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The title complex, [Ag(C7H4NO3S)(C10H8N2)], has a mononuclear structure in which the AgI ion is coordinated by two N atoms from 2,2′-bipyridine and one N atom from saccharinate, forming a distorted T-shaped (or trigonal-planar) AgN3 arrangement. The bite angle of bpy is 71.69 (6)°, which contributes significantly to the distortion of the coordination geometry. Mol­ecules are connected by C—H...O and π(bpy)–π(bpy) inter­actions with a centroid–centroid separation of 3.6741 (13) Å.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705845X/bt2607sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680705845X/bt2607Isup2.hkl
Contains datablock I

CCDC reference: 672699

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](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

Comment top

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 CgCgi separation of 3.6741 (13) Å (i = 1 - x, 1 - y, -z).

Related literature top

For related literature, see: Weber et al. (1993); Yilmaz et al. (2004); Liu et al. (2006); Baran & Yilmaz (2006).

Experimental top

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.

Refinement top

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).

Computing details top

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).

Figures top
[Figure 1] 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.
(2,2'-Bipyridine)saccharinatosilver(I) top
Crystal data top
[Ag(C7H4NO3S)(C10H8N2)]F(000) = 888
Mr = 446.23Dx = 1.831 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3928 reflections
a = 10.7803 (2) Åθ = 2.9–27.5°
b = 9.7683 (1) ŵ = 1.40 mm1
c = 15.6176 (2) ÅT = 120 K
β = 100.1975 (8)°Needle, colourless
V = 1618.64 (4) Å30.40 × 0.04 × 0.02 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
3713 independent reflections
Radiation source: fine-focus sealed tube3194 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω and ϕ scansθmax = 27.5°, θmin = 3.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
h = 1413
Tmin = 0.605, Tmax = 0.973k = 1212
25291 measured reflectionsl = 2020
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)] = 0.025H-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 reflectionsΔρmax = 0.43 e Å3
227 parametersΔρmin = 0.46 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00128 (18)
Crystal data top
[Ag(C7H4NO3S)(C10H8N2)]V = 1618.64 (4) Å3
Mr = 446.23Z = 4
Monoclinic, P21/nMo Kα radiation
a = 10.7803 (2) ŵ = 1.40 mm1
b = 9.7683 (1) ÅT = 120 K
c = 15.6176 (2) Å0.40 × 0.04 × 0.02 mm
β = 100.1975 (8)°
Data collection top
Nonius KappaCCD
diffractometer
3713 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)
3194 reflections with I > 2σ(I)
Tmin = 0.605, Tmax = 0.973Rint = 0.038
25291 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.056H-atom parameters constrained
S = 1.08Δρmax = 0.43 e Å3
3713 reflectionsΔρmin = 0.46 e Å3
227 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.501633 (17)0.793746 (18)0.021427 (11)0.02327 (7)
C10.4298 (2)1.0121 (2)0.15235 (13)0.0158 (4)
C20.33090 (19)1.1138 (2)0.16617 (13)0.0145 (4)
C30.3360 (2)1.2084 (2)0.23278 (14)0.0185 (4)
H30.40931.21690.27630.022*
C40.2318 (2)1.2901 (2)0.23427 (14)0.0229 (5)
H40.23391.35610.27920.028*
C50.1232 (2)1.2772 (2)0.17078 (15)0.0221 (5)
H50.05261.33410.17350.026*
C60.1172 (2)1.1826 (2)0.10380 (14)0.0190 (5)
H60.04391.17290.06050.023*
C70.2232 (2)1.1032 (2)0.10334 (13)0.0144 (4)
N10.39147 (17)0.93554 (19)0.07890 (11)0.0182 (4)
O10.53026 (15)0.99921 (17)0.20193 (10)0.0240 (4)
O20.16452 (15)0.85874 (16)0.03892 (11)0.0271 (4)
O30.24637 (18)1.02164 (18)0.05562 (10)0.0295 (4)
S10.24856 (5)0.97131 (6)0.03116 (3)0.01733 (12)
C80.7656 (2)0.6447 (2)0.08002 (15)0.0244 (5)
H80.77340.71130.12500.029*
C90.8607 (2)0.5498 (2)0.08214 (15)0.0237 (5)
H90.93240.55090.12730.028*
C100.8489 (2)0.4530 (2)0.01676 (15)0.0224 (5)
H100.91240.38570.01650.027*
C110.7438 (2)0.4551 (2)0.04827 (14)0.0182 (5)
H110.73450.38940.09380.022*
C120.6517 (2)0.5545 (2)0.04641 (13)0.0147 (4)
C130.5363 (2)0.5625 (2)0.11505 (13)0.0158 (4)
C140.5170 (2)0.4753 (3)0.18644 (15)0.0248 (5)
H140.57740.40700.19270.030*
C150.4087 (2)0.4890 (3)0.24846 (15)0.0283 (6)
H150.39430.43070.29790.034*
C160.3221 (2)0.5881 (3)0.23762 (15)0.0268 (5)
H160.24640.59860.27870.032*
C170.3481 (2)0.6718 (3)0.16543 (16)0.0265 (5)
H170.28880.74080.15810.032*
N20.66271 (17)0.64772 (19)0.01771 (11)0.0184 (4)
N30.45297 (17)0.6604 (2)0.10520 (12)0.0197 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.02769 (11)0.01844 (10)0.02661 (11)0.00675 (7)0.01280 (7)0.00129 (7)
C10.0157 (11)0.0180 (11)0.0142 (10)0.0019 (9)0.0041 (8)0.0016 (8)
C20.0166 (10)0.0129 (10)0.0144 (10)0.0002 (8)0.0039 (8)0.0027 (8)
C30.0216 (11)0.0183 (11)0.0149 (10)0.0024 (9)0.0016 (9)0.0011 (9)
C40.0347 (13)0.0165 (11)0.0189 (11)0.0021 (10)0.0082 (10)0.0039 (9)
C50.0256 (12)0.0180 (12)0.0240 (11)0.0085 (10)0.0084 (10)0.0026 (9)
C60.0180 (11)0.0178 (11)0.0204 (11)0.0027 (9)0.0017 (9)0.0025 (9)
C70.0183 (11)0.0116 (10)0.0135 (10)0.0004 (8)0.0034 (8)0.0004 (8)
N10.0172 (9)0.0196 (10)0.0173 (9)0.0048 (8)0.0018 (7)0.0030 (7)
O10.0152 (8)0.0314 (10)0.0235 (8)0.0034 (7)0.0015 (7)0.0012 (7)
O20.0234 (9)0.0167 (8)0.0379 (10)0.0006 (7)0.0040 (7)0.0056 (7)
O30.0416 (11)0.0304 (10)0.0147 (8)0.0090 (8)0.0002 (7)0.0023 (7)
S10.0194 (3)0.0152 (3)0.0157 (2)0.0030 (2)0.0016 (2)0.0033 (2)
C80.0290 (13)0.0225 (12)0.0195 (11)0.0017 (10)0.0014 (10)0.0054 (9)
C90.0233 (12)0.0214 (12)0.0230 (12)0.0017 (10)0.0057 (9)0.0012 (10)
C100.0201 (12)0.0173 (11)0.0289 (12)0.0058 (9)0.0020 (10)0.0021 (9)
C110.0202 (11)0.0151 (11)0.0195 (11)0.0004 (9)0.0037 (9)0.0024 (9)
C120.0158 (11)0.0138 (10)0.0152 (10)0.0015 (9)0.0042 (8)0.0014 (8)
C130.0167 (11)0.0150 (10)0.0163 (10)0.0027 (9)0.0044 (8)0.0019 (8)
C140.0239 (12)0.0254 (13)0.0238 (12)0.0005 (10)0.0004 (10)0.0054 (10)
C150.0291 (14)0.0314 (14)0.0221 (12)0.0062 (11)0.0020 (10)0.0048 (10)
C160.0186 (12)0.0366 (15)0.0228 (12)0.0070 (11)0.0028 (9)0.0063 (10)
C170.0181 (12)0.0334 (14)0.0274 (12)0.0049 (10)0.0023 (10)0.0046 (11)
N20.0204 (10)0.0164 (9)0.0177 (9)0.0035 (8)0.0017 (8)0.0021 (7)
N30.0166 (9)0.0236 (10)0.0184 (9)0.0030 (8)0.0018 (7)0.0000 (8)
Geometric parameters (Å, º) top
C1—O11.221 (3)C9—H90.9500
C1—N11.370 (3)C10—C111.381 (3)
C1—C21.500 (3)C10—H100.9500
C2—C71.385 (3)C11—C121.393 (3)
C2—C31.385 (3)C11—H110.9500
C3—C41.382 (3)C12—N21.343 (3)
C3—H30.9500C12—C131.493 (3)
C4—C51.399 (3)C13—N31.339 (3)
C4—H40.9500C13—C141.389 (3)
C5—C61.389 (3)C14—C151.385 (3)
C5—H50.9500C14—H140.9500
C6—C71.383 (3)C15—C161.375 (4)
C6—H60.9500C15—H150.9500
C7—S11.764 (2)C16—C171.381 (3)
N1—S11.6262 (18)C16—H160.9500
O2—S11.4434 (17)C17—N31.341 (3)
O3—S11.4379 (17)C17—H170.9500
C8—N21.340 (3)Ag1—N12.1241 (18)
C8—C91.378 (3)Ag1—N22.2559 (18)
C8—H80.9500Ag1—N32.3488 (18)
C9—C101.381 (3)
O1—C1—N1125.2 (2)C10—C9—H9120.9
O1—C1—C2123.36 (19)C9—C10—C11119.3 (2)
N1—C1—C2111.43 (18)C9—C10—H10120.3
C7—C2—C3119.95 (19)C11—C10—H10120.3
C7—C2—C1112.09 (18)C10—C11—C12119.3 (2)
C3—C2—C1127.95 (19)C10—C11—H11120.3
C4—C3—C2118.3 (2)C12—C11—H11120.3
C4—C3—H3120.9N2—C12—C11121.25 (19)
C2—C3—H3120.9N2—C12—C13116.89 (18)
C3—C4—C5121.1 (2)C11—C12—C13121.86 (19)
C3—C4—H4119.4N3—C13—C14121.4 (2)
C5—C4—H4119.4N3—C13—C12116.45 (18)
C6—C5—C4121.0 (2)C14—C13—C12122.1 (2)
C6—C5—H5119.5C15—C14—C13119.4 (2)
C4—C5—H5119.5C15—C14—H14120.3
C7—C6—C5116.7 (2)C13—C14—H14120.3
C7—C6—H6121.7C16—C15—C14119.2 (2)
C5—C6—H6121.7C16—C15—H15120.4
C6—C7—C2122.98 (19)C14—C15—H15120.4
C6—C7—S1129.37 (16)C15—C16—C17118.2 (2)
C2—C7—S1107.61 (15)C15—C16—H16120.9
C1—N1—S1112.78 (15)C17—C16—H16120.9
C1—N1—Ag1126.97 (14)N3—C17—C16123.2 (2)
S1—N1—Ag1120.10 (10)N3—C17—H17118.4
O3—S1—O2115.70 (11)C16—C17—H17118.4
O3—S1—N1111.21 (10)C8—N2—C12118.60 (19)
O2—S1—N1110.83 (10)C8—N2—Ag1122.51 (15)
O3—S1—C7111.97 (10)C12—N2—Ag1118.75 (14)
O2—S1—C7109.39 (10)C13—N3—C17118.6 (2)
N1—S1—C796.03 (10)C13—N3—Ag1115.99 (14)
N2—C8—C9123.3 (2)C17—N3—Ag1125.41 (16)
N2—C8—H8118.3N1—Ag1—N2156.02 (7)
C9—C8—H8118.3N1—Ag1—N3131.25 (7)
C8—C9—C10118.2 (2)N2—Ag1—N371.69 (6)
C8—C9—H9120.9
O1—C1—C2—C7176.8 (2)N2—C8—C9—C100.1 (4)
N1—C1—C2—C72.0 (3)C8—C9—C10—C110.5 (4)
O1—C1—C2—C31.4 (4)C9—C10—C11—C120.2 (3)
N1—C1—C2—C3179.7 (2)C10—C11—C12—N20.5 (3)
C7—C2—C3—C40.0 (3)C10—C11—C12—C13179.7 (2)
C1—C2—C3—C4178.1 (2)N2—C12—C13—N31.4 (3)
C2—C3—C4—C50.6 (3)C11—C12—C13—N3178.4 (2)
C3—C4—C5—C60.5 (3)N2—C12—C13—C14177.3 (2)
C4—C5—C6—C70.2 (3)C11—C12—C13—C142.9 (3)
C5—C6—C7—C20.8 (3)N3—C13—C14—C150.6 (4)
C5—C6—C7—S1178.26 (17)C12—C13—C14—C15179.2 (2)
C3—C2—C7—C60.7 (3)C13—C14—C15—C160.5 (4)
C1—C2—C7—C6177.67 (19)C14—C15—C16—C171.0 (4)
C3—C2—C7—S1178.69 (17)C15—C16—C17—N30.6 (4)
C1—C2—C7—S10.3 (2)C9—C8—N2—C120.5 (4)
O1—C1—N1—S1175.89 (18)C9—C8—N2—Ag1175.15 (18)
C2—C1—N1—S12.9 (2)C11—C12—N2—C80.8 (3)
O1—C1—N1—Ag18.7 (3)C13—C12—N2—C8179.33 (19)
C2—C1—N1—Ag1172.54 (14)C11—C12—N2—Ag1175.03 (16)
N2—Ag1—N1—C121.5 (3)C13—C12—N2—Ag14.8 (2)
N3—Ag1—N1—C1177.96 (16)N1—Ag1—N2—C815.4 (3)
N2—Ag1—N1—S1163.35 (13)N3—Ag1—N2—C8179.9 (2)
N3—Ag1—N1—S12.81 (17)N1—Ag1—N2—C12160.26 (17)
C1—N1—S1—O3118.83 (16)N3—Ag1—N2—C124.44 (15)
Ag1—N1—S1—O356.97 (14)C14—C13—N3—C171.0 (3)
C1—N1—S1—O2110.97 (16)C12—C13—N3—C17179.76 (19)
Ag1—N1—S1—O273.23 (14)C14—C13—N3—Ag1178.83 (17)
C1—N1—S1—C72.44 (17)C12—C13—N3—Ag12.5 (2)
Ag1—N1—S1—C7173.36 (11)C16—C17—N3—C130.5 (4)
C6—C7—S1—O365.3 (2)C16—C17—N3—Ag1178.04 (18)
C2—C7—S1—O3116.97 (16)N1—Ag1—N3—C13168.24 (14)
C6—C7—S1—O264.4 (2)N2—Ag1—N3—C133.56 (15)
C2—C7—S1—O2113.41 (15)N1—Ag1—N3—C179.4 (2)
C6—C7—S1—N1179.0 (2)N2—Ag1—N3—C17178.8 (2)
C2—C7—S1—N11.19 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.952.513.458 (3)173
C16—H16···O1ii0.952.493.235 (3)136
Symmetry codes: (i) x, y+2, z; (ii) x1/2, y+3/2, z1/2.

Experimental details

Crystal data
Chemical formula[Ag(C7H4NO3S)(C10H8N2)]
Mr446.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)10.7803 (2), 9.7683 (1), 15.6176 (2)
β (°) 100.1975 (8)
V3)1618.64 (4)
Z4
Radiation typeMo Kα
µ (mm1)1.40
Crystal size (mm)0.40 × 0.04 × 0.02
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2003)
Tmin, Tmax0.605, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
25291, 3713, 3194
Rint0.038
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.056, 1.08
No. of reflections3713
No. of parameters227
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.43, 0.46

Computer programs: COLLECT (Enraf–Nonius, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997).

Selected geometric parameters (Å, º) top
Ag1—N12.1241 (18)Ag1—N32.3488 (18)
Ag1—N22.2559 (18)
N1—Ag1—N2156.02 (7)N2—Ag1—N371.69 (6)
N1—Ag1—N3131.25 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O2i0.952.513.458 (3)173
C16—H16···O1ii0.952.493.235 (3)136
Symmetry codes: (i) x, y+2, z; (ii) x1/2, y+3/2, z1/2.
 

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