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
Key indicators
- Single-crystal X-ray study
- T = 300 K
- Mean (C-C) = 0.004 Å
- R factor = 0.034
- wR factor = 0.096
- Data-to-parameter ratio = 15.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT355_ALERT_3_B Long O-H Bond (0.82A) O6 - H6A ... 1.11 Ang.
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct... 1 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.68 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.68 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for N4 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C22 PLAT716_ALERT_1_C H...A Unknown or Inconsistent Label .......... O7^I^ H6A O7^I^ PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... O7^I^ O6 O7^I^ PLAT718_ALERT_1_C D-H..A Unknown or Inconsistent Label .......... O7^I^ O6 H6A O7^I^ PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C3 H7 N O
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 12 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion
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) |