catena-Poly[[bis-[μ-2-(3-pyrid-yl)-1H-benzimidazole]-κN:N;κN:N-disilver(I)]-μ-2,5-dicarboxy-benzene-1,4-dicarboxyl-ato-κO:O].

The title coordination polymer, [Ag(2)(C(10)H(4)O(8))(C(12)H(9)N(3))(2)](n), was prepared by a hydro-thermal method. The Ag(I) atom exists in a strongly distorted trigonal coordination environment. Two Ag(I) ions related by an inversion centre are coordinated by two 2-(3-pyrid-yl)benzimidazole ligands, forming a centrosymmetric cyclic dimer. The bridging bidentate 2,5-dicarboxy-benzene-1,4-dicarboxyl-ate 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 intra-molecular O-H⋯O hydrogen bond. Finally, inter-molecular N-H⋯O hydrogen bonds aggregate the chains into a three-dimensional framework.

Related literature

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

Crystal data

[Ag2(C10H4O8)(C12H9N3)2]

M = 858.32

Monoclinic,

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 ▶) 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 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

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

[Ag2(C10H4O8)(C12H9N3)2]	F000 = 852
Mr = 858.32	Dx = 1.909 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3641 reflections
a = 4.8940 (11) Å	θ = 2.5–27.5º
b = 16.011 (4) Å	µ = 1.38 mm−1
c = 19.077 (4) Å	T = 293 (2) K
β = 92.393 (3)º	Prism, colourless
V = 1493.6 (6) Å3	0.48 × 0.13 × 0.13 mm
Z = 2

Rigaku Mercury CCD diffractometer	3405 independent reflections
Radiation source: fine-focus sealed tube	3079 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
T = 293(2) K	θmax = 27.5º
ω scans	θmin = 2.5º
Absorption correction: multi-scan(CrystalClear; Rigaku, 2000)	h = −6→6
Tmin = 0.806, Tmax = 0.842	k = −20→20
11420 measured reflections	l = −18→24

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030	H 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 reflections	Δρmax = 0.50 e Å−3
230 parameters	Δρmin = −0.85 e Å−3
1 restraint	Extinction correction: none
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Ag1	0.71244 (4)	0.134099 (11)	1.018347 (10)	0.04125 (9)
C1	1.1680 (5)	−0.15500 (14)	1.13812 (13)	0.0343 (5)
H1A	1.2997	−0.1963	1.1336	0.041*
C2	1.0649 (5)	−0.14053 (14)	1.20320 (14)	0.0359 (5)
H2A	1.1275	−0.1717	1.2418	0.043*
C3	0.8688 (5)	−0.07976 (15)	1.21087 (12)	0.0329 (5)
H3B	0.7980	−0.0695	1.2545	0.039*
C4	0.7781 (4)	−0.03380 (13)	1.15231 (12)	0.0265 (4)
C5	0.8913 (5)	−0.05275 (13)	1.08884 (12)	0.0324 (5)
H5A	0.8300	−0.0232	1.0493	0.039*
C6	0.5728 (4)	0.03242 (13)	1.15806 (11)	0.0264 (4)
C7	0.3021 (5)	0.13812 (13)	1.13776 (12)	0.0269 (4)
C8	0.1575 (5)	0.20687 (14)	1.11051 (13)	0.0347 (5)
H8A	0.1860	0.2269	1.0656	0.042*
C9	−0.0299 (5)	0.24392 (16)	1.15313 (14)	0.0386 (6)
H9A	−0.1287	0.2900	1.1365	0.046*
C10	−0.0745 (5)	0.21380 (16)	1.22058 (14)	0.0383 (6)
H10A	−0.2039	0.2399	1.2474	0.046*
C11	0.0682 (5)	0.14644 (15)	1.24842 (13)	0.0332 (5)
H11A	0.0396	0.1267	1.2934	0.040*
C12	0.2577 (4)	0.10963 (13)	1.20541 (11)	0.0264 (4)
C13	0.5075 (5)	0.32005 (13)	0.96973 (12)	0.0322 (5)
C14	0.4884 (5)	0.41435 (13)	0.98108 (11)	0.0271 (4)
C15	0.3175 (5)	0.47238 (13)	0.94531 (11)	0.0271 (4)
C16	0.1144 (5)	0.45603 (15)	0.88456 (12)	0.0320 (5)
C17	0.3352 (5)	0.55568 (14)	0.96571 (12)	0.0297 (5)
H17A	0.2214	0.5939	0.9422	0.036*
N1	1.0845 (4)	−0.11132 (12)	1.08101 (11)	0.0347 (4)
N2	0.5015 (4)	0.08847 (11)	1.10831 (9)	0.0273 (4)
N3	0.4299 (4)	0.04296 (11)	1.21627 (9)	0.0273 (4)
H3A	0.4443	0.0131	1.2537	0.033*
O1	0.6918 (4)	0.28180 (11)	1.00119 (11)	0.0484 (5)
O2	0.3341 (4)	0.28260 (11)	0.92949 (12)	0.0486 (5)
H2B	0.217 (7)	0.316 (2)	0.912 (2)	0.082 (13)*
O3	0.0298 (4)	0.51666 (11)	0.84962 (9)	0.0440 (4)
O4	0.0356 (4)	0.38153 (11)	0.87095 (10)	0.0456 (5)

	U11	U22	U33	U12	U13	U23
Ag1	0.05515 (15)	0.02899 (12)	0.04086 (13)	0.01185 (8)	0.01680 (9)	0.00789 (7)
C1	0.0358 (12)	0.0225 (10)	0.0449 (14)	0.0059 (9)	0.0042 (10)	0.0043 (9)
C2	0.0383 (13)	0.0301 (12)	0.0393 (13)	0.0058 (10)	0.0011 (10)	0.0093 (9)
C3	0.0362 (12)	0.0305 (12)	0.0320 (12)	0.0041 (10)	0.0018 (9)	0.0010 (9)
C4	0.0274 (11)	0.0187 (9)	0.0333 (11)	−0.0010 (8)	0.0010 (8)	−0.0001 (8)
C5	0.0411 (13)	0.0216 (10)	0.0347 (12)	0.0054 (9)	0.0037 (10)	0.0026 (8)
C6	0.0283 (11)	0.0205 (10)	0.0303 (11)	−0.0005 (8)	−0.0007 (8)	−0.0007 (8)
C7	0.0263 (11)	0.0219 (10)	0.0323 (11)	−0.0002 (8)	−0.0002 (8)	−0.0008 (8)
C8	0.0368 (13)	0.0280 (11)	0.0386 (13)	0.0034 (10)	−0.0037 (10)	0.0050 (9)
C9	0.0372 (13)	0.0284 (12)	0.0492 (15)	0.0097 (10)	−0.0073 (11)	−0.0006 (10)
C10	0.0324 (12)	0.0360 (13)	0.0463 (14)	0.0081 (10)	0.0001 (10)	−0.0107 (10)
C11	0.0319 (12)	0.0337 (12)	0.0339 (12)	0.0015 (9)	0.0014 (9)	−0.0027 (9)
C12	0.0259 (11)	0.0223 (10)	0.0307 (11)	0.0005 (8)	−0.0023 (8)	−0.0012 (8)
C13	0.0455 (14)	0.0189 (10)	0.0327 (12)	0.0017 (9)	0.0057 (10)	−0.0001 (8)
C14	0.0379 (12)	0.0173 (9)	0.0261 (10)	0.0030 (8)	0.0037 (9)	0.0002 (7)
C15	0.0347 (12)	0.0219 (10)	0.0249 (10)	0.0022 (9)	0.0035 (8)	0.0003 (8)
C16	0.0380 (13)	0.0309 (11)	0.0269 (11)	0.0029 (9)	0.0012 (9)	−0.0016 (9)
C17	0.0400 (13)	0.0207 (10)	0.0282 (11)	0.0055 (9)	−0.0013 (9)	0.0031 (8)
N1	0.0428 (12)	0.0208 (9)	0.0410 (11)	0.0040 (8)	0.0082 (9)	0.0028 (8)
N2	0.0303 (10)	0.0220 (9)	0.0297 (9)	0.0025 (7)	0.0020 (7)	0.0016 (7)
N3	0.0304 (10)	0.0244 (9)	0.0272 (9)	0.0038 (7)	0.0014 (7)	0.0023 (7)
O1	0.0691 (13)	0.0194 (8)	0.0554 (11)	0.0126 (8)	−0.0126 (10)	0.0003 (7)
O2	0.0545 (12)	0.0220 (8)	0.0680 (13)	0.0009 (8)	−0.0133 (10)	−0.0091 (8)
O3	0.0638 (12)	0.0335 (9)	0.0334 (9)	0.0062 (9)	−0.0137 (8)	−0.0009 (7)
O4	0.0538 (12)	0.0345 (9)	0.0471 (11)	−0.0065 (8)	−0.0147 (9)	−0.0035 (8)

Ag1—N2	2.1663 (18)	C9—H9A	0.9300
Ag1—N1i	2.207 (2)	C10—C11	1.379 (3)
Ag1—O1	2.3889 (18)	C10—H10A	0.9300
C1—N1	1.344 (3)	C11—C12	1.394 (3)
C1—C2	1.379 (4)	C11—H11A	0.9300
C1—H1A	0.9300	C12—N3	1.370 (3)
C2—C3	1.379 (3)	C13—O1	1.226 (3)
C2—H2A	0.9300	C13—O2	1.271 (3)
C3—C4	1.395 (3)	C13—C14	1.529 (3)
C3—H3B	0.9300	C14—C17ii	1.390 (3)
C4—C5	1.386 (3)	C14—C15	1.407 (3)
C4—C6	1.468 (3)	C15—C17	1.391 (3)
C5—N1	1.344 (3)	C15—C16	1.518 (3)
C5—H5A	0.9300	C16—O3	1.239 (3)
C6—N3	1.347 (3)	C16—O4	1.277 (3)
C6—N2	1.342 (3)	C16—O4	1.277 (3)
C7—C8	1.397 (3)	C17—H17A	0.9300
C7—N2	1.395 (3)	N3—O3iii	2.742 (3)
C7—C12	1.394 (3)	N3—H3A	0.8600
C8—C9	1.384 (4)	O2—O4	2.399 (3)
C8—H8A	0.9300	O2—H2B	0.846 (19)
C9—C10	1.400 (4)
N2—Ag1—N1i	150.61 (7)	C12—C11—H11A	121.9
N2—Ag1—O1	115.06 (7)	N3—C12—C11	131.3 (2)
N1i—Ag1—O1	93.66 (7)	N3—C12—C7	106.02 (18)
N1—C1—C2	122.1 (2)	C11—C12—C7	122.7 (2)
N1—C1—H1A	118.9	O1—C13—O2	121.3 (2)
C2—C1—H1A	118.9	O1—C13—C14	118.2 (2)
C3—C2—C1	119.8 (2)	O2—C13—C14	120.5 (2)
C3—C2—H2A	120.1	C17ii—C14—C15	117.68 (19)
C1—C2—H2A	120.1	C17ii—C14—C13	113.86 (19)
C2—C3—C4	119.1 (2)	C15—C14—C13	128.5 (2)
C2—C3—H3B	120.4	C17—C15—C14	117.9 (2)
C4—C3—H3B	120.4	C17—C15—C16	114.22 (19)
C5—C4—C3	117.3 (2)	C14—C15—C16	127.83 (19)
C5—C4—C6	121.6 (2)	O3—C16—O4	122.1 (2)
C3—C4—C6	121.1 (2)	O3—C16—O4	122.1 (2)
N1—C5—C4	124.0 (2)	O3—C16—C15	118.0 (2)
N1—C5—H5A	118.0	O4—C16—C15	119.9 (2)
C4—C5—H5A	118.0	O4—C16—C15	119.9 (2)
N3—C6—N2	111.75 (19)	C15—C17—C14ii	124.4 (2)
N3—C6—C4	122.18 (19)	C15—C17—H17A	117.8
N2—C6—C4	126.1 (2)	C14ii—C17—H17A	117.8
C8—C7—N2	130.6 (2)	C5—N1—C1	117.7 (2)
C8—C7—C12	120.4 (2)	C5—N1—Ag1i	123.69 (16)
N2—C7—C12	108.97 (19)	C1—N1—Ag1i	118.53 (16)
C9—C8—C7	117.2 (2)	C6—N2—C7	105.18 (18)
C9—C8—H8A	121.4	C6—N2—Ag1	131.88 (15)
C7—C8—H8A	121.4	C7—N2—Ag1	119.44 (14)
C8—C9—C10	121.7 (2)	C6—N3—C12	108.07 (18)
C8—C9—H9A	119.2	C6—N3—O3iii	129.98 (14)
C10—C9—H9A	119.2	C12—N3—O3iii	119.74 (14)
C11—C10—C9	121.9 (2)	C6—N3—H3A	126.0
C11—C10—H10A	119.1	C12—N3—H3A	126.0
C9—C10—H10A	119.1	C13—O1—Ag1	125.98 (17)
C10—C11—C12	116.3 (2)	C13—O2—O4	110.37 (15)
C10—C11—H11A	121.9	C13—O2—H2B	111 (3)
N1—C1—C2—C3	0.3 (4)	C14—C15—C17—C14ii	0.3 (4)
C1—C2—C3—C4	0.0 (4)	C16—C15—C17—C14ii	−178.4 (2)
C2—C3—C4—C5	0.4 (3)	C4—C5—N1—C1	1.3 (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—N1	178.3 (2)	C2—C1—N1—Ag1i	175.50 (19)
C5—C4—C6—N3	169.4 (2)	N3—C6—N2—C7	0.7 (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—Ag1	158.67 (15)
C3—C4—C6—N2	169.2 (2)	C4—C6—N2—Ag1	−21.7 (3)
N2—C7—C8—C9	−179.8 (2)	C8—C7—N2—C6	179.0 (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—Ag1	17.7 (3)
C8—C9—C10—C11	0.9 (4)	C12—C7—N2—Ag1	−161.64 (14)
C9—C10—C11—C12	−0.5 (4)	N1i—Ag1—N2—C6	57.2 (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—C7	19.57 (18)
N2—C7—C12—N3	−0.1 (2)	N2—C6—N3—C12	−0.8 (2)
C8—C7—C12—C11	0.9 (4)	C4—C6—N3—C12	179.6 (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—O3iii	17.0 (3)
O2—C13—C14—C17ii	170.6 (2)	C11—C12—N3—C6	−180.0 (2)
O1—C13—C14—C15	172.0 (2)	C7—C12—N3—C6	0.5 (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—O3iii	165.26 (14)
C13—C14—C15—C17	179.3 (2)	O2—C13—O1—Ag1	−15.7 (4)
C17ii—C14—C15—C16	178.2 (2)	C14—C13—O1—Ag1	163.34 (15)
C13—C14—C15—C16	−2.1 (4)	N2—Ag1—O1—C13	−85.5 (2)
C17—C15—C16—O3	15.1 (3)	N1i—Ag1—O1—C13	88.1 (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—O4	6.0 (3)
C14—C15—C16—O4	16.6 (4)	O3—C16—O4—O4	0.0 (4)
C17—C15—C16—O4	−164.8 (2)	C15—C16—O4—O4	0.0 (3)
C14—C15—C16—O4	16.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O4	0.846 (19)	1.56 (2)	2.399 (3)	171 (4)
N3—H3A···O3iii	0.86	1.92	2.742 (3)	159

Ag1—N2	2.1663 (18)
Ag1—N1i	2.207 (2)
Ag1—O1	2.3889 (18)

N2—Ag1—N1i	150.61 (7)
N2—Ag1—O1	115.06 (7)
N1i—Ag1—O1	93.66 (7)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O4	0.846 (19)	1.56 (2)	2.399 (3)	171 (4)
N3—H3A⋯O3ii	0.86	1.92	2.742 (3)	159

Symmetry code: (ii) .