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Silver(I) complexes with sulfur-donor ligands have a broad range of pharma­cological applications. One of the most important factors for tuning the biological activity is the type of donor atom and the ease of ligand replacement. Silver thio­saccharinates display a wide range of structures from mono- to polynuclear complexes. We report the synthesis, crystal structure and vibrational spectroscopic analysis of a two-dimensional AgI–thio­saccharinate coordination polymer, namely poly[tris­(μ2-4,4′-bi­pyridine-κ2N:N′)bis­(μ3-1,1-dioxo-1,2-benz­iso­thia­zole-3-thiol­ato-κ3N:S3:S3)bis­(μ2-1,1-dioxo-1,2-benziso­thia­zole-3-thiol­ato-κ2S3:S3)tetra­silver(I)], [Ag2(C7H4NO2S2)2(C10H8N2)1.5]n, with 4,4′-bi­pyridine acting as a spacer. A relevant feature of the structure is the presence of an unusually short Ag...Ag separation of 2.8859 (10) Å, well within the range of argentophilic inter­actions and confirmed as such by Raman analysis of the low-frequency spectrum. From a topological point of view, the structure presents inter­penetration in the form of a threefold entangled 2D→2D mesh (2D is two-dimensional).

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616009645/fn3217sup1.cif
Contains datablocks Global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229616009645/fn3217Isup2.hkl
Contains datablock I

CCDC reference: 1485531

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008) and ToposPro (Blatov et al. (2014); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and PLATON (Spek, 2009).

Bis(µ3-1,1-dioxo-1,2-benzisothiazole-3-thiolato-κ3N:S3:S3)bis(µ2-1,1-dioxo-1,2-benzisothiazole-3-thiolato-κ2S3:S3)tetrasilver(I)] top
Crystal data top
[Ag2(C7H4NO2S2)2(C10H8N2)1.5]F(000) = 1676
Mr = 846.48Dx = 1.869 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 15.3542 (4) ÅCell parameters from 19239 reflections
b = 7.9565 (2) Åθ = 3.7–28.8°
c = 24.8986 (6) ŵ = 1.63 mm1
β = 98.477 (2)°T = 294 K
V = 3008.52 (13) Å3Plate, pale_yellow
Z = 40.24 × 0.18 × 0.10 mm
Data collection top
Oxford Diffraction Gemini CCD S Ultra
diffractometer
7674 reflections with I > 2σ(I)
ω scans, thick slicesθmax = 29.3°, θmin = 3.6°
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
h = 2021
k = 1010
8912 measured reflectionsl = 3333
8912 independent reflections
Refinement top
Refinement on F2403 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.171 w = 1/[σ2(Fo2) + (0.0545P)2 + 36.2817P]
where P = (Fo2 + 2Fc2)/3
S = 1.17(Δ/σ)max = 0.001
8912 reflectionsΔρmax = 1.05 e Å3
398 parametersΔρmin = 1.29 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refined as a 2-component twin

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Ag10.77241 (5)0.43764 (9)0.04029 (3)0.02539 (16)
Ag20.60461 (5)0.43249 (10)0.02934 (3)0.03308 (19)
S1A0.71399 (14)0.6533 (3)0.15914 (8)0.0199 (4)
S2A0.57103 (15)0.7075 (3)0.00667 (9)0.0227 (4)
N1A0.6780 (5)0.6002 (9)0.0956 (3)0.0219 (8)
O1A0.8078 (4)0.6691 (9)0.1679 (3)0.0303 (14)
O2A0.6766 (4)0.5412 (8)0.1947 (2)0.0276 (13)
C1A0.6659 (5)0.8530 (10)0.1558 (3)0.0155 (12)
C2A0.6708 (6)0.9772 (12)0.1946 (4)0.0287 (16)
H2A0.69870.95860.22980.034*
C3A0.6323 (7)1.1321 (14)0.1792 (4)0.0340 (17)
H3A0.63431.21900.20440.041*
C4A0.5917 (7)1.1558 (14)0.1271 (4)0.0374 (19)
H4A0.56851.26120.11720.045*
C5A0.5835 (6)1.0279 (10)0.0878 (4)0.0237 (15)
H5A0.55441.04570.05280.028*
C6A0.6208 (5)0.8742 (10)0.1037 (3)0.0137 (12)
C7A0.6276 (6)0.7184 (10)0.0710 (3)0.0160 (12)
S1B0.82646 (19)0.2697 (3)0.14337 (11)0.0331 (5)
S2B0.70851 (15)0.1810 (3)0.00764 (9)0.0246 (3)
N1B0.7919 (5)0.3130 (9)0.0849 (3)0.0267 (13)
O1B0.7743 (6)0.3588 (9)0.1864 (3)0.0452 (17)
O2B0.9194 (6)0.2911 (10)0.1374 (4)0.054 (2)
C1B0.7973 (6)0.0520 (11)0.1444 (4)0.0236 (14)
C2B0.8052 (7)0.0666 (13)0.1822 (4)0.0330 (18)
H2B0.82730.04150.21410.040*
C3B0.7786 (8)0.2282 (14)0.1709 (5)0.044 (2)
H3B0.78370.31440.19550.053*
C4B0.7447 (7)0.2623 (13)0.1239 (4)0.0319 (17)
H4B0.72990.37220.11630.038*
C5B0.7324 (6)0.1354 (10)0.0876 (4)0.0234 (15)
H5B0.70560.15720.05710.028*
C6B0.7610 (5)0.0242 (10)0.0979 (3)0.0150 (11)
C7B0.7587 (6)0.1815 (10)0.0654 (3)0.0193 (12)
N1C0.8708 (5)0.3277 (10)0.1144 (3)0.0250 (13)
N2C1.0747 (5)0.1100 (11)0.3764 (3)0.0290 (15)
C1C0.8476 (6)0.1934 (13)0.1409 (4)0.0285 (16)
H1C0.79790.13330.12600.034*
C2C0.8943 (6)0.1394 (13)0.1897 (4)0.0273 (16)
H2C0.87750.04290.20660.033*
C3C0.9665 (6)0.2319 (12)0.2128 (4)0.0258 (15)
C4C0.9909 (6)0.3704 (12)0.1859 (4)0.0245 (15)
H4C1.03920.43490.20040.029*
C5C0.9414 (6)0.4112 (13)0.1366 (4)0.0278 (16)
H5C0.95890.50340.11780.033*
C6C1.0531 (6)0.0117 (14)0.3392 (4)0.0292 (17)
H6C1.06030.12320.35020.035*
C7C1.0211 (6)0.0213 (14)0.2860 (4)0.0305 (17)
H7C1.00610.06610.26160.037*
C8C1.0115 (6)0.1871 (13)0.2690 (4)0.0285 (16)
C9C1.0388 (6)0.3137 (13)0.3059 (4)0.0281 (17)
H9C1.03660.42580.29520.034*
C10C1.0697 (6)0.2687 (13)0.3594 (4)0.0274 (16)
H10C1.08760.35340.38440.033*
N1D0.8591 (6)0.6615 (10)0.0215 (3)0.0295 (13)
C1D0.8627 (9)0.8027 (14)0.0499 (5)0.052 (2)
H1D0.82710.81200.07690.062*
C2D0.9154 (9)0.9350 (14)0.0419 (6)0.056 (2)
H2D0.91321.03240.06230.067*
C3D0.9708 (5)0.9267 (9)0.0047 (4)0.0254 (15)
C4D0.9664 (10)0.7839 (17)0.0263 (6)0.074 (3)
H4D1.00180.77310.05340.088*
C5D0.9094 (9)0.6560 (17)0.0174 (6)0.061 (2)
H5D0.90610.56180.03970.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ag10.0296 (3)0.0237 (3)0.0211 (3)0.0026 (3)0.0021 (2)0.0025 (3)
Ag20.0338 (3)0.0364 (3)0.0262 (3)0.0085 (3)0.0050 (3)0.0129 (3)
S1A0.0197 (9)0.0220 (9)0.0172 (6)0.0037 (7)0.0003 (6)0.0005 (6)
S2A0.0230 (10)0.0312 (5)0.0127 (7)0.0039 (5)0.0013 (6)0.0048 (5)
N1A0.0293 (9)0.0175 (15)0.0173 (6)0.0017 (10)0.0019 (5)0.0012 (7)
O1A0.0198 (9)0.038 (4)0.032 (3)0.0022 (8)0.0001 (7)0.003 (3)
O2A0.035 (3)0.026 (2)0.0222 (19)0.001 (2)0.006 (2)0.0004 (18)
C1A0.012 (3)0.0204 (10)0.0124 (13)0.0003 (13)0.0025 (14)0.0016 (7)
C2A0.027 (4)0.0326 (17)0.0261 (17)0.005 (2)0.004 (2)0.0145 (15)
C3A0.026 (4)0.0349 (19)0.044 (3)0.004 (2)0.012 (2)0.0069 (17)
C4A0.036 (5)0.033 (2)0.044 (2)0.001 (3)0.009 (2)0.0090 (19)
C5A0.025 (4)0.0186 (14)0.028 (2)0.0043 (16)0.005 (2)0.0062 (12)
C6A0.013 (3)0.0137 (14)0.0127 (12)0.0027 (12)0.0033 (13)0.0014 (8)
C7A0.022 (2)0.0131 (15)0.0121 (8)0.0031 (12)0.0005 (12)0.0006 (7)
S1B0.0460 (14)0.0188 (9)0.0377 (11)0.0079 (9)0.0167 (10)0.0039 (7)
S2B0.0234 (5)0.0284 (4)0.0224 (6)0.0001 (3)0.0050 (4)0.0062 (3)
N1B0.030 (3)0.0187 (15)0.0322 (14)0.0003 (15)0.0071 (17)0.0000 (10)
O1B0.066 (4)0.031 (3)0.040 (2)0.006 (3)0.013 (2)0.004 (2)
O2B0.0464 (14)0.038 (4)0.081 (6)0.0102 (10)0.0187 (11)0.004 (4)
C1B0.031 (3)0.0179 (10)0.0252 (18)0.0040 (12)0.016 (2)0.0041 (8)
C2B0.041 (5)0.0277 (16)0.033 (2)0.001 (2)0.014 (3)0.0123 (16)
C3B0.059 (5)0.0292 (18)0.049 (3)0.003 (3)0.024 (3)0.0114 (18)
C4B0.032 (4)0.0238 (19)0.042 (3)0.003 (2)0.010 (3)0.0090 (19)
C5B0.024 (4)0.0146 (14)0.034 (3)0.0018 (16)0.013 (3)0.0010 (13)
C6B0.013 (3)0.0134 (14)0.0197 (17)0.0006 (14)0.0063 (17)0.0022 (10)
C7B0.021 (3)0.0149 (15)0.0217 (12)0.0034 (15)0.0038 (17)0.0039 (9)
N1C0.0232 (16)0.031 (2)0.0206 (14)0.0012 (15)0.0020 (13)0.0023 (15)
N2C0.022 (4)0.038 (2)0.025 (2)0.001 (2)0.004 (2)0.0119 (15)
C1C0.025 (3)0.034 (2)0.026 (2)0.000 (2)0.0010 (18)0.0061 (18)
C2C0.022 (2)0.034 (3)0.025 (2)0.001 (2)0.0019 (19)0.0066 (16)
C3C0.021 (3)0.033 (3)0.0238 (18)0.000 (2)0.0028 (17)0.0061 (15)
C4C0.020 (3)0.032 (3)0.021 (2)0.000 (2)0.0021 (14)0.0048 (19)
C5C0.026 (2)0.033 (3)0.023 (2)0.001 (2)0.0012 (17)0.0056 (18)
C6C0.020 (4)0.041 (2)0.026 (2)0.003 (2)0.001 (2)0.0096 (14)
C7C0.024 (4)0.040 (2)0.026 (2)0.004 (2)0.000 (2)0.0096 (14)
C8C0.020 (3)0.040 (2)0.0249 (18)0.0031 (19)0.0022 (18)0.0093 (13)
C9C0.022 (4)0.037 (2)0.0233 (19)0.001 (2)0.0014 (19)0.0116 (15)
C10C0.020 (4)0.038 (2)0.023 (2)0.002 (2)0.000 (2)0.0114 (16)
N1D0.034 (2)0.0230 (12)0.032 (3)0.0021 (15)0.007 (2)0.0055 (14)
C1D0.084 (5)0.0292 (17)0.053 (4)0.021 (2)0.048 (4)0.017 (2)
C2D0.083 (4)0.026 (2)0.072 (4)0.018 (3)0.055 (3)0.017 (3)
C3D0.029 (3)0.024 (3)0.023 (3)0.001 (2)0.004 (2)0.000 (2)
C4D0.088 (5)0.054 (3)0.094 (5)0.038 (3)0.064 (4)0.046 (3)
C5D0.075 (4)0.054 (4)0.063 (3)0.034 (3)0.042 (3)0.037 (3)
Geometric parameters (Å, º) top
Ag1—N1D2.312 (8)C4B—C5B1.387 (12)
Ag1—N1C2.373 (7)C4B—H4B0.9300
Ag1—S2B2.492 (2)C5B—C6B1.380 (11)
Ag1—N1A2.502 (8)C5B—H5B0.9300
Ag1—Ag22.8859 (10)C6B—C7B1.493 (11)
Ag2—N2Ci2.349 (8)N1C—C5C1.320 (12)
Ag2—S2A2.448 (2)N1C—C1C1.332 (12)
Ag2—S2B2.566 (2)N2C—C10C1.330 (12)
S1A—O1A1.430 (7)N2C—C6C1.346 (13)
S1A—O2A1.434 (6)C1C—C2C1.385 (12)
S1A—N1A1.652 (7)C1C—H1C0.9300
S1A—C1A1.749 (8)C2C—C3C1.383 (13)
S2A—C7A1.708 (8)C2C—H2C0.9300
N1A—C7A1.311 (10)C3C—C4C1.371 (12)
C1A—C2A1.376 (11)C3C—C8C1.508 (10)
C1A—C6A1.389 (10)C4C—C5C1.385 (12)
C2A—C3A1.395 (14)C4C—H4C0.9300
C2A—H2A0.9300C5C—H5C0.9300
C3A—C4A1.368 (15)C6C—C7C1.370 (13)
C3A—H3A0.9300C6C—H6C0.9300
C4A—C5A1.405 (13)C7C—C8C1.386 (14)
C4A—H4A0.9300C7C—H7C0.9300
C5A—C6A1.383 (11)C8C—C9C1.387 (14)
C5A—H5A0.9300C9C—C10C1.394 (12)
C6A—C7A1.494 (11)C9C—H9C0.9300
S1B—O2B1.423 (9)C10C—H10C0.9300
S1B—O1B1.427 (8)N1D—C1D1.324 (12)
S1B—N1B1.659 (8)N1D—C5D1.325 (14)
S1B—C1B1.788 (9)C1D—C2D1.361 (15)
S2B—C7B1.730 (9)C1D—H1D0.9300
N1B—C7B1.289 (11)C2D—C3D1.347 (13)
C1B—C2B1.351 (12)C2D—H2D0.9300
C1B—C6B1.375 (11)C3D—C4D1.370 (14)
C2B—C3B1.391 (15)C3D—C3Dii1.510 (11)
C2B—H2B0.9300C4D—C5D1.382 (16)
C3B—C4B1.376 (15)C4D—H4D0.9300
C3B—H3B0.9300C5D—H5D0.9300
Ag2···S2Aiii3.046 (2)
N1D—Ag1—N1C97.0 (3)C2B—C3B—H3B119.5
N1D—Ag1—S2B137.1 (2)C3B—C4B—C5B121.1 (10)
N1C—Ag1—S2B103.3 (2)C3B—C4B—H4B119.4
N1D—Ag1—N1A96.3 (3)C5B—C4B—H4B119.4
N1C—Ag1—N1A96.7 (2)C6B—C5B—C4B118.0 (8)
S2B—Ag1—N1A117.91 (18)C6B—C5B—H5B121.0
N1D—Ag1—Ag2112.3 (2)C4B—C5B—H5B121.0
N1C—Ag1—Ag2150.65 (19)C1B—C6B—C5B119.0 (8)
S2B—Ag1—Ag256.43 (6)C1B—C6B—C7B111.5 (7)
N1A—Ag1—Ag278.43 (17)C5B—C6B—C7B129.5 (7)
N2Ci—Ag2—S2A118.3 (2)N1B—C7B—C6B115.8 (7)
N2Ci—Ag2—S2B97.0 (2)N1B—C7B—S2B124.3 (7)
S2A—Ag2—S2B141.04 (8)C6B—C7B—S2B119.9 (6)
N2Ci—Ag2—Ag1128.9 (2)C5C—N1C—C1C117.4 (8)
S2A—Ag2—Ag189.13 (6)C5C—N1C—Ag1121.9 (6)
S2B—Ag2—Ag154.01 (5)C1C—N1C—Ag1119.7 (6)
O1A—S1A—O2A116.5 (4)C10C—N2C—C6C118.0 (8)
O1A—S1A—N1A110.8 (4)N1C—C1C—C2C122.8 (9)
O2A—S1A—N1A109.0 (4)N1C—C1C—H1C118.6
O1A—S1A—C1A109.6 (4)C2C—C1C—H1C118.6
O2A—S1A—C1A112.9 (4)C3C—C2C—C1C118.7 (9)
N1A—S1A—C1A96.2 (4)C3C—C2C—H2C120.7
C7A—S2A—Ag2106.5 (3)C1C—C2C—H2C120.7
C7A—N1A—S1A110.8 (6)C4C—C3C—C2C119.0 (8)
C7A—N1A—Ag1117.7 (5)C4C—C3C—C8C121.5 (8)
S1A—N1A—Ag1121.3 (4)C2C—C3C—C8C119.4 (8)
C2A—C1A—C6A122.4 (8)C3C—C4C—C5C117.9 (9)
C2A—C1A—S1A129.9 (7)C3C—C4C—H4C121.0
C6A—C1A—S1A107.7 (6)C5C—C4C—H4C121.0
C1A—C2A—C3A117.8 (9)N1C—C5C—C4C124.2 (9)
C1A—C2A—H2A121.1N1C—C5C—H5C117.9
C3A—C2A—H2A121.1C4C—C5C—H5C117.9
C4A—C3A—C2A119.8 (10)N2C—C6C—C7C122.9 (10)
C4A—C3A—H3A120.1N2C—C6C—H6C118.5
C2A—C3A—H3A120.1C7C—C6C—H6C118.5
C3A—C4A—C5A122.9 (10)C6C—C7C—C8C119.0 (10)
C3A—C4A—H4A118.5C6C—C7C—H7C120.5
C5A—C4A—H4A118.5C8C—C7C—H7C120.5
C6A—C5A—C4A116.8 (9)C7C—C8C—C9C118.7 (8)
C6A—C5A—H5A121.6C7C—C8C—C3C121.4 (9)
C4A—C5A—H5A121.6C9C—C8C—C3C119.7 (9)
C5A—C6A—C1A120.2 (8)C8C—C9C—C10C118.3 (9)
C5A—C6A—C7A129.6 (7)C8C—C9C—H9C120.8
C1A—C6A—C7A110.0 (7)C10C—C9C—H9C120.8
N1A—C7A—C6A115.2 (7)N2C—C10C—C9C122.8 (10)
N1A—C7A—S2A125.8 (6)N2C—C10C—H10C118.6
C6A—C7A—S2A119.1 (6)C9C—C10C—H10C118.6
O2B—S1B—O1B117.5 (5)C1D—N1D—C5D115.8 (9)
O2B—S1B—N1B109.3 (5)C1D—N1D—Ag1121.7 (7)
O1B—S1B—N1B109.8 (5)C5D—N1D—Ag1122.5 (7)
O2B—S1B—C1B111.2 (5)N1D—C1D—C2D123.8 (10)
O1B—S1B—C1B111.0 (5)N1D—C1D—H1D118.1
N1B—S1B—C1B95.9 (4)C2D—C1D—H1D118.1
C7B—S2B—Ag1101.8 (3)C3D—C2D—C1D120.9 (10)
C7B—S2B—Ag299.4 (3)C3D—C2D—H2D119.6
Ag1—S2B—Ag269.56 (7)C1D—C2D—H2D119.6
C7B—N1B—S1B110.9 (6)C2D—C3D—C4D116.4 (8)
C2B—C1B—C6B124.3 (9)C2D—C3D—C3Dii121.2 (10)
C2B—C1B—S1B129.7 (7)C4D—C3D—C3Dii122.2 (11)
C6B—C1B—S1B106.0 (6)C3D—C4D—C5D120.0 (11)
C1B—C2B—C3B116.4 (10)C3D—C4D—H4D120.0
C1B—C2B—H2B121.8C5D—C4D—H4D120.0
C3B—C2B—H2B121.8N1D—C5D—C4D123.0 (11)
C4B—C3B—C2B120.9 (10)N1D—C5D—H5D118.5
C4B—C3B—H3B119.5C4D—C5D—H5D118.5
Symmetry codes: (i) x1/2, y+1/2, z1/2; (ii) x+2, y+2, z; (iii) x+1, y+1, z.
DX···A interactions in (I) (Å, °) top
DX···ADXX···AD···ADX···AType
C1D—H1D···O1A0.932.593.345 (13)139I
C1D—H1D···Cg10.932.933.759 (14)150I
S1B—O1B···Cg3iii1.427 (8)3.564 (10)4.332 (5)113.3 (4)I
C5C—H5C···O2Biv0.932.483.189 (13)134II
C1C—H1C···Cg4v0.932.893.704 (10)147II
C2A—H2A···O2Avi0.932.563.383 (11)147III
S1A—O2A···Cg3vi1.434 (6)3.469 (7)4.065 (4)104.2 (3)III
Symmetry codes: (iii) x-1/2, -y+1/2, z-1/2; (iv) -x+2, -y+1, -z; (v) x, y-1, z; (vi) -x+3/2, y+1/2, -z+1/2; (vii) -x+3/2, y-1/2, -z+1/2.

Ring codes: Cg1 is the centroid of the S1A/N1A/C7A/C6A/C1A ring, Cg2 is the centroid of the N1D/C1D–C5D ring, Cg3 is the centroid of the N2C/C6C–C10C ring, Cg4 is the centroid of the C1A–C6A ring and Cg5 is the centroid of the C1B–C6B ring.
ππ contacts for (I) top
Group1···Group2ccd (Å)da (°)mipd (Å)Type
Cg5···Cg2v4.068 (7)19.8 (6)3.5 (2)II
Cg3···Cg4vii4.061 (6)16.4 (4)3.3 (3)III
Symmetry codes: (v) x, y-1, z; (vii) -x+3/2, y-1/2, -z+1/2.

For Ring codes, see Table 3.

Notes: ccd is the centre-to-centre distance (distance between ring centroids); da is the dihedral angle; ipd is the (mean) interplanar distance (distance from one plane to the neighbouring centroid). For details, see Janiak (2000).
 

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