Polyhedron 28 (2009) 2983–2988

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Polyhedron

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Influence of dicarboxylic acids on self-assembly process: Synthesesand structural characterization of new Ag(I) complexes derivedfrom mixed ligands

Di Sun a, Geng-Geng Luo a, Na Zhang a, Jian-Hua Chen a, Rong-Bin Huang a,*, Li-Rong Lin a, Lan-Sun Zheng a,b

a Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Chinab State Key Laboratory for Physical Chemistry of Solid Surfaces, Xiamen University, Xiamen 361005, China

a r t i c l e i n f o a b s t r a c t

Article history:Received 5 January 2009Accepted 8 July 2009Available online 12 July 2009

Keywords:Ag(I)2-AminopyrimidineDicarboxylic acidsCoordination polymerAg���Ag interactions

0277-5387/$ - see front matter � 2009 Elsevier Ltd. Adoi:10.1016/j.poly.2009.07.013

* Corresponding author.E-mail address: rbhuang@xmu.edu.cn (R.-B. Huang

Using the principle of crystal engineering, three new silver metal–organic coordination polymers,[Ag2(L1)2(L2)]�2H2O (1), [Ag2(L1)2(L3)]�H2O (2), [Ag2(L1)2(L4)]�2H2O (3) (L1 = 2-aminopyrimidine,L2 = oxalate anion, L3 = glutarate anion and L4 = 1,4-naphthalenedicarboxylate anion) have been synthe-sized by solution phase reactions of silver nitrate with various dicarboxylic acids and cooperative hetero-cyclic 2-aminopyrimidine ligand under the ammoniacal conditions. All the complexes have beencharacterized by elemental analyses, IR spectra and X-ray diffraction. In complex 1, L1 ligands are coor-dinated to Ag(I) metal centers in rare tridentate fashions, forming one-dimensional (1-D) ladder-likestructure, which is interlinked by L2 anions to generate 2-D pleated molecular sheet. Complex 2 displaysan interesting two-dimensional (2-D) tongue-and-groove structure containing a new kind of ‘‘T-shaped”unit. Meanwhile, each of 2-D bilayers is interlocked by four adjacent identical motifs to form three-dimensional (3-D) 5-fold interpenetrating conformation with weak Ag���Ag interactions. In complex 3,L1 ligands are coordinated to the Ag(I) ions to form 1-D polymeric chain. And L4 anions, acting as bridginglinkers through corresponding l2-carboxylates, link a pair of Ag(I) atoms from adjacent chains to yield3-D supramolecular network. The structures of complexes 1–3 which span from 2-D to 3-D networkssuggest that dicarboxylate anions play important role in the formation of such coordination architectures.

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1. Introduction

The current interest in coordination polymeric frameworksstems not only from their intriguing variety of architectures andtopologies, but also their potential applications in luminescence,nonlinear optics, porous materials, and catalysis [1–10]. The con-struction of molecular architecture depends on the combinationof several factors, such as the solvent system, template, tempera-ture, counter ion, ratio of ligands to metal ions, coordination geom-etry of central metals and organic ligands [11–14]. In this regard,the organic anions play important roles in directing the final struc-tures and topologies of their coordination polymers. The dicarbox-ylates, as important organic anions, have attracted intense interestfrom chemists due to its versatile coordination modes in theassembly of polymeric structures [15–22]. So far, although dicar-boxylates are widely utilized in the construction of coordinationpolymers [6,15–30], metal–organic frameworks (especially forcentral metal silver) built by dicarboxylates and heterocyclicpyrimidine and its derivatives, are relatively rare [31,32].

ll rights reserved.

).

On the other hand, heterocyclic pyrimidine and its derivatives,in spite of their simplicity, are very versatile systems. Their abilityfor giving specific H-bonding patterns as a key step in the storageand transmission of genetic information is a well-known process[33]. Moreover, their efficiency in binding transition metal ions isalso well known. Indeed, they are very useful to develop polymericmetal–organic hybrid frameworks (MOFs) owing to their demon-strated ability to coordinate to the metal centers through variousbonding modes, and to form very stable hydrogen-bonded chainarrays via their stereochemically associative amino and hetero ringnitrogens [34–43]. In our recent studies, 2-aminopyrimidine andits derivatives have been successfully used to construct a seriesof Ag(I) complexes with dinuclear, tetranuclear, 1-D and 2-D struc-tures [44,45]. However, we also noticed that it is difficult to gethigh-dimensional structure only using 2-aminopyrimidine or itsderivatives without other secondary ligands. As a continuation ofour work, we try to introduce dicarboxylates into previous silver/aminopyrimidine system, and obtain surprisingly three new coor-dination polymers spanning from 2-D to 3-D frameworks.

Herein, we describe syntheses and crystal structures of thethree silver(I) complexes: [Ag2(L1)2(L2)]�2H2O (1), [Ag2(L1)2(L3)]�H2O (2), [Ag2(L1)2(L4)]�2H2O (3) (where L1 = 2-aminopyrimidine,

2984 D. Sun et al. / Polyhedron 28 (2009) 2983–2988

L2 = oxalate anion, L3 = glutarate anion and L4 = 1,4-naphthalen-edicarboxylate anion). Our study shows that the structures ofdicarboxylate anions play important role in the formation of thesesilver(I) complexes.

2. Experimental

2.1. Materials and Instrumentation

All reagents and solvents in the syntheses were of reagentgrade, and they were used without further purification. Infraredspectra were recorded on a Nicolet AVATAT FT-IR360 spectrometeras KBr pellets in the frequency range 4000–400 cm�1. The elemen-tal analyses (C, H, N contents) were determined on a CE instru-ments EA 1110 analyzer. Photoluminescence measurements wereperformed on a Hitachi F-4500 fluorescence spectrophotometerwith solid powder on a 1 cm quartz round plate.

2.2. Synthesis of complex [Ag2(L1)2(L2)]�2H2O (1)

A mixture of AgNO3 (170 mg, 1 mmol), 2-aminopyrimidine(94 mg, 1 mmol) and oxalate (90 mg, 1 mmol) were stirred inCH3OH–H2O mixed solvent (10 mL, v/v: 1/1). Then aqueous NH3

solution (25%) was dropped into the mixture to give a clear solu-tion. The resultant solution was allowed slowly to evaporate indarkness at room temperature for several days to give colorlesscrystals of 1 (Yield, 50%). They were washed with a small volumeof cold CH3OH and diethyl ether. Anal. Calc. for Ag2C10H14N6O6:C, 22.66; H, 2.66; N, 15.85. Found: C, 22.61; H, 2.71; N, 15.76%. IR(KBr): m(cm�1) = 3398 (m), 3296 (m), 2962 (m), 2925 (m), 1625(s), 1600 (s), 1569 (s), 1478 (s), 1351 (m), 1313 (m), 1223 (m),788 (m), 660 (w), 520 (w), 462 (m).

2.3. Synthesis of complex [Ag2(L1)2(L3)]�H2O (2)

The synthesis of 2 was similar to that of 1, but with glutarate(132 mg, 1 mmol) in place of oxalate. Colorless crystals of 2 wereobtained in 62% yield. Anal. Calc. for Ag2C13H17N6O5: C, 28.23; H,3.09; N, 15.19. Found: C, 28.31; H, 3.14; N, 15.25%. IR (KBr):m(cm�1) = 3400 (m), 3300 (m), 2958 (m), 2924 (m), 1630 (s),

Table 1Crystallographic data for complexes 1–3.

Complexes 1

Formula Ag2C10H14N6O6

Mr 530.02Crystal system monoclinicSpace group C2/ca (Å) 15.0954(4)b (Å) 6.4357(2)c (Å) 14.9699(5)a (�) 90b (�) 95.793(3)c (�) 90Z 4V (Å3) 1446.91(8)Dc (g cm�3) 2.433l (mm�1) 2.752F(0 0 0) 1032Number of unique reflections 1235Number of observed reflections [I > 2r(I)] 1176Parameters 117Goodness-of-fit (GOF) 0.985Final R indices [I > 2r(I)]a,b R1 = 0.0223, wR2 = 0.0579R indices (all data) R1 = 0.0240, wR2 = 0.0592Largest difference peak and hole (e Å�3) 0.700 and �0.719

a R1 =P

||Fo|�|Fc||/P

|Fo|.b wR2 = [

Pw(F2

o � F2c )2/

Pw(F2

o)2]0.5.

1567 (s), 1472 (s), 1396 (m), 1349 (m), 1219 (m), 1185 (m),1056(w), 790 (m), 660 (w), 517 (w), 462 (m).

2.4. Synthesis of complex [Ag2(L1)2(L4)]�2H2O (3)

The synthesis of 3 was similar to that of 1, but with 1,4-naph-thalenedicarboxylate (216 mg, 1 mmol) in place of oxalate. Color-less crystals of 3 were obtained in 55% yield. Anal. Calc. forAg2C20H20N6O6: C, 36.61; H, 3.07; N, 12.81. Found: C, 36.70; H,3.12; N, 12.88%. IR (KBr): m(cm�1) = 3393 (m), 3301 (m), 1626 (s),1570 (s), 1479 (s), 1410(m), 1364 (m), 1223 (m), 789 (m), 660(w), 512 (w), 468 (m).

2.5. X-ray crystallography

Single crystals of the complexes 1–3 with appropriate dimen-sions were mounted on a glass fiber and used for data collection.Data was collected on a Bruker-AXS CCD diffractometerequipped with a graphite-monochromated Mo Ka radiationsource (k = 0.71073 Å) for 1–3. All absorption corrections wereperformed with the SADABS program [46]. All the structures weresolved by direct methods using SHELXS-97 [47] and refined byfull-matrix least-squares techniques using SHELXL-97 [48]. All thenon-hydrogen atoms were treated anisotropically. The positionsof hydrogen atoms were generated geometrically. The crystallo-graphic details of 1–3 are summarized in Table 1. Selected bondlengths and bond angles of 1–3 are displayed in Table 2. Thehydrogen bond geometries are shown in Table S1 (in the Supple-mentary data).

3. Results and discussion

3.1. Syntheses and IR spectra

The syntheses of complexes 1–3 are carried out in the dark-ness to avoid photodecomposition and summarized in SchemeS1, in the Supplementary data. The formation of the products isnot significantly affected by changes of the reaction mole ratioof organic ligands to metal ions, and the resultant crystals areinsoluble in water and common organic solvents. The infrared

2 3

Ag2C13H17N6O5 Ag2C20H20N6O6

553.06 656.16monoclinic orthorhombicC2/c Pnna8.3565(9) 12.4033(5)9.8212(9) 17.4377(8)20.530(2) 10.0645(4)90 9095.071(5) 9090 904 41678.3(3) 2176.8(2)2.189 2.0022.374 1.8511084 12961627 18711270 1524123 1550.934 1.076R1 = 0.0470, wR2 = 0.1130 R1 = 0.0379, wR2 = 0.0938R1 = 0.0617, wR2 = 0.1262 R1 = 0.0482, wR2 = 0.09781.371 and �1.318 0.635 and �0.505

Table 2Selected bond distances (Å) and angles (�) for 1–3.

Complex 1Ag(1)–N(1) 2.313(2) Ag(1)––N(3)ii 2.540(3) Ag(1)iii–N(2) 2.312(2)Ag(1)–O(2) 2.630(4)N(2)i–Ag(1)–N(1) 123.33(9) N(2)i–Ag(1)–N(3)ii 104.81(8)N(1)–Ag(1)–N(3)ii 100.47(8)

Complex 2Ag(1)–N(2) 2.219(5) Ag(1)–O(2) 2.290(5) Ag(1)–N(1)i 2.317(5)Ag(1)–Ag(1)ii 3.241(1) Ag(1)–Ag(1)iii 3.269(1) Ag(2)–O(2) 2.485(5)Ag(2)–O(3) 2.674(5)N(2)–Ag(1)–O(2) 135.2(2) N(2)–Ag(1)–N(1)i 127.8(2)O(2)–Ag(1)–N(1)i 95.2(2) N(2)–Ag(1)–Ag(1)ii 99.1(1)O(2)–Ag(1)–Ag(1)ii 76.2(1) N(1)i–Ag(1)–Ag(1)ii 77.6(1)N(2)–Ag(1)–Ag(1)iii 72.1(1) O(2)–Ag(1)–Ag(1)iii 119.4(1)Ag(1)ii–Ag(1)–Ag(1)iii 164.18(3)

Complex 3Ag(1)–N(3) 2.322(4) Ag(1)–O(1) 2.406(3) Ag(2)–N(1) 2.180(4)Ag(2)–O(1)iii 2.579(3)N(3)–Ag(1)–N(3)i 105.0(2) N(3)–Ag(1)–O(1)i 104.9(1)N(3)–Ag(1)–O(1) 132.9(1) N(1)ii–Ag(2)–N(1) 148.6(2)O(1)i–Ag(1)–O(1) 79.3(2) N(1)–Ag(2)–O(1)iii 102.0(1)N(1)–Ag(2)–O(1)iv 103.2(1) O(1)iii–Ag(2)–O(1)iv 73.1(2)Ag(1)–O(1)–Ag(2)iii 103.8(1)

Symmetry transformations used to generate equivalent atoms: (i), x, y + 1, z, (ii), �x + 1/2, y + 1/2, �z + 1/2, (iii), x, y�1, z, for 1; (i), x�1/2, y + 1/2, z, (ii), �x�1/2, �y + 1/2, �z,(iii), �x�1, �y, �z, for 2; (i), �x�1/2, �y + 1, z, (ii), �x + 1/2, �y + 1, z, (iii), �x, �y + 1, �z + 2, (iv), x + 1/2, y, �z + 2, for 3.

D. Sun et al. / Polyhedron 28 (2009) 2983–2988 2985

spectra and elemental analyses of 1–3 are fully consistent withtheir formations. Their IR spectra exhibit the absorptions in therange of �3296 to �3400 cm�1, corresponding to the N–Hstretching vibrations of the amide group. Strong characteristic

Fig. 1. (a) ORTEP drawing of 1 showing the coordination environment around Ag(I) centeL1 ligands in 1 along the c axis. (c) A view of the 2-D pleated molecular sheets in 1 alonglines correspond to the hydrogen bonds. Ag stressed in bigger ball.

bands of carboxylic groups are observed in the range of �1630to �1560 cm�1 for the asymmetric vibrations and �1480 to�1350 cm�1 for symmetric vibrations, respectively. The absenceof the characteristic bands at around �1700 cm�1 attributed to

rs at 40% probability level. (b) A view of the 1-D ladder formed by silver centers andthe c axis. Hydrogen atoms in pyrimidyl groups were omitted for clarity. The dashed

2986 D. Sun et al. / Polyhedron 28 (2009) 2983–2988

the protonated carboxylic groups, indicating that the completedeprotonation of all carboxylate groups in 1-3 upon reaction withAg ions [49].

3.2. Crystal structure of [Ag2(L1)2(L2)]�2H2O (1)

The present X-ray crystal structure analysis suggests that com-plex 1 crystallizes in the monoclinic space group C2/c. The C2 axislies in the midpoint of C–C single bond of L2 anion, hence, eachasymmetric unit contains one Ag(I) ion, one L1 ligand, a half L2 an-ion and one uncoordinated water. As shown in Fig. 1a, each four-coordinate Ag, which adopts a distorted tetrahedral geometry, iscoordinated by two bridging L1 nitrogen atoms, one amino nitro-gen atom and one deprotonated oxalic acid oxygen atom. The larg-est N(2)–Ag(1)–O(2) angle opened up to 132.69(8)� from the idealtetrahedral angle while the remaining angles are in the range from104.81(8) to 123.33(9)�. It is noteworthy that the Ag–N distancesto amino nitrogen atoms [Ag(1)–N(3A) = 2.540(3) Å] are signifi-cantly longer than those to the pyrimidyl nitrogen atoms [Ag(1)–N(1) = 2.313(2) and Ag(1)–N(2B) = 2.312(2) Å]. This differencemay partially be due to the electronic effect between amino nitro-gen and pyrimidyl nitrogen atoms. Interestingly, As far as weknow, most of aminopyrimidine derivatives often adopt N-mono-dentate and N,N0-bidentate coordination modes with silver atomsvia pyrimidyl nitrogen atoms, and the only example with triden-tate fashion was ever reported by Wang [40]. Here, L1 ligandsare coordinated to the Ag(I) metal centers by taking this rareN,N0,N00-tridentate modes to form 1-D ladder structures (Fig. 1b),which were interlinked by L2 anions [Ag(1)–O(2) = 2.630(4) Å] togenerate 2-D pleated molecular sheets (Fig. 1c). Each L2 anion is

Fig. 2. (a) ORTEP drawing of 2 showing the coordination environment around Ag(I) centand-groove structure along the c axis. All hydrogen atoms and solvent molecules have be

coordinated to the metal centers in a bidentate l1-O, l1-O0-bond-ing mode.

In addition, as shown in Fig. 1c, in each molecular sheet, theAg(I) ions, L1 ligands and L2 anions are interlinked to form chair-like eight-membered binuclear ring and 18-membered metallocy-cles in each molecular sheet. Two kinds of intermolecular hydro-gen bonds are observed in the 18-membered metallocycles,including N–H���O hydrogen bonds where the amino group of L1 li-gands serve as donors while the uncoordinated oxygen atoms onthe L2 anions act as acceptors [N(3)–H(3C)���O(1)i, 2.843(4) Å,\N–H���O, 141.7�; symmetry code: (i), x, y�1, z], and O–H���Ohydrogen bonds where oxygen atoms of L2 anions serve as accep-tors while hydrogen atoms of uncoordinated water act as donors[O(1W)–H(1WB)���O(2)ii, 2.957(6) Å, \O–H���O, 157.0�; symmetrycode: (ii), �x + 1, y + 1, �z + 1/2].

3.3. Crystal structure of [Ag2(L1)2(L3)]�H2O (2)

When oxalate is replaced by more flexible glutarate and reactedwith AgNO3 and L1 ligand under the similar synthetic conditions, afascinating 3-D structure of 2 is produced. The molecular ORTEPdrawing of 2 together with the atom-numbering scheme is de-picted in Fig. 2a. X-ray crystal structure determination displaysthat 2 consists of molecular bilayers with T-shaped blocks as thefundamental building units, in which each central Ag(I) cationadopts a T-shaped coordination configuration with two pyrimidylnitrogen donors [Ag(1)–N(1A) = 2.317(5) and Ag(1)–N(2) = 2.219(5) Å] of L1 ligand in the horizontal direction. Thecoordination sphere is completed by one oxygen donor [Ag(1)–O(2) = 2.290(5) Å] of one deprotonated glutarate (L3) in the axial

ers at 40% probability level. (b) Packing diagram of 2 showing microporous tongue-en omitted for clarity. (c) Schematic representation of molecular bilayer motif of 2.

D. Sun et al. / Polyhedron 28 (2009) 2983–2988 2987

direction, forming a new type of T-shaped unit. Fig. 2b shows that 2contains molecular bilayer motifs, and Fig. 2c gives the schematicrepresentation of corresponding bilayer motif. Each L1 as a biden-tate ligand links Ag(I) centers to form infinite 1-D chains in the abplane, and intramolecular N–H���O hydrogen bonds occur in the 1-D chains where oxygen atoms of L3 anions serve as acceptors whilethe uncoordinated amino groups of L1 ligands act as donors [H���O,2.02–2.06 Å, N���O, 2.863(6)–2.897(7) Å, \N–H���O, 163.7–167.5�].Interestingly, two kinds of extended modes are observed for these1-D chains (herein designated as A and B). When viewed fromabove the ab plane, Fig. 2b shows that two related [Ag(L1)]1 chainsare interlaced. The complete deprotonated L3 anions, acting as pil-lars, interlink the upper and lower chains to generate bilayer gal-leries. The width of the galleries is determined by the length ofL1 ligand (6.448 Å), and their height is fixed by the length of L3 an-ion (9.847 Å).

To the best of our knowledge, most of the reported silver(I) me-tal–organic frameworks containing such bilayer motifs have fo-cused on the structures based on single ligand 4,40-bipy or othermixed ligands with 4,40-bipy bridges. However, there are no sucha distinctive tongue-and-groove structure of 3-D frameworks ofcoordination polymers with aminopyrimidine bridges reported inthe literature. Furthermore, a remarkable feature of the structureof 2 is that the bilayer is sustained by the long L3 anion and shortL1 ligand and displays an unusual entanglement (see Fig. S1, in theSupplementary data). Its structure belongs to a kind of 2-D to 3-Dparallel interpenetration of ‘‘thick” layers: the 2-D layers interpen-

Fig. 3. (a) ORTEP drawing of 3 showing the coordination environment around Ag(I) center3. (c) The 3-D supramolecular structure of 3. All hydrogen atoms and solvent molecules

etrate each other in quintuple mode and the 5-fold interpenetrat-ing results in Ag���Ag interactions. The separations between silversare alternatively 3.269 and 3.241 Å, which are slightly shorter thanthe summed van der Waal radius of two silver atoms (3.44 Å)[50,51], indicating the existence of weak Ag���Ag interactions. Inthe molecular bilayer, the lattice water molecule is enclathratedin the cavity of the bilayer and it forms a hydrogen bond withthe O1 atom of L3 anion [O(1w)���O(1)i = 2.809(7) Å, symmetrycode: (i), �x�1/2, y + 1/2, �z�1/2].

Obvious changes are observed from the structures and dimen-sions (2-D(1) to 3-D(2)) of 1 and 2. The striking structural differ-ence between 1 and 2 is simply caused by different –CH2–spacers in the dicarboxylate anions, i.e., L3 anion with longer spac-ers than L2 anion shows more flexible in nature, which allows theanion to bend and rotate freely when coordinating to metalcenters.

3.4. Crystal structure of [Ag2(L1)2(L4)]�2H2O (3)

When using rigid aromatic 1,4-naphthalenedicarboxylate in-stead of oxalate to react with AgNO3 and L1 under the similar syn-thetic conditions, complex 3 with a different structural type fromothers has been obtained. Single crystal X-ray analysis reveals thatcomplex 3 crystallizes in the orthorhombic space group Pnna. Theasymmetric unit consists of two Ag(I) ions, two L1 ligands, one L4anion, and two uncoordinated water molecules. The charge neu-trality is achieved by the fully deprotonated carboxylate groups

s at 40% probability level. (b) A packing diagram showing the 1-D ladder structure inhave been omitted for clarity.

2988 D. Sun et al. / Polyhedron 28 (2009) 2983–2988

of 1,4-naphthalenedicarboxylate. As shown in Fig. 3a, twoindependent Ag(I) ions have similar coordination environments,and each central Ag(I) ion is coordinated by two nitrogen atoms[Ag(1)–N(3) = 2.322(4), Ag(1)–N(3A) = 2.322(4) Å; Ag(2)–N(1) =2.180(4), Ag(2)–N(1A) = 2.180(4) Å] from two L1 ligands and twooxygen atoms [Ag(1)–O(1) = 2.406(3), Ag(1)–O(1A) = 2.406(3) Å;Ag(2)–O(1B) = 2.579(3), Ag(2)–O(1C) = 2.579(3) Å] from differentL4 anions in a tetrahedral geometry. All the Ag–N and Ag–O bonddistances are within the normal range [35,52,53]. Two such asym-metric units are connected to form a centrosymmetrically tetranu-clear 12-membered metallocycle [Ag4(L1)2(L4)2]. There is aquadrangle core in the discrete tetranuclear unit. The interatomicdistances of Ag–Ag are 6.287 Å on the long sides of the quadrangleand 3.925 Å on the short sides of the quadrangle, excluding any di-rect metal–metal interaction. The 12-membered rings are inter-connected each other through L1 ligands to generate 1-D doublepolymeric chains (Fig. 3b). Each L1 ligand has similar N,N0-biden-tate coordination mode. Moreover, acting as bridging linkersthrough corresponding l2-carboxylates, L4 anions connect a pairof adjacent Ag(I) atoms to yield 3-D supramolecular networks(Fig. 3c). It is noteworthy that L4 anions hold the same coordina-tion mode with different naphthyl orientation. In addition, latticewater molecules occupy the residual space and are hydrogenbonded to the carboxylate groups from L4 anions[O(1w)���O(2) = 2.941(6) and O(1w)���O(2)i = 2.944(5) Å, symmetrycode: (i) x, �y + 3/2, �z + 5/2].

4. Conclusions

With the principal aim of obtaining new high-dimensionalcoordination polymers with interesting photoluminescence, wetry to introduce dicarboxylates into previous silver/aminopyrimi-dine system, and get three new silver(I) coordination polymersspanning from 2-D to 3-D frameworks. The analysis of the crystal-lographic data of 1–3 clearly shows that the structures of dicarbox-ylate anions are the key factors in directing self-assembly suchdiverse structures of these silver(I) complexes.

Acknowledgments

This work was financially supported by the National NaturalScience Foundation of China (No. 20721001) and 973 Project(Grant 2007CB815301) from MSTC.

Appendix A. Supplementary data

CCDC 714483, 714484 and 714485 contain the supplementarycrystallographic data for 1, 2 and 3. These data can be obtained freeof charge via http://www.ccdc.cam.ac.uk/conts/retrieving.html, orfrom the Cambridge Crystallographic Data Centre, 12 Union Road,Cambridge CB2 1EZ, UK; fax: (+44) 1223-336-033; or e-mail: de-posit@ccdc.cam.ac.uk. Supplementary data associated with thisarticle can be found, in the online version, at doi:10.1016/j.poly.2009.07.013.

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