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The new asymmetrical organic ligand 2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole (L, C17H13N5O), containing pyridine and imidazole terminal groups, as well as potential oxdiazole coordination sites, was designed and synthesized. The coordination chemistry of L with soft AgI, CuI and CdII metal ions was investigated and three new coordination polymers (CPs), namely, catena-poly[[silver(I)-μ-2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole] hexafluoridophosphate], {[Ag(L)]PF6}n, catena-poly[[copper(I)-di-μ-iodido-copper(I)-bis(μ-2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole)] 1,4-dioxane monosolvate], {[Cu2I2(L)2]·C4H8O2}n, and catena-poly[[[dinitratocopper(II)]-bis(μ-2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole)]–methanol–water (1/1/0.65)], {[Cd(L)2(NO3)2]·2CH4O·0.65H2O}n, were obtained. The experimental results show that ligand L coordinates easily with linear AgI, tetrahedral CuI and octahedral CdII metal atoms to form one-dimensional polymeric structures. The intermediate oxadiazole ring does not participate in the coordination interactions with the metal ions. In all three CPs, weak π–π interactions between the nearly coplanar pyridine, oxadiazole and benzene rings play an important role in the packing of the polymeric chains.
Supporting information
CCDC references: 1966737; 1966736; 1966735
For all structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
catena-Poly[[silver(I)-µ-2-{4-[(1
H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole] hexafluoridophosphate] (1)
top
Crystal data top
[Ag(C17H13N5O)]PF6 | F(000) = 548 |
Mr = 556.16 | Dx = 1.950 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 5.1714 (3) Å | Cell parameters from 1418 reflections |
b = 22.8649 (14) Å | θ = 10.4–69.9° |
c = 8.0202 (5) Å | µ = 10.09 mm−1 |
β = 92.875 (6)° | T = 150 K |
V = 947.14 (10) Å3 | Plate, clear light colourless |
Z = 2 | 0.27 × 0.14 × 0.02 mm |
Data collection top
Rigaku SuperNova Dual Source diffractometer with an Eos detector | 2390 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 2183 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.041 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 71.1°, θmin = 3.9° |
ω scans | h = −2→6 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −20→27 |
Tmin = 0.793, Tmax = 1.000 | l = −9→9 |
3357 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0923P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
2390 reflections | Δρmax = 2.34 e Å−3 |
280 parameters | Δρmin = −0.99 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.016 (13) |
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. 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C17 | 1.2663 (18) | 1.0326 (4) | 0.0865 (11) | 0.0244 (19) | |
H17 | 1.4028 | 1.0161 | 0.0318 | 0.029* | |
C16 | 1.0951 (19) | 1.0735 (4) | 0.0265 (12) | 0.026 (2) | |
H16 | 1.0941 | 1.0900 | −0.0795 | 0.032* | |
N4 | 0.9259 (14) | 1.0863 (3) | 0.1447 (10) | 0.0213 (16) | |
C15 | 0.998 (2) | 1.0538 (5) | 0.2757 (14) | 0.025 (2) | |
H15 | 0.9175 | 1.0545 | 0.3768 | 0.030* | |
N5 | 1.1937 (13) | 1.0210 (3) | 0.2459 (9) | 0.0211 (15) | |
Ag1 | −0.60580 (10) | 0.64592 (3) | 0.87628 (7) | 0.0276 (2) | |
P1 | 0.3755 (4) | 0.6448 (3) | 0.3708 (2) | 0.0264 (5) | |
N1 | −0.3054 (14) | 0.7104 (4) | 0.8853 (10) | 0.0243 (16) | |
F2 | 0.2244 (13) | 0.6721 (3) | 0.2109 (8) | 0.0456 (16) | |
O1 | 0.4412 (11) | 0.8443 (3) | 0.7663 (8) | 0.0228 (13) | |
N2 | 0.3712 (17) | 0.8716 (4) | 1.0241 (12) | 0.028 (2) | |
N3 | 0.5732 (16) | 0.9052 (4) | 0.9659 (11) | 0.0263 (19) | |
F6 | 0.1588 (16) | 0.6666 (4) | 0.4874 (10) | 0.076 (3) | |
C3 | 0.0951 (16) | 0.7928 (4) | 0.8984 (12) | 0.0221 (18) | |
C9 | 0.9622 (18) | 0.9542 (5) | 0.7500 (13) | 0.028 (2) | |
H9 | 0.9595 | 0.9690 | 0.8579 | 0.034* | |
C13 | 0.8001 (18) | 0.8867 (4) | 0.5381 (12) | 0.0249 (19) | |
H13 | 0.6883 | 0.8568 | 0.5033 | 0.030* | |
C7 | 0.6054 (17) | 0.8878 (4) | 0.8154 (11) | 0.0222 (18) | |
C11 | 1.1488 (17) | 0.9538 (5) | 0.4831 (13) | 0.028 (2) | |
C6 | 0.3027 (18) | 0.8360 (4) | 0.9045 (12) | 0.0259 (19) | |
C10 | 1.1340 (18) | 0.9760 (5) | 0.6424 (13) | 0.029 (2) | |
H10 | 1.2433 | 1.0064 | 0.6771 | 0.035* | |
F4 | 0.513 (2) | 0.7067 (4) | 0.4021 (12) | 0.082 (3) | |
C14 | 1.3304 (18) | 0.9801 (5) | 0.3616 (13) | 0.030 (2) | |
H14A | 1.4688 | 1.0007 | 0.4231 | 0.036* | |
H14B | 1.4074 | 0.9491 | 0.2982 | 0.036* | |
C12 | 0.9794 (19) | 0.9091 (5) | 0.4296 (13) | 0.029 (2) | |
H12 | 0.9860 | 0.8942 | 0.3220 | 0.035* | |
C1 | −0.2450 (18) | 0.7410 (4) | 1.0257 (13) | 0.024 (2) | |
H1 | −0.3408 | 0.7343 | 1.1189 | 0.029* | |
C2 | −0.0464 (18) | 0.7821 (5) | 1.0379 (12) | 0.028 (2) | |
H2 | −0.0092 | 0.8019 | 1.1375 | 0.034* | |
C5 | −0.1660 (18) | 0.7211 (4) | 0.7520 (13) | 0.027 (2) | |
H5 | −0.2102 | 0.7015 | 0.6531 | 0.033* | |
C8 | 0.7902 (16) | 0.9097 (5) | 0.6995 (12) | 0.0257 (19) | |
F5 | 0.5252 (13) | 0.6171 (3) | 0.5312 (8) | 0.0464 (17) | |
F3 | 0.5933 (16) | 0.6246 (4) | 0.2582 (11) | 0.085 (3) | |
C4 | 0.0398 (19) | 0.7597 (5) | 0.7536 (13) | 0.025 (2) | |
H4 | 0.1393 | 0.7637 | 0.6609 | 0.030* | |
F1 | 0.228 (2) | 0.5853 (4) | 0.3462 (10) | 0.080 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C17 | 0.024 (5) | 0.028 (5) | 0.021 (4) | 0.003 (4) | 0.000 (3) | −0.009 (4) |
C16 | 0.033 (5) | 0.022 (5) | 0.024 (4) | −0.011 (4) | 0.000 (4) | −0.001 (4) |
N4 | 0.020 (3) | 0.013 (4) | 0.032 (4) | 0.000 (3) | 0.006 (3) | 0.000 (3) |
C15 | 0.024 (5) | 0.026 (6) | 0.025 (5) | −0.002 (4) | 0.003 (4) | 0.007 (4) |
N5 | 0.016 (3) | 0.020 (4) | 0.028 (4) | 0.003 (3) | 0.004 (3) | −0.002 (3) |
Ag1 | 0.0234 (3) | 0.0255 (3) | 0.0344 (3) | −0.0054 (4) | 0.0058 (2) | −0.0023 (4) |
P1 | 0.0263 (9) | 0.0325 (12) | 0.0208 (8) | −0.0002 (15) | 0.0053 (7) | −0.0012 (13) |
N1 | 0.022 (4) | 0.020 (4) | 0.032 (4) | 0.004 (3) | 0.006 (3) | 0.006 (3) |
F2 | 0.056 (4) | 0.043 (4) | 0.037 (3) | 0.005 (3) | −0.004 (3) | 0.002 (3) |
O1 | 0.023 (3) | 0.019 (3) | 0.027 (3) | −0.004 (3) | 0.008 (2) | −0.001 (3) |
N2 | 0.030 (5) | 0.018 (4) | 0.035 (5) | −0.003 (4) | 0.003 (3) | −0.007 (4) |
N3 | 0.022 (4) | 0.027 (5) | 0.030 (4) | 0.006 (4) | −0.001 (3) | −0.002 (4) |
F6 | 0.080 (5) | 0.095 (8) | 0.056 (5) | 0.036 (5) | 0.029 (4) | −0.003 (4) |
C3 | 0.016 (4) | 0.013 (4) | 0.037 (5) | 0.001 (3) | 0.001 (3) | 0.005 (4) |
C9 | 0.025 (4) | 0.028 (5) | 0.032 (5) | −0.007 (4) | 0.006 (4) | −0.004 (4) |
C13 | 0.032 (5) | 0.013 (4) | 0.031 (4) | −0.006 (4) | 0.004 (4) | 0.001 (4) |
C7 | 0.023 (4) | 0.019 (5) | 0.024 (4) | −0.002 (4) | 0.000 (3) | 0.000 (4) |
C11 | 0.020 (4) | 0.033 (6) | 0.032 (5) | 0.005 (4) | 0.003 (4) | 0.010 (4) |
C6 | 0.024 (4) | 0.024 (5) | 0.031 (5) | 0.006 (4) | 0.009 (4) | 0.001 (4) |
C10 | 0.029 (5) | 0.022 (5) | 0.036 (5) | −0.006 (4) | 0.002 (4) | 0.006 (4) |
F4 | 0.119 (8) | 0.052 (5) | 0.072 (6) | −0.038 (6) | −0.037 (6) | 0.015 (4) |
C14 | 0.020 (4) | 0.033 (5) | 0.038 (5) | 0.008 (4) | 0.003 (4) | 0.010 (5) |
C12 | 0.028 (5) | 0.026 (5) | 0.034 (5) | 0.002 (4) | 0.007 (4) | 0.002 (4) |
C1 | 0.019 (4) | 0.018 (5) | 0.037 (5) | −0.009 (4) | 0.006 (4) | −0.003 (4) |
C2 | 0.033 (5) | 0.025 (5) | 0.028 (5) | 0.008 (4) | 0.005 (4) | 0.001 (4) |
C5 | 0.027 (5) | 0.023 (5) | 0.032 (5) | −0.008 (4) | 0.001 (4) | −0.004 (4) |
C8 | 0.013 (4) | 0.031 (5) | 0.033 (5) | 0.001 (4) | 0.001 (3) | 0.005 (4) |
F5 | 0.050 (4) | 0.055 (4) | 0.033 (3) | 0.000 (3) | −0.006 (3) | 0.011 (3) |
F3 | 0.074 (5) | 0.112 (9) | 0.072 (5) | 0.053 (6) | 0.039 (4) | 0.020 (5) |
C4 | 0.016 (5) | 0.036 (6) | 0.024 (5) | −0.006 (4) | 0.006 (4) | 0.002 (4) |
F1 | 0.127 (8) | 0.060 (5) | 0.050 (5) | −0.048 (6) | −0.026 (5) | 0.011 (4) |
Geometric parameters (Å, º) top
C17—H17 | 0.9300 | N3—C7 | 1.289 (13) |
C17—C16 | 1.359 (14) | C3—C6 | 1.457 (13) |
C17—N5 | 1.376 (12) | C3—C2 | 1.389 (13) |
C16—H16 | 0.9300 | C3—C4 | 1.403 (14) |
C16—N4 | 1.355 (12) | C9—H9 | 0.9300 |
N4—C15 | 1.326 (13) | C9—C10 | 1.364 (13) |
N4—Ag1i | 2.144 (8) | C9—C8 | 1.397 (14) |
C15—H15 | 0.9300 | C13—H13 | 0.9300 |
C15—N5 | 1.291 (13) | C13—C12 | 1.400 (14) |
N5—C14 | 1.473 (12) | C13—C8 | 1.400 (14) |
Ag1—N4ii | 2.144 (8) | C7—C8 | 1.456 (13) |
Ag1—N1 | 2.140 (8) | C11—C10 | 1.381 (15) |
P1—F2 | 1.596 (7) | C11—C14 | 1.512 (13) |
P1—F6 | 1.577 (8) | C11—C12 | 1.400 (15) |
P1—F4 | 1.599 (10) | C10—H10 | 0.9300 |
P1—F5 | 1.598 (7) | C14—H14A | 0.9700 |
P1—F3 | 1.549 (8) | C14—H14B | 0.9700 |
P1—F1 | 1.566 (10) | C12—H12 | 0.9300 |
N1—C1 | 1.350 (13) | C1—H1 | 0.9300 |
N1—C5 | 1.341 (13) | C1—C2 | 1.392 (14) |
O1—C7 | 1.353 (11) | C2—H2 | 0.9300 |
O1—C6 | 1.363 (11) | C5—H5 | 0.9300 |
N2—N3 | 1.395 (13) | C5—C4 | 1.382 (14) |
N2—C6 | 1.295 (13) | C4—H4 | 0.9300 |
| | | |
C16—C17—H17 | 127.5 | C10—C9—C8 | 120.5 (10) |
C16—C17—N5 | 104.9 (8) | C8—C9—H9 | 119.7 |
N5—C17—H17 | 127.5 | C12—C13—H13 | 120.2 |
C17—C16—H16 | 125.2 | C12—C13—C8 | 119.6 (9) |
N4—C16—C17 | 109.5 (8) | C8—C13—H13 | 120.2 |
N4—C16—H16 | 125.2 | O1—C7—C8 | 119.3 (8) |
C16—N4—Ag1i | 127.3 (7) | N3—C7—O1 | 113.0 (8) |
C15—N4—C16 | 105.5 (8) | N3—C7—C8 | 127.7 (9) |
C15—N4—Ag1i | 127.2 (7) | C10—C11—C14 | 121.1 (10) |
N4—C15—H15 | 124.1 | C10—C11—C12 | 119.3 (9) |
N5—C15—N4 | 111.7 (9) | C12—C11—C14 | 119.5 (10) |
N5—C15—H15 | 124.1 | O1—C6—C3 | 118.9 (8) |
C17—N5—C14 | 124.2 (8) | N2—C6—O1 | 112.3 (9) |
C15—N5—C17 | 108.3 (8) | N2—C6—C3 | 128.7 (9) |
C15—N5—C14 | 127.4 (8) | C9—C10—C11 | 121.3 (10) |
N1—Ag1—N4ii | 175.3 (3) | C9—C10—H10 | 119.3 |
F2—P1—F4 | 88.6 (5) | C11—C10—H10 | 119.3 |
F2—P1—F5 | 179.6 (5) | N5—C14—C11 | 111.4 (7) |
F6—P1—F2 | 91.0 (5) | N5—C14—H14A | 109.3 |
F6—P1—F4 | 87.2 (6) | N5—C14—H14B | 109.3 |
F6—P1—F5 | 88.7 (4) | C11—C14—H14A | 109.3 |
F5—P1—F4 | 91.7 (4) | C11—C14—H14B | 109.3 |
F3—P1—F2 | 89.4 (4) | H14A—C14—H14B | 108.0 |
F3—P1—F6 | 178.5 (7) | C13—C12—C11 | 120.0 (9) |
F3—P1—F4 | 91.4 (7) | C13—C12—H12 | 120.0 |
F3—P1—F5 | 90.9 (5) | C11—C12—H12 | 120.0 |
F3—P1—F1 | 91.8 (7) | N1—C1—H1 | 118.4 |
F1—P1—F2 | 91.4 (4) | N1—C1—C2 | 123.2 (9) |
F1—P1—F6 | 89.7 (6) | C2—C1—H1 | 118.4 |
F1—P1—F4 | 176.8 (7) | C3—C2—C1 | 118.6 (9) |
F1—P1—F5 | 88.3 (5) | C3—C2—H2 | 120.7 |
C1—N1—Ag1 | 121.5 (6) | C1—C2—H2 | 120.7 |
C5—N1—Ag1 | 121.2 (7) | N1—C5—H5 | 118.2 |
C5—N1—C1 | 117.3 (8) | N1—C5—C4 | 123.7 (9) |
C7—O1—C6 | 102.3 (7) | C4—C5—H5 | 118.2 |
C6—N2—N3 | 106.2 (8) | C9—C8—C13 | 119.3 (9) |
C7—N3—N2 | 106.1 (9) | C9—C8—C7 | 119.6 (9) |
C2—C3—C6 | 120.6 (9) | C13—C8—C7 | 121.1 (9) |
C2—C3—C4 | 118.5 (9) | C3—C4—H4 | 120.8 |
C4—C3—C6 | 120.8 (8) | C5—C4—C3 | 118.5 (9) |
C10—C9—H9 | 119.7 | C5—C4—H4 | 120.8 |
| | | |
C17—C16—N4—C15 | 0.8 (11) | C7—O1—C6—C3 | 178.0 (8) |
C17—C16—N4—Ag1i | −178.5 (6) | C6—O1—C7—N3 | −0.5 (10) |
C17—N5—C14—C11 | −151.6 (9) | C6—O1—C7—C8 | −180.0 (9) |
C16—C17—N5—C15 | −1.1 (10) | C6—N2—N3—C7 | 1.3 (10) |
C16—C17—N5—C14 | −178.2 (9) | C6—C3—C2—C1 | 179.2 (9) |
C16—N4—C15—N5 | −1.6 (11) | C6—C3—C4—C5 | −177.3 (9) |
N4—C15—N5—C17 | 1.7 (12) | C10—C9—C8—C13 | 1.6 (15) |
N4—C15—N5—C14 | 178.7 (9) | C10—C9—C8—C7 | −178.9 (9) |
N4ii—Ag1—N1—C1 | 106 (4) | C10—C11—C14—N5 | −98.2 (11) |
N4ii—Ag1—N1—C5 | −75 (4) | C10—C11—C12—C13 | −0.9 (15) |
C15—N5—C14—C11 | 31.8 (14) | C14—C11—C10—C9 | 177.0 (9) |
N5—C17—C16—N4 | 0.2 (10) | C14—C11—C12—C13 | −176.3 (9) |
Ag1i—N4—C15—N5 | 177.7 (6) | C12—C13—C8—C9 | −0.8 (14) |
Ag1—N1—C1—C2 | 178.2 (7) | C12—C13—C8—C7 | 179.7 (9) |
Ag1—N1—C5—C4 | −176.1 (8) | C12—C11—C10—C9 | 1.7 (16) |
N1—C1—C2—C3 | 0.8 (15) | C12—C11—C14—N5 | 77.0 (12) |
N1—C5—C4—C3 | −4.9 (16) | C1—N1—C5—C4 | 2.6 (15) |
O1—C7—C8—C9 | −179.3 (8) | C2—C3—C6—O1 | 178.5 (8) |
O1—C7—C8—C13 | 0.2 (14) | C2—C3—C6—N2 | −5.6 (16) |
N2—N3—C7—O1 | −0.5 (10) | C2—C3—C4—C5 | 4.9 (15) |
N2—N3—C7—C8 | 178.9 (9) | C5—N1—C1—C2 | −0.6 (15) |
N3—N2—C6—O1 | −1.7 (11) | C8—C9—C10—C11 | −2.0 (16) |
N3—N2—C6—C3 | −177.9 (9) | C8—C13—C12—C11 | 0.5 (15) |
N3—C7—C8—C9 | 1.3 (16) | C4—C3—C6—O1 | 0.7 (13) |
N3—C7—C8—C13 | −179.2 (9) | C4—C3—C6—N2 | 176.7 (10) |
C7—O1—C6—N2 | 1.4 (10) | C4—C3—C2—C1 | −3.0 (14) |
Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x, y−1/2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C16—H16···F3iii | 0.93 | 2.35 | 3.089 (12) | 136 |
C15—H15···F1iv | 0.93 | 2.48 | 3.382 (14) | 163 |
C1—H1···F4v | 0.93 | 2.51 | 3.416 (15) | 165 |
C5—H5···F6 | 0.93 | 2.51 | 3.039 (12) | 116 |
C5—H5···F4vi | 0.93 | 2.41 | 3.205 (13) | 143 |
C5—H5···F5vi | 0.93 | 2.53 | 3.325 (12) | 143 |
Symmetry codes: (iii) −x+2, y+1/2, −z; (iv) −x+1, y+1/2, −z+1; (v) x−1, y, z+1; (vi) x−1, y, z. |
catena-Poly[[copper(I)-di-µ-iodido-copper(I)-bis(µ-2-{4-[(1
H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole)]
1,4-dioxane monosolvate] (2)
top
Crystal data top
[Cu2I2(C17H13N5O)2]·C4H8O2 | Z = 1 |
Mr = 1075.63 | F(000) = 528 |
Triclinic, P1 | Dx = 1.614 Mg m−3 |
a = 9.6124 (6) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 9.7864 (8) Å | Cell parameters from 3236 reflections |
c = 12.7314 (10) Å | θ = 7.5–70.7° |
α = 96.787 (6)° | µ = 12.53 mm−1 |
β = 110.599 (6)° | T = 150 K |
γ = 93.325 (6)° | Plate, clear light red |
V = 1106.82 (14) Å3 | 0.21 × 0.07 × 0.01 mm |
Data collection top
Rigaku SuperNova Dual Source diffractometer with an Eos detector | 3936 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 3402 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.101 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 70.8°, θmin = 3.8° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −11→11 |
Tmin = 0.158, Tmax = 1.000 | l = −12→15 |
7144 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.224 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.1777P)2] where P = (Fo2 + 2Fc2)/3 |
3936 reflections | (Δ/σ)max < 0.001 |
253 parameters | Δρmax = 2.67 e Å−3 |
0 restraints | Δρmin = −2.60 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. 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 1.1366 (10) | 0.7074 (9) | 0.9883 (8) | 0.0354 (19) | |
H1 | 1.1985 | 0.7787 | 1.0423 | 0.042* | |
C2 | 0.9851 (10) | 0.6967 (9) | 0.9480 (8) | 0.0364 (19) | |
H2 | 0.9254 | 0.7585 | 0.9679 | 0.044* | |
C3 | 1.0652 (9) | 0.5235 (9) | 0.8697 (7) | 0.0298 (17) | |
H3 | 1.0656 | 0.4424 | 0.8237 | 0.036* | |
C4 | 0.7835 (9) | 0.5228 (9) | 0.8021 (7) | 0.0338 (18) | |
H4A | 0.7251 | 0.5215 | 0.8506 | 0.041* | |
H4B | 0.7818 | 0.4281 | 0.7687 | 0.041* | |
C5 | 0.7102 (9) | 0.6054 (9) | 0.7083 (7) | 0.0289 (17) | |
C6 | 0.5553 (9) | 0.5896 (9) | 0.6597 (7) | 0.0312 (17) | |
H6 | 0.5003 | 0.5330 | 0.6882 | 0.037* | |
C7 | 0.4818 (9) | 0.6566 (9) | 0.5698 (7) | 0.0307 (17) | |
H7 | 0.3781 | 0.6437 | 0.5372 | 0.037* | |
C8 | 0.5623 (9) | 0.7433 (8) | 0.5278 (6) | 0.0270 (16) | |
C9 | 0.7162 (10) | 0.7622 (10) | 0.5778 (7) | 0.0346 (18) | |
H9 | 0.7704 | 0.8219 | 0.5511 | 0.042* | |
C10 | 0.7908 (9) | 0.6942 (10) | 0.6666 (7) | 0.0340 (18) | |
H10 | 0.8946 | 0.7073 | 0.6987 | 0.041* | |
C11 | 0.4818 (9) | 0.8111 (8) | 0.4301 (7) | 0.0254 (16) | |
C12 | 0.4498 (9) | 0.9433 (8) | 0.3051 (6) | 0.0246 (16) | |
C13 | 0.4892 (9) | 1.0477 (8) | 0.2417 (7) | 0.0270 (16) | |
C14 | 0.3778 (9) | 1.0852 (9) | 0.1499 (7) | 0.0336 (19) | |
H14 | 0.2798 | 1.0448 | 0.1268 | 0.040* | |
C15 | 0.4164 (9) | 1.1842 (9) | 0.0938 (7) | 0.0320 (18) | |
H15 | 0.3428 | 1.2073 | 0.0303 | 0.038* | |
C16 | 0.6599 (9) | 1.2073 (8) | 0.2127 (7) | 0.0282 (16) | |
H16 | 0.7574 | 1.2475 | 0.2322 | 0.034* | |
C17 | 0.6344 (10) | 1.1100 (9) | 0.2747 (7) | 0.0314 (18) | |
H17 | 0.7111 | 1.0867 | 0.3363 | 0.038* | |
C18 | 0.8708 (11) | 0.5075 (11) | 0.4103 (8) | 0.043 (2) | |
H18A | 0.8020 | 0.5305 | 0.4485 | 0.051* | |
H18B | 0.8179 | 0.5037 | 0.3294 | 0.051* | |
C19 | 1.0019 (13) | 0.3832 (11) | 0.5509 (9) | 0.050 (2) | |
H19A | 1.0389 | 0.2947 | 0.5662 | 0.060* | |
H19B | 0.9368 | 0.4024 | 0.5930 | 0.060* | |
Cu1 | 1.40031 (13) | 0.58458 (12) | 0.95163 (10) | 0.0299 (3) | |
I1 | 1.40883 (5) | 0.34223 (5) | 0.83829 (4) | 0.0301 (3) | |
N1 | 1.1856 (8) | 0.5978 (8) | 0.9383 (6) | 0.0306 (15) | |
N2 | 0.9371 (8) | 0.5760 (7) | 0.8716 (6) | 0.0299 (14) | |
N3 | 0.3400 (8) | 0.7927 (8) | 0.3703 (6) | 0.0340 (16) | |
N4 | 0.3205 (8) | 0.8798 (7) | 0.2870 (6) | 0.0322 (16) | |
N5 | 0.5528 (7) | 1.2480 (7) | 0.1256 (6) | 0.0274 (14) | |
O1 | 0.5593 (6) | 0.9070 (6) | 0.3963 (4) | 0.0257 (11) | |
O2 | 0.9188 (8) | 0.3752 (7) | 0.4329 (6) | 0.0452 (16) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.021 (4) | 0.036 (4) | 0.036 (4) | −0.005 (3) | −0.006 (3) | 0.009 (4) |
C2 | 0.028 (5) | 0.036 (5) | 0.038 (5) | 0.007 (4) | 0.001 (4) | 0.007 (4) |
C3 | 0.015 (4) | 0.034 (4) | 0.032 (4) | 0.003 (3) | −0.003 (3) | 0.007 (3) |
C4 | 0.015 (4) | 0.040 (5) | 0.035 (4) | 0.002 (3) | −0.008 (3) | 0.013 (4) |
C5 | 0.021 (4) | 0.032 (4) | 0.024 (4) | 0.004 (3) | −0.004 (3) | 0.008 (3) |
C6 | 0.022 (4) | 0.037 (4) | 0.029 (4) | −0.003 (3) | 0.003 (3) | 0.009 (3) |
C7 | 0.012 (4) | 0.041 (4) | 0.032 (4) | 0.003 (3) | −0.002 (3) | 0.008 (3) |
C8 | 0.023 (4) | 0.026 (4) | 0.025 (4) | 0.005 (3) | −0.001 (3) | 0.007 (3) |
C9 | 0.031 (5) | 0.042 (5) | 0.029 (4) | 0.005 (4) | 0.004 (4) | 0.017 (4) |
C10 | 0.012 (4) | 0.045 (5) | 0.037 (4) | 0.001 (3) | −0.002 (3) | 0.016 (4) |
C11 | 0.020 (4) | 0.022 (3) | 0.027 (4) | 0.003 (3) | −0.001 (3) | 0.009 (3) |
C12 | 0.017 (4) | 0.022 (3) | 0.025 (4) | −0.002 (3) | −0.006 (3) | 0.008 (3) |
C13 | 0.024 (4) | 0.022 (4) | 0.027 (4) | 0.004 (3) | −0.001 (3) | 0.010 (3) |
C14 | 0.015 (4) | 0.040 (5) | 0.035 (4) | 0.002 (3) | −0.006 (3) | 0.012 (4) |
C15 | 0.019 (4) | 0.040 (4) | 0.030 (4) | 0.002 (3) | −0.004 (3) | 0.014 (3) |
C16 | 0.010 (4) | 0.030 (4) | 0.037 (4) | −0.004 (3) | −0.003 (3) | 0.013 (3) |
C17 | 0.026 (4) | 0.035 (4) | 0.022 (4) | 0.002 (3) | −0.006 (3) | 0.008 (3) |
C18 | 0.026 (5) | 0.065 (6) | 0.029 (4) | 0.008 (4) | −0.007 (3) | 0.024 (4) |
C19 | 0.043 (6) | 0.048 (6) | 0.049 (6) | 0.001 (5) | 0.001 (5) | 0.023 (5) |
Cu1 | 0.0144 (6) | 0.0339 (7) | 0.0350 (7) | 0.0020 (5) | −0.0016 (5) | 0.0140 (5) |
I1 | 0.0221 (4) | 0.0330 (4) | 0.0276 (4) | 0.0019 (2) | −0.0018 (2) | 0.0099 (2) |
N1 | 0.016 (3) | 0.038 (4) | 0.029 (3) | 0.003 (3) | −0.004 (3) | 0.009 (3) |
N2 | 0.018 (3) | 0.035 (4) | 0.029 (3) | 0.006 (3) | −0.004 (3) | 0.010 (3) |
N3 | 0.022 (4) | 0.040 (4) | 0.030 (4) | 0.001 (3) | −0.005 (3) | 0.014 (3) |
N4 | 0.023 (4) | 0.031 (4) | 0.033 (4) | 0.005 (3) | −0.005 (3) | 0.014 (3) |
N5 | 0.017 (3) | 0.029 (3) | 0.031 (3) | 0.001 (3) | 0.001 (3) | 0.012 (3) |
O1 | 0.021 (3) | 0.028 (3) | 0.022 (3) | 0.004 (2) | −0.003 (2) | 0.010 (2) |
O2 | 0.033 (4) | 0.045 (4) | 0.042 (4) | 0.000 (3) | −0.006 (3) | 0.007 (3) |
Geometric parameters (Å, º) top
C1—H1 | 0.9300 | C12—O1 | 1.365 (9) |
C1—C2 | 1.356 (13) | C13—C14 | 1.383 (11) |
C1—N1 | 1.373 (12) | C13—C17 | 1.387 (12) |
C2—H2 | 0.9300 | C14—H14 | 0.9300 |
C2—N2 | 1.380 (11) | C14—C15 | 1.376 (13) |
C3—H3 | 0.9300 | C15—H15 | 0.9300 |
C3—N1 | 1.293 (11) | C15—N5 | 1.321 (11) |
C3—N2 | 1.368 (11) | C16—H16 | 0.9300 |
C4—H4A | 0.9700 | C16—C17 | 1.370 (12) |
C4—H4B | 0.9700 | C16—N5 | 1.341 (10) |
C4—C5 | 1.510 (11) | C17—H17 | 0.9300 |
C4—N2 | 1.455 (10) | C18—H18A | 0.9700 |
C5—C6 | 1.388 (12) | C18—H18B | 0.9700 |
C5—C10 | 1.400 (12) | C18—C19i | 1.478 (15) |
C6—H6 | 0.9300 | C18—O2 | 1.426 (12) |
C6—C7 | 1.379 (12) | C19—C18i | 1.478 (15) |
C7—H7 | 0.9300 | C19—H19A | 0.9700 |
C7—C8 | 1.388 (12) | C19—H19B | 0.9700 |
C8—C9 | 1.380 (12) | C19—O2 | 1.422 (12) |
C8—C11 | 1.471 (10) | Cu1—Cu1ii | 2.668 (2) |
C9—H9 | 0.9300 | Cu1—I1ii | 2.6409 (13) |
C9—C10 | 1.377 (12) | Cu1—I1 | 2.6478 (13) |
C10—H10 | 0.9300 | Cu1—N1 | 2.023 (7) |
C11—N3 | 1.296 (11) | Cu1—N5iii | 2.113 (7) |
C11—O1 | 1.364 (10) | I1—Cu1ii | 2.6409 (13) |
C12—C13 | 1.484 (11) | N3—N4 | 1.407 (10) |
C12—N4 | 1.288 (11) | N5—Cu1iii | 2.113 (7) |
| | | |
C2—C1—H1 | 124.8 | C14—C15—H15 | 118.3 |
C2—C1—N1 | 110.4 (8) | N5—C15—C14 | 123.3 (7) |
N1—C1—H1 | 124.8 | N5—C15—H15 | 118.3 |
C1—C2—H2 | 126.8 | C17—C16—H16 | 118.0 |
C1—C2—N2 | 106.4 (8) | N5—C16—H16 | 118.0 |
N2—C2—H2 | 126.8 | N5—C16—C17 | 123.9 (7) |
N1—C3—H3 | 123.4 | C13—C17—H17 | 121.4 |
N1—C3—N2 | 113.3 (8) | C16—C17—C13 | 117.1 (7) |
N2—C3—H3 | 123.4 | C16—C17—H17 | 121.4 |
H4A—C4—H4B | 107.6 | H18A—C18—H18B | 107.9 |
C5—C4—H4A | 108.7 | C19i—C18—H18A | 109.3 |
C5—C4—H4B | 108.7 | C19i—C18—H18B | 109.3 |
N2—C4—H4A | 108.7 | O2—C18—H18A | 109.3 |
N2—C4—H4B | 108.7 | O2—C18—H18B | 109.3 |
N2—C4—C5 | 114.1 (7) | O2—C18—C19i | 111.7 (8) |
C6—C5—C4 | 118.0 (7) | C18i—C19—H19A | 109.3 |
C6—C5—C10 | 118.8 (7) | C18i—C19—H19B | 109.3 |
C10—C5—C4 | 123.2 (7) | H19A—C19—H19B | 108.0 |
C5—C6—H6 | 119.6 | O2—C19—C18i | 111.4 (8) |
C7—C6—C5 | 120.8 (8) | O2—C19—H19A | 109.3 |
C7—C6—H6 | 119.6 | O2—C19—H19B | 109.3 |
C6—C7—H7 | 119.9 | I1—Cu1—Cu1ii | 59.57 (5) |
C6—C7—C8 | 120.2 (7) | I1ii—Cu1—Cu1ii | 59.83 (5) |
C8—C7—H7 | 119.9 | I1ii—Cu1—I1 | 119.40 (4) |
C7—C8—C11 | 119.2 (7) | N1—Cu1—Cu1ii | 132.3 (2) |
C9—C8—C7 | 119.1 (7) | N1—Cu1—I1 | 107.2 (2) |
C9—C8—C11 | 121.6 (7) | N1—Cu1—I1ii | 112.6 (2) |
C8—C9—H9 | 119.4 | N1—Cu1—N5iii | 103.5 (3) |
C10—C9—C8 | 121.2 (8) | N5iii—Cu1—Cu1ii | 124.12 (19) |
C10—C9—H9 | 119.4 | N5iii—Cu1—I1 | 112.21 (19) |
C5—C10—H10 | 120.1 | N5iii—Cu1—I1ii | 100.82 (19) |
C9—C10—C5 | 119.9 (8) | Cu1ii—I1—Cu1 | 60.60 (4) |
C9—C10—H10 | 120.1 | C1—N1—Cu1 | 124.7 (6) |
N3—C11—C8 | 127.3 (8) | C3—N1—C1 | 105.0 (7) |
N3—C11—O1 | 113.5 (7) | C3—N1—Cu1 | 129.4 (6) |
O1—C11—C8 | 119.1 (7) | C2—N2—C4 | 127.0 (7) |
N4—C12—C13 | 128.3 (7) | C3—N2—C2 | 105.0 (7) |
N4—C12—O1 | 112.6 (7) | C3—N2—C4 | 127.8 (7) |
O1—C12—C13 | 119.1 (7) | C11—N3—N4 | 105.0 (7) |
C14—C13—C12 | 119.0 (8) | C12—N4—N3 | 107.0 (6) |
C14—C13—C17 | 119.9 (8) | C15—N5—C16 | 117.7 (7) |
C17—C13—C12 | 121.1 (7) | C15—N5—Cu1iii | 121.5 (5) |
C13—C14—H14 | 121.0 | C16—N5—Cu1iii | 120.7 (5) |
C15—C14—C13 | 118.0 (8) | C11—O1—C12 | 101.9 (6) |
C15—C14—H14 | 121.0 | C19—O2—C18 | 109.0 (7) |
| | | |
C1—C2—N2—C3 | −1.2 (10) | C17—C16—N5—C15 | −4.2 (13) |
C1—C2—N2—C4 | −177.0 (8) | C17—C16—N5—Cu1iii | 172.7 (6) |
C2—C1—N1—C3 | −0.2 (10) | C18i—C19—O2—C18 | −56.3 (12) |
C2—C1—N1—Cu1 | 169.5 (6) | C19i—C18—O2—C19 | 56.5 (12) |
C4—C5—C6—C7 | −176.7 (8) | Cu1ii—Cu1—N1—C1 | 114.1 (7) |
C4—C5—C10—C9 | 177.5 (8) | Cu1ii—Cu1—N1—C3 | −78.9 (8) |
C5—C4—N2—C2 | 70.2 (11) | I1ii—Cu1—I1—Cu1ii | 0.0 |
C5—C4—N2—C3 | −104.6 (10) | I1ii—Cu1—N1—C1 | 45.0 (7) |
C5—C6—C7—C8 | −1.2 (13) | I1—Cu1—N1—C1 | 178.3 (6) |
C6—C5—C10—C9 | −1.0 (13) | I1ii—Cu1—N1—C3 | −147.9 (7) |
C6—C7—C8—C9 | −0.5 (13) | I1—Cu1—N1—C3 | −14.7 (8) |
C6—C7—C8—C11 | 178.5 (8) | N1—C1—C2—N2 | 0.9 (10) |
C7—C8—C9—C10 | 1.5 (13) | N1—C3—N2—C2 | 1.2 (10) |
C7—C8—C11—N3 | −5.3 (13) | N1—C3—N2—C4 | 176.9 (8) |
C7—C8—C11—O1 | 173.4 (7) | N1—Cu1—I1—Cu1ii | −129.5 (2) |
C8—C9—C10—C5 | −0.7 (14) | N2—C3—N1—C1 | −0.7 (10) |
C8—C11—N3—N4 | −179.3 (8) | N2—C3—N1—Cu1 | −169.7 (6) |
C8—C11—O1—C12 | 179.0 (7) | N2—C4—C5—C6 | −161.4 (8) |
C9—C8—C11—N3 | 173.7 (9) | N2—C4—C5—C10 | 20.1 (12) |
C9—C8—C11—O1 | −7.6 (11) | N3—C11—O1—C12 | −2.1 (9) |
C10—C5—C6—C7 | 1.9 (13) | N4—C12—C13—C14 | −0.6 (13) |
C11—C8—C9—C10 | −177.6 (8) | N4—C12—C13—C17 | 177.9 (8) |
C11—N3—N4—C12 | −1.0 (9) | N4—C12—O1—C11 | 1.4 (8) |
C12—C13—C14—C15 | 178.8 (8) | N5—C16—C17—C13 | 2.2 (13) |
C12—C13—C17—C16 | −178.7 (7) | N5iii—Cu1—I1—Cu1ii | 117.6 (2) |
C13—C12—N4—N3 | −179.2 (8) | N5iii—Cu1—N1—C1 | −62.9 (7) |
C13—C12—O1—C11 | −179.6 (7) | N5iii—Cu1—N1—C3 | 104.1 (8) |
C13—C14—C15—N5 | −2.4 (13) | O1—C11—N3—N4 | 2.0 (9) |
C14—C13—C17—C16 | −0.2 (12) | O1—C12—C13—C14 | −179.4 (7) |
C14—C15—N5—C16 | 4.3 (13) | O1—C12—C13—C17 | −0.9 (11) |
C14—C15—N5—Cu1iii | −172.6 (7) | O1—C12—N4—N3 | −0.3 (9) |
C17—C13—C14—C15 | 0.3 (13) | | |
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+3, −y+1, −z+2; (iii) −x+2, −y+2, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···N3iv | 0.97 | 2.55 | 3.450 (12) | 154 |
C16—H16···O2v | 0.93 | 2.59 | 3.206 (10) | 124 |
Symmetry codes: (iv) −x+1, −y+1, −z+1; (v) x, y+1, z. |
catena-Poly[[[dinitratocopper(II)]-bis(µ-2-{4-[(1
H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole)]–methanol–water (1/1/0.65)] (3)
top
Crystal data top
[Cd(C17H13N5O)2(NO3)2]·2CH4O·0.65H2O | Z = 2 |
Mr = 918.86 | F(000) = 937 |
Triclinic, P1 | Dx = 1.556 Mg m−3 |
a = 9.4532 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 14.9309 (5) Å | Cell parameters from 7421 reflections |
c = 15.8386 (6) Å | θ = 5.8–70.8° |
α = 108.975 (3)° | µ = 5.11 mm−1 |
β = 99.904 (3)° | T = 150 K |
γ = 104.901 (3)° | Block, clear light colourless |
V = 1961.43 (12) Å3 | 0.15 × 0.11 × 0.06 mm |
Data collection top
Rigaku SuperNova Dual Source diffractometer with an Eos detector | 7388 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 6838 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.030 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 71.0°, θmin = 3.3° |
ω scans | h = −11→9 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −17→18 |
Tmin = 0.735, Tmax = 1.000 | l = −18→19 |
13771 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0389P)2 + 5.7114P] where P = (Fo2 + 2Fc2)/3 |
7388 reflections | (Δ/σ)max = 0.001 |
562 parameters | Δρmax = 0.99 e Å−3 |
32 restraints | Δρmin = −1.12 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. 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
N5 | −0.1502 (4) | 0.7569 (3) | −0.0437 (2) | 0.0268 (7) | |
C17 | −0.1825 (5) | 0.8351 (3) | 0.0064 (3) | 0.0288 (8) | |
H17 | −0.1216 | 0.9016 | 0.0246 | 0.035* | |
N4 | −0.3137 (4) | 0.8068 (3) | 0.0276 (2) | 0.0309 (7) | |
C14 | −0.3816 (5) | 0.8738 (4) | 0.0824 (3) | 0.0378 (10) | |
H14A | −0.4916 | 0.8436 | 0.0588 | 0.045* | |
H14B | −0.3531 | 0.9364 | 0.0731 | 0.045* | |
N10 | 0.2237 (4) | 0.6967 (2) | 1.8195 (2) | 0.0253 (7) | |
C34 | 0.3597 (4) | 0.7518 (3) | 1.8226 (3) | 0.0249 (8) | |
H34 | 0.4027 | 0.8208 | 1.8563 | 0.030* | |
N9 | 0.4286 (4) | 0.6959 (2) | 1.7709 (2) | 0.0248 (7) | |
C31 | 0.5788 (5) | 0.7328 (3) | 1.7579 (3) | 0.0297 (8) | |
H31A | 0.6412 | 0.6954 | 1.7746 | 0.036* | |
H31B | 0.6281 | 0.8030 | 1.7989 | 0.036* | |
C28 | 0.5680 (4) | 0.7220 (3) | 1.6587 (3) | 0.0251 (8) | |
Cd1 | 0.05763 (3) | 0.754134 (19) | 0.896575 (17) | 0.02292 (9) | |
O2 | 0.4335 (3) | 0.71826 (19) | 1.33306 (17) | 0.0254 (6) | |
O1 | −0.1644 (3) | 0.9169 (2) | 0.51523 (18) | 0.0286 (6) | |
O7 | 0.3592 (3) | 1.0320 (2) | 1.1053 (2) | 0.0389 (7) | |
N11 | 0.2750 (4) | 0.9581 (2) | 1.0353 (2) | 0.0237 (6) | |
O6 | 0.1322 (3) | 0.9331 (2) | 1.0200 (2) | 0.0332 (6) | |
O8 | 0.3270 (4) | 0.9055 (2) | 0.9789 (2) | 0.0388 (7) | |
N6 | 0.1669 (4) | 0.7226 (2) | 1.0265 (2) | 0.0266 (7) | |
N1 | 0.0124 (4) | 0.8392 (2) | 0.7960 (2) | 0.0262 (7) | |
O3 | −0.1315 (4) | 0.6248 (2) | 0.7570 (2) | 0.0410 (7) | |
C5 | −0.0581 (5) | 0.9073 (3) | 0.8200 (3) | 0.0287 (8) | |
H5 | −0.0699 | 0.9280 | 0.8796 | 0.034* | |
C23 | 0.4294 (5) | 0.6743 (3) | 1.2429 (3) | 0.0279 (8) | |
O9 | 0.6803 (5) | 0.5384 (3) | 0.1004 (3) | 0.0592 (10) | |
H9A | 0.6276 | 0.5551 | 0.1346 | 0.089* | |
C6 | −0.1623 (5) | 0.9566 (3) | 0.6062 (3) | 0.0297 (8) | |
N2 | −0.2252 (5) | 1.0247 (3) | 0.6233 (3) | 0.0439 (10) | |
O4 | −0.0814 (5) | 0.5453 (3) | 0.8428 (3) | 0.0574 (10) | |
N7 | 0.5139 (5) | 0.6187 (4) | 1.2315 (3) | 0.0490 (11) | |
C25 | 0.5435 (5) | 0.6992 (3) | 1.4747 (3) | 0.0277 (8) | |
C8 | −0.2704 (5) | 0.9429 (3) | 0.3770 (3) | 0.0295 (8) | |
C18 | 0.1860 (5) | 0.7783 (3) | 1.1161 (3) | 0.0298 (8) | |
H18 | 0.1410 | 0.8279 | 1.1291 | 0.036* | |
C7 | −0.2395 (5) | 0.9674 (3) | 0.4767 (3) | 0.0320 (9) | |
C19 | 0.2684 (5) | 0.7662 (3) | 1.1899 (3) | 0.0292 (8) | |
H19 | 0.2792 | 0.8068 | 1.2509 | 0.035* | |
C3 | −0.0966 (4) | 0.9172 (3) | 0.6712 (3) | 0.0269 (8) | |
N3 | −0.2760 (5) | 1.0320 (3) | 0.5379 (3) | 0.0467 (10) | |
C21 | 0.3114 (5) | 0.6305 (3) | 1.0784 (3) | 0.0289 (8) | |
H21 | 0.3512 | 0.5784 | 1.0635 | 0.035* | |
C27 | 0.6225 (5) | 0.6539 (3) | 1.6030 (3) | 0.0320 (9) | |
H27 | 0.6673 | 0.6156 | 1.6272 | 0.038* | |
C20 | 0.3350 (4) | 0.6914 (3) | 1.1705 (3) | 0.0254 (8) | |
C11 | −0.3365 (5) | 0.8977 (3) | 0.1858 (3) | 0.0286 (8) | |
C29 | 0.5033 (6) | 0.7794 (3) | 1.6217 (3) | 0.0364 (10) | |
H29 | 0.4683 | 0.8261 | 1.6591 | 0.044* | |
C15 | −0.3689 (5) | 0.7034 (4) | −0.0112 (3) | 0.0387 (10) | |
H15 | −0.4585 | 0.6620 | −0.0083 | 0.046* | |
C24 | 0.5242 (5) | 0.6797 (3) | 1.3765 (3) | 0.0311 (9) | |
C33 | 0.2064 (5) | 0.5999 (3) | 1.7628 (3) | 0.0381 (10) | |
H33 | 0.1209 | 0.5438 | 1.7471 | 0.046* | |
C9 | −0.2132 (5) | 0.8768 (3) | 0.3215 (3) | 0.0343 (9) | |
H9 | −0.1525 | 0.8473 | 0.3478 | 0.041* | |
C30 | 0.4898 (5) | 0.7686 (3) | 1.5302 (3) | 0.0345 (9) | |
H30 | 0.4455 | 0.8073 | 1.5061 | 0.041* | |
C2 | −0.0229 (5) | 0.8477 (3) | 0.6457 (3) | 0.0309 (9) | |
H2 | −0.0082 | 0.8265 | 0.5868 | 0.037* | |
C26 | 0.6105 (5) | 0.6428 (3) | 1.5119 (3) | 0.0346 (10) | |
H26 | 0.6476 | 0.5970 | 1.4750 | 0.042* | |
C10 | −0.2463 (5) | 0.8547 (4) | 0.2270 (3) | 0.0370 (10) | |
H10 | −0.2073 | 0.8101 | 0.1903 | 0.044* | |
C22 | 0.2274 (5) | 0.6489 (3) | 1.0093 (3) | 0.0291 (8) | |
H22 | 0.2122 | 0.6080 | 0.9477 | 0.035* | |
C4 | −0.1134 (5) | 0.9476 (3) | 0.7604 (3) | 0.0306 (9) | |
H4 | −0.1615 | 0.9947 | 0.7796 | 0.037* | |
C16 | −0.2678 (5) | 0.6737 (3) | −0.0544 (3) | 0.0350 (9) | |
H16 | −0.2763 | 0.6073 | −0.0865 | 0.042* | |
C1 | 0.0287 (5) | 0.8106 (3) | 0.7104 (3) | 0.0318 (9) | |
H1 | 0.0770 | 0.7634 | 0.6930 | 0.038* | |
N8 | 0.5768 (5) | 0.6224 (4) | 1.3197 (3) | 0.0510 (12) | |
C12 | −0.3920 (5) | 0.9649 (3) | 0.2422 (3) | 0.0370 (10) | |
H12 | −0.4515 | 0.9951 | 0.2161 | 0.044* | |
C32 | 0.3322 (6) | 0.5990 (3) | 1.7337 (3) | 0.0401 (11) | |
H32 | 0.3496 | 0.5431 | 1.6956 | 0.048* | |
C13 | −0.3600 (6) | 0.9873 (3) | 0.3365 (3) | 0.0387 (10) | |
H13 | −0.3984 | 1.0322 | 0.3733 | 0.046* | |
O5 | −0.2147 (7) | 0.4628 (3) | 0.7012 (4) | 0.111 (2) | |
C35 | 0.8345 (8) | 0.6034 (5) | 0.1432 (5) | 0.0714 (18) | |
H35A | 0.8524 | 0.6582 | 0.1227 | 0.107* | |
H35B | 0.9016 | 0.5666 | 0.1262 | 0.107* | |
H35C | 0.8532 | 0.6294 | 0.2096 | 0.107* | |
N12 | −0.1464 (5) | 0.5427 (3) | 0.7659 (3) | 0.0431 (9) | |
C36 | 0.0672 (19) | 0.7198 (15) | 0.3789 (15) | 0.078 (6) | 0.350 (9) |
H36A | 0.1548 | 0.7680 | 0.4284 | 0.117* | 0.350 (9) |
H36B | 0.0594 | 0.7386 | 0.3262 | 0.117* | 0.350 (9) |
H36C | 0.0774 | 0.6544 | 0.3616 | 0.117* | 0.350 (9) |
O12 | −0.0605 (19) | 0.7176 (15) | 0.4079 (12) | 0.108 (6) | 0.350 (9) |
H12A | −0.0990 | 0.6624 | 0.4092 | 0.162* | 0.350 (9) |
O10 | 0.1742 (12) | 0.5320 (9) | 0.4768 (7) | 0.128 (4) | 0.650 (9) |
H10A | 0.2097 | 0.4918 | 0.4423 | 0.193* | 0.650 (9) |
H10B | 0.0977 | 0.4985 | 0.4881 | 0.193* | 0.650 (9) |
O11 | 0.049 (3) | 0.6261 (18) | 0.5137 (14) | 0.247 (9) | 0.650 (9) |
H11 | 0.1158 | 0.6003 | 0.5122 | 0.370* | 0.650 (9) |
C37 | 0.073 (3) | 0.6971 (18) | 0.472 (2) | 0.213 (11) | 0.650 (9) |
H37A | 0.1337 | 0.7624 | 0.5181 | 0.320* | 0.650 (9) |
H37B | −0.0230 | 0.6990 | 0.4424 | 0.320* | 0.650 (9) |
H37C | 0.1260 | 0.6779 | 0.4256 | 0.320* | 0.650 (9) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N5 | 0.0261 (17) | 0.0336 (18) | 0.0213 (15) | 0.0110 (14) | 0.0042 (13) | 0.0119 (14) |
C17 | 0.030 (2) | 0.033 (2) | 0.0237 (19) | 0.0132 (17) | 0.0045 (16) | 0.0117 (16) |
N4 | 0.0305 (18) | 0.045 (2) | 0.0257 (17) | 0.0180 (16) | 0.0096 (14) | 0.0187 (15) |
C14 | 0.042 (3) | 0.057 (3) | 0.032 (2) | 0.032 (2) | 0.0155 (19) | 0.024 (2) |
N10 | 0.0297 (17) | 0.0264 (16) | 0.0186 (15) | 0.0119 (14) | 0.0052 (13) | 0.0063 (13) |
C34 | 0.029 (2) | 0.0241 (18) | 0.0201 (17) | 0.0115 (16) | 0.0053 (15) | 0.0054 (15) |
N9 | 0.0308 (17) | 0.0270 (16) | 0.0186 (15) | 0.0142 (14) | 0.0070 (13) | 0.0079 (13) |
C31 | 0.028 (2) | 0.038 (2) | 0.0222 (19) | 0.0149 (17) | 0.0050 (15) | 0.0084 (16) |
C28 | 0.0226 (18) | 0.0287 (19) | 0.0202 (18) | 0.0093 (15) | 0.0034 (14) | 0.0055 (15) |
Cd1 | 0.02404 (14) | 0.02516 (14) | 0.01865 (13) | 0.00986 (10) | 0.00333 (10) | 0.00748 (10) |
O2 | 0.0306 (14) | 0.0260 (13) | 0.0188 (12) | 0.0113 (11) | 0.0041 (11) | 0.0077 (10) |
O1 | 0.0356 (15) | 0.0304 (14) | 0.0242 (13) | 0.0169 (12) | 0.0066 (11) | 0.0125 (11) |
O7 | 0.0357 (16) | 0.0313 (16) | 0.0320 (16) | 0.0057 (13) | 0.0008 (13) | −0.0009 (13) |
N11 | 0.0269 (17) | 0.0197 (15) | 0.0213 (15) | 0.0073 (13) | 0.0044 (13) | 0.0057 (12) |
O6 | 0.0249 (14) | 0.0366 (16) | 0.0318 (15) | 0.0094 (12) | 0.0044 (12) | 0.0079 (12) |
O8 | 0.0425 (18) | 0.0378 (17) | 0.0359 (16) | 0.0217 (14) | 0.0152 (14) | 0.0053 (13) |
N6 | 0.0288 (17) | 0.0296 (17) | 0.0244 (16) | 0.0157 (14) | 0.0050 (13) | 0.0110 (13) |
N1 | 0.0285 (17) | 0.0281 (17) | 0.0238 (16) | 0.0129 (14) | 0.0048 (13) | 0.0109 (13) |
O3 | 0.0401 (18) | 0.0376 (17) | 0.0430 (18) | 0.0121 (14) | 0.0027 (14) | 0.0181 (14) |
C5 | 0.034 (2) | 0.029 (2) | 0.0196 (18) | 0.0111 (17) | 0.0055 (16) | 0.0056 (15) |
C23 | 0.035 (2) | 0.033 (2) | 0.0193 (18) | 0.0165 (18) | 0.0089 (16) | 0.0100 (16) |
O9 | 0.079 (3) | 0.059 (2) | 0.048 (2) | 0.038 (2) | 0.030 (2) | 0.0133 (18) |
C6 | 0.036 (2) | 0.031 (2) | 0.0219 (18) | 0.0129 (18) | 0.0054 (16) | 0.0098 (16) |
N2 | 0.069 (3) | 0.045 (2) | 0.0259 (18) | 0.036 (2) | 0.0103 (18) | 0.0134 (16) |
O4 | 0.072 (3) | 0.072 (3) | 0.061 (2) | 0.044 (2) | 0.033 (2) | 0.044 (2) |
N7 | 0.071 (3) | 0.074 (3) | 0.0212 (18) | 0.052 (3) | 0.0136 (18) | 0.0195 (19) |
C25 | 0.030 (2) | 0.030 (2) | 0.0208 (18) | 0.0120 (17) | 0.0052 (15) | 0.0066 (15) |
C8 | 0.032 (2) | 0.030 (2) | 0.029 (2) | 0.0117 (17) | 0.0064 (16) | 0.0136 (17) |
C18 | 0.037 (2) | 0.027 (2) | 0.0264 (19) | 0.0136 (17) | 0.0100 (17) | 0.0091 (16) |
C7 | 0.038 (2) | 0.031 (2) | 0.030 (2) | 0.0152 (18) | 0.0044 (17) | 0.0148 (17) |
C19 | 0.039 (2) | 0.029 (2) | 0.0201 (18) | 0.0132 (17) | 0.0089 (16) | 0.0077 (15) |
C3 | 0.029 (2) | 0.0248 (19) | 0.0239 (19) | 0.0069 (16) | 0.0053 (16) | 0.0083 (15) |
N3 | 0.073 (3) | 0.048 (2) | 0.0275 (19) | 0.039 (2) | 0.0096 (19) | 0.0138 (17) |
C21 | 0.039 (2) | 0.028 (2) | 0.0224 (19) | 0.0150 (17) | 0.0091 (16) | 0.0097 (16) |
C27 | 0.039 (2) | 0.038 (2) | 0.025 (2) | 0.0236 (19) | 0.0082 (17) | 0.0121 (17) |
C20 | 0.029 (2) | 0.0265 (19) | 0.0231 (18) | 0.0113 (16) | 0.0082 (15) | 0.0109 (15) |
C11 | 0.027 (2) | 0.036 (2) | 0.030 (2) | 0.0125 (17) | 0.0087 (16) | 0.0189 (17) |
C29 | 0.053 (3) | 0.036 (2) | 0.026 (2) | 0.027 (2) | 0.0138 (19) | 0.0087 (17) |
C15 | 0.034 (2) | 0.043 (3) | 0.045 (3) | 0.011 (2) | 0.016 (2) | 0.023 (2) |
C24 | 0.034 (2) | 0.038 (2) | 0.0237 (19) | 0.0183 (18) | 0.0054 (16) | 0.0105 (17) |
C33 | 0.045 (3) | 0.022 (2) | 0.038 (2) | 0.0041 (18) | 0.018 (2) | 0.0037 (17) |
C9 | 0.038 (2) | 0.044 (2) | 0.035 (2) | 0.025 (2) | 0.0112 (18) | 0.023 (2) |
C30 | 0.048 (3) | 0.036 (2) | 0.026 (2) | 0.024 (2) | 0.0096 (18) | 0.0126 (18) |
C2 | 0.038 (2) | 0.037 (2) | 0.0231 (19) | 0.0177 (19) | 0.0106 (17) | 0.0128 (17) |
C26 | 0.043 (2) | 0.042 (2) | 0.0230 (19) | 0.026 (2) | 0.0084 (18) | 0.0081 (18) |
C10 | 0.046 (3) | 0.048 (3) | 0.035 (2) | 0.032 (2) | 0.019 (2) | 0.022 (2) |
C22 | 0.036 (2) | 0.031 (2) | 0.0209 (18) | 0.0138 (17) | 0.0083 (16) | 0.0086 (16) |
C4 | 0.041 (2) | 0.028 (2) | 0.0252 (19) | 0.0184 (18) | 0.0087 (17) | 0.0083 (16) |
C16 | 0.041 (2) | 0.033 (2) | 0.034 (2) | 0.0117 (19) | 0.0132 (19) | 0.0151 (18) |
C1 | 0.039 (2) | 0.036 (2) | 0.029 (2) | 0.0222 (19) | 0.0122 (18) | 0.0139 (17) |
N8 | 0.073 (3) | 0.079 (3) | 0.0228 (18) | 0.059 (3) | 0.0150 (19) | 0.0202 (19) |
C12 | 0.046 (3) | 0.039 (2) | 0.032 (2) | 0.023 (2) | 0.0068 (19) | 0.0169 (19) |
C32 | 0.054 (3) | 0.025 (2) | 0.041 (2) | 0.015 (2) | 0.023 (2) | 0.0057 (18) |
C13 | 0.052 (3) | 0.040 (2) | 0.030 (2) | 0.028 (2) | 0.007 (2) | 0.0135 (19) |
O5 | 0.129 (5) | 0.047 (3) | 0.081 (3) | −0.039 (3) | 0.029 (3) | −0.019 (2) |
C35 | 0.078 (5) | 0.058 (4) | 0.077 (4) | 0.040 (4) | 0.009 (4) | 0.018 (3) |
N12 | 0.042 (2) | 0.029 (2) | 0.040 (2) | −0.0016 (17) | 0.0108 (18) | 0.0022 (17) |
C36 | 0.061 (8) | 0.071 (9) | 0.086 (10) | 0.039 (7) | 0.010 (7) | 0.002 (7) |
O12 | 0.103 (9) | 0.123 (10) | 0.097 (9) | 0.036 (7) | 0.031 (7) | 0.041 (7) |
O10 | 0.121 (7) | 0.153 (8) | 0.091 (6) | 0.034 (6) | 0.026 (5) | 0.032 (5) |
O11 | 0.266 (13) | 0.264 (13) | 0.209 (12) | 0.095 (9) | 0.068 (9) | 0.086 (9) |
C37 | 0.195 (13) | 0.204 (14) | 0.248 (15) | 0.105 (10) | 0.104 (10) | 0.047 (9) |
Geometric parameters (Å, º) top
N5—C17 | 1.322 (5) | C8—C9 | 1.382 (6) |
N5—Cd1i | 2.327 (3) | C8—C13 | 1.395 (6) |
N5—C16 | 1.376 (5) | C18—H18 | 0.9300 |
C17—H17 | 0.9300 | C18—C19 | 1.379 (6) |
C17—N4 | 1.340 (5) | C7—N3 | 1.291 (6) |
N4—C14 | 1.457 (5) | C19—H19 | 0.9300 |
N4—C15 | 1.375 (6) | C19—C20 | 1.393 (5) |
C14—H14A | 0.9700 | C3—C2 | 1.386 (6) |
C14—H14B | 0.9700 | C3—C4 | 1.386 (5) |
C14—C11 | 1.515 (6) | C21—H21 | 0.9300 |
N10—C34 | 1.319 (5) | C21—C20 | 1.387 (5) |
N10—Cd1ii | 2.315 (3) | C21—C22 | 1.383 (6) |
N10—C33 | 1.380 (5) | C27—H27 | 0.9300 |
C34—H34 | 0.9300 | C27—C26 | 1.380 (6) |
C34—N9 | 1.345 (5) | C11—C10 | 1.388 (6) |
N9—C31 | 1.461 (5) | C11—C12 | 1.389 (6) |
N9—C32 | 1.362 (6) | C29—H29 | 0.9300 |
C31—H31A | 0.9700 | C29—C30 | 1.384 (6) |
C31—H31B | 0.9700 | C15—H15 | 0.9300 |
C31—C28 | 1.509 (5) | C15—C16 | 1.351 (6) |
C28—C27 | 1.385 (5) | C24—N8 | 1.289 (5) |
C28—C29 | 1.387 (6) | C33—H33 | 0.9300 |
Cd1—N5ii | 2.327 (3) | C33—C32 | 1.349 (6) |
Cd1—N10i | 2.315 (3) | C9—H9 | 0.9300 |
Cd1—O6 | 2.572 (3) | C9—C10 | 1.383 (6) |
Cd1—N6 | 2.382 (3) | C30—H30 | 0.9300 |
Cd1—N1 | 2.386 (3) | C2—H2 | 0.9300 |
Cd1—O3 | 2.429 (3) | C2—C1 | 1.389 (6) |
O2—C23 | 1.353 (4) | C26—H26 | 0.9300 |
O2—C24 | 1.360 (5) | C10—H10 | 0.9300 |
O1—C6 | 1.362 (5) | C22—H22 | 0.9300 |
O1—C7 | 1.368 (5) | C4—H4 | 0.9300 |
O7—N11 | 1.237 (4) | C16—H16 | 0.9300 |
N11—O6 | 1.261 (4) | C1—H1 | 0.9300 |
N11—O8 | 1.244 (4) | C12—H12 | 0.9300 |
N6—C18 | 1.343 (5) | C12—C13 | 1.379 (6) |
N6—C22 | 1.340 (5) | C32—H32 | 0.9300 |
N1—C5 | 1.344 (5) | C13—H13 | 0.9300 |
N1—C1 | 1.331 (5) | O5—N12 | 1.213 (6) |
O3—N12 | 1.254 (5) | C35—H35A | 0.9600 |
C5—H5 | 0.9300 | C35—H35B | 0.9600 |
C5—C4 | 1.375 (6) | C35—H35C | 0.9600 |
C23—N7 | 1.285 (5) | C36—H36A | 0.9600 |
C23—C20 | 1.462 (5) | C36—H36B | 0.9600 |
O9—H9A | 0.8200 | C36—H36C | 0.9600 |
O9—C35 | 1.425 (8) | C36—O12 | 1.360 (10) |
C6—N2 | 1.285 (5) | O12—H12A | 0.8200 |
C6—C3 | 1.467 (5) | O10—H10A | 0.8503 |
N2—N3 | 1.404 (5) | O10—H10B | 0.8497 |
O4—N12 | 1.250 (5) | O10—H11 | 1.2977 |
N7—N8 | 1.397 (5) | O11—H11 | 0.8200 |
C25—C24 | 1.455 (5) | O11—C37 | 1.419 (10) |
C25—C30 | 1.391 (6) | C37—H37A | 0.9600 |
C25—C26 | 1.388 (6) | C37—H37B | 0.9600 |
C8—C7 | 1.457 (6) | C37—H37C | 0.9600 |
| | | |
C17—N5—Cd1i | 129.1 (3) | C4—C3—C6 | 119.0 (4) |
C17—N5—C16 | 105.3 (3) | C7—N3—N2 | 106.8 (4) |
C16—N5—Cd1i | 125.6 (3) | C20—C21—H21 | 120.7 |
N5—C17—H17 | 124.1 | C22—C21—H21 | 120.7 |
N5—C17—N4 | 111.8 (4) | C22—C21—C20 | 118.6 (4) |
N4—C17—H17 | 124.1 | C28—C27—H27 | 119.9 |
C17—N4—C14 | 125.9 (4) | C26—C27—C28 | 120.2 (4) |
C17—N4—C15 | 106.6 (4) | C26—C27—H27 | 119.9 |
C15—N4—C14 | 127.4 (4) | C19—C20—C23 | 122.9 (3) |
N4—C14—H14A | 108.5 | C21—C20—C23 | 118.2 (3) |
N4—C14—H14B | 108.5 | C21—C20—C19 | 118.9 (4) |
N4—C14—C11 | 115.1 (3) | C10—C11—C14 | 123.9 (4) |
H14A—C14—H14B | 107.5 | C10—C11—C12 | 118.3 (4) |
C11—C14—H14A | 108.5 | C12—C11—C14 | 117.8 (4) |
C11—C14—H14B | 108.5 | C28—C29—H29 | 119.3 |
C34—N10—Cd1ii | 126.2 (3) | C30—C29—C28 | 121.4 (4) |
C34—N10—C33 | 104.8 (3) | C30—C29—H29 | 119.3 |
C33—N10—Cd1ii | 129.0 (3) | N4—C15—H15 | 126.7 |
N10—C34—H34 | 124.1 | C16—C15—N4 | 106.7 (4) |
N10—C34—N9 | 111.7 (3) | C16—C15—H15 | 126.7 |
N9—C34—H34 | 124.1 | O2—C24—C25 | 120.2 (3) |
C34—N9—C31 | 126.2 (3) | N8—C24—O2 | 112.1 (3) |
C34—N9—C32 | 107.0 (3) | N8—C24—C25 | 127.6 (4) |
C32—N9—C31 | 126.8 (3) | N10—C33—H33 | 125.1 |
N9—C31—H31A | 109.3 | C32—C33—N10 | 109.8 (4) |
N9—C31—H31B | 109.3 | C32—C33—H33 | 125.1 |
N9—C31—C28 | 111.7 (3) | C8—C9—H9 | 120.0 |
H31A—C31—H31B | 107.9 | C8—C9—C10 | 120.0 (4) |
C28—C31—H31A | 109.3 | C10—C9—H9 | 120.0 |
C28—C31—H31B | 109.3 | C25—C30—H30 | 120.5 |
C27—C28—C31 | 120.1 (4) | C29—C30—C25 | 119.1 (4) |
C27—C28—C29 | 119.0 (4) | C29—C30—H30 | 120.5 |
C29—C28—C31 | 120.9 (4) | C3—C2—H2 | 120.8 |
N5ii—Cd1—O6 | 74.36 (11) | C3—C2—C1 | 118.4 (4) |
N5ii—Cd1—N6 | 86.97 (11) | C1—C2—H2 | 120.8 |
N5ii—Cd1—N1 | 98.34 (11) | C25—C26—H26 | 119.7 |
N5ii—Cd1—O3 | 84.39 (11) | C27—C26—C25 | 120.6 (4) |
N10i—Cd1—N5ii | 161.65 (12) | C27—C26—H26 | 119.7 |
N10i—Cd1—O6 | 123.26 (10) | C11—C10—H10 | 119.4 |
N10i—Cd1—N6 | 90.23 (11) | C9—C10—C11 | 121.3 (4) |
N10i—Cd1—N1 | 90.22 (11) | C9—C10—H10 | 119.4 |
N10i—Cd1—O3 | 82.10 (11) | N6—C22—C21 | 123.3 (4) |
N6—Cd1—O6 | 82.66 (10) | N6—C22—H22 | 118.3 |
N6—Cd1—N1 | 160.79 (12) | C21—C22—H22 | 118.3 |
N6—Cd1—O3 | 123.69 (11) | C5—C4—C3 | 119.1 (4) |
N1—Cd1—O6 | 81.06 (10) | C5—C4—H4 | 120.5 |
N1—Cd1—O3 | 75.35 (11) | C3—C4—H4 | 120.5 |
O3—Cd1—O6 | 145.45 (10) | N5—C16—H16 | 125.2 |
C23—O2—C24 | 102.7 (3) | C15—C16—N5 | 109.5 (4) |
C6—O1—C7 | 102.4 (3) | C15—C16—H16 | 125.2 |
O7—N11—O6 | 120.1 (3) | N1—C1—C2 | 123.3 (4) |
O7—N11—O8 | 121.9 (3) | N1—C1—H1 | 118.3 |
O8—N11—O6 | 118.0 (3) | C2—C1—H1 | 118.3 |
N11—O6—Cd1 | 98.8 (2) | C24—N8—N7 | 106.4 (4) |
C18—N6—Cd1 | 125.5 (3) | C11—C12—H12 | 119.5 |
C22—N6—Cd1 | 117.0 (2) | C13—C12—C11 | 120.9 (4) |
C22—N6—C18 | 117.1 (3) | C13—C12—H12 | 119.5 |
C5—N1—Cd1 | 118.2 (3) | N9—C32—H32 | 126.7 |
C1—N1—Cd1 | 123.1 (3) | C33—C32—N9 | 106.6 (4) |
C1—N1—C5 | 117.6 (3) | C33—C32—H32 | 126.7 |
N12—O3—Cd1 | 106.6 (3) | C8—C13—H13 | 119.9 |
N1—C5—H5 | 118.5 | C12—C13—C8 | 120.3 (4) |
N1—C5—C4 | 123.0 (4) | C12—C13—H13 | 119.9 |
C4—C5—H5 | 118.5 | O9—C35—H35A | 109.5 |
O2—C23—C20 | 120.5 (3) | O9—C35—H35B | 109.5 |
N7—C23—O2 | 112.7 (3) | O9—C35—H35C | 109.5 |
N7—C23—C20 | 126.8 (4) | H35A—C35—H35B | 109.5 |
C35—O9—H9A | 109.5 | H35A—C35—H35C | 109.5 |
O1—C6—C3 | 119.2 (3) | H35B—C35—H35C | 109.5 |
N2—C6—O1 | 113.0 (3) | O4—N12—O3 | 117.8 (4) |
N2—C6—C3 | 127.8 (4) | O5—N12—O3 | 121.7 (5) |
C6—N2—N3 | 105.9 (3) | O5—N12—O4 | 120.4 (5) |
C23—N7—N8 | 106.1 (3) | H36A—C36—H36B | 109.5 |
C30—C25—C24 | 121.8 (4) | H36A—C36—H36C | 109.5 |
C26—C25—C24 | 118.4 (4) | H36B—C36—H36C | 109.5 |
C26—C25—C30 | 119.7 (4) | O12—C36—H36A | 109.5 |
C9—C8—C7 | 121.7 (4) | O12—C36—H36B | 109.5 |
C9—C8—C13 | 119.2 (4) | O12—C36—H36C | 109.5 |
C13—C8—C7 | 119.1 (4) | C36—O12—H12A | 109.6 |
N6—C18—H18 | 118.1 | H10A—O10—H10B | 109.5 |
N6—C18—C19 | 123.8 (4) | H10A—O10—H11 | 165.8 |
C19—C18—H18 | 118.1 | H10B—O10—H11 | 78.1 |
O1—C7—C8 | 119.3 (4) | C37—O11—H11 | 110.0 |
N3—C7—O1 | 111.9 (4) | O11—C37—H37A | 109.5 |
N3—C7—C8 | 128.8 (4) | O11—C37—H37B | 109.5 |
C18—C19—H19 | 120.9 | O11—C37—H37C | 109.5 |
C18—C19—C20 | 118.1 (4) | H37A—C37—H37B | 109.5 |
C20—C19—H19 | 120.9 | H37A—C37—H37C | 109.5 |
C2—C3—C6 | 122.3 (4) | H37B—C37—H37C | 109.5 |
C2—C3—C4 | 118.6 (4) | | |
| | | |
N5—C17—N4—C14 | 179.6 (3) | N1—Cd1—N6—C18 | 53.6 (5) |
N5—C17—N4—C15 | 0.2 (5) | N1—Cd1—N6—C22 | −119.7 (4) |
N5ii—Cd1—O6—N11 | 159.3 (2) | N1—Cd1—O3—N12 | 172.0 (3) |
N5ii—Cd1—N6—C18 | −53.3 (3) | N1—C5—C4—C3 | 0.1 (6) |
N5ii—Cd1—N6—C22 | 133.5 (3) | O3—Cd1—O6—N11 | −146.6 (2) |
N5ii—Cd1—N1—C5 | 29.9 (3) | O3—Cd1—N6—C18 | −134.5 (3) |
N5ii—Cd1—N1—C1 | −138.0 (3) | O3—Cd1—N6—C22 | 52.3 (3) |
N5ii—Cd1—O3—N12 | −87.8 (3) | O3—Cd1—N1—C5 | 111.8 (3) |
C17—N5—C16—C15 | 0.4 (5) | O3—Cd1—N1—C1 | −56.1 (3) |
C17—N4—C14—C11 | −91.5 (5) | C5—N1—C1—C2 | 0.2 (6) |
C17—N4—C15—C16 | 0.1 (5) | C23—O2—C24—C25 | −172.6 (4) |
N4—C14—C11—C10 | −4.4 (7) | C23—O2—C24—N8 | 3.2 (5) |
N4—C14—C11—C12 | 177.1 (4) | C23—N7—N8—C24 | 0.3 (6) |
N4—C15—C16—N5 | −0.3 (5) | C6—O1—C7—C8 | −177.7 (4) |
C14—N4—C15—C16 | −179.3 (4) | C6—O1—C7—N3 | 1.2 (5) |
C14—C11—C10—C9 | −177.7 (4) | C6—N2—N3—C7 | 0.1 (6) |
C14—C11—C12—C13 | 177.7 (4) | C6—C3—C2—C1 | −176.7 (4) |
N10—C34—N9—C31 | 179.2 (3) | C6—C3—C4—C5 | 177.1 (4) |
N10—C34—N9—C32 | −1.0 (5) | N2—C6—C3—C2 | −175.8 (5) |
N10i—Cd1—O6—N11 | −15.1 (3) | N2—C6—C3—C4 | 6.5 (7) |
N10i—Cd1—N6—C18 | 144.9 (3) | N7—C23—C20—C19 | −168.3 (5) |
N10i—Cd1—N6—C22 | −28.4 (3) | N7—C23—C20—C21 | 11.6 (7) |
N10i—Cd1—N1—C5 | −166.4 (3) | C25—C24—N8—N7 | 173.2 (5) |
N10i—Cd1—N1—C1 | 25.7 (3) | C8—C7—N3—N2 | 177.9 (4) |
N10i—Cd1—O3—N12 | 79.7 (3) | C8—C9—C10—C11 | 0.0 (7) |
N10—C33—C32—N9 | −1.0 (5) | C18—N6—C22—C21 | −2.3 (6) |
C34—N10—C33—C32 | 0.3 (5) | C18—C19—C20—C23 | 177.7 (4) |
C34—N9—C31—C28 | −113.6 (4) | C18—C19—C20—C21 | −2.2 (6) |
C34—N9—C32—C33 | 1.2 (5) | C7—O1—C6—N2 | −1.1 (5) |
N9—C31—C28—C27 | −111.7 (4) | C7—O1—C6—C3 | 176.9 (4) |
N9—C31—C28—C29 | 68.2 (5) | C7—C8—C9—C10 | 179.4 (4) |
C31—N9—C32—C33 | −179.1 (4) | C7—C8—C13—C12 | −179.5 (4) |
C31—C28—C27—C26 | 179.0 (4) | C3—C6—N2—N3 | −177.1 (4) |
C31—C28—C29—C30 | −178.6 (4) | C3—C2—C1—N1 | −0.8 (7) |
C28—C27—C26—C25 | −0.2 (7) | C27—C28—C29—C30 | 1.2 (7) |
C28—C29—C30—C25 | −0.5 (7) | C20—C23—N7—N8 | −177.7 (4) |
Cd1i—N5—C17—N4 | 179.6 (2) | C20—C21—C22—N6 | −0.2 (6) |
Cd1i—N5—C16—C15 | −179.6 (3) | C11—C12—C13—C8 | 0.3 (7) |
Cd1ii—N10—C34—N9 | 179.3 (2) | C29—C28—C27—C26 | −0.9 (7) |
Cd1ii—N10—C33—C32 | −178.5 (3) | C15—N4—C14—C11 | 87.7 (5) |
Cd1—N6—C18—C19 | −170.6 (3) | C24—O2—C23—N7 | −3.0 (5) |
Cd1—N6—C22—C21 | 171.5 (3) | C24—O2—C23—C20 | 176.5 (4) |
Cd1—N1—C5—C4 | −168.3 (3) | C24—C25—C30—C29 | 176.1 (4) |
Cd1—N1—C1—C2 | 168.1 (3) | C24—C25—C26—C27 | −175.9 (4) |
Cd1—O3—N12—O4 | 8.2 (5) | C33—N10—C34—N9 | 0.4 (4) |
Cd1—O3—N12—O5 | −168.0 (5) | C9—C8—C7—O1 | −6.3 (6) |
O2—C23—N7—N8 | 1.8 (6) | C9—C8—C7—N3 | 174.9 (5) |
O2—C23—C20—C19 | 12.3 (6) | C9—C8—C13—C12 | 0.5 (7) |
O2—C23—C20—C21 | −167.8 (4) | C30—C25—C24—O2 | −9.7 (6) |
O2—C24—N8—N7 | −2.3 (6) | C30—C25—C24—N8 | 175.2 (5) |
O1—C6—N2—N3 | 0.7 (5) | C30—C25—C26—C27 | 0.9 (7) |
O1—C6—C3—C2 | 6.5 (6) | C2—C3—C4—C5 | −0.7 (6) |
O1—C6—C3—C4 | −171.2 (4) | C26—C25—C24—O2 | 167.1 (4) |
O1—C7—N3—N2 | −0.9 (6) | C26—C25—C24—N8 | −8.0 (7) |
O7—N11—O6—Cd1 | −164.4 (3) | C26—C25—C30—C29 | −0.6 (7) |
O6—Cd1—N6—C18 | 21.4 (3) | C10—C11—C12—C13 | −0.9 (7) |
O6—Cd1—N6—C22 | −151.9 (3) | C22—N6—C18—C19 | 2.6 (6) |
O6—Cd1—N1—C5 | −42.7 (3) | C22—C21—C20—C23 | −177.4 (4) |
O6—Cd1—N1—C1 | 149.4 (3) | C22—C21—C20—C19 | 2.5 (6) |
O6—Cd1—O3—N12 | −139.5 (3) | C4—C3—C2—C1 | 1.0 (6) |
O8—N11—O6—Cd1 | 14.5 (4) | C16—N5—C17—N4 | −0.4 (4) |
N6—Cd1—O6—N11 | 70.4 (2) | C1—N1—C5—C4 | 0.2 (6) |
N6—Cd1—N1—C5 | −75.1 (5) | C12—C11—C10—C9 | 0.7 (7) |
N6—Cd1—N1—C1 | 117.0 (4) | C32—N9—C31—C28 | 66.7 (5) |
N6—Cd1—O3—N12 | −5.2 (3) | C13—C8—C7—O1 | 173.7 (4) |
N6—C18—C19—C20 | −0.4 (6) | C13—C8—C7—N3 | −5.1 (7) |
N1—Cd1—O6—N11 | −99.4 (2) | C13—C8—C9—C10 | −0.6 (7) |
Symmetry codes: (i) x, y, z−1; (ii) x, y, z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C22—H22···O9iii | 0.93 | 2.59 | 3.196 (5) | 123 |
O9—H9A···N7i | 0.82 | 2.14 | 2.949 (5) | 172 |
Symmetry codes: (i) x, y, z−1; (iii) −x+1, −y+1, −z+1. |
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