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

The title compound, [Ag₂(C₆H₄O₆S₂)(C₁₂H₉N₃)₂]_n, is a coordination polymer prepared by a hydro­thermal reaction. Two Ag^I 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.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.061
• wR factor = 0.188
• Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT213_ALERT_2_C Atom O2      has ADP max/min Ratio .............       3.30 prola
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         S1

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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 Ag^I 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, Ag^I exhibits a distorted trigonal planar geometry (Fig. 1). Each two Ag^I atoms are connected with two 2-(3-pyridyl)benzimidazole ligands in the end to end mode via N_py and N_BIm donor atoms, forming a binuclear macrocyclic. The coordination sphere of Ag^I 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

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

S2. Experimental

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.

S3. Refinement

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 U_eq(C,N).

Computing details

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

	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.]
	Fig. 2. A view of the one-dimensional chain of the title compound. The hydrogen atoms are omitted for clarity.
	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.
	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]

Crystal data

[Ag2(C6H4S2O6)(C12H9N3)2]	Z = 2
Mr = 421.20	F(000) = 418
Triclinic, P1	Dx = 1.979 Mg m^−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.547 (3) Å	Cell parameters from 2133 reflections
b = 10.060 (4) Å	θ = 2.9–27.5°
c = 10.286 (4) Å	µ = 1.59 mm^−1
α = 77.262 (11)°	T = 293 K
β = 69.963 (11)°	Prism, colorless
γ = 77.409 (10)°	0.60 × 0.35 × 0.10 mm
V = 706.9 (5) Å^3

Data collection

Rigaku Mercury CCD diffractometer	3152 independent reflections
Radiation source: Rotating Anode	2784 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
ω scan	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (CrystalStructure; Rigaku, 2000)	h = −9→9
Tmin = 0.518, Tmax = 0.850	k = −13→13
5340 measured reflections	l = −8→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.188	H-atom parameters constrained
S = 1.11	w = 1/[σ^2(Fo^2) + (0.1114P)^2 + 1.6836P] where P = (Fo^2 + 2Fc^2)/3
3152 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.85 e Å^−3
0 restraints	Δρmin = −1.86 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
Ag1	0.21136 (7)	0.66405 (5)	0.12969 (4)	0.0504 (2)
S1	−0.2367 (3)	0.7926 (2)	0.1437 (2)	0.0657 (5)
C1	0.7242 (8)	0.1820 (6)	0.1720 (6)	0.0411 (12)
H1A	0.8100	0.1153	0.1224	0.049*
C2	0.6483 (9)	0.1494 (6)	0.3124 (7)	0.0450 (13)
H2A	0.6849	0.0623	0.3579	0.054*
C3	0.5173 (8)	0.2445 (6)	0.3881 (6)	0.0406 (12)
H3A	0.4635	0.2218	0.4845	0.049*
C4	0.4660 (7)	0.3754 (5)	0.3187 (5)	0.0288 (9)
C5	0.5556 (8)	0.4020 (6)	0.1745 (6)	0.0378 (11)
H5A	0.5274	0.4899	0.1269	0.045*
C6	0.3252 (7)	0.4808 (5)	0.3941 (5)	0.0283 (9)
C7	0.1248 (7)	0.6644 (5)	0.4484 (5)	0.0304 (9)
C8	0.0034 (8)	0.7919 (6)	0.4505 (6)	0.0393 (12)
H8A	−0.0086	0.8474	0.3678	0.047*
C9	−0.0988 (9)	0.8330 (6)	0.5804 (7)	0.0446 (13)
H9A	−0.1781	0.9178	0.5850	0.054*
C10	−0.0815 (10)	0.7451 (7)	0.7058 (7)	0.0476 (14)
H10A	−0.1530	0.7730	0.7915	0.057*
C11	0.0369 (8)	0.6208 (6)	0.7045 (6)	0.0394 (11)
H11A	0.0479	0.5646	0.7871	0.047*
C12	0.1399 (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	−0.6305	0.8677	0.2134	0.042*
C15	−0.3035 (7)	0.9905 (5)	−0.0596 (6)	0.0357 (11)
H15A	−0.1718	0.9843	−0.0990	0.043*
N1	0.6796 (7)	0.3085 (5)	0.1011 (5)	0.0400 (10)
N2	0.2393 (6)	0.5984 (4)	0.3372 (4)	0.0307 (8)
N3	0.2692 (6)	0.4672 (4)	0.5352 (4)	0.0327 (9)
H3B	0.3074	0.3988	0.5909	0.039*
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ag1	0.0630 (4)	0.0477 (3)	0.0345 (3)	0.0168 (2)	−0.0243 (2)	−0.0043 (2)
S1	0.0677 (12)	0.0610 (11)	0.0589 (11)	0.0008 (9)	−0.0245 (9)	0.0067 (9)
C1	0.043 (3)	0.035 (3)	0.046 (3)	0.007 (2)	−0.023 (2)	−0.008 (2)
C2	0.051 (3)	0.025 (2)	0.051 (3)	0.002 (2)	−0.016 (3)	0.003 (2)
C3	0.040 (3)	0.032 (2)	0.039 (3)	−0.001 (2)	−0.009 (2)	0.006 (2)
C4	0.028 (2)	0.025 (2)	0.033 (2)	−0.0015 (17)	−0.0134 (18)	0.0005 (18)
C5	0.043 (3)	0.033 (3)	0.032 (3)	0.010 (2)	−0.016 (2)	−0.003 (2)
C6	0.031 (2)	0.027 (2)	0.026 (2)	−0.0049 (18)	−0.0126 (18)	0.0012 (17)
C7	0.030 (2)	0.028 (2)	0.033 (2)	−0.0055 (18)	−0.0107 (18)	−0.0022 (18)
C8	0.042 (3)	0.028 (2)	0.044 (3)	0.000 (2)	−0.014 (2)	−0.003 (2)
C9	0.051 (3)	0.037 (3)	0.047 (3)	−0.005 (2)	−0.014 (3)	−0.012 (2)
C10	0.056 (4)	0.048 (3)	0.040 (3)	−0.011 (3)	−0.007 (3)	−0.019 (3)
C11	0.044 (3)	0.044 (3)	0.031 (3)	−0.011 (2)	−0.010 (2)	−0.006 (2)
C12	0.034 (2)	0.029 (2)	0.031 (2)	−0.0069 (18)	−0.0118 (19)	−0.0027 (18)
C13	0.033 (2)	0.022 (2)	0.037 (3)	0.0004 (18)	−0.010 (2)	−0.0032 (18)
C14	0.035 (2)	0.031 (2)	0.029 (2)	−0.0045 (19)	−0.0035 (19)	0.0011 (19)
C15	0.025 (2)	0.036 (2)	0.039 (3)	−0.0014 (19)	−0.0043 (19)	−0.004 (2)
N1	0.042 (2)	0.039 (2)	0.034 (2)	0.0123 (19)	−0.0174 (19)	−0.0069 (18)
N2	0.033 (2)	0.0275 (19)	0.029 (2)	−0.0023 (16)	−0.0105 (16)	−0.0005 (15)
N3	0.039 (2)	0.028 (2)	0.030 (2)	−0.0018 (17)	−0.0138 (17)	0.0006 (16)
O1	0.036 (2)	0.087 (4)	0.070 (3)	0.006 (2)	−0.026 (2)	0.016 (3)
O2	0.069 (3)	0.105 (5)	0.058 (3)	−0.004 (3)	−0.030 (3)	0.050 (3)
O3	0.280 (16)	0.066 (5)	0.213 (12)	0.038 (7)	−0.158 (12)	−0.039 (6)

Geometric parameters (Å, º)

Ag1—N2	2.159 (4)	C7—N2	1.379 (7)
Ag1—N1^i	2.205 (5)	C7—C8	1.404 (7)
Ag1—O1	2.489 (5)	C7—C12	1.399 (7)
S1—O1	1.344 (6)	C8—C9	1.396 (8)
S1—O2	1.355 (6)	C8—H8A	0.9300
S1—O3	1.491 (10)	C9—C10	1.422 (9)
S1—C13	1.674 (5)	C9—H9A	0.9300
C1—C2	1.352 (9)	C10—C11	1.369 (9)
C1—N1	1.355 (7)	C10—H10A	0.9300
C1—H1A	0.9300	C11—C12	1.391 (7)
C2—C3	1.374 (8)	C11—H11A	0.9300
C2—H2A	0.9300	C12—N3	1.377 (7)
C3—C4	1.396 (7)	C13—C15	1.388 (7)
C3—H3A	0.9300	C13—C14	1.396 (7)
C4—C5	1.395 (7)	C14—C15^ii	1.371 (8)
C4—C6	1.471 (7)	C14—H14A	0.9300
C5—N1	1.333 (7)	C15—C14^ii	1.371 (8)
C5—H5A	0.9300	C15—H15A	0.9300
C6—N2	1.335 (6)	N3—O2^iii	2.677 (6)
C6—N3	1.349 (6)	N3—H3B	0.8600
N2—Ag1—N1^i	153.94 (18)	C8—C9—C10	120.0 (6)
N2—Ag1—O1	114.05 (18)	C8—C9—H9A	120.0
N1^i—Ag1—O1	90.56 (18)	C10—C9—H9A	120.0
O1—S1—O2	119.3 (4)	C11—C10—C9	122.2 (6)
O1—S1—O3	105.1 (8)	C11—C10—H10A	118.9
O2—S1—O3	106.4 (7)	C9—C10—H10A	118.9
O1—S1—C13	109.6 (3)	C10—C11—C12	117.1 (5)
O2—S1—C13	107.7 (3)	C10—C11—H11A	121.5
O3—S1—C13	108.3 (5)	C12—C11—H11A	121.5
C2—C1—N1	122.3 (5)	N3—C12—C11	132.2 (5)
C2—C1—H1A	118.9	N3—C12—C7	105.2 (4)
N1—C1—H1A	118.9	C11—C12—C7	122.6 (5)
C1—C2—C3	120.2 (5)	C15—C13—C14	119.9 (5)
C1—C2—H2A	119.9	C15—C13—S1	119.9 (4)
C3—C2—H2A	119.9	C14—C13—S1	120.1 (4)
C2—C3—C4	119.2 (5)	C15^ii—C14—C13	120.0 (5)
C2—C3—H3A	120.4	C15^ii—C14—H14A	120.0
C4—C3—H3A	120.4	C13—C14—H14A	120.0
C3—C4—C5	116.9 (5)	C14^ii—C15—C13	120.1 (5)
C3—C4—C6	121.6 (5)	C14^ii—C15—H15A	120.0
C5—C4—C6	121.5 (4)	C13—C15—H15A	120.0
N1—C5—C4	123.6 (5)	C5—N1—C1	117.8 (5)
N1—C5—H5A	118.2	C5—N1—Ag1^i	124.4 (4)
C4—C5—H5A	118.2	C1—N1—Ag1^i	117.3 (4)
N2—C6—N3	111.8 (4)	C6—N2—C7	105.5 (4)
N2—C6—C4	126.7 (4)	C6—N2—Ag1	131.1 (4)
N3—C6—C4	121.6 (4)	C7—N2—Ag1	121.9 (3)
N2—C7—C8	130.4 (5)	C6—N3—C12	108.0 (4)
N2—C7—C12	109.6 (4)	C6—N3—O2^iii	129.2 (4)
C8—C7—C12	120.0 (5)	C12—N3—O2^iii	122.3 (4)
C7—C8—C9	118.0 (5)	C6—N3—H3B	126.0
C7—C8—H8A	121.0	C12—N3—H3B	126.0
C9—C8—H8A	121.0	S1—O1—Ag1	116.3 (4)
N1—C1—C2—C3	1.8 (10)	S1—C13—C15—C14^ii	175.0 (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—Ag1^i	169.8 (4)
C2—C3—C4—C6	179.4 (5)	C2—C1—N1—C5	−0.4 (9)
C3—C4—C5—N1	2.6 (8)	C2—C1—N1—Ag1^i	−172.7 (5)
C6—C4—C5—N1	−177.9 (5)	N3—C6—N2—C7	1.2 (5)
C3—C4—C6—N2	−166.6 (5)	C4—C6—N2—C7	−178.3 (4)
C5—C4—C6—N2	14.0 (8)	N3—C6—N2—Ag1	−164.2 (3)
C3—C4—C6—N3	14.0 (7)	C4—C6—N2—Ag1	16.3 (7)
C5—C4—C6—N3	−165.5 (5)	C8—C7—N2—C6	179.5 (5)
N2—C7—C8—C9	179.2 (5)	C12—C7—N2—C6	−1.5 (5)
C12—C7—C8—C9	0.4 (8)	C8—C7—N2—Ag1	−13.4 (7)
C7—C8—C9—C10	−1.4 (9)	C12—C7—N2—Ag1	165.5 (3)
C8—C9—C10—C11	1.6 (9)	N1^i—Ag1—N2—C6	−46.3 (6)
C9—C10—C11—C12	−0.6 (9)	O1—Ag1—N2—C6	154.2 (4)
C10—C11—C12—N3	179.8 (5)	N1^i—Ag1—N2—C7	150.3 (4)
C10—C11—C12—C7	−0.5 (8)	O1—Ag1—N2—C7	−9.2 (4)
N2—C7—C12—N3	1.3 (5)	N2—C6—N3—C12	−0.4 (5)
C8—C7—C12—N3	−179.6 (4)	C4—C6—N3—C12	179.1 (4)
N2—C7—C12—C11	−178.5 (5)	N2—C6—N3—O2^iii	171.1 (4)
C8—C7—C12—C11	0.6 (7)	C4—C6—N3—O2^iii	−9.3 (7)
O1—S1—C13—C15	35.5 (6)	C11—C12—N3—C6	179.2 (5)
O2—S1—C13—C15	166.7 (6)	C7—C12—N3—C6	−0.6 (5)
O3—S1—C13—C15	−78.7 (9)	C11—C12—N3—O2^iii	6.9 (8)
O1—S1—C13—C14	−148.6 (5)	C7—C12—N3—O2^iii	−172.8 (3)
O2—S1—C13—C14	−17.4 (7)	O2—S1—O1—Ag1	79.7 (5)
O3—S1—C13—C14	97.2 (9)	O3—S1—O1—Ag1	−39.4 (6)
C15—C13—C14—C15^ii	0.8 (9)	C13—S1—O1—Ag1	−155.6 (3)
S1—C13—C14—C15^ii	−175.0 (4)	N2—Ag1—O1—S1	−86.9 (4)
C14—C13—C15—C14^ii	−0.8 (9)	N1^i—Ag1—O1—S1	101.9 (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, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···O2^iii	0.86	1.83	2.677 (6)	169

Symmetry code: (iii) −x, −y+1, −z+1.