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Acta Cryst. (2007). E63, m3000    [ doi:10.1107/S1600536807057248 ]

(3-Aminopyridine-[kappa]N1)(saccharinato-[kappa]N)silver(I)

V. T. Yilmaz, S. Hamamci and C. Kazak

Abstract top

The AgI atom in the title complex, [Ag(C7H4NO3S)(C5H6N2)], adopts an almost linear AgN2 geometry with a saccharinate anion and a 3-aminopyridine ligand. Discrete molecules are linked by N-H...O hydrogen bonds into a three-dimensional network.

Comment top

Saccharin is a well known artificial sweetener and its deprotonated form, the saccharinate ion (sac), shows interesting ligation properties (Baran & Yilmaz 2006). Two different silver(I) complex of sac were reported by Weber et al. (1993) and Yilmaz et al. (2004). As part of our studies of mixed-ligand silver(I)-sac complexes with pyridine derivaties, the title compound (I) was prepared and characterized.

As shown in (Fig. 1), the AgI atom in (I) is coordinated by a sac ion and a neutral 3-aminopyridine ligand. The coordination geometry of the AgI atom is two-coordinate (linear) (Table 1). The shortest Ag···Ag distance between adjacent molecules in the crystal is 3.529 (2) Å which is considerably longer than the upper limit of 3.30 Å suggested for an argentophilic interaction in the silver(I) complexes (Jansen, 1987). Individual molecules are connected by N—H···O hydrogen bonds, involving the amine H atoms of 3-aminopyridine and the carbonyl and sulfonyl O atoms of the sac anion, thus forming a three-dimensional network (Table 2).

Related literature top

For background, see: Jansen (1987); Weber et al. (1993); Yilmaz et al. (2004); Baran & Yilmaz (2006).

Experimental top

Na(sac)·2H2O (0.24 g, 1 mmol) and 3-aminopyridine (0.09 g, 1 mmol) were added to a 20 ml solution of AgNO3 (0.17 g, 1 mmol) dissolved in a mixture of water and acetonitryl (1:1, v/v). The solution was stirred for an hour at room temperature. Colourless prisms of (I) were obtained after 3 days by slow evoparation of the solution at room temperature.

Refinement top

All hydrogen atoms were placed in idealized locations (C—H = 0.93 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(parent atom).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids (arbitrary spheres for the H atoms). The C-bound hydrogen atoms are omitted for clarity.
(3-Aminopyridine-κN1)(saccharinato-KN)silver(I) top
Crystal data top
[Ag(C7H4NO3S)(C5H6N2)]Z = 2
Mr = 384.17F000 = 380
Triclinic, P1Dx = 1.949 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 6.7294 (7) ÅCell parameters from 21946 reflections
b = 8.0205 (8) Åθ = 2.8–28.0º
c = 13.5187 (14) ŵ = 1.71 mm−1
α = 82.149 (8)ºT = 296 (2) K
β = 80.111 (8)ºPrism, colourless
γ = 65.952 (7)º0.52 × 0.45 × 0.33 mm
V = 654.62 (12) Å3
Data collection top
Stoe IPDS 2
diffractometer		3078 independent reflections
Radiation source: fine-focus sealed tube2773 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.044
Detector resolution: 6.67 pixels mm-1θmax = 27.8º
T = 296(2) Kθmin = 2.8º
rotation method scansh = −8→8
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)		k = −10→10
Tmin = 0.466, Tmax = 0.560l = −17→17
11027 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.023  w = 1/[σ2(Fo2) + (0.0369P)2 + 0.1071P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.061(Δ/σ)max = 0.014
S = 1.04Δρmax = 0.39 e Å−3
3078 reflectionsΔρmin = −0.56 e Å−3
182 parametersExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.102 (3)
Secondary atom site location: difference Fourier map
Crystal data top
[Ag(C7H4NO3S)(C5H6N2)]γ = 65.952 (7)º
Mr = 384.17V = 654.62 (12) Å3
Triclinic, P1Z = 2
a = 6.7294 (7) ÅMo Kα
b = 8.0205 (8) ŵ = 1.71 mm−1
c = 13.5187 (14) ÅT = 296 (2) K
α = 82.149 (8)º0.52 × 0.45 × 0.33 mm
β = 80.111 (8)º
Data collection top
Stoe IPDS 2
diffractometer		3078 independent reflections
Absorption correction: integration
(X-RED; Stoe & Cie, 2002)		2773 reflections with I > 2σ(I)
Tmin = 0.466, Tmax = 0.560Rint = 0.044
11027 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.023182 parameters
wR(F2) = 0.061H-atom parameters constrained
S = 1.04Δρmax = 0.39 e Å−3
3078 reflectionsΔρmin = −0.56 e Å−3
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
C10.1263 (3)1.0814 (3)0.71084 (13)0.0378 (4)
C20.0605 (3)1.1547 (3)0.81218 (13)0.0370 (4)
C3−0.1290 (3)1.3000 (3)0.84509 (16)0.0478 (5)
H3−0.23731.36250.80340.057*
C4−0.1522 (4)1.3493 (3)0.94175 (18)0.0571 (6)
H4−0.27701.44760.96520.068*
C50.0064 (4)1.2554 (4)1.00394 (17)0.0588 (6)
H5−0.01431.29101.06880.071*
C60.1957 (4)1.1095 (4)0.97232 (16)0.0511 (5)
H60.30241.04531.01450.061*
C70.2184 (3)1.0637 (3)0.87496 (14)0.0389 (4)
C80.5785 (4)0.6660 (3)0.36057 (16)0.0463 (4)
H80.46120.77480.34670.056*
C90.6889 (4)0.5513 (3)0.28488 (15)0.0511 (5)
H90.64580.58250.22080.061*
C100.8629 (4)0.3906 (3)0.30389 (15)0.0471 (4)
H100.94090.31380.25250.057*
C110.9213 (3)0.3438 (3)0.40059 (14)0.0384 (4)
C120.8017 (3)0.4666 (3)0.47316 (13)0.0371 (4)
H120.83900.43720.53830.044*
N10.3306 (3)0.9470 (2)0.70220 (12)0.0415 (3)
N20.6354 (3)0.6253 (2)0.45379 (12)0.0400 (3)
N31.0955 (3)0.1840 (3)0.42523 (14)0.0503 (4)
H3A1.17200.10960.37980.060*
H3B1.12710.15930.48600.060*
O10.0082 (3)1.1362 (2)0.64384 (11)0.0520 (4)
O20.4685 (3)0.7160 (2)0.84633 (14)0.0675 (5)
O30.6308 (3)0.9409 (3)0.79346 (13)0.0614 (4)
S10.43996 (8)0.89815 (7)0.80659 (4)0.04355 (12)
Ag10.49733 (3)0.80193 (2)0.574282 (11)0.04861 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0397 (9)0.0380 (9)0.0337 (8)−0.0128 (7)−0.0045 (7)−0.0046 (7)
C20.0367 (9)0.0388 (9)0.0327 (8)−0.0116 (7)−0.0037 (7)−0.0046 (7)
C30.0398 (10)0.0461 (10)0.0460 (10)−0.0054 (8)−0.0040 (8)−0.0053 (8)
C40.0512 (12)0.0544 (12)0.0496 (12)−0.0054 (10)0.0067 (9)−0.0174 (10)
C50.0631 (14)0.0688 (15)0.0387 (10)−0.0190 (12)0.0039 (9)−0.0203 (10)
C60.0467 (11)0.0682 (14)0.0348 (9)−0.0166 (10)−0.0067 (8)−0.0090 (9)
C70.0349 (9)0.0432 (9)0.0340 (8)−0.0102 (7)−0.0027 (7)−0.0069 (7)
C80.0473 (11)0.0473 (11)0.0455 (10)−0.0196 (9)−0.0075 (8)−0.0023 (8)
C90.0610 (13)0.0641 (13)0.0342 (9)−0.0291 (11)−0.0089 (9)−0.0049 (9)
C100.0529 (11)0.0581 (12)0.0340 (9)−0.0238 (10)−0.0014 (8)−0.0142 (8)
C110.0376 (9)0.0460 (10)0.0364 (8)−0.0207 (8)0.0006 (7)−0.0121 (7)
C120.0374 (9)0.0456 (10)0.0330 (8)−0.0205 (8)−0.0007 (7)−0.0101 (7)
N10.0412 (8)0.0436 (8)0.0340 (7)−0.0090 (7)−0.0035 (6)−0.0110 (6)
N20.0385 (8)0.0453 (8)0.0389 (8)−0.0191 (7)0.0015 (6)−0.0114 (7)
N30.0451 (9)0.0541 (10)0.0453 (9)−0.0084 (8)−0.0050 (7)−0.0192 (8)
O10.0499 (8)0.0629 (9)0.0390 (7)−0.0139 (7)−0.0143 (6)−0.0060 (6)
O20.0731 (11)0.0435 (8)0.0581 (10)0.0030 (8)−0.0080 (8)0.0024 (7)
O30.0366 (7)0.0903 (13)0.0507 (8)−0.0148 (8)−0.0054 (6)−0.0166 (8)
S10.0372 (2)0.0457 (3)0.0351 (2)−0.00214 (19)−0.00529 (17)−0.00619 (18)
Ag10.05145 (12)0.04605 (11)0.04045 (11)−0.01003 (7)0.00057 (6)−0.01523 (6)
Geometric parameters (Å, °) top
C1—O11.224 (2)C8—H80.9300
C1—N11.355 (2)C9—C101.371 (3)
C1—C21.489 (2)C9—H90.9300
C2—C71.375 (3)C10—C111.388 (3)
C2—C31.385 (3)C10—H100.9300
C3—C41.382 (3)C11—N31.386 (3)
C3—H30.9300C11—C121.388 (2)
C4—C51.376 (4)C12—N21.338 (3)
C4—H40.9300C12—H120.9300
C5—C61.382 (3)N1—S11.6301 (17)
C5—H50.9300N3—H3A0.8600
C6—C71.381 (3)N3—H3B0.8600
C6—H60.9300O2—S11.4322 (19)
C7—S11.7576 (19)O3—S11.4361 (18)
C8—N21.339 (3)Ag1—N12.103 (2)
C8—C91.373 (3)Ag1—N22.136 (2)
O1—C1—N1124.38 (18)C8—C9—H9120.0
O1—C1—C2123.60 (17)C9—C10—C11119.28 (19)
N1—C1—C2112.02 (15)C9—C10—H10120.4
C7—C2—C3120.21 (17)C11—C10—H10120.4
C7—C2—C1112.00 (15)N3—C11—C10122.46 (18)
C3—C2—C1127.75 (17)N3—C11—C12120.05 (18)
C4—C3—C2117.9 (2)C10—C11—C12117.46 (19)
C4—C3—H3121.1N2—C12—C11123.09 (17)
C2—C3—H3121.1N2—C12—H12118.5
C5—C4—C3121.1 (2)C11—C12—H12118.5
C5—C4—H4119.4C1—N1—S1112.45 (13)
C3—C4—H4119.4C1—N1—Ag1126.52 (13)
C4—C5—C6121.6 (2)S1—N1—Ag1120.98 (9)
C4—C5—H5119.2C12—N2—C8118.52 (17)
C6—C5—H5119.2C12—N2—Ag1115.95 (12)
C7—C6—C5116.7 (2)C8—N2—Ag1125.39 (15)
C7—C6—H6121.7C11—N3—H3A120.0
C5—C6—H6121.7C11—N3—H3B120.0
C2—C7—C6122.51 (18)H3A—N3—H3B120.0
C2—C7—S1107.76 (13)O2—S1—O3116.39 (12)
C6—C7—S1129.68 (16)O2—S1—N1110.23 (11)
N2—C8—C9121.7 (2)O3—S1—N1110.56 (10)
N2—C8—H8119.1O2—S1—C7111.72 (10)
C9—C8—H8119.1O3—S1—C7110.33 (10)
C10—C9—C8119.90 (19)N1—S1—C795.70 (9)
C10—C9—H9120.0N1—Ag1—N2170.00 (6)
O1—C1—C2—C7177.0 (2)O1—C1—N1—Ag10.7 (3)
N1—C1—C2—C7−2.7 (2)C2—C1—N1—Ag1−179.66 (13)
O1—C1—C2—C3−5.2 (3)C11—C12—N2—C81.4 (3)
N1—C1—C2—C3175.2 (2)C11—C12—N2—Ag1−174.39 (14)
C7—C2—C3—C40.2 (3)C9—C8—N2—C12−1.3 (3)
C1—C2—C3—C4−177.5 (2)C9—C8—N2—Ag1174.05 (16)
C2—C3—C4—C5−0.9 (4)C1—N1—S1—O2113.94 (16)
C3—C4—C5—C60.6 (4)Ag1—N1—S1—O2−63.80 (14)
C4—C5—C6—C70.5 (4)C1—N1—S1—O3−115.95 (16)
C3—C2—C7—C60.9 (3)Ag1—N1—S1—O366.30 (14)
C1—C2—C7—C6178.9 (2)C1—N1—S1—C7−1.73 (16)
C3—C2—C7—S1−176.67 (17)Ag1—N1—S1—C7−179.47 (11)
C1—C2—C7—S11.3 (2)C2—C7—S1—O2−114.31 (16)
C5—C6—C7—C2−1.3 (3)C6—C7—S1—O268.3 (2)
C5—C6—C7—S1175.75 (19)C2—C7—S1—O3114.56 (15)
N2—C8—C9—C10−0.3 (3)C6—C7—S1—O3−62.8 (2)
C8—C9—C10—C111.8 (3)C2—C7—S1—N10.14 (16)
C9—C10—C11—N3−179.8 (2)C6—C7—S1—N1−177.2 (2)
C9—C10—C11—C12−1.6 (3)C1—N1—Ag1—N2−83.7 (4)
N3—C11—C12—N2178.24 (18)S1—N1—Ag1—N293.8 (4)
C10—C11—C12—N20.1 (3)C12—N2—Ag1—N1−81.7 (4)
O1—C1—N1—S1−176.92 (18)C8—N2—Ag1—N1102.8 (4)
C2—C1—N1—S12.7 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O3i0.862.483.251 (2)149
N3—H3B···O1ii0.862.162.916 (2)147
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y−1, z.
Table 1
Selected geometric parameters (Å, °) top
Ag1—N12.103 (2)Ag1—N22.136 (2)
N1—Ag1—N2170.00 (6)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O3i0.862.483.251 (2)149
N3—H3B···O1ii0.862.162.916 (2)147
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y−1, z.
references
References top

Baran, E. J. & Yilmaz, V. T. (2006). Coord. Chem. Rev. 250, 1980–1999.

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565–?.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Jansen, M. (1987). Angew. Chem. Int. Ed. Engl. 26, 1098–1110.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Stoe & Cie (2002). X-AREA (Version 1.18) and X-RED (Version 1.04). Stoe & Cie. Darmstadt, Germany.

Weber, R., Gilles, M. & Bergerhoff, G. (1993). Z. Kristallogr. 206, 273–274.

Yilmaz, V. T., Hamamci, S. & Thone, C. (2004). Z. Anorg. Allg. Chem. 630, 1641–1644.