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Acta Cryst. (2007). E63, m2964    [ doi:10.1107/S1600536807055213 ]

catena-Poly[[bis[[mu]-2-(3-pyridyl)-1H-benzimidazole]disilver(I)]-[mu]-benzene-1,4-disulfonato]

J. Chen and Y. Ruan

Abstract top

The title compound, [Ag2(C6H4O6S2)(C12H9N3)2]n, is a coordination polymer prepared by a hydrothermal reaction. Two AgI atoms are connected by two 2-(3-pyridyl)benzimidazole ligands, resulting in a binuclear macrocycle. The bridging benzene-1,4-disulfonate ligands link the binuclear units, forming a chain. The crystal packing is stabilized by N-H...O hydrogen bonds.

Comment top

4-sulfobenzoic acid is an efficient O donor ligand, exhibiting versatile coordination mode and hydrogen bonding interaction in the assembly of metal-organic coordination polymers (Yuan et al., 2001), 4-sulfobenzoic acid could be in situ synthesized into benzene-1,4-disulfonate (Xiong et al., 2001). 2-(3-pyridyl)benzimidazole has been reported to connect the AgI ions, resulting in a binuclear macrocyclic (Su et al., 1999). Herein, we report the synthesis and structure of the coordination polymer on the basis of bridging benzene-1,4-disulfonate ligands and [Ag2(C12H9N3)2] binuclear units.

In the title compound, AgI exhibits a distorted trigonal planar geometry (Fig. 1). Each two AgI atoms are connected with two 2-(3-pyridyl)benzimidazole ligands in the end to end mode via Npy and NBIm donor atoms, forming a binuclear macrocyclic. The coordination sphere of AgI is completed by an oxygen atom from benzene-1,4-disulfonate with bis(monodentate) coordination fashion. The bridging benzene-1,4-disulfonate ligands link the binuclear units, forming a chain (Fig. 2). The chains are assembled into a two-dimensional network by the N—H···O hydrogen bonds as well as π-π interactions between the benzimidazolyl rings of 2-(3-pyridyl)benzimidazole ligands (the perpendicular distance is about 3.43 Å) (Fig. 3). The crystal packing can be viewed as layered arrangement of the two-dimensional supramolecular networks (Fig. 4).

Related literature top

For related structures, see: Yuan et al. (2001); Xiong et al. (2001); Su et al. (1999). For related literature, see: Alcade et al. (1992).

Experimental top

A solution of Ag2O (0.07 g, 0.30 mmol), 2-(3-pyridyl)benzimidazole (Alcade et al., 1992) (0.14 g, 0.61 mmol) 4-sulfobenzoic acid (0.06 g, 0.30 mmol) and H2O (15 ml) was stirred under ambient condition and then sealed in teflon-lined stainless steel vessel, heated at 403 K for 4 days and cooled to room temperature for 3 days, creating the colorless crystals of the title compound.

Refinement top

All H atoms were fixed geometrically and allowed to ride on their attached atoms with C—H=0.93 Å, N—H=0.86 Å and U(H) = 1.2 Ueq(C,N).

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku, 2000); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. A view of the molecular structue of the title compound. Displacement ellipsoids are drawn at the 30% probbability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i)1 − x, 1 − y, −z; (ii)-1 − x, 2 − y, −z.]
[Figure 2] Fig. 2. A view of the one-dimensional chain of the title compound. The hydrogen atoms are omitted for clarity.
[Figure 3] Fig. 3. A view of the two-dimensional sheet of the title compound. The hydrogen atoms are omitted for clarity. Hydrogen bonds are shown as dashed lines.
[Figure 4] Fig. 4. The crystal packing of the title compound. The hydrogen atoms are omitted for clarity. Hydrogen bonds are shown as dashed lines.
catena-Poly[[bis[µ-2-(3-pyridyl)-1H-benzimidazole]disilver(I)]- µ-benzene-1,4-disulfonato] top
Crystal data top
[Ag2(C6H4S2O6)(C12H9N3)2]Z = 2
Mr = 421.20F000 = 418
Triclinic, P1Dx = 1.979 Mg m−3
Hall symbol: -p 1Mo Kα radiation
λ = 0.71073 Å
a = 7.547 (3) ÅCell parameters from 2133 reflections
b = 10.060 (4) Åθ = 2.9–27.5º
c = 10.286 (4) ŵ = 1.59 mm−1
α = 77.262 (11)ºT = 293 (2) K
β = 69.963 (11)ºPrism, colorless
γ = 77.409 (10)º0.60 × 0.35 × 0.10 mm
V = 706.9 (5) Å3
Data collection top
Rigaku Mercury CCD
diffractometer		3152 independent reflections
Radiation source: Rotating Anode2784 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 293(2) Kθmax = 27.5º
ω scanθmin = 2.9º
Absorption correction: multi-scan
(CrystalStructure; Rigaku, 2000)		h = −9→9
Tmin = 0.518, Tmax = 0.850k = −13→13
5340 measured reflectionsl = −8→13
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)] = 0.061H-atom parameters constrained
wR(F2) = 0.188  w = 1/[σ2(Fo2) + (0.1114P)2 + 1.6836P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
3152 reflectionsΔρmax = 0.85 e Å−3
208 parametersΔρmin = −1.86 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Ag2(C6H4S2O6)(C12H9N3)2]γ = 77.409 (10)º
Mr = 421.20V = 706.9 (5) Å3
Triclinic, P1Z = 2
a = 7.547 (3) ÅMo Kα
b = 10.060 (4) ŵ = 1.59 mm−1
c = 10.286 (4) ÅT = 293 (2) K
α = 77.262 (11)º0.60 × 0.35 × 0.10 mm
β = 69.963 (11)º
Data collection top
Rigaku Mercury CCD
diffractometer		3152 independent reflections
Absorption correction: multi-scan
(CrystalStructure; Rigaku, 2000)		2784 reflections with I > 2σ(I)
Tmin = 0.518, Tmax = 0.850Rint = 0.020
5340 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.061208 parameters
wR(F2) = 0.188H-atom parameters constrained
S = 1.11Δρmax = 0.85 e Å−3
3152 reflectionsΔρmin = −1.86 e Å−3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.21136 (7)0.66405 (5)0.12969 (4)0.0504 (2)
S1−0.2367 (3)0.7926 (2)0.1437 (2)0.0657 (5)
C10.7242 (8)0.1820 (6)0.1720 (6)0.0411 (12)
H1A0.81000.11530.12240.049*
C20.6483 (9)0.1494 (6)0.3124 (7)0.0450 (13)
H2A0.68490.06230.35790.054*
C30.5173 (8)0.2445 (6)0.3881 (6)0.0406 (12)
H3A0.46350.22180.48450.049*
C40.4660 (7)0.3754 (5)0.3187 (5)0.0288 (9)
C50.5556 (8)0.4020 (6)0.1745 (6)0.0378 (11)
H5A0.52740.48990.12690.045*
C60.3252 (7)0.4808 (5)0.3941 (5)0.0283 (9)
C70.1248 (7)0.6644 (5)0.4484 (5)0.0304 (9)
C80.0034 (8)0.7919 (6)0.4505 (6)0.0393 (12)
H8A−0.00860.84740.36780.047*
C9−0.0988 (9)0.8330 (6)0.5804 (7)0.0446 (13)
H9A−0.17810.91780.58500.054*
C10−0.0815 (10)0.7451 (7)0.7058 (7)0.0476 (14)
H10A−0.15300.77300.79150.057*
C110.0369 (8)0.6208 (6)0.7045 (6)0.0394 (11)
H11A0.04790.56460.78710.047*
C120.1399 (7)0.5822 (5)0.5741 (5)0.0306 (10)
C13−0.3807 (7)0.9099 (5)0.0677 (6)0.0321 (10)
C14−0.5786 (7)0.9207 (5)0.1275 (5)0.0346 (10)
H14A−0.63050.86770.21340.042*
C15−0.3035 (7)0.9905 (5)−0.0596 (6)0.0357 (11)
H15A−0.17180.9843−0.09900.043*
N10.6796 (7)0.3085 (5)0.1011 (5)0.0400 (10)
N20.2393 (6)0.5984 (4)0.3372 (4)0.0307 (8)
N30.2692 (6)0.4672 (4)0.5352 (4)0.0327 (9)
H3B0.30740.39880.59090.039*
O1−0.0735 (7)0.8405 (6)0.1194 (6)0.0690 (16)
O2−0.3410 (9)0.7512 (7)0.2775 (6)0.087 (2)
O3−0.179 (3)0.6689 (9)0.0723 (15)0.173 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0630 (4)0.0477 (3)0.0345 (3)0.0168 (2)−0.0243 (2)−0.0043 (2)
S10.0677 (12)0.0610 (11)0.0589 (11)0.0008 (9)−0.0245 (9)0.0067 (9)
C10.043 (3)0.035 (3)0.046 (3)0.007 (2)−0.023 (2)−0.008 (2)
C20.051 (3)0.025 (2)0.051 (3)0.002 (2)−0.016 (3)0.003 (2)
C30.040 (3)0.032 (2)0.039 (3)−0.001 (2)−0.009 (2)0.006 (2)
C40.028 (2)0.025 (2)0.033 (2)−0.0015 (17)−0.0134 (18)0.0005 (18)
C50.043 (3)0.033 (3)0.032 (3)0.010 (2)−0.016 (2)−0.003 (2)
C60.031 (2)0.027 (2)0.026 (2)−0.0049 (18)−0.0126 (18)0.0012 (17)
C70.030 (2)0.028 (2)0.033 (2)−0.0055 (18)−0.0107 (18)−0.0022 (18)
C80.042 (3)0.028 (2)0.044 (3)0.000 (2)−0.014 (2)−0.003 (2)
C90.051 (3)0.037 (3)0.047 (3)−0.005 (2)−0.014 (3)−0.012 (2)
C100.056 (4)0.048 (3)0.040 (3)−0.011 (3)−0.007 (3)−0.019 (3)
C110.044 (3)0.044 (3)0.031 (3)−0.011 (2)−0.010 (2)−0.006 (2)
C120.034 (2)0.029 (2)0.031 (2)−0.0069 (18)−0.0118 (19)−0.0027 (18)
C130.033 (2)0.022 (2)0.037 (3)0.0004 (18)−0.010 (2)−0.0032 (18)
C140.035 (2)0.031 (2)0.029 (2)−0.0045 (19)−0.0035 (19)0.0011 (19)
C150.025 (2)0.036 (2)0.039 (3)−0.0014 (19)−0.0043 (19)−0.004 (2)
N10.042 (2)0.039 (2)0.034 (2)0.0123 (19)−0.0174 (19)−0.0069 (18)
N20.033 (2)0.0275 (19)0.029 (2)−0.0023 (16)−0.0105 (16)−0.0005 (15)
N30.039 (2)0.028 (2)0.030 (2)−0.0018 (17)−0.0138 (17)0.0006 (16)
O10.036 (2)0.087 (4)0.070 (3)0.006 (2)−0.026 (2)0.016 (3)
O20.069 (3)0.105 (5)0.058 (3)−0.004 (3)−0.030 (3)0.050 (3)
O30.280 (16)0.066 (5)0.213 (12)0.038 (7)−0.158 (12)−0.039 (6)
Geometric parameters (Å, °) top
Ag1—N22.159 (4)C7—N21.379 (7)
Ag1—N1i2.205 (5)C7—C81.404 (7)
Ag1—O12.489 (5)C7—C121.399 (7)
S1—O11.344 (6)C8—C91.396 (8)
S1—O21.355 (6)C8—H8A0.9300
S1—O31.491 (10)C9—C101.422 (9)
S1—C131.674 (5)C9—H9A0.9300
C1—C21.352 (9)C10—C111.369 (9)
C1—N11.355 (7)C10—H10A0.9300
C1—H1A0.9300C11—C121.391 (7)
C2—C31.374 (8)C11—H11A0.9300
C2—H2A0.9300C12—N31.377 (7)
C3—C41.396 (7)C13—C151.388 (7)
C3—H3A0.9300C13—C141.396 (7)
C4—C51.395 (7)C14—C15ii1.371 (8)
C4—C61.471 (7)C14—H14A0.9300
C5—N11.333 (7)C15—C14ii1.371 (8)
C5—H5A0.9300C15—H15A0.9300
C6—N21.335 (6)N3—O2iii2.677 (6)
C6—N31.349 (6)N3—H3B0.8600
N2—Ag1—N1i153.94 (18)C8—C9—C10120.0 (6)
N2—Ag1—O1114.05 (18)C8—C9—H9A120.0
N1i—Ag1—O190.56 (18)C10—C9—H9A120.0
O1—S1—O2119.3 (4)C11—C10—C9122.2 (6)
O1—S1—O3105.1 (8)C11—C10—H10A118.9
O2—S1—O3106.4 (7)C9—C10—H10A118.9
O1—S1—C13109.6 (3)C10—C11—C12117.1 (5)
O2—S1—C13107.7 (3)C10—C11—H11A121.5
O3—S1—C13108.3 (5)C12—C11—H11A121.5
C2—C1—N1122.3 (5)N3—C12—C11132.2 (5)
C2—C1—H1A118.9N3—C12—C7105.2 (4)
N1—C1—H1A118.9C11—C12—C7122.6 (5)
C1—C2—C3120.2 (5)C15—C13—C14119.9 (5)
C1—C2—H2A119.9C15—C13—S1119.9 (4)
C3—C2—H2A119.9C14—C13—S1120.1 (4)
C2—C3—C4119.2 (5)C15ii—C14—C13120.0 (5)
C2—C3—H3A120.4C15ii—C14—H14A120.0
C4—C3—H3A120.4C13—C14—H14A120.0
C3—C4—C5116.9 (5)C14ii—C15—C13120.1 (5)
C3—C4—C6121.6 (5)C14ii—C15—H15A120.0
C5—C4—C6121.5 (4)C13—C15—H15A120.0
N1—C5—C4123.6 (5)C5—N1—C1117.8 (5)
N1—C5—H5A118.2C5—N1—Ag1i124.4 (4)
C4—C5—H5A118.2C1—N1—Ag1i117.3 (4)
N2—C6—N3111.8 (4)C6—N2—C7105.5 (4)
N2—C6—C4126.7 (4)C6—N2—Ag1131.1 (4)
N3—C6—C4121.6 (4)C7—N2—Ag1121.9 (3)
N2—C7—C8130.4 (5)C6—N3—C12108.0 (4)
N2—C7—C12109.6 (4)C6—N3—O2iii129.2 (4)
C8—C7—C12120.0 (5)C12—N3—O2iii122.3 (4)
C7—C8—C9118.0 (5)C6—N3—H3B126.0
C7—C8—H8A121.0C12—N3—H3B126.0
C9—C8—H8A121.0S1—O1—Ag1116.3 (4)
N1—C1—C2—C31.8 (10)S1—C13—C15—C14ii175.0 (4)
C1—C2—C3—C4−0.9 (9)C4—C5—N1—C1−1.9 (9)
C2—C3—C4—C5−1.1 (8)C4—C5—N1—Ag1i169.8 (4)
C2—C3—C4—C6179.4 (5)C2—C1—N1—C5−0.4 (9)
C3—C4—C5—N12.6 (8)C2—C1—N1—Ag1i−172.7 (5)
C6—C4—C5—N1−177.9 (5)N3—C6—N2—C71.2 (5)
C3—C4—C6—N2−166.6 (5)C4—C6—N2—C7−178.3 (4)
C5—C4—C6—N214.0 (8)N3—C6—N2—Ag1−164.2 (3)
C3—C4—C6—N314.0 (7)C4—C6—N2—Ag116.3 (7)
C5—C4—C6—N3−165.5 (5)C8—C7—N2—C6179.5 (5)
N2—C7—C8—C9179.2 (5)C12—C7—N2—C6−1.5 (5)
C12—C7—C8—C90.4 (8)C8—C7—N2—Ag1−13.4 (7)
C7—C8—C9—C10−1.4 (9)C12—C7—N2—Ag1165.5 (3)
C8—C9—C10—C111.6 (9)N1i—Ag1—N2—C6−46.3 (6)
C9—C10—C11—C12−0.6 (9)O1—Ag1—N2—C6154.2 (4)
C10—C11—C12—N3179.8 (5)N1i—Ag1—N2—C7150.3 (4)
C10—C11—C12—C7−0.5 (8)O1—Ag1—N2—C7−9.2 (4)
N2—C7—C12—N31.3 (5)N2—C6—N3—C12−0.4 (5)
C8—C7—C12—N3−179.6 (4)C4—C6—N3—C12179.1 (4)
N2—C7—C12—C11−178.5 (5)N2—C6—N3—O2iii171.1 (4)
C8—C7—C12—C110.6 (7)C4—C6—N3—O2iii−9.3 (7)
O1—S1—C13—C1535.5 (6)C11—C12—N3—C6179.2 (5)
O2—S1—C13—C15166.7 (6)C7—C12—N3—C6−0.6 (5)
O3—S1—C13—C15−78.7 (9)C11—C12—N3—O2iii6.9 (8)
O1—S1—C13—C14−148.6 (5)C7—C12—N3—O2iii−172.8 (3)
O2—S1—C13—C14−17.4 (7)O2—S1—O1—Ag179.7 (5)
O3—S1—C13—C1497.2 (9)O3—S1—O1—Ag1−39.4 (6)
C15—C13—C14—C15ii0.8 (9)C13—S1—O1—Ag1−155.6 (3)
S1—C13—C14—C15ii−175.0 (4)N2—Ag1—O1—S1−86.9 (4)
C14—C13—C15—C14ii−0.8 (9)N1i—Ag1—O1—S1101.9 (4)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x−1, −y+2, −z; (iii) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O2iii0.861.832.677 (6)169
Symmetry codes: (iii) −x, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3B···O2i0.861.832.677 (6)169
Symmetry codes: (i) −x, −y+1, −z+1.
Acknowledgements top

We gratefully acknowledge the financial support of the Key Science and Technology Project of Fujian Province (No. 2005H045)

references
References top

Alcade, E., Dinares, I., Perez-Garcia, L. & Roca, T. (1992). Synthesis, pp. 295–398.

Rigaku (2000). CrystalClear (Version 1.36) and CrystalStructure. MSC, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97, University of Göttingen, Germany.

Su, C. Y., Yang, X. P., Liao, S., Mak, T. C. W. & Kang, B. S. (1999). Inorg. Chem. Commun. 2, 383–385.

Xiong, R. G., Zhang, J., Chen, Z. F., You, X. Z., Che, C. M. & Fun, H. K. (2001). J. Chem. Soc. Dalton Trans. pp. 780–782.

Yuan, R. X., Xiong, R. G., Xie, Y. L., You, X. Z., Peng, S. M. & Lee, G. H. (2001). Inorg. Chem. Commun. 4, 384–387.