A novel ladder-type coordination polymer (CP), poly[(μ-4,4′-bipyridine-κ2N:N′){μ-4-[(4-carboxybenzyloxy)methyl]benzoato-κO}silver(I)](Ag—Ag), [Ag(C16H13O5)(C10H8N2)]n or [Ag(HL)(4,4′-bpy)]n {H2L is 4,4′-[oxybis(methylene)]dibenzoic acid and 4,4′-bpy is 4,4′-bipyridine}, was synthesized using hydrothermal methods. The complex was characterized by IR spectroscopy, elemental analysis and single-crystal X-ray diffraction, and is a ladder-type CP which exhibits an obvious Ag—Ag interaction. The legs of the ladder are formed by parallel 4,4′-bipy ligands and silver ions, and the rungs are constructed by Ag—Ag interactions. A Hirshfeld surface analysis was carried out and is discussed in detail. The complex also displays favourable fluorescence properties.
Supporting information
CCDC reference: 2025969
Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SHELXT2015 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
Poly[(µ-4,4'-bipyridine-
κ2N:
N'){µ-4-[(4-carboxybenzyloxy)methyl]benzoato-
κO}silver(I)](
Ag—
Ag)
top
Crystal data top
[Ag(C16H13O5)(C10H8N2)] | Z = 2 |
Mr = 549.32 | F(000) = 556 |
Triclinic, P1 | Dx = 1.612 Mg m−3 |
a = 7.9269 (6) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.3939 (8) Å | Cell parameters from 2207 reflections |
c = 13.6589 (8) Å | θ = 3.7–21.0° |
α = 78.610 (5)° | µ = 0.93 mm−1 |
β = 81.339 (6)° | T = 289 K |
γ = 70.031 (6)° | Plate, colourless |
V = 1132.01 (14) Å3 | 0.22 × 0.21 × 0.11 mm |
Data collection top
Agilent SuperNova Single Source diffractometer with an E detector | 4035 independent reflections |
Radiation source: SuperNova (Mo) X-ray Source | 2501 reflections with I > 2σ(I) |
Detector resolution: 16.0233 pixels mm-1 | Rint = 0.073 |
ω scans | θmax = 25.1°, θmin = 3.4° |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2014) | h = −9→9 |
Tmin = 0.429, Tmax = 0.871 | k = −13→13 |
14148 measured reflections | l = −16→16 |
Refinement top
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0304P)2 + 0.7458P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
4035 reflections | Δρmax = 0.55 e Å−3 |
303 parameters | Δρmin = −0.57 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. The diffraction data of 1 were collected on a SuperNova
(Single source at offset, Eos) with graphite monochromated Mo-Ka
radiation (λ = 0.71073 Å), using the ω scan mode in the
range 3.35° ≤ θ ≤ 25.10°. The raw frame data were integrated with
the CrysAlis PRO program. The structure 1 were solved by direct methods
using SHELXT (Sheldrick, 2008, 2015) and refined by full-matrix
least-squares
on F2 using SHELXL2018 within the OLEX-2 GUI (Dolomanov, et al.
2009). An empirical absorption correction was
applied with spherical
harmonics, implemented in SCALE3 ABSPACK scaling algorithm. All non-hydrogen
atoms were refined anisotropically. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Ag1 | 0.32970 (6) | 0.44453 (4) | 0.51821 (4) | 0.0608 (2) | |
O3 | 1.3458 (5) | 1.1536 (4) | 0.8164 (3) | 0.0667 (12) | |
O4 | 1.1040 (5) | 1.3147 (4) | 0.7749 (4) | 0.0672 (12) | |
H4 | 1.1793 | 1.3508 | 0.7555 | 0.101* | |
O9 | 0.8298 (6) | 0.7584 (4) | 0.9504 (3) | 0.0701 (12) | |
O2 | 0.2698 (6) | 0.4736 (4) | 0.7553 (3) | 0.0665 (12) | |
N1 | −0.4973 (6) | 1.2490 (4) | 0.5112 (4) | 0.0486 (12) | |
C2 | −0.4494 (8) | 1.1724 (5) | 0.5962 (5) | 0.0626 (18) | |
H2 | −0.4953 | 1.2033 | 0.6562 | 0.075* | |
O1 | 0.5166 (6) | 0.4518 (4) | 0.6490 (3) | 0.0688 (13) | |
C5 | −0.2613 (7) | 0.9992 (5) | 0.5134 (4) | 0.0389 (13) | |
C13 | 0.6773 (8) | 0.5348 (5) | 0.7796 (4) | 0.0481 (15) | |
H13 | 0.7507 | 0.4985 | 0.7264 | 0.058* | |
C12 | 0.4989 (7) | 0.5410 (5) | 0.7932 (4) | 0.0405 (13) | |
C25 | 1.0642 (7) | 1.1175 (5) | 0.8342 (4) | 0.0420 (13) | |
C3 | −0.3356 (8) | 1.0498 (5) | 0.6004 (4) | 0.0569 (17) | |
H3A | −0.3081 | 1.0003 | 0.6623 | 0.068* | |
C20 | 0.8453 (8) | 0.9639 (5) | 0.8833 (4) | 0.0470 (14) | |
C4 | −0.3119 (8) | 1.0796 (5) | 0.4259 (4) | 0.0555 (17) | |
H4A | −0.2671 | 1.0514 | 0.3647 | 0.067* | |
C21 | 1.0303 (8) | 0.9131 (5) | 0.8847 (4) | 0.0578 (16) | |
H21 | 1.0826 | 0.8262 | 0.9022 | 0.069* | |
C26 | 1.1854 (8) | 1.1954 (6) | 0.8081 (4) | 0.0493 (15) | |
C11 | 0.4235 (9) | 0.4830 (5) | 0.7270 (5) | 0.0488 (15) | |
C24 | 1.1391 (8) | 0.9893 (5) | 0.8607 (4) | 0.0548 (16) | |
H24 | 1.2633 | 0.9534 | 0.8624 | 0.066* | |
C14 | 0.3926 (8) | 0.5997 (5) | 0.8701 (4) | 0.0497 (15) | |
H14 | 0.2712 | 0.6065 | 0.8801 | 0.060* | |
C23 | 0.8791 (7) | 1.1698 (5) | 0.8328 (4) | 0.0497 (15) | |
H23 | 0.8270 | 1.2567 | 0.8153 | 0.060* | |
C16 | 0.7486 (8) | 0.5810 (5) | 0.8427 (5) | 0.0579 (16) | |
H16 | 0.8702 | 0.5736 | 0.8328 | 0.069* | |
C17 | 0.6419 (9) | 0.6388 (5) | 0.9213 (4) | 0.0506 (15) | |
C22 | 0.7710 (7) | 1.0929 (5) | 0.8574 (4) | 0.0483 (15) | |
H22 | 0.6467 | 1.1289 | 0.8564 | 0.058* | |
C19 | 0.7263 (8) | 0.8831 (5) | 0.9132 (5) | 0.0580 (16) | |
H19A | 0.6332 | 0.9172 | 0.9644 | 0.070* | |
H19B | 0.6683 | 0.8828 | 0.8556 | 0.070* | |
C15 | 0.4634 (8) | 0.6489 (5) | 0.9332 (4) | 0.0569 (16) | |
H15 | 0.3886 | 0.6892 | 0.9842 | 0.068* | |
C1 | −0.4279 (8) | 1.2011 (5) | 0.4271 (4) | 0.0584 (17) | |
H1 | −0.4593 | 1.2521 | 0.3661 | 0.070* | |
C18 | 0.7241 (10) | 0.6800 (6) | 0.9958 (5) | 0.075 (2) | |
H18A | 0.6283 | 0.7254 | 1.0409 | 0.090* | |
H18B | 0.7993 | 0.6054 | 1.0356 | 0.090* | |
C6 | −0.1344 (9) | 0.8662 (5) | 0.5141 (6) | 0.0401 (13) | 0.677 (11) |
C8 | −0.1265 (10) | 0.7734 (7) | 0.5979 (5) | 0.045 (3) | 0.677 (11) |
H8A | −0.2039 | 0.7919 | 0.6552 | 0.054* | 0.677 (11) |
C9 | −0.0031 (11) | 0.6529 (6) | 0.5961 (5) | 0.047 (3) | 0.677 (11) |
H9A | 0.0022 | 0.5908 | 0.6522 | 0.057* | 0.677 (11) |
N2 | 0.1125 (8) | 0.6252 (5) | 0.5105 (6) | 0.0433 (16) | 0.677 (11) |
C10 | 0.1046 (10) | 0.7180 (7) | 0.4267 (5) | 0.041 (2) | 0.677 (11) |
H10A | 0.1819 | 0.6995 | 0.3694 | 0.049* | 0.677 (11) |
C7 | −0.0188 (11) | 0.8385 (6) | 0.4284 (5) | 0.044 (3) | 0.677 (11) |
H7A | −0.0241 | 0.9007 | 0.3724 | 0.053* | 0.677 (11) |
C6' | −0.133 (2) | 0.8703 (11) | 0.5145 (13) | 0.0401 (13) | 0.323 (11) |
C8' | −0.071 (2) | 0.8059 (15) | 0.6064 (11) | 0.045 (3) | 0.323 (11) |
H8'A | −0.1065 | 0.8458 | 0.6628 | 0.054* | 0.323 (11) |
C9' | 0.044 (3) | 0.6817 (15) | 0.6141 (11) | 0.047 (3) | 0.323 (11) |
H9'A | 0.0855 | 0.6386 | 0.6756 | 0.057* | 0.323 (11) |
N2' | 0.097 (2) | 0.6221 (12) | 0.5298 (14) | 0.0433 (16) | 0.323 (11) |
C10' | 0.035 (2) | 0.6865 (16) | 0.4379 (11) | 0.041 (2) | 0.323 (11) |
H10B | 0.0707 | 0.6466 | 0.3815 | 0.049* | 0.323 (11) |
C7' | −0.080 (2) | 0.8107 (15) | 0.4302 (11) | 0.044 (3) | 0.323 (11) |
H7'A | −0.1213 | 0.8538 | 0.3687 | 0.053* | 0.323 (11) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ag1 | 0.0548 (3) | 0.0338 (3) | 0.0852 (4) | 0.0053 (2) | −0.0155 (3) | −0.0179 (2) |
O3 | 0.039 (3) | 0.075 (3) | 0.087 (3) | −0.020 (2) | −0.011 (2) | −0.008 (2) |
O4 | 0.052 (3) | 0.056 (3) | 0.100 (4) | −0.027 (2) | −0.019 (3) | −0.001 (2) |
O9 | 0.081 (3) | 0.054 (3) | 0.089 (3) | −0.037 (3) | −0.019 (3) | −0.007 (2) |
O2 | 0.067 (3) | 0.061 (3) | 0.087 (3) | −0.036 (2) | −0.016 (3) | −0.014 (2) |
N1 | 0.048 (3) | 0.030 (3) | 0.063 (3) | −0.002 (2) | −0.009 (3) | −0.012 (2) |
C2 | 0.082 (5) | 0.039 (4) | 0.056 (4) | −0.003 (3) | −0.001 (4) | −0.015 (3) |
O1 | 0.074 (3) | 0.067 (3) | 0.067 (3) | −0.013 (2) | −0.009 (3) | −0.031 (2) |
C5 | 0.043 (3) | 0.032 (3) | 0.038 (3) | −0.008 (3) | −0.006 (3) | −0.004 (2) |
C13 | 0.047 (4) | 0.050 (4) | 0.048 (4) | −0.016 (3) | 0.005 (3) | −0.016 (3) |
C12 | 0.046 (4) | 0.028 (3) | 0.045 (3) | −0.009 (3) | −0.006 (3) | −0.005 (2) |
C25 | 0.037 (3) | 0.047 (4) | 0.049 (3) | −0.016 (3) | −0.009 (3) | −0.014 (3) |
C3 | 0.076 (5) | 0.042 (4) | 0.038 (3) | 0.002 (3) | −0.005 (3) | −0.008 (3) |
C20 | 0.050 (4) | 0.049 (4) | 0.051 (4) | −0.026 (3) | −0.003 (3) | −0.011 (3) |
C4 | 0.071 (4) | 0.042 (4) | 0.041 (4) | 0.004 (3) | −0.009 (3) | −0.016 (3) |
C21 | 0.051 (4) | 0.039 (4) | 0.084 (5) | −0.012 (3) | −0.010 (3) | −0.012 (3) |
C26 | 0.050 (4) | 0.055 (4) | 0.050 (4) | −0.023 (3) | −0.006 (3) | −0.013 (3) |
C11 | 0.059 (4) | 0.029 (3) | 0.053 (4) | −0.007 (3) | −0.016 (3) | −0.002 (3) |
C24 | 0.041 (4) | 0.048 (4) | 0.075 (4) | −0.006 (3) | −0.010 (3) | −0.018 (3) |
C14 | 0.042 (4) | 0.043 (3) | 0.065 (4) | −0.013 (3) | −0.004 (3) | −0.010 (3) |
C23 | 0.043 (4) | 0.045 (4) | 0.059 (4) | −0.012 (3) | −0.011 (3) | −0.006 (3) |
C16 | 0.049 (4) | 0.057 (4) | 0.075 (5) | −0.026 (3) | −0.003 (3) | −0.013 (3) |
C17 | 0.070 (5) | 0.041 (4) | 0.052 (4) | −0.030 (3) | −0.014 (3) | −0.005 (3) |
C22 | 0.039 (3) | 0.042 (4) | 0.063 (4) | −0.010 (3) | −0.013 (3) | −0.006 (3) |
C19 | 0.058 (4) | 0.054 (4) | 0.069 (4) | −0.027 (3) | −0.004 (3) | −0.011 (3) |
C15 | 0.064 (4) | 0.051 (4) | 0.058 (4) | −0.018 (3) | −0.001 (3) | −0.020 (3) |
C1 | 0.078 (5) | 0.040 (4) | 0.046 (4) | −0.004 (3) | −0.013 (3) | −0.002 (3) |
C18 | 0.108 (6) | 0.071 (5) | 0.064 (4) | −0.050 (4) | −0.021 (4) | −0.003 (4) |
C6 | 0.033 (3) | 0.033 (3) | 0.047 (3) | 0.001 (2) | −0.004 (3) | −0.010 (3) |
C8 | 0.051 (6) | 0.023 (5) | 0.053 (4) | −0.007 (4) | 0.006 (4) | −0.005 (4) |
C9 | 0.060 (7) | 0.036 (5) | 0.040 (5) | −0.009 (4) | −0.004 (4) | −0.004 (4) |
N2 | 0.048 (3) | 0.036 (3) | 0.042 (4) | −0.004 (2) | −0.008 (3) | −0.009 (3) |
C10 | 0.037 (6) | 0.041 (5) | 0.044 (4) | −0.003 (4) | −0.004 (4) | −0.019 (4) |
C7 | 0.057 (7) | 0.027 (5) | 0.050 (4) | −0.007 (4) | −0.011 (4) | −0.016 (3) |
C6' | 0.033 (3) | 0.033 (3) | 0.047 (3) | 0.001 (2) | −0.004 (3) | −0.010 (3) |
C8' | 0.051 (6) | 0.023 (5) | 0.053 (4) | −0.007 (4) | 0.006 (4) | −0.005 (4) |
C9' | 0.060 (7) | 0.036 (5) | 0.040 (5) | −0.009 (4) | −0.004 (4) | −0.004 (4) |
N2' | 0.048 (3) | 0.036 (3) | 0.042 (4) | −0.004 (2) | −0.008 (3) | −0.009 (3) |
C10' | 0.037 (6) | 0.041 (5) | 0.044 (4) | −0.003 (4) | −0.004 (4) | −0.019 (4) |
C7' | 0.057 (7) | 0.027 (5) | 0.050 (4) | −0.007 (4) | −0.011 (4) | −0.016 (3) |
Geometric parameters (Å, º) top
Ag1—N2 | 2.182 (6) | C24—H24 | 0.9300 |
Ag1—N1i | 2.194 (4) | C14—C15 | 1.387 (7) |
Ag1—N2' | 2.238 (13) | C14—H14 | 0.9300 |
Ag1—O1 | 2.517 (4) | C23—C22 | 1.388 (7) |
Ag1—Ag1ii | 3.2883 (10) | C23—H23 | 0.9300 |
O3—C26 | 1.211 (6) | C16—C17 | 1.388 (7) |
O4—C26 | 1.310 (6) | C16—H16 | 0.9300 |
O4—H4 | 0.8200 | C17—C15 | 1.367 (8) |
O9—C19 | 1.412 (6) | C17—C18 | 1.510 (7) |
O9—C18 | 1.422 (7) | C22—H22 | 0.9300 |
O2—C11 | 1.256 (7) | C19—H19A | 0.9700 |
N1—C2 | 1.326 (7) | C19—H19B | 0.9700 |
N1—C1 | 1.332 (6) | C15—H15 | 0.9300 |
N1—Ag1iii | 2.193 (4) | C1—H1 | 0.9300 |
C2—C3 | 1.375 (7) | C18—H18A | 0.9700 |
C2—H2 | 0.9300 | C18—H18B | 0.9700 |
O1—C11 | 1.241 (6) | C6—C8 | 1.3900 |
C5—C4 | 1.375 (7) | C6—C7 | 1.3900 |
C5—C3 | 1.385 (7) | C8—C9 | 1.3900 |
C5—C6' | 1.472 (13) | C8—H8A | 0.9300 |
C5—C6 | 1.505 (7) | C9—N2 | 1.3900 |
C13—C16 | 1.366 (7) | C9—H9A | 0.9300 |
C13—C12 | 1.378 (7) | N2—C10 | 1.3900 |
C13—H13 | 0.9300 | C10—C7 | 1.3900 |
C12—C14 | 1.373 (7) | C10—H10A | 0.9300 |
C12—C11 | 1.510 (7) | C7—H7A | 0.9300 |
C25—C24 | 1.372 (7) | C6'—C8' | 1.3900 |
C25—C23 | 1.384 (7) | C6'—C7' | 1.3900 |
C25—C26 | 1.481 (7) | C8'—C9' | 1.3900 |
C3—H3A | 0.9300 | C8'—H8'A | 0.9300 |
C20—C22 | 1.377 (7) | C9'—N2' | 1.3900 |
C20—C21 | 1.382 (7) | C9'—H9'A | 0.9300 |
C20—C19 | 1.494 (7) | N2'—C10' | 1.3900 |
C4—C1 | 1.377 (7) | C10'—C7' | 1.3900 |
C4—H4A | 0.9300 | C10'—H10B | 0.9300 |
C21—C24 | 1.385 (7) | C7'—H7'A | 0.9300 |
C21—H21 | 0.9300 | | |
| | | |
N2—Ag1—N1i | 166.4 (2) | C17—C16—H16 | 119.6 |
N1i—Ag1—N2' | 165.3 (4) | C15—C17—C16 | 118.0 (5) |
N2—Ag1—O1 | 104.10 (19) | C15—C17—C18 | 121.1 (6) |
N1i—Ag1—O1 | 88.46 (15) | C16—C17—C18 | 120.7 (6) |
N2'—Ag1—O1 | 100.8 (4) | C20—C22—C23 | 120.9 (5) |
N2—Ag1—Ag1ii | 97.87 (17) | C20—C22—H22 | 119.6 |
N1i—Ag1—Ag1ii | 93.78 (12) | C23—C22—H22 | 119.6 |
N2'—Ag1—Ag1ii | 100.9 (4) | O9—C19—C20 | 109.7 (5) |
O1—Ag1—Ag1ii | 52.96 (11) | O9—C19—H19A | 109.7 |
C26—O4—H4 | 109.5 | C20—C19—H19A | 109.7 |
C19—O9—C18 | 113.6 (5) | O9—C19—H19B | 109.7 |
C2—N1—C1 | 116.2 (5) | C20—C19—H19B | 109.7 |
C2—N1—Ag1iii | 118.7 (4) | H19A—C19—H19B | 108.2 |
C1—N1—Ag1iii | 125.0 (4) | C17—C15—C14 | 120.8 (5) |
N1—C2—C3 | 123.6 (5) | C17—C15—H15 | 119.6 |
N1—C2—H2 | 118.2 | C14—C15—H15 | 119.6 |
C3—C2—H2 | 118.2 | N1—C1—C4 | 123.2 (5) |
C11—O1—Ag1 | 112.2 (4) | N1—C1—H1 | 118.4 |
C4—C5—C3 | 115.1 (5) | C4—C1—H1 | 118.4 |
C4—C5—C6' | 122.5 (8) | O9—C18—C17 | 113.5 (5) |
C3—C5—C6' | 122.4 (8) | O9—C18—H18A | 108.9 |
C4—C5—C6 | 122.2 (5) | C17—C18—H18A | 108.9 |
C3—C5—C6 | 122.7 (5) | O9—C18—H18B | 108.9 |
C16—C13—C12 | 121.3 (5) | C17—C18—H18B | 108.9 |
C16—C13—H13 | 119.3 | H18A—C18—H18B | 107.7 |
C12—C13—H13 | 119.3 | C8—C6—C7 | 120.0 |
C14—C12—C13 | 117.8 (5) | C8—C6—C5 | 122.0 (5) |
C14—C12—C11 | 121.1 (5) | C7—C6—C5 | 117.9 (5) |
C13—C12—C11 | 121.1 (5) | C6—C8—C9 | 120.0 |
C24—C25—C23 | 119.3 (5) | C6—C8—H8A | 120.0 |
C24—C25—C26 | 118.4 (5) | C9—C8—H8A | 120.0 |
C23—C25—C26 | 122.2 (5) | N2—C9—C8 | 120.0 |
C2—C3—C5 | 120.8 (5) | N2—C9—H9A | 120.0 |
C2—C3—H3A | 119.6 | C8—C9—H9A | 120.0 |
C5—C3—H3A | 119.6 | C10—N2—C9 | 120.0 |
C22—C20—C21 | 118.3 (5) | C10—N2—Ag1 | 120.7 (4) |
C22—C20—C19 | 120.1 (5) | C9—N2—Ag1 | 118.7 (4) |
C21—C20—C19 | 121.5 (5) | N2—C10—C7 | 120.0 |
C5—C4—C1 | 121.2 (5) | N2—C10—H10A | 120.0 |
C5—C4—H4A | 119.4 | C7—C10—H10A | 120.0 |
C1—C4—H4A | 119.4 | C10—C7—C6 | 120.0 |
C20—C21—C24 | 121.2 (5) | C10—C7—H7A | 120.0 |
C20—C21—H21 | 119.4 | C6—C7—H7A | 120.0 |
C24—C21—H21 | 119.4 | C8'—C6'—C7' | 120.0 |
O3—C26—O4 | 122.4 (6) | C8'—C6'—C5 | 116.8 (11) |
O3—C26—C25 | 123.5 (6) | C7'—C6'—C5 | 123.1 (11) |
O4—C26—C25 | 114.1 (5) | C9'—C8'—C6' | 120.0 |
O1—C11—O2 | 126.1 (6) | C9'—C8'—H8'A | 120.0 |
O1—C11—C12 | 117.4 (6) | C6'—C8'—H8'A | 120.0 |
O2—C11—C12 | 116.5 (5) | C8'—C9'—N2' | 120.0 |
C25—C24—C21 | 120.1 (5) | C8'—C9'—H9'A | 120.0 |
C25—C24—H24 | 119.9 | N2'—C9'—H9'A | 120.0 |
C21—C24—H24 | 119.9 | C9'—N2'—C10' | 120.0 |
C12—C14—C15 | 121.1 (5) | C9'—N2'—Ag1 | 124.6 (8) |
C12—C14—H14 | 119.5 | C10'—N2'—Ag1 | 113.7 (9) |
C15—C14—H14 | 119.5 | C7'—C10'—N2' | 120.0 |
C25—C23—C22 | 120.1 (5) | C7'—C10'—H10B | 120.0 |
C25—C23—H23 | 119.9 | N2'—C10'—H10B | 120.0 |
C22—C23—H23 | 119.9 | C10'—C7'—C6' | 120.0 |
C13—C16—C17 | 120.9 (5) | C10'—C7'—H7'A | 120.0 |
C13—C16—H16 | 119.6 | C6'—C7'—H7'A | 120.0 |
| | | |
C1—N1—C2—C3 | −0.3 (9) | C18—C17—C15—C14 | −173.7 (5) |
Ag1iii—N1—C2—C3 | −177.2 (5) | C12—C14—C15—C17 | −0.9 (9) |
C16—C13—C12—C14 | 2.5 (8) | C2—N1—C1—C4 | −0.3 (9) |
C16—C13—C12—C11 | −176.4 (5) | Ag1iii—N1—C1—C4 | 176.4 (5) |
N1—C2—C3—C5 | 0.8 (10) | C5—C4—C1—N1 | 0.4 (10) |
C4—C5—C3—C2 | −0.7 (9) | C19—O9—C18—C17 | 74.5 (7) |
C6'—C5—C3—C2 | 177.3 (8) | C15—C17—C18—O9 | −131.7 (6) |
C6—C5—C3—C2 | 179.2 (6) | C16—C17—C18—O9 | 53.1 (8) |
C3—C5—C4—C1 | 0.2 (9) | C4—C5—C6—C8 | −159.2 (6) |
C6'—C5—C4—C1 | −177.9 (8) | C3—C5—C6—C8 | 20.8 (8) |
C6—C5—C4—C1 | −179.8 (6) | C6'—C5—C6—C8 | 101 (34) |
C22—C20—C21—C24 | −0.1 (9) | C4—C5—C6—C7 | 22.8 (8) |
C19—C20—C21—C24 | −177.5 (5) | C3—C5—C6—C7 | −157.2 (6) |
C24—C25—C26—O3 | −6.0 (9) | C6'—C5—C6—C7 | −77 (34) |
C23—C25—C26—O3 | 173.9 (5) | C7—C6—C8—C9 | 0.0 |
C24—C25—C26—O4 | 173.9 (5) | C5—C6—C8—C9 | −177.9 (6) |
C23—C25—C26—O4 | −6.1 (8) | C6—C8—C9—N2 | 0.0 |
Ag1—O1—C11—O2 | 22.2 (7) | C8—C9—N2—C10 | 0.0 |
Ag1—O1—C11—C12 | −156.2 (3) | C8—C9—N2—Ag1 | 171.1 (4) |
C14—C12—C11—O1 | 167.6 (5) | C9—N2—C10—C7 | 0.0 |
C13—C12—C11—O1 | −13.5 (8) | Ag1—N2—C10—C7 | −170.9 (4) |
C14—C12—C11—O2 | −10.9 (7) | N2—C10—C7—C6 | 0.0 |
C13—C12—C11—O2 | 167.9 (5) | C8—C6—C7—C10 | 0.0 |
C23—C25—C24—C21 | 0.6 (8) | C5—C6—C7—C10 | 178.0 (6) |
C26—C25—C24—C21 | −179.4 (5) | C4—C5—C6'—C8' | 170.1 (8) |
C20—C21—C24—C25 | −0.4 (9) | C3—C5—C6'—C8' | −7.8 (13) |
C13—C12—C14—C15 | −1.2 (8) | C6—C5—C6'—C8' | −109 (35) |
C11—C12—C14—C15 | 177.7 (5) | C4—C5—C6'—C7' | −12.9 (13) |
C24—C25—C23—C22 | −0.4 (8) | C3—C5—C6'—C7' | 169.2 (8) |
C26—C25—C23—C22 | 179.7 (5) | C6—C5—C6'—C7' | 68 (34) |
C12—C13—C16—C17 | −1.7 (9) | C7'—C6'—C8'—C9' | 0.0 |
C13—C16—C17—C15 | −0.4 (9) | C5—C6'—C8'—C9' | 177.1 (12) |
C13—C16—C17—C18 | 174.9 (5) | C6'—C8'—C9'—N2' | 0.0 |
C21—C20—C22—C23 | 0.4 (8) | C8'—C9'—N2'—C10' | 0.0 |
C19—C20—C22—C23 | 177.8 (5) | C8'—C9'—N2'—Ag1 | 164.0 (11) |
C25—C23—C22—C20 | −0.1 (8) | C9'—N2'—C10'—C7' | 0.0 |
C18—O9—C19—C20 | 170.2 (5) | Ag1—N2'—C10'—C7' | −165.7 (9) |
C22—C20—C19—O9 | −171.3 (5) | N2'—C10'—C7'—C6' | 0.0 |
C21—C20—C19—O9 | 6.1 (8) | C8'—C6'—C7'—C10' | 0.0 |
C16—C17—C15—C14 | 1.7 (9) | C5—C6'—C7'—C10' | −176.9 (13) |
Symmetry codes: (i) x+1, y−1, z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y+1, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O4—H4···O2iv | 0.82 | 1.78 | 2.530 (5) | 152 |
Symmetry code: (iv) x+1, y+1, z. |