metal-organic compounds
The title compound, [Ni3(C17H20N2O2)2(C2H3O2)2(C3H7NO)2]·2C3H7NO, is a centrosymmetric trinuclear nickel(II) complex. The central and terminal nickel(II) atoms have distorted octahedral coordination, the central NiII atom by six O atoms, and the terminal NiII atoms by four O atoms and two N atoms each. The average Ni—O and Ni—N distances for the terminal Ni ions are 2.062 (17) and 2.082 (2) Å, respectively. The NiNi distance is 3.035 (2) Å.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005976/cf2005sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005976/cf2005Isup2.hkl |
CCDC reference: 601131
Computing details top
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1993); cell refinement: CAD-4 EXPRESS; data reduction: X-RED (Stoe & Cie, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
Bis{[µ-N,N'-bis(2-hydroxybenzyl)-2-hydroxy-1,3
propandiaminato](acetato)
(N,N'-dimethylformamide)nickel(II)}nickel(II) top
Crystal data top
[(C44H60N6Ni3O12)].2C3H7NO | Z = 1 |
Mr = 1187.24 | F(000) = 626 |
Triclinic, P1 | Dx = 1.396 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.373 (3) Å | Cell parameters from 25 reflections |
b = 12.125 (1) Å | θ = 1.8–26.0° |
c = 12.863 (1) Å | µ = 1.06 mm−1 |
α = 107.99 (1)° | T = 300 K |
β = 107.99 (1)° | Prism, blue |
γ = 98.18 (1)° | 0.40 × 0.13 × 0.10 mm |
V = 1412.1 (5) Å3 |
Data collection top
Enraf-Nonius CAD-4 diffractometer | 4342 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed X-ray tube | Rint = 0.0 |
Graphite monochromator | θmax = 26.0°, θmin = 1.8° |
ω/2θ scans | h = −12→11 |
Absorption correction: ψ scan ψ scan (Fair, 1990) | k = −14→14 |
Tmin = 0.848, Tmax = 0.900 | l = 0→15 |
5524 measured reflections | 3 standard reflections every 120 min |
5524 independent reflections | intensity decay: 1.5% |
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)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0558P)2 + 0.5368P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
5524 reflections | Δρmax = 0.52 e Å−3 |
356 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
C1 | 0.2252 (2) | 0.1753 (2) | 0.4682 (2) | 0.0342 (5) | |
C2 | 0.3260 (3) | 0.1106 (3) | 0.4832 (3) | 0.0461 (6) | |
H2 | 0.3059 | 0.0394 | 0.4953 | 0.055* | |
C3 | 0.4562 (3) | 0.1519 (3) | 0.4801 (3) | 0.0589 (8) | |
H3 | 0.5224 | 0.1079 | 0.4904 | 0.071* | |
C4 | 0.4886 (3) | 0.2560 (3) | 0.4623 (3) | 0.0630 (9) | |
H4 | 0.5751 | 0.2817 | 0.4582 | 0.076* | |
C5 | 0.3918 (3) | 0.3224 (3) | 0.4504 (3) | 0.0546 (7) | |
H5 | 0.4143 | 0.3940 | 0.4395 | 0.066* | |
C6 | 0.2607 (3) | 0.2845 (2) | 0.4544 (2) | 0.0397 (6) | |
C7 | 0.1600 (3) | 0.3625 (2) | 0.4521 (3) | 0.0459 (6) | |
H7A | 0.1403 | 0.3798 | 0.5236 | 0.055* | |
H7B | 0.2047 | 0.4382 | 0.4516 | 0.055* | |
C8 | −0.0569 (3) | 0.3958 (2) | 0.3421 (3) | 0.0513 (7) | |
H8A | −0.0002 | 0.4660 | 0.3410 | 0.062* | |
H8B | −0.0796 | 0.4211 | 0.4121 | 0.062* | |
C9 | −0.1926 (3) | 0.3468 (3) | 0.2334 (3) | 0.0490 (7) | |
H9 | −0.2320 | 0.4143 | 0.2268 | 0.059* | |
C10 | −0.3015 (3) | 0.2552 (3) | 0.2392 (2) | 0.0458 (6) | |
H10A | −0.3102 | 0.2857 | 0.3152 | 0.055* | |
H10B | −0.3916 | 0.2430 | 0.1789 | 0.055* | |
C11 | −0.3831 (3) | 0.0472 (3) | 0.2142 (2) | 0.0454 (6) | |
H11A | −0.4694 | 0.0467 | 0.1562 | 0.054* | |
H11B | −0.3938 | 0.0693 | 0.2896 | 0.054* | |
C12 | −0.3631 (3) | −0.0765 (2) | 0.1808 (2) | 0.0407 (6) | |
C13 | −0.4583 (3) | −0.1684 (3) | 0.0788 (3) | 0.0579 (8) | |
H13 | −0.5307 | −0.1506 | 0.0283 | 0.069* | |
C14 | −0.4485 (4) | −0.2846 (3) | 0.0507 (3) | 0.0704 (10) | |
H14 | −0.5125 | −0.3448 | −0.0187 | 0.084* | |
C15 | −0.3424 (3) | −0.3109 (3) | 0.1269 (3) | 0.0647 (9) | |
H15 | −0.3358 | −0.3898 | 0.1092 | 0.078* | |
C16 | −0.2455 (3) | −0.2214 (2) | 0.2295 (3) | 0.0504 (7) | |
H16 | −0.1758 | −0.2410 | 0.2807 | 0.061* | |
C17 | −0.2517 (2) | −0.1022 (2) | 0.2567 (2) | 0.0362 (5) | |
C18 | −0.1170 (2) | 0.2176 (2) | 0.5754 (2) | 0.0336 (5) | |
C19 | −0.1459 (4) | 0.3059 (3) | 0.6718 (3) | 0.0555 (8) | |
H19A | −0.2282 | 0.2682 | 0.6799 | 0.083* | |
H19B | −0.1610 | 0.3744 | 0.6520 | 0.083* | |
H19C | −0.0670 | 0.3314 | 0.7448 | 0.083* | |
C20 | 0.0522 (3) | −0.0066 (3) | 0.2061 (2) | 0.0434 (6) | |
H20 | 0.042 (3) | −0.063 (3) | 0.239 (3) | 0.052* | |
C21 | 0.1896 (4) | 0.0686 (4) | 0.1101 (4) | 0.0752 (10) | |
H21A | 0.2261 | 0.1476 | 0.1706 | 0.090* | |
H21B | 0.1096 | 0.0674 | 0.0471 | 0.090* | |
H21C | 0.2608 | 0.0475 | 0.0805 | 0.090* | |
C22 | 0.2276 (5) | −0.1048 (4) | 0.1663 (4) | 0.0904 (13) | |
H22A | 0.3243 | −0.0644 | 0.2151 | 0.136* | |
H22B | 0.2209 | −0.1525 | 0.0888 | 0.136* | |
H22C | 0.1904 | −0.1559 | 0.2000 | 0.136* | |
C23 | −0.2527 (7) | 0.4419 (6) | −0.0712 (6) | 0.121 (2) | |
H23 | −0.3247 | 0.3713 | −0.1118 | 0.145* | |
C24 | −0.3784 (11) | 0.4995 (10) | −0.2248 (7) | 0.242 (6) | |
H24A | −0.4632 | 0.4915 | −0.2090 | 0.291* | |
H24B | −0.3850 | 0.4274 | −0.2867 | 0.291* | |
H24C | −0.3655 | 0.5665 | −0.2487 | 0.291* | |
C25 | −0.1574 (9) | 0.6274 (8) | −0.0699 (10) | 0.224 (6) | |
H25C | −0.1789 | 0.6741 | −0.1180 | 0.269* | |
H25B | −0.0680 | 0.6114 | −0.0646 | 0.269* | |
H25A | −0.1538 | 0.6712 | 0.0076 | 0.269* | |
N1 | −0.2663 (2) | 0.1395 (2) | 0.22258 (19) | 0.0375 (5) | |
N2 | 0.0254 (2) | 0.30725 (19) | 0.3489 (2) | 0.0386 (5) | |
N3 | 0.1482 (2) | −0.0169 (2) | 0.1586 (2) | 0.0492 (6) | |
N4 | −0.2611 (6) | 0.5190 (5) | −0.1203 (4) | 0.1183 (18) | |
O1 | 0.09779 (16) | 0.13624 (15) | 0.46627 (15) | 0.0335 (4) | |
O2 | −0.15778 (16) | −0.01314 (15) | 0.35182 (14) | 0.0348 (4) | |
O3 | −0.07922 (17) | 0.12989 (15) | 0.59423 (15) | 0.0363 (4) | |
O4 | −0.13317 (18) | 0.24065 (16) | 0.48391 (15) | 0.0393 (4) | |
O5 | −0.01479 (19) | 0.06959 (17) | 0.20482 (16) | 0.0452 (4) | |
O6 | −0.1650 (3) | 0.2953 (2) | 0.1308 (2) | 0.0698 (6) | |
H6A | −0.169 (4) | 0.365 (3) | 0.092 (3) | 0.084* | |
O7 | −0.1694 (4) | 0.4448 (4) | 0.0165 (4) | 0.1244 (14) | |
Ni1 | −0.07870 (3) | 0.14768 (3) | 0.34931 (3) | 0.03056 (10) | |
Ni2 | 0.0000 | 0.0000 | 0.5000 | 0.02874 (11) | |
H1' | −0.252 (3) | 0.120 (2) | 0.162 (3) | 0.037 (7)* | |
H2' | 0.041 (3) | 0.287 (2) | 0.289 (3) | 0.040 (8)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0246 (11) | 0.0415 (13) | 0.0345 (12) | 0.0058 (10) | 0.0102 (10) | 0.0139 (10) |
C2 | 0.0309 (13) | 0.0522 (16) | 0.0616 (18) | 0.0161 (12) | 0.0192 (12) | 0.0256 (14) |
C3 | 0.0299 (14) | 0.072 (2) | 0.078 (2) | 0.0180 (14) | 0.0233 (14) | 0.0272 (18) |
C4 | 0.0308 (15) | 0.087 (2) | 0.077 (2) | 0.0075 (15) | 0.0266 (15) | 0.0348 (19) |
C5 | 0.0393 (15) | 0.0611 (18) | 0.0612 (19) | −0.0022 (13) | 0.0160 (14) | 0.0297 (15) |
C6 | 0.0305 (12) | 0.0443 (14) | 0.0423 (14) | 0.0045 (11) | 0.0118 (11) | 0.0177 (12) |
C7 | 0.0434 (15) | 0.0365 (14) | 0.0541 (16) | 0.0066 (11) | 0.0121 (13) | 0.0201 (12) |
C8 | 0.0558 (17) | 0.0423 (15) | 0.0604 (18) | 0.0185 (13) | 0.0176 (14) | 0.0268 (14) |
C9 | 0.0592 (17) | 0.0577 (17) | 0.0483 (16) | 0.0331 (14) | 0.0225 (14) | 0.0334 (14) |
C10 | 0.0449 (15) | 0.0594 (17) | 0.0419 (14) | 0.0304 (13) | 0.0149 (12) | 0.0244 (13) |
C11 | 0.0251 (12) | 0.0666 (18) | 0.0481 (15) | 0.0177 (12) | 0.0109 (11) | 0.0266 (14) |
C12 | 0.0272 (12) | 0.0540 (16) | 0.0374 (13) | 0.0076 (11) | 0.0096 (10) | 0.0162 (12) |
C13 | 0.0366 (15) | 0.072 (2) | 0.0454 (16) | 0.0067 (14) | 0.0010 (12) | 0.0139 (15) |
C14 | 0.054 (2) | 0.071 (2) | 0.0493 (18) | 0.0001 (17) | −0.0001 (15) | 0.0012 (16) |
C15 | 0.058 (2) | 0.0467 (17) | 0.069 (2) | 0.0085 (15) | 0.0154 (17) | 0.0060 (15) |
C16 | 0.0377 (14) | 0.0469 (16) | 0.0568 (17) | 0.0094 (12) | 0.0106 (13) | 0.0142 (13) |
C17 | 0.0269 (12) | 0.0430 (14) | 0.0344 (13) | 0.0051 (10) | 0.0101 (10) | 0.0120 (11) |
C18 | 0.0260 (11) | 0.0400 (13) | 0.0374 (13) | 0.0097 (10) | 0.0135 (10) | 0.0162 (11) |
C19 | 0.074 (2) | 0.0586 (18) | 0.0533 (17) | 0.0313 (16) | 0.0386 (16) | 0.0247 (15) |
C20 | 0.0497 (16) | 0.0479 (15) | 0.0417 (15) | 0.0172 (13) | 0.0252 (13) | 0.0188 (12) |
C21 | 0.067 (2) | 0.101 (3) | 0.090 (3) | 0.028 (2) | 0.050 (2) | 0.054 (2) |
C22 | 0.101 (3) | 0.097 (3) | 0.129 (4) | 0.067 (3) | 0.082 (3) | 0.061 (3) |
C23 | 0.170 (6) | 0.158 (5) | 0.138 (5) | 0.115 (5) | 0.116 (5) | 0.101 (4) |
C24 | 0.330 (13) | 0.406 (14) | 0.135 (6) | 0.295 (12) | 0.136 (8) | 0.154 (8) |
C25 | 0.211 (9) | 0.252 (10) | 0.438 (17) | 0.143 (8) | 0.238 (11) | 0.278 (12) |
N1 | 0.0350 (11) | 0.0516 (13) | 0.0337 (11) | 0.0190 (10) | 0.0149 (9) | 0.0209 (10) |
N2 | 0.0421 (12) | 0.0409 (12) | 0.0396 (12) | 0.0149 (10) | 0.0162 (10) | 0.0213 (10) |
N3 | 0.0505 (14) | 0.0594 (15) | 0.0540 (14) | 0.0242 (12) | 0.0335 (12) | 0.0243 (12) |
N4 | 0.176 (4) | 0.175 (4) | 0.132 (3) | 0.134 (4) | 0.120 (4) | 0.124 (4) |
O1 | 0.0227 (8) | 0.0408 (9) | 0.0430 (9) | 0.0093 (7) | 0.0129 (7) | 0.0228 (8) |
O2 | 0.0278 (8) | 0.0379 (9) | 0.0345 (9) | 0.0068 (7) | 0.0046 (7) | 0.0157 (7) |
O3 | 0.0364 (9) | 0.0424 (10) | 0.0380 (9) | 0.0149 (8) | 0.0177 (7) | 0.0197 (8) |
O4 | 0.0423 (10) | 0.0477 (10) | 0.0405 (10) | 0.0238 (8) | 0.0202 (8) | 0.0229 (8) |
O5 | 0.0474 (11) | 0.0566 (11) | 0.0434 (10) | 0.0257 (9) | 0.0238 (9) | 0.0221 (9) |
O6 | 0.0927 (18) | 0.0818 (16) | 0.0644 (14) | 0.0410 (14) | 0.0414 (13) | 0.0461 (13) |
O7 | 0.151 (3) | 0.164 (3) | 0.159 (3) | 0.090 (3) | 0.098 (3) | 0.132 (3) |
Ni1 | 0.02683 (16) | 0.03788 (18) | 0.03269 (17) | 0.01335 (13) | 0.01192 (13) | 0.01779 (13) |
Ni2 | 0.0234 (2) | 0.0350 (2) | 0.0318 (2) | 0.00978 (17) | 0.01017 (17) | 0.01697 (18) |
Geometric parameters (Å, º) top
C1—O1 | 1.329 (3) | C18—C19 | 1.509 (4) |
C1—C2 | 1.396 (3) | C19—H19A | 0.960 |
C1—C6 | 1.402 (3) | C19—H19B | 0.960 |
C2—C3 | 1.388 (4) | C19—H19C | 0.960 |
C2—H2 | 0.930 | C20—O5 | 1.234 (3) |
C3—C4 | 1.366 (4) | C20—N3 | 1.320 (3) |
C3—H3 | 0.930 | C20—H20 | 0.92 (3) |
C4—C5 | 1.375 (5) | C21—N3 | 1.444 (4) |
C4—H4 | 0.930 | C21—H21A | 0.960 |
C5—C6 | 1.395 (4) | C21—H21B | 0.960 |
C5—H5 | 0.930 | C21—H21C | 0.960 |
C6—C7 | 1.504 (4) | C22—N3 | 1.445 (4) |
C7—N2 | 1.484 (3) | C22—H22A | 0.960 |
C7—H7A | 0.970 | C22—H22B | 0.960 |
C7—H7B | 0.970 | C22—H22C | 0.960 |
C8—N2 | 1.471 (3) | C23—O7 | 1.177 (7) |
C8—C9 | 1.525 (4) | C23—N4 | 1.279 (6) |
C8—H8A | 0.970 | C23—H23 | 0.930 |
C8—H8B | 0.970 | C24—N4 | 1.435 (9) |
C9—O6 | 1.411 (4) | C24—H24A | 0.960 |
C9—C10 | 1.504 (4) | C24—H24B | 0.960 |
C9—H9 | 0.980 | C24—H24C | 0.960 |
C10—N1 | 1.468 (3) | C25—N4 | 1.395 (9) |
C10—H10A | 0.970 | C25—H25C | 0.960 |
C10—H10B | 0.970 | C25—H25B | 0.960 |
C11—N1 | 1.480 (3) | C25—H25A | 0.960 |
C11—C12 | 1.491 (4) | N1—Ni1 | 2.084 (2) |
C11—H11A | 0.970 | N1—H1' | 0.81 (3) |
C11—H11B | 0.970 | N2—Ni1 | 2.080 (2) |
C12—C13 | 1.387 (4) | N2—H2' | 0.81 (3) |
C12—C17 | 1.408 (3) | O1—Ni1 | 2.0339 (16) |
C13—C14 | 1.369 (5) | O1—Ni2 | 2.0453 (15) |
C13—H13 | 0.930 | O2—Ni1 | 2.0189 (16) |
C14—C15 | 1.380 (5) | O2—Ni2 | 2.0374 (16) |
C14—H14 | 0.930 | O3—Ni2 | 2.1044 (16) |
C15—C16 | 1.384 (4) | O4—Ni1 | 2.0412 (17) |
C15—H15 | 0.930 | O5—Ni1 | 2.1545 (18) |
C16—C17 | 1.394 (4) | O6—H6A | 1.11 (4) |
C16—H16 | 0.930 | Ni2—O2i | 2.0374 (16) |
C17—O2 | 1.327 (3) | Ni2—O1i | 2.0453 (15) |
C18—O3 | 1.250 (3) | Ni2—O3i | 2.1044 (16) |
C18—O4 | 1.259 (3) | ||
O1—C1—C2 | 122.0 (2) | H21A—C21—H21C | 109.5 |
O1—C1—C6 | 119.6 (2) | H21B—C21—H21C | 109.5 |
C2—C1—C6 | 118.4 (2) | N3—C22—H22A | 109.5 |
C3—C2—C1 | 120.4 (3) | N3—C22—H22B | 109.5 |
C3—C2—H2 | 119.8 | H22A—C22—H22B | 109.5 |
C1—C2—H2 | 119.8 | N3—C22—H22C | 109.5 |
C4—C3—C2 | 121.1 (3) | H22A—C22—H22C | 109.5 |
C4—C3—H3 | 119.5 | H22B—C22—H22C | 109.5 |
C2—C3—H3 | 119.5 | O7—C23—N4 | 131.1 (7) |
C3—C4—C5 | 119.2 (3) | O7—C23—H23 | 114.5 |
C3—C4—H4 | 120.4 | N4—C23—H23 | 114.5 |
C5—C4—H4 | 120.4 | N4—C24—H24A | 109.5 |
C4—C5—C6 | 121.3 (3) | N4—C24—H24B | 109.5 |
C4—C5—H5 | 119.3 | H24A—C24—H24B | 109.5 |
C6—C5—H5 | 119.3 | N4—C24—H24C | 109.5 |
C5—C6—C1 | 119.5 (3) | H24A—C24—H24C | 109.5 |
C5—C6—C7 | 121.1 (3) | H24B—C24—H24C | 109.5 |
C1—C6—C7 | 119.3 (2) | N4—C25—H25C | 109.5 |
N2—C7—C6 | 113.6 (2) | N4—C25—H25B | 109.5 |
N2—C7—H7A | 108.8 | H25C—C25—H25B | 109.5 |
C6—C7—H7A | 108.8 | N4—C25—H25A | 109.5 |
N2—C7—H7B | 108.8 | H25C—C25—H25A | 109.5 |
C6—C7—H7B | 108.8 | H25B—C25—H25A | 109.5 |
H7A—C7—H7B | 107.7 | C10—N1—C11 | 111.0 (2) |
N2—C8—C9 | 112.8 (2) | C10—N1—Ni1 | 114.39 (17) |
N2—C8—H8A | 109.0 | C11—N1—Ni1 | 110.44 (15) |
C9—C8—H8A | 109.0 | C10—N1—H1' | 106.9 (19) |
N2—C8—H8B | 109.0 | C11—N1—H1' | 110.0 (19) |
C9—C8—H8B | 109.0 | Ni1—N1—H1' | 104 (2) |
H8A—C8—H8B | 107.8 | C8—N2—C7 | 110.3 (2) |
O6—C9—C10 | 108.9 (2) | C8—N2—Ni1 | 115.29 (17) |
O6—C9—C8 | 110.4 (2) | C7—N2—Ni1 | 110.42 (16) |
C10—C9—C8 | 113.3 (2) | C8—N2—H2' | 107 (2) |
O6—C9—H9 | 108.0 | C7—N2—H2' | 110 (2) |
C10—C9—H9 | 108.0 | Ni1—N2—H2' | 104 (2) |
C8—C9—H9 | 108.0 | C20—N3—C21 | 121.0 (3) |
N1—C10—C9 | 112.3 (2) | C20—N3—C22 | 121.1 (3) |
N1—C10—H10A | 109.1 | C21—N3—C22 | 117.4 (3) |
C9—C10—H10A | 109.1 | C23—N4—C25 | 120.1 (6) |
N1—C10—H10B | 109.1 | C23—N4—C24 | 121.6 (8) |
C9—C10—H10B | 109.1 | C25—N4—C24 | 118.2 (6) |
H10A—C10—H10B | 107.9 | C1—O1—Ni1 | 122.38 (14) |
N1—C11—C12 | 113.9 (2) | C1—O1—Ni2 | 135.92 (15) |
N1—C11—H11A | 108.8 | Ni1—O1—Ni2 | 96.17 (7) |
C12—C11—H11A | 108.8 | C17—O2—Ni1 | 122.60 (15) |
N1—C11—H11B | 108.8 | C17—O2—Ni2 | 135.79 (15) |
C12—C11—H11B | 108.8 | Ni1—O2—Ni2 | 96.89 (7) |
H11A—C11—H11B | 107.7 | C18—O3—Ni2 | 130.82 (15) |
C13—C12—C17 | 119.5 (3) | C18—O4—Ni1 | 123.88 (16) |
C13—C12—C11 | 120.5 (2) | C20—O5—Ni1 | 120.68 (17) |
C17—C12—C11 | 119.9 (2) | C9—O6—H6A | 103.1 (19) |
C14—C13—C12 | 121.7 (3) | O2—Ni1—O1 | 81.90 (6) |
C14—C13—H13 | 119.1 | O2—Ni1—O4 | 93.19 (7) |
C12—C13—H13 | 119.1 | O1—Ni1—O4 | 90.77 (7) |
C13—C14—C15 | 119.0 (3) | O2—Ni1—N2 | 173.05 (8) |
C13—C14—H14 | 120.5 | O1—Ni1—N2 | 92.44 (8) |
C15—C14—H14 | 120.5 | O4—Ni1—N2 | 90.90 (8) |
C14—C15—C16 | 120.9 (3) | O2—Ni1—N1 | 92.57 (8) |
C14—C15—H15 | 119.6 | O1—Ni1—N1 | 173.91 (8) |
C16—C15—H15 | 119.6 | O4—Ni1—N1 | 92.09 (8) |
C15—C16—C17 | 120.5 (3) | N2—Ni1—N1 | 92.90 (9) |
C15—C16—H16 | 119.7 | O2—Ni1—O5 | 93.57 (7) |
C17—C16—H16 | 119.7 | O1—Ni1—O5 | 91.17 (7) |
O2—C17—C16 | 122.5 (2) | O4—Ni1—O5 | 173.17 (7) |
O2—C17—C12 | 119.2 (2) | N2—Ni1—O5 | 82.47 (9) |
C16—C17—C12 | 118.3 (2) | N1—Ni1—O5 | 86.61 (8) |
O3—C18—O4 | 126.8 (2) | O2i—Ni2—O2 | 180.0 |
O3—C18—C19 | 117.2 (2) | O2i—Ni2—O1 | 98.83 (7) |
O4—C18—C19 | 116.1 (2) | O2—Ni2—O1 | 81.17 (6) |
C18—C19—H19A | 109.5 | O2i—Ni2—O1i | 81.17 (6) |
C18—C19—H19B | 109.5 | O2—Ni2—O1i | 98.83 (7) |
H19A—C19—H19B | 109.5 | O1—Ni2—O1i | 180.00 (6) |
C18—C19—H19C | 109.5 | O2i—Ni2—O3i | 86.69 (7) |
H19A—C19—H19C | 109.5 | O2—Ni2—O3i | 93.31 (7) |
H19B—C19—H19C | 109.5 | O1—Ni2—O3i | 94.15 (7) |
O5—C20—N3 | 123.3 (3) | O1i—Ni2—O3i | 85.85 (7) |
O5—C20—H20 | 125.3 (19) | O2i—Ni2—O3 | 93.31 (7) |
N3—C20—H20 | 111.4 (19) | O2—Ni2—O3 | 86.69 (7) |
N3—C21—H21A | 109.5 | O1—Ni2—O3 | 85.85 (7) |
N3—C21—H21B | 109.5 | O1i—Ni2—O3 | 94.15 (7) |
H21A—C21—H21B | 109.5 | O3i—Ni2—O3 | 180.00 (9) |
N3—C21—H21C | 109.5 | ||
O1—C1—C2—C3 | 177.5 (3) | Ni2—O2—Ni1—O4 | −75.36 (7) |
C6—C1—C2—C3 | −2.3 (4) | C17—O2—Ni1—N1 | 33.29 (18) |
C1—C2—C3—C4 | −0.1 (5) | Ni2—O2—Ni1—N1 | −167.59 (8) |
C2—C3—C4—C5 | 1.8 (5) | C17—O2—Ni1—O5 | −53.47 (18) |
C3—C4—C5—C6 | −1.0 (5) | Ni2—O2—Ni1—O5 | 105.65 (7) |
C4—C5—C6—C1 | −1.4 (4) | C1—O1—Ni1—O2 | 142.66 (18) |
C4—C5—C6—C7 | 174.6 (3) | Ni2—O1—Ni1—O2 | −14.89 (7) |
O1—C1—C6—C5 | −176.8 (2) | C1—O1—Ni1—O4 | −124.23 (18) |
C2—C1—C6—C5 | 3.0 (4) | Ni2—O1—Ni1—O4 | 78.22 (7) |
O1—C1—C6—C7 | 7.1 (4) | C1—O1—Ni1—N2 | −33.29 (19) |
C2—C1—C6—C7 | −173.1 (3) | Ni2—O1—Ni1—N2 | 169.16 (8) |
C5—C6—C7—N2 | 118.6 (3) | C1—O1—Ni1—O5 | 49.22 (18) |
C1—C6—C7—N2 | −65.3 (3) | Ni2—O1—Ni1—O5 | −108.33 (7) |
N2—C8—C9—O6 | −51.2 (3) | C18—O4—Ni1—O2 | 42.82 (19) |
N2—C8—C9—C10 | 71.3 (3) | C18—O4—Ni1—O1 | −39.10 (19) |
O6—C9—C10—N1 | 50.1 (3) | C18—O4—Ni1—N2 | −131.55 (19) |
C8—C9—C10—N1 | −73.3 (3) | C18—O4—Ni1—N1 | 135.51 (19) |
N1—C11—C12—C13 | −119.7 (3) | C8—N2—Ni1—O1 | −142.47 (19) |
N1—C11—C12—C17 | 64.3 (3) | C7—N2—Ni1—O1 | −16.68 (18) |
C17—C12—C13—C14 | 1.2 (5) | C8—N2—Ni1—O4 | −51.7 (2) |
C11—C12—C13—C14 | −174.9 (3) | C7—N2—Ni1—O4 | 74.13 (18) |
C12—C13—C14—C15 | 1.0 (6) | C8—N2—Ni1—N1 | 40.5 (2) |
C13—C14—C15—C16 | −1.0 (6) | C7—N2—Ni1—N1 | 166.27 (18) |
C14—C15—C16—C17 | −1.3 (5) | C8—N2—Ni1—O5 | 126.7 (2) |
C15—C16—C17—O2 | −177.4 (3) | C7—N2—Ni1—O5 | −107.54 (18) |
C15—C16—C17—C12 | 3.5 (4) | C10—N1—Ni1—O2 | 142.47 (17) |
C13—C12—C17—O2 | 177.4 (2) | C11—N1—Ni1—O2 | 16.41 (18) |
C11—C12—C17—O2 | −6.5 (4) | C10—N1—Ni1—O4 | 49.18 (18) |
C13—C12—C17—C16 | −3.4 (4) | C11—N1—Ni1—O4 | −76.87 (17) |
C11—C12—C17—C16 | 172.7 (2) | C10—N1—Ni1—N2 | −41.83 (19) |
C9—C10—N1—C11 | −173.0 (2) | C11—N1—Ni1—N2 | −167.88 (18) |
C9—C10—N1—Ni1 | 61.2 (3) | C10—N1—Ni1—O5 | −124.11 (18) |
C12—C11—N1—C10 | 172.0 (2) | C11—N1—Ni1—O5 | 109.84 (17) |
C12—C11—N1—Ni1 | −60.0 (2) | C20—O5—Ni1—O2 | −48.7 (2) |
C9—C8—N2—C7 | 176.4 (2) | C20—O5—Ni1—O1 | 33.3 (2) |
C9—C8—N2—Ni1 | −57.7 (3) | C20—O5—Ni1—N2 | 125.6 (2) |
C6—C7—N2—C8 | −170.6 (2) | C20—O5—Ni1—N1 | −141.1 (2) |
C6—C7—N2—Ni1 | 60.8 (3) | C17—O2—Ni2—O1 | 139.6 (2) |
O5—C20—N3—C21 | 5.4 (5) | Ni1—O2—Ni2—O1 | −14.91 (6) |
O5—C20—N3—C22 | 177.7 (3) | C17—O2—Ni2—O1i | −40.4 (2) |
O7—C23—N4—C25 | 1.7 (8) | Ni1—O2—Ni2—O1i | 165.09 (6) |
O7—C23—N4—C24 | −175.8 (5) | C17—O2—Ni2—O3i | 45.9 (2) |
C2—C1—O1—Ni1 | −138.0 (2) | Ni1—O2—Ni2—O3i | −108.60 (7) |
C6—C1—O1—Ni1 | 41.8 (3) | C17—O2—Ni2—O3 | −134.1 (2) |
C2—C1—O1—Ni2 | 8.9 (4) | Ni1—O2—Ni2—O3 | 71.40 (7) |
C6—C1—O1—Ni2 | −171.28 (17) | C1—O1—Ni2—O2i | 42.4 (2) |
C16—C17—O2—Ni1 | 138.8 (2) | Ni1—O1—Ni2—O2i | −165.22 (6) |
C12—C17—O2—Ni1 | −42.1 (3) | C1—O1—Ni2—O2 | −137.6 (2) |
C16—C17—O2—Ni2 | −10.7 (4) | Ni1—O1—Ni2—O2 | 14.78 (6) |
C12—C17—O2—Ni2 | 168.41 (17) | C1—O1—Ni2—O3i | −44.9 (2) |
O4—C18—O3—Ni2 | 9.9 (4) | Ni1—O1—Ni2—O3i | 107.49 (7) |
C19—C18—O3—Ni2 | −169.85 (18) | C1—O1—Ni2—O3 | 135.1 (2) |
O3—C18—O4—Ni1 | −7.4 (4) | Ni1—O1—Ni2—O3 | −72.51 (7) |
C19—C18—O4—Ni1 | 172.35 (18) | C18—O3—Ni2—O2i | 134.1 (2) |
N3—C20—O5—Ni1 | −146.7 (2) | C18—O3—Ni2—O2 | −45.9 (2) |
C17—O2—Ni1—O1 | −144.15 (18) | C18—O3—Ni2—O1 | 35.5 (2) |
Ni2—O2—Ni1—O1 | 14.97 (7) | C18—O3—Ni2—O1i | −144.5 (2) |
C17—O2—Ni1—O4 | 125.53 (17) |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1′···O6 | 0.81 (3) | 2.39 (3) | 2.765 (3) | 109 (2) |
N2—H2′···O6 | 0.81 (3) | 2.49 (3) | 2.836 (3) | 107 (2) |
O6—H6A···O7i | 1.11 (4) | 1.57 (4) | 2.660 (4) | 168 (3) |