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In the CuII compound catena-poly[[copper(II)-μ-[2-({2-[2-(naphthalen-2-yloxy)-1-oxidoethylidene]hydrazin-1-ylidene}methyl)phenolato]] dimethylformamide monosolvate monohydrate], {[Cu(C19H14N2O3)]·C3H7NO·H2O}n, (I), the CuII cation is O,N,O′-chelated by one ligand and further N,O-chelated by a second ligand, and exhibits a distorted square-pyramidal coordination environment. The ligand acts as an overall pentadentate bridge between two metal ions, thus forming a novel coordination polymer. In the trinuclear NiII compound diaquabis(1H-imidazole)bis[μ-2-oxido-N′-(1-oxido-2-phenoxyethylidene)benzohydrazidato]trinickel(II) dimethylformamide tetrasolvate, [Ni3(C15H11N2O4)2(C3H4N2)2(H2O)2]·4C3H7NO, (II), the three NiII cations are directly linked by two trans diazine (N—N) bridges and are strictly collinear by symmetry. The central NiII cation, located on an inversion centre, is coordinated by two water O atoms and is further N,O-chelated by two 2-oxido-N′-(1-oxido-2-phenoxyethylidene)benzohydrazidate(3−) ligands in an elongated octahedral coordination geometry. The two terminal centrosymmetrically related NiII cations are coordinated by an imidazole ligand and O,N,O′-chelated by a hydrazidate ligand in a distorted square-planar coordination geometry. Hydrogen bonds link individual molecules of (II) into a chain along [100].
Supporting information
CCDC references: 828188; 966097
For both compounds, data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: SHELXL97/2 (Sheldrick, 2008).
(I)
catena-Poly[[copper(II)-µ-[2-({2-[2-(naphthalen-2-yloxy)-1-oxidoethylidene]hydrazin-1-ylidene}methyl)phenolato]] dimethylformamide
monosolvate monohydrate]
top
Crystal data top
[Cu(C19H14N2O3)]·C3H7NO·H2O | F(000) = 980 |
Mr = 472.97 | Dx = 1.454 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3261 reflections |
a = 10.874 (4) Å | θ = 3.1–27.5° |
b = 22.702 (8) Å | µ = 1.05 mm−1 |
c = 9.137 (3) Å | T = 293 K |
β = 106.701 (8)° | Prism, green |
V = 2160.4 (13) Å3 | 0.38 × 0.24 × 0.16 mm |
Z = 4 | |
Data collection top
Rigaku R-AXIS RAPID imaging-plate diffractometer | 4922 independent reflections |
Radiation source: fine-focus sealed tube | 3261 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.064 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999) | h = −12→14 |
Tmin = 0.746, Tmax = 0.845 | k = −29→29 |
20932 measured reflections | l = −11→10 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0449P)2] where P = (Fo2 + 2Fc2)/3 |
4922 reflections | (Δ/σ)max = 0.001 |
290 parameters | Δρmax = 0.45 e Å−3 |
2 restraints | Δρmin = −0.41 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cu1 | 0.22469 (3) | 0.276839 (14) | 0.76683 (3) | 0.04085 (12) | |
O1 | 0.09165 (19) | 0.32967 (9) | 0.77090 (17) | 0.0529 (5) | |
O2 | 0.35735 (19) | 0.22366 (8) | 0.74037 (17) | 0.0510 (5) | |
O3 | 0.3858 (2) | 0.15040 (9) | 0.41410 (18) | 0.0568 (5) | |
N1 | 0.1897 (2) | 0.28199 (9) | 0.5478 (2) | 0.0390 (5) | |
N2 | 0.2614 (2) | 0.24276 (9) | 0.48768 (19) | 0.0392 (5) | |
C1 | 0.0278 (3) | 0.36435 (13) | 0.6588 (3) | 0.0492 (7) | |
C2 | 0.0334 (3) | 0.35888 (12) | 0.5050 (3) | 0.0486 (7) | |
C3 | −0.0398 (3) | 0.39776 (15) | 0.3933 (3) | 0.0702 (10) | |
H3A | −0.0370 | 0.3941 | 0.2929 | 0.084* | |
C4 | −0.1145 (4) | 0.44055 (18) | 0.4283 (4) | 0.0882 (13) | |
H4A | −0.1621 | 0.4659 | 0.3532 | 0.106* | |
C5 | −0.1182 (4) | 0.44561 (17) | 0.5791 (4) | 0.0865 (12) | |
H5A | −0.1682 | 0.4749 | 0.6047 | 0.104* | |
C6 | −0.0496 (3) | 0.40836 (15) | 0.6895 (3) | 0.0689 (10) | |
H6A | −0.0548 | 0.4126 | 0.7888 | 0.083* | |
C7 | 0.1100 (3) | 0.31659 (12) | 0.4573 (3) | 0.0451 (7) | |
H7A | 0.1018 | 0.3138 | 0.3534 | 0.054* | |
C8 | 0.3453 (3) | 0.21523 (11) | 0.5988 (2) | 0.0419 (6) | |
C9 | 0.4375 (3) | 0.17330 (13) | 0.5631 (3) | 0.0509 (7) | |
H9A | 0.5178 | 0.1933 | 0.5701 | 0.061* | |
H9B | 0.4549 | 0.1413 | 0.6367 | 0.061* | |
C10 | 0.4468 (3) | 0.10244 (13) | 0.3743 (3) | 0.0497 (7) | |
C11 | 0.5663 (3) | 0.08353 (13) | 0.4510 (3) | 0.0553 (8) | |
H11A | 0.6121 | 0.1029 | 0.5396 | 0.066* | |
C12 | 0.6220 (3) | 0.03484 (13) | 0.3982 (3) | 0.0557 (8) | |
C13 | 0.7478 (4) | 0.01502 (17) | 0.4716 (4) | 0.0773 (11) | |
H13A | 0.7966 | 0.0344 | 0.5587 | 0.093* | |
C14 | 0.7983 (4) | −0.03162 (19) | 0.4173 (5) | 0.0876 (12) | |
H14A | 0.8812 | −0.0440 | 0.4676 | 0.105* | |
C15 | 0.7280 (4) | −0.06119 (17) | 0.2874 (5) | 0.0834 (11) | |
H15A | 0.7640 | −0.0932 | 0.2511 | 0.100* | |
C16 | 0.6073 (4) | −0.04367 (15) | 0.2131 (4) | 0.0720 (9) | |
H16A | 0.5608 | −0.0640 | 0.1266 | 0.086* | |
C17 | 0.5506 (3) | 0.00532 (13) | 0.2654 (3) | 0.0571 (8) | |
C18 | 0.4268 (3) | 0.02601 (15) | 0.1906 (4) | 0.0661 (9) | |
H18A | 0.3787 | 0.0067 | 0.1031 | 0.079* | |
C19 | 0.3755 (3) | 0.07322 (14) | 0.2419 (3) | 0.0601 (8) | |
H19A | 0.2935 | 0.0862 | 0.1897 | 0.072* | |
O4 | −0.1633 (3) | 0.23117 (16) | 0.5544 (4) | 0.1252 (13) | |
N3 | −0.2914 (3) | 0.29975 (15) | 0.6060 (3) | 0.0806 (9) | |
C20 | −0.1981 (4) | 0.2612 (2) | 0.6446 (5) | 0.0867 (12) | |
H20A | −0.1557 | 0.2566 | 0.7480 | 0.104* | |
C21 | −0.3523 (5) | 0.3130 (3) | 0.4469 (5) | 0.140 (2) | |
H21A | −0.3191 | 0.2873 | 0.3839 | 0.209* | |
H21B | −0.3349 | 0.3532 | 0.4267 | 0.209* | |
H21C | −0.4433 | 0.3074 | 0.4245 | 0.209* | |
C22 | −0.3309 (5) | 0.3340 (2) | 0.7182 (6) | 0.1239 (18) | |
H22A | −0.2875 | 0.3198 | 0.8187 | 0.186* | |
H22B | −0.4220 | 0.3302 | 0.7002 | 0.186* | |
H22C | −0.3095 | 0.3746 | 0.7100 | 0.186* | |
O1W | 0.0435 (3) | 0.16060 (13) | 0.5727 (3) | 0.0790 (7) | |
H1W | −0.026 (2) | 0.1801 (15) | 0.555 (4) | 0.083 (13)* | |
H2W | 0.052 (3) | 0.1599 (16) | 0.488 (2) | 0.077 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cu1 | 0.0545 (2) | 0.0497 (2) | 0.02148 (15) | 0.00126 (16) | 0.01581 (13) | −0.00012 (12) |
O1 | 0.0627 (12) | 0.0693 (13) | 0.0306 (8) | 0.0124 (10) | 0.0195 (8) | −0.0002 (9) |
O2 | 0.0647 (12) | 0.0661 (12) | 0.0226 (7) | 0.0156 (10) | 0.0130 (8) | 0.0006 (8) |
O3 | 0.0711 (13) | 0.0633 (13) | 0.0326 (8) | 0.0201 (11) | 0.0096 (9) | −0.0056 (8) |
N1 | 0.0526 (13) | 0.0421 (12) | 0.0252 (9) | 0.0011 (10) | 0.0160 (9) | −0.0010 (8) |
N2 | 0.0542 (13) | 0.0441 (12) | 0.0231 (9) | 0.0060 (10) | 0.0173 (10) | 0.0022 (8) |
C1 | 0.0558 (17) | 0.0569 (17) | 0.0360 (12) | 0.0039 (14) | 0.0148 (13) | −0.0043 (12) |
C2 | 0.0581 (17) | 0.0527 (17) | 0.0359 (12) | 0.0085 (14) | 0.0150 (13) | 0.0010 (12) |
C3 | 0.091 (3) | 0.075 (2) | 0.0450 (15) | 0.029 (2) | 0.0210 (16) | 0.0076 (15) |
C4 | 0.112 (3) | 0.093 (3) | 0.0593 (19) | 0.053 (3) | 0.025 (2) | 0.0144 (18) |
C5 | 0.100 (3) | 0.091 (3) | 0.068 (2) | 0.046 (2) | 0.023 (2) | −0.004 (2) |
C6 | 0.078 (2) | 0.083 (2) | 0.0483 (15) | 0.0262 (19) | 0.0229 (16) | −0.0055 (16) |
C7 | 0.0586 (17) | 0.0519 (16) | 0.0263 (11) | 0.0008 (14) | 0.0144 (11) | 0.0028 (11) |
C8 | 0.0526 (16) | 0.0497 (16) | 0.0274 (11) | −0.0001 (13) | 0.0177 (11) | −0.0017 (10) |
C9 | 0.0625 (18) | 0.0597 (18) | 0.0311 (11) | 0.0064 (15) | 0.0142 (12) | −0.0034 (12) |
C10 | 0.0613 (19) | 0.0522 (17) | 0.0390 (13) | 0.0053 (14) | 0.0196 (13) | −0.0001 (12) |
C11 | 0.067 (2) | 0.0593 (19) | 0.0405 (13) | 0.0061 (15) | 0.0171 (14) | −0.0030 (13) |
C12 | 0.071 (2) | 0.0548 (18) | 0.0486 (14) | 0.0086 (16) | 0.0286 (15) | 0.0065 (13) |
C13 | 0.080 (2) | 0.086 (3) | 0.0643 (19) | 0.030 (2) | 0.0176 (19) | 0.0040 (18) |
C14 | 0.090 (3) | 0.090 (3) | 0.088 (3) | 0.035 (2) | 0.032 (2) | 0.015 (2) |
C15 | 0.105 (3) | 0.058 (2) | 0.107 (3) | 0.020 (2) | 0.063 (3) | 0.010 (2) |
C16 | 0.095 (3) | 0.053 (2) | 0.081 (2) | −0.0040 (19) | 0.047 (2) | −0.0072 (17) |
C17 | 0.077 (2) | 0.0449 (16) | 0.0603 (16) | 0.0017 (16) | 0.0376 (17) | 0.0002 (13) |
C18 | 0.074 (2) | 0.066 (2) | 0.0602 (17) | −0.0120 (18) | 0.0209 (17) | −0.0189 (16) |
C19 | 0.0603 (19) | 0.066 (2) | 0.0525 (15) | 0.0028 (16) | 0.0146 (14) | −0.0125 (14) |
O4 | 0.124 (3) | 0.137 (3) | 0.114 (2) | 0.051 (2) | 0.033 (2) | −0.029 (2) |
N3 | 0.072 (2) | 0.094 (2) | 0.0735 (18) | 0.0150 (18) | 0.0172 (16) | −0.0088 (17) |
C20 | 0.077 (3) | 0.103 (3) | 0.077 (2) | 0.021 (2) | 0.017 (2) | −0.006 (2) |
C21 | 0.130 (4) | 0.163 (5) | 0.092 (3) | 0.039 (4) | −0.021 (3) | −0.011 (3) |
C22 | 0.138 (4) | 0.126 (4) | 0.127 (4) | 0.038 (4) | 0.069 (3) | −0.018 (3) |
O1W | 0.091 (2) | 0.099 (2) | 0.0561 (13) | 0.0245 (16) | 0.0344 (14) | 0.0229 (14) |
Geometric parameters (Å, º) top
Cu1—O1 | 1.888 (2) | C11—C12 | 1.411 (4) |
Cu1—N1 | 1.9304 (19) | C11—H11A | 0.9300 |
Cu1—O2 | 1.949 (2) | C12—C17 | 1.408 (4) |
Cu1—N2i | 1.9915 (18) | C12—C13 | 1.413 (5) |
Cu1—O3i | 2.5008 (19) | C13—C14 | 1.351 (5) |
O1—C1 | 1.320 (3) | C13—H13A | 0.9300 |
O2—C8 | 1.277 (3) | C14—C15 | 1.387 (5) |
O3—C10 | 1.377 (3) | C14—H14A | 0.9300 |
O3—C9 | 1.414 (3) | C15—C16 | 1.352 (5) |
N1—C7 | 1.280 (3) | C15—H15A | 0.9300 |
N1—N2 | 1.396 (3) | C16—C17 | 1.419 (5) |
N2—C8 | 1.312 (3) | C16—H16A | 0.9300 |
N2—Cu1ii | 1.9915 (18) | C17—C18 | 1.404 (5) |
C1—C6 | 1.386 (4) | C18—C19 | 1.353 (4) |
C1—C2 | 1.430 (4) | C18—H18A | 0.9300 |
C2—C3 | 1.410 (4) | C19—H19A | 0.9300 |
C2—C7 | 1.419 (4) | O4—C20 | 1.212 (5) |
C3—C4 | 1.362 (5) | N3—C20 | 1.309 (5) |
C3—H3A | 0.9300 | N3—C21 | 1.445 (5) |
C4—C5 | 1.395 (5) | N3—C22 | 1.446 (5) |
C4—H4A | 0.9300 | C20—H20A | 0.9300 |
C5—C6 | 1.363 (4) | C21—H21A | 0.9600 |
C5—H5A | 0.9300 | C21—H21B | 0.9600 |
C6—H6A | 0.9300 | C21—H21C | 0.9600 |
C7—H7A | 0.9300 | C22—H22A | 0.9600 |
C8—C9 | 1.485 (4) | C22—H22B | 0.9600 |
C9—H9A | 0.9700 | C22—H22C | 0.9600 |
C9—H9B | 0.9700 | O1W—H1W | 0.850 (18) |
C10—C11 | 1.356 (4) | O1W—H2W | 0.808 (18) |
C10—C19 | 1.402 (4) | | |
| | | |
O1—Cu1—N1 | 93.34 (8) | C11—C10—O3 | 125.2 (2) |
O1—Cu1—O2 | 174.20 (6) | C11—C10—C19 | 120.4 (3) |
N1—Cu1—O2 | 80.86 (8) | O3—C10—C19 | 114.4 (3) |
O1—Cu1—N2i | 93.08 (8) | C10—C11—C12 | 120.9 (3) |
N1—Cu1—N2i | 170.55 (9) | C10—C11—H11A | 119.6 |
O2—Cu1—N2i | 92.70 (8) | C12—C11—H11A | 119.6 |
O1—Cu1—O3i | 89.55 (8) | C17—C12—C11 | 118.9 (3) |
O2—Cu1—O3i | 92.68 (8) | C17—C12—C13 | 118.4 (3) |
N1—Cu1—O3i | 114.62 (8) | C11—C12—C13 | 122.7 (3) |
N2i—Cu1—O3i | 72.36 (8) | C14—C13—C12 | 121.0 (3) |
C1—O1—Cu1 | 126.80 (17) | C14—C13—H13A | 119.5 |
C8—O2—Cu1 | 110.76 (16) | C12—C13—H13A | 119.5 |
C10—O3—C9 | 117.2 (2) | C13—C14—C15 | 120.8 (4) |
C7—N1—N2 | 119.25 (19) | C13—C14—H14A | 119.6 |
C7—N1—Cu1 | 126.97 (18) | C15—C14—H14A | 119.6 |
N2—N1—Cu1 | 113.78 (14) | C16—C15—C14 | 120.2 (4) |
C8—N2—N1 | 110.02 (18) | C16—C15—H15A | 119.9 |
C8—N2—Cu1ii | 124.75 (17) | C14—C15—H15A | 119.9 |
N1—N2—Cu1ii | 124.68 (14) | C15—C16—C17 | 121.0 (3) |
O1—C1—C6 | 119.2 (2) | C15—C16—H16A | 119.5 |
O1—C1—C2 | 123.3 (2) | C17—C16—H16A | 119.5 |
C6—C1—C2 | 117.5 (2) | C18—C17—C12 | 118.3 (3) |
C3—C2—C7 | 117.4 (2) | C18—C17—C16 | 123.1 (3) |
C3—C2—C1 | 118.9 (3) | C12—C17—C16 | 118.5 (3) |
C7—C2—C1 | 123.7 (2) | C19—C18—C17 | 122.0 (3) |
C4—C3—C2 | 121.8 (3) | C19—C18—H18A | 119.0 |
C4—C3—H3A | 119.1 | C17—C18—H18A | 119.0 |
C2—C3—H3A | 119.1 | C18—C19—C10 | 119.6 (3) |
C3—C4—C5 | 118.6 (3) | C18—C19—H19A | 120.2 |
C3—C4—H4A | 120.7 | C10—C19—H19A | 120.2 |
C5—C4—H4A | 120.7 | C20—N3—C21 | 120.4 (4) |
C6—C5—C4 | 121.0 (3) | C20—N3—C22 | 122.2 (4) |
C6—C5—H5A | 119.5 | C21—N3—C22 | 117.2 (4) |
C4—C5—H5A | 119.5 | O4—C20—N3 | 124.2 (4) |
C5—C6—C1 | 122.2 (3) | O4—C20—H20A | 117.9 |
C5—C6—H6A | 118.9 | N3—C20—H20A | 117.9 |
C1—C6—H6A | 118.9 | N3—C21—H21A | 109.5 |
N1—C7—C2 | 124.4 (2) | N3—C21—H21B | 109.5 |
N1—C7—H7A | 117.8 | H21A—C21—H21B | 109.5 |
C2—C7—H7A | 117.8 | N3—C21—H21C | 109.5 |
O2—C8—N2 | 124.0 (2) | H21A—C21—H21C | 109.5 |
O2—C8—C9 | 116.0 (2) | H21B—C21—H21C | 109.5 |
N2—C8—C9 | 119.9 (2) | N3—C22—H22A | 109.5 |
O3—C9—C8 | 109.9 (2) | N3—C22—H22B | 109.5 |
O3—C9—H9A | 109.7 | H22A—C22—H22B | 109.5 |
C8—C9—H9A | 109.7 | N3—C22—H22C | 109.5 |
O3—C9—H9B | 109.7 | H22A—C22—H22C | 109.5 |
C8—C9—H9B | 109.7 | H22B—C22—H22C | 109.5 |
H9A—C9—H9B | 108.2 | H1W—O1W—H2W | 99 (3) |
| | | |
N1—Cu1—O1—C1 | −13.2 (2) | Cu1—O2—C8—C9 | −177.4 (2) |
O2—Cu1—O1—C1 | −11.2 (10) | N1—N2—C8—O2 | 0.3 (4) |
N2i—Cu1—O1—C1 | 173.8 (2) | Cu1ii—N2—C8—O2 | −171.5 (2) |
O1—Cu1—O2—C8 | −8.3 (10) | N1—N2—C8—C9 | −176.9 (2) |
N1—Cu1—O2—C8 | −6.38 (18) | Cu1ii—N2—C8—C9 | 11.3 (4) |
N2i—Cu1—O2—C8 | 166.65 (19) | C10—O3—C9—C8 | −167.3 (2) |
O1—Cu1—N1—C7 | 6.5 (2) | O2—C8—C9—O3 | 157.0 (2) |
O2—Cu1—N1—C7 | −173.3 (2) | N2—C8—C9—O3 | −25.6 (4) |
N2i—Cu1—N1—C7 | 139.2 (5) | C9—O3—C10—C11 | −15.4 (4) |
O1—Cu1—N1—N2 | −173.39 (17) | C9—O3—C10—C19 | 165.4 (3) |
O2—Cu1—N1—N2 | 6.81 (17) | O3—C10—C11—C12 | −178.1 (3) |
N2i—Cu1—N1—N2 | −40.7 (6) | C19—C10—C11—C12 | 1.0 (5) |
C7—N1—N2—C8 | 174.2 (2) | C10—C11—C12—C17 | −1.1 (5) |
Cu1—N1—N2—C8 | −5.9 (3) | C10—C11—C12—C13 | 177.7 (3) |
C7—N1—N2—Cu1ii | −14.0 (3) | C17—C12—C13—C14 | −0.8 (6) |
Cu1—N1—N2—Cu1ii | 165.92 (11) | C11—C12—C13—C14 | −179.6 (4) |
Cu1—O1—C1—C6 | −167.8 (2) | C12—C13—C14—C15 | 0.3 (6) |
Cu1—O1—C1—C2 | 12.5 (4) | C13—C14—C15—C16 | −0.1 (7) |
O1—C1—C2—C3 | 179.3 (3) | C14—C15—C16—C17 | 0.5 (6) |
C6—C1—C2—C3 | −0.4 (4) | C11—C12—C17—C18 | 0.4 (5) |
O1—C1—C2—C7 | −1.4 (5) | C13—C12—C17—C18 | −178.5 (3) |
C6—C1—C2—C7 | 178.9 (3) | C11—C12—C17—C16 | −179.9 (3) |
C7—C2—C3—C4 | −178.8 (4) | C13—C12—C17—C16 | 1.2 (5) |
C1—C2—C3—C4 | 0.6 (5) | C15—C16—C17—C18 | 178.6 (3) |
C2—C3—C4—C5 | −0.1 (7) | C15—C16—C17—C12 | −1.1 (5) |
C3—C4—C5—C6 | −0.5 (7) | C12—C17—C18—C19 | 0.4 (5) |
C4—C5—C6—C1 | 0.7 (6) | C16—C17—C18—C19 | −179.3 (3) |
O1—C1—C6—C5 | −179.9 (3) | C17—C18—C19—C10 | −0.5 (5) |
C2—C1—C6—C5 | −0.2 (5) | C11—C10—C19—C18 | −0.2 (5) |
N2—N1—C7—C2 | −179.0 (3) | O3—C10—C19—C18 | 178.9 (3) |
Cu1—N1—C7—C2 | 1.1 (4) | C21—N3—C20—O4 | −6.1 (8) |
C3—C2—C7—N1 | 173.6 (3) | C22—N3—C20—O4 | 179.0 (5) |
C1—C2—C7—N1 | −5.8 (5) | Cu1—N1—N2—Cu1ii | 165.92 (11) |
Cu1—O2—C8—N2 | 5.3 (3) | | |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O4 | 0.85 (2) | 1.89 (2) | 2.726 (4) | 168 (4) |
O1W—H2W···O1ii | 0.81 (2) | 2.16 (2) | 2.959 (3) | 171 (4) |
Symmetry code: (ii) x, −y+1/2, z−1/2. |
(II) Diaquabis(1
H-imidazole)bis[µ-2-oxido-
N'-(1-oxido-2-phenoxyethylidene)benzohydrazidato]trinickel(II) dimethylformamide tetrasolvate
top
Crystal data top
[Ni3(C15H11N2O4)2(C3H4N2)2(H2O)2]·4C3H7NO | Z = 1 |
Mr = 1207.23 | F(000) = 630 |
Triclinic, P1 | Dx = 1.474 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.978 (5) Å | Cell parameters from 3982 reflections |
b = 11.653 (5) Å | θ = 3.1–27.5° |
c = 12.276 (8) Å | µ = 1.10 mm−1 |
α = 80.87 (2)° | T = 293 K |
β = 64.41 (2)° | Block, red |
γ = 74.069 (16)° | 0.37 × 0.24 × 0.10 mm |
V = 1360.5 (13) Å3 | |
Data collection top
Rigaku R-AXIS RAPID imaging-plate diffractometer | 6158 independent reflections |
Radiation source: fine-focus sealed tube | 3982 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999) | h = −13→14 |
Tmin = 0.735, Tmax = 0.896 | k = −13→15 |
13399 measured reflections | l = −15→15 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0476P)2] where P = (Fo2 + 2Fc2)/3 |
6158 reflections | (Δ/σ)max < 0.001 |
362 parameters | Δρmax = 0.39 e Å−3 |
2 restraints | Δρmin = −0.43 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R-factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.10852 (3) | 0.36024 (3) | 0.74443 (3) | 0.03282 (12) | |
Ni2 | 0.5000 | 0.5000 | 0.5000 | 0.03116 (14) | |
O1 | 0.15613 (19) | 0.22377 (17) | 0.82605 (19) | 0.0415 (5) | |
O2 | 0.52233 (18) | 0.33601 (16) | 0.58391 (18) | 0.0370 (5) | |
O3 | 0.06367 (18) | 0.49903 (16) | 0.65818 (18) | 0.0388 (5) | |
O4 | 0.0477 (2) | 0.74215 (17) | 0.5630 (2) | 0.0462 (6) | |
O5 | 0.5317 (2) | 0.4245 (2) | 0.3412 (2) | 0.0424 (5) | |
N1 | 0.2857 (2) | 0.37863 (18) | 0.6615 (2) | 0.0308 (5) | |
N2 | 0.2978 (2) | 0.48165 (19) | 0.5835 (2) | 0.0322 (5) | |
N3 | −0.0818 (2) | 0.3510 (2) | 0.8266 (2) | 0.0387 (6) | |
N4 | −0.3041 (3) | 0.3797 (2) | 0.8768 (3) | 0.0526 (7) | |
H4B | −0.3846 | 0.4076 | 0.8755 | 0.063* | |
C1 | 0.2829 (3) | 0.1683 (2) | 0.8166 (3) | 0.0332 (6) | |
C2 | 0.4054 (3) | 0.2033 (2) | 0.7367 (2) | 0.0306 (6) | |
C3 | 0.5337 (3) | 0.1366 (2) | 0.7377 (3) | 0.0404 (7) | |
H3A | 0.6149 | 0.1601 | 0.6853 | 0.049* | |
C4 | 0.5412 (3) | 0.0388 (3) | 0.8138 (3) | 0.0493 (9) | |
H4A | 0.6265 | −0.0044 | 0.8130 | 0.059* | |
C5 | 0.4198 (3) | 0.0045 (3) | 0.8925 (3) | 0.0501 (9) | |
H5A | 0.4241 | −0.0619 | 0.9450 | 0.060* | |
C6 | 0.2937 (3) | 0.0671 (3) | 0.8940 (3) | 0.0428 (8) | |
H6A | 0.2138 | 0.0421 | 0.9471 | 0.051* | |
C7 | 0.4086 (3) | 0.3095 (2) | 0.6555 (2) | 0.0310 (6) | |
C8 | 0.1745 (3) | 0.5372 (2) | 0.5889 (3) | 0.0338 (7) | |
C9 | 0.1631 (3) | 0.6452 (3) | 0.5060 (3) | 0.0419 (8) | |
H9A | 0.2482 | 0.6728 | 0.4749 | 0.050* | |
H9B | 0.1540 | 0.6223 | 0.4378 | 0.050* | |
C10 | 0.0570 (3) | 0.8096 (3) | 0.6401 (3) | 0.0418 (8) | |
C11 | −0.0517 (3) | 0.9084 (3) | 0.6809 (3) | 0.0557 (10) | |
H11A | −0.1227 | 0.9253 | 0.6545 | 0.067* | |
C12 | −0.0556 (4) | 0.9817 (3) | 0.7600 (4) | 0.0682 (11) | |
H12A | −0.1292 | 1.0480 | 0.7869 | 0.082* | |
C13 | 0.0485 (4) | 0.9578 (4) | 0.7999 (4) | 0.0689 (11) | |
H13A | 0.0460 | 1.0070 | 0.8539 | 0.083* | |
C14 | 0.1571 (4) | 0.8593 (3) | 0.7579 (3) | 0.0606 (10) | |
H14A | 0.2279 | 0.8427 | 0.7846 | 0.073* | |
C15 | 0.1639 (3) | 0.7851 (3) | 0.6779 (3) | 0.0487 (8) | |
H15A | 0.2385 | 0.7199 | 0.6499 | 0.058* | |
C16 | −0.1875 (3) | 0.4122 (3) | 0.8004 (3) | 0.0425 (7) | |
H16A | −0.1812 | 0.4698 | 0.7376 | 0.051* | |
C17 | −0.2741 (3) | 0.2950 (3) | 0.9566 (4) | 0.0645 (11) | |
H17A | −0.3356 | 0.2565 | 1.0200 | 0.077* | |
C18 | −0.1366 (3) | 0.2781 (3) | 0.9255 (3) | 0.0589 (10) | |
H18A | −0.0867 | 0.2251 | 0.9650 | 0.071* | |
O6 | 0.5779 (2) | 0.5577 (2) | 0.1243 (2) | 0.0542 (6) | |
N5 | 0.7505 (3) | 0.6389 (2) | −0.0199 (2) | 0.0457 (7) | |
C19 | 0.6996 (4) | 0.5670 (3) | 0.0738 (3) | 0.0485 (8) | |
H19A | 0.7611 | 0.5187 | 0.1048 | 0.063 (11)* | |
C20 | 0.6587 (4) | 0.7181 (4) | −0.0693 (4) | 0.0812 (13) | |
H20A | 0.5845 | 0.7675 | −0.0072 | 0.122* | |
H20B | 0.6209 | 0.6720 | −0.0999 | 0.122* | |
H20C | 0.7094 | 0.7677 | −0.1339 | 0.122* | |
C21 | 0.8948 (4) | 0.6467 (3) | −0.0728 (3) | 0.0690 (11) | |
H21A | 0.9439 | 0.5905 | −0.0311 | 0.103* | |
H21B | 0.8995 | 0.7261 | −0.0658 | 0.103* | |
H21C | 0.9362 | 0.6287 | −0.1567 | 0.103* | |
O7 | 0.3056 (3) | 0.3641 (2) | 0.3476 (3) | 0.0723 (8) | |
N6 | 0.3083 (3) | 0.1840 (3) | 0.4486 (3) | 0.0583 (8) | |
C22 | 0.2463 (4) | 0.2906 (3) | 0.4188 (4) | 0.0618 (10) | |
H22A | 0.1498 | 0.3115 | 0.4548 | 0.074* | |
C23 | 0.2280 (5) | 0.1080 (4) | 0.5404 (4) | 0.0883 (14) | |
H23A | 0.1310 | 0.1458 | 0.5672 | 0.132* | |
H23B | 0.2538 | 0.0950 | 0.6075 | 0.132* | |
H23C | 0.2457 | 0.0328 | 0.5073 | 0.132* | |
C24 | 0.4589 (4) | 0.1474 (3) | 0.4003 (4) | 0.0773 (12) | |
H24A | 0.4979 | 0.1923 | 0.3261 | 0.116* | |
H24B | 0.4880 | 0.0637 | 0.3852 | 0.116* | |
H24C | 0.4901 | 0.1619 | 0.4577 | 0.116* | |
H5B | 0.463 (3) | 0.401 (3) | 0.349 (3) | 0.068 (13)* | |
H5C | 0.546 (3) | 0.469 (2) | 0.282 (2) | 0.051 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.02582 (19) | 0.0346 (2) | 0.0349 (2) | −0.00864 (16) | −0.01102 (16) | 0.00576 (15) |
Ni2 | 0.0233 (2) | 0.0335 (3) | 0.0319 (3) | −0.0087 (2) | −0.0091 (2) | 0.0085 (2) |
O1 | 0.0275 (10) | 0.0423 (11) | 0.0487 (14) | −0.0116 (9) | −0.0139 (10) | 0.0154 (9) |
O2 | 0.0228 (9) | 0.0377 (10) | 0.0412 (12) | −0.0076 (9) | −0.0083 (9) | 0.0108 (9) |
O3 | 0.0262 (10) | 0.0413 (11) | 0.0428 (13) | −0.0065 (9) | −0.0130 (9) | 0.0094 (9) |
O4 | 0.0334 (11) | 0.0400 (11) | 0.0646 (16) | −0.0013 (10) | −0.0256 (11) | 0.0032 (10) |
O5 | 0.0409 (13) | 0.0503 (13) | 0.0376 (14) | −0.0197 (11) | −0.0162 (11) | 0.0102 (10) |
N1 | 0.0253 (11) | 0.0315 (11) | 0.0340 (14) | −0.0078 (10) | −0.0130 (10) | 0.0080 (10) |
N2 | 0.0257 (12) | 0.0339 (12) | 0.0344 (14) | −0.0091 (10) | −0.0117 (10) | 0.0080 (10) |
N3 | 0.0324 (13) | 0.0395 (13) | 0.0434 (16) | −0.0121 (11) | −0.0152 (12) | 0.0065 (11) |
N4 | 0.0294 (13) | 0.0582 (17) | 0.067 (2) | −0.0102 (13) | −0.0188 (14) | 0.0029 (15) |
C1 | 0.0314 (14) | 0.0328 (14) | 0.0352 (17) | −0.0067 (12) | −0.0152 (13) | 0.0024 (12) |
C2 | 0.0265 (13) | 0.0307 (14) | 0.0323 (16) | −0.0047 (12) | −0.0119 (12) | 0.0012 (11) |
C3 | 0.0303 (15) | 0.0390 (16) | 0.0466 (19) | −0.0060 (13) | −0.0143 (14) | 0.0051 (14) |
C4 | 0.0370 (17) | 0.0438 (17) | 0.060 (2) | −0.0001 (15) | −0.0236 (17) | 0.0116 (16) |
C5 | 0.053 (2) | 0.0404 (17) | 0.053 (2) | −0.0091 (16) | −0.0258 (17) | 0.0186 (15) |
C6 | 0.0394 (16) | 0.0423 (16) | 0.0425 (19) | −0.0159 (14) | −0.0136 (14) | 0.0119 (14) |
C7 | 0.0290 (14) | 0.0333 (14) | 0.0300 (16) | −0.0072 (12) | −0.0117 (12) | −0.0007 (12) |
C8 | 0.0300 (15) | 0.0378 (15) | 0.0300 (16) | −0.0087 (13) | −0.0101 (13) | 0.0036 (12) |
C9 | 0.0350 (16) | 0.0423 (17) | 0.0430 (19) | −0.0075 (14) | −0.0154 (14) | 0.0083 (14) |
C10 | 0.0364 (16) | 0.0408 (16) | 0.047 (2) | −0.0148 (14) | −0.0174 (15) | 0.0123 (14) |
C11 | 0.0326 (17) | 0.052 (2) | 0.075 (3) | −0.0006 (16) | −0.0203 (17) | −0.0030 (18) |
C12 | 0.054 (2) | 0.061 (2) | 0.075 (3) | −0.0054 (19) | −0.013 (2) | −0.019 (2) |
C13 | 0.061 (2) | 0.086 (3) | 0.056 (3) | −0.030 (2) | −0.011 (2) | −0.012 (2) |
C14 | 0.050 (2) | 0.077 (3) | 0.061 (3) | −0.031 (2) | −0.0234 (19) | 0.010 (2) |
C15 | 0.0366 (17) | 0.0447 (18) | 0.062 (2) | −0.0120 (15) | −0.0189 (16) | 0.0065 (16) |
C16 | 0.0329 (16) | 0.0484 (18) | 0.044 (2) | −0.0109 (14) | −0.0150 (14) | 0.0030 (14) |
C17 | 0.0385 (18) | 0.059 (2) | 0.086 (3) | −0.0238 (17) | −0.0197 (19) | 0.029 (2) |
C18 | 0.0419 (19) | 0.054 (2) | 0.070 (3) | −0.0146 (17) | −0.0210 (18) | 0.0246 (18) |
O6 | 0.0391 (12) | 0.0726 (15) | 0.0465 (14) | −0.0204 (12) | −0.0134 (11) | 0.0101 (11) |
N5 | 0.0456 (15) | 0.0464 (14) | 0.0380 (16) | −0.0106 (13) | −0.0113 (13) | 0.0005 (12) |
C19 | 0.050 (2) | 0.0524 (19) | 0.040 (2) | −0.0083 (17) | −0.0187 (17) | 0.0018 (15) |
C20 | 0.085 (3) | 0.073 (3) | 0.082 (3) | −0.017 (2) | −0.044 (3) | 0.033 (2) |
C21 | 0.053 (2) | 0.073 (2) | 0.059 (3) | −0.023 (2) | 0.0033 (19) | −0.0058 (19) |
O7 | 0.0782 (18) | 0.0684 (16) | 0.100 (2) | −0.0377 (15) | −0.0624 (17) | 0.0309 (15) |
N6 | 0.076 (2) | 0.0545 (17) | 0.057 (2) | −0.0305 (17) | −0.0332 (17) | 0.0094 (14) |
C22 | 0.061 (2) | 0.071 (2) | 0.074 (3) | −0.030 (2) | −0.042 (2) | 0.008 (2) |
C23 | 0.128 (4) | 0.085 (3) | 0.072 (3) | −0.066 (3) | −0.045 (3) | 0.029 (2) |
C24 | 0.073 (3) | 0.060 (2) | 0.098 (4) | −0.010 (2) | −0.037 (3) | −0.003 (2) |
Geometric parameters (Å, º) top
Ni1—O1 | 1.8156 (19) | C9—H9B | 0.9700 |
Ni1—N1 | 1.821 (2) | C10—C11 | 1.383 (4) |
Ni1—O3 | 1.8571 (19) | C10—C15 | 1.386 (4) |
Ni1—N3 | 1.914 (3) | C11—C12 | 1.372 (5) |
Ni2—O2i | 2.0271 (19) | C11—H11A | 0.9300 |
Ni2—O2 | 2.0271 (19) | C12—C13 | 1.374 (5) |
Ni2—N2i | 2.061 (2) | C12—H12A | 0.9300 |
Ni2—N2 | 2.061 (2) | C13—C14 | 1.383 (5) |
Ni2—O5i | 2.118 (3) | C13—H13A | 0.9300 |
Ni2—O5 | 2.118 (3) | C14—C15 | 1.374 (5) |
O1—C1 | 1.326 (3) | C14—H14A | 0.9300 |
O2—C7 | 1.267 (3) | C15—H15A | 0.9300 |
O3—C8 | 1.298 (3) | C16—H16A | 0.9300 |
O4—C10 | 1.373 (4) | C17—C18 | 1.351 (4) |
O4—C9 | 1.439 (3) | C17—H17A | 0.9300 |
O5—H5B | 0.832 (18) | C18—H18A | 0.9300 |
O5—H5C | 0.809 (17) | O6—C19 | 1.234 (4) |
N1—C7 | 1.346 (3) | N5—C19 | 1.316 (4) |
N1—N2 | 1.410 (3) | N5—C20 | 1.441 (4) |
N2—C8 | 1.308 (3) | N5—C21 | 1.453 (4) |
N3—C16 | 1.324 (3) | C19—H19A | 0.9300 |
N3—C18 | 1.371 (4) | C20—H20A | 0.9600 |
N4—C16 | 1.334 (4) | C20—H20B | 0.9600 |
N4—C17 | 1.355 (4) | C20—H20C | 0.9600 |
N4—H4B | 0.8600 | C21—H21A | 0.9600 |
C1—C2 | 1.404 (4) | C21—H21B | 0.9600 |
C1—C6 | 1.404 (4) | C21—H21C | 0.9600 |
C2—C3 | 1.414 (4) | O7—C22 | 1.224 (4) |
C2—C7 | 1.458 (4) | N6—C22 | 1.322 (4) |
C3—C4 | 1.362 (4) | N6—C23 | 1.444 (4) |
C3—H3A | 0.9300 | N6—C24 | 1.453 (5) |
C4—C5 | 1.388 (4) | C22—H22A | 0.9300 |
C4—H4A | 0.9300 | C23—H23A | 0.9600 |
C5—C6 | 1.370 (4) | C23—H23B | 0.9600 |
C5—H5A | 0.9300 | C23—H23C | 0.9600 |
C6—H6A | 0.9300 | C24—H24A | 0.9600 |
C8—C9 | 1.501 (4) | C24—H24B | 0.9600 |
C9—H9A | 0.9700 | C24—H24C | 0.9600 |
| | | |
O1—Ni1—N1 | 94.50 (9) | O4—C9—H9B | 108.8 |
O1—Ni1—O3 | 178.74 (9) | C8—C9—H9B | 108.8 |
N1—Ni1—O3 | 84.39 (9) | H9A—C9—H9B | 107.7 |
O1—Ni1—N3 | 89.38 (9) | O4—C10—C11 | 115.0 (3) |
N1—Ni1—N3 | 176.11 (9) | O4—C10—C15 | 125.1 (3) |
O3—Ni1—N3 | 91.74 (9) | C11—C10—C15 | 119.9 (3) |
O2i—Ni2—O2 | 180.000 (1) | C12—C11—C10 | 120.5 (3) |
O2i—Ni2—N2i | 78.33 (8) | C12—C11—H11A | 119.7 |
O2—Ni2—N2i | 101.67 (8) | C10—C11—H11A | 119.7 |
O2i—Ni2—N2 | 101.67 (8) | C11—C12—C13 | 120.4 (4) |
O2—Ni2—N2 | 78.33 (8) | C11—C12—H12A | 119.8 |
N2i—Ni2—N2 | 180.00 (12) | C13—C12—H12A | 119.8 |
O2i—Ni2—O5i | 91.17 (9) | C12—C13—C14 | 118.6 (4) |
O2—Ni2—O5i | 88.83 (9) | C12—C13—H13A | 120.7 |
N2i—Ni2—O5i | 91.58 (9) | C14—C13—H13A | 120.7 |
N2—Ni2—O5i | 88.42 (9) | C15—C14—C13 | 122.1 (4) |
O2i—Ni2—O5 | 88.83 (9) | C15—C14—H14A | 119.0 |
O2—Ni2—O5 | 91.17 (9) | C13—C14—H14A | 119.0 |
N2i—Ni2—O5 | 88.42 (9) | C14—C15—C10 | 118.5 (3) |
N2—Ni2—O5 | 91.58 (9) | C14—C15—H15A | 120.7 |
O5i—Ni2—O5 | 180.00 (6) | C10—C15—H15A | 120.7 |
C1—O1—Ni1 | 126.76 (18) | N3—C16—N4 | 110.5 (3) |
C7—O2—Ni2 | 114.01 (16) | N3—C16—H16A | 124.8 |
C8—O3—Ni1 | 110.19 (16) | N4—C16—H16A | 124.8 |
C10—O4—C9 | 118.7 (2) | C18—C17—N4 | 106.0 (3) |
Ni2—O5—H5B | 112 (3) | C18—C17—H17A | 127.0 |
Ni2—O5—H5C | 115 (2) | N4—C17—H17A | 127.0 |
H5B—O5—H5C | 105 (3) | C17—C18—N3 | 109.5 (3) |
C7—N1—N2 | 113.5 (2) | C17—C18—H18A | 125.2 |
C7—N1—Ni1 | 132.28 (19) | N3—C18—H18A | 125.2 |
N2—N1—Ni1 | 114.14 (15) | C19—N5—C20 | 119.1 (3) |
C8—N2—N1 | 108.6 (2) | C19—N5—C21 | 122.9 (3) |
C8—N2—Ni2 | 139.81 (19) | C20—N5—C21 | 117.8 (3) |
N1—N2—Ni2 | 111.55 (15) | O6—C19—N5 | 126.2 (3) |
C16—N3—C18 | 105.7 (3) | O6—C19—H19A | 116.9 |
C16—N3—Ni1 | 127.8 (2) | N5—C19—H19A | 116.9 |
C18—N3—Ni1 | 126.6 (2) | N5—C20—H20A | 109.5 |
C16—N4—C17 | 108.3 (2) | N5—C20—H20B | 109.5 |
C16—N4—H4B | 125.8 | H20A—C20—H20B | 109.5 |
C17—N4—H4B | 125.8 | N5—C20—H20C | 109.5 |
O1—C1—C2 | 125.3 (2) | H20A—C20—H20C | 109.5 |
O1—C1—C6 | 116.6 (3) | H20B—C20—H20C | 109.5 |
C2—C1—C6 | 118.1 (2) | N5—C21—H21A | 109.5 |
C1—C2—C3 | 119.2 (2) | N5—C21—H21B | 109.5 |
C1—C2—C7 | 123.8 (2) | H21A—C21—H21B | 109.5 |
C3—C2—C7 | 117.0 (2) | N5—C21—H21C | 109.5 |
C4—C3—C2 | 121.5 (3) | H21A—C21—H21C | 109.5 |
C4—C3—H3A | 119.2 | H21B—C21—H21C | 109.5 |
C2—C3—H3A | 119.2 | C22—N6—C23 | 120.4 (4) |
C3—C4—C5 | 119.0 (3) | C22—N6—C24 | 120.5 (3) |
C3—C4—H4A | 120.5 | C23—N6—C24 | 118.7 (3) |
C5—C4—H4A | 120.5 | O7—C22—N6 | 125.3 (4) |
C6—C5—C4 | 121.0 (3) | O7—C22—H22A | 117.4 |
C6—C5—H5A | 119.5 | N6—C22—H22A | 117.4 |
C4—C5—H5A | 119.5 | N6—C23—H23A | 109.5 |
C5—C6—C1 | 121.1 (3) | N6—C23—H23B | 109.5 |
C5—C6—H6A | 119.4 | H23A—C23—H23B | 109.5 |
C1—C6—H6A | 119.4 | N6—C23—H23C | 109.5 |
O2—C7—N1 | 121.7 (2) | H23A—C23—H23C | 109.5 |
O2—C7—C2 | 121.2 (2) | H23B—C23—H23C | 109.5 |
N1—C7—C2 | 117.1 (2) | N6—C24—H24A | 109.5 |
O3—C8—N2 | 122.6 (2) | N6—C24—H24B | 109.5 |
O3—C8—C9 | 119.1 (2) | H24A—C24—H24B | 109.5 |
N2—C8—C9 | 118.2 (2) | N6—C24—H24C | 109.5 |
O4—C9—C8 | 113.7 (2) | H24A—C24—H24C | 109.5 |
O4—C9—H9A | 108.8 | H24B—C24—H24C | 109.5 |
C8—C9—H9A | 108.8 | | |
| | | |
N1—Ni1—O1—C1 | −0.3 (2) | C2—C3—C4—C5 | −0.4 (5) |
O3—Ni1—O1—C1 | 28 (4) | C3—C4—C5—C6 | 0.4 (5) |
N3—Ni1—O1—C1 | 180.0 (2) | C4—C5—C6—C1 | −0.4 (5) |
O2i—Ni2—O2—C7 | −111 (100) | O1—C1—C6—C5 | −179.1 (3) |
N2i—Ni2—O2—C7 | 171.37 (19) | C2—C1—C6—C5 | 0.5 (5) |
N2—Ni2—O2—C7 | −8.63 (19) | Ni2—O2—C7—N1 | 8.3 (3) |
O5i—Ni2—O2—C7 | 80.0 (2) | Ni2—O2—C7—C2 | −170.6 (2) |
O5—Ni2—O2—C7 | −100.0 (2) | N2—N1—C7—O2 | −1.3 (4) |
O1—Ni1—O3—C8 | −29 (4) | Ni1—N1—C7—O2 | 174.7 (2) |
N1—Ni1—O3—C8 | −1.22 (19) | N2—N1—C7—C2 | 177.7 (2) |
N3—Ni1—O3—C8 | 178.5 (2) | Ni1—N1—C7—C2 | −6.3 (4) |
O1—Ni1—N1—C7 | 5.1 (3) | C1—C2—C7—O2 | −178.9 (3) |
O3—Ni1—N1—C7 | −174.3 (3) | C3—C2—C7—O2 | 4.3 (4) |
N3—Ni1—N1—C7 | −179 (67) | C1—C2—C7—N1 | 2.1 (4) |
O1—Ni1—N1—N2 | −178.89 (18) | C3—C2—C7—N1 | −174.7 (3) |
O3—Ni1—N1—N2 | 1.71 (18) | Ni1—O3—C8—N2 | 0.5 (4) |
N3—Ni1—N1—N2 | −2.7 (17) | Ni1—O3—C8—C9 | 176.8 (2) |
C7—N1—N2—C8 | 175.0 (2) | N1—N2—C8—O3 | 0.8 (4) |
Ni1—N1—N2—C8 | −1.8 (3) | Ni2—N2—C8—O3 | −177.6 (2) |
C7—N1—N2—Ni2 | −6.2 (3) | N1—N2—C8—C9 | −175.5 (2) |
Ni1—N1—N2—Ni2 | 177.09 (11) | Ni2—N2—C8—C9 | 6.1 (5) |
O2i—Ni2—N2—C8 | 6.1 (3) | C10—O4—C9—C8 | 75.6 (3) |
O2—Ni2—N2—C8 | −173.9 (3) | O3—C8—C9—O4 | 45.5 (4) |
N2i—Ni2—N2—C8 | −170 (100) | N2—C8—C9—O4 | −138.0 (3) |
O5i—Ni2—N2—C8 | 97.0 (3) | C9—O4—C10—C11 | 173.5 (3) |
O5—Ni2—N2—C8 | −83.0 (3) | C9—O4—C10—C15 | −6.8 (4) |
O2i—Ni2—N2—N1 | −172.25 (17) | O4—C10—C11—C12 | 178.9 (3) |
O2—Ni2—N2—N1 | 7.75 (17) | C15—C10—C11—C12 | −0.9 (5) |
N2i—Ni2—N2—N1 | 12 (100) | C10—C11—C12—C13 | 0.0 (6) |
O5i—Ni2—N2—N1 | −81.38 (18) | C11—C12—C13—C14 | 0.5 (6) |
O5—Ni2—N2—N1 | 98.62 (18) | C12—C13—C14—C15 | 0.0 (6) |
O1—Ni1—N3—C16 | −166.9 (3) | C13—C14—C15—C10 | −0.9 (5) |
N1—Ni1—N3—C16 | 16.9 (18) | O4—C10—C15—C14 | −178.4 (3) |
O3—Ni1—N3—C16 | 12.5 (3) | C11—C10—C15—C14 | 1.3 (5) |
O1—Ni1—N3—C18 | 12.7 (3) | C18—N3—C16—N4 | −0.9 (4) |
N1—Ni1—N3—C18 | −163.4 (15) | Ni1—N3—C16—N4 | 178.8 (2) |
O3—Ni1—N3—C18 | −167.8 (3) | C17—N4—C16—N3 | 0.7 (4) |
Ni1—O1—C1—C2 | −2.8 (4) | C16—N4—C17—C18 | −0.1 (4) |
Ni1—O1—C1—C6 | 176.6 (2) | N4—C17—C18—N3 | −0.4 (5) |
O1—C1—C2—C3 | 179.0 (3) | C16—N3—C18—C17 | 0.8 (4) |
C6—C1—C2—C3 | −0.5 (4) | Ni1—N3—C18—C17 | −178.9 (3) |
O1—C1—C2—C7 | 2.3 (5) | C20—N5—C19—O6 | 1.8 (5) |
C6—C1—C2—C7 | −177.2 (3) | C21—N5—C19—O6 | 178.6 (3) |
C1—C2—C3—C4 | 0.5 (5) | C23—N6—C22—O7 | 175.5 (4) |
C7—C2—C3—C4 | 177.4 (3) | C24—N6—C22—O7 | 2.9 (6) |
Symmetry code: (i) −x+1, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5B···O7 | 0.83 (2) | 1.90 (2) | 2.727 (4) | 171 (4) |
O5—H5C···O6 | 0.81 (2) | 1.98 (2) | 2.777 (3) | 171 (3) |
N4—H4B···O6ii | 0.86 | 2.05 | 2.897 (4) | 170 |
C16—H16A···O7ii | 0.93 | 2.42 | 3.232 (4) | 146 |
C22—H22A···O4ii | 0.93 | 2.52 | 3.262 (4) | 137 |
C9—H9A···O2i | 0.97 | 2.28 | 3.200 (4) | 159 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1. |
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