Novel Network Polymers Formed by Self-Assembly of Silver Nitrate

This article describes four novel network polymers self-assemblied by AgNO3 and .... IP diffractometer with Mo Kα radiation (λ = 0.71073 Å) at room...
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Novel Network Polymers Formed by Self-Assembly of Silver Nitrate and Pyrrol-2-yl-methyleneamine Ligands with Flexible Spacers Guoqi Zhang,† Guoqiang Yang,*,† Qingqi Chen,‡ and Jin Shi Ma*,†

CRYSTAL GROWTH & DESIGN 2005 VOL. 5, NO. 2 661-666

CAS Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100080, P. R. China, and BioMarin Pharmaceutical Inc., 46 Galli Drive, Novato, California 94949 Received May 23, 2004;

Revised Manuscript Received August 9, 2004

ABSTRACT: This paper reports on four novel network polymers formed by self-assembly of AgNO3 and pyrrol-2yl-methyleneamine ligands with alkyl chain spacers. The reaction of 1,3-bis(pyrrol-2-yl-methyleneamino)propane (1) with 1 or 2 equiv of AgNO3 gives network polymers 3 and 4, respectively. The structures of 3 and 4 are very similar, in which two ligands 1 are bound to two Ag(I) ions to form a distorted rectangle. These metallic rectangles are further constructed into 1D and 2D networks by nitrate ion acting as a bridge. The reaction of 1,4-bis(pyrrol2-yl-methyleneamino)butane (2) with 1 and 2 equiv of AgNO3 is found to give network polymers 5 and 6, respectively. X-ray crystal analysis reveals that the structures of 5 and 6 are very similar, in which the 1D network is formed by direct coordination of Ag (I) with ligand 2 in a ratio of 1:1. The 1D network is further constructed to a 2D network by the nitrate ion acting as a bridge. Weak hydrogen-metal bonding (C-H‚‚‚Ag) is observed in crystals of 5 and 6 and plays a crucial role on the formation of a 3D network. Introduction Metal-ion-mediated self-assembly is one of most powerful approaches to supramolecular architectures.1 This strategy typically utilizes metal-ligand interactions to organize small molecules into large assemblies. Obviously, ligands are the key for such research. Inspired by the chemical structures and the self-assembly chemistry of bipyridines1 and dipyrromethene ligands,2,3 our group recently is exploring pyrrol-2-yl-metheneamine ligands I as building blocks for supramolecular architectures.4

bly.4 By varying the spacers between two pyrrol-2-ylmethyleneamine units, multidimensional network polymers,4c,4d dinuclear dimeric helicates,4 trinuclear trimeric triangle,4a and tetranuclear tetrameric square4a complexes were generated, which demonstrated that pyrrol-2-yl-methyleneamine ligands are ideal building blocks for self-assembly. In this paper, we report the first 1D, 2D, and 3D network polymers formed by self-assembly of AgNO3 with the flexible alkyl chain bridged bis(pyrrol-2-ylmethyleneamine) ligands 1 and 2. Experimental Procedures

Ligands I, a pyrrol-2-yl Schiff base or pyrrol-2-ylmethyleneamine, could be easily prepared by condensation of 2-formylpyrrole with a primary amine. The complexes II formed by the reaction of I with metal ions have been long known.5 Macrocycles containing pyrrol2-yl-methyleneamine units, such as texaphyrins and expanded porphyrins,6 have been extensively investigated. Linear spaced bis(pyrrol-2-yl-methyleneamine) and their complexes with metal ions were reported,7 which showed that both the preparation of ligands and the complexes were highly efficient, and the metal complexes formed by pyrrol-2-yl-methyleneamines possessed good solubility in common solvents. Attracted by those properties, our group recently investigated the use of pyrrol-2-yl-methyleneamine ligands for self-assem* To whom correspondence should be addressed. E-mail: gqyang@ iccas.ac.cn or [email protected]; fax: +86-10-82617315. † Chinese Academy of Sciences. ‡ BioMarin Pharmaceutical Inc.

General. All starting materials were purchased from Aldrich and used without further purification and solvents were disposed according to standard methods before use. Ligands 1 and 2 were synthesized by previously reported procedures and well characterized.4d Samples for C, H, N analyses were dried under a vacuum and the analysis were performed with a Carlo Erba-1106 instrument. FT-IR spectra were recorded on a BIO-RAD FT-165 IR spectrometer. The ESI-MS measurements were carried out with a Brucker APEX II instrument. Synthesis of [Ag(1)(NO3)]2‚CH3OH‚H2O (3). To a solution of 1 (45.6 mg, 0.2 mmol) in 10 mL of dichloromethane was carefully added a solution of AgNO3 (34.0 mg, 0.2 mmol) in 5 mL of methanol under dark. The resulting colorless solution was stirred for 30 min at room temperature and then filtered. The filtrate was allowed to evaporate slowly at 5 °C. After one week, colorless crystalline products appeared, which were collected, washed with absolute methanol, and dried under a vacuum. Yield: 72% (57.3 mg). mp: 113-115 °C; ESI-MS: m/z (%): 777.0(15.8)[M3L2+], 671.1(73.5)[M2L2+], 563.2(39.7)[ML2+], 335.0(100)[ML+], 229.1(85)[L+]; FT-IR (KBr pellets, cm-1): ν ) 3116, 3080, 2944, 2850, 2751, 1762, 1637, 1387, 1315, 1247, 1131, 1097, 1034, 989, 881, 828, 751, 608; Anal. Calcd for C26H32Ag2N8‚2NO3‚2H2O‚CH3OH: C, 37.52; H, 4.66; N, 16.62. Found: C, 37.45; H, 4.29; N, 16.52. Synthesis of [Ag(1)(NO3)]2‚CH2Cl2 (4). Complex 4 was prepared by a procedure similar to that of 3 except that 2 equiv of AgNO3 (68.0 mg, 0.4 mmol) was added during the reaction. Colorless blocklike crystals were obtained by slow evaporation

10.1021/cg049833h CCC: $30.25 © 2005 American Chemical Society Published on Web 09/21/2004

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Table 1. Crystallographic Data for Silver Complexes 3-6 formula fw cryst color crystal system space group T, K λ, Å a/Å b/Å c/Å R, deg β, deg γ, deg V, Å3 Z F(000) Fcalc (g/cm3) goodness-of-fit µ, mm-1 Ra Rwb a

3

4

5

6

C27H36 Ag2 N10O8 844.40 colorless orthorhombic P2(1)2(1)2(1) 293(2) 0.71073 9.4230(19) 17.386(4) 19.934(4) 90.00 90.00 90.00 3265.8(11) 4 1704 1.709 0.937 1.263 0.0376 0.0494

C28H36Ag2Cl4N10O12 1062.21 colorless monoclinic P2(1)/n 293(2) 0.71073 11.693(2) 10.006(2) 17.434(4) 90.00 102.59(3) 90.00 1990.7(7) 2 1064 1.772 0.970 1.322 0.0382 0.1120

C14H18AgN5O3 412.20 colorless monoclinic Cc 293(2) 0.71073 14.354(3) 14.127(3) 8.0576(16) 90.00 101.91(3) 90.00 1598.8(6) 4 832 1.713 1.059 1.283 0.0358 0.0826

C14H18AgN5O3 412.20 colorless monoclinic Cc 293(2) 0.71073 14.142(4) 14.381(4) 8.033(3) 90.00 101.35(2) 90.00 1601.7(9) 4 832 1.709 1.106 1.280 0.0318 0.0827

R ) ∑(Fo - Fc)/∑(Fo). b Rw )∑w(Fo2 - Fc2)2/∑w(Fo2)2)1/2.

of the reaction solution during a period of two weeks. The analytical samples were washed with absolute methanol and dried under a vacuum. Yield: 75% (59.7 mg) based on 1, mp: 108-110°C. ESI-MS: m/z (%): 777.0(10.8)[M3L2+], 671.1(65.9)[M2L2+], 563.2(34.1)[ML2+], 335.1(100)[ML+], 229.1(80)[L+]; FT-IR (KBr pellets, cm-1): ν ) 3115, 2943, 2850, 2751, 2583, 1760, 1635, 1387, 1200, 1133, 1097, 1035, 989, 967, 881, 828, 749, 605; Anal. Calcd: C26H32Ag2N8‚2NO3‚2H2O: C, 37.52; H, 4.36; N, 16.83. Found: C, 37.72; H, 4.45; N, 16.37. Synthesis of [Ag(2)(NO3)]n (5). To a solution of 2 (48.4 mg, 0.2 mmol) in 10 mL of dichloromethane was carefully added a solution of AgNO3 (34.0 mg, 0.2 mmol) in 5 mL of methanol under dark. The resulting colorless solution was stirred for ca. 30 min at room temperature and then filtered. The filtrate was allowed to evaporate slowly at 5 °C. Colorless crystalline products were obtained after two weeks. The analytical samples were washed with absolute methanol and dried under a vacuum. Yield: 81% (66.7 mg) mp: 140 °C (dec). ESI-MS: m/z (%): 805.0(4.0)[M3L2+], 699(26.2)[M2L2+], 349.0(84.1)[ML+], 243.2(100)[L+]; FT-IR (KBr pellets, cm-1): ν ) 3172, 2928, 2850, 1642, 1553, 1386, 1185, 1133, 1099, 1036, 966, 880, 828, 772, 731, 606; Anal. Calcd for (C14H18AgN4‚NO3‚ 0.5H2O)n: C, 39.89; H, 4.51; N, 16.62. Found: C, 40.20; H, 4.46; N, 16.59. Synthesis of [Ag(2)(NO3)]n (6). Complex 6 was prepared by a procedure similar to that of 5 except that 2 equiv of AgNO3 (68 mg, 0.4 mmol) was added during the reaction. Colorless prisms were obtained by slow evaporation of the reaction solution during a period of two weeks. The analytical samples were washed with absolute methanol and dried completely under a vacuum. Yield: 78% (64.3 mg) based on 2, mp: 147 °C (dec); ESI-MS: m/z (%): 805.0 (1.1) [M3L2+], 699.4 (5.2) [M2L2+], 349.2(27.1)[ML+], 243.2(100)[L+]; FT-IR (KBr pellets, cm-1): ν ) 3181, 2927, 2851, 1628, 1552, 1382, 1313, 1185, 1130, 1099, 1036, 967, 880, 828, 774, 606; Anal. Calcd for (C14H18AgN4‚NO3‚0.5H2O)n: C, 39.89; H, 4.51; N, 16.62. Found: C, 40.28; H, 4.42; N, 16.66. X-ray Crystallography. Crystals suitable for X-ray diffraction studies were obtained by slow evaporation from CH2Cl2-MeOH solutions. Accurate unit cell parameters were determined by a least-squares fit of 2θ values, measured for 200 strong reflections, and intensity data sets were measured on a Bruker Smart 1000 CCD or Rigaku Raxis Rapid IP diffractometer with Mo KR radiation (λ ) 0.71073 Å) at room temperature. The intensities were corrected for Lorentz and polarization effects, but no corrections for extinction were made. All structures were solved by direct methods. The nonhydrogen atoms were located in successive difference Fourier

Scheme 1

synthesis. The final refinement was performed by full matrix least-squares methods with anisotropic thermal parameters for non-hydrogen atoms on F2. The hydrogen atoms were added theoretically and riding on the concerned atoms. Crystallographic data and experimental details for structure analyses are summarized in Table 1.

Results and Discussion Syntheses and General Characterization. The pyrrole-based bis-Schiff base ligands 1 and 2 were prepared in high yields as shown in Scheme 1 according to the previous methods;4 thus, silver complexes 3 and 4 were prepared by treating ligand 1 with 1 and 2 equiv of silver nitrate in methanol-dichloromethane (5/10, v/v), respectively (Scheme 2). Similarly, complexes 5 and 6 were prepared by treating ligand 2 with 1 and 2 equiv of silver nitrate under the same solvent system and reaction conditions (Scheme 2). All reactions were carried out in the dark. These complexes are soluble in methanol and acetonitrile and slightly soluble in THF, acetone, and dichloromethane. The ESI-MS spectroscopy and infrared spectra for 3-6 support the formation of the corresponding silver complexes (see Experimental Section). In the case of complexes 3 and 4, both ESIMS show the maximum peaks with 100% abundance at m/z ) 335.1, which corresponds to the formation of [ML]+ species in solution. This suggests that the [ML]+ subunit may be the key building block for the formation of stable dimeric dinuclear metallomacrocycles 3 and 4, which is similar with the Ag+ complex reported by Amouri and cowokers.1g,1h Instantaneous formation of other species such as [M3L2]+, [ML2]+ is not as stable as the final complexes. For both 5 and 6 the maximum peak is at m/z ) 243.2, which corresponds to the species of [L]+ in solution, and less abundances are [ML]+,

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Scheme 2. Rectangle Metallocylic Structure of Complexes 3 and 4, and 1D Network Structure of Complexes 5 and 6, in which the Ligand 2 Is Linked together by Silver (I) Ions with a Ratio of 1:1 for Ag:2

[M2L2]+, and [M3L2]+; thus the suggestion of [ML]+ as a building block is reasonable for the final formation of stable complexes of 5 and 6. Single crystals suitable for X-ray diffraction analysis are grown up under dark and low temperatures by slow evaporation. Accordingly, X-ray structure analysis confirmed the structures of all four complexes in the solid state. Description of the Crystal Structures of Complexes 3 and 4. The ORTEP drawings of 3 and 4 including the atomic numbering scheme are shown in Figures 1a and 2a, respectively. The structures of 3 and 4 are very similar except for slight differences of some bond distances and bond angles (for comparison see Table 2). Moreover, in unit cells of 3 one methanol and one solvate water molecules are observed, while in that of 4, only one dichloromethane molecule is observed. In the unit cells of both 3 and 4 ligands and silver(I) ions are bound together in a 2:2 ratio of ligand/metal to form a metallocycle shaped as a distorted rectangle. Ag centers are found to adopt nearly linear geometry in two-coordinated with two nitrogen atoms of imine groups in two distict ligands in 3 and 4. Moreover, X-ray structure analysis clearly reveals that nitrate ion acts as a powerful bridging linker and plays crucial roles in the formation of the 2D or 1D network (see Figures 1b and 2b). For 3, three oxygen atoms in nitrate ion are the bridging arms, in which two oxygen atoms are weakly bound to the Ag(I) center, and the residual oxygen atom is responsible for the construction of a 1D zigzag network by linking rectangle metallocyles through the hydrogen bonding between nitrate ion and pyrroleNH group, i.e., (nitrate)NdO‚‚‚H-N(pyrrole) (see Table 3 for details). One of the oxygen atoms bound to Ag(I) serves to construct an expanded 2D network by linking another 1D chain through another (nitrate)NdO‚‚‚HN(pyrrole) hydrogen bonding; thus, all rectangle metallocycles are connected together by an interlaced pattern (see Figure 1b). In comparison to 3, only a 1D zigzag network exists formed by nitrate ions as bridging arms in 4, and similarly, two oxygen atoms of nitrate ion are weakly bound to the Ag(I) center and another

Figure 1. (a) ORTEP drawing of complex 3 showing the atomic numbering scheme with 30% thermal ellipsoid probability. Hydrogen atoms were omitted for clarity. (b) 2D hydrogen-bonded network of 3 constructed by nitrate ions.

Figure 2. (a) ORTEP drawing of complex 4 showing the atomic numbering scheme with 30% thermal ellipsoid probability. Hydrogen atoms were omitted for clarity. (b) 1D polymeric chain bridged by nitrate ions in 4.

oxygen atom contributes to link rectangle metallocyles through the same hydrogen-bonding model as that found in 3. In the macrocycle units of 3 and 4, the Ag-Ag distances are 5.01-5.03 Å, and the shortest distances between carbon atoms at opposite sides are 4.34 and

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Table 2. Selected Bond Lengths (Å) and Angles (deg) for 3-6 3 Ag(1)-N(6) Ag(2)-N(3) N(6)-Ag(1)-N(2) C(6)-N(2)-Ag(1) C(8)-N(3)-Ag(2)

2.1420(16) 2.1348(16) 163.86(7) 112.58(11) 115.37(12)

Ag(1)-N(3) N(2)-C(5) N(3)-C(11) N(3)-Ag(1)-N(2) C(6)-N(2)-Ag(1) C(12)-N(3)-Ag(1)

2.1316(12) 1.275(2) 1.2860(19) 170.12(5) 115.10(10) 115.31(9)

Ag(1)-N(2) Ag(2)-N(7) N(3)-Ag(2)-N(7) C(19)-N(6)-Ag(1) C(21)-N(7)-Ag(2)

2.1455(15) 2.1467(15) 168.01(7) 119.92(13) 116.01(11)

Ag(1)-N(2) N(2)-C(6) N(3)-C(12) C(5)-N(2)-Ag(1) C(11)-N(3)-Ag(1)

2.1358(13) 1.479(2) 1.467(2) 127.90(10) 127.16(11)

4

5 Ag(1)-N(3) Ag(1)‚‚‚O(3) N(3)-Ag(1)-N(2) C(5)-N(2)-Ag(1) C(11)-N(3)-Ag(1)

2.113(7) 2.641 169.4(3) 124.6(5) 113.9(5)

Ag(1)-N(3B) Ag(1)-O(1) N(3B)-Ag(1)-N(2) C(6)-N(2)-Ag(1) C(5)-N(2)-Ag(1)

2.105(5) 2.570(14) 168.2(3) 118.4(4) 123.8(4)

Ag(1)-N(2)

2.142(7)

N(2)-Ag(1)-O(3) N(3)-Ag(1)-O(3) O(1)-N(5)-O(3)

90.8 98.9 120.9(9)

Ag(1)-N(2)

2.123(5)

N(3B)-Ag(1)-O(1) N(2)-Ag(1)-O(1) O(1)-N(5)-O(3)

102.1(3) 89.7(3) 120.7(9)

6

Table 3. Summary of Hydrogen Bonds (Å) for Complexes 3-6 d(D‚‚‚A)

< (DHA)

N(1)-H(1A)‚‚‚O(1) N(1)-H(1A)‚‚‚O(3) N(4)-H(4A)‚‚‚O(3)1# N(8)-H(8C)‚‚‚O(4)2#

3 2.08 2.61 2.13 2.03

2.901(2) 3.354(2) 2.936(2) 2.869(2)

160.4 146.1 155.7 166.5

N(1)-H(1A)‚‚‚O(2)3# N(4)-H(4A)‚‚‚O(2)4# N(4)-H(4A)‚‚‚O(1)4#

4 2.142 2.169 2.459

2.925 2.984 3.211

151.20 157.89 146.40

N(4)-H(4A)‚‚‚O(3)5# N(4)-H(4A)‚‚‚O(2)5# N(4)-H(4A)‚‚‚N(5)5# C(2BE)-H(2AI)‚‚‚O(2BB) C(3BL)-H(3AT)‚‚‚O(2BB)

5 2.082 2.485 2.660 2.268 2.101

2.930 3.154 3.489 3.173 2.927

168.78 135.18 162.49 164.2 147.3

N(4D)-H(4AD)‚‚‚N(5B) N(4D)-H(4AD)‚‚‚O(3B) N(4D)-H(4AD)‚‚‚O(1B) C(3F)-H(3BF)‚‚‚O(3G) C(2G)-H(2AG)‚‚‚O(3A)

6 2.640 2.570 2.050 2.062 2.193

3.483 3.280 2.897 2.904 3.105

165.9 139.5 166.5 145.4 158.1

D-H‚‚‚Aa

d(H‚‚‚A)

a Symmetry transformations used to generate equivalent atoms: 1#, x - 1/2, -y + 3/2, -z + 1; 2#, -x + 1/2, -y + 1, z + 1/2; 3#, -x, -y + 2, -z; 4#, -x + 1/2, y - 1/2, -z + 1/2; 5#, x - 1/2, -y + 1/2, z - 1/2.

4.25 Å, respectively. The Ag-Nimine bond distances are in the range of 2.13-2.16 Å, which are consistent with the reported data.8,9 The N-Ag-N angles are 164-171°, which proves two silver ions have almost linear coordination geometry. In addition, four pyrrole rings are found to have no interaction with silver ions and the planes of two adjacent pyrrole rings on one side of the macrocycle distort strongly with 46° and 125° dihedral angles, respectively. Description of the Crystal Structures of Complexes 5 and 6. Although ligand 2 is structurally very similar to ligand 1, to our surprise, the crystal structures of 5 and 6 (Figures 3 and 4) are completely

Figure 3. (a) ORTEP drawing of complex 5 showing the atomic numbering scheme with 30% thermal ellipsoid probability. Hydrogen atoms were omitted for clarity. (b) 2D Structure of 5 formed by the C-H‚‚‚Ag weak hydrogen bonding. (c) Crystal packing along the a axis showing the formation of 3D supramolecular architecture by hydrogenbonding interactions.

different from 3 and 4. Thus, just slightly adjusting the flexible bridging spacer between two pyrrol-2-yl-methyleneamine units has greatly changed the self-assembly manner of the resulting metal complexes. ORTEP views of partial chain units of complexes 5 and 6 are shown in Figures 3a and 4a, respectively, and the selected bond lengths and angles are shown in Table 2. Like the silver complexes 3 and 4, the structures of 5 and 6 are almost identical except for some slight differences regarding the bond lengths of Ag-N and Ag-O, and bond angles of N-Ag-N, N-Ag-O (see Table 2 for details). In both 5 and 6, Ag(I) is bound to the nitrogen atom of the imine group in ligand 2 at a ratio 1:1 of Ag:2 to directly construct the 1D network polymer. Unlike complexes 3 and 4, the nitrate ions are not involved in 1D network formation in 5 and 6. However, the nitrate ion acts as a bridging arm to link two adjacent rows through the coordination interaction of oxygen atoms and the Ag(I) center, and hydrogen bonding of NdO‚‚‚H-N-pyrrole and NdO‚‚‚H-C (see Table 3 for details). Distinctly, two oxygen atoms are weakly bound to Ag(I) in 5, while one oxygen atom is well coordinated to Ag(I) in 6, which, correspondingly, results in different hydrogen-bonding modes in the 3D network. The nonbonding Ag‚‚‚Onitrate distances are 2.641 and 3.576 Å in 5, and the Ag‚‚‚Onitrate distance is 2.556 Å in 6, which are consistent with the reported results in the literature.10-12 The Ag-Nimine bond distances are 2.113 and 2.142 Å in 5 and 2.105 and 2.122Å in 6, respectively, which are even shorter than that found in 3 and 4, indicating a stronger interaction between the Ag(I) center and ligand 2. The N-Ag-N angles are 169.4(3)° in 5 and 168.2(3)° in 6, respectively, while the N-Ag-O angles are 90.8 and 98.9° in 5 and 89.5(3)° and 102.1(3)° in 6, respectively.

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complexes 3 and 4, respectively, both of which are very similar except for slight differences between bond lengths and bond angles around the silver centers. In 3 and 4, ligands 1 and Ag(I) ions are bound together in a 2:2 ratio of 1:Ag to form distorted rectangle metallocycles, which are constructed into 2D and 1D networks by nitrate ions, respectively. The reaction of 1,4-bis(pyrrol-2-ylmethyleneamine)butane (2) with 1 or 2 equiv of AgNO3 gives complexes 5 and 6, respectively. 5 and 6 have almost identical structures except for slight differences regarding bond lengths and angles around the Ag(I) centers. In 5 and 6, ligand 2 and Ag(I) ions are bound together in a 1:1 ratio of 2:Ag to directly form a 1D network, which is further constructed into 2D and 3D networks through nitrate ions and C-H‚‚‚Ag weak hydrogen bonding. In all four complexes, silver ions are coordinated to imine N atoms but not pyrrole N, and the metal-ligand ratio does not remarkably influence the coordination model but results in different spatial networks. Acknowledgment. This work was financially supported by the major state basic research development program (G2000078100) and NSFC (50221201).

Figure 4. (a) ORTEP drawing of complex 6 showing the atomic numbering scheme with 30% thermal ellipsoid probability. (b) 2D structure of 6 formed by the C-H‚‚‚Ag weak hydrogen bonding. (c) View along the polymeric chain showing the infinite 3D hydrogen-bonded network forced by the weak C-H‚‚‚Ag interactions and nitrate ion bridges. Table 4. Parameters for C-H‚‚‚Ag Intermolecular Hydrogen Bonding in Complexes 5 and 6 5 6

d(H‚‚‚Ag) (Å)

D (C‚‚‚Ag) (Å)

θ(C-H‚‚‚Ag) (°)

2.977 3.279 3.010 3.313

3.840 4.004 3.874 4.043

148.8 133.0 149.0 133.6

Most interestingly, in complexes 5 and 6, weak hydrogen bonding of C-H‚‚‚Ag is found and is responsible for the formation of the 3D network (Figures 3b and 4b), in which Ag(I) centers interact with two hydrogen atoms from two bridging CH2 groups of another polymeric chain. Although weak hydrogen bonding is common in many metal complexes,13 weak hydrogen bonding involved in Ag(I) is less reported. In complex 5, the H‚‚‚Ag separations (d) of (C-H)2‚‚‚Ag weak hydrogen bonding are 2.977 and 3.279Å, with C-H‚‚‚Ag separations (D) of 3.840 and 4.004 Å, respectively, and the C-H‚‚‚Ag angles (θ) are 148.8° and 133.0°, which are well in the range of weak hydrogen bonding in the literature.13,14 Similarly, complex 6 contains the same pattern of (C-H)2‚‚‚Ag weak hydrogen bonding, besides ca. 0.033 and 0.034 Å longer than that of complex 5 for H‚‚‚Ag separations (d). As a result, the C-H‚‚‚Ag separations (D) are 3.874 and 4.043 Å, with the C-H‚‚‚Ag angles (θ) of 149.0 and 133.6°, which are very close to the case of 5 and all are among the reported weak hydrogen bonding.14 A summary of parameters of weak hydrogen bonding is listed in Table 4. In conclusion, the reaction of 1,3-bis(pyrrol-2-yl-methyleneamine)propane (1) with 1 or 2 equiv of AgNO3 gives

Supporting Information Available: X-ray crystallographic information files (CIF) for 3-6. This material is available free of charge via the Internet at http://pubs.acs.org.

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