catena-Poly[[bis­[(2-carboxy­benzoato-κO)silver(I)](Ag—Ag)]bis­(μ-isonicotinic acid-κ2N:O)]

Li, X.-F.; An, Y.; Yin, Y.-S.

doi:10.1107/S1600536808009586

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page m779

doi:10.1107/S1600536808009586

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catena-Poly[[bis[(2-carboxybenzoato-κO)silver(I)](Ag—Ag)]bis(μ-isonicotinic acid-κ²N:O)]

Xiao-Feng Li,^a ^* Yan An ^a and Yan-Sheng Yin ^a

^aInstitute of Marine Materials and Engineering, Shanghai Maritime University, Shanghai 200135, People's Republic of China
^*Correspondence e-mail: lxf_shmtu@yahoo.com.cn

(Received 20 February 2008; accepted 7 April 2008; online 7 May 2008)

The title compound, [Ag(C₈H₅O₄)(C₆H₅NO₂)]_n, contains one Ag^I atom, one phthalate ligand and one isonicotinic acid molecule in the asymmetric unit. Each Ag atom is three-coordinated in a T-shaped geometry by two O atoms and one N atom from one phthalate ligand and two isonicotinic acid ligands. The isonicotinic acid ligand bridges two Ag atoms, forming a one-dimensional chain. Adjacent chains are linked by Ag—Ag interactions, leading to a double-chain. These double-chains are further linked via hydrogen bonds into a two-dimensional layer.

Related literature

For related literature, see: He et al. (2007 ); Xie et al. (2005 ).

Experimental

Crystal data

[Ag(C₈H₅O₄)(C₆H₅NO₂)]
M_r = 396.10
Monoclinic, C 2/c
a = 13.540 (3) Å
b = 8.160 (2) Å
c = 24.223 (5) Å
β = 99.546 (15)°
V = 2639 (1) Å³
Z = 8
Mo Kα radiation
μ = 1.56 mm⁻¹
T = 293 (2) K
0.37 × 0.32 × 0.27 mm

Data collection

Siemens P4 four-circle diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.597, T_max = 0.680
3909 measured reflections
3037 independent reflections
1879 reflections with I > 2σ(I)
R_int = 0.034
3 standard reflections every 97 reflections intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.00
3037 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.99 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Ag1—N1	2.179 (4)
Ag1—O3	2.185 (3)
Ag1—O2ⁱ	2.621 (3)
Ag1—Ag1ⁱⁱ	3.2123 (11)

N1—Ag1—O3	164.57 (14)
N1—Ag1—O2ⁱ	93.52 (12)
O3—Ag1—O2ⁱ	101.74 (11)
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O6ⁱⁱⁱ	0.82	1.80	2.616 (5)	175
O5—H5A⋯O4	0.82	1.57	2.390 (5)	180
Symmetry code: (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: XSCANS (Siemens, 1994 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009586/hy2121sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009586/hy2121Isup2.hkl

checkCIF report

Comment top

Silver ion reacts with isonicotinic acid and imidazole under hydrothermal conditions to form [Ag₈(in)₆(NO₃)₂] and [Ag(in)(Hin)]_0.5[Ag(in)] (Hin = isonicotinic acid) (Xie et al., 2005). With phthalic acid in place of imidazole, the reaction yields the title compound.

In the title compound, the Ag^I atom is three-coordinated by two O atoms and one N atom from one phthalate ligand and two isonicotinic acid ligands in a T-like geometry, with an O—Ag—N bond angle being 164.57 (14)° (Fig. 1; Table 1), giving a chain structure. Furthermore, the adjacent chains are linked by Ag···Ag interactions (He et al., 2007) to form a one-dimensional double-chain (Fig. 2). These double-chains are further linked via O—H···O hydrogen bonds (Table 2) into a two-dimensional layer. The hydrogen bonding interactions enhance the stability of the complex.

Related literature top

For related literature, see: He et al. (2007); Xie et al. (2005).

Experimental top

A mixture of Ag(NO₃) (0.085 g, 0.5 mmol), isonicotinic acid (0.123 g, 1 mmol), phthalic acid (0.166 g, 1 mmol) and water (10 ml) was sealed in a 23 ml Teflon-lined reactor, which was heated at 473 K for 4 d and then cooled to room temperature at a rate of 5 K h^-1 (yield 72%). Analysis calculated for C₁₄H₁₀AgNO₆: C 42.45, H 2.54, N 3.54%; found: C 42.39, H 2.61, N 3.48%.

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS (Siemens, 1994); data reduction: XSCANS (Siemens, 1994); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

	Fig. 1. The coordination geometry of the Ag atom in the title compound. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) x, -1 + y, z.]
	Fig. 2. The one-dimensional double-chain connected by Ag···Ag interactions.

catena-Poly[[bis[(2-carboxybenzoato-κO)silver(I)](Ag—Ag)]bis(µ-isonicotinic acid-κ²N:O)] top

Crystal data top

[Ag(C₈H₅O₄)(C₆H₅NO₂)]	F(000) = 1568
M_r = 396.10	D_x = 1.994 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 28 reflections
a = 13.540 (3) Å	θ = 5.2–12.4°
b = 8.160 (2) Å	µ = 1.56 mm⁻¹
c = 24.223 (5) Å	T = 293 K
β = 99.546 (15)°	Block, purple
V = 2639 (1) Å³	0.37 × 0.32 × 0.27 mm
Z = 8

Data collection top

Siemens P4 four-circle diffractometer	1879 reflections with I > 2σ(I)
Radiation source: medium-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 27.5°, θ_min = 1.7°
ω–2θ scans	h = −17→1
Absorption correction: ψ scan (North et al., 1968)	k = −1→10
T_min = 0.597, T_max = 0.680	l = −31→31
3909 measured reflections	3 standard reflections every 97 reflections
3037 independent reflections	intensity decay: 1.0%

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0526P)²] where P = (F_o² + 2F_c²)/3
3037 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.99 e Å⁻³
0 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Ag(C₈H₅O₄)(C₆H₅NO₂)]	V = 2639 (1) Å³
M_r = 396.10	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 13.540 (3) Å	µ = 1.56 mm⁻¹
b = 8.160 (2) Å	T = 293 K
c = 24.223 (5) Å	0.37 × 0.32 × 0.27 mm
β = 99.546 (15)°

Data collection top

Siemens P4 four-circle diffractometer	1879 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.034
T_min = 0.597, T_max = 0.680	3 standard reflections every 97 reflections
3909 measured reflections	intensity decay: 1.0%
3037 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.00	Δρ_max = 0.99 e Å⁻³
3037 reflections	Δρ_min = −0.72 e Å⁻³
199 parameters

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

	x	y	z	U_iso*/U_eq
Ag1	0.40822 (3)	0.04719 (5)	0.698630 (15)	0.05417 (17)
C1	0.4164 (4)	0.7535 (6)	0.58243 (19)	0.0405 (11)
C2	0.4211 (3)	0.5872 (5)	0.60835 (17)	0.0347 (10)
C3	0.4339 (4)	0.4453 (6)	0.57882 (17)	0.0397 (10)
H3A	0.4417	0.4514	0.5415	0.048*
C4	0.4348 (4)	0.2962 (6)	0.60478 (18)	0.0413 (11)
H4A	0.4430	0.2020	0.5844	0.050*
C5	0.4137 (4)	0.4183 (6)	0.68640 (19)	0.0442 (12)
H5B	0.4070	0.4087	0.7239	0.053*
C6	0.4119 (4)	0.5724 (6)	0.66396 (19)	0.0455 (12)
H6A	0.4046	0.6644	0.6856	0.055*
C7	0.3575 (4)	−0.0952 (6)	0.80056 (17)	0.0383 (11)
C8	0.3373 (3)	−0.2215 (5)	0.84252 (16)	0.0307 (9)
C9	0.3225 (3)	−0.3796 (6)	0.82196 (17)	0.0368 (10)
H9A	0.3240	−0.3975	0.7842	0.044*
C10	0.3056 (4)	−0.5119 (6)	0.8547 (2)	0.0437 (11)
H10A	0.2958	−0.6164	0.8394	0.052*
C11	0.3036 (4)	−0.4842 (6)	0.9109 (2)	0.0453 (12)
H11A	0.2927	−0.5711	0.9340	0.054*
C12	0.3177 (4)	−0.3304 (6)	0.93258 (18)	0.0403 (11)
H12A	0.3159	−0.3145	0.9704	0.048*
C13	0.3346 (3)	−0.1963 (5)	0.89994 (17)	0.0321 (9)
C14	0.3497 (4)	−0.0355 (6)	0.93203 (18)	0.0411 (11)
N1	0.4245 (3)	0.2820 (5)	0.65827 (15)	0.0414 (9)
O1	0.3992 (3)	0.7496 (5)	0.52779 (12)	0.0626 (11)
H1A	0.3896	0.8431	0.5156	0.094*
O2	0.4267 (3)	0.8778 (4)	0.60899 (13)	0.0513 (9)
O3	0.3817 (3)	−0.1459 (4)	0.75691 (13)	0.0579 (10)
O4	0.3483 (3)	0.0565 (4)	0.80925 (14)	0.0619 (11)
O5	0.3438 (3)	0.1015 (4)	0.90631 (14)	0.0579 (10)
H5A	0.3454	0.0858	0.8730	0.087*
O6	0.3672 (3)	−0.0408 (4)	0.98320 (13)	0.0641 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0797 (3)	0.0432 (2)	0.0430 (2)	0.0001 (2)	0.02032 (19)	0.01176 (18)
C1	0.046 (3)	0.038 (3)	0.037 (2)	0.002 (2)	0.007 (2)	0.002 (2)
C2	0.037 (2)	0.037 (2)	0.030 (2)	−0.001 (2)	0.0055 (18)	0.0028 (18)
C3	0.055 (3)	0.036 (2)	0.028 (2)	−0.003 (2)	0.008 (2)	0.0023 (19)
C4	0.055 (3)	0.037 (2)	0.034 (2)	0.000 (2)	0.012 (2)	−0.0002 (19)
C5	0.061 (3)	0.039 (3)	0.034 (2)	−0.002 (2)	0.012 (2)	0.0022 (19)
C6	0.065 (3)	0.042 (3)	0.031 (2)	0.005 (3)	0.014 (2)	−0.002 (2)
C7	0.046 (3)	0.042 (3)	0.027 (2)	−0.001 (2)	0.0060 (19)	0.0026 (19)
C8	0.038 (2)	0.028 (2)	0.0250 (18)	−0.0007 (19)	0.0035 (17)	0.0007 (17)
C9	0.050 (3)	0.034 (2)	0.0278 (19)	−0.001 (2)	0.0098 (19)	−0.0021 (18)
C10	0.045 (3)	0.027 (2)	0.057 (3)	−0.003 (2)	0.004 (2)	−0.001 (2)
C11	0.058 (3)	0.037 (3)	0.042 (2)	−0.005 (2)	0.009 (2)	0.010 (2)
C12	0.051 (3)	0.040 (3)	0.030 (2)	−0.003 (2)	0.007 (2)	0.0033 (19)
C13	0.038 (2)	0.028 (2)	0.031 (2)	0.002 (2)	0.0056 (18)	0.0000 (17)
C14	0.053 (3)	0.036 (3)	0.035 (2)	−0.004 (2)	0.012 (2)	−0.006 (2)
N1	0.053 (2)	0.038 (2)	0.0349 (18)	−0.0020 (19)	0.0101 (18)	0.0034 (17)
O1	0.112 (3)	0.042 (2)	0.0295 (16)	−0.002 (2)	−0.0001 (19)	0.0104 (15)
O2	0.075 (3)	0.0364 (18)	0.0425 (18)	0.0043 (19)	0.0082 (17)	0.0005 (16)
O3	0.101 (3)	0.0417 (19)	0.0379 (17)	0.004 (2)	0.0313 (19)	0.0044 (16)
O4	0.116 (3)	0.0339 (18)	0.0379 (17)	−0.003 (2)	0.019 (2)	0.0053 (15)
O5	0.107 (3)	0.0303 (17)	0.0380 (17)	−0.006 (2)	0.017 (2)	−0.0037 (15)
O6	0.117 (3)	0.047 (2)	0.0278 (15)	−0.004 (2)	0.0086 (19)	−0.0078 (16)

Geometric parameters (Å, º) top

Ag1—N1	2.179 (4)	C7—O4	1.265 (6)
Ag1—O3	2.185 (3)	C7—C8	1.504 (6)
Ag1—O2ⁱ	2.621 (3)	C8—C9	1.385 (6)
Ag1—Ag1ⁱⁱ	3.2123 (11)	C8—C13	1.412 (5)
C1—O2	1.197 (6)	C9—C10	1.380 (6)
C1—O1	1.306 (5)	C9—H9A	0.9300
C1—C2	1.492 (6)	C10—C11	1.387 (7)
C2—C6	1.379 (6)	C10—H10A	0.9300
C2—C3	1.386 (6)	C11—C12	1.361 (7)
C3—C4	1.368 (6)	C11—H11A	0.9300
C3—H3A	0.9300	C12—C13	1.391 (6)
C4—N1	1.331 (5)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.521 (6)
C5—N1	1.325 (6)	C14—O6	1.223 (5)
C5—C6	1.368 (7)	C14—O5	1.276 (6)
C5—H5B	0.9300	O1—H1A	0.8200
C6—H6A	0.9300	O5—H5A	0.8200
C7—O3	1.229 (5)

N1—Ag1—O3	164.57 (14)	C9—C8—C7	115.3 (3)
N1—Ag1—O2ⁱ	93.52 (12)	C13—C8—C7	127.1 (4)
O3—Ag1—O2ⁱ	101.74 (11)	C10—C9—C8	123.4 (4)
N1—Ag1—Ag1ⁱⁱ	102.98 (11)	C10—C9—H9A	118.3
O3—Ag1—Ag1ⁱⁱ	71.85 (11)	C8—C9—H9A	118.3
O2—C1—O1	123.4 (4)	C9—C10—C11	117.9 (4)
O2—C1—C2	123.5 (4)	C9—C10—H10A	121.0
O1—C1—C2	113.1 (4)	C11—C10—H10A	121.0
C6—C2—C3	118.0 (4)	C12—C11—C10	120.3 (4)
C6—C2—C1	119.1 (4)	C12—C11—H11A	119.8
C3—C2—C1	122.9 (4)	C10—C11—H11A	119.8
C4—C3—C2	119.8 (4)	C11—C12—C13	122.2 (4)
C4—C3—H3A	120.1	C11—C12—H12A	118.9
C2—C3—H3A	120.1	C13—C12—H12A	118.9
N1—C4—C3	122.0 (4)	C12—C13—C8	118.6 (4)
N1—C4—H4A	119.0	C12—C13—C14	114.1 (4)
C3—C4—H4A	119.0	C8—C13—C14	127.3 (4)
N1—C5—C6	124.3 (4)	O6—C14—O5	120.8 (4)
N1—C5—H5B	117.9	O6—C14—C13	118.3 (4)
C6—C5—H5B	117.9	O5—C14—C13	120.9 (4)
C5—C6—C2	118.0 (5)	C5—N1—C4	117.8 (4)
C5—C6—H6A	121.0	C5—N1—Ag1	118.6 (3)
C2—C6—H6A	121.0	C4—N1—Ag1	123.3 (3)
O3—C7—O4	121.4 (4)	C1—O1—H1A	109.5
O3—C7—C8	117.0 (4)	C7—O3—Ag1	114.1 (3)
O4—C7—C8	121.6 (4)	C14—O5—H5A	109.5
C9—C8—C13	117.6 (4)

O2—C1—C2—C6	16.8 (8)	C9—C8—C13—C12	0.2 (7)
O1—C1—C2—C6	−162.7 (4)	C7—C8—C13—C12	−178.0 (4)
O2—C1—C2—C3	−163.7 (5)	C9—C8—C13—C14	179.3 (4)
O1—C1—C2—C3	16.8 (7)	C7—C8—C13—C14	1.1 (8)
C6—C2—C3—C4	1.3 (7)	C12—C13—C14—O6	15.3 (7)
C1—C2—C3—C4	−178.2 (5)	C8—C13—C14—O6	−163.8 (5)
C2—C3—C4—N1	−0.5 (8)	C12—C13—C14—O5	−164.4 (5)
N1—C5—C6—C2	0.4 (8)	C8—C13—C14—O5	16.5 (8)
C3—C2—C6—C5	−1.3 (7)	C6—C5—N1—C4	0.4 (8)
C1—C2—C6—C5	178.3 (5)	C6—C5—N1—Ag1	−173.0 (4)
O3—C7—C8—C9	−16.1 (6)	C3—C4—N1—C5	−0.4 (7)
O4—C7—C8—C9	162.6 (5)	C3—C4—N1—Ag1	172.6 (4)
O3—C7—C8—C13	162.1 (5)	O3—Ag1—N1—C5	4.1 (8)
O4—C7—C8—C13	−19.2 (8)	Ag1ⁱⁱ—Ag1—N1—C5	−64.4 (4)
C13—C8—C9—C10	−0.1 (7)	O3—Ag1—N1—C4	−168.9 (5)
C7—C8—C9—C10	178.3 (4)	Ag1ⁱⁱ—Ag1—N1—C4	122.6 (4)
C8—C9—C10—C11	−0.1 (8)	O4—C7—O3—Ag1	0.9 (6)
C9—C10—C11—C12	0.3 (8)	C8—C7—O3—Ag1	179.6 (3)
C10—C11—C12—C13	−0.2 (8)	N1—Ag1—O3—C7	0.2 (8)
C11—C12—C13—C8	−0.1 (7)	Ag1ⁱⁱ—Ag1—O3—C7	72.7 (4)
C11—C12—C13—C14	−179.3 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6ⁱⁱⁱ	0.82	1.80	2.616 (5)	175
O5—H5A···O4	0.82	1.57	2.390 (5)	180

Symmetry code: (iii) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	[Ag(C₈H₅O₄)(C₆H₅NO₂)]
M_r	396.10
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	13.540 (3), 8.160 (2), 24.223 (5)
β (°)	99.546 (15)
V (Å³)	2639 (1)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.56
Crystal size (mm)	0.37 × 0.32 × 0.27

Data collection
Diffractometer	Siemens P4 four-circle diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.597, 0.680
No. of measured, independent and observed [I > 2σ(I)] reflections	3909, 3037, 1879
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.00
No. of reflections	3037
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.99, −0.72

Computer programs: XSCANS (Siemens, 1994), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Selected geometric parameters (Å, º) top

Ag1—N1	2.179 (4)	Ag1—O2ⁱ	2.621 (3)
Ag1—O3	2.185 (3)	Ag1—Ag1ⁱⁱ	3.2123 (11)

N1—Ag1—O3	164.57 (14)	O3—Ag1—O2ⁱ	101.74 (11)
N1—Ag1—O2ⁱ	93.52 (12)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O6ⁱⁱⁱ	0.82	1.80	2.616 (5)	175
O5—H5A···O4	0.82	1.57	2.390 (5)	180

Symmetry code: (iii) x, −y+1, z−1/2.

Acknowledgements

The authors thank Shanghai Maritime University for supporting this work.

References

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