research communications
catena-poly[[silver(I)-bis{μ-4-[1-(5′-isopropyl-[1,1′:3′,1′′-terphenyl]-2′-yl)-1H-imidazol-2-yl]pyridine-κ2N:N′}] nitrate methanol monosolvate monohydrate]
of a one-dimensional looped-chain silver(I) coordination polymer:aDepartment of Food and Nutrition, Kyungnam College of Information and Technology, Busan 47011, Republic of Korea, bResearch institute of Natural Science, Gyeongsang National University, Jinju 52828, Republic of Korea, and cDivision of Science Education, Kangwon National University, Chuncheon 24341, Republic of Korea
*Correspondence e-mail: kmpark@gnu.ac.kr, kangy@kangwon.ac.kr
In the title compound, {[Ag(C29H25N3)2]NO3·CH3OH·H2O}n, the AgI cation is four-coordinated by two pyridine N atoms and two imidazole N atoms from four individual 4-(1-(5′-isopropyl-[1,1′:3′,1′′-terphenyl]-2′-yl)-1H-imidazol-2-yl)pyridine (i-pro-pyim) ligands. This gives rise to a highly distorted tetrahedral geometry with bond angles falling in the range 100.33 (19)–122.76 (19)°. Two crystallographically independent i-pro-pyim ligands (A and B) adopt very similar conformations to one another, such that the dihedral angles between the pyridyl and imidazolyl rings in the two ligands are 40.7 (3) and 42.2 (3)°, respectively. Each i-pro-pyim ligand binds two symmetry-related Ag+ cations, leading to the formation of 14-membered cyclic dimers, in which the AgI atoms are separated by 6.963 (2) Å for the Ag–A2–Ag dimer and 7.020 (2) Å for Ag–B2–Ag. These cyclic dimers are alternately connected to each other by sharing AgI atoms, resulting in the formation of a looped-chain structure extending along the [100] direction. Moreover, adjacent looped chains are connected by intermolecular π–π interactions [centroid-to-centroid distance = 3.689 (4) Å], giving rise to the formation of a two-dimensional supramolecular network propagating parallel to (110). Several intermolecular C—H⋯O and O—H⋯O hydrogen bonds further contribute to the stabilization of the crystal structure.
CCDC reference: 1484735
1. Chemical context
Group-9 metal complexes bearing phenylimidazole-based ligands are considered to be suitable triplet emitters for use in phosphorescent organic light-emitting diodes (PHOLEDs) because of their high efficiency and long-term stability (Cho et al., 2016). However, there are relatively few reports of the structures of metal complexes that exhibit coordination of pyridylimidazole (pyim) ligands with an L-type coordination sphere, which is similar to a phenylimidazole system. Recently, AgI coordination polymers built from pyim ligands have attracted much attention due to their structural diversity and properties which have been shown to depend on the nature of the counter-anion (Lee et al., 2016). The structural topology of AgI is quite sensitive to both the counter-anion and solvent molecules (Durá et al., 2014). Herein, we describe the structure of an AgI compound with 4-(1-(5′-isopropyl-[1,1′:3′,1′′-terphenyl]-2′-yl)-1H-imidazol-2-yl)pyridine, i-pro-pyim, as the pyim ligand. The coordination polymer is obtained by addition of the ligand to AgNO3 in methanol/acetonitrile. The title nitrate salt is closely related to the perchlorate salt (Lee et al., 2016).
2. Structural commentary
The title compound crystallizes with one AgI atom, two pyim ligands (A and B), one nitrate anion, one methanol solvent molecule, and two water solvent molecules, each with an occupancy factor of 0.5, in the As shown in Fig. 1, the AgI atom is coordinated by two pyridine N atoms and two imidazole N atoms from four individual i-pro-pyim ligands, giving rise to a highly distorted tetrahedral geometry with bond angles falling in the range of 100.33 (19)–122.76 (19)° (Table 1). The average Ag—N distance is 2.31 Å, similar to that found in the related perchlorate salt (Lee et al., 2016).
In the title compound there are two crystallographically independent ligands, A and B, and their conformations are very similar, such that the dihedral angles between the pyridyl and imidazolyl rings in the two ligands are 40.7 (3) and 42.2 (3)°, respectively. Moreover, there are intramolecular π–π interactions between the pyridyl and phenyl rings of both ligand types, N3,C4–C8 and C21–C26 [centroid-to-centroid distance = 3.760 (4) Å] for A and N6,C33–C37 and C51–C56 [centroid-to-centroid distance = 3.716 (4) Å] for B.
Two symmetry-related A ligands link two AgI atoms, resulting in the formation of a 14-membered cyclic dimer with an Ag⋯Ag distance of 6.963 (2) Å and a π–π interaction [centroid-to-centroid distance = 3.890 (4) Å] between N3-containing pyridine rings (Fig. 2). Similarly, two symmetry-related B ligands also connect two AgI atoms to form another 14-membered cyclic dimer with an Ag⋯Ag separation of 7.020 (2) Å and a π–π interaction [centroid-to-centroid distance = 3.922 (4) Å] between N6-containing pyridine rings. The two cyclic dimers are connected alternately by sharing AgI atoms, leading to the formation of a looped-chain structure extending along the a axis (Fig. 2).
3. Supramolecular features
Adjacent looped chains in the structure are connected by intermolecular π–π interactions [centroid-to-centroid distance = 3.689 (4) Å] between the C50–C55 and C50v–C55v phenyl rings [symmetry code: (v) −x + 2, −y, −z + 1], resulting in the formation of a two-dimensional supramolecular network propagating parallel to (110) (Fig. 3). No notable interactions are found between the two-dimensional networks. The nitrate anions and lattice solvent molecules occupy the void volume between the layers. The of the title compound is further stabilized by weak C—H⋯O hydrogen bonds between the looped chains and the lattice solvent molecules/nitrate anions, and by O—H⋯O hydrogen bonds between the lattice methanol/water molecules or the nitrate anions (Table 2).
4. Synthesis and crystallization
The i-pro-pyim ligand was synthesized according to literature procedures (Lee et al., 2016). Crystals of the title compound were obtained by combining AgNO3 with the i-pro-pyim ligand in a 1:1 molar ratio in a mixture of methanol/acetonitrile (1:1) and allowing the solution to evaporate slowly at room temperature.
5. Refinement
Crystal data, data collection and structure . The anisotropic displacement ellipsoids of some atoms (C53, N7, O1, O2, and O3) were very elongated which indicates static disorder. For these atoms, ISOR restraints were applied (McArdle, 1995; Sheldrick, 2008). Two crystallographically independent water O atoms (O1W and O2W) were refined with site-occupancy factors of 0.5, and their H atoms were not included in the model. All H atoms except those of the water molecules were positioned geometrically and refined using a riding model, with d(C—H) = 0.95 Å for Csp2—H, 1.00 Å for methine, C—H, 0.98 Å for methyl, and O—H 0.84 Å for hydroxyl H atoms. For all H atoms, Uiso(H) = 1.2–1.5Ueq of the parent atom.
details are summarized in Table 3
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Supporting information
CCDC reference: 1484735
https://doi.org/10.1107/S205698901600949X/sj5501sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901600949X/sj5501Isup2.hkl
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Ag(C29H25N3)2]NO3·CH4O·H2O | Z = 2 |
Mr = 1050.97 | F(000) = 1092 |
Triclinic, P1 | Dx = 1.314 Mg m−3 |
a = 13.301 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 13.797 (3) Å | Cell parameters from 5559 reflections |
c = 16.527 (3) Å | θ = 2.4–24.4° |
α = 75.919 (13)° | µ = 0.44 mm−1 |
β = 71.129 (12)° | T = 173 K |
γ = 69.383 (12)° | Block, colourless |
V = 2657.3 (10) Å3 | 0.13 × 0.12 × 0.10 mm |
Bruker APEXII CCD diffractometer | 6302 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.117 |
Absorption correction: multi-scan (SADABS; Bruker 2013) | θmax = 26.0°, θmin = 1.3° |
Tmin = 0.598, Tmax = 0.746 | h = −16→16 |
38791 measured reflections | k = −17→16 |
9965 independent reflections | l = −20→20 |
Refinement on F2 | 30 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.083 | H-atom parameters constrained |
wR(F2) = 0.208 | w = 1/[σ2(Fo2) + (0.0873P)2 + 5.0611P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.001 |
9965 reflections | Δρmax = 1.39 e Å−3 |
658 parameters | Δρmin = −0.88 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 | Occ. (<1) | |
Ag1 | 0.71139 (4) | 0.57116 (4) | 0.52858 (3) | 0.03240 (18) | |
N1 | 0.3957 (4) | 0.4105 (4) | 0.3338 (3) | 0.0331 (13) | |
N2 | 0.4907 (4) | 0.4700 (4) | 0.2062 (3) | 0.0265 (12) | |
N3 | 0.6602 (4) | 0.5156 (4) | 0.4312 (3) | 0.0321 (13) | |
C1 | 0.3570 (5) | 0.3989 (5) | 0.2695 (4) | 0.0345 (16) | |
H1 | 0.2984 | 0.3699 | 0.2790 | 0.041* | |
C2 | 0.4143 (5) | 0.4346 (5) | 0.1920 (4) | 0.0347 (16) | |
H2 | 0.4041 | 0.4353 | 0.1375 | 0.042* | |
C3 | 0.4762 (5) | 0.4539 (5) | 0.2935 (4) | 0.0253 (14) | |
C4 | 0.5408 (5) | 0.4770 (5) | 0.3385 (4) | 0.0276 (14) | |
C5 | 0.5718 (5) | 0.5678 (5) | 0.3150 (4) | 0.0311 (15) | |
H5 | 0.5535 | 0.6174 | 0.2669 | 0.037* | |
C6 | 0.6300 (6) | 0.5842 (5) | 0.3635 (4) | 0.0353 (16) | |
H6 | 0.6498 | 0.6473 | 0.3484 | 0.042* | |
C7 | 0.6311 (5) | 0.4286 (5) | 0.4517 (4) | 0.0301 (15) | |
H7 | 0.6523 | 0.3793 | 0.4990 | 0.036* | |
C8 | 0.5718 (5) | 0.4058 (5) | 0.4082 (4) | 0.0289 (15) | |
H8 | 0.5523 | 0.3425 | 0.4254 | 0.035* | |
C9 | 0.5755 (5) | 0.5037 (5) | 0.1370 (4) | 0.0251 (14) | |
C10 | 0.6864 (5) | 0.4467 (5) | 0.1271 (4) | 0.0263 (14) | |
C11 | 0.7635 (5) | 0.4756 (5) | 0.0540 (4) | 0.0327 (16) | |
H11 | 0.8400 | 0.4378 | 0.0473 | 0.039* | |
C12 | 0.7329 (5) | 0.5578 (5) | −0.0100 (4) | 0.0311 (15) | |
C13 | 0.6231 (5) | 0.6146 (5) | 0.0038 (4) | 0.0299 (15) | |
H13 | 0.6016 | 0.6726 | −0.0382 | 0.036* | |
C14 | 0.5417 (5) | 0.5917 (5) | 0.0760 (4) | 0.0278 (14) | |
C15 | 0.4242 (5) | 0.6556 (5) | 0.0871 (4) | 0.0321 (16) | |
C16 | 0.3730 (6) | 0.6716 (6) | 0.0228 (5) | 0.046 (2) | |
H16 | 0.4142 | 0.6420 | −0.0287 | 0.055* | |
C17 | 0.2634 (7) | 0.7296 (7) | 0.0319 (6) | 0.060 (2) | |
H17 | 0.2290 | 0.7394 | −0.0129 | 0.072* | |
C18 | 0.2035 (6) | 0.7735 (6) | 0.1058 (5) | 0.049 (2) | |
H18 | 0.1276 | 0.8137 | 0.1123 | 0.059* | |
C19 | 0.2533 (7) | 0.7591 (6) | 0.1696 (5) | 0.052 (2) | |
H19 | 0.2116 | 0.7895 | 0.2207 | 0.062* | |
C20 | 0.3635 (6) | 0.7012 (6) | 0.1613 (4) | 0.0422 (18) | |
H20 | 0.3977 | 0.6926 | 0.2060 | 0.051* | |
C21 | 0.7238 (5) | 0.3561 (5) | 0.1921 (4) | 0.0300 (15) | |
C22 | 0.6830 (6) | 0.2708 (5) | 0.2178 (4) | 0.0384 (17) | |
H22 | 0.6300 | 0.2671 | 0.1925 | 0.046* | |
C23 | 0.7198 (6) | 0.1903 (5) | 0.2808 (5) | 0.0437 (19) | |
H23 | 0.6919 | 0.1317 | 0.2982 | 0.052* | |
C24 | 0.7957 (7) | 0.1952 (6) | 0.3178 (5) | 0.049 (2) | |
H24 | 0.8190 | 0.1411 | 0.3620 | 0.059* | |
C25 | 0.8386 (6) | 0.2790 (6) | 0.2910 (5) | 0.0428 (18) | |
H25 | 0.8926 | 0.2816 | 0.3158 | 0.051* | |
C26 | 0.8034 (5) | 0.3584 (5) | 0.2288 (4) | 0.0331 (16) | |
H26 | 0.8337 | 0.4154 | 0.2105 | 0.040* | |
C27 | 0.8183 (6) | 0.5811 (6) | −0.0920 (5) | 0.047 (2) | |
H27 | 0.7774 | 0.6408 | −0.1288 | 0.057* | |
C28 | 0.9017 (8) | 0.6172 (9) | −0.0742 (6) | 0.082 (3) | |
H28A | 0.8628 | 0.6755 | −0.0406 | 0.124* | |
H28B | 0.9471 | 0.5593 | −0.0412 | 0.124* | |
H28C | 0.9498 | 0.6404 | −0.1290 | 0.124* | |
C29 | 0.8737 (8) | 0.4911 (8) | −0.1437 (6) | 0.075 (3) | |
H29A | 0.8167 | 0.4696 | −0.1541 | 0.112* | |
H29B | 0.9215 | 0.5132 | −0.1991 | 0.112* | |
H29C | 0.9189 | 0.4321 | −0.1114 | 0.112* | |
N4 | 1.2737 (5) | 0.2683 (4) | 0.5446 (4) | 0.0344 (13) | |
N5 | 1.2046 (4) | 0.1589 (4) | 0.6505 (3) | 0.0280 (12) | |
N6 | 0.8659 (5) | 0.4337 (4) | 0.5544 (4) | 0.0349 (13) | |
C30 | 1.3587 (6) | 0.1915 (5) | 0.5721 (4) | 0.0362 (17) | |
H30 | 1.4353 | 0.1868 | 0.5492 | 0.043* | |
C31 | 1.3177 (5) | 0.1237 (5) | 0.6365 (4) | 0.0324 (15) | |
H31 | 1.3594 | 0.0630 | 0.6664 | 0.039* | |
C32 | 1.1813 (5) | 0.2470 (5) | 0.5931 (4) | 0.0287 (15) | |
C33 | 1.0702 (5) | 0.3098 (5) | 0.5830 (4) | 0.0281 (15) | |
C34 | 1.0579 (5) | 0.3465 (5) | 0.4996 (4) | 0.0311 (15) | |
H34 | 1.1196 | 0.3299 | 0.4510 | 0.037* | |
C35 | 0.9558 (6) | 0.4067 (5) | 0.4890 (4) | 0.0356 (17) | |
H35 | 0.9480 | 0.4308 | 0.4317 | 0.043* | |
C36 | 0.8792 (6) | 0.3971 (5) | 0.6346 (4) | 0.0367 (17) | |
H36 | 0.8163 | 0.4146 | 0.6823 | 0.044* | |
C37 | 0.9780 (5) | 0.3363 (5) | 0.6512 (4) | 0.0337 (16) | |
H37 | 0.9833 | 0.3124 | 0.7090 | 0.040* | |
C38 | 1.1304 (5) | 0.1053 (5) | 0.7122 (4) | 0.0281 (15) | |
C39 | 1.0600 (5) | 0.0720 (5) | 0.6869 (4) | 0.0280 (15) | |
C40 | 0.9917 (5) | 0.0189 (5) | 0.7494 (4) | 0.0292 (15) | |
H40 | 0.9396 | 0.0001 | 0.7330 | 0.035* | |
C41 | 0.9963 (5) | −0.0081 (5) | 0.8356 (4) | 0.0326 (16) | |
C42 | 1.0678 (5) | 0.0260 (5) | 0.8584 (4) | 0.0330 (16) | |
H42 | 1.0722 | 0.0090 | 0.9166 | 0.040* | |
C43 | 1.1335 (5) | 0.0842 (5) | 0.7994 (4) | 0.0332 (16) | |
C44 | 1.2032 (6) | 0.1244 (7) | 0.8286 (4) | 0.0449 (19) | |
C45 | 1.2835 (8) | 0.0553 (9) | 0.8681 (6) | 0.071 (3) | |
H45 | 1.2930 | −0.0177 | 0.8769 | 0.086* | |
C46 | 1.3503 (10) | 0.0920 (12) | 0.8949 (7) | 0.104 (4) | |
H46 | 1.4077 | 0.0435 | 0.9194 | 0.125* | |
C47 | 1.3352 (12) | 0.1956 (15) | 0.8867 (8) | 0.113 (5) | |
H47 | 1.3806 | 0.2199 | 0.9063 | 0.136* | |
C48 | 1.2547 (12) | 0.2647 (10) | 0.8505 (6) | 0.092 (4) | |
H48 | 1.2438 | 0.3375 | 0.8452 | 0.110* | |
C49 | 1.1866 (8) | 0.2310 (7) | 0.8203 (5) | 0.061 (2) | |
H49 | 1.1306 | 0.2803 | 0.7948 | 0.074* | |
C50 | 1.0550 (5) | 0.0902 (5) | 0.5951 (4) | 0.0276 (14) | |
C51 | 1.1497 (6) | 0.0635 (5) | 0.5277 (4) | 0.0314 (15) | |
H51 | 1.2208 | 0.0346 | 0.5393 | 0.038* | |
C52 | 1.1414 (6) | 0.0786 (5) | 0.4438 (4) | 0.0380 (17) | |
H52 | 1.2064 | 0.0585 | 0.3982 | 0.046* | |
C53 | 1.0395 (6) | 0.1226 (5) | 0.4269 (5) | 0.0412 (18) | |
H53 | 1.0341 | 0.1351 | 0.3691 | 0.049* | |
C54 | 0.9447 (6) | 0.1488 (5) | 0.4930 (5) | 0.0381 (17) | |
H54 | 0.8739 | 0.1784 | 0.4811 | 0.046* | |
C55 | 0.9528 (6) | 0.1321 (5) | 0.5764 (4) | 0.0329 (16) | |
H55 | 0.8871 | 0.1496 | 0.6220 | 0.039* | |
C56 | 0.9249 (6) | −0.0709 (6) | 0.9032 (5) | 0.0447 (19) | |
H56 | 0.8819 | −0.0264 | 0.9500 | 0.054* | |
C57 | 0.9958 (6) | −0.1685 (6) | 0.9451 (5) | 0.0470 (19) | |
H57A | 1.0499 | −0.1509 | 0.9630 | 0.071* | |
H57B | 0.9485 | −0.1999 | 0.9958 | 0.071* | |
H57C | 1.0354 | −0.2185 | 0.9037 | 0.071* | |
C58 | 0.8412 (8) | −0.0886 (9) | 0.8739 (6) | 0.084 (3) | |
H58A | 0.7983 | −0.0219 | 0.8474 | 0.126* | |
H58B | 0.8781 | −0.1371 | 0.8313 | 0.126* | |
H58C | 0.7912 | −0.1185 | 0.9234 | 0.126* | |
N7 | 0.6365 (10) | 0.1663 (11) | 0.6358 (9) | 0.111 (4) | |
O1 | 0.6669 (6) | 0.2327 (6) | 0.6388 (5) | 0.092 (2) | |
O2 | 0.6229 (8) | 0.1637 (9) | 0.5617 (8) | 0.155 (4) | |
O3 | 0.6181 (12) | 0.1000 (10) | 0.6888 (9) | 0.203 (5) | |
O4 | 0.5246 (6) | −0.0588 (6) | 0.6947 (4) | 0.093 (2) | |
H4 | 0.5785 | −0.0525 | 0.7067 | 0.139* | |
C59 | 0.5631 (9) | −0.1052 (9) | 0.6195 (7) | 0.092 (3) | |
H59A | 0.5676 | −0.0510 | 0.5688 | 0.138* | |
H59B | 0.5116 | −0.1415 | 0.6197 | 0.138* | |
H59C | 0.6370 | −0.1556 | 0.6175 | 0.138* | |
O1W | 0.6345 (13) | 0.8346 (9) | 0.8223 (9) | 0.100 (5) | 0.5 |
O2W | 0.1582 (18) | 0.2821 (16) | 0.2921 (13) | 0.147 (7) | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.0315 (3) | 0.0367 (3) | 0.0290 (3) | −0.0147 (2) | −0.0060 (2) | −0.0007 (2) |
N1 | 0.031 (3) | 0.039 (3) | 0.032 (3) | −0.018 (3) | −0.003 (2) | −0.006 (3) |
N2 | 0.024 (3) | 0.029 (3) | 0.024 (3) | −0.007 (2) | −0.003 (2) | −0.006 (2) |
N3 | 0.034 (3) | 0.035 (3) | 0.029 (3) | −0.013 (3) | −0.008 (2) | −0.002 (2) |
C1 | 0.031 (4) | 0.041 (4) | 0.038 (4) | −0.015 (3) | −0.004 (3) | −0.016 (3) |
C2 | 0.029 (4) | 0.043 (4) | 0.036 (4) | −0.010 (3) | −0.008 (3) | −0.015 (3) |
C3 | 0.025 (3) | 0.024 (3) | 0.027 (3) | −0.006 (3) | −0.004 (3) | −0.008 (3) |
C4 | 0.027 (4) | 0.031 (4) | 0.022 (3) | −0.010 (3) | 0.000 (3) | −0.005 (3) |
C5 | 0.036 (4) | 0.035 (4) | 0.022 (3) | −0.014 (3) | −0.003 (3) | −0.005 (3) |
C6 | 0.042 (4) | 0.037 (4) | 0.029 (4) | −0.018 (4) | −0.006 (3) | −0.003 (3) |
C7 | 0.027 (4) | 0.036 (4) | 0.027 (3) | −0.007 (3) | −0.007 (3) | −0.006 (3) |
C8 | 0.026 (4) | 0.025 (4) | 0.029 (3) | −0.008 (3) | 0.000 (3) | −0.002 (3) |
C9 | 0.023 (3) | 0.034 (4) | 0.020 (3) | −0.009 (3) | −0.004 (3) | −0.008 (3) |
C10 | 0.027 (4) | 0.028 (4) | 0.024 (3) | −0.007 (3) | −0.006 (3) | −0.006 (3) |
C11 | 0.020 (3) | 0.036 (4) | 0.036 (4) | −0.002 (3) | −0.005 (3) | −0.006 (3) |
C12 | 0.029 (4) | 0.036 (4) | 0.025 (3) | −0.012 (3) | −0.002 (3) | −0.001 (3) |
C13 | 0.034 (4) | 0.027 (4) | 0.030 (3) | −0.006 (3) | −0.011 (3) | −0.005 (3) |
C14 | 0.026 (4) | 0.033 (4) | 0.026 (3) | −0.009 (3) | −0.004 (3) | −0.010 (3) |
C15 | 0.027 (4) | 0.031 (4) | 0.035 (4) | −0.002 (3) | −0.010 (3) | −0.007 (3) |
C16 | 0.030 (4) | 0.054 (5) | 0.051 (5) | 0.005 (4) | −0.014 (4) | −0.025 (4) |
C17 | 0.039 (5) | 0.074 (6) | 0.070 (6) | 0.007 (5) | −0.026 (4) | −0.035 (5) |
C18 | 0.030 (4) | 0.046 (5) | 0.068 (6) | 0.003 (4) | −0.012 (4) | −0.023 (4) |
C19 | 0.044 (5) | 0.048 (5) | 0.044 (5) | 0.005 (4) | 0.002 (4) | −0.017 (4) |
C20 | 0.044 (5) | 0.042 (4) | 0.034 (4) | −0.001 (4) | −0.009 (3) | −0.013 (3) |
C21 | 0.024 (4) | 0.032 (4) | 0.024 (3) | 0.000 (3) | 0.000 (3) | −0.009 (3) |
C22 | 0.040 (4) | 0.033 (4) | 0.039 (4) | −0.008 (4) | −0.005 (3) | −0.011 (3) |
C23 | 0.053 (5) | 0.026 (4) | 0.045 (4) | −0.008 (4) | −0.006 (4) | −0.007 (3) |
C24 | 0.052 (5) | 0.038 (5) | 0.038 (4) | 0.005 (4) | −0.011 (4) | −0.001 (3) |
C25 | 0.037 (4) | 0.046 (5) | 0.039 (4) | 0.001 (4) | −0.016 (3) | −0.006 (3) |
C26 | 0.025 (4) | 0.030 (4) | 0.037 (4) | −0.001 (3) | −0.007 (3) | −0.006 (3) |
C27 | 0.041 (5) | 0.045 (5) | 0.040 (4) | −0.009 (4) | 0.001 (4) | 0.002 (4) |
C28 | 0.080 (7) | 0.108 (8) | 0.071 (7) | −0.068 (7) | 0.008 (5) | −0.013 (6) |
C29 | 0.070 (6) | 0.086 (7) | 0.048 (5) | −0.026 (6) | 0.023 (5) | −0.021 (5) |
N4 | 0.032 (3) | 0.031 (3) | 0.041 (3) | −0.013 (3) | −0.006 (3) | −0.006 (3) |
N5 | 0.030 (3) | 0.023 (3) | 0.029 (3) | −0.009 (3) | −0.007 (2) | 0.000 (2) |
N6 | 0.038 (3) | 0.032 (3) | 0.035 (3) | −0.012 (3) | −0.009 (3) | −0.003 (3) |
C30 | 0.025 (4) | 0.033 (4) | 0.046 (4) | −0.008 (3) | −0.007 (3) | −0.005 (3) |
C31 | 0.022 (4) | 0.030 (4) | 0.044 (4) | −0.005 (3) | −0.009 (3) | −0.008 (3) |
C32 | 0.031 (4) | 0.026 (4) | 0.030 (3) | −0.011 (3) | −0.004 (3) | −0.006 (3) |
C33 | 0.034 (4) | 0.019 (3) | 0.032 (4) | −0.010 (3) | −0.008 (3) | −0.003 (3) |
C34 | 0.027 (4) | 0.027 (4) | 0.035 (4) | −0.007 (3) | −0.002 (3) | −0.006 (3) |
C35 | 0.051 (5) | 0.030 (4) | 0.031 (4) | −0.021 (4) | −0.011 (3) | 0.000 (3) |
C36 | 0.033 (4) | 0.031 (4) | 0.035 (4) | −0.007 (3) | 0.001 (3) | −0.003 (3) |
C37 | 0.031 (4) | 0.030 (4) | 0.033 (4) | −0.005 (3) | −0.006 (3) | −0.001 (3) |
C38 | 0.026 (4) | 0.021 (3) | 0.034 (4) | −0.006 (3) | −0.002 (3) | −0.006 (3) |
C39 | 0.024 (3) | 0.023 (3) | 0.031 (3) | −0.002 (3) | −0.003 (3) | −0.006 (3) |
C40 | 0.028 (4) | 0.023 (3) | 0.037 (4) | −0.008 (3) | −0.009 (3) | −0.005 (3) |
C41 | 0.032 (4) | 0.028 (4) | 0.032 (4) | −0.009 (3) | −0.001 (3) | −0.003 (3) |
C42 | 0.037 (4) | 0.028 (4) | 0.029 (4) | −0.008 (3) | −0.006 (3) | −0.001 (3) |
C43 | 0.032 (4) | 0.029 (4) | 0.038 (4) | −0.006 (3) | −0.010 (3) | −0.008 (3) |
C44 | 0.051 (5) | 0.062 (5) | 0.029 (4) | −0.030 (4) | −0.004 (4) | −0.008 (4) |
C45 | 0.076 (7) | 0.094 (8) | 0.065 (6) | −0.039 (6) | −0.030 (5) | −0.012 (5) |
C46 | 0.111 (10) | 0.151 (13) | 0.095 (9) | −0.065 (10) | −0.056 (8) | −0.018 (8) |
C47 | 0.131 (12) | 0.192 (16) | 0.077 (8) | −0.122 (12) | −0.015 (8) | −0.034 (9) |
C48 | 0.155 (12) | 0.113 (10) | 0.045 (6) | −0.104 (9) | 0.010 (6) | −0.030 (6) |
C49 | 0.094 (7) | 0.065 (6) | 0.041 (5) | −0.052 (6) | −0.002 (5) | −0.013 (4) |
C50 | 0.036 (4) | 0.019 (3) | 0.029 (3) | −0.011 (3) | −0.012 (3) | 0.002 (3) |
C51 | 0.032 (4) | 0.023 (4) | 0.036 (4) | −0.010 (3) | −0.007 (3) | 0.001 (3) |
C52 | 0.040 (4) | 0.034 (4) | 0.038 (4) | −0.008 (4) | −0.006 (3) | −0.012 (3) |
C53 | 0.049 (4) | 0.039 (3) | 0.038 (3) | −0.011 (3) | −0.016 (3) | −0.008 (3) |
C54 | 0.041 (4) | 0.029 (4) | 0.051 (4) | −0.008 (3) | −0.023 (4) | −0.007 (3) |
C55 | 0.036 (4) | 0.030 (4) | 0.037 (4) | −0.015 (3) | −0.009 (3) | −0.004 (3) |
C56 | 0.046 (5) | 0.054 (5) | 0.034 (4) | −0.025 (4) | −0.004 (3) | 0.000 (3) |
C57 | 0.055 (5) | 0.036 (4) | 0.041 (4) | −0.017 (4) | −0.002 (4) | 0.001 (3) |
C58 | 0.086 (7) | 0.118 (9) | 0.068 (6) | −0.075 (7) | −0.023 (6) | 0.022 (6) |
N7 | 0.104 (5) | 0.109 (5) | 0.110 (5) | −0.023 (4) | −0.015 (4) | −0.028 (4) |
O1 | 0.085 (5) | 0.083 (5) | 0.115 (5) | −0.018 (4) | −0.032 (4) | −0.027 (4) |
O2 | 0.124 (6) | 0.170 (8) | 0.183 (8) | −0.016 (6) | −0.060 (6) | −0.062 (6) |
O3 | 0.243 (9) | 0.132 (7) | 0.177 (8) | −0.079 (7) | 0.045 (7) | −0.023 (6) |
O4 | 0.080 (5) | 0.106 (6) | 0.076 (5) | 0.004 (4) | −0.031 (4) | −0.015 (4) |
C59 | 0.075 (7) | 0.115 (9) | 0.073 (7) | −0.010 (7) | −0.006 (6) | −0.036 (7) |
O1W | 0.152 (14) | 0.049 (8) | 0.112 (11) | 0.005 (8) | −0.106 (11) | 0.011 (7) |
O2W | 0.20 (2) | 0.142 (16) | 0.138 (16) | −0.106 (16) | −0.062 (15) | 0.020 (13) |
Ag1—N1i | 2.279 (5) | N4—Ag1ii | 2.293 (5) |
Ag1—N4ii | 2.293 (5) | N5—C32 | 1.355 (8) |
Ag1—N3 | 2.306 (5) | N5—C31 | 1.367 (8) |
Ag1—N6 | 2.330 (6) | N5—C38 | 1.434 (8) |
N1—C3 | 1.321 (8) | N6—C35 | 1.336 (8) |
N1—C1 | 1.384 (8) | N6—C36 | 1.345 (8) |
N1—Ag1i | 2.279 (5) | C30—C31 | 1.343 (9) |
N2—C3 | 1.366 (7) | C30—H30 | 0.9500 |
N2—C2 | 1.373 (8) | C31—H31 | 0.9500 |
N2—C9 | 1.440 (7) | C32—C33 | 1.466 (9) |
N3—C7 | 1.323 (8) | C33—C37 | 1.379 (9) |
N3—C6 | 1.348 (8) | C33—C34 | 1.389 (9) |
C1—C2 | 1.338 (9) | C34—C35 | 1.362 (9) |
C1—H1 | 0.9500 | C34—H34 | 0.9500 |
C2—H2 | 0.9500 | C35—H35 | 0.9500 |
C3—C4 | 1.454 (8) | C36—C37 | 1.359 (9) |
C4—C5 | 1.383 (9) | C36—H36 | 0.9500 |
C4—C8 | 1.389 (8) | C37—H37 | 0.9500 |
C5—C6 | 1.381 (9) | C38—C39 | 1.384 (9) |
C5—H5 | 0.9500 | C38—C43 | 1.411 (9) |
C6—H6 | 0.9500 | C39—C40 | 1.387 (8) |
C7—C8 | 1.375 (9) | C39—C50 | 1.496 (8) |
C7—H7 | 0.9500 | C40—C41 | 1.398 (9) |
C8—H8 | 0.9500 | C40—H40 | 0.9500 |
C9—C10 | 1.382 (8) | C41—C42 | 1.379 (9) |
C9—C14 | 1.417 (8) | C41—C56 | 1.525 (9) |
C10—C11 | 1.385 (8) | C42—C43 | 1.385 (9) |
C10—C21 | 1.490 (9) | C42—H42 | 0.9500 |
C11—C12 | 1.393 (9) | C43—C44 | 1.477 (10) |
C11—H11 | 0.9500 | C44—C45 | 1.380 (12) |
C12—C13 | 1.365 (9) | C44—C49 | 1.387 (11) |
C12—C27 | 1.510 (9) | C45—C46 | 1.388 (13) |
C13—C14 | 1.385 (8) | C45—H45 | 0.9500 |
C13—H13 | 0.9500 | C46—C47 | 1.350 (18) |
C14—C15 | 1.475 (9) | C46—H46 | 0.9500 |
C15—C16 | 1.375 (9) | C47—C48 | 1.354 (18) |
C15—C20 | 1.388 (9) | C47—H47 | 0.9500 |
C16—C17 | 1.373 (10) | C48—C49 | 1.409 (13) |
C16—H16 | 0.9500 | C48—H48 | 0.9500 |
C17—C18 | 1.372 (10) | C49—H49 | 0.9500 |
C17—H17 | 0.9500 | C50—C55 | 1.380 (9) |
C18—C19 | 1.360 (11) | C50—C51 | 1.388 (9) |
C18—H18 | 0.9500 | C51—C52 | 1.386 (9) |
C19—C20 | 1.380 (10) | C51—H51 | 0.9500 |
C19—H19 | 0.9500 | C52—C53 | 1.367 (10) |
C20—H20 | 0.9500 | C52—H52 | 0.9500 |
C21—C22 | 1.386 (9) | C53—C54 | 1.377 (10) |
C21—C26 | 1.391 (9) | C53—H53 | 0.9500 |
C22—C23 | 1.393 (10) | C54—C55 | 1.375 (9) |
C22—H22 | 0.9500 | C54—H54 | 0.9500 |
C23—C24 | 1.367 (11) | C55—H55 | 0.9500 |
C23—H23 | 0.9500 | C56—C58 | 1.458 (11) |
C24—C25 | 1.381 (11) | C56—C57 | 1.503 (10) |
C24—H24 | 0.9500 | C56—H56 | 1.0000 |
C25—C26 | 1.371 (9) | C57—H57A | 0.9800 |
C25—H25 | 0.9500 | C57—H57B | 0.9800 |
C26—H26 | 0.9500 | C57—H57C | 0.9800 |
C27—C28 | 1.496 (11) | C58—H58A | 0.9800 |
C27—C29 | 1.509 (11) | C58—H58B | 0.9800 |
C27—H27 | 1.0000 | C58—H58C | 0.9800 |
C28—H28A | 0.9800 | N7—O3 | 1.137 (14) |
C28—H28B | 0.9800 | N7—O1 | 1.141 (13) |
C28—H28C | 0.9800 | N7—O2 | 1.304 (14) |
C29—H29A | 0.9800 | O4—C59 | 1.400 (11) |
C29—H29B | 0.9800 | O4—H4 | 0.8400 |
C29—H29C | 0.9800 | C59—H59A | 0.9800 |
N4—C32 | 1.320 (8) | C59—H59B | 0.9800 |
N4—C30 | 1.364 (8) | C59—H59C | 0.9800 |
N1i—Ag1—N4ii | 109.11 (19) | C30—N4—Ag1ii | 123.4 (4) |
N1i—Ag1—N3 | 122.76 (19) | C32—N5—C31 | 106.8 (5) |
N4ii—Ag1—N3 | 100.33 (19) | C32—N5—C38 | 129.2 (5) |
N1i—Ag1—N6 | 100.96 (19) | C31—N5—C38 | 123.9 (5) |
N4ii—Ag1—N6 | 121.95 (19) | C35—N6—C36 | 116.6 (6) |
N3—Ag1—N6 | 103.27 (19) | C35—N6—Ag1 | 119.7 (4) |
C3—N1—C1 | 105.7 (5) | C36—N6—Ag1 | 121.7 (4) |
C3—N1—Ag1i | 124.6 (4) | C31—C30—N4 | 109.8 (6) |
C1—N1—Ag1i | 123.3 (4) | C31—C30—H30 | 125.1 |
C3—N2—C2 | 106.8 (5) | N4—C30—H30 | 125.1 |
C3—N2—C9 | 130.1 (5) | C30—C31—N5 | 106.8 (6) |
C2—N2—C9 | 122.6 (5) | C30—C31—H31 | 126.6 |
C7—N3—C6 | 117.3 (6) | N5—C31—H31 | 126.6 |
C7—N3—Ag1 | 120.8 (4) | N4—C32—N5 | 110.6 (6) |
C6—N3—Ag1 | 119.4 (4) | N4—C32—C33 | 123.5 (6) |
C2—C1—N1 | 110.0 (6) | N5—C32—C33 | 125.9 (6) |
C2—C1—H1 | 125.0 | C37—C33—C34 | 118.1 (6) |
N1—C1—H1 | 125.0 | C37—C33—C32 | 123.9 (6) |
C1—C2—N2 | 106.9 (6) | C34—C33—C32 | 118.0 (6) |
C1—C2—H2 | 126.6 | C35—C34—C33 | 118.8 (6) |
N2—C2—H2 | 126.6 | C35—C34—H34 | 120.6 |
N1—C3—N2 | 110.7 (5) | C33—C34—H34 | 120.6 |
N1—C3—C4 | 123.0 (5) | N6—C35—C34 | 123.8 (6) |
N2—C3—C4 | 126.3 (5) | N6—C35—H35 | 118.1 |
C5—C4—C8 | 118.7 (6) | C34—C35—H35 | 118.1 |
C5—C4—C3 | 122.4 (6) | N6—C36—C37 | 123.5 (6) |
C8—C4—C3 | 118.9 (6) | N6—C36—H36 | 118.3 |
C6—C5—C4 | 118.0 (6) | C37—C36—H36 | 118.3 |
C6—C5—H5 | 121.0 | C36—C37—C33 | 119.2 (6) |
C4—C5—H5 | 121.0 | C36—C37—H37 | 120.4 |
N3—C6—C5 | 123.6 (6) | C33—C37—H37 | 120.4 |
N3—C6—H6 | 118.2 | C39—C38—C43 | 120.6 (6) |
C5—C6—H6 | 118.2 | C39—C38—N5 | 121.1 (6) |
N3—C7—C8 | 123.5 (6) | C43—C38—N5 | 118.2 (6) |
N3—C7—H7 | 118.3 | C38—C39—C40 | 118.4 (6) |
C8—C7—H7 | 118.3 | C38—C39—C50 | 122.9 (6) |
C7—C8—C4 | 118.9 (6) | C40—C39—C50 | 118.7 (6) |
C7—C8—H8 | 120.6 | C39—C40—C41 | 122.7 (6) |
C4—C8—H8 | 120.6 | C39—C40—H40 | 118.7 |
C10—C9—C14 | 121.1 (6) | C41—C40—H40 | 118.7 |
C10—C9—N2 | 120.5 (5) | C42—C41—C40 | 117.2 (6) |
C14—C9—N2 | 118.2 (5) | C42—C41—C56 | 120.3 (6) |
C9—C10—C11 | 118.2 (6) | C40—C41—C56 | 122.5 (6) |
C9—C10—C21 | 121.7 (5) | C41—C42—C43 | 122.4 (6) |
C11—C10—C21 | 120.1 (6) | C41—C42—H42 | 118.8 |
C10—C11—C12 | 122.5 (6) | C43—C42—H42 | 118.8 |
C10—C11—H11 | 118.7 | C42—C43—C38 | 118.6 (6) |
C12—C11—H11 | 118.7 | C42—C43—C44 | 120.1 (6) |
C13—C12—C11 | 117.4 (6) | C38—C43—C44 | 121.3 (6) |
C13—C12—C27 | 121.7 (6) | C45—C44—C49 | 119.0 (8) |
C11—C12—C27 | 120.8 (6) | C45—C44—C43 | 119.7 (7) |
C12—C13—C14 | 123.3 (6) | C49—C44—C43 | 121.2 (8) |
C12—C13—H13 | 118.4 | C44—C45—C46 | 120.3 (11) |
C14—C13—H13 | 118.4 | C44—C45—H45 | 119.9 |
C13—C14—C9 | 117.4 (6) | C46—C45—H45 | 119.9 |
C13—C14—C15 | 120.8 (6) | C47—C46—C45 | 121.1 (13) |
C9—C14—C15 | 121.8 (6) | C47—C46—H46 | 119.5 |
C16—C15—C20 | 118.8 (6) | C45—C46—H46 | 119.5 |
C16—C15—C14 | 119.8 (6) | C46—C47—C48 | 119.4 (11) |
C20—C15—C14 | 121.4 (6) | C46—C47—H47 | 120.3 |
C17—C16—C15 | 121.1 (7) | C48—C47—H47 | 120.3 |
C17—C16—H16 | 119.5 | C47—C48—C49 | 121.6 (11) |
C15—C16—H16 | 119.5 | C47—C48—H48 | 119.2 |
C18—C17—C16 | 119.9 (8) | C49—C48—H48 | 119.2 |
C18—C17—H17 | 120.0 | C44—C49—C48 | 118.6 (10) |
C16—C17—H17 | 120.0 | C44—C49—H49 | 120.7 |
C19—C18—C17 | 119.7 (7) | C48—C49—H49 | 120.7 |
C19—C18—H18 | 120.2 | C55—C50—C51 | 118.5 (6) |
C17—C18—H18 | 120.2 | C55—C50—C39 | 119.3 (6) |
C18—C19—C20 | 121.1 (7) | C51—C50—C39 | 122.1 (6) |
C18—C19—H19 | 119.5 | C52—C51—C50 | 120.5 (6) |
C20—C19—H19 | 119.5 | C52—C51—H51 | 119.8 |
C19—C20—C15 | 119.5 (7) | C50—C51—H51 | 119.8 |
C19—C20—H20 | 120.2 | C53—C52—C51 | 119.8 (7) |
C15—C20—H20 | 120.2 | C53—C52—H52 | 120.1 |
C22—C21—C26 | 118.8 (6) | C51—C52—H52 | 120.1 |
C22—C21—C10 | 123.3 (6) | C52—C53—C54 | 120.4 (7) |
C26—C21—C10 | 117.8 (6) | C52—C53—H53 | 119.8 |
C21—C22—C23 | 120.0 (7) | C54—C53—H53 | 119.8 |
C21—C22—H22 | 120.0 | C55—C54—C53 | 119.8 (7) |
C23—C22—H22 | 120.0 | C55—C54—H54 | 120.1 |
C24—C23—C22 | 120.3 (7) | C53—C54—H54 | 120.1 |
C24—C23—H23 | 119.9 | C54—C55—C50 | 121.0 (6) |
C22—C23—H23 | 119.9 | C54—C55—H55 | 119.5 |
C23—C24—C25 | 119.9 (7) | C50—C55—H55 | 119.5 |
C23—C24—H24 | 120.0 | C58—C56—C57 | 113.9 (7) |
C25—C24—H24 | 120.0 | C58—C56—C41 | 114.8 (6) |
C26—C25—C24 | 120.3 (7) | C57—C56—C41 | 111.0 (6) |
C26—C25—H25 | 119.9 | C58—C56—H56 | 105.4 |
C24—C25—H25 | 119.9 | C57—C56—H56 | 105.4 |
C25—C26—C21 | 120.6 (7) | C41—C56—H56 | 105.4 |
C25—C26—H26 | 119.7 | C56—C57—H57A | 109.5 |
C21—C26—H26 | 119.7 | C56—C57—H57B | 109.5 |
C28—C27—C29 | 111.8 (7) | H57A—C57—H57B | 109.5 |
C28—C27—C12 | 111.4 (7) | C56—C57—H57C | 109.5 |
C29—C27—C12 | 113.0 (6) | H57A—C57—H57C | 109.5 |
C28—C27—H27 | 106.7 | H57B—C57—H57C | 109.5 |
C29—C27—H27 | 106.7 | C56—C58—H58A | 109.5 |
C12—C27—H27 | 106.7 | C56—C58—H58B | 109.5 |
C27—C28—H28A | 109.5 | H58A—C58—H58B | 109.5 |
C27—C28—H28B | 109.5 | C56—C58—H58C | 109.5 |
H28A—C28—H28B | 109.5 | H58A—C58—H58C | 109.5 |
C27—C28—H28C | 109.5 | H58B—C58—H58C | 109.5 |
H28A—C28—H28C | 109.5 | O3—N7—O1 | 128.4 (17) |
H28B—C28—H28C | 109.5 | O3—N7—O2 | 115.0 (16) |
C27—C29—H29A | 109.5 | O1—N7—O2 | 116.6 (14) |
C27—C29—H29B | 109.5 | C59—O4—H4 | 109.5 |
H29A—C29—H29B | 109.5 | O4—C59—H59A | 109.5 |
C27—C29—H29C | 109.5 | O4—C59—H59B | 109.5 |
H29A—C29—H29C | 109.5 | H59A—C59—H59B | 109.5 |
H29B—C29—H29C | 109.5 | O4—C59—H59C | 109.5 |
C32—N4—C30 | 106.1 (5) | H59A—C59—H59C | 109.5 |
C32—N4—Ag1ii | 126.3 (4) | H59B—C59—H59C | 109.5 |
C3—N1—C1—C2 | 0.3 (8) | C32—N4—C30—C31 | 0.5 (8) |
Ag1i—N1—C1—C2 | 153.2 (5) | Ag1ii—N4—C30—C31 | 158.6 (5) |
N1—C1—C2—N2 | −0.2 (8) | N4—C30—C31—N5 | −0.6 (8) |
C3—N2—C2—C1 | 0.0 (7) | C32—N5—C31—C30 | 0.5 (7) |
C9—N2—C2—C1 | 173.1 (6) | C38—N5—C31—C30 | 177.4 (6) |
C1—N1—C3—N2 | −0.2 (7) | C30—N4—C32—N5 | −0.2 (7) |
Ag1i—N1—C3—N2 | −152.7 (4) | Ag1ii—N4—C32—N5 | −157.5 (4) |
C1—N1—C3—C4 | −178.5 (6) | C30—N4—C32—C33 | −178.6 (6) |
Ag1i—N1—C3—C4 | 29.0 (8) | Ag1ii—N4—C32—C33 | 24.2 (9) |
C2—N2—C3—N1 | 0.1 (7) | C31—N5—C32—N4 | −0.2 (7) |
C9—N2—C3—N1 | −172.2 (6) | C38—N5—C32—N4 | −176.9 (6) |
C2—N2—C3—C4 | 178.3 (6) | C31—N5—C32—C33 | 178.1 (6) |
C9—N2—C3—C4 | 6.0 (10) | C38—N5—C32—C33 | 1.4 (10) |
N1—C3—C4—C5 | −140.1 (6) | N4—C32—C33—C37 | −138.1 (7) |
N2—C3—C4—C5 | 41.9 (9) | N5—C32—C33—C37 | 43.8 (10) |
N1—C3—C4—C8 | 39.3 (9) | N4—C32—C33—C34 | 40.6 (9) |
N2—C3—C4—C8 | −138.7 (6) | N5—C32—C33—C34 | −137.5 (6) |
C8—C4—C5—C6 | −1.5 (9) | C37—C33—C34—C35 | 0.0 (9) |
C3—C4—C5—C6 | 177.9 (6) | C32—C33—C34—C35 | −178.8 (6) |
C7—N3—C6—C5 | −0.5 (10) | C36—N6—C35—C34 | −0.9 (9) |
Ag1—N3—C6—C5 | −162.8 (5) | Ag1—N6—C35—C34 | 163.4 (5) |
C4—C5—C6—N3 | 1.5 (10) | C33—C34—C35—N6 | 0.6 (10) |
C6—N3—C7—C8 | −0.4 (9) | C35—N6—C36—C37 | 0.7 (10) |
Ag1—N3—C7—C8 | 161.5 (5) | Ag1—N6—C36—C37 | −163.3 (5) |
N3—C7—C8—C4 | 0.4 (9) | N6—C36—C37—C33 | −0.1 (10) |
C5—C4—C8—C7 | 0.6 (9) | C34—C33—C37—C36 | −0.2 (9) |
C3—C4—C8—C7 | −178.8 (5) | C32—C33—C37—C36 | 178.5 (6) |
C3—N2—C9—C10 | 58.9 (9) | C32—N5—C38—C39 | 55.6 (9) |
C2—N2—C9—C10 | −112.3 (7) | C31—N5—C38—C39 | −120.6 (7) |
C3—N2—C9—C14 | −125.8 (7) | C32—N5—C38—C43 | −126.5 (7) |
C2—N2—C9—C14 | 63.0 (8) | C31—N5—C38—C43 | 57.3 (8) |
C14—C9—C10—C11 | −2.4 (9) | C43—C38—C39—C40 | 1.0 (9) |
N2—C9—C10—C11 | 172.7 (6) | N5—C38—C39—C40 | 178.8 (5) |
C14—C9—C10—C21 | 177.9 (6) | C43—C38—C39—C50 | −178.7 (6) |
N2—C9—C10—C21 | −6.9 (9) | N5—C38—C39—C50 | −0.8 (9) |
C9—C10—C11—C12 | −1.3 (10) | C38—C39—C40—C41 | −4.3 (9) |
C21—C10—C11—C12 | 178.3 (6) | C50—C39—C40—C41 | 175.4 (6) |
C10—C11—C12—C13 | 3.7 (10) | C39—C40—C41—C42 | 4.0 (9) |
C10—C11—C12—C27 | −174.9 (6) | C39—C40—C41—C56 | −177.1 (6) |
C11—C12—C13—C14 | −2.4 (10) | C40—C41—C42—C43 | −0.4 (10) |
C27—C12—C13—C14 | 176.2 (6) | C56—C41—C42—C43 | −179.3 (6) |
C12—C13—C14—C9 | −1.1 (9) | C41—C42—C43—C38 | −2.8 (10) |
C12—C13—C14—C15 | −179.7 (6) | C41—C42—C43—C44 | 176.1 (6) |
C10—C9—C14—C13 | 3.6 (9) | C39—C38—C43—C42 | 2.4 (9) |
N2—C9—C14—C13 | −171.7 (5) | N5—C38—C43—C42 | −175.5 (5) |
C10—C9—C14—C15 | −177.8 (6) | C39—C38—C43—C44 | −176.4 (6) |
N2—C9—C14—C15 | 6.9 (9) | N5—C38—C43—C44 | 5.7 (9) |
C13—C14—C15—C16 | 53.8 (9) | C42—C43—C44—C45 | 59.3 (10) |
C9—C14—C15—C16 | −124.8 (7) | C38—C43—C44—C45 | −121.9 (8) |
C13—C14—C15—C20 | −125.6 (7) | C42—C43—C44—C49 | −118.0 (8) |
C9—C14—C15—C20 | 55.8 (9) | C38—C43—C44—C49 | 60.8 (9) |
C20—C15—C16—C17 | −1.4 (12) | C49—C44—C45—C46 | −3.3 (13) |
C14—C15—C16—C17 | 179.2 (7) | C43—C44—C45—C46 | 179.3 (9) |
C15—C16—C17—C18 | 0.6 (13) | C44—C45—C46—C47 | 3.1 (17) |
C16—C17—C18—C19 | 0.0 (13) | C45—C46—C47—C48 | −1.1 (19) |
C17—C18—C19—C20 | 0.2 (13) | C46—C47—C48—C49 | −0.5 (18) |
C18—C19—C20—C15 | −0.9 (12) | C45—C44—C49—C48 | 1.7 (11) |
C16—C15—C20—C19 | 1.5 (11) | C43—C44—C49—C48 | 179.0 (7) |
C14—C15—C20—C19 | −179.1 (7) | C47—C48—C49—C44 | 0.2 (14) |
C9—C10—C21—C22 | 55.9 (9) | C38—C39—C50—C55 | −130.6 (7) |
C11—C10—C21—C22 | −123.7 (7) | C40—C39—C50—C55 | 49.8 (8) |
C9—C10—C21—C26 | −123.8 (7) | C38—C39—C50—C51 | 51.3 (9) |
C11—C10—C21—C26 | 56.6 (8) | C40—C39—C50—C51 | −128.3 (7) |
C26—C21—C22—C23 | 1.5 (9) | C55—C50—C51—C52 | −0.1 (9) |
C10—C21—C22—C23 | −178.2 (6) | C39—C50—C51—C52 | 178.0 (6) |
C21—C22—C23—C24 | 0.3 (10) | C50—C51—C52—C53 | 1.6 (10) |
C22—C23—C24—C25 | −1.8 (11) | C51—C52—C53—C54 | −2.1 (10) |
C23—C24—C25—C26 | 1.4 (11) | C52—C53—C54—C55 | 1.0 (10) |
C24—C25—C26—C21 | 0.4 (10) | C53—C54—C55—C50 | 0.7 (10) |
C22—C21—C26—C25 | −1.8 (9) | C51—C50—C55—C54 | −1.1 (9) |
C10—C21—C26—C25 | 177.9 (6) | C39—C50—C55—C54 | −179.2 (6) |
C13—C12—C27—C28 | 115.4 (8) | C42—C41—C56—C58 | 171.2 (8) |
C11—C12—C27—C28 | −66.0 (9) | C40—C41—C56—C58 | −7.7 (11) |
C13—C12—C27—C29 | −117.7 (8) | C42—C41—C56—C57 | −57.8 (9) |
C11—C12—C27—C29 | 60.8 (10) | C40—C41—C56—C57 | 123.3 (7) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, −y+1, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O2W | 0.95 | 2.49 | 3.434 (19) | 174 |
C30—H30···O2iii | 0.95 | 2.47 | 3.350 (12) | 154 |
C31—H31···O4iii | 0.95 | 2.36 | 3.239 (9) | 154 |
O4—H4···O3 | 0.84 | 2.27 | 2.846 (16) | 126 |
O4—H4···O1Wiv | 0.84 | 2.30 | 2.778 (13) | 117 |
Symmetry codes: (iii) x+1, y, z; (iv) x, y−1, z. |
Acknowledgements
This study was supported by a 2015 Research Grant from Kangwon National University (No. 520150194).
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