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The bis(4-aminopyridine)silver(I) cation in [Ag(C5H6N2)2]NO3 has the Ag atom on a twofold axis and displays an N-Ag-N angle of 174.43 (15)° and an Ag-N distance of 2.122 (3) Å. The two ligands are planar and the angle between the two ligand planes is 79.45 (9)°. The pyridine rings are stacked in piles with an interplanar distance of 3.614 (5) Å, a distance that strongly suggests that pyridine [pi]-[pi] interactions have an appreciable importance with respect to the non-bonded crystal organization. The tris(2,6-diaminopyridine)­silver(I) cation in [Ag(C5H7N3)3]NO3 has Ag-N distances of 2.243 (2), 2.2613 (17) and 2.4278 (18) Å, and N-Ag-N angles of 114.33 (7), 134.91 (7) and 114.33 (7)°. The Ag+ ion is situated 0.1531 (2) Å from the plane defined by the three pyridine N atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270199014432/os1082sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199014432/os1082Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270199014432/os1082IIsup3.hkl
Contains datablock pynim

CCDC references: 142730; 142731

Comment top

Silver is an often used metal in the construction of coordination polymers and related supramolecular systems with multidentate pyridine derivatives (Aakeroy at al., 1998, Wu et al., 1999, and references therein). The silver(I)ion exhibits a large flexibility in its coordination with nitrogen-containing aromatic ligands with coordination numbers ranging from two to eight. The geometries of the complexes are however usually determined by the coordination requirements of multidentate ligands. With monodentate pyridine or functionalized pyridine ligands, virtually linear complexes are the most frequently encountered. For the two-coordinate complexes so far structurally characterized, the N—Ag—N angle and Ag—N distance average 169 (9) ° and 2.167 (17) Å, respectively (Allen & Kennard, 1993). Exceptions from two-coordinate complexes are the tris(isonicotinamide)silver(I) cation with a nearly trigonal geometry (Aakeroy et al., 1998) and the tetrahedral tetrapyridinesilver(I) cation (Nilsson & Oskarsson, 1982, Dyason et al., 1985). In this contribution, we wish to present the crystal structures of silver(I) complexes with the 4-aminopyridine and 2,6-diaminopyridine ligands.

The Bis(4-aminopyridine)silver(I) cation has a N1 - Ag1 - N1i angle of 174.43 (15) ° (Figure 1). The Ag1—N1 distance is equal to 2.122 (3) Å. The 4-aminopyridine ligands are planar with a mean deviation from the plane defined by the seven non-hydrogen atoms of 0.008 (2) Å. The angle between the planes defined by the two ligands is 79.45 (9) °. The hydrogen bonds formed between the amino group and the nitrate anions are weak, with N - O distances of 2.963 (4) and 3.189 (5) Å. The unit-cell content is shown in Figure 2 where it is seen that cations are packed to form parallell "tubes" along the c axis. Viewed perpendicular to the c axis, the pyridine rings are seen to be stacked into piles (Figure 3). The interplane distance between the 4-aminopyridine ligands in a pile is 3.614 (5) Å, a distance strongly suggesting that pyridine π-π interactions have an appreciable importance for the non-bonded crystal organization (e.g. Kiralj et al., 1999, Iswhow et al., 1998, Wu et al., 1999, Yoshida et al., 1998).

In tris(2,6-diaminopyridine)silver(I)nitrate is the Ag+ ion coordinated by three 2,6-diaminopyridine ligands with Ag—N distances of 2.243 (2), 2.2613 (17) and 2.4278 (18) Å in a distorted trigonal geometry (Figure 4). The N1—Ag—N11, N11—Ag1—N21 and N21—Ag1—N1 angles are 114.33 (7), 134.91 (7) and 114.33 (7) °, respectively. The Ag+ ion is situated 0.1531 (2) Å from the plane defined by the N1, N11 and N21 atoms. These values can be compared with those of the tris(isonicotinamide)silver(I) cation where Ag—N distances ranging from 2.213 (2) to 2.321 (2) Å are observed (Aakeroy et al.,1998). The N1—C1 and N1—C5 distances are 1.358 (3) and 1.360 (3) Å, respectively. The C1—N2 and C5—N3 distances are 1.333 (3) and 1.343 (4) Å, respectively, and the N1—C1—N2 and N1—C5—N3 angles are both 117.4 (3) °. The geometry of the ligand remains virtually unchanged upon coordination with the Ag+ cation as compared with the geometry of the 2,6.diaminopyridinium cation (Kristiansson, 1999). Eight of the twelwe amino-H atoms participate in hydrogen bonds with the nitrate anions. The hydrogen bonds are relatively weak, with N—O distances ranging from 3.001 (4) to 3.344 (4) Å. No π - π stacking is apparent in the crystal edification of this compound. It is interesting that the silver(I) ion prefer a trigonal arrangement with the relatively bulky 2,6-diaminopyridine ligand instead of the more commonly preferred linear geometry. Considering the Mulliken charges onthe pyridine-N atoms, a value of −0.723 is obtained for 2,6-diaminopyridine as compared with −0.559 for 4-aminopyridine and −0.515 for pyridine as obtained from ab initio calculations at the 6–31 G+ level (Kristiansson, 1999). One possible explanation might then be that the higher coordination number with 2,6-diaminopyridine as compared to 4-aminopyridine (at similar ligand concentrations) is a result of the increased electrostatic interaction energy. For pyridine complexes obtained from e.g. silver nitrate in pyridine solutions, the composition of the solid solvate appears to be the result of the varying solubility of the salt at different temperatures. Thus at relatively high temperatures the formation of the dipyridine complex is favoured while at low temperatures the existance of the hexa-solvate has been suggested on the basis of solubility measurements (Linke, W·F., 1958).

Experimental top

A mixture of AgNO3 and either 4-aminopyridine or 2,6-diaminopyridine (6 equivalents)in water/ethanol (50:50) was stirred while boiling. The solutions were allowed to slowly evaporate which afforded X-ray quality crystals. The chosen crystals were coated with a hydrocarbon oil and mounted on a glass fibre.

Refinement top

The fraction of Friedel pairs measured for (II) is 0.65.

Computing details top

For both compounds, data collection: Bruker SMART (1998b); cell refinement: Bruker SMART and SAINT (1998b); data reduction: Bruker SAINT (1998b); program(s) used to solve structure: Bruker SHELXTL (1998a); program(s) used to refine structure: Bruker SHELXTL (1998a); molecular graphics: Bruker SHELXTL (1998a); software used to prepare material for publication: Bruker SHELXTL (1998a).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
Figure 1. The molecular structure of bis(4-aminopyridine)silver(I)nitrate. The displacement ellipsoids are shown at the 30% probability level for non-H atoms.

Figure 2. View along the c axis of the packing of bis(4-aminopyridine)silver(I)nitrate in the unit cell.

Figure 3. View perpendicular to the c axis of the packing of bis(4-aminopyridine)silver(I)nitrate in the unit cell.

Figure 4. Molecular structure of the tris(2,6-diaminopyridine)silver(I) cation. The displacement ellipsoids are shown at the 30% probability level for non-H atoms.
(I) Bis(4-aminopyridine)silver(I)nitrate top
Crystal data top
C10H12AgN5O3F(000) = 712
Mr = 358.12Dx = 1.809 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 7.2661 (10) ÅCell parameters from 1507 reflections
b = 12.2749 (18) Åθ = 2.8–28.0°
c = 14.803 (2) ŵ = 1.55 mm1
β = 95.084 (2)°T = 295 K
V = 1315.1 (3) Å3Prism, colourless
Z = 40.31 × 0.29 × 0.29 mm
Data collection top
Bruker SMART CCD
diffractometer
1126 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 28.0°, θmin = 2.8°
ω scansh = 99
3818 measured reflectionsk = 1115
1507 independent reflectionsl = 1818
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.094 w = 1/[σ2(Fo2) + (0.0538P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
1507 reflectionsΔρmax = 0.60 e Å3
90 parametersΔρmin = 0.41 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0009 (6)
Crystal data top
C10H12AgN5O3V = 1315.1 (3) Å3
Mr = 358.12Z = 4
Monoclinic, C2/cMo Kα radiation
a = 7.2661 (10) ŵ = 1.55 mm1
b = 12.2749 (18) ÅT = 295 K
c = 14.803 (2) Å0.31 × 0.29 × 0.29 mm
β = 95.084 (2)°
Data collection top
Bruker SMART CCD
diffractometer
1126 reflections with I > 2σ(I)
3818 measured reflectionsRint = 0.023
1507 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.094H-atom parameters constrained
S = 0.98Δρmax = 0.60 e Å3
1507 reflectionsΔρmin = 0.41 e Å3
90 parameters
Special details top

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.

For both compounds, a hemisphere of data (1375 frames) was collected with 0.3 ° frame width and a detector - crystal distance of 5.00 cm. The detector was positioned with Θ = 28.0 °. Data were recorded in three series with ϕ = 0, 88 and 180 ° with 20 s exposure time. For Ag(C5H6N2)2NO3 is the data set is complete to 95.0% with Θmax = 27.88 °.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.00000.60940 (4)0.25000.0685 (2)
N10.0803 (4)0.6178 (2)0.3912 (2)0.0592 (7)
C30.1602 (5)0.6251 (3)0.5803 (2)0.0540 (8)
C40.0369 (5)0.6976 (3)0.5353 (2)0.0581 (9)
H40.02180.75030.56750.070*
N20.1959 (5)0.6261 (3)0.6715 (2)0.0724 (9)
H2A0.14170.67270.70350.087*
H2B0.27290.58020.69740.087*
C20.2433 (5)0.5484 (3)0.5263 (2)0.0565 (8)
H20.32660.49770.55280.068*
C50.0030 (5)0.6905 (3)0.4434 (2)0.0591 (9)
H50.08000.74000.41490.071*
C10.2008 (5)0.5489 (3)0.4350 (2)0.0583 (9)
H10.25910.49820.40060.070*
O10.00000.0151 (4)0.25000.0911 (13)
O20.1263 (4)0.1650 (3)0.2919 (2)0.0856 (9)
N30.00000.1143 (4)0.25000.0601 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0669 (3)0.0882 (4)0.0502 (3)0.0000.00321 (17)0.000
N10.0619 (17)0.0617 (18)0.0541 (16)0.0130 (15)0.0057 (14)0.0014 (14)
C30.0559 (19)0.052 (2)0.0548 (19)0.0121 (15)0.0069 (15)0.0008 (15)
C40.058 (2)0.051 (2)0.065 (2)0.0056 (16)0.0089 (16)0.0032 (16)
N20.088 (2)0.074 (2)0.0542 (18)0.0077 (17)0.0008 (17)0.0018 (14)
C20.0559 (19)0.051 (2)0.063 (2)0.0026 (16)0.0071 (16)0.0030 (16)
C50.056 (2)0.056 (2)0.065 (2)0.0028 (17)0.0060 (16)0.0073 (17)
C10.059 (2)0.055 (2)0.062 (2)0.0052 (17)0.0153 (17)0.0046 (17)
O10.097 (3)0.068 (3)0.104 (3)0.0000.017 (2)0.000
O20.0672 (18)0.099 (2)0.089 (2)0.0134 (17)0.0057 (15)0.0198 (19)
N30.061 (3)0.069 (3)0.051 (2)0.0000.0077 (19)0.000
Geometric parameters (Å, º) top
Ag1—N12.122 (3)C3—C21.405 (5)
Ag1—N1i2.122 (3)C4—C51.363 (5)
N1—C51.336 (5)C2—C11.359 (5)
N1—C11.342 (5)O1—N31.218 (5)
C3—N21.351 (5)O2—N31.230 (4)
C3—C41.390 (5)N3—O2i1.230 (4)
N1—Ag1—N1i174.43 (15)C5—C4—C3119.3 (3)
C5—N1—C1115.5 (3)C1—C2—C3119.4 (3)
C5—N1—Ag1120.6 (2)N1—C5—C4124.8 (3)
C1—N1—Ag1123.8 (2)N1—C1—C2124.4 (3)
N2—C3—C4122.1 (3)O1—N3—O2120.4 (3)
N2—C3—C2121.3 (3)O1—N3—O2i120.4 (3)
C4—C3—C2116.6 (3)O2—N3—O2i119.2 (5)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2ii0.862.393.189 (5)154
N2—H2B···O1iii0.862.112.963 (4)169
Symmetry codes: (ii) x, y+1, z+1/2; (iii) x+1/2, y+1/2, z+1.
(II) Tris(2,6-diaminopyridine)silver(I)nitrate ? top
Crystal data top
C15H21AgN10O3Dx = 1.683 Mg m3
Mr = 497.29Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4447 reflections
a = 8.9276 (7) Åθ = 2.1–28.0°
b = 11.1291 (9) ŵ = 1.07 mm1
c = 19.7562 (15) ÅT = 293 K
V = 1962.9 (3) Å3Block, colourless
Z = 40.30 × 0.30 × 0.30 mm
F(000) = 1008
Data collection top
Bruker SMART CCD
diffractometer
3705 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 28.0°, θmin = 2.1°
ω scansh = 119
11558 measured reflectionsk = 1414
4447 independent reflectionsl = 2523
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.024 w = 1/[σ2(Fo2) + (0.028P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.055(Δ/σ)max = 0.001
S = 0.94Δρmax = 0.93 e Å3
4447 reflectionsΔρmin = 0.50 e Å3
265 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0035 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.017 (19)
Crystal data top
C15H21AgN10O3V = 1962.9 (3) Å3
Mr = 497.29Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.9276 (7) ŵ = 1.07 mm1
b = 11.1291 (9) ÅT = 293 K
c = 19.7562 (15) Å0.30 × 0.30 × 0.30 mm
Data collection top
Bruker SMART CCD
diffractometer
3705 reflections with I > 2σ(I)
11558 measured reflectionsRint = 0.018
4447 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.024H-atom parameters constrained
wR(F2) = 0.055Δρmax = 0.93 e Å3
S = 0.94Δρmin = 0.50 e Å3
4447 reflectionsAbsolute structure: Flack H D (1983), Acta Cryst. A39, 876-881
265 parametersAbsolute structure parameter: 0.017 (19)
0 restraints
Special details top

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.

For both compounds, a hemisphere of data (1375 frames) was collected with 0.3 ° frame width and a detector - crystal distance of 5.00 cm. The detector was positioned with Θ = 28.0 °. Data were recorded in three series with ϕ = 0, 88 and 180 ° with 20 s exposure time. For Ag(C5H6N2)2NO3 is the data set is complete to 95.0% with Θmax = 27.88 °.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.25781 (2)0.906800 (16)0.890818 (8)0.04821 (7)
N10.20668 (19)0.69940 (17)0.92146 (9)0.0396 (5)
N20.0435 (3)0.6636 (2)0.83339 (13)0.0569 (7)
H2A0.07390.72910.81490.068*
H2B0.02380.62060.81370.068*
N30.3762 (3)0.7418 (2)1.00625 (13)0.0619 (6)
H3A0.40290.80410.98350.074*
H3B0.41830.72611.04440.074*
C10.2651 (3)0.6667 (2)0.98144 (11)0.0425 (5)
C20.2155 (3)0.5695 (2)1.01815 (13)0.0537 (7)
H20.25170.55341.06130.064*
C30.1083 (3)0.4961 (2)0.98760 (16)0.0583 (8)
H30.07390.42811.01010.070*
C40.0542 (3)0.5229 (2)0.92576 (14)0.0509 (7)
H40.01420.47220.90470.061*
C50.1020 (2)0.6276 (2)0.89383 (12)0.0391 (5)
N110.1056 (2)1.04105 (19)0.93975 (10)0.0413 (5)
N120.0502 (3)1.1212 (3)0.83489 (14)0.0696 (9)
H12A0.11421.07230.81760.084*
H12B0.00201.17020.80930.084*
N130.1712 (3)0.9651 (3)1.04435 (11)0.0719 (8)
H13A0.23020.91591.02400.086*
H13B0.16450.96401.08780.086*
C110.0898 (3)1.0437 (3)1.00840 (14)0.0495 (7)
C120.0060 (3)1.1250 (3)1.03973 (14)0.0604 (8)
H120.01311.12721.08670.073*
C130.0893 (3)1.2014 (3)1.00115 (18)0.0675 (9)
H130.15621.25401.02170.081*
C140.0748 (3)1.2008 (3)0.93232 (16)0.0594 (8)
H140.13081.25290.90570.071*
C150.0252 (3)1.1209 (2)0.90300 (13)0.0477 (6)
N210.4794 (2)0.91718 (18)0.83581 (9)0.0373 (4)
N220.4608 (3)1.1251 (2)0.84209 (14)0.0598 (8)
H22A0.37741.11710.86340.072*
H22B0.49541.19570.83370.072*
N230.4955 (3)0.7096 (2)0.83155 (14)0.0569 (7)
H23A0.41220.70530.85330.068*
H23B0.54120.64490.81960.068*
C210.5550 (3)0.8186 (2)0.81608 (12)0.0412 (6)
C220.6914 (3)0.8252 (3)0.78223 (15)0.0569 (8)
H220.74250.75590.76960.068*
C230.7486 (4)0.9371 (2)0.76800 (15)0.0637 (7)
H230.83830.94380.74440.076*
C240.6750 (3)1.0383 (3)0.78819 (15)0.0588 (8)
H240.71491.11410.77990.071*
C250.5385 (3)1.0253 (2)0.82144 (13)0.0414 (6)
N40.2330 (2)0.41597 (18)0.78434 (9)0.0437 (4)
O10.3116 (3)0.3419 (2)0.81126 (12)0.0965 (9)
O20.1363 (2)0.3861 (2)0.74148 (11)0.0757 (7)
O30.2468 (3)0.52299 (15)0.79814 (9)0.0618 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.05157 (11)0.05046 (11)0.04259 (10)0.00398 (12)0.00858 (10)0.00002 (8)
N10.0396 (11)0.0371 (11)0.0421 (10)0.0036 (8)0.0045 (8)0.0004 (8)
N20.0667 (15)0.0538 (17)0.0501 (15)0.0138 (12)0.0094 (12)0.0035 (12)
N30.0663 (15)0.0487 (15)0.0707 (16)0.0084 (12)0.0259 (13)0.0037 (12)
C10.0405 (13)0.0387 (12)0.0482 (12)0.0027 (12)0.0006 (12)0.0027 (9)
C20.0608 (18)0.0517 (16)0.0485 (14)0.0038 (13)0.0019 (12)0.0097 (11)
C30.0589 (17)0.0418 (17)0.074 (2)0.0092 (13)0.0041 (15)0.0168 (14)
C40.0477 (15)0.0425 (16)0.0625 (18)0.0118 (12)0.0030 (13)0.0018 (13)
C50.0386 (11)0.0378 (13)0.0409 (13)0.0009 (9)0.0061 (11)0.0025 (11)
N110.0406 (11)0.0433 (12)0.0399 (12)0.0025 (9)0.0003 (9)0.0049 (9)
N120.0756 (17)0.083 (2)0.0504 (16)0.0142 (16)0.0038 (13)0.0160 (16)
N130.0746 (17)0.105 (2)0.0361 (14)0.0257 (16)0.0043 (11)0.0005 (13)
C110.0427 (14)0.0593 (17)0.0464 (15)0.0036 (12)0.0043 (12)0.0094 (13)
C120.0658 (18)0.070 (2)0.0451 (16)0.0038 (16)0.0024 (13)0.0239 (14)
C130.0631 (19)0.054 (2)0.085 (2)0.0112 (15)0.0077 (17)0.0266 (17)
C140.0639 (19)0.0444 (17)0.070 (2)0.0087 (14)0.0059 (15)0.0006 (14)
C150.0501 (13)0.0421 (16)0.0509 (17)0.0094 (11)0.0007 (12)0.0006 (11)
N210.0414 (9)0.0350 (11)0.0356 (10)0.0005 (10)0.0012 (8)0.0012 (9)
N220.0737 (17)0.0324 (15)0.073 (2)0.0059 (12)0.0148 (14)0.0080 (13)
N230.0550 (14)0.0364 (14)0.0793 (18)0.0033 (11)0.0217 (13)0.0037 (12)
C210.0425 (14)0.0386 (15)0.0426 (14)0.0003 (11)0.0014 (11)0.0017 (11)
C220.0435 (15)0.0518 (18)0.076 (2)0.0074 (12)0.0146 (13)0.0008 (15)
C230.0422 (13)0.0629 (18)0.0859 (19)0.0066 (17)0.0182 (17)0.0092 (14)
C240.0520 (17)0.0486 (17)0.076 (2)0.0114 (14)0.0054 (14)0.0043 (15)
C250.0459 (14)0.0357 (14)0.0427 (14)0.0012 (11)0.0013 (11)0.0023 (11)
N40.0526 (12)0.0428 (11)0.0357 (9)0.0016 (14)0.0087 (10)0.0009 (8)
O10.135 (2)0.0707 (16)0.0834 (16)0.0463 (15)0.0098 (14)0.0215 (13)
O20.0661 (13)0.0861 (18)0.0749 (15)0.0173 (12)0.0076 (11)0.0242 (13)
O30.0741 (12)0.0378 (10)0.0736 (12)0.0011 (13)0.0029 (13)0.0109 (8)
Geometric parameters (Å, º) top
Ag1—N112.239 (2)N11—C151.354 (3)
Ag1—N212.2601 (18)N11—C111.364 (3)
Ag1—N12.4295 (19)N13—C111.341 (4)
N2—C51.363 (3)C15—N121.364 (3)
N1—C11.345 (3)C15—C141.386 (4)
N1—C51.345 (3)C11—C121.390 (4)
C5—C41.392 (3)C14—C131.366 (4)
C1—C21.376 (3)C13—C121.363 (4)
C1—N31.386 (3)N21—C251.345 (3)
C23—C241.364 (4)N21—C211.346 (3)
C23—C221.374 (4)C25—N221.371 (4)
C22—C211.392 (4)N23—C211.359 (3)
C2—C31.396 (4)O3—N41.228 (2)
C24—C251.392 (4)N4—O11.206 (3)
C3—C41.347 (4)N4—O21.254 (3)
N11—Ag1—N21134.81 (7)N11—C15—C14122.5 (3)
N11—Ag1—N1114.35 (7)N12—C15—C14121.1 (3)
N21—Ag1—N1109.44 (7)N13—C11—N11117.2 (2)
C1—N1—C5117.8 (2)N13—C11—C12121.5 (3)
C1—N1—Ag1113.82 (15)N11—C11—C12121.4 (3)
C5—N1—Ag1126.40 (15)C3—C4—C5119.1 (3)
N1—C5—N2116.6 (2)C13—C14—C15118.7 (3)
N1—C5—C4121.7 (2)C12—C13—C14120.1 (3)
N2—C5—C4121.7 (2)C13—C12—C11119.5 (3)
N1—C1—C2123.5 (2)C25—N21—C21118.2 (2)
N1—C1—N3115.2 (2)C25—N21—Ag1119.39 (16)
C2—C1—N3121.2 (2)C21—N21—Ag1122.45 (16)
C24—C23—C22120.6 (3)N21—C25—N22117.6 (2)
C23—C22—C21118.1 (3)N21—C25—C24122.4 (2)
C1—C2—C3116.9 (3)N22—C25—C24119.9 (2)
C23—C24—C25118.3 (3)N21—C21—N23117.8 (2)
C4—C3—C2120.5 (3)N21—C21—C22122.3 (2)
C15—N11—C11117.7 (2)N23—C21—C22119.8 (2)
C15—N11—Ag1121.89 (17)O1—N4—O3120.4 (3)
C11—N11—Ag1120.44 (17)O1—N4—O2121.2 (3)
N11—C15—N12116.3 (3)O3—N4—O2118.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.153.002 (3)173
N2—H2B···O30.862.293.106 (3)159
N13—H13A···N30.862.363.177 (4)159
N13—H13B···O3ii0.862.393.199 (3)156
N12—H12A···O2i0.862.393.116 (4)143
N12—H12A···O3i0.862.633.344 (4)141
N23—H23A···N10.862.283.133 (3)174
N23—H23B···O3iii0.862.373.169 (3)155
N22—H22B···O1iv0.862.413.213 (4)155
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x+1/2, y+3/2, z+2; (iii) x+1, y, z; (iv) x+1, y+1, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC10H12AgN5O3C15H21AgN10O3
Mr358.12497.29
Crystal system, space groupMonoclinic, C2/cOrthorhombic, P212121
Temperature (K)295293
a, b, c (Å)7.2661 (10), 12.2749 (18), 14.803 (2)8.9276 (7), 11.1291 (9), 19.7562 (15)
α, β, γ (°)90, 95.084 (2), 9090, 90, 90
V3)1315.1 (3)1962.9 (3)
Z44
Radiation typeMo KαMo Kα
µ (mm1)1.551.07
Crystal size (mm)0.31 × 0.29 × 0.290.30 × 0.30 × 0.30
Data collection
DiffractometerBruker SMART CCD
diffractometer
Bruker SMART CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3818, 1507, 1126 11558, 4447, 3705
Rint0.0230.018
(sin θ/λ)max1)0.6600.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.094, 0.98 0.024, 0.055, 0.94
No. of reflections15074447
No. of parameters90265
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.60, 0.410.93, 0.50
Absolute structure?Flack H D (1983), Acta Cryst. A39, 876-881
Absolute structure parameter?0.017 (19)

Computer programs: Bruker SMART (1998b), Bruker SMART and SAINT (1998b), Bruker SAINT (1998b), Bruker SHELXTL (1998a).

Selected geometric parameters (Å, º) for (I) top
Ag1—N12.122 (3)C3—C41.390 (5)
N1—C51.336 (5)C3—C21.405 (5)
N1—C11.342 (5)C4—C51.363 (5)
C3—N21.351 (5)C2—C11.359 (5)
N1—Ag1—N1i174.43 (15)C4—C3—C2116.6 (3)
C5—N1—C1115.5 (3)C5—C4—C3119.3 (3)
C5—N1—Ag1120.6 (2)C1—C2—C3119.4 (3)
C1—N1—Ag1123.8 (2)N1—C5—C4124.8 (3)
N2—C3—C4122.1 (3)N1—C1—C2124.4 (3)
N2—C3—C2121.3 (3)
Symmetry code: (i) x, y, z+1/2.
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2ii0.862.393.189 (5)154.3
N2—H2B···O1iii0.862.112.963 (4)169.2
Symmetry codes: (ii) x, y+1, z+1/2; (iii) x+1/2, y+1/2, z+1.
Selected geometric parameters (Å, º) for (II) top
Ag1—N112.239 (2)N1—C11.345 (3)
Ag1—N212.2601 (18)N1—C51.345 (3)
Ag1—N12.4295 (19)C1—N31.386 (3)
N2—C51.363 (3)
N11—Ag1—N21134.81 (7)C1—N1—Ag1113.82 (15)
N11—Ag1—N1114.35 (7)C5—N1—Ag1126.40 (15)
N21—Ag1—N1109.44 (7)N1—C5—N2116.6 (2)
C1—N1—C5117.8 (2)N1—C1—N3115.2 (2)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N2—H2A···O2i0.862.153.002 (3)173.4
N2—H2B···O30.862.293.106 (3)158.7
N13—H13A···N30.862.363.177 (4)158.5
N13—H13B···O3ii0.862.393.199 (3)156.2
N12—H12A···O2i0.862.393.116 (4)143.0
N12—H12A···O3i0.862.633.344 (4)140.9
N23—H23A···N10.862.283.133 (3)173.5
N23—H23B···O3iii0.862.373.169 (3)155.2
N22—H22B···O1iv0.862.413.213 (4)155.3
Symmetry codes: (i) x, y+1/2, z+3/2; (ii) x+1/2, y+3/2, z+2; (iii) x+1, y, z; (iv) x+1, y+1, z.
 

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