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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619015663/yp3198sup1.cif
Contains datablocks global, 2, 3, 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015663/yp31981sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015663/yp31982sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229619015663/yp31983sup4.hkl
Contains datablock 3

CCDC references: 1966737; 1966736; 1966735

Computing details top

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-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole] hexafluoridophosphate] (1) top
Crystal data top
[Ag(C17H13N5O)]PF6F(000) = 548
Mr = 556.16Dx = 1.950 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 5.1714 (3) ÅCell parameters from 1418 reflections
b = 22.8649 (14) Åθ = 10.4–69.9°
c = 8.0202 (5) ŵ = 10.09 mm1
β = 92.875 (6)°T = 150 K
V = 947.14 (10) Å3Plate, clear light colourless
Z = 20.27 × 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 Source2183 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.041
Detector resolution: 16.0793 pixels mm-1θmax = 71.1°, θmin = 3.9°
ω scansh = 26
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 2027
Tmin = 0.793, Tmax = 1.000l = 99
3357 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.051H 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 reflectionsΔρmax = 2.34 e Å3
280 parametersΔρmin = 0.99 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute 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
xyzUiso*/Ueq
C171.2663 (18)1.0326 (4)0.0865 (11)0.0244 (19)
H171.40281.01610.03180.029*
C161.0951 (19)1.0735 (4)0.0265 (12)0.026 (2)
H161.09411.09000.07950.032*
N40.9259 (14)1.0863 (3)0.1447 (10)0.0213 (16)
C150.998 (2)1.0538 (5)0.2757 (14)0.025 (2)
H150.91751.05450.37680.030*
N51.1937 (13)1.0210 (3)0.2459 (9)0.0211 (15)
Ag10.60580 (10)0.64592 (3)0.87628 (7)0.0276 (2)
P10.3755 (4)0.6448 (3)0.3708 (2)0.0264 (5)
N10.3054 (14)0.7104 (4)0.8853 (10)0.0243 (16)
F20.2244 (13)0.6721 (3)0.2109 (8)0.0456 (16)
O10.4412 (11)0.8443 (3)0.7663 (8)0.0228 (13)
N20.3712 (17)0.8716 (4)1.0241 (12)0.028 (2)
N30.5732 (16)0.9052 (4)0.9659 (11)0.0263 (19)
F60.1588 (16)0.6666 (4)0.4874 (10)0.076 (3)
C30.0951 (16)0.7928 (4)0.8984 (12)0.0221 (18)
C90.9622 (18)0.9542 (5)0.7500 (13)0.028 (2)
H90.95950.96900.85790.034*
C130.8001 (18)0.8867 (4)0.5381 (12)0.0249 (19)
H130.68830.85680.50330.030*
C70.6054 (17)0.8878 (4)0.8154 (11)0.0222 (18)
C111.1488 (17)0.9538 (5)0.4831 (13)0.028 (2)
C60.3027 (18)0.8360 (4)0.9045 (12)0.0259 (19)
C101.1340 (18)0.9760 (5)0.6424 (13)0.029 (2)
H101.24331.00640.67710.035*
F40.513 (2)0.7067 (4)0.4021 (12)0.082 (3)
C141.3304 (18)0.9801 (5)0.3616 (13)0.030 (2)
H14A1.46881.00070.42310.036*
H14B1.40740.94910.29820.036*
C120.9794 (19)0.9091 (5)0.4296 (13)0.029 (2)
H120.98600.89420.32200.035*
C10.2450 (18)0.7410 (4)1.0257 (13)0.024 (2)
H10.34080.73431.11890.029*
C20.0464 (18)0.7821 (5)1.0379 (12)0.028 (2)
H20.00920.80191.13750.034*
C50.1660 (18)0.7211 (4)0.7520 (13)0.027 (2)
H50.21020.70150.65310.033*
C80.7902 (16)0.9097 (5)0.6995 (12)0.0257 (19)
F50.5252 (13)0.6171 (3)0.5312 (8)0.0464 (17)
F30.5933 (16)0.6246 (4)0.2582 (11)0.085 (3)
C40.0398 (19)0.7597 (5)0.7536 (13)0.025 (2)
H40.13930.76370.66090.030*
F10.228 (2)0.5853 (4)0.3462 (10)0.080 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C170.024 (5)0.028 (5)0.021 (4)0.003 (4)0.000 (3)0.009 (4)
C160.033 (5)0.022 (5)0.024 (4)0.011 (4)0.000 (4)0.001 (4)
N40.020 (3)0.013 (4)0.032 (4)0.000 (3)0.006 (3)0.000 (3)
C150.024 (5)0.026 (6)0.025 (5)0.002 (4)0.003 (4)0.007 (4)
N50.016 (3)0.020 (4)0.028 (4)0.003 (3)0.004 (3)0.002 (3)
Ag10.0234 (3)0.0255 (3)0.0344 (3)0.0054 (4)0.0058 (2)0.0023 (4)
P10.0263 (9)0.0325 (12)0.0208 (8)0.0002 (15)0.0053 (7)0.0012 (13)
N10.022 (4)0.020 (4)0.032 (4)0.004 (3)0.006 (3)0.006 (3)
F20.056 (4)0.043 (4)0.037 (3)0.005 (3)0.004 (3)0.002 (3)
O10.023 (3)0.019 (3)0.027 (3)0.004 (3)0.008 (2)0.001 (3)
N20.030 (5)0.018 (4)0.035 (5)0.003 (4)0.003 (3)0.007 (4)
N30.022 (4)0.027 (5)0.030 (4)0.006 (4)0.001 (3)0.002 (4)
F60.080 (5)0.095 (8)0.056 (5)0.036 (5)0.029 (4)0.003 (4)
C30.016 (4)0.013 (4)0.037 (5)0.001 (3)0.001 (3)0.005 (4)
C90.025 (4)0.028 (5)0.032 (5)0.007 (4)0.006 (4)0.004 (4)
C130.032 (5)0.013 (4)0.031 (4)0.006 (4)0.004 (4)0.001 (4)
C70.023 (4)0.019 (5)0.024 (4)0.002 (4)0.000 (3)0.000 (4)
C110.020 (4)0.033 (6)0.032 (5)0.005 (4)0.003 (4)0.010 (4)
C60.024 (4)0.024 (5)0.031 (5)0.006 (4)0.009 (4)0.001 (4)
C100.029 (5)0.022 (5)0.036 (5)0.006 (4)0.002 (4)0.006 (4)
F40.119 (8)0.052 (5)0.072 (6)0.038 (6)0.037 (6)0.015 (4)
C140.020 (4)0.033 (5)0.038 (5)0.008 (4)0.003 (4)0.010 (5)
C120.028 (5)0.026 (5)0.034 (5)0.002 (4)0.007 (4)0.002 (4)
C10.019 (4)0.018 (5)0.037 (5)0.009 (4)0.006 (4)0.003 (4)
C20.033 (5)0.025 (5)0.028 (5)0.008 (4)0.005 (4)0.001 (4)
C50.027 (5)0.023 (5)0.032 (5)0.008 (4)0.001 (4)0.004 (4)
C80.013 (4)0.031 (5)0.033 (5)0.001 (4)0.001 (3)0.005 (4)
F50.050 (4)0.055 (4)0.033 (3)0.000 (3)0.006 (3)0.011 (3)
F30.074 (5)0.112 (9)0.072 (5)0.053 (6)0.039 (4)0.020 (5)
C40.016 (5)0.036 (6)0.024 (5)0.006 (4)0.006 (4)0.002 (4)
F10.127 (8)0.060 (5)0.050 (5)0.048 (6)0.026 (5)0.011 (4)
Geometric parameters (Å, º) top
C17—H170.9300N3—C71.289 (13)
C17—C161.359 (14)C3—C61.457 (13)
C17—N51.376 (12)C3—C21.389 (13)
C16—H160.9300C3—C41.403 (14)
C16—N41.355 (12)C9—H90.9300
N4—C151.326 (13)C9—C101.364 (13)
N4—Ag1i2.144 (8)C9—C81.397 (14)
C15—H150.9300C13—H130.9300
C15—N51.291 (13)C13—C121.400 (14)
N5—C141.473 (12)C13—C81.400 (14)
Ag1—N4ii2.144 (8)C7—C81.456 (13)
Ag1—N12.140 (8)C11—C101.381 (15)
P1—F21.596 (7)C11—C141.512 (13)
P1—F61.577 (8)C11—C121.400 (15)
P1—F41.599 (10)C10—H100.9300
P1—F51.598 (7)C14—H14A0.9700
P1—F31.549 (8)C14—H14B0.9700
P1—F11.566 (10)C12—H120.9300
N1—C11.350 (13)C1—H10.9300
N1—C51.341 (13)C1—C21.392 (14)
O1—C71.353 (11)C2—H20.9300
O1—C61.363 (11)C5—H50.9300
N2—N31.395 (13)C5—C41.382 (14)
N2—C61.295 (13)C4—H40.9300
C16—C17—H17127.5C10—C9—C8120.5 (10)
C16—C17—N5104.9 (8)C8—C9—H9119.7
N5—C17—H17127.5C12—C13—H13120.2
C17—C16—H16125.2C12—C13—C8119.6 (9)
N4—C16—C17109.5 (8)C8—C13—H13120.2
N4—C16—H16125.2O1—C7—C8119.3 (8)
C16—N4—Ag1i127.3 (7)N3—C7—O1113.0 (8)
C15—N4—C16105.5 (8)N3—C7—C8127.7 (9)
C15—N4—Ag1i127.2 (7)C10—C11—C14121.1 (10)
N4—C15—H15124.1C10—C11—C12119.3 (9)
N5—C15—N4111.7 (9)C12—C11—C14119.5 (10)
N5—C15—H15124.1O1—C6—C3118.9 (8)
C17—N5—C14124.2 (8)N2—C6—O1112.3 (9)
C15—N5—C17108.3 (8)N2—C6—C3128.7 (9)
C15—N5—C14127.4 (8)C9—C10—C11121.3 (10)
N1—Ag1—N4ii175.3 (3)C9—C10—H10119.3
F2—P1—F488.6 (5)C11—C10—H10119.3
F2—P1—F5179.6 (5)N5—C14—C11111.4 (7)
F6—P1—F291.0 (5)N5—C14—H14A109.3
F6—P1—F487.2 (6)N5—C14—H14B109.3
F6—P1—F588.7 (4)C11—C14—H14A109.3
F5—P1—F491.7 (4)C11—C14—H14B109.3
F3—P1—F289.4 (4)H14A—C14—H14B108.0
F3—P1—F6178.5 (7)C13—C12—C11120.0 (9)
F3—P1—F491.4 (7)C13—C12—H12120.0
F3—P1—F590.9 (5)C11—C12—H12120.0
F3—P1—F191.8 (7)N1—C1—H1118.4
F1—P1—F291.4 (4)N1—C1—C2123.2 (9)
F1—P1—F689.7 (6)C2—C1—H1118.4
F1—P1—F4176.8 (7)C3—C2—C1118.6 (9)
F1—P1—F588.3 (5)C3—C2—H2120.7
C1—N1—Ag1121.5 (6)C1—C2—H2120.7
C5—N1—Ag1121.2 (7)N1—C5—H5118.2
C5—N1—C1117.3 (8)N1—C5—C4123.7 (9)
C7—O1—C6102.3 (7)C4—C5—H5118.2
C6—N2—N3106.2 (8)C9—C8—C13119.3 (9)
C7—N3—N2106.1 (9)C9—C8—C7119.6 (9)
C2—C3—C6120.6 (9)C13—C8—C7121.1 (9)
C2—C3—C4118.5 (9)C3—C4—H4120.8
C4—C3—C6120.8 (8)C5—C4—C3118.5 (9)
C10—C9—H9119.7C5—C4—H4120.8
C17—C16—N4—C150.8 (11)C7—O1—C6—C3178.0 (8)
C17—C16—N4—Ag1i178.5 (6)C6—O1—C7—N30.5 (10)
C17—N5—C14—C11151.6 (9)C6—O1—C7—C8180.0 (9)
C16—C17—N5—C151.1 (10)C6—N2—N3—C71.3 (10)
C16—C17—N5—C14178.2 (9)C6—C3—C2—C1179.2 (9)
C16—N4—C15—N51.6 (11)C6—C3—C4—C5177.3 (9)
N4—C15—N5—C171.7 (12)C10—C9—C8—C131.6 (15)
N4—C15—N5—C14178.7 (9)C10—C9—C8—C7178.9 (9)
N4ii—Ag1—N1—C1106 (4)C10—C11—C14—N598.2 (11)
N4ii—Ag1—N1—C575 (4)C10—C11—C12—C130.9 (15)
C15—N5—C14—C1131.8 (14)C14—C11—C10—C9177.0 (9)
N5—C17—C16—N40.2 (10)C14—C11—C12—C13176.3 (9)
Ag1i—N4—C15—N5177.7 (6)C12—C13—C8—C90.8 (14)
Ag1—N1—C1—C2178.2 (7)C12—C13—C8—C7179.7 (9)
Ag1—N1—C5—C4176.1 (8)C12—C11—C10—C91.7 (16)
N1—C1—C2—C30.8 (15)C12—C11—C14—N577.0 (12)
N1—C5—C4—C34.9 (16)C1—N1—C5—C42.6 (15)
O1—C7—C8—C9179.3 (8)C2—C3—C6—O1178.5 (8)
O1—C7—C8—C130.2 (14)C2—C3—C6—N25.6 (16)
N2—N3—C7—O10.5 (10)C2—C3—C4—C54.9 (15)
N2—N3—C7—C8178.9 (9)C5—N1—C1—C20.6 (15)
N3—N2—C6—O11.7 (11)C8—C9—C10—C112.0 (16)
N3—N2—C6—C3177.9 (9)C8—C13—C12—C110.5 (15)
N3—C7—C8—C91.3 (16)C4—C3—C6—O10.7 (13)
N3—C7—C8—C13179.2 (9)C4—C3—C6—N2176.7 (10)
C7—O1—C6—N21.4 (10)C4—C3—C2—C13.0 (14)
Symmetry codes: (i) x, y+1/2, z+1; (ii) x, y1/2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C16—H16···F3iii0.932.353.089 (12)136
C15—H15···F1iv0.932.483.382 (14)163
C1—H1···F4v0.932.513.416 (15)165
C5—H5···F60.932.513.039 (12)116
C5—H5···F4vi0.932.413.205 (13)143
C5—H5···F5vi0.932.533.325 (12)143
Symmetry codes: (iii) x+2, y+1/2, z; (iv) x+1, y+1/2, z+1; (v) x1, y, z+1; (vi) x1, y, z.
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] (2) top
Crystal data top
[Cu2I2(C17H13N5O)2]·C4H8O2Z = 1
Mr = 1075.63F(000) = 528
Triclinic, P1Dx = 1.614 Mg m3
a = 9.6124 (6) ÅCu Kα radiation, λ = 1.54184 Å
b = 9.7864 (8) ÅCell parameters from 3236 reflections
c = 12.7314 (10) Åθ = 7.5–70.7°
α = 96.787 (6)°µ = 12.53 mm1
β = 110.599 (6)°T = 150 K
γ = 93.325 (6)°Plate, clear light red
V = 1106.82 (14) Å30.21 × 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 Source3402 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.101
Detector resolution: 16.0793 pixels mm-1θmax = 70.8°, θmin = 3.8°
ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1111
Tmin = 0.158, Tmax = 1.000l = 1215
7144 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.076Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.224H 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 parametersΔρmax = 2.67 e Å3
0 restraintsΔρmin = 2.60 e Å3
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
xyzUiso*/Ueq
C11.1366 (10)0.7074 (9)0.9883 (8)0.0354 (19)
H11.19850.77871.04230.042*
C20.9851 (10)0.6967 (9)0.9480 (8)0.0364 (19)
H20.92540.75850.96790.044*
C31.0652 (9)0.5235 (9)0.8697 (7)0.0298 (17)
H31.06560.44240.82370.036*
C40.7835 (9)0.5228 (9)0.8021 (7)0.0338 (18)
H4A0.72510.52150.85060.041*
H4B0.78180.42810.76870.041*
C50.7102 (9)0.6054 (9)0.7083 (7)0.0289 (17)
C60.5553 (9)0.5896 (9)0.6597 (7)0.0312 (17)
H60.50030.53300.68820.037*
C70.4818 (9)0.6566 (9)0.5698 (7)0.0307 (17)
H70.37810.64370.53720.037*
C80.5623 (9)0.7433 (8)0.5278 (6)0.0270 (16)
C90.7162 (10)0.7622 (10)0.5778 (7)0.0346 (18)
H90.77040.82190.55110.042*
C100.7908 (9)0.6942 (10)0.6666 (7)0.0340 (18)
H100.89460.70730.69870.041*
C110.4818 (9)0.8111 (8)0.4301 (7)0.0254 (16)
C120.4498 (9)0.9433 (8)0.3051 (6)0.0246 (16)
C130.4892 (9)1.0477 (8)0.2417 (7)0.0270 (16)
C140.3778 (9)1.0852 (9)0.1499 (7)0.0336 (19)
H140.27981.04480.12680.040*
C150.4164 (9)1.1842 (9)0.0938 (7)0.0320 (18)
H150.34281.20730.03030.038*
C160.6599 (9)1.2073 (8)0.2127 (7)0.0282 (16)
H160.75741.24750.23220.034*
C170.6344 (10)1.1100 (9)0.2747 (7)0.0314 (18)
H170.71111.08670.33630.038*
C180.8708 (11)0.5075 (11)0.4103 (8)0.043 (2)
H18A0.80200.53050.44850.051*
H18B0.81790.50370.32940.051*
C191.0019 (13)0.3832 (11)0.5509 (9)0.050 (2)
H19A1.03890.29470.56620.060*
H19B0.93680.40240.59300.060*
Cu11.40031 (13)0.58458 (12)0.95163 (10)0.0299 (3)
I11.40883 (5)0.34223 (5)0.83829 (4)0.0301 (3)
N11.1856 (8)0.5978 (8)0.9383 (6)0.0306 (15)
N20.9371 (8)0.5760 (7)0.8716 (6)0.0299 (14)
N30.3400 (8)0.7927 (8)0.3703 (6)0.0340 (16)
N40.3205 (8)0.8798 (7)0.2870 (6)0.0322 (16)
N50.5528 (7)1.2480 (7)0.1256 (6)0.0274 (14)
O10.5593 (6)0.9070 (6)0.3963 (4)0.0257 (11)
O20.9188 (8)0.3752 (7)0.4329 (6)0.0452 (16)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.021 (4)0.036 (4)0.036 (4)0.005 (3)0.006 (3)0.009 (4)
C20.028 (5)0.036 (5)0.038 (5)0.007 (4)0.001 (4)0.007 (4)
C30.015 (4)0.034 (4)0.032 (4)0.003 (3)0.003 (3)0.007 (3)
C40.015 (4)0.040 (5)0.035 (4)0.002 (3)0.008 (3)0.013 (4)
C50.021 (4)0.032 (4)0.024 (4)0.004 (3)0.004 (3)0.008 (3)
C60.022 (4)0.037 (4)0.029 (4)0.003 (3)0.003 (3)0.009 (3)
C70.012 (4)0.041 (4)0.032 (4)0.003 (3)0.002 (3)0.008 (3)
C80.023 (4)0.026 (4)0.025 (4)0.005 (3)0.001 (3)0.007 (3)
C90.031 (5)0.042 (5)0.029 (4)0.005 (4)0.004 (4)0.017 (4)
C100.012 (4)0.045 (5)0.037 (4)0.001 (3)0.002 (3)0.016 (4)
C110.020 (4)0.022 (3)0.027 (4)0.003 (3)0.001 (3)0.009 (3)
C120.017 (4)0.022 (3)0.025 (4)0.002 (3)0.006 (3)0.008 (3)
C130.024 (4)0.022 (4)0.027 (4)0.004 (3)0.001 (3)0.010 (3)
C140.015 (4)0.040 (5)0.035 (4)0.002 (3)0.006 (3)0.012 (4)
C150.019 (4)0.040 (4)0.030 (4)0.002 (3)0.004 (3)0.014 (3)
C160.010 (4)0.030 (4)0.037 (4)0.004 (3)0.003 (3)0.013 (3)
C170.026 (4)0.035 (4)0.022 (4)0.002 (3)0.006 (3)0.008 (3)
C180.026 (5)0.065 (6)0.029 (4)0.008 (4)0.007 (3)0.024 (4)
C190.043 (6)0.048 (6)0.049 (6)0.001 (5)0.001 (5)0.023 (5)
Cu10.0144 (6)0.0339 (7)0.0350 (7)0.0020 (5)0.0016 (5)0.0140 (5)
I10.0221 (4)0.0330 (4)0.0276 (4)0.0019 (2)0.0018 (2)0.0099 (2)
N10.016 (3)0.038 (4)0.029 (3)0.003 (3)0.004 (3)0.009 (3)
N20.018 (3)0.035 (4)0.029 (3)0.006 (3)0.004 (3)0.010 (3)
N30.022 (4)0.040 (4)0.030 (4)0.001 (3)0.005 (3)0.014 (3)
N40.023 (4)0.031 (4)0.033 (4)0.005 (3)0.005 (3)0.014 (3)
N50.017 (3)0.029 (3)0.031 (3)0.001 (3)0.001 (3)0.012 (3)
O10.021 (3)0.028 (3)0.022 (3)0.004 (2)0.003 (2)0.010 (2)
O20.033 (4)0.045 (4)0.042 (4)0.000 (3)0.006 (3)0.007 (3)
Geometric parameters (Å, º) top
C1—H10.9300C12—O11.365 (9)
C1—C21.356 (13)C13—C141.383 (11)
C1—N11.373 (12)C13—C171.387 (12)
C2—H20.9300C14—H140.9300
C2—N21.380 (11)C14—C151.376 (13)
C3—H30.9300C15—H150.9300
C3—N11.293 (11)C15—N51.321 (11)
C3—N21.368 (11)C16—H160.9300
C4—H4A0.9700C16—C171.370 (12)
C4—H4B0.9700C16—N51.341 (10)
C4—C51.510 (11)C17—H170.9300
C4—N21.455 (10)C18—H18A0.9700
C5—C61.388 (12)C18—H18B0.9700
C5—C101.400 (12)C18—C19i1.478 (15)
C6—H60.9300C18—O21.426 (12)
C6—C71.379 (12)C19—C18i1.478 (15)
C7—H70.9300C19—H19A0.9700
C7—C81.388 (12)C19—H19B0.9700
C8—C91.380 (12)C19—O21.422 (12)
C8—C111.471 (10)Cu1—Cu1ii2.668 (2)
C9—H90.9300Cu1—I1ii2.6409 (13)
C9—C101.377 (12)Cu1—I12.6478 (13)
C10—H100.9300Cu1—N12.023 (7)
C11—N31.296 (11)Cu1—N5iii2.113 (7)
C11—O11.364 (10)I1—Cu1ii2.6409 (13)
C12—C131.484 (11)N3—N41.407 (10)
C12—N41.288 (11)N5—Cu1iii2.113 (7)
C2—C1—H1124.8C14—C15—H15118.3
C2—C1—N1110.4 (8)N5—C15—C14123.3 (7)
N1—C1—H1124.8N5—C15—H15118.3
C1—C2—H2126.8C17—C16—H16118.0
C1—C2—N2106.4 (8)N5—C16—H16118.0
N2—C2—H2126.8N5—C16—C17123.9 (7)
N1—C3—H3123.4C13—C17—H17121.4
N1—C3—N2113.3 (8)C16—C17—C13117.1 (7)
N2—C3—H3123.4C16—C17—H17121.4
H4A—C4—H4B107.6H18A—C18—H18B107.9
C5—C4—H4A108.7C19i—C18—H18A109.3
C5—C4—H4B108.7C19i—C18—H18B109.3
N2—C4—H4A108.7O2—C18—H18A109.3
N2—C4—H4B108.7O2—C18—H18B109.3
N2—C4—C5114.1 (7)O2—C18—C19i111.7 (8)
C6—C5—C4118.0 (7)C18i—C19—H19A109.3
C6—C5—C10118.8 (7)C18i—C19—H19B109.3
C10—C5—C4123.2 (7)H19A—C19—H19B108.0
C5—C6—H6119.6O2—C19—C18i111.4 (8)
C7—C6—C5120.8 (8)O2—C19—H19A109.3
C7—C6—H6119.6O2—C19—H19B109.3
C6—C7—H7119.9I1—Cu1—Cu1ii59.57 (5)
C6—C7—C8120.2 (7)I1ii—Cu1—Cu1ii59.83 (5)
C8—C7—H7119.9I1ii—Cu1—I1119.40 (4)
C7—C8—C11119.2 (7)N1—Cu1—Cu1ii132.3 (2)
C9—C8—C7119.1 (7)N1—Cu1—I1107.2 (2)
C9—C8—C11121.6 (7)N1—Cu1—I1ii112.6 (2)
C8—C9—H9119.4N1—Cu1—N5iii103.5 (3)
C10—C9—C8121.2 (8)N5iii—Cu1—Cu1ii124.12 (19)
C10—C9—H9119.4N5iii—Cu1—I1112.21 (19)
C5—C10—H10120.1N5iii—Cu1—I1ii100.82 (19)
C9—C10—C5119.9 (8)Cu1ii—I1—Cu160.60 (4)
C9—C10—H10120.1C1—N1—Cu1124.7 (6)
N3—C11—C8127.3 (8)C3—N1—C1105.0 (7)
N3—C11—O1113.5 (7)C3—N1—Cu1129.4 (6)
O1—C11—C8119.1 (7)C2—N2—C4127.0 (7)
N4—C12—C13128.3 (7)C3—N2—C2105.0 (7)
N4—C12—O1112.6 (7)C3—N2—C4127.8 (7)
O1—C12—C13119.1 (7)C11—N3—N4105.0 (7)
C14—C13—C12119.0 (8)C12—N4—N3107.0 (6)
C14—C13—C17119.9 (8)C15—N5—C16117.7 (7)
C17—C13—C12121.1 (7)C15—N5—Cu1iii121.5 (5)
C13—C14—H14121.0C16—N5—Cu1iii120.7 (5)
C15—C14—C13118.0 (8)C11—O1—C12101.9 (6)
C15—C14—H14121.0C19—O2—C18109.0 (7)
C1—C2—N2—C31.2 (10)C17—C16—N5—C154.2 (13)
C1—C2—N2—C4177.0 (8)C17—C16—N5—Cu1iii172.7 (6)
C2—C1—N1—C30.2 (10)C18i—C19—O2—C1856.3 (12)
C2—C1—N1—Cu1169.5 (6)C19i—C18—O2—C1956.5 (12)
C4—C5—C6—C7176.7 (8)Cu1ii—Cu1—N1—C1114.1 (7)
C4—C5—C10—C9177.5 (8)Cu1ii—Cu1—N1—C378.9 (8)
C5—C4—N2—C270.2 (11)I1ii—Cu1—I1—Cu1ii0.0
C5—C4—N2—C3104.6 (10)I1ii—Cu1—N1—C145.0 (7)
C5—C6—C7—C81.2 (13)I1—Cu1—N1—C1178.3 (6)
C6—C5—C10—C91.0 (13)I1ii—Cu1—N1—C3147.9 (7)
C6—C7—C8—C90.5 (13)I1—Cu1—N1—C314.7 (8)
C6—C7—C8—C11178.5 (8)N1—C1—C2—N20.9 (10)
C7—C8—C9—C101.5 (13)N1—C3—N2—C21.2 (10)
C7—C8—C11—N35.3 (13)N1—C3—N2—C4176.9 (8)
C7—C8—C11—O1173.4 (7)N1—Cu1—I1—Cu1ii129.5 (2)
C8—C9—C10—C50.7 (14)N2—C3—N1—C10.7 (10)
C8—C11—N3—N4179.3 (8)N2—C3—N1—Cu1169.7 (6)
C8—C11—O1—C12179.0 (7)N2—C4—C5—C6161.4 (8)
C9—C8—C11—N3173.7 (9)N2—C4—C5—C1020.1 (12)
C9—C8—C11—O17.6 (11)N3—C11—O1—C122.1 (9)
C10—C5—C6—C71.9 (13)N4—C12—C13—C140.6 (13)
C11—C8—C9—C10177.6 (8)N4—C12—C13—C17177.9 (8)
C11—N3—N4—C121.0 (9)N4—C12—O1—C111.4 (8)
C12—C13—C14—C15178.8 (8)N5—C16—C17—C132.2 (13)
C12—C13—C17—C16178.7 (7)N5iii—Cu1—I1—Cu1ii117.6 (2)
C13—C12—N4—N3179.2 (8)N5iii—Cu1—N1—C162.9 (7)
C13—C12—O1—C11179.6 (7)N5iii—Cu1—N1—C3104.1 (8)
C13—C14—C15—N52.4 (13)O1—C11—N3—N42.0 (9)
C14—C13—C17—C160.2 (12)O1—C12—C13—C14179.4 (7)
C14—C15—N5—C164.3 (13)O1—C12—C13—C170.9 (11)
C14—C15—N5—Cu1iii172.6 (7)O1—C12—N4—N30.3 (9)
C17—C13—C14—C150.3 (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···AD—HH···AD···AD—H···A
C4—H4B···N3iv0.972.553.450 (12)154
C16—H16···O2v0.932.593.206 (10)124
Symmetry codes: (iv) x+1, y+1, z+1; (v) x, y+1, z.
catena-Poly[[[dinitratocopper(II)]-bis(µ-2-{4-[(1H-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·0.65H2OZ = 2
Mr = 918.86F(000) = 937
Triclinic, P1Dx = 1.556 Mg m3
a = 9.4532 (3) ÅCu Kα radiation, λ = 1.54184 Å
b = 14.9309 (5) ÅCell parameters from 7421 reflections
c = 15.8386 (6) Åθ = 5.8–70.8°
α = 108.975 (3)°µ = 5.11 mm1
β = 99.904 (3)°T = 150 K
γ = 104.901 (3)°Block, clear light colourless
V = 1961.43 (12) Å30.15 × 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 Source6838 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.030
Detector resolution: 16.0793 pixels mm-1θmax = 71.0°, θmin = 3.3°
ω scansh = 119
Absorption correction: multi-scan
(CrysAlis PRO; Rigaku OD, 2015)
k = 1718
Tmin = 0.735, Tmax = 1.000l = 1819
13771 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H 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 parametersΔρmax = 0.99 e Å3
32 restraintsΔρmin = 1.12 e Å3
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
xyzUiso*/UeqOcc. (<1)
N50.1502 (4)0.7569 (3)0.0437 (2)0.0268 (7)
C170.1825 (5)0.8351 (3)0.0064 (3)0.0288 (8)
H170.12160.90160.02460.035*
N40.3137 (4)0.8068 (3)0.0276 (2)0.0309 (7)
C140.3816 (5)0.8738 (4)0.0824 (3)0.0378 (10)
H14A0.49160.84360.05880.045*
H14B0.35310.93640.07310.045*
N100.2237 (4)0.6967 (2)1.8195 (2)0.0253 (7)
C340.3597 (4)0.7518 (3)1.8226 (3)0.0249 (8)
H340.40270.82081.85630.030*
N90.4286 (4)0.6959 (2)1.7709 (2)0.0248 (7)
C310.5788 (5)0.7328 (3)1.7579 (3)0.0297 (8)
H31A0.64120.69541.77460.036*
H31B0.62810.80301.79890.036*
C280.5680 (4)0.7220 (3)1.6587 (3)0.0251 (8)
Cd10.05763 (3)0.754134 (19)0.896575 (17)0.02292 (9)
O20.4335 (3)0.71826 (19)1.33306 (17)0.0254 (6)
O10.1644 (3)0.9169 (2)0.51523 (18)0.0286 (6)
O70.3592 (3)1.0320 (2)1.1053 (2)0.0389 (7)
N110.2750 (4)0.9581 (2)1.0353 (2)0.0237 (6)
O60.1322 (3)0.9331 (2)1.0200 (2)0.0332 (6)
O80.3270 (4)0.9055 (2)0.9789 (2)0.0388 (7)
N60.1669 (4)0.7226 (2)1.0265 (2)0.0266 (7)
N10.0124 (4)0.8392 (2)0.7960 (2)0.0262 (7)
O30.1315 (4)0.6248 (2)0.7570 (2)0.0410 (7)
C50.0581 (5)0.9073 (3)0.8200 (3)0.0287 (8)
H50.06990.92800.87960.034*
C230.4294 (5)0.6743 (3)1.2429 (3)0.0279 (8)
O90.6803 (5)0.5384 (3)0.1004 (3)0.0592 (10)
H9A0.62760.55510.13460.089*
C60.1623 (5)0.9566 (3)0.6062 (3)0.0297 (8)
N20.2252 (5)1.0247 (3)0.6233 (3)0.0439 (10)
O40.0814 (5)0.5453 (3)0.8428 (3)0.0574 (10)
N70.5139 (5)0.6187 (4)1.2315 (3)0.0490 (11)
C250.5435 (5)0.6992 (3)1.4747 (3)0.0277 (8)
C80.2704 (5)0.9429 (3)0.3770 (3)0.0295 (8)
C180.1860 (5)0.7783 (3)1.1161 (3)0.0298 (8)
H180.14100.82791.12910.036*
C70.2395 (5)0.9674 (3)0.4767 (3)0.0320 (9)
C190.2684 (5)0.7662 (3)1.1899 (3)0.0292 (8)
H190.27920.80681.25090.035*
C30.0966 (4)0.9172 (3)0.6712 (3)0.0269 (8)
N30.2760 (5)1.0320 (3)0.5379 (3)0.0467 (10)
C210.3114 (5)0.6305 (3)1.0784 (3)0.0289 (8)
H210.35120.57841.06350.035*
C270.6225 (5)0.6539 (3)1.6030 (3)0.0320 (9)
H270.66730.61561.62720.038*
C200.3350 (4)0.6914 (3)1.1705 (3)0.0254 (8)
C110.3365 (5)0.8977 (3)0.1858 (3)0.0286 (8)
C290.5033 (6)0.7794 (3)1.6217 (3)0.0364 (10)
H290.46830.82611.65910.044*
C150.3689 (5)0.7034 (4)0.0112 (3)0.0387 (10)
H150.45850.66200.00830.046*
C240.5242 (5)0.6797 (3)1.3765 (3)0.0311 (9)
C330.2064 (5)0.5999 (3)1.7628 (3)0.0381 (10)
H330.12090.54381.74710.046*
C90.2132 (5)0.8768 (3)0.3215 (3)0.0343 (9)
H90.15250.84730.34780.041*
C300.4898 (5)0.7686 (3)1.5302 (3)0.0345 (9)
H300.44550.80731.50610.041*
C20.0229 (5)0.8477 (3)0.6457 (3)0.0309 (9)
H20.00820.82650.58680.037*
C260.6105 (5)0.6428 (3)1.5119 (3)0.0346 (10)
H260.64760.59701.47500.042*
C100.2463 (5)0.8547 (4)0.2270 (3)0.0370 (10)
H100.20730.81010.19030.044*
C220.2274 (5)0.6489 (3)1.0093 (3)0.0291 (8)
H220.21220.60800.94770.035*
C40.1134 (5)0.9476 (3)0.7604 (3)0.0306 (9)
H40.16150.99470.77960.037*
C160.2678 (5)0.6737 (3)0.0544 (3)0.0350 (9)
H160.27630.60730.08650.042*
C10.0287 (5)0.8106 (3)0.7104 (3)0.0318 (9)
H10.07700.76340.69300.038*
N80.5768 (5)0.6224 (4)1.3197 (3)0.0510 (12)
C120.3920 (5)0.9649 (3)0.2422 (3)0.0370 (10)
H120.45150.99510.21610.044*
C320.3322 (6)0.5990 (3)1.7337 (3)0.0401 (11)
H320.34960.54311.69560.048*
C130.3600 (6)0.9873 (3)0.3365 (3)0.0387 (10)
H130.39841.03220.37330.046*
O50.2147 (7)0.4628 (3)0.7012 (4)0.111 (2)
C350.8345 (8)0.6034 (5)0.1432 (5)0.0714 (18)
H35A0.85240.65820.12270.107*
H35B0.90160.56660.12620.107*
H35C0.85320.62940.20960.107*
N120.1464 (5)0.5427 (3)0.7659 (3)0.0431 (9)
C360.0672 (19)0.7198 (15)0.3789 (15)0.078 (6)0.350 (9)
H36A0.15480.76800.42840.117*0.350 (9)
H36B0.05940.73860.32620.117*0.350 (9)
H36C0.07740.65440.36160.117*0.350 (9)
O120.0605 (19)0.7176 (15)0.4079 (12)0.108 (6)0.350 (9)
H12A0.09900.66240.40920.162*0.350 (9)
O100.1742 (12)0.5320 (9)0.4768 (7)0.128 (4)0.650 (9)
H10A0.20970.49180.44230.193*0.650 (9)
H10B0.09770.49850.48810.193*0.650 (9)
O110.049 (3)0.6261 (18)0.5137 (14)0.247 (9)0.650 (9)
H110.11580.60030.51220.370*0.650 (9)
C370.073 (3)0.6971 (18)0.472 (2)0.213 (11)0.650 (9)
H37A0.13370.76240.51810.320*0.650 (9)
H37B0.02300.69900.44240.320*0.650 (9)
H37C0.12600.67790.42560.320*0.650 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N50.0261 (17)0.0336 (18)0.0213 (15)0.0110 (14)0.0042 (13)0.0119 (14)
C170.030 (2)0.033 (2)0.0237 (19)0.0132 (17)0.0045 (16)0.0117 (16)
N40.0305 (18)0.045 (2)0.0257 (17)0.0180 (16)0.0096 (14)0.0187 (15)
C140.042 (3)0.057 (3)0.032 (2)0.032 (2)0.0155 (19)0.024 (2)
N100.0297 (17)0.0264 (16)0.0186 (15)0.0119 (14)0.0052 (13)0.0063 (13)
C340.029 (2)0.0241 (18)0.0201 (17)0.0115 (16)0.0053 (15)0.0054 (15)
N90.0308 (17)0.0270 (16)0.0186 (15)0.0142 (14)0.0070 (13)0.0079 (13)
C310.028 (2)0.038 (2)0.0222 (19)0.0149 (17)0.0050 (15)0.0084 (16)
C280.0226 (18)0.0287 (19)0.0202 (18)0.0093 (15)0.0034 (14)0.0055 (15)
Cd10.02404 (14)0.02516 (14)0.01865 (13)0.00986 (10)0.00333 (10)0.00748 (10)
O20.0306 (14)0.0260 (13)0.0188 (12)0.0113 (11)0.0041 (11)0.0077 (10)
O10.0356 (15)0.0304 (14)0.0242 (13)0.0169 (12)0.0066 (11)0.0125 (11)
O70.0357 (16)0.0313 (16)0.0320 (16)0.0057 (13)0.0008 (13)0.0009 (13)
N110.0269 (17)0.0197 (15)0.0213 (15)0.0073 (13)0.0044 (13)0.0057 (12)
O60.0249 (14)0.0366 (16)0.0318 (15)0.0094 (12)0.0044 (12)0.0079 (12)
O80.0425 (18)0.0378 (17)0.0359 (16)0.0217 (14)0.0152 (14)0.0053 (13)
N60.0288 (17)0.0296 (17)0.0244 (16)0.0157 (14)0.0050 (13)0.0110 (13)
N10.0285 (17)0.0281 (17)0.0238 (16)0.0129 (14)0.0048 (13)0.0109 (13)
O30.0401 (18)0.0376 (17)0.0430 (18)0.0121 (14)0.0027 (14)0.0181 (14)
C50.034 (2)0.029 (2)0.0196 (18)0.0111 (17)0.0055 (16)0.0056 (15)
C230.035 (2)0.033 (2)0.0193 (18)0.0165 (18)0.0089 (16)0.0100 (16)
O90.079 (3)0.059 (2)0.048 (2)0.038 (2)0.030 (2)0.0133 (18)
C60.036 (2)0.031 (2)0.0219 (18)0.0129 (18)0.0054 (16)0.0098 (16)
N20.069 (3)0.045 (2)0.0259 (18)0.036 (2)0.0103 (18)0.0134 (16)
O40.072 (3)0.072 (3)0.061 (2)0.044 (2)0.033 (2)0.044 (2)
N70.071 (3)0.074 (3)0.0212 (18)0.052 (3)0.0136 (18)0.0195 (19)
C250.030 (2)0.030 (2)0.0208 (18)0.0120 (17)0.0052 (15)0.0066 (15)
C80.032 (2)0.030 (2)0.029 (2)0.0117 (17)0.0064 (16)0.0136 (17)
C180.037 (2)0.027 (2)0.0264 (19)0.0136 (17)0.0100 (17)0.0091 (16)
C70.038 (2)0.031 (2)0.030 (2)0.0152 (18)0.0044 (17)0.0148 (17)
C190.039 (2)0.029 (2)0.0201 (18)0.0132 (17)0.0089 (16)0.0077 (15)
C30.029 (2)0.0248 (19)0.0239 (19)0.0069 (16)0.0053 (16)0.0083 (15)
N30.073 (3)0.048 (2)0.0275 (19)0.039 (2)0.0096 (19)0.0138 (17)
C210.039 (2)0.028 (2)0.0224 (19)0.0150 (17)0.0091 (16)0.0097 (16)
C270.039 (2)0.038 (2)0.025 (2)0.0236 (19)0.0082 (17)0.0121 (17)
C200.029 (2)0.0265 (19)0.0231 (18)0.0113 (16)0.0082 (15)0.0109 (15)
C110.027 (2)0.036 (2)0.030 (2)0.0125 (17)0.0087 (16)0.0189 (17)
C290.053 (3)0.036 (2)0.026 (2)0.027 (2)0.0138 (19)0.0087 (17)
C150.034 (2)0.043 (3)0.045 (3)0.011 (2)0.016 (2)0.023 (2)
C240.034 (2)0.038 (2)0.0237 (19)0.0183 (18)0.0054 (16)0.0105 (17)
C330.045 (3)0.022 (2)0.038 (2)0.0041 (18)0.018 (2)0.0037 (17)
C90.038 (2)0.044 (2)0.035 (2)0.025 (2)0.0112 (18)0.023 (2)
C300.048 (3)0.036 (2)0.026 (2)0.024 (2)0.0096 (18)0.0126 (18)
C20.038 (2)0.037 (2)0.0231 (19)0.0177 (19)0.0106 (17)0.0128 (17)
C260.043 (2)0.042 (2)0.0230 (19)0.026 (2)0.0084 (18)0.0081 (18)
C100.046 (3)0.048 (3)0.035 (2)0.032 (2)0.019 (2)0.022 (2)
C220.036 (2)0.031 (2)0.0209 (18)0.0138 (17)0.0083 (16)0.0086 (16)
C40.041 (2)0.028 (2)0.0252 (19)0.0184 (18)0.0087 (17)0.0083 (16)
C160.041 (2)0.033 (2)0.034 (2)0.0117 (19)0.0132 (19)0.0151 (18)
C10.039 (2)0.036 (2)0.029 (2)0.0222 (19)0.0122 (18)0.0139 (17)
N80.073 (3)0.079 (3)0.0228 (18)0.059 (3)0.0150 (19)0.0202 (19)
C120.046 (3)0.039 (2)0.032 (2)0.023 (2)0.0068 (19)0.0169 (19)
C320.054 (3)0.025 (2)0.041 (2)0.015 (2)0.023 (2)0.0057 (18)
C130.052 (3)0.040 (2)0.030 (2)0.028 (2)0.007 (2)0.0135 (19)
O50.129 (5)0.047 (3)0.081 (3)0.039 (3)0.029 (3)0.019 (2)
C350.078 (5)0.058 (4)0.077 (4)0.040 (4)0.009 (4)0.018 (3)
N120.042 (2)0.029 (2)0.040 (2)0.0016 (17)0.0108 (18)0.0022 (17)
C360.061 (8)0.071 (9)0.086 (10)0.039 (7)0.010 (7)0.002 (7)
O120.103 (9)0.123 (10)0.097 (9)0.036 (7)0.031 (7)0.041 (7)
O100.121 (7)0.153 (8)0.091 (6)0.034 (6)0.026 (5)0.032 (5)
O110.266 (13)0.264 (13)0.209 (12)0.095 (9)0.068 (9)0.086 (9)
C370.195 (13)0.204 (14)0.248 (15)0.105 (10)0.104 (10)0.047 (9)
Geometric parameters (Å, º) top
N5—C171.322 (5)C8—C91.382 (6)
N5—Cd1i2.327 (3)C8—C131.395 (6)
N5—C161.376 (5)C18—H180.9300
C17—H170.9300C18—C191.379 (6)
C17—N41.340 (5)C7—N31.291 (6)
N4—C141.457 (5)C19—H190.9300
N4—C151.375 (6)C19—C201.393 (5)
C14—H14A0.9700C3—C21.386 (6)
C14—H14B0.9700C3—C41.386 (5)
C14—C111.515 (6)C21—H210.9300
N10—C341.319 (5)C21—C201.387 (5)
N10—Cd1ii2.315 (3)C21—C221.383 (6)
N10—C331.380 (5)C27—H270.9300
C34—H340.9300C27—C261.380 (6)
C34—N91.345 (5)C11—C101.388 (6)
N9—C311.461 (5)C11—C121.389 (6)
N9—C321.362 (6)C29—H290.9300
C31—H31A0.9700C29—C301.384 (6)
C31—H31B0.9700C15—H150.9300
C31—C281.509 (5)C15—C161.351 (6)
C28—C271.385 (5)C24—N81.289 (5)
C28—C291.387 (6)C33—H330.9300
Cd1—N5ii2.327 (3)C33—C321.349 (6)
Cd1—N10i2.315 (3)C9—H90.9300
Cd1—O62.572 (3)C9—C101.383 (6)
Cd1—N62.382 (3)C30—H300.9300
Cd1—N12.386 (3)C2—H20.9300
Cd1—O32.429 (3)C2—C11.389 (6)
O2—C231.353 (4)C26—H260.9300
O2—C241.360 (5)C10—H100.9300
O1—C61.362 (5)C22—H220.9300
O1—C71.368 (5)C4—H40.9300
O7—N111.237 (4)C16—H160.9300
N11—O61.261 (4)C1—H10.9300
N11—O81.244 (4)C12—H120.9300
N6—C181.343 (5)C12—C131.379 (6)
N6—C221.340 (5)C32—H320.9300
N1—C51.344 (5)C13—H130.9300
N1—C11.331 (5)O5—N121.213 (6)
O3—N121.254 (5)C35—H35A0.9600
C5—H50.9300C35—H35B0.9600
C5—C41.375 (6)C35—H35C0.9600
C23—N71.285 (5)C36—H36A0.9600
C23—C201.462 (5)C36—H36B0.9600
O9—H9A0.8200C36—H36C0.9600
O9—C351.425 (8)C36—O121.360 (10)
C6—N21.285 (5)O12—H12A0.8200
C6—C31.467 (5)O10—H10A0.8503
N2—N31.404 (5)O10—H10B0.8497
O4—N121.250 (5)O10—H111.2977
N7—N81.397 (5)O11—H110.8200
C25—C241.455 (5)O11—C371.419 (10)
C25—C301.391 (6)C37—H37A0.9600
C25—C261.388 (6)C37—H37B0.9600
C8—C71.457 (6)C37—H37C0.9600
C17—N5—Cd1i129.1 (3)C4—C3—C6119.0 (4)
C17—N5—C16105.3 (3)C7—N3—N2106.8 (4)
C16—N5—Cd1i125.6 (3)C20—C21—H21120.7
N5—C17—H17124.1C22—C21—H21120.7
N5—C17—N4111.8 (4)C22—C21—C20118.6 (4)
N4—C17—H17124.1C28—C27—H27119.9
C17—N4—C14125.9 (4)C26—C27—C28120.2 (4)
C17—N4—C15106.6 (4)C26—C27—H27119.9
C15—N4—C14127.4 (4)C19—C20—C23122.9 (3)
N4—C14—H14A108.5C21—C20—C23118.2 (3)
N4—C14—H14B108.5C21—C20—C19118.9 (4)
N4—C14—C11115.1 (3)C10—C11—C14123.9 (4)
H14A—C14—H14B107.5C10—C11—C12118.3 (4)
C11—C14—H14A108.5C12—C11—C14117.8 (4)
C11—C14—H14B108.5C28—C29—H29119.3
C34—N10—Cd1ii126.2 (3)C30—C29—C28121.4 (4)
C34—N10—C33104.8 (3)C30—C29—H29119.3
C33—N10—Cd1ii129.0 (3)N4—C15—H15126.7
N10—C34—H34124.1C16—C15—N4106.7 (4)
N10—C34—N9111.7 (3)C16—C15—H15126.7
N9—C34—H34124.1O2—C24—C25120.2 (3)
C34—N9—C31126.2 (3)N8—C24—O2112.1 (3)
C34—N9—C32107.0 (3)N8—C24—C25127.6 (4)
C32—N9—C31126.8 (3)N10—C33—H33125.1
N9—C31—H31A109.3C32—C33—N10109.8 (4)
N9—C31—H31B109.3C32—C33—H33125.1
N9—C31—C28111.7 (3)C8—C9—H9120.0
H31A—C31—H31B107.9C8—C9—C10120.0 (4)
C28—C31—H31A109.3C10—C9—H9120.0
C28—C31—H31B109.3C25—C30—H30120.5
C27—C28—C31120.1 (4)C29—C30—C25119.1 (4)
C27—C28—C29119.0 (4)C29—C30—H30120.5
C29—C28—C31120.9 (4)C3—C2—H2120.8
N5ii—Cd1—O674.36 (11)C3—C2—C1118.4 (4)
N5ii—Cd1—N686.97 (11)C1—C2—H2120.8
N5ii—Cd1—N198.34 (11)C25—C26—H26119.7
N5ii—Cd1—O384.39 (11)C27—C26—C25120.6 (4)
N10i—Cd1—N5ii161.65 (12)C27—C26—H26119.7
N10i—Cd1—O6123.26 (10)C11—C10—H10119.4
N10i—Cd1—N690.23 (11)C9—C10—C11121.3 (4)
N10i—Cd1—N190.22 (11)C9—C10—H10119.4
N10i—Cd1—O382.10 (11)N6—C22—C21123.3 (4)
N6—Cd1—O682.66 (10)N6—C22—H22118.3
N6—Cd1—N1160.79 (12)C21—C22—H22118.3
N6—Cd1—O3123.69 (11)C5—C4—C3119.1 (4)
N1—Cd1—O681.06 (10)C5—C4—H4120.5
N1—Cd1—O375.35 (11)C3—C4—H4120.5
O3—Cd1—O6145.45 (10)N5—C16—H16125.2
C23—O2—C24102.7 (3)C15—C16—N5109.5 (4)
C6—O1—C7102.4 (3)C15—C16—H16125.2
O7—N11—O6120.1 (3)N1—C1—C2123.3 (4)
O7—N11—O8121.9 (3)N1—C1—H1118.3
O8—N11—O6118.0 (3)C2—C1—H1118.3
N11—O6—Cd198.8 (2)C24—N8—N7106.4 (4)
C18—N6—Cd1125.5 (3)C11—C12—H12119.5
C22—N6—Cd1117.0 (2)C13—C12—C11120.9 (4)
C22—N6—C18117.1 (3)C13—C12—H12119.5
C5—N1—Cd1118.2 (3)N9—C32—H32126.7
C1—N1—Cd1123.1 (3)C33—C32—N9106.6 (4)
C1—N1—C5117.6 (3)C33—C32—H32126.7
N12—O3—Cd1106.6 (3)C8—C13—H13119.9
N1—C5—H5118.5C12—C13—C8120.3 (4)
N1—C5—C4123.0 (4)C12—C13—H13119.9
C4—C5—H5118.5O9—C35—H35A109.5
O2—C23—C20120.5 (3)O9—C35—H35B109.5
N7—C23—O2112.7 (3)O9—C35—H35C109.5
N7—C23—C20126.8 (4)H35A—C35—H35B109.5
C35—O9—H9A109.5H35A—C35—H35C109.5
O1—C6—C3119.2 (3)H35B—C35—H35C109.5
N2—C6—O1113.0 (3)O4—N12—O3117.8 (4)
N2—C6—C3127.8 (4)O5—N12—O3121.7 (5)
C6—N2—N3105.9 (3)O5—N12—O4120.4 (5)
C23—N7—N8106.1 (3)H36A—C36—H36B109.5
C30—C25—C24121.8 (4)H36A—C36—H36C109.5
C26—C25—C24118.4 (4)H36B—C36—H36C109.5
C26—C25—C30119.7 (4)O12—C36—H36A109.5
C9—C8—C7121.7 (4)O12—C36—H36B109.5
C9—C8—C13119.2 (4)O12—C36—H36C109.5
C13—C8—C7119.1 (4)C36—O12—H12A109.6
N6—C18—H18118.1H10A—O10—H10B109.5
N6—C18—C19123.8 (4)H10A—O10—H11165.8
C19—C18—H18118.1H10B—O10—H1178.1
O1—C7—C8119.3 (4)C37—O11—H11110.0
N3—C7—O1111.9 (4)O11—C37—H37A109.5
N3—C7—C8128.8 (4)O11—C37—H37B109.5
C18—C19—H19120.9O11—C37—H37C109.5
C18—C19—C20118.1 (4)H37A—C37—H37B109.5
C20—C19—H19120.9H37A—C37—H37C109.5
C2—C3—C6122.3 (4)H37B—C37—H37C109.5
C2—C3—C4118.6 (4)
N5—C17—N4—C14179.6 (3)N1—Cd1—N6—C1853.6 (5)
N5—C17—N4—C150.2 (5)N1—Cd1—N6—C22119.7 (4)
N5ii—Cd1—O6—N11159.3 (2)N1—Cd1—O3—N12172.0 (3)
N5ii—Cd1—N6—C1853.3 (3)N1—C5—C4—C30.1 (6)
N5ii—Cd1—N6—C22133.5 (3)O3—Cd1—O6—N11146.6 (2)
N5ii—Cd1—N1—C529.9 (3)O3—Cd1—N6—C18134.5 (3)
N5ii—Cd1—N1—C1138.0 (3)O3—Cd1—N6—C2252.3 (3)
N5ii—Cd1—O3—N1287.8 (3)O3—Cd1—N1—C5111.8 (3)
C17—N5—C16—C150.4 (5)O3—Cd1—N1—C156.1 (3)
C17—N4—C14—C1191.5 (5)C5—N1—C1—C20.2 (6)
C17—N4—C15—C160.1 (5)C23—O2—C24—C25172.6 (4)
N4—C14—C11—C104.4 (7)C23—O2—C24—N83.2 (5)
N4—C14—C11—C12177.1 (4)C23—N7—N8—C240.3 (6)
N4—C15—C16—N50.3 (5)C6—O1—C7—C8177.7 (4)
C14—N4—C15—C16179.3 (4)C6—O1—C7—N31.2 (5)
C14—C11—C10—C9177.7 (4)C6—N2—N3—C70.1 (6)
C14—C11—C12—C13177.7 (4)C6—C3—C2—C1176.7 (4)
N10—C34—N9—C31179.2 (3)C6—C3—C4—C5177.1 (4)
N10—C34—N9—C321.0 (5)N2—C6—C3—C2175.8 (5)
N10i—Cd1—O6—N1115.1 (3)N2—C6—C3—C46.5 (7)
N10i—Cd1—N6—C18144.9 (3)N7—C23—C20—C19168.3 (5)
N10i—Cd1—N6—C2228.4 (3)N7—C23—C20—C2111.6 (7)
N10i—Cd1—N1—C5166.4 (3)C25—C24—N8—N7173.2 (5)
N10i—Cd1—N1—C125.7 (3)C8—C7—N3—N2177.9 (4)
N10i—Cd1—O3—N1279.7 (3)C8—C9—C10—C110.0 (7)
N10—C33—C32—N91.0 (5)C18—N6—C22—C212.3 (6)
C34—N10—C33—C320.3 (5)C18—C19—C20—C23177.7 (4)
C34—N9—C31—C28113.6 (4)C18—C19—C20—C212.2 (6)
C34—N9—C32—C331.2 (5)C7—O1—C6—N21.1 (5)
N9—C31—C28—C27111.7 (4)C7—O1—C6—C3176.9 (4)
N9—C31—C28—C2968.2 (5)C7—C8—C9—C10179.4 (4)
C31—N9—C32—C33179.1 (4)C7—C8—C13—C12179.5 (4)
C31—C28—C27—C26179.0 (4)C3—C6—N2—N3177.1 (4)
C31—C28—C29—C30178.6 (4)C3—C2—C1—N10.8 (7)
C28—C27—C26—C250.2 (7)C27—C28—C29—C301.2 (7)
C28—C29—C30—C250.5 (7)C20—C23—N7—N8177.7 (4)
Cd1i—N5—C17—N4179.6 (2)C20—C21—C22—N60.2 (6)
Cd1i—N5—C16—C15179.6 (3)C11—C12—C13—C80.3 (7)
Cd1ii—N10—C34—N9179.3 (2)C29—C28—C27—C260.9 (7)
Cd1ii—N10—C33—C32178.5 (3)C15—N4—C14—C1187.7 (5)
Cd1—N6—C18—C19170.6 (3)C24—O2—C23—N73.0 (5)
Cd1—N6—C22—C21171.5 (3)C24—O2—C23—C20176.5 (4)
Cd1—N1—C5—C4168.3 (3)C24—C25—C30—C29176.1 (4)
Cd1—N1—C1—C2168.1 (3)C24—C25—C26—C27175.9 (4)
Cd1—O3—N12—O48.2 (5)C33—N10—C34—N90.4 (4)
Cd1—O3—N12—O5168.0 (5)C9—C8—C7—O16.3 (6)
O2—C23—N7—N81.8 (6)C9—C8—C7—N3174.9 (5)
O2—C23—C20—C1912.3 (6)C9—C8—C13—C120.5 (7)
O2—C23—C20—C21167.8 (4)C30—C25—C24—O29.7 (6)
O2—C24—N8—N72.3 (6)C30—C25—C24—N8175.2 (5)
O1—C6—N2—N30.7 (5)C30—C25—C26—C270.9 (7)
O1—C6—C3—C26.5 (6)C2—C3—C4—C50.7 (6)
O1—C6—C3—C4171.2 (4)C26—C25—C24—O2167.1 (4)
O1—C7—N3—N20.9 (6)C26—C25—C24—N88.0 (7)
O7—N11—O6—Cd1164.4 (3)C26—C25—C30—C290.6 (7)
O6—Cd1—N6—C1821.4 (3)C10—C11—C12—C130.9 (7)
O6—Cd1—N6—C22151.9 (3)C22—N6—C18—C192.6 (6)
O6—Cd1—N1—C542.7 (3)C22—C21—C20—C23177.4 (4)
O6—Cd1—N1—C1149.4 (3)C22—C21—C20—C192.5 (6)
O6—Cd1—O3—N12139.5 (3)C4—C3—C2—C11.0 (6)
O8—N11—O6—Cd114.5 (4)C16—N5—C17—N40.4 (4)
N6—Cd1—O6—N1170.4 (2)C1—N1—C5—C40.2 (6)
N6—Cd1—N1—C575.1 (5)C12—C11—C10—C90.7 (7)
N6—Cd1—N1—C1117.0 (4)C32—N9—C31—C2866.7 (5)
N6—Cd1—O3—N125.2 (3)C13—C8—C7—O1173.7 (4)
N6—C18—C19—C200.4 (6)C13—C8—C7—N35.1 (7)
N1—Cd1—O6—N1199.4 (2)C13—C8—C9—C100.6 (7)
Symmetry codes: (i) x, y, z1; (ii) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C22—H22···O9iii0.932.593.196 (5)123
O9—H9A···N7i0.822.142.949 (5)172
Symmetry codes: (i) x, y, z1; (iii) x+1, y+1, z+1.
 

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