Acta Cryst. (2009). E65, m1703 [ doi:10.1107/S1600536809050491 ]
![[mu]](/logos/entities/mu_rmgif.gif)
2-4,4'-bipyridine-![[kappa]](/logos/entities/kappa_rmgif.gif)
2N:N']In the title compound, [Ag2(C2N3)2(C10H8N2)]n, the Ag atoms, lying on inversion centers, are separated by 3.3226 (12) Å. Each Ag atom is connected by one bridging 4,4'-bipyridine [Ag-N = 2.177 (4)Å] and a terminal dicyanamide [Ag-N = 2.108 (4) Å]. The Ag-Ag interactions play a key role in constructing a unique neutral polymeric chain.
Ag(NO3) (68.0 mg, 0.4 mmol) and NaN(CN)2 (178.2 mg, 2 mmol) were added into 3 ml dimethylformamide with thorough stirring for 5 minutes. After filtration, the colorless filtrate was carefully laid on the surface of a solution of 4,4'-bipyridine (78.0 mg, 0.5 mmol) in 8 ml i-PrOH. Colorless prismatic crystals were obtained after five days.
H atoms were positioned geometrically and refined with riding model, with Uiso = 1.2Ueq for pyridyl H atoms, the C—H bonds are 0.93 Å in pyridyl.
Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./pv2240fig1thm.gif)
| Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids; H atoms have been omitted for clarity. Symmetry code: i = -x+2, -y+1, -z+1. |
| [Ag2(C2N3)2(C10H8N2)] | Z = 2 |
| Mr = 252.01 | F(000) = 242 |
| Triclinic, P1 | Dx = 2.232 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 6.1867 (12) Å | Cell parameters from 1687 reflections |
| b = 7.8344 (16) Å | θ = 2.6–28.7° |
| c = 7.9649 (16) Å | µ = 2.63 mm−1 |
| α = 88.83 (3)° | T = 293 K |
| β = 84.09 (3)° | Prism, colorless |
| γ = 77.54 (3)° | 0.2 × 0.16 × 0.12 mm |
| V = 374.95 (13) Å3 |
| Rigaku Saturn724+ diffractometer | 1358 independent reflections |
| Radiation source: fine-focus sealed tube | 1315 reflections with I > 2σ(I) |
| graphite | Rint = 0.022 |
| dtprofit.ref scans | θmax = 25.5°, θmin = 2.6° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −7→7 |
| Tmin = 0.407, Tmax = 0.664 | k = −6→9 |
| 2474 measured reflections | l = −9→9 |
| 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)] = 0.033 | H-atom parameters constrained |
| wR(F2) = 0.103 | w = 1/[σ2(Fo2) + (0.0601P)2 + 0.1547P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.24 | (Δ/σ)max < 0.001 |
| 1358 reflections | Δρmax = 0.67 e Å−3 |
| 110 parameters | Δρmin = −0.70 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: 0.055 (7) |
| [Ag2(C2N3)2(C10H8N2)] | γ = 77.54 (3)° |
| Mr = 252.01 | V = 374.95 (13) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 6.1867 (12) Å | Mo Kα radiation |
| b = 7.8344 (16) Å | µ = 2.63 mm−1 |
| c = 7.9649 (16) Å | T = 293 K |
| α = 88.83 (3)° | 0.2 × 0.16 × 0.12 mm |
| β = 84.09 (3)° |
| Rigaku Saturn724+ diffractometer | 1315 reflections with I > 2σ(I) |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | Rint = 0.022 |
| Tmin = 0.407, Tmax = 0.664 | θmax = 25.5° |
| 2474 measured reflections | Standard reflections: 0 |
| 1358 independent reflections |
| R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
| wR(F2) = 0.103 | Δρmax = 0.67 e Å−3 |
| S = 1.24 | Δρmin = −0.70 e Å−3 |
| 1358 reflections | Absolute structure: ? |
| 110 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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. |
| x | y | z | Uiso*/Ueq | ||
| Ag1 | 0.83031 (5) | 0.39268 (4) | 0.61182 (3) | 0.0570 (3) | |
| N1 | 0.6869 (7) | 0.6445 (6) | 0.3950 (4) | 0.0626 (10) | |
| N2 | 0.7664 (7) | 0.5131 (6) | −0.1486 (5) | 0.0544 (9) | |
| N3 | 0.6751 (7) | 0.7081 (5) | 0.0944 (5) | 0.0518 (9) | |
| N4 | 0.8957 (6) | 0.2168 (4) | 0.3957 (4) | 0.0432 (8) | |
| C1 | 0.6855 (6) | 0.6651 (5) | 0.2524 (5) | 0.0428 (8) | |
| C2 | 0.7278 (6) | 0.5953 (5) | −0.0277 (5) | 0.0416 (8) | |
| C3 | 0.9785 (6) | 0.0426 (5) | 0.0830 (5) | 0.0367 (8) | |
| C4 | 0.7354 (7) | 0.2209 (6) | 0.2947 (6) | 0.0521 (10) | |
| H4 | 0.5933 | 0.2842 | 0.3301 | 0.063* | |
| C5 | 0.7682 (7) | 0.1371 (6) | 0.1417 (6) | 0.0511 (10) | |
| H5 | 0.6497 | 0.1434 | 0.0772 | 0.061* | |
| C6 | 1.0962 (7) | 0.1231 (5) | 0.3420 (5) | 0.0447 (9) | |
| H6 | 1.2110 | 0.1175 | 0.4100 | 0.054* | |
| C7 | 1.1423 (6) | 0.0341 (5) | 0.1914 (5) | 0.0431 (8) | |
| H7 | 1.2844 | −0.0324 | 0.1617 | 0.052* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ag1 | 0.0661 (4) | 0.0685 (3) | 0.0347 (3) | −0.0119 (2) | 0.00158 (18) | −0.02256 (18) |
| N1 | 0.084 (3) | 0.067 (2) | 0.033 (2) | −0.008 (2) | −0.0024 (19) | −0.0116 (16) |
| N2 | 0.064 (2) | 0.064 (2) | 0.0322 (19) | −0.0080 (18) | −0.0025 (16) | −0.0155 (16) |
| N3 | 0.067 (2) | 0.0520 (19) | 0.0328 (19) | −0.0039 (16) | −0.0054 (16) | −0.0089 (14) |
| N4 | 0.0522 (19) | 0.0447 (17) | 0.0315 (17) | −0.0072 (14) | −0.0042 (14) | −0.0108 (13) |
| C1 | 0.046 (2) | 0.0467 (19) | 0.035 (2) | −0.0082 (15) | −0.0020 (16) | −0.0148 (15) |
| C2 | 0.0421 (19) | 0.051 (2) | 0.0298 (19) | −0.0065 (15) | −0.0029 (15) | −0.0036 (16) |
| C3 | 0.0445 (19) | 0.0327 (16) | 0.0321 (19) | −0.0068 (14) | −0.0026 (15) | −0.0023 (14) |
| C4 | 0.043 (2) | 0.060 (2) | 0.047 (2) | 0.0017 (17) | −0.0021 (18) | −0.0214 (19) |
| C5 | 0.043 (2) | 0.061 (2) | 0.045 (2) | 0.0015 (17) | −0.0080 (17) | −0.0224 (19) |
| C6 | 0.049 (2) | 0.049 (2) | 0.035 (2) | −0.0064 (16) | −0.0091 (17) | −0.0074 (16) |
| C7 | 0.0411 (19) | 0.046 (2) | 0.038 (2) | 0.0005 (15) | −0.0065 (16) | −0.0082 (15) |
| Ag1—N2i | 2.108 (4) | N4—C4 | 1.334 (6) |
| Ag1—N4 | 2.177 (4) | C3—C7 | 1.387 (6) |
| Ag1—N1 | 2.661 (4) | C3—C5 | 1.390 (6) |
| Ag1—Ag1ii | 3.3226 (12) | C3—C3iv | 1.467 (8) |
| N1—C1 | 1.144 (5) | C4—C5 | 1.372 (6) |
| N2—C2 | 1.145 (6) | C4—H4 | 0.9300 |
| N2—Ag1iii | 2.108 (4) | C5—H5 | 0.9300 |
| N3—C2 | 1.296 (6) | C6—C7 | 1.373 (6) |
| N3—C1 | 1.301 (6) | C6—H6 | 0.9300 |
| N4—C6 | 1.331 (5) | C7—H7 | 0.9300 |
| N2i—Ag1—N4 | 167.60 (15) | C7—C3—C3iv | 122.8 (4) |
| N2i—Ag1—N1 | 105.43 (14) | C5—C3—C3iv | 121.4 (4) |
| N4—Ag1—N1 | 86.07 (12) | N4—C4—C5 | 123.8 (4) |
| N2i—Ag1—Ag1ii | 105.25 (12) | N4—C4—H4 | 118.1 |
| N4—Ag1—Ag1ii | 84.71 (10) | C5—C4—H4 | 118.1 |
| N1—Ag1—Ag1ii | 57.43 (10) | C4—C5—C3 | 120.0 (4) |
| C1—N1—Ag1 | 139.3 (4) | C4—C5—H5 | 120.0 |
| C2—N2—Ag1iii | 172.6 (4) | C3—C5—H5 | 120.0 |
| C2—N3—C1 | 123.1 (4) | N4—C6—C7 | 123.4 (4) |
| C6—N4—C4 | 116.4 (4) | N4—C6—H6 | 118.3 |
| C6—N4—Ag1 | 123.9 (3) | C7—C6—H6 | 118.3 |
| C4—N4—Ag1 | 118.8 (3) | C6—C7—C3 | 120.5 (4) |
| N1—C1—N3 | 173.2 (5) | C6—C7—H7 | 119.7 |
| N2—C2—N3 | 171.4 (4) | C3—C7—H7 | 119.7 |
| C7—C3—C5 | 115.8 (4) |
| Symmetry codes: (i) x, y, z+1; (ii) −x+2, −y+1, −z+1; (iii) x, y, z−1; (iv) −x+2, −y, −z. |
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The designed syntheses of metal-organic compounds have attracted great attention in recent years because of not only their intriguing structures (Eddaoudi et al., 2001; Zhang et al., 2008) but also their potential applications.(Banerjee et al., 2008; Zhang et al., 2007). The flexible and rigid bridging ligands can play different roles in constructing metal-organic frameworks. The tilte compound, (I), was constructed by employing a flexible, dicyanamide, and a rigid, 4,4'-bipyridine ligand through diffusion reactions. In this paper, the crystal structure of (I) is presented.
As illustrated in Fig. 1, 4,4'-bipyridine acts as a bridgeing ligand to connect two Ag atoms. Dicyanamide usually acts as a briding ligand to construct metal-organic compounds (Zhang et al., 2009a,b). However, in the tilte compound, it is linked to only one Ag atom. Ag—Ag bonds [3.3226 (12) Å] play a key role in constructing a unique one-dimensional neutral chain.