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Acta Cryst. (2009). E65, m1176    [ doi:10.1107/S1600536809035193 ]

(2-Amino-4,6-dimethylpyrimidine-[kappa]N1)(2-amino-4-methylpyrimidine-[kappa]N1)silver(I) perchlorate

H. Yang

Abstract top

Colourless crystals of the title mixed ligand complex, [Ag(C5H7N3)(C6H9N3)]ClO4, were obtained from a solution of 2-amino-4-methylpyrimidine, 2-amino-4,6-dimethylpyrimidine and silver perchlorate in water and methanol. The crystal structure is stabilized by intermolecular N-H...O and N-H...N hydrogen bonds and [pi]-[pi] stacking interactions of the aromatic rings of the two ligands [interplanar distance = 3.652 (10) Å]. The AgI atom shows a linear coordination [N-Ag-N = 174.6 (1)°].

Comment top

The structure of the title compound (I) comprises of uncoordinated ClO4- anions and [Ag(2-amino-4-methylpyrimidine)(2-amino-4,6-dimethylpyrimidine)]+ cations. The central silver(I) ion, possessing its vacant s and p orbitals, coordinated to two nitrogen atoms from those two different pyrimidine derivative ligands, presenting nearly linear N-Ag-N geometry Greenwood et al., 1997). An one dimensional framework was built by multiple intermolecular N–H–N hydrogen bonds along one of the diagonals of a and c axial plane, while pi–pi stacking interaction of the aromatic rings with an interplane distance 3.65 Å stabilized the whole crystal structure (Munakata et al., 2000).

Related literature top

For N—Ag—N geometry, see: Greenwood & Earnshaw et al. (1997). For π–π stacking, see: Munakata et al. (2000). For related literature [on what subject?], see: Shimizu et al. (1999); Seward et al. (2004).

Experimental top

A solution of 108 mg (1 mmol) 2-amino-4-methylpyrimidine and 123 mg (1 mmol) of 2-amino-4,6-dimethylpyrimidine in distilled water-CH3OH (1:1 v/v, 10 mL) was added to an aqueous solution of AgClO4 208 mg (1 mmol) in 3 ml distilled water at 333 K. A small amount of white precipitate was removed from the resulting solution. Prism colorless crystals were obtained by slow evaporation at room temperature over a period of 3 days.

Refinement top

All H atoms were placed in calculated positions and refined as riding, with C–H = 0.96–0.98 Å, and N–H = 0.86 Å, and Uiso(H) = 1.2 or 1.5Ueq(C,N). The final difference map had a peak near Ag1.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure with atom labels and 30% probability displacement ellipsoids for non-H atoms.
[Figure 2] Fig. 2. The packing diagram of molecules, viewed down the b axis, with the weak interactions shown as dashed lines.
(2-Amino-4,6-dimethylpyrimidine-κN1)(2-amino-4-methylpyrimidine- κN1)silver(I) perchlorate top
Crystal data top
[Ag(C5H7N3)(C6H9N3)]ClO4F(000) = 880
Mr = 439.62Dx = 1.886 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2795 reflections
a = 12.3952 (5) Åθ = 2.6–32.8°
b = 7.8324 (4) ŵ = 1.50 mm−1
c = 15.9956 (5) ÅT = 120 K
β = 94.339 (3)°Prism, colourless
V = 1548.47 (11) Å30.40 × 0.40 × 0.25 mm
Z = 4
Data collection top
Bruker APEXII
diffractometer		2678 independent reflections
Radiation source: fine-focus sealed tube2254 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −14→14
Tmin = 0.553, Tmax = 0.678k = −8→9
8880 measured reflectionsl = −19→19
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0544P)2 + 2.3112P]
where P = (Fo2 + 2Fc2)/3
2678 reflections(Δ/σ)max = 0.001
211 parametersΔρmax = 1.36 e Å−3
0 restraintsΔρmin = −0.52 e Å−3
Crystal data top
[Ag(C5H7N3)(C6H9N3)]ClO4V = 1548.47 (11) Å3
Mr = 439.62Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.3952 (5) ŵ = 1.50 mm−1
b = 7.8324 (4) ÅT = 120 K
c = 15.9956 (5) Å0.40 × 0.40 × 0.25 mm
β = 94.339 (3)°
Data collection top
Bruker APEXII
diffractometer		2254 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		Rint = 0.028
Tmin = 0.553, Tmax = 0.678θmax = 25.0°
8880 measured reflectionsStandard reflections: 0
2678 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.100Δρmax = 1.36 e Å−3
S = 1.07Δρmin = −0.52 e Å−3
2678 reflectionsAbsolute structure: ?
211 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.19079 (3)0.45483 (5)0.720510 (19)0.04423 (15)
C10.1554 (4)0.3648 (7)0.3245 (3)0.0544 (12)
H1A0.11080.26820.30870.082*
H1B0.22610.34870.30510.082*
H1C0.12350.46630.29980.082*
C20.1644 (3)0.3818 (5)0.4169 (3)0.0373 (9)
C30.0929 (3)0.3330 (5)0.5423 (2)0.0332 (9)
C40.2530 (4)0.4782 (6)0.5433 (3)0.0398 (10)
H4A0.31060.53450.57200.048*
C50.2516 (4)0.4648 (6)0.4585 (3)0.0410 (10)
H5A0.30730.50970.42940.049*
C60.3056 (3)0.4035 (5)0.8973 (2)0.0316 (8)
C70.1481 (3)0.5552 (5)0.9020 (3)0.0369 (9)
C80.0587 (4)0.6489 (7)0.8581 (3)0.0566 (13)
H8A0.08710.73650.82400.085*
H8B0.01490.70000.89830.085*
H8C0.01530.57170.82310.085*
C90.1577 (4)0.5429 (6)0.9877 (3)0.0419 (10)
H9A0.10750.59531.01970.050*
C100.2424 (4)0.4521 (5)1.0253 (3)0.0380 (9)
C110.2548 (5)0.4273 (8)1.1177 (3)0.0606 (14)
H11A0.32690.45821.13840.091*
H11B0.24200.30971.13070.091*
H11C0.20370.49791.14370.091*
N10.2212 (3)0.4824 (4)0.8553 (2)0.0319 (7)
N20.3831 (3)0.3336 (4)0.8522 (2)0.0383 (8)
H2A0.43660.27980.87740.046*
H2B0.37850.34300.79850.046*
N30.3176 (3)0.3841 (5)0.9803 (2)0.0365 (8)
N40.1743 (3)0.4133 (4)0.5875 (2)0.0350 (8)
N50.0136 (3)0.2635 (5)0.5824 (2)0.0455 (9)
H5B−0.03860.21130.55450.055*
H5C0.01440.27080.63600.055*
N60.0857 (3)0.3161 (4)0.4580 (2)0.0361 (8)
Cl10.50494 (9)0.64276 (14)0.68793 (6)0.0412 (3)
O10.4928 (3)0.6816 (5)0.6012 (2)0.0629 (10)
O20.4001 (3)0.6130 (5)0.7187 (2)0.0617 (9)
O30.5697 (3)0.4961 (5)0.7031 (3)0.0666 (10)
O40.5523 (4)0.7822 (6)0.7327 (3)0.0775 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0420 (2)0.0623 (3)0.02780 (19)−0.00167 (16)−0.00078 (13)−0.00457 (14)
C10.062 (3)0.071 (3)0.030 (2)−0.007 (3)0.003 (2)0.006 (2)
C20.044 (2)0.037 (2)0.031 (2)0.0077 (19)0.0058 (18)0.0064 (17)
C30.036 (2)0.035 (2)0.0282 (19)0.0065 (17)0.0038 (16)0.0023 (16)
C40.035 (2)0.043 (2)0.041 (2)0.0017 (19)−0.0023 (18)0.0003 (19)
C50.041 (2)0.045 (2)0.038 (2)−0.001 (2)0.0064 (19)0.0027 (19)
C60.036 (2)0.032 (2)0.0266 (19)−0.0052 (17)0.0030 (16)−0.0023 (15)
C70.038 (2)0.031 (2)0.041 (2)−0.0037 (18)0.0006 (18)−0.0006 (17)
C80.060 (3)0.062 (3)0.047 (3)0.008 (3)0.001 (2)0.007 (2)
C90.049 (3)0.038 (2)0.041 (2)−0.005 (2)0.018 (2)−0.0107 (19)
C100.045 (2)0.037 (2)0.032 (2)−0.004 (2)0.0037 (18)−0.0054 (17)
C110.074 (4)0.078 (4)0.031 (2)0.008 (3)0.009 (2)−0.006 (2)
N10.0344 (17)0.0330 (17)0.0285 (16)−0.0038 (14)0.0044 (14)−0.0037 (13)
N20.0432 (19)0.047 (2)0.0250 (16)0.0066 (16)0.0074 (14)0.0008 (14)
N30.0381 (18)0.0430 (19)0.0288 (17)−0.0001 (16)0.0050 (14)−0.0035 (15)
N40.0326 (17)0.0402 (19)0.0318 (17)0.0028 (15)−0.0010 (14)0.0000 (14)
N50.047 (2)0.063 (2)0.0269 (17)−0.0130 (19)0.0049 (15)−0.0005 (17)
N60.0416 (19)0.0403 (19)0.0264 (16)0.0019 (16)0.0011 (14)0.0031 (14)
Cl10.0467 (6)0.0444 (6)0.0331 (5)−0.0052 (5)0.0068 (4)0.0038 (4)
O10.064 (2)0.090 (3)0.0356 (17)−0.004 (2)0.0119 (16)0.0148 (17)
O20.053 (2)0.086 (3)0.049 (2)−0.0050 (19)0.0193 (16)0.0121 (18)
O30.067 (2)0.058 (2)0.074 (3)0.0125 (18)0.000 (2)0.0080 (19)
O40.092 (3)0.077 (3)0.063 (2)−0.031 (2)−0.001 (2)−0.007 (2)
Geometric parameters (Å, °) top
Ag1—N42.146 (3)C7—C81.465 (7)
Ag1—N12.171 (3)C8—H8A0.9600
C1—C21.479 (6)C8—H8B0.9600
C1—H1A0.9600C8—H8C0.9600
C1—H1B0.9600C9—C101.370 (7)
C1—H1C0.9600C9—H9A0.9300
C2—N61.322 (6)C10—N31.330 (6)
C2—C51.387 (6)C10—C111.487 (6)
C3—N51.330 (6)C11—H11A0.9600
C3—N61.351 (5)C11—H11B0.9600
C3—N41.352 (5)C11—H11C0.9600
C4—N41.347 (6)N2—H2A0.8600
C4—C51.360 (6)N2—H2B0.8600
C4—H4A0.9300N5—H5B0.8600
C5—H5A0.9300N5—H5C0.8600
C6—N31.334 (5)Cl1—O41.409 (4)
C6—N11.350 (5)Cl1—O31.412 (4)
C6—N21.359 (5)Cl1—O11.417 (3)
C7—N11.344 (6)Cl1—O21.443 (4)
C7—C91.370 (6)
N4—Ag1—N1174.61 (13)C7—C9—H9A120.6
C2—C1—H1A109.5C10—C9—H9A120.6
C2—C1—H1B109.5N3—C10—C9121.0 (4)
H1A—C1—H1B109.5N3—C10—C11117.4 (4)
C2—C1—H1C109.5C9—C10—C11121.5 (4)
H1A—C1—H1C109.5C10—C11—H11A109.5
H1B—C1—H1C109.5C10—C11—H11B109.5
N6—C2—C5121.4 (4)H11A—C11—H11B109.5
N6—C2—C1117.3 (4)C10—C11—H11C109.5
C5—C2—C1121.3 (4)H11A—C11—H11C109.5
N5—C3—N6116.4 (4)H11B—C11—H11C109.5
N5—C3—N4118.8 (4)C7—N1—C6116.6 (3)
N6—C3—N4124.7 (4)C7—N1—Ag1121.4 (3)
N4—C4—C5122.7 (4)C6—N1—Ag1121.2 (3)
N4—C4—H4A118.6C6—N2—H2A120.0
C5—C4—H4A118.6C6—N2—H2B120.0
C4—C5—C2117.7 (4)H2A—N2—H2B120.0
C4—C5—H5A121.1C10—N3—C6117.6 (4)
C2—C5—H5A121.1C4—N4—C3115.8 (4)
N3—C6—N1124.8 (4)C4—N4—Ag1116.4 (3)
N3—C6—N2116.9 (4)C3—N4—Ag1127.7 (3)
N1—C6—N2118.2 (3)C3—N5—H5B120.0
N1—C7—C9121.1 (4)C3—N5—H5C120.0
N1—C7—C8117.6 (4)H5B—N5—H5C120.0
C9—C7—C8121.3 (4)C2—N6—C3117.6 (4)
C7—C8—H8A109.5O4—Cl1—O3109.5 (3)
C7—C8—H8B109.5O4—Cl1—O1109.9 (2)
H8A—C8—H8B109.5O3—Cl1—O1111.1 (3)
C7—C8—H8C109.5O4—Cl1—O2107.6 (3)
H8A—C8—H8C109.5O3—Cl1—O2109.0 (3)
H8B—C8—H8C109.5O1—Cl1—O2109.6 (2)
C7—C9—C10118.8 (4)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5C···O4i0.862.323.131 (5)158
N5—H5B···N3ii0.862.203.050 (5)172
N2—H2B···O20.862.503.077 (5)126
N2—H2A···N6iii0.862.303.147 (5)169
C1—H1C···O4iv0.962.383.339 (7)177
C4—H4A···O10.932.553.437 (6)160
C4—H4A···O20.932.593.396 (6)145
C8—H8C···O4i0.962.553.456 (7)157
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2; (iv) x−1/2, −y+3/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N5—H5C···O4i0.862.323.131 (5)158
N5—H5B···N3ii0.862.203.050 (5)172
N2—H2B···O20.862.503.077 (5)126
N2—H2A···N6iii0.862.303.147 (5)169
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) x−1/2, −y+1/2, z−1/2; (iii) x+1/2, −y+1/2, z+1/2.
Acknowledgements top

The author thanks the Natural Science Foundation of Heilongjiang Province for finacial support.

references
References top

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