/hb5626sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035348/hb5626Isup2.hkl

checkCIF report

Comment top

The structural diversity in the supramolecular structures of silver salts is well documented (Kundu et al., 2010). The title compound, (I), was was isolated and characterized as a continuation of recent structural studies of such structures (Arman et al., 2010).

The crystallographic asymmetric unit of (I) comprises half a Ag cation, situated on a crystallographic 2-fold axis, a monodentate 2-pyridone ligand, coordinating via the carbonyl-O atom, a bidentate 2-pyridone ligand, bridging two Ag cations via a carbonyl-O atom, and half a PF₆^- anion, situated about a crystallographic centre of inversion, Fig. 1. The resulting Ag^I atom coordination geomerty is based on a distorted octahedron defined by an O₆ donor set, with the Ag—O bond distances lying in the range 2.3543 (19) to 2.6278 (19) Å, Table 1. The coordination geometry is stabilized by intramolecular N—H···O hydrogen bonds, Table 2. As the carbonyl-O2 atom is bidentate bridging, a supramolecular chain along the c axis is generated, Fig. 2. The chains are consolidated in the 3-D structure by C—H···F interactions, Fig. 3.

Related literature top

For structural diversity in the supramolecular structures of silver salts, see: Kundu et al. (2010). For a related Ag structure, see: Arman et al. (2010).

Experimental top

The title salt, (I), was isolated as colourless blocks from the 1:2 reaction of silver hexafluorophosphate (Aldrich) and 2-hydroxypyridine (Aldrich) in methanol solution; m. pt 393–399 K.

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Asymmetric unit in the structure of (I) showing displacement ellipsoids at the 50% probability level. The Ag (lying on a 2-fold axis of symmetry) and P (lying on a centre of inversion) atom environments have been expanded to show the respective coordination geometries.
	Fig. 2. Portion of the supramolecular chain aligned along the c axis in (I).
	Fig. 3. A view in projection down the c axis of the crystal packing in (I), emphasizing the Ag octahedra and interspersing of the PF₆^- anions.

catena-Poly[[[(2-pyridone-κO)silver(I)]-µ-2-pyridone- κ²O:O] hexafluoridophosphate] top

Crystal data top

[Ag(C₅H₅NO)₂]PF₆	F(000) = 1264
M_r = 633.24	D_x = 1.775 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -C 2yc	Cell parameters from 4745 reflections
a = 13.519 (5) Å	θ = 3.1–40.6°
b = 24.187 (9) Å	µ = 1.00 mm⁻¹
c = 7.301 (3) Å	T = 293 K
β = 96.918 (5)°	Block, colourless
V = 2369.9 (16) Å³	0.48 × 0.40 × 0.14 mm
Z = 4

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	2703 independent reflections
Radiation source: fine-focus sealed tube	2573 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→17
T_min = 0.535, T_max = 1.000	k = −30→31
8382 measured reflections	l = −9→9

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.036P)² + 3.3853P] where P = (F_o² + 2F_c²)/3
2703 reflections	(Δ/σ)_max = 0.001
165 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Ag(C₅H₅NO)₂]PF₆	V = 2369.9 (16) Å³
M_r = 633.24	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 13.519 (5) Å	µ = 1.00 mm⁻¹
b = 24.187 (9) Å	T = 293 K
c = 7.301 (3) Å	0.48 × 0.40 × 0.14 mm
β = 96.918 (5)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	2703 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2573 reflections with I > 2σ(I)
T_min = 0.535, T_max = 1.000	R_int = 0.033
8382 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.080	H-atom parameters constrained
S = 1.14	Δρ_max = 0.78 e Å⁻³
2703 reflections	Δρ_min = −0.47 e Å⁻³
165 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
Ag	0.0000	0.0000	0.0000	0.02327 (9)
P1	−0.5000	0.14921 (3)	0.2500	0.02229 (17)
O1	0.00398 (11)	0.09711 (7)	−0.0200 (2)	0.0243 (3)
N1	−0.13089 (13)	0.11598 (7)	0.1275 (2)	0.0206 (3)
H1	−0.1378	0.0811	0.1457	0.025*
F1	−0.52808 (12)	0.14954 (6)	0.4566 (2)	0.0349 (3)
O2	−0.13415 (13)	0.00438 (6)	0.2083 (2)	0.0239 (3)
C6	−0.19943 (16)	−0.03274 (9)	0.2224 (3)	0.0214 (4)
N2	−0.18133 (13)	−0.08533 (7)	0.1662 (2)	0.0223 (4)
H2	−0.1265	−0.0916	0.1210	0.027*
C1	−0.05410 (15)	0.13279 (8)	0.0342 (3)	0.0195 (4)
F2	−0.58219 (11)	0.19640 (6)	0.1951 (2)	0.0340 (3)
F3	−0.58231 (11)	0.10246 (6)	0.1955 (2)	0.0356 (3)
C5	−0.19677 (17)	0.15108 (9)	0.1932 (3)	0.0240 (4)
H5	−0.2478	0.1371	0.2544	0.029*
C10	−0.24535 (18)	−0.12841 (9)	0.1781 (3)	0.0261 (4)
H10	−0.2291	−0.1632	0.1369	0.031*
C2	−0.04687 (17)	0.19098 (9)	0.0059 (3)	0.0237 (4)
H2A	0.0028	0.2048	−0.0591	0.028*
C3	−0.11206 (18)	0.22646 (9)	0.0732 (3)	0.0279 (5)
H3	−0.1059	0.2643	0.0548	0.033*
C7	−0.29123 (17)	−0.02432 (10)	0.2950 (3)	0.0263 (5)
H7	−0.3080	0.0108	0.3333	0.032*
C9	−0.33255 (17)	−0.12096 (10)	0.2493 (3)	0.0293 (5)
H9	−0.3762	−0.1503	0.2585	0.035*
C4	−0.18849 (18)	0.20657 (9)	0.1700 (3)	0.0283 (5)
H4	−0.2324	0.2308	0.2171	0.034*
C8	−0.35494 (17)	−0.06760 (11)	0.3087 (3)	0.0296 (5)
H8	−0.4142	−0.0616	0.3584	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag	0.02195 (14)	0.01698 (14)	0.03202 (15)	0.00192 (7)	0.00785 (10)	0.00250 (8)
P1	0.0220 (4)	0.0201 (4)	0.0267 (4)	0.000	0.0106 (3)	0.000
O1	0.0232 (8)	0.0203 (8)	0.0304 (8)	0.0016 (5)	0.0076 (6)	0.0000 (6)
N1	0.0225 (8)	0.0173 (8)	0.0225 (8)	0.0008 (6)	0.0045 (7)	0.0029 (7)
F1	0.0418 (8)	0.0363 (8)	0.0298 (7)	0.0041 (7)	0.0174 (6)	0.0042 (6)
O2	0.0225 (8)	0.0191 (8)	0.0308 (9)	−0.0005 (5)	0.0063 (7)	0.0036 (6)
C6	0.0217 (10)	0.0204 (10)	0.0220 (10)	0.0003 (8)	0.0023 (8)	0.0040 (8)
N2	0.0218 (8)	0.0215 (9)	0.0244 (9)	−0.0021 (7)	0.0062 (7)	0.0015 (7)
C1	0.0198 (9)	0.0201 (10)	0.0186 (9)	−0.0001 (7)	0.0019 (7)	0.0017 (7)
F2	0.0328 (8)	0.0300 (7)	0.0408 (8)	0.0092 (6)	0.0106 (6)	0.0067 (6)
F3	0.0307 (7)	0.0292 (7)	0.0480 (9)	−0.0084 (6)	0.0086 (6)	−0.0009 (6)
C5	0.0239 (10)	0.0258 (11)	0.0228 (10)	0.0027 (8)	0.0055 (8)	0.0020 (8)
C10	0.0327 (11)	0.0213 (10)	0.0245 (10)	−0.0065 (9)	0.0043 (9)	0.0013 (8)
C2	0.0277 (11)	0.0197 (10)	0.0239 (10)	−0.0026 (8)	0.0039 (8)	0.0021 (8)
C3	0.0364 (12)	0.0165 (10)	0.0311 (11)	0.0019 (9)	0.0056 (10)	0.0018 (8)
C7	0.0234 (10)	0.0283 (12)	0.0278 (11)	0.0032 (8)	0.0048 (9)	0.0021 (9)
C9	0.0272 (11)	0.0320 (12)	0.0286 (11)	−0.0115 (9)	0.0025 (9)	0.0052 (9)
C4	0.0316 (12)	0.0234 (11)	0.0312 (11)	0.0070 (9)	0.0092 (9)	−0.0008 (9)
C8	0.0208 (10)	0.0406 (14)	0.0278 (11)	−0.0022 (9)	0.0042 (9)	0.0049 (10)

Geometric parameters (Å, º) top

Ag—O1ⁱ	2.3543 (19)	C6—C7	1.422 (3)
Ag—O1	2.3543 (19)	N2—C10	1.364 (3)
Ag—O2ⁱ	2.5055 (18)	N2—H2	0.8600
Ag—O2	2.5055 (18)	C1—C2	1.427 (3)
Ag—O2ⁱⁱ	2.6278 (19)	C5—C4	1.359 (3)
Ag—O2ⁱⁱⁱ	2.6278 (19)	C5—H5	0.9300
P1—F1	1.5993 (15)	C10—C9	1.356 (3)
P1—F1^iv	1.5993 (15)	C10—H10	0.9300
P1—F3^iv	1.6026 (15)	C2—C3	1.363 (3)
P1—F3	1.6026 (15)	C2—H2A	0.9300
P1—F2^iv	1.6095 (15)	C3—C4	1.405 (3)
P1—F2	1.6095 (15)	C3—H3	0.9300
O1—C1	1.262 (3)	C7—C8	1.367 (3)
N1—C5	1.359 (3)	C7—H7	0.9300
N1—C1	1.370 (3)	C9—C8	1.406 (4)
N1—H1	0.8600	C9—H9	0.9300
O2—C6	1.272 (3)	C4—H4	0.9300
C6—N2	1.368 (3)	C8—H8	0.9300

O1—Ag—O1ⁱ	180	C6—O2—Ag	125.40 (14)
O1—Ag—O2	91.09 (5)	O2—C6—N2	118.79 (19)
O1—Ag—O2ⁱ	88.91 (5)	O2—C6—C7	125.1 (2)
O1—Ag—O2ⁱⁱ	89.50 (5)	N2—C6—C7	116.14 (19)
O1—Ag—O2ⁱⁱⁱ	90.50 (5)	C10—N2—C6	123.64 (19)
O1ⁱ—Ag—O2	88.91 (5)	C10—N2—H2	118.2
O1ⁱ—Ag—O2ⁱ	91.09 (5)	C6—N2—H2	118.2
O1ⁱ—Ag—O2ⁱⁱ	90.50 (5)	O1—C1—N1	119.33 (19)
O1ⁱ—Ag—O2ⁱⁱⁱ	89.50 (5)	O1—C1—C2	124.96 (19)
O2—Ag—O2ⁱ	180	N1—C1—C2	115.70 (18)
O2—Ag—O2ⁱⁱ	89.18 (5)	N1—C5—C4	120.4 (2)
O2—Ag—O2ⁱⁱⁱ	90.82 (5)	N1—C5—H5	119.8
O2ⁱ—Ag—O2ⁱⁱ	90.82 (5)	C4—C5—H5	119.8
O2ⁱ—Ag—O2ⁱⁱⁱ	89.18 (5)	C9—C10—N2	120.7 (2)
O2ⁱⁱ—Ag—O2ⁱⁱⁱ	180	C9—C10—H10	119.7
F1—P1—F1^iv	179.43 (13)	N2—C10—H10	119.7
F1—P1—F3^iv	90.33 (8)	C3—C2—C1	120.7 (2)
F1^iv—P1—F3^iv	90.07 (8)	C3—C2—H2A	119.7
F1—P1—F3	90.07 (8)	C1—C2—H2A	119.7
F1^iv—P1—F3	90.33 (8)	C2—C3—C4	120.8 (2)
F3^iv—P1—F3	90.26 (12)	C2—C3—H3	119.6
F1—P1—F2^iv	89.82 (8)	C4—C3—H3	119.6
F1^iv—P1—F2^iv	89.78 (8)	C8—C7—C6	120.3 (2)
F3^iv—P1—F2^iv	90.03 (8)	C8—C7—H7	119.9
F3—P1—F2^iv	179.68 (9)	C6—C7—H7	119.9
F1—P1—F2	89.78 (8)	C10—C9—C8	118.0 (2)
F1^iv—P1—F2	89.82 (8)	C10—C9—H9	121.0
F3^iv—P1—F2	179.69 (9)	C8—C9—H9	121.0
F3—P1—F2	90.03 (8)	C5—C4—C3	118.5 (2)
F2^iv—P1—F2	89.67 (12)	C5—C4—H4	120.7
C1—O1—Ag	130.04 (14)	C3—C4—H4	120.7
C5—N1—C1	123.91 (18)	C7—C8—C9	121.3 (2)
C5—N1—H1	118.0	C7—C8—H8	119.4
C1—N1—H1	118.0	C9—C8—H8	119.4

O2ⁱ—Ag—O1—C1	170.23 (18)	C1—N1—C5—C4	−0.7 (3)
O2—Ag—O1—C1	−9.77 (18)	C6—N2—C10—C9	−0.4 (3)
O1ⁱ—Ag—O2—C6	−28.01 (17)	O1—C1—C2—C3	−178.6 (2)
O1—Ag—O2—C6	151.99 (17)	N1—C1—C2—C3	1.5 (3)
Ag—O2—C6—N2	20.6 (3)	C1—C2—C3—C4	−0.7 (4)
Ag—O2—C6—C7	−160.21 (16)	O2—C6—C7—C8	−178.1 (2)
O2—C6—N2—C10	178.9 (2)	N2—C6—C7—C8	1.1 (3)
C7—C6—N2—C10	−0.4 (3)	N2—C10—C9—C8	0.5 (3)
Ag—O1—C1—N1	3.3 (3)	N1—C5—C4—C3	1.5 (3)
Ag—O1—C1—C2	−176.67 (15)	C2—C3—C4—C5	−0.8 (4)
C5—N1—C1—O1	179.28 (19)	C6—C7—C8—C9	−1.1 (4)
C5—N1—C1—C2	−0.8 (3)	C10—C9—C8—C7	0.2 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.91	2.765 (2)	171
N2—H2···O1ⁱ	0.86	1.90	2.754 (3)	174
C3—H3···F1^v	0.93	2.48	3.353 (3)	157
C5—H5···F3^iv	0.93	2.51	3.398 (3)	159

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

Experimental details

Crystal data
Chemical formula	[Ag(C₅H₅NO)₂]PF₆
M_r	633.24
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	13.519 (5), 24.187 (9), 7.301 (3)
β (°)	96.918 (5)
V (Å³)	2369.9 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.00
Crystal size (mm)	0.48 × 0.40 × 0.14

Data collection
Diffractometer	Rigaku AFC12K/SATURN724 diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.535, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8382, 2703, 2573
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.080, 1.14
No. of reflections	2703
No. of parameters	165
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.47

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Ag—O1	2.3543 (19)	Ag—O2ⁱ	2.6278 (19)
Ag—O2	2.5055 (18)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.91	2.765 (2)	171
N2—H2···O1ⁱⁱ	0.86	1.90	2.754 (3)	174
C3—H3···F1ⁱⁱⁱ	0.93	2.48	3.353 (3)	157
C5—H5···F3^iv	0.93	2.51	3.398 (3)	159

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

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