Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057248/hb2641sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057248/hb2641Isup2.hkl |
CCDC reference: 672648
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.023
- wR factor = 0.061
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT432_ALERT_2_C Short Inter X...Y Contact C12 .. C12 .. 3.14 Ang.
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1 (9) 0.97
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
For background, see: Jansen (1987); Weber et al. (1993); Yilmaz et al. (2004); Baran & Yilmaz (2006).
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.
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).
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).
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. |
[Ag(C7H4NO3S)(C5H6N2)] | Z = 2 |
Mr = 384.17 | F(000) = 380 |
Triclinic, P1 | Dx = 1.949 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7294 (7) Å | Cell parameters from 21946 reflections |
b = 8.0205 (8) Å | θ = 2.8–28.0° |
c = 13.5187 (14) Å | µ = 1.71 mm−1 |
α = 82.149 (8)° | T = 296 K |
β = 80.111 (8)° | Prism, colourless |
γ = 65.952 (7)° | 0.52 × 0.45 × 0.33 mm |
V = 654.62 (12) Å3 |
Stoe IPDS 2 diffractometer | 3078 independent reflections |
Radiation source: fine-focus sealed tube | 2773 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.8°, θmin = 2.8° |
rotation method scans | h = −8→8 |
Absorption correction: integration (X-RED; Stoe & Cie, 2002) | k = −10→10 |
Tmin = 0.466, Tmax = 0.560 | l = −17→17 |
11027 measured reflections |
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)] = 0.023 | H-atom parameters constrained |
wR(F2) = 0.061 | w = 1/[σ2(Fo2) + (0.0369P)2 + 0.1071P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.014 |
3078 reflections | Δρmax = 0.39 e Å−3 |
182 parameters | Δρmin = −0.56 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.102 (3) |
[Ag(C7H4NO3S)(C5H6N2)] | γ = 65.952 (7)° |
Mr = 384.17 | V = 654.62 (12) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.7294 (7) Å | Mo Kα radiation |
b = 8.0205 (8) Å | µ = 1.71 mm−1 |
c = 13.5187 (14) Å | T = 296 K |
α = 82.149 (8)° | 0.52 × 0.45 × 0.33 mm |
β = 80.111 (8)° |
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 = 0.560 | Rint = 0.044 |
11027 measured reflections |
R[F2 > 2σ(F2)] = 0.023 | 0 restraints |
wR(F2) = 0.061 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.39 e Å−3 |
3078 reflections | Δρmin = −0.56 e Å−3 |
182 parameters |
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 | ||
C1 | 0.1263 (3) | 1.0814 (3) | 0.71084 (13) | 0.0378 (4) | |
C2 | 0.0605 (3) | 1.1547 (3) | 0.81218 (13) | 0.0370 (4) | |
C3 | −0.1290 (3) | 1.3000 (3) | 0.84509 (16) | 0.0478 (5) | |
H3 | −0.2373 | 1.3625 | 0.8034 | 0.057* | |
C4 | −0.1522 (4) | 1.3493 (3) | 0.94175 (18) | 0.0571 (6) | |
H4 | −0.2770 | 1.4476 | 0.9652 | 0.068* | |
C5 | 0.0064 (4) | 1.2554 (4) | 1.00394 (17) | 0.0588 (6) | |
H5 | −0.0143 | 1.2910 | 1.0688 | 0.071* | |
C6 | 0.1957 (4) | 1.1095 (4) | 0.97232 (16) | 0.0511 (5) | |
H6 | 0.3024 | 1.0453 | 1.0145 | 0.061* | |
C7 | 0.2184 (3) | 1.0637 (3) | 0.87496 (14) | 0.0389 (4) | |
C8 | 0.5785 (4) | 0.6660 (3) | 0.36057 (16) | 0.0463 (4) | |
H8 | 0.4612 | 0.7748 | 0.3467 | 0.056* | |
C9 | 0.6889 (4) | 0.5513 (3) | 0.28488 (15) | 0.0511 (5) | |
H9 | 0.6458 | 0.5825 | 0.2208 | 0.061* | |
C10 | 0.8629 (4) | 0.3906 (3) | 0.30389 (15) | 0.0471 (4) | |
H10 | 0.9409 | 0.3138 | 0.2525 | 0.057* | |
C11 | 0.9213 (3) | 0.3438 (3) | 0.40059 (14) | 0.0384 (4) | |
C12 | 0.8017 (3) | 0.4666 (3) | 0.47316 (13) | 0.0371 (4) | |
H12 | 0.8390 | 0.4372 | 0.5383 | 0.044* | |
N1 | 0.3306 (3) | 0.9470 (2) | 0.70220 (12) | 0.0415 (3) | |
N2 | 0.6354 (3) | 0.6253 (2) | 0.45379 (12) | 0.0400 (3) | |
N3 | 1.0955 (3) | 0.1840 (3) | 0.42523 (14) | 0.0503 (4) | |
H3A | 1.1720 | 0.1096 | 0.3798 | 0.060* | |
H3B | 1.1271 | 0.1593 | 0.4860 | 0.060* | |
O1 | 0.0082 (3) | 1.1362 (2) | 0.64384 (11) | 0.0520 (4) | |
O2 | 0.4685 (3) | 0.7160 (2) | 0.84633 (14) | 0.0675 (5) | |
O3 | 0.6308 (3) | 0.9409 (3) | 0.79346 (13) | 0.0614 (4) | |
S1 | 0.43996 (8) | 0.89815 (7) | 0.80659 (4) | 0.04355 (12) | |
Ag1 | 0.49733 (3) | 0.80193 (2) | 0.574282 (11) | 0.04861 (9) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0397 (9) | 0.0380 (9) | 0.0337 (8) | −0.0128 (7) | −0.0045 (7) | −0.0046 (7) |
C2 | 0.0367 (9) | 0.0388 (9) | 0.0327 (8) | −0.0116 (7) | −0.0037 (7) | −0.0046 (7) |
C3 | 0.0398 (10) | 0.0461 (10) | 0.0460 (10) | −0.0054 (8) | −0.0040 (8) | −0.0053 (8) |
C4 | 0.0512 (12) | 0.0544 (12) | 0.0496 (12) | −0.0054 (10) | 0.0067 (9) | −0.0174 (10) |
C5 | 0.0631 (14) | 0.0688 (15) | 0.0387 (10) | −0.0190 (12) | 0.0039 (9) | −0.0203 (10) |
C6 | 0.0467 (11) | 0.0682 (14) | 0.0348 (9) | −0.0166 (10) | −0.0067 (8) | −0.0090 (9) |
C7 | 0.0349 (9) | 0.0432 (9) | 0.0340 (8) | −0.0102 (7) | −0.0027 (7) | −0.0069 (7) |
C8 | 0.0473 (11) | 0.0473 (11) | 0.0455 (10) | −0.0196 (9) | −0.0075 (8) | −0.0023 (8) |
C9 | 0.0610 (13) | 0.0641 (13) | 0.0342 (9) | −0.0291 (11) | −0.0089 (9) | −0.0049 (9) |
C10 | 0.0529 (11) | 0.0581 (12) | 0.0340 (9) | −0.0238 (10) | −0.0014 (8) | −0.0142 (8) |
C11 | 0.0376 (9) | 0.0460 (10) | 0.0364 (8) | −0.0207 (8) | 0.0006 (7) | −0.0121 (7) |
C12 | 0.0374 (9) | 0.0456 (10) | 0.0330 (8) | −0.0205 (8) | −0.0007 (7) | −0.0101 (7) |
N1 | 0.0412 (8) | 0.0436 (8) | 0.0340 (7) | −0.0090 (7) | −0.0035 (6) | −0.0110 (6) |
N2 | 0.0385 (8) | 0.0453 (8) | 0.0389 (8) | −0.0191 (7) | 0.0015 (6) | −0.0114 (7) |
N3 | 0.0451 (9) | 0.0541 (10) | 0.0453 (9) | −0.0084 (8) | −0.0050 (7) | −0.0192 (8) |
O1 | 0.0499 (8) | 0.0629 (9) | 0.0390 (7) | −0.0139 (7) | −0.0143 (6) | −0.0060 (6) |
O2 | 0.0731 (11) | 0.0435 (8) | 0.0581 (10) | 0.0030 (8) | −0.0080 (8) | 0.0024 (7) |
O3 | 0.0366 (7) | 0.0903 (13) | 0.0507 (8) | −0.0148 (8) | −0.0054 (6) | −0.0166 (8) |
S1 | 0.0372 (2) | 0.0457 (3) | 0.0351 (2) | −0.00214 (19) | −0.00529 (17) | −0.00619 (18) |
Ag1 | 0.05145 (12) | 0.04605 (11) | 0.04045 (11) | −0.01003 (7) | 0.00057 (6) | −0.01523 (6) |
C1—O1 | 1.224 (2) | C8—H8 | 0.9300 |
C1—N1 | 1.355 (2) | C9—C10 | 1.371 (3) |
C1—C2 | 1.489 (2) | C9—H9 | 0.9300 |
C2—C7 | 1.375 (3) | C10—C11 | 1.388 (3) |
C2—C3 | 1.385 (3) | C10—H10 | 0.9300 |
C3—C4 | 1.382 (3) | C11—N3 | 1.386 (3) |
C3—H3 | 0.9300 | C11—C12 | 1.388 (2) |
C4—C5 | 1.376 (4) | C12—N2 | 1.338 (3) |
C4—H4 | 0.9300 | C12—H12 | 0.9300 |
C5—C6 | 1.382 (3) | N1—S1 | 1.6301 (17) |
C5—H5 | 0.9300 | N3—H3A | 0.8600 |
C6—C7 | 1.381 (3) | N3—H3B | 0.8600 |
C6—H6 | 0.9300 | O2—S1 | 1.4322 (19) |
C7—S1 | 1.7576 (19) | O3—S1 | 1.4361 (18) |
C8—N2 | 1.339 (3) | Ag1—N1 | 2.103 (2) |
C8—C9 | 1.373 (3) | Ag1—N2 | 2.136 (2) |
O1—C1—N1 | 124.38 (18) | C8—C9—H9 | 120.0 |
O1—C1—C2 | 123.60 (17) | C9—C10—C11 | 119.28 (19) |
N1—C1—C2 | 112.02 (15) | C9—C10—H10 | 120.4 |
C7—C2—C3 | 120.21 (17) | C11—C10—H10 | 120.4 |
C7—C2—C1 | 112.00 (15) | N3—C11—C10 | 122.46 (18) |
C3—C2—C1 | 127.75 (17) | N3—C11—C12 | 120.05 (18) |
C4—C3—C2 | 117.9 (2) | C10—C11—C12 | 117.46 (19) |
C4—C3—H3 | 121.1 | N2—C12—C11 | 123.09 (17) |
C2—C3—H3 | 121.1 | N2—C12—H12 | 118.5 |
C5—C4—C3 | 121.1 (2) | C11—C12—H12 | 118.5 |
C5—C4—H4 | 119.4 | C1—N1—S1 | 112.45 (13) |
C3—C4—H4 | 119.4 | C1—N1—Ag1 | 126.52 (13) |
C4—C5—C6 | 121.6 (2) | S1—N1—Ag1 | 120.98 (9) |
C4—C5—H5 | 119.2 | C12—N2—C8 | 118.52 (17) |
C6—C5—H5 | 119.2 | C12—N2—Ag1 | 115.95 (12) |
C7—C6—C5 | 116.7 (2) | C8—N2—Ag1 | 125.39 (15) |
C7—C6—H6 | 121.7 | C11—N3—H3A | 120.0 |
C5—C6—H6 | 121.7 | C11—N3—H3B | 120.0 |
C2—C7—C6 | 122.51 (18) | H3A—N3—H3B | 120.0 |
C2—C7—S1 | 107.76 (13) | O2—S1—O3 | 116.39 (12) |
C6—C7—S1 | 129.68 (16) | O2—S1—N1 | 110.23 (11) |
N2—C8—C9 | 121.7 (2) | O3—S1—N1 | 110.56 (10) |
N2—C8—H8 | 119.1 | O2—S1—C7 | 111.72 (10) |
C9—C8—H8 | 119.1 | O3—S1—C7 | 110.33 (10) |
C10—C9—C8 | 119.90 (19) | N1—S1—C7 | 95.70 (9) |
C10—C9—H9 | 120.0 | N1—Ag1—N2 | 170.00 (6) |
O1—C1—C2—C7 | 177.0 (2) | O1—C1—N1—Ag1 | 0.7 (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—C8 | 1.4 (3) |
N1—C1—C2—C3 | 175.2 (2) | C11—C12—N2—Ag1 | −174.39 (14) |
C7—C2—C3—C4 | 0.2 (3) | C9—C8—N2—C12 | −1.3 (3) |
C1—C2—C3—C4 | −177.5 (2) | C9—C8—N2—Ag1 | 174.05 (16) |
C2—C3—C4—C5 | −0.9 (4) | C1—N1—S1—O2 | 113.94 (16) |
C3—C4—C5—C6 | 0.6 (4) | Ag1—N1—S1—O2 | −63.80 (14) |
C4—C5—C6—C7 | 0.5 (4) | C1—N1—S1—O3 | −115.95 (16) |
C3—C2—C7—C6 | 0.9 (3) | Ag1—N1—S1—O3 | 66.30 (14) |
C1—C2—C7—C6 | 178.9 (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—S1 | 1.3 (2) | C2—C7—S1—O2 | −114.31 (16) |
C5—C6—C7—C2 | −1.3 (3) | C6—C7—S1—O2 | 68.3 (2) |
C5—C6—C7—S1 | 175.75 (19) | C2—C7—S1—O3 | 114.56 (15) |
N2—C8—C9—C10 | −0.3 (3) | C6—C7—S1—O3 | −62.8 (2) |
C8—C9—C10—C11 | 1.8 (3) | C2—C7—S1—N1 | 0.14 (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—N2 | 178.24 (18) | S1—N1—Ag1—N2 | 93.8 (4) |
C10—C11—C12—N2 | 0.1 (3) | C12—N2—Ag1—N1 | −81.7 (4) |
O1—C1—N1—S1 | −176.92 (18) | C8—N2—Ag1—N1 | 102.8 (4) |
C2—C1—N1—S1 | 2.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3i | 0.86 | 2.48 | 3.251 (2) | 149 |
N3—H3B···O1ii | 0.86 | 2.16 | 2.916 (2) | 147 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C7H4NO3S)(C5H6N2)] |
Mr | 384.17 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 6.7294 (7), 8.0205 (8), 13.5187 (14) |
α, β, γ (°) | 82.149 (8), 80.111 (8), 65.952 (7) |
V (Å3) | 654.62 (12) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.71 |
Crystal size (mm) | 0.52 × 0.45 × 0.33 |
Data collection | |
Diffractometer | Stoe IPDS 2 diffractometer |
Absorption correction | Integration (X-RED; Stoe & Cie, 2002) |
Tmin, Tmax | 0.466, 0.560 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11027, 3078, 2773 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.656 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.023, 0.061, 1.04 |
No. of reflections | 3078 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.39, −0.56 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···O3i | 0.86 | 2.48 | 3.251 (2) | 149 |
N3—H3B···O1ii | 0.86 | 2.16 | 2.916 (2) | 147 |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x+1, y−1, z. |
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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).