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Acta Cryst. (2008). E64, m498-m499    [ doi:10.1107/S1600536808004984 ]

catena-Poly[[bis[[mu]-2-(3-pyridyl)-1H-benzimidazole]-[kappa]2N2:N3;[kappa]2N3:N2-disilver(I)]-[mu]-2,5-dicarboxybenzene-1,4-dicarboxylato-[kappa]2O2:O5]

J. Chen

Abstract top

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.

Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] 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].
[Figure 2] Fig. 2. A view of the one-dimensional chain of (I). H atoms are omitted for clarity.
[Figure 3] Fig. 3. The crystal packing of (I). H atoms are omitted for clarity.
catena-Poly[[bis[µ-2-(3-pyridyl)-1H-benzimidazole]- κ2N2:N3;κ2N3:N2-disilver(I)]-µ-2,5-dicarboxybenzene-1,4- dicarboxylato-κ2O2:O5] top
Crystal data top
[Ag2(C10H4O8)(C12H9N3)2]F000 = 852
Mr = 858.32Dx = 1.909 Mg m−3
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 mm−1
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 top
Rigaku Mercury CCD
diffractometer		3405 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 top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H 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 Å−3
230 parametersΔρmin = −0.85 e Å−3
1 restraintExtinction correction: none
Primary atom site location: structure-invariant direct methods
Crystal data top
[Ag2(C10H4O8)(C12H9N3)2]V = 1493.6 (6) Å3
Mr = 858.32Z = 2
Monoclinic, P21/nMo Kα
a = 4.8940 (11) ŵ = 1.38 mm−1
b = 16.011 (4) ÅT = 293 (2) K
c = 19.077 (4) Å0.48 × 0.13 × 0.13 mm
β = 92.393 (3)º
Data collection top
Rigaku Mercury CCD
diffractometer		3405 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku, 2000)		3079 reflections with I > 2σ(I)
Tmin = 0.806, Tmax = 0.842Rint = 0.023
11420 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0301 restraint
wR(F2) = 0.075H atoms treated by a mixture of
independent and constrained refinement
S = 1.07Δρmax = 0.50 e Å−3
3405 reflectionsΔρmin = −0.85 e Å−3
230 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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, °) top
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.
Table 1
Selected geometric parameters (Å, °) top
Ag1—N22.1663 (18)Ag1—O12.3889 (18)
Ag1—N1i2.207 (2)
N2—Ag1—N1i150.61 (7)N1i—Ag1—O193.66 (7)
N2—Ag1—O1115.06 (7)
Symmetry codes: (i) −x+2, −y, −z+2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2B···O40.846 (19)1.56 (2)2.399 (3)171 (4)
N3—H3A···O3ii0.861.922.742 (3)159
Symmetry codes: (ii) x+1/2, −y+1/2, z+1/2.
Acknowledgements top

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

references
References top

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