Acta Cryst. (2007). E63, m2227 [ doi:10.1107/S1600536807036215 ]
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N3)silver(I) nitrateIn the title compound, [Ag(C3H4N2)2)]NO3, the AgI atom exhibits an approximately linear coordination geometry formed by two N atoms of imidazolium cations. The uncoordinated nitrate anion is linked to the AgI complex via N-H
O hydrogen bonding, generating a one-dimensional supramolecular chain.
A solution of AgNO3 (17 mg, 0.10 mmol) in CH3OH (10 ml) was slowly added to a solution of imidazole (14 mg, 0.20 mmol) in CH3OH (10 ml). The resultant solution was stirred for 10 min at room temperature and then filtered. After addition of diethyl ether (10 ml), the filtrate was cooled to 253 K. Microcrystalline material was collected after 24 h and dried under vacuum (yield: 20.8 mg, 68%). Colorless crystals suitable for X-ray diffraction were obtained in 2 d by slow diffusion of diethyl ether into a dilute solution of the title complex in methanol. The elemental analysis: calculated for C6H8N5AgO3 C 23.53, H 2.61, N 22.88%; found: C 23.48, H 2.68, N 22.75%.
H atoms were placed in idealized positions with C—H = 0.93 and N—H = 0.86 Å, and refined in riding mode with Uiso(H) = 1.2Ueq(C,N).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
![[Figure 1]](./xu2302fig1thm.gif)
| Fig. 1. The structure of the cation of the title compound. The atom-numbering scheme is shown at the 50% probability level. |
![[Figure 2]](./xu2302fig2thm.gif)
| Fig. 2. One-dimensional chain constructed by N—H···O hydrogen bonds. |
| [Ag(C3H4N2)2)]NO3 | F(000) = 600 |
| Mr = 306.04 | Dx = 2.062 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 4145 reflections |
| a = 4.9941 (4) Å | θ = 2.9–27.6° |
| b = 10.9250 (8) Å | µ = 2.04 mm−1 |
| c = 18.0729 (12) Å | T = 298 K |
| V = 986.07 (13) Å3 | Block, colourless |
| Z = 4 | 0.22 × 0.20 × 0.16 mm |
| Bruker SMART CCD area-detector diffractometer | 2266 independent reflections |
| Radiation source: fine-focus sealed tube | 2175 reflections with I > 2σ(I) |
| graphite | Rint = 0.034 |
| φ and ω scans | θmax = 27.6°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −6→4 |
| Tmin = 0.630, Tmax = 0.720 | k = −14→9 |
| 5440 measured reflections | l = −22→23 |
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.023 | w = 1/[σ2(Fo2) + (0.019P)2 + 0.36P] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.054 | (Δ/σ)max = 0.001 |
| S = 1.06 | Δρmax = 0.34 e Å−3 |
| 2266 reflections | Δρmin = −0.24 e Å−3 |
| 137 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| 0 restraints | Extinction coefficient: 0.0093 (6) |
| Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with 896 Friedel pairs |
| Secondary atom site location: difference Fourier map | Flack parameter: 0.01 (4) |
| [Ag(C3H4N2)2)]NO3 | V = 986.07 (13) Å3 |
| Mr = 306.04 | Z = 4 |
| Orthorhombic, P212121 | Mo Kα radiation |
| a = 4.9941 (4) Å | µ = 2.04 mm−1 |
| b = 10.9250 (8) Å | T = 298 K |
| c = 18.0729 (12) Å | 0.22 × 0.20 × 0.16 mm |
| Bruker SMART CCD area-detector diffractometer | 2266 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 2175 reflections with I > 2σ(I) |
| Tmin = 0.630, Tmax = 0.720 | Rint = 0.034 |
| 5440 measured reflections | θmax = 27.6° |
| R[F2 > 2σ(F2)] = 0.023 | H-atom parameters constrained |
| wR(F2) = 0.054 | Δρmax = 0.34 e Å−3 |
| S = 1.06 | Δρmin = −0.24 e Å−3 |
| 2266 reflections | Absolute structure: Flack (1983), with 896 Friedel pairs |
| 137 parameters | Flack parameter: 0.01 (4) |
| 0 restraints |
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 | 0.05263 (5) | 0.56829 (2) | 0.394887 (14) | 0.04765 (9) | |
| O1 | 1.0937 (6) | −0.0388 (3) | 0.25932 (16) | 0.0760 (9) | |
| O2 | 1.1043 (5) | 0.0848 (2) | 0.35189 (14) | 0.0635 (7) | |
| O3 | 0.8259 (7) | 0.1125 (3) | 0.26385 (16) | 0.0848 (10) | |
| N1 | −0.2176 (4) | 0.7170 (2) | 0.39330 (15) | 0.0402 (5) | |
| N2 | −0.5210 (5) | 0.8442 (2) | 0.35437 (16) | 0.0509 (7) | |
| H2 | −0.6496 | 0.8741 | 0.3284 | 0.061* | |
| N3 | 0.3587 (5) | 0.4350 (2) | 0.40299 (14) | 0.0432 (5) | |
| N4 | 0.6233 (6) | 0.2898 (3) | 0.36536 (18) | 0.0565 (7) | |
| H4 | 0.6916 | 0.2342 | 0.3375 | 0.068* | |
| N5 | 1.0102 (5) | 0.0531 (2) | 0.29229 (14) | 0.0464 (6) | |
| C1 | −0.4085 (7) | 0.7350 (3) | 0.34523 (19) | 0.0484 (8) | |
| H1 | −0.4593 | 0.6788 | 0.3092 | 0.058* | |
| C2 | −0.3967 (7) | 0.8998 (3) | 0.4119 (2) | 0.0526 (8) | |
| H2A | −0.4331 | 0.9772 | 0.4308 | 0.063* | |
| C3 | −0.2096 (7) | 0.8205 (3) | 0.43611 (19) | 0.0473 (7) | |
| H3 | −0.0937 | 0.8338 | 0.4756 | 0.057* | |
| C4 | 0.4128 (8) | 0.3589 (3) | 0.3494 (2) | 0.0549 (9) | |
| H4A | 0.3160 | 0.3537 | 0.3055 | 0.066* | |
| C5 | 0.7112 (7) | 0.3224 (3) | 0.4332 (2) | 0.0532 (9) | |
| H5 | 0.8571 | 0.2898 | 0.4584 | 0.064* | |
| C6 | 0.5441 (7) | 0.4125 (3) | 0.45737 (18) | 0.0479 (7) | |
| H6 | 0.5540 | 0.4519 | 0.5029 | 0.058* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ag1 | 0.04804 (13) | 0.03896 (13) | 0.05596 (14) | 0.01227 (10) | −0.00079 (11) | 0.00013 (11) |
| O1 | 0.0810 (18) | 0.0742 (18) | 0.0727 (17) | 0.0439 (16) | −0.0231 (15) | −0.0295 (14) |
| O2 | 0.0756 (18) | 0.0613 (15) | 0.0537 (14) | 0.0062 (14) | −0.0167 (12) | −0.0076 (13) |
| O3 | 0.097 (2) | 0.093 (2) | 0.0643 (17) | 0.0642 (18) | −0.0247 (16) | −0.0118 (15) |
| N1 | 0.0386 (11) | 0.0367 (12) | 0.0453 (13) | 0.0026 (9) | −0.0026 (12) | 0.0025 (12) |
| N2 | 0.0406 (15) | 0.0531 (15) | 0.0592 (16) | 0.0129 (12) | −0.0048 (13) | 0.0106 (13) |
| N3 | 0.0435 (11) | 0.0367 (12) | 0.0494 (13) | 0.0065 (10) | 0.0037 (11) | 0.0005 (14) |
| N4 | 0.0585 (18) | 0.0440 (15) | 0.0671 (18) | 0.0162 (13) | 0.0129 (15) | −0.0032 (15) |
| N5 | 0.0491 (15) | 0.0461 (14) | 0.0441 (13) | 0.0118 (12) | −0.0015 (11) | 0.0010 (12) |
| C1 | 0.0458 (19) | 0.0465 (17) | 0.0529 (17) | 0.0003 (14) | −0.0083 (14) | 0.0007 (14) |
| C2 | 0.0551 (19) | 0.0413 (16) | 0.061 (2) | 0.0132 (14) | 0.0013 (15) | −0.0004 (14) |
| C3 | 0.0483 (17) | 0.0399 (17) | 0.0536 (18) | 0.0074 (14) | −0.0072 (14) | −0.0026 (14) |
| C4 | 0.060 (2) | 0.0515 (19) | 0.0530 (18) | 0.0147 (17) | −0.0017 (16) | −0.0076 (15) |
| C5 | 0.0415 (17) | 0.0454 (19) | 0.073 (2) | 0.0072 (14) | −0.0014 (16) | 0.0157 (18) |
| C6 | 0.0528 (16) | 0.0402 (16) | 0.0508 (17) | 0.0020 (15) | −0.0040 (15) | 0.0039 (13) |
| Ag1—N1 | 2.112 (2) | N4—C4 | 1.326 (4) |
| Ag1—N3 | 2.116 (2) | N4—C5 | 1.350 (5) |
| O1—N5 | 1.240 (3) | N4—H4 | 0.8600 |
| O2—N5 | 1.225 (3) | C1—H1 | 0.9300 |
| O3—N5 | 1.238 (3) | C2—C3 | 1.348 (4) |
| N1—C1 | 1.305 (4) | C2—H2A | 0.9300 |
| N1—C3 | 1.371 (4) | C3—H3 | 0.9300 |
| N2—C1 | 1.328 (4) | C4—H4A | 0.9300 |
| N2—C2 | 1.355 (4) | C5—C6 | 1.362 (5) |
| N2—H2 | 0.8600 | C5—H5 | 0.9300 |
| N3—C4 | 1.305 (4) | C6—H6 | 0.9300 |
| N3—C6 | 1.373 (4) | ||
| N1—Ag1—N3 | 172.62 (10) | N1—C1—H1 | 124.4 |
| C1—N1—C3 | 105.8 (3) | N2—C1—H1 | 124.4 |
| C1—N1—Ag1 | 126.3 (2) | C3—C2—N2 | 106.1 (3) |
| C3—N1—Ag1 | 127.5 (2) | C3—C2—H2A | 126.9 |
| C1—N2—C2 | 107.7 (3) | N2—C2—H2A | 126.9 |
| C1—N2—H2 | 126.1 | C2—C3—N1 | 109.1 (3) |
| C2—N2—H2 | 126.1 | C2—C3—H3 | 125.4 |
| C4—N3—C6 | 106.1 (3) | N1—C3—H3 | 125.4 |
| C4—N3—Ag1 | 122.4 (2) | N3—C4—N4 | 111.4 (3) |
| C6—N3—Ag1 | 131.3 (2) | N3—C4—H4A | 124.3 |
| C4—N4—C5 | 107.8 (3) | N4—C4—H4A | 124.3 |
| C4—N4—H4 | 126.1 | N4—C5—C6 | 106.4 (3) |
| C5—N4—H4 | 126.1 | N4—C5—H5 | 126.8 |
| O2—N5—O3 | 120.1 (3) | C6—C5—H5 | 126.8 |
| O2—N5—O1 | 121.5 (3) | C5—C6—N3 | 108.2 (3) |
| O3—N5—O1 | 118.4 (3) | C5—C6—H6 | 125.9 |
| N1—C1—N2 | 111.2 (3) | N3—C6—H6 | 125.9 |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1i | 0.86 | 2.03 | 2.879 (4) | 171 |
| N4—H4···O3 | 0.86 | 2.00 | 2.853 (5) | 174 |
| Symmetry codes: (i) x−2, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N2—H2···O1i | 0.86 | 2.03 | 2.879 (4) | 171 |
| N4—H4···O3 | 0.86 | 2.00 | 2.853 (5) | 174 |
| Symmetry codes: (i) x−2, y+1, z. |
The work was supported by the National Natural Science Foundation of China and the NSF of Guangdong Province, China (grant No. 06025033).
Bruker (1998). SMART (Version 5.0) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT. Version 6.12. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, Y.-P., Chen, C.-L., Zhang, L., Shi, J.-L., Xu, A.-W., Su, C.-Y. & Kang, B.-S. (2003). Inorg. Chim. Acta, 342, 107–113.
Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (2002). SADABS. Version 2.03. University of Göttingen, Germany.
Xu, A.-W., Cai, Y.-P., Zhang, L.-Z., Su, C.-Y. & Kang, B.-S. (2002). Acta Cryst. E58, m770–m771.
As part of the structural studies of AgI compounds involving the N-heterocycle ligand (Cai et al., 2003; Xu et al., 2002), we report here the synthesis and structure of the title compound.
The crystal of the compound consists of [Ag(C3N2H4)2)]+ cations and (NO3)- anions. Fig. 1 shows the structure of the cation. The AgI atom exhibits a AgN2 linear coordination geometry arising from two N atoms of imidazole molecules (Table 1). The uncoordinated nitrate anion interacts with imidazole by hydrogen bonding (Table 2), generating a one-dimensional supramolecular chain (Fig. 2).