research communications
κO)(imidazolidine-2-thione-κS)bis(triphenylphosphane-κP)silver(I)] di-μ-imidazolidine-2-thione-κ4S:S-bis[(imidazolidine-2-thione-κS)bis(triphenylphosphane-κP)silver(I)] diacetate acetonitrile disolvate tetrahydrate
of bis[(acetato-aDepartment of Chemistry, Youngstown State University, 1 University Plaza, 44555 Youngstown, OH, USA, and bDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat Yai, Songkhla 90112, Thailand
*Correspondence e-mail: yupa.t@psu.ac.th
In the title compound, [Ag2(C3H6N2S)4(C18H15P)2](C2H3O2)2·[Ag(C2H3O2)(C3H6N2S)(C18H15P)2]2·2C2H3N·4H2O, the AgI ion in the mononuclear neutral complex exhibits a distorted tetrahedral environment with coordination by two P atoms from triphenylphosphane (PPh3) ligands, one S atom of an imidazolidine-2-thione (etu) ligand and one O atom of an acetate anion. The binuclear cationic complex comprises two inversion-related [Ag(C3H6N2S)2(C18H15P)] units with AgI ions bridged by two S atoms from etu ligands forming a four-membered Ag–S–Ag–S ring. Each AgI ion is coordinated by a P atom of a PPh3 ligand, two S atoms of bridging etu ligands and the terminal S atom of an etu ligand in a distorted tetrahedral environment. In the crystal, the mononuclear complex is linked to lattice water molecules through O—H⋯O and N—H⋯O hydrogen bonds, forming a chain along [100]. In addition, the binuclear complex molecules are connected to acetate anions and lattice water molecules via O—H⋯O, N—H⋯O and O—H⋯S hydrogen bonds, also along [100].
Keywords: crystal structure; imidazolidine-2-thione; silver complex.
CCDC reference: 1452047
1. Chemical context
Silver(I) complexes containing S- or P-donor ligands have received much attention because of their potential applications in biochemistry (Isab et al., 2010; Nawaz et al., 2011) and their luminescent properties (Ferrari et al., 2007). The of the title compound, [Ag(CH3COO)(C3H6N2S)(C18H15P)2]2·[Ag2(C3H6N2S)4(C18H15P)2](CH3COO)2·2CH3CN·4H2O, is presented herein.
2. Structural commentary
The structures of the molecular components of the title compound are shown in Fig. 1. The consists of a mononuclear neutral AgI complex, a discrete cationic binuclear AgI complex, acetate anions, acetonitrile solvent molecules and water molecules of crystallization. In the mononuclear complex, the AgI ion exhibits a distorted tetrahedral environment, being coordinated by two P atoms of triphenylphosphane (PPh3) ligands, one terminal S atom of a imidazolidine-2-thione (or ethylenethiourea; etu) ligand and an O atom of an acetate anion. The molecule of the binuclear complex lies across a crystallographic inversion center which is at the center of the Ag2S2 core. The two AgI ions are bridged by two S atoms of etu ligands forming a four-membered Ag–S–Ag–S ring. Each AgI ion is in a distorted tetrahedral coordination geometry formed by a P atom of a PPh3 ligand, the S atoms of two bridging etu ligands and a terminal S atom of an etu ligand.
3. Supramolecular features
In the A⋯O6, O7—H7B⋯O6iv, N6—H6⋯O4 and N5—H5⋯O7iii hydrogen bonds (symmetry codes as in Table 1) link the mononuclear complexes and water molecules into chains along [100] (Fig. 2). In addition, N1—H1⋯O1, N2—H2⋯O8i, N3—H3⋯O1, N4—H4⋯O2ii, O8—H8C⋯O2 and O8—H8D⋯S2iii hydrogen bonds connect the discrete binuclear complexes with acetate anions and water molecules, forming another chain along [100] (Fig. 3).
O7—H74. Synthesis and crystallization
Triphenylphosphane (0.31 g, 1.18 mmol) was dissolved in 30 cm3 of acetonitrile at 335 K. Ag(OAc) (0.10 g, 0.60 mmol) was added and the mixture was stirred for 3 h. Ethylenethiourea (0.06 g, 0.59 mmol) was added and the new reaction mixture was heated under reflux for 5 h. The resulting clear solution was filtered off and left to evaporate at room temperature. Crystals suitable for X-ray diffraction, which were deposited upon standing for a week, were filtered off and dried under reduced pressure.
5. Refinement
Crystal data, data collection and structure . All C- and N-bound H atoms were constrained with a riding model: 0.95 Å (aryl H) and Uiso(H) = 1.2Ueq(C); 0.99 Å (CH2) and Uiso(H) = 1.2Ueq(C); 0.98 Å (CH3) and Uiso(H) = 1.5Ueq(C); 0.88 Å (NH) and Uiso(H) = 1.2Ueq(N). Water hydrogen atoms were located from a difference Fourier map and were refined with an O—H distance restraint of 0.84 (2) Å and Uiso(H) = 1.2Ueq(O).
details are summarized in Table 2
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Supporting information
CCDC reference: 1452047
https://doi.org/10.1107/S205698901600308X/wm5275sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901600308X/wm5275Isup2.hkl
Data collection: APEX2 (Bruker, 2014); cell
SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015) and SHELXLE (Hübschle et al., 2011); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).[Ag2(C3H6N2S)4(C18H15P)2](C2H3O2)2·[Ag(C2H3O2)(C3H6N2S)(C18H15P)2]2·2C2H3N·4H2O | Z = 1 |
Mr = 3008.39 | F(000) = 1548 |
Triclinic, P1 | Dx = 1.449 Mg m−3 |
a = 9.5867 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.3018 (7) Å | Cell parameters from 9707 reflections |
c = 22.8548 (10) Å | θ = 2.4–30.6° |
α = 104.179 (2)° | µ = 0.78 mm−1 |
β = 94.449 (2)° | T = 100 K |
γ = 91.992 (2)° | Block, colourless |
V = 3447.2 (3) Å3 | 0.16 × 0.15 × 0.13 mm |
Bruker AXS D8 Quest CMOS diffractometer | 20957 independent reflections |
Radiation source: I-mu-S microsource X-ray tube | 18898 reflections with I > 2σ(I) |
Laterally graded multilayer (Goebel) mirror monochromator | Rint = 0.026 |
ω and φ scans | θmax = 30.6°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2014) | h = −13→13 |
Tmin = 0.882, Tmax = 0.903 | k = −23→23 |
71762 measured reflections | l = −32→32 |
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)] = 0.042 | Hydrogen site location: mixed |
wR(F2) = 0.088 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.26 | w = 1/[σ2(Fo2) + (0.0001P)2 + 7.6382P] where P = (Fo2 + 2Fc2)/3 |
20957 reflections | (Δ/σ)max = 0.002 |
826 parameters | Δρmax = 1.05 e Å−3 |
6 restraints | Δρmin = −0.97 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
Ag1 | 0.35807 (2) | 0.29775 (2) | 0.13070 (2) | 0.01524 (4) | |
Ag2 | 0.00978 (2) | 0.12147 (2) | 0.53974 (2) | 0.01655 (4) | |
S1 | 0.19225 (6) | 0.01029 (4) | 0.50712 (3) | 0.01504 (10) | |
S2 | −0.08966 (6) | 0.20987 (4) | 0.47189 (3) | 0.01634 (11) | |
S3 | 0.51845 (7) | 0.36676 (4) | 0.07081 (3) | 0.02254 (13) | |
P1 | 0.05184 (6) | 0.15244 (4) | 0.64996 (3) | 0.01168 (10) | |
P2 | 0.41455 (6) | 0.32402 (4) | 0.24144 (3) | 0.01230 (10) | |
P3 | 0.21550 (6) | 0.17470 (4) | 0.07067 (3) | 0.01362 (11) | |
N1 | 0.3296 (2) | 0.11367 (13) | 0.45141 (10) | 0.0187 (4) | |
H1 | 0.2904 | 0.1591 | 0.4711 | 0.022* | |
N2 | 0.3752 (2) | −0.01974 (14) | 0.42198 (10) | 0.0212 (4) | |
H2 | 0.3663 | −0.0748 | 0.4178 | 0.025* | |
N3 | 0.0389 (2) | 0.34962 (14) | 0.54878 (11) | 0.0213 (4) | |
H3 | 0.1202 | 0.3263 | 0.5496 | 0.026* | |
N4 | −0.1850 (2) | 0.36111 (14) | 0.52721 (11) | 0.0237 (5) | |
H4 | −0.2693 | 0.3491 | 0.5081 | 0.028* | |
N5 | 0.6169 (2) | 0.53077 (15) | 0.10791 (12) | 0.0261 (5) | |
H5 | 0.6987 | 0.5204 | 0.0935 | 0.031* | |
N6 | 0.4141 (2) | 0.50600 (14) | 0.13962 (11) | 0.0218 (4) | |
H6 | 0.3336 | 0.4795 | 0.1415 | 0.026* | |
C1 | 0.3025 (2) | 0.03624 (14) | 0.45799 (10) | 0.0140 (4) | |
C2 | 0.4331 (3) | 0.11450 (16) | 0.40730 (11) | 0.0200 (5) | |
H2A | 0.5159 | 0.1527 | 0.4258 | 0.024* | |
H2B | 0.3917 | 0.1322 | 0.3716 | 0.024* | |
C3 | 0.4719 (3) | 0.02121 (17) | 0.39010 (12) | 0.0213 (5) | |
H3A | 0.4573 | −0.0029 | 0.3458 | 0.026* | |
H3B | 0.5706 | 0.0154 | 0.4041 | 0.026* | |
C4 | −0.0783 (2) | 0.31014 (15) | 0.51795 (11) | 0.0161 (4) | |
C5 | 0.0153 (3) | 0.43661 (19) | 0.58100 (17) | 0.0362 (8) | |
H5A | 0.0616 | 0.4782 | 0.5626 | 0.043* | |
H5B | 0.0499 | 0.4480 | 0.6243 | 0.043* | |
C6 | −0.1436 (3) | 0.43931 (17) | 0.57316 (14) | 0.0265 (6) | |
H6A | −0.1855 | 0.4400 | 0.6115 | 0.032* | |
H6B | −0.1717 | 0.4896 | 0.5591 | 0.032* | |
C7 | 0.5159 (3) | 0.47123 (16) | 0.10718 (12) | 0.0190 (5) | |
N7 | 0.2420 (3) | 0.76608 (18) | 0.14911 (13) | 0.0381 (6) | |
C8 | 0.5723 (3) | 0.61517 (18) | 0.13593 (16) | 0.0312 (6) | |
H8A | 0.5381 | 0.6447 | 0.1050 | 0.037* | |
H8B | 0.6492 | 0.6504 | 0.1629 | 0.037* | |
C9 | 0.4533 (3) | 0.59427 (17) | 0.17195 (13) | 0.0246 (5) | |
H9A | 0.4864 | 0.5991 | 0.2148 | 0.030* | |
H9B | 0.3743 | 0.6313 | 0.1701 | 0.030* | |
C11 | −0.0123 (2) | 0.24930 (14) | 0.69579 (10) | 0.0142 (4) | |
C12 | 0.0554 (3) | 0.29479 (15) | 0.75139 (11) | 0.0180 (4) | |
H12 | 0.1400 | 0.2756 | 0.7666 | 0.022* | |
C13 | −0.0003 (3) | 0.36812 (17) | 0.78470 (12) | 0.0232 (5) | |
H13 | 0.0460 | 0.3985 | 0.8224 | 0.028* | |
C14 | −0.1231 (3) | 0.39624 (17) | 0.76243 (14) | 0.0264 (6) | |
H14 | −0.1606 | 0.4464 | 0.7847 | 0.032* | |
C15 | −0.1915 (3) | 0.35125 (17) | 0.70770 (14) | 0.0261 (6) | |
H15 | −0.2767 | 0.3703 | 0.6930 | 0.031* | |
C16 | −0.1362 (3) | 0.27823 (16) | 0.67406 (12) | 0.0207 (5) | |
H16 | −0.1831 | 0.2482 | 0.6363 | 0.025* | |
C21 | 0.2363 (2) | 0.15765 (14) | 0.67815 (10) | 0.0136 (4) | |
C22 | 0.2822 (3) | 0.13182 (16) | 0.72991 (11) | 0.0175 (4) | |
H22 | 0.2181 | 0.1040 | 0.7494 | 0.021* | |
C23 | 0.4223 (3) | 0.14682 (17) | 0.75313 (12) | 0.0222 (5) | |
H23 | 0.4528 | 0.1304 | 0.7889 | 0.027* | |
C24 | 0.5172 (3) | 0.18550 (17) | 0.72422 (12) | 0.0229 (5) | |
H24 | 0.6122 | 0.1965 | 0.7405 | 0.027* | |
C25 | 0.4728 (3) | 0.20824 (17) | 0.67126 (12) | 0.0212 (5) | |
H25 | 0.5384 | 0.2333 | 0.6508 | 0.025* | |
C26 | 0.3329 (2) | 0.19467 (15) | 0.64797 (11) | 0.0170 (4) | |
H26 | 0.3032 | 0.2104 | 0.6118 | 0.020* | |
C31 | −0.0272 (2) | 0.06841 (14) | 0.67890 (10) | 0.0131 (4) | |
C30 | 0.3989 (2) | 0.33050 (16) | 0.51551 (11) | 0.0175 (4) | |
C32 | −0.1146 (2) | 0.08315 (16) | 0.72606 (11) | 0.0175 (4) | |
H32 | −0.1337 | 0.1395 | 0.7457 | 0.021* | |
C33 | −0.1739 (3) | 0.01499 (18) | 0.74438 (12) | 0.0225 (5) | |
H33 | −0.2336 | 0.0251 | 0.7764 | 0.027* | |
C34 | −0.1459 (3) | −0.06732 (18) | 0.71596 (12) | 0.0235 (5) | |
H34 | −0.1862 | −0.1134 | 0.7287 | 0.028* | |
C35 | −0.0590 (3) | −0.08267 (16) | 0.66897 (12) | 0.0218 (5) | |
H35 | −0.0397 | −0.1392 | 0.6497 | 0.026* | |
C36 | −0.0004 (3) | −0.01517 (15) | 0.65027 (11) | 0.0172 (4) | |
H36 | 0.0582 | −0.0258 | 0.6179 | 0.021* | |
C41 | 0.5210 (2) | 0.42249 (15) | 0.27211 (10) | 0.0145 (4) | |
C40 | 0.3705 (3) | 0.41859 (18) | 0.50781 (15) | 0.0291 (6) | |
H40A | 0.4002 | 0.4241 | 0.4688 | 0.044* | |
H40B | 0.4229 | 0.4611 | 0.5407 | 0.044* | |
H40C | 0.2700 | 0.4273 | 0.5089 | 0.044* | |
C42 | 0.6444 (3) | 0.43300 (16) | 0.24514 (12) | 0.0190 (5) | |
H42 | 0.6721 | 0.3887 | 0.2135 | 0.023* | |
C43 | 0.7267 (3) | 0.50853 (17) | 0.26481 (13) | 0.0232 (5) | |
H43 | 0.8117 | 0.5149 | 0.2472 | 0.028* | |
C44 | 0.6852 (3) | 0.57443 (17) | 0.30988 (13) | 0.0251 (5) | |
H44 | 0.7412 | 0.6259 | 0.3229 | 0.030* | |
C45 | 0.5623 (3) | 0.56490 (16) | 0.33580 (12) | 0.0237 (5) | |
H45 | 0.5330 | 0.6103 | 0.3662 | 0.028* | |
C46 | 0.4808 (3) | 0.48901 (16) | 0.31759 (11) | 0.0195 (5) | |
H46 | 0.3973 | 0.4826 | 0.3363 | 0.023* | |
C51 | 0.5182 (2) | 0.24246 (15) | 0.26282 (10) | 0.0141 (4) | |
C50 | 0.0661 (2) | 0.41834 (15) | 0.11199 (11) | 0.0161 (4) | |
C52 | 0.4795 (3) | 0.15807 (15) | 0.23323 (11) | 0.0171 (4) | |
H52 | 0.4037 | 0.1458 | 0.2025 | 0.021* | |
C53 | 0.5502 (3) | 0.09187 (17) | 0.24805 (12) | 0.0217 (5) | |
H53 | 0.5226 | 0.0348 | 0.2277 | 0.026* | |
C54 | 0.6620 (3) | 0.10971 (17) | 0.29293 (12) | 0.0218 (5) | |
H54 | 0.7109 | 0.0648 | 0.3032 | 0.026* | |
C55 | 0.7016 (3) | 0.19306 (18) | 0.32251 (12) | 0.0227 (5) | |
H55 | 0.7778 | 0.2050 | 0.3530 | 0.027* | |
C56 | 0.6304 (3) | 0.25949 (17) | 0.30779 (11) | 0.0195 (5) | |
H56 | 0.6581 | 0.3164 | 0.3283 | 0.023* | |
C61 | 0.2704 (2) | 0.33088 (14) | 0.29028 (10) | 0.0138 (4) | |
C60 | −0.0750 (3) | 0.39096 (18) | 0.12854 (13) | 0.0230 (5) | |
H60A | −0.1242 | 0.3505 | 0.0935 | 0.034* | |
H60B | −0.1308 | 0.4406 | 0.1405 | 0.034* | |
H60C | −0.0614 | 0.3641 | 0.1624 | 0.034* | |
C62 | 0.2795 (3) | 0.30307 (16) | 0.34366 (11) | 0.0178 (4) | |
H62 | 0.3643 | 0.2817 | 0.3566 | 0.021* | |
C63 | 0.1651 (3) | 0.30661 (16) | 0.37794 (11) | 0.0193 (5) | |
H63 | 0.1717 | 0.2873 | 0.4140 | 0.023* | |
C64 | 0.0407 (3) | 0.33849 (16) | 0.35943 (11) | 0.0199 (5) | |
H64 | −0.0376 | 0.3406 | 0.3827 | 0.024* | |
C65 | 0.0315 (3) | 0.36712 (18) | 0.30680 (12) | 0.0223 (5) | |
H65 | −0.0528 | 0.3897 | 0.2945 | 0.027* | |
C66 | 0.1455 (3) | 0.36293 (17) | 0.27185 (11) | 0.0188 (5) | |
H66 | 0.1382 | 0.3818 | 0.2356 | 0.023* | |
C71 | 0.2823 (2) | 0.07331 (15) | 0.07579 (10) | 0.0159 (4) | |
C72 | 0.4256 (3) | 0.06359 (19) | 0.07134 (13) | 0.0255 (5) | |
H72 | 0.4830 | 0.1080 | 0.0640 | 0.031* | |
C73 | 0.4845 (3) | −0.0111 (2) | 0.07757 (15) | 0.0324 (6) | |
H73 | 0.5818 | −0.0176 | 0.0740 | 0.039* | |
C74 | 0.4020 (3) | −0.07579 (19) | 0.08886 (13) | 0.0299 (6) | |
H74 | 0.4428 | −0.1263 | 0.0937 | 0.036* | |
C75 | 0.2597 (3) | −0.06688 (18) | 0.09311 (13) | 0.0283 (6) | |
H75 | 0.2027 | −0.1115 | 0.1004 | 0.034* | |
C76 | 0.2004 (3) | 0.00746 (17) | 0.08673 (12) | 0.0224 (5) | |
H76 | 0.1028 | 0.0133 | 0.0899 | 0.027* | |
C81 | 0.0388 (2) | 0.17016 (15) | 0.09452 (11) | 0.0161 (4) | |
C82 | 0.0243 (3) | 0.17916 (18) | 0.15620 (12) | 0.0234 (5) | |
H82 | 0.1054 | 0.1864 | 0.1840 | 0.028* | |
C83 | −0.1077 (3) | 0.1775 (2) | 0.17707 (13) | 0.0307 (6) | |
H83 | −0.1167 | 0.1828 | 0.2189 | 0.037* | |
C84 | −0.2265 (3) | 0.1683 (2) | 0.13677 (14) | 0.0336 (7) | |
H84 | −0.3169 | 0.1678 | 0.1510 | 0.040* | |
C85 | −0.2131 (3) | 0.1599 (2) | 0.07591 (14) | 0.0320 (7) | |
H85 | −0.2947 | 0.1537 | 0.0485 | 0.038* | |
C86 | −0.0806 (3) | 0.16040 (18) | 0.05428 (12) | 0.0238 (5) | |
H86 | −0.0723 | 0.1541 | 0.0123 | 0.029* | |
C91 | 0.1855 (2) | 0.16749 (15) | −0.00985 (10) | 0.0146 (4) | |
C92 | 0.1600 (2) | 0.09072 (16) | −0.05353 (11) | 0.0168 (4) | |
H92 | 0.1673 | 0.0387 | −0.0421 | 0.020* | |
C93 | 0.1239 (3) | 0.09019 (18) | −0.11384 (11) | 0.0218 (5) | |
H93 | 0.1083 | 0.0379 | −0.1436 | 0.026* | |
C94 | 0.1108 (3) | 0.16631 (18) | −0.13052 (11) | 0.0231 (5) | |
H94 | 0.0826 | 0.1659 | −0.1714 | 0.028* | |
C95 | 0.1388 (3) | 0.24292 (17) | −0.08762 (12) | 0.0224 (5) | |
H95 | 0.1314 | 0.2948 | −0.0993 | 0.027* | |
C96 | 0.1776 (3) | 0.24370 (16) | −0.02761 (11) | 0.0197 (5) | |
H96 | 0.1989 | 0.2961 | 0.0015 | 0.024* | |
O1 | 0.29782 (18) | 0.28441 (11) | 0.52369 (8) | 0.0178 (3) | |
O2 | 0.52335 (19) | 0.30909 (13) | 0.51366 (10) | 0.0287 (4) | |
O4 | 0.17335 (17) | 0.40868 (11) | 0.14454 (8) | 0.0181 (3) | |
O6 | 0.0685 (2) | 0.45087 (16) | 0.06758 (10) | 0.0339 (5) | |
O7 | −0.1503 (2) | 0.54379 (13) | 0.04566 (9) | 0.0258 (4) | |
H7A | −0.088 (3) | 0.5092 (18) | 0.0496 (16) | 0.031* | |
H7B | −0.153 (4) | 0.543 (2) | 0.0086 (6) | 0.031* | |
O8 | 0.6376 (2) | 0.17707 (13) | 0.54856 (9) | 0.0254 (4) | |
H8C | 0.591 (3) | 0.2133 (17) | 0.5363 (15) | 0.030* | |
H8D | 0.699 (3) | 0.172 (2) | 0.5241 (12) | 0.030* | |
C10 | 0.2216 (3) | 0.71407 (19) | 0.10551 (14) | 0.0289 (6) | |
C20 | 0.1970 (4) | 0.6458 (2) | 0.05039 (15) | 0.0396 (8) | |
H20A | 0.1073 | 0.6525 | 0.0288 | 0.059* | |
H20B | 0.1943 | 0.5911 | 0.0610 | 0.059* | |
H20C | 0.2728 | 0.6480 | 0.0243 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.01534 (8) | 0.01640 (8) | 0.01295 (8) | −0.00237 (6) | −0.00027 (6) | 0.00259 (6) |
Ag2 | 0.01955 (9) | 0.01800 (9) | 0.01197 (8) | 0.00333 (6) | 0.00106 (6) | 0.00327 (6) |
S1 | 0.0137 (2) | 0.0150 (3) | 0.0165 (3) | −0.00022 (19) | 0.00441 (19) | 0.0032 (2) |
S2 | 0.0175 (3) | 0.0181 (3) | 0.0138 (2) | −0.0006 (2) | −0.0003 (2) | 0.0055 (2) |
S3 | 0.0233 (3) | 0.0220 (3) | 0.0224 (3) | −0.0022 (2) | 0.0107 (2) | 0.0033 (2) |
P1 | 0.0120 (2) | 0.0129 (3) | 0.0099 (2) | 0.00055 (19) | 0.00173 (19) | 0.00199 (19) |
P2 | 0.0120 (2) | 0.0137 (3) | 0.0110 (2) | −0.0001 (2) | 0.00039 (19) | 0.0031 (2) |
P3 | 0.0127 (3) | 0.0154 (3) | 0.0118 (2) | −0.0029 (2) | 0.0012 (2) | 0.0020 (2) |
N1 | 0.0195 (10) | 0.0164 (10) | 0.0210 (10) | 0.0005 (8) | 0.0085 (8) | 0.0038 (8) |
N2 | 0.0245 (11) | 0.0150 (10) | 0.0255 (11) | 0.0020 (8) | 0.0122 (9) | 0.0045 (8) |
N3 | 0.0115 (9) | 0.0175 (10) | 0.0316 (12) | 0.0023 (7) | −0.0015 (8) | 0.0007 (9) |
N4 | 0.0117 (9) | 0.0199 (11) | 0.0378 (13) | 0.0011 (8) | −0.0014 (9) | 0.0051 (9) |
N5 | 0.0183 (10) | 0.0225 (11) | 0.0388 (14) | −0.0011 (8) | 0.0103 (9) | 0.0081 (10) |
N6 | 0.0159 (10) | 0.0192 (10) | 0.0301 (12) | −0.0022 (8) | 0.0063 (8) | 0.0046 (9) |
C1 | 0.0126 (10) | 0.0140 (10) | 0.0142 (10) | −0.0011 (8) | 0.0010 (8) | 0.0016 (8) |
C2 | 0.0204 (12) | 0.0207 (12) | 0.0191 (11) | −0.0028 (9) | 0.0065 (9) | 0.0042 (9) |
C3 | 0.0200 (12) | 0.0243 (13) | 0.0225 (12) | 0.0031 (9) | 0.0106 (9) | 0.0083 (10) |
C4 | 0.0135 (10) | 0.0167 (11) | 0.0200 (11) | −0.0002 (8) | 0.0024 (8) | 0.0082 (9) |
C5 | 0.0166 (12) | 0.0214 (14) | 0.060 (2) | 0.0029 (10) | −0.0037 (13) | −0.0095 (13) |
C6 | 0.0192 (12) | 0.0206 (13) | 0.0376 (15) | 0.0052 (10) | 0.0014 (11) | 0.0032 (11) |
C7 | 0.0157 (11) | 0.0209 (12) | 0.0225 (12) | −0.0014 (9) | 0.0033 (9) | 0.0092 (9) |
N7 | 0.0502 (17) | 0.0299 (14) | 0.0330 (14) | 0.0094 (12) | −0.0059 (12) | 0.0074 (11) |
C8 | 0.0243 (14) | 0.0217 (13) | 0.0487 (18) | −0.0023 (11) | 0.0091 (12) | 0.0094 (12) |
C9 | 0.0216 (12) | 0.0203 (12) | 0.0329 (14) | 0.0025 (10) | 0.0040 (10) | 0.0076 (11) |
C11 | 0.0142 (10) | 0.0136 (10) | 0.0147 (10) | −0.0002 (8) | 0.0034 (8) | 0.0031 (8) |
C12 | 0.0200 (11) | 0.0167 (11) | 0.0165 (11) | −0.0005 (9) | 0.0032 (9) | 0.0023 (9) |
C13 | 0.0264 (13) | 0.0185 (12) | 0.0215 (12) | −0.0042 (10) | 0.0077 (10) | −0.0021 (9) |
C14 | 0.0273 (13) | 0.0164 (12) | 0.0351 (15) | 0.0033 (10) | 0.0168 (11) | 0.0008 (10) |
C15 | 0.0201 (12) | 0.0205 (13) | 0.0388 (16) | 0.0064 (10) | 0.0070 (11) | 0.0072 (11) |
C16 | 0.0172 (11) | 0.0196 (12) | 0.0232 (12) | 0.0030 (9) | 0.0013 (9) | 0.0014 (9) |
C21 | 0.0139 (10) | 0.0128 (10) | 0.0132 (10) | 0.0005 (8) | 0.0019 (8) | 0.0013 (8) |
C22 | 0.0174 (11) | 0.0190 (11) | 0.0166 (11) | 0.0026 (9) | 0.0016 (8) | 0.0052 (9) |
C23 | 0.0210 (12) | 0.0243 (13) | 0.0198 (12) | 0.0059 (10) | −0.0027 (9) | 0.0034 (10) |
C24 | 0.0148 (11) | 0.0221 (12) | 0.0276 (13) | 0.0020 (9) | −0.0006 (9) | −0.0010 (10) |
C25 | 0.0155 (11) | 0.0217 (12) | 0.0246 (12) | −0.0030 (9) | 0.0070 (9) | 0.0011 (10) |
C26 | 0.0160 (11) | 0.0173 (11) | 0.0173 (11) | 0.0002 (8) | 0.0039 (8) | 0.0030 (9) |
C31 | 0.0117 (9) | 0.0152 (10) | 0.0119 (9) | −0.0014 (8) | −0.0009 (7) | 0.0035 (8) |
C30 | 0.0147 (10) | 0.0178 (11) | 0.0203 (11) | −0.0007 (8) | −0.0004 (8) | 0.0059 (9) |
C32 | 0.0165 (11) | 0.0212 (12) | 0.0136 (10) | −0.0009 (9) | 0.0026 (8) | 0.0018 (9) |
C33 | 0.0209 (12) | 0.0299 (14) | 0.0177 (11) | −0.0035 (10) | 0.0045 (9) | 0.0074 (10) |
C34 | 0.0216 (12) | 0.0262 (13) | 0.0251 (13) | −0.0058 (10) | −0.0003 (10) | 0.0127 (10) |
C35 | 0.0236 (12) | 0.0172 (11) | 0.0256 (13) | −0.0007 (9) | 0.0025 (10) | 0.0074 (10) |
C36 | 0.0187 (11) | 0.0166 (11) | 0.0165 (11) | 0.0002 (9) | 0.0040 (8) | 0.0037 (9) |
C41 | 0.0162 (10) | 0.0154 (10) | 0.0121 (10) | −0.0008 (8) | −0.0012 (8) | 0.0049 (8) |
C40 | 0.0271 (14) | 0.0197 (13) | 0.0434 (17) | −0.0021 (10) | 0.0022 (12) | 0.0143 (12) |
C42 | 0.0168 (11) | 0.0184 (11) | 0.0212 (12) | −0.0023 (9) | 0.0027 (9) | 0.0043 (9) |
C43 | 0.0172 (11) | 0.0233 (13) | 0.0299 (14) | −0.0054 (9) | 0.0009 (10) | 0.0093 (10) |
C44 | 0.0254 (13) | 0.0175 (12) | 0.0308 (14) | −0.0034 (10) | −0.0065 (11) | 0.0064 (10) |
C45 | 0.0304 (14) | 0.0160 (11) | 0.0213 (12) | −0.0001 (10) | −0.0025 (10) | −0.0004 (9) |
C46 | 0.0209 (12) | 0.0199 (12) | 0.0167 (11) | 0.0019 (9) | 0.0022 (9) | 0.0023 (9) |
C51 | 0.0137 (10) | 0.0167 (10) | 0.0130 (10) | 0.0006 (8) | 0.0032 (8) | 0.0054 (8) |
C50 | 0.0168 (11) | 0.0163 (11) | 0.0160 (10) | 0.0029 (8) | 0.0036 (8) | 0.0047 (8) |
C52 | 0.0169 (11) | 0.0180 (11) | 0.0168 (11) | 0.0002 (8) | 0.0032 (8) | 0.0049 (9) |
C53 | 0.0241 (12) | 0.0178 (12) | 0.0237 (12) | 0.0023 (9) | 0.0053 (10) | 0.0051 (9) |
C54 | 0.0200 (12) | 0.0257 (13) | 0.0245 (12) | 0.0067 (10) | 0.0070 (9) | 0.0133 (10) |
C55 | 0.0176 (11) | 0.0305 (14) | 0.0226 (12) | 0.0019 (10) | −0.0022 (9) | 0.0124 (10) |
C56 | 0.0170 (11) | 0.0210 (12) | 0.0199 (11) | −0.0007 (9) | −0.0020 (9) | 0.0054 (9) |
C61 | 0.0127 (10) | 0.0148 (10) | 0.0131 (10) | −0.0015 (8) | 0.0015 (8) | 0.0022 (8) |
C60 | 0.0142 (11) | 0.0269 (13) | 0.0304 (14) | 0.0000 (9) | 0.0018 (9) | 0.0122 (11) |
C62 | 0.0189 (11) | 0.0210 (12) | 0.0145 (10) | 0.0020 (9) | 0.0016 (8) | 0.0062 (9) |
C63 | 0.0240 (12) | 0.0194 (11) | 0.0159 (11) | −0.0015 (9) | 0.0045 (9) | 0.0069 (9) |
C64 | 0.0177 (11) | 0.0216 (12) | 0.0200 (11) | −0.0020 (9) | 0.0070 (9) | 0.0031 (9) |
C65 | 0.0165 (11) | 0.0315 (14) | 0.0214 (12) | 0.0062 (10) | 0.0049 (9) | 0.0093 (10) |
C66 | 0.0158 (11) | 0.0267 (13) | 0.0163 (11) | 0.0034 (9) | 0.0031 (8) | 0.0096 (9) |
C71 | 0.0153 (10) | 0.0197 (11) | 0.0120 (10) | −0.0001 (8) | 0.0003 (8) | 0.0031 (8) |
C72 | 0.0166 (12) | 0.0298 (14) | 0.0309 (14) | 0.0018 (10) | 0.0053 (10) | 0.0082 (11) |
C73 | 0.0232 (14) | 0.0375 (17) | 0.0369 (16) | 0.0122 (12) | 0.0029 (12) | 0.0085 (13) |
C74 | 0.0380 (16) | 0.0276 (14) | 0.0237 (13) | 0.0110 (12) | −0.0027 (11) | 0.0059 (11) |
C75 | 0.0359 (15) | 0.0226 (13) | 0.0267 (14) | 0.0001 (11) | −0.0005 (11) | 0.0080 (11) |
C76 | 0.0211 (12) | 0.0211 (12) | 0.0245 (13) | −0.0007 (9) | 0.0012 (10) | 0.0050 (10) |
C81 | 0.0155 (10) | 0.0158 (11) | 0.0163 (10) | −0.0026 (8) | 0.0044 (8) | 0.0024 (8) |
C82 | 0.0228 (12) | 0.0295 (14) | 0.0182 (12) | −0.0027 (10) | 0.0054 (9) | 0.0058 (10) |
C83 | 0.0321 (15) | 0.0379 (16) | 0.0224 (13) | −0.0029 (12) | 0.0153 (11) | 0.0046 (12) |
C84 | 0.0222 (13) | 0.0395 (17) | 0.0350 (16) | −0.0066 (12) | 0.0158 (12) | −0.0014 (13) |
C85 | 0.0150 (12) | 0.0482 (19) | 0.0289 (14) | −0.0052 (12) | 0.0057 (10) | 0.0020 (13) |
C86 | 0.0155 (11) | 0.0340 (15) | 0.0197 (12) | −0.0047 (10) | 0.0042 (9) | 0.0024 (10) |
C91 | 0.0106 (9) | 0.0182 (11) | 0.0142 (10) | −0.0019 (8) | 0.0015 (8) | 0.0030 (8) |
C92 | 0.0158 (10) | 0.0185 (11) | 0.0156 (10) | −0.0012 (8) | 0.0038 (8) | 0.0025 (8) |
C93 | 0.0214 (12) | 0.0270 (13) | 0.0145 (11) | −0.0012 (10) | 0.0035 (9) | 0.0001 (9) |
C94 | 0.0211 (12) | 0.0337 (14) | 0.0141 (11) | −0.0007 (10) | 0.0019 (9) | 0.0057 (10) |
C95 | 0.0247 (13) | 0.0245 (13) | 0.0197 (12) | 0.0006 (10) | 0.0022 (9) | 0.0088 (10) |
C96 | 0.0209 (12) | 0.0191 (12) | 0.0188 (11) | −0.0010 (9) | 0.0028 (9) | 0.0039 (9) |
O1 | 0.0140 (8) | 0.0153 (8) | 0.0240 (9) | −0.0006 (6) | 0.0032 (6) | 0.0045 (7) |
O2 | 0.0113 (8) | 0.0303 (11) | 0.0466 (13) | 0.0004 (7) | 0.0039 (8) | 0.0133 (9) |
O4 | 0.0128 (8) | 0.0234 (9) | 0.0193 (8) | 0.0024 (6) | 0.0015 (6) | 0.0075 (7) |
O6 | 0.0216 (10) | 0.0611 (15) | 0.0306 (11) | 0.0087 (10) | 0.0066 (8) | 0.0312 (11) |
O7 | 0.0241 (10) | 0.0294 (10) | 0.0280 (10) | 0.0050 (8) | 0.0099 (8) | 0.0124 (8) |
O8 | 0.0221 (9) | 0.0290 (10) | 0.0298 (10) | 0.0070 (8) | 0.0111 (8) | 0.0126 (8) |
C10 | 0.0291 (14) | 0.0287 (15) | 0.0308 (15) | 0.0032 (11) | 0.0002 (11) | 0.0117 (12) |
C20 | 0.0369 (17) | 0.0422 (19) | 0.0332 (17) | −0.0070 (14) | 0.0029 (13) | −0.0016 (14) |
Ag1—P3 | 2.4381 (6) | C34—H34 | 0.9500 |
Ag1—P2 | 2.4744 (6) | C35—C36 | 1.391 (3) |
Ag1—S3 | 2.5424 (7) | C35—H35 | 0.9500 |
Ag1—O4 | 2.5564 (17) | C36—H36 | 0.9500 |
Ag2—P1 | 2.4431 (6) | C41—C46 | 1.394 (3) |
Ag2—S2 | 2.5200 (6) | C41—C42 | 1.400 (3) |
Ag2—S1 | 2.5810 (6) | C40—H40A | 0.9800 |
Ag2—S1i | 2.7883 (6) | C40—H40B | 0.9800 |
S1—C1 | 1.715 (2) | C40—H40C | 0.9800 |
S1—Ag2i | 2.7883 (6) | C42—C43 | 1.395 (3) |
S2—C4 | 1.708 (3) | C42—H42 | 0.9500 |
S3—C7 | 1.704 (3) | C43—C44 | 1.387 (4) |
P1—C11 | 1.824 (2) | C43—H43 | 0.9500 |
P1—C21 | 1.826 (2) | C44—C45 | 1.380 (4) |
P1—C31 | 1.827 (2) | C44—H44 | 0.9500 |
P2—C51 | 1.824 (2) | C45—C46 | 1.395 (4) |
P2—C41 | 1.826 (2) | C45—H45 | 0.9500 |
P2—C61 | 1.832 (2) | C46—H46 | 0.9500 |
P3—C91 | 1.814 (2) | C51—C52 | 1.399 (3) |
P3—C71 | 1.820 (3) | C51—C56 | 1.399 (3) |
P3—C81 | 1.824 (2) | C50—O6 | 1.256 (3) |
N1—C1 | 1.327 (3) | C50—O4 | 1.259 (3) |
N1—C2 | 1.470 (3) | C50—C60 | 1.514 (3) |
N1—H1 | 0.8800 | C52—C53 | 1.390 (3) |
N2—C1 | 1.327 (3) | C52—H52 | 0.9500 |
N2—C3 | 1.462 (3) | C53—C54 | 1.395 (4) |
N2—H2 | 0.8800 | C53—H53 | 0.9500 |
N3—C4 | 1.333 (3) | C54—C55 | 1.386 (4) |
N3—C5 | 1.463 (3) | C54—H54 | 0.9500 |
N3—H3 | 0.8800 | C55—C56 | 1.395 (4) |
N4—C4 | 1.337 (3) | C55—H55 | 0.9500 |
N4—C6 | 1.460 (4) | C56—H56 | 0.9500 |
N4—H4 | 0.8800 | C61—C66 | 1.399 (3) |
N5—C7 | 1.343 (3) | C61—C62 | 1.399 (3) |
N5—C8 | 1.462 (4) | C60—H60A | 0.9800 |
N5—H5 | 0.8800 | C60—H60B | 0.9800 |
N6—C7 | 1.330 (3) | C60—H60C | 0.9800 |
N6—C9 | 1.468 (3) | C62—C63 | 1.392 (3) |
N6—H6 | 0.8800 | C62—H62 | 0.9500 |
C2—C3 | 1.541 (4) | C63—C64 | 1.394 (4) |
C2—H2A | 0.9900 | C63—H63 | 0.9500 |
C2—H2B | 0.9900 | C64—C65 | 1.391 (4) |
C3—H3A | 0.9900 | C64—H64 | 0.9500 |
C3—H3B | 0.9900 | C65—C66 | 1.397 (3) |
C5—C6 | 1.523 (4) | C65—H65 | 0.9500 |
C5—H5A | 0.9900 | C66—H66 | 0.9500 |
C5—H5B | 0.9900 | C71—C76 | 1.391 (3) |
C6—H6A | 0.9900 | C71—C72 | 1.397 (3) |
C6—H6B | 0.9900 | C72—C73 | 1.394 (4) |
N7—C10 | 1.138 (4) | C72—H72 | 0.9500 |
C8—C9 | 1.533 (4) | C73—C74 | 1.382 (5) |
C8—H8A | 0.9900 | C73—H73 | 0.9500 |
C8—H8B | 0.9900 | C74—C75 | 1.385 (4) |
C9—H9A | 0.9900 | C74—H74 | 0.9500 |
C9—H9B | 0.9900 | C75—C76 | 1.391 (4) |
C11—C16 | 1.394 (3) | C75—H75 | 0.9500 |
C11—C12 | 1.401 (3) | C76—H76 | 0.9500 |
C12—C13 | 1.398 (3) | C81—C86 | 1.391 (3) |
C12—H12 | 0.9500 | C81—C82 | 1.400 (3) |
C13—C14 | 1.384 (4) | C82—C83 | 1.388 (4) |
C13—H13 | 0.9500 | C82—H82 | 0.9500 |
C14—C15 | 1.386 (4) | C83—C84 | 1.387 (5) |
C14—H14 | 0.9500 | C83—H83 | 0.9500 |
C15—C16 | 1.396 (4) | C84—C85 | 1.380 (4) |
C15—H15 | 0.9500 | C84—H84 | 0.9500 |
C16—H16 | 0.9500 | C85—C86 | 1.398 (4) |
C21—C22 | 1.395 (3) | C85—H85 | 0.9500 |
C21—C26 | 1.400 (3) | C86—H86 | 0.9500 |
C22—C23 | 1.396 (3) | C91—C92 | 1.397 (3) |
C22—H22 | 0.9500 | C91—C96 | 1.401 (3) |
C23—C24 | 1.385 (4) | C92—C93 | 1.393 (3) |
C23—H23 | 0.9500 | C92—H92 | 0.9500 |
C24—C25 | 1.391 (4) | C93—C94 | 1.391 (4) |
C24—H24 | 0.9500 | C93—H93 | 0.9500 |
C25—C26 | 1.394 (3) | C94—C95 | 1.389 (4) |
C25—H25 | 0.9500 | C94—H94 | 0.9500 |
C26—H26 | 0.9500 | C95—C96 | 1.390 (3) |
C31—C32 | 1.396 (3) | C95—H95 | 0.9500 |
C31—C36 | 1.402 (3) | C96—H96 | 0.9500 |
C30—O2 | 1.255 (3) | O7—H7A | 0.848 (10) |
C30—O1 | 1.259 (3) | O7—H7B | 0.844 (10) |
C30—C40 | 1.520 (4) | O8—H8C | 0.842 (10) |
C32—C33 | 1.398 (4) | O8—H8D | 0.837 (10) |
C32—H32 | 0.9500 | C10—C20 | 1.459 (4) |
C33—C34 | 1.385 (4) | C20—H20A | 0.9800 |
C33—H33 | 0.9500 | C20—H20B | 0.9800 |
C34—C35 | 1.390 (4) | C20—H20C | 0.9800 |
P3—Ag1—P2 | 123.16 (2) | C34—C33—H33 | 119.9 |
P3—Ag1—S3 | 114.75 (2) | C32—C33—H33 | 119.9 |
P2—Ag1—S3 | 118.40 (2) | C33—C34—C35 | 120.2 (2) |
P3—Ag1—O4 | 99.89 (4) | C33—C34—H34 | 119.9 |
P2—Ag1—O4 | 91.92 (4) | C35—C34—H34 | 119.9 |
S3—Ag1—O4 | 97.56 (4) | C34—C35—C36 | 119.9 (2) |
P1—Ag2—S2 | 130.88 (2) | C34—C35—H35 | 120.1 |
P1—Ag2—S1 | 100.98 (2) | C36—C35—H35 | 120.1 |
S2—Ag2—S1 | 122.99 (2) | C35—C36—C31 | 120.4 (2) |
P1—Ag2—S1i | 112.706 (19) | C35—C36—H36 | 119.8 |
S2—Ag2—S1i | 92.547 (19) | C31—C36—H36 | 119.8 |
S1—Ag2—S1i | 86.195 (19) | C46—C41—C42 | 119.1 (2) |
C1—S1—Ag2 | 113.31 (8) | C46—C41—P2 | 123.41 (19) |
C1—S1—Ag2i | 117.47 (8) | C42—C41—P2 | 117.39 (18) |
Ag2—S1—Ag2i | 93.806 (19) | C30—C40—H40A | 109.5 |
C4—S2—Ag2 | 103.55 (8) | C30—C40—H40B | 109.5 |
C7—S3—Ag1 | 101.86 (9) | H40A—C40—H40B | 109.5 |
C11—P1—C21 | 103.14 (10) | C30—C40—H40C | 109.5 |
C11—P1—C31 | 103.96 (10) | H40A—C40—H40C | 109.5 |
C21—P1—C31 | 103.77 (10) | H40B—C40—H40C | 109.5 |
C11—P1—Ag2 | 119.00 (8) | C43—C42—C41 | 119.9 (2) |
C21—P1—Ag2 | 114.48 (8) | C43—C42—H42 | 120.0 |
C31—P1—Ag2 | 110.90 (7) | C41—C42—H42 | 120.0 |
C51—P2—C41 | 104.65 (11) | C44—C43—C42 | 120.5 (2) |
C51—P2—C61 | 102.56 (10) | C44—C43—H43 | 119.8 |
C41—P2—C61 | 104.66 (11) | C42—C43—H43 | 119.8 |
C51—P2—Ag1 | 113.13 (8) | C45—C44—C43 | 119.7 (2) |
C41—P2—Ag1 | 111.70 (7) | C45—C44—H44 | 120.1 |
C61—P2—Ag1 | 118.76 (7) | C43—C44—H44 | 120.1 |
C91—P3—C71 | 105.22 (11) | C44—C45—C46 | 120.4 (2) |
C91—P3—C81 | 103.32 (11) | C44—C45—H45 | 119.8 |
C71—P3—C81 | 103.63 (11) | C46—C45—H45 | 119.8 |
C91—P3—Ag1 | 116.27 (8) | C41—C46—C45 | 120.4 (2) |
C71—P3—Ag1 | 114.34 (8) | C41—C46—H46 | 119.8 |
C81—P3—Ag1 | 112.68 (8) | C45—C46—H46 | 119.8 |
C1—N1—C2 | 111.9 (2) | C52—C51—C56 | 118.8 (2) |
C1—N1—H1 | 124.0 | C52—C51—P2 | 117.31 (17) |
C2—N1—H1 | 124.0 | C56—C51—P2 | 123.89 (19) |
C1—N2—C3 | 111.8 (2) | O6—C50—O4 | 124.2 (2) |
C1—N2—H2 | 124.1 | O6—C50—C60 | 118.0 (2) |
C3—N2—H2 | 124.1 | O4—C50—C60 | 117.7 (2) |
C4—N3—C5 | 111.5 (2) | C53—C52—C51 | 121.0 (2) |
C4—N3—H3 | 124.3 | C53—C52—H52 | 119.5 |
C5—N3—H3 | 124.3 | C51—C52—H52 | 119.5 |
C4—N4—C6 | 111.2 (2) | C52—C53—C54 | 119.6 (2) |
C4—N4—H4 | 124.4 | C52—C53—H53 | 120.2 |
C6—N4—H4 | 124.4 | C54—C53—H53 | 120.2 |
C7—N5—C8 | 110.7 (2) | C55—C54—C53 | 120.0 (2) |
C7—N5—H5 | 124.6 | C55—C54—H54 | 120.0 |
C8—N5—H5 | 124.6 | C53—C54—H54 | 120.0 |
C7—N6—C9 | 111.3 (2) | C54—C55—C56 | 120.5 (2) |
C7—N6—H6 | 124.4 | C54—C55—H55 | 119.8 |
C9—N6—H6 | 124.4 | C56—C55—H55 | 119.8 |
N1—C1—N2 | 110.7 (2) | C55—C56—C51 | 120.2 (2) |
N1—C1—S1 | 125.64 (18) | C55—C56—H56 | 119.9 |
N2—C1—S1 | 123.62 (18) | C51—C56—H56 | 119.9 |
N1—C2—C3 | 102.27 (19) | C66—C61—C62 | 119.4 (2) |
N1—C2—H2A | 111.3 | C66—C61—P2 | 117.91 (17) |
C3—C2—H2A | 111.3 | C62—C61—P2 | 122.62 (18) |
N1—C2—H2B | 111.3 | C50—C60—H60A | 109.5 |
C3—C2—H2B | 111.3 | C50—C60—H60B | 109.5 |
H2A—C2—H2B | 109.2 | H60A—C60—H60B | 109.5 |
N2—C3—C2 | 102.88 (19) | C50—C60—H60C | 109.5 |
N2—C3—H3A | 111.2 | H60A—C60—H60C | 109.5 |
C2—C3—H3A | 111.2 | H60B—C60—H60C | 109.5 |
N2—C3—H3B | 111.2 | C63—C62—C61 | 120.4 (2) |
C2—C3—H3B | 111.2 | C63—C62—H62 | 119.8 |
H3A—C3—H3B | 109.1 | C61—C62—H62 | 119.8 |
N3—C4—N4 | 110.2 (2) | C62—C63—C64 | 120.1 (2) |
N3—C4—S2 | 124.90 (19) | C62—C63—H63 | 120.0 |
N4—C4—S2 | 124.93 (19) | C64—C63—H63 | 120.0 |
N3—C5—C6 | 102.7 (2) | C65—C64—C63 | 119.9 (2) |
N3—C5—H5A | 111.2 | C65—C64—H64 | 120.1 |
C6—C5—H5A | 111.2 | C63—C64—H64 | 120.1 |
N3—C5—H5B | 111.2 | C64—C65—C66 | 120.4 (2) |
C6—C5—H5B | 111.2 | C64—C65—H65 | 119.8 |
H5A—C5—H5B | 109.1 | C66—C65—H65 | 119.8 |
N4—C6—C5 | 102.9 (2) | C65—C66—C61 | 119.9 (2) |
N4—C6—H6A | 111.2 | C65—C66—H66 | 120.1 |
C5—C6—H6A | 111.2 | C61—C66—H66 | 120.1 |
N4—C6—H6B | 111.2 | C76—C71—C72 | 118.8 (2) |
C5—C6—H6B | 111.2 | C76—C71—P3 | 123.77 (19) |
H6A—C6—H6B | 109.1 | C72—C71—P3 | 117.33 (19) |
N6—C7—N5 | 109.7 (2) | C73—C72—C71 | 120.2 (3) |
N6—C7—S3 | 125.12 (19) | C73—C72—H72 | 119.9 |
N5—C7—S3 | 125.2 (2) | C71—C72—H72 | 119.9 |
N5—C8—C9 | 101.7 (2) | C74—C73—C72 | 120.3 (3) |
N5—C8—H8A | 111.4 | C74—C73—H73 | 119.8 |
C9—C8—H8A | 111.4 | C72—C73—H73 | 119.8 |
N5—C8—H8B | 111.4 | C73—C74—C75 | 119.9 (3) |
C9—C8—H8B | 111.4 | C73—C74—H74 | 120.1 |
H8A—C8—H8B | 109.3 | C75—C74—H74 | 120.1 |
N6—C9—C8 | 101.2 (2) | C74—C75—C76 | 120.0 (3) |
N6—C9—H9A | 111.5 | C74—C75—H75 | 120.0 |
C8—C9—H9A | 111.5 | C76—C75—H75 | 120.0 |
N6—C9—H9B | 111.5 | C71—C76—C75 | 120.8 (3) |
C8—C9—H9B | 111.5 | C71—C76—H76 | 119.6 |
H9A—C9—H9B | 109.4 | C75—C76—H76 | 119.6 |
C16—C11—C12 | 119.0 (2) | C86—C81—C82 | 119.3 (2) |
C16—C11—P1 | 117.51 (18) | C86—C81—P3 | 122.70 (18) |
C12—C11—P1 | 123.49 (18) | C82—C81—P3 | 118.02 (19) |
C13—C12—C11 | 120.6 (2) | C83—C82—C81 | 120.5 (3) |
C13—C12—H12 | 119.7 | C83—C82—H82 | 119.7 |
C11—C12—H12 | 119.7 | C81—C82—H82 | 119.7 |
C14—C13—C12 | 119.7 (2) | C84—C83—C82 | 119.9 (3) |
C14—C13—H13 | 120.2 | C84—C83—H83 | 120.0 |
C12—C13—H13 | 120.2 | C82—C83—H83 | 120.0 |
C13—C14—C15 | 120.1 (2) | C85—C84—C83 | 119.9 (3) |
C13—C14—H14 | 120.0 | C85—C84—H84 | 120.0 |
C15—C14—H14 | 120.0 | C83—C84—H84 | 120.0 |
C14—C15—C16 | 120.5 (3) | C84—C85—C86 | 120.6 (3) |
C14—C15—H15 | 119.7 | C84—C85—H85 | 119.7 |
C16—C15—H15 | 119.7 | C86—C85—H85 | 119.7 |
C11—C16—C15 | 120.0 (2) | C81—C86—C85 | 119.7 (2) |
C11—C16—H16 | 120.0 | C81—C86—H86 | 120.1 |
C15—C16—H16 | 120.0 | C85—C86—H86 | 120.1 |
C22—C21—C26 | 119.6 (2) | C92—C91—C96 | 119.3 (2) |
C22—C21—P1 | 122.98 (18) | C92—C91—P3 | 123.29 (18) |
C26—C21—P1 | 117.27 (17) | C96—C91—P3 | 117.23 (18) |
C21—C22—C23 | 120.0 (2) | C93—C92—C91 | 120.2 (2) |
C21—C22—H22 | 120.0 | C93—C92—H92 | 119.9 |
C23—C22—H22 | 120.0 | C91—C92—H92 | 119.9 |
C24—C23—C22 | 120.4 (2) | C94—C93—C92 | 120.0 (2) |
C24—C23—H23 | 119.8 | C94—C93—H93 | 120.0 |
C22—C23—H23 | 119.8 | C92—C93—H93 | 120.0 |
C23—C24—C25 | 119.7 (2) | C95—C94—C93 | 120.2 (2) |
C23—C24—H24 | 120.2 | C95—C94—H94 | 119.9 |
C25—C24—H24 | 120.2 | C93—C94—H94 | 119.9 |
C24—C25—C26 | 120.6 (2) | C94—C95—C96 | 120.0 (2) |
C24—C25—H25 | 119.7 | C94—C95—H95 | 120.0 |
C26—C25—H25 | 119.7 | C96—C95—H95 | 120.0 |
C25—C26—C21 | 119.6 (2) | C95—C96—C91 | 120.3 (2) |
C25—C26—H26 | 120.2 | C95—C96—H96 | 119.9 |
C21—C26—H26 | 120.2 | C91—C96—H96 | 119.9 |
C32—C31—C36 | 119.2 (2) | C50—O4—Ag1 | 132.75 (16) |
C32—C31—P1 | 123.68 (18) | H7A—O7—H7B | 104 (3) |
C36—C31—P1 | 117.06 (17) | H8C—O8—H8D | 99 (3) |
O2—C30—O1 | 124.5 (2) | N7—C10—C20 | 178.5 (3) |
O2—C30—C40 | 117.0 (2) | C10—C20—H20A | 109.5 |
O1—C30—C40 | 118.5 (2) | C10—C20—H20B | 109.5 |
C31—C32—C33 | 120.0 (2) | H20A—C20—H20B | 109.5 |
C31—C32—H32 | 120.0 | C10—C20—H20C | 109.5 |
C33—C32—H32 | 120.0 | H20A—C20—H20C | 109.5 |
C34—C33—C32 | 120.2 (2) | H20B—C20—H20C | 109.5 |
C2—N1—C1—N2 | −0.9 (3) | C41—C42—C43—C44 | −1.8 (4) |
C2—N1—C1—S1 | 177.63 (18) | C42—C43—C44—C45 | 0.6 (4) |
C3—N2—C1—N1 | 5.0 (3) | C43—C44—C45—C46 | 1.0 (4) |
C3—N2—C1—S1 | −173.59 (18) | C42—C41—C46—C45 | 0.1 (4) |
Ag2—S1—C1—N1 | 22.0 (2) | P2—C41—C46—C45 | −175.3 (2) |
Ag2i—S1—C1—N1 | 129.75 (19) | C44—C45—C46—C41 | −1.3 (4) |
Ag2—S1—C1—N2 | −159.64 (18) | C41—P2—C51—C52 | −164.80 (18) |
Ag2i—S1—C1—N2 | −51.9 (2) | C61—P2—C51—C52 | 86.16 (19) |
C1—N1—C2—C3 | −3.1 (3) | Ag1—P2—C51—C52 | −43.0 (2) |
C1—N2—C3—C2 | −6.6 (3) | C41—P2—C51—C56 | 17.0 (2) |
N1—C2—C3—N2 | 5.5 (3) | C61—P2—C51—C56 | −92.1 (2) |
C5—N3—C4—N4 | −2.1 (3) | Ag1—P2—C51—C56 | 138.78 (19) |
C5—N3—C4—S2 | 176.5 (2) | C56—C51—C52—C53 | 0.2 (4) |
C6—N4—C4—N3 | −6.6 (3) | P2—C51—C52—C53 | −178.08 (19) |
C6—N4—C4—S2 | 174.8 (2) | C51—C52—C53—C54 | −0.3 (4) |
Ag2—S2—C4—N3 | 54.9 (2) | C52—C53—C54—C55 | 0.1 (4) |
Ag2—S2—C4—N4 | −126.7 (2) | C53—C54—C55—C56 | 0.1 (4) |
C4—N3—C5—C6 | 9.1 (4) | C54—C55—C56—C51 | −0.1 (4) |
C4—N4—C6—C5 | 11.8 (3) | C52—C51—C56—C55 | 0.0 (4) |
N3—C5—C6—N4 | −11.9 (3) | P2—C51—C56—C55 | 178.18 (19) |
C9—N6—C7—N5 | −7.6 (3) | C51—P2—C61—C66 | −156.93 (19) |
C9—N6—C7—S3 | 171.8 (2) | C41—P2—C61—C66 | 94.0 (2) |
C8—N5—C7—N6 | −8.6 (3) | Ag1—P2—C61—C66 | −31.4 (2) |
C8—N5—C7—S3 | 172.0 (2) | C51—P2—C61—C62 | 21.0 (2) |
Ag1—S3—C7—N6 | −23.8 (2) | C41—P2—C61—C62 | −88.0 (2) |
Ag1—S3—C7—N5 | 155.5 (2) | Ag1—P2—C61—C62 | 146.59 (17) |
C7—N5—C8—C9 | 19.8 (3) | C66—C61—C62—C63 | 0.5 (4) |
C7—N6—C9—C8 | 19.2 (3) | P2—C61—C62—C63 | −177.46 (19) |
N5—C8—C9—N6 | −22.1 (3) | C61—C62—C63—C64 | −0.4 (4) |
C21—P1—C11—C16 | 160.75 (19) | C62—C63—C64—C65 | −0.3 (4) |
C31—P1—C11—C16 | −91.2 (2) | C63—C64—C65—C66 | 1.0 (4) |
Ag2—P1—C11—C16 | 32.7 (2) | C64—C65—C66—C61 | −0.9 (4) |
C21—P1—C11—C12 | −20.0 (2) | C62—C61—C66—C65 | 0.2 (4) |
C31—P1—C11—C12 | 88.0 (2) | P2—C61—C66—C65 | 178.2 (2) |
Ag2—P1—C11—C12 | −148.05 (18) | C91—P3—C71—C76 | −99.6 (2) |
C16—C11—C12—C13 | 0.0 (4) | C81—P3—C71—C76 | 8.6 (2) |
P1—C11—C12—C13 | −179.19 (19) | Ag1—P3—C71—C76 | 131.61 (19) |
C11—C12—C13—C14 | −0.3 (4) | C91—P3—C71—C72 | 83.7 (2) |
C12—C13—C14—C15 | 0.8 (4) | C81—P3—C71—C72 | −168.2 (2) |
C13—C14—C15—C16 | −1.1 (4) | Ag1—P3—C71—C72 | −45.1 (2) |
C12—C11—C16—C15 | −0.3 (4) | C76—C71—C72—C73 | 0.2 (4) |
P1—C11—C16—C15 | 178.9 (2) | P3—C71—C72—C73 | 177.2 (2) |
C14—C15—C16—C11 | 0.9 (4) | C71—C72—C73—C74 | −0.7 (5) |
C11—P1—C21—C22 | 82.9 (2) | C72—C73—C74—C75 | 1.0 (5) |
C31—P1—C21—C22 | −25.3 (2) | C73—C74—C75—C76 | −0.7 (4) |
Ag2—P1—C21—C22 | −146.29 (18) | C72—C71—C76—C75 | 0.0 (4) |
C11—P1—C21—C26 | −92.77 (19) | P3—C71—C76—C75 | −176.8 (2) |
C31—P1—C21—C26 | 159.03 (18) | C74—C75—C76—C71 | 0.3 (4) |
Ag2—P1—C21—C26 | 38.0 (2) | C91—P3—C81—C86 | 1.9 (2) |
C26—C21—C22—C23 | 3.3 (4) | C71—P3—C81—C86 | −107.7 (2) |
P1—C21—C22—C23 | −172.32 (19) | Ag1—P3—C81—C86 | 128.2 (2) |
C21—C22—C23—C24 | −1.5 (4) | C91—P3—C81—C82 | −176.4 (2) |
C22—C23—C24—C25 | −1.0 (4) | C71—P3—C81—C82 | 74.0 (2) |
C23—C24—C25—C26 | 1.8 (4) | Ag1—P3—C81—C82 | −50.1 (2) |
C24—C25—C26—C21 | −0.1 (4) | C86—C81—C82—C83 | 0.6 (4) |
C22—C21—C26—C25 | −2.4 (4) | P3—C81—C82—C83 | 179.0 (2) |
P1—C21—C26—C25 | 173.39 (19) | C81—C82—C83—C84 | −1.0 (5) |
C11—P1—C31—C32 | −0.4 (2) | C82—C83—C84—C85 | 0.6 (5) |
C21—P1—C31—C32 | 107.2 (2) | C83—C84—C85—C86 | 0.2 (5) |
Ag2—P1—C31—C32 | −129.43 (18) | C82—C81—C86—C85 | 0.1 (4) |
C11—P1—C31—C36 | 177.69 (18) | P3—C81—C86—C85 | −178.1 (2) |
C21—P1—C31—C36 | −74.73 (19) | C84—C85—C86—C81 | −0.5 (5) |
Ag2—P1—C31—C36 | 48.66 (19) | C71—P3—C91—C92 | 25.0 (2) |
C36—C31—C32—C33 | 0.2 (3) | C81—P3—C91—C92 | −83.4 (2) |
P1—C31—C32—C33 | 178.25 (19) | Ag1—P3—C91—C92 | 152.64 (17) |
C31—C32—C33—C34 | 0.2 (4) | C71—P3—C91—C96 | −159.91 (19) |
C32—C33—C34—C35 | −0.2 (4) | C81—P3—C91—C96 | 91.7 (2) |
C33—C34—C35—C36 | −0.2 (4) | Ag1—P3—C91—C96 | −32.3 (2) |
C34—C35—C36—C31 | 0.6 (4) | C96—C91—C92—C93 | −1.5 (3) |
C32—C31—C36—C35 | −0.6 (4) | P3—C91—C92—C93 | 173.51 (19) |
P1—C31—C36—C35 | −178.78 (19) | C91—C92—C93—C94 | −1.1 (4) |
C51—P2—C41—C46 | −115.2 (2) | C92—C93—C94—C95 | 2.5 (4) |
C61—P2—C41—C46 | −7.7 (2) | C93—C94—C95—C96 | −1.1 (4) |
Ag1—P2—C41—C46 | 122.04 (19) | C94—C95—C96—C91 | −1.5 (4) |
C51—P2—C41—C42 | 69.4 (2) | C92—C91—C96—C95 | 2.8 (4) |
C61—P2—C41—C42 | 176.87 (19) | P3—C91—C96—C95 | −172.5 (2) |
Ag1—P2—C41—C42 | −53.4 (2) | O6—C50—O4—Ag1 | −80.3 (3) |
C46—C41—C42—C43 | 1.4 (4) | C60—C50—O4—Ag1 | 101.4 (2) |
P2—C41—C42—C43 | 177.1 (2) |
Symmetry code: (i) −x, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1 | 0.88 | 2.10 | 2.908 (3) | 153 |
N2—H2···O8ii | 0.88 | 2.00 | 2.808 (3) | 152 |
N3—H3···O1 | 0.88 | 1.94 | 2.780 (3) | 160 |
N4—H4···O2iii | 0.88 | 2.09 | 2.864 (3) | 146 |
N5—H5···O7iv | 0.88 | 1.96 | 2.767 (3) | 152 |
N6—H6···O4 | 0.88 | 1.91 | 2.780 (3) | 172 |
O7—H7A···O6 | 0.85 (1) | 1.88 (1) | 2.716 (3) | 169 (4) |
O7—H7B···O6v | 0.84 (1) | 2.00 (2) | 2.782 (3) | 154 (3) |
O8—H8C···O2 | 0.84 (1) | 1.88 (1) | 2.709 (3) | 167 (3) |
O8—H8D···S2iv | 0.84 (1) | 2.56 (2) | 3.357 (2) | 159 (3) |
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x−1, y, z; (iv) x+1, y, z; (v) −x, −y+1, −z. |
Acknowledgements
We are grateful to the Department of Chemistry, Faculty of Science, Prince of Songkla University, for financial assistance. We would like to thank Dr Matthias Zeller for collecting data at the Youngstown State University X-ray diffraction facility, funded in part by NSF grant DMR 1337296.
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