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metal-organic compounds
The NiII atom in the title compound, [Ni(C25H22N3O)2(C2H6O)], is chelated by two deprotonated 4-[(Z)-(2,4-dimethylphenylamino)phenylmethylene]-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one ligands through their amide N and carbonyl O atoms and coordinated by an ethanol molecule in a five-coordinate trigonal–bipyramidal geometry.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680603844X/bt2183sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680603844X/bt2183Isup2.hkl |
CCDC reference: 624008
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.057
- wR factor = 0.151
- Data-to-parameter ratio = 14.2
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.07 Ratio
Author Response: The ethanol is somewhat disordered, but the disorder was not treated. |
Alert level B PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.00 Ratio PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C51 .. 19.01 su
Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Ni1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1 PLAT731_ALERT_1_C Bond Calc 1.476(12), Rep 1.478(5) ...... 2.40 su-Ra C51 -C52 1.555 1.555
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Computing details top
Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.
Bis{4-[(Z)-(2,4-dimethylphenylamino)phenylmethylene]-3-methyl-1-phenyl-1H-
pyrazol-5(4H)-onatoκ2N,O}(ethanol-κO)nickel(II) top
Crystal data top
[Ni(C25H22N3O)2(C2H6O)] | F(000) = 1824 |
Mr = 865.69 | Dx = 1.262 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6181 reflections |
a = 24.478 (1) Å | θ = 2.2–21.3° |
b = 14.8835 (6) Å | µ = 0.48 mm−1 |
c = 12.6757 (5) Å | T = 295 K |
β = 99.366 (1)° | Block, green |
V = 4556.4 (3) Å3 | 0.20 × 0.10 × 0.10 mm |
Z = 4 |
Data collection top
Bruker SMART area-detector diffractometer | 8022 independent reflections |
Radiation source: fine-focus sealed tube | 5347 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.097 |
ω and φ scans | θmax = 25.0°, θmin = 0.8° |
Absorption correction: multi-scan SADABS (Sheldrick, 1996) | h = −29→29 |
Tmin = 0.911, Tmax = 0.954 | k = −17→17 |
43522 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)] = 0.057 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.151 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0811P)2] where P = (Fo2 + 2Fc2)/3 |
8022 reflections | (Δ/σ)max = 0.001 |
565 parameters | Δρmax = 0.60 e Å−3 |
20 restraints | Δρmin = −0.58 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.735525 (17) | 0.47477 (3) | 0.56797 (3) | 0.04315 (16) | |
O1 | 0.69442 (10) | 0.37465 (15) | 0.62216 (18) | 0.0518 (6) | |
O2 | 0.77269 (9) | 0.55354 (16) | 0.47710 (18) | 0.0510 (6) | |
O3 | 0.71478 (16) | 0.3998 (2) | 0.4273 (2) | 0.1100 (13) | |
H3O | 0.7029 | 0.3471 | 0.4359 | 0.132* | |
N1 | 0.66967 (12) | 0.30073 (19) | 0.7689 (2) | 0.0520 (7) | |
N2 | 0.69085 (13) | 0.2884 (2) | 0.8777 (2) | 0.0578 (8) | |
N3 | 0.79942 (11) | 0.46261 (17) | 0.6898 (2) | 0.0451 (7) | |
N4 | 0.81215 (11) | 0.69196 (19) | 0.4499 (2) | 0.0517 (7) | |
N5 | 0.80716 (12) | 0.7817 (2) | 0.4793 (2) | 0.0576 (8) | |
N6 | 0.69457 (10) | 0.57912 (17) | 0.6216 (2) | 0.0419 (6) | |
C1 | 0.61568 (16) | 0.2695 (2) | 0.7303 (3) | 0.0537 (9) | |
C2 | 0.59412 (19) | 0.2717 (3) | 0.6237 (4) | 0.0874 (15) | |
H2 | 0.6157 | 0.2919 | 0.5746 | 0.105* | |
C3 | 0.5398 (2) | 0.2438 (4) | 0.5888 (4) | 0.1010 (17) | |
H3 | 0.5250 | 0.2483 | 0.5167 | 0.121* | |
C4 | 0.5083 (2) | 0.2103 (3) | 0.6579 (4) | 0.0933 (15) | |
H4 | 0.4724 | 0.1903 | 0.6335 | 0.112* | |
C5 | 0.5300 (2) | 0.2064 (4) | 0.7640 (4) | 0.1025 (17) | |
H5 | 0.5087 | 0.1839 | 0.8126 | 0.123* | |
C6 | 0.58346 (19) | 0.2358 (3) | 0.7998 (4) | 0.0836 (14) | |
H6 | 0.5978 | 0.2326 | 0.8724 | 0.100* | |
C7 | 0.70465 (14) | 0.3524 (2) | 0.7205 (3) | 0.0453 (8) | |
C8 | 0.75121 (14) | 0.3712 (2) | 0.7993 (3) | 0.0451 (8) | |
C9 | 0.73865 (16) | 0.3304 (2) | 0.8944 (3) | 0.0530 (9) | |
C10 | 0.77083 (18) | 0.3296 (3) | 1.0061 (3) | 0.0795 (13) | |
H10A | 0.7491 | 0.3014 | 1.0534 | 0.119* | |
H10B | 0.7793 | 0.3901 | 1.0293 | 0.119* | |
H10C | 0.8046 | 0.2966 | 1.0070 | 0.119* | |
C11 | 0.79856 (14) | 0.4209 (2) | 0.7807 (3) | 0.0455 (8) | |
C12 | 0.84809 (14) | 0.4233 (2) | 0.8664 (3) | 0.0494 (9) | |
C13 | 0.88322 (17) | 0.3510 (3) | 0.8847 (3) | 0.0731 (12) | |
H13 | 0.8760 | 0.2992 | 0.8438 | 0.088* | |
C14 | 0.9293 (2) | 0.3550 (4) | 0.9638 (4) | 0.0944 (16) | |
H14 | 0.9528 | 0.3057 | 0.9756 | 0.113* | |
C15 | 0.9408 (2) | 0.4301 (4) | 1.0244 (4) | 0.0952 (16) | |
H15 | 0.9719 | 0.4322 | 1.0772 | 0.114* | |
C16 | 0.9063 (2) | 0.5025 (3) | 1.0070 (3) | 0.0804 (13) | |
H16 | 0.9140 | 0.5539 | 1.0484 | 0.096* | |
C17 | 0.86028 (17) | 0.5001 (3) | 0.9288 (3) | 0.0626 (11) | |
H17 | 0.8371 | 0.5499 | 0.9176 | 0.075* | |
C18 | 0.85002 (14) | 0.5064 (2) | 0.6746 (3) | 0.0484 (9) | |
C19 | 0.85793 (16) | 0.5962 (3) | 0.7029 (3) | 0.0603 (10) | |
H19 | 0.8312 | 0.6271 | 0.7329 | 0.072* | |
C20 | 0.9058 (2) | 0.6395 (3) | 0.6863 (3) | 0.0748 (13) | |
H20 | 0.9104 | 0.7001 | 0.7032 | 0.090* | |
C21 | 0.94639 (19) | 0.5951 (4) | 0.6455 (4) | 0.0801 (14) | |
C22 | 0.93680 (18) | 0.5079 (4) | 0.6138 (4) | 0.0770 (13) | |
H22 | 0.9634 | 0.4783 | 0.5822 | 0.092* | |
C23 | 0.88931 (16) | 0.4620 (3) | 0.6266 (3) | 0.0600 (10) | |
C24 | 1.0014 (2) | 0.6409 (4) | 0.6354 (4) | 0.123 (2) | |
H24A | 0.9956 | 0.7045 | 0.6265 | 0.185* | |
H24B | 1.0153 | 0.6171 | 0.5745 | 0.185* | |
H24C | 1.0278 | 0.6299 | 0.6989 | 0.185* | |
C25 | 0.8808 (2) | 0.3672 (3) | 0.5903 (4) | 0.0988 (16) | |
H25A | 0.9061 | 0.3529 | 0.5424 | 0.148* | |
H25B | 0.8435 | 0.3597 | 0.5540 | 0.148* | |
H25C | 0.8872 | 0.3279 | 0.6511 | 0.148* | |
C26 | 0.85622 (15) | 0.6665 (3) | 0.3970 (3) | 0.0548 (10) | |
C27 | 0.85144 (19) | 0.5927 (3) | 0.3331 (4) | 0.0827 (14) | |
H27 | 0.8188 | 0.5595 | 0.3231 | 0.099* | |
C28 | 0.8953 (2) | 0.5667 (4) | 0.2827 (4) | 0.1015 (17) | |
H28 | 0.8923 | 0.5154 | 0.2402 | 0.122* | |
C29 | 0.9428 (2) | 0.6162 (5) | 0.2953 (4) | 0.0951 (17) | |
H29 | 0.9718 | 0.5997 | 0.2600 | 0.114* | |
C30 | 0.94767 (19) | 0.6883 (4) | 0.3583 (4) | 0.0892 (16) | |
H30 | 0.9804 | 0.7212 | 0.3676 | 0.107* | |
C31 | 0.90419 (17) | 0.7157 (3) | 0.4111 (3) | 0.0748 (12) | |
H31 | 0.9079 | 0.7663 | 0.4548 | 0.090* | |
C32 | 0.77607 (13) | 0.6380 (2) | 0.4921 (3) | 0.0446 (8) | |
C33 | 0.74543 (13) | 0.6953 (2) | 0.5496 (3) | 0.0431 (8) | |
C34 | 0.76731 (14) | 0.7834 (2) | 0.5365 (3) | 0.0515 (9) | |
C35 | 0.75288 (18) | 0.8717 (3) | 0.5797 (4) | 0.0743 (12) | |
H35A | 0.7785 | 0.9166 | 0.5636 | 0.112* | |
H35B | 0.7549 | 0.8674 | 0.6558 | 0.112* | |
H35C | 0.7160 | 0.8882 | 0.5476 | 0.112* | |
C36 | 0.70392 (13) | 0.6653 (2) | 0.6090 (2) | 0.0405 (8) | |
C37 | 0.67006 (13) | 0.7349 (2) | 0.6529 (3) | 0.0424 (8) | |
C38 | 0.62550 (16) | 0.7727 (3) | 0.5871 (3) | 0.0647 (11) | |
H38 | 0.6167 | 0.7534 | 0.5166 | 0.078* | |
C39 | 0.59395 (17) | 0.8383 (3) | 0.6236 (4) | 0.0833 (14) | |
H39 | 0.5637 | 0.8623 | 0.5786 | 0.100* | |
C40 | 0.60746 (19) | 0.8685 (3) | 0.7284 (4) | 0.0808 (13) | |
H40 | 0.5867 | 0.9135 | 0.7538 | 0.097* | |
C41 | 0.65155 (18) | 0.8313 (3) | 0.7936 (3) | 0.0681 (11) | |
H41 | 0.6605 | 0.8512 | 0.8639 | 0.082* | |
C42 | 0.68273 (15) | 0.7654 (2) | 0.7574 (3) | 0.0554 (9) | |
H42 | 0.7126 | 0.7409 | 0.8031 | 0.067* | |
C43 | 0.65425 (13) | 0.5545 (2) | 0.6869 (3) | 0.0429 (8) | |
C44 | 0.66932 (15) | 0.5512 (2) | 0.7965 (3) | 0.0515 (9) | |
H44 | 0.7048 | 0.5691 | 0.8273 | 0.062* | |
C45 | 0.63270 (17) | 0.5219 (2) | 0.8614 (3) | 0.0610 (10) | |
H45 | 0.6437 | 0.5194 | 0.9351 | 0.073* | |
C46 | 0.57977 (18) | 0.4963 (3) | 0.8166 (4) | 0.0645 (11) | |
C47 | 0.56553 (16) | 0.4988 (3) | 0.7073 (4) | 0.0687 (12) | |
H47 | 0.5302 | 0.4804 | 0.6767 | 0.082* | |
C48 | 0.60162 (15) | 0.5274 (3) | 0.6409 (3) | 0.0570 (10) | |
C49 | 0.5389 (2) | 0.4628 (3) | 0.8855 (4) | 0.0980 (17) | |
H49A | 0.5567 | 0.4594 | 0.9586 | 0.147* | |
H49B | 0.5258 | 0.4043 | 0.8615 | 0.147* | |
H49C | 0.5081 | 0.5036 | 0.8799 | 0.147* | |
C50 | 0.58494 (17) | 0.5256 (3) | 0.5203 (3) | 0.0855 (14) | |
H50A | 0.5505 | 0.4939 | 0.5020 | 0.128* | |
H50B | 0.6131 | 0.4956 | 0.4888 | 0.128* | |
H50C | 0.5806 | 0.5860 | 0.4936 | 0.128* | |
C51 | 0.7177 (3) | 0.4244 (4) | 0.3156 (4) | 0.154 (3) | |
H51A | 0.7160 | 0.4890 | 0.3053 | 0.185* | |
H51B | 0.6883 | 0.3962 | 0.2661 | 0.185* | |
C52 | 0.7725 (4) | 0.3881 (6) | 0.3038 (8) | 0.206 (4) | |
H52A | 0.7799 | 0.4011 | 0.2333 | 0.310* | |
H52B | 0.7729 | 0.3243 | 0.3146 | 0.310* | |
H52C | 0.8005 | 0.4155 | 0.3558 | 0.310* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0507 (3) | 0.0407 (3) | 0.0398 (3) | −0.0023 (2) | 0.0125 (2) | 0.00241 (19) |
O1 | 0.0670 (16) | 0.0483 (14) | 0.0410 (14) | −0.0152 (12) | 0.0116 (12) | 0.0015 (11) |
O2 | 0.0636 (16) | 0.0476 (14) | 0.0460 (14) | −0.0051 (12) | 0.0213 (12) | 0.0012 (11) |
O3 | 0.214 (4) | 0.075 (2) | 0.0544 (18) | −0.065 (2) | 0.063 (2) | −0.0199 (15) |
N1 | 0.066 (2) | 0.0477 (17) | 0.0431 (18) | −0.0096 (15) | 0.0125 (15) | 0.0058 (14) |
N2 | 0.070 (2) | 0.0549 (19) | 0.0502 (19) | −0.0031 (17) | 0.0155 (16) | 0.0116 (15) |
N3 | 0.0450 (16) | 0.0386 (16) | 0.0523 (18) | 0.0017 (13) | 0.0099 (14) | 0.0039 (13) |
N4 | 0.0515 (18) | 0.0517 (19) | 0.0562 (19) | −0.0035 (14) | 0.0213 (15) | 0.0066 (15) |
N5 | 0.061 (2) | 0.0460 (18) | 0.069 (2) | −0.0060 (15) | 0.0218 (17) | 0.0098 (15) |
N6 | 0.0398 (15) | 0.0441 (17) | 0.0434 (16) | 0.0009 (13) | 0.0111 (12) | 0.0079 (13) |
C1 | 0.065 (2) | 0.047 (2) | 0.050 (2) | −0.0111 (18) | 0.0145 (19) | 0.0005 (17) |
C2 | 0.091 (3) | 0.108 (4) | 0.063 (3) | −0.050 (3) | 0.014 (3) | 0.000 (3) |
C3 | 0.112 (4) | 0.117 (4) | 0.071 (3) | −0.052 (3) | 0.005 (3) | 0.003 (3) |
C4 | 0.077 (3) | 0.111 (4) | 0.095 (4) | −0.034 (3) | 0.020 (3) | −0.010 (3) |
C5 | 0.085 (4) | 0.146 (5) | 0.083 (4) | −0.046 (3) | 0.033 (3) | 0.005 (3) |
C6 | 0.081 (3) | 0.108 (4) | 0.064 (3) | −0.028 (3) | 0.021 (2) | 0.007 (3) |
C7 | 0.059 (2) | 0.0341 (18) | 0.046 (2) | −0.0019 (16) | 0.0164 (18) | 0.0035 (16) |
C8 | 0.052 (2) | 0.0387 (19) | 0.046 (2) | 0.0031 (16) | 0.0136 (17) | 0.0046 (16) |
C9 | 0.064 (2) | 0.049 (2) | 0.046 (2) | 0.0039 (19) | 0.0089 (19) | 0.0075 (17) |
C10 | 0.091 (3) | 0.096 (3) | 0.051 (3) | −0.010 (3) | 0.010 (2) | 0.023 (2) |
C11 | 0.054 (2) | 0.0350 (18) | 0.048 (2) | 0.0073 (16) | 0.0103 (17) | −0.0007 (16) |
C12 | 0.052 (2) | 0.049 (2) | 0.049 (2) | 0.0030 (17) | 0.0126 (17) | 0.0035 (17) |
C13 | 0.075 (3) | 0.060 (3) | 0.079 (3) | 0.022 (2) | −0.001 (2) | −0.002 (2) |
C14 | 0.076 (3) | 0.104 (4) | 0.097 (4) | 0.032 (3) | −0.008 (3) | 0.014 (3) |
C15 | 0.075 (3) | 0.125 (5) | 0.076 (3) | −0.005 (3) | −0.016 (3) | 0.012 (3) |
C16 | 0.100 (4) | 0.083 (3) | 0.053 (3) | −0.020 (3) | −0.003 (3) | −0.005 (2) |
C17 | 0.078 (3) | 0.059 (2) | 0.051 (2) | 0.008 (2) | 0.010 (2) | −0.0014 (19) |
C18 | 0.048 (2) | 0.052 (2) | 0.045 (2) | −0.0012 (17) | 0.0052 (17) | 0.0059 (16) |
C19 | 0.071 (3) | 0.056 (2) | 0.054 (2) | −0.011 (2) | 0.010 (2) | −0.0021 (19) |
C20 | 0.096 (3) | 0.068 (3) | 0.058 (3) | −0.032 (3) | 0.007 (2) | 0.004 (2) |
C21 | 0.070 (3) | 0.108 (4) | 0.061 (3) | −0.032 (3) | 0.008 (2) | 0.016 (3) |
C22 | 0.057 (3) | 0.105 (4) | 0.072 (3) | 0.001 (3) | 0.021 (2) | 0.006 (3) |
C23 | 0.056 (2) | 0.062 (3) | 0.065 (3) | 0.001 (2) | 0.017 (2) | 0.000 (2) |
C24 | 0.092 (4) | 0.171 (6) | 0.105 (4) | −0.066 (4) | 0.010 (3) | 0.028 (4) |
C25 | 0.088 (3) | 0.088 (4) | 0.129 (4) | 0.005 (3) | 0.043 (3) | −0.032 (3) |
C26 | 0.057 (2) | 0.064 (2) | 0.047 (2) | 0.0019 (19) | 0.0197 (18) | 0.0168 (19) |
C27 | 0.089 (3) | 0.094 (4) | 0.076 (3) | −0.013 (3) | 0.045 (3) | −0.004 (3) |
C28 | 0.117 (4) | 0.117 (4) | 0.081 (4) | 0.003 (4) | 0.047 (3) | −0.008 (3) |
C29 | 0.085 (4) | 0.129 (5) | 0.081 (4) | 0.029 (4) | 0.042 (3) | 0.025 (3) |
C30 | 0.058 (3) | 0.129 (5) | 0.084 (4) | 0.005 (3) | 0.023 (3) | 0.034 (3) |
C31 | 0.063 (3) | 0.090 (3) | 0.074 (3) | −0.004 (2) | 0.020 (2) | 0.017 (2) |
C32 | 0.047 (2) | 0.046 (2) | 0.041 (2) | −0.0036 (17) | 0.0070 (16) | 0.0079 (16) |
C33 | 0.043 (2) | 0.0428 (19) | 0.043 (2) | −0.0020 (15) | 0.0068 (16) | 0.0052 (15) |
C34 | 0.049 (2) | 0.047 (2) | 0.060 (2) | −0.0024 (17) | 0.0110 (18) | 0.0082 (17) |
C35 | 0.079 (3) | 0.049 (2) | 0.101 (3) | −0.008 (2) | 0.032 (3) | 0.003 (2) |
C36 | 0.0366 (18) | 0.048 (2) | 0.0357 (18) | 0.0007 (15) | 0.0018 (14) | 0.0049 (15) |
C37 | 0.0385 (19) | 0.045 (2) | 0.044 (2) | −0.0006 (15) | 0.0073 (16) | 0.0034 (16) |
C38 | 0.060 (2) | 0.082 (3) | 0.050 (2) | 0.018 (2) | 0.003 (2) | −0.011 (2) |
C39 | 0.062 (3) | 0.104 (4) | 0.081 (3) | 0.034 (3) | 0.001 (2) | −0.009 (3) |
C40 | 0.077 (3) | 0.086 (3) | 0.081 (3) | 0.027 (3) | 0.016 (3) | −0.017 (3) |
C41 | 0.087 (3) | 0.068 (3) | 0.050 (2) | 0.010 (2) | 0.013 (2) | −0.008 (2) |
C42 | 0.062 (2) | 0.052 (2) | 0.050 (2) | 0.0044 (19) | 0.0016 (18) | −0.0004 (18) |
C43 | 0.0408 (19) | 0.0391 (18) | 0.051 (2) | 0.0010 (15) | 0.0152 (17) | 0.0038 (15) |
C44 | 0.051 (2) | 0.053 (2) | 0.053 (2) | −0.0068 (17) | 0.0150 (18) | 0.0021 (17) |
C45 | 0.078 (3) | 0.057 (2) | 0.055 (2) | −0.007 (2) | 0.030 (2) | 0.0021 (19) |
C46 | 0.070 (3) | 0.059 (2) | 0.076 (3) | −0.012 (2) | 0.043 (2) | −0.004 (2) |
C47 | 0.048 (2) | 0.078 (3) | 0.084 (3) | −0.019 (2) | 0.023 (2) | −0.008 (2) |
C48 | 0.048 (2) | 0.064 (3) | 0.060 (2) | −0.0049 (19) | 0.0131 (19) | 0.003 (2) |
C49 | 0.110 (4) | 0.095 (4) | 0.106 (4) | −0.030 (3) | 0.068 (3) | −0.005 (3) |
C50 | 0.058 (3) | 0.123 (4) | 0.073 (3) | −0.018 (3) | 0.004 (2) | 0.001 (3) |
C51 | 0.202 (6) | 0.099 (5) | 0.166 (6) | −0.072 (5) | 0.045 (5) | −0.026 (4) |
C52 | 0.278 (8) | 0.151 (6) | 0.204 (7) | −0.040 (6) | 0.081 (7) | −0.025 (6) |
Geometric parameters (Å, º) top
Ni1—O1 | 1.982 (2) | C23—C25 | 1.488 (6) |
Ni1—O2 | 1.967 (2) | C24—H24A | 0.9600 |
Ni1—O3 | 2.094 (3) | C24—H24B | 0.9600 |
Ni1—N3 | 2.020 (3) | C24—H24C | 0.9600 |
Ni1—N6 | 2.025 (3) | C25—H25A | 0.9600 |
O1—C7 | 1.275 (4) | C25—H25B | 0.9600 |
O2—C32 | 1.272 (4) | C25—H25C | 0.9600 |
O3—C51 | 1.475 (4) | C26—C27 | 1.358 (6) |
O3—H3O | 0.8500 | C26—C31 | 1.371 (5) |
N1—C7 | 1.368 (4) | C27—C28 | 1.391 (6) |
N1—N2 | 1.404 (4) | C27—H27 | 0.9300 |
N1—C1 | 1.411 (4) | C28—C29 | 1.364 (7) |
N2—C9 | 1.314 (4) | C28—H28 | 0.9300 |
N3—C11 | 1.312 (4) | C29—C30 | 1.332 (7) |
N3—C18 | 1.440 (4) | C29—H29 | 0.9300 |
N4—C32 | 1.366 (4) | C30—C31 | 1.407 (6) |
N4—N5 | 1.398 (4) | C30—H30 | 0.9300 |
N4—C26 | 1.412 (4) | C31—H31 | 0.9300 |
N5—C34 | 1.308 (4) | C32—C33 | 1.415 (4) |
N6—C36 | 1.317 (4) | C33—C36 | 1.431 (4) |
N6—C43 | 1.434 (4) | C33—C34 | 1.436 (4) |
C1—C2 | 1.368 (5) | C34—C35 | 1.488 (5) |
C1—C6 | 1.371 (5) | C35—H35A | 0.9600 |
C2—C3 | 1.395 (6) | C35—H35B | 0.9600 |
C2—H2 | 0.9300 | C35—H35C | 0.9600 |
C3—C4 | 1.353 (6) | C36—C37 | 1.490 (4) |
C3—H3 | 0.9300 | C37—C38 | 1.381 (5) |
C4—C5 | 1.365 (6) | C37—C42 | 1.387 (5) |
C4—H4 | 0.9300 | C38—C39 | 1.370 (5) |
C5—C6 | 1.385 (6) | C38—H38 | 0.9300 |
C5—H5 | 0.9300 | C39—C40 | 1.391 (6) |
C6—H6 | 0.9300 | C39—H39 | 0.9300 |
C7—C8 | 1.416 (5) | C40—C41 | 1.365 (5) |
C8—C9 | 1.426 (5) | C40—H40 | 0.9300 |
C8—C11 | 1.426 (5) | C41—C42 | 1.368 (5) |
C9—C10 | 1.505 (5) | C41—H41 | 0.9300 |
C10—H10A | 0.9600 | C42—H42 | 0.9300 |
C10—H10B | 0.9600 | C43—C44 | 1.379 (5) |
C10—H10C | 0.9600 | C43—C48 | 1.385 (5) |
C11—C12 | 1.490 (5) | C44—C45 | 1.382 (5) |
C12—C13 | 1.373 (5) | C44—H44 | 0.9300 |
C12—C17 | 1.394 (5) | C45—C46 | 1.381 (6) |
C13—C14 | 1.384 (6) | C45—H45 | 0.9300 |
C13—H13 | 0.9300 | C46—C47 | 1.374 (6) |
C14—C15 | 1.359 (7) | C46—C49 | 1.515 (5) |
C14—H14 | 0.9300 | C47—C48 | 1.383 (5) |
C15—C16 | 1.364 (7) | C47—H47 | 0.9300 |
C15—H15 | 0.9300 | C48—C50 | 1.517 (5) |
C16—C17 | 1.374 (6) | C49—H49A | 0.9600 |
C16—H16 | 0.9300 | C49—H49B | 0.9600 |
C17—H17 | 0.9300 | C49—H49C | 0.9600 |
C18—C23 | 1.386 (5) | C50—H50A | 0.9600 |
C18—C19 | 1.390 (5) | C50—H50B | 0.9600 |
C19—C20 | 1.382 (5) | C50—H50C | 0.9600 |
C19—H19 | 0.9300 | C51—C52 | 1.478 (5) |
C20—C21 | 1.363 (6) | C51—H51A | 0.9700 |
C20—H20 | 0.9300 | C51—H51B | 0.9700 |
C21—C22 | 1.367 (6) | C52—H52A | 0.9600 |
C21—C24 | 1.534 (6) | C52—H52B | 0.9600 |
C22—C23 | 1.381 (6) | C52—H52C | 0.9600 |
C22—H22 | 0.9300 | ||
O1—Ni1—O2 | 163.8 (1) | H24A—C24—H24C | 109.5 |
O1—Ni1—O3 | 80.1 (1) | H24B—C24—H24C | 109.5 |
O1—Ni1—N3 | 92.4 (1) | C23—C25—H25A | 109.5 |
O1—Ni1—N6 | 98.8 (1) | C23—C25—H25B | 109.5 |
O2—Ni1—O3 | 83.7 (1) | H25A—C25—H25B | 109.5 |
O2—Ni1—N3 | 97.3 (1) | C23—C25—H25C | 109.5 |
O2—Ni1—N6 | 92.4 (1) | H25A—C25—H25C | 109.5 |
O3—Ni1—N3 | 130.8 (1) | H25B—C25—H25C | 109.5 |
O3—Ni1—N6 | 129.0 (1) | C27—C26—C31 | 119.9 (4) |
N3—Ni1—N6 | 100.1 (1) | C27—C26—N4 | 120.1 (4) |
C7—O1—Ni1 | 120.3 (2) | C31—C26—N4 | 119.9 (4) |
C32—O2—Ni1 | 121.8 (2) | C26—C27—C28 | 120.0 (5) |
C51—O3—Ni1 | 130.0 (3) | C26—C27—H27 | 120.0 |
C51—O3—H3O | 115.0 | C28—C27—H27 | 120.0 |
Ni1—O3—H3O | 115.0 | C29—C28—C27 | 120.2 (5) |
C7—N1—N2 | 110.8 (3) | C29—C28—H28 | 119.9 |
C7—N1—C1 | 130.5 (3) | C27—C28—H28 | 119.9 |
N2—N1—C1 | 118.2 (3) | C30—C29—C28 | 119.7 (5) |
C9—N2—N1 | 105.8 (3) | C30—C29—H29 | 120.1 |
C11—N3—C18 | 118.0 (3) | C28—C29—H29 | 120.1 |
C11—N3—Ni1 | 126.4 (2) | C29—C30—C31 | 121.3 (5) |
C18—N3—Ni1 | 115.6 (2) | C29—C30—H30 | 119.4 |
C32—N4—N5 | 111.6 (3) | C31—C30—H30 | 119.4 |
C32—N4—C26 | 128.4 (3) | C26—C31—C30 | 118.8 (5) |
N5—N4—C26 | 119.3 (3) | C26—C31—H31 | 120.6 |
C34—N5—N4 | 105.8 (3) | C30—C31—H31 | 120.6 |
C36—N6—C43 | 117.9 (3) | O2—C32—N4 | 123.6 (3) |
C36—N6—Ni1 | 126.9 (2) | O2—C32—C33 | 130.3 (3) |
C43—N6—Ni1 | 115.0 (2) | N4—C32—C33 | 106.1 (3) |
C2—C1—C6 | 118.3 (4) | C32—C33—C36 | 124.4 (3) |
C2—C1—N1 | 121.5 (3) | C32—C33—C34 | 104.6 (3) |
C6—C1—N1 | 120.1 (4) | C36—C33—C34 | 131.0 (3) |
C1—C2—C3 | 120.0 (4) | N5—C34—C33 | 111.9 (3) |
C1—C2—H2 | 120.0 | N5—C34—C35 | 117.6 (3) |
C3—C2—H2 | 120.0 | C33—C34—C35 | 130.4 (3) |
C4—C3—C2 | 121.3 (5) | C34—C35—H35A | 109.5 |
C4—C3—H3 | 119.4 | C34—C35—H35B | 109.5 |
C2—C3—H3 | 119.4 | H35A—C35—H35B | 109.5 |
C3—C4—C5 | 118.8 (5) | C34—C35—H35C | 109.5 |
C3—C4—H4 | 120.6 | H35A—C35—H35C | 109.5 |
C5—C4—H4 | 120.6 | H35B—C35—H35C | 109.5 |
C4—C5—C6 | 120.4 (4) | N6—C36—C33 | 121.3 (3) |
C4—C5—H5 | 119.8 | N6—C36—C37 | 120.9 (3) |
C6—C5—H5 | 119.8 | C33—C36—C37 | 117.7 (3) |
C1—C6—C5 | 121.1 (4) | C38—C37—C42 | 118.4 (3) |
C1—C6—H6 | 119.4 | C38—C37—C36 | 119.4 (3) |
C5—C6—H6 | 119.4 | C42—C37—C36 | 122.2 (3) |
O1—C7—N1 | 123.1 (3) | C39—C38—C37 | 121.3 (4) |
O1—C7—C8 | 130.2 (3) | C39—C38—H38 | 119.4 |
N1—C7—C8 | 106.6 (3) | C37—C38—H38 | 119.4 |
C7—C8—C9 | 104.6 (3) | C38—C39—C40 | 119.6 (4) |
C7—C8—C11 | 124.6 (3) | C38—C39—H39 | 120.2 |
C9—C8—C11 | 130.8 (3) | C40—C39—H39 | 120.2 |
N2—C9—C8 | 112.1 (3) | C41—C40—C39 | 119.3 (4) |
N2—C9—C10 | 117.6 (3) | C41—C40—H40 | 120.4 |
C8—C9—C10 | 130.3 (4) | C39—C40—H40 | 120.4 |
C9—C10—H10A | 109.5 | C40—C41—C42 | 121.1 (4) |
C9—C10—H10B | 109.5 | C40—C41—H41 | 119.5 |
H10A—C10—H10B | 109.5 | C42—C41—H41 | 119.5 |
C9—C10—H10C | 109.5 | C41—C42—C37 | 120.4 (3) |
H10A—C10—H10C | 109.5 | C41—C42—H42 | 119.8 |
H10B—C10—H10C | 109.5 | C37—C42—H42 | 119.8 |
N3—C11—C8 | 121.3 (3) | C44—C43—C48 | 119.4 (3) |
N3—C11—C12 | 120.1 (3) | C44—C43—N6 | 119.6 (3) |
C8—C11—C12 | 118.6 (3) | C48—C43—N6 | 120.8 (3) |
C13—C12—C17 | 118.4 (4) | C43—C44—C45 | 121.2 (3) |
C13—C12—C11 | 121.1 (3) | C43—C44—H44 | 119.4 |
C17—C12—C11 | 120.5 (3) | C45—C44—H44 | 119.4 |
C12—C13—C14 | 120.2 (4) | C46—C45—C44 | 119.9 (4) |
C12—C13—H13 | 119.9 | C46—C45—H45 | 120.0 |
C14—C13—H13 | 119.9 | C44—C45—H45 | 120.0 |
C15—C14—C13 | 120.9 (5) | C47—C46—C45 | 118.3 (4) |
C15—C14—H14 | 119.5 | C47—C46—C49 | 120.5 (4) |
C13—C14—H14 | 119.5 | C45—C46—C49 | 121.2 (4) |
C14—C15—C16 | 119.5 (5) | C46—C47—C48 | 122.7 (4) |
C14—C15—H15 | 120.2 | C46—C47—H47 | 118.7 |
C16—C15—H15 | 120.2 | C48—C47—H47 | 118.7 |
C15—C16—C17 | 120.6 (4) | C47—C48—C43 | 118.4 (4) |
C15—C16—H16 | 119.7 | C47—C48—C50 | 120.9 (4) |
C17—C16—H16 | 119.7 | C43—C48—C50 | 120.6 (3) |
C16—C17—C12 | 120.4 (4) | C46—C49—H49A | 109.5 |
C16—C17—H17 | 119.8 | C46—C49—H49B | 109.5 |
C12—C17—H17 | 119.8 | H49A—C49—H49B | 109.5 |
C23—C18—C19 | 119.7 (3) | C46—C49—H49C | 109.5 |
C23—C18—N3 | 121.1 (3) | H49A—C49—H49C | 109.5 |
C19—C18—N3 | 119.1 (3) | H49B—C49—H49C | 109.5 |
C20—C19—C18 | 119.6 (4) | C48—C50—H50A | 109.5 |
C20—C19—H19 | 120.2 | C48—C50—H50B | 109.5 |
C18—C19—H19 | 120.2 | H50A—C50—H50B | 109.5 |
C21—C20—C19 | 121.4 (4) | C48—C50—H50C | 109.5 |
C21—C20—H20 | 119.3 | H50A—C50—H50C | 109.5 |
C19—C20—H20 | 119.3 | H50B—C50—H50C | 109.5 |
C20—C21—C22 | 118.1 (4) | O3—C51—C52 | 101.1 (6) |
C20—C21—C24 | 121.4 (5) | O3—C51—H51A | 111.5 |
C22—C21—C24 | 120.6 (5) | C52—C51—H51A | 111.5 |
C21—C22—C23 | 122.9 (4) | O3—C51—H51B | 111.5 |
C21—C22—H22 | 118.6 | C52—C51—H51B | 111.5 |
C23—C22—H22 | 118.6 | H51A—C51—H51B | 109.4 |
C22—C23—C18 | 118.2 (4) | C51—C52—H52A | 109.5 |
C22—C23—C25 | 120.8 (4) | C51—C52—H52B | 109.5 |
C18—C23—C25 | 121.0 (4) | H52A—C52—H52B | 109.5 |
C21—C24—H24A | 109.5 | C51—C52—H52C | 109.5 |
C21—C24—H24B | 109.5 | H52A—C52—H52C | 109.5 |
H24A—C24—H24B | 109.5 | H52B—C52—H52C | 109.5 |
C21—C24—H24C | 109.5 | ||
O2—Ni1—O1—C7 | 149.2 (3) | C11—N3—C18—C19 | −91.6 (4) |
N3—Ni1—O1—C7 | 22.6 (3) | Ni1—N3—C18—C19 | 87.0 (3) |
N6—Ni1—O1—C7 | −78.0 (3) | C23—C18—C19—C20 | −2.2 (5) |
O3—Ni1—O1—C7 | 153.7 (3) | N3—C18—C19—C20 | −178.5 (3) |
O1—Ni1—O2—C32 | 151.9 (3) | C18—C19—C20—C21 | −2.1 (6) |
N3—Ni1—O2—C32 | −82.1 (3) | C19—C20—C21—C22 | 4.9 (7) |
N6—Ni1—O2—C32 | 18.4 (3) | C19—C20—C21—C24 | −175.1 (4) |
O3—Ni1—O2—C32 | 147.4 (3) | C20—C21—C22—C23 | −3.6 (7) |
O2—Ni1—O3—C51 | −14.3 (5) | C24—C21—C22—C23 | 176.3 (4) |
O1—Ni1—O3—C51 | 166.9 (5) | C21—C22—C23—C18 | −0.5 (7) |
N3—Ni1—O3—C51 | −108.5 (5) | C21—C22—C23—C25 | 179.8 (5) |
N6—Ni1—O3—C51 | 73.6 (5) | C19—C18—C23—C22 | 3.4 (6) |
C7—N1—N2—C9 | −1.3 (4) | N3—C18—C23—C22 | 179.6 (3) |
C1—N1—N2—C9 | −174.1 (3) | C19—C18—C23—C25 | −176.9 (4) |
O2—Ni1—N3—C11 | 175.3 (3) | N3—C18—C23—C25 | −0.6 (6) |
O1—Ni1—N3—C11 | −17.8 (3) | C32—N4—C26—C27 | 35.5 (6) |
N6—Ni1—N3—C11 | 81.6 (3) | N5—N4—C26—C27 | −155.0 (4) |
O3—Ni1—N3—C11 | −96.7 (3) | C32—N4—C26—C31 | −143.8 (4) |
O2—Ni1—N3—C18 | −3.1 (2) | N5—N4—C26—C31 | 25.8 (5) |
O1—Ni1—N3—C18 | 163.8 (2) | C31—C26—C27—C28 | 0.5 (7) |
N6—Ni1—N3—C18 | −96.8 (2) | N4—C26—C27—C28 | −178.8 (4) |
O3—Ni1—N3—C18 | 84.8 (3) | C26—C27—C28—C29 | −1.4 (8) |
C32—N4—N5—C34 | −1.7 (4) | C27—C28—C29—C30 | 1.8 (8) |
C26—N4—N5—C34 | −173.0 (3) | C28—C29—C30—C31 | −1.2 (8) |
O2—Ni1—N6—C36 | −11.8 (3) | C27—C26—C31—C30 | 0.1 (6) |
O1—Ni1—N6—C36 | −179.9 (3) | N4—C26—C31—C30 | 179.4 (3) |
N3—Ni1—N6—C36 | 86.1 (3) | C29—C30—C31—C26 | 0.2 (7) |
O3—Ni1—N6—C36 | −95.5 (3) | Ni1—O2—C32—N4 | 163.4 (2) |
O2—Ni1—N6—C43 | 173.3 (2) | Ni1—O2—C32—C33 | −18.0 (5) |
O1—Ni1—N6—C43 | 5.2 (2) | N5—N4—C32—O2 | −179.9 (3) |
N3—Ni1—N6—C43 | −88.8 (2) | C26—N4—C32—O2 | −9.6 (6) |
O3—Ni1—N6—C43 | 89.6 (2) | N5—N4—C32—C33 | 1.3 (4) |
C7—N1—C1—C2 | 14.8 (6) | C26—N4—C32—C33 | 171.5 (3) |
N2—N1—C1—C2 | −174.0 (4) | O2—C32—C33—C36 | 3.0 (6) |
C7—N1—C1—C6 | −165.2 (4) | N4—C32—C33—C36 | −178.2 (3) |
N2—N1—C1—C6 | 5.9 (5) | O2—C32—C33—C34 | −179.1 (3) |
C6—C1—C2—C3 | 2.7 (7) | N4—C32—C33—C34 | −0.3 (3) |
N1—C1—C2—C3 | −177.3 (4) | N4—N5—C34—C33 | 1.5 (4) |
C1—C2—C3—C4 | −3.1 (8) | N4—N5—C34—C35 | 179.7 (3) |
C2—C3—C4—C5 | 1.8 (9) | C32—C33—C34—N5 | −0.8 (4) |
C3—C4—C5—C6 | −0.4 (9) | C36—C33—C34—N5 | 176.9 (3) |
C2—C1—C6—C5 | −1.4 (7) | C32—C33—C34—C35 | −178.7 (4) |
N1—C1—C6—C5 | 178.7 (4) | C36—C33—C34—C35 | −1.1 (6) |
C4—C5—C6—C1 | 0.2 (8) | C43—N6—C36—C33 | 176.8 (3) |
Ni1—O1—C7—N1 | 163.2 (2) | Ni1—N6—C36—C33 | 2.1 (4) |
Ni1—O1—C7—C8 | −18.3 (5) | C43—N6—C36—C37 | −5.5 (4) |
N2—N1—C7—O1 | −178.8 (3) | Ni1—N6—C36—C37 | 179.7 (2) |
C1—N1—C7—O1 | −7.1 (6) | C32—C33—C36—N6 | 5.9 (5) |
N2—N1—C7—C8 | 2.4 (4) | C34—C33—C36—N6 | −171.3 (3) |
C1—N1—C7—C8 | 174.1 (3) | C32—C33—C36—C37 | −171.8 (3) |
O1—C7—C8—C9 | 178.9 (3) | C34—C33—C36—C37 | 10.9 (5) |
N1—C7—C8—C9 | −2.5 (4) | N6—C36—C37—C38 | −96.3 (4) |
O1—C7—C8—C11 | −1.1 (6) | C33—C36—C37—C38 | 81.4 (4) |
N1—C7—C8—C11 | 177.6 (3) | N6—C36—C37—C42 | 85.7 (4) |
N1—N2—C9—C8 | −0.3 (4) | C33—C36—C37—C42 | −96.6 (4) |
N1—N2—C9—C10 | 179.2 (3) | C42—C37—C38—C39 | −0.6 (6) |
C7—C8—C9—N2 | 1.8 (4) | C36—C37—C38—C39 | −178.7 (4) |
C11—C8—C9—N2 | −178.3 (3) | C37—C38—C39—C40 | 1.1 (7) |
C7—C8—C9—C10 | −177.7 (4) | C38—C39—C40—C41 | −0.9 (7) |
C11—C8—C9—C10 | 2.2 (6) | C39—C40—C41—C42 | 0.4 (7) |
C18—N3—C11—C8 | −176.0 (3) | C40—C41—C42—C37 | 0.1 (6) |
Ni1—N3—C11—C8 | 5.5 (4) | C38—C37—C42—C41 | 0.0 (5) |
C18—N3—C11—C12 | 2.8 (4) | C36—C37—C42—C41 | 178.0 (3) |
Ni1—N3—C11—C12 | −175.6 (2) | C36—N6—C43—C44 | −82.7 (4) |
C7—C8—C11—N3 | 8.4 (5) | Ni1—N6—C43—C44 | 92.7 (3) |
C9—C8—C11—N3 | −171.5 (3) | C36—N6—C43—C48 | 102.3 (4) |
C7—C8—C11—C12 | −170.5 (3) | Ni1—N6—C43—C48 | −82.3 (3) |
C9—C8—C11—C12 | 9.6 (5) | C48—C43—C44—C45 | −0.4 (5) |
N3—C11—C12—C13 | −102.6 (4) | N6—C43—C44—C45 | −175.5 (3) |
C8—C11—C12—C13 | 76.3 (4) | C43—C44—C45—C46 | −0.8 (6) |
N3—C11—C12—C17 | 76.4 (4) | C44—C45—C46—C47 | 1.6 (6) |
C8—C11—C12—C17 | −104.7 (4) | C44—C45—C46—C49 | 179.3 (4) |
C17—C12—C13—C14 | 0.2 (6) | C45—C46—C47—C48 | −1.3 (6) |
C11—C12—C13—C14 | 179.2 (4) | C49—C46—C47—C48 | −179.0 (4) |
C12—C13—C14—C15 | −0.1 (8) | C46—C47—C48—C43 | 0.1 (6) |
C13—C14—C15—C16 | 0.1 (8) | C46—C47—C48—C50 | 177.5 (4) |
C14—C15—C16—C17 | −0.1 (8) | C44—C43—C48—C47 | 0.8 (5) |
C15—C16—C17—C12 | 0.2 (7) | N6—C43—C48—C47 | 175.8 (3) |
C13—C12—C17—C16 | −0.3 (6) | C44—C43—C48—C50 | −176.7 (4) |
C11—C12—C17—C16 | −179.3 (4) | N6—C43—C48—C50 | −1.7 (5) |
C11—N3—C18—C23 | 92.1 (4) | Ni1—O3—C51—C52 | 94.4 (6) |
Ni1—N3—C18—C23 | −89.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3o···N2i | 0.85 | 2.15 | 2.910 (4) | 148 |
Symmetry code: (i) x, −y+1/2, z−1/2. |
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