Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110054697/sq3280sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110054697/sq3280Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270110054697/sq3280IIsup3.hkl |
CCDC references: 817032; 817033
K2CO3 (6.91 g, 50 mmol) was added with stirring to a solution of 1,2-bis(2-bromomethylphenoxy)ethane (2.00 g, 5 mmol) and indoline-2,3-dione (1.47 g, 10 mmol) in anhydrous CH3CN (50 ml). The mixture was stirred for 12 h at ambient temperature and monitored by thin-layer chromatography (TLC). After removal of the solvent under vacuum, the residue was purified on silica gel by column chromatography using CH2Cl2:MeOH (30:1 v/v) as eluent to afford (I) as a red crystalline solid (1.09 g, 2.05 mmol; yield 41%). Spectroscopic analysis: IR (KBr pellet, ν, cm-1): 1737 (s), 1615 (s), 1471 (s), 1351 (s), 1256 (m), 1119 (w), 1055 (w), 752 (s), 630 (m), 469 (m); 1H NMR (300 MHz, CDCl3, 298 K, TMS, δ, p.p.m.): 7.51 (d, 2H, o-C6H4), 7.31 (m, 2H, m-C6H4), 7.28 (m, 2H, p-C6H4), 7.23–6.98 (aabb, 8H, –C6H4), 6.78 (d, 2H, m-C6H4), 4.91 (s, 4H, –CH2–), 4.42 (s, 4H, –CH2–). Elemental analysis, calculated for C32H24N2O6: C 72.18, H 4.51, N 5.26, O 18.05%; found: C 72.19, H 4.50, N 5.25, O 18.06%.
A solution of AgSbF6 (6.46 mg, 0.019 mmol) in benzene (5 ml) was layered on a solution of (I) (10.0 mg, 0.019 mmol) in CH2Cl2 (7 ml). The system was left for about one week at room temperature and red crystals of (II) were obtained (7.90 mg, yield 48%). Spectroscopic analysis: IR (KBr pellet, ν, cm-1): 1712 (s), 1611 (s), 1491 (s), 1343 (s), 1245 (m), 1119 (w), 1062 (w), 759 (s), 662 (s), 472 (m).
The H atoms in both structures were placed in idealized positions and treated as riding, with C—H = 0.93 (aromatic), 0.97 (CH2) and, in (II), 0.98 Å (CH with C coordinated to Ag), and with Uiso(H) = 1.2Ueq(C). The [SbF6]- anion was statistically disordered over two orientations, with site-occupation factors set at 0.50:0.50. The Sb1—F3/Sb1—F3', Sb1—F6/Sb1—F6' and Sb1—F4/Sb1—F4' pairs of bond lengths were restrained to be the same within a standard deviation of 0.01 Å. Atom F2' was constrained to have the same anisotropic displacement parameters as atom F2.
For both compounds, data collection: SMART (Bruker, 2003); cell refinement: SMART (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C32H24N2O6 | F(000) = 556 |
Mr = 532.53 | Dx = 1.367 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P2yn | Cell parameters from 857 reflections |
a = 4.8272 (17) Å | θ = 2.6–20.9° |
b = 14.194 (5) Å | µ = 0.10 mm−1 |
c = 18.883 (7) Å | T = 298 K |
β = 91.472 (7)° | Bar, red |
V = 1293.4 (8) Å3 | 0.55 × 0.14 × 0.04 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 1506 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
Graphite monochromator | θmax = 25.5°, θmin = 1.8° |
ϕ and ω scans | h = −5→5 |
6683 measured reflections | k = −17→17 |
2398 independent reflections | l = −22→17 |
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)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0677P)2 + 0.1059P] where P = (Fo2 + 2Fc2)/3 |
2398 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.13 e Å−3 |
C32H24N2O6 | V = 1293.4 (8) Å3 |
Mr = 532.53 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 4.8272 (17) Å | µ = 0.10 mm−1 |
b = 14.194 (5) Å | T = 298 K |
c = 18.883 (7) Å | 0.55 × 0.14 × 0.04 mm |
β = 91.472 (7)° |
Bruker SMART CCD area-detector diffractometer | 1506 reflections with I > 2σ(I) |
6683 measured reflections | Rint = 0.046 |
2398 independent reflections |
R[F2 > 2σ(F2)] = 0.065 | 0 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.17 e Å−3 |
2398 reflections | Δρmin = −0.13 e Å−3 |
181 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0460 (6) | 0.34667 (18) | 0.22697 (14) | 0.0505 (7) | |
C2 | −0.1003 (6) | 0.2714 (2) | 0.25147 (15) | 0.0648 (8) | |
H2 | −0.0792 | 0.2113 | 0.2328 | 0.078* | |
C3 | −0.2851 (7) | 0.2899 (3) | 0.30652 (17) | 0.0831 (11) | |
H3 | −0.3859 | 0.2403 | 0.3252 | 0.100* | |
C4 | −0.3202 (8) | 0.3788 (3) | 0.33323 (18) | 0.0871 (11) | |
H4 | −0.4466 | 0.3886 | 0.3688 | 0.105* | |
C5 | −0.1735 (8) | 0.4526 (3) | 0.30853 (18) | 0.0816 (11) | |
H5 | −0.1965 | 0.5128 | 0.3269 | 0.098* | |
C6 | 0.0111 (6) | 0.4361 (2) | 0.25532 (15) | 0.0604 (8) | |
C7 | 0.1959 (7) | 0.4991 (2) | 0.21878 (16) | 0.0711 (9) | |
C8 | 0.3527 (7) | 0.4360 (2) | 0.16718 (16) | 0.0621 (8) | |
C9 | 0.3228 (6) | 0.26742 (19) | 0.13121 (14) | 0.0562 (8) | |
H9A | 0.3734 | 0.2157 | 0.1626 | 0.067* | |
H9B | 0.4857 | 0.2840 | 0.1049 | 0.067* | |
C10 | 0.1012 (6) | 0.23380 (17) | 0.07975 (13) | 0.0471 (7) | |
C11 | 0.0150 (6) | 0.14134 (19) | 0.07931 (15) | 0.0593 (8) | |
H11 | 0.0934 | 0.0997 | 0.1121 | 0.071* | |
C12 | −0.1832 (7) | 0.1087 (2) | 0.03189 (18) | 0.0701 (9) | |
H12 | −0.2372 | 0.0459 | 0.0329 | 0.084* | |
C13 | −0.3014 (7) | 0.1690 (2) | −0.01692 (17) | 0.0683 (9) | |
H13 | −0.4379 | 0.1473 | −0.0485 | 0.082* | |
C14 | −0.2181 (6) | 0.2615 (2) | −0.01915 (14) | 0.0606 (8) | |
H14 | −0.2956 | 0.3020 | −0.0529 | 0.073* | |
C15 | −0.0193 (6) | 0.29457 (17) | 0.02871 (14) | 0.0480 (7) | |
C16 | −0.0569 (7) | 0.45357 (16) | −0.01211 (15) | 0.0606 (8) | |
H16A | −0.2558 | 0.4513 | −0.0061 | 0.073* | |
H16B | −0.0190 | 0.4433 | −0.0617 | 0.073* | |
N1 | 0.2453 (5) | 0.34815 (14) | 0.17423 (11) | 0.0510 (6) | |
O1 | 0.2339 (6) | 0.58289 (16) | 0.22527 (15) | 0.1163 (10) | |
O2 | 0.5383 (5) | 0.46048 (15) | 0.12861 (13) | 0.0868 (8) | |
O3 | 0.0785 (4) | 0.38421 (12) | 0.03087 (10) | 0.0592 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0492 (18) | 0.0577 (17) | 0.0443 (15) | 0.0053 (14) | −0.0080 (14) | 0.0005 (13) |
C2 | 0.066 (2) | 0.0686 (19) | 0.0592 (18) | −0.0006 (17) | 0.0003 (17) | 0.0024 (15) |
C3 | 0.071 (2) | 0.119 (3) | 0.060 (2) | −0.013 (2) | 0.0062 (18) | 0.010 (2) |
C4 | 0.073 (3) | 0.131 (3) | 0.058 (2) | 0.014 (2) | 0.0031 (19) | −0.021 (2) |
C5 | 0.080 (3) | 0.100 (3) | 0.065 (2) | 0.026 (2) | −0.007 (2) | −0.022 (2) |
C6 | 0.060 (2) | 0.0674 (19) | 0.0529 (18) | 0.0106 (16) | −0.0094 (16) | −0.0108 (15) |
C7 | 0.085 (3) | 0.0549 (19) | 0.072 (2) | −0.0029 (18) | −0.0220 (19) | −0.0064 (16) |
C8 | 0.067 (2) | 0.066 (2) | 0.0534 (19) | −0.0078 (17) | −0.0093 (17) | 0.0048 (15) |
C9 | 0.0537 (18) | 0.0578 (17) | 0.0570 (17) | 0.0100 (14) | 0.0017 (14) | 0.0022 (13) |
C10 | 0.0478 (17) | 0.0470 (15) | 0.0472 (15) | 0.0074 (13) | 0.0134 (13) | −0.0017 (12) |
C11 | 0.068 (2) | 0.0515 (17) | 0.0592 (18) | 0.0094 (15) | 0.0079 (17) | 0.0028 (14) |
C12 | 0.087 (3) | 0.0508 (18) | 0.073 (2) | −0.0077 (17) | 0.018 (2) | −0.0077 (16) |
C13 | 0.072 (2) | 0.072 (2) | 0.060 (2) | −0.0107 (17) | 0.0041 (17) | −0.0183 (17) |
C14 | 0.069 (2) | 0.0665 (19) | 0.0462 (16) | 0.0011 (16) | 0.0016 (15) | −0.0010 (14) |
C15 | 0.0511 (18) | 0.0454 (15) | 0.0482 (16) | 0.0033 (13) | 0.0133 (14) | −0.0020 (12) |
C16 | 0.068 (2) | 0.0561 (17) | 0.0573 (18) | 0.0048 (15) | −0.0027 (16) | 0.0124 (14) |
N1 | 0.0551 (15) | 0.0532 (14) | 0.0447 (13) | −0.0005 (11) | 0.0030 (12) | 0.0013 (10) |
O1 | 0.152 (3) | 0.0580 (16) | 0.138 (3) | −0.0148 (16) | −0.016 (2) | −0.0214 (14) |
O2 | 0.0849 (18) | 0.0991 (18) | 0.0763 (15) | −0.0311 (14) | −0.0021 (14) | 0.0117 (13) |
O3 | 0.0627 (14) | 0.0505 (11) | 0.0639 (13) | 0.0010 (9) | −0.0089 (10) | 0.0117 (9) |
C1—C2 | 1.368 (4) | C9—H9A | 0.9700 |
C1—C6 | 1.390 (3) | C9—H9B | 0.9700 |
C1—N1 | 1.402 (3) | C10—C11 | 1.377 (4) |
C2—C3 | 1.412 (4) | C10—C15 | 1.408 (3) |
C2—H2 | 0.9300 | C11—C12 | 1.374 (4) |
C3—C4 | 1.372 (5) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.371 (4) |
C4—C5 | 1.353 (5) | C12—H12 | 0.9300 |
C4—H4 | 0.9300 | C13—C14 | 1.373 (4) |
C5—C6 | 1.380 (5) | C13—H13 | 0.9300 |
C5—H5 | 0.9300 | C14—C15 | 1.383 (4) |
C6—C7 | 1.450 (4) | C14—H14 | 0.9300 |
C7—O1 | 1.209 (3) | C15—O3 | 1.357 (3) |
C7—C8 | 1.537 (4) | C16—O3 | 1.424 (3) |
C8—O2 | 1.219 (4) | C16—C16i | 1.495 (5) |
C8—N1 | 1.358 (3) | C16—H16A | 0.9700 |
C9—N1 | 1.459 (3) | C16—H16B | 0.9700 |
C9—C10 | 1.504 (4) | ||
C2—C1—C6 | 121.0 (3) | H9A—C9—H9B | 107.5 |
C2—C1—N1 | 128.4 (3) | C11—C10—C15 | 117.4 (3) |
C6—C1—N1 | 110.6 (2) | C11—C10—C9 | 121.1 (2) |
C1—C2—C3 | 116.5 (3) | C15—C10—C9 | 121.5 (2) |
C1—C2—H2 | 121.8 | C12—C11—C10 | 122.0 (3) |
C3—C2—H2 | 121.8 | C12—C11—H11 | 119.0 |
C4—C3—C2 | 121.9 (3) | C10—C11—H11 | 119.0 |
C4—C3—H3 | 119.1 | C13—C12—C11 | 119.9 (3) |
C2—C3—H3 | 119.1 | C13—C12—H12 | 120.0 |
C5—C4—C3 | 121.0 (4) | C11—C12—H12 | 120.0 |
C5—C4—H4 | 119.5 | C12—C13—C14 | 120.0 (3) |
C3—C4—H4 | 119.5 | C12—C13—H13 | 120.0 |
C4—C5—C6 | 118.2 (3) | C14—C13—H13 | 120.0 |
C4—C5—H5 | 120.9 | C13—C14—C15 | 120.2 (3) |
C6—C5—H5 | 120.9 | C13—C14—H14 | 119.9 |
C5—C6—C1 | 121.5 (3) | C15—C14—H14 | 119.9 |
C5—C6—C7 | 131.2 (3) | O3—C15—C14 | 124.9 (2) |
C1—C6—C7 | 107.3 (3) | O3—C15—C10 | 114.6 (2) |
O1—C7—C6 | 130.7 (3) | C14—C15—C10 | 120.4 (2) |
O1—C7—C8 | 124.2 (3) | O3—C16—C16i | 106.0 (3) |
C6—C7—C8 | 105.1 (3) | O3—C16—H16A | 110.5 |
O2—C8—N1 | 127.5 (3) | C16i—C16—H16A | 110.5 |
O2—C8—C7 | 126.4 (3) | O3—C16—H16B | 110.5 |
N1—C8—C7 | 106.1 (3) | C16i—C16—H16B | 110.5 |
N1—C9—C10 | 114.9 (2) | H16A—C16—H16B | 108.7 |
N1—C9—H9A | 108.6 | C8—N1—C1 | 110.7 (2) |
C10—C9—H9A | 108.6 | C8—N1—C9 | 124.2 (2) |
N1—C9—H9B | 108.6 | C1—N1—C9 | 125.0 (2) |
C10—C9—H9B | 108.6 | C15—O3—C16 | 118.5 (2) |
C6—C1—C2—C3 | −0.2 (4) | C10—C11—C12—C13 | 0.0 (4) |
N1—C1—C2—C3 | 178.7 (3) | C11—C12—C13—C14 | 1.1 (5) |
C1—C2—C3—C4 | 1.2 (5) | C12—C13—C14—C15 | −1.4 (4) |
C2—C3—C4—C5 | −1.3 (5) | C13—C14—C15—O3 | 179.6 (3) |
C3—C4—C5—C6 | 0.5 (5) | C13—C14—C15—C10 | 0.5 (4) |
C4—C5—C6—C1 | 0.5 (5) | C11—C10—C15—O3 | −178.6 (2) |
C4—C5—C6—C7 | −179.6 (3) | C9—C10—C15—O3 | −0.7 (3) |
C2—C1—C6—C5 | −0.6 (4) | C11—C10—C15—C14 | 0.6 (4) |
N1—C1—C6—C5 | −179.7 (3) | C9—C10—C15—C14 | 178.5 (2) |
C2—C1—C6—C7 | 179.4 (3) | O2—C8—N1—C1 | 176.4 (3) |
N1—C1—C6—C7 | 0.4 (3) | C7—C8—N1—C1 | −2.8 (3) |
C5—C6—C7—O1 | −0.7 (6) | O2—C8—N1—C9 | −5.1 (5) |
C1—C6—C7—O1 | 179.2 (3) | C7—C8—N1—C9 | 175.7 (2) |
C5—C6—C7—C8 | 178.1 (3) | C2—C1—N1—C8 | −177.3 (3) |
C1—C6—C7—C8 | −2.0 (3) | C6—C1—N1—C8 | 1.6 (3) |
O1—C7—C8—O2 | 2.6 (5) | C2—C1—N1—C9 | 4.2 (4) |
C6—C7—C8—O2 | −176.2 (3) | C6—C1—N1—C9 | −176.9 (2) |
O1—C7—C8—N1 | −178.2 (3) | C10—C9—N1—C8 | −110.2 (3) |
C6—C7—C8—N1 | 2.9 (3) | C10—C9—N1—C1 | 68.1 (3) |
N1—C9—C10—C11 | −125.7 (3) | C14—C15—O3—C16 | 9.3 (4) |
N1—C9—C10—C15 | 56.5 (3) | C10—C15—O3—C16 | −171.6 (2) |
C15—C10—C11—C12 | −0.8 (4) | C16i—C16—O3—C15 | 168.8 (3) |
C9—C10—C11—C12 | −178.7 (3) |
Symmetry code: (i) −x, −y+1, −z. |
[Ag2(C32H24N2O6)2][SbF6]2 | Z = 1 |
Mr = 1752.30 | F(000) = 860 |
Triclinic, P1 | Dx = 1.898 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.193 (2) Å | Cell parameters from 2230 reflections |
b = 11.594 (3) Å | θ = 2.5–22.0° |
c = 14.220 (3) Å | µ = 1.61 mm−1 |
α = 111.121 (3)° | T = 298 K |
β = 91.073 (3)° | Block, red |
γ = 100.819 (3)° | 0.30 × 0.17 × 0.10 mm |
V = 1533.0 (6) Å3 |
Bruker SMART CCD area-detector diffractometer | 5593 independent reflections |
Radiation source: fine-focus sealed tube | 4279 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 25.5°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | h = −10→12 |
Tmin = 0.645, Tmax = 0.856 | k = −13→14 |
8087 measured reflections | l = −17→17 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0582P)2 + 1.8707P] where P = (Fo2 + 2Fc2)/3 |
5593 reflections | (Δ/σ)max = 0.001 |
481 parameters | Δρmax = 1.07 e Å−3 |
3 restraints | Δρmin = −1.02 e Å−3 |
[Ag2(C32H24N2O6)2][SbF6]2 | γ = 100.819 (3)° |
Mr = 1752.30 | V = 1533.0 (6) Å3 |
Triclinic, P1 | Z = 1 |
a = 10.193 (2) Å | Mo Kα radiation |
b = 11.594 (3) Å | µ = 1.61 mm−1 |
c = 14.220 (3) Å | T = 298 K |
α = 111.121 (3)° | 0.30 × 0.17 × 0.10 mm |
β = 91.073 (3)° |
Bruker SMART CCD area-detector diffractometer | 5593 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2003) | 4279 reflections with I > 2σ(I) |
Tmin = 0.645, Tmax = 0.856 | Rint = 0.024 |
8087 measured reflections |
R[F2 > 2σ(F2)] = 0.053 | 3 restraints |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.03 | Δρmax = 1.07 e Å−3 |
5593 reflections | Δρmin = −1.02 e Å−3 |
481 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Ag1 | −0.20269 (7) | 0.35357 (5) | 0.42128 (4) | 0.0796 (2) | |
C1 | 0.3205 (6) | 0.4053 (6) | 0.4483 (4) | 0.0485 (13) | |
C2 | 0.3631 (5) | 0.2907 (5) | 0.3880 (4) | 0.0462 (13) | |
C3 | 0.4572 (6) | 0.2677 (6) | 0.3178 (5) | 0.0564 (15) | |
H3 | 0.5081 | 0.3334 | 0.3029 | 0.068* | |
C4 | 0.4733 (6) | 0.1456 (7) | 0.2707 (5) | 0.0652 (18) | |
H4 | 0.5343 | 0.1279 | 0.2223 | 0.078* | |
C5 | 0.3994 (7) | 0.0490 (7) | 0.2948 (6) | 0.072 (2) | |
H5 | 0.4129 | −0.0328 | 0.2628 | 0.086* | |
C6 | 0.3050 (6) | 0.0708 (6) | 0.3658 (5) | 0.0637 (17) | |
H6 | 0.2558 | 0.0054 | 0.3818 | 0.076* | |
C7 | 0.2882 (6) | 0.1932 (5) | 0.4109 (4) | 0.0490 (13) | |
C8 | 0.2091 (6) | 0.3630 (5) | 0.5067 (4) | 0.0474 (13) | |
C9 | 0.1080 (6) | 0.1641 (6) | 0.5282 (4) | 0.0538 (15) | |
H9A | 0.1402 | 0.1903 | 0.5989 | 0.065* | |
H9B | 0.1114 | 0.0757 | 0.4950 | 0.065* | |
C10 | −0.0341 (6) | 0.1780 (5) | 0.5215 (4) | 0.0489 (13) | |
C11 | −0.1097 (6) | 0.1270 (5) | 0.4280 (4) | 0.0457 (13) | |
C12 | −0.2450 (6) | 0.1377 (6) | 0.4212 (5) | 0.0545 (15) | |
H12 | −0.3059 | 0.0717 | 0.3659 | 0.065* | |
C13 | −0.3004 (7) | 0.2012 (6) | 0.5085 (6) | 0.0663 (18) | |
H13 | −0.3981 | 0.1807 | 0.5084 | 0.080* | |
C14 | −0.2259 (8) | 0.2535 (7) | 0.6004 (6) | 0.079 (2) | |
H14 | −0.2633 | 0.2979 | 0.6582 | 0.095* | |
C15 | −0.0950 (7) | 0.2398 (6) | 0.6064 (5) | 0.0670 (18) | |
H15 | −0.0458 | 0.2729 | 0.6694 | 0.080* | |
C16 | −0.1128 (6) | 0.0250 (6) | 0.2483 (4) | 0.0520 (14) | |
H16A | −0.1530 | 0.0908 | 0.2403 | 0.062* | |
H16B | −0.1831 | −0.0491 | 0.2367 | 0.062* | |
C17 | −0.0094 (6) | −0.0064 (5) | 0.1752 (4) | 0.0512 (14) | |
H17A | 0.0473 | −0.0537 | 0.1952 | 0.061* | |
H17B | −0.0525 | −0.0576 | 0.1078 | 0.061* | |
C18 | 0.1676 (5) | 0.1032 (5) | 0.1116 (4) | 0.0424 (12) | |
C19 | 0.1988 (6) | −0.0095 (5) | 0.0491 (4) | 0.0516 (14) | |
H19 | 0.1500 | −0.0863 | 0.0481 | 0.062* | |
C20 | 0.3029 (7) | −0.0071 (6) | −0.0117 (5) | 0.0622 (17) | |
H20 | 0.3266 | −0.0822 | −0.0513 | 0.075* | |
C21 | 0.3712 (7) | 0.1053 (7) | −0.0139 (5) | 0.0643 (17) | |
H21 | 0.4388 | 0.1064 | −0.0567 | 0.077* | |
C22 | 0.3393 (6) | 0.2162 (6) | 0.0475 (5) | 0.0540 (15) | |
H22 | 0.3871 | 0.2924 | 0.0465 | 0.065* | |
C23 | 0.2377 (5) | 0.2176 (5) | 0.1108 (4) | 0.0429 (12) | |
C24 | 0.2107 (6) | 0.3421 (5) | 0.1799 (4) | 0.0499 (14) | |
H24A | 0.2366 | 0.3539 | 0.2493 | 0.060* | |
H24B | 0.2666 | 0.4095 | 0.1648 | 0.060* | |
C25 | −0.0144 (6) | 0.3522 (5) | 0.2435 (4) | 0.0460 (13) | |
C26 | −0.1544 (6) | 0.3407 (5) | 0.1955 (4) | 0.0483 (13) | |
C27 | −0.1344 (5) | 0.3430 (5) | 0.0945 (4) | 0.0458 (13) | |
C28 | 0.0010 (5) | 0.3467 (4) | 0.0833 (4) | 0.0407 (12) | |
C29 | 0.0543 (6) | 0.3441 (5) | −0.0062 (4) | 0.0500 (14) | |
H29 | 0.1450 | 0.3466 | −0.0141 | 0.060* | |
C30 | −0.0357 (7) | 0.3376 (6) | −0.0835 (5) | 0.0612 (17) | |
H30 | −0.0037 | 0.3350 | −0.1449 | 0.073* | |
C31 | −0.1695 (8) | 0.3348 (6) | −0.0733 (5) | 0.0680 (19) | |
H31 | −0.2259 | 0.3308 | −0.1271 | 0.082* | |
C32 | −0.2207 (6) | 0.3381 (5) | 0.0165 (5) | 0.0574 (15) | |
H32 | −0.3113 | 0.3370 | 0.0244 | 0.069* | |
N1 | 0.1959 (4) | 0.2378 (4) | 0.4823 (3) | 0.0442 (10) | |
N2 | 0.0707 (4) | 0.3528 (4) | 0.1717 (3) | 0.0439 (10) | |
O1 | 0.3549 (5) | 0.5140 (4) | 0.4556 (3) | 0.0641 (11) | |
O2 | 0.1461 (5) | 0.4326 (4) | 0.5649 (3) | 0.0619 (11) | |
O3 | −0.0450 (4) | 0.0677 (4) | 0.3484 (3) | 0.0510 (9) | |
O4 | 0.0687 (4) | 0.1091 (3) | 0.1757 (3) | 0.0493 (9) | |
O5 | 0.0114 (4) | 0.3543 (4) | 0.3278 (3) | 0.0572 (11) | |
O6 | −0.2563 (4) | 0.3242 (4) | 0.2363 (3) | 0.0633 (11) | |
Sb1 | 0.58932 (4) | 0.65652 (4) | 0.22306 (3) | 0.05775 (17) | |
F1 | 0.5908 (17) | 0.557 (2) | 0.0941 (13) | 0.173 (9) | 0.50 |
F2 | 0.553 (3) | 0.773 (3) | 0.1718 (17) | 0.213 (8) | 0.50 |
F3 | 0.7705 (10) | 0.7206 (18) | 0.225 (2) | 0.141 (8) | 0.50 |
F4 | 0.5995 (16) | 0.777 (2) | 0.3467 (10) | 0.154 (8) | 0.50 |
F5 | 0.625 (2) | 0.551 (3) | 0.273 (3) | 0.224 (10) | 0.50 |
F6 | 0.4088 (10) | 0.645 (3) | 0.212 (3) | 0.170 (12) | 0.50 |
F3' | 0.7694 (8) | 0.6482 (18) | 0.2339 (17) | 0.132 (8) | 0.50 |
F4' | 0.606 (3) | 0.8212 (9) | 0.258 (3) | 0.267 (16) | 0.50 |
F1' | 0.5596 (15) | 0.4808 (10) | 0.176 (2) | 0.154 (7) | 0.50 |
F5' | 0.5852 (15) | 0.656 (4) | 0.3504 (12) | 0.191 (12) | 0.50 |
F2' | 0.601 (3) | 0.642 (3) | 0.0948 (17) | 0.213 (8) | 0.50 |
F6' | 0.4072 (7) | 0.615 (2) | 0.219 (2) | 0.112 (7) | 0.50 |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ag1 | 0.1191 (5) | 0.0646 (3) | 0.0787 (4) | 0.0429 (3) | 0.0489 (4) | 0.0407 (3) |
C1 | 0.050 (3) | 0.051 (3) | 0.049 (3) | 0.011 (3) | −0.001 (3) | 0.025 (3) |
C2 | 0.040 (3) | 0.049 (3) | 0.051 (3) | 0.011 (3) | 0.001 (2) | 0.019 (3) |
C3 | 0.041 (3) | 0.074 (4) | 0.057 (4) | 0.013 (3) | 0.006 (3) | 0.027 (3) |
C4 | 0.047 (4) | 0.094 (5) | 0.058 (4) | 0.031 (4) | 0.011 (3) | 0.023 (4) |
C5 | 0.057 (4) | 0.065 (4) | 0.083 (5) | 0.027 (4) | 0.001 (4) | 0.008 (4) |
C6 | 0.053 (4) | 0.049 (4) | 0.083 (5) | 0.009 (3) | 0.002 (3) | 0.018 (3) |
C7 | 0.048 (3) | 0.052 (3) | 0.044 (3) | 0.013 (3) | −0.004 (3) | 0.013 (3) |
C8 | 0.048 (3) | 0.048 (3) | 0.044 (3) | 0.015 (3) | 0.000 (3) | 0.013 (3) |
C9 | 0.060 (4) | 0.059 (4) | 0.048 (3) | 0.008 (3) | 0.000 (3) | 0.029 (3) |
C10 | 0.054 (3) | 0.050 (3) | 0.049 (3) | 0.011 (3) | 0.008 (3) | 0.026 (3) |
C11 | 0.053 (3) | 0.040 (3) | 0.048 (3) | 0.007 (3) | 0.010 (3) | 0.021 (3) |
C12 | 0.044 (3) | 0.062 (4) | 0.065 (4) | 0.012 (3) | 0.008 (3) | 0.032 (3) |
C13 | 0.053 (4) | 0.074 (4) | 0.085 (5) | 0.019 (3) | 0.028 (4) | 0.041 (4) |
C14 | 0.090 (6) | 0.081 (5) | 0.075 (5) | 0.034 (4) | 0.045 (4) | 0.029 (4) |
C15 | 0.075 (5) | 0.078 (5) | 0.046 (4) | 0.015 (4) | 0.016 (3) | 0.020 (3) |
C16 | 0.051 (3) | 0.051 (3) | 0.050 (3) | −0.002 (3) | 0.001 (3) | 0.021 (3) |
C17 | 0.064 (4) | 0.042 (3) | 0.039 (3) | 0.005 (3) | 0.006 (3) | 0.008 (2) |
C18 | 0.043 (3) | 0.050 (3) | 0.035 (3) | 0.015 (3) | 0.007 (2) | 0.014 (2) |
C19 | 0.058 (4) | 0.044 (3) | 0.052 (3) | 0.013 (3) | 0.012 (3) | 0.015 (3) |
C20 | 0.069 (4) | 0.063 (4) | 0.055 (4) | 0.029 (3) | 0.016 (3) | 0.013 (3) |
C21 | 0.054 (4) | 0.081 (5) | 0.064 (4) | 0.027 (4) | 0.022 (3) | 0.027 (4) |
C22 | 0.044 (3) | 0.062 (4) | 0.061 (4) | 0.013 (3) | 0.011 (3) | 0.028 (3) |
C23 | 0.037 (3) | 0.046 (3) | 0.048 (3) | 0.013 (2) | 0.005 (2) | 0.018 (3) |
C24 | 0.046 (3) | 0.047 (3) | 0.055 (3) | 0.010 (3) | 0.002 (3) | 0.016 (3) |
C25 | 0.055 (3) | 0.037 (3) | 0.048 (3) | 0.017 (3) | 0.013 (3) | 0.015 (3) |
C26 | 0.050 (3) | 0.040 (3) | 0.055 (3) | 0.017 (3) | 0.014 (3) | 0.013 (3) |
C27 | 0.044 (3) | 0.041 (3) | 0.053 (3) | 0.013 (2) | 0.005 (3) | 0.016 (3) |
C28 | 0.050 (3) | 0.029 (3) | 0.045 (3) | 0.012 (2) | 0.005 (2) | 0.014 (2) |
C29 | 0.062 (4) | 0.043 (3) | 0.051 (3) | 0.020 (3) | 0.016 (3) | 0.020 (3) |
C30 | 0.085 (5) | 0.057 (4) | 0.052 (4) | 0.028 (4) | 0.014 (3) | 0.025 (3) |
C31 | 0.090 (5) | 0.060 (4) | 0.055 (4) | 0.020 (4) | −0.011 (4) | 0.022 (3) |
C32 | 0.049 (3) | 0.053 (4) | 0.070 (4) | 0.018 (3) | 0.001 (3) | 0.020 (3) |
N1 | 0.045 (3) | 0.044 (3) | 0.046 (3) | 0.009 (2) | 0.004 (2) | 0.020 (2) |
N2 | 0.043 (3) | 0.044 (2) | 0.048 (3) | 0.015 (2) | 0.008 (2) | 0.017 (2) |
O1 | 0.071 (3) | 0.054 (3) | 0.073 (3) | 0.014 (2) | 0.014 (2) | 0.029 (2) |
O2 | 0.078 (3) | 0.058 (3) | 0.056 (3) | 0.025 (2) | 0.022 (2) | 0.023 (2) |
O3 | 0.049 (2) | 0.061 (2) | 0.045 (2) | 0.0156 (19) | 0.0097 (18) | 0.0187 (19) |
O4 | 0.059 (2) | 0.038 (2) | 0.048 (2) | 0.0104 (18) | 0.0190 (18) | 0.0109 (17) |
O5 | 0.076 (3) | 0.061 (3) | 0.046 (2) | 0.034 (2) | 0.019 (2) | 0.023 (2) |
O6 | 0.051 (3) | 0.069 (3) | 0.076 (3) | 0.023 (2) | 0.026 (2) | 0.029 (2) |
Sb1 | 0.0471 (3) | 0.0648 (3) | 0.0586 (3) | 0.0053 (2) | 0.00704 (19) | 0.0227 (2) |
F1 | 0.147 (12) | 0.180 (16) | 0.106 (10) | 0.095 (13) | −0.045 (9) | −0.074 (11) |
F2 | 0.284 (19) | 0.28 (2) | 0.189 (15) | 0.124 (16) | 0.108 (13) | 0.180 (16) |
F3 | 0.070 (8) | 0.155 (17) | 0.145 (12) | −0.032 (8) | 0.042 (8) | 0.019 (14) |
F4 | 0.103 (11) | 0.217 (18) | 0.073 (9) | 0.058 (13) | −0.005 (7) | −0.039 (10) |
F5 | 0.25 (3) | 0.22 (2) | 0.32 (3) | 0.11 (2) | 0.05 (2) | 0.21 (3) |
F6 | 0.145 (17) | 0.23 (3) | 0.132 (17) | 0.112 (16) | −0.017 (13) | 0.036 (17) |
F3' | 0.045 (6) | 0.181 (19) | 0.114 (11) | 0.009 (7) | 0.007 (6) | −0.005 (14) |
F4' | 0.28 (3) | 0.042 (6) | 0.46 (4) | 0.027 (10) | 0.20 (3) | 0.061 (15) |
F1' | 0.119 (11) | 0.057 (6) | 0.25 (2) | 0.018 (6) | 0.017 (12) | 0.018 (9) |
F5' | 0.083 (8) | 0.41 (4) | 0.079 (9) | −0.004 (17) | −0.001 (7) | 0.121 (17) |
F2' | 0.284 (19) | 0.28 (2) | 0.189 (15) | 0.124 (16) | 0.108 (13) | 0.180 (16) |
F6' | 0.028 (5) | 0.116 (10) | 0.176 (19) | −0.009 (6) | 0.011 (8) | 0.046 (10) |
Ag1—O2i | 2.372 (4) | C18—C23 | 1.387 (7) |
Ag1—C12 | 2.458 (6) | C18—C19 | 1.389 (7) |
Ag1—O6 | 2.562 (5) | C19—C20 | 1.384 (8) |
Ag1—C13 | 2.572 (6) | C19—H19 | 0.9300 |
Ag1—O5 | 2.577 (4) | C20—C21 | 1.368 (9) |
C1—O1 | 1.209 (7) | C20—H20 | 0.9300 |
C1—C2 | 1.448 (8) | C21—C22 | 1.372 (9) |
C1—C8 | 1.529 (8) | C21—H21 | 0.9300 |
C2—C7 | 1.385 (8) | C22—C23 | 1.384 (7) |
C2—C3 | 1.389 (8) | C22—H22 | 0.9300 |
C3—C4 | 1.374 (9) | C23—C24 | 1.504 (7) |
C3—H3 | 0.9300 | C24—N2 | 1.462 (7) |
C4—C5 | 1.382 (10) | C24—H24A | 0.9700 |
C4—H4 | 0.9300 | C24—H24B | 0.9700 |
C5—C6 | 1.398 (9) | C25—O5 | 1.213 (7) |
C5—H5 | 0.9300 | C25—N2 | 1.353 (7) |
C6—C7 | 1.378 (8) | C25—C26 | 1.532 (8) |
C6—H6 | 0.9300 | C26—O6 | 1.217 (7) |
C7—N1 | 1.422 (7) | C26—C27 | 1.464 (8) |
C8—O2 | 1.217 (7) | C27—C32 | 1.381 (8) |
C8—N1 | 1.344 (7) | C27—C28 | 1.386 (7) |
C9—N1 | 1.448 (7) | C28—C29 | 1.386 (7) |
C9—C10 | 1.492 (8) | C28—N2 | 1.406 (7) |
C9—H9A | 0.9700 | C29—C30 | 1.390 (9) |
C9—H9B | 0.9700 | C29—H29 | 0.9300 |
C10—C15 | 1.389 (8) | C30—C31 | 1.369 (9) |
C10—C11 | 1.391 (8) | C30—H30 | 0.9300 |
C11—O3 | 1.351 (6) | C31—C32 | 1.380 (9) |
C11—C12 | 1.412 (8) | C31—H31 | 0.9300 |
C12—C13 | 1.387 (9) | C32—H32 | 0.9300 |
C12—H12 | 0.9800 | O2—Ag1i | 2.372 (4) |
C13—C14 | 1.368 (10) | Sb1—F5 | 1.702 (15) |
C13—H13 | 0.9800 | Sb1—F4' | 1.765 (9) |
C14—C15 | 1.378 (10) | Sb1—F2' | 1.777 (18) |
C14—H14 | 0.9300 | Sb1—F1 | 1.784 (12) |
C15—H15 | 0.9300 | Sb1—F4 | 1.793 (9) |
C16—O3 | 1.441 (7) | Sb1—F5' | 1.816 (12) |
C16—C17 | 1.496 (8) | Sb1—F6 | 1.819 (9) |
C16—H16A | 0.9700 | Sb1—F6' | 1.824 (6) |
C16—H16B | 0.9700 | Sb1—F2 | 1.84 (2) |
C17—O4 | 1.421 (6) | Sb1—F3 | 1.854 (8) |
C17—H17A | 0.9700 | Sb1—F1' | 1.862 (11) |
C17—H17B | 0.9700 | Sb1—F3' | 1.863 (8) |
C18—O4 | 1.367 (6) | ||
O2i—Ag1—C12 | 174.39 (18) | O5—C25—C26 | 125.7 (5) |
O2i—Ag1—O6 | 80.32 (14) | N2—C25—C26 | 106.3 (5) |
C12—Ag1—O6 | 104.62 (18) | O6—C26—C27 | 131.2 (6) |
O2i—Ag1—C13 | 145.85 (19) | O6—C26—C25 | 123.1 (5) |
C12—Ag1—C13 | 31.9 (2) | C27—C26—C25 | 105.5 (5) |
O6—Ag1—C13 | 126.5 (2) | C32—C27—C28 | 120.8 (5) |
O2i—Ag1—O5 | 78.73 (14) | C32—C27—C26 | 133.1 (6) |
C12—Ag1—O5 | 100.40 (16) | C28—C27—C26 | 106.1 (5) |
O6—Ag1—O5 | 68.87 (13) | C29—C28—C27 | 121.6 (5) |
C13—Ag1—O5 | 127.52 (17) | C29—C28—N2 | 126.9 (5) |
O1—C1—C2 | 132.5 (6) | C27—C28—N2 | 111.5 (5) |
O1—C1—C8 | 122.4 (5) | C28—C29—C30 | 116.1 (6) |
C2—C1—C8 | 105.1 (5) | C28—C29—H29 | 122.0 |
C7—C2—C3 | 120.9 (5) | C30—C29—H29 | 122.0 |
C7—C2—C1 | 106.9 (5) | C31—C30—C29 | 123.0 (6) |
C3—C2—C1 | 132.2 (5) | C31—C30—H30 | 118.5 |
C4—C3—C2 | 118.4 (6) | C29—C30—H30 | 118.5 |
C4—C3—H3 | 120.8 | C30—C31—C32 | 120.2 (6) |
C2—C3—H3 | 120.8 | C30—C31—H31 | 119.9 |
C3—C4—C5 | 120.4 (6) | C32—C31—H31 | 119.9 |
C3—C4—H4 | 119.8 | C31—C32—C27 | 118.4 (6) |
C5—C4—H4 | 119.8 | C31—C32—H32 | 120.8 |
C4—C5—C6 | 121.8 (6) | C27—C32—H32 | 120.8 |
C4—C5—H5 | 119.1 | C8—N1—C7 | 109.2 (5) |
C6—C5—H5 | 119.1 | C8—N1—C9 | 124.4 (5) |
C7—C6—C5 | 117.1 (6) | C7—N1—C9 | 126.3 (5) |
C7—C6—H6 | 121.5 | C25—N2—C28 | 110.4 (5) |
C5—C6—H6 | 121.5 | C25—N2—C24 | 124.3 (5) |
C6—C7—C2 | 121.3 (6) | C28—N2—C24 | 124.6 (5) |
C6—C7—N1 | 127.4 (6) | C8—O2—Ag1i | 114.6 (4) |
C2—C7—N1 | 111.2 (5) | C11—O3—C16 | 118.0 (4) |
O2—C8—N1 | 127.4 (5) | C18—O4—C17 | 118.1 (4) |
O2—C8—C1 | 125.0 (5) | C25—O5—Ag1 | 109.9 (4) |
N1—C8—C1 | 107.6 (5) | C26—O6—Ag1 | 111.3 (4) |
N1—C9—C10 | 113.0 (5) | F5—Sb1—F4' | 139.3 (16) |
N1—C9—H9A | 109.0 | F5—Sb1—F2' | 125.2 (12) |
C10—C9—H9A | 109.0 | F4'—Sb1—F2' | 89.5 (14) |
N1—C9—H9B | 109.0 | F5—Sb1—F1 | 95.7 (12) |
C10—C9—H9B | 109.0 | F4'—Sb1—F1 | 121.0 (15) |
H9A—C9—H9B | 107.8 | F2'—Sb1—F1 | 31.5 (8) |
C15—C10—C11 | 118.2 (6) | F5—Sb1—F4 | 91.6 (12) |
C15—C10—C9 | 122.0 (6) | F4'—Sb1—F4 | 50.5 (10) |
C11—C10—C9 | 119.7 (5) | F2'—Sb1—F4 | 139.9 (12) |
O3—C11—C10 | 115.4 (5) | F1—Sb1—F4 | 171.0 (13) |
O3—C11—C12 | 124.5 (5) | F5—Sb1—F5' | 48.3 (11) |
C10—C11—C12 | 120.1 (5) | F4'—Sb1—F5' | 96.3 (14) |
C13—C12—C11 | 119.2 (6) | F2'—Sb1—F5' | 173.5 (13) |
C13—C12—Ag1 | 78.6 (4) | F1—Sb1—F5' | 142.6 (14) |
C11—C12—Ag1 | 97.3 (4) | F4—Sb1—F5' | 45.8 (9) |
C13—C12—H12 | 117.5 | F5—Sb1—F6 | 109.5 (14) |
C11—C12—H12 | 117.5 | F4'—Sb1—F6 | 86.9 (14) |
Ag1—C12—H12 | 117.5 | F2'—Sb1—F6 | 92.1 (14) |
C14—C13—C12 | 121.0 (6) | F1—Sb1—F6 | 93.5 (12) |
C14—C13—Ag1 | 101.9 (5) | F4—Sb1—F6 | 89.1 (11) |
C12—C13—Ag1 | 69.5 (4) | F5'—Sb1—F6 | 91.1 (12) |
C14—C13—H13 | 117.5 | F5—Sb1—F6' | 97.0 (11) |
C12—C13—H13 | 117.5 | F4'—Sb1—F6' | 97.8 (11) |
Ag1—C13—H13 | 117.5 | F2'—Sb1—F6' | 98.4 (12) |
C13—C14—C15 | 119.2 (6) | F1—Sb1—F6' | 93.2 (11) |
C13—C14—H14 | 120.4 | F4—Sb1—F6' | 91.2 (11) |
C15—C14—H14 | 120.4 | F5'—Sb1—F6' | 83.7 (10) |
C14—C15—C10 | 122.2 (7) | F6—Sb1—F6' | 12.6 (17) |
C14—C15—H15 | 118.9 | F5—Sb1—F2 | 178.8 (14) |
C10—C15—H15 | 118.9 | F4'—Sb1—F2 | 39.5 (12) |
O3—C16—C17 | 106.8 (5) | F2'—Sb1—F2 | 55.7 (9) |
O3—C16—H16A | 110.4 | F1—Sb1—F2 | 85.4 (10) |
C17—C16—H16A | 110.4 | F4—Sb1—F2 | 87.3 (10) |
O3—C16—H16B | 110.4 | F5'—Sb1—F2 | 130.8 (13) |
C17—C16—H16B | 110.4 | F6—Sb1—F2 | 71.0 (13) |
H16A—C16—H16B | 108.6 | F6'—Sb1—F2 | 83.5 (11) |
O4—C17—C16 | 107.9 (4) | F5—Sb1—F3 | 91.1 (11) |
O4—C17—H17A | 110.1 | F4'—Sb1—F3 | 74.3 (10) |
C16—C17—H17A | 110.1 | F2'—Sb1—F3 | 78.7 (12) |
O4—C17—H17B | 110.1 | F1—Sb1—F3 | 88.4 (11) |
C16—C17—H17B | 110.1 | F4—Sb1—F3 | 86.1 (10) |
H17A—C17—H17B | 108.4 | F5'—Sb1—F3 | 100.0 (10) |
O4—C18—C23 | 116.5 (5) | F6—Sb1—F3 | 159.1 (12) |
O4—C18—C19 | 123.3 (5) | F6'—Sb1—F3 | 171.6 (10) |
C23—C18—C19 | 120.2 (5) | F2—Sb1—F3 | 88.4 (11) |
C20—C19—C18 | 119.7 (6) | F5—Sb1—F1' | 46.0 (9) |
C20—C19—H19 | 120.2 | F4'—Sb1—F1' | 174.4 (15) |
C18—C19—H19 | 120.2 | F2'—Sb1—F1' | 86.7 (10) |
C21—C20—C19 | 120.3 (6) | F1—Sb1—F1' | 55.3 (8) |
C21—C20—H20 | 119.8 | F4—Sb1—F1' | 133.4 (12) |
C19—C20—H20 | 119.8 | F5'—Sb1—F1' | 87.7 (12) |
C20—C21—C22 | 119.6 (6) | F6—Sb1—F1' | 89.0 (12) |
C20—C21—H21 | 120.2 | F6'—Sb1—F1' | 78.6 (9) |
C22—C21—H21 | 120.2 | F2—Sb1—F1' | 135.2 (11) |
C21—C22—C23 | 121.6 (6) | F3—Sb1—F1' | 108.9 (8) |
C21—C22—H22 | 119.2 | F5—Sb1—F3' | 64.2 (10) |
C23—C22—H22 | 119.2 | F4'—Sb1—F3' | 99.9 (11) |
C22—C23—C18 | 118.5 (5) | F2'—Sb1—F3' | 89.6 (11) |
C22—C23—C24 | 119.5 (5) | F1—Sb1—F3' | 84.5 (8) |
C18—C23—C24 | 122.0 (5) | F4—Sb1—F3' | 93.9 (8) |
N2—C24—C23 | 114.0 (4) | F5'—Sb1—F3' | 86.5 (10) |
N2—C24—H24A | 108.8 | F6—Sb1—F3' | 173.0 (12) |
C23—C24—H24A | 108.8 | F6'—Sb1—F3' | 160.6 (10) |
N2—C24—H24B | 108.8 | F2—Sb1—F3' | 115.5 (11) |
C23—C24—H24B | 108.8 | F3—Sb1—F3' | 27.8 (8) |
H24A—C24—H24B | 107.7 | F1'—Sb1—F3' | 84.3 (7) |
O5—C25—N2 | 127.9 (6) | ||
O1—C1—C2—C7 | −180.0 (6) | C19—C18—C23—C24 | −177.7 (5) |
C8—C1—C2—C7 | −1.7 (6) | C22—C23—C24—N2 | 127.6 (6) |
O1—C1—C2—C3 | −0.6 (11) | C18—C23—C24—N2 | −55.4 (7) |
C8—C1—C2—C3 | 177.7 (6) | O5—C25—C26—O6 | −4.8 (9) |
C7—C2—C3—C4 | 0.6 (9) | N2—C25—C26—O6 | 172.1 (5) |
C1—C2—C3—C4 | −178.7 (6) | O5—C25—C26—C27 | 179.7 (5) |
C2—C3—C4—C5 | −1.4 (9) | N2—C25—C26—C27 | −3.3 (6) |
C3—C4—C5—C6 | 1.0 (10) | O6—C26—C27—C32 | 6.1 (11) |
C4—C5—C6—C7 | 0.2 (10) | C25—C26—C27—C32 | −178.9 (6) |
C5—C6—C7—C2 | −1.0 (9) | O6—C26—C27—C28 | −171.3 (6) |
C5—C6—C7—N1 | 177.8 (6) | C25—C26—C27—C28 | 3.6 (6) |
C3—C2—C7—C6 | 0.6 (9) | C32—C27—C28—C29 | −0.7 (8) |
C1—C2—C7—C6 | −179.9 (5) | C26—C27—C28—C29 | 177.1 (5) |
C3—C2—C7—N1 | −178.3 (5) | C32—C27—C28—N2 | 179.4 (5) |
C1—C2—C7—N1 | 1.1 (6) | C26—C27—C28—N2 | −2.8 (6) |
O1—C1—C8—O2 | −0.4 (9) | C27—C28—C29—C30 | 0.0 (8) |
C2—C1—C8—O2 | −178.9 (5) | N2—C28—C29—C30 | 179.9 (5) |
O1—C1—C8—N1 | −179.8 (5) | C28—C29—C30—C31 | 0.5 (9) |
C2—C1—C8—N1 | 1.7 (6) | C29—C30—C31—C32 | −0.2 (10) |
N1—C9—C10—C15 | −111.3 (6) | C30—C31—C32—C27 | −0.5 (9) |
N1—C9—C10—C11 | 69.4 (7) | C28—C27—C32—C31 | 1.0 (9) |
C15—C10—C11—O3 | −179.8 (5) | C26—C27—C32—C31 | −176.2 (6) |
C9—C10—C11—O3 | −0.4 (7) | O2—C8—N1—C7 | 179.6 (6) |
C15—C10—C11—C12 | −0.5 (8) | C1—C8—N1—C7 | −1.1 (6) |
C9—C10—C11—C12 | 178.9 (5) | O2—C8—N1—C9 | −4.6 (9) |
O3—C11—C12—C13 | −179.9 (5) | C1—C8—N1—C9 | 174.8 (5) |
C10—C11—C12—C13 | 1.0 (8) | C6—C7—N1—C8 | −178.9 (6) |
O3—C11—C12—Ag1 | −98.9 (5) | C2—C7—N1—C8 | 0.0 (6) |
C10—C11—C12—Ag1 | 81.9 (5) | C6—C7—N1—C9 | 5.4 (9) |
O2i—Ag1—C12—C13 | 70.6 (18) | C2—C7—N1—C9 | −175.8 (5) |
O6—Ag1—C12—C13 | −138.1 (4) | C10—C9—N1—C8 | 54.9 (7) |
O5—Ag1—C12—C13 | 151.2 (4) | C10—C9—N1—C7 | −130.0 (6) |
O2i—Ag1—C12—C11 | −47.8 (19) | O5—C25—N2—C28 | 178.6 (5) |
O6—Ag1—C12—C11 | 103.5 (4) | C26—C25—N2—C28 | 1.7 (5) |
C13—Ag1—C12—C11 | −118.4 (6) | O5—C25—N2—C24 | 7.2 (9) |
O5—Ag1—C12—C11 | 32.8 (4) | C26—C25—N2—C24 | −169.7 (4) |
C11—C12—C13—C14 | 0.2 (10) | C29—C28—N2—C25 | −179.3 (5) |
Ag1—C12—C13—C14 | −91.9 (7) | C27—C28—N2—C25 | 0.6 (6) |
C11—C12—C13—Ag1 | 92.1 (5) | C29—C28—N2—C24 | −7.9 (8) |
O2i—Ag1—C13—C14 | −51.6 (6) | C27—C28—N2—C24 | 172.0 (5) |
C12—Ag1—C13—C14 | 118.9 (6) | C23—C24—N2—C25 | 108.7 (6) |
O6—Ag1—C13—C14 | 172.4 (4) | C23—C24—N2—C28 | −61.5 (7) |
O5—Ag1—C13—C14 | 82.2 (5) | N1—C8—O2—Ag1i | −178.3 (4) |
O2i—Ag1—C13—C12 | −170.5 (3) | C1—C8—O2—Ag1i | 2.4 (7) |
O6—Ag1—C13—C12 | 53.5 (5) | C10—C11—O3—C16 | −173.4 (5) |
O5—Ag1—C13—C12 | −36.7 (5) | C12—C11—O3—C16 | 7.4 (8) |
C12—C13—C14—C15 | −1.7 (11) | C17—C16—O3—C11 | 166.1 (4) |
Ag1—C13—C14—C15 | −74.9 (7) | C23—C18—O4—C17 | 177.1 (5) |
C13—C14—C15—C10 | 2.2 (11) | C19—C18—O4—C17 | −2.7 (8) |
C11—C10—C15—C14 | −1.1 (10) | C16—C17—O4—C18 | −178.0 (5) |
C9—C10—C15—C14 | 179.5 (6) | N2—C25—O5—Ag1 | 179.4 (4) |
O3—C16—C17—O4 | −76.1 (6) | C26—C25—O5—Ag1 | −4.3 (6) |
O4—C18—C19—C20 | −178.3 (5) | O2i—Ag1—O5—C25 | −77.5 (4) |
C23—C18—C19—C20 | 1.9 (9) | C12—Ag1—O5—C25 | 108.1 (4) |
C18—C19—C20—C21 | −2.9 (10) | O6—Ag1—O5—C25 | 6.4 (3) |
C19—C20—C21—C22 | 2.4 (10) | C13—Ag1—O5—C25 | 126.9 (4) |
C20—C21—C22—C23 | −1.1 (10) | C27—C26—O6—Ag1 | −175.1 (5) |
C21—C22—C23—C18 | 0.2 (9) | C25—C26—O6—Ag1 | 10.7 (6) |
C21—C22—C23—C24 | 177.3 (6) | O2i—Ag1—O6—C26 | 72.8 (4) |
O4—C18—C23—C22 | 179.6 (5) | C12—Ag1—O6—C26 | −104.5 (4) |
C19—C18—C23—C22 | −0.6 (8) | C13—Ag1—O6—C26 | −130.5 (4) |
O4—C18—C23—C24 | 2.5 (8) | O5—Ag1—O6—C26 | −8.8 (4) |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | C32H24N2O6 | [Ag2(C32H24N2O6)2][SbF6]2 |
Mr | 532.53 | 1752.30 |
Crystal system, space group | Monoclinic, P21/n | Triclinic, P1 |
Temperature (K) | 298 | 298 |
a, b, c (Å) | 4.8272 (17), 14.194 (5), 18.883 (7) | 10.193 (2), 11.594 (3), 14.220 (3) |
α, β, γ (°) | 90, 91.472 (7), 90 | 111.121 (3), 91.073 (3), 100.819 (3) |
V (Å3) | 1293.4 (8) | 1533.0 (6) |
Z | 2 | 1 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 0.10 | 1.61 |
Crystal size (mm) | 0.55 × 0.14 × 0.04 | 0.30 × 0.17 × 0.10 |
Data collection | ||
Diffractometer | Bruker SMART CCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | – | Multi-scan (SADABS; Bruker, 2003) |
Tmin, Tmax | – | 0.645, 0.856 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6683, 2398, 1506 | 8087, 5593, 4279 |
Rint | 0.046 | 0.024 |
(sin θ/λ)max (Å−1) | 0.606 | 0.606 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.065, 0.160, 1.05 | 0.053, 0.134, 1.03 |
No. of reflections | 2398 | 5593 |
No. of parameters | 181 | 481 |
No. of restraints | 0 | 3 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.17, −0.13 | 1.07, −1.02 |
Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
The design and construction of molecular architectures based on transition metals and organic spacers is currently attracting significant attention (Leininger et al., 2000; Moulton & Zaworotko, 2001; Kitagawa et al., 2004). Over the past decade, numerous supramolecular networks based on metal-containing molecular building blocks linked through weak intermolecular interactions have been successfully achieved (Liu et al., 2006; Reger et al., 2009). Compared with hydrogen bond-driven networks, supramolecular networks driven by π–π stacking have received less attention. The π–π interaction undoubtedly plays an important role in determining the arrangement of discrete molecular complexes in the solid state (Khavasi & Fard, 2010).
In order to investigate further how π–π interactions participate in the arrangement of molecular complexes in self-assembled aggregates, we synthesized a new ethylene glycol ether bridging ligand, 1,1'-[(ethane-1,2-diyldioxy)di-o-phenylene]bis(indoline-2,3-dione), L or (I), in which two large aromatic indoline-2,3-dione groups are introduced. The combination of (I) with AgSbF6 afforded [Ag2L2][SbF6]2, (II), which features a π–π stacking driven one-dimensional chain consisting of novel dinuclear [Ag2L2]2+ complexes.
The molecule of compound (I) is on a centre of inversion located at the midpoint of the central C16—C16i bond [symmetry code: (i) -x, -y + 1, -z] (Fig. 1) and consequently adopts a trans conformation in the solid state, with the two terminal indoline-2,3-dione groups located on opposite sides of the central bridging ether group. The results are similar to previously reported ethylene glycol ether bridging molecules, which typically adopt trans conformations in the free state (Han & Zhen, 2005). In addition, the terminal indoline-2,3-dione group is nearly perpendicular to the adjacent phenoxy arene ring. The corresponding dihedral angle is 83.28 (5)°. In the crystal structure, the molecules of (I) are arranged in chains running along the a axis, with π–π interactions [3.655 (1) Å] between adjacent parallel indoline-2,3-dione groups (Fig. 2).
In (II), two L ligands connect to each of two AgI centres, leading to a discrete binuclear AgI metallocycle complex, [Ag2L2]2+, with a centre of inversion located between the AgI atoms [Ag1···Ag1i distance 4.749 (1) Å; symmetry code: (i) -x, -y + 1, -z + 1] (Fig. 3). Each AgI centre lies in a five-coordinated environment defined by three O-atom donors (O2i, O5 and O6) from two ligands and two π-donor C atoms from a phenoxy arene ring. The Ag—O [2.372 (4)–2.577 (4) Å] and Ag—C [2.458 (6) and 2.572 (6) Å] distances are consistent with what we have previously observed in related complexes (Dong et al., 2006). In the metallacycle formed by each AgI atom and its primary coordinating L ligand, an open rectangular-like loop of dimensions ca 4.74 (1) × 7.60 (4) Å is found.
Compared with (I), the torsion angle of the central ether group, O3—C16—C17—O4, has changed from 180 to 76.1 (5)° in (II). Thus, L adopts a trans conformation about its central core in the free state, (I), but a gauche conformation after coordinating to the AgI centre in (II). The freedom of rotation around the central C—C single bond gives rise to varied conformations which may be frozen by metal-directed interactions. It is well known that flexible ethylene glycol ether bridging ligands with two terminal coordination donors can adopt different conformations under different conditions. For example, we have reported previously a study of a flexible ethylene glycol ether bridging ligand adopting different conformations at different temperatures (Dong et al., 2007). The relationship of the indoline-2,3-dione rings to the adjacent phenoxy rings is similar to that observed in the free ligand, as the corresponding dihedral angles are 89.1 (1) and 81.9 (1)°.
In the solid state, the dinuclear complexes of (II) are linked to each other through π–π interactions between indoline-2,3-dione groups from two different [Ag2L2]2+ units [centroid-to-centroid distance 3.825 (5) Å], resulting in one-dimensional chains along the crystallographic c axis (Fig. 4). These π–π interaction-driven one-dimensional chains are stacked in an –AA– parallel fashion in the b direction. Although there appear to be π–π interactions between arene rings in different chains, the corresponding centroid-to-centroid distance is 5.503 (8) Å, which is far too long for such interactions. The uncoordinated SbF6- counterions, which are rotationally disordered, are located in the spaces between the chains (Fig. 4).
In summary, the flexible ligand L with terminal indoline-2,3-dione groups can be used as a polydentate or chelating ligand to coordinate transition metal ions. A novel one-dimensional supramolecular chain was obtained successfully based on such coordination. This study demonstrates that π–π interactions play an important role in constructing aggregate supramolecular compounds. We are currently extending this result by preparing new ligands of this type with different substituted functional groups. We anticipate this approach to be useful for constructing novel superamolecular complexes.