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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): m779.
Published online 2008 May 7. doi:  10.1107/S1600536808009586
PMCID: PMC2961433

catena-Poly[[bis­[(2-carboxy­benzoato-κO)silver(I)](AgAg)]bis­(μ-isonicotinic acid-κ2 N:O)]

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0m779-scheme1.jpg

Experimental

Crystal data

  • [Ag(C8H5O4)(C6H5NO2)]
  • M r = 396.10
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m779-efi1.jpg
  • 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 [triangle]) 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[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.119
  • S = 1.00
  • 3037 reflections
  • 199 parameters
  • H-atom parameters constrained
  • Δρmax = 0.99 e Å−3
  • Δρmin = −0.71 e Å−3

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

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank Shanghai Maritime University for supporting this work.

supplementary crystallographic information

Comment

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.

Experimental

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

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).

Figures

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.

Crystal data

[Ag(C8H5O4)(C6H5NO2)]F000 = 1568
Mr = 396.10Dx = 1.994 Mg m3
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 mm1
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

Siemens P4 four-circle diffractometerRint = 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

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 Å3
199 parametersΔρmin = −0.71 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HY2121).

References

  • 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. [PubMed]
  • 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.

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