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 Ag
I–thiosaccharinate coordination polymer, namely poly[tris(μ
2-4,4′-bipyridine-κ
2N:
N′)bis(μ
3-1,1-dioxo-1,2-benzisothiazole-3-thiolato-κ
3N:
S3:
S3)bis(μ
2-1,1-dioxo-1,2-benzisothiazole-3-thiolato-κ
2S3:
S3)tetrasilver(I)], [Ag
2(C
7H
4NO
2S
2)
2(C
10H
8N
2)
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
CCDC reference: 1485531
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(µ
3-1,1-dioxo-1,2-benzisothiazole-3-thiolato-
κ3N:
S3:
S3)bis(µ
2-1,1-dioxo-1,2-benzisothiazole-3-thiolato-
κ2S3:
S3)tetrasilver(I)]
top
Crystal data top
[Ag2(C7H4NO2S2)2(C10H8N2)1.5] | F(000) = 1676 |
Mr = 846.48 | Dx = 1.869 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 15.3542 (4) Å | Cell parameters from 19239 reflections |
b = 7.9565 (2) Å | θ = 3.7–28.8° |
c = 24.8986 (6) Å | µ = 1.63 mm−1 |
β = 98.477 (2)° | T = 294 K |
V = 3008.52 (13) Å3 | Plate, pale_yellow |
Z = 4 | 0.24 × 0.18 × 0.10 mm |
Data collection top
Oxford Diffraction Gemini CCD S Ultra diffractometer | 7674 reflections with I > 2σ(I) |
ω scans, thick slices | θmax = 29.3°, θmin = 3.6° |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | h = −20→21 |
| k = −10→10 |
8912 measured reflections | l = −33→33 |
8912 independent reflections | |
Refinement top
Refinement on F2 | 403 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.066 | H-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 reflections | Δρmax = 1.05 e Å−3 |
398 parameters | Δρmin = −1.29 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
Ag1 | 0.77241 (5) | 0.43764 (9) | 0.04029 (3) | 0.02539 (16) | |
Ag2 | 0.60461 (5) | 0.43249 (10) | −0.02934 (3) | 0.03308 (19) | |
S1A | 0.71399 (14) | 0.6533 (3) | 0.15914 (8) | 0.0199 (4) | |
S2A | 0.57103 (15) | 0.7075 (3) | 0.00667 (9) | 0.0227 (4) | |
N1A | 0.6780 (5) | 0.6002 (9) | 0.0956 (3) | 0.0219 (8) | |
O1A | 0.8078 (4) | 0.6691 (9) | 0.1679 (3) | 0.0303 (14) | |
O2A | 0.6766 (4) | 0.5412 (8) | 0.1947 (2) | 0.0276 (13) | |
C1A | 0.6659 (5) | 0.8530 (10) | 0.1558 (3) | 0.0155 (12) | |
C2A | 0.6708 (6) | 0.9772 (12) | 0.1946 (4) | 0.0287 (16) | |
H2A | 0.6987 | 0.9586 | 0.2298 | 0.034* | |
C3A | 0.6323 (7) | 1.1321 (14) | 0.1792 (4) | 0.0340 (17) | |
H3A | 0.6343 | 1.2190 | 0.2044 | 0.041* | |
C4A | 0.5917 (7) | 1.1558 (14) | 0.1271 (4) | 0.0374 (19) | |
H4A | 0.5685 | 1.2612 | 0.1172 | 0.045* | |
C5A | 0.5835 (6) | 1.0279 (10) | 0.0878 (4) | 0.0237 (15) | |
H5A | 0.5544 | 1.0457 | 0.0528 | 0.028* | |
C6A | 0.6208 (5) | 0.8742 (10) | 0.1037 (3) | 0.0137 (12) | |
C7A | 0.6276 (6) | 0.7184 (10) | 0.0710 (3) | 0.0160 (12) | |
S1B | 0.82646 (19) | 0.2697 (3) | −0.14337 (11) | 0.0331 (5) | |
S2B | 0.70851 (15) | 0.1810 (3) | −0.00764 (9) | 0.0246 (3) | |
N1B | 0.7919 (5) | 0.3130 (9) | −0.0849 (3) | 0.0267 (13) | |
O1B | 0.7743 (6) | 0.3588 (9) | −0.1864 (3) | 0.0452 (17) | |
O2B | 0.9194 (6) | 0.2911 (10) | −0.1374 (4) | 0.054 (2) | |
C1B | 0.7973 (6) | 0.0520 (11) | −0.1444 (4) | 0.0236 (14) | |
C2B | 0.8052 (7) | −0.0666 (13) | −0.1822 (4) | 0.0330 (18) | |
H2B | 0.8273 | −0.0415 | −0.2141 | 0.040* | |
C3B | 0.7786 (8) | −0.2282 (14) | −0.1709 (5) | 0.044 (2) | |
H3B | 0.7837 | −0.3144 | −0.1955 | 0.053* | |
C4B | 0.7447 (7) | −0.2623 (13) | −0.1239 (4) | 0.0319 (17) | |
H4B | 0.7299 | −0.3722 | −0.1163 | 0.038* | |
C5B | 0.7324 (6) | −0.1354 (10) | −0.0876 (4) | 0.0234 (15) | |
H5B | 0.7056 | −0.1572 | −0.0571 | 0.028* | |
C6B | 0.7610 (5) | 0.0242 (10) | −0.0979 (3) | 0.0150 (11) | |
C7B | 0.7587 (6) | 0.1815 (10) | −0.0654 (3) | 0.0193 (12) | |
N1C | 0.8708 (5) | 0.3277 (10) | 0.1144 (3) | 0.0250 (13) | |
N2C | 1.0747 (5) | 0.1100 (11) | 0.3764 (3) | 0.0290 (15) | |
C1C | 0.8476 (6) | 0.1934 (13) | 0.1409 (4) | 0.0285 (16) | |
H1C | 0.7979 | 0.1333 | 0.1260 | 0.034* | |
C2C | 0.8943 (6) | 0.1394 (13) | 0.1897 (4) | 0.0273 (16) | |
H2C | 0.8775 | 0.0429 | 0.2066 | 0.033* | |
C3C | 0.9665 (6) | 0.2319 (12) | 0.2128 (4) | 0.0258 (15) | |
C4C | 0.9909 (6) | 0.3704 (12) | 0.1859 (4) | 0.0245 (15) | |
H4C | 1.0392 | 0.4349 | 0.2004 | 0.029* | |
C5C | 0.9414 (6) | 0.4112 (13) | 0.1366 (4) | 0.0278 (16) | |
H5C | 0.9589 | 0.5034 | 0.1178 | 0.033* | |
C6C | 1.0531 (6) | −0.0117 (14) | 0.3392 (4) | 0.0292 (17) | |
H6C | 1.0603 | −0.1232 | 0.3502 | 0.035* | |
C7C | 1.0211 (6) | 0.0213 (14) | 0.2860 (4) | 0.0305 (17) | |
H7C | 1.0061 | −0.0661 | 0.2616 | 0.037* | |
C8C | 1.0115 (6) | 0.1871 (13) | 0.2690 (4) | 0.0285 (16) | |
C9C | 1.0388 (6) | 0.3137 (13) | 0.3059 (4) | 0.0281 (17) | |
H9C | 1.0366 | 0.4258 | 0.2952 | 0.034* | |
C10C | 1.0697 (6) | 0.2687 (13) | 0.3594 (4) | 0.0274 (16) | |
H10C | 1.0876 | 0.3534 | 0.3844 | 0.033* | |
N1D | 0.8591 (6) | 0.6615 (10) | 0.0215 (3) | 0.0295 (13) | |
C1D | 0.8627 (9) | 0.8027 (14) | 0.0499 (5) | 0.052 (2) | |
H1D | 0.8271 | 0.8120 | 0.0769 | 0.062* | |
C2D | 0.9154 (9) | 0.9350 (14) | 0.0419 (6) | 0.056 (2) | |
H2D | 0.9132 | 1.0324 | 0.0623 | 0.067* | |
C3D | 0.9708 (5) | 0.9267 (9) | 0.0047 (4) | 0.0254 (15) | |
C4D | 0.9664 (10) | 0.7839 (17) | −0.0263 (6) | 0.074 (3) | |
H4D | 1.0018 | 0.7731 | −0.0534 | 0.088* | |
C5D | 0.9094 (9) | 0.6560 (17) | −0.0174 (6) | 0.061 (2) | |
H5D | 0.9061 | 0.5618 | −0.0397 | 0.073* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0296 (3) | 0.0237 (3) | 0.0211 (3) | 0.0026 (3) | −0.0021 (2) | −0.0025 (3) |
Ag2 | 0.0338 (3) | 0.0364 (3) | 0.0262 (3) | 0.0085 (3) | −0.0050 (3) | −0.0129 (3) |
S1A | 0.0197 (9) | 0.0220 (9) | 0.0172 (6) | 0.0037 (7) | −0.0003 (6) | −0.0005 (6) |
S2A | 0.0230 (10) | 0.0312 (5) | 0.0127 (7) | 0.0039 (5) | −0.0013 (6) | −0.0048 (5) |
N1A | 0.0293 (9) | 0.0175 (15) | 0.0173 (6) | 0.0017 (10) | −0.0019 (5) | 0.0012 (7) |
O1A | 0.0198 (9) | 0.038 (4) | 0.032 (3) | 0.0022 (8) | −0.0001 (7) | −0.003 (3) |
O2A | 0.035 (3) | 0.026 (2) | 0.0222 (19) | −0.001 (2) | 0.006 (2) | −0.0004 (18) |
C1A | 0.012 (3) | 0.0204 (10) | 0.0124 (13) | 0.0003 (13) | −0.0025 (14) | −0.0016 (7) |
C2A | 0.027 (4) | 0.0326 (17) | 0.0261 (17) | −0.005 (2) | 0.004 (2) | −0.0145 (15) |
C3A | 0.026 (4) | 0.0349 (19) | 0.044 (3) | −0.004 (2) | 0.012 (2) | −0.0069 (17) |
C4A | 0.036 (5) | 0.033 (2) | 0.044 (2) | 0.001 (3) | 0.009 (2) | −0.0090 (19) |
C5A | 0.025 (4) | 0.0186 (14) | 0.028 (2) | 0.0043 (16) | 0.005 (2) | 0.0062 (12) |
C6A | 0.013 (3) | 0.0137 (14) | 0.0127 (12) | −0.0027 (12) | −0.0033 (13) | −0.0014 (8) |
C7A | 0.022 (2) | 0.0131 (15) | 0.0121 (8) | −0.0031 (12) | −0.0005 (12) | −0.0006 (7) |
S1B | 0.0460 (14) | 0.0188 (9) | 0.0377 (11) | −0.0079 (9) | 0.0167 (10) | −0.0039 (7) |
S2B | 0.0234 (5) | 0.0284 (4) | 0.0224 (6) | 0.0001 (3) | 0.0050 (4) | −0.0062 (3) |
N1B | 0.030 (3) | 0.0187 (15) | 0.0322 (14) | 0.0003 (15) | 0.0071 (17) | 0.0000 (10) |
O1B | 0.066 (4) | 0.031 (3) | 0.040 (2) | 0.006 (3) | 0.013 (2) | −0.004 (2) |
O2B | 0.0464 (14) | 0.038 (4) | 0.081 (6) | −0.0102 (10) | 0.0187 (11) | −0.004 (4) |
C1B | 0.031 (3) | 0.0179 (10) | 0.0252 (18) | −0.0040 (12) | 0.016 (2) | −0.0041 (8) |
C2B | 0.041 (5) | 0.0277 (16) | 0.033 (2) | 0.001 (2) | 0.014 (3) | −0.0123 (16) |
C3B | 0.059 (5) | 0.0292 (18) | 0.049 (3) | −0.003 (3) | 0.024 (3) | −0.0114 (18) |
C4B | 0.032 (4) | 0.0238 (19) | 0.042 (3) | 0.003 (2) | 0.010 (3) | −0.0090 (19) |
C5B | 0.024 (4) | 0.0146 (14) | 0.034 (3) | −0.0018 (16) | 0.013 (3) | −0.0010 (13) |
C6B | 0.013 (3) | 0.0134 (14) | 0.0197 (17) | 0.0006 (14) | 0.0063 (17) | −0.0022 (10) |
C7B | 0.021 (3) | 0.0149 (15) | 0.0217 (12) | 0.0034 (15) | 0.0038 (17) | −0.0039 (9) |
N1C | 0.0232 (16) | 0.031 (2) | 0.0206 (14) | 0.0012 (15) | 0.0020 (13) | 0.0023 (15) |
N2C | 0.022 (4) | 0.038 (2) | 0.025 (2) | 0.001 (2) | −0.004 (2) | 0.0119 (15) |
C1C | 0.025 (3) | 0.034 (2) | 0.026 (2) | 0.000 (2) | 0.0010 (18) | 0.0061 (18) |
C2C | 0.022 (2) | 0.034 (3) | 0.025 (2) | −0.001 (2) | 0.0019 (19) | 0.0066 (16) |
C3C | 0.021 (3) | 0.033 (3) | 0.0238 (18) | 0.000 (2) | 0.0028 (17) | 0.0061 (15) |
C4C | 0.020 (3) | 0.032 (3) | 0.021 (2) | 0.000 (2) | 0.0021 (14) | 0.0048 (19) |
C5C | 0.026 (2) | 0.033 (3) | 0.023 (2) | −0.001 (2) | −0.0012 (17) | 0.0056 (18) |
C6C | 0.020 (4) | 0.041 (2) | 0.026 (2) | −0.003 (2) | 0.001 (2) | 0.0096 (14) |
C7C | 0.024 (4) | 0.040 (2) | 0.026 (2) | −0.004 (2) | 0.000 (2) | 0.0096 (14) |
C8C | 0.020 (3) | 0.040 (2) | 0.0249 (18) | −0.0031 (19) | 0.0022 (18) | 0.0093 (13) |
C9C | 0.022 (4) | 0.037 (2) | 0.0233 (19) | −0.001 (2) | −0.0014 (19) | 0.0116 (15) |
C10C | 0.020 (4) | 0.038 (2) | 0.023 (2) | 0.002 (2) | 0.000 (2) | 0.0114 (16) |
N1D | 0.034 (2) | 0.0230 (12) | 0.032 (3) | 0.0021 (15) | 0.007 (2) | −0.0055 (14) |
C1D | 0.084 (5) | 0.0292 (17) | 0.053 (4) | −0.021 (2) | 0.048 (4) | −0.017 (2) |
C2D | 0.083 (4) | 0.026 (2) | 0.072 (4) | −0.018 (3) | 0.055 (3) | −0.017 (3) |
C3D | 0.029 (3) | 0.024 (3) | 0.023 (3) | 0.001 (2) | 0.004 (2) | 0.000 (2) |
C4D | 0.088 (5) | 0.054 (3) | 0.094 (5) | −0.038 (3) | 0.064 (4) | −0.046 (3) |
C5D | 0.075 (4) | 0.054 (4) | 0.063 (3) | −0.034 (3) | 0.042 (3) | −0.037 (3) |
Geometric parameters (Å, º) top
Ag1—N1D | 2.312 (8) | C4B—C5B | 1.387 (12) |
Ag1—N1C | 2.373 (7) | C4B—H4B | 0.9300 |
Ag1—S2B | 2.492 (2) | C5B—C6B | 1.380 (11) |
Ag1—N1A | 2.502 (8) | C5B—H5B | 0.9300 |
Ag1—Ag2 | 2.8859 (10) | C6B—C7B | 1.493 (11) |
Ag2—N2Ci | 2.349 (8) | N1C—C5C | 1.320 (12) |
Ag2—S2A | 2.448 (2) | N1C—C1C | 1.332 (12) |
Ag2—S2B | 2.566 (2) | N2C—C10C | 1.330 (12) |
S1A—O1A | 1.430 (7) | N2C—C6C | 1.346 (13) |
S1A—O2A | 1.434 (6) | C1C—C2C | 1.385 (12) |
S1A—N1A | 1.652 (7) | C1C—H1C | 0.9300 |
S1A—C1A | 1.749 (8) | C2C—C3C | 1.383 (13) |
S2A—C7A | 1.708 (8) | C2C—H2C | 0.9300 |
N1A—C7A | 1.311 (10) | C3C—C4C | 1.371 (12) |
C1A—C2A | 1.376 (11) | C3C—C8C | 1.508 (10) |
C1A—C6A | 1.389 (10) | C4C—C5C | 1.385 (12) |
C2A—C3A | 1.395 (14) | C4C—H4C | 0.9300 |
C2A—H2A | 0.9300 | C5C—H5C | 0.9300 |
C3A—C4A | 1.368 (15) | C6C—C7C | 1.370 (13) |
C3A—H3A | 0.9300 | C6C—H6C | 0.9300 |
C4A—C5A | 1.405 (13) | C7C—C8C | 1.386 (14) |
C4A—H4A | 0.9300 | C7C—H7C | 0.9300 |
C5A—C6A | 1.383 (11) | C8C—C9C | 1.387 (14) |
C5A—H5A | 0.9300 | C9C—C10C | 1.394 (12) |
C6A—C7A | 1.494 (11) | C9C—H9C | 0.9300 |
S1B—O2B | 1.423 (9) | C10C—H10C | 0.9300 |
S1B—O1B | 1.427 (8) | N1D—C1D | 1.324 (12) |
S1B—N1B | 1.659 (8) | N1D—C5D | 1.325 (14) |
S1B—C1B | 1.788 (9) | C1D—C2D | 1.361 (15) |
S2B—C7B | 1.730 (9) | C1D—H1D | 0.9300 |
N1B—C7B | 1.289 (11) | C2D—C3D | 1.347 (13) |
C1B—C2B | 1.351 (12) | C2D—H2D | 0.9300 |
C1B—C6B | 1.375 (11) | C3D—C4D | 1.370 (14) |
C2B—C3B | 1.391 (15) | C3D—C3Dii | 1.510 (11) |
C2B—H2B | 0.9300 | C4D—C5D | 1.382 (16) |
C3B—C4B | 1.376 (15) | C4D—H4D | 0.9300 |
C3B—H3B | 0.9300 | C5D—H5D | 0.9300 |
| | | |
Ag2···S2Aiii | 3.046 (2) | | |
| | | |
N1D—Ag1—N1C | 97.0 (3) | C2B—C3B—H3B | 119.5 |
N1D—Ag1—S2B | 137.1 (2) | C3B—C4B—C5B | 121.1 (10) |
N1C—Ag1—S2B | 103.3 (2) | C3B—C4B—H4B | 119.4 |
N1D—Ag1—N1A | 96.3 (3) | C5B—C4B—H4B | 119.4 |
N1C—Ag1—N1A | 96.7 (2) | C6B—C5B—C4B | 118.0 (8) |
S2B—Ag1—N1A | 117.91 (18) | C6B—C5B—H5B | 121.0 |
N1D—Ag1—Ag2 | 112.3 (2) | C4B—C5B—H5B | 121.0 |
N1C—Ag1—Ag2 | 150.65 (19) | C1B—C6B—C5B | 119.0 (8) |
S2B—Ag1—Ag2 | 56.43 (6) | C1B—C6B—C7B | 111.5 (7) |
N1A—Ag1—Ag2 | 78.43 (17) | C5B—C6B—C7B | 129.5 (7) |
N2Ci—Ag2—S2A | 118.3 (2) | N1B—C7B—C6B | 115.8 (7) |
N2Ci—Ag2—S2B | 97.0 (2) | N1B—C7B—S2B | 124.3 (7) |
S2A—Ag2—S2B | 141.04 (8) | C6B—C7B—S2B | 119.9 (6) |
N2Ci—Ag2—Ag1 | 128.9 (2) | C5C—N1C—C1C | 117.4 (8) |
S2A—Ag2—Ag1 | 89.13 (6) | C5C—N1C—Ag1 | 121.9 (6) |
S2B—Ag2—Ag1 | 54.01 (5) | C1C—N1C—Ag1 | 119.7 (6) |
O1A—S1A—O2A | 116.5 (4) | C10C—N2C—C6C | 118.0 (8) |
O1A—S1A—N1A | 110.8 (4) | N1C—C1C—C2C | 122.8 (9) |
O2A—S1A—N1A | 109.0 (4) | N1C—C1C—H1C | 118.6 |
O1A—S1A—C1A | 109.6 (4) | C2C—C1C—H1C | 118.6 |
O2A—S1A—C1A | 112.9 (4) | C3C—C2C—C1C | 118.7 (9) |
N1A—S1A—C1A | 96.2 (4) | C3C—C2C—H2C | 120.7 |
C7A—S2A—Ag2 | 106.5 (3) | C1C—C2C—H2C | 120.7 |
C7A—N1A—S1A | 110.8 (6) | C4C—C3C—C2C | 119.0 (8) |
C7A—N1A—Ag1 | 117.7 (5) | C4C—C3C—C8C | 121.5 (8) |
S1A—N1A—Ag1 | 121.3 (4) | C2C—C3C—C8C | 119.4 (8) |
C2A—C1A—C6A | 122.4 (8) | C3C—C4C—C5C | 117.9 (9) |
C2A—C1A—S1A | 129.9 (7) | C3C—C4C—H4C | 121.0 |
C6A—C1A—S1A | 107.7 (6) | C5C—C4C—H4C | 121.0 |
C1A—C2A—C3A | 117.8 (9) | N1C—C5C—C4C | 124.2 (9) |
C1A—C2A—H2A | 121.1 | N1C—C5C—H5C | 117.9 |
C3A—C2A—H2A | 121.1 | C4C—C5C—H5C | 117.9 |
C4A—C3A—C2A | 119.8 (10) | N2C—C6C—C7C | 122.9 (10) |
C4A—C3A—H3A | 120.1 | N2C—C6C—H6C | 118.5 |
C2A—C3A—H3A | 120.1 | C7C—C6C—H6C | 118.5 |
C3A—C4A—C5A | 122.9 (10) | C6C—C7C—C8C | 119.0 (10) |
C3A—C4A—H4A | 118.5 | C6C—C7C—H7C | 120.5 |
C5A—C4A—H4A | 118.5 | C8C—C7C—H7C | 120.5 |
C6A—C5A—C4A | 116.8 (9) | C7C—C8C—C9C | 118.7 (8) |
C6A—C5A—H5A | 121.6 | C7C—C8C—C3C | 121.4 (9) |
C4A—C5A—H5A | 121.6 | C9C—C8C—C3C | 119.7 (9) |
C5A—C6A—C1A | 120.2 (8) | C8C—C9C—C10C | 118.3 (9) |
C5A—C6A—C7A | 129.6 (7) | C8C—C9C—H9C | 120.8 |
C1A—C6A—C7A | 110.0 (7) | C10C—C9C—H9C | 120.8 |
N1A—C7A—C6A | 115.2 (7) | N2C—C10C—C9C | 122.8 (10) |
N1A—C7A—S2A | 125.8 (6) | N2C—C10C—H10C | 118.6 |
C6A—C7A—S2A | 119.1 (6) | C9C—C10C—H10C | 118.6 |
O2B—S1B—O1B | 117.5 (5) | C1D—N1D—C5D | 115.8 (9) |
O2B—S1B—N1B | 109.3 (5) | C1D—N1D—Ag1 | 121.7 (7) |
O1B—S1B—N1B | 109.8 (5) | C5D—N1D—Ag1 | 122.5 (7) |
O2B—S1B—C1B | 111.2 (5) | N1D—C1D—C2D | 123.8 (10) |
O1B—S1B—C1B | 111.0 (5) | N1D—C1D—H1D | 118.1 |
N1B—S1B—C1B | 95.9 (4) | C2D—C1D—H1D | 118.1 |
C7B—S2B—Ag1 | 101.8 (3) | C3D—C2D—C1D | 120.9 (10) |
C7B—S2B—Ag2 | 99.4 (3) | C3D—C2D—H2D | 119.6 |
Ag1—S2B—Ag2 | 69.56 (7) | C1D—C2D—H2D | 119.6 |
C7B—N1B—S1B | 110.9 (6) | C2D—C3D—C4D | 116.4 (8) |
C2B—C1B—C6B | 124.3 (9) | C2D—C3D—C3Dii | 121.2 (10) |
C2B—C1B—S1B | 129.7 (7) | C4D—C3D—C3Dii | 122.2 (11) |
C6B—C1B—S1B | 106.0 (6) | C3D—C4D—C5D | 120.0 (11) |
C1B—C2B—C3B | 116.4 (10) | C3D—C4D—H4D | 120.0 |
C1B—C2B—H2B | 121.8 | C5D—C4D—H4D | 120.0 |
C3B—C2B—H2B | 121.8 | N1D—C5D—C4D | 123.0 (11) |
C4B—C3B—C2B | 120.9 (10) | N1D—C5D—H5D | 118.5 |
C4B—C3B—H3B | 119.5 | C4D—C5D—H5D | 118.5 |
Symmetry codes: (i) x−1/2, −y+1/2, z−1/2; (ii) −x+2, −y+2, −z; (iii) −x+1, −y+1, −z. |
D—X···A interactions in (I) (Å, °) topD—X···A | D—X | X···A | D···A | D—X···A | Type |
C1D—H1D···O1A | 0.93 | 2.59 | 3.345 (13) | 139 | I |
C1D—H1D···Cg1 | 0.93 | 2.93 | 3.759 (14) | 150 | I |
S1B—O1B···Cg3iii | 1.427 (8) | 3.564 (10) | 4.332 (5) | 113.3 (4) | I |
C5C—H5C···O2Biv | 0.93 | 2.48 | 3.189 (13) | 134 | II |
C1C—H1C···Cg4v | 0.93 | 2.89 | 3.704 (10) | 147 | II |
C2A—H2A···O2Avi | 0.93 | 2.56 | 3.383 (11) | 147 | III |
S1A—O2A···Cg3vi | 1.434 (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. |
π–π contacts for (I) topGroup1···Group2 | ccd (Å) | da (°) | mipd (Å) | Type |
Cg5···Cg2v | 4.068 (7) | 19.8 (6) | 3.5 (2) | II |
Cg3···Cg4vii | 4.061 (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). |