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Acta Cryst. (2008). E64, m779    [ doi:10.1107/S1600536808009586 ]

catena-Poly[[bis[(2-carboxybenzoato-[kappa]O)silver(I)](Ag-Ag)]bis([mu]-isonicotinic acid-[kappa]2N:O)]

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

Abstract top

The title compound, [Ag(C8H5O4)(C6H5NO2)]n, contains one AgI 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.

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 AgI 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%.

Refinement top

H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 and O—H = 0.82Å and Uiso(H) = 1.2Ueq(C,O).

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
[Figure 1] 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.]
[Figure 2] 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)]F000 = 1568
Mr = 396.10Dx = 1.994 Mg m−3
Monoclinic, C2/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 28 reflections
a = 13.540 (3) Åθ = 5.2–12.4º
b = 8.160 (2) ŵ = 1.56 mm−1
c = 24.223 (5) ÅT = 293 (2) K
β = 99.546 (15)ºBlock, purple
V = 2639 (1) Å30.37 × 0.32 × 0.27 mm
Z = 8
Data collection top
Siemens P4 four-circle
diffractometer		Rint = 0.034
Radiation source: medium-focus sealed tubeθmax = 27.5º
Monochromator: graphiteθmin = 1.7º
T = 293(2) Kh = −17→1
ω–2θ scansk = −1→10
Absorption correction: ψ scan
(North et al., 1968)		l = −31→31
Tmin = 0.597, Tmax = 0.6803 standard reflections
3909 measured reflections every 97 reflections
3037 independent reflections intensity decay: 1.0%
1879 reflections with I > 2σ(I)
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.119  w = 1/[σ2(Fo2) + (0.0526P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
3037 reflectionsΔρmax = 0.99 e Å−3
199 parametersΔρmin = −0.71 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ag(C8H5O4)(C6H5NO2)]V = 2639 (1) Å3
Mr = 396.10Z = 8
Monoclinic, C2/cMo Kα
a = 13.540 (3) ŵ = 1.56 mm−1
b = 8.160 (2) ÅT = 293 (2) K
c = 24.223 (5) Å0.37 × 0.32 × 0.27 mm
β = 99.546 (15)º
Data collection top
Siemens P4 four-circle
diffractometer		1879 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)		Rint = 0.034
Tmin = 0.597, Tmax = 0.6803 standard reflections
3909 measured reflections every 97 reflections
3037 independent reflections intensity decay: 1.0%
Refinement top
R[F2 > 2σ(F2)] = 0.042199 parameters
wR(F2) = 0.119H-atom parameters constrained
S = 1.00Δρmax = 0.99 e Å−3
3037 reflectionsΔρmin = −0.71 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.40822 (3)0.04719 (5)0.698630 (15)0.05417 (17)
C10.4164 (4)0.7535 (6)0.58243 (19)0.0405 (11)
C20.4211 (3)0.5872 (5)0.60835 (17)0.0347 (10)
C30.4339 (4)0.4453 (6)0.57882 (17)0.0397 (10)
H3A0.44170.45140.54150.048*
C40.4348 (4)0.2962 (6)0.60478 (18)0.0413 (11)
H4A0.44300.20200.58440.050*
C50.4137 (4)0.4183 (6)0.68640 (19)0.0442 (12)
H5B0.40700.40870.72390.053*
C60.4119 (4)0.5724 (6)0.66396 (19)0.0455 (12)
H6A0.40460.66440.68560.055*
C70.3575 (4)−0.0952 (6)0.80056 (17)0.0383 (11)
C80.3373 (3)−0.2215 (5)0.84252 (16)0.0307 (9)
C90.3225 (3)−0.3796 (6)0.82196 (17)0.0368 (10)
H9A0.3240−0.39750.78420.044*
C100.3056 (4)−0.5119 (6)0.8547 (2)0.0437 (11)
H10A0.2958−0.61640.83940.052*
C110.3036 (4)−0.4842 (6)0.9109 (2)0.0453 (12)
H11A0.2927−0.57110.93400.054*
C120.3177 (4)−0.3304 (6)0.93258 (18)0.0403 (11)
H12A0.3159−0.31450.97040.048*
C130.3346 (3)−0.1963 (5)0.89994 (17)0.0321 (9)
C140.3497 (4)−0.0355 (6)0.93203 (18)0.0411 (11)
N10.4245 (3)0.2820 (5)0.65827 (15)0.0414 (9)
O10.3992 (3)0.7496 (5)0.52779 (12)0.0626 (11)
H1A0.38960.84310.51560.094*
O20.4267 (3)0.8778 (4)0.60899 (13)0.0513 (9)
O30.3817 (3)−0.1459 (4)0.75691 (13)0.0579 (10)
O40.3483 (3)0.0565 (4)0.80925 (14)0.0619 (11)
O50.3438 (3)0.1015 (4)0.90631 (14)0.0579 (10)
H5A0.34540.08580.87300.087*
O60.3672 (3)−0.0408 (4)0.98320 (13)0.0641 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0797 (3)0.0432 (2)0.0430 (2)0.0001 (2)0.02032 (19)0.01176 (18)
C10.046 (3)0.038 (3)0.037 (2)0.002 (2)0.007 (2)0.002 (2)
C20.037 (2)0.037 (2)0.030 (2)−0.001 (2)0.0055 (18)0.0028 (18)
C30.055 (3)0.036 (2)0.028 (2)−0.003 (2)0.008 (2)0.0023 (19)
C40.055 (3)0.037 (2)0.034 (2)0.000 (2)0.012 (2)−0.0002 (19)
C50.061 (3)0.039 (3)0.034 (2)−0.002 (2)0.012 (2)0.0022 (19)
C60.065 (3)0.042 (3)0.031 (2)0.005 (3)0.014 (2)−0.002 (2)
C70.046 (3)0.042 (3)0.027 (2)−0.001 (2)0.0060 (19)0.0026 (19)
C80.038 (2)0.028 (2)0.0250 (18)−0.0007 (19)0.0035 (17)0.0007 (17)
C90.050 (3)0.034 (2)0.0278 (19)−0.001 (2)0.0098 (19)−0.0021 (18)
C100.045 (3)0.027 (2)0.057 (3)−0.003 (2)0.004 (2)−0.001 (2)
C110.058 (3)0.037 (3)0.042 (2)−0.005 (2)0.009 (2)0.010 (2)
C120.051 (3)0.040 (3)0.030 (2)−0.003 (2)0.007 (2)0.0033 (19)
C130.038 (2)0.028 (2)0.031 (2)0.002 (2)0.0056 (18)0.0000 (17)
C140.053 (3)0.036 (3)0.035 (2)−0.004 (2)0.012 (2)−0.006 (2)
N10.053 (2)0.038 (2)0.0349 (18)−0.0020 (19)0.0101 (18)0.0034 (17)
O10.112 (3)0.042 (2)0.0295 (16)−0.002 (2)−0.0001 (19)0.0104 (15)
O20.075 (3)0.0364 (18)0.0425 (18)0.0043 (19)0.0082 (17)0.0005 (16)
O30.101 (3)0.0417 (19)0.0379 (17)0.004 (2)0.0313 (19)0.0044 (16)
O40.116 (3)0.0339 (18)0.0379 (17)−0.003 (2)0.019 (2)0.0053 (15)
O50.107 (3)0.0303 (17)0.0380 (17)−0.006 (2)0.017 (2)−0.0037 (15)
O60.117 (3)0.047 (2)0.0278 (15)−0.004 (2)0.0086 (19)−0.0078 (16)
Geometric parameters (Å, °) top
Ag1—N12.179 (4)C7—O41.265 (6)
Ag1—O32.185 (3)C7—C81.504 (6)
Ag1—O2i2.621 (3)C8—C91.385 (6)
Ag1—Ag1ii3.2123 (11)C8—C131.412 (5)
C1—O21.197 (6)C9—C101.380 (6)
C1—O11.306 (5)C9—H9A0.9300
C1—C21.492 (6)C10—C111.387 (7)
C2—C61.379 (6)C10—H10A0.9300
C2—C31.386 (6)C11—C121.361 (7)
C3—C41.368 (6)C11—H11A0.9300
C3—H3A0.9300C12—C131.391 (6)
C4—N11.331 (5)C12—H12A0.9300
C4—H4A0.9300C13—C141.521 (6)
C5—N11.325 (6)C14—O61.223 (5)
C5—C61.368 (7)C14—O51.276 (6)
C5—H5B0.9300O1—H1A0.8200
C6—H6A0.9300O5—H5A0.8200
C7—O31.229 (5)
N1—Ag1—O3164.57 (14)C9—C8—C7115.3 (3)
N1—Ag1—O2i93.52 (12)C13—C8—C7127.1 (4)
O3—Ag1—O2i101.74 (11)C10—C9—C8123.4 (4)
N1—Ag1—Ag1ii102.98 (11)C10—C9—H9A118.3
O3—Ag1—Ag1ii71.85 (11)C8—C9—H9A118.3
O2—C1—O1123.4 (4)C9—C10—C11117.9 (4)
O2—C1—C2123.5 (4)C9—C10—H10A121.0
O1—C1—C2113.1 (4)C11—C10—H10A121.0
C6—C2—C3118.0 (4)C12—C11—C10120.3 (4)
C6—C2—C1119.1 (4)C12—C11—H11A119.8
C3—C2—C1122.9 (4)C10—C11—H11A119.8
C4—C3—C2119.8 (4)C11—C12—C13122.2 (4)
C4—C3—H3A120.1C11—C12—H12A118.9
C2—C3—H3A120.1C13—C12—H12A118.9
N1—C4—C3122.0 (4)C12—C13—C8118.6 (4)
N1—C4—H4A119.0C12—C13—C14114.1 (4)
C3—C4—H4A119.0C8—C13—C14127.3 (4)
N1—C5—C6124.3 (4)O6—C14—O5120.8 (4)
N1—C5—H5B117.9O6—C14—C13118.3 (4)
C6—C5—H5B117.9O5—C14—C13120.9 (4)
C5—C6—C2118.0 (5)C5—N1—C4117.8 (4)
C5—C6—H6A121.0C5—N1—Ag1118.6 (3)
C2—C6—H6A121.0C4—N1—Ag1123.3 (3)
O3—C7—O4121.4 (4)C1—O1—H1A109.5
O3—C7—C8117.0 (4)C7—O3—Ag1114.1 (3)
O4—C7—C8121.6 (4)C14—O5—H5A109.5
C9—C8—C13117.6 (4)
O2—C1—C2—C616.8 (8)C9—C8—C13—C120.2 (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—C14179.3 (4)
O1—C1—C2—C316.8 (7)C7—C8—C13—C141.1 (8)
C6—C2—C3—C41.3 (7)C12—C13—C14—O615.3 (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—C20.4 (8)C8—C13—C14—O516.5 (8)
C3—C2—C6—C5−1.3 (7)C6—C5—N1—C40.4 (8)
C1—C2—C6—C5178.3 (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—C9162.6 (5)C3—C4—N1—Ag1172.6 (4)
O3—C7—C8—C13162.1 (5)O3—Ag1—N1—C54.1 (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—C10178.3 (4)Ag1ii—Ag1—N1—C4122.6 (4)
C8—C9—C10—C11−0.1 (8)O4—C7—O3—Ag10.9 (6)
C9—C10—C11—C120.3 (8)C8—C7—O3—Ag1179.6 (3)
C10—C11—C12—C13−0.2 (8)N1—Ag1—O3—C70.2 (8)
C11—C12—C13—C8−0.1 (7)Ag1ii—Ag1—O3—C772.7 (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, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O6iii0.821.802.616 (5)175
O5—H5A···O40.821.572.390 (5)180
Symmetry codes: (iii) x, −y+1, z−1/2.
Table 1
Selected geometric parameters (Å, °) top
Ag1—N12.179 (4)Ag1—O2i2.621 (3)
Ag1—O32.185 (3)Ag1—Ag1ii3.2123 (11)
N1—Ag1—O3164.57 (14)O3—Ag1—O2i101.74 (11)
N1—Ag1—O2i93.52 (12)
Symmetry codes: (i) x, y−1, z; (ii) −x+1, y, −z+3/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O6iii0.821.802.616 (5)175
O5—H5A···O40.821.572.390 (5)180
Symmetry codes: (iii) x, −y+1, z−1/2.
Acknowledgements top

The authors thank Shanghai Maritime University for supporting this work.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

He, Y.-K., Han, Z.-B., Ma, Y. & Zhang, X.-D. (2007). Inorg. Chem. Commun. 10, 829–832.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Siemens (1994). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Westrip, S. P. (2008). PublCIF. In preparation.

Xie, F.-T., Bie, H.-Y., Duan, L.-M., Li, G.-H., Zhang, X. & Xu, J.-Q. (2005). J. Solid State Chem. 178, 2858–2866.