Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705845X/bt2607sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705845X/bt2607Isup2.hkl |
CCDC reference: 672699
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.003 Å
- R factor = 0.025
- wR factor = 0.056
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Ag1 (9) 0.48
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 0 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 0 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 related literature, see: Weber et al. (1993); Yilmaz et al. (2004); Liu et al. (2006); Baran & Yilmaz (2006).
Na(sac)·2H2O (0.24 g, 1 mmol) was added to a 320 ml solution of AgNO3 (0.17 g, 1 mmol) dissolved in a mixture of water, methanol and dichloromethane (1:1:1, v/v) with stirring. The solution immediately became milky and the addition of bpy (0.16 g, 1 mmol) to the milky suspension resulted in a clear solution. The resulting solution was stirred for 30 min at room temperature and was allowed to stand in darkness at room temperature. Colorless crystals of the title compound were obtained after a week.
All hydrogen atoms were placed in idealized locations and refined by riding, with C—H = 0.95 Å and Uiso(H) = 1.2 x Ueq(C).
Data collection: COLLECT (Enraf–Nonius, 1999); cell refinement: COLLECT (Enraf–Nonius, 1999); data reduction: COLLECT (Enraf–Nonius, 1999); 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: SHELXL97 (Sheldrick, 1997).
Fig. 1. The molecular structure of (I) showing 40% displacement ellipsoids (arbitrary spheres for the H atoms). C—H hydrogen atoms were removed for clarity. |
[Ag(C7H4NO3S)(C10H8N2)] | F(000) = 888 |
Mr = 446.23 | Dx = 1.831 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3928 reflections |
a = 10.7803 (2) Å | θ = 2.9–27.5° |
b = 9.7683 (1) Å | µ = 1.40 mm−1 |
c = 15.6176 (2) Å | T = 120 K |
β = 100.1975 (8)° | Needle, colourless |
V = 1618.64 (4) Å3 | 0.40 × 0.04 × 0.02 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3713 independent reflections |
Radiation source: fine-focus sealed tube | 3194 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω and ϕ scans | θmax = 27.5°, θmin = 3.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −14→13 |
Tmin = 0.605, Tmax = 0.973 | k = −12→12 |
25291 measured reflections | l = −20→20 |
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)] = 0.025 | H-atom parameters constrained |
wR(F2) = 0.056 | w = 1/[σ2(Fo2) + (0.0156P)2 + 1.822P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.001 |
3713 reflections | Δρmax = 0.43 e Å−3 |
227 parameters | Δρmin = −0.46 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: 0.00128 (18) |
[Ag(C7H4NO3S)(C10H8N2)] | V = 1618.64 (4) Å3 |
Mr = 446.23 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 10.7803 (2) Å | µ = 1.40 mm−1 |
b = 9.7683 (1) Å | T = 120 K |
c = 15.6176 (2) Å | 0.40 × 0.04 × 0.02 mm |
β = 100.1975 (8)° |
Nonius KappaCCD diffractometer | 3713 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 3194 reflections with I > 2σ(I) |
Tmin = 0.605, Tmax = 0.973 | Rint = 0.038 |
25291 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.056 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.43 e Å−3 |
3713 reflections | Δρmin = −0.46 e Å−3 |
227 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 | ||
Ag1 | 0.501633 (17) | 0.793746 (18) | 0.021427 (11) | 0.02327 (7) | |
C1 | 0.4298 (2) | 1.0121 (2) | 0.15235 (13) | 0.0158 (4) | |
C2 | 0.33090 (19) | 1.1138 (2) | 0.16617 (13) | 0.0145 (4) | |
C3 | 0.3360 (2) | 1.2084 (2) | 0.23278 (14) | 0.0185 (4) | |
H3 | 0.4093 | 1.2169 | 0.2763 | 0.022* | |
C4 | 0.2318 (2) | 1.2901 (2) | 0.23427 (14) | 0.0229 (5) | |
H4 | 0.2339 | 1.3561 | 0.2792 | 0.028* | |
C5 | 0.1232 (2) | 1.2772 (2) | 0.17078 (15) | 0.0221 (5) | |
H5 | 0.0526 | 1.3341 | 0.1735 | 0.026* | |
C6 | 0.1172 (2) | 1.1826 (2) | 0.10380 (14) | 0.0190 (5) | |
H6 | 0.0439 | 1.1729 | 0.0605 | 0.023* | |
C7 | 0.2232 (2) | 1.1032 (2) | 0.10334 (13) | 0.0144 (4) | |
N1 | 0.39147 (17) | 0.93554 (19) | 0.07890 (11) | 0.0182 (4) | |
O1 | 0.53026 (15) | 0.99921 (17) | 0.20193 (10) | 0.0240 (4) | |
O2 | 0.16452 (15) | 0.85874 (16) | 0.03892 (11) | 0.0271 (4) | |
O3 | 0.24637 (18) | 1.02164 (18) | −0.05562 (10) | 0.0295 (4) | |
S1 | 0.24856 (5) | 0.97131 (6) | 0.03116 (3) | 0.01733 (12) | |
C8 | 0.7656 (2) | 0.6447 (2) | 0.08002 (15) | 0.0244 (5) | |
H8 | 0.7734 | 0.7113 | 0.1250 | 0.029* | |
C9 | 0.8607 (2) | 0.5498 (2) | 0.08214 (15) | 0.0237 (5) | |
H9 | 0.9324 | 0.5509 | 0.1273 | 0.028* | |
C10 | 0.8489 (2) | 0.4530 (2) | 0.01676 (15) | 0.0224 (5) | |
H10 | 0.9124 | 0.3857 | 0.0165 | 0.027* | |
C11 | 0.7438 (2) | 0.4551 (2) | −0.04827 (14) | 0.0182 (5) | |
H11 | 0.7345 | 0.3894 | −0.0938 | 0.022* | |
C12 | 0.6517 (2) | 0.5545 (2) | −0.04641 (13) | 0.0147 (4) | |
C13 | 0.5363 (2) | 0.5625 (2) | −0.11505 (13) | 0.0158 (4) | |
C14 | 0.5170 (2) | 0.4753 (3) | −0.18644 (15) | 0.0248 (5) | |
H14 | 0.5774 | 0.4070 | −0.1927 | 0.030* | |
C15 | 0.4087 (2) | 0.4890 (3) | −0.24846 (15) | 0.0283 (6) | |
H15 | 0.3943 | 0.4307 | −0.2979 | 0.034* | |
C16 | 0.3221 (2) | 0.5881 (3) | −0.23762 (15) | 0.0268 (5) | |
H16 | 0.2464 | 0.5986 | −0.2787 | 0.032* | |
C17 | 0.3481 (2) | 0.6718 (3) | −0.16543 (16) | 0.0265 (5) | |
H17 | 0.2888 | 0.7408 | −0.1581 | 0.032* | |
N2 | 0.66271 (17) | 0.64772 (19) | 0.01771 (11) | 0.0184 (4) | |
N3 | 0.45297 (17) | 0.6604 (2) | −0.10520 (12) | 0.0197 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.02769 (11) | 0.01844 (10) | 0.02661 (11) | 0.00675 (7) | 0.01280 (7) | −0.00129 (7) |
C1 | 0.0157 (11) | 0.0180 (11) | 0.0142 (10) | −0.0019 (9) | 0.0041 (8) | 0.0016 (8) |
C2 | 0.0166 (10) | 0.0129 (10) | 0.0144 (10) | 0.0002 (8) | 0.0039 (8) | 0.0027 (8) |
C3 | 0.0216 (11) | 0.0183 (11) | 0.0149 (10) | −0.0024 (9) | 0.0016 (9) | −0.0011 (9) |
C4 | 0.0347 (13) | 0.0165 (11) | 0.0189 (11) | 0.0021 (10) | 0.0082 (10) | −0.0039 (9) |
C5 | 0.0256 (12) | 0.0180 (12) | 0.0240 (11) | 0.0085 (10) | 0.0084 (10) | 0.0026 (9) |
C6 | 0.0180 (11) | 0.0178 (11) | 0.0204 (11) | 0.0027 (9) | 0.0017 (9) | 0.0025 (9) |
C7 | 0.0183 (11) | 0.0116 (10) | 0.0135 (10) | −0.0004 (8) | 0.0034 (8) | 0.0004 (8) |
N1 | 0.0172 (9) | 0.0196 (10) | 0.0173 (9) | 0.0048 (8) | 0.0018 (7) | −0.0030 (7) |
O1 | 0.0152 (8) | 0.0314 (10) | 0.0235 (8) | 0.0034 (7) | −0.0015 (7) | −0.0012 (7) |
O2 | 0.0234 (9) | 0.0167 (8) | 0.0379 (10) | −0.0006 (7) | −0.0040 (7) | −0.0056 (7) |
O3 | 0.0416 (11) | 0.0304 (10) | 0.0147 (8) | 0.0090 (8) | 0.0002 (7) | −0.0023 (7) |
S1 | 0.0194 (3) | 0.0152 (3) | 0.0157 (2) | 0.0030 (2) | −0.0016 (2) | −0.0033 (2) |
C8 | 0.0290 (13) | 0.0225 (12) | 0.0195 (11) | 0.0017 (10) | −0.0014 (10) | −0.0054 (9) |
C9 | 0.0233 (12) | 0.0214 (12) | 0.0230 (12) | 0.0017 (10) | −0.0057 (9) | 0.0012 (10) |
C10 | 0.0201 (12) | 0.0173 (11) | 0.0289 (12) | 0.0058 (9) | 0.0020 (10) | 0.0021 (9) |
C11 | 0.0202 (11) | 0.0151 (11) | 0.0195 (11) | 0.0004 (9) | 0.0037 (9) | −0.0024 (9) |
C12 | 0.0158 (11) | 0.0138 (10) | 0.0152 (10) | −0.0015 (9) | 0.0042 (8) | 0.0014 (8) |
C13 | 0.0167 (11) | 0.0150 (10) | 0.0163 (10) | −0.0027 (9) | 0.0044 (8) | 0.0019 (8) |
C14 | 0.0239 (12) | 0.0254 (13) | 0.0238 (12) | 0.0005 (10) | 0.0004 (10) | −0.0054 (10) |
C15 | 0.0291 (14) | 0.0314 (14) | 0.0221 (12) | −0.0062 (11) | −0.0020 (10) | −0.0048 (10) |
C16 | 0.0186 (12) | 0.0366 (15) | 0.0228 (12) | −0.0070 (11) | −0.0028 (9) | 0.0063 (10) |
C17 | 0.0181 (12) | 0.0334 (14) | 0.0274 (12) | 0.0049 (10) | 0.0023 (10) | 0.0046 (11) |
N2 | 0.0204 (10) | 0.0164 (9) | 0.0177 (9) | 0.0035 (8) | 0.0017 (8) | −0.0021 (7) |
N3 | 0.0166 (9) | 0.0236 (10) | 0.0184 (9) | 0.0030 (8) | 0.0018 (7) | 0.0000 (8) |
C1—O1 | 1.221 (3) | C9—H9 | 0.9500 |
C1—N1 | 1.370 (3) | C10—C11 | 1.381 (3) |
C1—C2 | 1.500 (3) | C10—H10 | 0.9500 |
C2—C7 | 1.385 (3) | C11—C12 | 1.393 (3) |
C2—C3 | 1.385 (3) | C11—H11 | 0.9500 |
C3—C4 | 1.382 (3) | C12—N2 | 1.343 (3) |
C3—H3 | 0.9500 | C12—C13 | 1.493 (3) |
C4—C5 | 1.399 (3) | C13—N3 | 1.339 (3) |
C4—H4 | 0.9500 | C13—C14 | 1.389 (3) |
C5—C6 | 1.389 (3) | C14—C15 | 1.385 (3) |
C5—H5 | 0.9500 | C14—H14 | 0.9500 |
C6—C7 | 1.383 (3) | C15—C16 | 1.375 (4) |
C6—H6 | 0.9500 | C15—H15 | 0.9500 |
C7—S1 | 1.764 (2) | C16—C17 | 1.381 (3) |
N1—S1 | 1.6262 (18) | C16—H16 | 0.9500 |
O2—S1 | 1.4434 (17) | C17—N3 | 1.341 (3) |
O3—S1 | 1.4379 (17) | C17—H17 | 0.9500 |
C8—N2 | 1.340 (3) | Ag1—N1 | 2.1241 (18) |
C8—C9 | 1.378 (3) | Ag1—N2 | 2.2559 (18) |
C8—H8 | 0.9500 | Ag1—N3 | 2.3488 (18) |
C9—C10 | 1.381 (3) | ||
O1—C1—N1 | 125.2 (2) | C10—C9—H9 | 120.9 |
O1—C1—C2 | 123.36 (19) | C9—C10—C11 | 119.3 (2) |
N1—C1—C2 | 111.43 (18) | C9—C10—H10 | 120.3 |
C7—C2—C3 | 119.95 (19) | C11—C10—H10 | 120.3 |
C7—C2—C1 | 112.09 (18) | C10—C11—C12 | 119.3 (2) |
C3—C2—C1 | 127.95 (19) | C10—C11—H11 | 120.3 |
C4—C3—C2 | 118.3 (2) | C12—C11—H11 | 120.3 |
C4—C3—H3 | 120.9 | N2—C12—C11 | 121.25 (19) |
C2—C3—H3 | 120.9 | N2—C12—C13 | 116.89 (18) |
C3—C4—C5 | 121.1 (2) | C11—C12—C13 | 121.86 (19) |
C3—C4—H4 | 119.4 | N3—C13—C14 | 121.4 (2) |
C5—C4—H4 | 119.4 | N3—C13—C12 | 116.45 (18) |
C6—C5—C4 | 121.0 (2) | C14—C13—C12 | 122.1 (2) |
C6—C5—H5 | 119.5 | C15—C14—C13 | 119.4 (2) |
C4—C5—H5 | 119.5 | C15—C14—H14 | 120.3 |
C7—C6—C5 | 116.7 (2) | C13—C14—H14 | 120.3 |
C7—C6—H6 | 121.7 | C16—C15—C14 | 119.2 (2) |
C5—C6—H6 | 121.7 | C16—C15—H15 | 120.4 |
C6—C7—C2 | 122.98 (19) | C14—C15—H15 | 120.4 |
C6—C7—S1 | 129.37 (16) | C15—C16—C17 | 118.2 (2) |
C2—C7—S1 | 107.61 (15) | C15—C16—H16 | 120.9 |
C1—N1—S1 | 112.78 (15) | C17—C16—H16 | 120.9 |
C1—N1—Ag1 | 126.97 (14) | N3—C17—C16 | 123.2 (2) |
S1—N1—Ag1 | 120.10 (10) | N3—C17—H17 | 118.4 |
O3—S1—O2 | 115.70 (11) | C16—C17—H17 | 118.4 |
O3—S1—N1 | 111.21 (10) | C8—N2—C12 | 118.60 (19) |
O2—S1—N1 | 110.83 (10) | C8—N2—Ag1 | 122.51 (15) |
O3—S1—C7 | 111.97 (10) | C12—N2—Ag1 | 118.75 (14) |
O2—S1—C7 | 109.39 (10) | C13—N3—C17 | 118.6 (2) |
N1—S1—C7 | 96.03 (10) | C13—N3—Ag1 | 115.99 (14) |
N2—C8—C9 | 123.3 (2) | C17—N3—Ag1 | 125.41 (16) |
N2—C8—H8 | 118.3 | N1—Ag1—N2 | 156.02 (7) |
C9—C8—H8 | 118.3 | N1—Ag1—N3 | 131.25 (7) |
C8—C9—C10 | 118.2 (2) | N2—Ag1—N3 | 71.69 (6) |
C8—C9—H9 | 120.9 | ||
O1—C1—C2—C7 | −176.8 (2) | N2—C8—C9—C10 | −0.1 (4) |
N1—C1—C2—C7 | 2.0 (3) | C8—C9—C10—C11 | 0.5 (4) |
O1—C1—C2—C3 | 1.4 (4) | C9—C10—C11—C12 | −0.2 (3) |
N1—C1—C2—C3 | −179.7 (2) | C10—C11—C12—N2 | −0.5 (3) |
C7—C2—C3—C4 | 0.0 (3) | C10—C11—C12—C13 | 179.7 (2) |
C1—C2—C3—C4 | −178.1 (2) | N2—C12—C13—N3 | −1.4 (3) |
C2—C3—C4—C5 | 0.6 (3) | C11—C12—C13—N3 | 178.4 (2) |
C3—C4—C5—C6 | −0.5 (3) | N2—C12—C13—C14 | 177.3 (2) |
C4—C5—C6—C7 | −0.2 (3) | C11—C12—C13—C14 | −2.9 (3) |
C5—C6—C7—C2 | 0.8 (3) | N3—C13—C14—C15 | −0.6 (4) |
C5—C6—C7—S1 | 178.26 (17) | C12—C13—C14—C15 | −179.2 (2) |
C3—C2—C7—C6 | −0.7 (3) | C13—C14—C15—C16 | −0.5 (4) |
C1—C2—C7—C6 | 177.67 (19) | C14—C15—C16—C17 | 1.0 (4) |
C3—C2—C7—S1 | −178.69 (17) | C15—C16—C17—N3 | −0.6 (4) |
C1—C2—C7—S1 | −0.3 (2) | C9—C8—N2—C12 | −0.5 (4) |
O1—C1—N1—S1 | 175.89 (18) | C9—C8—N2—Ag1 | 175.15 (18) |
C2—C1—N1—S1 | −2.9 (2) | C11—C12—N2—C8 | 0.8 (3) |
O1—C1—N1—Ag1 | −8.7 (3) | C13—C12—N2—C8 | −179.33 (19) |
C2—C1—N1—Ag1 | 172.54 (14) | C11—C12—N2—Ag1 | −175.03 (16) |
N2—Ag1—N1—C1 | 21.5 (3) | C13—C12—N2—Ag1 | 4.8 (2) |
N3—Ag1—N1—C1 | −177.96 (16) | N1—Ag1—N2—C8 | −15.4 (3) |
N2—Ag1—N1—S1 | −163.35 (13) | N3—Ag1—N2—C8 | 179.9 (2) |
N3—Ag1—N1—S1 | −2.81 (17) | N1—Ag1—N2—C12 | 160.26 (17) |
C1—N1—S1—O3 | 118.83 (16) | N3—Ag1—N2—C12 | −4.44 (15) |
Ag1—N1—S1—O3 | −56.97 (14) | C14—C13—N3—C17 | 1.0 (3) |
C1—N1—S1—O2 | −110.97 (16) | C12—C13—N3—C17 | 179.76 (19) |
Ag1—N1—S1—O2 | 73.23 (14) | C14—C13—N3—Ag1 | 178.83 (17) |
C1—N1—S1—C7 | 2.44 (17) | C12—C13—N3—Ag1 | −2.5 (2) |
Ag1—N1—S1—C7 | −173.36 (11) | C16—C17—N3—C13 | −0.5 (4) |
C6—C7—S1—O3 | 65.3 (2) | C16—C17—N3—Ag1 | −178.04 (18) |
C2—C7—S1—O3 | −116.97 (16) | N1—Ag1—N3—C13 | −168.24 (14) |
C6—C7—S1—O2 | −64.4 (2) | N2—Ag1—N3—C13 | 3.56 (15) |
C2—C7—S1—O2 | 113.41 (15) | N1—Ag1—N3—C17 | 9.4 (2) |
C6—C7—S1—N1 | −179.0 (2) | N2—Ag1—N3—C17 | −178.8 (2) |
C2—C7—S1—N1 | −1.19 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.95 | 2.51 | 3.458 (3) | 173 |
C16—H16···O1ii | 0.95 | 2.49 | 3.235 (3) | 136 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1/2, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | [Ag(C7H4NO3S)(C10H8N2)] |
Mr | 446.23 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 120 |
a, b, c (Å) | 10.7803 (2), 9.7683 (1), 15.6176 (2) |
β (°) | 100.1975 (8) |
V (Å3) | 1618.64 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.40 |
Crystal size (mm) | 0.40 × 0.04 × 0.02 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | 0.605, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25291, 3713, 3194 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.056, 1.08 |
No. of reflections | 3713 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.46 |
Computer programs: COLLECT (Enraf–Nonius, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).
Ag1—N1 | 2.1241 (18) | Ag1—N3 | 2.3488 (18) |
Ag1—N2 | 2.2559 (18) | ||
N1—Ag1—N2 | 156.02 (7) | N2—Ag1—N3 | 71.69 (6) |
N1—Ag1—N3 | 131.25 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
C6—H6···O2i | 0.95 | 2.51 | 3.458 (3) | 173 |
C16—H16···O1ii | 0.95 | 2.49 | 3.235 (3) | 136 |
Symmetry codes: (i) −x, −y+2, −z; (ii) x−1/2, −y+3/2, z−1/2. |
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Saccharin is a well known artificial sweetener and it readily coordinates metal ions in the deprotonated form, saccharinate (sac) (Baran & Yilmaz 2006). The first silver(I) complexes of sac were reported by Weber et al. (1993) and Yilmaz et al. (2004). In this paper, the structure of the title compound, (I) (Fig. 1), containing a 2,2'-bipyridine (bpy) molecule and a sac anion is described.
In (I), Ag(I)I ion is coordinated by two N atoms from 2,2'-bipyridine and one N atom from saccharinate, forming a highly distorted T-shaped (or trigonal planar) coordination geometry (Table 1). The small bite angle of bpy [71.69 (6)°] is responsible for the distortion of the coordination geometry similar to that of a silver(I) complex of bpy (Liu et al., 2006). Both ligands are essentially planar and the dihedral angle between the two pyridine rings of the bipy ligand is only 2.48 (11)°, while the dihedral angle between the sac benzene ring and sac 5-membered ring is 0.50 (8)°. The sac ion makes a dihedral angle of 7.20 (8)° with the complete bipy molecule.
The closest Ag···Agi contact is 4.0838 (3) Å (i = 1 - x, 2 - y, -z). There are two intramolecular CH···O hydrogen bonds involving the sac and bpy ring H atoms and sulfonly and carbony O atoms (Table 2). Furthermore, the molecules are further linked by π(bpy)···π(bpy) interactions with a Cg—Cgi separation of 3.6741 (13) Å (i = 1 - x, 1 - y, -z).