Poly[4-(dimethyl-amino)pyridinium [(μ(6)-5-carboxy-benzene-1,2,4-tricarboxy-ato-κO:O:O:O:O:O)diargentate(I)]].

In the title compound, {(C(7)H(11)N(2))[Ag(2)(C(10)H(3)O(8))]}(n), the polymeric anion consists of two Ag(I) atoms and a Hbtc(3-) ligand (H(4)btc = benzene-1,2,4,5-tetra-carboxylic acid). Each Ag(I) atom is coordinated by four O atoms from three different Hbtc(3-) ligands. The two Ag(I) atoms are bridged by two bidentate carboxyl-ate groups into an Ag(2)O(4) cyclic unit, with an Ag⋯Ag distance of 2.8189 (3) Å. In this way, the Ag atoms are connected by the Hbtc(3-) ligands into an extended two-dimensional layer structure. A three-dimensional network is accomplished through O-H⋯O hydrogen bonds between the anionic layers. The cationic guest Hdmap(+) [dmap = 4-(dimethyl-amino)pyridine] is trapped in the network and adheres to the layer by an N-H⋯O hydrogen bond.

Related literature

For general background to metal-organic frameworks with 1,2,4,5-benzene­tetra­carboxyl­ate liganda, see: Cao et al. (2002 ▶); Hu et al. (2004 ▶); Li et al. (2003 ▶). For related complexes, see: Chen (2008 ▶); Sun et al. (2003 ▶); Zheng et al. (2002 ▶, 2003 ▶).

Experimental

Crystal data

(C7H11N2)[Ag2(C10H3O8)]

M = 590.04

Triclinic,

a = 9.7192 (3) Å

b = 9.9936 (5) Å

c = 10.4968 (3) Å

α = 113.304 (4)°

β = 97.140 (3)°

γ = 103.260 (3)°

V = 884.65 (7) Å3

Z = 2

Mo Kα radiation

μ = 2.27 mm−1

T = 293 K

0.24 × 0.18 × 0.14 mm

Data collection

Oxford Diffraction Gemini R Ultra diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006 ▶) T min = 0.611, T max = 0.725

7226 measured reflections

3124 independent reflections

2808 reflections with I > 2σI)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.018

wR(F 2) = 0.046

S = 1.06

3124 reflections

265 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.47 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809028839/hy2204sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809028839/hy2204Isup2.hkl

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

(C7H11N2)[Ag2(C10H3O8)]	Z = 2
Mr = 590.04	F(000) = 576
Triclinic, P1	Dx = 2.215 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7192 (3) Å	Cell parameters from 3901 reflections
b = 9.9936 (5) Å	θ = 4.4–25.0°
c = 10.4968 (3) Å	µ = 2.27 mm−1
α = 113.304 (4)°	T = 293 K
β = 97.140 (3)°	Block, colorless
γ = 103.260 (3)°	0.24 × 0.18 × 0.14 mm
V = 884.65 (7) Å3

Oxford Diffraction Gemini R Ultra diffractometer	3124 independent reflections
Radiation source: fine-focus sealed tube	2808 reflections with I > 2σ(I)
graphite	Rint = 0.012
Detector resolution: 10.0 pixels mm-1	θmax = 25.0°, θmin = 4.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006)	k = −11→11
Tmin = 0.611, Tmax = 0.725	l = −12→12
7226 measured reflections

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)] = 0.018	H-atom parameters constrained
wR(F2) = 0.046	w = 1/[σ2(Fo2) + (0.0251P)2 + 0.4969P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.003
3124 reflections	Δρmax = 0.35 e Å−3
265 parameters	Δρmin = −0.47 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0157 (6)

	x	y	z	Uiso*/Ueq
Ag1	0.421397 (19)	0.410977 (18)	0.802682 (17)	0.02690 (8)
Ag2	0.421385 (19)	0.385653 (19)	1.290598 (17)	0.02889 (9)
O1	0.22857 (16)	0.20334 (17)	0.81649 (18)	0.0277 (4)
O2	0.10698 (15)	−0.04467 (17)	0.71974 (19)	0.0329 (4)
H2	0.0364	−0.0126	0.7220	0.049*
O3	0.57621 (18)	0.37804 (17)	1.02125 (17)	0.0326 (4)
O4	0.4252 (2)	0.21751 (18)	1.07819 (17)	0.0344 (4)
O5	0.41174 (19)	−0.39642 (18)	0.45762 (18)	0.0357 (4)
O6	0.5636 (2)	−0.23946 (18)	0.39821 (17)	0.0341 (4)
O7	0.75751 (16)	−0.21312 (17)	0.65497 (17)	0.0251 (3)
O8	0.87465 (16)	0.03113 (17)	0.7214 (2)	0.0336 (4)
C1	0.2265 (2)	0.0702 (2)	0.7685 (2)	0.0178 (4)
C2	0.4977 (2)	0.2487 (2)	0.9985 (2)	0.0173 (4)
C3	0.4930 (2)	0.1181 (2)	0.8600 (2)	0.0160 (4)
C4	0.3628 (2)	−0.0996 (2)	0.6355 (2)	0.0177 (4)
H4	0.2755	−0.1617	0.5684	0.021*
C5	0.3627 (2)	0.0251 (2)	0.7570 (2)	0.0160 (4)
C6	0.6223 (2)	−0.0377 (2)	0.7128 (2)	0.0157 (4)
C7	0.4913 (2)	−0.1332 (2)	0.6121 (2)	0.0153 (4)
C8	0.6218 (2)	0.0862 (2)	0.8348 (2)	0.0185 (4)
H8	0.7093	0.1493	0.9012	0.022*
C9	0.4888 (2)	−0.2673 (2)	0.4775 (2)	0.0168 (4)
C10	0.7617 (2)	−0.0765 (2)	0.6939 (2)	0.0192 (4)
N1	0.0720 (2)	0.4030 (2)	0.1392 (2)	0.0333 (5)
N2	−0.1309 (2)	0.6318 (3)	0.4369 (2)	0.0378 (5)
H	−0.1683	0.6777	0.5021	0.045*
C11	0.0048 (2)	0.4765 (3)	0.2354 (2)	0.0271 (5)
C12	−0.0362 (3)	0.7091 (3)	0.3890 (3)	0.0354 (6)
H12	−0.0172	0.8144	0.4240	0.042*
C13	−0.1624 (3)	0.4795 (3)	0.3866 (3)	0.0375 (6)
H13	−0.2296	0.4279	0.4204	0.045*
C14	−0.0985 (3)	0.3988 (3)	0.2872 (3)	0.0343 (6)
H14	−0.1223	0.2931	0.2533	0.041*
C15	0.0325 (3)	0.6369 (3)	0.2906 (3)	0.0333 (6)
H15	0.0981	0.6930	0.2592	0.040*
C16	0.0426 (3)	0.2378 (3)	0.0780 (3)	0.0407 (6)
H16A	−0.0540	0.1883	0.0172	0.061*
H16B	0.0505	0.2065	0.1535	0.061*
H16C	0.1119	0.2095	0.0231	0.061*
C17	0.1797 (3)	0.4867 (4)	0.0902 (3)	0.0423 (7)
H17A	0.2588	0.5591	0.1700	0.063*
H17B	0.1351	0.5400	0.0473	0.063*
H17C	0.2160	0.4161	0.0210	0.063*

	U11	U22	U33	U12	U13	U23
Ag1	0.03846 (13)	0.01606 (11)	0.01917 (11)	0.00464 (7)	0.01347 (8)	0.00093 (7)
Ag2	0.04268 (13)	0.01682 (11)	0.02185 (11)	0.00567 (8)	0.01695 (8)	0.00245 (8)
O1	0.0209 (8)	0.0163 (8)	0.0436 (10)	0.0084 (6)	0.0142 (7)	0.0076 (7)
O2	0.0123 (7)	0.0184 (8)	0.0581 (11)	0.0053 (6)	0.0090 (7)	0.0065 (8)
O3	0.0409 (10)	0.0154 (8)	0.0288 (9)	0.0006 (7)	0.0191 (7)	−0.0016 (7)
O4	0.0535 (11)	0.0211 (8)	0.0240 (8)	0.0075 (7)	0.0231 (8)	0.0037 (7)
O5	0.0431 (10)	0.0148 (8)	0.0356 (9)	−0.0001 (7)	0.0255 (8)	−0.0019 (7)
O6	0.0553 (11)	0.0201 (8)	0.0233 (8)	0.0081 (7)	0.0245 (8)	0.0034 (7)
O7	0.0233 (8)	0.0173 (8)	0.0361 (9)	0.0103 (6)	0.0155 (7)	0.0084 (7)
O8	0.0143 (8)	0.0191 (8)	0.0614 (12)	0.0046 (6)	0.0133 (7)	0.0108 (8)
C1	0.0168 (10)	0.0168 (11)	0.0191 (10)	0.0056 (8)	0.0084 (8)	0.0058 (9)
C2	0.0181 (10)	0.0166 (10)	0.0149 (9)	0.0087 (8)	0.0047 (8)	0.0027 (8)
C3	0.0185 (10)	0.0132 (10)	0.0154 (10)	0.0056 (8)	0.0061 (8)	0.0045 (8)
C4	0.0146 (10)	0.0155 (10)	0.0173 (10)	0.0036 (8)	0.0026 (8)	0.0026 (8)
C5	0.0151 (10)	0.0132 (10)	0.0199 (10)	0.0049 (7)	0.0079 (8)	0.0061 (8)
C6	0.0144 (10)	0.0132 (10)	0.0185 (10)	0.0047 (7)	0.0067 (8)	0.0050 (8)
C7	0.0173 (10)	0.0130 (9)	0.0160 (9)	0.0063 (8)	0.0073 (8)	0.0049 (8)
C8	0.0155 (10)	0.0143 (10)	0.0187 (10)	0.0028 (8)	0.0031 (8)	0.0016 (8)
C9	0.0168 (10)	0.0164 (10)	0.0150 (10)	0.0071 (8)	0.0035 (8)	0.0036 (8)
C10	0.0181 (10)	0.0173 (11)	0.0199 (10)	0.0063 (8)	0.0074 (8)	0.0045 (9)
N1	0.0372 (11)	0.0354 (11)	0.0322 (11)	0.0154 (9)	0.0194 (9)	0.0141 (9)
N2	0.0413 (12)	0.0458 (13)	0.0318 (11)	0.0272 (10)	0.0174 (10)	0.0123 (10)
C11	0.0270 (12)	0.0322 (13)	0.0235 (11)	0.0108 (10)	0.0076 (9)	0.0122 (10)
C12	0.0420 (14)	0.0289 (13)	0.0338 (13)	0.0143 (11)	0.0061 (11)	0.0113 (11)
C13	0.0364 (14)	0.0422 (15)	0.0414 (14)	0.0136 (11)	0.0216 (12)	0.0213 (13)
C14	0.0383 (14)	0.0280 (13)	0.0401 (14)	0.0111 (11)	0.0188 (12)	0.0150 (12)
C15	0.0369 (13)	0.0308 (13)	0.0344 (13)	0.0097 (10)	0.0128 (11)	0.0156 (11)
C16	0.0437 (15)	0.0410 (16)	0.0369 (14)	0.0218 (12)	0.0152 (12)	0.0102 (13)
C17	0.0371 (14)	0.0576 (18)	0.0399 (15)	0.0176 (13)	0.0225 (12)	0.0236 (14)

Ag1—O1	2.5220 (15)	C6—C8	1.387 (3)
Ag1—O3i	2.1784 (15)	C6—C7	1.400 (3)
Ag1—O3	2.7573 (19)	C6—C10	1.507 (3)
Ag1—O6ii	2.1765 (15)	C7—C9	1.507 (3)
Ag2—O4	2.2091 (15)	C8—H8	0.9300
Ag2—O5iii	2.2224 (16)	N1—C11	1.336 (3)
Ag2—O5iv	2.873 (2)	N1—C16	1.455 (3)
Ag2—O7iv	2.4442 (15)	N1—C17	1.460 (3)
Ag1—Ag2i	2.8189 (3)	N2—C12	1.339 (3)
O1—C1	1.216 (3)	N2—C13	1.341 (3)
O2—C1	1.306 (2)	N2—H	0.84
O2—H2	0.82	C11—C15	1.417 (3)
O3—C2	1.252 (3)	C11—C14	1.420 (3)
O4—C2	1.244 (3)	C12—C15	1.355 (3)
O5—C9	1.255 (3)	C12—H12	0.9300
O6—C9	1.240 (3)	C13—C14	1.361 (3)
O7—C10	1.249 (3)	C13—H13	0.9300
O8—C10	1.257 (2)	C14—H14	0.9300
C1—C5	1.496 (3)	C15—H15	0.9300
C2—C3	1.508 (3)	C16—H16A	0.9600
C3—C8	1.392 (3)	C16—H16B	0.9600
C3—C5	1.401 (3)	C16—H16C	0.9600
C4—C5	1.387 (3)	C17—H17A	0.9600
C4—C7	1.392 (3)	C17—H17B	0.9600
C4—H4	0.9300	C17—H17C	0.9600
O6ii—Ag1—O3i	165.22 (6)	C4—C7—C6	118.95 (18)
O6ii—Ag1—O1	88.08 (6)	C4—C7—C9	120.01 (17)
O3i—Ag1—O1	104.84 (6)	C6—C7—C9	120.99 (17)
O6ii—Ag1—Ag2i	82.64 (4)	C6—C8—C3	121.33 (18)
O3i—Ag1—Ag2i	83.04 (4)	C6—C8—H8	119.3
O1—Ag1—Ag2i	162.98 (4)	C3—C8—H8	119.3
O3—Ag1—O1	80.23 (5)	O6—C9—O5	126.56 (19)
O3—Ag1—O3i	82.06 (6)	O6—C9—C7	117.07 (18)
O3—Ag1—O6ii	107.63 (5)	O5—C9—C7	116.36 (17)
O3—Ag1—Ag2i	116.16 (4)	O7—C10—O8	124.57 (19)
O4—Ag2—O5iii	158.69 (7)	O7—C10—C6	117.63 (17)
O4—Ag2—O7iv	97.68 (6)	O8—C10—C6	117.78 (18)
O5iii—Ag2—O7iv	97.08 (5)	C11—N1—C16	122.5 (2)
O4—Ag2—Ag1i	81.08 (4)	C11—N1—C17	120.8 (2)
O5iii—Ag2—Ag1i	81.40 (4)	C16—N1—C17	116.8 (2)
O7iv—Ag2—Ag1i	168.58 (4)	C12—N2—C13	120.7 (2)
O5iv—Ag2—O4	119.23 (5)	C12—N2—H	120.9
O5iv—Ag2—O5iii	78.86 (6)	C13—N2—H	118.3
O5iv—Ag2—O7iv	78.31 (5)	N1—C11—C15	121.4 (2)
O5iv—Ag2—Ag1i	112.29 (4)	N1—C11—C14	122.1 (2)
C1—O1—Ag1	123.41 (13)	C15—C11—C14	116.4 (2)
C1—O2—H2	109.5	N2—C12—C15	121.3 (2)
C2—O3—Ag1i	123.07 (13)	N2—C12—H12	119.3
C2—O4—Ag2	124.47 (14)	C15—C12—H12	119.3
C9—O5—Ag2v	123.12 (13)	N2—C13—C14	121.5 (2)
C9—O6—Ag1ii	124.62 (14)	N2—C13—H13	119.3
C10—O7—Ag2iv	121.06 (12)	C14—C13—H13	119.3
O1—C1—O2	123.50 (18)	C13—C14—C11	119.7 (2)
O1—C1—C5	122.02 (17)	C13—C14—H14	120.1
O2—C1—C5	114.46 (17)	C11—C14—H14	120.1
O4—C2—O3	126.86 (19)	C12—C15—C11	120.3 (2)
O4—C2—C3	117.34 (18)	C12—C15—H15	119.8
O3—C2—C3	115.79 (17)	C11—C15—H15	119.8
C8—C3—C5	118.74 (18)	N1—C16—H16A	109.5
C8—C3—C2	119.06 (17)	N1—C16—H16B	109.5
C5—C3—C2	122.18 (17)	H16A—C16—H16B	109.5
C5—C4—C7	121.14 (18)	N1—C16—H16C	109.5
C5—C4—H4	119.4	H16A—C16—H16C	109.5
C7—C4—H4	119.4	H16B—C16—H16C	109.5
C4—C5—C3	119.97 (18)	N1—C17—H17A	109.5
C4—C5—C1	119.38 (17)	N1—C17—H17B	109.5
C3—C5—C1	120.24 (17)	H17A—C17—H17B	109.5
C8—C6—C7	119.81 (18)	N1—C17—H17C	109.5
C8—C6—C10	120.10 (17)	H17A—C17—H17C	109.5
C7—C6—C10	119.93 (17)	H17B—C17—H17C	109.5
O6ii—Ag1—O1—C1	31.61 (18)	C10—C6—C7—C9	−5.6 (3)
O3i—Ag1—O1—C1	−155.65 (17)	C7—C6—C8—C3	0.1 (3)
Ag2i—Ag1—O1—C1	88.4 (2)	C10—C6—C8—C3	−175.26 (19)
O5iii—Ag2—O4—C2	43.7 (3)	C5—C3—C8—C6	−2.1 (3)
O7iv—Ag2—O4—C2	177.18 (18)	C2—C3—C8—C6	176.43 (19)
Ag1i—Ag2—O4—C2	8.66 (17)	Ag1ii—O6—C9—O5	1.1 (3)
Ag1—O1—C1—O2	−150.04 (16)	Ag1ii—O6—C9—C7	−179.62 (13)
Ag1—O1—C1—C5	28.3 (3)	Ag2v—O5—C9—O6	11.0 (3)
Ag2—O4—C2—O3	−2.3 (3)	Ag2v—O5—C9—C7	−168.32 (13)
Ag2—O4—C2—C3	177.08 (13)	C4—C7—C9—O6	120.2 (2)
Ag1i—O3—C2—O4	−9.4 (3)	C6—C7—C9—O6	−57.5 (3)
Ag1i—O3—C2—C3	171.21 (13)	C4—C7—C9—O5	−60.4 (3)
O4—C2—C3—C8	−119.5 (2)	C6—C7—C9—O5	121.9 (2)
O3—C2—C3—C8	60.0 (3)	Ag2iv—O7—C10—O8	151.16 (17)
O4—C2—C3—C5	59.0 (3)	Ag2iv—O7—C10—C6	−27.2 (2)
O3—C2—C3—C5	−121.6 (2)	C8—C6—C10—O7	132.8 (2)
C7—C4—C5—C3	−1.1 (3)	C7—C6—C10—O7	−42.6 (3)
C7—C4—C5—C1	171.50 (18)	C8—C6—C10—O8	−45.6 (3)
C8—C3—C5—C4	2.6 (3)	C7—C6—C10—O8	139.0 (2)
C2—C3—C5—C4	−175.89 (19)	C16—N1—C11—C15	−178.3 (2)
C8—C3—C5—C1	−170.00 (18)	C17—N1—C11—C15	1.6 (3)
C2—C3—C5—C1	11.5 (3)	C16—N1—C11—C14	1.2 (4)
O1—C1—C5—C4	−138.5 (2)	C17—N1—C11—C14	−178.8 (2)
O2—C1—C5—C4	39.9 (3)	C13—N2—C12—C15	−1.2 (4)
O1—C1—C5—C3	34.1 (3)	C12—N2—C13—C14	0.9 (4)
O2—C1—C5—C3	−147.48 (19)	N2—C13—C14—C11	0.3 (4)
C5—C4—C7—C6	−0.8 (3)	N1—C11—C14—C13	179.2 (2)
C5—C4—C7—C9	−178.56 (19)	C15—C11—C14—C13	−1.2 (3)
C8—C6—C7—C4	1.3 (3)	N2—C12—C15—C11	0.2 (4)
C10—C6—C7—C4	176.73 (18)	N1—C11—C15—C12	−179.5 (2)
C8—C6—C7—C9	179.04 (19)	C14—C11—C15—C12	0.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H···O7vi	0.84	1.88	2.720 (2)	177
O2—H2···O8vii	0.82	1.73	2.541 (2)	173

Table 1

Selected bond lengths (Å)

Ag1—O1	2.5220 (15)
Ag1—O3i	2.1784 (15)
Ag1—O3	2.7573 (19)
Ag1—O6ii	2.1765 (15)
Ag2—O4	2.2091 (15)
Ag2—O5iii	2.2224 (16)
Ag2—O5iv	2.873 (2)
Ag2—O7iv	2.4442 (15)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H⋯O7v	0.84	1.88	2.720 (2)	177
O2—H2⋯O8vi	0.82	1.73	2.541 (2)	173

Symmetry codes: (v) ; (vi) .