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Acta Crystallogr Sect E Struct Rep Online. 2008 March 1; 64(Pt 3): m498–m499.
Published online 2008 February 27. doi:  10.1107/S1600536808004984
PMCID: PMC2960835

catena-Poly[[bis­[μ-2-(3-pyrid­yl)-1H-benzimidazole]-κ2 N 2:N 32 N 3:N 2-disilver(I)]-μ-2,5-dicarboxy­benzene-1,4-dicarboxyl­ato-κ2 O 2:O 5]

Jie Chena,*

Abstract

The title coordination polymer, [Ag2(C10H4O8)(C12H9N3)2]n, was prepared by a hydro­thermal method. The AgI atom exists in a strongly distorted trigonal coordination environment. Two AgI ions related by an inversion centre are coordinated by two 2-(3-pyrid­yl)benzimidazole ligands, forming a centrosymmetric cyclic dimer. The bridging bidentate 2,5-dicarboxy­benzene-1,4-dicarboxyl­ate ligand is also located on an inversion centre and connects the binuclear units, generating a one-dimensional polymer. The almost-planar conformation of this ligand allows it to form a strong intra­molecular O—H(...)O hydrogen bond. Finally, inter­molecular N—H(...)O hydrogen bonds aggregate the chains into a three-dimensional framework.

Related literature

For related literature, see: Alcalde et al. (1992 [triangle]); Cao et al. (2002 [triangle]); Hu et al. (2004 [triangle]); Li et al. (2003 [triangle]); Xia et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m498-scheme1.jpg

Experimental

Crystal data

  • [Ag2(C10H4O8)(C12H9N3)2]
  • M r = 858.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m498-efi1.jpg
  • a = 4.8940 (11) Å
  • b = 16.011 (4) Å
  • c = 19.077 (4) Å
  • β = 92.393 (3)°
  • V = 1493.6 (6) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.38 mm−1
  • T = 293 (2) K
  • 0.48 × 0.13 × 0.13 mm

Data collection

  • Rigaku Mercury CCD diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2000 [triangle]) T min = 0.806, T max = 0.842
  • 11420 measured reflections
  • 3405 independent reflections
  • 3079 reflections with I > 2σ(I)
  • R int = 0.023

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.075
  • S = 1.07
  • 3405 reflections
  • 230 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.50 e Å−3
  • Δρmin = −0.85 e Å−3

Data collection: CrystalClear (Rigaku, 2000 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: CrystalStructure (Rigaku, 2000 [triangle]); software used to prepare material for publication: SHELXL97.

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

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808004984/bh2158sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808004984/bh2158Isup2.hkl

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

Acknowledgments

The author gratefully acknowledges the financial support of the Key Science and Technology Project of Fujian Province (grant No. 2005H045).

supplementary crystallographic information

Comment

1,2,4,5-Benzenetetracarboxylic acid (H4BTEC) has been regarded as an excellent candidate for the construction of multi-dimensional coordination polymers for its versatile coordination modes and rich hydrogen bonding (Cao et al., 2002; Hu et al., 2004; Li et al., 2003). The coordination supramolecular architectures are controlled by the extent of the deprotonation of H4BTEC, nature of the auxiliary ligands, and metal coordination centers.

In the title coordination polymer, (I), the AgI is three coordinated (Fig. 1). Two symmetry related AgI ions are bonded by four N atoms from two 2-(3-pyridyl)-1H-benzimidazole ligands in the head to end mode, forming a centrosymmetric cyclic dimer. The coordination sphere of the cyclic dimer is completed by the 2,5-dicarboxybenzene-1,4-dicarboxylate coordinating in a bis(monodentate) fashion, which is similar to the coordination mode reported by Xia et al. (2007). The centrosymmetric bridging 2,5-dicarboxybenzene-1,4-dicarboxylate ligands link the binuclear units into a one-dimensional polymeric chain (Fig. 2). Interestingly, the coordinating O atom is provided by the undeprotonated carboxylic group rather than the deprotonated one. The O2—H group in the undeprotonated carboxylic group forms a strong intramolecular hydrogen bond with the adjacent carboxylate group [O2···O4: 2.399 (3) Å]. This contact allows planarity for the bridging ligand, which may be related to the non-coordinating character of carboxylate functionalities. The uncoordinated carboxylate group also provides another O atom for the formation of intermolecular hydrogen bonds [N3···O3: 2.742 (3) Å], forming a three-dimensional framework (Fig. 3). Despite of the presence of aromatic rings, no apparent π···π stacking interactions are found in the crystal structure.

Experimental

A solution of Ag2O (0.07 g, 0.30 mmol), 2-(3-pyridyl)-1H-benzimidazole (Alcalde et al., 1992) (0.14 g, 0.61 mmol), 1,2,4,5-benzenetetracarboxylic acid (0.066 g, 0.30 mmol) and H2O (15 ml) was stirred under ambient conditions. The solution was sealed in a 25 ml Teflon-lined stainless steel vessel, heated at 413 K for 4 days and cooled to room temperature for 3 days. The resulting product was recovered by filtration, washed with distilled water and dried in air (65% yield).

Refinement

Anisotropic thermal parameters were applied to all non-hydrogen atoms. The carboxylic acid H atom H2B was initially located in a difference map, and then refined with a restrained O—H bond length of 0.83 (1) Å. Other H atoms were fixed geometrically and allowed to ride on their parent atoms, with C—H = 0.93 Å, N—H = 0.86 Å, and Uiso(H) = 1.2Ueq(carrier atom).

Figures

Fig. 1.
The structure of (I), with the atomic labels and 30% probability displacement ellipsoids for non-H atoms. [Symmetry codes: (i) 2 - x, -y, 2 - z; (ii) 1 - x, 1 - y, 2 - z].
Fig. 2.
A view of the one-dimensional chain of (I). H atoms are omitted for clarity.
Fig. 3.
The crystal packing of (I). H atoms are omitted for clarity.

Crystal data

[Ag2(C10H4O8)(C12H9N3)2]F000 = 852
Mr = 858.32Dx = 1.909 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3641 reflections
a = 4.8940 (11) Åθ = 2.5–27.5º
b = 16.011 (4) ŵ = 1.38 mm1
c = 19.077 (4) ÅT = 293 (2) K
β = 92.393 (3)ºPrism, colourless
V = 1493.6 (6) Å30.48 × 0.13 × 0.13 mm
Z = 2

Data collection

Rigaku Mercury CCD diffractometer3405 independent reflections
Radiation source: fine-focus sealed tube3079 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.023
T = 293(2) Kθmax = 27.5º
ω scansθmin = 2.5º
Absorption correction: multi-scan(CrystalClear; Rigaku, 2000)h = −6→6
Tmin = 0.806, Tmax = 0.842k = −20→20
11420 measured reflectionsl = −18→24

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.075  w = 1/[σ2(Fo2) + (0.0366P)2 + 0.9191P] where P = (Fo2 + 2Fc2)/3
S = 1.07(Δ/σ)max = 0.005
3405 reflectionsΔρmax = 0.50 e Å3
230 parametersΔρmin = −0.85 e Å3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods

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

xyzUiso*/Ueq
Ag10.71244 (4)0.134099 (11)1.018347 (10)0.04125 (9)
C11.1680 (5)−0.15500 (14)1.13812 (13)0.0343 (5)
H1A1.2997−0.19631.13360.041*
C21.0649 (5)−0.14053 (14)1.20320 (14)0.0359 (5)
H2A1.1275−0.17171.24180.043*
C30.8688 (5)−0.07976 (15)1.21087 (12)0.0329 (5)
H3B0.7980−0.06951.25450.039*
C40.7781 (4)−0.03380 (13)1.15231 (12)0.0265 (4)
C50.8913 (5)−0.05275 (13)1.08884 (12)0.0324 (5)
H5A0.8300−0.02321.04930.039*
C60.5728 (4)0.03242 (13)1.15806 (11)0.0264 (4)
C70.3021 (5)0.13812 (13)1.13776 (12)0.0269 (4)
C80.1575 (5)0.20687 (14)1.11051 (13)0.0347 (5)
H8A0.18600.22691.06560.042*
C9−0.0299 (5)0.24392 (16)1.15313 (14)0.0386 (6)
H9A−0.12870.29001.13650.046*
C10−0.0745 (5)0.21380 (16)1.22058 (14)0.0383 (6)
H10A−0.20390.23991.24740.046*
C110.0682 (5)0.14644 (15)1.24842 (13)0.0332 (5)
H11A0.03960.12671.29340.040*
C120.2577 (4)0.10963 (13)1.20541 (11)0.0264 (4)
C130.5075 (5)0.32005 (13)0.96973 (12)0.0322 (5)
C140.4884 (5)0.41435 (13)0.98108 (11)0.0271 (4)
C150.3175 (5)0.47238 (13)0.94531 (11)0.0271 (4)
C160.1144 (5)0.45603 (15)0.88456 (12)0.0320 (5)
C170.3352 (5)0.55568 (14)0.96571 (12)0.0297 (5)
H17A0.22140.59390.94220.036*
N11.0845 (4)−0.11132 (12)1.08101 (11)0.0347 (4)
N20.5015 (4)0.08847 (11)1.10831 (9)0.0273 (4)
N30.4299 (4)0.04296 (11)1.21627 (9)0.0273 (4)
H3A0.44430.01311.25370.033*
O10.6918 (4)0.28180 (11)1.00119 (11)0.0484 (5)
O20.3341 (4)0.28260 (11)0.92949 (12)0.0486 (5)
H2B0.217 (7)0.316 (2)0.912 (2)0.082 (13)*
O30.0298 (4)0.51666 (11)0.84962 (9)0.0440 (4)
O40.0356 (4)0.38153 (11)0.87095 (10)0.0456 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Ag10.05515 (15)0.02899 (12)0.04086 (13)0.01185 (8)0.01680 (9)0.00789 (7)
C10.0358 (12)0.0225 (10)0.0449 (14)0.0059 (9)0.0042 (10)0.0043 (9)
C20.0383 (13)0.0301 (12)0.0393 (13)0.0058 (10)0.0011 (10)0.0093 (9)
C30.0362 (12)0.0305 (12)0.0320 (12)0.0041 (10)0.0018 (9)0.0010 (9)
C40.0274 (11)0.0187 (9)0.0333 (11)−0.0010 (8)0.0010 (8)−0.0001 (8)
C50.0411 (13)0.0216 (10)0.0347 (12)0.0054 (9)0.0037 (10)0.0026 (8)
C60.0283 (11)0.0205 (10)0.0303 (11)−0.0005 (8)−0.0007 (8)−0.0007 (8)
C70.0263 (11)0.0219 (10)0.0323 (11)−0.0002 (8)−0.0002 (8)−0.0008 (8)
C80.0368 (13)0.0280 (11)0.0386 (13)0.0034 (10)−0.0037 (10)0.0050 (9)
C90.0372 (13)0.0284 (12)0.0492 (15)0.0097 (10)−0.0073 (11)−0.0006 (10)
C100.0324 (12)0.0360 (13)0.0463 (14)0.0081 (10)0.0001 (10)−0.0107 (10)
C110.0319 (12)0.0337 (12)0.0339 (12)0.0015 (9)0.0014 (9)−0.0027 (9)
C120.0259 (11)0.0223 (10)0.0307 (11)0.0005 (8)−0.0023 (8)−0.0012 (8)
C130.0455 (14)0.0189 (10)0.0327 (12)0.0017 (9)0.0057 (10)−0.0001 (8)
C140.0379 (12)0.0173 (9)0.0261 (10)0.0030 (8)0.0037 (9)0.0002 (7)
C150.0347 (12)0.0219 (10)0.0249 (10)0.0022 (9)0.0035 (8)0.0003 (8)
C160.0380 (13)0.0309 (11)0.0269 (11)0.0029 (9)0.0012 (9)−0.0016 (9)
C170.0400 (13)0.0207 (10)0.0282 (11)0.0055 (9)−0.0013 (9)0.0031 (8)
N10.0428 (12)0.0208 (9)0.0410 (11)0.0040 (8)0.0082 (9)0.0028 (8)
N20.0303 (10)0.0220 (9)0.0297 (9)0.0025 (7)0.0020 (7)0.0016 (7)
N30.0304 (10)0.0244 (9)0.0272 (9)0.0038 (7)0.0014 (7)0.0023 (7)
O10.0691 (13)0.0194 (8)0.0554 (11)0.0126 (8)−0.0126 (10)0.0003 (7)
O20.0545 (12)0.0220 (8)0.0680 (13)0.0009 (8)−0.0133 (10)−0.0091 (8)
O30.0638 (12)0.0335 (9)0.0334 (9)0.0062 (9)−0.0137 (8)−0.0009 (7)
O40.0538 (12)0.0345 (9)0.0471 (11)−0.0065 (8)−0.0147 (9)−0.0035 (8)

Geometric parameters (Å, °)

Ag1—N22.1663 (18)C9—H9A0.9300
Ag1—N1i2.207 (2)C10—C111.379 (3)
Ag1—O12.3889 (18)C10—H10A0.9300
C1—N11.344 (3)C11—C121.394 (3)
C1—C21.379 (4)C11—H11A0.9300
C1—H1A0.9300C12—N31.370 (3)
C2—C31.379 (3)C13—O11.226 (3)
C2—H2A0.9300C13—O21.271 (3)
C3—C41.395 (3)C13—C141.529 (3)
C3—H3B0.9300C14—C17ii1.390 (3)
C4—C51.386 (3)C14—C151.407 (3)
C4—C61.468 (3)C15—C171.391 (3)
C5—N11.344 (3)C15—C161.518 (3)
C5—H5A0.9300C16—O31.239 (3)
C6—N31.347 (3)C16—O41.277 (3)
C6—N21.342 (3)C16—O41.277 (3)
C7—C81.397 (3)C17—H17A0.9300
C7—N21.395 (3)N3—O3iii2.742 (3)
C7—C121.394 (3)N3—H3A0.8600
C8—C91.384 (4)O2—O42.399 (3)
C8—H8A0.9300O2—H2B0.846 (19)
C9—C101.400 (4)
N2—Ag1—N1i150.61 (7)C12—C11—H11A121.9
N2—Ag1—O1115.06 (7)N3—C12—C11131.3 (2)
N1i—Ag1—O193.66 (7)N3—C12—C7106.02 (18)
N1—C1—C2122.1 (2)C11—C12—C7122.7 (2)
N1—C1—H1A118.9O1—C13—O2121.3 (2)
C2—C1—H1A118.9O1—C13—C14118.2 (2)
C3—C2—C1119.8 (2)O2—C13—C14120.5 (2)
C3—C2—H2A120.1C17ii—C14—C15117.68 (19)
C1—C2—H2A120.1C17ii—C14—C13113.86 (19)
C2—C3—C4119.1 (2)C15—C14—C13128.5 (2)
C2—C3—H3B120.4C17—C15—C14117.9 (2)
C4—C3—H3B120.4C17—C15—C16114.22 (19)
C5—C4—C3117.3 (2)C14—C15—C16127.83 (19)
C5—C4—C6121.6 (2)O3—C16—O4122.1 (2)
C3—C4—C6121.1 (2)O3—C16—O4122.1 (2)
N1—C5—C4124.0 (2)O3—C16—C15118.0 (2)
N1—C5—H5A118.0O4—C16—C15119.9 (2)
C4—C5—H5A118.0O4—C16—C15119.9 (2)
N3—C6—N2111.75 (19)C15—C17—C14ii124.4 (2)
N3—C6—C4122.18 (19)C15—C17—H17A117.8
N2—C6—C4126.1 (2)C14ii—C17—H17A117.8
C8—C7—N2130.6 (2)C5—N1—C1117.7 (2)
C8—C7—C12120.4 (2)C5—N1—Ag1i123.69 (16)
N2—C7—C12108.97 (19)C1—N1—Ag1i118.53 (16)
C9—C8—C7117.2 (2)C6—N2—C7105.18 (18)
C9—C8—H8A121.4C6—N2—Ag1131.88 (15)
C7—C8—H8A121.4C7—N2—Ag1119.44 (14)
C8—C9—C10121.7 (2)C6—N3—C12108.07 (18)
C8—C9—H9A119.2C6—N3—O3iii129.98 (14)
C10—C9—H9A119.2C12—N3—O3iii119.74 (14)
C11—C10—C9121.9 (2)C6—N3—H3A126.0
C11—C10—H10A119.1C12—N3—H3A126.0
C9—C10—H10A119.1C13—O1—Ag1125.98 (17)
C10—C11—C12116.3 (2)C13—O2—O4110.37 (15)
C10—C11—H11A121.9C13—O2—H2B111 (3)
N1—C1—C2—C30.3 (4)C14—C15—C17—C14ii0.3 (4)
C1—C2—C3—C40.0 (4)C16—C15—C17—C14ii−178.4 (2)
C2—C3—C4—C50.4 (3)C4—C5—N1—C11.3 (4)
C2—C3—C4—C6−179.0 (2)C4—C5—N1—Ag1i−174.85 (17)
C3—C4—C5—N1−1.1 (4)C2—C1—N1—C5−0.9 (4)
C6—C4—C5—N1178.3 (2)C2—C1—N1—Ag1i175.50 (19)
C5—C4—C6—N3169.4 (2)N3—C6—N2—C70.7 (2)
C3—C4—C6—N3−11.2 (3)C4—C6—N2—C7−179.8 (2)
C5—C4—C6—N2−10.2 (3)N3—C6—N2—Ag1158.67 (15)
C3—C4—C6—N2169.2 (2)C4—C6—N2—Ag1−21.7 (3)
N2—C7—C8—C9−179.8 (2)C8—C7—N2—C6179.0 (2)
C12—C7—C8—C9−0.6 (3)C12—C7—N2—C6−0.3 (2)
C7—C8—C9—C10−0.3 (4)C8—C7—N2—Ag117.7 (3)
C8—C9—C10—C110.9 (4)C12—C7—N2—Ag1−161.64 (14)
C9—C10—C11—C12−0.5 (4)N1i—Ag1—N2—C657.2 (3)
C10—C11—C12—N3−179.8 (2)O1—Ag1—N2—C6−135.92 (19)
C10—C11—C12—C7−0.4 (4)N1i—Ag1—N2—C7−147.28 (17)
C8—C7—C12—N3−179.5 (2)O1—Ag1—N2—C719.57 (18)
N2—C7—C12—N3−0.1 (2)N2—C6—N3—C12−0.8 (2)
C8—C7—C12—C110.9 (4)C4—C6—N3—C12179.6 (2)
N2—C7—C12—C11−179.7 (2)N2—C6—N3—O3iii−163.40 (15)
O1—C13—C14—C17ii−8.4 (3)C4—C6—N3—O3iii17.0 (3)
O2—C13—C14—C17ii170.6 (2)C11—C12—N3—C6−180.0 (2)
O1—C13—C14—C15172.0 (2)C7—C12—N3—C60.5 (2)
O2—C13—C14—C15−9.0 (4)C11—C12—N3—O3iii−15.2 (3)
C17ii—C14—C15—C17−0.3 (4)C7—C12—N3—O3iii165.26 (14)
C13—C14—C15—C17179.3 (2)O2—C13—O1—Ag1−15.7 (4)
C17ii—C14—C15—C16178.2 (2)C14—C13—O1—Ag1163.34 (15)
C13—C14—C15—C16−2.1 (4)N2—Ag1—O1—C13−85.5 (2)
C17—C15—C16—O315.1 (3)N1i—Ag1—O1—C1388.1 (2)
C14—C15—C16—O3−163.5 (2)O1—C13—O2—O4−175.0 (2)
C17—C15—C16—O4−164.8 (2)C14—C13—O2—O46.0 (3)
C14—C15—C16—O416.6 (4)O3—C16—O4—O40.0 (4)
C17—C15—C16—O4−164.8 (2)C15—C16—O4—O40.0 (3)
C14—C15—C16—O416.6 (4)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2B···O40.846 (19)1.56 (2)2.399 (3)171 (4)
N3—H3A···O3iii0.861.922.742 (3)159

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2158).

References

  • Alcalde, E., Dinarés, I., Pérez-García, L. & Roca, T. (1992). Synthesis, pp. 395–398.
  • Cao, R., Sun, D., Liang, Y., Hong, M., Tatsumi, K. & Shi, Q. (2002). Inorg. Chem.41, 2087–2094. [PubMed]
  • Hu, M.-L., Xiao, H.-P. & Yuan, J.-X. (2004). Acta Cryst. C60, m112–m113. [PubMed]
  • Li, Y., Hao, N., Lu, Y., Wang, E., Kang, Z. & Hu, C. (2003). Inorg. Chem.42, 3119–3124. [PubMed]
  • Rigaku (2000). CrystalStructure (Version 3.7.0) and CrystalClear (Version 1.36). Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Xia, C.-K., Wu, W., Qiu, L. & Xie, J.-M. (2007). Acta Cryst. E63, m2881.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography