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The bifunctional pyridine-2,3-dicarboxylic acid (H
2pdc) ligand has one N atom and four O atoms, which could bind more than one Ag
I centre with diverse binding modes. A novel infinite one-dimensional Ag
I coordination polymer, namely
catena-poly[[silver(I)-(μ
2-pyridine-2,3-dicarboxylato-κ
2N:
O3)-silver(I)-tris(μ
2-5-methyl-1,3,4-thiodiazol-2-amine-κ
2N:
N′)] monohydrate ethanol monosolvate], {[Ag
2(C
7H
3NO
4)(C
3H
5N
3S)
3]·H
2O·C
2H
5OH}
n, has been synthesized using H
2pdc and 5-methyl-1,3,4-thiadiazol-2-amine (tda), and characterized by single-crystal X-ray diffraction. One Ag
I atom is located in a four-coordinated AgN
4 tetrahedral geometry and the other Ag
I atom is in a tetrahedral AgN
3O geometry. A dinuclear Ag
I cluster formed by three tda ligands with a paddelwheel configuration is bridged by the dianionic pdc
2− ligand into a one-dimensional coordination polymer. Interchain N—H
O hydrogen bonds extend the one-dimensional chains into an undulating two-dimensional sheet. The sheets are further packed into a three-dimensional supramolecular framework by interchain N—H
O hydrogen bonds.
Supporting information
CCDC reference: 1551913
Data collection: SMART (Bruker, 2012); cell refinement: SMART (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXT (Sheldrick, 2015a) and OLEX2 (Dolomanov et al.,
2009); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b) and OLEX2 (Dolomanov et al.,
2009); molecular graphics: DIAMOND (Brandenburg, 2008); software used to prepare material for publication: publCIF (Westrip, 2010) and PLATON (Spek, 2009).
catena-Poly[[silver(I)-(µ
2-pyridine-2,3-dicarboxylato-
κ2N:
O3)-silver(I)-tris(µ
2-5-methyl-1,3,4-thiodiazol-2-amine-
κ2N:
N')] monohydrate ethanol monosolvate]
top
Crystal data top
[Ag2(C7H3NO4)(C3H5N3S)3]·H2O·C2H6O | F(000) = 1576 |
Mr = 790.38 | Dx = 2.016 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3665 (4) Å | Cell parameters from 8981 reflections |
b = 23.1277 (11) Å | θ = 2.8–27.6° |
c = 13.5984 (7) Å | µ = 1.80 mm−1 |
β = 98.221 (1)° | T = 100 K |
V = 2604.2 (2) Å3 | Block, yellow |
Z = 4 | 0.22 × 0.20 × 0.18 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 5458 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
phi and ω scans | θmax = 27.6°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2012) | h = −6→10 |
Tmin = 0.705, Tmax = 0.728 | k = −30→29 |
15594 measured reflections | l = −16→16 |
5918 independent reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | Hydrogen site location: mixed |
wR(F2) = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0262P)2 + 4.0926P] where P = (Fo2 + 2Fc2)/3 |
5918 reflections | (Δ/σ)max = 0.001 |
337 parameters | Δρmax = 1.34 e Å−3 |
7 restraints | Δρmin = −0.82 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ag1 | 0.31342 (2) | 0.12131 (2) | 0.21967 (2) | 0.01782 (6) | |
Ag2 | 0.26584 (2) | 0.26895 (2) | 0.20782 (2) | 0.01788 (6) | |
S1 | −0.04351 (9) | 0.17446 (3) | −0.07942 (5) | 0.01951 (14) | |
S2 | 0.82115 (8) | 0.22203 (3) | 0.17491 (6) | 0.02212 (15) | |
S3 | −0.01904 (10) | 0.18514 (4) | 0.46437 (6) | 0.02778 (16) | |
N1 | 0.5476 (3) | 0.17953 (10) | 0.19762 (17) | 0.0175 (5) | |
N2 | 0.5309 (3) | 0.23914 (9) | 0.20876 (18) | 0.0179 (5) | |
N3 | 0.6849 (3) | 0.32419 (11) | 0.2079 (2) | 0.0281 (6) | |
H3A | 0.603 (3) | 0.3452 (14) | 0.216 (3) | 0.034* | |
H3B | 0.781 (3) | 0.3381 (15) | 0.201 (3) | 0.034* | |
N4 | 0.1506 (3) | 0.22545 (10) | 0.33860 (17) | 0.0181 (5) | |
N5 | 0.1617 (3) | 0.16546 (10) | 0.33185 (17) | 0.0189 (5) | |
N6 | 0.0645 (4) | 0.08011 (12) | 0.3967 (2) | 0.0309 (6) | |
H6A | 0.026 (4) | 0.0638 (15) | 0.449 (2) | 0.037* | |
H6B | 0.096 (4) | 0.0587 (14) | 0.348 (2) | 0.037* | |
N7 | 0.1589 (3) | 0.21290 (9) | 0.06377 (17) | 0.0164 (4) | |
N8 | 0.1552 (3) | 0.15329 (9) | 0.07817 (17) | 0.0172 (5) | |
N9 | 0.0245 (3) | 0.07007 (10) | 0.00749 (18) | 0.0205 (5) | |
H9A | 0.050 (4) | 0.0502 (13) | 0.0639 (17) | 0.025* | |
H9B | −0.061 (3) | 0.0589 (14) | −0.033 (2) | 0.025* | |
N10 | 0.0586 (3) | 0.54262 (9) | 0.19787 (17) | 0.0156 (4) | |
O1 | 0.2551 (2) | 0.37189 (8) | 0.16865 (16) | 0.0248 (4) | |
O2 | 0.0125 (3) | 0.34120 (8) | 0.19185 (18) | 0.0310 (5) | |
O3 | 0.2492 (3) | 0.44391 (9) | 0.35920 (16) | 0.0290 (5) | |
O4 | 0.3729 (2) | 0.51789 (9) | 0.29542 (17) | 0.0285 (5) | |
C1 | 0.7371 (4) | 0.10357 (14) | 0.1620 (3) | 0.0308 (7) | |
H1A | 0.6515 | 0.0774 | 0.1766 | 0.046* | |
H1B | 0.8377 | 0.0944 | 0.2055 | 0.046* | |
H1C | 0.7531 | 0.0990 | 0.0925 | 0.046* | |
C2 | 0.6898 (3) | 0.16445 (12) | 0.1796 (2) | 0.0190 (5) | |
C3 | 0.6649 (3) | 0.26732 (12) | 0.1997 (2) | 0.0174 (5) | |
C4 | 0.0213 (4) | 0.30328 (13) | 0.4228 (2) | 0.0260 (6) | |
H4A | 0.0814 | 0.3289 | 0.3838 | 0.039* | |
H4B | 0.0516 | 0.3117 | 0.4937 | 0.039* | |
H4C | −0.0948 | 0.3097 | 0.4040 | 0.039* | |
C5 | 0.0604 (3) | 0.24235 (13) | 0.4031 (2) | 0.0211 (6) | |
C6 | 0.0783 (3) | 0.13841 (13) | 0.3920 (2) | 0.0210 (6) | |
C7 | 0.0401 (4) | 0.29227 (12) | −0.0412 (2) | 0.0236 (6) | |
H7A | −0.0682 | 0.3046 | −0.0307 | 0.035* | |
H7B | 0.0523 | 0.2974 | −0.1113 | 0.035* | |
H7C | 0.1212 | 0.3156 | 0.0003 | 0.035* | |
C8 | 0.0631 (3) | 0.23028 (11) | −0.01375 (19) | 0.0156 (5) | |
C9 | 0.0535 (3) | 0.12705 (11) | 0.01016 (19) | 0.0153 (5) | |
C10 | 0.1095 (3) | 0.38008 (11) | 0.1771 (2) | 0.0181 (5) | |
C11 | 0.0427 (3) | 0.44062 (11) | 0.16195 (19) | 0.0143 (5) | |
C12 | −0.0946 (3) | 0.44998 (12) | 0.0934 (2) | 0.0184 (5) | |
H12 | −0.1476 | 0.4184 | 0.0579 | 0.022* | |
C13 | −0.1540 (3) | 0.50573 (12) | 0.0768 (2) | 0.0196 (5) | |
H13 | −0.2474 | 0.5131 | 0.0300 | 0.023* | |
C14 | −0.0728 (3) | 0.55029 (12) | 0.1306 (2) | 0.0186 (5) | |
H14 | −0.1127 | 0.5885 | 0.1191 | 0.022* | |
C15 | 0.1163 (3) | 0.48839 (11) | 0.21378 (19) | 0.0141 (5) | |
C16 | 0.2591 (3) | 0.48240 (11) | 0.2964 (2) | 0.0177 (5) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.01853 (11) | 0.01312 (10) | 0.02070 (11) | 0.00154 (7) | −0.00094 (8) | 0.00353 (8) |
Ag2 | 0.01827 (11) | 0.01277 (10) | 0.02191 (11) | 0.00216 (7) | 0.00051 (8) | −0.00142 (8) |
S1 | 0.0245 (3) | 0.0156 (3) | 0.0155 (3) | −0.0007 (3) | −0.0070 (3) | 0.0005 (3) |
S2 | 0.0139 (3) | 0.0261 (4) | 0.0271 (4) | −0.0035 (3) | 0.0051 (3) | −0.0011 (3) |
S3 | 0.0295 (4) | 0.0347 (4) | 0.0210 (4) | −0.0026 (3) | 0.0097 (3) | −0.0007 (3) |
N1 | 0.0173 (11) | 0.0159 (11) | 0.0197 (12) | 0.0000 (9) | 0.0038 (9) | 0.0005 (9) |
N2 | 0.0160 (11) | 0.0139 (11) | 0.0236 (12) | −0.0004 (8) | 0.0018 (9) | 0.0022 (9) |
N3 | 0.0290 (14) | 0.0201 (12) | 0.0359 (15) | −0.0058 (11) | 0.0075 (12) | 0.0002 (11) |
N4 | 0.0148 (11) | 0.0206 (12) | 0.0182 (12) | 0.0020 (9) | 0.0000 (9) | −0.0008 (9) |
N5 | 0.0182 (11) | 0.0181 (11) | 0.0199 (12) | −0.0004 (9) | 0.0006 (9) | 0.0007 (9) |
N6 | 0.0386 (16) | 0.0251 (14) | 0.0297 (15) | −0.0040 (12) | 0.0077 (12) | 0.0043 (11) |
N7 | 0.0183 (11) | 0.0114 (10) | 0.0181 (11) | 0.0001 (8) | −0.0017 (9) | 0.0013 (9) |
N8 | 0.0205 (11) | 0.0111 (10) | 0.0179 (11) | 0.0000 (9) | −0.0044 (9) | 0.0004 (9) |
N9 | 0.0245 (13) | 0.0148 (11) | 0.0191 (12) | −0.0029 (9) | −0.0070 (9) | −0.0002 (9) |
N10 | 0.0163 (11) | 0.0118 (10) | 0.0180 (11) | 0.0007 (8) | 0.0003 (8) | 0.0003 (8) |
O1 | 0.0244 (11) | 0.0165 (10) | 0.0331 (12) | 0.0063 (8) | 0.0030 (9) | 0.0015 (8) |
O2 | 0.0390 (13) | 0.0119 (9) | 0.0432 (14) | −0.0060 (9) | 0.0099 (10) | 0.0016 (9) |
O3 | 0.0268 (11) | 0.0323 (12) | 0.0246 (11) | 0.0014 (9) | −0.0074 (9) | 0.0081 (9) |
O4 | 0.0218 (11) | 0.0238 (11) | 0.0355 (12) | −0.0049 (8) | −0.0108 (9) | 0.0004 (9) |
C1 | 0.0291 (17) | 0.0258 (16) | 0.0396 (19) | 0.0036 (13) | 0.0122 (14) | −0.0013 (14) |
C2 | 0.0176 (13) | 0.0211 (13) | 0.0186 (13) | −0.0021 (11) | 0.0039 (10) | 0.0002 (11) |
C3 | 0.0156 (12) | 0.0196 (13) | 0.0164 (13) | −0.0012 (10) | 0.0008 (10) | 0.0017 (10) |
C4 | 0.0271 (16) | 0.0274 (16) | 0.0232 (15) | 0.0073 (12) | 0.0027 (12) | −0.0049 (12) |
C5 | 0.0202 (14) | 0.0269 (15) | 0.0148 (13) | 0.0018 (11) | −0.0024 (10) | −0.0032 (11) |
C6 | 0.0166 (13) | 0.0276 (15) | 0.0177 (13) | −0.0023 (11) | −0.0019 (10) | 0.0028 (11) |
C7 | 0.0331 (16) | 0.0160 (13) | 0.0189 (14) | −0.0004 (11) | −0.0064 (12) | 0.0028 (11) |
C8 | 0.0147 (12) | 0.0177 (13) | 0.0141 (12) | −0.0002 (10) | 0.0011 (9) | 0.0010 (10) |
C9 | 0.0171 (12) | 0.0158 (12) | 0.0126 (12) | 0.0012 (10) | 0.0012 (9) | 0.0000 (10) |
C10 | 0.0282 (15) | 0.0105 (12) | 0.0151 (13) | 0.0005 (10) | 0.0012 (11) | −0.0012 (10) |
C11 | 0.0164 (12) | 0.0118 (12) | 0.0147 (12) | −0.0014 (9) | 0.0027 (9) | 0.0006 (9) |
C12 | 0.0187 (13) | 0.0186 (13) | 0.0172 (13) | −0.0051 (10) | −0.0005 (10) | −0.0014 (10) |
C13 | 0.0140 (12) | 0.0237 (14) | 0.0195 (14) | 0.0018 (10) | −0.0028 (10) | 0.0030 (11) |
C14 | 0.0186 (13) | 0.0158 (13) | 0.0206 (14) | 0.0056 (10) | 0.0002 (10) | 0.0037 (10) |
C15 | 0.0151 (12) | 0.0126 (12) | 0.0143 (12) | 0.0002 (9) | 0.0014 (9) | −0.0012 (10) |
C16 | 0.0191 (13) | 0.0140 (12) | 0.0178 (13) | 0.0059 (10) | −0.0043 (10) | −0.0064 (10) |
Geometric parameters (Å, º) top
Ag1—N8 | 2.296 (2) | N9—H9A | 0.894 (18) |
Ag1—N10i | 2.318 (2) | N9—H9B | 0.874 (18) |
Ag1—N5 | 2.352 (2) | N10—C14 | 1.338 (3) |
Ag1—N1 | 2.431 (2) | N10—C15 | 1.350 (3) |
Ag2—N2 | 2.320 (2) | N10—Ag1ii | 2.318 (2) |
Ag2—N4 | 2.365 (2) | O1—C10 | 1.255 (3) |
Ag2—N7 | 2.412 (2) | O2—C10 | 1.246 (3) |
Ag2—O1 | 2.4386 (19) | O3—C16 | 1.244 (3) |
S1—C8 | 1.741 (3) | O4—C16 | 1.259 (3) |
S1—C9 | 1.750 (3) | C1—C2 | 1.491 (4) |
S2—C2 | 1.733 (3) | C1—H1A | 0.9800 |
S2—C3 | 1.745 (3) | C1—H1B | 0.9800 |
S3—C6 | 1.740 (3) | C1—H1C | 0.9800 |
S3—C5 | 1.745 (3) | C4—C5 | 1.480 (4) |
N1—C2 | 1.296 (3) | C4—H4A | 0.9800 |
N1—N2 | 1.396 (3) | C4—H4B | 0.9800 |
N2—C3 | 1.318 (3) | C4—H4C | 0.9800 |
N3—C3 | 1.328 (4) | C7—C8 | 1.487 (4) |
N3—H3A | 0.864 (18) | C7—H7A | 0.9800 |
N3—H3B | 0.884 (18) | C7—H7B | 0.9800 |
N4—C5 | 1.297 (4) | C7—H7C | 0.9800 |
N4—N5 | 1.395 (3) | C10—C11 | 1.511 (3) |
N5—C6 | 1.308 (4) | C11—C12 | 1.389 (4) |
N6—C6 | 1.355 (4) | C11—C15 | 1.404 (3) |
N6—H6A | 0.901 (18) | C12—C13 | 1.389 (4) |
N6—H6B | 0.894 (18) | C12—H12 | 0.9500 |
N7—C8 | 1.294 (3) | C13—C14 | 1.384 (4) |
N7—N8 | 1.393 (3) | C13—H13 | 0.9500 |
N8—C9 | 1.312 (3) | C14—H14 | 0.9500 |
N9—C9 | 1.340 (3) | C15—C16 | 1.525 (3) |
| | | |
N8—Ag1—N10i | 146.03 (8) | N1—C2—C1 | 123.8 (3) |
N8—Ag1—N5 | 95.96 (8) | N1—C2—S2 | 113.8 (2) |
N10i—Ag1—N5 | 106.36 (8) | C1—C2—S2 | 122.4 (2) |
N8—Ag1—N1 | 95.54 (8) | N2—C3—N3 | 125.4 (3) |
N10i—Ag1—N1 | 99.78 (8) | N2—C3—S2 | 113.1 (2) |
N5—Ag1—N1 | 111.02 (8) | N3—C3—S2 | 121.5 (2) |
N2—Ag2—N4 | 111.20 (8) | C5—C4—H4A | 109.5 |
N2—Ag2—N7 | 95.04 (8) | C5—C4—H4B | 109.5 |
N4—Ag2—N7 | 103.79 (8) | H4A—C4—H4B | 109.5 |
N2—Ag2—O1 | 107.25 (7) | C5—C4—H4C | 109.5 |
N4—Ag2—O1 | 124.98 (7) | H4A—C4—H4C | 109.5 |
N7—Ag2—O1 | 110.46 (7) | H4B—C4—H4C | 109.5 |
C8—S1—C9 | 87.42 (12) | N4—C5—C4 | 125.1 (3) |
C2—S2—C3 | 87.59 (13) | N4—C5—S3 | 113.1 (2) |
C6—S3—C5 | 87.71 (14) | C4—C5—S3 | 121.8 (2) |
C2—N1—N2 | 113.3 (2) | N5—C6—N6 | 124.2 (3) |
C2—N1—Ag1 | 130.69 (18) | N5—C6—S3 | 113.0 (2) |
N2—N1—Ag1 | 115.99 (16) | N6—C6—S3 | 122.7 (2) |
C3—N2—N1 | 112.2 (2) | C8—C7—H7A | 109.5 |
C3—N2—Ag2 | 132.68 (18) | C8—C7—H7B | 109.5 |
N1—N2—Ag2 | 113.80 (16) | H7A—C7—H7B | 109.5 |
C3—N3—H3A | 118 (2) | C8—C7—H7C | 109.5 |
C3—N3—H3B | 117 (2) | H7A—C7—H7C | 109.5 |
H3A—N3—H3B | 124 (3) | H7B—C7—H7C | 109.5 |
C5—N4—N5 | 113.3 (2) | N7—C8—C7 | 123.2 (2) |
C5—N4—Ag2 | 136.0 (2) | N7—C8—S1 | 113.6 (2) |
N5—N4—Ag2 | 109.59 (16) | C7—C8—S1 | 123.2 (2) |
C6—N5—N4 | 112.8 (2) | N8—C9—N9 | 124.8 (2) |
C6—N5—Ag1 | 125.70 (19) | N8—C9—S1 | 112.97 (19) |
N4—N5—Ag1 | 121.47 (16) | N9—C9—S1 | 122.2 (2) |
C6—N6—H6A | 120 (2) | O2—C10—O1 | 124.7 (2) |
C6—N6—H6B | 119 (2) | O2—C10—C11 | 117.0 (2) |
H6A—N6—H6B | 122 (3) | O1—C10—C11 | 118.2 (2) |
C8—N7—N8 | 113.5 (2) | C12—C11—C15 | 118.4 (2) |
C8—N7—Ag2 | 127.54 (18) | C12—C11—C10 | 119.4 (2) |
N8—N7—Ag2 | 115.52 (15) | C15—C11—C10 | 122.3 (2) |
C9—N8—N7 | 112.6 (2) | C11—C12—C13 | 119.8 (2) |
C9—N8—Ag1 | 132.80 (18) | C11—C12—H12 | 120.1 |
N7—N8—Ag1 | 114.49 (15) | C13—C12—H12 | 120.1 |
C9—N9—H9A | 118 (2) | C14—C13—C12 | 117.9 (2) |
C9—N9—H9B | 116 (2) | C14—C13—H13 | 121.0 |
H9A—N9—H9B | 117 (3) | C12—C13—H13 | 121.0 |
C14—N10—C15 | 118.2 (2) | N10—C14—C13 | 123.8 (2) |
C14—N10—Ag1ii | 120.29 (17) | N10—C14—H14 | 118.1 |
C15—N10—Ag1ii | 121.49 (17) | C13—C14—H14 | 118.1 |
C10—O1—Ag2 | 97.66 (16) | N10—C15—C11 | 122.0 (2) |
C2—C1—H1A | 109.5 | N10—C15—C16 | 115.3 (2) |
C2—C1—H1B | 109.5 | C11—C15—C16 | 122.6 (2) |
H1A—C1—H1B | 109.5 | O3—C16—O4 | 126.7 (2) |
C2—C1—H1C | 109.5 | O3—C16—C15 | 116.7 (2) |
H1A—C1—H1C | 109.5 | O4—C16—C15 | 116.6 (2) |
H1B—C1—H1C | 109.5 | | |
| | | |
C2—N1—N2—C3 | −0.8 (3) | N8—N7—C8—C7 | 176.7 (2) |
Ag1—N1—N2—C3 | 177.41 (18) | Ag2—N7—C8—C7 | 18.9 (4) |
C2—N1—N2—Ag2 | 167.85 (19) | N8—N7—C8—S1 | −0.4 (3) |
Ag1—N1—N2—Ag2 | −14.0 (2) | Ag2—N7—C8—S1 | −158.19 (13) |
C5—N4—N5—C6 | 0.2 (3) | C9—S1—C8—N7 | 0.9 (2) |
Ag2—N4—N5—C6 | −169.88 (18) | C9—S1—C8—C7 | −176.2 (3) |
C5—N4—N5—Ag1 | 179.07 (18) | N7—N8—C9—N9 | −178.8 (3) |
Ag2—N4—N5—Ag1 | 9.0 (2) | Ag1—N8—C9—N9 | −3.4 (4) |
C8—N7—N8—C9 | −0.6 (3) | N7—N8—C9—S1 | 1.2 (3) |
Ag2—N7—N8—C9 | 160.06 (18) | Ag1—N8—C9—S1 | 176.65 (14) |
C8—N7—N8—Ag1 | −176.86 (18) | C8—S1—C9—N8 | −1.2 (2) |
Ag2—N7—N8—Ag1 | −16.2 (2) | C8—S1—C9—N9 | 178.8 (2) |
N2—N1—C2—C1 | −178.3 (3) | Ag2—O1—C10—O2 | −5.8 (3) |
Ag1—N1—C2—C1 | 3.9 (4) | Ag2—O1—C10—C11 | 178.3 (2) |
N2—N1—C2—S2 | 0.3 (3) | O2—C10—C11—C12 | −50.2 (4) |
Ag1—N1—C2—S2 | −177.51 (13) | O1—C10—C11—C12 | 125.9 (3) |
C3—S2—C2—N1 | 0.1 (2) | O2—C10—C11—C15 | 130.9 (3) |
C3—S2—C2—C1 | 178.7 (3) | O1—C10—C11—C15 | −52.9 (4) |
N1—N2—C3—N3 | −179.2 (3) | C15—C11—C12—C13 | 0.8 (4) |
Ag2—N2—C3—N3 | 15.1 (4) | C10—C11—C12—C13 | −178.1 (2) |
N1—N2—C3—S2 | 0.9 (3) | C11—C12—C13—C14 | −0.3 (4) |
Ag2—N2—C3—S2 | −164.92 (14) | C15—N10—C14—C13 | 0.5 (4) |
C2—S2—C3—N2 | −0.6 (2) | Ag1ii—N10—C14—C13 | 178.6 (2) |
C2—S2—C3—N3 | 179.4 (3) | C12—C13—C14—N10 | −0.4 (4) |
N5—N4—C5—C4 | −177.3 (3) | C14—N10—C15—C11 | 0.1 (4) |
Ag2—N4—C5—C4 | −10.8 (4) | Ag1ii—N10—C15—C11 | −177.95 (18) |
N5—N4—C5—S3 | 0.8 (3) | C14—N10—C15—C16 | −176.0 (2) |
Ag2—N4—C5—S3 | 167.31 (15) | Ag1ii—N10—C15—C16 | 6.0 (3) |
C6—S3—C5—N4 | −1.2 (2) | C12—C11—C15—N10 | −0.8 (4) |
C6—S3—C5—C4 | 176.9 (2) | C10—C11—C15—N10 | 178.1 (2) |
N4—N5—C6—N6 | 177.4 (3) | C12—C11—C15—C16 | 175.0 (2) |
Ag1—N5—C6—N6 | −1.4 (4) | C10—C11—C15—C16 | −6.1 (4) |
N4—N5—C6—S3 | −1.1 (3) | N10—C15—C16—O3 | 130.6 (3) |
Ag1—N5—C6—S3 | −179.95 (12) | C11—C15—C16—O3 | −45.5 (4) |
C5—S3—C6—N5 | 1.3 (2) | N10—C15—C16—O4 | −47.6 (3) |
C5—S3—C6—N6 | −177.2 (3) | C11—C15—C16—O4 | 136.3 (3) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (ii) −x+1/2, y+1/2, −z+1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3B···O2iii | 0.88 (3) | 1.96 (3) | 2.808 (4) | 161 (3) |
N6—H6B···O4i | 0.90 (3) | 2.22 (3) | 3.092 (4) | 166 (3) |
N9—H9A···O4i | 0.89 (3) | 2.07 (2) | 2.953 (3) | 170 (3) |
N9—H9B···O3iv | 0.88 (3) | 2.00 (3) | 2.854 (3) | 164 (3) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+1/2; (iii) x+1, y, z; (iv) x−1/2, −y+1/2, z−1/2. |
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